含肉桂酰基自增感光敏聚酰亚胺的合成及光刻工艺探索

郭嘉隽; 步颜倩; 李琇廷; 董杰; 赵昕; 张清华

doi:10.11777/j.issn1000-3304.2024.24074

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含肉桂酰基自增感光敏聚酰亚胺的合成及光刻工艺探索

研究论文 | 更新时间：2024-11-15

- 含肉桂酰基自增感光敏聚酰亚胺的合成及光刻工艺探索
- Synthesis of Cinnamoyl-containing Self-enhancing Photosensitive Polyimides and Exploration of Lithographic Processes
- 高分子学报 2024年55卷第10期页码：1325-1334
- 作者机构：
  
  东华大学纤维材料改性国家重点实验室上海 201620
- 作者简介：
  
  E-mail: dj01@dhu.edu.cn
- 基金信息：
  
  国家重点研发计划课题(2022YFB3603102);中央高校基本科研业务费资助
- DOI：10.11777/j.issn1000-3304.2024.24074
  中图分类号：
- 纸质出版日期：2024-10-20，
  
  网络出版日期：2024-07-08，
  
  收稿日期：2024-03-20，
  
  录用日期：2024-05-22
- 稿件说明：
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郭嘉隽, 步颜倩, 李琇廷, 董杰, 赵昕, 张清华. 含肉桂酰基自增感光敏聚酰亚胺的合成及光刻工艺探索. 高分子学报, 2024, 55(10), 1325-1334

Guo, J. J.; Bu, Y. Q.; Li, X. T.; Dong, J.; Zhao, X.; Zhang, Q. H. Synthesis of cinnamoyl-containing self-enhancing photosensitive polyimides and exploration of lithographic processes. Acta Polymerica Sinica, 2024, 55(10), 1325-1334
郭嘉隽, 步颜倩, 李琇廷, 董杰, 赵昕, 张清华. 含肉桂酰基自增感光敏聚酰亚胺的合成及光刻工艺探索. 高分子学报, 2024, 55(10), 1325-1334 DOI： 10.11777/j.issn1000-3304.2024.24074.

Guo, J. J.; Bu, Y. Q.; Li, X. T.; Dong, J.; Zhao, X.; Zhang, Q. H. Synthesis of cinnamoyl-containing self-enhancing photosensitive polyimides and exploration of lithographic processes. Acta Polymerica Sinica, 2024, 55(10), 1325-1334 DOI： 10.11777/j.issn1000-3304.2024.24074.

摘要

以含氟二酐4

4'-(六氟异亚丙基)二邻苯二甲酸酐(6FDA)和含活性羧基的二胺3

5-二氨基苯甲酸(DABA)为单体，通过高温一步法合成可溶性的聚酰亚胺(PI)，利用酯化反应在其侧链羧基上接枝自增感光敏基团肉桂酰基. 控制6FDA与DABA加入量比例分别合成了3种不同分子量的光敏聚酰亚胺树脂PI95、PI97.5和PI100. 系统探究了3种不同分子量光敏聚酰亚胺的光刻工艺参数，并根据光刻图案质量优选出PI97.5样品. PI97.5样品的灵敏度为785 mJ/cm

，分辨率可达7 μm，线宽可达14 μm；固化后薄膜5%失重温度高于340 ℃，玻璃化转变温度可达274.2 ℃，且显示出良好的力学性能. 研究结果为开发新型负性光敏聚酰亚胺光刻胶提供了研究基础.

Abstract

A soluble polyimide (PI) was synt

hesized in a high-temperature one-step process using fluorinated dianhydride 4

‍4'-‍(hexafluoroisopropylidene)bis(phthalic anhydride) (6FDA) and reactive carboxyl-containing diamine 3

5-diaminobenzoic acid (DABA) as monomers

with the self-enhancing photosensitive cinnamoyl group grafted on the carboxyl group of the PI through the esterification reaction. Three kinds of photosensitive polyimide resins with different molecular weights

PI95

PI97.5 and PI100

were synthesized by controlling the molar ratio of 6FDA to DABA. The photolithographic process parameters of the three kinds of photosensitive polyimides with different molecular weights were systematically explored

and the PI97.5 sample was preferred according to the quality of the photolithographic pattern. The sensitivity of the PI97.5 sample is 785 mJ/cm

the resolution is up to 7 μm

and the line width is up to 14 μm. The 5% weight loss temperature of the cured film is higher than 340 ℃

and the glass transition temperature is up to 274.2 ℃

which shows good mechanical properties. The results provide a research basis for the development of new negative photosensitive polyimide photoresists.

关键词

光敏聚酰亚胺肉桂酰基自增感光刻工艺光敏特性

Keywords

Photosensitive polyimideCinnamoyl groupSelf-photosensitivePhotolithography processPhotosensitive properties

references

丁孟贤. 聚酰亚胺: 化学、结构与性能的关系及材料. 第二版. 北京: 科学出版社, 2012. 1-4.

蒋大伟, 姜其斌, 刘跃军, 李强军. 聚酰亚胺的研究及应用进展. 绝缘材料, 2009, 42(2), 33-35. doi:10.3969/j.issn.1009-9239.2009.02.010http://dx.doi.org/10.3969/j.issn.1009-9239.2009.02.010

Fang Y. T.; Dong J.; Zhao X.; Chen T. T.; Xiang L. P.; Xie Y. S.; Zhang Q. H. Covalently linked polydopamine-modified boron nitride nanosheets/polyimide composite fibers with enhanced heat diffusion and mechanical behaviors. Compos. Part B, 2020, 199, 108281. doi:10.1016/j.compositesb.2020.108281http://dx.doi.org/10.1016/j.compositesb.2020.108281

Li X. T.; Liu T.; Jiao Y. Z.; Dong J.; Gan F.; Zhao X.; Zhang Q. H. Novel high-performance poly(benzoxazole-co-imide) resins with low dielectric constants and superior thermal stabilities derived from thermal rearrangement of ortho-hydroxy polyimide oligomers. Chem. Eng. J., 2019, 359, 641-651. doi:10.1016/j.cej.2018.11.175http://dx.doi.org/10.1016/j.cej.2018.11.175

Li M. N.; Zhang Z. J.; Yin Y. T.; Guo W. C.; Bai Y. G.; Zhang F.; Zhao B.; Shen F.; Han X. G. Novel polyimide separator prepared with two porogens for safe lithium-ion batteries. ACS Appl. Mater. Interfaces, 2020, 12(3), 3610-3616. doi:10.1021/acsami.9b19049http://dx.doi.org/10.1021/acsami.9b19049

Xu Z.; Croft Z. L.; Guo D.; Cao K.; Liu G. L. Recent development of polyimides: Synthesis, processing, and application in gas separation. J. Polym. Sci., 2021, 59(11), 943-962. doi:10.1002/pol.20210001http://dx.doi.org/10.1002/pol.20210001

郭海泉, 杨正华, 高连勋. 光敏聚酰亚胺光刻胶研究进展. 应用化学, 2021, 38(9), 1119-1137. doi:10.19894/j.issn.1000-0518.210274http://dx.doi.org/10.19894/j.issn.1000-0518.210274

Fu M. C.; Higashihara T.; Ueda M. Recent progress in thermally stable and photosensitive polymers. Polym. J., 2018, 50(1), 57-76. doi:10.1038/pj.2017.46http://dx.doi.org/10.1038/pj.2017.46

Oyama T. Photosensitive engineering plastics based on reaction development patterning. Polym. J., 2018, 50, 419-429. doi:10.1038/s41428-018-0028-8http://dx.doi.org/10.1038/s41428-018-0028-8

Sezer Hicyilmaz A.; Celik Bedeloglu A. Applications of polyimide coatings: a review. SN Appl. Sci., 2021, 3(3), 363. doi:10.1007/s42452-021-04362-5http://dx.doi.org/10.1007/s42452-021-04362-5

Fukukawa K. I.; Ueda M. Recent progress of photosensitive polyimides. Polym. J., 2008, 40(4), 281-296. doi:10.1295/polymj.pj2007178http://dx.doi.org/10.1295/polymj.pj2007178

Tseng L. Y.; Lin Y. C.; Kuo C. C.; Kuo C. C.; Ueda M.; Chen W. C. An ultra heat-resistant polyimide formulated with photo-base generator for alkaline-developable, negative-type photoresist. React. Funct. Polym., 2020, 157, 104760. doi:10.1016/j.reactfunctpolym.2020.104760http://dx.doi.org/10.1016/j.reactfunctpolym.2020.104760

Lee S. W.; Kim S. I.; Lee B.; Choi W.; Chae B.; Bin Kim S.; Ree M. Photoreactions and photoinduced molecular orientations of films of a photoreactive polyimide and their alignment of liquid crystals. Macromolecules, 2003, 36(17), 6527-6536. doi:10.1021/ma034445uhttp://dx.doi.org/10.1021/ma034445u

Hahm S.; Lee T. J.; Ree M. Photo- and rubbing-alignable brush polyimides bearing three different chromophores. Adv. Funct. Mater., 2007, 17(8), 1359-1370. doi:10.1002/adfm.200600369http://dx.doi.org/10.1002/adfm.200600369

Won J. M.; Suk H. J.; Wee D.; Kim Y. H.; Ka J. W.; Kim J.; Ahn T.; Yi M. H.; Jang K. S. Photo-patternable polyimide gate insulator with fluorine groups for improving performance of 2,‍7-didecyl [1]benzothieno [3,‍2-b][1]benzothiopeneC10-BTBT) thin-film transistors. Org. Electron., 2013, 14(7), 1777-1786. doi:10.1016/j.orgel.2013.04.002http://dx.doi.org/10.1016/j.orgel.2013.04.002

Gupta P.; Trenor S. R.; Long T. E.; Wilkes G. L. In situ photo-cross-linking of cinnamate functionalized poly(methyl methacrylate-co-2-hydroxyethyl acrylate) fibers during electrospinning. Macromolecules, 2004, 37(24), 9211-9218. doi:10.1021/ma048844ghttp://dx.doi.org/10.1021/ma048844g

Kitayama Y.; Harada A. Carboxy-functionalized pH responsive capsule polymer particles fabricated by particulate interfacial photocrosslinking. J. Mater. Chem. B, 2022, 10(37), 7570-7580. doi:10.1039/d1tb02866ahttp://dx.doi.org/10.1039/d1tb02866a

Li M. M.; Gan F.; Dong J.; Fang Y. T.; Zhao X.; Zhang Q. H. Facile preparation of continuous and porous polyimide aerogel fibers for multifunctional applications. ACS Appl. Mater. Interfaces, 2021, 13(8), 10416-10427. doi:10.1021/acsami.0c21842http://dx.doi.org/10.1021/acsami.0c21842

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