248 nm深紫外光刻胶用成膜树脂的研究进展

doi:10.7517/issn.1674-0475.191014

摘要/Abstract

摘要： 综述了用于248 nm化学增幅型深紫外光刻胶的不同种类和结构的成膜树脂，以及所使用单体的研发进展，包括聚甲基丙烯酸甲酯及其衍生物、聚对羟基苯乙烯及其衍生物、N取代的马来酰亚胺衍生物，以及其他聚合物等，对不同结构成膜树脂的曝光条件、对光刻胶性能的影响进行了介绍。

关键词: 光刻胶, 成膜树脂, 化学增幅型, 曝光

Abstract: Different kinds of matrix resins and structures used in 248 nm chemically amplified deep UV photoresist were summarized,including poly(methyl methacrylate) and its derivatives, poly(p-hydroxystyrene) and its derivatives, N-substituted maleimide derivatives and other polymers, and the influences of the structure and exposure conditions of film-forming resins or monomers on photoresist properties were discussed.

Key words: photoresist, matrix resin, chemical amplification, exposure

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.

WEI Zibo, MA Wenchao, QIU Yingxin. Development of Matrix Resins for 248 nm Deep UV Photoresist[J]. Imaging Science and Photochemistry, 2020, 38(3): 430-435.

参考文献

[1] 庞玉莲,邹应全. 光刻材料的发展及应用[J]. 信息记录材料, 2015,16(1):36-51. Pang Y L, Zou Y Q. Development and Application of Lithography Materials[J]. Information Recording Materials, 2015,16(1):36-51.
[2] Bruning J H. Optical lithography-thirty years and three orders of magnitude:the evolution of optical lithography tools[J]. Proceedings of SPIE, 1997,3049:14-27.
[3] Ito H. Chemical amplification resists:Inception, implementation in device manufacture, and new developments[J]. Journal of Polymer Science Part A Polymer Chemistry, 2003,41(24):3863-3870.
[4] Sturtevant J L, Conley W E, Webber S E. Photosensitization in dyed and undyed APEX-E DUV resist[C]. Advances in Resist Technology and Processing XIII. International Society for Optics and Photonics, 1996-6-14.
[5] 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. Liu J G, Jiang M, Zeng X Y. Research on the synthesis and properties of a matrix resin to be used for 248 nm photoresist[J]. Imaging Science and Photochemistry, 2013,31(5):349-360.
[6] Kim J B, Jung M H, Chang K H. Synthesis and polymerization of 3-(t-butoxycarbonyl)-1-vinylcaprolactam and application as deep UV resists[J]. Polymer Bulletin, 1997,38(3):241-247.
[7] Kim J B, Choi J H, Kwon Y G, et al. Acid diffusion control in chemically amplified resists[J]. Polymer, 1999,40(4):1087-1089.
[8] 冯波, 艾照全, 朱超. 光刻胶成膜树脂的研究进展[J]. 粘接, 2015,2:78-81. Feng B, Ai Z Q, Zhu C. Research progress of matrix resin for photoresist[J]. Adhension, 2015,2:78-81.
[9] 刘敬成,李虎.一种基于RAFT聚合法制备248 nm深紫外光刻胶成膜树脂[P].中国专利, CN105237669B.2018-5-11. Liu J C, Li H. Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method[P]. Chinese patent, CN105237669B.2018-5-11.
[10] 冉瑞成, 沈吉. 含倍半萜内酯成膜树脂及其正性248 nm光刻胶[P]. 中国专利, CN104592436B. 2018-5-8. Ran R C, Shen J. Sesquiterpene lactone-containing film-forming resin and positive 248 nm photoresist[P]. Chinese patent, CN104592436B. 2018-5-8.
[11] 冉瑞成,魏正华,宋红波.一种丙烯酸酯共聚物及包含其的光刻胶组合物[P]. 中国专利,CN108373520A.2018-8-7. Ran R C, Wei Z H, Song H B. An acrylate copolymer and a photoresist composition thereof[P].Chinese patent, CN104592436A. 2018-8-7.
[12] Kotani T, Sano M, Hayashi K I, et al. Characteristics of new KrF excimer laser resist[J]. Proceedings of SPIE-The International Society for Optical Engineering, 1990,1262:468-475.
[13] Fujimoto H H, Sasago M, Tani Y, et al. Evaluation of resist materials for KrF excimer laser lithography[J]. Proceedings of SPIE-The International Society for Optical Engineering, 1990,1262:331-343.
[14] 郑金红, 黄志齐, 侯洪森. 248 nm深紫外光刻胶[J]. 影像科学与光化学, 2003,21(5):346-256. Zheng J H, Huang Z Q, Hou H S. 248 nm deep UV photoresists[J]. Imaging Science and Photochemistry, 2003,21(5):346-356.
[15] 毛国平,霍建辉. 一种包含聚对羟基苯乙烯类聚合物和丙烯酸酯共聚物的光刻胶组合物[P]. 中国专利, CN108132584A. 2018-6-8. Mao G P, Huo J H. Photoresist composition comprising polyhydroxy styrene polymer and acrylate copolymer[P]. Chinese patent, CN108132584A. 2018-6-8.
[16] Conley W E, Breyta G, Brunsvold W R, et al. Lithographic performance of an environmentally stable chemically amplified photoresist (ESCAP)[J]. Proceedings of SPIE-The International Society for Optical Engineering, 1996, 2724:34-60.
[17] Kunz R R. PED-stabilized chemically amplified photoresist[J]. Advances in Resist Technology & Processing XIII, 1996,2724:61-69.
[18] Choi S J, Jung S Y, Kim C H, et al. Design and properties of new deep-UV positive photoresist[J]. Proceedings of SPIE-The International Society for Optical Engineering, 1996,2724:323-331.
[19] 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]. 感光科学与光化学, 2006,24(1):67-74. Liu J G, Zheng J S, Li P. Applications and syntheses of polyhydroxystyrene in deep UV Photoresist[J]. Photographic Science and Photochemistry, 2006,24(1):67-74.
[20] Ahn K D, Koo J S, Chung C M. Photoacid generating polymers based on sulfonyloxymaleimides and application as single-component resists[J]. Journal of Polymer Science Part A Polymer Chemistry, 2015,34(2):183-191.
[21] Malik S, Blakeney A J, Ferreira L, et al. Polymer structural variation towards enhancing krf resist lithographic properties[J]. Journal of Photopolymer Science and Technology, 1998,11(3):431-438.
[22] Lee C W, Kim A Y, Lee S H. Synthesis and properties of tailor-made supramolecular photo acid generators for conducting patterns of polyaniline[J]. Chemistry of Materials, 2005,17(2):366-372.
[23] Antonios M D, Frieda V R, Mieke G, et al. Partially fluorinated, polyhedral oligomeric silsesquioxane-functionalized (meth) acrylate resists for 193 nm bilayer lithography[J]. Chemistry of Materials, 2012,18(17):4040.
[24] 杨刚.含苯并噁嗪结构的共聚物成膜树脂及其深紫外负性化学增幅型光刻胶[P]. 中国专利, CN101463106B. 2010-7-28. Yang G. Copolymer film forming resin containing benzoxazine structure and deep UV negativity chemical amplification type photo resist[P]. Chinese patent, CN101463106B. 2010-7-28.
[25] 邹应全.包含聚对羟基苯乙烯类氧杂环丁烷树脂作为成膜树脂的光刻胶组合物[P]. 中国专利, CN108303851B. 2019-9-10. Zou Y Q. Photoresist composition comprising poly (p-hydroxy styrene) oxetane resin used as film formation resin[P]. Chinese patent, CN108303851B. 2019-9-10.
[26] 邹应全.包含聚对羟基苯乙烯类环氧树脂作为成膜树脂的光刻胶组合物[P]. 中国专利, CN108255018A. 2018-7-6. Zou Y Q. Photoresist composition containing poly-p-hydroxystyrene epoxy resin serving as film-forming resin[P]. Chinese patent, CN108255018A. 2018-7-6.
[27] Kazuyoshi M, Shinichi S. Positive resist composition and pattern forming method using the same[P]. US patent,8142977B2. 2012-3-27.
[28] Sou K, Yasutomo K, Kenji W, et al. Resist composition containing novel sulfonium compound, pattern-forming method using the resist composition and novel sulfonium compound[P]. US patent, 8110333B2. 2012-2-7.
[29] 刘敬成.一种可用于248 nm光刻胶的支化型聚对羟基苯乙烯共聚物[P]. 中国专利, CN105254791A. 2016-1-20. Liu J C. Branched poly (p-hydroxystyrene) copolymer used for 248nm photoresist[P]. Chinese patent, CN105254791A. 2016-1-20.
[30] DiPietro R A, Sooriyakumaran R, Swanson S A, et al. Low outgassing photoresist compositions[P]. US patent, 7951525B2. 2011-5-31.
[31] 许箭,秦龙.一种聚合物树脂及其制备方法和应用[P]. 中国专利, CN109679023A.2019-4-26. Xu J, Qin L. Polymer resin as well as preparation method and application thereof[P]. Chinese patent, CN109679023A. 2019-4-26.
[32] Barclay,George G,Cronin M F, et al. Copolymers and photoresist compositions comprising copolymer resin binder component[P]. US patent, 5861231A. 1999-1-19.
[33] Namba K, Nakanishi J, Uetani Y. A chemical amplifying type positive resist composition[P]. EU patent, 1225479B1. 2012-12-5.
[34] Turner S R, Arcus R A, Houle C G, et al. High-TG base-soluble copolymers as novolac replacements for positive photoresists[J]. Polymer Engineering and Science, 1986,26(16):1096-1100.
[35] 徐文佳,郑祥飞,纪昌炜,等. 248 nm光刻胶用丙烯酸酯共聚物的合成与性能[J]. 高分子材料科学与工程, 2017,33(11):5-9. Xu W J,Zheng X F,Ji C W, et al. Synthesis of methacrylic copolymers applied in 248 nm photoresist[J]. Polymer Materials Science and Engineering, 2017,33(11):5-9.
[36] Zheng X F, Ji C W, Liu J C, et al. Novel star polymers as chemically amplified positive-tone photoresists for KrF lithography applications[J]. Industrial & Engineering Chemistry Research, 2018,57:6790-6796.
[37] Li H, Liu J C, Zheng X F, et al. Synthesis of chemically amplified photoresist polymer containing four (meth)acrylate monomers via RAFT polymerization and its application for KrF lithography[J]. Journal of Polymer Research, 2018,23(5):102.
[38] Jacob J, Shanmugavelu P, Balasubramaniam R, et al. Study of excimer laser ablation of photoresist polymer in presence of hydrogen gas environment for micro-fluidic applications[J]. Materials Research Express, 2019,6(8):085316.
[39] Jacob J, Shanmugavelu P, Balasubramaniam R. Investigation of the performance of 248 nm excimer laser assisted photoresist removal process in gaseous media by response surface methodology and artificial neural network[J]. Journal of Manufacturing Processes, 2019,38:516-29.
[40] Wang Q Q, Zhang C, Yan C, et al. One-component chemically amplified resist composed of polymeric sulfonium salt PAGs for high resolution patterning[J]. European Polymer Journal, 2019,114:11-18.
[41] 冉瑞城.含硅烷偶联剂共聚物成膜树脂及其有机防反射膜[P]. 中国专利, CN1847274A. 2006-10-18. Ran R C. Filming copolymer resin containing silicon coupler and its organic antiflecting coating[P]. Chinese patent, CN1847274A. 2006-10-18.
[42] 冉瑞城,沈吉.含纳米硅深紫外正性光刻胶及其成膜树脂[P]. 中国专利, CN101974119B. 2012-10-3. Ran R C, Shen J. Nano silicon containing deep ultraviolet positive photoresist and forming resin thereof[P]. Chinese patent, CN101974119B. 2012-10-3.
[43] Ji C, Liu J, Zheng X, et al. Photo-sensitive bio-based copolymer containing cholic acids:novel functional materials for 248 nm photoresist[J]. Journal of Polymer Research, 2018,25(9):192.