Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Characterization of Novel Red-Light-Emitting Materials with Push-Pull Structure Based on Benzo[1,2,5]thiadiazole Containing Arylamine as an Electron Donor and Cyanide as an Electron Acceptor

  • Ju, Jin-Uk (School of Nano & Advanced Materials Science and Engineering and ERI, Gyeongsang National University) ;
  • Jung, Sung-Ouk (School of Nano & Advanced Materials Science and Engineering and ERI, Gyeongsang National University) ;
  • Zhao, Qinghua (School of Nano & Advanced Materials Science and Engineering and ERI, Gyeongsang National University) ;
  • Kim, Yun-Hi (Department of Chemistry and RINS, Gyeongsang National University) ;
  • Je, Jong-Tae (SFC CO., LTD.) ;
  • Kwon, Soon-Ki (School of Nano & Advanced Materials Science and Engineering and ERI, Gyeongsang National University)
  • Published : 2008.02.20
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Abstract

New efficient red emitter having short p?-conjugation length and asymmetric bulky structure, 2-(7-diphenylamino-benzo[1,2,5]thiadiazole-4-ylmethylene)-malononitrile, was synthesized and characterized. Using this material as a dopant, we fabricated electroluminescence device with a structure of ITO/DNTPD/NPD/BTZA (5 wt% in Alq3)/Alq3/LiF/Al. The device exhibited a high brightness of 761 cd/m2 at a driving voltage of 4.8 V, and current efficiency is 0.75 cd/A. The Commission International de IEclairage (CIE) coordinates of the EL device were found to be (0.62, 0.37) at 10 mA/cm2.

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References

  1. Masayoshi, N.; Shibasaki, Y.; Mitsuru, U.; Tugita, K.; Ichikawa, M.; Taniguchi, Y. Macromolecules 2004, 37, 1204 https://doi.org/10.1021/ma0355709
  2. Kim, Y. H.; Jeong, H. C.; Kim, S. H.; Yang, K. Y.; Kwan, S. K. Adv. Funct. Mater. 2005, 15, 1799 https://doi.org/10.1002/adfm.200500051
  3. Ikai, M.; Ishikawa, F.; Osuka, N. A. A.; Kawabata, S.; Kajioka, T.; Takeuchi, H.; Fujikawa, H.; Taga, Y. Adv. Funct. Mater. 2006, 16, 515 https://doi.org/10.1002/adfm.200500492
  4. Kim, Y. H.; Lee, S. J.; Jung, S. Y.; Byeon, K. N.; Kim, J. S.; Shin, S. C.; Kwon, S. K. Bull. Korean Chem. Soc. 2007, 28(3), 443 https://doi.org/10.5012/bkcs.2007.28.3.443
  5. Kwon, S. K.; Kim, Y. H.; Shin, S. C. Bull. Korean Chem. Soc. 2002, 23(1), 17 https://doi.org/10.5012/bkcs.2002.23.1.017
  6. Yao, Y. S.; Xiao, J.; Wang, X. S.; Deng, Z. B.; Zhang, B. W. Adv. Funct. Mater. 2006, 16, 709 https://doi.org/10.1002/adfm.200500558
  7. Kim, Y. H.; Kwon, S. K. J. Appl. Polym. Sci. 2006, 100, 2151 https://doi.org/10.1002/app.23602
  8. Kim, Y. H.; Ahn, J. H.; Shin, D. C.; Kim, J. H.; Park, Y. W.; Choi, D. S.; Kim, Y. K.; Kwon, S. K. Bull. Korean Chem. Soc. 2001, 22(11), 1181
  9. Qiu, Y.; Wei, P.; Zhang, D.; Qiao, J.; Duan, L.; Li, Y.; Gao, Y.; Wang, L. Adv. Mater. 2006, 18, 1607 https://doi.org/10.1002/adma.200600290
  10. Kim, Y. H.; Jung, S. Y.; Jung, S. O.; Park, M. H.; Kwon, S. K. J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 4923 https://doi.org/10.1002/pola.21579
  11. Lim, S. T.; Chun, M. H.; Lee, K. W.; Shin, D. M. Optical Materials 2002, 21, 217
  12. Choi, K. S.; Lee, C. H.; Lee, K. H.; Park, S. J.; Son, S. U.; Chung, Y. K.; Hong, J. I. Bull. Korean Chem. Soc. 2006, 27(10), 1549 https://doi.org/10.5012/bkcs.2006.27.10.1549
  13. Fang, Q.; Jiang, B. X. B.; Chen, H. F.; Cao, A. Chem. Commun. 2005, 1468
  14. Hsieh, B. R. Macromol. Symp. 1997, 49, 125
  15. Zhao, Q. H.; Kim, Y. H.; Dang, T. T. M.; Shin, D. C.; You, H.; Kwon, S. K. J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 341 https://doi.org/10.1002/pola.21740
  16. Picciolo, L. C.; Murata, H.; Kafafi, Z. H. Appl. Phys. Lett. 2001, 78, 2378 https://doi.org/10.1063/1.1362259
  17. O'Brien, D. F.; Baldo, M. A.; Thompson, M. E.; Forrest, S. R. J. Appl. Phys. Lett. 1999, 74, 442 https://doi.org/10.1063/1.123055
  18. Suzuki, H.; Hoshino, S. J. Appl. Phys. 1996, 79, 8816. (b) Kido, J.; Hongawa, K.; Okuyama, K.; Nagai, K. J. Appl. Phys. Lett. 1994, 64, 815 https://doi.org/10.1063/1.111023
  19. Choi, K. S.; Lee, C. H.; Lee, K. H.; Park, S. J.; Son, S. U.; Chung, Y. K.; Hong, J. I. Bull. Korean Chem. Soc. 2006, 27(10), 1549 https://doi.org/10.5012/bkcs.2006.27.10.1549
  20. Wang, P. W.; Xie, Z.; Tong, S.; Wong, O.; Lee, C.-S.; Wong, N.; Hung, L.; Lee, S. Chem. Mater. 2003, 15, 1913 https://doi.org/10.1021/cm0209214
  21. Kim, Y. H.; Shin, D. C.; Kim, S. H.; Ko, C. H.; Yu, H. S.; Chae, Y. S.; Kwon, S. K. Adv. Mater. 2001, 13(22), 1690 https://doi.org/10.1002/1521-4095(200111)13:22<1690::AID-ADMA1690>3.0.CO;2-K
  22. Jung, S, O.; Kang, Y. J.; Kim, H. S.; Kim, Y. H.; Lee, C. L.; Kim, J. J.; Lee, S. K.; Kwon, S. K. Eur. J. Inorg. Chem. 2004, 3415

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