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
1. [1]
  Fuzheng Zhang , Chao Shi , Jiale Li , Fulin Jia , Xinyu Liu , Feiyang Li , Xinyu Bai , Qiuxia Li , Aihua Yuan , Guohua Xie . B-embedded narrowband pure near-infrared (NIR) phosphorescent iridium(Ⅲ) complexes and solution-processed OLED application. Chinese Chemical Letters, 2025, 36(1): 109596-. doi: 10.1016/j.cclet.2024.109596
2. [2]
  Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791
3. [3]
  Tong-Tong Zhou , Guan-Yu Ding , Xue Li , Li-Li Wen , Xiao-Xu Pang , Ying-Chen Duan , Ju-Yang He , Guo-Gang Shan , Zhong-Min Su . Design of near-infrared aggregation-induced emission photosensitizers by π-bridge engineering for boosting theranostic efficacy. Chinese Chemical Letters, 2025, 36(6): 110341-. doi: 10.1016/j.cclet.2024.110341
4. [4]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
5. [5]
  Jun-Jie Fang , Zheng Liu , Yun-Peng Xie , Xing Lu . Superatomic Ag₅₈ nanoclusters incorporating a [MS₄@Ag₁₂]²⁺ (M = Mo or W) kernel show aggregation-induced emission. Chinese Chemical Letters, 2024, 35(10): 109345-. doi: 10.1016/j.cclet.2023.109345
6. [6]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168
7. [7]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
8. [8]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
9. [9]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
10. [10]
  Jun Jiang , Hui Dai , Tao Tu . Two vicinal C(sp³)-F bonds functionalization of perfluoroalkyl halides (PFAHs). Chinese Chemical Letters, 2025, 36(7): 111054-. doi: 10.1016/j.cclet.2025.111054
11. [11]
  Jing Ren , Feng-Huan Du , Xiaowei Chen , Chi Zhang . Monofluoroiodane(Ⅲ) reagent mediated Wagner−Meerwein rearrangement fluorination: Construction of quaternary C(sp³)−F bond. Chinese Chemical Letters, 2026, 37(5): 111407-. doi: 10.1016/j.cclet.2025.111407
12. [12]
  Xin-Han Wang , Ying Huang , Chun-Lin Zhang , Song Ye . γ-C(sp³)-H acylation of aliphatic amines enabled by cooperative photoredox NHC/Pd catalysis. Chinese Chemical Letters, 2026, 37(5): 111484-. doi: 10.1016/j.cclet.2025.111484
13. [13]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
14. [14]
  Xiu-Mei Xie , Hongyang Zhang , Shao-Xuan Gong , Hong-Xia Sun , Yu-Ting Liu , Xue-Ling Chen , Shuming Chen , Tian-Yu Gao , Wai-Yeung Wong , Zhen Zhang , Da-Gang Yu . Carbonylation of C(sp³)–H bonds with CO₂: Facile synthesis of 2,4-quinolinediones and related luminescent materials. Chinese Chemical Letters, 2026, 37(3): 112003-. doi: 10.1016/j.cclet.2025.112003
15. [15]
  Huai-Gui Li , Can-Ming Zhu , Weidong Yuan , Hongyi Chen , Zhengyuan Bo , Chao Deng , Yingguang Zhu , Kang Chen , Qing-Yuan Meng . Stereodivergent reductive C(sp²)-C(sp³) coupling between cycloketone oximes and vinyl halides enabled by tunable photoredox/Ti dual catalysis. Chinese Chemical Letters, 2026, 37(7): 111941-. doi: 10.1016/j.cclet.2025.111941
16. [16]
  Rui WU , Yankun ZHANG , Jiufu LU , Pengfei ZHANG , Yang WANG . Research process on radioactive ¹⁸F-labelled chemical agents as positron emission tomography imaging probes for tumour detection. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1702-1718. doi: 10.11862/CJIC.20240387
17. [17]
  Xiaobo Li , Qunyan Wu , Congzhi Wang , Jianhui Lan , Meng Zhang , Weiqun Shi . Theoretical perspectives on the reduction of Pu(Ⅳ) and Np(Ⅵ) by methylhydrazine in HNO₃ solution: Implications for Np/Pu separation. Chinese Chemical Letters, 2024, 35(7): 109359-. doi: 10.1016/j.cclet.2023.109359
18. [18]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
19. [19]
  Fengrui Yang , Debing Wang , Xinying Zhang , Jie Zhang , Zhichao Wu , Qiaoying Wang . Synergistic effects of peroxydisulfate on UV/O₃ process for tetracycline degradation: Mechanism and pathways. Chinese Chemical Letters, 2024, 35(10): 109599-. doi: 10.1016/j.cclet.2024.109599
20. [20]
  Bin Chen , Chaoyang Zheng , Dehuan Shi , Yi Huang , Renxia Deng , Yang Wei , Zheyuan Liu , Yan Yu , Shenghong Zhong . p-d orbital hybridization induced by CuGa2 promotes selective N2 electroreduction. Chinese Journal of Structural Chemistry, 2025, 44(1): 100468-100468. doi: 10.1016/j.cjsc.2024.100468

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1784)
HTML views(178)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142