中文
Announcement
More
Progress in Chemistry 2007, Vol. 19 Issue (10): 1553-1562 Previous Articles   Next Articles

• Review •

Polyfluorenes and Its Derivatives for Electroluminescent Materials

Tang Chao1;Liu Feng2;Xu Hui3;Huang Wei1**   

  1. 1. Institute of Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing, 210003,China;

    2. Institute of Advanced Materials, Fudan University, Shanghai, 200433,China;

    3. School of Optoelectronic Engineering, Nanjing University of Posts and Telecommunications, Nanjing, 210003,China

  • Received: Revised: Online: Published:
PDF ( 3083 ) Cited
Export

EndNote

Ris

BibTeX

As an important class of electroluminescent polymers, polyfluorene and its derivatives have been paid much attention by hundreds of materials chemists because they have advantages of easy modification and high photoluminescence efficiency. As a whole in this review, the chemical modification aims at developing new electroluminescent materials through tuning frontier molecular orbitals, thermal and luminescent stability. So the focus in this review is on the relationships between the structures of polymers and their light emission properties. The synthesis methods of the polymers are firstly concisely introduced. Then the polymers have been divided into two kinds according to the difference of chemical structure. The one kind is the polymers that the main conjugation chains are only comprised of fluorene units, whose chemical modification is based on the active C9 of fluorene moiety. The other is the polymers that the main chains are comprised of fluorene and other functional groups through copolymerization.

CLC Number: 

[ 1 ] 黄春辉(Huang C H) , 李富友(Li F Y) , 黄维(Huang W) .有机电致发光材料与器件导论( Introduction to Organic Light Emitting Materials and Devices) . 上海(Shanghai ) : 复旦大学出版社(Fudan University Press) , 2005. 4
[ 2 ] Tang C W. Development of Organic Light Emitting Diodes-a Historical Perspective , The 6th International Conference on Electroluminescence of Molecular Materials and Related Phenomena ( ICEL-6) . Hong Kong , 2006
[ 3 ] Pope M, Kallmann H P , Magnante P J . Chem. Phys. , 1963 ,38 : 2042 —2043
[ 4 ] Tang C W, van Slyke S A. Appl . Phys. Lett . , 1987 , 5 : 913 —915
[ 5 ] Burroughes J H , Bradley D D C , Brown A B , Marks R N ,Mackay K, Friend R H , Burn P L , Holmes A B. Nature , 1990 ,347 : 539 —541
[ 6 ] Braun D , Heeger A J . Appl . Phys. Lett . , 1991 , 58 : 1982 —1984
[ 7 ] Gustufsson G, Cao Y, Treacy G M, Klavetter F , Colaneri N ,Heeger A J . Nature , 1992 , 357 : 477 —479
[ 8 ] Neher D. Macromol . Rapid Commun. , 2001 , 22 : 1365 —1385
[ 9 ] Yu W L , Meng H , Pei J , Huang W. J . Am. Chem. Soc. ,1998 , 120 : 11808 —11809
[10] Huang W, Meng H , Yu W L , Gao J , Heeger AJ . Adv. Mater. ,1998 , 10 : 593 —596
[11] Fukuda M, Sawada M, Yoshino K. Jpn. J . Appl . Phys. , 1989 ,28 : L1433 —L1435
[12] Pei Q B , Yang Y. J . Am. Chem. Soc. , 1996 , 118 : 7416 —7417
[13] Miyaura N , Suzuki A. Chem. Rev. , 1995 , 95 : 2457 —2483
[14] Yu W L , Pei J , Huang W, Heeger A J . Adv. Mater. , 2000 ,12 : 828 —831
[15] Zeng G, Yu W L , Chua S J , Huang W. Macromolecules , 2002 ,35 : 6907 —6914
[16] Wu Y G, Li J , Fu YQ , Bo Z S. Org. Lett . , 2004 , 6 : 3485 —3487
[17] Su H J , Wu F I , Shu C F. Macromolecules , 2004 , 34 : 7197 —7209
[18] Vak D , Chun C , Lee C L , Kim J J , Kim D Y. J . Mater.Chem. , 2004 , 14 : 1342 —1346
[19] Tseng Y H , Shih P I , Chien C H , Dixit A K, Shu C F , Liu YH ,Lee G H. Macromolecules , 2005 , 38 : 10055 —10060
[20] Setayesh S , Grimsdale A C , Weil T , Enkelmann V , Müllen K,Meghdadi F , List E J W, Leising G. J . Am. Chem. Soc. ,2001 , 123 : 946 —953
[21] Marsitzky D , Vestberg R , Blainey P , Tang B T , Hawker C J ,Carter K R. J . Am. Chem. Soc. , 2001 , 123 : 6965 —6972
[22] Lee J H , Hwang D H. Chem. Commun. , 2003 : 2836 —2837
[23] Ego B C , Grimsdale F U , Yu G, Srdanov G, Müllen K. Adv.Mater. , 2002 , 14 : 809 —811
[24] Wu F I , Reddy D S , Shu C F , Liu M S , Jen A K Y. Chem.Mater. , 2003 , 15 : 269 —274
[25] Shu C F , Dodda R , Wu F I. Macromolecules , 2003 , 36 : 6698 —6703
[26] Zhu R , Wen GA , Feng J C , Chen R F , Zhao L , Yao H P , Fan Q L , Wei W, Peng B , Huang W. Macromol . Rapid Commun. ,2005 , 26 : 1729 —1735
[27] Hwang D H , Park M J , Lee J H , Choc N S , Shim H K, Lee C.Synth. Met . , 2004 , 146 : 145 —150
[28] Bliznyuk V N , Carter S A , Scott J C , Kl? rner G, Miller R D ,Miller D C. Macromolecules , 1999 , 32 : 361 —369
[29] Uckert F , Tak Y H , Müllen K, B? ssler H. Adv. Mater. , 2000 ,12 : 905 —908
[30] Panozzo S , Vial J C , Kervella Y, Stéphan O. J . Appl . Phys. ,2002 , 92 : 3495 —3502
[31] Xiao S , Nguyen M, Gong X, Cao Y, Wu H B , Moses D , Heeger A J . Adv. Funct . Mater. , 2003 , 13 : 25 —29
[32] Lee J , Cho H J , Jung B J , Cho N S , Shim H K.Macromolecules , 2004 , 37 : 8523 —8529
[33] Chou C H , Hsu S L , Dinakaran K, Chiu M Y, Wei K H.Macromolecules , 2005 , 38 : 745 —751
[34] Pu K Y, Zhang B , Ma Z , Wang P , Qi X Y, Chen R F , Wang L H , Fan Q L , Huang W. Polymer , 2006 , 47 : 1970 —1978
[35] List E J W, Güntner R , Freitas P S D , Scherf U. Adv. Mater. ,2002 , 14 : 374 —378
[36] Lupton J M, Craig M R , Meijer E W. Appl . Phys. Lett . , 2002 ,80 : 4439 —4444
[37] Gaal M, List E J W, Scherf U. Macromolecules , 2003 , 36 :4236 —4237
[38] Chan K L , McKiernan M J , Towns C R , Holmes A B. J . Am.Chem. Soc. , 2005 , 127 : 7662 —7663
[39] Chen R F , Fan Q L , Zheng C , Huang W. Org. Lett . , 2006 , 8 :203 —205
[40] Yu W L , Pei J , Cao Y, Huang W, Heeger A J . Chem.Commum. , 1999 , 1837 —1838
[41] Yu WL , Cao Y, Pei J , Huang W, Heeger A J . Appl . Phys.Lett . , 1999 , 75 : 3270 —3272
[42] Liu B , Yu W L , Lai Y H , Huang W. Chem. Commum. , 2000 ,551 —552
[43] Zeng G, Chua S J , Huang W. Thin Solid Films , 2002 , 417 :194 —197
[44] Sung H H , Lin H C. Macromolecules , 2004 , 37 : 7945 —7954
[45] Tang R P , Tan Z A , Li Y F , Xi F. Chem. Mater. , 2006 , 18 :1053 —1061
[46] Burn P L , Holmes A B , Kraft A , Bradley D D C , Brown A R ,Friend R H , Gymer R W. Nature , 1992 , 356 : 47 —49
[47] Chao N S , Hwang D H , Lee J I , Jung B J , Shim H K.Macromolecules , 2002 , 35 : 1224 —1228
[48] Cho N S , Hwang D H , Jung B J , Lim E , Lee J , Shim H K.Macromolecules , 2004 , 37 : 5265 —5273
[49] Yang R Q , Tian R Y, Hou Q , Yang W, Cao Y. Macromolecules ,2003 , 36 : 7453 —7460
[50] Yang J , Jiang C Y, Zhang Y, Yang R Q , Yang W, Hou Q , Cao Y. Macromolecules , 2004 , 37 : 1211 —1218
[51] Hou Q , Zhou Q M, Zhang Y, Yang W, Yang R , Cao Y.Macromolecules , 2004 , 37 : 6299 —6305
[52] Huang F , Hou L T , Wu H B , Wang X H , Shen H L , Cao W,Yang W, Cao Y. J . Am. Chem. Soc. , 2004 , 126 : 9845 —9853
[53] Ego C , Marsitzky D , Becker S , Zhang J Y, Grimasdale A C ,Müllen K, Machenzie J D , Silva C , Friend R H. J . Am. Chem.Soc. , 2003 , 125 : 437 —443
[54] Lu S , Fan Q L , Xiao Y, Chua SJ , Huang W. Thin Solid Films ,2002 , 417 : 215 —220
[55] Liu J , Zhou Q G, Cheng Y X, Geng Y H , Wang L X, Ma D G,Jing X B , Wang F S. Adv. Mater. , 2005 , 17 : 2974 —2978
[56] Tu GL , Mei C Y, Zhou Q G, Cheng Y X, Geng Y H , Wang L X, Ma D G, Jing X B , Wang F S. Adv. Funct . Mater. , 2006 ,16 : 101 —106
[57] Liu J , Zhou Q G, Cheng Y X, Geng Y H , Wang L X, Ma D G,Jing XB , Wang F S. Adv. Funct . Mater. , 2006 , 16 : 957 —965
[58] Ling Q D , Kang E T , Neoh K G, Huang W. Macromolecules ,2003 , 36 : 6995 —7003
[59] Chen X, Liao J L , Liang Y, Ahmed M O , Tseng H E , Chen S A. J . Am. Chem. Soc. , 2003 , 125 : 636 —637
[60] Jiang J X, Jiang C Y, Yang W, Zhen H Y, Huang F , Cao Y.Macromolecules , 2005 , 38 : 4072 —4080
[61] Jiang J X, Xu Y H , Yang W, Guan R , Liu Z Q , Zhen H Y, Cao Y. Adv. Mater. , 2006 , 18 : 1769 —1773
[62] Liu S J , Zhao Q , Chen R F , Deng Y, Fan Q L , Li F Y, Wang L H , Huang C H , Huang W. Chem. Eur. J . , 2006 , 12 : 4351 —4361
[63] Ding J F , Day M, Robertson G, Roovers J . Macromolecules ,2002 , 35 : 3474 —3483
[64] Zhan X W, Liu Y Q , Wu X, Wang S , Zhu D B.Macromolecules , 2002 , 35 : 2529 —2537
[65] Liu B , Yu W L , Lai Y H , Huang W. Chem. Mater. , 2001 , 13 :1984 —1991.
[66] Zhan X W, Wang S , Liu Y Q , Wu X, Zhu D B. Chem.Mater. , 2003 , 15 : 1963 —1969
[67] Jin Y, Ju J , Kim J , Lee S , Kim J Y, Park S H , Son S M, Jin S H , Lee K, Suh H. Macromolecules , 2003 , 36 : 6970 —6975
[68] Liu M S , Luo J L , Jen A K Y. Chem. Mater. 2003 , 15 : 3496 —3500
[69] Peng Q , Lu Z Y, Huang Y, Xie M G, Han S H , Peng J B , Cao Y. Macromolecules , 2004 , 37 : 260 —266
[70] Miteva T , Meisel A , Knoll W, Nothofer H G, Scherf U , Müller D C , Meerholz K, Yasuda A , Nether D. Adv. Mater. , 2001 , 13 :565 —570
[71] Liu B , Huang W. Thin Solid Films , 2002 , 417 : 206 —210
[72] Wu F I , Shih P I , Shu C F , Tung Y L , Chi Y. Macromolecules ,2005 , 38 : 9028 —9036
[73] Lu S , Liu T , Ke L , Ma D G, Chua S J , Huang W.Macromolecules , 2005 , 38 : 8494 —8502
[74] Wong W Y, Liu L , Cui D M, LeungL M, Kwong C F , Lee T H ,Ng H F. Macromolecules , 2005 , 38 : 4970 —4976
[75] Cao Y, Yu G, Zhang R , Menon R , Heeger A J . Synth. Met . ,1997 , 87 : 171 —174
[76] Brown T M, Kim J S , Friend R H , Cacialli F , Daik R , Feast WJ . Appl . Phys. Lett . , 1999 , 75 : 1679 —1681
[77] Pei J , Yu W L , Huang W, Heeger A J . Chem. Commun. ,2000 : 1631 —1632
[78] Liu B , Niu Y H , Yu W L , Cao Y, Huang W. Synth. Met . ,2002 , 129 : 129 —134

[1] Yumeng Wang, Rong Yang, Qijiu Deng, Chaojiang Fan, Suzhen Zhang, Yinglin Yan. Application of Bimetallic MOFs and Their Derivatives in Electrochemical Energy Storage [J]. Progress in Chemistry, 2022, 34(2): 460-473.
[2] Zhichao Liu, Hongliang Mu, Yan Li, Liu Feng, Dong Wang, Guangwu Wen. Application of Metal-Organic Frameworks-Derived Conversion-Type Anodes in Alkali Metal-Ion Batteries [J]. Progress in Chemistry, 2021, 33(11): 2002-2023.
[3] Ni Huang, Feng Xu, Jiangbin Xia. Solid State Polymerization of Polythiophene and Its Applications [J]. Progress in Chemistry, 2019, 31(8): 1103-1115.
[4] Kun Cao, Bei Yuan, Xue Liu, Minfang Wu, Zhen Yao*. Preparation and Applications of the Chiral Norbornene Derivatives [J]. Progress in Chemistry, 2017, 29(6): 605-616.
[5] Fu Kaiqiao, Zhang Guangyan, Jiang Xulin. Synthesis and Application of Polyaspartamide Derivatives for Drug/Gene Delivery [J]. Progress in Chemistry, 2016, 28(8): 1196-1206.
[6] Hu Xiangzheng, Wang Jianmin. Preparation and Application of Chenodeoxycholic Acid and Its Derivatives [J]. Progress in Chemistry, 2016, 28(6): 814-828.
[7] Gao Peng, Gao Binbin, Gao Jianqiang, Zhang Kai, Yang Yongping, Chen Hongwei. Chitosan and Its Composites for Removal of Mercury Ion from Aqueous Solution [J]. Progress in Chemistry, 2016, 28(12): 1834-1846.
[8] Guan Li, Zhang Xiaoyuan, Sun Fuqiang, Jiang Yue, Zhong Yiping, Liu Ping. Oligothiophene Derivatives in Organic Photovoltaic Devices [J]. Progress in Chemistry, 2015, 27(10): 1435-1447.
[9] Weng Xilun, Bao Zongbi, Luo Fei, Su Baogen, Yang Yiwen, Ren Qilong. Progress in Preparation and Applications of Cellulose Derivatives-Based Chiral Stationary Phase [J]. Progress in Chemistry, 2014, 26(0203): 415-423.
[10] Zhou Guifeng, Wang Qin, Zeng Renquan, Fu Xiangkai, Yang Xinbin. Preparation and Application of Zirconium Phosphate and Its Derivatives [J]. Progress in Chemistry, 2014, 26(01): 87-99.
[11] Su Bin, Zhao Jing, Liu Chunbo, Che Guangbo, Wang Qingwei, Xu Zhanlin. Small Molecular Organic Electroluminescent Materials Based on 8-Hydroxyquinoline and Its Derivatives [J]. Progress in Chemistry, 2013, 25(07): 1090-1101.
[12] Peng Lianhui, Zhu Pengcheng, Zhang Chun*, Xu Huibi. Synthesis and Applications of Hexaphenylbenzene Derivatives [J]. Progress in Chemistry, 2013, 25(01): 77-85.
[13] Hou Chen, Zhu Hao, Li Yijing, Li Yanfeng. Immobilized Proline and Its Derivatives Employed in the Catalysis of Asymmetric Organic Synthesis [J]. Progress in Chemistry, 2012, (9): 1729-1741.
[14] Hu Huiyuan, Zhu Hong. Adsorption of Heavy Metal Ions by Chitosan and Its Derivatives [J]. Progress in Chemistry, 2012, 24(11): 2212-2223.
[15] Wan Wubo, Zhao Zongbin, Fan Yanru, Hu Han, Zhou Quan, Qiu Jieshan. Graphene Derivatives: Synthesis and Applications [J]. Progress in Chemistry, 2011, 23(9): 1883-1891.