Author: "Cyril Poriel" - Searchworks@Jio Institute Digital Library Search Results

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156 results on '"Cyril Poriel"'

1. Grafting Electron‐Accepting Fragments on [4]cyclo‐2,7‐carbazole Scaffold: Tuning the Structural and Electronic Properties of Nanohoops

Author: Clément Brouillac, Nemo McIntosh, Benoît Heinrich, Olivier Jeannin, Olivier De Sagazan, Nathalie Coulon, Joëlle Rault‐Berthelot, Jérôme Cornil, Emmanuel Jacques, Cassandre Quinton, and Cyril Poriel
Subjects: bridged cyclo‐oligophenylenes, charge transport, nanohoops, organic electronics, organic semiconductors, Science
Abstract: Abstract Since the first applications of nanohoops in organic electronics appear promising, the time has come to go deeper into their rational design in order to reach high‐efficiency materials. To do so, systematic studies dealing with the incorporation of electron‐rich and/or electron‐poor functional units on nanohoops have to be performed. Herein, the synthesis, the electrochemical, photophysical, thermal, and structural properties of two [4]cyclo‐2,7‐carbazoles, [4]C‐Py‐Cbz, and [4]C‐Pm‐Cbz, possessing electron‐withdrawing units on their nitrogen atoms (pyridine or pyrimidine) are reported. The synthesis of these nanohoops is first optimized and a high yield above 50% is reached. Through a structure‐properties relationship study, it is shown that the substituent has a significant impact on some physicochemical properties (eg HOMO/LUMO levels) while others are kept unchanged (eg fluorescence). Incorporation in electronic devices shows that the most electrically efficient Organic Field‐Effect transistors are obtained with [4]C‐Py‐Cbz although this compound does not present the best‐organized semiconductor layer. These experimental data are finally confronted with the electronic couplings between the nanohoops determined at the DFT level and have highlighted the origin in the difference of charge transport properties. [4]C‐Py‐Cbz has the advantage of a more 2D‐like transport character than [4]C‐Pm‐Cbz, which alleviates the impact of defects and structural organization.
Published: 2024
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2. Quinolinoacridine as High Efficiency Building Unit in Single‐Layer Phosphorescent Organic Light‐Emitting Diodes

Author: Clément Brouillac, Fabien Lucas, Denis Ari, Denis Tondelier, Jonathan Meot, Marc Malvaux, Cyril Jadaud, Christophe Lebreton, Joëlle Rault‐Berthelot, Cassandre Quinton, Emmanuel Jacques, and Cyril Poriel
Subjects: charge transport, host materials, quinolinoacridine, single‐layer phosphorescent OLED, Electric apparatus and materials. Electric circuits. Electric networks, TK452-454.4, Physics, QC1-999
Abstract: Abstract The performances of simplified single‐layer phosphorescent organic light‐emitting diodes (SL‐PhOLEDs) have significantly increased and they now appear to be a promising alternative to multi‐layer PhOLEDs. The blue and white emissions, far more challenging than all the other colours, are still particularly desired. Herein, a high efficiency host material for blue emitting SL‐PhOLED using the blue emitter FIr6 is reported, which is particularly interesting as it displays an emission at shorter wavelengths than the well‐known FIrpic emitter, almost exclusively reported in the SL‐PhOLEDs literature. The host material investigated herein is constructed on the electron‐rich quinolinoacridine and displays when incorporated in FIr6‐based SL‐PhOLEDs, an external quantum efficiency (EQE)⟩10% and a low Von of 3.1 V. This is the first work passing an EQE of 10% with FIr6 as an emitter. This host also reaches a very high EQE of 19% when used with the green emitter Ir(ppy)2acac, this performance being among the highest recorded for green SL‐PhOLEDs. Finally, as white SL‐PhOLEDs involve blue emitting SL‐PhOLEDs, this host is also used with a combination of blue and yellow emitters. An extremely high EQE of 24% is reached with CIE coordinates of (0.40;0.48). These findings show the real potential of the quinolinoacridine fragment to reach high performance multi‐colour SL‐PhOLEDs.
Published: 2024
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3. When Poor Light‐Emitting Spiro Compounds in Solution Turn into Emissive Pure Layers in Organic Light‐Emitting Diodes: The Key Role of Phosphine Substituents

Author: Pauline Tourneur, Fabien Lucas, Clément Brouillac, Cassandre Quinton, Roberto Lazzaroni, Yoann Olivier, Pascal Viville, Cyril Poriel, and Jérôme Cornil
Subjects: density functional theory, electroluminescence, light emission, phosphine groups, spiro compounds, Applied optics. Photonics, TA1501-1820, Optics. Light, QC350-467
Abstract: Spiro compounds are widely used as host matrices in organic light‐emitting diodes (OLEDs). Here, inspired by the recent developments in thermally activated delayed fluorescence (TADF) materials, the potential as a light emitter of two spiro‐configured organic semi‐conductors is investigated, constructed by the association of quinolinophenothiazine (QPTZ) or indoloacridine (IA) as the electron‐rich fragment and diphenylphosphine oxide fluorene as the electron‐poor fragment. By comparison with structural analogues lacking phosphine oxides, the crucial role played by these electron‐accepting substituents not only on the photo‐physical properties but also on the device performances is evidenced. Despite a very low quantum yield in solution, these two compounds unexpectedly display good emission properties when incorporated as a pure layer in OLEDs, thus highlighting the role of intermolecular effects.
Published: 2022
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4. An expedient approach to the 2,3,5,6-tetrasubstituted pyridine core of nosiheptide using oxidative cleavage of 2,3,5,8-tetrasubstituted quinolines

Author: David Taddei, Cyril Poriel, and Christopher J. Moody
Subjects: Organic chemistry, QD241-441
Published: 2006
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5. Electronic and Charge Transport Properties in Bridged versus Unbridged Nanohoops: The Role of the Nanohoop Size

Author: Fabien Lucas, Clement Brouillac, Nemo Mcintosh, Samuele Giannini, Joëlle Rault-Berthelot, Chirstophe Lebreton, David Beljonne, Jérôme Cornil, Emmanuel Jacques, Cassandre Quinton, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), University of Mons [Belgium] (UMONS), Institut d'Électronique et des Technologies du numéRique (IETR), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Nantes Université - pôle Sciences et technologie, Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ), This project has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement No 699648 (FRODO). We thankGENCI (N°AD0100805032R1) for computing time, the ANR (n°19-CE05-0024 and ANR-22-CE07-0041) for funding and for post-doctoral fellow (FL), the Region Bretagne (DIADEM project) and the ADEME (ECOELEC project) for PhD grants (FL and CB respectively), Nanorennes (Rennes) for the access to clean room facilities and CRMPO (Rennes) for mass analyses and variable temperatures NMR studies. We also thank Dr J.F Bergamini for the graphical abstract design. The work in Mons has been supported by the Marie Curie ITN project UHMob (GA-811284) and the Consortium des Équipements de Calcul Intensif (CÉCI), funded by the Fonds de la Recherche Scientifique de Belgique (F.R.S.-FNRS) under grant # 2.5020.11. J.C. and D.B. are FNRS research directors., and ANR-22-CE07-0041,Evolution,Evolution des matrices hôtes organiques pour des OLEDs phosphorescentes bleue et blanche à haute performance: Nouvelles générations de matériaux(2022)
Subjects: Organic Chemistry, [CHIM]Chemical Sciences, General Chemistry, hoop size effect, nanohoops, Catalysis, charge transport, cyclocarbazole
Abstract: International audience; In the field of p-conjugated nanohoops, the size of the macrocycle has a huge impact on its structural characteristics, which in turn affect its electronic properties. In this work, we report the first experimental investigations linking the size of a nanohoop to its charge transport properties, a key property in organic electronics. We describe the synthesis and the study of the first example of cyclocarbazole possessing five constituting building units, namely [5]-cyclo-N-butyl-2,7-carbazole [5]C-Bu-Cbz. By comparison with a shorter analogue, [4]-cyclo-N-butyl-2,7-carbazole [4]C-Bu-Cbz, we detail the photophysical, electrochemical, morphological and charge transport properties, highlighting the key role played by the hoop size. Particularly, we show that the saturated field effect mobility of [5]C-Bu-Cbz is four times higher than that of its smaller analogue [4]C-Bu-Cbz (4.22 × 10-5vs 1.04 × 10-5 cm².V-1.s-1). However, the study of the other OFET characteristics (threshold voltage VTH and subthreshold slope SS) suggest that a small nanohoop is beneficial for a good organization of the molecules in thin films whereas a large one increases the density of structural defects, and hence of traps for the charge carriers. The present findings are of interest for the further development of nanohoops in electronics.
Published: 2023

6. Pure Hydrocarbons: An Efficient Molecular Design Strategy for the Next Generation of Host Materials for Phosphorescent Organic Light-Emitting Diodes

Author: Cyril Poriel, Joëlle Rault-Berthelot, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Molecular design, Polymers and Plastics, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Oligomers, Materials Science (miscellaneous), Materials Chemistry, Chemical Engineering (miscellaneous), [CHIM.MATE]Chemical Sciences/Material chemistry, External quantum efficiency, Diodes, Materials
Abstract: International audience; Fantastic progresses have been made since the discovery of phosphorescent organic light-emitting diodes (PhOLEDs) in 1998 ( Nature 1998, 395, 151). In the emissive layer of a PhOLED, a heavy-metal complex (emitter) is dispersed as a guest in an organic semiconductor (host) in order to harvest both singlet and triplet excitons. This host/guest technique is essential to reach high-performance PhOLEDs. Undoubtedly, designing high-efficiency host materials for red, green, and blue phosphors has been the main driving force of the field. Nowadays, the most efficient PhOLEDs report very high external quantum efficiency (EQE) above 27% for the three colors. The molecular design of these high-efficiency host materials is based on small functional units, which have a crucial role in the device performance. These functional units are constructed on the assembly of electron-rich and/or electron-poor molecular fragments (such as carbazole, phenylamine, phosphine oxide, oxadiazole, pyridine, sulfone, etc.), which allows to finely tune the molecular orbitals energy levels (HOMO and LUMO) and the mobility of the charge carriers (hole and electrons). However, these molecular fragments incorporate heteroatoms, which in turn increase the molecular design complexity and production cost of the target materials and also create potential instability in the device. Indeed, the fragile C–N, C–P, and C–S bonds of such heteroatom-based hosts are involved, in part, in the OLED instability. As the instability of OLEDs is one of the most important problem to address at the current stage of development, developing new generations of host materials, without heteroatoms, has appeared as an important challenge in the field. In recent years, this new generation of host materials, called Pure HydroCarbons (PHC), only incorporating carbon and hydrogen atoms, has drawn the attention of the scientific community. PHC host materials only contain benzene rings, one of the most robust and inert building unit, which are assemble with suitable linkages to adjust their energy levels. However, reaching high-performance PhOLEDs with PHC-based hosts has been a real challenge. In the present account, thanks to a structure–properties relationship study, we recount the history of PHC-based host materials for PhOLEDs from the first example published in 2005 ( Org. Lett. 2005, 7, 5131), to the recent advances, which have shown that PHC hosts can overpass the performance of heteroatom-based hosts ( Chem. Sci. 2020, 11, 4887). Our group has contributed over the years to unravel the design principles of PHC hosts in order to improve the devices performance. In the light of recent results, PHC hosts now enter a new era and this work shows that the PHC design strategy is promising for the future development of OLED industry as a high-performance and low-cost option.
Published: 2022

7. Synthesis and electronic properties of bridged [8]-, [12]- and [16]-cyclo-para-phenylenes

Author: Fabien Lucas, Joëlle Rault-Berthelot, Cassandre Quinton, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), European Union [699648], Region Bretagne (DIADEM project), GENCI [AD010805032R1], and European Project: 699648,H2020,H2020-MSCA-IF-2015,FRODO(2016)
Subjects: Materials Chemistry, [CHIM]Chemical Sciences, General Chemistry
Abstract: International audience; Hoop-shaped pi-conjugated macrocycles constitute a new family of pi-conjugated systems displaying unique properties induced by their radially directed pi-orbitals. The electronic properties of these nanohoops are deeply dependent on their budding units and their size. We report herein the first size dependence study of [8]-, [12]- and [16] cyclo-para-phenylenes bridged by nitrogen atoms. The properties were elucidated by H-1 NMR, cyclic voltammetry, UV-vis absorption and fluorescence spectroscopy (in solution and in thin film). Thus, this work reports one of the largest bridged nanohoops synthesized, namely [4]cyclo-para-9-ethylhexyl-2,7-diphenyl-carbazole [16]CPP4N, an analog of [16]CPP, which displays an alternation of four unbridged biphenylenes and four nitrogen bridged biphenylenes. Removing either all the unbridged phenylenes ([4]cyclo-para-9-ethylhexyl-carbazole [8]CPP4N, an analog of [8]CPP) or one budding unit ([3]cyclo-para-9-ethylhexyl-2,7-diphenyl-carbazole [12]CPP3N, an analog of [12]CPP) allows decreasing the size of the nanohoop with nevertheless drastically different consequences on the properties. This is what we aim at reporting in this work.
Published: 2022

8. Dispiroacridine-indacenobisthiophene positional isomers: impact of the bridge on the physicochemical properties

Author: Bertrand Donnio, Jean-David Peltier, Joëlle Rault-Berthelot, Benoît Heinrich, Nicolas Leclerc, Cyril Poriel, Thomas Heiser, Olzhas A. Ibraikulov, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des sciences de l'ingénieur, de l'informatique et de l'imagerie (ICube), École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Université de Strasbourg (UNISTRA)-Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de Recherche en Informatique et en Automatique (Inria)-Les Hôpitaux Universitaires de Strasbourg (HUS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Region Bretagne Region Bretagne, Agence de l'Environnement et de la Maitrise de l'Energie (ADEME), CNRS Centre National de la Recherche Scientifique (CNRS) European Commission, Universite de Strasbourg (UNISTRA), GENCI [2021-A0100805032], poriel, cyril, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE)
Subjects: Materials science, business.industry, 02 engineering and technology, Structural engineering, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Bridge (interpersonal), 0104 chemical sciences, [CHIM] Chemical Sciences, Materials Chemistry, Structural isomer, [CHIM]Chemical Sciences, General Materials Science, 0210 nano-technology, business
Abstract: International audience; We report the influence of positional isomerism on the electronic (electrochemical HOMO/LUMO energy levels), photophysical and physical properties (molecular organization, crystallinity and phase transitions) and charge transport properties of dispiroacridine-indacenobisthiophene positional isomers. The isomers differ from the central indacenobisthiophene (IDT) core, which displays either para or meta linkages. We show that the spiro-connected phenylacridine bridges have a significant influence on all these properties and particularly on the charge transport mobility values, which were found to be higher in the meta isomer than in the para isomer. This finding is different to what was reported in the literature for the other couples of IDT-based isomers and shows the key role played by the spiro-connected fragments in these molecular systems.
Published: 2022

9. Are pure hydrocarbons the future of host materials for blue phosphorescent organic light-emitting diodes?

Author: Cyril Poriel, Joëlle Rault-Berthelot, Zuo-Quan Jiang, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Soochow University
Subjects: Materials Chemistry, [CHIM]Chemical Sciences, General Materials Science
Abstract: International audience; The fantastic development of phosphorescent organic light-emitting diodes (PhOLEDs) has been undoubtedly driven by the molecular design of high-efficiency host materials for red, green and blue phosphors. Fine tuning the electronic and physical properties of the host materials has allowed very high External Quantum Efficiencies (EQEs) to be reached, reported nowadays above 30% for the three colours. The most used molecular design strategy consists of judiciously assembling small functional units to maintain a high triplet energy level (E-T), essential to ensure efficient energy transfer from the host to the guest phosphor. To adjust the molecular orbital energy levels and the charge transport, these functional units display electron-donating (for hole transport) and electron-accepting (for electron transport) capabilities. Hundreds of host materials have been reported in the literature since the discovery of PhOLEDs in 1998. However, they all have a common characteristic: they incorporate heteroatoms. However, although these functional units are highly beneficial for the device performance, several works have highlighted their potential instability in the device. As the stability of blue-emitting PhOLEDs is a central concern in the field, finding alternatives to heteroatom-based hosts is a mandatory step. In recent years, pure hydrocarbon (PHC) materials, only built with carbon and hydrogen atoms, have shown real potential for the next generation of PhOLEDs. In the light of the literature, it appears nowadays that the PHC design strategy is very promising for the future development of the OLED industry as a high-performance and low-cost option. This is the purpose of the present Chemistry Frontiers.
Published: 2022

10. [4]-Cyclo-2,7-carbazole as host material in high-efficiency phosphorescent OLEDs: A new perspective for nanohoops in organic electronics

Author: Clément Brouillac, Fabien Lucas, Denis Tondelier, Joëlle Rault‐Berthelot, Christophe Lebreton, Emmanuel Jacques, Cassandre Quinton, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Institut d'Électronique et des Technologies du numéRique (IETR), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Nantes Université - pôle Sciences et technologie, Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ), European Union [AD0100805032R1], ANR ANR-19-CE05-0024, CRMPO (Rennes), GENCI, Agence de l'Environnement et de la Maitrise de l'energie (ADEME), Dr. Bruno Lafitte (ADEME), 699648, 19-CE05-0024, ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019), and European Project: 699648,H2020,H2020-MSCA-IF-2015,FRODO(2016)
Subjects: host material, organic semiconductor, nanohoops organic semiconductor host material phosphorescent organic light -emitting diode structure-properties relationship curved -conjugated systems, curved -conjugated systems, [CHIM]Chemical Sciences, nanohoops, structure-properties relationship, Atomic and Molecular Physics, and Optics, Electronic, Optical and Magnetic Materials, phosphorescent organic light -emitting diode
Abstract: International audience
Published: 2023

11. Simplified green-emitting single-layer phosphorescent organic light-emitting diodes with an external quantum efficiency > 22%

Author: Fabien Lucas, Clément Brouillac, Sadiara Fall, Nicolas Zimmerman, Denis Tondelier, Bernard Geffroy, Nicolas Leclerc, Thomas Heiser, Christophe Lebreton, Emmanuel Jacques, Cassandre Quinton, Joëlle Rault-Berthelot, Cyril Poriel, Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des sciences de l'ingénieur, de l'informatique et de l'imagerie (ICube), École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Université de Strasbourg (UNISTRA)-Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de Recherche en Informatique et en Automatique (Inria)-Les Hôpitaux Universitaires de Strasbourg (HUS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Institut d'Électronique et des Technologies du numéRique (IETR), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Nantes Université - pôle Sciences et technologie, Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ), ADEME, GENCI (project no. AD0100805032R1), ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019), Palacin, Serge, SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches - - SPIRO-QUEST2019 - ANR-19-CE05-0024 - AAPG2019 - VALID, and Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685)
Subjects: [CHIM.MATE] Chemical Sciences/Material chemistry, General Chemical Engineering, Materials Chemistry, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, Charge transport, Layers, Diodes, Electrodes, External quantum efficiency
Abstract: International audience; Nowadays, phosphorescent organic light-emitting diodes (PhOLEDs) is a widespread technology, in which all the high-performance devices are constructed on a stack of different organic layers called multi-layer devices (ML-PhOLEDs). Thanks to these functional layers, the injection, the transport, and the recombination of holes and electrons in the emissive layer (EML) are significantly improved, allowing to reach high performances. In this technology, the ideal devices are the single-layer PhOLEDs (SL-PhOLEDs), with a very simple stack only constituted by the electrodes and the EML. These devices are simple, very easy to fabricate, and can hence significantly decrease their costs. Nevertheless, removing the functional layers of an OLED drastically decreases the performances and there is, so far, only a few examples of high-performance SL-PhOLEDs. Thus, in SL-PhOLEDs, the role of the functional layer should be performed by the EML, which should allow an excellent injection, transport, and recombination of holes and electrons. In this work, thanks to a rational molecular design of the EML, we report a green-emitting SL-PhOLED, displaying a very high external quantum efficiency of 22.7%. The EML of this device is constructed on the barely studied Ir(ppy)2acac phosphor and a high efficiency host material possessing a Donor-spiro-Acceptor design. This performance is, to the best of our knowledge, the highest reported to date for SL-PhOLEDs (all colors considered). Through a structure/property/device performance relationship study combining morphological (AFM), photophysical (time-resolved spectroscopy) and charge transport studies, we show that the EML presents all the required characteristics such as smooth surface, quick radiative deactivation, and ambipolarity. In addition, the comparison with Ir(ppy)3, the most famous green emitter used in PhOLEDs, highlights the high potential of Ir(ppy)2acac. The impact of the phosphorescent emitter on the ambipolarity of the charge transport is particularly evidenced.
Published: 2022

12. Pure Hydrocarbon Materials as Highly Efficient Host for White Phosphorescent Organic Light‐Emitting Diodes: A New Molecular Design Approach

Author: Fan‐Cheng Kong, Yuan‐Lan Zhang, Cassandre Quinton, Nemo McIntosh, Sheng‐Yi Yang, Joëlle Rault‐Berthelot, Fabien Lucas, Clément Brouillac, Olivier Jeannin, Jérôme Cornil, Zuo‐Quan Jiang, Liang‐Sheng Liao, Cyril Poriel, Soochow University, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Mons (UMons)
Subjects: Pure Aromatic Hydrocarbons, [CHIM.ORGA]Chemical Sciences/Organic chemistry, White Emission, Host Materials, Phosphorescent Organic Light-Emitting Diodes, General Chemistry, General Medicine, Catalysis, Blue emission, [SPI.TRON]Engineering Sciences [physics]/Electronics
Abstract: International audience; To date, all efficient host materials reported for phosphorescent OLEDs (PhOLEDs) are constructed with heteroatoms, which have a crucial role in the device performance. However, it has been shown in recent years that the heteroatoms not only increase the design complexity but can also be involved in the instability of the PhOLED, which is nowadays the most important obstacle to overcome. Herein, we design pure aromatic hydrocarbon materials (PHC) as very efficient hosts in high-performance white and blue PhOLEDs. With EQE of 27.7 %, the PHC-based white PhOLEDs display similar efficiency as the best reported with heteroatom-based hosts. Incorporated as a host in a blue PhOLED, which are still the weakest links of the technology, a very high EQE of 25.6 % is reached, overpassing, for the first time, the barrier of 25 % for a PHC and FIrpic blue emitter. These performance show that the PHC strategy represents an effective alternative for the future development of the OLED industry.
Published: 2022

13. Quinolinophenothiazine as an electron rich fragment for high efficiency RGB single-layer phosphorescent organic light-emitting diodes

Author: Thomas Heiser, Nicolas Leclerc, Clément Brouillac, Bernard Geffroy, Cassandre Quinton, Olzhas A. Ibraikulov, Denis Tondelier, Fabien Lucas, Cyril Poriel, and Joëlle Rault-Berthelot
Subjects: Organic electronics, Materials science, Fragment (computer graphics), business.industry, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Atom, Materials Chemistry, OLED, Molecule, Optoelectronics, General Materials Science, Quantum efficiency, 0210 nano-technology, Phosphorescence, business, Diode
Abstract: The quinolinophenothiazine (QPTZ) fragment is a phenylacridine bridged by a sulphur atom. Despite appealing properties induced by this bridging (e.g. strong electron rich character), this fragment remains almost unexplored to date in organic electronics. Based on this QPTZ fragment, we report herein a high efficiency host for the new generation of simplified Phosphorescent Organic Light-Emitting Diodes so called Single-Layer (SL-PhOLEDs). This host material is constructed on the association of an electron rich fragment (QPTZ), and an electron-deficient fragment (2,7-bis (diphenylphosphineoxide)-fluorene). This molecule displays all the necessary properties to be used in universal SL-PhOLEDs. Red, green and blue SL-PhOLEDs were successfully fabricated and yielded an average external quantum efficiency of ca 10%. High luminances of ca 10000 cd/m$^2$ for red and blue devices and 40000 cd/m$^2$ for green devices were obtained. These luminances are higher than the best reported to date with structurally related analogues and highlight the strong interest of the QPTZ fragment in such devices. Thanks to its high HOMO level, the QPTZ unit also allows to decrease the threshold voltage, which is a key characteristic in the OLED technology. This work shows the potential of the QPTZ fragment in the design of host materials for high performance single-layer PhOLEDs.
Published: 2021

14. [ n ]‐Cyclo‐9,9‐dibutyl‐2,7‐fluorene ( n =4, 5): Nanoring Size Influence in Carbon‐Bridged Cyclo‐ para ‐phenylenes

Author: Cyril Poriel, Cassandre Quinton, Joëlle Rault-Berthelot, Lambert Sicard, Fabien Lucas, Olivier Jeannin, Pierre-Antoine Bouit, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), 699648, H2020 Marie Skłodowska-Curie Actions, n°14-CE05-0024, Agence Nationale de la Recherche, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, ring bridging, chemistry.chemical_element, General Medicine, General Chemistry, Fluorene, 010402 general chemistry, Electrochemistry, 01 natural sciences, Catalysis, Fluorescence spectroscopy, 0104 chemical sciences, Ring size, chemistry.chemical_compound, Crystallography, chemistry, ring size effect, cyclofluorene, nanorings, Absorption (chemistry), Cyclic voltammetry, Carbon, Nanoring
Abstract: International audience; For the last ten years, ring-shaped -conjugated macrocycles possessing radially directed -orbitals have been subject to intense research. The electronic properties of these rings are deeply dependent on their size. However, most studies involve the flagship family of nanorings: the cyclo-para-phenylenes. We report herein the synthesis and study of the first examples of cyclofluorenes possessing five constituting fluorene units. The structural, optical and electrochemical properties were elucidated by X-ray crystallography, UV-vis absorption and fluorescence spectroscopy, and cyclic voltammetry. By comparison with a shorter analogue, [4]-cyclofluorene, we show how the electronic properties of [5]-cyclofluorenes are drastically different from those of [4]-cyclofluorenes, highlighting the key role played by the ring size in the cyclofluorene family.
Published: 2020

15. White-light electroluminescence from a layer incorporating a single fully-organic spiro compound with phosphine oxide substituents

Author: Roberto Lazzaroni, Cassandre Quinton, Fabien Lucas, Yoann Olivier, P Viville, P Tourneur, Jérôme Cornil, Cyril Poriel, Université de Mons (UMons), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Namur [Namur] (UNamur), 2.5020.11, Fonds De La Recherche Scientifique - FNRS, 19-CE05-0024, Agence Nationale de la Recherche, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019)
Subjects: Phosphine oxide, chemistry.chemical_classification, Materials science, Spiro compound, Intermolecular force, 02 engineering and technology, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, Electroluminescence, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Fluorescence, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Intramolecular force, Materials Chemistry, OLED, 0210 nano-technology, Phosphine
Abstract: International audience; We have investigated the potential as an OLED emitter of a spiro compound with phosphine substituents initially designed as a host layer for triplet emitters. This is motivated by the fact that the spiro architecture is expected to reduce the detrimental impact of intermolecular interactions, thus allowing for the use of a single-component layer. Moreover, theoretical calculations suggest that this compound displays all features required for a thermally-assisted delayed fluorescence (TADF) behavior. The photophysical properties of the compound in solution are extremely unusual, as illustrated in particular by a dual emission band with relative intensities strongly depending on the experimental conditions. Although no TADF behavior is evidenced in OLED devices, the compound unexpectedly generates a white light signal, which is interpreted as the result of the formation of both intramolecular and intermolecular (exciplex) charge-transfer states.
Published: 2020

16. Spiro-configured dibenzosuberene compounds as deep-blue emitters for organic light-emitting diodes with a CIEy of 0.04

Author: Clément Brouillac, Wan-Shan Shen, Joëlle Rault-Berthelot, Olivier Jeannin, Cassandre Quinton, Zuo-Quan Jiang, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Soochow University, ANR [ANR-19-CE05-0024], Agence de l'Environnement et de la Maitrise de l'Energie (ADEME), and ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019)
Subjects: spiro compounds, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Materials Chemistry, organic light-emitting diode, General Materials Science, Dibenzosuberene, deep-blue emitter
Abstract: International audience; Deep blue electroluminescence is highly required for organic light-emitting diode (OLED) technology. However, designing fluorophores displaying adequate CIE coordinates and particularly a low CIEy is far from an easy task. We report in this work the synthesis, the physico-chemical properties and the application of deep blue emitters constructed using the dibenzosuberene (DBS) molecular fragment in OLEDs. Three emitters, SPA-DBS, SIA-DBS and SQPTZ-DBS, have been constructed following a similar molecular design strategy that is the spiro connection of an electron rich unit, namely N-phenylacridine (PA), indoloacridine (IA) or quinolinophenothiazine (QPTZ) to the DBS core. The PA, IA and QPTZ fragments are known to be efficient hole injecters due to their strong electron-rich character. Through a structure/property relationship study, we analyse the electrochemical, photophysical and thermal behaviours of these three emitters. When used as an emitter in an OLED, a deep-blue emission with CIE of (0.16, 0.04) is obtained with SPA-DBS, reaching an EQE of ca. 1% and a V-on of 4 V. The CIEy coordinate of 0.04 appears to be particularly low and fits the NSTC, ITU and EBU standards.
Published: 2022

17. Spirobifluorene Dimers: Understanding How The Molecular Assemblies Drive The Electronic Properties

Author: Cassandre Quinton, Olivier Jeannin, Cyril Poriel, Fabien Lucas, Joëlle Rault-Berthelot, Zuo-Quan Jiang, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Soochow University, ANR (SPIROQUEST) French National Research Agency (ANR) [19-CE05-024], Region Bretagne (DIADEM), ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Organic electronics, Materials science, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, organic semi-conductors, Nanotechnology, triplet state energy level, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, Biomaterials, organic electronics, Electrochemistry, [CHIM]Chemical Sciences, structure-properties relationship study, spirobifluorene, Electronic properties
Abstract: International audience; Spirobifluorene (SBF) is one of the most important scaffolds used in the design of organic semi-conductors (OSCs) for electronics. In recent years, among all the structures developed for these applications, SBF dimers have been highlighted due to their great potential in thermally activated delayed fluorescence and in phosphorescent organic light-emitting diodes. Attaching two SBF units generate 10 dimers, each possessing its own structural specificity, which in turn drives its electronic properties. These ten SBF dimers are gathered herein. Understanding how the molecular assembly determines the electronic properties has been one of the pillars of organic electronics. This is the goal of this article. As positional isomerism is a key tool to design OSCs, defining the design guidelines for the SBF scaffold appears of interest for the future of this building block. Herein, the importance of the two main parameters involved in the electrochemical and photophysical properties, namely the nature of the phenyl linkages and the steric congestion between the two SBF units is discussed. The combination of these two parameters drives the electronic properties but their respective weight is different as a function of the regioisomer involved or of the property considered (frontier orbitals energy level, absorption, fluorescence, phosphorescence).
Published: 2021

18. Designing Host Materials for the Emissive Layer of Single-Layer Phosphorescent Organic Light-Emitting Diodes: Toward Simplified Organic Devices

Author: Joëlle Rault-Berthelot, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR French National Research Agency (ANR) [19-CE05-0024], Region Bretagne (DIADEM project), ADEME, ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Materials science, Organic devices, frontier molecular orbitals, molecular design, 02 engineering and technology, Electroluminescence, 010402 general chemistry, 01 natural sciences, singleand#8208, electroluminescence, Biomaterials, host material, emitting diode, Electrochemistry, OLED, ambipolar charge transport, [CHIM]Chemical Sciences, Organic electronics, business.industry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, triplet energy, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, organic electronics, layer phosphorescent organic lightand#8208, Optoelectronics, 0210 nano-technology, Phosphorescence, business, Host (network), Layer (electronics), Single layer
Abstract: International audience; Thanks to the tremendous effort over the last 20 years, phosphorescent organic light-emitting diodes (PhOLEDs) represent a prevalent technology. In this technology, all the high-efficiency PhOLEDs are multi-layer devices constituting, in addition to the emissive layer (EML), of a stack of functional organic layers. These layers play a crucial role in the device performance as they improve the injection, transport, and recombination of charges within the EML. Single-layer PhOLEDs (SL-PhOLEDs) represent ideal OLEDs, consisting only of the electrodes and the EML. However, reaching high-performance SL-PhOLED is far from easy, as removing the functional layers of an OLED stack dramatically decreases the performance. To achieve high SL-PhOLED efficiency, the efficient injection, transport, and recombination of charges should be insured by the EML, and particularly, by the host material. In the present exhaustive review, the different molecular design strategies are analyzed, which have been used to construct high-efficiency hosts for SL-PhOLED. The impact of the electronic properties (triplet energy, HOMO/LUMO energy, mobility etc.) on the device characteristics (threshold voltage, electroluminescent spectrum, external quantum efficiency, etc.) are discussed. This allows to draw a structure/properties/device performance relationship map of interest for the future design of functional materials for SL-PhOLEDs.
Published: 2021

19. Diodes électroluminescentes organiques : quatre technologies différentes

Author: Joëlle Rault-Berthelot, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Physics, électronique organique, phosphorescence, thermally activated delayed fluorescence, OLED, fluorescence retardée activée thermiquement, organic electronic, hyperfluorescence, [CHIM]Chemical Sciences, fluorescence, Humanities
Abstract: International audience; Les diodes organiques électroluminescentes (OLEDs) sont des dispositifs électroniques capables d’émettre de la lumière sous l’effet d’un champ électrique. L’architecture de base d’une OLED consiste en un film mince émetteur de lumière (EML) déposé entre deux électrodes. Il existe quatre générations d’OLEDs différenciées par le processus photo-physique conduisant à l’émission de la lumière : l’OLED fluorescente, l’OLED phosphorescente, l’OLED TADF et l’OLED hyperfluorescente. Cet article présente les quatre générations d’OLEDs pour lesquelles le mécanisme d’émission de lumière est discuté à la lumière d’exemples sélectionnés dans la littérature.
Published: 2021

20. A-pi-A, D-pi-D and D-pi-A blue emitting fluorophores based on dispiro[fluorene-9,6 '-indeno[1,2-b]fluorene-12 ',9 '-fluorene]

Author: Maxime Romain, Joëlle Rault-Berthelot, Damien Thirion, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Region Bretagne, Agence de l'Environnement et de la Maitrise de l'Energie (ADEME), ANR (SPIROQUEST) French National Research Agency (ANR) [19-CE05-024], Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Materials science, 010405 organic chemistry, 02 engineering and technology, Fluorene, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Crystallography, chemistry, Chemistry (miscellaneous), Blue emitting, Surface modification, [CHIM]Chemical Sciences, General Materials Science, 0210 nano-technology
Abstract: International audience; We report a series of blue fluorophores based on the dispiro[fluorene-9,6 '-indeno[1,2-b]fluorene-12 ',9 ''-fluorene] (DSF-IF) scaffold. The DSF-IF scaffold, introduced in 2006 in the literature for organic electronic applications, is nowadays a very useful building block to construct functional materials. However, the functionalization of the DSF-IF scaffold has been poorly investigated to date. In this work, we focus on three different molecular architectures incorporating at each extremity of the central dihydroindenofluorenyl core either an electron accepting unit (A-pi-A), an electron donating unit (D-pi-D) or one of each (D-pi-A). The different substitutions of the dihydroindeno[1,2-b]fluorenyl core has allowed the strong modulation of the properties of the dyes and the precise study of the effect of this fragment as a pi-conjugated bridge.
Published: 2021

21. Journal of Materials Chemistry C Editor's choice web collection: 'Spiro compounds for electronics'

Author: Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Solid-state chemistry, Materials science, Materials Chemistry, [CHIM]Chemical Sciences, Nanotechnology, 02 engineering and technology, General Chemistry, Electronics, 010402 general chemistry, 021001 nanoscience & nanotechnology, 0210 nano-technology, 01 natural sciences, 0104 chemical sciences
Abstract: Cyril Poriel introduces the Journal of Materials Chemistry C Editor's choice web collection on advances in ‘Spiro compounds for electronics’.
Published: 2021

22. Persistent Organic Room-Temperature Phosphorescence in Cyclohexane

Author: Ludovic, Favereau, Cassandre, Quinton, Cyril, Poriel, Thierry, Roisnel, Denis, Jacquemin, and Jeanne, Crassous
Abstract: Persistent metal-free room-temperature phosphorescence (RTP) materials attract significant interest owing to the production of long-lived triplet excited states. Although several organic designs show RTP, the impact of intermolecular interactions on the triplet excitons stabilization and migrations remains hardly understood because obtaining different ordered intermolecular interactions while conserving identical molecular electronic properties is very challenging. We propose here a new strategy to circumvent this problem by taking advantage of the distinct molecular packing that can be found between enantiomer and racemic forms of a chiral molecule. Structural, photophysical, and chiroptical investigations of chiral cyclohexane bisphthalimide derivatives showed that heterochiral and homochiral dimer interactions play a crucial role on the triplet excited state stabilization, resulting in higher RTP efficiency for enantiopure systems than for racemic one. This study paves the way to the use of molecular chirality to rationalize supramolecular properties arising from subtle intermolecular interactions.
Published: 2020

23. Evolution of pure hydrocarbon hosts: simpler structure, higher performance and universal application in RGB phosphorescent organic light-emitting diodes

Author: Fan-Cheng Kong, Zuo-Quan Jiang, Liang-Sheng Liao, Sheng-Yi Yang, Joëlle Rault-Berthelot, Cassandre Quinton, Yang-Kun Qu, Olivier Jeannin, Cyril Poriel, Fabien Lucas, Sarvendra Kumar, Qiang Wang, Soochow University, Humboldt-Universität zu Berlin, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), National Key RandD Program of China [2016YFB0400700], National Natural Science Foundation of China National Natural Science Foundation of China [51773141, 51873139, 21572152], Natural Science Foundation of Jiangsu Province of ChinaNatural Science Foundation of Jiangsu Province [BK20181442], CINES [2019-A0040805032], ANR French National Research Agency (ANR) [14-CE05-0024-Men, 19-CE05-0024-SpiroQuest], Region Bretagne (DIADEM project), Collaborative Innovation Center of Suzhou Nano Science Technology, Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), 111 Project Ministry of Education, China - 111 Project, Humboldt University Of Berlin, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019)
Subjects: chemistry.chemical_classification, Materials science, business.industry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Heteroatom, Phosphor, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 7. Clean energy, 01 natural sciences, 0104 chemical sciences, [SPI.TRON]Engineering Sciences [physics]/Electronics, Chemistry, Hydrocarbon, chemistry, OLED, Optoelectronics, RGB color model, 0210 nano-technology, business, Phosphorescence, Diode
Abstract: In the field of phosphorescent organic light-emitting diodes (PhOLEDs), designing high-efficiency universal host materials for red, green and blue (RGB) phosphors has been quite a challenge. To date, most of the high-efficiency universal hosts reported incorporate heteroatoms, which have a crucial role in the device performance. However, the introduction of different kinds of heterocycles increases the design complexity and cost of the target material and also creates potential instability in the device performance. In this work, we show that pure aromatic hydrocarbon hosts designed with the 9,9′-spirobifluorene scaffold are high-efficiency and versatile hosts for PhOLEDs. With external quantum efficiencies of 27.3%, 26.0% and 27.1% for RGB PhOLEDs respectively, this work not only reports the first examples of high-efficiency pure hydrocarbon materials used as hosts in RGB PhOLEDs but also the highest performance reported to date for a universal host (including heteroatom-based hosts). This work shows that the PHC design strategy is promising for the future development of the OLED industry as a high-performance and low-cost option., In this work, we propose pure hydrocarbon materials as universal hosts for high-efficiency red, green and blue phosphorescent organic light-emitting diodes.
Published: 2020

24. Blue Single-Layer Organic Light-Emitting Diodes Using Fluorescent Materials: A Molecular Design View Point

Author: Joëlle Rault-Berthelot, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 11‐BS07‐020‐01/14‐CE05‐0024, Agence Nationale de la Recherche, Agence de l'Environnement et de la Maîtrise de l'Energie, Région Bretagne, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Organic electronics, Materials science, Single-Layer Organic Light-Emitting Diodes, Blue fluorescence, business.industry, 02 engineering and technology, organic light-emitting diodes, 010402 general chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, Biomaterials, organic electronics, Electrochemistry, Fluorescent materials, OLED, Optoelectronics, [CHIM]Chemical Sciences, Point (geometry), 0210 nano-technology, business, Single layer
Abstract: International audience; Since the beginning of organic light-emitting diodes (OLEDs), blue emission has attracted the most attention and many research groups worldwide have worked on the design of materials for stable and highly efficient blue OLEDs. However, almost all the high-efficiency blue OLEDs using fluorescent materials are multilayer devices, which are constituted of a stack of organic layers to improve the injection, transport, and recombination of charges within the emissive layer. Although the technology has been mastered, it suffers from real complexity and high cost and is time-consuming. Simplifying the multilayer structure with a single-layer one, the simplest devices made only of electrodes and the emissive layer have appeared as an appealing strategy for this technology. However, removing the functional organic layers of an OLED stack leads to a dramatic decrease of the performance and achieving high-efficiency blue single-layer OLEDs requires intense research especially in terms of materials design. Herein, an exhaustive review of blue emitting fluorophores that have been incorporated in single-layer OLEDs is reported, and the links between their electronic properties and the device performance are discussed. Thus, a structure/properties/device performance relationship map is drawn, which is of interest for the future design of organic materials.
Published: 2020

25. Modulation of circularly polarized luminescence through excited-state symmetry breaking and interbranched exciton coupling in helical push–pull organic systems

Author: Jochen Autschbach, Cassandre Quinton, Thierry Roisnel, Clément Cabanetos, Monika Srebro-Hooper, Lorenzo Arrico, Kais Dhbaibi, Jeanne Crassous, Nicolas Vanthuyne, Bassem Jamoussi, Cyril Poriel, Ludovic Favereau, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Jagiellonian University [Krakow] (UJ), Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Centre National de la Recherche Scientifique (CNRS), University of Pisa - Università di Pisa, Faculty of Sciences, Gabès, Tunisia, MOLTECH-Anjou, Université d'Angers (UA)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry [Buffalo], University at Buffalo [SUNY] (SUNY Buffalo), State University of New York (SUNY)-State University of New York (SUNY), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), University of Gabes, Synthèse Caractérisation Analyse de la Matière (ScanMAT), Université de Rennes (UR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Uniwersytet Jagielloński w Krakowie = Jagiellonian University (UJ), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), King Abdulaziz University, Université d'Angers (UA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), University of Rennes 1, Campus France, National Science FoundationNational Science Foundation (NSF) [CHE-1855470], Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut de Chimie du CNRS (INC), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)
Subjects: Coupling, Quantitative Biology::Biomolecules, Materials science, Condensed Matter::Other, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Exciton, General Chemistry, 010402 general chemistry, 01 natural sciences, Molecular physics, Symmetry (physics), 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Condensed Matter::Materials Science, Chemistry, Excited state, [CHIM]Chemical Sciences, Symmetry breaking, Solvent effects, Spectroscopy, Luminescence, ComputingMilieux_MISCELLANEOUS
Abstract: Solvent polarity effect on circularly polarized luminescence intensity was assessed in helical push–pull organic systems through excited-state symmetry breaking and interbranched exciton coupling., π-Helical push–pull dyes were prepared and their (chir)optical properties were investigated both experimentally and computationally. Specific fluorescent behaviour of bis-substituted system was observed with unprecedented solvent effect on the intensity of circularly polarized luminescence (CPL, dissymmetry factor decreasing from 10–2 to 10–3 with an increase in solvent polarity) that was linked to a change in symmetry of chiral excited state and suppression of interbranched exciton coupling. The results highlight the potential of CPL spectroscopy to study and provide a deeper understanding of electronic photophysical processes in chiral π-conjugated molecules.
Published: 2020

26. Universal host materials for red, green and blue high-efficiency single-layer phosphorescent organic light-emitting diodes

Author: Sadiara Fall, Cassandre Quinton, Joëlle Rault-Berthelot, Thomas Heiser, Fabien Lucas, Cyril Poriel, Nicolas Leclerc, Bernard Geffroy, Denis Tondelier, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des sciences de l'ingénieur, de l'informatique et de l'imagerie (ICube), École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Université de Strasbourg (UNISTRA)-Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de Recherche en Informatique et en Automatique (Inria)-Les Hôpitaux Universitaires de Strasbourg (HUS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), ANR-19-CE05-0024,SPIRO-QUEST,SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches(2019), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), 19-CE05-0024, Agence Nationale de la Recherche, Jonchère, Laurent, and SPIRO-QUinolinophenothiazine: semi-conducteurs haute-performance pour des OLEDs Phosphorescentes monocouches - - SPIRO-QUEST2019 - ANR-19-CE05-0024 - AAPG2019 - VALID
Subjects: Materials science, Positional isomerism TOC, 02 engineering and technology, Single-layer red, Fluorene, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, [CHIM] Chemical Sciences, Materials Chemistry, OLED, [CHIM]Chemical Sciences, Ambipolar charge transport, green and blue phosphorescent organic light-emitting diode, Common emitter, Diode, [CHIM.MATE] Chemical Sciences/Material chemistry, business.industry, Host materials, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Threshold voltage, Phosphine oxide, chemistry, Spiro compounds, Optoelectronics, RGB color model, Quantum efficiency, 0210 nano-technology, business, Phosphorescence
Abstract: International audience; Simplifying the structure of Organic Light-Emitting Diodes (OLEDs) has been for the last twenty years the purpose of many studies. However, despite these efforts, only a few materials provide high efficiency devices. We report herein efficient design strategies to construct universal host materials for red, green and blue Single-Layer Phosphorescent OLEDs (SL-PhOLEDs). The three materials investigated, SPA-2,7-F(POPh$_2$)$_2$, SPA-3,6-F(POPh$_2$)$_2$ and SPA-2-FPOPh$_2$, have been synthesized via an efficient approach and are constructed on the association of an electron rich phenylacridine unit connected by a spiro carbon atom to three different electron-deficient diphenylphosphineoxide-substituted fluorenes. Electrochemical, spectroscopic, thermal and transport properties are discussed. The position (C2 and C7 vs. C3 and C6) and the number (1 vs. 2) of diphenylphosphineoxide units on the fluorene backbone have been particularly studied to highlight the best combination in term of device performances. Red, green and blue SL-PhOLEDs (RGB SL-PhOLEDs) have been fabricated and characterized and their performances discussed. Of particular interest, we managed to reach a FIr6-based SL-PhOLED (with SPA-2-FPOPh$_2$) possessing an external quantum efficiency of 9.1% and a low threshold voltage (below 3 V). As far as we know, this is the first example of SL-PhOLED using this blue phosphorescent emitter. On the other hand, with notably a very high external quantum efficiency of 18% with FIrpic as sky blue emitter, SPA-2,7-F(POPh$_2$)$_2$ displays the highest overall performance in the series and the highest overall performance ever reported for RGB SL-PhOLEDs using a universal host. This not only shows that the association of phenylacridine and diphenylphosphineoxide units fulfils the required criteria for an universal host for high efficiency SL-PhOLEDs but also highlights that the arrangement of these fragments drives the device performance.
Published: 2020

27. Highly Efficient Thermally Activated Delayed Fluorescence via an Unconjugated Donor–Acceptor System Realizing EQE of Over 30%

Author: Sheng-Yi Yang, Hong-Cheng Li, Liang-Sheng Liao, Guohua Xie, Sheng-Nan Zou, Chen-Chen Peng, Zuo-Quan Jiang, Lin-Song Cui, Cyril Poriel, Soochow University, Wuhan University [China], University of Cambridge [UK] (CAM), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), National Key Research and Development Program of China. Grant Number: 2016YFB0400700, National Natural Science Foundation of China. Grant Numbers: 51773141, 51873139, 21572152, Natural Science Foundation of Jiangsu Province. Grant Number: BK20181442, Collaborative Innovation Centre of Suzhou Nano Science & Technology, Priority Academic Program Development of Jiangsu Higher Education Institutions, 111 Project, State Administration of Foreign Experts Affairs, China, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: thermally activated delayed fluorescence, Materials science, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, OLED, General Materials Science, intramolecular spatial charge transfer, Common emitter, Diode, Improved solubility, business.industry, Mechanical Engineering, [CHIM.MATE]Chemical Sciences/Material chemistry, organic light-emitting diodes, 021001 nanoscience & nanotechnology, Acceptor, Fluorescence, 0104 chemical sciences, Mechanics of Materials, Optoelectronics, Quantum efficiency, 0210 nano-technology, Donor acceptor, business, unconjugated system
Abstract: International audience; In this work, two novel thermally activated delayed fluorescence (TADF) emitters, 2tDMG and 3tDMG, are synthesized for high‐efficiency organic light‐emitting diodes (OLEDs), The two emitters have a tilted face‐to‐face alignment of donor (D)/acceptor (A) units presenting intramolecular noncovalent interactions. The two TADF materials are deposited either by an evaporation‐process or by a solution‐process, both of them leading to high OLED performance. 2tDMG used as the emitter in evaporation‐processed OLEDs achieves a high external quantum efficiency (EQE) of 30.8% with a very flat efficiency roll‐off of 7% at 1000 cd m−2. The solution‐processed OLEDs also display an interesting EQE of 16.2%. 3tDMG shows improved solubility and solution processability as compared to 2tDMG, and thus a high EQE of 20.2% in solution‐processed OLEDs is recorded. The corresponding evaporation‐processed OLEDs also reach a reasonably high EQE of 26.3%. Encouragingly, this work provides a novel strategy to address the imperious demands for OLEDs with high EQE and low roll‐off.
Published: 2020

28. Emerging organic electronics

Author: Zuo-Quan Jiang, Nicolas Leclerc, Cyril Poriel, Soochow University, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire des Matériaux, Surfaces et Procédés pour la Catalyse (LMSPC), Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Organic electronics, Materials science, Materials Chemistry, [CHIM]Chemical Sciences, General Materials Science, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 0210 nano-technology, 01 natural sciences, 0104 chemical sciences
Abstract: Zuo-Quan Jiang, Cyril Poriel and Nicolas Leclerc introduce the Materials Chemistry Frontiers themed collection on emerging organic electronics.
Published: 2020

29. 9,9 '-Spirobifluorene based zinc coordination polymers: a study on linker geometry and topology

Author: Cyril Poriel, Florian Moreau, Nathalie Audebrand, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), MENSR, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, 010405 organic chemistry, Ligand, chemistry.chemical_element, Tetrahedral molecular geometry, General Chemistry, Zinc, Crystal structure, 010402 general chemistry, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Crystallography, chemistry, Octahedron, [CHIM]Chemical Sciences, General Materials Science, Linker, Geometry and topology, Topology (chemistry)
Abstract: International audience; We report four Zn-based coordination polymers (CPs), synthesized from three spirobifluorene (SBF) tetracarboxylate ligands, possessing different topologies and dimensionalities. Zn-SBF-1, Zn-SBF-2 and Zn-SBF-3 CPs have 2D crystal structures with an sql topology built from square planar ligands (L1 and L3) and paddle-wheels for Zn-SBF-1 or original dimers of zinc for Zn-SBF-2 and Zn-SBF-3. Zn-SBF-4 is built from a ligand with a distorted tetrahedral geometry (L2) and an inorganic octahedral building unit resulting in a non-interpenetrated 3D porous framework with a toc topology. Structural relationships evidence that the meta (L2) versus para (L1 and L3) position of the carboxylic functions on the benzoate group of the SBF ligand increases the connectivity of the inorganic building unit and then the dimensionality of the framework.
Published: 2020

30. Spirophenylacridine‐2,7‐(diphenylphosphineoxide)‐fluorene: A Bipolar Host for High‐Efficiency Single‐Layer Blue Phosphorescent Organic Light‐Emitting Diodes

Author: Nicolas Leclerc, Cyril Poriel, Lambert Sicard, Olzhas A. Ibraikulov, Denis Tondelier, Joëlle Rault-Berthelot, Bernard Geffroy, Thomas Heiser, Fabien Lucas, Cassandre Quinton, Palacin, Serge, Appel à projets générique - Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires - - Men in blue2014 - ANR-14-CE05-0024 - Appel à projets générique - VALID, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des sciences de l'ingénieur, de l'informatique et de l'imagerie (ICube), École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Université de Strasbourg (UNISTRA)-Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de Recherche en Informatique et en Automatique (Inria)-Les Hôpitaux Universitaires de Strasbourg (HUS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut d'Electronique du Solide et des Systèmes (InESS), Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), CINES (Montpellier No.2019-A0060805032), Région Bretagne (DIADEM project), ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-École Nationale du Génie de l'Eau et de l'Environnement de Strasbourg (ENGEES)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685)
Subjects: Materials science, spiro compounds, 02 engineering and technology, Electron, Fluorene, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, OLED, ambipolar charge transport, HOMO/LUMO, Diode, [CHIM.MATE] Chemical Sciences/Material chemistry, high E T host materials, business.industry, Single-layer blue phosphorescent organic light-emitting diode, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, chemistry, Optoelectronics, Quantum efficiency, 0210 nano-technology, Phosphorescence, business, Electrical efficiency
Abstract: International audience; Herein, a high-efficiency host material for single-layer phosphorescent organic light-emitting diodes (SL-PhOLEDs) is reported. This host material is synthesized via an efficient approach and is constructed on the association of an electron-rich phenylacridine unit connected by a spiro carbon atom to an electron-deficient 2,7-bis(diphenylphosphineoxide)-fluorene. In addition to a high ET value and adequate highest occupied molecular orbital/lowest unoccupied molecular orbital energy levels, the key point in this molecular design is the suitable balance between hole and electron mobilities, which leads to a high-performance blue SL-PhOLED with an external quantum efficiency of 17.6% (current efficiency = 37.8 cd A−1 and power efficiency = 37.1 lm W−1) and a low Von of 2.5 V. This performance shows that the molecular design of the present host fulfills the criteria required for high-efficiency SL-PhOLEDs. The present performance is one of the highest reported to date for blue SL-PhOLEDs and more importantly shows the potential of such a molecular design to reach very high-performance single-layer devices.
Published: 2020

31. Synthesis, photophysical and electropolymerization properties of thiophene-substituted 2,3-diphenylbuta-1,3-dienes

Author: Joëlle Rault-Berthelot, Arie van der Lee, Philippe Gerbier, Sébastien Clément, Mathias Quiot, Sébastien Richeter, Maxime Roger, Cyril Poriel, Kassem Amro, Centre d'Energétique et de Thermique de Lyon (CETHIL), Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), Université de Montpellier, Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), and Université de Montpellier (UM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Molecular interactions, 010405 organic chemistry, Band gap, Solid-state, New materials, General Chemistry, Polymer, 010402 general chemistry, Electrochemistry, Photochemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Materials Chemistry, Thiophene, [CHIM]Chemical Sciences, Aggregation-induced emission, ComputingMilieux_MISCELLANEOUS
Abstract: International audience; A series of 2,3-diphenylbuta-1,3-dienes (DPBs) bearing thiophene (T-DPB), bithiophene (BT-DPB) and ethylenedioxythiophene (EDOT-DPB) electropolymerizable units were prepared through desilylation reactions of the corresponding 3,4-diphenylsiloles derivatives. These DPBs derivatives exhibit remarkable different aggregation induced emission (AIE) or aggregation enhanced emission (AEE) behaviour depending on the strength of the molecular interactions occuring in the solid state. Indeed, T-DPB and EDOT-DPB were found to be good AIEgens while BT-DPB exhibited AEE behaviour. Finally, the electrochemical properties of these new materials were investigated revealing for all DPBs the occurrence of electropolymerization processes leading potentially to low band gap polymers.
Published: 2020

32. Persistent Organic Room-Temperature Phosphorescence inCyclohexane-Trans-1,2-Bisphthalimide Derivatives: The DramaticImpact of Heterochiral vs. Homochiral Interactions

Author: Cassandre Quinton, Cyril Poriel, Thierry Roisnel, Denis Jacquemin, Ludovic Favereau, Jeanne Crassous, Synthèse Caractérisation Analyse de la Matière (ScanMAT), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - Faculté des Sciences et des Techniques, Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université de Rennes (UR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)
Subjects: Quantitative Biology::Biomolecules, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Dimer, Intermolecular force, Supramolecular chemistry, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Enantiopure drug, chemistry, Computational chemistry, Excited state, [CHIM]Chemical Sciences, General Materials Science, Physical and Theoretical Chemistry, Enantiomer, 0210 nano-technology, Phosphorescence, Chirality (chemistry)
Abstract: Persistent metal-free Room-Temperature Phosphorescence (RTP) materials attract significant interest owing to the production of long-lived triplet excited states. Although several organic designs show RTP, the impact of intermolecular interactions on the triplet excitons stabilization and migrations remains hardly understood because obtaining different ordered intermolecular interactions while conserving identical molecular electronic properties is very challenging. We propose here a new strategy to circumvent this problem by taking advantage of the distinct molecular packing that can be found between enantiomer and racemic forms of a chiral molecule. Structural, photophysical and chiroptical investigations of chiral cyclohexane bisphthalimide derivatives showed that heterochiral and homochiral dimer interactions play a crucial role on the triplet excited state stabilization, resulting in higher RTP efficiency for enantiopure systems than for racemic one. This study paves the way to the use of molecular chirality to rationalize supramolecular properties arising from subtle intermolecular interactions.
Published: 2020

33. Influence of Fluorene and Spirobifluorene Regioisomerism on the Structure, Organization, and Permeation Properties of Monolayers

Author: Yann R. Leroux, Cyril Poriel, Joanna Jalkh, Sébastien Thiery, Jean-François Bergamini, Philippe Hapiot, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Region Bretagne [461-ARED], HOME-OLED [11-BS07-020-01], ANR-11-BS07-0020,HOME-OLED,Design de Matériaux hôtes pour des Diodes Organiques Electrophosphorescentes bleues haute performance : une nouvelle approche(2011), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, [CHIM.MATE]Chemical Sciences/Material chemistry, 02 engineering and technology, Fluorene, Permeation, 010402 general chemistry, 021001 nanoscience & nanotechnology, Electrochemistry, Photochemistry, 01 natural sciences, Coupling reaction, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, Scanning electrochemical microscopy, General Energy, Chemical engineering, chemistry, Monolayer, Click chemistry, Physical and Theoretical Chemistry, Thin film, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract: 9,9′-Spirobifluorene (SBF) and fluorene derivatives are extensively used as active layer in many organic electronic devices nowadays; thus, careful examination of their structure and organization in thin films and monolayers is of primary importance. In the present work, immobilization of SBF and fluorene isomers was performed via Click Chemistry coupling reaction onto well-ordered ethynylbenzene monolayers on carbon substrates. Characterization of the as-prepared monolayers was performed by classical electrochemical techniques (CV), scanning electrochemical microscopy, and atomic force microscopy, highlighting the effect of SBF and fluorene onto the structure and organization of the obtained monolayers. The significant impact of their positional isomerism on the monolayers structuration was clearly evidenced. Indeed, 2-substituted SBF and fluorene monolayers appear to be more compact and ordered than their 4-substituted analogues and are orientated parallel to the surface. These findings should have an i...
Published: 2017

34. New generations of spirobifluorene regioisomers for organic electronics tuning electronic properties with the substitution pattern

Author: Lambert Sicard, Cyril Poriel, Joëlle Rault-Berthelot, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 11-BS07-020-01, Agence Nationale de la Recherche, Agence de l'Environnement et de la Maîtrise de l'Energie, Région Bretagne, ANR-11-BS07-0020,HOME-OLED,Design de Matériaux hôtes pour des Diodes Organiques Electrophosphorescentes bleues haute performance : une nouvelle approche(2011), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Steric effects, Materials science, Nanotechnology, 010402 general chemistry, 01 natural sciences, Catalysis, Materials Chemistry, Structural isomer, OLED, Molecule, [CHIM]Chemical Sciences, Spiro Compounds, Electronics, Diode, Organic electronics, Fluorenes, Molecular Structure, 010405 organic chemistry, Metals and Alloys, Stereoisomerism, General Chemistry, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Ceramics and Composites, Phosphorescence
Abstract: International audience; The spirobifluorene (SBF) fragment constitutes one of the most important scaffolds used in the design of Organic Semi-Conductors (OSCs) for organic electronics. In the last ten years, new generations of SBF positional isomers have appeared in the literature. The different positions of substitution (C1, C3 or C4) have allowed the tuning of the electronic properties of great interest for the further design of functional materials. The high potential of these new generations of organic semi-conductors in electronics has been demonstrated notably when they are used as host materials for Phosphorescent Organic Light-Emitting Diodes (OLEDs) or for Thermally Activated Delayed Fluorescence OLEDs. In the present feature article, we present these new generations of SBF compounds and the impact of positional isomerism on the electronic properties and device performance. Particularly, we show how the different structural and electronic parameters (nature of the linkages, bridge substitution and steric hindrance) drive the electrochemical and photophysical properties of SBF regioisomers and can be modulated. Such studies lay the foundation for material design for organic electronics.
Published: 2019

35. Cyclization of terphenyl-bisfluorenol a mechanistic study of the regioselectvity

Author: Cyril Poriel, Frédéric Barrière, Damien Thirion, Joëlle Rault-Berthelot, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Région Bretagne, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Reaction mechanism, cyclization, 010405 organic chemistry, Chemistry, spiro compounds, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Regioselectivity, Fluorenol, General Chemistry, Fluorene, pi-conjugated systems, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Computational chemistry, Mechanism (philosophy), Terphenyl, regioselectivity, mechanistic investigations
Abstract: International audience; The mechanism of the bicyclization reaction of a series of terphenyl-bisfluorenols into dispiro[fluorene-9,6'-indeno[1,2-b]fluorene-12',9''-fluorene] and dispiro[fluorene-9,6'-indeno[2,1-a]fluorene-12',9''-fluorene] is reported. Through a combined experimental and theoretical study, the different parameters that drive the regioselectivity of this cyclization reaction have been studied and are presented.
Published: 2019

36. 1-Carbazolyl Spirobifluorene Synthesis, Structural, Electrochemical, and Photophysical Properties

Author: Cassandre Quinton, Cyril Poriel, Lambert Sicard, Joëlle Rault-Berthelot, Olivier Jeannin, Fabien Lucas, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR [14-CE05-0024], CINES [2018-A0040805032], ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Materials science, Carbazole, Substituent, 02 engineering and technology, Fluorene, 010402 general chemistry, 021001 nanoscience & nanotechnology, Electrochemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, General Energy, chemistry, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, 0210 nano-technology, Electronic properties
Abstract: International audience; The present work reports one of the rare examples of a new emerging family of spirobifluorene derivatives, namely, 1-substituted spirobifluorenes. We report the synthesis and the structural, electrochemical, and photophysical properties of 9-(9,9′-spirobi[fluorene]-1-yl)-9H-carbazole 1-Cbz-SBF, constructed from the connection of the widely known electron-rich carbazole fragment at the C1 position of spirobifluorene. We show with 1-Cbz-SBF that the substitution at C1 induces two important characteristics which drive the electronic properties. First, there is a complete π-conjugation breaking between the pending substituent, herein, carbazole, and the substituted fluorene. Second, there is a through-space interaction between the carbazole and its cofacial fluorene. Thanks to a structure–property relationship approach with its constituting building blocks 9,9′-spirobifluorene SBF and carbazole Cbz, we show how some electronic properties are driven by the carbazole unit such as the highest occupied molecular orbital energy level, whereas others are driven by the fluorene unit such as the triplet-state energy level. As 1-substituted spirobifluorenyl represents a new and promising molecular scaffold for phosphorescent organic light-emitting diode applications and more generally for organic electronics, such a study provides fundamental knowledge to design future organic materials for specific applications.
Published: 2019

37. 9H-Quinolino[3,2,1-k]phenothiazine: A New Electron-Rich Fragment for Organic Electronics

Author: Denis Tondelier, Cassandre Quinton, Urelle Biapo, Bernard Geffroy, Joëlle Rault-Berthelot, Cyril Poriel, Olivier Jeannin, Sébastien Thiery, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), We thank the CDIFX and CRMPO (Rennes), GENCI (France) and CINES (Montpellier, c2016085032), the ISN (Gif Sur Yvette) and the ANR (n°11-BS07-020-01 and 14-CE05-0024) for financial support and for a studentship (S.T.)., ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), ANR-11-BS07-0020,HOME-OLED,Design de Matériaux hôtes pour des Diodes Organiques Electrophosphorescentes bleues haute performance : une nouvelle approche(2011), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: spiro compounds, Stereochemistry, Context (language use), 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Catalysis, chemistry.chemical_compound, symbols.namesake, OLED, organic semiconductors, HOMO/LUMO, Organic electronics, Chemistry, Carbazole, Organic Chemistry, Fermi level, quinolinophenothiazine, [CHIM.MATE]Chemical Sciences/Material chemistry, General Chemistry, organic light-emitting diodes, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Organic semiconductor, Crystallography, symbols, 0210 nano-technology, Phosphorescence
Abstract: International audience; A new electron-rich fragment, namely the qui-nolinophenothiazine (QPTZ) is reported. TheQ PTZ fragment incorporated in spiroconfigured materials leads to higher performance in blue Phosphorescent OLEDs than structurally related phenylacridine and indoloacridine based materials (increasing the HOMO energy level,m od-ulating the spin-orbit coupling, etc.) and leads to highly efficient blue phosphorescent organic light emitting diodes, indicatingt he strongp otential of this new molecular fragment in organic electronics. Over the last 30 years,t he fantastic emergence of organic electronics is assignable to the design,t he synthesis and the study of thousands of organic semiconductors (OSCs) with specific properties fitting with the different electronic devices. [1–4] Since the discoveryo ft he " host/guest concept " in phosphorescent organic light-emitting diodes (PhOLEDs), [5] the designo fO SCs usable as host materials for blue-emitting phosphors has been an intense research field worldwide. [4] In addition to its high thermal/morphological stabilitya nd its high triplet energy (E T), an ideal host should also possess ab ipolar character,w ith HOMO and LUMO energy levels adapted to the Fermi levels of the electrodes. [6–9] However,t here is ac ertaina ntinomy between ah igh E T (essential to insure efficient energy transfers) and as hort HOMO/LUMO gap (essential to insure efficient charge injection) and the best trade-off should be found for the ideal host. If the nature of the linkage [10] between the electron rich and the electron-poor units is of key importance to control the E T as well as the HOMO/LUMO gap, their intrinsic properties remainn everthelesst he most important characteristics. In this context, the widely known electron-rich carbazole fragment has led to impressive breakthroughs and is nowadays an important buildingb lock in organic electronics. [11, 12] Around the molecular structure of carbazole, many other car-bazole-like fragments have been developed in the recent years sometimes surpassing the performance of the carbazole fragment in electronics. Thus, indolocarbazole (IC), [13] phenylacri-dine (PA) [14–16] and more recentlyi ndoloacridine (IA) [17] are nowadays key building blocks, widely used in all organic electronic devices (Scheme 1). As the future of organic electronics strongly relies on the discoveryo fn ovel elementarym olecular fragments, such as the new bithiophenesulfonamide building block recently reported by Marks,F acchettie ta l., [19] we wish to report herein an ew promising electron-rich core, namely the quinolinophe-Scheme1.Phenylacridine (PA, left), [14, 18] indoloacridine(IA, middle) [17] and quinolinophenothiazine (QPTZ,r ight) based semiconductors.
Published: 2016

38. Annealing effect on the electrical proprieties of IF(CN2)2-meta based OTFTs: Thermal behavior and modeling of charge transport

Author: Ramzi Bourguiga, Emmanuel Jacques, Sarah Bebiche, N. Arfaoui, Ismaïl Bouhadda, Cyril Poriel, M. Mahdouani, M. Chevrier, Université de Carthage - University of Carthage, Franche-Comté Électronique Mécanique, Thermique et Optique - Sciences et Technologies (UMR 6174) (FEMTO-ST), Université de Technologie de Belfort-Montbeliard (UTBM)-Ecole Nationale Supérieure de Mécanique et des Microtechniques (ENSMM)-Université de Franche-Comté (UFC), Université Bourgogne Franche-Comté [COMUE] (UBFC)-Université Bourgogne Franche-Comté [COMUE] (UBFC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut d'Électronique et des Technologies du numéRique (IETR), Nantes Université (NU)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), This work has been supported by the Tunisian Ministry of Higher Education and Scientific Research, University of Carthage., Université de Technologie de Belfort-Montbeliard (UTBM)-Ecole Nationale Supérieure de Mécanique et des Microtechniques (ENSMM)-Centre National de la Recherche Scientifique (CNRS)-Université de Franche-Comté (UFC), Université Bourgogne Franche-Comté [COMUE] (UBFC)-Université Bourgogne Franche-Comté [COMUE] (UBFC), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Nantes (UN)-Université de Rennes 1 (UR1)
Subjects: Materials science, Annealing (metallurgy), 02 engineering and technology, Activation energy, Photoresist, Modeling the charge transport, 010402 general chemistry, 7. Clean energy, 01 natural sciences, Variable-range hopping, Crystallinity, [CHIM]Chemical Sciences, General Materials Science, Electrical and Electronic Engineering, business.industry, N type-OTFTs, Density of states, Atmospheric temperature range, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, Thin-film transistor, Temperature dependence, Optoelectronics, Annealing effect, 0210 nano-technology, business
Abstract: International audience; N-type organic thin film transistors (OTFT) based on IF(CN2)2-meta were fabricated in bottom gate-bottom contact configuration at substrate temperature of 80 °C and deposition rate dr of 0,4 Å/s, using the epoxy based photoresist SU-8 as gate insulator. A thermal annealing of fabricated devices under nitrogen for 90 min at 150 °C has enhanced their performances. In order to understand the annealing effect on the performance of IF(CN2)2-meta based OFETs, we have analyzed their thermal behavior by characterizing them electrically over a temperature range from 300 up to 380 K while 10 K step was used. Accordingly, we have estimated and compared the activation energy of the mobility Ea and the density of state DOS before and after annealing treatment. The present study has shown that the improvement of OFETs performances is due to the increased crystallinity of IF(CN2)2-meta layer thereby to the enhanced SU-8/IF(CN2)2-meta and Au/IF(CN2)2-meta interfaces. Finally, to understand the charge transport mechanism dominating in the IF(CN2)2-meta molecule and to model the fabricated OFETs, we have successfully reproduced the dependence of mobility with temperature and the transfer and output characteristics using an analytical model based on variable range hopping (VRH) theory.
Published: 2018

39. Confining Nitrogen Inversion to Yield Enantiopure Quinolino[3,2,1-k]Phenothiazine Derivatives

Author: Lambert Sicard, Nicolas Vanthuyne, Olivier Jeannin, Cassandre Quinton, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), GENCI [2017-A0020805032], [ANR14-CE05-0024], ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: nitrogen inversion, Materials science, spiro architecture, quinolinophenothiazine, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 01 natural sciences, diastereocontrol, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, Biomaterials, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Enantiopure drug, chemistry, Phenothiazine, Yield (chemistry), Electrochemistry, Organic chemistry, Nitrogen inversion, 0210 nano-technology
Abstract: International audience; The first examples of optically pure 9H-quinolino[3,2,1-k]phenothiazine (QPTZ)-based molecules are reported. The inversion of the nitrogen atom, locked in the QPTZ fragment, is confined with a high-energy barrier that has allowed the isolation at room temperature of each stereoisomer. Considering the growing necessity in molecular electronics to introduce chiral characteristics within highly efficient molecular fragments, a molecular strategy to generate enantiopure derivatives constructed on the very promising electron rich core QPTZ is provided. As this work aims to report the foundations of the QPTZ chirality, the present findings may open avenues towards the use of this fragment in its optically pure form.
Published: 2018

40. A Dihydrodinaphthoheptacene

Author: Maxime Romain, Cassandre Quinton, Thierry Roisnel, Emmanuel Jacques, Joëlle Rault-Berthelot, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut d'Électronique et des Technologies du numéRique (IETR), Nantes Université (NU)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), 2017-A0020805032, 14-CE05-0024, ANR, Agence Nationale de la Recherche, ADEME, Agence de l'Environnement et de la Maîtrise de l'Energie, ISN, Indian Society of Nephrology, Conseil Régional de Bretagne, ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Rennes 1 (UR1), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)
Subjects: cyclization, synthesis, 010405 organic chemistry, Organic Chemistry, article, 010402 general chemistry, 01 natural sciences, Intramolecular cyclizations, 0104 chemical sciences, Photophysical properties, [SPI.TRON]Engineering Sciences [physics]/Electronics, [INFO.INFO-NI]Computer Science [cs]/Networking and Internet Architecture [cs.NI], Regioselectivity, Regio-selective, electrophilicity
Abstract: International audience; We report the first example of a dihydrodinaphthoheptacene derivative and the mechanistic investigations of the regioselective electrophilic intramolecular cyclization reaction involved in the synthesis. The structural, electrochemical, and photophysical properties have been investigated.
Published: 2018

41. Dihydroindenofluorene Positional Isomers

Author: Cyril Poriel, Joëlle Rault-Berthelot, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), CINES [2018-A0040805032-GENCI-Montpellier], ANR [11-BS07-020-01/14-CE05-0024], ANR-11-BS07-0020,HOME-OLED,Design de Matériaux hôtes pour des Diodes Organiques Electrophosphorescentes bleues haute performance : une nouvelle approche(2011), ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Biphenyl, Organic electronics, Stereochemistry, 02 engineering and technology, General Medicine, General Chemistry, Fluorene, 010402 general chemistry, 021001 nanoscience & nanotechnology, Ring (chemistry), 01 natural sciences, 0104 chemical sciences, Organic semiconductor, chemistry.chemical_compound, chemistry, Group (periodic table), Structural isomer, [CHIM]Chemical Sciences, Indene, 0210 nano-technology
Abstract: International audience; Bridged oligophenylenes are very important organic semiconductors (OSCs) in organic electronics (OE). The fluorene unit, which is a bridged biphenyl, is the spearhead of this class of materials and has, over the last 20 years, led to fantastic breakthroughs in organic light-emitting diodes. Dihydroindenofluorenes belong to the family of bridged terphenyls and can be viewed as the fusion of a fluorene unit with an indene fragment. Dihydroindenofluorenes have also appeared as very promising building blocks for OE applications. In the dihydroindenofluorene family, there are five positional isomers, with three different phenyl linkages ( para/ meta/ ortho) and two different ring bridge arrangements ( anti/ syn). We have focused on the concept of positional isomerism. Indeed, the structural differences of the dihydroindenofluorenyl cores lead to unusual electronic properties, which our group has described since 2006, thanks to the five dispirofluorene-indenofluorene positional isomers (dihydroindenofluorenes substituted on the bridges by fluorenyl units). 6,12-Dihydroindeno[1,2- b]fluorene (the para-anti isomer) is constructed on a p-terphenyl core and possesses an anti geometry. Although this isomer has been widely investigated over the last 20 years, studies of the four other isomers remain very scarce. 11,12-Dihydroindeno[2,1- a]fluorene (the para-syn isomer) is also built on a bridged p-terphenyl core but possesses a syn geometry. This particular geometry has been advantageously used by our group to drastically tune the electronic properties, and this isomer has emerged as a promising scaffold to obtain stable blue emission arising from conformationally controllable intramolecular excimers. These preliminary studies have shown the crucial influence of the geometry on the electronic properties of the dihydroindenofluorenes. Modification of the arrangement of the phenyl linkages from para to meta provides the meta isomers, namely, 7,12-dihydroindeno[1,2- a]fluorene (the meta-anti isomer) and 5,7-dihydroindeno[2,1- b]fluorene (the meta-syn isomer). With these two regioisomers, the strong impacts of both the linkage and the geometry on the electronic properties have been particularly highlighted over the years. The last positional isomer of the family is 5,8-dihydroindeno[2,1- c]fluorene, which possesses a central o-terphenyl backbone and a syn geometry. This isomer is unique because of its ortho linkage, which induces a particular helicoidal turn of the dihydroindenofluorenyl core. Using a structure-property relationship approach, in the present Account we describe the molecular diversity of the five dispirofluorene-indenofluorene positional isomers and the consequences both in terms of their organic synthesis and electronic properties. This Account shows how positional isomerism can be a powerful tool to tune the electronic properties of OSCs.
Published: 2018

42. Discrimination of positional isomers by ion mobility mass spectrometry Application to organic semiconductors

Author: Corentin Tonneaux, Julien De Winter, Pascal Gerbaux, Maxime Romain, Vincent Lemaur, Jérôme Cornil, Quentin Duez, Cyril Poriel, University of Mons [Belgium] ( UMONS ), Organic Synthesis and Mass Spectrometry Laboratory, Institut des Sciences Chimiques de Rennes ( ISCR ), Université de Rennes 1 ( UR1 ), Université de Rennes ( UNIV-RENNES ) -Université de Rennes ( UNIV-RENNES ) -Ecole Nationale Supérieure de Chimie de Rennes-Institut National des Sciences Appliquées ( INSA ) -Centre National de la Recherche Scientifique ( CNRS ), Laboratory for Chemistry of Novel Materials, University of Mons [Belgium] (UMONS), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Ion-mobility spectrometry, General Chemical Engineering, 010402 general chemistry, Optoelectronic devices, 01 natural sciences, [ CHIM ] Chemical Sciences, Analytical Chemistry, Isomers, Regioselectivity, Computational chemistry, Ion mobility spectrometers, Structural isomer, Synthetic approach, [CHIM]Chemical Sciences, Regio-selective, Chromatography, Positional isomers, Mass spectrometry, Chemistry, Direct method, Regioselective routes, 010401 analytical chemistry, General Engineering, 0104 chemical sciences, Organic semiconductor, Ion mobility-mass spectrometry
Abstract: International audience; Organic semiconductors are increasingly being used in organic-based opto-electronic devices. Since regioselective synthetic approaches are not always controlled, promising compounds are sometimes prepared following non-regioselective routes. Ion mobility mass spectrometry is here introduced as a direct method to distinguish isomers in mixtures, instead of undertaking time-consuming analytical chromatography procedures. © 2018 The Royal Society of Chemistry.
Published: 2018

43. Influence of the gate bias stress on the stability of n-type organic field-effect transistors based on dicyanovinylene-dihydroindenofluorene semiconductors

Author: Maxime Harnois, Tayeb Mohammed-Brahim, Joëlle Rault-Berthelot, Sarah Bebiche, P. A. Cisneros-Perez, Cyril Poriel, Emmanuel Jacques, Institut d'Électronique et des Technologies du numéRique (IETR), Nantes Université (NU)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), 2015–2020 MATECOM-ORGAFLEX, Région Bretagne, MESR, Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche, EGU, European Geosciences Union, FEDER, European Regional Development Fund, Université de Nantes (UN)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Rennes 1 (UR1), Université de Rennes 1 (UR1), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Electrical Instability, Materials science, 02 engineering and technology, Fluorene, Photoresist, 010402 general chemistry, 01 natural sciences, law.invention, chemistry.chemical_compound, law, Materials Chemistry, Insulator Charge Trapping, Molecule, General Materials Science, Leakage Current, business.industry, Transistor, n-type Organic Field-Effect Transistors, Epoxy, 021001 nanoscience & nanotechnology, 0104 chemical sciences, [SPI.TRON]Engineering Sciences [physics]/Electronics, Gate Bias Stress, Semiconductor, chemistry, visual_art, visual_art.visual_art_medium, Optoelectronics, Field-effect transistor, 0210 nano-technology, business, Voltage, Dicyanovinylene-Dihydroindenofluorene
Abstract: International audience; The electrical stabilities of n-type Organic Field-Effect Transistors (OFETs) based on dihydroindeno[1,2-b]fluorene and dihydroindeno[2,1-b]fluorene derivatives have been studied. These OFETs incorporate epoxy-based photoresist SU-8 as the gate insulator. The comparison of the electrical stability through gate bias stress measurements as a function of voltage and temperature stress shows that the instabilities of these OFETs result from different phenomena. Different models have been used to analyse the instabilities of the devices and these are discussed. As the two molecules only differ by their geometry and their substitution, this study shows how slight structural modifications of the semiconductor molecular structure induce electrical instabilities in the corresponding OFETs arising from different features.
Published: 2018

44. ortho-, meta-, andpara-Dihydroindenofluorene Derivatives as Host Materials for Phosphorescent OLEDs

Author: Bernard Geffroy, Anna Shirinskaya, Céline Declairieux, Rémi Métivier, Denis Tondelier, Cyril Poriel, Maxime Romain, Sébastien Thiery, Joëlle Rault-Berthelot, Olivier Jeannin, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), École normale supérieure - Cachan (ENS Cachan)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), and Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN)
Subjects: dihydroindenofluorenes, Materials science, Phosphorescent oleds, 010405 organic chemistry, LEDs, [SDV]Life Sciences [q-bio], General Chemistry, General Medicine, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, Molecule, Organic chemistry, [CHIM]Chemical Sciences, Triplet state, Phosphorescence, organic semiconductors, Electronic properties
Abstract: International audience; This work reports the first structure-properties relationship study of ortho [2,1-c]-, meta [1,2-a]-, and para [1,2-b]dihydroindenofluorenes, highlighting the influence of bridge rigidification on the electronic properties. This study has made it possible to devise an extended π-conjugated molecule with both a high triplet state energy level and excellent thermal and morphological stability. As a proof of concept, dihydroindenofluorenes were used as the host in sky-blue phosphorescent organic light-emitting diodes (PhOLEDs) with high performance.
Published: 2014

45. Modulating the Physical and Electronic Properties over Positional Isomerism: The Dispirofluorene-Dihydroindacenodithiophene (DSF-IDT) Family

Author: Olivier Jeannin, Jean-David Peltier, Joëlle Rault-Berthelot, Cyril Poriel, Bertrand Donnio, Benoît Heinrich, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), 2017-A0020805032, Conseil Régional de Bretagne, ADEME, Agence de l'Environnement et de la Maîtrise de l'Energie, Université de Strasbourg, CNRS, Centre National de la Recherche Scientifique, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), and Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique
Subjects: Phase transition, isomerism, 3π-2spiro architecture, spiro compounds, Solid-state, 02 engineering and technology, 010402 general chemistry, Photochemistry, Electrochemistry, 01 natural sciences, Catalysis, Crystallinity, [CHIM]Chemical Sciences, HOMO/LUMO, Electronic properties, Chemistry, Organic Chemistry, structure-activity relationships, dispirofluorene–indacenodithiophenes, electropolymerization, General Chemistry, 021001 nanoscience & nanotechnology, Fluorescence spectra, 0104 chemical sciences, DiSpiroFluorene-Indacenodithiophenes, Polymerization, Chemical physics, structure–activity relationships, 0210 nano-technology, 3π–2spiro architecture
Abstract: International audience; We report the first studies on the intrinsic properties of a meta-substituted dihydroindacenodithienyl fragment and more generally the strong impact of positional isomerism on dihydroindacenodithiophene derivatives. The influence of the para and meta linkages has notably been highlighted not only for the electronic properties in solution (electrochemical properties, anodic polymerization, HOMO/LUMO energy levels, optical transitions, fluorescence spectra) but also on the physical properties in the solid state (molecular organization, crystallinity, and phase transitions). The positional isomerism hence appears to be a very efficient tool to drastically tune the properties of dihydroindacenodithiophene derivatives. © 2017 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim
Published: 2017

46. Zinc Tetraphenylporphyrin as High Performance Visible Light Photoinitiator of Cationic Photosensitive Resins for LED Projector 3D Printing Applications

Author: Assi Al Mousawi, Frédéric Dumur, Tayssir Hamieh, Cyril Poriel, Jacques Lalevée, Joumana Toufaily, Jean Pierre Fouassier, Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Lebanese University [Beirut] (LU), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR, Agence Nationale de la Recherche, Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, Polymers and Plastics, Organic Chemistry, Radical polymerization, Cationic polymerization, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, 0104 chemical sciences, law.invention, Inorganic Chemistry, chemistry.chemical_compound, Photopolymer, chemistry, Polymerization, law, Tetraphenylporphyrin, Materials Chemistry, [CHIM]Chemical Sciences, 0210 nano-technology, Photoinitiator, Light-emitting diode, Visible spectrum
Abstract: International audience; Zinc tetraphenylporphyrin (ZnTPP) is proposed as a high performance visible light photoinitiator for both the free radical polymerization (FRP) of methacrylates (thick films) and the cationic polymerization (CP) of epoxides (thin films) upon visible light exposure using light emitting diodes (LEDs) at 405, 455, 477, and 530 nm. ZnTPP combined with an iodonium salt shows excellent polymerization initiating abilities and high final conversions were obtained. Remarkably, for the ligand alone (tetraphenylporphyrin derivative, H2TPMP) used as photoinitiator, no polymerization occurs, indicating the importance of the metal in the initiating complex for an efficient process. A full picture of the involved chemical mechanisms is given. The high performance of ZnTPP as cationic initiating system is also well shown for new cationic 3D printing resins upon exposure to LED projector at 405 nm. © 2017 American Chemical Society.
Published: 2017

47. Electron-Deficient Dihydroindaceno-Dithiophene Regioisomers for n-Type Organic Field-Effect Transistors

Author: Bertrand Donnio, Joëlle Rault-Berthelot, Benoît Heinrich, Emmanuel Jacques, Cyril Poriel, Jean-David Peltier, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut d'Électronique et des Technologies du numéRique (IETR), Nantes Université (NU)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), 11-BS07-020-01, Agence Nationale de la Recherche, Université de Strasbourg, Agence de l'Environnement et de la Maîtrise de l'Energie, Centre National de la Recherche Scientifique, Université de Rennes 1, Institut d'?lectronique et de T?l?communications de Rennes, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Nantes (UN)-Université de Rennes 1 (UR1)
Subjects: Materials science, Molecular model, Absorption spectroscopy, Stereochemistry, Supramolecular chemistry, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, flexible electronics, dihydroindaceno−dithiophene, Structural isomer, Molecule, General Materials Science, organic semiconductors, metal−semiconductor interface, Diketone, Organic field-effect transistor, [CHIM.ORGA]Chemical Sciences/Organic chemistry, FET mobility, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, organic field-effect transistor, 0104 chemical sciences, [SPI.TRON]Engineering Sciences [physics]/Electronics, Organic semiconductor, Crystallography, 0210 nano-technology
Abstract: This paper was published on the Web on February 21, 2017. Table 1 was reformatted, and the corrected version was reposted on February 22, 2017.; International audience; In this work, we wish to report the first member of a new family of organic semiconductors constructed on a meta dihydroindacenodithiophene core, that is, 2,2'-(2,8-dihexyl-4,6-dihydro-s-indaceno[1,2-b:7,6-b']dithiophene-4,6-diylidene)dimalononitrile (called meta-IDT(═C(CN)2)2). The properties of this molecule were studied in detail through a structure-properties relationship study with its regioisomer, that is, 2,2'-(2,7-dihexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-diylidene)dimalononitrile (para-IDT(═C(CN)2)2) (see isomer structures in blue in Chart 2). The influence of the bridge functionalization was also investigated by comparison with their diketone analogues meta-IDT(═O)2 and para-IDT(═O)2. This study sheds light on the impact of regioisomerism on the electronic properties at the molecular level (electrochemistry, absorption spectroscopy, molecular modeling) and also on the supramolecular arrangement, and finally on the organic field-effect transistors (OFET) performances and stabilities. The significant effect of self-assembled monolayers of 4-(dimethylamino)benzenethiol grafted on the gold drain and source electrodes or of the use of flexible substrate (polyethylene naphtalate) instead of glass on the OFET performances and stabilities are also reported. In the light of these results (maximum mobility reaching 7.1 × 10(-2) cm(2) V(-1) cm(-1), high IDon/IDoff of 2.3 × 10(7), and subthreshold swing of 1.2 V/dec), we believe that the present OFETs can be further used to construct electronic circuits.
Published: 2017

48. Electron-Rich 4-Substituted Spirobifluorenes: Toward a New Family of High Triplet Energy Host Materials for High-Efficiency Green and Sky Blue Phosphorescent OLEDs

Author: Cassandre Quinton, Emmanuel Jacques, Denis Tondelier, Joëlle Rault-Berthelot, Bernard Geffroy, Sébastien Thiery, Olivier Jeannin, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique des interfaces et des couches minces [Palaiseau] (LPICM), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut d'Électronique et des Technologies du numéRique (IETR), Université de Nantes (UN)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), ANR-14-CE05-0024, Agence Nationale de la Recherche, ANR-14-CE05-0024,Men in blue,Ingénierie moléculaire de l'état triplet de semi-conducteurs organiques bipolaires : Vers de nouveaux designs moléculaires(2014), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Nantes Université (NU)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Nantes (UN)-Université de Rennes 1 (UR1)
Subjects: Ortho position, Materials science, 02 engineering and technology, Electron, 010402 general chemistry, Photochemistry, host materials, 01 natural sciences, chemistry.chemical_compound, General Materials Science, Thermal stability, organic semiconductors, Biphenyl, Phosphorescent oleds, business.industry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Fluorescence, 0104 chemical sciences, organic electronics, Semiconductor, chemistry, conjugation disruption, 4-substituted spirobifluorene, 0210 nano-technology, Phosphorescence, business, blue phosphorescent organic light-emitting diode
Abstract: International audience; We report herein a detailed structure-properties relationship study of the first examples of electron-rich 4-substituted spirobifluorenes for organic electronic applications, namely, 4-phenyl-N-carbazole-spirobifluorene (4-PhCz-SBF) and 4-(3,4,5-trimethoxyphenyl)-spirobifluorene (4-Ph(OMe)-SBF). The incorporation of the electron-rich moieties in the ortho position of the biphenyl linkage (position C4) induces unique properties, very different from those previously described in the literature for this family of semiconductors. Both dyes can be readily synthesized, possess high triplet energies and excellent thermal stability, and their HOMO energy levels are highly increased compared to those of other 4-substituted SBFs. We also provide in this work the first rationalization of the peculiar fluorescence of 4-substituted SBFs. Finally, the present dyes have been successfully incorporated as host in green and blue phosphorescent organic light-emitting diodes with high performance either for the green (EQE of 20.2%) or the blue color (EQE of 9.6%). These performances are, to the best of our knowledge, among the highest reported to date for 4-substituted SBF derivatives.
Published: 2017

49. Performance improvement of IF(CN2)2 meta based N-channel OTFTs and their integration into a stable CMOS inverter

Author: Tayeb Mohammed-Brahim, Cyril Poriel, Ismaïl Bouhadda, Emmanuel Jacques, Sarah Bebiche, Nathalie Coulon, Jean Francois Bergamini, Institut d'Electronique et de Télécommunications de Rennes (IETR), Université de Nantes (UN)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), Institut d'Électronique et des Technologies du numéRique (IETR), Nantes Université (NU)-Université de Rennes 1 (UR1), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, Evaporation, Electrical stability, Field effect, 02 engineering and technology, Substrate (electronics), 010402 general chemistry, 01 natural sciences, 7. Clean energy, law.invention, Pentacene, chemistry.chemical_compound, Field-effect mobilities, [INFO.INFO-NI]Computer Science [cs]/Networking and Internet Architecture [cs.NI], Indenofluorene, law, Peak-to-peak magnitude, Deposition rates, Materials Chemistry, Electrical and Electronic Engineering, Deposition, ComputingMilieux_MISCELLANEOUS, Organic electronics, Evaporation conditions, business.industry, Transistor, Temperature, Molecules, 021001 nanoscience & nanotechnology, Condensed Matter Physics, CMOS integrated circuits, Computer circuits, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, [SPI.TRON]Engineering Sciences [physics]/Electronics, CMOS inverters, chemistry, Logic gate, Optoelectronics, Inverter, Single crystals, 0210 nano-technology, business, Output voltage swings
Abstract: In this work we report the fabrication of N channel transistors based on IF(CN2)2 meta molecule. The effect of IF(CN2)2 meta evaporation parameters on corresponding TFTs performances, is evaluated and highlighted here. Since the effect of deposition conditions for this molecule type has not been reported yet, here we report an improvement about 20 times of field effect mobility when deposited at substrate temperature of 80 °C and deposition rate of 0.7 A/s, and then annealed at low temperature. Reached mobility of 2.2 × 10−3 cm2/V·s, is comparable to reported μFE of single crystal indenofluorene TFTs. The optimum mobility in these evaporation conditions was explained by the best compromise between the grain size and packing density of films. Fabricated IF(CN2)2 meta based devices are combined to 6,13-Bis(triisopropylsilylethynyl)pentacene devices and then integrated into a CMOS inverter logic circuit. The inverter’s VTC shows large output voltage swing. Electrical stability of the performed inverter was also evaluated and the inverter shows a correct electrical stability, after 3 h of non-stop operation and the peak to peak magnitude corresponding to VOUT decreases only by 2.6%.
Published: 2017

50. Dérivés du 4-spirobifluorène Une nouvelle famille de matrices hôtes pour des PhOLED

Author: Joëlle Rault-Berthelot, Cyril Poriel, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Jonchère, Laurent, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: [CHIM] Chemical Sciences, [CHIM]Chemical Sciences
Abstract: National audience; Cet article a pour objectif de faire un état des lieux exhaustif d’une nouvelle famille de semi-conducteurs organiques dérivés du 9,9’-spirobifluorène (SBF) ,substitués en positon 4 (4-SBF) possédant un fort potentiel en tant que matrices hôtes dans des diodes électroluminescentes organiques phosphorescentes (PhOLED). Cet article couvrira plusieurs aspects: après une approche générale sur la stratégie de synthèse des molécules 4-SBF, il donnera une analyse détaillée et comparative de l'ensemble des propriétés (optiques, électrochimiques et thermiques) et mettra en exergue les applications des dérivés 4-SBF en tant que matrice hôte dans des PhOLED.
Published: 2017

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