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2. Controlling the Dissolution Behavior of (Meth)acrylate-Based Photoresist Polymers in Tetramethylammonium Hydroxide by Introducing Adamantyl Groups.

Author

Kim, Jinyoung, Lee, Choong-Jae, Lee, Dong-Gun, Lee, Geon-Ho, Hyeon, Jayoung, Choi, Yura, and Cho, Namchul

Subjects
*POLYMER solutions, *PHOTORESISTS, *PHOTOLITHOGRAPHY, *FUNCTIONAL groups, *METHAMPHETAMINE
Abstract

(Meth)acrylate polymers are commonly used as photoresist materials in photolithography. However, these polymers encounter the problem of swelling during the development process. To address this, we explored the use of a hydrophobic group to control the solubility in the hydrophilic developer. In this study, we synthesized two types of polymers to evaluate the impact of the developer on (meth)acrylate polymers for photoresist applications. Adamantyl methacrylate (AdMA) was selected as the hydrophobic group, while 2-ethoxyethyl acrylate (2-EEA) served as the hydrophilic group, enabling the synthesis of both hydrophilic and hydrophobic polymers. Our goal was to assess how the presence of adamantyl monomers influenced the solubility of the polymer. This study demonstrated that solubility was primarily influenced by functional groups, particularly hydrophobic groups, rather than other factors. Polymers with more than 50% hydrophobic groups can be effectively controlled for their solubility in TMAH. These findings show that the solubility of photoresist polymers in TMAH can be tuned by incorporating a high proportion of hydrophobic groups. The study further confirms the role of adamantyl monomers as effective hydrophobic (aliphatic) groups in modulating the solubility of (meth)acrylate polymers in developer solutions. [ABSTRACT FROM AUTHOR]

Published
2025
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9. Swelling Behavior of Acrylate-Based Photoresist Polymers Containing Cycloaliphatic Groups of Various Sizes.

Author

Lee, Choong-Jae, Kim, Jinyoung, Lee, Geon-Ho, Hyeon, Jayoung, Choi, Yura, and Cho, Namchul

Subjects
*MOLECULAR volume, *FUNCTIONAL groups, *THERMAL properties, *PHOTORESISTS, *THERMAL resistance
Abstract

Photoresist polymers containing cycloaliphatic acrylic monomers have been synthesized for use in the microcircuits of semiconductors. Although cycloaliphatic acrylic monomers exhibit a high etch resistance and excellent thermal properties, their large size increases the distance between the main chains of the resulting polymers. This increased distance facilitates the penetration of a developer between the main chains, which leads to swelling and thus pattern collapse, distortion, and delamination, thereby complicating the fabrication of microcircuits. To solve this problem, various large developers were used in previous studies to reduce the swelling effect. However, these developers could not easily dissolve the unexposed regions of the resist. To overcome this issue, we designed photoresist polymers with smaller functional groups to decrease the degree of swelling. Specifically, ArF photoresist polymers were synthesized from monomers with various sizes of functional groups. We confirmed that the polymer synthesized using cyclohexyl methacrylate (CHMA), which had the smallest functional group, exhibited the shortest distance between the main chains. Consequently, this polymer showed the least swelling, with a swelling ratio of 109%. In contrast, the polymers synthesized using isobornyl acrylate (IBOA) and dicyclopentanyl methacrylate (TCDMA), which have large functional groups, exhibited greater distances between the main chains, resulting in swelling ratios of 114% and 112%, respectively. The polymer with a swelling ratio of 109% showed excellent patterning properties, while those with swelling ratios of 114% and 112% were delaminated by the developer. Our work introduces a novel approach to help reduce the swelling effect and achieve high-quality patterns in negative photoresists. [ABSTRACT FROM AUTHOR]

Published
2024
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