Phosphorescent cyclometalated iridium (III) complexes that contain substituted 2-acetylbenzo[b]thiophen-3-olate ligand for red organic light-emitting devices

Chemistry - An Asian Journal

Volumn 9, Issue 12, 2014, Pages 3572-3585

  Yang, Chen ^a,b   Lai, Shiu Lun ^a   Chan, Sharon Lai Fung ^c   Low, Kam Hung ^a,d   Cheng, Gang ^a,b   Yeung, Kwan Ting ^a   Kwok, Chi Chung ^a   Che, Chi Ming ^a,b  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b UNIVERSITY OF HONG KONG   (China)

^c HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^d Guangdong Aglaia Optoelectronic Materials Co Ltd   (China)

Author keywords

Iridium; Ligand effects; Light emitting diodes; Luminescence; Metalation

Indexed keywords

CHELATION; FABRICATION; IRIDIUM; LIGANDS; LIGHT; LUMINESCENCE; ORGANIC LIGHT EMITTING DIODES (OLED); QUANTUM EFFICIENCY; SYNTHESIS (CHEMICAL); TELEVISION SYSTEMS;

CYCLOMETALATED IRIDIUM(III) COMPLEXES; DECOMPOSITION TEMPERATURE; EXTERNAL QUANTUM EFFICIENCY; LIGAND EFFECT; METALATIONS; NATIONAL TELEVISION SYSTEM COMMITTEES; ORGANIC LIGHT EMITTING DIODES(OLEDS); ORGANIC LIGHT-EMITTING DEVICES;

IRIDIUM COMPOUNDS;

EID: 84915820568     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201402782     Document Type: Article

References (74)

1. a) H. Yersin, W. J. Finkenzeller in Highly Efficient OLEDs with Phosphorescent Materials, Wiley-VCH, 2008, pp. 1-97
2. b) S. R. Forrest, Nature 2004, 428, 911-918
3. c) H. Xu, R. F. Chen, Q. Sun, W. Y. Lai, Q. Q. Su, W. Huang, X. G. Liu, Chem. Soc. Rev. 2014, 43, 3259-3302.
4. a) Y. Ma, H. Zhang, J. Shen, C. Che, Synth. Met. 1998, 94, 245-248
5. 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
6. c) M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett. 1999, 75, 4-6
7. d) M. A. Baldo, M. E. Thompson, S. R. Forrest, Nature 2000, 403, 750-753.
8. a) B. Carlson, G. D. Phelan, W. Kaminsky, L. Dalton, X. Jiang, S. Liu, A. K. Y. Jen, J. Am. Chem. Soc. 2002, 124, 14162-14172
9. b) S.-H. Chang, C.-F. Chang, J.-L. Liao, Y. Chi, D.-Y. Zhou, L.-S. Liao, T.-Y. Jiang, T.-P. Chou, E. Y. Li, G.-H. Lee, T.-Y. Kuo, P.-T. Chou, Inorg. Chem. 2013, 52, 5867-5875.
10. a) S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304-4312
11. b) Y. Tao, Q. Wang, C. Yang, C. Zhong, J. Qin, D. Ma, Adv. Funct. Mater. 2010, 20, 2923-2929
12. c) L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, J. Kido, Adv. Mater. 2011, 23, 926-952
13. d) G. Zhou, W.-Y. Wong, Z. Xie, L. Wang, Angew. Chem. Int. Ed. 2007, 46, 1149-1151
14. Angew. Chem. 2007, 119, 1167-1169
15. e) W.-Y. Wong, C.-L. Ho, Coord. Chem. Rev. 2009, 253, 1709-1758
16. f) C. Shi, H. Sun, X. Tang, W. Lv, H. Yan, Q. Zhao, J. Wang, W. Huang, Angew. Chem. Int. Ed. 2013, 52, 13434-13438
17. Angew. Chem. 2013, 125, 13676-13680
18. g) T. Kim, H. Kim, K. M. Lee, Y. S. Lee, M. H. Lee, Inorg. Chem. 2013, 52, 160-168
19. h) G. Zhou, C.-L. Ho, W.-Y. Wong, Q. Wang, D. Ma, L. Wang, Z. Lin, T. Marder, A. Beeby, Adv. Funct. Mater. 2008, 18, 499-511.
20. a) W. Lu, B.-X. Mi, M. C. W. Chan, Z. Hui, C.-M. Che, N. Y. Zhu, S.-T. Lee, J. Am. Chem. Soc. 2004, 126, 4958-4971
21. b) S. C. F. Kui, I. H. T. Sham, C. C. C. Cheung, C.-W. Ma, B. Yan, N. Zhu, C.-M. Che, W.-F. Fu, Chem. Eur. J. 2007, 13, 417-435
22. c) K. Li, X. Guan, C. -W. Ma, W. Lu, Y. Chen, C.-M. Che, Chem. Commun. 2011, 47, 9075-9077
23. d) S. C. F. Kui, F.-F. Hung, S.-L. Lai, M.-Y. Yuen, C.-C. Kwok, K.-H. Low, S. S.-Y. Chui, C.-M. Che, Chem. Eur. J. 2012, 18, 96-109
24. e) K. Li, G. Cheng, C. Ma, X. Guan, W.-M. Kwok, Y. Chen, W. Lu, C.-M. Che, Chem. Sci. 2013, 4, 2630-2644
25. f) E. S.-H. Lam, D. P.-K. Tsang, W. H. Lam, A. Y.-Y. Tam, M.-Y. Chan, W.-T. Wong, V. W.-W. Yam, Chem. Eur. J. 2013,19, 6385-6397
26. g) G. Zhou, W.-Y. Wong, X. Yang, Chem. Asian J. 2011, 6, 1706-1727
27. h) G. Zhou, Q. Wang, X. Wang, C.-L. Ho, W.-Y. Wong, D. Ma, L. Wang, Z. Lin, J. Mater. Chem. 2010, 20, 7472.
28. a) K. M.-C. Wong, X. Zhu, L.-L. Hung, N. Zhu, V. W.-W. Yam, H.-S. Kwok, Chem. Commun. 2005, 2906-2908
29. b) V. K.-M. Au, K. M.-C. Wong, D. P.-K. Tsang, M.-Y. Chan, N. Zhu, V. W.-W. Yam, J. Am. Chem. Soc. 2010, 132, 14273-14278
30. c) M.-C. Tang, D. P.-K. Tsang, M. M.-Y. Chan, K. M.-C. Wong, V. W.-W. Yam, Angew. Chem. Int. Ed. 2013, 52, 446-449
31. Angew. Chem. 2013, 125, 464-467
32. d) V. K.-M. An, D. P.-K. Tsang, K. M.-C. Wong, M.-Y. Chan, N. Zhu, V. W.-W. Yam, Inorg. Chem. 2013, 52, 12713-12725.
33. A. F. Rausch, M. E. Thompson, H. Yersin, J. Phys. Chem. A 2009, 113, 5927-5932.
34. a) C.-H. Fan, P. Sun, T.-H. Su, C.-H. Cheng, Adv. Mater. 2011, 23, 2981-2985
35. b) J. P. Duan, P. P. Sun, C. H. Cheng, Adv. Mater. 2003, 15, 224-228
36. c) C. L. Ho, W. Y. Wong, Z. Q. Gao, C. H. Chen, K. W. Cheah, B. Yao, Z. Y. Xie, Q. Wang, D. G. Ma, L. X. Wang, X. M. Yu, H. S. Kwok, Z. Y. Lin, Adv. Funct. Mater. 2008, 18, 319-331
37. d) K. Wang, S. Wang, J. Wei, S. Chen, D. Liu, Y. Liu, Y. Wang, J. Mater. Chem. C 2014, 2, 6817-6826
38. e) I. G. Hilla, A. Kahn, J. Appl. Phys. 1999, 86, 4515-4519
39. f) Z.-Y. Liu, S.-R. Tseng, Y.-C. Chao, C.- Y. Chen, H.-F. Meng, S.-F. Homg, Y.-H. Wu, S.-H. Chen, Synth. Met. 2011,161, 426-430.
40. J. V. Caspar, T. J. Meyer, J. Phys. Chem. 1983, 87, 952-957.
41. a) D. H. Kim, N. S. Cho, H.-Y. Oh, J. H. Yang, W. S. Jeon, J. S. Park, M. C. Suh, J. H. Kwon, Adv. Mater. 2011, 23, 2721-2726
42. b) W. S. Jeon, T. J. Park, S. Y. Kim, R. Pode, J. Jang, J. H. Kwon, Org. Electron. 2009,10, 240-246
43. c) M.-S. Lin, L.-C. Chi, H.-W. Chang, Y.-H. Huang, K.-C. Tien, C.-C. Chen, C.-H. Chang, C.-C. Wu, A. Chaskar, S.-H. Chou, H.-C. Ting, K.-T. Wong, Y.-H. Liu, Y. Chi, J. Mater. Chem. 2012, 22, 870-876
44. d) H.-F. Chen, L.-C. Chi, W.-Y. Hung, W.- J. Chen, T.-Y. Hwu, Y.-H. Chen, S.-H. Chou, E. Mondal, Y.-H. Liu, K.-T. Wong, Org. Electron. 2012, 13, 2671-2681
45. e) J.-H. Jou, S.-M. Shen, S.-H. Chen, M.-H. Wu, W.-B. Wang, H.-C. Wang, C.-R. Lin, Y.-C. Chou, P.-H. Wu, J.-J. Shyue, Appl. Phys. Lett. 2010, 96, 143306
46. f) R. Meerheim, S. Scholz, S. Olthof, G. Schwartz, S. Reineke, K. Walzer, K. Leo, J. Appl. Phys. 2008,104, 014510
47. g) H. Fukagawa, T. Shimizu, H. Hanashima, Y. Osada, M. Suzuki, H. Fujikake, Adv. Mater. 2012, 24, 5099-5103
48. h) S.-J. Su, C. Cai, J. Kido, Chem. Mater. 2011, 23, 274-284
49. i) Q. Mei, L. Wang, Y. Guo, J. Weng, F. Yan, B. Tian, B. Tong, J. Mater. Chem. 2012, 22, 6878-6884
50. j) H.-H. Chou, C.-H. Cheng, Adv. Mater. 2010, 22, 2468-2471.
51. a) D. Y. Kondakov, W. C. Lenhart, W. F. Nichols, J. Appl. Phys. 2007, 101, 024512
52. b) S. Schmidbauer, A. Hohenleutner, B. Konig, Adv. Mater. 2013, 25, 2114-2129.
53. S. L.-F. Chan, K.-H. Low, C. Yang, S. H.-F. Cheung, C.-M. Che, Chem. Eur. J. 2011, 17, 4709-4714.
54. S. Smiles, E. W. McClelland, J. Chem. Soc. Trans. 1921, 119, 1810-1816.
55. a) E. N. Shepelenko, L. S. Minkina, S. G. Kochin, A. V. Khokhlov, V. A. Bren, A. D. Garnovskii, Zh. Obshch. Khim. 1987, 57, 2342-2346
56. b) V. G. Zaletov, L. S. Minkina, S. G. Kochin, E. N. Shepelen-ko, V. A. Bren, A. D. Garnovskii, Zh. Neorg. Khim. 1989, 34, 664-668.
57. S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, R. Kwong, I. Tsyba, M. Bortz, B. Mui, R. Bau, M. E. Thompson, Inorg. Chem. 2001, 40, 1704-1711.
58. M. A. Esteruelas, F. J. Lahoz, E. Onate, L. A. Oro, L. Rodriguez, Organometallics 1996,15, 823-834.
59. a) F. Neve, A. Crispini, Eur. J. Inorg. Chem. 2000, 1039-1043
60. b) C.- H. Yang, J. Beltran, V. Lemaur, J. Cornil, D. Hartmann, W. Sarfert, R. Frohlich, C. Bizzarri, L. De Cola, Inorg. Chem. 2010, 49, 9891-9901.
61. S.-L. Lai, S.-L. Tao, M.-Y. Chan, M.-F. Lo, T.-W. Ng, S.-T. Lee, W.-M. Zhao, C.-S. Lee, J. Mater. Chem. 2011, 21, 4983-4988.
62. D. N. Kozhevnikov, V. N. Kozhevnikov, M. Z. Shafikov, A. M. Pro-khorov, D. W. Bruce, J. A. Gareth Williams, Inorg. Chem. 2011, 50, 3804-3815.
63. C. Shi, H. Sun, Q. Jiang, Q. Zhao, J. Wang, W. Huang, H. Yan, Chem. Commun. 2013, 49, 4746-4748.
64. B. W. D'Andrade, S. Datta, S. R. Forrest, P. Djurovich, E. Polikar-pov, M. E. Thompson, Org. Electron. 2005, 6, 11-20.
65. R. Wang, D. Liu, H. Ren, T. Zhang, H. Yin, G. Liu, J. Li, Adv. Mater. 2011, 23, 2823-2827.
66. G. A. Crosby, J. N. Demas, J. Phys. Chem. 1971, 75, 991-1024.
67. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
68. G. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
69. Gaussian 09, Revision C.01, M.J. Frisch, G. W. Trucks, H. B. Schle-gel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Son-nenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr. , J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, 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, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
70. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654.
71. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310.
72. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6170.
73. a) O. Tapia, J. Math. Chem. 1992,10, 139-181
74. b) J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094.