화학 증폭형 포토레지스트의 감도 증진을 위한 산 증식제로 시클로헥산디올의 p-스티렌술폰산 에스테르 유도체에 관한 연구

홍경일; 이은주; 임권택; 정용석; 정연태; Kyong Il Hong; Eun Ju Lee; Kwon Taek Lim; Yong Seok Jeong; Yeon Tae Jeong

Journal of the Korean Industrial and Engineering Chemistry, Vol.14, No.5, 605-608, August, 2003

p-Styrenesulfonate Derivatives of Cyclohexandiol as Acid Amplifiers to Enhance Photosensitivity of Chemically Amplified Photoresists

홍경일, 이은주, 임권택 , 정용석, 정연태^†

부경대학교 공과대학 화상정보공학부, 부산 608-739

Kyong Il Hong, Eun Ju Lee, Kwon Taek Lim , Yong Seok Jeong, and Yeon Tae Jeong^†

Division of Image and Information Engineering, Pukyong National University, Busan 608-739, Korea

E-mail:

초록

본 연구에서는 1-hydroxy-4-p-styrenesulfonyloxy cyclohexane (1), 1,4-di-p-styrene-sulfonyloxy cyclohexane (2), 그리고 1-p-styrenesulfonyloxy-4-tosyloxy cyclohexane (3)을 산 증식제로 합성하고 그 성능을 평가하였다. 이러한 산 증식제들(1~3)은 레지스트 공정온도에 대하여 충분한 열적 안정성을 나타내었다. 또한 산 증식제를 사용한 경우에 광산 발생제만 사용한 poly(tert-butyl methacrylate) 필름에 비교하여 2배에서 5배 정도의 감도 증진이 일어나 광화상 제조에 효과적으로 응용할 수 있음을 확인하였다.

In this research, we synthesized and evaluated 1-hydroxy-4-p-styrenesulfonyloxy cyclohexane, 1,4-di-p-styrenesulfonyloxy cyclohexane, and 1-p-styrenesulfonyloxy-4-tosyloxy cyclohexane as novel acid amplifiers. These acid amplifiers showed reasonable thermal stability for resist processing temperature. As estimated by the sensitivity curve, all the acid amplifiers were 2 ~ 5 times more sensitive than poly(tert-butyl methacrylate) film in the presence of a photoacid generator; and therefore, these can provided practical applicability in photoimaging.

Keywords:acid amplifier;photoacid generator;chemically amplified photoresist

[References]

Choi SJ, Park CG, Polym. Sci. Technol., 7(6), 716 (1996)
Kaur S, Crivello JV, Pascuzzi N, J. Polym. Sci. A: Polym. Chem., 37(2), 199 (1999)
Ito H, Proc. SPIE, 3678, 2 (1999)
Park SW, Arimitsu K, Ichimura K, Ohfugi T, Photopolym. Sci. Technol., 12, 293 (1999)
Ohfugi T, Takahashi M, Ogawa K, Ohtsuka H, Sasago M, Ichimura K, Proc. SPIE, 3049, 76 (1999)
Park SW, Arimitsu K, Lee SG, Ichimura K, Chem. Lett., 1036 (2000)
Ito H, Arimitsu K, Ichimura K, Macromol. Chem. Phys., 201, 132 (2000)
Huang WS, Kwong RE, Moreau W, Proc. SPIE, 3999, 591 (2000)
Choi SJ, Kim HW, Woo SG, Moon JT, Proc. SPIE, 3999, 54 (2000)
Park SW, Arimitsu K, Ichimura K, Macromol. Rapid Commun., 21, 1050 (2000)
Pawloski AR, Nealey PF, J. Am. Chem. Soc., 13, 4154 (2001)
Arimitsu K, Ichimura K, Macromol. Chem. Phys., 202, 453 (2001)
Jeong YT, Lee EJ, Park JY, J. Korean Soc. Imaging Sci. Technol., 7, 110 (2001)
Jeong YT, Lee EJ, Kuen KA, J. Korean Printing Soc., 20, 91 (2002)
Jeong YT, Lee EJ, Hong KI, Lim KT, Jeoung YS, Hong SS, J. Korean Chem. Soc., 46, 437 (2002)

[Referenced By]

[Related Articles]

[1] Choi SJ, Park CG, Polym. Sci. Technol., 7(6), 716 (1996)

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

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

[4] Park SW, Arimitsu K, Ichimura K, Ohfugi T, Photopolym. Sci. Technol., 12, 293 (1999)

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

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

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

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

[9] Choi SJ, Kim HW, Woo SG, Moon JT, Proc. SPIE, 3999, 54 (2000)

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

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

[12] Arimitsu K, Ichimura K, Macromol. Chem. Phys., 202, 453 (2001)

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

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

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