Citation: Hong-ji Jiang, Qing-wei Zhang, Xu He, Xiao-lin Zhang, Xin-wen Zhang. Triphenyl Phosphine Oxide and Carbazole-based Polymer Host Materials for Green Phosphorescent Organic Light-emitting Diodes[J]. Chinese Journal of Polymer Science, ;2017, 35(5): 611-622. doi: 10.1007/s10118-017-1926-5 shu

Triphenyl Phosphine Oxide and Carbazole-based Polymer Host Materials for Green Phosphorescent Organic Light-emitting Diodes

Key Laboratory of Organic Electronics and Information Displays, National Jiangsu Synergetic Innovation Center for Organic Electronics and Information Displays, Institute of Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing 210023, China

Corresponding author: Hong-ji Jiang, iamhjjiang@njupt.edu.cn
Received Date: 22 September 2016
Revised Date: 24 November 2016
Accepted Date: 24 November 2016

Fund Project: This work was financially supported by the Major Research Program from the State Ministry of Science and Technology 2012CB933301the Priority Academic Program Development of Jiangsu Higher Education Institutions YX03001Natural Science Foundation of the Jiangsu Higher Education Institutions of China 15KJB150022Natural Science Foundation of Jiangsu Province BM2012010the National Natural Science Foundation of China 21574068

Four novel polymers, poly (3, 6-9-decyl-carbazole-alt-1, 3-benzene) (PB13CZ), poly (3, 6-9-decyl-carbazole-alt-bis (4-phenyl) (phenyl) phosphine oxide) (PTPPO38CZ), poly (3, 6-9-decyl-carbazole-alt-2, 4-phenyl (diphenyl) phosphine oxide) (PTPPO13CZ) and poly (3, 6-9-decyl-carbazole-alt-bis (3-phenyl) (phenyl) phosphine oxide) (PTTPO27CZ) were synthesized, and their thermal, photophysical properties and device applications were further investigated to correlate the chemical structures with the photoelectric performance of bipolar host materials for phosphorescent organic light emitting diodes. All of them show high thermal stability as revealed by their high glass transition temperatures and thermal decomposition temperatures at 5% weight loss. These polymers have wide band gaps and relatively high triplet energy levels. As a result, the spin coating method was used to prepare the green phosphorescent organic light emitting diodes with polymers PTPPO38CZ, PTPPO13CZ and PTTPO27CZ as the typical host materials. The green device of polymer PTPPO38CZ as host material shows electroluminescent performance with maximum current efficiency of 2.16 cd·A^-1, maximum external quantum efficiency of 0.7%, maximum brightness of 1475 cd·m^-2 and reduced efficiency roll-off of 7.14% at 600 cd·m^-2, which are much better than those of the same devices hosted by polymers PTTPO27CZ and PTPPO13CZ.
- Triphenyl phosphine oxide,
- Phosphorescent organic light-emitting diode,
- Thermal stability,
- Triplet energy levels,
- Polymer host materials,
- Electroluminescent performance
1. [1]
  Baldo, M.A., O'Brien, D.F., You, Y., Shoustikov, A., Sibley, S., Thompson, M.E. and Forrest, S.R., Nature, 1998, 395(6698):151 doi: 10.1038/25954
2. [2]
  Baldo, M.A., Lamansky, S., Burrows, P.E., Thompson, M.E. and Forrest, S.R., Appl. Phys. Lett., 1999, 75(1):4 doi: 10.1063/1.124258
3. [3]
  Adachi, C., Baldo, M.A., Thompson, M.E. and Forrest, S.R., J. Appl. Phys., 2001, 90(10):5048 doi: 10.1063/1.1409582
4. [4]
  Sun, Y.R., Giebink, N.C., Kanno, H., Ma, B.W., Thompson, M.E. and Forrest, S.R., Nature, 2006, 440(7086):908 doi: 10.1038/nature04645
5. [5]
  Reineke, S., Lindner, F., Schwartz, G., Seidler, N., Walzer, K., Lussem, B. and Leo, K., Nature, 2009, 459(7244):234 doi: 10.1038/nature08003
6. [6]
  Zhang, B.H., Tan, G.P., Lam, C.S., Yao, B., Ho, C.L., Liu, L.H., Xie, Z.Y., Wong, W.Y., Ding, J.Q. and Wang, L.X., Adv. Mater., 2012, 24(14):1873 doi: 10.1002/adma.v24.14
7. [7]
  Baldo, M.A., O'Brien, D.F., Thompson, M.E. and Forrest, S.R., Phys. Rev. B., 1999, 60(20):14422 doi: 10.1103/PhysRevB.60.14422
8. [8]
  Yeh, S.J., Wu, M.F., Chen, C.T., Song, Y.H., Chi, Y., Ho, M.H., Hsu, S.F. and Chen, C.H., Adv. Mater., 2005, 17(3):285 doi: 10.1002/(ISSN)1521-4095
9. [9]
  Tao, Y.T., Yang, C.L. and Qin, J.G., Chem. Soc. Rev., 2011, 40(5):2943 doi: 10.1039/c0cs00160k
10. [10]
  Gong, S., Chang, Y.L., Wu, K., White, R., Lu, Z.H., Song, D. and Yang, C., Chem. Mater., 2014, 26(3):1463 doi: 10.1021/cm4037555
11. [11]
  Han, C., Zhu, L., Li, J., Zhao, F., Zhang, Z., Xu, H., Deng, Z., Ma, D. and Yan, P., Adv. Mater., 2014, 26(41):7070 doi: 10.1002/adma.201400710
12. [12]
  Xu, H., Chen, R., Sun, Q., Lai, W., Su, Q., Huang, W. and Liu, X., Chem. Soc. Rev., 2014, 43(10):3259 doi: 10.1039/c3cs60449g
13. [13]
  Yook, K.S. and Lee, J.Y., Adv. Mater., 2012, 24(24):3169 doi: 10.1002/adma.v24.24
14. [14]
  Mondal, E., Hung, W.Y., Dai, H.C. and Wong, K.T., Adv. Funct. Mater., 2013, 23(24):3096 doi: 10.1002/adfm.v23.24
15. [15]
  Xiao, L.X., Chen, Z.J., Qu, B., Luo, J.X., Kong, S., Gong, Q.H. and Kido, J.J., Adv. Mater., 2011, 23(8):926 doi: 10.1002/adma.v23.8
16. [16]
  Zhou, G.J., Wong, W.Y. and Yang, X.L., Chem. Asian. J., 2011, 6(7):1706 doi: 10.1002/asia.201000928
17. [17]
  Ho, C.L. and Wong, W.Y., Coord. Chem. Rev., 2013, 257(9-10):1614 doi: 10.1016/j.ccr.2012.08.023
18. [18]
  Mi, B.X., Gao, Z.Q., Liao, Z.J., Huang, W. and Chen, C.H., Sci. China Chem., 2010, 53(8):1679 doi: 10.1007/s11426-010-4043-7
19. [19]
  Lyu, Y.Y., Kwak, J., Jeon, W.S., Byun, Y., Lee, H.S., Kim, D., Lee, C. and Char, K., Adv. Funct. Mater., 2009, 19(3):420 doi: 10.1002/adfm.v19:3
20. [20]
  Tao, Y.T., Gong, S.L., Wang, Q., Zhong, C., Yang, C.L., Qin, J.G. and Ma, D.G., Phys. Chem. Chem. Phys., 2010, 12(10):2438 doi: 10.1039/b922110g
21. [21]
  Shih, P.I., Chien, C.H., Chuang, C.Y., Shu, C.F., Yang, C.H., Chen, J.H. and Chi, Y., J. Mater. Chem., 2007, 17(17):1692 doi: 10.1039/b616043c
22. [22]
  Hsu, F.M., Chien, C.H., Shu, C.F., Lai, C.H., Hsieh, C.C., Wang, K.W. and Chou, P.T., Adv. Funct. Mater., 2009, 19(17):2834 doi: 10.1002/adfm.v19:17
23. [23]
  Ge, Z.Y., Hayakawa, T., Ando, S., Ueda, M., Akiike, T., Miyamoto, H., Kajita, T. and Kakimoto, M.A., Adv. Funct. Mater., 2008, 18(4):584 doi: 10.1002/(ISSN)1616-3028
24. [24]
  Sun, D.M., Fu, Q., Ren, Z.J., Li, W., Li, H.H., Ma, D.G. and Yan, S.K., J. Mater. Chem. C., 2013, 1(34):5344 doi: 10.1039/c3tc31108b
25. [25]
  Gong, X., Robinson, M., Ostrowski, J., Moses, D., Bazan, G. and Heeger, A., Adv. Mater., 2002, 14(8):581 doi: 10.1002/1521-4095(20020418)14:8<>1.0.CO;2-F
26. [26]
  Yin, C.R., Ye, S.H., Zhao, J., Yi, M.D., Xie, L.H., Lin, Z.Q., Chang, Y.Z., Liu, F., Xu, H., Shi, N.E., Qian, Y. and Huang, W., Macromolecules, 2011, 44(12):4589 doi: 10.1021/ma200624u
27. [27]
  Jiang, H.J., Asian J. Org. Chem., 2014, 3(2):102 doi: 10.1002/ajoc.v3.2
28. [28]
  Liu, C., Li, Y.H., Li, Y.F., Yang, C.L., Wu, H.B., Qin, J.G. and Cao, Y., Chem. Mater., 2013, 25(16):3320 doi: 10.1021/cm401640v
29. [29]
  Shao, S.Y., Ding, J.Q., Ye, T.L., Xie, Z.Y., Wang, L.X., Jing, X.B. and Wang, F.S., Adv. Mater., 2011, 23(31):3570 doi: 10.1002/adma.201101074
30. [30]
  Zhang, Q.W., Fang, D., Jiang, H.J., Zhang, X.W. and Zhang, H.M., Org. Electron., 2015, 27:173 doi: 10.1016/j.orgel.2015.09.002
31. [31]
  Dumur, F., Beouch, L., Peralta, S., Wantz, G., Goubard, F. and Gigmes, D., Org. Electron., 2015, 25:21 doi: 10.1016/j.orgel.2015.06.013
32. [32]
  Lee, J.Y., Aizawa, N., Numata, M., Adachi, C. and Yasuda, T., Adv. Mater., 2016, DOI:10.1002/adma. 201604856 doi: 10.1002/adma.201604856
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