Synthesis and characterization of novel poly(arylenevinylene) derivative
Eun-Kyung Kim
Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea
Search for more papers by this authorCorresponding Author
Soon-Ki Kwon
School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea
Soon-Ki Kwon, School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea===
Yun-Hi Kim, Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea===
Search for more papers by this authorQinghua Zhao
School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea
Search for more papers by this authorWon-Ik Jung
Department of Materials Science and Engineering, Seoul National University, Korea
Search for more papers by this authorJang-Joo Kim
Department of Materials Science and Engineering, Seoul National University, Korea
Search for more papers by this authorCorresponding Author
Yun-Hi Kim
Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea
Soon-Ki Kwon, School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea===
Yun-Hi Kim, Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea===
Search for more papers by this authorEun-Kyung Kim
Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea
Search for more papers by this authorCorresponding Author
Soon-Ki Kwon
School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea
Soon-Ki Kwon, School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea===
Yun-Hi Kim, Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea===
Search for more papers by this authorQinghua Zhao
School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea
Search for more papers by this authorWon-Ik Jung
Department of Materials Science and Engineering, Seoul National University, Korea
Search for more papers by this authorJang-Joo Kim
Department of Materials Science and Engineering, Seoul National University, Korea
Search for more papers by this authorCorresponding Author
Yun-Hi Kim
Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea
Soon-Ki Kwon, School of Nano and Advaned Materials and Engineering Research Institute, Gyeongsang National University, Chinju 660-701, Korea===
Yun-Hi Kim, Department of Chemistry and RINS, Gyeongsang National University, Chinju 660-701, Korea===
Search for more papers by this authorAbstract
The new poly(arylenevinylene) derivative composed naphthalene phenylene vinylene backbone was developed. The theoretical calculation showed that the model compound of the obtained polymer was highly distorted between the stryl and naphthalene units as well as between the backbone and fluorene side units. The polymer was synthesized by the palladium catalyzed Suzuki coupling reaction with 2,6-(1′,2′-ethylborate)-1,5-dihexyloxynaphtalene and 1,2-bis(4′-bromophenyl)-1-(9″,9″-dihexyl-3-fluorenyl)ethene. The structure of the polymer was confirmed by 1H NMR, IR, and elemental analysis. The weight–average molecular weight of the polymer is 29,800 with the polydispersity index of 1.87. The new polymer showed good thermal stability with high Tg of 195°C. The bright blue fluorescence (λmax = 475 nm) was observed both in solution and film of new polymer with naphthalene phenylene vinylene backbone. Double layer LED devices with the configuration of ITO/PEDOT/polymer/LiF/Ca/Al showed a turn-on voltage at around 4.5 V, the maximum luminance of 150 cd/m2, and the maximum efficiency of 0.1 cd/A. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008
References
- 1 Bernius, M. T.;Inbasekaran, M.;O'Brien, J.;Wu, W. Adv Mater 2000, 12, 1737.
- 2 Kim, D. Y.;Cho, H. N.;Kim, C. Y. Progr Polym Sci 2000, 25, 1089.
- 3 Akcelrud, L. Progr Polym Sci 2003, 28, 875.
- 4 Inbasekaran, M.;Woo, E.;Wu, W.;Bernius, M.;Wujkowski, L. Synth Met 2000, 111, 397.
- 5
Kraft, A.;Grimsdale, A. C.;Holmes, A. B.
Angew Chem Int Ed
1998,
37,
402.
10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9 CAS PubMed Web of Science® Google Scholar
- 6 Scherf, U.;List, E. J. W. Adv Mater 2002, 14, 477.
- 7 Neher, D. Macromol Rapid Commun 2001, 22, 1365.
- 8 Kreyenschmidt, M.;Klaerner, G.;Fuhrer, T.;Ashenhurst, J.;Karg, S;Chen, W. D.;Lee, V. Y.;Scott, J. C.;Miller, R. D. Macromolecules 1998, 31, 1099.
- 9 Sohn, B. H.;Kim, K.;Choi, D. S.;Kim, Y. K.;Jeoung, S. C.;Jin, J. I. Macromolecules 2002, 35, 2876.
- 10 Zheng, M.;Ding, L.;Lin, Z.;Karasz, F. E. Macromolecules 2002, 35, 9939.
- 11 Lopez, L. C.;Strohriegl, P.;Stübinger, T. Macromol Chem Phys 2002, 203, 1926.
- 12 Hwang, D. H.;Lee, J. D.;Kang, J. M.;Lee, S.;Jin, S. H. J Mater Chem 2003, 13, 1540.
- 13 He, Y.;Gong, S.;Hattori, R.;Kanicki, J. Appl Phys Lett 1999, 74, 2265.
- 14
Poganstch, A.;Wenzl, F. P.;List, E. J. W.;Leising, G.;Grimsdale, A. C.;Müllen, K.
Adv Mater
2002,
14,
1061.
10.1002/1521-4095(20020805)14:15<1061::AID-ADMA1061>3.0.CO;2-6 Google Scholar
- 15 Ranger, M.;Leclerc, M. Can J Chem 1998, 76, 1571.
- 16 Wu, F. I.;Dodda, R.;Reddy, D. S.;Shu, C. F. J Mater Chem 2002, 12, 2893.
- 17 Kim, Y. H.;Kwon, S. K.;Yoo, D. S.;Rubner, M. F.;Wrighton, M. S. Chem Mater 1997, 9, 2699.
- 18 Lee, K. S.;Kim, Y. H.;Lee, Y.;Jin, J.;Kwon, S. K. J Polym Sci 2005, 43, 2316.
- 19 Kim, Y. H.;Kwon, S. K. J Appl Polym Sci 2006, 100, 2151.
- 20 Arias, A. C.;MacKenzie, J. D.;Stevenson, R.;Halls, J. J. M.;Inbasekaran, M.;Woo, E. P.;Richards, D.;Friend, R. H. Macromolecules 2001, 34, 6005.
- 21 Deng, X. Y.;Tong, S. W.;Hung, L. S.;Mo, Y. Q.;Cao, Y. Appl Phys Lett 2003, 82, 3104.
- 22 Müller, C. D.;Falcou, A.;Reckefuss, N.;Rojahn, M.;Wiederhirn, V.;Rudati, P.;Frohne, H.;Nuyken, O.;Becker, H.;Meerholz, K. Nature 2003, 421, 829.
- 23 Kim, Y. H.;Park, S. J.;Park, J. W.;Kim, J. H.;Kwon, S. K. Marcomol Res 2007, 15, 216.
- 24 Ego, C.;Grimsdale, A. C.;Uckert, F.;Yu, G.;Srdanov, G.;Müllen, K. Adv Mater 2002, 14, 809.
- 25 Friend, R. H.;Gymer, R. W.;Holmes, A. B.;Burroughes, J. H.;Marks, R. N.;Taliani, C.;Bradley, D. D. C.;Dos Santos, D. A.;Brédas, J. L.;Lögdlund, M.;Salaneck, W. R. Nature 1999, 397, 121.
- 26 Beaupre, S.;Leclerc, M. Adv Funct Mater 2002, 12, 192.
- 27 Beaupre, S.;Leclerc, M. Macromolecules 2003, 36, 8986.
- 28 An, B. K.;Kim, Y. H.;Shin, D. C.;Park, S. Y.;Yu, H. S.;Kwon, S. K. Macromolecules 2001, 34, 3993.
- 29 Kim, Y. H.;Shin, D. C.;Kwon, S. K.;Lee, J. H. J Mater Chem 2002, 12, 1280.
- 30 Kim, Y. H.;Ahn, J. H.;Shin, D. C.;Kim, H. S.;Kwon, S. K. Opt Mater 2002, 21, 175.
- 31 Kim, Y. H.;Park, J. C.;Kang, H. J.;Park, J. W.;Kim, H. S.;Kim, J. H.;Kwon, S. K. Marcomol Res 2005, 13, 403.
- 32 Kim, Y. H.;Ahn, J. H.;Shin, D. C.;Kwon, S. K. Polymer 2004, 45, 2525.
- 33 Kim, Y. H.;Jung, S. U.;Lee, G. H.;Kwon, S. K. Marcomol Res 2006, 14, 81.
- 34 Kim, Y. H.;Shin, D. C.;Kim, H. S.;Kwon, S. K. Polymer 2005, 46, 4647.
- 35 Kim, Y. H.;Jung, S. Y.;Kwon, S. K. Mol Cryst Liq Cryst 2006, 444, 257.
- 36 Kim, Y. H.;Jung, S. Y.;Jung, S. U.;Park, M. H.;Kwon, S. K. J Polym Sci 2006, 44, 4923.
- 37
Behnisch, B.;Ruiz, P. M.;Schweikart, K. H.;Hanack, M.
Eur J Org Chem
2000,
2000,
2541.
10.1002/1099-0690(200007)2000:14<2541::AID-EJOC2541>3.0.CO;2-J Google Scholar
- 38 Lee, N. H. S.;Chen, Z. K.;Huang, W.;Xu, Y. S.;Cao, Y. J Polym Sci 2004, 42, 1647.
- 39 Kim, Y. H.;Shin, D. C.;Kim, S. H.;Ko, H. S.;Yu, H. S.;Chae, Y. S.;Kwon, S. K. Adv Mater 2001, 13, 1690.