Charge transfer in aromatic polyimides

Polyimides: Fundamentals and Applications

Volumn , Issue , 2018, Pages 279-307

  Salley, Joseph M ^a   Frank, Curtis W ^b  

^a Milliken Chemical   (United States)

^b Stanford University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; DIELECTRIC PROPERTIES; POLYIMIDES;

AROMATIC POLYIMIDES; DEGREE OF ORDER; LANGMUIR BLODGETT TECHNIQUES; MOLECULAR ORDERING; PHYSICAL AGING; POLY(AMIC ACID); PROCESS CONDITION; VOLUME RELAXATION;

LANGMUIR BLODGETT FILMS;

EID: 85052863591     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9780203742945     Document Type: Chapter

References (123)

1. M. Kochi and H. Kambe, Polym. Eng. Rev. 3: 356 (1983).
2. S. Isoda, H. Shimada, M. Kochi, and H. Kambe, J. Polym. Sci., Polym. Phys. Ed., 13: 1293 (1980).
3. T. P. Russell, J. Polym. Sci., Polym. Phys. Ed. 22: 1105 (1984).
4. N. Takahashi, D. Yoon, and W. Parrish, Macromolecules 17: 2583 (1984).
5. Yu. G. Baklagina, N. V. Efanova, N. R. Prokopchuk, L. N. Korzhavin, A. V. Sidorovich, F. S. Florinskii, and M. M. Koton, Dokl. Akad. Nauk SSR. 221(3): 609 (1975).
6. Yu. G. Baklagina, G. I. Guryainov, N. V. Yefanova, A. I. Kol’tsov, L. N. Korzhavin, N. V. Mikhailova, V. N. Nikitin, and N. P. Prokopchuk, Polym. Sci. USSR A18(6): 1489 (1976).
7. I. S. Milevskaya, Yu. G. Baklagina, A. V. Sidorovich, L. N. Korzhavin, and N. V. Lukasheva, J. Struct. Chem. 22(3): 345 (1981).
8. M. I. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Laius, in Polyimides, Thermally Stable Polymers. (W. W. Wright, ed.), Consultants Bureau, New York, 1987, p. 112.
9. B. Factor, Phys. Rev. Lett. 66(9): 1181 (1991).
10. D. A. Hoffmann, H. Ansari, and C. W. Frank, in High Temperature Polymers for Microelectronics (D. T. Grubb, I. Mita, D. Y. Yoon, eds.) Materials Research Society, Pittsburgh, 1991, pp. 131-136.
11. I. S. Milevskaya, A. V. Sidorovich, Yu. G. Baklagina, N. V. Efanova, V. K. Lavrent’ev, and N. R. Prokopchuk, J. Struct. Chem. 19: 86 (1978).
12. Yu. G. Baklagina, I. S. Milevskaya, N. V. Yefanova, A. V. Sidorovich, and V. A. Zubkov, Polym. Sci. USSR A18(6): 1417 (1976).
13. S. Ito, K. Kanno, S. Ohmori, O. Yoshihiko, and M. Yamamoto, Macromolecules 24(3): 659 (1991).
14. H. Ikeno, A. Oh-saki, N. Ozaki, M. Nitt, K. Nakaya, and S. Kobayashi, SID Digest 45 (1988).
15. M. Kakimoto, A. Morikawa, Y. Nishikata, M. Suzuki, and Y. Imai, J. Colloid Interface Sci. 121(2): 599 (1988).
16. M. Kakimoto, M. Suzuki, T. Konishi, Y. Imai, Yoshio, M. Iwamoto, and T. Hino, Chem. Letts. 823 (1986).
17. M. Kakimoto, M. Suzuki, Y. Imai, M. Iwamoto, and T. Hino, Polym. High Tech. 485 (1987).
18. E. Wachsman and C. W. Frank, Polymer 29: 1191 (1988).
19. M. Hasegawa, M. Kochi, I. Mita, and R. Yokota, Eur. Polym. J. 25(4): 349 (1989).
20. R. S. Dine-Hart and W. W. Wright, Makromol. Chem. 143: 189 (1971).
21. A. K. St. Clair, T. L. St. Clair, and W. S. Slemp, in Recent Advances in Polyimide Technology (W. D. Weber and M. R. Gupta, eds.), Mid-Hudson Section of the Soc. of Plast. Eng., Pough-keepsie, New York, 1987, p. 16.
22. D. Creed, C. E. Hoyle, E. T. Anzures, R. Nagarajan, and P. Subramanian, Polym. Preprints, (Am. Chem. Soc. Div. Polym. Chem.) 33: 855 (1992).
23. G. Arjavalingam, G. Hougham, and J. P. LaFemina, Polymer 31: 840 (1990).
24. S. C. Freilich, Macromolecules 20: 973 (1987).
25. R. Pariser, Polym. J. 19: 127 (1987).
26. Y. B. Fainshtein, L. A. Igonin, G. A. Lushcheiken, and L. N. Yelmel’Yanova, Polym. Sci. USSR 18(3): 580 (1976).
27. M. Fryd, in Polyimides: Synthesis, Characterization, and Applications (K. L. Mittal, ed.), Plenum Press, New York, 1984, p. 377.
28. L. R. Caswell, P. Palacios, S. J.Schmidt, R. Anvar, and A. Garcia, J. Heterocycl. Chem. 15(7): 33 (1978).
29. P. S. Ho, Appl. Surface Sci. 41: 559 (1989).
30. P. S. Ho, B. D. Silverman, R. A. Haight, R. C. White, R. C, P. N. Sanda, and A. R. Rossi, IBM J. Res. Dev. 32(5): 658 (1988).
31. M. J. Goldberg, J. G. Clabes, and C. A. Kovac, J. Vac. Sci. Technol. A. 6(3): 991 (1988).
32. J. G. Clabes, J. Vac. Sci. Technol. A. 6(5): 2887 (1988).
33. J. G. Clabes, M. J. Goldberg, A. Viebeck, and C. A. Kovac, J. Vac. Sci. Technol. A. 6(3): 985 (1988).
34. W. R. Salaneck, S. Stafstrom, J. L. Bredas, S. Anderson, P. Bodo, S. P. Kowalczyk, and J. J. Ritsko, J. Vac. Sci. Technol. A. 6(6): 3134 (1988).
35. R. Haight, R. C. White, B. D. Silverman, and P. S. Ho, J. Vac. Sci. Technol. A. 6(4): 2188 (1988).
36. Lj Atanasoska, S. G. Anderson, H. M. Meyer, L. Zhangda, and J. H. Weaver, J. Vac. Sci. Technol. A. 5(6): 3325 (1987).
37. C. J. Lee, J. Macromol. Sci. Rev. Macromol Chem. Phys. C29(4): 431 (1989).
38. J. M. Salley and C. W. Frank, Polym. Preprints, (Am. Chem. Soc. Div. Polym. Chem.) 33: 855 (1992).
39. N. N. Barashkov, L. I. Semenova, and R. N. Normukhametov, Vysokomol. Soyed. A25: 1090 (1983).
40. E. N. Konstantinova, E. E. Kever, K. K. Kalnin’sh, G. S. Dedovets, and V. S. Ivanov, Z. Org. Khim., 14(1): 98 (1978) (Engl, transl. J. Org. Chem. USSR. 88 [1978]).
41. D. V. Pebalk, Y. L. Spasibin, B. V. Kotov, Y. S. Vygodskii, and A. N. Pravednikov, Doklady Chem., 242(3): 453 (1979).
42. R. S. Mulliken, Molecular Complexes, John Wiley & Sons, New York, 1969.
43. S. Nagakura, J. Chem. Phys. 23(8): 1441 (1955).
44. M. J. S. Dewar, J. Chem. Soc. 2329 (1950).
45. H. C. Longuet-Higgins and J. N. Murrell, Proc. Phys. Soc. A68: 601 (1955).
46. H. B. Klevens and J. R. Piatt, J. Am. Chem. Soc, 71, 1713 (1949).
47. H. Suzuki, Electronic Absorption Spectra and Geometry of Organic Molecules, Academic Press, New York, 1967, p. 390.
48. G. I. Kagan, V. A. Kosobutskii, V. K. Belyakov, and O. G. Tarakoanov, Chem. Heterocycl. Compounds, USSR 8: 949 (1972).
49. D. Haarer, C. P. Keijzers, and R. Silbey, J. Chem. Phys. 66(2): 563 (1977).
50. V. M. Vozzhennikov, I. V. Bulgarovskaya, V. P. Krasavin, and B. V. Kotov, Z. Fizich. Khim. 56: 1758 (1982). (Engl, transl. Russian J. Phys. Chem. 56(7): 1065 [1982]).
51. V. M. Vozzhennikov, B. V. Kotov, and V. P. Krasavin, Z. Fizich. Khim. 51: 1828-1830 (1977). (Engl, transl. Russian J. Phys. Chem. 51(7): 1074 [1977]).
52. I. V. Bulgarovskaya, V.M. Vozzhennikov, and A. I. Stash, Z. Fizich. Khim. 61: 419 (1987) (Engl, transl. Russian J. Phys. Chem. 61(2): 217 [1987]).
53. N. Karl and J. Ziegler, Chem. Phys. Lett. 32(3): 438 (1975).
54. D. V. Pebalk, B. V. Kotov, O. Y. Neiland, I. V. Mazere, V. Z. Tilika, and A. N. Pravednikov, Doklady Chem. 236(6): 610 (1977).
55. O. V. Kolninov, Z. V. Zvonkova, and V. P. Glushkova, Russian J. Phys. Chem. 43(6): 832 (1969).
56. I. V. Bulgarovskaya, E. M. Smelyanskaya, Yu. G. Feorov, and Z. V. Zvonkova, Sov. Phys. Crystallogr. 19(2): 157 (1974).
57. Z. V. Zvonkova, I. V. Bulgarovskaya, and O. V. Kolninov, Doklady Akad. Nauk SSR. 229: 1141 (1976). Engl, transl. Doklady Phys. Chem. 229: 715 [1976].
58. M. Chowdhury, J. Phys. Chem. 66: 353 (1960).
59. A. I. Konovalov, V. D. Kiselev, and O. A. Vigdorovich, Z. Org. Khim. 3(12): 2085 (1967). Engl, transl. J. Org. Chem., USSR 3(72), 2034 [1967].
60. A. I. Konovalov, V. D. Kiselev, and M. B. Metelina, Z. Org. Khim. 6(8): 1548 (1970). Engl, transl. J. Org. Chem., USSR 6(8): 1561 [1970].
61. W. J. Sep, J. W. Verhoeven, and Th. J. de Boer, Tetrahedron 31(8): 1065 (1975).
62. L. Frankevich, B. M. Rumyantsev, V. I. Lesin, and B. V. Kotov, Opt. Spektosk. 42: 905 (1977). Engl, transl. Opt. Spectrosc. 42(5): 520 [1977].
63. D. Haarer and N. Karl. Chem., Phys. Lett. 21(1): 49 (1973).
64. L. L. Ferstandig, W. G. Toland, and C. D. Heaton, J. Am. Chem. Soc. 83, 1151 (1961).
65. Y. Nakayama, Y. Ichikawa, and T. Matsuo, J. Chem. Soc. Jpn. 38: 1674 (1965).
66. I. Ilmet and P. Rashba, J. Phys. Chem. 71(4): 1140 (1967).
67. S. R. Rafikov, G. P. Naletova, O. A. Ponomarev, and N. S. Vshivtseva, Z. Obshchei Khim. 47(7): 187-193 (1990). (Engl, transl. J. Gen. Chem., USSR. 47(1): 172-176 [1977]).
68. S. R. Rafikov, G. P. Naletova, and N. S. Vshivtseva, Z. Obshchei Khim. 47(11): 2610 (1977). (Engl, transl. J. Gen. Chem., USSR. 47(4): 2382 [1977]).
69. I. V. Bulgarovskaya, E. M. Smelyanskaya, Yu. G. Feorov, and Z. V. Zvonkova, Sov. Phys. Crystallogr. 22(1): 104 (1977).
70. J. C. A. Boeyens and F. H. Herbstein, J. Phys. Chem. 69: 2160 (1965).
71. B. E. Robertson and J. J. Stezowski, Acta Cryst. B24: 3005 (1978).
72. I. V. Bulgarovskaya and Z. V. Zvonkova, Sov. Phys. Crystallogr. 21(3): 335 (1976).
73. H. M. Rosenburg, and E. C. Eimutis, J. Phys. Chem. 70(11): 3494 (1966).
74. O. V. Kolninov, Yu. P. Popov, V. M. Bozzhennikov, A. V. Dzyabchenko, and Z. V. Zvonkova, Doklady Akad. Nauk SSSR. 205(1): 110 (1972). Engl, transl. Doklady Phys. Chem. 205: 547 [1972].
75. F. J. Dinan, W. T. Schwartz, R. A. Wolfe, D. S. Hojnicki, T. St. Clair, and J. R. Pratt, J. Polym. Sci.: Polym. Chem. Ed., 30: 111 (1992).
76. J. M. Salley and C. W. Frank, to be published.
77. S. Iwata, J. Tanaka, and S. Nagakura, J. Am. Chem. Soc. 88: 894 (1966).
78. L. D. Orgel, J. Chem. Phys. 1352 (1955).
79. E. M. Voigt, J. Am. Chem. Soc. 86: 3611 (1964).
80. L. G. Schroff, A. J. A. van der Weerdt, D. J. H. Staalman, J. W. Verhoeven, and Th. J. de Boer, Tetrahedron Lett. 1649 (1973).
81. L. G. Schroff, R. L. J. Zsom, A. J. A. van der Weerdt, P. I. Schrier, J. P. Geerts, N. M. M. Nibbering, J. W. Verhoeven, and Th. J. de Boer, Regu. Trav. Chim. Pays-Bas. 95: 89 (1976).
82. J. H. Borkent, J. W. Verhoeven, and Th. J. de Boer, Chem. Phys. Lett. 42(1): 50 (1976).
83. N. N. Barashkov, L. I. Semenova, and R. N. Normukhametov, Polym. Sci. USSR. 242(3): 625 (1978).
84. H. Ishida, S. T. Wellinghoff, E. Baer, and J. L. Koenig, Macromolecules 13: 826 (1980).
85. J. LaFemina, G. Arjavalingam, and G. Hougham, J. Chem. Phys. 90(9): 5154 (1989).
86. J. M. Salley, T. Miwa, and C. W. Frank, in High Temperature Polymers for Microelectronics, (D. T. Grubb, I. Mita, D. Y. Yoon, eds.), Materials Research Society, Pittsburgh, 1991, p. 137.
87. J. M. Salley, C. W. Frank, T. Miwa, and R. Roginski, in Advances in Polyimide Science and Technology (C. Feger, M. Khojasteh, and M. Htoo, eds.), Technomic, Lancaster, PA, 1993, p. 441.
88. M. Hasegawa, H. Arai, K. Horie, R. Yokota, and I. Mita, in High Temperature Polymers for Microelectronics, (D. T. Grubb, I. Mita, D. Y. Yoon, eds.), Materials Research Society, Pittsburgh, 1991, p. 125.
89. J. M. Salley and C. W. Frank, unpublished results.
90. B. V. Kotov, T. A. Gordina, V. S. Voishechev, O. V. Kolninov, and A. N. Pravednikov, Vysokomol. Soyed. A19(3): 613 (1977).
91. Engl, transl. Polym. Sci. USSR 711 [1977].
92. E. V. Lamskaya and B. V. Kotov, Doklady Akad. Nauk SSR 296(6): 1397 (1987). (Engl, transl. Doklady Phys. Chem. 1020 [1987]).
93. J. Prochorow and R. Siegoczynski, Chem. Phys. Lett. 3(8): 635 (1969).
94. S. Numata, K. Fujisaki, and N. Kinjo, Polymer 28: 2282 (1987).
95. R. O. Waldbauer, M. E. Rogers, C. A. Arnold, G. A. York, Y. Kim, and J. E. McGrath, Polym. Preprints, (Am. Chem. Soc. Div., Polym. Chem.) 31(2): 432 (1990).
96. E. L. Frankevich, A. I. Pristupa, and V. I. Lesin, Chem. Phys. Lett. 47(2): 304 (1977).
97. J. Prochorow and E. Bernard, J. Luminesc. 471 (1974).
98. E. D. Wachsman, P. S. Martin, and C. W. Frank, in Polym. Mater. Electron. Packag. Interconnect: A.C.S. Symposium Series. 407, Amer. Chem. Soc. Washington, D.C, 1989, p. 27.
99. M. Hasegawa, H. Arai, I. Mita, and R. Yokota, Polym. J. 22(10): 875 (1990).
100. P. S. Martin, E. D. Wachsman, and C. W. Frank, in Polyimides: Materials, Chemistry and Characterization (C. Feger, M. M. Khojasteh, and J. E. McGrath, eds.), Elsevier, Amsterdam, 1989, p. 371.
101. M. Hasegawa and I. Mita, J. Polym. Sci. Polym. Lett. 27: 263 (1989).
102. B. V. Kotov. Z. Fizich. Khim. 62: 2709 (1989). (Engl, transl. Russ. J. Phys. Chem. 62(10): 1408 [1988]).
103. M. I. Bessonov, M. M. Koton, and L. A. Laius, Polyimides. Thermally Stable Polymers. Consultants Bureau, New York, 1987, p. 181.
104. S. A. Khafafi, J. P. LaFemina, and J. L. Nauss, J.Am. Chem. Soc. 112: 8742 (1990).
105. S. A. Khafafi, Chem. Phys. Lett. 169(6): 561 (1990).
106. R. N. Nurmukhametov, L. I. Semenova, N. V. Korol’kova, G. A. Val’kova, and I. Ponomarev, Z. Fizich. Khim. 64: 2972 (1990). (Engl, trans. Russ. J. Phys. Chem. 64(11): 1604 [1990]).
107. S. C. Freilich and K. H. Gardner, in Polyimides: Materials, Chemistry and Characterization (C. Feger, M. M. Khojasteh, and J. E. McGrath, eds.), Elsevier, Amsterdam, 1989, p. 513.
108. L. Kan and K. C. Kao, J. Chem. Phys. 98(4): 3445-3451 (1993).
109. L. Kan and K. C. Kao, Proc. IEEE Int. Symp. Elect. Insulation, 84 (1990).
110. J. P. LaFemina, Chem. Phys. Lett. 159(4): 307 (1989).
111. K. Iida, T. Nohara, S. Nakamura, and G. Sawa, Jpn. J. Appl. Phys. 28(8): 1390 (1989).
112. A. Viebeck, M. J. Goldberg, and C. A. Kovac, J. Electrochem. Soc. 137(5): 1460 (1990).
113. T. A. Gordina, B. V. Kotov, O. V. Kolnlvov, and A. N. Pravednikov. Vysokomol. Soyed. B15: 378 (1973).
114. L. J. Krause and R. C. Haushalter, Thin Solid Films. 102: 161 (1983).
115. K. Iida, T. Tankmoto, S. Nakamura, M. Ieda, and G. Sawa, Jpn. J. Appl. Phys. 25: 1542 (1986).
116. V. A. Zubkov and I. S. Milevskaya, Polym. Sci. USSR 2: 320-327 (1983).
117. A. P. Rudakov; M. I. Bessonov, Sh. Tuichiev, M. M. Koton, F. S. Florinskii, and B. M. Ginzburg, Polym. Sci. USSR A12(3): 720 (1970).
118. L. G. Kazaryan, D. Ya. Tsvankin, B. M. Ginzburg, Sh. Tuichiev, L. N. Korzhavin, and S. Ya. Frenkel, Polym. Sci. USSR A14(5): 1344 (1972).
119. C. A. O’Mahoney, D. J. Williams, H. M. Colquhoun, R. Mayo, S. M. Young, A. Askari, J. Kendrick, and E. Robson, Macromolecules 24(42): 6527 (1991).
120. W. G. Blann, C. A. Fyfe, J. R. Lyerla, and C. S. Yannoni, J. Am. Chem. Soc. 103: 4030 (1981).
121. C. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc. 112: 5525 (1990).
122. M. O. Aboelfotoh and C. Feger, Phys. Rev. B. 47: 13395 (1993).
123. D. A. Hoffmann, H. Ansari, and C. W. Frank, to be published.