Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials

Angewandte Chemie - International Edition

Volumn 54, Issue 19, 2015, Pages 5677-5682

  Albrecht, Ken ^a   Matsuoka, Kenichi ^b   Fujita, Katsuhiko ^b   Yamamoto, Kimihisa ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

carbazoles; dendrimers; electroluminescence; fluorescence

Indexed keywords

DENDRIMERS; DOPING (ADDITIVES); ELECTROLUMINESCENCE; ELECTRONIC STRUCTURE; ELECTROPOLYMERIZATION; EXCITONS; FLUORESCENCE; LIGHT; LIGHT EMITTING DIODES; MOLECULAR WEIGHT; ORGANIC LIGHT EMITTING DIODES (OLED); POLYCYCLIC AROMATIC HYDROCARBONS; POLYOLS; SPIN COATING;

CARBAZOLES; EXTERNAL QUANTUM EFFICIENCY; HIGH MOLECULAR WEIGHT; LUMINESCENCE LIFETIME; ORGANIC LIGHT EMITTING DIODES(OLEDS); TEMPERATURE DEPENDENT; TERT-BUTYLDIMETHYLSILYL; THERMALLY ACTIVATED DELAYED FLUORESCENCES;

QUANTUM EFFICIENCY;

EID: 85027938778     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201500203     Document Type: Article

References (90)

1. C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913
2. C. W. Tang, S. A. VanSlyke, C. H. Chen, J. Appl. Phys. 1989, 65, 3610
3. C. W. Tang, Appl. Phys. Lett. 1986, 48, 183.
4. B. Geffroy, P. le Roy, C. Prat, Polym. Int. 2006, 55, 572
5. J. Kido, M. Kimura, K. Nagai, Science 1995, 267, 1332
6. O. Nuyken, S. Jungermann, V. Wiederhirn, E. Bacher, K. Meerholz, Monatsh. Chem. 2006, 137, 811
7. A. P. Kulkarni, C. J. Tonzola, A. Babel, S. A. Jenekhe, Chem. Mater. 2004, 16, 4556.
8. C. J. Brabec, J. R. Durrant, MRS Bull. 2008, 33, 670
9. Y. J. Cheng, S. H. Yang, C. S. Hsu, Chem. Rev. 2009, 109, 5868
10. A. W. Hains, Z. Liang, M. A. Woodhouse, B. A. Gregg, Chem. Rev. 2010, 110, 6689
11. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, H. Pettersson, Chem. Rev. 2010, 110, 6595
12. T. M. Clarke, J. R. Durrant, Chem. Rev. 2010, 110, 6736
13. P. V. Kamat, K. Tvrdy, D. R. Baker, J. G. Radich, Chem. Rev. 2010, 110, 6664.
14. J. Zaumseil, H. Sirringhaus, Chem. Rev. 2007, 107, 1296.
15. Q. D. Ling, D. J. Liaw, C. Zhu, D. S. H. Chan, E. T. Kang, K. G. Neoh, Prog. Polym. Sci. 2008, 33, 917
16. P. Heremans, G. H. Gelinck, R. Müller, K. J. Baeg, D. Y. Kim, Y. Y. Noh, Chem. Mater. 2011, 23, 341
17. Y. Yonekuta, K. Susuki, K. Oyaizu, K. Honda, H. Nishide, J. Am. Chem. Soc. 2007, 129, 14128.
18. C. Zhong, C. Duan, F. Huang, H. Wu, Y. Cao, Chem. Mater. 2011, 23, 326
19. C. Sekine, Y. Tsubata, T. Yamada, M. Kitano, S. Doi, Sci. Technol. Adv. Mater. 2014, 15, 034203.
20. L. Duan, L. Hou, T. Lee, J. Qiao, D. Zhang, G. Dong, L. Wanga, Y. Qiu, J. Mater. Chem. 2010, 20, 6392.
21. D. Astruc, E. Boisselier, C. Ornelas, Chem. Rev. 2010, 110, 1857
22. M. Fischer, F. Vögtle, Angew. Chem. Int. Ed. 1999, 38, 884
23. Angew. Chem. 1999, 111, 934
24. A. W. Bosman, H. M. Janssen, E. W. Meijer, Chem. Rev. 1999, 99, 1665
25. G. R. Newkome, C. Shreiner, Chem. Rev. 2010, 110, 6338
26. S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819.
27. P. L. Burn, S. C. Lo, I. D. W. Samuel, Adv. Mater. 2007, 19, 1675
28. P. Furuta, J. Brooks, M. E. Thompson, J. M. J. Fréchet, J. Am. Chem. Soc. 2003, 125, 13165
29. T. W. Kwon, M. M. Alam, S. A. Jenekhe, Chem. Mater. 2004, 16, 4657
30. D. Ma, J. M. Lupton, I. D. W. Samuel, S. C. Lo, P. L. Burn, Appl. Phys. Lett. 2002, 81, 2285
31. T. Qin, G. Zhou, H. Scheiber, R. E. Bauer, M. Baumgarten, C. E. Anson, E. J. W. List, K. Müllen, Angew. Chem. Int. Ed. 2008, 47, 8292
32. Angew. Chem. 2008, 120, 8416
33. S. Hwang, C. N. Moorefield, G. R. Newkome, Chem. Soc. Rev. 2008, 37, 2543.
34. K. Albrecht, K. Yamamoto, J. Am. Chem. Soc. 2009, 131, 2244
35. N. D. McClenaghan, R. Passalacqua, F. Loiseau, S. Campagna, B. Verheyde, A. Hameurlaine, W. Dehaen, J. Am. Chem. Soc. 2003, 125, 5356
36. Y. Xing, H. Lin, F. Wang, P. Lu, Sens. Actuators B 2006, 114, 28
37. K. A. Knights, S. G. Stevenson, C. P. Shipley, S.-C. Lo, S. Olsen, R. E. Harding, S. Gambino, P. L. Burn, I. D. W. Samuel, J. Mater. Chem. 2008, 18, 2121
38. T. Xu, R. Lu, M. Jin, X. Qiu, P. Xue, C. Bao, Y. Zhao, Tetrahedron Lett. 2005, 46, 6883
39. A. Kimoto, J. Cho, M. Higuchi, K. Yamamoto, Macromolecules 2004, 37, 5531
40. S. Gambino, S. G. Stevenson, K. A. Knights, P. L. Burn, I. D. W. Samuel, Adv. Funct. Mater. 2009, 19, 317
41. K. Mutkins, S. S. Y. Chen, A. Pivrikas, M. Aljada, P. L. Burn, P. Meredith, B. J. Powell, Polym. Chem. 2013, 4, 916.
42. Q. Zhang, Y. F. Hu, Y. X. Cheng, G. P. Su, D. G. Ma, L. X. Wang, X. B. Jing, F. S. Wang, Synth. Met. 2003, 137, 1111
43. V. Promarak, M. Ichikawa, D. Meunmart, T. Sudyoadsuk, S. Saengsuwan, T. Keawin, Tetrahedron Lett. 2006, 47, 8949
44. P. Moonsin, N. Prachumrak, R. Rattanawan, T. Keawin, S. Jungsuttiwong, T. Sudyoadsuk, V. Promarak, Chem. Commun. 2012, 48, 3382
45. K. Albrecht, Y. Kasai, A. Kimoto, K. Yamamoto, Macromolecules 2008, 41, 3793.
46. M.-H. Tsai, Y.-H. Hong, C.-H. Chang, H.-C. Su, C.-C. Wu, A. Matoliukstyte, J. Simokaitiene, S. Grigalevicius, J. V. Grazulevicius, C.-P. Hsu, Adv. Mater. 2007, 19, 862
47. J. Ding, B. Zhang, J. Lü, Z. Xie, L. Wang, X. Jing, F. Wang, Adv. Mater. 2009, 21, 4983
48. W. Jiang, L. Duan, J. Qiao, G. Dong, D. Zhang, L. Wang, Y. Qiu, J. Mater. Chem. 2011, 21, 4918
49. B. Zhang, G. Tan, C.-S. Lam, B. Yao, C.-L. Ho, L. Liu, Z. Xie, W.-Y. Wong, J. Ding, L. Wang, Adv. Mater. 2012, 24, 1873
50. E. Orselli, J. Maunoury, D. Bascour, J.-P. Catinat, Org. Electron. 2012, 13, 1506
51. J. Li, T. Zhang, Y. Liang, R. Yang, Adv. Funct. Mater. 2013, 23, 619.
52. Y. Li, A. Rizzo, M. Salerno, M. Mazzeo, C. Huo, Y. Wang, K. Li, R. Cingolani, G. Gigli, Appl. Phys. Lett. 2006, 89, 061125
53. K. Albrecht, Y. Kasai, K. Yamamoto, J. Inorg. Organomet. Polym. Mater. 2009, 19, 118
54. H. Zhang, S. Wang, Y. Li, B. Zhang, C. Du, X. Wan, Y. Chen, Tetrahedron 2009, 65, 4455
55. Z. Zhao, H. Jin, Y.-X. Zhang, Z. Shen, D.-C. Zou, X.-H. Fan, Macromolecules 2011, 44, 1405
56. P. Moonsin, N. Prachumrak, S. Namuangruk, S. Jungsuttiwong, T. Keawin, T. Sudyoadsuk, V. Promarak, Chem. Commun. 2013, 49, 6388
57. Ö. Usluer, S. Demic, M. Kus, F. Özel, N. Serdar Sariciftci, J. Lumin. 2014, 146, 6.
58. J. Ding, J. Gao, Y. Cheng, Z. Xie, L. Wang, D. Ma, X. Jing, F. Wang, Adv. Funct. Mater. 2006, 16, 575
59. J. Ding, B. Wang, Z. Yue, B. Yao, Z. Xie, Y. Cheng, L. Wang, X. Jing, F. Wang, Angew. Chem. Int. Ed. 2009, 48, 6664
60. Angew. Chem. 2009, 121, 6792
61. 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
62. Angew. Chem. 2013, 125, 464
63. D. Xia, B. Wang, B. Chen, S. Wang, B. Zhang, J. Ding, L. Wang, X. Jing, F. Wang, Angew. Chem. Int. Ed. 2014, 53, 1048
64. Angew. Chem. 2014, 126, 1066.
65. A. Kimoto, J. Cho, K. Ito, D. Aoki, T. Miyake, K. Yamamoto, Macromol. Rapid Commun. 2005, 26, 597
66. K. Albrecht, R. Pernites, M. J. Felipe, R. C. Advincula, K. Yamamoto, Macromolecules 2012, 45, 1288
67. N. Aizawa, Y. Pu, T. Chiba, S. Kawata, H. Sasabe, J. Kido, Adv. Mater. 2014, 26, 754
68. C. A. Zuniga, S. Barlow, S. R. Marder, Chem. Mater. 2011, 23, 658.
69. M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151
70. C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, J. Appl. Phys. 2001, 90, 5048.
71. A. P. Monkman, ISRN Mater. Sci. 2013, 2013, 670130.
72. A. Endo, M. Ogasawara, A. Takahashi, D. Yokoyama, Y. Kato, C. Adachi, Adv. Mater. 2009, 21, 4802
73. H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234
74. Q. Zhang, B. Li, S. Huang, H. Nomura, H. Tanaka, C. Adachi, Nat. Photonics 2014, 8, 326
75. H. Wang, L. Xie, Q. Peng, L. Meng, Y. Wang, Y. Yi, P. Wang, Adv. Mater. 2014, 26, 5198
76. S. Y. Lee, T. Yasuda, Y. S. Yang, Q. Zhang, C. Adachi, Angew. Chem. Int. Ed. 2014, 53, 6402
77. Angew. Chem. 2014, 126, 6520
78. H. Tanaka, K. Shizu, H. Nakanotani, C. Adachi, Chem. Mater. 2013, 25, 3766
79. Y. Tao, K. Yuan, T. Chen, P. Xu, H. Li, R. Chen, C. Zheng, L. Zhang, W. Huang, Adv. Mater. 2014, 26, 7931.
80. Y. Maegawa, Y. Goto, S. Inagaki, T. Shimada, Tetrahedron Lett. 2006, 47, 6957
81. J. Barluenga, J. M. Gonzalez, P. J. Campos, G. Asensio, Angew. Chem. Int. Ed. Engl. 1985, 24, 319
82. Angew. Chem. 1985, 97, 341
83. J. M. Chalker, C. S. C. Wood, B. G. Davis, J. Am. Chem. Soc. 2009, 131, 16346.
84. R. Berger, J. Hauser, G. Labat, E. Weber, J. Hulliger, CrystEngComm 2012, 14, 768.
85. The calculations (optimizations) were executed at the HF/6-31G level of theory for G2TAZ and G3TAZ, and at the semi-empirical PM6 level of theory for G4TAZ as implemented in the Gaussian09 C.01 software package; see: M. J. Frisch et al. Gaussian 09, Revision C.01; Gaussian Inc.: Wallingford, CT, 2010.
86. J. Lee, K. Shizu, H. Tanaka, H. Nomura, T. Yasuda, C. Adachi, J. Mater. Chem. C 2013, 1, 4599.
87. K. Goushi, K. Yoshida, K. Sato, C. Adachi, Nat. Photonics 2012, 6, 253.
88. T. Serevičius, T. Nakagawa, M. Kuo, S. Cheng, K. Wong, C. Chang, R. C. Kwong, S. Xia, C. Adachi, Phys. Chem. Chem. Phys. 2013, 15, 15850.
89. S. Kim, J. Kim, Org. Electron. 2010, 11, 1010.
90. M. A. Baldo, C. Adachi, S. R. Forrest, Phys. Rev. B 2000, 62, 10967.