Preparation of a Kind of Positive Chemically Amplified Deep UV Photoresist Material with High Sensitivity

doi:10.7503/cjcu20160804

Abstract

Abstract:

With the reaction of poly(4-hydroxystyrene)(PHS) and cyclohexyl vinyl ether(CVE), a partly protected product with acetal groups was prepared. The product PHS-CVE shows good solubilities in common photoresist solvents, high thermal stability and good transparency at 248 nm wavelength. A new kind of positive chemically amplified 248-nm photoresist can be formed by this polymer, disulfone PAG and copolymer of 4-hydroxy styrene and 3-hydroxy-1-adamantyl methacrylate. Lithographic performance was investigated via KrF laser exposure tool. A clear positive-tone pattern with 180 nm line width was obtained under low post exposure bake(PEB) temperature. Poly(4-hydroxy styrene-co-3-hydroxy-1-adamantyl methacrylate) incorporated to the resist can increase the glass transition temperature of the photoresist film, which makes the resist material applicable for 248-nm lithography process.

Key words: Photoresist, Deep ultraviolet, Chemical amplification, Poly(4-hydroxylstyrene), Acetal

CLC Number:

O632.4

TrendMD:

WU Liping, HU Fanhua, WANG Qianqian, WANG Jing, WANG Liyuan. Preparation of a Kind of Positive Chemically Amplified Deep UV Photoresist Material with High Sensitivity[J]. Chem. J. Chinese Universities, 2017, 38(5): 896.

References

[1] Willson C. G., Trinque B. C., Journal of Photopolymer Science & Technology, 2003, 16, 621-627
[2] Ito H., Ibm Journal of Research & Development, 2000, 44, 119-130
[3] Kumada T., Kubota S., Koezuka H., Hanawa T., Kishimura S. Nagata H., Journal of Photopolymer Science & Technology, 1991, 4, 469-472
[4] Hayashi N., Schlegel L., Ueno T., Shiraishi H., Iwayanagi T., Proceedings of SPIE:the International Society for Optical Engineering, 1991, 1466, 377-383
[5] Barkakaty B., Matsumoto K., Endo T., Macromolecules, 2009, 42, 9481-9485
[6] Koyama H., Inoue K., Iwahama T., Sumida M., Unsaturated Carboxylic Acid Hemiacetal Ester, Polymer and Resin Compositiom for Photorisist, WO 2005/075446 A1, 2005-08-18
[7] Matsukawa D., Okamura H., Shirai M., Journal of Materials Chemistry, 2011, 21, 10407-10414
[8] Matsukawa D., Wakayama H., Mitsukura K., Okamura H., Hirai Y., Shirai M., Journal of Materials Chemistry, 2009, 19(24), 4085-4087
[9] Hattori T., Schlegel L., Imai A., Hayashi N., Ueno T., In SPIE's 1993 Symposium on Microlithography, 1993, 1925, 146-154
[10] Hattori T., Schlegel L., Imai A., Hayashi N., Ueno T., Journal of Photopolymer Science & Technology, 1993, 6, 497-504
[11] Malik S., Blakeney A. J., Ferreira L., Maxwell B., Whewell A., Sarubbi T. R., Bowden M. J., Driessche V V., Fujimori T., Tan S., Proceedings of SPIE-the International Society for Optical Engineering, 1999, 3678, 388-400
[12] Malik S., Blakeney A. J., Ferreira L., Sizensky J., Maxwell B., Kocab T., Sarubbi T. R., Blachowicz B. A., Bowden M. J., Journal of Photopolymer Science & Technology, 1998, 11, 431-438
[13] Malik S., Blakeney A. J., Ferreira L., Sizensky J. J., Maxwell B. E., Production of Acetal Derivatized Hydroxyl Aromatic Polymers and Their Use in Radiation Sensitive Formulations, EP 6133412, 2000-10-17.
[14] Yu J., Xu N., Liu Z., Wang L., ACS Applied Materials & Interfaces, 2012, 4, 2591-2596
[15] Yu J., Xu N., Wei Q., Wang L., Journal of Materials Chemistry C, 2013, 1(6), 1160-1167
[16] Wei Q., Wang L., Chem. Res. Chinese Universities, 2015, 31(4), 585-589
[17] Kim J. B., Park J. J., Jang J. H., Polymer, 2000, 41, 149-153
[18] Toma T., Shimokawa J., Fukuyama T., Organic Letters, 2007, 9, 3195-3197
[19] Maioli A. T., Anselme J. P., Tetrahedron Letters, 1995, 36, 1221-1222