p-Toluenesulfonate Esters of 1,2-Benzenediol as Novel Acid Amplifiers

Kyong Il Hong; Yong Seok Jeong; Kwon Taek Lim; Sang-Jun Choi; Yeon Tae Jeong

Journal of Industrial and Engineering Chemistry, Vol.10, No.5, 864-867, September, 2004

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p-Toluenesulfonate Esters of 1,2-Benzenediol as Novel Acid Amplifiers

Kyong Il Hong, Yong Seok Jeong, Kwon Taek Lim , Sang-Jun Choi¹, and Yeon Tae Jeong^†

Division of Image and Information Engineering, Pukyong National University, Busan, Korea
¹Process Development Team, Semiconductor R&D Center, Samsung Electronics Co., Ltd., Korea

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Aiming at the development of novel aromatic acid amplifiers, 1-hydroxy and 1-p-toluenesulfonyloxy-2-p-toluenesulfonyloxybenzenes were synthesized to generate p-toluenesulfonic acid autocatalytically in the presence of a small amount of the acid evolved from a photoacid generator. These aromatic sulfonates possess excellent thermal stability in ptBMA film and are the first aromatic acid amplifiers that act as photosensitivity enhancers. Of the two compounds, 1-hydroxy-2-p-toluenesulfonyloxybenzene demonstrated the superior photosensitivity improvement. When this compound was coupled with a chemically amplified photoresist system, the photosensitivity was enhanced up to 6-fold.

Keywords:acid amplifier;photoacid generator;chemically amplified photoresist

[References]

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[Referenced By]

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[1] Ito H, Proc. SPIE., 3678, 2 (1999)

[2] Ito H, Arimitsu K, Ichimura K, Macromol. Chem. Phys., 201, 132 (2000)

[3] Hwang WS, Kwong RE, Moreau W, Proc. SPIE, 591, 3999 (2000)

[4] Ohfugi T, Takahashi M, Kuhara K, Ogawa K, Ohtsuka H, Sasago M, Ichimura K, Proc. SPIE, 3049, 76 (1999)

[5] Kim KS, Kang SH, Shin JS, J. Ind. Eng. Chem., 2(1), 45 (1996)

[6] Park DW, Yoon SH, Kim GJ, Sekiguchi H, J. Ind. Eng. Chem., 8(4), 393 (2002)

[7] Park SW, Arimitsu K, Lee SG, Ichimura K, Chem. Lett., 1036 (2000)

[8] Park SW, Arimitsu K, Ichimura K, Macromol. Rapid Commun., 21, 1050 (2000)

[9] Jeong YT, Lee EJ, Park JY, J. Kor. Soc. Imaging Sci. Technol., 7, 110 (2001)

[10] Jeong YT, Lee EJ, Kuen KA, J. Kor. Printing. Soc., 20, 91 (2002)

[11] Jeong YT, Lee EJ, Hong KI, Lim KT, Jeong YS, Hong SS, J. Kor. Chem. Soc., 46, 437 (2002)

[12] Pawloski AR, Christian R, Nealey PF, J. Am. Chem. Soc., 13, 4154 (2001)