两种耐高温紫外正型光刻胶成膜树脂的制备及性能

doi:10.7517/j.issn.1674-0475.2012.05.330

影像科学与光化学 ›› 2012, Vol. ›› Issue (5): 330-337.DOI: 10.7517/j.issn.1674-0475.2012.05.330

两种耐高温紫外正型光刻胶成膜树脂的制备及性能

刘建国

华中科技大学武汉光电国家实验室激光与太赫兹功能实验室, 湖北武汉 430074

收稿日期:2012-01-13 修回日期:2012-03-14 出版日期:2012-09-15 发布日期:2012-05-25
通讯作者: 刘建国(1973-),工学博士,副研究员,主要从事光电材料化学与激光先进制造技术的研究,E-mail:ljg712@yahoo.com.cn.
基金资助:
国家自然科学基金面上项目(51172081).

Preparation and Properties of Two High-Thermostability Matrix Resins for UV Positive Photoresist

LIU Jian-guo

Laser and Terahertz Functional Laboratory, Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan 430074, Hubei, P. R. China

Received:2012-01-13 Revised:2012-03-14 Online:2012-09-15 Published:2012-05-25

摘要/Abstract

摘要： 分别通过N-(p-羟基苯基)甲基丙烯酰胺与N-苯基马来酰亚胺、N-苯基甲基丙烯酰胺与N-(p-羟基苯基)马来酰亚胺的共聚合,制备了两种聚合物树脂聚N-(p-羟基苯基)甲基丙烯酰胺共N-苯基马来酰亚胺(poly(HPMA-co-PMI))和聚N-苯基甲基丙烯酰胺共N-(p-羟基苯基)马来酰亚胺(poly(MPA-co-HPMI)).结果表明,这两种聚合物都是按1:1的摩尔比交替共聚的,它们都具有良好的溶解性、成膜性和亲水性,并且它们的玻璃化温度T_g都在280℃以上.将它们分别与感光剂2,1,5-磺酰氯的衍生物、助剂二苯甲酮等复配成两种紫外正型光刻胶,初步光刻实验表明,其最大分辨率都可以达到1 μm,并且都可以耐270℃的高温.

关键词: 紫外正型光刻胶, 成膜树脂, 耐热性, 聚N-(p-羟基苯基)甲基丙烯酰胺共N-苯基马来酰亚胺, 聚N-苯基甲基丙烯酰胺共N-(p-羟基苯基)马来酰亚胺

Abstract: Two copolymers poly ((N-(p-hydroxyphenyl)methacrylamide)-co-(N-phenylmaleimide)) poly(HPMI-co-PMA) and poly ((N-phenylmethacrylamide)-co-(N-(p-hydroxyphenyl)maleimide)) poly (PMA-co-HPMI) were prepared from the copolymerizations of N-(p-hydroxyphenyl)methacrylamide and N-phenylmaleimide, and N-phenylmethacrylamide and N-(p-hydroxyphenyl)maleimide, respectively. It showed that both copolymers were 1:1 in molar composition and were alternating. Both had good solubility in organic solvent, film-forming characteristics, hydrophilicity, and high glass transition temperature (T_g > 280℃).As matrix resins,they were mixed respectively with photosensitizer derivative of 2,1,5-diazonaphthoquinone sulfochloride (DNS), additive benzophenone, etc. to obtain two UV positive photoresist. Preliminary photolithographic experiments testified that both photoresists had a resolution of no less than 1 μm and a high-thermostability of up to 270℃.

Key words: UV positive photoresist, matrix resin, thermostability, poly ((N-(p-hydroxyphenyl)methacrylamide)-co-(N-phenylmaleimide)), poly((N-phenylmethacrylamide)-co-(N-(p-hydroxyphenyl)maleimide))

中图分类号:

刘建国. 两种耐高温紫外正型光刻胶成膜树脂的制备及性能[J]. 影像科学与光化学, 2012, (5): 330-337.

LIU Jian-guo. Preparation and Properties of Two High-Thermostability Matrix Resins for UV Positive Photoresist[J]. Imaging Science and Photochemistry, 2012, (5): 330-337.

参考文献

[1] 许箭,陈力,田凯军,等. 先进光刻胶材料的研究进展[J]. 影像科学与光化学,2011,29(6): 417-429. Xu J, Chen L, Tian K J, et al. Molecular structure of advanced photoresists[J]. Imaging Science and Photochemisty, 2011,29(6): 417-429.
[2] Liu J G,Li P,Liu H P, et al. A novel amide-imide copolymer as a matrix resin for ultraviolet photoresists: preparation, properties, and application[J]. J. Appl. Polym. Sci., 2010, 117(6): 3715-3721.
[3] Conley W. Considerations in the development of deep UV photoresist material & processes[J]. Proc. SPIE, 1995, 2438: 40-52.
[4] Richard S T, Robert A A, Aonrad G H, et al. High-T_g base-soluble copolymers as novolac replacements for positive photoreists[J]. Polym. Eng. Sci., 1986, 26(16): 1096-1100.
[5] Chiang W Y, Lu J Y. Preparation and properties of Si-containing copolymer for near-UV resist. I. Poly(N-(4-hydrophenyl)maleimide-alt-p-trimethylsilylstyrene)[J]. J. Polym. Sci.: Part A: Polym. Chem., 1991, 29: 399-410.
[6] 彭进,张琳琪,邹文俊,等. N-(4-羟基苯基)马来酰亚胺的合成研究[J]. 河南化工,2003,7:13-16. Peng J, Zhang L Q, Zou W J, et al. Study on synthesis of N-(4-hydroxyphenyl)maleimide[J]. Henan Chemical Industry, 2003, 7: 13-16.
[7] 袁明荣,黄建兵,龚本民. 聚苯乙烯-N-(4-羟基苯基)-马来酰亚胺合成的研究[J]. 高分子材料科学与工程,1990,1:84-88. Yuan M R, Huang J B, Gong B M. The study of the synthetic methods of poly (styrene-alt-N-(p-hydroxyphenyl)maleimide)[J]. Polymeric Materials Science and Engineering, 1990, 1: 84-88.
[8] Tawney P O, Synder R H, Bryan C E. The chemistry of maleimide and its derivatives. I. N-carbamylmaleimide[J]. J. Org. Chem., 1960, 25(1): 56-60.
[9] Tawney P O, Synder R H, Conger R P. The chemistry of maleimide and its derivatives. II. Maleimide and N-methylolmaleimide[J]. J. Org. Chem., 1961, 26(1): 15-21.
[10] Bauer L, Miarka S V. Stereospecific lossen rearrangements[J]. J. Org. Chem., 1959, 24(12): 1293-1296.
[11] Jun O, Uozumi Y. Copolymer, image-forming composition and plate for lithography. European Patent, 1557330A1. 2005-09-21.
[12] 谢文,刘建国,李平. 一种新型紫外正型光刻胶成膜树脂的制备及其光刻性能研究[J]. 影像科学与光化学,2010,28(1):52-58. Xie W, Liu J G, Li P. A novel UV photoresist matrix resin and its photolithographic process[J]. Imaging Science and Photochemistry, 2010, 28(1): 52-58.
[13] Liang J L, Bell J P. Properties of electopolymerized polycarboxyphenylmethacrylamide matrices/graphite fiber composites: crosslinking effect[J]. Polym. Eng. Sci., 1994, 34(4): 341-351.
[14] Bell J P, Scola D A, Liang J L. Process for forming methacrylamide polymer prepreg composite by electropolymerization. US Patent, 5238542. 1993-08-24.
[15] 刘建国,李平,李萍,等. 甲基丙烯酰氯制备方法的改进[J]. 化学试剂,2007,29(11): 699-700. Liu J G, Li P, Li P, et al. Improvement in synthesis of methacryloyl chloride[J]. Chemical Reagents, 2007, 29(11): 699-700.
[16] 李艳华,杨开梅,许永廷,等. 两种新的卟啉化合物的合成及其性能研究[J]. 沈阳工业大学学报,2000,22(1): 84-86. Li Y H, Yang K M, Xu Y T, et al. Synthesis and studies of two new porphyrins[J]. Journal of Shengyang University of Technology, 2000, 22(1): 84-86.
[17] 李云. N-苯基马来酰亚胺的开发[J]. 石化技术与应用,1987,2: 9-12. Li Y. Development of N-phenylmaleimide[J]. Petrochemical Technology and Application, 1987, 2: 9-12.
[18] 王慧,游凤祥,陈明,等. 高玻璃化温度化学增幅光致抗蚀剂的制备[J]. 感光科学与光化学,1998,16(3):245-249. Wang H, You F X, Chen M, et al. Preparation of water-based negative chemical amplified photoresist with high glass transition temperature[J]. Photographic Science and Photochemistry, 1998, 16(3): 245-249.
[19] 刘建国,李平,杨坤涛,等. N-(p-羟基苯基)甲基丙烯酰胺的合成与表征[J]. 化学研究与应用,2008,20(7): 876-878. Liu J G, Li P, Yang K T, et al. Synthesis and characterization of N-(p-hydroxyphenyl)methacrylamide[J]. Chemical Research and Application, 2008, 20(7): 876-878.
[20] 复旦大学高分子科学系高分子科学研究所编著. 高分子实验技术[M]. 上海:复旦大学出版社,1996. 318. Polymer Research Institute, Department of Polymer Science, Fudan University. Polymer Experiment Technology[M]. Shanghai: Fudan University Press, 1996. 318.

两种耐高温紫外正型光刻胶成膜树脂的制备及性能

Preparation and Properties of Two High-Thermostability Matrix Resins for UV Positive Photoresist

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 10

编辑推荐

Metrics

本文评价

[1]	郑祥飞, 孙小侠, 刘敬成, 穆启道, 刘仁, 刘晓亚. 化学增幅型光刻胶材料研究进展[J]. 影像科学与光化学, 2020, 38(3): 392-408.
[2]	魏孜博, 马文超, 邱迎昕. 193 nm深紫外光刻胶用成膜树脂的研究进展[J]. 影像科学与光化学, 2020, 38(3): 409-415.
[3]	魏孜博, 马文超, 邱迎昕. 248 nm深紫外光刻胶用成膜树脂的研究进展[J]. 影像科学与光化学, 2020, 38(3): 430-435.
[4]	刘建国, 蒋明, 曾晓雁. 一种248 nm光刻胶成膜树脂的合成及相关性能研究[J]. 影像科学与光化学, 2013, 31(5): 349-360.
[5]	谢文, 刘建国, 李平. 一种新型紫外正型光刻胶成膜树脂的制备及光刻性能研究[J]. 影像科学与光化学, 2010, 28(1): 52-58.
[6]	刘建国, 郑家燊, 李平. 聚羟基苯乙烯在光致抗蚀剂中的应用及其合成[J]. 影像科学与光化学, 2006, 24(1): 67-74.
[7]	刘世雄, 顾陈斌, 王东军, 王歆秋, 甄珍, 刘新厚. 耐热性有机高分子的性能研究及其在塑料光纤中的应用[J]. 影像科学与光化学, 2001, 19(4): 304-309.
[8]	薛永薰, 邬兰, 王鹏. 成膜树脂对重氮萘醌体系正性光致抗蚀材料性能的影响[J]. 影像科学与光化学, 2000, 18(1): 85-94.
[9]	曹曙光, 王仁祥, 曹维孝. 阴图PS版感光层的光交朕[J]. 影像科学与光化学, 1996, 14(1): 44-47.
[10]	白宗武, 张秋红, 黄小力, 黄毓礼. 光敏聚酰亚胺光刻胶及光刻工艺的研究[J]. 影像科学与光化学, 1995, 13(4): 366-370.