주쇄에 광분해성 방향족 술포닐옥시이미드기를 함유한 감광성 폴리이미드

오세용; 이지영; 조성열; 정찬문; Se Young Oh; Ji-Young Lee; Sung-Youl Cho; Chan-Moon Chung

Polymer(Korea), Vol.24, No.3, 407-417, May, 2000

Export Citation

주쇄에 광분해성 방향족 술포닐옥시이미드기를 함유한 감광성 폴리이미드

Photosensitive Polyimides Having Aromatic Sulfonyloxyimide Groups in the Main Chain

오세용^†, 이지영, 조성열¹, 정찬문¹

서강대학교 공과대학 화학공학과
¹연세대학교 문리대학 화학과

Se Young Oh^†, Ji-Young Lee, Sung-Youl Cho¹, and Chan-Moon Chung¹

Department of Chemical Engineering, Sogang University, Seoul 121-742, Korea
¹Department of Chemistry, Yonsei University, Wonju, Kangwon-do 220-710, Korea

E-mail:

초록

고분자 주쇄에 cyclobutane 또는 페닐과 방향족 술포닐옥시이미드 구조를 갖는 감광성 폴리이미드를 합성하여 광분해 특성에 있어서 고분자의 구조가 미치는 영향을 조사하였다. 폴리이미드는 N-히드록시와 염화 술포닐의 축중합에 의해 제조하였다. 합성된 폴리이미드는 250℃까지 열분해가 일어나지 않고 안정하였다. 254nm의 광조사에 따른 폴리이미드의 광분해는 분광학적 측정에 의해 N-O 결합의 절단 또는 이미드 moiety의 계열에 기인되는 것을 알 수 있었다. 본 연구의 폴리이미드는 포지티브형의 광분해성 고분자로의 활용이 가능한 것이 확인되었으며, 특히 pyromellitic diimide moiety를 함유하는 폴리이미드의 포지티브 화상은 높은 감도와 해상도를 나타내었다.

Photosensitive polyimides having cyclobutane or phenyl and aromatic sulfonyloxyimide units in the main chain have been synthesized and the photodegradation behavior was investigated in relation with the polymer structure. The polyimides were prepared by condensation polymerization of N-hydroxyl and sulfonyl chloride. The prepared polyimides were stable up to 250℃ without thermal degradation. It has been found that the photodegradation of polyimides upon irradiation of 254 nm UV light results from scission of N-O bonds or ring opening of imides moiety by spectroscopic measurements. The polyimides were useful as positive working photodegradable polymers. Especially, the positive tone image of polyimide containing a pyromellitic diimide moiety exhibited high sensitivity and resolution.

Keywords:Photosensitive polyimide;Photodegradation of aromatic sulfonyloxyimide;Positive-tone image

[References]

Reichmanis E, Houlihan FM, Nalamasu O, Neenan TX, Chem. Mater., 3, 394 (1991)
MacDonald SA, Willson CG, Frechet JMJ, Acct. Chem. Res., 27, 151 (1994)
McCord MA, Pease RFW, J. Vac. Sci. Technol. B, B4, 86 (1991)
Takimoto A, Ogawa H, J. Photopolym. Sci. Technol., 5, 397 (1992)
Inoue T, Seino K, Tamura K, Hasegawa S, Kimbara K, J. Photopolym. Sci. Technol., 5, 385 (1992)
Pottiger MT, Solid State Technol., S1-S4, December (1989)
Tabata Y, Mita I, Nonogaki S, Horie K, Tagawa S, "Polymers for Microelectronics," p. 601-844, Kodansha Publisher, Tokyo, 1990 (1990)
Arjavalingam G, Hougham G, Lafemina JP, Polymer, 31, 840 (1990)
Yamaoka T, Morita H, "Kangkosei Jushi," ed. by Kobunshi Gakkai, p. 58, Kyouritu Publisher, Tokyo, 1989 (1989)
Fujii H, Omote T, Kobunshi, 44, 240 (1995)
Ohkita H, Tsuchida A, Yamamoto M, Moore JA, Gamble DR, Macromol. Chem. Phys., 197, 2493 (1996)
Mittal KL, "Polyimides: Synthesis, Characterization and Applications," p. 905-918, Plenum Press, New York, 1984 (1984)
Feely WE, Imhof JC, Stein CM, Polym. Eng. Sci., 26, 1101 (1986)
Burns A, Luethje H, Vollenbroek FA, Spiertz EJ, Microelectronic Eng., 6, 467 (1987)
Rohde O, Riediker M, Schaffner A, Proc. SPIE, 539, 175 (1985)
Chae KH, Park JS, Kim ES, Han MJ, Bull. Korean Chem. Soc., 18, 243 (1997)
Oba M, Kawamonzen Y, J. Appl. Polym. Sci., 58(9), 1535 (1995)
Khanna DN, Mueller WH, Polym. Eng. Sci., 29, 954 (1989)
Cadogan JIG, Rowley AG, Macromol. Symp., 142, 145 (1999)
Ortica F, Scaiano JC, Pohlers G, Cameron JF, Zampini A, Chem. Mater., 12, 414 (2000)
Oh SY, Lee JY, Cho SY, Chung CM, Polym.(Korea), 23(4), 604 (1999)
Oh SY, Lee JY, Cho SY, Chung CM, Mol. Cryst. Liq. Cryst.(Korea), in press
Oh SY, Lee JY, Cho SY, Chung CM, "Evaluation of Resist and Photodegradable Characteristics of Photosensitive Polyimide," The Korean Society of Industrial and Engineering Chemistry, Kyungwon University, 1999 (1999)

[Referenced By]

[1] Reichmanis E, Houlihan FM, Nalamasu O, Neenan TX, Chem. Mater., 3, 394 (1991)

[2] MacDonald SA, Willson CG, Frechet JMJ, Acct. Chem. Res., 27, 151 (1994)

[3] McCord MA, Pease RFW, J. Vac. Sci. Technol. B, B4, 86 (1991)

[4] Takimoto A, Ogawa H, J. Photopolym. Sci. Technol., 5, 397 (1992)

[5] Inoue T, Seino K, Tamura K, Hasegawa S, Kimbara K, J. Photopolym. Sci. Technol., 5, 385 (1992)

[6] Pottiger MT, Solid State Technol., S1-S4, December (1989)

[7] Tabata Y, Mita I, Nonogaki S, Horie K, Tagawa S, "Polymers for Microelectronics," p. 601-844, Kodansha Publisher, Tokyo, 1990 (1990)

[8] Arjavalingam G, Hougham G, Lafemina JP, Polymer, 31, 840 (1990)

[9] Yamaoka T, Morita H, "Kangkosei Jushi," ed. by Kobunshi Gakkai, p. 58, Kyouritu Publisher, Tokyo, 1989 (1989)

[10] Fujii H, Omote T, Kobunshi, 44, 240 (1995)

[11] Ohkita H, Tsuchida A, Yamamoto M, Moore JA, Gamble DR, Macromol. Chem. Phys., 197, 2493 (1996)

[12] Mittal KL, "Polyimides: Synthesis, Characterization and Applications," p. 905-918, Plenum Press, New York, 1984 (1984)

[13] Feely WE, Imhof JC, Stein CM, Polym. Eng. Sci., 26, 1101 (1986)

[14] Burns A, Luethje H, Vollenbroek FA, Spiertz EJ, Microelectronic Eng., 6, 467 (1987)

[15] Rohde O, Riediker M, Schaffner A, Proc. SPIE, 539, 175 (1985)

[16] Chae KH, Park JS, Kim ES, Han MJ, Bull. Korean Chem. Soc., 18, 243 (1997)

[17] Oba M, Kawamonzen Y, J. Appl. Polym. Sci., 58(9), 1535 (1995)

[18] Khanna DN, Mueller WH, Polym. Eng. Sci., 29, 954 (1989)

[19] Cadogan JIG, Rowley AG, Macromol. Symp., 142, 145 (1999)

[20] Ortica F, Scaiano JC, Pohlers G, Cameron JF, Zampini A, Chem. Mater., 12, 414 (2000)

[21] Oh SY, Lee JY, Cho SY, Chung CM, Polym.(Korea), 23(4), 604 (1999)

[22] Oh SY, Lee JY, Cho SY, Chung CM, Mol. Cryst. Liq. Cryst.(Korea), in press

[23] Oh SY, Lee JY, Cho SY, Chung CM, "Evaluation of Resist and Photodegradable Characteristics of Photosensitive Polyimide," The Korean Society of Industrial and Engineering Chemistry, Kyungwon University, 1999 (1999)