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2019 , Vol. 39 >Issue 12: 3460 - 3466

DOI: https://doi.org/10.6023/cjoc201906019

研究论文

基于苊并[1,2-b]喹喔嗪为受体单元设计合成新型红光热活化延迟荧光分子

  • 俞佳 ,
  • 肖雅方 ,
  • 陈嘉雄
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  • a 苏州大学功能纳米与软物质研究院 苏州大学纳米协同创新中心 江苏省碳基功能重点实验室 江苏苏州 215123;
    b 香港城市大学化学系 香港九龙塘

收稿日期: 2019-06-17

  修回日期: 2019-07-22

  网络出版日期: 2019-08-30

基金资助

中国博士后科学基金（No.2018M640517）资助项目.

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Design and Synthesis of Novel Red Thermally Activated Delayed Fluorescent Molecule Based on Acenaphtho[1,2-b]quinoxaline Electron-Acceptor

  • Yu Jia ,
  • Xiao Yafang ,
  • Chen Jiaxiong
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  • a Institute of Functional Nano & Soft Materials (FUNSOM), Collaborative Innovation Center of Suzhou Nano Science and Technology, Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou 215123;
    b Department of Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong

Received date: 2019-06-17

  Revised date: 2019-07-22

  Online published: 2019-08-30

Supported by

Project supported by the China Postdoctoral Science Foundation (No. 2018M640517).

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摘要

采用苊并[1，2-b]喹喔嗪（AQ）作为一种新的热活化延迟荧光（TADF）电子受体（A）基团，通过与强电子给体（D）基团吩噁嗪连接成D-A结构，合成出一种新型TADF分子10，10'，10''-（苊并[1，2-b]喹喔嗪-3，9，10-三基）-三（10H-吩噁嗪）（AQ-TPXZ），该分子材料发射红色荧光.理论计算表明，该分子的轨道电子云重叠度很小.通过荧光和磷光光谱计算得出，其单线态-三线态能隙差为0.02 eV.瞬态衰减测试显示AQ-TPXZ具有瞬时寿命和延迟寿命两种组分.以AQ-TPXZ为发光材料的有机电致发光器件（OLED）实现了红光发射，峰值位于624 nm处.该器件的最大外量子效率为7.4%，高于传统的OLED的理论最大外量子效率（5%），这一结果不仅表明AQ-TPXZ为红光TADF分子，同时表明AQ可作为一种新的红光TADF电子受体片段.

关键词： 热活化延迟荧光; 苊并[1,2-b]喹喔嗪; 吩噁嗪; 红光发光分子; 有机发光器件

本文引用格式

俞佳 , 肖雅方 , 陈嘉雄 . 基于苊并[1,2-b]喹喔嗪为受体单元设计合成新型红光热活化延迟荧光分子[J]. 有机化学, 2019 , 39(12) : 3460 -3466 . DOI: 10.6023/cjoc201906019

Abstract

A new thermally activated delayed fluorescence (TADF) acceptor (A) segment, acenaphtho[1,2-b]quinoxaline (AQ) group, is designed. And a novel red TADF material 10,10',10''-(acenaphtho[1,2-b]quinoxaline-3,9,10-triyl)tris(10H-phenoxazine) (AQ-TPXZ) is developed by the conjunction of AQ group with phenoxazine as donor (D) moieties. The density functional theory calculation shows that this D-A molecule has a well separation between the highest occupied molecular orbital and the lowest unoccupied molecular orbital. And the energy splitting between the lowest singlet state and the lowest triplet state is calculated to be 0.02 eV. The transient photoluminescence decays of AQ-TPXZ doped 4,4'-di(9H-carbazol-9-yl)-1,1'-biphenyl film exhibit double-component emission decay profiles. The organic light-emitting diode (OLED) using AQ-TPXZ as dopant realizes red emission with a peak at 624 nm. Moreover, the device obtains maximum external quantum efficiency (EQE) up to 7.4%, which is higher than the theoretical maximum EQE (5%) of traditional fluorescent OLEDs. This result not only indicates that AQ-TPXZ is a red TADF material but also provides a newly electron acceptor segment for designing novel red TADF emitters.

Key words： thermally activated delayed fluorescent; acenaphtho[1,2-b]quinoxaline; phenoxazine; red emitter; organic light-emitting diode

参考文献

[1] Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610.
[2] Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lüssem, B.; Leo, K. Nature 2009, 459, 234.
[3] Di, D.; Romanov, A. S.; Yang, L.; Richter, J. M.; Rivett, J. P. H.; Jones, S.; Thomas, T. H.; Abdi Jalebi, M.; Friend, R. H.; Linnolahti, M.; Bochmann, M.; Credgington, D. Science 2017, 356, 159.
[4] Ye, Z.; Yang, J.; Ling, Z.; Zhao, Y.; Chen, G.; Zheng, Y.; Wei, B.; Shi, Y. Chin. J. Org. Chem. 2019, 39, 449(in Chinese). (叶中华, 杨佳丽, 凌志天, 赵艺, 陈果, 郑燕琼, 魏斌, 施鹰, 有机化学, 2019, 39, 449.)
[5] Xu, Y.; Liang, X.; Zhou, X.; Yuan, P.; Zhou, J.; Wang, C.; Li, B.; Hu, D.; Qiao, X.; Jiang, X.; Liu, L.; Su, S.; Ma, D.; Ma, Y. Adv. Mater. 2019, 31, 1807388.
[6] Guo, F.; Karl, A.; Xue, Q.-F.; Tam, K. C.; Forberich, K.; Brabec, C. J. Light Sci. Appl. 2017, 6, e17094.
[7] Lin, D.; Song, S.; Chen, Z.; Guo, P.; Chen, J.; Shi, H.; Mai, Y.; Song, H. Chin. J. Org. Chem. 2018, 38, 103(in Chinese). (林丹燕, 宋森川, 陈智勇, 郭鹏然, 陈江韩, 史华红, 麦裕良, 宋化灿, 有机化学, 2018, 38, 103.)
[8] Kaji, H.; Suzuki, H.; Fukushima, T.; Shizu, K.; Suzuki, K.; Kubo, S.; Komino, T.; Oiwa, H.; Suzuki, F.; Wakamiya, A.; Murata, Y.; Adachi, C. Nat. Commun. 2015, 6, 8476.
[9] Wang, Z.; Li, X.-L.; Ma, Z.; Cai, X.; Cai, C.; Su, S.-J. Adv. Funct. Mater. 2018, 28, 1706922.
[10] Chen, S.; Dai, J.; Zhou, K.; Luo, Y.; Su, S.; Pu, X.; Huang, Y.; Lu, Z. Acta Chim. Sin. 2017, 75, 367(in Chinese). (陈仕琦, 代军, 周凯峰, 罗艳菊, 苏仕健, 蒲雪梅, 黄艳, 卢志云, 化学学报, 2017, 75, 367.)
[11] Zhen, C.-G.; Dai, Y.-F.; Zeng, W.-J.; Ma, Z.; Chen, Z.-K.; Kieffer, J. Adv. Funct. Mater. 2011, 21, 699.
[12] Yuan, Y.; Chen, J.-X.; Chen, W.-C.; Ni, S.-F.; Wei, H.-X.; Ye, J.; Wong, F.-L.; Zhou, Z.-W.; Tong, Q.-X.; Lee, C.-S. Org. Electron. 2015, 18, 61.
[13] Wu, Y.; Ren, H.; Wu, Y.; Wang, B. Acta Chim. Sin. 2015, 73, 53(in Chinese). (巫友雄, 任泓扬, 吴义芳, 王炳喜, 化学学报, 2015, 73, 53.)
[14] Yang, X.; Jiao, B.; Dang, J.-S.; Sun, Y.; Wu, Y.; Zhou, G.; Wong, W.-Y. ACS Appl. Mater. Interfaces 2018, 10, 10227.
[15] Li, X.; Zhang, J.; Zhao, Z.; Wang, L.; Yang, H.; Chang, Q.; Jiang, N.; Liu, Z.; Bian, Z.; Liu, W.; Lu, Z.; Huang, C. Adv. Mater. 2018, 30, 1705005.
[16] Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 4.
[17] Chi, Y.; Tong, B.; Chou, P.-T. Coord. Chem. Rev. 2014, 281, 1.
[18] Xu, H.; Chen, R.; Sun, Q.; Huang, W.; Liu, X. Chem. Soc. Rev. 2014, 43, 3259.
[19] Yang, X.; Guo, H.; Liu, B.; Zhao, J.; Zhou, G.; Wu, Z.; Wong, W.-Y. Adv. Sci. 2018, 5, 1701067.
[20] Ai, X.; Evans, E. W.; Dong, S.; Gillett, A. J.; Guo, H.; Chen, Y.; Hele, T. J. H.; Friend, R. H.; Li, F. Nature 2018, 563, 536.
[21] Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234.
[22] Leitl, M. J.; Krylova, V. A.; Djurovich, P. I.; Thompson, M. E.; Yersin, H. J. Am. Chem. Soc. 2014, 136, 16032.
[23] Shao, S. Y.; Ding, J. Q.; Wang, L. X. Chin. J. Appl. Chem. 2018, 993(in Chinese). (邵世洋, 丁军桥, 王利祥, 应用化学, 2018, 993.)
[24] Dias, F. B.; Santos, J.; Graves, D. R.; Data, P.; Nobuyasu, R. S.; Fox, M. A.; Batsanov, A. S.; Palmeira, T.; Berberan-Santos, M. N.; Bryce, M. R.; Monkman, A. P. Adv. Sci. 2016, 3, 1600080.
[25] Chen, J.-X.; Liu, W.; Zheng, C.-J.; Wang, K.; Liang, K.; Shi, Y.-Z.; Ou, X.-M.; Zhang, X.-H. ACS Appl. Mater. Interfaces 2017, 9, 8848.
[26] Godumala, M.; Choi, S.; Park, S. Y.; Cho, M. J.; Kim, H. J.; Ahn, D. H.; Moon, J. S.; Kwon, J. H.; Choi, D. H. Chem. Mater. 2018, 30, 5005.
[27] Wang, T.-T,; Huang, X. C.; Yu, Y. J.; Yuan, Y.; Feng, M. Q.; Jiang, Z. Q. Chin. J. Org. Chem. 2019, 39, 1436(in Chinese). (王彤彤, 华晓晨, 郁友军, 袁熠, 冯敏强, 蒋佐权, 有机化学, 2019, 39, 1436.)
[28] Guo, X. G.; Feng, S. Y. Chem. Res. 2019, 30, 111(in Chinese). (郭续更, 冯松燕, 化学研究, 2019, 30, 111.)
[29] Chen, X.-L.; Jia, J.-H.; Yu, R.; Liao, J.-Z.; Yang, M.-X.; Lu, C.-Z. Angew. Chem. Int. Ed. 2017, 56, 15006.
[30] Tan, J. H.; Huo, Y. P.; Cai, N.; Ji, S. M.; Li, Z.-Z.; Zhang, L. Chin. J. Org. Chem. 2017, 37, 2457(in Chinese). (谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.)
[31] Zhang, Q.; Li, B.; Huang, S.; Nomura, H.; Tanaka, H.; Adachi, C. Nat. Photonics 2014, 8, 326.
[32] Sun, J. W.; Lee, J.-H.; Moon, C.-K.; Kim, K.-H.; Shin, H.; Kim, J.-J. Adv. Mater. 2014, 26, 5684.
[33] Pan, K.-C.; Li, S.-W.; Ho, Y.-Y.; Shiu, Y.-J.; Tsai, W.-L.; Jiao, M.; Lee, W.-K.; Wu, C.-C.; Chung, C.-L.; Chatterjee, T.; Li. Y.-S.; Wong, K.-T.; Hu, H.-C.; Chen, C.-C.; Lee, M.-T. Adv. Funct. Mater. 2016, 26, 7560.
[34] Lee, S. Y.; Yasuda, T.; Yang, Y. S.; Zhang, Q.; Adachi, C. Angew. Chem. Int. Ed. 2014, 53, 6402.
[35] Hirata, S.; Sakai, Y.; Masui, K.; Tanaka, H.; Lee, S. Y.; Nomura, H.; Nakamura, N.; Yasumatsu, M.; Nakanotani, H.; Zhang, Q.; Shizu, K.; Miyazaki, H.; Adachi, C. Nat. Mater. 2015, 14, 330.
[36] Li, J.; Nakagawa, T.; MacDonald, J.; Zhang, Q.; Nomura, H.; Miyazaki, H.; Adachi, C. Adv. Mater. 2013, 25, 3319.
[37] Zhang, Q.; Kuwabara, H.; Potscavage, W. J.; Huang, S.; Hatae, Y.; Shibata, T.; Adachi, C. J. Am. Chem. Soc. 2014, 136, 18070.
[38] Wang, S.; Cheng, Z.; Song, X.; Yan, X.; Ye, K.; Liu, Y.; Yang, G.; Wang, Y. ACS Appl. Mater. Interfaces 2017, 9, 9892.
[39] Yuan, Y.; Hu, Y.; Zhang, Y.-X.; Lin, J.-D.; Wang, Y.-K.; Jiang, Z.-Q.; Liao, L.-S.; Lee, S.-T. Adv. Funct. Mater. 2017, 27, 1700986.
[40] Chen, J.-X.; Wang, K.; Zheng, C.-J.; Zhang, M.; Shi, Y.-Z.; Tao, S.-L.; Lin, H.; Liu, W.; Tao, W.-W.; Ou, X.-M.; Zhang, X.-H. Adv. Sci. 2018, 5, 1800436.
[41] Yang, Y.; Zhao, L.; Wang, S. M.; Ding, J. Q.; Wang, L. X. Acta Polym. Sin. 2019, 50, 1(in Chinese). (杨云, 赵磊, 王淑萌, 丁军桥, 王利祥, 高分子学报, 2019, 50, 1.)
[42] Yu, L.; Wu, Z.; Xie, G.; Zeng, W.; Ma, D.; Yang, C. Chem. Sci. 2018, 9, 1385.
[43] Yuan, Y.; Chen, J.-X.; Chen, W.-C.; Ni, S.-F.; Wei, H.-X.; Ye, J.; Wong, F.-L.; Zhou, Z.-W.; Tong, Q.-X.; Lee, C.-S. Org. Electron. 2015, 18, 61.
[44] Chen, J.-X.; Liu, W.; Zheng, C.-J.; Wang, K.; Liang, K.; Shi, Y.-Z.; Ou, X.-M.; Zhang, X.-H. ACS Appl. Mater. Interfaces 2017, 9, 8848.
[45] Park, I. S.; Lee, S. Y.; Adachi, C.; Yasuda, T. Adv. Funct. Mater. 2016, 26, 1813.
[46] Lee, S. Y.; Adachi, C.; Yasuda, T. Adv. Mater. 2016, 28, 4626.
[47] Park, H.-J.; Han, S. H.; Lee, J. Y.; Han, H.; Kim, E.-G. Chem. Mater. 2018, 30, 3215.
[48] Xie, G.; Li, X.; Chen, D.; Wang, Z.; Cai, X.; Chen, D.; Li, Y.; Liu, K.; Cao, Y.; Su, S.-J. Adv. Mater. 2016, 28, 181.
[49] Zhang, D.; Song, X.; Cai, M.; Kaji, H.; Duan, L. Adv. Mater. 2018, 30, 1705406.
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