中文
Announcement
More
Progress in Chemistry 2009, Vol. 21 Issue (10): 2153-2163 Previous Articles   Next Articles

• Review •

Silole Derivatives-Based Electroluminescent Materials

Mao Linyan; Wan Junhua; Li Zhifang; Tao Lan; Qiu Huayu   

  1. (Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China)
  • Received: Revised: Online: Published:
  • Contact: Qiu Huayu E-mail:huayuqiu@163.com
  • Supported by:

    National Natural Science Foundation of China

PDF ( 2819 ) Cited
Export

EndNote

Ris

BibTeX

Silole-based π-conjugated compounds and their derivatives have been actively studied as promising electroluminescent materials because of their unique electronic structure (low-lying LUMO level), formed by σ*-π* conjugation. This article summarizes recent progress in the synthesis of silole derivatives and the applications as both emitter and electron-transport materials, respectively by 1,1,2,3,4,5-substituted siloles, silicon-bridged stilbene, dithienosilole, spiro-silole derivatives. This article explains how the silicon to tune up the electronic structure of the heterocyclic systems. The influence of molecular structures achieved by changeing the substitutes on the electronic properties of silole derivatives is discussed in detail. The future research direction of silole derivatives is also mentioned.

Contents
1 Introduction
2 Silole derivatives-based electroluminescent materials
2.1 2,3,4,5-substituted silole derivatives-based electroluminescent materials
2.2 Silicon-bridged stilbene based electroluminescent materials
2.3 Dithienosilole derivatives-based electroluminescent materials
2.4 Spiro-silole derivatives-based electroluminescent materials
3 Conclusion

CLC Number: 

[ 1 ]  Yamaguchi S , Tamao K. Bull . Chem. Soc. Jpn. , 1996 , 69 :2327 —2334
[ 2 ]  Tamao K, Uchida M, Izumizawa T, Furukawa K, Yamag-uchi S. J .Am. Chem. Soc. , 1996 , 118 : 11974 —11975
[ 3 ]  Yamaguchi S , Tamao K. Chichester : John Wiley &Sons. , 2001 , 3 :647 —694
[ 4 ]  Yamaguchi S , Tamao K. Dord-echr : Kluwer Academic Publishers ,2000 , 461 —498
[ 5 ]  Dubac J , Laporterie A , Manuel G. Chem. Rev. , 1990 , 90 : 215 —263
[ 6 ]  Colomer E , Corriu R J P , Lheureux M. Chem. Rev. , 1990 , 90 :265 —282
[ 7 ]  Hermanns J , Schmidt B. J . Chem. Soc. Perkin Trans. , 1998 , 1 :2209 —2230
[ 8 ]  Dubac J , Guerin C , Meunier P. The Chemistry of Organic Silicon Compounds. Vol . 2 (eds. Rappoport Z, Apeloig Y) , John Wiley & Sons , 1999 , Chapter 34
[ 9 ]  Braye E H , Hubel W. Chem. Ind. (Lond. ) , 1959 : 1250 —1251
[10 ]  Hissler M, Dyer P W, Reau R. Coordination Chemistry Reviews ,2003 , 244 : 1 —44
[11 ]  朱林晖(Zhu L H) , 夏海平(Xia H P) , 丁马太(DingM T) . 功能材料(Journal of Functional Materials) , 2005 , 36 (2) : 169 —172
[12 ]  Chen J W, Cao Y. Macromol . Rapid Commun. , 2007 , 28 : 1714 —1742
[13 ]  陈润峰(Chen R F) , 范曲立(Fan Q L) , 郑超(Zheng C) , 汪联辉(Wang L H) , 黄维(Huang W) . 科学通报(Chinese Science Bulletin) , 2006 , 51 : 121 —128
[14 ]  Yamaguchi S , Endo T, Uchida M, Izumizawa T, Furukawa K,Tamao K. Chem. Eur. J . , 2000 , 6 : 1683 —1692
[15 ]  Chen J W, Law C C W, Lam J W Y, Dong Y P , Lo S M F ,Williams I D , Zhu D B , Tang B Z. Chem. Mater. , 2003 , 15 :1535 —1546
[16 ]  Curtis M D. J . Am. Chem. Soc. , 1969 , 91 : 6012 —6018
[17 ]  Tang B Z, Zhu D B , Liu Y Q , et al . Chem. Commun. , 2001 ,1740 —1741
[18 ]  Yu G, Yin S , Chen J , et al . J . Am. Chem. Soc. , 2005 , 127 :6335 —6346
[19 ]  Li Z, Dong YQ , Mi B X, et al . J . Phys. Chem. B , 2005 , 109 :10061 —10066
[20 ]  Tamao K,Yamaguchi S ,Shirot M. J . Am. Chem. Soc. , 1994 , 116 :11715 —11722
[21 ]  Uchida M, Izumizawa T, Tamao K, et al . Chem. Mater. , 2001 ,13 : 2680 —2683
[22 ]  Murata H ,Malliaras G G,Uchida M, et al . Chem. Phys. Lett . ,2001 , 339 : 161 —166
[23 ]  Lee J , Liu Q D , Motala M, et al . Chem. Mater. , 2004 , 16 :1869 —1877
[24 ]  Aubouy L , Huby N , Wantz G, et al . C. R. Chimie , 2005 , 8 :1262 —1267
[25 ]  Geramita K, McBee J , Tilley D ,et al . Chem. Mater. , 2006 , 18 :3261 —3269
[26 ]  Li L , Li W, Yu J S , Li Q , et al . Proc. of SPIE , 2007 , 6722 :672242-1 —672242-6
[27 ]  Boydston A J , Yin Y, Pagenkopf B L. J . Am. Chem. Soc. , 2004 ,126 : 3724 —3725
[28 ]  Boydston AJ , Pagenkopf B L. Angew. Chem. Int . Ed. , 2004 , 43 :6336 —6338
[29 ]  Sartin M M, Boydston A J , Pagenkopf B L , Bard A J . J . Am.Chem. Soc. , 2006 , 128 : 10163 —10170
[30 ]  Kanno K I , Kira M. Chem. Lett . , 1999 , 1127 —1128
[31 ]  Tamao K, Yamaguchi S , Shiozaki M, et al . J . Am. Chem. Soc. ,1992 , 114 : 5867 —5869
[32 ]  Lee J , Liu Q D , Wang S , et al . Organometallics , 2004 , 23 :6205 —6213
[33 ]  Tang B Z, Zhan X W, Yu G, et al . J . Mater. Chem. , 2001 , 11 :2974 —2978
[34 ]  Zhan X W, Risko C , Brédas J L , et al . J . Am. Chem. Soc. ,2005 , 127 : 9021 —9029
[35 ]  Marder S R ,Risko C ,Zhan X W,et al . J . Mater. Chem. , 2006 ,16 : 3814 —3822
[36 ]  Son HJ , Han W S , Kang S O , et al . Organometallics , 2007 , 26 :519 —526
[37 ]  Zhan XW, Haldi A , Risko C , et al . J . Mater. Chem. , 2008 , 18 :3157 —3166
[38 ]  Serby M, Ijadi-Maghsoodi S , Barton T. J . 33rd Symposium on Organosilicaon Chemistry. Saginaw , MI , 2000 , PA235
[39 ]  Yamaguchi S , Xu C H , Tamao K. J . Am. Chem. Soc. , 2003 ,125 : 13662 —13663
[40 ]  Sudo T, Asao N , Yamamoto Y. J . Org. Chem. , 2000 , 65 : 8919 —8923
[41 ]  Xu C , Wakamiya A ,Yamada H. Org. Lett . , 2004 , 6 : 3707 —3710
[42 ]  Xu C. Yamada H , Wakamiya A , et al . Macromolecules , 2004 , 37 :8978 —8983
[43 ]  Kan Y H , Su Z M, Yan L K, et al . Synth. Metal . , 2005 , 152 :269 —272
[44 ]  Matsuda T, Kadowaki S , Murakami M, et al . Org. Lett . , 2007 , 9 :133 —136
[45 ]  Li L C , Xiang J F , Xu C H. Org. Lett . , 2007 , 9 : 4877 —4879
[46 ]  Shimizu M, Tatsumi H , Mochida K, et al . Chem. Asian J . 2008 ,3 : 1238 —1247
[47 ]  Ohshita J , Nodono M, Watanabe T, et al . J . Organomet . Chem. ,1998 , 553 : 487 —491
[48 ]  Ohshita J , Nodono M. Kai H , et al . Organometallics , 1999 , 18 :1453 —1459
[49 ]  Ohshita J , Lee K H , Kimura K, Kunai A. Organometallics , 2004 ,23 :5622 —5625
[50 ]  Ohshita J , Kai H , Takata A , et al . Organometallics , 2001 , 20 :4800 —4805
[51 ]  Ohshita J , Kai H , Sumida T, et al . J . Org. Chem. , 2002 , 642 :137 —142
[52 ]  Ohshita J , Kurushima Y, Lee K H. Organometallics , 2007 , 26 :6591 —6595
[53 ]  Son HJ , Han W S , Chun J Y, et al . Organometallics , 2008 , 27 :2464 —2473
[54 ]  Yu W L , Pei J , Huang W, Heeger A. Adv. Mater. , 2000 , 12 :828 —831
[55 ]  Lee S H , Jang B B , H Z. J . Am. Chem. Soc. , 2005 , 127 :9071 —9078
[56 ]  Xiao H B , Leng B , Tian H. Polymer , 2005 , 46 : 5707 —5713
[57 ]  Lee B J , Yuan Y Y, Kang YJ , et al . Adv. Funct . Mater. , 2006 ,16 : 681 —686
[58 ]  Yan D C , Ala J M, Auner N. Chem. Eur. J . , 2007 , 13 : 7204 —7214
[59 ]  Ohshita J , Lee K H , Kunai A , et al . Chem. Lett . , 2004 , 33 :892 —893

[1] Jiang Hongji*, Zhang Qingwei. Applications of Triphenyl Phosphine Oxide Derivative-Based Chromophores in the Synthesis of Organic Electroluminescent Materials [J]. Progress in Chemistry, 2016, 28(10): 1515-1527.
[2] Ma Zhijun, Lei Ting, Pei Jian*, Liu Chenjiang*. Blue Host Materials for Phosphorescent Organic Light-Emitting Diodes [J]. Progress in Chemistry, 2013, 25(06): 961-974.
[3] Zhang Lihong, Yu Qingcai, Wan Junhua*. Silole-Containing Polymer Photovoltaic Donor Materials [J]. Progress in Chemistry, 2013, 25(05): 752-760.
[4] Liu Zhitian, Hu Zhao, Shen Zhi, Hu Shuangqiang, Wang Zixing, Qi Xin. Optoelectronic Properties of Silole-Containing Polymers [J]. Progress in Chemistry, 2012, 24(0203): 377-384.
[5] . Phosphorus-Containing Organic Electroluminescent Materials [J]. Progress in Chemistry, 2010, 22(05): 898-904.
[6] . Molecular Design of Polymeric Electroluminescent Materials [J]. Progress in Chemistry, 2010, 22(04): 696-705.
[7] Meng Xianle, Zhu Weihong**,Tian He** . Dendrimeric Electroluminescent Materials [J]. Progress in Chemistry, 2007, 19(11): 1671-1680.
[8] Tang Chao1,Liu Feng2,Xu Hui3,Huang Wei1**. Polyfluorenes and Its Derivatives for Electroluminescent Materials [J]. Progress in Chemistry, 2007, 19(10): 1553-1562.
[9] Chunpeng Chai,Xinghe Fan**,Xiaofang Chen,Qifeng Zhou**. Polymer Electroluminescent Materials with 1,3,4- Oxadiazole [J]. Progress in Chemistry, 2006, 18(11): 1498-1507.