Citation: OUYANG Mi, WU Qi-Chao, YU Zhen-Wei, LI Hong-Fei, ZHANG Cheng. Synthesis and Photoelectrical Properties of Two Potential Solution-Processed Blue Fluorescent Emitters Based on Fluorene-Arylamine Derivatives End-Capped with Anthracene/Pyrene Molecules[J]. Acta Physico-Chimica Sinica, ;2014, 30(7): 1341-1346. doi: 10.3866/PKU.WHXB201405041 shu

Synthesis and Photoelectrical Properties of Two Potential Solution-Processed Blue Fluorescent Emitters Based on Fluorene-Arylamine Derivatives End-Capped with Anthracene/Pyrene Molecules

1.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China

Received Date: 24 January 2014
Available Online: 4 May 2014
Fund Project:

Two novel potential solution-processed blue fluorescent emitters composed of a core fluorenediphenylamine unit capped with either anthracene (FAn) or pyrene (FPy) were synthesized and characterized. They were both soluble in common organic solvents and solutions gave smooth films after spin coating. Their optical properties in solution and in the film were investigated by UV-visible and photoluminescence (PL) spectroscopy. The PL emission maximum of FAn and FPy in the film state were found to be 449 and 465 nm, respectively. The electrochemical properties of the as-prepared samples were studied by cyclic voltammetry. The estimated highest occupied molecular orbital (HOMO) energy levels were -5.37 and -5.36 eV for FAn and FPy, respectively. These results indicate that the introduction of diphenylamine effectively prevents plane stacking of the molecules in the solid state, which suppresses the formation of long-wavelength aggregates, and the high HOMO levels enhance the hole-injection ability of the compounds. The results of differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) indicate that the two materials have excellent thermal stability with the glass transition temperature of FAn reaching 207 ℃ and the thermal decomposition temperature as high as 439 ℃. The od performance of the fluorescent emitters makes them promising candidates as solution-processed blue organic light-emitting diodes.
- Solution-processing,
- Blue fluorescent,
- Hole-injection,
- Fluorene,
- Pyrene,
- Anthracene
1. [1]
  
  (1) Tang, C.W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51 (12), 913. doi: 10.1063/1.98799
2. [2]
  (2) Uoyama, H.; ushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492 (7428), 234. doi: 10.1038/nature11687
3. [3]
  (3) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267 (5202), 1332. doi: 10.1126/science.267.5202.1332
4. [4]
  (4) Muller, C. D.; Falcou, A.; Reckefuss, N.; Rojahn, M.; Wiederhirn, V.; Rudati, P.; Frohne, H.; Nuyken, O.; Becker, H.; Meerholz, K. Nature 2003, 421 (6925), 829. doi: 10.1038/nature01390
5. [5]
  (5) Liu, C.; Li, Y. H.; Li, Y. F.; Yang, C. L.;Wu, H. B.; Qin, J. G.; Cao, Y. Chem. Mat. 2013, 25 (16), 3320. doi: 10.1021/cm401640v
6. [6]
  (6) Trattnig, R.; Pevzner, L.; Jager, M.; Schlesinger, R.; Nardi, M. V.; Li rio, G.; Christodoulou, C.; Koch, N.; Baumgarten, M.; Mullen, K.; List, E. J.W. Adv. Funct. Mater. 2013, 23 (39), 4897. doi: 10.1002/adfm.v23.39
7. [7]
  (7) Wang, C. F.; Hung,W. Y.; Cheng, M. H.; Hwang, J. S.; Leung, M. K.;Wong, K. T. Org. Electron. 2013, 14 (8), 1958. doi: 10.1016/j.orgel.2013.04.047
8. [8]
  (8) Zuniga, C. A.; Barlow, S.; Marder, S. R. Chem. Mat. 2011, 23 (3), 658. doi: 10.1021/cm102401k
9. [9]
  (9) Okumoto, K.; Kanno, H.; Hamaa, Y.; Takahashi, H.; Shibata, K. Appl. Phys. Lett. 2006, 89 (6), 063504. doi: 10.1063/1.2266452
10. [10]
  (10) Zhu, M. R.; Yang, C. L. Chem. Soc. Rev. 2013, 42 (12), 4963. doi: 10.1039/c3cs35440g
11. [11]
  (11) Chen, C. T. Chem. Mat. 2004, 16 (23), 4389. doi: 10.1021/cm049679m
12. [12]
  (12) Xiao, L. X.; Hu, S. Y.; Kong, S.; Chen, Z. J.; Qu, B.; ng, Q. H. Acta Phys. -Chim. Sin. 2011, 27 (4), 977. [肖立新, 胡双元, 孔胜, 陈志坚, 曲波, 龚旗煌. 物理化学学报, 2011, 27 (4), 977.]
13. [13]
  (13) Zhang, L.; Lin, Z. Q.; Gu, J. F.; Yin, C. R.; Hou, X. Y.; Liu, F.; Liu, Y. Y.; Xie, L. H.; Chen, S. F.; Huang,W. Acta Phys.-Chim. Sin. 2010, 26 (7), 1934. [张龙, 林宗琼, 顾菊芬, 殷成蓉, 侯晓雅, 刘烽, 刘玉玉, 解令海, 陈淑芬, 黄维. 物理化学学报, 2012, 26 (7), 1934.]
14. [14]
  (14) Chu, Z. Z.;Wang, D.; Zhang, C.; Zou, D. C. Acta Phys. -Chim. Sin. 2012, 28 (8), 2000. [初增泽, 王丹, 张超, 邹德春.物理化学学报, 2012, 28 (8), 2000.]
15. [15]
  (15) Wu, K. C.; Ku, P. J.; Lin, C. S.; Shih, H. T.;Wu, F. I.; Huang, M. J.; Lin, J. J.; Chen, I. C.; Cheng, C. H. Adv. Funct. Mater. 2008, 18 (1), 67.
16. [16]
  (16) Chan, K. L.; Lim, J. P. F.; Yang, X. H.; Dodabalapur, A.; Jabbour, G. E.; Sellinger, A. Chem. Commun. 2012, 48 (42), 5106. doi: 10.1039/c2cc30995e
17. [17]
  (17) Hu, J. Y.; Era, M.; Else od, M. R. J.; Yamato, T. Eur. J. Org. Chem. 2010, 2010 (1), 72. doi: 10.1002/ejoc.200900806
18. [18]
  (18) Kim, R.; Lee, S.; Kim, K. H.; Lee, Y. J.; Kwon, S. K.; Kim, J. J.; Kim, Y. H. Chem. Commun. 2013, 49 (41), 4664. doi: 10.1039/c3cc41441h
19. [19]
  (19) Park, H.; Lee, J.; Kang, I.; Chu, H. Y.; Lee, J. I.; Kwon, S. K.; Kim, Y. H. J. Mater. Chem. 2012, 22 (6), 2695. doi: 10.1039/c2jm16056k
20. [20]
  (20) Kumar, D.; Thomas, K. R. J.; Chen, Y. L.; Jou, Y. C.; Jou, J. H. Tetrahedron 2013, 69 (12), 2594. doi: 10.1016/j.tet.2013.01.046
21. [21]
  (21) Yao, L.; Sun, S. H.; Xue, S. F.; Zhang, S. T.;Wu, X. Y.; Zhang, H. H.; Pan, Y. Y.; Gu, C.; Li, F. H.; Ma, Y. G. J. Phys. Chem. C 2013, 117 (27), 14189. doi: 10.1021/jp403463k
22. [22]
  (22) Zhang, Y. J.; Jin, Y. X.; Bai, R.; Yu, Z.W.; Hu, B.; Ouyang, M.; Sun, J.W.; Yu, C. H.; Liu, J. L.; Zhang, C. J. Photochem. Photobiol. A-Chem. 2012, 227 (1), 59. doi: 10.1016/j.jphotochem.2011.11.003
23. [23]
  (23) Taguchi, Y.; Uyama, H.; Kobayashi, S. J. Polym. Sci. Pol. Chem. 1996, 34 (4), 561.
24. [24]
  (24) Hong, Y.; Liao, J. Y.; Cao, D.; Zang, X.; Kuang, D. B.;Wang, L.; Meier, H.; Su, C. Y. J. Org. Chem. 2011, 76 (19), 8015. doi: 10.1021/jo201057b
25. [25]
  (25) Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. J. Org. Chem. 2010, 75 (12), 4124. doi: 10.1021/jo100277v
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