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A novel fluorinated aromatic dianhydride, 4,4′-[2,2,2-trifluoro-1-(3-trifluoromethyl-phenyl)ethylidene]diphthalic anhydride (TFDA) was synthesized by coupling of 3′-trifluoromethyl-2,2,2-trifluoroacetophenone with o-xylene under the catalysis of trifluoromethanesulfonic acid, followed by oxidation of KMnO4 and dehydration. A series of fluorinated aromatic polyimides derived from the novel fluorinated aromatic dianhydride TFDA with various aromatic diamines, such as p-phenylenediamine (p-PDA), 4,4′-oxydianiline (ODA), 1,4-bis(4-aminophenoxy)benzene (p-APB), 1,3-bis(4-amino-phenoxy)benzene (m-APB), 4-(4-aminophenoxy)-3-trifluoromethylphenylamine (3FODA) and 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene (6FAPB), were prepared by polycondensation procedure. All the fluorinated polyimides were soluble in many polar organic solvents such as NMP, DMAc, DMF, and m-cresol, as well as some of low boiling point organic solvents such as CHCl3, THF, and acetone. Homogeneous and stable polyimide solutions with solid content as high as 35–40 wt % could be achieved, which were prepared by strong and flexible polyimide films or coatings. The polymer films have good thermal stability with the glass transition temperature of 232–322 °C, the temperature at 5% weight loss of 500–530 °C in nitrogen, and have outstanding mechanical properties with the tensile strengths of 80.5–133.2 MPa as well as elongations at breakage of 7.1–12.6%. It was also found that the polyimide films derived from TFDA and fluorinated aromatic diamines possess low dielectric constants of 2.75–3.02, a low dissipation factor in the range of 1.27–4.50 × 10−3, and low moisture absorptions

A series of fluorinated poly(amide imide)s were prepared from 1,4-bis(2′-trifluoromethyl-4′-trimellitimidophenoxy)benzene and various aromatic diamines [3,3′,5,5′-tetramethyl-4,4′-diaminediphenylmethane, α,α-bis(4-amino-3,5-dimethyl phenyl)-3′-trifluoromethylphenylmethane, 1,4-bis(4′-amino-2′-trifluoromethylphenoxy)benzene, 4-(3′-trifluoromethylphenyl)-2,6-bis(3′-aminophenyl)pyridine, and 1,1-bis(4′-aminophenyl)-1-(3′-trifluoromethylphenyl)-2,2,2-trifluoroethane]. The fluorinated poly(amide imide)s, prepared by a one-step polycondensation procedure, had good solubility both in strong aprotic solvents, such as N-methyl-2-pyrrolidinone, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, and cyclopentanone, and in common organic solvents, such as tetrahydrofuran and m-cresol. Strong and flexible polymer films with tensile strengths of 84–99 MPa and ultimate elongation values of 6–9% were prepared by the casting of polymer solutions onto glass substrates, followed by thermal baking. The poly(amide imide) films exhibited high thermal stability, with glass-transition temperatures of 257–266 °C and initial thermal decomposition temperatures of greater than 540 °C. The polymer films also had good dielectric properties, with dielectric constants of 3.26–3.52 and dissipation factors of 3.0–7.7 × 10−3, and acceptable electrical insulating properties. The balance of excellent solubility and thermal stability associated with good mechanical and electrical properties made the poly(amide imide)s potential candidates for practical applications in the microelectronics industry and other related fields. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 1831–1840, 2003