지방족고리 구조를 함유하는 감광성 폴리이미드 수지의 합성 및 특성 평가

심종천; 최성묵; 심현보; 권수한; 이미혜; Jong Chun Shim; Sung Mook Choi; Hyun Bo Sim; Soo-Han Kwon; Mi Hye Yi

Polymer(Korea), Vol.28, No.6, 494-501, November, 2004

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지방족고리 구조를 함유하는 감광성 폴리이미드 수지의 합성 및 특성 평가

Synthesis and Characterization of Photosensitive Polyimides Containing Alicyclic Structure

심종천, 최성묵, 심현보, 권수한¹, 이미혜 ^†

한국화학연구원 화학소재연구부
¹충북대학교 화학과

Jong Chun Shim, Sung Mook Choi, Hyun Bo Sim, Soo-Han Kwon¹, and Mi Hye Yi^†

Advanced Materials Division, Korea Research Institute of Chemical Technology, 100 Jangdong, Yusong, Daejeon 305-600, Korea
¹Department of Chemistry, Chungbuk National University, Chongju, Chungbuk 361-763, Korea

E-mail:

초록

시클로부탄-1,2,3,4-테트라카복실산 이무수물, 2-(메타크릴로일옥시)에틸-3,5-디아미노벤조에이트 및 1,3-비스(3-아미노프로필)-1,1,3,3-테트라메틸디실록산을 N-메틸-2-피롤리돈 하에서 용액 중합 반응시켜 알칼리 수용액에서 현상이 가능할 뿐만 아니라 가시광선 영역에서 우수한 광투과성을 보이는 신규 감광성 폴리이미드 전구체인 폴리암산 (PAA-0)을 제조하였다. 광개시제의 존재 하에서 노광 후 열경화된 폴리이미드 박막은 2.38 wt%의 테트라메틸암모니움 히드록사이드 수용액에 용해되지 않는 특성을 보였으며, 이를 이용하여 광에 의한 미세 화상 형성 연구를 수행하였다. 폴리이미드 전구체 박막의 광반응에 적합한 광개시제는 2, 2-디메톡시-2-페닐아세토페논임을 알 수 있었고, 최적 광량은 400~600 mj/cm²의 범위에 있음이 확인되었다. 감광성 폴리이미드 전구체는 250 ℃의 온도에서 50분간 열경화시킴으로써 투명한 폴리이미드 박막으로 전환이 되었으며, 유기용제를 비롯한 포토레지스트 제거제에 대한 우수한 내용제성 및 가시광선 영역에서의 우수한 광투과 특성을 나타내었다.

A new alkali developable photosensitive poly(amic acid) (PAA-0) with transmittance at 400 nm was synthesized from cyclobutane-1,2,3,4-tetracarboxylic dianhydride, 2-(methacryloyloxy)ethyl-3,5-diaminobenzoate and 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyl disiloxane in N-methyl-2-pyrrolidinone. Photosensitivity of the PAA-0 was investigated at 365-400 nm in the presence of a photoinitiator using a high pressure mercury lamp. The photo-cured poly(amic acid) was insoluble toward aqueous 2.38 wt% tetramethylammonium hydroxide solution. Negative pattern of the PAA-0 with 25 μm resolution was obtained by developing with 2.38 wt% tetramethylammonium hydroxide solution after exposure of 600 mJ/cm² in the presence of 2,2-dimethoxy-2-phenyl- acetophenone as a photoinitiator. The patterned poly(amic acid) was converted to polyimide by thermal curing at 250 ℃ for 50 min, which showed chemical resistance against photoresist stripper as well as good transmittance at 400 nm.

Keywords:photosensitive;polyimide;alkali developable;good transmittance;photopatterning;alicyclic chain polymer

[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)
Ahne H, Rubner R, "Photosensitive Polyimides: Applications of Polyimides in Electronics", K. Horie and T. Yamashita, Editors, Chapter 2, Technomic publishing company, Lancaster, 13 (1995)
Bureau JM, Droguet JP, "Polyimides:Applications of Polyimides as Photosensitive Materials", M. K. Ghosh and K. L. Mittal, Editors, Marcel Dekker Inc, New York (1996)
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)
Matsumoto T, Macromolecules, 32(15), 4933 (1999)
Kikkawa H, Shoji F, Tanaka J, Kataoka F, Polym. Adv. Technol., 4, 268 (1992)
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)
Ahn BH, Lee DW, Lee JK, Korea Polym. J., 9(5), 247 (2001)
Suzuki H, Abe T, Takaishi K, Narita M, Hamada F, J. Polym. Sci. A: Polym. Chem., 38(1), 108 (2000)
Crivello JV, Dietliker K, "Photoinitiatiors for Free Radical Cationic and Anionic Photo-Polymerisation", G. Bradley, Editor, John Wiley & Sons Ltd, New York, 115 (1998)

[Referenced By]

[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, Chapter 2, Technomic publishing company, Lancaster, 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 (1996)

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

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

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

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

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

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

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

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

[13] Ahn BH, Lee DW, Lee JK, Korea Polym. J., 9(5), 247 (2001)

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

[15] Crivello JV, Dietliker K, "Photoinitiatiors for Free Radical Cationic and Anionic Photo-Polymerisation", G. Bradley, Editor, John Wiley & Sons Ltd, New York, 115 (1998)