Citation: Yu Yun, Yang Jie, Ren Zichun, Xie Guohua, Li Qianqian, Li Zhen. Synthesis of Solution Processable Blue AIEgens and the Device Performance[J]. Acta Chimica Sinica, ;2016, 74(11): 865-870. doi: 10.6023/A16070372 shu

Synthesis of Solution Processable Blue AIEgens and the Device Performance

Yu Yun ^† ,
Yang Jie ^† ,
Ren Zichun ,
Xie Guohua ^*,, ,
Li Qianqian ,
Li Zhen ^*,,

1.
Department of Chemistry, Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, Wuhan University, Wuhan 430072

Corresponding author: Xie Guohua, xgh-008@163.com Li Zhen, lizhen@whu.edu.cn; lichemlab@163.com

^†

Received Date: 28 July 2016

Fund Project: and the National Natural Science Foundation of China 51573140and the National Natural Science Foundation of China 21325416National Fundamental Key Research Program 2013CB834701and the National Natural Science Foundation of China 6715751469

Figures(3)

By utilizing the special sp³ hybridization of tetraphenylmethane to break and control the intramolecular conjugation, and using silicon atom to replace the carbon atom in tetraphenylsilane, six molecules of C-4pTPE, C-4mTPE, C-4triPE, Si-4pTPE, Si-4mTPE, and Si-4triPE, were designed and successfully obtained, with tetraphenylethylene (TPE) and triphenylethylene (triPE) introduced to the core of tetraphenylmethane or tetraphenylsilane as rotors. These six molecules all possess typical aggregation induced emission (AIE) properties, they are all nearly nonemissive when readily dissolved in pure THF, but with the water fraction increasing, the PL intensity gradually increased. Due to their good AIE properties and thermal stability, they were fabricated in OLED devices by the solution process conveniently, with the maximum luminance (L_max), maximum current efficiency (η_{C, max}), maximum power efficiency (η_{p, max}) and maximum external quantum efficiency (η_{ext, max}) at 1730 cd·m^-2, 2.21 cd·A^-1, 0.77 lm·W^-1 and 1.01%, respectively.
- aggregation induced emission,
- sp³ hybridization,
- OLED device,
- solution process
1. [1]
  Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913. doi: 10.1063/1.98799
2. [2]
  Ma, Y. G.; Zhang, H.; Shen, J. C.; Che, C. Synth. Met. 1998, 94, 245. doi: 10.1016/S0379-6779(97)04166-0
3. [3]
  D'Andrade, B. W.; Forrest, S. R. Adv. Mater. 2004, 16, 1585. doi: 10.1002/(ISSN)1521-4095
4. [4]
  Li, J. Y.; Ma, C. W.; Tang, J. X.; Lee, C. S.; Lee, S. T. Chem. Mater. 2005, 17, 615. doi: 10.1021/cm048337d
5. [5]
  Li, J.; Liu, D.; Li, Y.; Lee, C. S.; Kwong, H.; Lee, S. Chem. Mater. 2005, 17, 1208. doi: 10.1021/cm034731k
6. [6]
  Braun, D.; Heeger, A. J. Appl. Phys. Lett. 1991, 58, 1982. doi: 10.1063/1.105039
7. [7]
  Wu, W. S.; Inbasekaran, M.; Hudack, M.; Welsh, D.; Yu, W. L.; Cheng, Y.; Wang, C.; Kram, S.; Tacey, M.; Bernius, M.; Fletcher, R.; Kiszka, K.; Munger, S.; O'Brien, J. Microelectron. J. 2004, 35, 343. doi: 10.1016/j.mejo.2003.07.001
8. [8]
  Bernius, M. T.; Inbasekaran, M.; O'Brien, J. J.; Wu, W. Adv. Mater. 2000, 12, 1737. doi: 10.1002/(ISSN)1521-4095
9. [9]
  Förster, T.; Kasper, K. Z. Phys. Chem.(Muenchen, Ger), 1954, 1, 275; (b) Jakubiak, R.; Collision, C. J.; Wan, W. C.; Rothberg, L. J. Phys. Chem. A 1999, 103, 2394. (c) Lemmer, U.; Heun, S.; Mahrt, R. F.; Schert, U.; Hopmeier, M.; Siegner, U.; Göbel, E. O.; Müllen, K.; Bassler, H. Chem. Phys. Lett. 1995, 240, 373.
10. [10]
  Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740; (b) Qian, L. J.; Tong, B.; Zhi, J. G.; Yang, F.; Shen, J. B.; Shi, J. B.; Dong, Y. P. Acta Chim. Sinica 2008, 66, 1134(in Chinese). (钱立军, 佟斌, 支俊格, 杨帆, 申进波, 石建兵, 董宇平, 化学学报, 2008, 66, 1134.); (c) Xun, Z. Q.; Tang, H. Y.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Zhang, X. H.; Li, Y. Acta Chim. Sinica 2015, 73, 819(in Chinese). (寻知庆, 唐海云, 曾毅, 陈金平, 于天君, 张小辉, 李嫕, 化学学报, 2015, 73, 819.)
11. [11]
  Yang, J.; Huang, J.; Li, Q.; Li, Z. J. Mater. Chem. C 2016, 4, 2663. (b) Li, Z. Sci. China Chem. 2015, 58, 969. (c) Li, Q.; Li, Z. Sci. China Chem. 2015, 58, 1800. (d) Zhang, X.; Zhang, X.; Yang, B.; Wei, Y. Chin. J. Polym. Sci. 2014, 32, 1479. (e) Wang, R.; Yuan, W.; Zhu, X. Chin. J. Polym. Sci. 2015, 33, 680. (f) Wu, W.; Tang, R.; Li, Q.; Li, Z. Chem. Soc. Rev. 2015, 44, 3997.
12. [12]
  Tung, Y. J.; Nago, T.; Hack, M.; Brown, J.; Koide, N.; Nagara, Y.; Kato, Y.; Ito, H. Dig. Tech. Pap.-Soc. Inf. Disp. Int. Symp 2004, 35, 48. (b) Lee, M. T.; Liao, C. H.; Tsai, C. H.; Chen, C. H. Adv. Mater. 2005, 17, 2493. (c) Lee, S. J.; Park, J. S.; Yoon, K. J.; Kim, Y. I.; Jin, S. H.; Kang, S. K.; Gal, Y. S.; Kang, S.; Lee, J. Y.; Kang, J. W.; Lee, S. H.; Park, H. D.; Kim, J. J. Adv. Funct. Mater. 2008, 18, 3922. (d) Lai, M. Y.; Chen, C. H.; Huang, W. S.; Lin, J. T.; Ke, T. H.; Chen, L. Y.; Tsai, M. H.; Wu, C. C. Angew. Chem., Int. Ed. 2008, 47, 581. (e) Chen, C. H.; Huang, W. S.; Lai, M. Y.; Tsao, W. C.; Lin, J. T.; Wu, Y. H.; Ke, T. H.; Chen, L. Y.; Wu, C. C. Adv. Funct. Mater. 2009, 19, 2661. (f) Zheng, C. J.; Wang, J.; Ye, J.; Lo, M. F.; Liu, X. K.; Fung, M. K.; Zhang, X. H.; Lee, C. S. Adv. Mater. 2013, 25, 2205.
13. [13]
  Farinola, G. M.; Ragni, R. Chem. Soc. Rev. 2011, 40, 3467. (b) Gather, M. C.; Köhnen, A.; Meerholz, K. Adv. Mater. 2011, 23, 233.
14. [14]
  Kang, D. M.; Kang, J. W.; Park, J. W.; Jung, S. O.; Lee, S. H.; Park, H. D.; Kim, Y. H.; Shun, S. C.; Kim, J. J.; Kwon, S. K. Adv. Mater. 2008, 20, 2003. (b) Park, T. J.; Jeon, W. S.; Park, J. J.; Kim, S. Y.; Lee, Y. K.; Jang, J.; Kwon, J. H.; Pode, R. Appl. Phys. Lett. 2008, 92, 113308.
15. [15]
  Yang, J.; Huang, J.; Sun, N.; Peng, Q.; Li, Q. Q.; Ma, D. G.; Li, Z. Chem. Eur. J. 2015, 21, 1. (b) Huang, J.; Tang, R. L.; Zhang, T.; Li, Q. Q.; Yu, G.; Xie, S. Y.; Liu, Y. Q.; Ye, S. H.; Qin, J. G.; Li, Z. Chem. Eur. J. 2014, 20, 5317. (c) Huang, J.; Sun, N.; Dong, Y.; Tang, R.; Lu, P.; Cai, P.; Li, Q.; Ma, D.; Qin, J.; Li, Z. Adv. Funct. Mater. 2013, 23, 2329. (d) Huang, J.; Sun, N.; Yang, J.; Tang, R.; Li, Q.; Ma, D.; Li, Z. Adv. Funct. Mater. 2014, 24, 7645. (e) Huang, J.; Yang, M.; Yang, J.; Tang, R.; Ye, S.; Li, Q.; Li, Z. Org. Chem. Front. 2015, 2, 1608.
16. [16]
  Wang, S. J.; Oldham Jr., W. J.; Hudack Jr., R. A.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 5695. doi: 10.1021/ja992924w
17. [17]
  Parker, C. A.; Rees, W. T. Analyst 1960, 85, 587. doi: 10.1039/an9608500587
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