Versatile benzimidazole/triphenylamine hybrids: Efficient nondoped deep-blue electroluminescence and good host materials for phosphorescent emitters

Chemistry - An Asian Journal

Volumn 5, Issue 9, 2010, Pages 2093-2099

  Gong, Shaolong ^a   Zhao, Yongbiao ^b   Wang, Meng ^a   Yang, Chuluo ^a   Zhong, Cheng ^a   Qin, Jingui ^a   Ma, Dongge ^b  

^a WUHAN UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

Benzimidazole; Host guest systems; Materials science; Phosphorescence; Triphenylamine

Indexed keywords

BENZIMIDAZOLES; BLUE ELECTROLUMINESCENCE; BLUE EMITTER; CIE COORDINATES; CURRENT EFFICIENCY; DONOR AND ACCEPTOR; EXTERNAL EFFICIENCY; FLUORESCENCE QUANTUM YIELD; GLASS TRANSITION TEMPERATURE; GREEN AND RED PHOSPHORS; HIGH EFFICIENCY; HOST MATERIALS; HOST-GUEST SYSTEM; MAXIMUM POWER; NATIONAL TELEVISION SYSTEM COMMITTEES; NON-DOPED; OPTOELECTRONIC PROPERTIES; PHOSPHORESCENT DEVICES; PHOSPHORESCENT EMITTERS; PHOTOPHYSICAL; TERPHENYLS; THERMAL DECOMPOSITION TEMPERATURE; THERMAL STABILITY; TRIPHENYL AMINES;

ELECTROCHEMICAL PROPERTIES; FLUORESCENCE; GLASS TRANSITION; LIGHT EMITTING DIODES; LUMINESCENT DEVICES; MATERIALS SCIENCE; ORGANIC LIGHT EMITTING DIODES (OLED); PHOSPHORESCENCE; PYROLYSIS; QUANTUM YIELD; SOUND INSULATING MATERIALS; TELEVISION SYSTEMS;

LIGHT EMISSION;

EID: 77956470930     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000206     Document Type: Article

References (54)

1. a) C. J. Tonzola, A. P. Kulkarni, A. P. Gifford, W. Kaminsky, S. A. Je-nekhe, Adv. Fund. Mater. 2007, 17, 863-874
2. b) Y. Wei, C.-T. Chen, J. Am. Chem. Soc. 2007, 129, 7478-7479
3. c) S. Tao, Y. Zhou, C.-S. Lee, S.-T. Lee, D. Huang, X. Zhang, J. Phys. Chem. C 2008, 112, 14603-14606
4. d) Y. Jiang, L. Wang, Y. Zhou, Y.-X. Cui, J. Wang, Y. Cao, J. Pei, Chem. Asian J. 2009, 4, 548-553.
5. a) M.-T. Lee, C.-H. Liao, C.-H. Tsai, C. H. Chen, Adv. Mater. 2005, 17, 2493-2497
6. b) S.-L. Lin, L.-H. Chan, R.-H. Lee, M.-Y. Yen, W.-J. Kuo, C.-T. Chen, R.-J. Jeng, Adv. Mater. 2008, 20, 3947-3952
7. c) C.-H. Wu, C.-H. Chien, F.-M. Hsu, P.-I. Shih, C.-F. Shu, J. Mater. Chem. 2009,19, 1464-1470.
8. M.-T. Lee, H.-H. Chen, C.-H. Liao, C.-H. Tsai, C. H. Chen, Appl. Phys. Lett. 2004, 85, 3301-3303.
9. a) M.-Y. Lai, C.-H. Chen, W.-S. Huang, J. T. Lin, T.-H. Ke, L.-Y. Chen, M.-H. Tsai, C.-C. Wu, Angew. Chem. 2008, 120, 591-595
10. Angew. Chem. Int. Ed. 2008,47, 581-585
11. b) C.-H. Chen, W.-S. Huang, M.-Y. Lai, W.-C. Tsao, J. T. Lin, Y.-H. Wu, T.-H. Ke, L.-Y. Chen, C.-C. Wu, Adv. Funct. Mater. 2009,19, 2661-2670.
12. a) C. W. Tang, S. A. VanSlyke, C. H. Chen, J. Appl. Phys. 1989, 65, 3610-3616
13. b) C.-G. Zhen, Z.-K. Chen, Q.-D. Liu, Y.-F. Dai, R. Y. C. Shin, S.-Y. Chang, J. Kieffer, Adv. Mater. 2009,21, 2425-2429.
14. a) Y. Shirota, M. Kinoshita, T. Noda, K. Okumoto, T. Ohara, J. Am. Chem. Soc. 2000, 122, 11021-11022
15. b) C.-C. Chi, C.-L. Chiang, S.-W. Liu, H. Yueh, C.-T. Chen, C.-T. Chen, J. Mater. Chem. 2009,19, 5561-5571
16. c) C.-T. Chen, Y. Wei, J.-S. Lin, M. V. R. K. Moturu, W.-S. Chao, Y.-T. Tao, C.-H. Chien, J. Am. Chem. Soc. 2006, 128, 10992-10993.
17. a) C. W. Tang, S. A. VanSlye, Appl. Phys. Lett. 1987,51, 913-915
18. b) M. A. Baldo, D.F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151-154
19. c) Y. Sun, N. C. Giebink, H. Kanno, B. Ma, M. E. Thompson, S. R. Forrest, Nature 2006,440, 908-912.
20. a) Y.-J. Su, H.-L. Huang, C.-L. Li, C.-H. Chien, Y.-T. Tao, P.-T. Chou, S. Datta, R.-S. Liu, Adv. Mater. 2003, 15, 884-888
21. b) S.-J. Yeh, M.-F. Wu, C.-T. Chen, Y.-H. Song, Y. Chi, M.-H. Ho, S.-F. Hsu, C. H. Chen, Adv. Mater. 2005, 17, 285-289
22. c) N. Rehmann, C. Ul-bricht, A. Köhnen, P. Zacharias, M. C. Gather, D. Hertel, E. Holder, K. Meerholz, U. S. Schubert, Adv. Mater. 2008,20, 129-133
23. d) C.-L. Ho, Q. Wang, C.-S. Lam, W.-Y. Wong, D. Ma, L. Wang, Z.-Q. Gao, C.-H. Chen, K.-W. Cheah, Z. Lin, Chem. Asian J. 2009, 4, 89-103.
24. a) W.-Y. Wong, C.-L. Ho, Z.-Q. Gao, B.-X. Mi, C.-H. Chen, K.-W. Cheah, Z. Lin, Angew. Chem. 2006,118, 7964-7967
25. Angew. Chem. Int. Ed. 2006,45, 7800-7803
26. b) C.-L. Ho, W.-Y. Wong, Q. Wang, D. Ma, L. Wang, Z. Lin, Adv. Funct. Mater. 2008, 18, 928-937
27. c) G. Zhou, C.-L. Ho, W.-Y. Wong, Q. Wang, D. Ma, L. Wang, Z. Lin, T. B. Marder, A. Beeby, Adv. Funct. Mater. 2008,18, 499-511.
28. a) Y. Tao, Q. Wang, C. Yang, Q. Wang, Z. Zhang, T. Zou, J. Qin, D. Ma, Angew. Chem. 2008,120, 8224-8227
29. Angew. Chem. Int. Ed. 2008,47, 8104-8107
30. b) T.-C. Lee, C.-F. Chang, Y.-C. Chiu, Y. Chi, T.-Y. Chan, Y.-M. Cheng, C.-H. Lai, P.-T. Chou, G.-H. Lee, C.-H. Chien, C.-F. Shu, J. Leonhardt, Chem. Asian J. 2009,4, 742-753
31. c) J.-L. Chen, S.-Y. Chang, Y. Chi, K. Chen, Y.-M. Cheng, C.-W. Lin, G.-H. Lee, P.-T. Chou, C.-H. Wu, P.-I. Shih, C.-F. Shu, Chem. Asian J. 2008,3, 2112-2123
32. d) Y. Tao, L. Ao, Q. Wang, C. Zhong, C. Yang, J. Qin, D. Ma, Chem. Asian J. 2010,5, 278-284.
33. M. A. Baldo, C. Adachi, S. R. Forrest, Phys. Rev. B 2000, 62, 10967-10977.
34. Y. Tao, Q. Wang, Y. Shang, C. Yang, L. Ao, J. Qin, D. Ma, Z. Shuai, Chem. Commun. 2009, 77-79.
35. Y. Q. Li, M. K. Fung, Z. Xie, S.-T. Lee, L.-S. Hung, J. Shi, Adv. Mater. 2002,14, 1317-1321.
36. a) P.-I. Shih, C.-H. Chien, F.-I. Wu, C.-F. Shu, Adv. Funct. Mater. 2007, 17, 3514-3520
37. b) S.-y. Takizawa, V. A. Montes, P. Anzenbacher, Jr., Chem. Mater. 2009,21, 2452-2458.
38. N. Miyaura, A. Suzuki, Chem. Rev. 1995,95, 2457-2483.
39. Y. Shirota, J. Mater. Chem. 2000,10, 1-25.
40. a) Z. Ge, T. Hayakawa, S. Ando, M. Ueda, T. Akiike, H. Miyamoto, T. Kajita, M.-a. Kakimoto, Adv. Funct. Mater. 2008, 18, 584-590
41. b) Z. Ge, T. Hayakawa, S. Ando, M. Ueda, T. Akiike, H. Miyamoto, T. Kajita, M.-a. Kakimoto, Org. Lett. 2008, 10, 421-424.
42. W.-Y. Lai, R. Xia, Q.-Y. He, P. A. Levermore, W. Huang, D. D. C. Bradley, Adv. Mater. 2009,21, 355-360.
43. a) C.-C. Wu, Y.-T. Lin, K.-T. Wong, R.-T. Chen, Y.-Y. Chien, Adv. Mater. 2004,16, 61-65
44. b) J. N. Moorthy, P. Venkatakrishnan, D.-F. Huang, T. J. Chow, Chem. Commun. 2008, 2146-2148
45. c) Z. Jiang, Z. Liu, C. Yang, C. Zhong, J. Qin, G. Yu, Y. Liu, Adv. Funct. Mater. 2009,19, 3987-3995.
46. a) Z. Q. Gao, Z. H. Li, P. F. Xia, M. S. Wong, K. W. Cheah, C. H. Chen, Adv. Funct. Mater. 2007,17, 3194-3199
47. b) L. Wang, Y. Jiang, J. Luo, Y. Zhou, J. Zhou, J. Wang, J. Pei, Y. Cao, Adv. Mater. 2009,21, 4854-4858
48. c) C.-H. Chien, C.-K. Chen, F.-M. Hsu, C.-F. Shu, P.-T. Chou, C.-H. Lai, Adv. Funct. Mater. 2009,19, 560-566.
49. K.-T. Wong, Y.-M. Chen, Y.-T. Lin, H.-C. Su, C.-C. Wu, Org. Lett. 2005,7, 5361-5364.
50. C.-L. Li, Y.-J. Su, Y.-T. Tao, P.-T. Chou, C.-H. Chien, C.-C. Cheng, R.-S. Liu, Adv. Funct. Mater. 2005,15, 387-395.
51. Z. Ge, T. Hayakawa, S. Ando, M. Ueda, T. Akiike, H. Miyamoto, T. Kajita, M.-a. Kakimoto, Chem. Mater. 2008,20, 2532-2537.
52. Guassian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schle-gel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgom-ery, Jr., T. Vreven, K.N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cio-slowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaro-mi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc. , Wall-ingford CT, 2004.
53. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100
54. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988,37, 785-789.