Development of Photoresist Resins and Their Synthesis Methods for Extreme Ultraviolet Lithography

doi:10.7517/issn.1674-0475.210122

Abstract

Abstract: Extreme ultraviolet lithography (EUVL) has become the most productive technology to achieve the manufacturing of integrated circuit at 22 nm node and beyond. In this paper, the structural characteristics of the EUV photoresist resins and their effects on photolithographic properties were introduced. Based on the structures and synthesis methods of photoresists, the polymeric synthesis methods of chemically and non-chemically amplified EUV resists were mainly reviewed. Finally, the direction of structural design for EUV photoresist in the future was forecasted.

Key words: photoresist resin, extreme ultraviolet lithography, synthesis, modification

WEN Shuai, LIU Qiang. Development of Photoresist Resins and Their Synthesis Methods for Extreme Ultraviolet Lithography[J]. IMAGING SCIENCE AND PHOTOCHEMISTRY, 2021, 39(4): 504-511.

References

[1] Murase S, Kinoshita K, Horie K, et al. Photo-optical control with large refractive index changes by photodimerization of poly(vinyl cinnamate) film[J]. Macromolecules, 1997,30(25):8088-8090.
[2] 张玉军, 郑岩, 张明艳. 环化聚丁二烯的合成及其在光刻胶中的应用[J]. 化学与粘合, 2006,28(3):191-193.
[3] Narasimhan B, Wanat S F, Rahman M D. Novel strategies for novolak resin fractionation:consequences for advanced photoresist applications[J]. Polymer Engineering and Science, 2000,40(10):2251-2261.
[4] Liu J, Qiao Y, Liu Z, et al. The preparation of a novel polymeric sulfonium salt photoacid generator and its application for advanced photoresists[J]. RSC Advances, 2014,4:21093-21100.
[5] Fukuhara T, Shibasaki Y, Ando S, et al. Synthesis of poly[N-(1-adamantyl)vinylsulfonamide-co-2-(2-methyl)adamanty-l methacrylate] for 193 nm lithography[J]. Macromolecules, 2005,38(8):3041-3043.
[6] 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.
[7] Kemp K, Wurm S. EUV lithography[J]. Comptes Rendus Physique, 2006,7(8):875-886.
[8] 耿永友, 邓常猛, 吴谊群. 极紫外光刻材料研究进展[J]. 红外与激光工程, 2014,43(6):1850-1856.
[9] Kudo H, Suyama Y, Oizumi H, et al. Novel extreme ultraviolet (EUV)-resist material based on noria (water wheel-like cyclic oligomer)[J]. Journal of Materials Chemistry, 2010,20(21):4445-4450.
[10] Prabhu V M, Kang S, Sha J, et al. Neutron reflectivity characterization of the photoacid reaction-diffusion latent and developed images of molecular resists for extreme ultraviolet lithography[J]. Langmuir, 2012,28(20):7665-7678.
[11] Yu M, Xu H, Kosma V, et al. Positive tone nanoparticle photoresists:new insight on the patterning mechanism[J]. Journal of Photopolymer Science and Technology, 2016,29(3):509-512.
[12] Yang K, Xu H, Sakai K, et al. Radical sensitive zinc-based nanoparticle EUV photoresists[C]. Advances in Patterning Materials and Processes XXXVI,2019.109601R (1-7).
[13] Zhang Y. Organotin photoresists for extreme ultraviolet lithography[D]. Amsterdam:University of Amsterdam, 2019.
[14] Ekinci Y, Solak H, Padeste C, et al. 20 nm Line/space patterns in HSQ fabricated by EUV interference lithogra-phy[J]. Microelectronic Engineering, 2007,84(5-8):700-704.
[15] Kwark Y J, Bravo-Vasquez J P, Ober C K, et al. Novel silicon-containing polymers as photoresist materials for EUV lithography[J]. Proceedings of SPIE, 2003,5039:1204-1211.
[16] Choi J H, Kang P H, Nho Y C, et al. POSS-containing nanocomposite materials for next generation nanolithography[J]. Solid State Phenomena, 2007,119:299-302.
[17] Yamashita T, Morita M, Tanaka Y, et al. High-sensitivity EUV resists based on fluorinated polymers[C]. SPIE Advanced Lithography, 2011. 79721G (1-13).
[18] Iwashita J, Hirayama T, Takagi I, et al. Characteristics of main chain decomposable STAR polymer for EUV resist[J]. Proceedings of SPIE, 2011,7972:79720L (1-10).
[19] Kudo H, Fukunaga M, Shiotsuki K, et al. Synthesis of hyperbranched polyacetals containing C-(4-t-butylbenz)calix
[4] resorcinarene:resist properties for extreme ultraviolet (EUV) lithography[J]. Reactive and Functional Polymers, 2018,131:361-167.
[20] Ober M S, Romer D R, Etienne J, et al. Backbone degradable poly(aryl acetal) photoresist polymers:synthesis, acid sensitivity, and extreme ultraviolet lithography performance[J].Macromolecules, 2019,52(3):886-895.
[21] Ali M A, Gonsalves K E, Golovkina V, et al. High sensitivity nanocomposite resists for EUV lithography[J]. Microelectronic Engineering, 2003,65(4):454-462.
[22] Lee C T, Henderson C L, Wang M, et al. The effect of direct PAG incorporation into the polymer main chain on reactive ion etch resistance of 193 nm and EUV chemically amplified resists[J]. Microelectronic Engineering, 2008,85(5-6):963-965.
[23] Pujari N S, Wang M, Gonsalves K E. Co and terpolymer reactivity ratios of chemically amplified resists[J]. Polymer, 2017,118(2):201-214.
[24] Gonsalves K E, Wang M, Lee C T, et al. Novel chemically amplified resists incorporating anionic photoacid generator functional groups for sub-50-nm half-pitch lithography[J]. Journal of Materials Chemistry, 2009,19(18):2797-2802.
[25] Wang M, Gonsalves K E, Rabinovich M, et al. Novel anionic photoacid generators (PAGs) and corresponding PAG bound polymers for sub-50 nm EUV lithography[J]. Journal of Materials Chemistry, 2007,17(17):1699-1706.
[26] Kim J, Lee J W, Kim D, et al. Measurement of EUV resists performances RLS by DUV light source[J]. Proceedings of SPIE, 2010,7636:76362Y(1-7).
[27] Jain V, Coley S M, Lee J J, et al. Impact of polymerization process and OOB on lithographic performance of a EUV resist[J].Proceedings of SPIE, 2011,7969:796912(1-10).
[28] Lawrie K, Blakey I, Blinco J, et al. Extreme ultraviolet (EUV) degradation of poly(olefin sulfone)s:towards applications as EUV photoresists[J]. Radiation Physics and Chemistry, 2011,80(2):236-241.
[29] Lawrie K J, Blakey I, Blinco J P, et al. Chain scission resists for extreme ultraviolet lithography based on high performance polysulfone-containing polymers[J]. Journal of Materials Chemistry, 2011,21(15):5629-5637.
[30] Blakey A I, Yu A, Blinco J, et al. Polycarbonate based nonchemically amplified photoresists for extreme ultraviolet lithography[J]. Proceedings of SPIE, 2010,7636:763635(1-8).
[31] Shirai M, Maki K, Okamura H, et al. Negative EUV resist based on thiol-ene system[J]. Journal of Photopolymer Science and Technology, 2010,23(5):687-691.
[32] Satyanarayana V S V, Singh V, Kalyani V, et al. A hybrid polymeric material bearing a ferrocene-based pendant organometallic functionality:synthesis and applications in nanopatterning using EUV lithography[J]. RSC Advances, 2014,4(104):59817-59820.
[33] Satyanarayana V S V, Kessler F, Singh V, et al. Radiation-sensitive novel polymeric resist materials:iterative synthesis and their EUV fragmentation studies[J]. ACS Applied Materials and Interfaces, 2014,6(6):4223-4232.
[34] Reddy P G, Kumar P, Ghosh S, et al. Organic-inorganic hybrid photoresists containing hexafluoroantimonate:design, synthesis and high resolution EUV lithography studies[J]. Materials Chemistry Frontiers, 2017,1:2613-2619.