신규 양성형 감광성 폴리암산의 합성 및 특성 연구

심현보; 유영임; 이미혜; Hyun Bo Sim; Yeong Im Yu; Mi Hye Yi

Polymer(Korea), Vol.30, No.2, 162-167, March, 2006

Export Citation

신규 양성형 감광성 폴리암산의 합성 및 특성 연구

Synthesis and Characterization of New Positive Type Photosensitive Poly(amic acid)s

심현보, 유영임, 이미혜 ^†

한국화학연구원 화학소재연구부

Hyun Bo Sim, Yeong Im Yu, and Mi Hye Yi^†

Advanced Materials Division, Korea Research Institute of Chemical Technology, 100 Jangdong, Yusong, Daejeon 305-600, Korea

E-mail:

초록

1,2,3,4-시클로부탄 테트라카복시산 이무수물과 4,4′-디아미노디페닐에테르(DDE)를 용액 중합 반응하여 폴리암산(PAA) 용액을 제조한 후, 1,2-에폭시-3-페녹시프로판과 반응시켜 폴리암산에스테르(PAE)를 합성하였다. 여기에 용해억제재로서 30 wt%의 디아조나프토퀴논 유도체(DI)를 첨가하였다. 365∼400 nm의 파장에서 200 mJ/cm2의 자외광을 조사한 후, 0.95 wt%의 테트라메틸암모니움히드록사이드 수용액으로 현상한 결과 25 μm 해상도의 양성형 미세 화상을 얻었다. 비노광부에 잔존하는 폴리이미드 박막은 400 nm에서 92% 이상의 우수한 광투과도를 나타내었다.

Polyamic acid (PAA) was prepared from cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA) and 4,4′-diaminodiphenyl ether (DDE). In order to impart a photosensitivity to the PAA, diazonaphthoquinone (DNQ) derivative (DI) was added. However, the addition of the DI was not enough to inhibit the dissolution of the PAA for a aqueous alkali solution. Therefore, we had synthesized poly(amic acid ester)s by an adding 1,2-epoxy-3-phenoxypropane to the PAA. That is, an acidity of the PAA could be controlled by an esterification reaction of 1,2-epoxy-3-phenoxypropane with the PAA. Significant difference of a dissolution rate of the poly(amic acid ester) between an exposed and unexposed area was observed at an acid content of 60% and less. Resolution of the positively patterned film showed about 25 μm at the exposure dose of 200 mJ/cm2.

Keywords:photosensitive;polyimide;alkali developable;good transmittance;photopatterning

[References]

Sillion B, Verdet L, Polyimides and Other High-Temperature Polymers, M. J. M. Abadie and B. Sillion, Editors, Elsevier Science, Amsterdam, 363 (1991)
Feger C, Franke H, Polyimides in High-Performance Electronics Packaging and Optoelectronic Applications M.K. Ghosh and K.L.Mittal, Editors, Marcel Dekker Inc, New York, 759 (1996)
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Bureau JM, Droguet JP, Polyimides: Applications of Polyimides as Photosensitive Materials, M.K. Ghosh and K.L. Mittal, Editors, Marcel Dekker Inc, New York, pp743-757 (1996)
Kerwin RE, Goldrick MR, Polym. Eng. Sci., 11, 426 (1971)
Rubner R, Siemens Forsch. Entwickl. Ber., 5, 92 (1976)
Rubner R, Barter B, Bald G, Siemens Forsch. Entwickl, Ber., 5, 235 (1976)
Rubner R, Ahne H, Ruhn E, Koloddieg C, Photogr. Sci. Eng., 23, 303 (1979)
Matsumoto T, Macromolecules, 32(15), 4933 (1999)
Kikkawa H, Shoji F, Tanaka J, Kataoka F, Polym. Adv. Technol., 4, 268 (1992)
Suzuki H, Abe T, Takaishi K, Narita M, Hamada F, J. Polym. Sci. A: Polym. Chem., 38(1), 108 (2000)
Crivello JV, Dietliker K, Photoinitiators for Free Radical Cationic and Anionic Photo- Polymerisation, G. Bradley, Editor, John Wiley & Sons Ltd, New York, pp115-122 (1998)
Chae KH, Park JS, Cho CH, Chang JY, Korea Polym. J., 6(2), 174 (1998)
Chae KH, Park JS, Kim ES, Han MJ, Bull. Korean Chem. Soc., 18, 243 (1997)
Choi SM, Kim KJ, Choi KY, Yi MH, J. Appl. Polym. Sci., 96(6), 2300 (2005)

[Related Articles]

[1] Sillion B, Verdet L, Polyimides and Other High-Temperature Polymers, M. J. M. Abadie and B. Sillion, Editors, Elsevier Science, Amsterdam, 363 (1991)

[2] Feger C, Franke H, Polyimides in High-Performance Electronics Packaging and Optoelectronic Applications M.K. Ghosh and K.L.Mittal, Editors, Marcel Dekker Inc, New York, 759 (1996)

[3] Ahne H, Rubner R, Photosensitive Polyimides: Applications of Polyimides in Electronics, K. Horie and T. Yamashita, Editors, Technomic Publishing Company, Lancaster, 2, 13 (1995)

[4] Bureau JM, Droguet JP, Polyimides: Applications of Polyimides as Photosensitive Materials, M.K. Ghosh and K.L. Mittal, Editors, Marcel Dekker Inc, New York, pp743-757 (1996)

[5] Kerwin RE, Goldrick MR, Polym. Eng. Sci., 11, 426 (1971)

[6] Rubner R, Siemens Forsch. Entwickl. Ber., 5, 92 (1976)

[7] Rubner R, Barter B, Bald G, Siemens Forsch. Entwickl, Ber., 5, 235 (1976)

[8] Rubner R, Ahne H, Ruhn E, Koloddieg C, Photogr. Sci. Eng., 23, 303 (1979)

[9] Matsumoto T, Macromolecules, 32(15), 4933 (1999)

[10] Kikkawa H, Shoji F, Tanaka J, Kataoka F, Polym. Adv. Technol., 4, 268 (1992)

[11] Suzuki H, Abe T, Takaishi K, Narita M, Hamada F, J. Polym. Sci. A: Polym. Chem., 38(1), 108 (2000)

[12] Crivello JV, Dietliker K, Photoinitiators for Free Radical Cationic and Anionic Photo- Polymerisation, G. Bradley, Editor, John Wiley & Sons Ltd, New York, pp115-122 (1998)

[13] Chae KH, Park JS, Cho CH, Chang JY, Korea Polym. J., 6(2), 174 (1998)

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

[15] Choi SM, Kim KJ, Choi KY, Yi MH, J. Appl. Polym. Sci., 96(6), 2300 (2005)