새로운 감광성 고분자의 개발-아미노기의 생성과 포토레지스트의 이용

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Polymer(Korea), Vol.17, No.6, 695-702, November, 1993

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새로운 감광성 고분자의 개발-아미노기의 생성과 포토레지스트의 이용

Development of Novel Photofunctional Polymers Formation of Amino Groups and Applications to Photoresists

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초록

측쇄에 아식옥시이미노기를 갖는 고분자의 고상 광반응에 있어 아미노기의 생성에 대해 검토하였으며, 광반응에 의해 폴리머 매트릭스에 도입된 아미노기를 이용하여 포토레지스트에의 이용 가능성을 알아보기 위하여 각종 용매에 대한, 용해도 변화 실험을 행하였다. 광조사후 HCl 수용액에 처리한 폴리머 박막은 메탄올에 가용화되었다. 광조사시간과 잔막율과의 실험 결과 1분간의 광조사에 의해 잔막율이 0에 도달하였으며 광반응에 의해 폴리머가 메탄올에 완전히 용해되었을 때 요구되는 아미노기의 도입량은 AAPO-St에서는 10 mol%이었으나 AAPO-MMA에서는 3mol%의 적은 양으로도 가용화되었다.

Photosensitive copolymers bearing acyloximino groups were prepared and the formation of amino groups by the photoreaction in the solid phase was investigated. The change in solubilities for various solvents was investigated for application of the copolymers to photoresists, and the copolymer films treated with an aqueous solution of HCl after irradiation became soluble in methanol and ethanol. The amounts of critical amino groups for complete dissolution of MMA copolymers were lower than those of styrene copolymer the former being 3mol% , and the latter being 10 mol%.

[References]

Bowden MJ, "Materials for Microlithography: Radiation-Sensitive Polymers," ed. by L.F. Thompson, ACS Symp. SEr, 266, p. 39, American Chemical Society, Washington, D.C. (1984)
BASF A.G., Ger. Patent, 2150691 (1971)
Weigert FJ, Proskow S, J. Imaging Sci., 31, 11 (1987)
Frechet JMJ, Tessier TG, Willson CG, Ito H, Macromolecules, 18, 317 (1985)
Shirai M, Tsunooka M, Tanaka M, Nishijima K, Ishikawa K, Chem. Express, 2, 707 (1987)
Hayase S, Onishi Y, Horiguchi R, J. Electrochem. Soc., 134, 2275 (1987)
Delzenne GA, Laridon U, Peeters H, Eur. Polym. J., 6, 93 (1970)
Reichmanis E, Wilkins CW, Chandross EA, J. Electrochem. Soc., 127, 2514 (1980)
Reichmanis E, Wilkins CW, "Polymer Materials for Electronic Applications," ed. by E.D. Feit, ACS Symp. Ser., 184, p. 29, American Chemical Society, Washington, D.C. (1982)
Reichmanis E, Wilkins CW, J. Electrochem. Soc., 132, 1178 (1985)
Hong SI, Kurosaki T, Okawara M, J. Polym. Sci. A: Polym. Chem., 12, 2553 (1974)
Tsunooka M, Kotera K, Tanaka M, J. Polym. Sci. A: Polym. Chem., 15, 107 (1977)
Tsunooka M, Imono S, Nakayama K, Kuwabara H, Tanaka M, J. Polym. Sci. A: Polym. Chem., 24, 317 (1986)
Song KH, Tsunooka M, Tanaka M, J. Photochem. Photobiol. A-Chem., 44, 197 (1988)
Song KH, Tonogai S, Tsunooka M, Tanaka M, J. Photochem. Photobiol. A-Chem., 49, 269 (1989)
Song KH, Urano A, Tsunooka M, Tanaka M, J. Polym. Sci. C: Polym. Lett., 25, 417 (1987)

[1] Bowden MJ, "Materials for Microlithography: Radiation-Sensitive Polymers," ed. by L.F. Thompson, ACS Symp. SEr, 266, p. 39, American Chemical Society, Washington, D.C. (1984)

[2] BASF A.G., Ger. Patent, 2150691 (1971)

[3] Weigert FJ, Proskow S, J. Imaging Sci., 31, 11 (1987)

[4] Frechet JMJ, Tessier TG, Willson CG, Ito H, Macromolecules, 18, 317 (1985)

[5] Shirai M, Tsunooka M, Tanaka M, Nishijima K, Ishikawa K, Chem. Express, 2, 707 (1987)

[6] Hayase S, Onishi Y, Horiguchi R, J. Electrochem. Soc., 134, 2275 (1987)

[7] Delzenne GA, Laridon U, Peeters H, Eur. Polym. J., 6, 93 (1970)

[8] Reichmanis E, Wilkins CW, Chandross EA, J. Electrochem. Soc., 127, 2514 (1980)

[9] Reichmanis E, Wilkins CW, "Polymer Materials for Electronic Applications," ed. by E.D. Feit, ACS Symp. Ser., 184, p. 29, American Chemical Society, Washington, D.C. (1982)

[10] Reichmanis E, Wilkins CW, J. Electrochem. Soc., 132, 1178 (1985)

[11] Hong SI, Kurosaki T, Okawara M, J. Polym. Sci. A: Polym. Chem., 12, 2553 (1974)

[12] Tsunooka M, Kotera K, Tanaka M, J. Polym. Sci. A: Polym. Chem., 15, 107 (1977)

[13] Tsunooka M, Imono S, Nakayama K, Kuwabara H, Tanaka M, J. Polym. Sci. A: Polym. Chem., 24, 317 (1986)

[14] Song KH, Tsunooka M, Tanaka M, J. Photochem. Photobiol. A-Chem., 44, 197 (1988)

[15] Song KH, Tonogai S, Tsunooka M, Tanaka M, J. Photochem. Photobiol. A-Chem., 49, 269 (1989)

[16] Song KH, Urano A, Tsunooka M, Tanaka M, J. Polym. Sci. C: Polym. Lett., 25, 417 (1987)