Iridium(I) pyridyl azolate complexes with saturated red metal-to-ligand charge transfer phosphorescence; Fundamental and potential applications in organic light-emitting diodes

Chemistry - A European Journal

Volumn 13, Issue 9, 2007, Pages 2686-2694

  Fang, Chung Hong ^a   Chen, Yao Lun ^a   Yang, Cheng Han ^a   Chi, Yun ^a   Yeh, Yu Shan ^b   Li, Elisa Y ^b   Cheng, Yi Ming ^b   Hsu, Chia Jung ^b   Chou, Pi Tai ^b   Chen, Chin Ti ^c  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

Cyclooctene; Iridium; Phosphorescence; Photochemistry; Pyridyl azolate

Indexed keywords

COMPLEXATION; LIGHT EMITTING DIODES; PHOSPHORESCENCE; PHOTOCHEMICAL REACTIONS; X RAY DIFFRACTION ANALYSIS;

CYCLOOCTENE; PYRIDYL AZOLATE; SQUARE-PLANAR GEOMETRY;

IRIDIUM COMPOUNDS;

EID: 34250783313     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601019     Document Type: Article

References (75)

1. a) M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151;
2. b) E. Holder, B. M. W. Langeveld, U.S. Schubert, Adv. Mater. 2005, 17, 1109;
3. c) R. C. Evans, P. Douglas, C. J. Winscom, Coord. Chem. Rev. 2006, 250, 2093.
4. a) P.-T. Chou, Y. Chi, Eur. J. Inorg. Chem. 2006, 3319;
5. b) S. Tokito, T. Iijima, T. Tsuzuki, F. Sato, Appl. Phys. Lett. 2003, 83, 2459;
6. c) S.-C. Lo, E. B. Namdas, P. L. Burn, I. D. W. Samuel, Macromolecules 2003, 36, 9721;
7. d) R. C. Kwong, M. R. Nugent, L. Michalski, T. Ngo, K. Rajan, Y.-J. Tung, M. S. Weaver, T. X. Zhou, M. Hack, M. E. Thompson, S. R. Forrest, J. J. Brown, Appl. Phys. Lett. 2002, 81, 162;
8. e) O. He, S.-C. Chang, F.-C. Chen, Y. Li, Y. Yang, Appl. Phys. Lett. 2002, 81, 1509;
9. f) C.-L. Lee, K. B. Lee, J.-J. Kim, Appl. Phys. Lett. 2000, 77, 2280.
10. a) K. Koike, N. Okoshi, H. Hori, K. Takeuchi, O. Ishitani, H. Tsubaki, I. P. Clark, M. W. George, F. P. A. Johnson, J. J. Turner, J. Am. Chem. Soc. 2002, 124, 11448;
11. b) J.-K. Yu, Y.-H. Hu, Y.-M. Cheng, P.-T. Chou, S.-M. Peng, G.-H. Lee, A. J. Carty, Y.-L. Tung, S.-W. Lee, Y. Chi, C.-S. Liu, Chem. Eur. J. 2004, 10, 6255;
12. c) Y.-L. Tung, S.-W. Lee, Y. Chi, L.-S. Chen, C.-F. Shu, F.-I. Wu, A. J. Carty, P.-T. Chou, S.-M. Peng, G.-H. Lee, Adv. Mater. 2005, 17, 1059.
13. a) B.-H. Xia, H.-X. Zhang, C.-M. Che, K.-H. Leung, D. L. Phillips, N. Zhu, Z.-Y. Zhou, J. Am. Chem. Soc. 2003, 125, 10362;
14. b) W. Lu, M. C. W. Chan, N. Zhu, C.-M. Che, C. Li, Z. Hui, J. Am. Chem. Soc. 2004, 126, 7639;
15. c) B. Ma, J. Li, P. I. Djurovich, M. Yousufuddin, R. Bau, M. E. Thompson, J. Am. Chem. Soc. 2005, 127, 28.
16. a) T. J. Wadas, S. Chakraborty, R. J. Lachicotte, Q.-M. Wang, R. Eisenberg, Inorg. Chem. 2005, 44, 2628;
17. b) F. Guo, W. Sun, Y. Liu, K. Schanze, Inorg. Chem. 2005, 44, 4055;
18. c) A. Diez, J. Fornies, A. Garcia, E. Lalinde, M. T. Moreno, Inorg. Chem. 2005, 44, 2443;
19. d) C.-H. Tao, N. Zhu, V. W.-W. Yam, Chem. Eur. J. 2005, 11, 1647;
20. e) H. Jude, J. A. Krause Bauer, W. B. Connick, Inorg. Chem. 2005, 44, 1211;
21. f) S.J. Farley, D. L. Rochester, A. L. Thompson, J. A. K. Howard, J. A. G. Williams, Inorg. Chem. 2005, 44, 9690.
22. a) S.-W. Lai, C.-M. Che, Top. Curr. Chem. 2004, 241, 27;
23. b) A. S. Ionkin, W.J. Marshall, Y. Wang, Organometallics 2005, 24, 619;
24. c) P. T. Furuta, L. Deng, S. Garon, M. E. Thompson, J. M. J. Frechet, J. Am. Chem. Soc. 2004, 126, 15388;
25. d) W. Sotoyama, T. Satoh, N. Sawatari, H. Inoue, Appl. Phys. Lett. 2005, 86, 153505.
26. a) R. C. Kwong, S. Sibley, T. Dubovoy, M. Baldo, S. R. Forrest, M. E. Thompson, Chem. Mater. 1999, 11, 3709;
27. b) C.-M. Che, Y.-J. Hou, M. C. W. Chan, J. Guo, Y. Liu, Y. Wang, J. Mater. Chem. 2003, 13, 1362;
28. c) Q. Hou, Y. Zhang, F. Li, J. Peng, Y. Cao, Organometallics 2005, 24, 4509;
29. d) M. Ikai, F. Ishikawa, N. Aratani, A. Osuka, S. Kawabata, T. Kajioka, H. Takeuchi, H. Fujikawa, Y. Taga, Adv. Funct. Mater. 2006, 16, 515.
30. a) J. Brooks, Y. Babayan, S. Lamansky, P. I. Djurovich, I. Tsyba, R. Bau, M. E. Thompson, Inorg. Chem. 2002, 41, 3055;
31. b) Y.-Y. Lin, S.-C. Chan, M. C. W. Chan, Y.-J. Hou, N. Zhu, C.-M. Che, Y. Liu, Y. Wang, Chem. Eur. J. 2003, 9, 1263;
32. c) C.-M. Che, S.-C. Chan, H.-F. Xiang, M.C.W. Chan, Y. Liu, Y. Wang, Chem. Commun. 2004, 1484;
33. d) C.-C. Kwok, H. M. Y. Ngai, S.-C. Chan, I. H. T. Sham, C-M. Che, N. Zhu, Inorg. Chem. 2005, 44, 4442;
34. e) W.-Y. Wong, Z. He, S.-K. So, K.-L. Tong, Z. Lin, Organometallics 2005, 24, 4079;
35. f) F. Galbrecht, X. H. Yang, B. S. Nehls, D. Neher, T. Farrell, U. Scherf, Chem. Commun. 2005, 2378.
36. a) H.-F. Xiang, S.-C. Chan, K. K.-Y. Wu, C.-M. Che, P. T. Lai, Chem. Commun. 2005, 1408;
37. b) J. Kavitha, S.-Y. Chang, Y. Chi, J.-K. Yu, Y.-H. Hu, P.-T. Chou, S.-M. Peng, G.-H. Lee, Y.-T. Tao, C.-H. Chien, A. J. Carty, Adv. Funct. Mater. 2005, 15, 223;
38. c) S.-Y. Chang, J. Kavitha, S.-W. Li, C.-S. Hsu, Y. Chi, Y.-S. Yeh, P.-T. Chou, G.-H. Lee, A. J. Carty, Y.-T. Tao, C.-H. Chien, Inorg. Chem. 2006, 45, 137.
39. a) W. A. Fordyce, G. A. Crosby, Inorg. Chem. 1982, 21, 1455;
40. b) M. I. S. Kenney, J. W. Kenney III, G. A. Crosby, Organometallics 1986, 5, 230;
41. c) H. Kunkely, A. Vogler, Inorg. Chem. Commun. 2005, 5, 119.
42. C.-C. Cheng, W.-S. Yu, P.-T. Chou, S.-M. Peng, G.-H. Lee, P.-C. Wu, Y.-H. Song, Y. Chi, Chem. Commun. 2003, 2628.
43. a) Y.-L. Tung, P.-C. Wu, C.-S. Liu, Y. Chi, J.-K. Yu, Y.-H. Hu, P.-T. Chou, S.-M. Peng, G.-H. Lee, Y.-T. Tao, A. J. Carty, C.-F. Shu, F.-I. Wu, Organometallics 2004, 23, 3745;
44. b) Y.-H. Song, S.-J. Yeh, C.-T. Chen, Y. Chi, C.-S. Liu, J.-K. Yu, Y.-H. Hu, P.-T. Chou, S.-M. Peng, G.-H. Lee, Adv. Funct. Mater. 2004, 14, 1221.
45. a) C.-H. Yang, S.-W. Li, Y. Chi, Y.-M. Cheng, Y.-S. Yeh, P.-T. Chou, G.-H. Lee, C.-H. Wang, C.-F. Shu, Inorg. Chem. 2005, 44, 7770;
46. b) C. S. K. Mak, A. Hayer, S. I. Pascu, S. E. Watkins, A. B. Holmes, A. Koehler, R. H. Friend, Chem. Commun. 2005, 4708.
47. P.-C. Wu, J.-K. Yu, Y.-H. Song, Y. Chi, P.-T. Chou, S.-M. Peng, G.-H. Lee, Organometallics 2003, 22, 4938.
48. J. DePriest, G. Y. Zheng, N. Goswami, D. M. Eichhorn, C. Woods, D. P. Rillema, Inorg. Chem. 2000, 39, 1955.
49. A. Tsuboyama, H. Iwawaki, M. Furugori, T. Mukaide, J. Kamatani, S. Igawa, T. Moriyama, S. Miura, T. Takiguchi, S. Okada, M. Hoshino, K. Ueno, J. Am. Chem. Soc. 2003, 125, 12971.
50. C. Adachi, M. A. Baldo, S. R. Forrest, M. E. Thompson, Appl. Phys. Lett. 2000, 77, 904.
51. V. Adamovich, J. Brooks, A. Tamayo, A. M. Alexander, P. Djurovich, B. W. D'Andrade, C. Adachi, S. R. Forrest, M. E. Thompson, New J. Chem. 2002, 26, 1171.
52. a) F.-M. Hwang, H.-Y. Chen, P.-S. Chen, C.-S. Liu, Y. Chi, C.-F. Shu, F.-I. Wu, P.-T. Chou, S.-M. Peng, G.-H. Lee, Inorg. Chem. 2005, 44, 1344;
53. b) Y.-H. Niu, B. Chen, S. Liu, H. Yip, J. Bardecker, A. K.-Y. Jen, J. Kavitha, Y. Chi, C.-F. Shu, Y.-H. Tseng, C.-H. Chien, Appl. Phys. Lett. 2004, 85, 1619.
54. a) H. Yersin, J. Strasser, Coord. Chem. Rev. 2000, 208, 331;
55. b) H. Yersin, D. Donges, Top. Curr. Chem. 2001, 214, 81;
56. c) H. Yersin, Top. Curr. Chem. 2004, 241, 1.
57. J. L. Herde, J. C. Lambert, C. V. Senoff, Inorg. Synth. 1974, 15, 18.
58. a) W. R. Thiel, J. Eppinger, Chem. Eur. J. 1997, 3, 696;
59. b) S. P. Singh, D. Kumar, B. G. Jones, M. D. Threadgill, J. Fluorine Chem. 1999, 94, 199.
60. J. C. de Mello, H. F. Wittmann, R. H. Friend, Adv. Mater. 1997, 9, 230.
61. J. M. Darke, M. L. Lesiecki, D. M. Camaioni, Chem. Phys. Lett. 1985, 113, 530.
62. H.-Y. Chen, Y. Chi, C.-S. Liu, J.-K. Yu, Y.-M. Cheng, K.-S. Chen, P.-T. Chou, S.-M. Peng, G.-H. Lee, A. J. Carty, S.-J. Yeh, C.-T. Chen, Adv. Funct. Mater. 2005, 15, 567.
63. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
64. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
65. a) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270;
66. b) W. R. Wadt, P. J. Hay, J. Chem. Phys. 1985, 82, 284;
67. c) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299.
68. P. C. Hariharan, A. Pople, J. Mol. Phys. 1974, 27, 209.
69. a) C. Jamorski, M. E. Casida, D. R. Salahub, J. Chem. Phys. 1996, 104, 5134;
70. b) M. Petersilka, U. J. Grossmann, E. K. U Gross, Phys. Rev. Lett. 1996, 76, 1212;
71. c) R. Bauernschmitt, R. Ahlrichs, F. H. Hennrich, M. M. Kappes, J. Am. Chem. Soc. 1998, 120, 5052;
72. d) M. E. Casida, J. Chem. Phys. 1998, 108, 4439;
73. e) R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218.
74. Y.-L. Chen, S.-W. Li, Y. Chi, Y.-M. Cheng, S.-C. Pu, Y.-S. Yeh, P.-T. Chou, ChemPhysChem 2005, 6, 2012.
75. S. I. Gorelsky, SWizard program, http://www.sg-chem.net/.