New Soluble and Intrinsically Photosensitive Polyimide: Synthesis and Properties of Poly(amide-co-imide) Containing p-Phenylenediacryloyl Moiety

Myong Hoon Lee; Yun Sang Cheong; Myoung Seon Gong

Korea Polymer Journal, Vol.9, No.6, 327-331, December, 2001

Myong Hoon Lee^†, Yun Sang Cheong, and Myoung Seon Gong¹

Department of Polymer Science and Technology, Chonbuk National University, Chonju, Chonbuk 561-756, Korea
¹Department of Chemistry, Dankook University, Cheonan, Chungnam 330-714, Korea

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A new soluble photosensitive poly(amide-co-imide) containing p-phenylenediacryloyl moiety was synthesized and its photoreactivity was characterized. The copolymer was synthesized from p-phenylenediacryloyl chloride, 4,4-(hexafluoroisopropylidene)diphthalic anhydride and two equivalents of bis(4-aminophenyl) ether in NMP with a subsequent chemical imidization of the resulting poly[amide-co-(amic acid)] by acetic anhydride and pyridine. The structure and thermal properties of the polymer were characterized by spectroscopic methods and thermal analyses. The polymer was stable up to 350℃, showed good solubility in polar aprotic solvents, and became insoluble after UV irradiation due to the [2+2] cycloaddition of phenylenediacryloyl moiety. Photoreactivity of the polymer was investigated in solution or as a film with respect to the various exposure conditions by UV/Vis spectroscopy. The photosensitivity was noticeably increased with the irradiation temperature, especially in the presense of photosensitizer. The reason for the increased sensitivity was speculated based on the flexibilization of main chain at elevated temperature. Exposure characteristic curves were obtained from the gel fraction experiments after UV irradiation. The sensitivity and contrast at 160 ℃ were measured to be 293 mJ/cm2 and 1.64, respectively.

[References]

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Endo A, Yoda T, J. Electrochem. Soc., 132, 155 (1985)
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Schlitz A, IEEE Trans. on Components, Hybrides, and Manufacturing Technology, 15, 226 (1992)
Darrow D, Vilmer-Bagen S, Proceedings of 43rd ECTC, 544 (1993)
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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)
Yoda N, Hiramoto H, J. Macromol. Sci.-Chem., A21, 1641 (1984)
Kataoka E, Shoji F, Takemoto I, Obara I, Kojima M, Yokono H, Isogai T, Polyimides: Synthesis, Characterization, and Applications, K.L. Mittal Ed., Plenum Press New York, 1984, vol. 2, pp 933 (1984)
Hiramoto H, Mater. Res. Soc. Symp., 169, 87 (1990)
Ahne H, Leuschner R, Rubner R, Polym. Adv. Technol., 4, 217 (1992)
Pfeifer J, Rohde O, Proc. 2nd Int. Conf. Polyimides, Ellenville, Soc. Plastics Eng., New York, 1985, pp. 130 (1985)
Nakano T, Proc. 2nd Int. Conf. Polyimides, Ellenville, Soc. Plastics Eng., New York, 1985, pp. 163 (1985)
Lee HR, Lee YD, J. Polym. Sci. A-Polym. Chem., 27, 1481 (1988)
Egerton PL, Trigg J, Hyde EM, Reiser A, Macromolecules, 14, 100 (1984)
Chienhui L, Tehchou L, Kehying H, J. Polym. Sci. A-Polym. Chem., 31, 1119 (1993)
Kehying H, Chenhui L, Tehchou C, Tsuyao C, J. Polym. Sci. A-Polym. Chem., 31, 971 (1993)
Tanaka H, Sasai K, Sato T, Tadatoshi O, Macromolecules, 21, 3536 (1988)
Ruggli P, Theiheimer W, Helv. Chim. Acta, 24, 899 (1941)
Navarro F, Serrano JL, J. Polym. Sci. A-Polym. Chem., 27, 3691 (1989)
Iwata K, Hagiwara T, Matsuzawa H, J. Polym. Sci. A-Polym. Chem., 23, 2361 (1985)
Spiliopoulos IK, Mikroyannidis JA, J. Polym. Sci. A-Polym. Chem., 34(13), 2799 (1996)
Chenhui L, Tehchou C, Tsuyao C, J. Polym. Sci. A-Polym. Chem., 31, 1125 (1993)
Nishikubo T, Iizawa T, Shiozaki Y, J. Polym. Sci. A-Polym. Chem., 30, 449 (1992)

[Related Articles]

[1] Polyimides and Other High-Temperature Polymers, M.J.M. Abadie, B. Sillion Eds., Elsevier, Amsterdam (1991)

[2] Hiramoto H, Mater. Res. Soc. Proc., 167, 87 (1990)

[3] Endo A, Yoda T, J. Electrochem. Soc., 132, 155 (1985)

[4] Wilson AM, Thin Solid Films, 83, 145 (1981)

[5] Schlitz A, IEEE Trans. on Components, Hybrides, and Manufacturing Technology, 15, 226 (1992)

[6] Darrow D, Vilmer-Bagen S, Proceedings of 43rd ECTC, 544 (1993)

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

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

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

[10] Yoda N, Hiramoto H, J. Macromol. Sci.-Chem., A21, 1641 (1984)

[11] Kataoka E, Shoji F, Takemoto I, Obara I, Kojima M, Yokono H, Isogai T, Polyimides: Synthesis, Characterization, and Applications, K.L. Mittal Ed., Plenum Press New York, 1984, vol. 2, pp 933 (1984)

[12] Hiramoto H, Mater. Res. Soc. Symp., 169, 87 (1990)

[13] Ahne H, Leuschner R, Rubner R, Polym. Adv. Technol., 4, 217 (1992)

[14] Pfeifer J, Rohde O, Proc. 2nd Int. Conf. Polyimides, Ellenville, Soc. Plastics Eng., New York, 1985, pp. 130 (1985)

[15] Nakano T, Proc. 2nd Int. Conf. Polyimides, Ellenville, Soc. Plastics Eng., New York, 1985, pp. 163 (1985)

[16] Lee HR, Lee YD, J. Polym. Sci. A-Polym. Chem., 27, 1481 (1988)

[17] Egerton PL, Trigg J, Hyde EM, Reiser A, Macromolecules, 14, 100 (1984)

[18] Chienhui L, Tehchou L, Kehying H, J. Polym. Sci. A-Polym. Chem., 31, 1119 (1993)

[19] Kehying H, Chenhui L, Tehchou C, Tsuyao C, J. Polym. Sci. A-Polym. Chem., 31, 971 (1993)

[20] Tanaka H, Sasai K, Sato T, Tadatoshi O, Macromolecules, 21, 3536 (1988)

[21] Ruggli P, Theiheimer W, Helv. Chim. Acta, 24, 899 (1941)

[22] Navarro F, Serrano JL, J. Polym. Sci. A-Polym. Chem., 27, 3691 (1989)

[23] Iwata K, Hagiwara T, Matsuzawa H, J. Polym. Sci. A-Polym. Chem., 23, 2361 (1985)

[24] Spiliopoulos IK, Mikroyannidis JA, J. Polym. Sci. A-Polym. Chem., 34(13), 2799 (1996)

[25] Chenhui L, Tehchou C, Tsuyao C, J. Polym. Sci. A-Polym. Chem., 31, 1125 (1993)

[26] Nishikubo T, Iizawa T, Shiozaki Y, J. Polym. Sci. A-Polym. Chem., 30, 449 (1992)