193 nm化学放大光刻胶研究进展

doi:10.19894/j.issn.1000-0518.210264

摘要/Abstract

摘要： 193 nm光刻胶主要有化学/非化学放大、分子玻璃和无机-有机杂化等类型。目前,商业化193 nm光刻胶基本为化学放大型,主要成分包括聚合物树脂、光致产酸剂、添加剂(碱性添加剂、溶解抑制剂等)和溶剂等。本文从光刻胶的成分出发介绍193 nm化学放大胶的研究进展,概述目前应用及研究中出现的代表性193 nm化学放大胶,总结其优缺点及未来可能的发展方向。

关键词: 化学放大胶, 聚合物树脂, 光致产酸剂, 碱性添加剂, 溶解抑制剂

Abstract: There are several platforms for 193 nm photoresists, including chemically/non-chemically amplified photoresists, molecular glass and inorganic-organic hybrid systems. This review mainly focueses on chemically amplified photoresists due to their predominante role in industrial applications. The main components of the 193 nm chemically amplified photoresist include polymer resins, photoacid generators, additives (alkaline additives, dissolution inhibitors, etc.) and solvents. We review the current status of representative 193 nm photoresists and their main components and their advantages, disadvantages and possible development directions are also discussed.

Key words: Chemically amplified photoresist, Polymer resin, Photoacid generator, Alkaline additive, Dissolution inhibitor

中图分类号:

O644

李小欧, 顾雪松, 刘亚栋, 季生象. 193 nm化学放大光刻胶研究进展[J]. 应用化学, 2021, 38(9): 1105-1118.

LI Xiao-Ou, GU Xue-Song, LIU Ya-Dong, JI Sheng-Xiang. Research Progress on Chemically Amplified 193 nm Photoresists[J]. Chinese Journal of Applied Chemistry, 2021, 38(9): 1105-1118.

参考文献

[1] WILLSON C G, ITO H, FRECHET J M J, et al. Approaches to the design of radiation-sensitive polymeric imaging-systems with improved sensitivity and resolution[J]. J Electrochem Soc, 1986, 133(1), 181-187.
[2] HOFER D C, KAUFMAN F B, KRAMER S R, et al. New high-resolution charge-transfer X-ray and electron-beam negative resist[J]. Appl Phys Lett, 1980, 37(3): 314-316.
[3] REICHMANIS E, NALAMASU O, HOULIHAN F M. Organic materials challenges for 193 nm imaging[J]. Acc Chem Res, 1999, 32: 659-667.
[4] KAJITA T, NISHIMURA Y, YAMAMOTOA 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]. Proc SPIE, 2001, 4345: 712-724.
[5] 郑金红, 黄志齐, 武文. ULSI用193nm光刻胶的研究进展[J]. 精细化工, 2005, 22: 349-353.
ZHENG J H, HUANG W Q, WU W, et al. Progress of 193 nm photoresist for ULSI supporting materials[J]. Fine Chem, 2005, 22: 349-353.
[6] WEI W, LIU J, LI H, et al. Development and application of microelectronic photoresist[J]. Prog Chem, 2014, 26(11): 1867-1888.
[7] ALLEN R D, WALLRAFF G M, HOFER D C, et al. Photoresists for 193-nm lithography[J]. IBM J Res Dev, 1997, 41(1/2): 95-104.
[8] CHOI S J, KANG Y, JUNG D W, et al. Novel single-layer chemically amplified resist for 193-nm lithography[M]. 1997, 3049: 104-112.
[9] UZODINMA O, TSUTOMU S, JEFFREY B, et al. Alicyclic polymers for 193 nm resist applications: synthesis and characterization[J]. Chem Mater, 1998, 10: 3319-3327.
[10] KUDO T, BAE J B, DAMMEL R R, et al. CD changes of 193 nm resists during SEM measurement[J]. Proc SPIE, 2001, 4345: 179-189.
[11] UESUGI T, OKADA T, WADA A, et al. Novel ArF photoresist polymer to suppress the formation of roughness in plasma etching processes[J]. J Vac Sci Technol A, 2013, 31(6): 95-104.
[12] KATO K, YASUDA A, MAEDA S I, et al. Novel ArF photoresist polymer to suppress the roughness formation in plasma etching processes[M]//SOMERVELL M H, WALLOW T I. Advances in resist materials and processing technology XXX. 2013, 8682: 86821R-1-10.
[13] STURTEVANT J L, VARANASI P R, KWONG R W, et al. 193nm single layer photoresists: defeating tradeoffs with a new class of fluoropolymers[Z]. Advances in resist technology and processing XXII. 2005, 5753: 131-139.
[14] WANG Z J, WYLIE K, MARIC M. Synthesis of narrow molecular weight distribution copolymers for ArF photoresist materials by nitroxide mediated polymerization[J]. Macromol React Eng, 2017, 11(3): 1600029.
[15] MARIC M, SEOK J, METAFIOT A, et al. Nitroxide-mediated polymerization of adamantyl-functional methacrylates for 193 nm photoresists[J]. Can J Chem Eng, 2017, 95(4): 708-716.
[16] WANG Z J, MARIC M. Synthesis of narrow molecular weight distribution norbornene-lactone functionalized polymers by nitroxide-mediated polymerization: candidates for 193-nm photoresist materials[J]. Polymers, 2014, 6(2): 565-582.
[17] 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]. 影像科学与光科学, 2020, 38: 409-15.
WEI Z B, MA W C,QIU Y X, et al. Development of matrix resins for 193 nm deep UV photoresist[J]. Imaging Sci Photochem, 2020, 38: 409-415.
[18] OKOROANYANWU U, SHIMOKAWA T, BYERS J, et al. New single layer positive photoresists for 193 nm photolithography[M]. 1997, 3049: 92-103.
[19] JUNG J C, BOK C K, BAIK K H. Design of cycloolefin maleic anhydride resist for ArF lithography[M]//CONLEY W. Advances in resist technology and processing XV, Pts 1 and 2. 1998: 11-25.
[20] DOUKI K, KAJITA T, SHIMOKAWA T. High-performance 193-nm positive resist using alternating polymer system of functionalized cyclic olefins maleic anhydride[M]//HOULIHAN F M. Advances in resist technology and processing xvii, Pts 1 and 2. 2000: 1128-1135.
[21] RAHMAN M D, ALEMY E, CONLEY W, et al. High performance 193 nm resist composition using hybrid high performance 193 nm resist composition using hybrid copolymers of cycloolefin/maleic anhydride (COMA)/methacrylate[J]. Proc SPIE, 2002, 4690: 127-135.
[22] YOON K S, JUNG D W, LEE S, et al. Novel 193nm photoresist based on olefin-containing Lactones[M]//HOULIHAN F M. Advances in resist technology and processing xviii, Pts 1 and 2. 2001: 688-694.
[23] CHOI S J, CHOI Y J, KIM Y S, et al. Improved lithographic performance of 193nm photoresists based on cycloolefin maleic anhydride copolymer by employing mixed PAGs[J]. Proc SPIE, 2001, 4345: 94-105.
[24] UESUGI T, OKADA T, WADA A, et al. Dependence of polymer main-chain structure on roughness formation of ArF photoresists in the plasma etching processes[J]. J Phys D-Appl Phys, 2012, 45(9) : 095501 1-6.
[25] CHOI S J, KIM H W, WOO S G, et al. Design and synthesis of new photoresist materials for ArF lithography[J]. Proc SPIE, 2000, 3999: 54-61.
[26] KIM H W, CHOI S J, JUNG D W, et al. Improved lithographic performance for resists based on polymers having a vinyl ether-maleic anhydride (VEMA) backbone[M]//HOULIHAN F M. Advances in resist technology and processing xviii, Pts 1 and 2. 2001: 119-130.
[27] KIM H W, JUNG D W, LEE S, et al. Design and performance of photoresist materials for ArF lithography[J]. Proc SPIE, 2001, 4345: 778-783.
[28] VARANASI P R, MANISCALCO J, MEWHERTER A M, et al. Design and development of high performance 193 nm positive resist based on functionalized poly(cyclicolefins)[M]//CONLEY W. Microlithography 1999: advances in resist technology and processing xvi, Pts 1 and 2. 1999: 51-63.
[29] ALLEN R D, OPITZ J, WALLOW T I, et al. Design of an etch-resistant cyclic olefin photoresist[M]//CONLEY W. Advances in resist technology and processing xv, Pts 1 and 2. 1998: 463-471.
[30] PATTERSON K, OKOROANYANWU U, SHIMOKAWA T, et al. Improving the performance of 193 nm photoresists based on alicyclic polymers[M]//CONLEY W. Advances in resist technology and processing xv, Pts 1 and 2. 1998: 425-437.
[31] SUWA M, IWASAWA H, KAJITA T, et al. ArF single layer photoresists based on alkaline-developable ROMP-H resin[M]//CONLEY W. Advances in resist technology and processing xv, Pts 1 and 2. 1998: 26-31.
[32] KLOPP J M, PASINI D, FRECHET J M J, et al. Structurally variable cyclopolymers with excellent etch resistance and their application to 193 nm lithography[M]//HOULIHAN F M. Advances in resist technology and processing xvii, Pts 1 and 2. 2000: 23-30.
[33] NAITO T, ASAKAWA K, SHIDA N, et al. Highly transparent chemically amplified ArF excimer-laser resists by absorption-band shift for 193 nm wavelength[J]. Jpn J Appl Phys Part 1, 1994, 33(12B): 7028-7032.
[34] CAMERON J F, CHAN N, MOORE K, et al. Comparison of acid generating efficiencies in 248 and 193 nm photoresists[M]//HOULIHAN F M. Advances in resist technology and processing xviii, Pts 1 and 2. 2001: 106-118.
[35] NALAMASU O. 193 nm single layer resist strategies, concepts, and recent results[J]. J Vac Sci Technol B: Microelectron Nanometer Struct, 1998, 16(6): 3716-3721.
[36] ISHII H, USUI S, DOUKI K, et al. Design and lithographic performances of 193-specific photoacid generators[M]//HOULIHAN F M. Advances in resist technology and processing xvii, Pts 1 and 2. 2000: 1120-1127.
[37] WANG L Y, WANG W J, GUO X. The synthesis and properties of N-hydroxy maleopimarimide sulfonate derivatives as PAG and inhibitor for deep UV photoresist[M]//STURTEVANT J L. Advances in resist technology and processing xxi, Pts 1 and 2. 2004: 608-615.
[38] 郑金红, 黄志齐, 昕陈, 等. 193 nm光刻胶的研制[J]. 感光科学与光科学, 2005, 23: 300-11.
ZHENG J H, HUANG Z Q, CHEN X, et al. The study of 193 nm photoresist[J]. Photogr Sci Photochem, 2005, 23: 300-311.
[39] SO J, JEONG Y, TAE J Y, et al. Synthesis and characterization of novel acid amplifiers with a low absorbance at 193 nm[J]. J Korean Inst Electr Electron Mater Eng, 2004, 17(8): 806-811.
[40] TAHARA M, ARIMITSU K, PARK S W, et al. Monitoring the acidolytic behavior of latent pigment enhanced by an acid amplifier in polymer film[J]. J Photopolym Sci Technol, 2000, 13: 221-222.
[41] EARLEY W, SOUCIE D, HOSOI K, et al. Double-deprotected chemically amplified photoresists (DD-CAMP): higher-order lithography[M]//HOHLE C K. Advances in resist technology and processing xxxiv. 2017, 10146: 101460H-1-15.
[42] SOUCIE D, EARLEY W, HOSOI K, et al. Higher-order lithography: double-deprotected chemically amplified photoresists (DD-CAMP)[J]. J Photopolym Sci Technol, 2017, 30(3): 351-359.
[43] LIU S, GLODDE M, VARANASI P R. Design, synthesis and characterization of fluorine-free PAGs for 193 nm lithography[M]//ALLEN R D, SOMERVELL M H. Advances in resist materials and processing technology xxvii, Pts 1 and 2. 2010, 7639: 76390D-1-8.
[44] WANG M, JARNAGIN N D, LEE C T, et al. Novel polymeric anionic photoacid generators (PAGs) and corresponding polymers for 193 nm lithography[J]. J Mater Chem, 2006, 16(37): 3701-3707.
[45] PADMANABAN M, BAE J B, COOK M, et al. Application of photodecomposable base concept to 193 nm resists[J]. Proc SPIE, 2000, 3999: 1136-1146.
[46] ASAKAWA K, USHIROGOUCHI T, NAKASE M. Effect of basic additives on sensitivity and diffusion of acid in chemical amplification resists[M]. 1995, 2438: 563-570.
[47] HOULIHAN F M, KOMETANI J M, TIMKO A G, et al. Photogenerators of sulfamic acids; use in chemically amplified single layer resists[J]. J Photopolym Sci Technol, 1998, 11: 419-429.