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化学进展 2015, Vol. 27 Issue (8): 986-1001 DOI: 10.7536/PC150151 前一篇   后一篇

• 综述与评论 •

有机电致发光器件中的双极性蓝光荧光材料

钟渤凡1,2,3, 王世荣1,2,3, 肖殷1,2,3, 李祥高*1,2,3   

  1. 1. 天津大学化工学院 天津 30007;
    2. 天津化学化工协同创新中心 天津 300072;
    3. 天津市功能精细化学品技术工程中心 天津 300072
  • 收稿日期:2015-01-01 修回日期:2015-04-01 出版日期:2015-08-15 发布日期:2015-06-05
  • 通讯作者: 李祥高 E-mail:lixianggao@tju.edu.cn
  • 基金资助:
    国家高技术研究发展计划(863) 项目(No. 2015AA033402)和天津市科技计划项目(No. 14TXGCCX00017)资助

Bipolar Blue Fluorescent Materials for Organic Light-Emitting Devices

Zhong Bofan1,2,3, Wang Shirong1,2,3, Xiao Yin1,2,3, Li Xianggao*1,2,3   

  1. 1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 30007;
    2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China;
    3. Tianjin Engineering Center of Functional Fine Chemicals, Tianjin 300072, China
  • Received:2015-01-01 Revised:2015-04-01 Online:2015-08-15 Published:2015-06-05
  • Supported by:
    The work was supported by the National High Technology Research and Development Program of China (863 Program)(No. 2015AA033402) and the Tianjin Sci?Tech Project(No. 14TXGCCX00017).
双极性蓝光荧光材料因其双极传输特性和发光特性,为有机电致发光器件性能提升及结构简化提供了新途径。大多数双极性蓝光荧光材料在结构上符合电子给体-π桥-电子受体(D-π-A),根据电子受体单元,本文将其分为二苯磷/磺酰类、二米基硼类、五元杂环类、六元氮杂环类等,讨论了各类材料结构特点及在器件中的应用性能,对非D-π-A型材料也进行了总结。同时,介绍了热活化延迟荧光特性的双极性蓝光荧光材料的进展情况。最后,对双极性蓝光荧光材料中存在的问题进行了提炼,并展望了其发展前景。
Bipolar blue fluorescent materials capable of bipolar charge transport and possessing high photoluminescence quantum yields have paved the way for the development of high-performance and simple structure organic light-emitting devices. Bipolar blue fluorescent materials with the general architecture of “donor-π bridge-acceptor” mainly include diphenyl phosphoryl/sulfonyl based compounds, dimesitylboryl-based compounds, five-membered heterocyclic based compounds, six-membered N-heterocyclic based compounds, their molecular structure and device performances are reviewed in this article, materials without the “D-π-A” structure are also introduced. In addition, materials with thermally activated delayed fluorescence properties, which have received much attention, are summarized. Finally, the challenges and prospective tendency of the bipolar blue fluorescent materials are given based on the current research.

Contents
1 Introduction
2 D-π-A type bipolar blue fluorescent materials
2.1 Diphenyl phosphoryl/sulfonyl based compounds
2.2 Dimesitylboryl-based compounds
2.3 Five-membered heterocyclic based compounds
2.4 Six-membered N-heterocyclic based compounds
2.5 Other D-π-A type bipolar compounds
3 Non D-π-A type bipolar blue fluorescent materials
4 Bipolar blue fluorescent materials with thermally activated delayed fluorescence properties
5 Problems and outlook

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[1] 陈金鑫(Chen J X), 黄孝文(Huang X W). OLED 梦幻显示器——材料与器件(OLED Dream Display——Materials and Devices). 北京:人民邮电出版社(Beijing:Posts & Telecom Press), 2011. 2.
[2] 陈金鑫(Chen J X), 陈锦地(Chen J D), 吴忠帜(Wu Z Z). 白光 OLED 照明(White OLED for Lighting). 上海: 上海交通大学出版社(Shanghai: Shanghai Jiaotong University Press), 2009. 3.
[3] Lüssem B, Meerheim R, Hofmann S, Furno M, Reineke S, Thomschke M, Leo K. Proceedings of the SID Symposium Digest of Technical Papers. Wiley Online Library, 2010, 691.
[4] Li J, Nakagawa T, MacDonald J, Zhang Q, Nomura H, Miyazaki H, Adachi C. Adv. Mater., 2013, 25: 3319.
[5] Helander M G, Wang Z B, Qiu J, Greiner M T, Puzzo D P, Liu Z W, Lu Z H. Science, 2011, 332: 944.
[6] Sun J W, Lee J H, Moon C K, Kim K H, Shin H, Kim J J. Adv. Mater., 2014, 26: 5684.
[7] Kim M, Lee J Y. Adv. Funct. Mater., 2014, 24: 4164.
[8] 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.
[9] Kang Y, Chang Y L, Lu J S, Ko S B, Rao Y, Varlan M, Lu Z H, Wang S. J. Mater. Chem. C, 2013, 1: 441.
[10] Tung Y J, Ngo T, Hack M, Brown J, Koide N, Nagara Y, Kato Y, Ito H. Proceedings of the SID Symposium Digest of Technical Papers. Wiley Online Library, 2004, 48.
[11] Sun Y, Giebink N C, Kanno H, Ma B, Thompson M E, Forrest S R. Nature, 2006, 440: 908.
[12] Yang C H, Cheng Y M, Chi Y, Hsu C J, Fang F C, Wong K T, Chou P T, Chang C H, Tsai M H, Wu C C. Angew. Chem. Int. Ed., 2007, 46: 2418.
[13] Chang C F, Cheng Y M, Chi Y, Chiu Y C, Lin C C, Lee G H, Chou P T, Chen C C, Chang C H, Wu C C. Angew. Chem. Int. Ed., 2008, 47: 4542.
[14] Ye J, Zheng C J, Ou X M, Zhang X H, Fung M K, Lee C S. Adv. Mater., 2012, 24: 3410.
[15] Duan L, Qiao J, Sun Y, Qiu Y. Adv. Mater., 2011, 23: 1137.
[16] Yamaguchi Y, Fujiyama T, Tanaka H, Yokoyama M. Chem. Mater., 1990, 2: 341.
[17] Jeon S O, Lee J Y. J. Mater. Chem., 2012, 22: 4233.
[18] Liu X K, Zheng C J, Lo M F, Xiao J, Lee C S, Fung M K, Zhang X H. Chem. Commun., 2014, 50: 2027.
[19] Yu D, Zhao F, Zhang Z, Han C, Xu H, Li J, Ma D, Yan P. Chem. Commun., 2012, 48: 6157.
[20] 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.
[21] Ye J, Chen Z, Fung M K, Zheng C, Ou X, Zhang X, Yuan Y, Lee C S. Chem. Mater., 2013, 25: 2630.
[22] Jia W L, Feng X D, Bai D R, Lu Z H, Wang S, Vamvounis G. Chem. Mater., 2005, 17: 164.
[23] Zhang W, He Z, Wang Y, Zhao S. Synthetic Met., 2011, 161: 2323.
[24] Lin S L, Chan L H, Lee R H, Yen M Y, Kuo W J, Chen C T, Jeng R J. Adv. Mater., 2008, 20: 3947.
[25] Shi H, Zhang W, Dong X, Wu X, Wu Y, Fang L, Miao Y, Wang H. Dyes Pigments, 2014, 104: 34.
[26] Thirion D, Rault Berthelot J, Vignau L, Poriel C. Org. Lett., 2011, 13: 4418.
[27] 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.
[28] Liao Y L, Lin C Y, Wong K T, Hou T H, Hung W Y. Org. Lett., 2007, 9: 4511.
[29] Gong S, Zhao Y, Wang M, Yang C, Zhong C, Qin J, Ma D. Chem. Asian J., 2010, 5: 2093.
[30] Huang J, Su J H, Li X, Lam M K, Fung K M, Fan H H, Cheah K W, Chen C H, Tian H. J. Mater. Chem., 2011, 21: 2957.
[31] Yang X, Zheng S, Bottger R, Chae H S, Tanaka T, Li S, Mochizuki A, Jabbour G E. J. Phys. Chem. C, 2011, 115: 14347.
[32] Hung W Y, Chi L C, Chen W J, Chen Y M, Chou S H, Wong K T. J. Mater. Chem., 2010, 20: 10113.
[33] Zhang Y, Lai S L, Tong Q X, Lo M F, Ng T W, Chan M Y, Wen Z C, He J, Jeff K S, Tang X L. Chem. Mater., 2012, 24: 61.
[34] Gao Z, Wang Z, Shan T, Liu Y, Shen F, Pan Y, Zhang H, He X, Lu P, Yang B. Org. Electron., 2014, 15: 2667.
[35] Yuan Y, Chen J X, Lu F, Tong Q X, Yang Q D, Mo H W, Ng T W, Wong F L, Guo Z Q, Ye J. Chem. Mater., 2013, 25: 4957.
[36] Li W, Liu D, Shen F, Ma D, Wang Z, Feng T, Xu Y, Yang B, Ma Y. Adv. Funct. Mater., 2012, 22: 2797.
[37] Li W, Yao L, Liu H, Wang Z, Zhang S, Xiao R, Zhang H, Lu P, Yang B, Ma Y. J. Mater. Chem. C, 2014, 2: 4733.
[38] Hamada Y, Adachi C, Tsutsui T, Saito S. Jpn. J. Appl. Phys., 1992, 31: 1812.
[39] Tao Y, Wang Q, Shang Y, Yang C, Ao L, Qin J, Ma D, Shuai Z. Chem. Commun., 2009, (1): 77.
[40] Kamtekar K T, Wang C, Bettington S, Batsanov A S, Perepichka I F, Bryce M R, Ahn J H, Rabinal M, Petty M C. J. Mater. Chem., 2006, 16: 3823.
[41] Fisher A L, Linton K E, Kamtekar K T, Pearson C, Bryce M R, Petty M C. Chem. Mater., 2011, 23: 1640.
[42] Li Z H, Wong M S, Fukutani H, Tao Y. Org. Lett., 2006, 8: 4271.
[43] Feng X J, Chen S F, Ni Y, Wong M S, Lam M M K, Cheah K W, Lai G Q. Org. Electron., 2014, 15: 57.
[44] Su S J, Chiba T, Takeda T, Kido J. Adv. Mater., 2008, 20: 2125.
[45] Chi C C, Chiang C L, Liu S W, Yueh H, Chen C T, Chen C T. J. Mater. Chem., 2009, 19: 5561.
[46] Tang X, Yao L, Liu H, Shen F, Zhang S, Zhang H, Lu P, Ma Y. Chemistry-A European Journal, 2014, 20: 7589.
[47] Liu C L, Zheng C J, Liu X K, Chen Z, Yang J P, Li F, Ou X M, Zhang X H. J. Mater. Chem. C, 2015.
[48] Tonzola C J, Alam M M, Kaminsky W, Jenekhe S A. J. Am. Chem. Soc., 2003, 125: 13548.
[49] 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. Adv. Funct. Mater., 2008, 18: 3922.
[50] Tao S, Li L, Yu J, Jiang Y, Zhou Y, Lee C S, Lee S T, Zhang X, Kwon O. Chem. Mater., 2009, 21: 1284.
[51] Hancock J M, Gifford A P, Zhu Y, Lou Y, Jenekhe S A. Chem. Mater., 2006, 18: 4924.
[52] Liu J, Teng M Y, Zhang X P, Wang K, Li C H, Zheng Y X, You X Z. Org. Electron., 2012, 13: 2177.
[53] Liu X K, Zheng C J, Lo M F, Xiao J, Chen Z, Liu C L, Lee C S, Fung M K, Zhang X H. Chem. Mater., 2013, 25: 4454.
[54] Hu J Y, Pu Y J, Satoh F, Kawata S, Katagiri H, Sasabe H, Kido J. Adv. Funct. Mater., 2014, 24: 2064.
[55] Wu C C, Liu T L, Hung W Y, Lin Y T, Wong K T, Chen R T, Chen Y M, Chien Y Y. J. Am. Chem. Soc., 2003, 125: 3710.
[56] Wu C C, Lin Y T, Wong K T, Chen R T, Chien Y Y. Adv. Mater., 2004, 16: 61.
[57] Tao S, Lee C S, Lee S T, Zhang X. Appl. Phys. Lett., 2007, 91: 013507.
[58] Park Y, Lee J H, Jung D H, Liu S H, Lin Y H, Chen L Y, Wu C C, Park J. J. Mater. Chem., 2010, 20: 5930.
[59] Tao S, Jiang Y, Lai S L, Fung M K, Zhou Y, Zhang X, Zhao W, Lee C S. Org. Electron., 2011, 12: 358.
[60] Chen W C, Yuan Y, Wu G F, Wei H X, Ye J, Chen M, Lu F, Tong Q X, Wong F L, Lee C S. Org. Electron., 2015, 17: 159.
[61] Kondakov D Y, Pawlik T D, Hatwar T K, Spindler J P. J. Appl. Phys., 2009, 106: 124510.
[62] King S M, Cass M, Pintani M, Coward C, Dias F B, Monkman A P, Roberts M. J. Appl. Phys., 2011, 109: 074502.
[63] Czerwieniec R, Yu J, Yersin H. Inorg. Chem., 2011, 50: 8293.
[64] Chen X L, Yu R, Zhang Q K, Zhou L J, Wu X Y, Zhang Q, Lu C Z. Chem. Mater., 2013, 25: 3910.
[65] Osawa M. Chem.Commun., 2014, 50: 1801.
[66] Uoyama H, Goushi K, Shizu K, Nomura H, Adachi C. Nature, 2012, 492: 234.
[67] Zhang D, Duan L, Li C, Li Y, Li H, Zhang D, Qiu Y. Adv. Mater., 2014, 26: 5050.
[68] Masui K, Nakanotani H, Adachi C. Org. Electron., 2013, 14: 2721.
[69] Huang B, Qi Q, Jiang W, Tang J, Liu Y, Fan W, Yin Z, Shi F, Ban X, Xu H. Dyes Pigments, 2014, 111:135.
[70] Endo A, Sato K, Yoshimura K, Kai T, Kawada A, Miyazaki H, Adachi C. Appl. Phys. Lett., 2011, 98: 083302.
[71] Zhang Q, Li J, Shizu K, Huang S, Hirata S, Miyazaki H, Adachi C. J. Am. Chem. Soc., 2012, 134: 14706.
[72] Wu S, Aonuma M, Zhang Q, Huang S, Nakagawa T, Kuwabara K, Adachi C. J. Mater. Chem. C, 2014, 2: 421.
[73] Lee Y S, Yasuda T, Nomura H, Adachi C. Appl. Phys. Lett., 2012, 101: 0933061.
[74] Lee J, Shizu K, Tanaka H, Nomura H, Yasuda T, Adachi C. J. Mater. Chem. C, 2013, 1: 4599.
[75] Zhang Q, Li B, Huang S, Nomura H, Tanaka H, Adachi C. Nat. Photonics, 2014, 8: 326.
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