咔唑與苯並咪唑碳氮連接之雙極性衍生物為主體材料之藍色磷光及熱活性型螢光有機發光二極體之研究

Study of Carbazole-N-Benzimidazole Bipolar Materials as Host Materials of Blue Phosphorescent and Thermally Activated Delayed Fluorescence Organic Light-emitting Diodes

10.6342/NTU201702827

李政頡

有機發光二極體 ； 效率 ； 磷光 ； 熱活性型螢光 ； Organic light-emitting diode ； efficiency ； phosphorescence ； thermally activated delayed fluorescence.

臺灣大學光電工程學研究所學位論文

2017年

碩士

李君浩

英文

本篇論文研究包含兩部分。在本篇論文的第一部分，我們使用台大化學所梁文傑實驗室所提供的咔唑與苯並咪唑碳氮連接之雙極性衍生物9-(2-(2-phenyl-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole (A-o-CBZBIZ) 、 和9-(3-(9H-carbazol-9-yl)-2-(2-phenyl-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole (A-dio-CBZBIZ)作為主體材料，與bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic)作為客體材料，進行藍色磷光有機發光二極體之研究，藉由調變元件結構，在A-o-CBZBIZ系統中得到57.45 cd/A 的最高電流效率、50.16 lm/W 的最高功率效率及27.87% 的最高外部量子效率。 而在第二部分，我們使用台大化學所梁文傑實驗室所提供的9,9'-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)-1,3-phenylene)bis(9H-carbazole) (o-DiCbzBz) 以及9,9',9',9'-(3-(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene- 1,2,4,5tetrayl)tetrakis(9H-carbazole) (o-4CzBz)作為主體材料，並分別搭配bis[4-(9,9-dimethyl-9,10-dihydroacridine) phenyl]sulfone (DMAC-DPS)和(4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN)作為客體材料，來製作藍色和綠色熱活性型螢光有機發光二極體。藉由調變元件結構，在藍色熱活性型螢光有機發光二極體，我們得到32.37 cd/A 的最高電流效率、33.15 lm/W 的最高功率效率及18.46% 的最高外部量子效率，以及在綠色熱活性型螢光有機發光二極體，我們得到102.70 cd/A 的最高電流效率、103.60 lm/W 的最高功率效率及29.55% 的最高外部量子效率。

There are two topics in this thesis. In the first part, carbazole-N-benzimidazole bipolar materials 9-(2-(2-phenyl-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole (A-o-CBZBIZ) and 9-(3-(9H-carbazol-9-yl)-2-(2-phenyl-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole (A-dio-CBZBIZ) provided by Prof. Man-Kit Leung’s group, Department of Chemistry in National Taiwan University, were used as the host materials for blue phosphorescent organic light-emitting diodes (OLEDs), doped with bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic). By tuning the device structure, maximum current efficiency of 57.45 cd/A, maximum power efficiency of 50.16 lm/W and maximum EQE of 27.87% were obtained in A-o-CBZBIZ system. In the second part, (2-(1-phenyl-1H-benzo[d]imidazol-2-yl)-1,3-phenylene)bis(9H-carbazole) (o-DiCbzBz) and 9,9',9',9'-(3-(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene- 1,2,4,5tetrayl)tetrakis(9H-carbazole) (o-4CzBz), provided by Prof. Man-Kit Leung’s group, Department of Chemistry in National Taiwan University, were utilized as host materials of the blue and green thermally activated delayed fluorescence (TADF) OLEDs. bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (DMAC-DPS) and (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) were used as blue and green TADF dopant materials, respectively. By tuning the device structure, in o-DiCbzBz-DMAC-DPS-based blue TADF OLEDs, maximum current efficiency of 32.37 cd/A, maximum power efficiency of 33.15 lm/W and maximum EQE of 18.46% were obtained. In o-4CzBz-4CzIPN-based green TADF OLEDs, we obtained a good performance with maximum current efficiency 102.7 cd/A, maximum power efficiency of 103.6 lm/W and maximum EQE of 29.55%.

1. [6]Huang, J. J., Hung, Y. H., Ting, P. L., Tsai, Y. N., Gao, H. J., Chiu, T. L., Leung, M. K., Org. Lett., 2016, 18(4), 672-675.
   連結：
2. [8]Tang, C. W., VanSlyke, S. A., Appl. Phys. Lett., 1987, 51(12), 913-915.
   連結：
3. [9]Watanabe, S., Ide, N., Kido, J., Jpn. J. Appl. Phys., 2007, 46(3R), 1186.
   連結：
4. [15]Tang, C. W., VanSlyke, S. A., Chen, C. H., J. Appl. Phys., 1989, 65(9), 3610-3616.
   連結：
5. [16]Főrster, T., Discussions of the Faraday Society, 1959, 27, 7-17.
   連結：
6. [17]Förster, T., Annalen der physik, 1948, 437(1‐2), 55-75.
   連結：
7. [18]Dexter, D. L., J. Chem. Phys., 1953, 21(5), 836-850.
   連結：
8. [27]Lin, M. S., Yang, S. J., Chang, H. W., Huang, Y. H., Tsai, Y. T., Wu, C. C., Wong, K. T., J. Mater. Chem., 2012, 22(31), 16114-16120.
   連結：
9. [28]Huang, J. J., Leung, M. K., Chiu, T. L., Chuang, Y. T., Chou, P. T., Hung, Y. H., Org. Lett., 2014, 16(20), 5398-5401.
   連結：
10. [32]Hung, W. Y., Chi, L. C., Chen, W. J., Chen, Y. M., Chou, S. H., Wong, K. T., J. Mater. Chem., 2010, 20(45), 10113-10119.
    連結：
11. [35]Higuchi, T., Nakanotani, H., Adachi, C., Adv. Mater., 2015, 27(12), 2019-2023.
    連結：
12. [42]Wang, H., Xie, L., Peng, Q., Meng, L., Wang, Y., Yi, Y., Wang, P., Adv. Mater., 2014, 26(30), 5198-5204.
    連結：
13. [43]Adachi, C., Jpn. J. Appl. Phys, 2014, 53(6), 060101.
    連結：
14. [46]P. H. Chen, Transient Electroluminescence of Blue Phosphorescence Organic Light-emitting Diode with Different Host Materials and Dynamic of Exciton in Organic Thin Film on Silicon Surface, National Taiwan University Master Thesis, 2014.
    連結：
15. [1]Park, J. S., Chae, H., Chung, H. K., Lee, S. I., Semicond. Sci. Technol, 2011, 26(3), 034001.
16. [2]Gu, G., Burrows, P. E., Venkatesh, S., Forrest, S. R., Thompson, M. E., Opt. Lett., 1997, 22(3), 172-174.
17. [3]Gustafsson, G., Treacy, G. M., Cao, Y., Klavetter, F., Colaneri, N., Heeger, A. J., Synth. Met., 1993, 57(1), 4123-4127.
18. [4]Baldo, M. A., O'brien, D. F., You, Y., Shoustikov, A., Sibley, S., Thompson, M. E., Forrest, S. R., Nature, 1998, 395(6698), 151-154.
19. [5]Baldo, M. A., Thompson, M. E., Forrest, S. R., Nature, 2000, 403(6771), 750-753.
20. [7]Uoyama, H., Goushi, K., Shizu, K., Nomura, H., Adachi, C., Nature, 2012, 492(7428), 234-238.
21. [10]Chen, Y., Chen, J., Zhao, Y., Ma, D., Appl. Phys. Lett., 2012, 100(21), 114.
22. [11]Yang, X., Huang, H., Pan, B., Zhuang, S., Aldred, M. P., Wang, L., Ma, D., J. Mater. Chem., 2012, 22(43), 23129-23135.
23. [12]Tsutsui, T., Saito, S., Intrinsically Conducting Polymers: An Emerging Technology, 1993, (pp. 123-134). Springer Netherlands.
24. [13]Rothberg, L. J., Lovinger, A. J., J. Mater. Res., 1996, 11(12), 3174-3187.
25. [14]Adachi, C., Baldo, M. A., Thompson, M. E., Forrest, S. R., J. Appl. Phys., 2001, 90(10), 5048-5051.
26. [19]Uchida, M., Adachi, C., Koyama, T., Taniguchi, Y., J. Appl. Phys., 1999, 86(3), 1680-1687.
27. [20]Chin, B. D., Suh, M. C., Kim, M. H., Lee, S. T., Kim, H. D., Chung, H. K., Appl. Phys. Lett., 2005, 86(13), 133505.
28. [21]Hamada, Y., Matsusue, N., Kanno, H., Fujii, H., Tsujioka, T., Takahashi, H., Jpn. J. Appl. Phys., 2001, 40(7B), L753.
29. [22]Holmes, R. J., D’Andrade, B. W., Forrest, S. R., Ren, X., Li, J., Thompson, M. E., Appl. Phys. Lett., 2003, 83(18), 3818-3820.
30. [23]Adachi, C., Kwong, R. C., Djurovich, P., Adamovich, V., Baldo, M. A., Thompson, M. E., Forrest, S. R., Appl. Phys. Lett., 2001, 79(13), 2082-2084.
31. [24]Holmes, R. J., Forrest, S. R., Tung, Y. J., Kwong, R. C., Brown, J. J., Garon, S., Thompson, M. E., Appl. Phys. Lett., 2003, 82(15), 2422-2424.
32. [25]Tokito, S., Iijima, T., Suzuri, Y., Kita, H., Tsuzuki, T., Sato, F., Appl. Phys. Lett., 2003, 83(3), 569-571.
33. [26]Goushi, K., Kwong, R., Brown, J. J., Sasabe, H., Adachi, C., J. Appl. Phys., 2004, 95(12), 7798-7802.
34. [29]P. S. Wang, Blue Phosphorescent Organic Light-Emitting Diodes with Bipolar Carbazole-triazole Derivatives as Host Material, and Inverted Organic Photovoltaic Cells, National Taiwan University Master Thesis, 2014.
35. [30]Chopra, N., Lee, J., Zheng, Y., Eom, S. H., Xue, J., So, F., ACS Appl. Mat. Interfaces, 2009, 1(6), 1169-1172.
36. [31]Huang, H., Yang, X., Pan, B., Wang, L., Chen, J., Ma, D., Yang, C., J. Mater. Chem., 2012, 22(26), 13223-13230.
37. [33]Pan, B., Wang, B., Wang, Y., Xu, P., Wang, L., Chen, J., Ma, D., J. Mater. Chem. C, 2014, 2(14), 2466-2469.
38. [34]Luo, J., Gong, S., Gu, Y., Chen, T., Li, Y., Zhong, C., Yang, C., J. Phys. Chem. C, 2016, 4(13), 2442-2446.
39. [36]Zhang, Q., Li, B., Huang, S., Nomura, H., Tanaka, H., Adachi, C., Nat. Photon., 2014, 8(4), 326-332.
40. [37]Zhang, J., Ding, D., Wei, Y., Han, F., Xu, H., Huang, W., Adv. Mater., 2016, 28(3), 479-485.
41. [38]Kim, B. S., Lee, J. Y., ACS Appl. Mat. Interfaces, 2014, 6(11), 8396-8400.
42. [39]Cho, Y. J., Yook, K. S., Lee, J. Y., Adv. Mater, 2014, 26(24), 4050-4055.
43. [40]Lee, D. R., Kim, B. S., Lee, C. W., Im, Y., Yook, K. S., Hwang, S. H., Lee, J. Y., ACS Appl. Mat. Interfaces, 2015, 7(18), 9625-9629.
44. [41]Cho, Y. J., Jeon, S. K., Chin, B. D., Yu, E., Lee, J. Y., Angew. Chem. Int. Ed., 2015, 54(17), 5201-5204.
45. [44]Lee, D. R., Kim, M., Jeon, S. K., Hwang, S. H., Lee, C. W., Lee, J. Y., Adv. Mater., 2015, 27(39), 5861-5867.
46. [45]P. S. Wang, Blue Phosphorescent Organic Light-Emitting Diodes with Bipolar Carbazole-triazole Derivatives as Host Material, and Inverted Organic Photovoltaic Cells, National Taiwan University Master Thesis, 2014.