Skip to main content
Log in

Synthesis, characterization, and properties of fully aliphatic polyimides and their derivatives for microelectronics and optoelectronics applications

  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

Polyimides are one of the most important classes of polymers used in the microelectronics and photoelectronics industries. Because of their high thermal stability, chemical resistance, and good mechanical and electric properties, polyimides are often applied in photoresists, passivation and dielectric films, soft print circuit boards, and alignment films within displays. Recently, fully aliphatic and alicyclic polyimides have found applications as optoelectronics and inter layer dielectric materials, due to their good transparencies and low dielectric constants (ε). The low molecular density, polarity and rare probability of forming inter- or intra-molecular charge transfers, resulting in lowering of the dielectric constant and high transparency, are the most striking characteristics of aliphatic polyimide. However, the ultimate end use of polyimides derived from aliphatic monomers is in their targeted applications that need less stringent thermal requirements. Much research effort has been exerted in the development of aliphatic polyimide with increased thermal and mechanical stabilities, while maintaining their transparencies and low dielectric constants, by the incorporation of rigid moieties. In this article, the recent research process in synthesizing fully aliphatic polyimides, with improved dimensional stability, high transparency and low ε values, as well as the characterizations and future scope for their application in micro electric and photo-electronic industries, is reviewed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. K. L. Mittal, Ed.,Polyimides: Synthesis, Characterization and Applications, Plenum, New York, 1984.

    Google Scholar 

  2. C. Feger, M. M. Khojasteh, and J. E. McGrath, Eds.,Polyimides: Materials, Chemistry and Characterization, Elsevier, Amsterdam, 1989.

    Google Scholar 

  3. D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother, Eds.,Polyimides, Blackie, Glasgow, 1990.

    Google Scholar 

  4. M. K. Ghosh and K. L. Mittal, Eds.,Polyimides Fundamentals and Applications, Marcel Decker, New York, 1996.

    Google Scholar 

  5. K. Faghihi and M. Hagibeygi,Macromol. Res.,13, 14 (2005).

    Article  CAS  Google Scholar 

  6. M. Ree,Macromol. Res.,14, 1 (2006).

    Article  CAS  Google Scholar 

  7. Y. M. Jang, J. Y. Seo, K. H. Choe, and M. H. Yi,Macromol. Res.,14, 300 (2006).

    Article  CAS  Google Scholar 

  8. K. C. Cho, S. H. Choi, and T. G. Park,Macromol. Res.,14, 348 (2006).

    Article  CAS  Google Scholar 

  9. A. S. Argon and M. I. Bessonov,Polym. Eng. Sci.,17, 174 (1977).

    Article  CAS  Google Scholar 

  10. H. Ishida, S. T. Wellinghoff, E. Baer, and J. L. Koenig,Macromolecules, 13, 826 (1980).

    Article  CAS  Google Scholar 

  11. S. T. Wellinghoff, H. Ishida, J. L. Koenig, and E. Baer,Macromolecules,13, 834 (1980).

    Article  CAS  Google Scholar 

  12. J. R. Havens, H. Ishida, and J. L. Koenig,Macromolecules,14, 1327 (1981).

    Article  CAS  Google Scholar 

  13. X. D. Li, Z. X. Zhong, and G. Jin,Macromol. Res.,14, 257 (2006).

    Article  CAS  Google Scholar 

  14. M. Ree, D. Y. Yoon, and W. Volksen,J. Polym. Sci.; Part B: Polym. Phys.,29, 1203 (1991).

    Article  CAS  Google Scholar 

  15. F. W. Harris and S. L.-C. Hsu,High Perform. Polym.,1, 3 (1989).

    CAS  Google Scholar 

  16. H. Lim, W. J. Cho, C. S. Ha, S. Ando, Y. K. Kim, C. H. Park, and K. Lee,Adv. Mat.,14, 1275 (2002).

    Article  CAS  Google Scholar 

  17. C. S. Ha,Curr. Trends in Polym. Sci.,7, 85 (2002).

    CAS  Google Scholar 

  18. M. A. Wahab, I. Kim, and C. S. Ha,Polymer,44, 4705 (2003).

    Article  CAS  Google Scholar 

  19. Y. Kim, H. B. Kwan, Y. J. Young, K. C. Dong, and C. S. Ha,Chem. Mater.,24, 5051 (2004).

    Article  CAS  Google Scholar 

  20. Y. Kim, M. Ree, T. Chang, C. S. Ha, T. L. Nunes, and J. S. Lin,J. Polym. Sci.; Part B: Polym. Phys.,33, 2075 (1995).

    Article  CAS  Google Scholar 

  21. M. I. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A Laius,Polyimides Thermally Stable Polymers, Consultants Bureau, New York, 1987.

    Google Scholar 

  22. W. M. Edwards and I. M. Robinson, U.S. Patent 2, 867, 609 (1959).

    Google Scholar 

  23. J. A. Kreuz, U.S. Patent 3, 271, 366 (1966).

    Google Scholar 

  24. http://en.wikipedia.org/wiki/kapton.

  25. S. Rojstaczer, M. Ree, D. Y. Yoon, and W. Volksen,J. Polym. Sci.; Part B: Polym. Phys.,30, 133 (1992).

    Article  CAS  Google Scholar 

  26. J. K. Gillham and H. C. Gillham,Polym. Eng. Sci.,13, 447 (1973).

    Article  CAS  Google Scholar 

  27. M. Kochi, S. Isoda, R. Yokota, and H. J. Kambe,Polym. Sci.; Part B: Polym. Phys.,24, 1619 (1986).

    Article  CAS  Google Scholar 

  28. E. Butta, S. De Petris, and M. Pasquini,J. Appl. Polym. Sci.,13, 1073 (1969).

    Article  CAS  Google Scholar 

  29. W. Wrasidlo,J. Macromol. Sci.-Phys.,B3, 559 (1972).

    Google Scholar 

  30. Y. Kim, W. H. Goh, T. Chang, C. S. Ha, and M. Ree,Adv. Eng. Mater.,6, 39 (2004).

    Article  CAS  Google Scholar 

  31. K. H. Choi, J. C. Jung, H. S. Kim, B. H. Sohn, W. C. Zin, and M. Ree,Polymer,45, 1517 (2004).

    Article  CAS  Google Scholar 

  32. I. S. Chung, C. E. Park, M. Ree, and S. Y. Kim,Chem. Mater.,13, 2801 (2001).

    Article  CAS  Google Scholar 

  33. S. I. Kim, T. J. Shin, M. Ree, G. T. Hwang, B.H. Kim, H. Han, and J. Seo,J. Polym. Sci.; Part A: Polym. Chem.,37, 2013 (1999).

    Article  CAS  Google Scholar 

  34. Y. Kim, E. Kang, Y. S. Kwon, W. J. Cho, C. Chang, M. Ree, T. Chang, and C. S. Ha,Synth. Metals,85, 1399 (1997).

    Article  CAS  Google Scholar 

  35. Y. Kim, M. Ree, T. Chang, and C. S. Ha,Polym. Bull.,34, 175 (1995).

    Article  CAS  Google Scholar 

  36. W. M. Robertson, G. Arjavalingam, G. Hougham, G. V. Kopcsay, D. Edelstein, M. Ree, and J. P. Chapple-Sokol,Electronics Lett.,28, 62 (1992).

    Article  Google Scholar 

  37. J. H. Shin, J. W. Park, W. K. Lee, N. J. Jo, W.J. Cho, and C. S. Ha,Synth. Metals,137, 1017 (2003).

    Article  CAS  Google Scholar 

  38. Y. Kim, J. G. Lee, D. K. Choi, Y. Y. Jung, B. Park, J. H. Keum and C. S. Ha,Synth. Met.,91, 329 (1997).

    Article  CAS  Google Scholar 

  39. H. O. Ha, W. J. Cho, and C. S. Ha,Mol. Cryst. Liq. Cryst.,349, 443 (2000).

    Article  CAS  Google Scholar 

  40. L. F. Thompson, C. G. Willson, and S. Tagawa Eds.,Polymers for Microelectronics: Resists and Dielectrics (ACS. Symp. Ser. Vol. 537), Am. Chem. Soc., Washington, DC, 1994.

    Google Scholar 

  41. Y. Sakai, M. Ueda, A. Yahagi, and N. Tanno,Polymer,43, 3497 (2002).

    Article  CAS  Google Scholar 

  42. C. S. Ha, H. D. Park, and C. W. Frank,Chem. Mater.,12, 839 (2000).

    Article  CAS  Google Scholar 

  43. K. R. Carter, R. A. DiPietro, M. I. Sanchez, and S. A. Swanson,Chem. Mater.,13, 213 (2001).

    Article  CAS  Google Scholar 

  44. C. S. Ha, J. H. Shin, and H. T. Lim,Mater. Sci. Eng. B-Solid,85, 195 (2001).

    Article  Google Scholar 

  45. S. J. Lee, C. S. Ha, and J. K. Lee,J. Appl. Polym. Sci.,82, 2365 (2001).

    Article  CAS  Google Scholar 

  46. A. Mochizuki, T. Fukuoka, M. Kanada, N. Kinjou, and T. Yamamoto,J. Photopolym. Sci. Technol.,15, 159 (2002).

    Article  CAS  Google Scholar 

  47. S. Morino, T. Yamashita, K. Horie, T. Wada, and H. Sasabe,React. Funct. Polymers,44, 183 (2000).

    Article  CAS  Google Scholar 

  48. H. D. Park, K. Y. Ahn, M. A. Wahab, N. J. Jo, I. Kim, and C. S. Ha,Macromol. Res.,11, 172 (2004).

    Article  Google Scholar 

  49. S. W. Lee, S. I. Kim, B. Lee, W. Choi, B. Chae, S. B. Kim, and M. Ree,Macromolecules,36, 6527 (2003).

    Article  CAS  Google Scholar 

  50. S. W. Lee, T. Chang, and M. Ree,Macromol. Rapid Commun.,22, 941 (2001).

    Article  CAS  Google Scholar 

  51. H. J. Park, J. W. Park, S. Y. Jeong, and C. S. Ha,IEEE Proceedings,93, 1447 (2005).

    Article  CAS  Google Scholar 

  52. S. M. Pyo, S. I. Kim, T. J. Shin, M. Ree, K. H. Park, and J. S. Kang,Macromolecules,31, 4777 (1998).

    Article  CAS  Google Scholar 

  53. http://www.pslc.ws/macrog/imide.htm.

  54. P. Eliette, M. F. Barthe, J. D. Baerdemaeker, R. Mercier, S. Neyertz, N. D. Alberola, and C. Bas,J. Polym. Sci.; Part B: Polym. Phys.,41, 2998 (2003).

    Article  CAS  Google Scholar 

  55. H. Wang, T. Ugomori, K. Tanaka, H. Kita, K. I. Okamoto, and Y. Suma,J. Polym. Sci.; Part B: Polym. Phys.,38, 2954 (2004).

    Article  Google Scholar 

  56. F. W. Mercer and M. T. McKenzie,High Perform. Polym.,5, 97 (1993).

    Article  CAS  Google Scholar 

  57. Q. Jin, T. Yamashita, and K. Horie,J. Polym. Sci.; Part A: Polym. Chem.,32, 503 (1994).

    Article  CAS  Google Scholar 

  58. T. Matsumoto,High Perform. Polym.,13, S85-S92 (2001).

    Article  CAS  Google Scholar 

  59. H. Seino, T. Sasaki, A. Mochizuki, and M. Ueda,High Perform. Polym.,11, 255 (1999).

    Article  CAS  Google Scholar 

  60. T. Matsuura, M. Ishizawa, Y. Hasuda, and S. Nishi,Macromolecules,25, 3540 (1992).

    Article  CAS  Google Scholar 

  61. R. C. Fort and P. R. Jr., Schleyer,Chem Rev.,64, 277 (1964).

    Article  CAS  Google Scholar 

  62. Y. T. Chern and H. C. Shiue,Chem. Mater.,10, 210 (1998).

    Article  CAS  Google Scholar 

  63. J. J. Jensen, M. Grimsley, and L. J. Mathias,J. Polym. Sci.; Part A: Polym. Chem.,34, 397 (1996).

    Article  CAS  Google Scholar 

  64. Y. T. Chern and W. H. Chung,J. Polym. Sci.; Part A: Polym. Chem.,34, 117 (1996).

    Article  CAS  Google Scholar 

  65. Y. T. Chern, Y. T.Macromolecules,31, 5837 (1998).

    Article  CAS  Google Scholar 

  66. Y. Watanabe, Y. Sakai, M. Ueda, Y. Oishi, and K. Mori,Chem. Lett.,29, 450 (2000).

    Article  Google Scholar 

  67. Y. Watanabe, Y. Shibasaki, S. Ando, and M. Ueda,J. Polym. Sci.; Part A: Polym. Chem.,42, 144 (2004).

    Article  CAS  Google Scholar 

  68. Y. Watanabe, Y. Sakai, Y. Shibasaki, S. Ando, and M. Ueda,Macromolecules,35, 2277 (2002).

    Article  CAS  Google Scholar 

  69. H. Seino, A. Mochizuki, and M. Ueda,J. Polym. Sci.; Part A: Polym. Chem.,37, 3584 (1999).

    Article  CAS  Google Scholar 

  70. A. S. Mathews, I. Kim, and C. S. Ha,J. Appl. Polym. Sci.,102, 3316 (2006).

    Article  CAS  Google Scholar 

  71. A. S. Mathews, I. Kim, and C. S. Ha,J. Polym. Sci.; Part A: Polym. Chem.,44, 5254 (2006).

    Article  CAS  Google Scholar 

  72. Y. Oishi, S. Onodera, J. Oravec, K. Mori, S. Ando, Y. Terui, and K. Maeda,J. Photopolym. Sci. Technol.,16, 263 (2003).

    Article  CAS  Google Scholar 

  73. S. Ando,J. Photopolym. Sci. Technol.,17, 219 (2004).

    Article  CAS  Google Scholar 

  74. P. E. Hougham, P. E. Cassidy, K. Johns, and T. Davidson, Eds.,Fluoropolymers 1: Synthesis and Flouropolymers 2: Properties, Plenum Publishers, New York, 1999.

    Google Scholar 

  75. S. Ando, T. Matsuura, and S. Sasaki,Macromolecules,25, 5858 (1992).

    Article  CAS  Google Scholar 

  76. W. L. Zhou and F. C. Lu,Polymer,35, 590 (1994).

    Article  CAS  Google Scholar 

  77. Y. S. Li, X. Q. Wang, M. X. Ding, and J. P. Xu,J. Appl. Polym. Sci.,61, 741 (1996).

    Article  CAS  Google Scholar 

  78. C. Joly, M. Smaihi, L. Porcar, and R. D. Noble,Chem. Mater.,11, 2331 (1999).

    Article  CAS  Google Scholar 

  79. B. P. Lin, Y. Pan, Y. Qian, and C. W. Yuan,J. Appl. Polym. Sci.,94, 2363 (2004).

    Article  CAS  Google Scholar 

  80. Y. Kawakami, S. P. Yu, and T. Abe,Polym. J.,24, 1129 (1992).

    Article  CAS  Google Scholar 

  81. C. M. Mahoney and J. A. Gargella, Jr.,Macromolecules,35, 5256 (2002).

    Article  CAS  Google Scholar 

  82. H. Deligöz, T. Yalcýnyuva, and S. Özgümüs,Euro. Polym. J.,41, 771 (2005).

    Article  CAS  Google Scholar 

  83. Y. D. Moon and Y. M. Lee,J. Appl. Polym. Sci.,50, 1461 (1993).

    Article  CAS  Google Scholar 

  84. N. Furukawa, Y. Yamada, M. Furukawa, M. Yuasa, and Y. Kimura,J. Polym. Sci.; Part A: Polym. Chem.,35, 2239 (1997).

    Article  CAS  Google Scholar 

  85. M. Yamada, M. Kusama, T. Matsumoto, and T. Kurosaki,J. Org. Chem.,57, 6075 (1992).

    Article  CAS  Google Scholar 

  86. T. Ohno, M. Ozaki, A. Inagaki, T. Hirashima, and I. Nishiguchi,Tetrahedran Lett.,34, 2629 (1993).

    Article  CAS  Google Scholar 

  87. T. Matsumoto and T. Kurosaki,Macromolecules,30, 993 (1997).

    Article  CAS  Google Scholar 

  88. T. Matsumoto, Y. Maeda, and N. Takeshima,J. Photopolym. Sci. Technol.,13, 327 (2000).

    Article  CAS  Google Scholar 

  89. H. Seino, O. Haba, A. Mochizuki, M. Yosioka, and M. Ueda,High Perform. Polym.,9, 333 (1997).

    Article  CAS  Google Scholar 

  90. W. Volksen, H. J. Cha, M. I. Sanchez, and D. Y. Yoon,React. & Func. Polym.,30, 61 (1996).

    Article  CAS  Google Scholar 

  91. T. Kaneda, T. Katsura, K. Nakagawa, and H. Makino,J. Appl. Polym. Sci.,32, 3133 (1986).

    Article  CAS  Google Scholar 

  92. J. Y. Jeon and T. M. Tak,J. Appl. Polym. Sci.,61, 371 (1996).

    Article  CAS  Google Scholar 

  93. D. Wilson, H. D. Stenzenberger, and P. M. Her-genrother, Eds.,Polyimides, Blockie & Son, London, 1990.

    Google Scholar 

  94. Y. J. Kim, T. E. Glass, G. D. Lyle, and J. E. McGrath,Macromolecules,26, 1344 (1993).

    Article  CAS  Google Scholar 

  95. R. W. Lauver,J. Polym. Sci.,17, 2529 (1979).

    CAS  Google Scholar 

  96. Y. Oishi, N. Kikuchi, S. Mori, S. Ando, and K. Maeda,J Photopolym. Sci. Technol.,15, 213 (2002).

    Article  CAS  Google Scholar 

  97. S. Andre, F. G. Pietrasanta, A. Rousseau, B. Boutevin, and G. Caporiccio,Macromol. Chem. Phys.,205, 2420 (2004).

    Article  CAS  Google Scholar 

  98. R. L. Flemming and R. W. Luth,Am. Mineral,87, 25 (2002).

    CAS  Google Scholar 

  99. C. Zhang, F. Babonneau, C. Bonhomme, R. M. Laine, C. L. Soles, H. A. Hristov, and A. F. Yee,J. Am. Chem. Soc.,120, 8380 (1998).

    Article  CAS  Google Scholar 

  100. Y. T. Chern,Macromolecules,31, 1898 (1998).

    Article  CAS  Google Scholar 

  101. D. J. Liaw, B. Y. Liaw, P. N. Hsu, and C. Y. Hwang,Chem. Mater.,13, 1811 (2001).

    Article  CAS  Google Scholar 

  102. C. Suryanarayana and M. G. Norton, inX-Ray Diffraction A Practical Approach, Plenum, New York, 1998, Chapter 3, pp.80–87.

    Google Scholar 

  103. N. Takahasi, D. Y. Yoon, and W. Parrish,Macromolecules,17, 2583 (1984).

    Article  Google Scholar 

  104. S. Herminghaus, D. Boese, D. Y. Yoon, and B. A. Smith,Appl. Phys. Lett.,59, 1043 (1991).

    Article  CAS  Google Scholar 

  105. D. Boese, H. Lee, D. Y. Yoon, J. D. Swalen, and J. Rabolt,J. Polym. Sci. B,30, 1321 (1992).

    Article  CAS  Google Scholar 

  106. W. Volksen, H. J. Cha, M, I. Sanchez, and D. Y. Yoon,React. Funct. Polym.,30, 61 (1996).

    Article  CAS  Google Scholar 

  107. T. Matsumoto,Macromolecules,32, 4933 (1999).

    Article  CAS  Google Scholar 

  108. S. Kripotou, P. Pissis, V. A. Bershtein, P. Sysel, and R. Hobzova,Polymer,44, 2781 (2003).

    Article  CAS  Google Scholar 

  109. M. Kusama, T. Matsumoto, and T. Kurosaki,Macromolecules,27, 1117 (1994).

    Article  CAS  Google Scholar 

  110. J. C. Huang, Z. K. Zhu, J. Yin, D. M. Zhang, and X. F. Qian,J. Appl. Polym. Sci.,79, 794 (2001).

    Article  CAS  Google Scholar 

  111. A. Morikawa, Y. Iyoku, M. Kakimoto, and Y. Imai,Polym. J.,24, 107 (1992).

    Article  CAS  Google Scholar 

  112. J. J. Zarzycki,Sol-Gel Sci. Technol.,8, 17 (1997).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chang-Sik Ha.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mathews, A.S., Kim, I. & Ha, CS. Synthesis, characterization, and properties of fully aliphatic polyimides and their derivatives for microelectronics and optoelectronics applications. Macromol. Res. 15, 114–128 (2007). https://doi.org/10.1007/BF03218762

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03218762

Keywords

Navigation