Hydroxynaphthyridine-derived group III metal chelates: Wide band gap and dee blue analogues of green Alq (tris(8-hydroxyquinolate)aluminum) and their versatile applications for organic light-emitting diodes

Journal of the American Chemical Society

Volumn 131, Issue 2, 2009, Pages 763-777

  Liao, Szu Hung ^a,b   Shiu, Jin Ruei ^a,c   Liu, Shun Wei ^a,d   Yeh, Shi Jay ^a   Chen, Yu Hung ^d   Chen, Chin Ti ^a,e   Chow, Tahsin J ^a   Wu, Chih I ^d  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^c NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^d NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^e NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIPOLAR; BENZIMIDAZOLE; CHELATING LIGANDS; DEEP BLUE; DEPOSITION PROCESS; ELECTROLUMINANCE; ELECTRON TRANSPORTING MATERIALS; EXCIPLEX; EXTERNAL QUANTUM EFFICIENCY; GROUP III; HIGH EFFICIENCY; HIGH ELECTRON MOBILITY; HOLE-TRANSPORTING LAYERS; HOMO ENERGY LEVELS; HOST MATERIALS; LUMO ENERGY LEVELS; METAL CHELATE; NAPHTHYRIDINE; PERYLENE; RUBRENE; SOLID-STATE LIGHTING APPLICATION; SUBLIMATION PROCESS; SYNTHETIC METHODS; THERMAL STABILITY; WIDE BAND GAP;

ALUMINA; ALUMINUM; BERYLLIUM; CURRENT DENSITY; ELECTRIC FIELDS; ELECTRON MOBILITY; ENERGY GAP; FLUORESCENCE; HELMET MOUNTED DISPLAYS; LIGANDS; LIGHT; LIGHT EMISSION; LIGHT EMITTING DIODES; LUMINESCENT DEVICES; MATERIALS; METAL REFINING; METALS; ORGANIC LIGHT EMITTING DIODES (OLED); SOUND INSULATING MATERIALS; SULFUR COMPOUNDS; SUPERCOMPUTERS; VACUUM DEPOSITION;

CHELATION;

ALUMINUM DERIVATIVE; METAL CHELATE; NAPHTHYRIDINE DERIVATIVE;

ARTICLE; ELECTRIC FIELD; ELECTRON; ELECTRON TRANSPORT; FLUORESCENCE; LIGHT EMITTING DIODE; THERMOSTABILITY;

EID: 67749096005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807284e     Document Type: Article

References (99)

1. Tang, C. W.; Van Slyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
2. (a) Chen, C. H.; Shi, J. Coord. Chem. Rev. 1998, 171, 161.
3. (a) Tang, C. W.; Van Slyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610,
4. (b) Bulovic, V.; Baldo, M. A.; Forrest, S. R. In Organic Electronic Materials: Conjugated Polymers and Low Molecular Weight Organic Solids; Farchioni, R., Grosso, G., Eds.; Springer-Verlag: New York, 2001; p 391,
5. (c) Higginson, K. A.; Thomsen, D. L., III; Yang, B.; Papadimitrakopoulos, F. In Organic Light-Emitting Devices: A Survey; Shinar.J., Ed.; Springer-Verlag: New York, 2004; p 71,
6. (d) Chen, C-T. Chem. Mater. 2004, 16, 4389.
7. Brinkmann, M.; Gadret, G.; Muccini, M.; Taliani, C; Masciocchi, N.; Sironi, A. J. Am. Chem. Soc. 2000, 122, 5147.
8. (a) Van Slyke. S. A.; Brynn, P. S.; Levecchio, F. V. U.S. Patent No. 5150006, 1992,
9. (b) Burrow, P. E.; Shen, Z.; Bulvoic, V.; McCarty, D. M.; Forrest. S. R.; Cronin. J. A.; Thompson, M. E. J. Appl. Phys. 1996, 79, 7991
10. (c) Sugimoto, M.; Anzai, M.; Sakanoue. K.; Sakaki, S. Appl. Phys. Lett. 2001, 79, 2348.
11. (a) Hamada, Y.; Sano, T.; Fujita, M.; Fuji, T.; Nishio, Y.; Shibata, K. Jpn. Appl. Phys. 1993, 32, L514,
12. (b) IIopkins, T. A.; Meerholz, K.; Shaheen, S.; Anderson, M. L.; Schmidt, A.; Kippelen, B.; Padias, A. B.; Hall, H. K., Jr.; Peyghambarian, Armstrong, N. R. Chem. Mater. 1996, 8, 344.
13. (c) Kido, Jr.; Iizumi, Y. Chem. Lett. 1997, 963.
14. (d) Kido. J.; Iizumi, Y. Appl. Phys. Lett. 1998, 73, 2721.
15. (e) Mattoussi, H.; Murata, H.; Merritt, C. D.; Iizumi, Y.; Kido, J. J. Appl. Phys. 1999, 86, 2642.
16. (f) Sapochak, L. S.; Padmaperuma, A.; Washton, N.; Endrino. F.; Schmett. G. T.; Marshall, J.; Forgarty, D.; Burrows, P. E.; Forrest, S. R. J. Am. Chem. Soc. 2001, 123, 6300.
17. (g) Yu, J.; Chen, Z.; Sakuratani, Y.; Suzuki, H.; Tokita, M.; Miyata, S. Jpn. Appl. Phys 1999, 38, 6762.
18. (h) Pohl. R.; Anzenbacher, P.; Jr. Qrg. Lett. 2003; 5; 2769.
19. (i) Pohl, R.; Montes. V. A.; Shinar. J.; Anzenbacher, P., Jr. J. Org. Chem. 2004, 69, 1723.
20. (j) Montes, V. A.; Li, G.; Pohl, R.; Shinar, J.; Anzenbacher, P. Jr. Adv. Mater. 2004, 16, 2001.
21. (k) Cheng, J.-A.; Chen, C H. J. Mater Chem. 2005, 15, 1179.
22. (1) Montes, V. A.; Pohl, R.; Shinar, J.; Anzenbacher, P., Jr. Chem.-Eur. J. 2006, 12, 4523,
23. (m) Pérez-Bolivar, C; Montes, V. A.; Anzenbacher, P., Jr. Inorg. Chem. 2006, 45, 9610.
24. Paudler, W. W.; Kress, T. J. Adv. Heterocycl. Chem. 1970, 11, 123.
25. Eck. T. D.; Wehry. E. L., Jr.; Hercules. D. M. J. Inorg. Nucl. Chem. 1966, 28, 2439.
26. (a) Cassis, R.; Tapia. R.; Valderrama, J. A. Synth. Commun. 1985, 15, 125.
27. (b) Chen, B.; Hung, X.; Wang, J. Synthesis 1987, 482.
28. (c) Singh, B.; Laskowski, S. C; Lesher, G. Y. Synlett 1990, 549.
29. (d) Marcos, A.; Pedregel, C.; Avendaöo, C. Tetrahedron 1994, 50, 12941.
30. (e) Bontemps, N.; Delfourne. E.; Batide, J.; Francisco, C; Bracher, F. Tenahedron 1997, 53, 1743.
31. (f) Kitahara, Y.; Nakahara, S.; Yonezawa, T.; Nagatsu, M.; Shibano, Y.; Kubo, A. Tetrahedron 1997, 53, 17029.
32. (g) Jeon, M.-K.; Kim, K. Tdrahedron Lett. 2000, 41, 1943.
33. (h) Salon. J.; Milata, V.; Pronavova. N.; Lesko, J. Monatch Chem. 2000, 131, 293.
34. 2 was 0.977.
35. Sapnochak, L. S.; Ranasinghe, A.; Kohlmann, H.; Ferris, K. F.; BUITOWS, P. E. Chem. Mater. 2004, 16, 401.
36. Mason, S. F. J. Chem. Soc. 1957, 5010.
37. Burrow, P. E.; Sapochak, L. S.; McCarty, D. M.; Forrest, S. R.; Thompson, M. E. Appl. Phys. Lett. 1994, 64, 2718.
38. Adachi, C; Oyamada, T. Data Book on HOMO Levels of Organic Thin Films in Organic Semiconductor Devices; CMC Publishing: Tokyo, 2005.
39. Tse, S. C; Kwok, K. C; So, S. K. Appl. Phys. Lett. 2006, 89, 262102.
40. (a) Lee. J.-H.; Wu, C-L; Liu. S.-W.; Huang. C-A.; Chang, Y. Appl. Phys. Lett. 2005, 86, 103506.
41. (b) Lee, J.-H.; Ho, Y.-H.; Lin, T.-C; Wu. C-F. J. Electrochem. Soc. 2007. 154, J226.
42. Higginson, K. A.; Zhang, X.-M.; Papadimitrakopoulos, F. Chem. Mater. 1998, 10, 1017.
43. (a) Sano, K.; Kawata, Y.; Urano, T. L; Mon, Y. J. Mater.Chem. 1992, 2, 767.
44. (b) Braun. M.; Gmeiner. J.; Tzolov. M.; Colle. M.; Mever. F. D.; Milius. W.; Hillebrecht, H.; Wendland, O.; von Schütz, J.U.; Bratting, W. J. Chem. Phys. 2001, 114, 9625.
45. (c) Cölle, M.; Gmeiner, J.; Milius, W.; Hillebrecht, Br̈ utting, W. Adv. Funct. Mater 2003, 13, 108.
46. (d) Muccini, M.; Loi, M. A.; Kenevey, K.; Zamboni, R.; Masciocchi, N.; Sironi, A. Adv. Mater. 2004, 16, 861.
47. (e) Levichkova, M. M.; Assa, J. J.; Frob, H.; Leo, K. Appl. Phys. Lett. 2006, 88, 201912.
48. (a) Itano, K.; Ogawa, H.; Shirota, Y. Appl. Phvs. Lett. 1998, 72, 636.
49. (b) Chan, L.-H.: Lee, R.-H.; Hsieh, C.-R; Yeh, H.-C; Chen, C.-T. J. Am. Chem. Soc. 2002, 124, 6469.
50. (c) Guan, M.; Bian, Z. Q.; Zhou, Y. F.; Li, F. Y.; Li, Z. J.; Huang, C. H. Chem. Commun. 2003, 2708.
51. (d) Matsumoto, N.; Nishivama. M.; Adachi, C. J.Phys Chem. C 2008, 112, 7735.
52. Wu, M.-F.; Yeh, S.-.J.; Chen, C-T.; Murayama, H.; Tsuboi. T; Li, W.-S.; Chao. I; Liu. S.-W.; Wang. J.-K. J.-K. Funct Mater 2007, 17, 1887.
53. Hill, I. G.; Rajagopai, A.; Kahn, A. J. Appl. Phys. 1998, 84, 3236.
54. Chen, Chin Hsin, Department of Photonics and Display Institute, National Chiao Tung University, private communication.
55. Berlman. I. B. Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed.; Academic Press: New York, 1971; pp 264 and 399.
56. Adachi, C.; Tsutsui, T.; Sato, S. Appl. Phys. Lett. 1990, 56, 799.
57. (a) Kojima, H.; Ozawa, A.; Takahshi, T.; Nagaoka, M.; Homma, T.; Nagatomo. T.; Omoto. O. .J. Electrochem. Soc. 1997, 144, 3628.
58. (b) Mi. B. X.; Gao, Z. Q.; Lee, C. S.; Lee, C. T; Kwong, H. L.; Wong, N. B. App. Phys. Lett. 1999, 7.5, 4055.
59. (c) Lu, P.; Hong, H.; Cai. G.; Djurovich, P.; Weber. W. P.; Thompson, M. E. J. Am. Chem. Soc. 2000, 122, 7480.
60. (d) Jiang, X.-Y.; Zhang. Z.-L.; Zheng, Z.-Y.; Wu, Y.-Z.; Xu, S.-H. Thin Solid Films 2001, 401, 251.
61. (e) Wu, C-C; Lin, Y.-T.; Chiang, H.-H.; Cho, T.-Y.; Chen, C-W.; Wong. K.-T.; Liao. Y.-L.; Lee, G.-H.; Peng, S.-M. Appl. Phys. Lett. 2002, 81, 577.
62. (f) Ni. S. Y.; Wang, X. R.; Wu, Y. Z.; Chen. H. Y.; Zhu, W. Q.; Jiang, X. Y.; Zhang, Z. L.; Sun. R. G. Appl. Phys. Lett. 2004, 85, 878.
63. (g) Jarikov, V. V. J. Appl. Phys. 2006, 100, 014901.
64. (h) Tse. S.-C; Tsung, K.-K.; So, S.-K. Appl. Phys. Lett. 2007, 90, 213502.
65. (i) Lee. R.-H.; IIung, Y.-W.; Wang. Y.-Y.; Chang. II.-Y. Thin Solid Films 2008, 516, 5062.
66. (a) Xie. Z. Y.; Huang, J. S.; Li. C. N.; Liu, S. Y.; Wang, Y.; Li, Y. Q.; Shen, J. C. Appl. Phys. Lett. 1999, 74, 641.
67. (b) Steuber, F.; Staudigel, J.; Strössel. M.; Simmerer, J.; Winnacker, A.; Spreitzer, H.; Weissörtel, F.; Salbeck. J. Adv. Mater. 2000, 12, 130.
68. (c) Xie. Z. Y.; Feng, J.; Huang, J. S.; Liu, S. Y.; Wang, Y.; Shen, J. C. Synth. Met. 2000, 108, 81,
69. (d) Zhang, Z.; Jiang, X.; Xu, S. Thin Solid Films 2000, 363, 61.
70. (e) Liu. S.; Hunag. J.; Xie, Z.; Wang. Y.; Chen. B. Thin Solid Films 2000, 363, 294.
71. (f) Chuen, C. H.; Tao, Y. T. Appl. Phvs. Lett. 2002, 81, 4499.
72. (g) Li, G.; Shinar, J. Appl. Phys. Lett. 2003, 83, 5359.
73. (h) Cheng, G.; Zhao. Y.; Zhang, Y.; Liu, S.; He, F.; Zhang, H.; Ma. Y. Appl. Phys. Lett. 2004, 84, 4457.
74. (i) Liu, T.-H.; Wu, Y.-S.: Lee, M,T.; Chen, H.-H.; Liao, C-H.; Chen, C. H. Appl. Phys. Lett. 2004, SJ, 4304.
75. (j) Cheng, G.; Xie, Z.; Zhao, Y.; Zhang, Y.; Xia, H.; Ma, Y.; Liu. S. Thin Solid Films 2005, 484, 54.
76. (k) Xie, W.; Meng, M.; Li. C.; Zhao, Y.; Liu, S. Opt. Quant. Electron. 2005, 37, 943.
77. (1) Li. M.; Li, W.; Niu, J.; Chu. B.; Li, B.; Sun, X.; Zhang. Z.; Hu, Z. Solid-State Electron. 2005, 49, 1956.
78. (m) Tao. S.; Peng. Z.; Zhang. X.; Wu. S.J.Lumin. 2006, 121, 568.
79. (n) Zhang, G. H.; Hua, Y. L.; Petty, M. C; Wu, K. W.; Zhu. F. J.; Niu, X.; Hui, J. L.; Liu, S.; Wu, X. M.; Yin, S. G.; Deng, J. C. Displays 2006, 27, 187.
80. (o) Choukri, H.; Fischer, A.; Forget, S.; Chénais, S.; Castex. M.-C; Adés, D.; Slove. A.; Geffrov, B. Appl. Phvs. Lett. 2006, 89, 183513.
81. (p) Hsiao. C-H.; Lin, C.-F.; Lee, J.-H. J. Appl. Phys. 2007, 102, 094508.
82. (q) Huang, H.-H.; Chu, S.-Y.; Kao. P.-C: Chen, Y.-C. Thin Solid Films 2008, 516, 5669.
83. (r) Tang. S.; Liu, M.; Lu, P.; Cheng, G.; Zeng. M.; Xie, Z.; Xu, H.; Wang, H.; Yang, B.; Ma, Y.; Yan, D. Org. Electron. 2008, 9, 241.
84. (s) Duan, Y.; Mazzeo, M.; Maiorano, V.; Mariano, F.; Oin, D.; Cingolani, R.; Gigli, G. Appl. Phys. Lett. 2008, 92, 113304.
85. (a) Huang, J.; Li, G.; Wu, E.; Xu, Q.; Yang. Y. Adv. Mater. 2006, 18, 114.
86. (b) Huang, J.; Hou, W.-J.; Li, J.-H.; Li, G.; Yang, Y.Appl. Phys. Lett. 2006, 89, 133509.
87. (c) Tsai, Y.-C; Jou, J.-H. Appl. Phys. Lett. 2006, 89, 243521.
88. (a) D'Andrade, B. W.; Forrest, S. R. Adv. Mater. 2004, 16, 1585.
89. (b) Misra. A.; Kumar, P.; Kamalasanan, Chandra, S. Semicoma. Sci. Technol. 2006, 21, R35.
90. (c) Yeh, S.-J.; Chen. H.-Y.; Wu. M.-R; Chan, L.-H.: Chiang, C-L.: Yeh, H.-C: Chen, Lee, J.-H. Org. Electron. 2006, 7, 137.
91. See: Chiang, C.-L.; Tseng, S.-M.; Chen, C.-T.; Hsu, C.-.; Shu, C-F. Adv. Funct. Mater 2008, 18, 248, and references therein.
92. (a) de Mello, J. C; Wittmann. H. F.; Friend, R. H. Adp. Mater. 1997, 9, 230.
93. (b) Chiang, C-L.; Wu, M.-R; Dai, D.-C., Wen, Y.-S.; Wang, J.-K.; Chen. C-T. Adv: Fund. Mater 2005, 15, 231.
94. Wu, C-I.; Lee, G.-R.; Lin. C-T.; Chen, Y.-H.; Hong, Y.-H.; Liu. W.G.; Wu, C-C; Wong, K.-T.; Chao, T.-C. Appl. Phvs. Lett. 2005, 87, 242107.
95. (a) Wu, M.-F.; Yeh, S.-J.; Chen, C-T.; Murayama, H.; Tsuboi. T; Li, W.-S.; Chao, L; Liu, S.-W.; Wang, J.-K. Adv. Funct. Mater. 2007, 17, 1887.
96. (b) Liu, S.-W.; Lee, J.-H.; Lee, C.-C; Chen, C-T; Wang, J.-K. Appl. Phys. Lett. 2007, 91, 142106.
97. Yeh. S.-J.; Wu. M.-F.; Chen, C-T; Song, Y.-H.; Chi. Y.; Ho. M.-H.: Hsu, S.-F.; Chen. C. H. Adv. Mater. 2005, 17, 285.
98. Forrest, S. R.; Bradley, D. D. C; Thompson, M. E. Adv. Mater. 2003, 15, 1043.
99. Tanaka. I; Tokito, S. Jpn. J. Appl. Phys 2004, 43, 7733.