Carbazole photorefractive materials

Abstract

Considerable progress has been made in organic photorefractive materials, since the first observation of photorefractive phenomena from organic materials. Within recent years, a large number of organic photorefractive materials, especially amorphous materials, have been developed based on polymeric composites, fully functional polymers and the multifunctional chromophore approach. Among these organic photorefractive materials, some of them containing carbazole components as a charge transporting function have been demonstrated to exhibit high performance photorefractive effects. The carbazole building blocks with charge transporting functionality or multifunctions play a very important role in photorefraction and have been widely used in the molecular design approach to new organic photorefractive materials. Based on carbazole functional building blocks, amorphous multifunctional chromophores, amorphous monolithic chromophores and amorphous dendrimers have also been developed as new types of organic photorefractive materials. This paper reviews the recent progress of organic photorefractive materials, especially organic photorefractive materials containing carbazole functional components.

References

1. Photorefractive Materials and Their Applications I and II, ed. P. Gülnter and J.-P. Huignard, Springer Verlag, Berlin, 1988.
2. Introduction to Photorefractive Nonlinear Optics, ed. P. Yeh, Wiley, New York, 1993.
3. Laser-Induced Dynamic Grating, Springer Series in Optical Sciences, ed. H. J. Eichler, P. Gülnter and D. W. Pohl, Springer, Berlin, 1986, vol. 50.
4. Photochromism: Techniques of Chemistry, ed. G. H. Brown, Wiley-Interscience, New York, 1971, vol. I–III.
5. A. Ashkin, G. D. Boyd, J. M. Dziedzic, R. G. Smith, A. A. Ballmann and K. Nassau, Appl. Phys. Lett., 1966, 9, 72.
6. A. M. Glass, A. M. Johnson, D. H. Olson, W. Simpson and A. A. Ballman, Appl. Phys. Lett., 1984, 44, 948.
7. J. Feinberg, Physics Today, 1988, 41, 46.
8. G. Roosen, J.-P. Huignard and M. Cronin-Golomb, J. Opt. Soc. Am. B, 1990, 7, 2242.
9. J. Feinberg and B. Fischer, J. Opt. Soc. Am. B, 1992, 9, 1404.
10. L. Hesselink, E. Kratzig and K. H. Ringhofer, J. Opt. Soc. Am. B, 1994, 11, 1648.
11. K. Sutter, J. Hullinger and P. Cülnter, Solid State Commun., 1990, 74, 867.
12. K. Sutter and P. Gülnter, J. Opt. Soc. Am. B, 1990, 7, 2274.
13. S. Ducharme, J. C. Scott, R. J. Twieg and W. E. Moerner, Phys. Rev. Lett., 1991, 66, 1846.
14. W. E. Moerner and S. M. Silence, Chem. Rev., 1994, 94, 127.
15. Nonlinear Optical Properties of Organic Molecules and Crystals, ed. D. S. Chemla and J. Zyss, Academic Press, Orlando, 1987, vol. 1 and 2.
16. G. C. Valley and N. B. Klein, Opt. Eng., 1983, 22, 704.
17. Y. Zhang, R. Burzynski, S. Ghosal and M. K. Casstevens, Adv. Mater., 1996, 8, 111.
18. L. Yu, W. K. Chan, Z. Peng and A. Gharavi, Acc. Chem. Res., 1996, 29, 13.
19. P. M. Lundquist, R. Wortmann, C. Geletneky, R. J. Twieg, M. Jurich, V. Y. Lee, C. R. Moylan and D. M. Burland, Science, 1996, 274, 1182.
20. Y. D. Zhang, T. Wada, L. Wang and H. Sasabe, Tetrahedron Lett., 1997, 38, 1758.
21. L. Wang, Y. D. Zhang, T. Wada and H. Sasabe, Appl. Phys. Lett., 1996, 69, 728.
22. H. J. Bolink, V. V. Krasnikov, G. G. Malliaras and G. Hadziioannou, Adv. Mater, 1994, 6, 574.
23. L. Onsager, Phys. Rev., 1938, 54, 554.
24. G. Pfister, Phys. Rev. B, 1977, 16, 3676.
25. J. S. Schildkraut, Appl. Phys. Lett., 1991, 58, 340.
26. E. Müller-Horsche, D. Haarer and H. Scher, Phys. Rev. B, 1987, 35, 1273.
27. J. C. Scott, L. Th. Pautmeier and W. E. Moerner, J. Opt. Soc. Am. B, 1992, 9, 2059.
28. C. C. Teng and H. T. Man, Appl. Phys. Lett., 1990, 56, 1734.
29. M. Siegelle and R. Hierle, J. Appl. Phys., 1981, 52, 4199.
30. K. D. Singer, M. G. Kuzyk, W. R. Holland, J. E. Sohn, S. J. Lalama, R. B. Comizzoli, H. E. Katz and M. L. Schilling, Appl. Phys. Lett., 1988, 53, 1800.
31. W. E. Moerner, S. M. Silence, F. Hache and G. C. Bjorklund, J. Opt. Soc. Am. B, 1994, 11, 320.
32. C. A. Walsh and W. E. Moerner, J. Opt. Soc. Am. B, 1992, 9, 1642.
33. J. P. Huignard and A. Marrakchi, Opt. Commun., 1981, 38, 249.
34. J. Feinberg, D. Heiman, A. R. Tanguay, Jr. and R. W. Hellwarth, J. Appl. Phys., 1980, 51, 1297.
35. D. H. Dunlap, E. P. Parris and V. M. Kenkre, Phys. Rev. Lett., 1996, 77, 542.
36. W. E. Moerner, C. Walsh, J. C. Scott, S. Ducharme, D. M. Burland, G. C. Bjorklund and R. J. Twieg, Proc. SPIE, 1991, 1560, 278.
37. S. Ducharme, B. Jones, J. M. Takacs and L. Zhang, Opt. Lett., 1993, 18, 152.
38. S. M. Silence, C. A. Walsh, J. C. Scott, T. J. Matray, R. J. Twieg, F. Hache, G. C. Bjorklund and W. E. Moerner, Opt. Lett., 1992, 17, 1107.
39. S. M. Silence, C. A. Walsh, J. C. Scott and W. E. Moerner, Appl. Phys. Lett, 1992, 61, 2967.
40. Y. Cui, Y. Zhang, P. N. Prasad, J. S. Schildkraut and D. J. Williams, Appl. Phys. Lett., 1992, 61, 2132.
41. S. M. Silence, F. Hache, M. Donckers, C. A. Walsh, D. M. Burland, G. C. Bjorklund, R. J. Twieg and W. E. Moerner, Proc. SPIE, 1993, 1852, 253.
42. M. Liphardt, A. Goonesekera, B. E. Jones, S. Ducharme, J. M. Takacs and L. Zhang, Science, 1994, 263, 367.
43. A. Darwish, N. Kukhtarev, R. Copland, R. Sliz, P. Venkatesewarlu, A. Williams, J. Caulfield, S. Ducharme, J. M. Takacs and L. Zhang, Proc. SPIE, 1996, 2850, 33.
44. A. Goonesekera, S. Ducharme, J. M. Takacs and L. Zhang, Proc. SPIE, 1996, 2850, 41.
45. S. M. Silence, J. C. Scott, F. Hache, E. J. Ginsburg, P. K. Jenkner, R. D. Miller, R. J. Twieg and W. E. Moerner, J. Opt. Soc. Am. B, 1993, 10, 2306.
46. K. Yokoyama, K. Arishima, T. Shimada and K. Sukegawa, Jpn. J. Appl. Phys., 1994, 33, 1029.
47. K. Yokoyama, K. Arishima and K. Sukegawa, Appl. Phys. Lett., 1994, 65, 132.
48. R. Burzynski, Y. Zhang, S. Ghosal and M. K. Casstevens, Polymeric Materials Science and Engineering, ACS Spring Meeting, Anaheim, California, 1995, vol. 72, p. 292 ACS, Washington DC.
49. R. Wortmann, C. Poga, R. J. Twieg, C. Geletneky, C. R. Moylan, P. M. Lundquist, R. G. DeVoe, P. M. Cotts, H. Horn, J. E. Rice and D. M. Burland, J. Chem. Phys., 1996, 105, 10 637.
50. S. Heun and P. M. Borsenberger, Chem. Phys., 1995, 200, 245.
51. C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton and R. D. Miller, J. Am. Chem. Soc., 1993, 115, 12 599.
52. J. J. Stankus, S. M. Silence, R. J. Twieg, D. M. Burland, R. D. Miller, J. C. Scott, W. E. Moerner and G. C. Bjorklund, Proc. SPIE, 1994, 2285, 204.
53. S. M. Silence, R. J. Twieg, G. C. Bjorklund and W. E. Moerner, Phys. Rev. Lett., 1994, 73, 2047.
54. S. M. Silence, J. C. Scott, J. J. Stankus, W. E. Moerner, C. R. Moylan, G. C. Bjorklund and R. J. Twieg, J. Phys. Chem., 1995, 99, 4096.
55. Y. Zhang, S. Ghosal, M. Casstevens and R. Burzynski, Appl. Phys. Lett., 1995, 66, 256.
56. Y. Zhang, S. Ghosal, M. Casstevens and R. Burzynski, J. Appl. Phys., 1996, 79, 8920.
57. H. J. Bolink, C. Arts, V. V. Krasnikov, G. G. Malliaras and G. Hadziioannou, Proc. SPIE, 1996, 2850, 69.
58. M. Stolka, J. F. Yanus and D. M. Pai, J. Phys. Chem., 1984, 88, 4707.
59. P. M. Lundquist, R. J. Twieg, R. Wortmann, R. M. Shelby, C. Geletneky, M. Jurich and D. M. Burland, Proc. SPIE, 1996, 2850, 78.
60. L. Yu, W. K. Chan, Z. N. Bao and S. Cao, Macromolecules, 1993, 26, 2216.
61. L. Yu, Y. M. Chen, W. K. Chan and Z. H. Peng, Appl. Phys. Lett., 1994, 64, 2489.
62. Z. H. Peng, Z. N. Bao, Y. M. Chen and L. Yu, J. Am. Chem. Soc., 1994, 116, 6003.
63. Z. H. Peng, A. R. Gharavi and L. Yu, Appl. Phys. Lett., 1996, 69, 4002.
64. M. Gailberger and H. Bassler, Phys. Rev. B, 1991, 44, 8643.
65. L. Li, K. G. Chittibabu, Z. Chen, J. I. Chen, S. Marturunkakul, J. Kumar and S. K. Tripathy, Opt. Commun., 1996, 125, 257.
66. W. D. Gill, J. Appl. Phys., 1972, 42, 5033.
67. H. Hoegl, J. Phys. Chem., 1965, 69, 755.
68. Poly(N-vinylcarbazole), ed. J. M. Pearson and M. Stolka, Gordon and Breach, New York, 1981.
69. Y. Zhang, Y. Cui and P. N. Prasad, Phys. Rev. B, 1992, 46, 9900.
70. K. Meerholz, B. L. Volodin, Sandalphon, K. Kippelen and N. Peyghambarian, Nature, 1994, 371, 497.
71. A. Gunnet-Jepsen, C. L. Thompson, R. J. Twieg and W. E. Moerner, Appl. Phys. Lett., 1997, 70, 1515.
72. P.-M. Allemand, A. Koch, F. Wudl, Y. Rubin, F. Diederich, M. M. Alvarez, S. J. Anz and R. L. Whetton, J. Am. Chem. Soc., 1991, 113, 1050.
73. J. W. Arbogast, C. S. Foote and M. Kao, J. Am. Chem. Soc., 1992, 114, 2277.
74. Y. Wang, Nature, 1992, 356, 585.
75. Y. Zhang, C. A. Spencer, S. Ghosal, M. Casstevens and R. Burzynski, Appl. Phys. Lett., 1994, 64, 1908.
76. Y. Zhang, C. A. Spencer, S. Ghosal, M. K. Casstevens and R. Burzynski, J. Appl. Phys., 1994, 76, 671.
77. M. C. J. M. Donckers, S. M. Silence, C. A. Walsh, F. Hache, D. M. Burland, W. E. Moerner and R. J. Twieg, Opt. Lett., 1993, 18, 1044.
78. G. Weiser, J. Appl. Phys., 1972, 43, 5028.
79. P. Yeh, Appl. Opt., 1987, 26, 602.
80. S. M. Silence, M. C. J. M. Donckers, C. A. Walsh, D. M. Burland, R. J. Twieg and W. E. Moerner, Appl. Opt., 1994, 33, 2218.
81. W. E. Moerner, S. M. Silence, F. Hache and G. C. Bjorklund, J. Opt. Soc. Am. B, 1994, 11, 320.
82. D. M. Burland, G. C. Bjorklund, W. E. Moerner, S. M. Silence and J. J. Stankus, Pure Appl. Chem., 1995, 67, 33.
83. D. M. Burland, R. G. Devoe, C. Geletneky, Y. Jia, V. Y. Lee, P. M. Lundquist, C. R. Moylan, C. Poga, R. J. Twieg and R. Wortmann, Pure Appl. Opt., 1996, 5, 513.
84. M. E. Orczyk, J. Zieba and P. N. Prasad, Appl. Phys. Lett., 1995, 63, 311.
85. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Appl. Phys. Lett., 1994, 65, 262.
86. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Proc. SPIE, 1995, 2526, 94.
87. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Appl. Phys. Lett., 1995, 66, 1038.
88. D. M. Pai, J. F. Yanus and M. Stolka, J. Phys. Chem., 1994, 88, 4714.
89. N. V. Kukhtarev, V. B. Markov, M. Soskin and V. L. Vinetskii, Ferroelectrics, 1979, 22, 949.
90. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Proc. SPIE, 1995, 2527, 250.
91. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Appl. Phys. Lett., 1995, 67, 455.
92. H. Scher and E. W. Montroll, Phys. Rev. B, 1975, 12, 2455.
93. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Phys. Rev. B, 1995, 52, 14 324.
94. G. G. Malliaras, H. Angerman, V. V. Krasnikov, G. ten Brinke and G. Hadziioannou, J. Phys. D: Appl. Phys., 1996, 29, 2045.
95. A. R. Tahmasbi and J. Hirsch, Solid State Commun., 1980, 34, 75.
96. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Proc. SPIE, 1996, 2850, 24.
97. D. Morichere, G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, J. Chim. Phys., 1995, 92, 927.
98. G. G. Malliaras, V. V. Krasnikov, H. J. Bolink and G. Hadziioannou, Pure Appl. Opt., 1996, 5, 631.
99. A. M. Cox, R. D. Blackburn, D. P. West, T. A. King, F. A. Wade and D. A. Leigh, Appl. Phys. Lett., 1996, 68, 2801.
100. B. Kippelen, Sandalphon, N. Peyghambarian, S. R. Lyon, A. B. Padias and H. K. Hall Jr., Electron. Lett., 1993, 29, 1873.
101. Sandalphon, B. Kippelen, N. Peyghambarian, S. R. Lyon, A. B. Padias and H. K. Hall Jr., Opt. Lett., 1994, 19, 68.
102. M. A. Smith, N. R. King, G. R. Mitchell and S. V. O'Leary, Proc. SPIE, 1996, 2850, 14.
103. M. E. Orczyk, J. Zieba and P. N. Prasad, J. Phys. Chem., 1994, 98, 8699.
104. M. E. Orczyk, B. Swedek, J. Zieba and P. N. Prasad, J. Appl. Phys., 1994, 76, 4995.
105. Introduction to Nonlinear Optical Effects in Molecules and Polymers, ed. P. N. Prasad and D. J. Williams, Wiley-Interscience, New York, 1991.
106. A. Twarowski, J. Appl. Phys., 1989, 65, 2833.
107. L. Pautmeier, R. Richert and H. Bassler, Synth. Met., 1990, 37, 271.
108. B. Swedek, P. N. Prasad, Y. Cui, N. Cheng, J. Zieba, J. Winiarz and K. S. Kim, Proc. SPIE, 1996, 2850, 89.
109. S. F. Wang, Z. W. Huang, Z. J. Chen, Q. H. Gong, Z. J. Zhang and H. Y. Chen, Chin. Phys. Lett., 1997, 14, 474.
110. O. Zobel, M. Eckl, P. Strohriegl and D. Haarer, Adv. Mater., 1995, 7, 911.
111. S. X. Dou, J. S. Zhang, P. X. Ye, H. P. Hong and C. Ye, Acta Phys. Sinica, 1995, 4, 663.
112. B. Volodin, K. Meerholz, Sandalphon, B. Kippelen and N. Peyghambarian, Proc. SPIE, 1994, 2144, 72.
113. Z. J. Chen, L. F. Xu, Z. W. Huang, Q. H. Gong, Z. J. Zhang, Y. K. He and H. Y. Chen, Chin. Phys. Lett., in press.
114. Sandalphon, B. Kippelen, K. Meerholz and N. Peyghambarian, Appl. Opt., 1996, 35, 2346.
115. B. Kippelen, Sandalphon, K. Meerholz and N. Peyghambarian, Appl. Phys. Lett., 1996, 68, 1748.
116. B. Kippelen, F. Meyer, N. Peyghambarian and S. R. Marder, J. Am. Chem. Soc., 1997, 119, 4559.
117. K. Meerholz, R. Bittner, C. Brauchle, B. L. Volodin, Sandalphon, B. Kippelen and N. Peyghambarian, Proc. SPIE, 1996, 2850, 100.
118. B. Volodin, K. Meerholz, Sandalphon, B. Kippelen and N. Peyghambarian, Proc. SPIE, 1995, 2405, 143.
119. B. Kippelen, K. Meerholz, Sandalphon, B. Volodin and N. Peyghambarian, Nonlinear Opt., 1995, 11, 263.
120. B. L. Volodin, Sandalphon, K. Meerholz, B. Kippelen, N. V. Kukhtarev and N. Peyghambarian, Opt. Eng., 1995, 34, 2213.
121. K. Meerholz, Angew. Chem., Int. Ed. Engl., 1997, 36, 945.
122. C. Halvorson, B. Kraabel, A. J. Heeger, B. L. Volodin, K. Meerholz, Sandalphon and N. Peyghambarian, Opt. Lett., 1995, 20, 76.
123. B. L. Volodin, B. Kippelen, K. Meerholz, B. Javidi and N. Peyghambarian, Nature, 1996, 383, 58.
124. H. J. Bolink, V. V. Krasnikov, G. G. Malliaras and G. Hadziioannou, J. Phys. Chem., 1996, 100, 16 356.
125. P. Strohriegl, Makromol. Chem. Rapid Commun., 1986, 7, 771.
126. M. Lux, P. Strohriegl and H. Hocker, Makromol. Chem., 1987, 188, 811.
127. P. Strohriegl, Makromol. Chem., 1993, 194, 363.
128. C. Poga, P. M. Lundquist, V. Lee, R. M. Shelby, R. J. Twieg and D. M. Burland, Appl. Phys. Lett., 1996, 69, 1047.
129. Sol–Gel Technology for Thin Films, Fibers, Preforms, Electronics and Specialty Shapes, ed. L. C. Klein, Noyes, Park Ridge, 1988.
130. Sol–Gel Science: The Physics and Chemistry of Sol–Gel Processing, ed. C. J. Brinker and G. Scherer, Academic Press, Boston, 1990.
131. S. Kalluri, Y. Shi, W. Steier, Z. Yang, C. Xu, B. Wu and L. R. Dalton, Appl. Phys. Lett., 1994, 65, 2651.
132. J. Chen, S. Marturunkakul, L. Li, R. J. Jeng, J. Kumar and S. K. Tripathy, Macromolecules, 1993, 26, 7379.
133. R. Burzynski, M. K. Casstevens, Y. Zhang and S. Ghosal, Opt. Eng., 1996, 35, 443.
134. F. Chaput, D. Riehl, J. P. Boilot, K. Cargnelli, M. Canva, Y. Levy and A. Brun, Chem. Mater., 1990, 8, 312.
135. K. Tamura, A. B. Padias, H. K. Hall Jr. and N. Peyghambarian, Appl. Phys. Lett., 1992, 60, 1803.
136. B. Kippelen, K. Tamura, N. Peyghambarian, A. B. Padias and H. K. Hall Jr., Phys. Rev., 1993, 48, 10 710.
137. T. Kawakami and N. Sonoda, Appl. Phys. Lett., 1993, 62, 2167.
138. C. Zhao, C. Park, P. N. Prasad, Y. Zhang, S. Ghosal and R. Burzynski, Chem. Mater., 1995, 7, 1237.
139. Y. D. Zhang, T. Wada, L. Wang, T. Aoyama and H. Sasabe, Chem. Commun., 1996, 2325.
140. T. Aoyama, T. Wada, Y. D. Zhang, H. Sasabe and K. Sasaki, Proc. SPIE, 1997, 3147, 103.
141. Y. D. Zhang, H. Kimura-Suda, T. Wada, L. Wang, T. Aoyama and H. Sasabe, to be published.
142. H. Sasabe, Supramol. Sci., 1996, 3, 91.
143. T. Wada, Y. D. Zhang, M. Yamakado and H. Sasabe, Mol. Cryst. Liq. Cryst., 1993, 227, 85.
144. Y. D. Zhang, L. Wang, T. Wada and H. Sasabe, Macromolecules, 1996, 29, 1569.
145. Y. D. Zhang, T. Wada and H. Sasabe, J. Polym. Sci. Part A: Polym. Chem., 1996, 34, 2289.
146. T. Wada, Y. D. Zhang, L. Wang and H. Sasabe, Nonlinear, Opt., 1995, 9, 276.
147. T. Wada, Y. D. Zhang, Y. S. Choi and H. Sasabe, J. Phys. D: Appl. Phys., 1993, 26, B221.
148. Y. D. Zhang, T. Wada, L. Wang and H. Sasabe, Chem. Mater., 1997, 9, 2798.
149. C. Beginn, J. V. Grazulevicius and P. Strohriegl, Macromol. Chem. Phys., 1994, 195, 2353.
150. D. Williams, Angew. Chem., Int. Ed. Engl., 1984, 23, 690.
151. S. R. Marder, D. N. Beratan and L.-T. Cheng, Science, 1991, 252, 103.
152. Y. D. Zhang, L. Wang, T. Wada and H. Sasabe, Appl. Phys. Lett., 1997, 70, 2949.
153. T. Wada, L. Wang, Y. D. Zhang, M. Tian and H. Sasabe, Nonlinear Opt., 1996, 15, 103.
154. I. C. Khoo, H. Li and Y. Liang, Opt. Lett., 1994, 19, 1723.
155. G. P. Wiederrecht, B. A. Yoon and M. R. Wasielewski, Science, 1995, 270, 1794.
156. G. P. Wiederrecht, B. A. Yoon, W. A. Svec and M. R. Wasielewski, J. Am. Chem. Soc., 1997, 119, 3358.