Novel nonlinear optical polymers based on poly(1,4-phenylenevinylene)

Abstract

A novel poly(1,4-phenylenevinylene) (PPV) derivative containing a nonlinear optical (NLO) moiety was synthesizedvia the methoxy-precursor pathway to give a highly rigid structure which still maintained good processability. Poly[2-butoxy-5-(2-{ethyl-[4-(4-nitrophenyldiazenyl)phenyl]amino}ethoxy)-1,4-phenylenevinylene] (PBDR1PV), containing a Disperse Red 1 (DR1)-type chromophore, was characterized by conventional spectroscopic methods (UV–VIS, FT-IR, NMR) and by thermal analyses. The synthetic approach has been applied for the preparation of high optical quality films for nonlinear optical applications. PBDR1PV films showed a high resonant d₃₃ value of 50 pm V^–1 when measured using the second harmonic generation (SHG) method. The nonlinearity of PBDR1PV was very stable at 90 °C for a month without detectable loss. In addition to second-order NLO properties, the PBDR1PV film showed third-order NLO properties simultaneously and the measured chi;⁽³⁾ value was found to be 2.5×10^–12 esu.

References

1. P. N. Prasad and D. J. Williams, in Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991.
2. R. W. Boyd, in Nonlinear Optics, Academic Press, New York, 1992.
3. J. Zyss and I. Ledoux, Chem. Rev., 1994, 94, 77.
4. L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen and K. J. Shea, Chem. Mater., 1995, 7, 1060.
5. L. R. Dalton, A. W. Harper, B. Wu, R. Ghosn, J. Laquindanum, Z. Liang, A. Hubibel and C. Xu, Adv. Mater., 1995, 7(6), 519.
6. J. A. F. Boogers, P. Th. A. Klasse, J. J. de Wlieger and A. H. A. Tinnemans, Macromolecules, 1994, 27, 205.
7. R. Levenson, J. Liang and J. Zyss, Polym. Prepr., 1994, 35, 162.
8. B. K. Mandal, Y. M. Chen, J. Y. Lee, J. Kumar and S. Tripathy, Appl. Phys. Lett., 1991, 58, 2459.
9. T. A. Chen, A. K. -Y. Jen and Y. Cai, J. Am. Chem. Soc., 1994, 117, 7295.
10. T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller and W. Volksen, Science, 1995, 268, 1604.
11. K. J. Moon, H. K. Shim, K. S. Lee, J. Zieba and P. N. Prasad, Macromolecules, 1996, 29(3), 861.
12. D. M. Burland, R. D. Miller and C. A. Walsh, Chem. Rev., 1995, 94, 31.
13. I. N. Kang, D. H. Hwang, H. K. Shim, T. Zyung and J. J. Kim, Macromolecules, 1996, 29(1), 165.
14. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burn and A. B. Holmes, Nature, 1990, 347, 539.
15. R. Ma. Gregorius, P. M. Lahti and F. E. Karasz, Chem. Mater., 1991, 3, 941.
16. J. I. Jin and H. K. Shim, in Polymers for Second-order Nonlinear Optics(ACS Symp. Ser.), 1995, p. 223.
17. D. H. Hwang, J. I. Lee, H. K. Shim, W. Y. Hwang, J. J. Kim and J. I. Jin, Macromolecules, 1994, 27(21), 6000.
18. B. Tatian, Appl. Opt., 1984, 23, 4477.
19. C. B. Yoon, K. J. Moon and H. K. Shim, Macromolecules, 1996, 29(17), 5754.
20. 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.
21. H. K. Shim, C. B. Yoon, J. I. Lee and D. H. Hwang, Polym. Bull., 1995, 34, 161.
22. W. N. Herman and L. M. Hayden, J. Opt. Soc. Am. B., 1995, 12, 416.
23. J. Jerphagnon and S. K. Kurtz, J. Appl. Phys., 1970, 41, 1667.
24. M. Kauranen, T. Verbiest, C. Boutton, M. N. Teerenstra, K. Clays, A. J. Schouten, R. J. M. Nolte and A. Persoons, Science, 1995, 270, 966.
25. B. R. Hsieh, H. Antoniadis, D. C. Bland and W. A. Feld, Adv. Mater., 1995, 7(1), 36.
26. T. Kaino, K. Kubodera, S. Tomaru, T. Kurihara, S. Saito, T. Tsutsui and S. Tokito, Electron. Lett., 1987, 23, 1095.
27. T. Kaino, H. Kobayash, K. I. Kubodera, T. Kurihara, S. Saito, T. Tsutsui and S. Tokito, Appl. Phys. Lett., 1989, 54, 1619.
28. D. H. Hwang, J. I. Lee, M. Lee and H. K. Shim, Bull. Korean Chem. Soc., 1994, 15, 25.