새로운 산증식제로 벤젠다이올의 p-톨루엔술폰산 에스터 유도체에 관한 연구

강지은; 홍경일; 임권택; 정연태; Ji Eun Kang; Kyong Il Hong; Kwon Taek Lim; Yeon Tae Jeong

Journal of the Korean Industrial and Engineering Chemistry, Vol.16, No.5, 660-663, October, 2005

Export Citation

새로운 산증식제로 벤젠다이올의 p-톨루엔술폰산 에스터 유도체에 관한 연구

p-Toluenesulfonate Ester Derivatives of Benzendiol as Novel Acid Amplifiers

강지은, 홍경일¹, 임권택 , 정연태^†

부경대학교 공과대학 화상정보공학부
¹한국화학연구원 복합기능환경소재팀

Ji Eun Kang, Kyong Il Hong¹, Kwon Taek Lim , and Yeon Tae Jeong^†

Pukyong National University, Pusan 608-739, Korea
¹Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea

E-mail:

초록

새로운 산증식제를 개발하기 위하여 2-hydroxyphenyl-4-methylbenzenesulfonate (1), 3-hydroxyphenyl-4-methylbenzene-sulfonate (2), 4-hydroxyphenyl-4-methylbenzenesulfonate (3)가 우수한 열적 성질을 갖는 방향족 산증식제로서 합성되었다. 이러한 새로운 산증식제들은 광산발생제로부터 생성된 소량의 산에 의해 자동촉매반응으로 p-톨루엔술포산을 생성하였다. 이러한 방향족 술포산 에스터들은 poly(tert-butyl methacrylate, PtBMA) 필름에서 우수한 열적 안정성을 보였고 감도증진제로서 작용하는 최초의 방향성 산증식제임이 증명되었다. 화학 증폭형 포토레지스트에 합성한 방향족 산중식제를 첨가한 경우에 감도가 3~6배 정도 증진되었다.

Aiming the development of novel acid amplifiers, 2-hydroxyphenyl-4-methylbenzenesulfonate (1), 3-hydroxyphenyl-4-methyl-benzene sulfonate (2), 4-hydroxyphenyl-4-methylbenzenesulfonate (3) were synthesized as the aromatic acid amplifiers with good thermal stability. They were autocatalytically generated p-toluenesulfonic acid in the presence of small amount of acid evolved from a photoacid generator. These aromatic sulfonates showed excellent thermal stability in PtBMA film and were proven to be the first aromatic acid amplifier to act as a photosensitivity enhancer. When these compounds were coupled with a chemically amplified photoresist system, photosensitivity was enhanced up to 3~6 folds.

Keywords:acid amplifier;photoacid generator;chemically amplified photoresist

[References]

Kaur S, Crivello JV, Pascuzzi N, J. Polym. Sci. A: Polym. Chem., 37(2), 199 (1999)
Bukofsky SJ, Feke GD, Wu Q, Grober RD, Dentinger PM, Taylor JW, Appl. Phys. Lett., 73, 408 (1998)
Park SW, Arimitsu K, Lee SG, Ichimura K, Chem. Lett., 1036 (2000)
Ito H, Proc. SPIE., 3678, 2 (1999)
Ito H, Arimitsu K, Ichimura K, Macromol. Chem. Phys., 201, 132 (2000)
Huang WS, Kwong RE, Moreau W, Proc. SPIE, 591, 3999 (2000)
Pawloski AR, Christian R, Nealey PF, J. Am. Chem. Soc., 13, 4154 (2001)
Lee EJ, Park JY, Jeong YT, J. Kor. Soc. Imaging Sci., 7, 110 (2001)
Lee EJ, Kuen KA, Jeong YT, J. Kor. Printing. Soc., 20, 91 (2002)
Lee EJ, Hong KI, Lim KT, Jeoung YS, Hong SS, Jeong YT, J. Kor. Chem. Soc., 46, 437 (2002)
Hong KI, Lee EJ, Lim KT, Jeong YS, Jeong YT, J. Korean Ind. Eng. Chem., 14(5), 605 (2003)
Hong KI, Jeong YS, Lim KT, Choi SJ, Jeong YT, J. Ind. Eng. Chem., 10(5), 864 (2004)

[Related Articles]

[1] Kaur S, Crivello JV, Pascuzzi N, J. Polym. Sci. A: Polym. Chem., 37(2), 199 (1999)

[2] Bukofsky SJ, Feke GD, Wu Q, Grober RD, Dentinger PM, Taylor JW, Appl. Phys. Lett., 73, 408 (1998)

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

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

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

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

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

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

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

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

[11] Hong KI, Lee EJ, Lim KT, Jeong YS, Jeong YT, J. Korean Ind. Eng. Chem., 14(5), 605 (2003)

[12] Hong KI, Jeong YS, Lim KT, Choi SJ, Jeong YT, J. Ind. Eng. Chem., 10(5), 864 (2004)