193 nm深紫外光刻胶用成膜树脂的研究进展

doi:10.7517/issn.1674-0475.191013

摘要/Abstract

摘要： 本文综述了用于193 nm深紫外光刻胶的主体成膜树脂的种类及常用合成单体的研究进展，包括聚（甲基）丙烯酸酯体系、环烯烃-马来酸酐共聚物（COMA）体系、乙烯醚-马来酸酐共聚物（VEMA）体系、降冰片烯加成聚合物体系、环化聚合物体系、有机-无机杂化树脂体系以及光致产酸剂（PAG）接枝聚合物主链型等，并分析了目前关于曝光、分辨率和抗蚀刻性能方面存在的问题及未来的发展方向。

关键词: 光刻胶, 成膜树脂, 曝光, 分辨率, 抗蚀刻性能

Abstract: The research progress of the main matrix resins and common synthetic monomers for 193 nm deep UV photoresist was reviewed. The film-forming resin includes poly(methyl)acrylate, cycloolefin-maleic anhydride (COMA), ethylene ether-maleic anhydride (VEMA), norborneene addendum polymer, cyclized polymer, organic-inorganic hybrid resin, and PAG graft on polymer backbone. The existing problems about exposure, resolution and etch resistance and the future development direction were also discussed.

Key words: photoresist, matrix resin, exposure, resolution, etch resistance

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.

WEI Zibo, MA Wenchao, QIU Yingxin. Development of Matrix Resins for 193 nm Deep UV Photoresist[J]. Imaging Science and Photochemistry, 2020, 38(3): 409-415.

参考文献

[1] Reichmanis A, Thompson L F. Polymer materials for microlithography[J]. Annual Review of Materials Research, 1987,17(1):235-271.
[2] Okoroanyanwu U, Byers J, Shimokawa T, et al. Alicyclic polymers for 193 nm resist applications:lithographic evaluation[J]. Chemistry of Materials, 1998,10(11):3319-3327.
[3] Ito H. Chemically amplified resists:past, present, and future[J]. Procedings of SPIE, 1999,3678:2-12.
[4] Sahoo P B, Vyas R, Wadhwa M, et al. Progress in deep-UV photoresists[J]. Bulletin of Materials Science, 2002,25(6):553-556.
[5] 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):346-356. Zheng J H, Huang Z Q, Hou H S. Evolution and progress of deep UV 248 nm photoresists[J]. Imaging Science and Photochemistry, 2003,21(5):346-356.
[6] 郑金红, 黄志齐, 文武. ULSI用193 nm光刻胶的研究进展[J]. 精细化工, 2005,22(5):348-353. Zheng J H, Huang Z Q, Wen W. Progress of 193 nm photoresist for ULSI supporting materials[J]. Fine Chemicals, 2005,22(5):348-353.
[7] Kajita T, Nishimura Y, Yamamoto M, et al. 193 nm single layer resist materials:total consideration on design, physical properties, and lithographic performances on all major alicyclic platform chemistries[J]. Proceedings of SPIE-The International Society for Optical Engineering, 2001,4345:712-724.
[8] Allen R D, Wallraff G M, Hofer D C, et al. Photoresists for 193-nm lithography[J]. IBM Journal of Research & Development, 1997,41(41):95-104.
[9] Allen R. Progress in 193 nm photoresists for sub-0.20μm devices, 193 nm photoresists may prove to be the best solution[J]. Semiconductor International, 1997,20(10):70-81.
[10] Reichmanis E, Omkaram N, Frank M H. Organic materials challenges for 193 nm imaging[J]. Accounts of Chemical Research, 1999,32(8):659-667.
[11] Ohnishi Y, Itoh M, Mizuno K, et al. Postirradiation polymerization of e-beam negative resists:theoretical analysis and method of inhibition[J]. Journal of Vacuum Science & Technology, 1981,19(4):1141-1144.
[12] Ito H. Chemical amplification resists for microlithography[J]. Advances in Polymer Science, 2005:37-245.
[13] Hasegawa E, Maeda K, Iwasa S. Molecular design and development of photoresists for ArF excimer laser lithography[J]. Polymers for Advanced Technologies, 2015,11(8-12):560-569.
[14] 冉瑞成, 沈吉, 孙友松, 等. 含倍半萜的成膜树脂及其正性干法曝光193 nm光刻胶[P]. 中国专利, CN104448114A. 2015-3-25. Ran R C, Shen J, Sun Y S, et al. Sesquiterpene containing film forming resin and its positive dry exposure to 193 nm photoresist[P]. Chinese Patent, CN104448114A. 2015-3-25.
[15] Wang M, Tang M, Her T H, et al. Synthesis, characterization and lithography performance of novel anionic photoacid generator (PAG) bound polymers[J]. Journal of Photopolymer Science and Technology, 2007,20(6):793-797.
[16] Yamamoto H, Kozawa T, Tagawa S. Dissolution kinetics in polymer-bound and polymer-blended photo-acid generators[J]. Journal of Photopolymer Science and Technology, 2012,25(5):693-698.
[17] Jarnagin N D, Wang M, Rabinobich M, et al. PAG incorporated polymeric resists for sub-100 nm patterning at 193 nm exposure[J]. Journal of Photopolymer Science and Techno-logy, 2006,19(6):719-725.
[18] Kim H W, Jung D W, Lee S, et al. Design and performance of new photoresist materials for ArF lithography[J]. Journal of Applied Polymer Science, 2004,92(1):165-170.
[19] 常磊. 193 nm远紫外光刻胶及其制备方法[P]. 中国专利, CN1869814A. 2006-11-29. Chang L. 193nm far-ultraviolet photoetching rubber and its preparation method[P]. Chinese Patent, CN1869814A. 2006-11-29.
[20] Ito H. Dissolution behavior of chemically amplified resist polymers for 248-, 193-, and 157-nm lithography[J]. IBM Journal of Research and Development, 2001,45(5):683-695.
[21] Okoroanyanwu U, Shimokawa T, Byers J D, et al. Pd(Ⅱ)-catalyzed addition polymerization and ring opening metathesis polymerization of alicyclic monomers:routes to new matrix resins for 193 nm photolithography[J]. Journal of Molecular Catalysis A:Chemical, 1998,133(1):93-114.
[22] Okoroanyanwu U, Shimokawa T, Byers J D, et al. New single-layer positive photoresists for 193-nm photolithography[J]. Proceedings of SPIE-The International Society for Optical Engineering, 1997,3049:92-103.
[23] Whittaker A K, Blakey I, Liu H, et al. High-RI resist polymers for 193 nm immersion lithography[J]. Proceedings of SPIE-The International Society for Optical Engineering, 2005,5753:827-835.
[24] 魏玮, 刘敬成, 李虎, 等. 微电子光致抗蚀剂的发展及应用[J]. 化学进展, 2014,26(11):1867-1888. Wei W, Liu J C, Li H, et al. Development and application of mircroelectronic photoresist[J]. Progress in Chemistry, 2014,26(11):1867-1888.
[25] Sanders D P. Advances in patterning materials for 193 nm immersion lithography[J]. Chemical Reviews, 2010,110(1):321-360.
[26] Zimmerman P A, Byers J, Piscani E, et al. Development of an operational high refractive index resist for 193nm immersion lithography[J]. Proceedings of the SPIE-Advanced Lithography, 2008,6923(6):1-10.
[27] Wang Q, Yan C, You F, et al. A new type of sulfonium salt copolymers generating polymeric photoacid:Preparation, properties and application[J]. Reactive and Functional Polymers, 2018,130:118-125.
[28] 冉瑞城, 沈吉, 庄学军. 含硅193 nm负性光刻胶及其成膜树脂[P].中国专利, CN1834785A. 2006-9-20. Ran R C, Shen J, Zhuang X J. Deep UV positive photoresist containing nano silicon and its film forming resin[P]. Chinese Patent, CN1834785A. 2006-9-20.