稠杂环化合物在红色磷光铱配合物中的应用

doi:10.3866/PKU.WHXB201205043

摘要/Abstract

摘要：

在过去的几十年里, 有机发光二极管(OLED)由于潜在的优势, 在全彩显示领域引起了高度重视. 电致磷光材料因其优异的发光性能, 引起了人们广泛关注. 对于实际应用的平板显示器, 蓝、绿、红三基色是必不可少的. 相对于高效的绿光材料, 红光磷光材料仍然存在色纯度差、效率低和亮度不足等问题, 因此设计合适的红光材料成为具有挑战性的问题. 稠杂环化合物因发光量子效率高、发光颜色可调、平衡电荷注入及迁移等优越性能而广泛应用于红色磷光铱配合物. 本文综述了近几年稠杂环化合物在小分子、树枝状及高分子红色磷光铱配合物中的应用, 阐述了铱配合物分子结构对材料光电性质及器件性能的影响, 最后展望了稠杂环化合物在红光磷光材料中的应用前景.

关键词: 磷光材料, 铱配合物, 稠杂环化合物, 树枝状分子, 高分子

Abstract:

Organic light-emitting diodes (OLEDs) have attracted considerable attention during the last decade because of the potential advantages associated with their usage in full-color displays. Electroluminescent phosphorescent materials have also enjoyed similar levels of attention because of their excellent luminescent properties. The three primary colors, blue, green, and red, are essential for the practical application of phosphorescent complexes in flat-panel displays. Relative to the efficient green phosphorescent materials, red phosphorescent materials suffer many problems, including poor color purity, low efficiency, and low luminance, and the design of appropriate red colored materials therefore represents a significant challenge. Fused-heterocyclic compounds have been widely used in red phosphorescent iridium(III) complexes because of their high quantum efficiency, color adjustability, and balanced charge injection and migration. This review summarizes the development and application of fused-heterocyclic compounds in recent years in small molecule, dendrimer and polymeric red phosphorescent iridium(III) complexes. The influence of the molecular structures of iridium(III) complexes on the optical and electrical properties and device performances has also been described. Finally, a discussion of the prospect of developing fused-heterocyclic compounds in the red phosphorescent materials has also been provided.

Key words: Phosphorescent material, Iridium(III) complexes, Fused-heterocyclic compound, Dendrimer, Polymer

MSC2000:

O644

王玲霞, 梅群波, 颜芳, 田波, 翁洁娜, 张彬, 黄维. 稠杂环化合物在红色磷光铱配合物中的应用[J]. 物理化学学报, 2012, 28(07): 1556-1569.

WANG Ling-Xia, MEI Qun-Bo, YAN Fang, TIAN Bo, WENG Jie-Na, ZHANG Bin, HUANG Wei. Application of Fused-Heterocyclic Compounds in Red Phosphorescent Iridium(III) Complexes[J]. Acta Phys. -Chim. Sin., 2012, 28(07): 1556-1569.

参考文献

(1) Baldo, M. A.; Thompson, M. E.; Forrest, S. R. Nature 2000,403, 750. doi: 10.1038/35001541
(2) Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.;Kwong, R.; Tsyba, I.; Bortz, M.; Mui, B.; Bau, R.; Thompson,M. E. Inorg. Chem. 2001, 40, 1704. doi: 10.1021/ic0008969
(3) Adamovich, V. I.; Cordero, S. R.; Djurovich, P. I.; Tamayo, A.;Thompson, M. E.; D'Andrade, B.W.; Forrest, S. R. Organic Electronics 2003, 44, 77.
(4) Hong, H.W.; Chen, T. M. Mater. Chem. Phys. 2007, 101, 170.doi: 10.1016/j.matchemphys.2006.03.011
(5) Wang, X. Synthesis of Red-emitting Iridium Complexes andTheir Electrophosphorescence Devices. Ph.D. Dissertation,Dalian University of Technology, Dalian, 2011. [王馨. 红光铱配合物的合成及电致磷光器件的性能研究[D]. 大连: 大连理工大学, 2011.]
(6) Tong, B. H. Synthesis and Properties of Electrophosphorescentand Molecular Hybrid Luminescent Materials. Ph.D.Dissertation, Sun Yat-sen University, Guangzhou, 2008. [童碧海. 电致磷光与分子杂化发光材料的制备与性能研究[D]. 广州: 中山大学, 2011.]
(7) Tsuboyama, A.; Iwawaki, H.; Furugori, M.; Mukaide, T.;Kamatani, J.; Igawa, S.; Moriyama, T.; Miura, S.; Takiguchi, T.;Okada, S.; Hoshino, M.; Ueno, K. J. Am. Chem. Soc. 2003, 125,12971. doi: 10.1021/ja034732d
(8) Baranoff, E.; Yum, J. H.; Grätzel, M.; Nazeeruddin, M. K.Journal of Organometallic Chemistry 2009, 694, 2661. doi: 10.1016/j.jorganchem.2009.02.033
(9) Li, C. L.; Su, Y. J.; Tao, Y. T.; Chou, P. T.; Chien, C. H.; Cheng,C. C.; Liu, R. S. Adv. Funct. Mater. 2005, 15, 387. doi: 10.1002/adfm.200305100
(10) Ho, C. L.;Wong,W. Y.; Gao, Z. Q.; Chen, C. H.; Cheah, K.W.;Yao, B.; Xie, Z.;Wang, Q.; Ma, D.;Wang, L.; Yu, X. M.; Kwok,H. S.; Lin, Z. Adv. Funct. Mater. 2008, 18, 319. doi: 10.1002/adfm.200700665
(11) Chao, Y. C.; Huang, S. Y.; Chen, C. Y.; Chang, Y. F.; Meng, H.F.; Yen, F.W.; Lin, I. F.; Zan, H.W.; Horng, S. F. Synthetic Metals 2011, 161, 148. doi: 10.1016/j.synthmet.2010.11.013
(12) Chuang, T. H.; Yang, C. H.; Kao, P. C. Inorg. Chim. Acta 2009,362, 5017. doi: 10.1016/j.ica.2009.08.002
(13) Ding, J. Q.; Gao, J.; Fu, Q.; Cheng, Y. X.; Ma, D. G.;Wang, L.X. Synthetic Metals 2005, 155, 539. doi: 10.1016/j.synthmet.2005.08.034
(14) Song, M.; Park, J. S.; Kim, C. H.; Im, M. J.; Kim, J. S.; Gal, Y.S.; Lee, J.W.; Jin, S. H. Organic Electronics 2009, 10, 1412.doi: 10.1016/j.orgel.2009.07.012
(15) Li, C. X.; Sun, P. P.; Yan, L. J.; Pan, Y.; Cheng, C. J. Thin Solid Films 2008, 516, 6186. doi: 10.1016/j.tsf.2007.11.094
(16) Li, H. C.; Chou, P. T.; Hu, Y. H.; Cheng, Y. M.; Liu, R. S.Organometallics 2005, 24, 1329. doi: 10.1021/om049192n
(17) Rayabarapu, D. K.; Paulose, B. M. J. S.; Duan, J. P.; Chen, C.H. Adv. Mater. 2005, 17, 349. doi: 10.1002/adma.200400813
(18) Shao, Y.; Qiu, Y. Advance Display 1998, 16, 32. [邵炎,邱勇. 现代显示, 1998, 16, 32.]
(19) You, X. Z. Molecular Materials-optical Function Compounds;Shanghai Science and Technology Press: Shanghai, 2001. [游效曾. 分子材料-光电功能化合物. 上海: 上海科学技术出版社, 2001.]
(20) Danel, A.; Gondek, E.; Kityk, I. V. Opt. Mater. 2009, 32, 267.doi: 10.1016/j.optmat.2009.09.008
(21) Pan, T.; Ning, J. H.; Cai, H. G. Fine Chemical Intermediates2009, 39, 50. [潘彤, 宁静恒, 蔡红革. 精细化工中间体,2009, 39, 50.]
(22) Wu, Q. H.;Wang, C. H.; Song, X. M.;Wu, S. Y.; Jiang, Y. C.;Zhang, G. L. Chin. J. Appl. Chem. 2009, 26, 863. [吴秋华, 王传红, 宋溪明, 吴抒遥, 姜玉春, 张国林. 应用化学, 2009, 26,863.]
(23) Zhang, G. L.; Guo, H. Q.; Chuo, Y. T.; Zou, D. C. Acta Chim. Sin. 2005, 63, 143. [张国林, 郭海清, 啜玉涛, 邹德春. 化学学报, 2005, 63, 143.]
(24) Schneidenbach, D.; Ammermann, S.; Debeaux, M.; Freund, A.;Zöllner, M.; Daniliuc, C.; Jones, P. G.; Kowalsky,W.; Johannes,H. H. Inorg. Chem. 2010, 49, 397. doi: 10.1021/ic9009898
(25) Ha, Y.; Seo, J. H.; Kim, Y. K. Synthetic Metals 2008, 158, 548.doi: 10.1016/j.synthmet.2008.03.019
(26) Wu, Q. H.;Wang, C. H.; Song, X. M.;Wu, S. Y.; Zhang, G. L.Chemical Regent 2011, 33, 111. [吴秋华, 王传红, 宋溪明, 吴抒遥, 张国林. 化学试剂, 2011, 33, 111.]
(27) Duan, J. P.; Sun, P. P.; Cheng, C. H. Adv. Mater. 2003, 15, 224.doi: 10.1002/adma.200390051
(28) Berard, N.; Paventi, M.; Chan, K. P.; Hay, A. S. Macromol. Symp. 1994, 77, 379. doi: 10.1002/masy.19940770139
(29) Hay, A. S. Polymers Derived from Phenolphthaleins. US Patent5254663, 1993.
(30) Mei, Q. B.;Wang, L. X.; Huang,W.; Tong, B. H.; Guo, Y. H.;Weng, J. N. Synthesis of Iridium Complexes PhosphorescentMaterial Containing Phthalazine Derivatives as Ligands. CNPatent CN102180909A, 2011-09-14. [梅群波, 王玲霞,黄维, 童碧海, 郭远辉, 翁洁娜. 以酞嗪衍生物为配体的铱配合物磷光材料及其制备方法: 中国, CN102180909A[P].2011-09-14.]
(31) Tong, B. H.; Mei, Q. B.;Wang, S. J.; Fang, Y.; Meng, Y. Z.;Wang, B. J. Mater. Chem. 2008, 18, 1636. doi: 10.1039/b800977e
(32) Mei, Q. B.; Zhang, Q. F.; Tong, B. H. Chin. J. Inorg. Chem.2009, 25, 264. [梅群波, 张千峰, 童碧海. 无机化学学报,2009, 25, 264.]
(33) Mi, B. X.;Wang, P. F.; Gao, Z. Q.; Lee, C. S.; Lee, S. T.; Hong,H. L.; Chen, X. M.;Wong, M. S.; Xia, P. F.; Cheah, K.W.;Chen, C. H.; Huang,W. Adv. Mater. 2009, 21, 339. doi: 10.1002/adma.200801604
(34) Fang, Y.; Tong, B. H.; Hu, S. J.;Wang, S. J.; Meng, Y. Z.; Peng,J. B.;Wang, B. Organic Electronics 2009, 10, 618. doi: 10.1016/j.orgel.2009.02.013
(35) Fang, Y.; Hu, S. J.; Meng, Y. Z.; Peng, J. B.;Wang, B. Inorg. Chim. Acta 2009, 362, 4985. doi: 10.1016/j.ica.2009.08.007
(36) Fang, Y.; Li, Y. H.;Wang, S. J.; Meng, T. Z.; Peng, J. B.;Wang,B. Synthetic Metals 2010, 160, 2231. doi: 10.1016/j.synthmet.2010.07.035
(37) Lee, J. Y.; Park, Y. K.; Seo, S. H.; So, I. S.; Chung, H. K.; Yang,B. S.; Lee, S. J.; Park, H.; Lee, Y. S. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 357. doi: 10.1002/1521-4184(200112)334:11<357::AID-ARDP357>3.0.CO;2-Q
(38) Wissner, A.; Overbeek, E.; Reich, M. F.; Floyd, M. B.; Johnson,B. D.; Mamuya, N.; Rosfjord, E. C.; Discafani, C.; Davis, R.;Shi, X. Q.; Rabindran, S. K.; Gruber, B. C.; Ye, F.; Hallett,W.A.; Nilakantan, R.; Shen, R.;Wang, Y. F.; Greenberger, L. M.;Tsou, H. R. J. Med. Chem. 2003, 46, 49. doi: 10.1021/jm020241c
(39) Xu, G. F.; Song, B. A.; Bhadury, P. S.; Yang, S.; Zhang, P. Q.;Jin, L. H.; Xue,W.; Hu, D. Y.; Lu, P. Bioorg. Med. Chem. 2007,15, 3768. doi: 10.1016/j.bmc.2007.03.037
(40) Song, Y. H.; Yeh, S. J.; Chen, C. T.; Chi, Y.; Liu, C. S.; Yu, J. K.;Hu, Y. H.; Chou, P. T.; Peng, S. M.; Lee, G. H. Adv. Funct. Mater. 2004, 14, 1221. doi: 10.1002/adfm.200400137
(41) Du, B. S.; Lin, C. H.; Chi, Y.; Hung, J. Y.; Chung, M.W.; Lin, T.Y.; Lee, G. H.;Wong, K. T.; Chou, P. T.; Hung,W. Y.; Chiu, H.C. Inorg. Chem. 2010, 49, 8713. doi: 10.1021/ic100935b
(42) Zhang, Y. X.; Du, H. M.; Hu, L. F.; Li, H. Y.; Sun, J.; Zhang, C.L.; Zhang, H. K.; Zhang, G. X.; Gao, R. X. Red OrganicElectroluminescent Phosphorescent Iridium ComplexContaining Aryl Linked Quinazoline Derivatives as Ligands andthe Light-emitting Diodes. CN Patent CN101899296, 2010-12-01. [张玉祥, 杜红梅, 胡灵峰, 李红燕, 孙军, 张春林, 张弘科, 张国选, 高仁孝. 含芳基联喹唑啉类金属铱配合物红色有机电致磷光材料及其有机电致发光器件. 中国, CN101899296[P]. 2010-12-01.]
(43) Hsu, N. M.; Li,W. R. Angew. Chem. 2006, 45, 4138. doi: 10.1002/anie.200600004
(44) Mei, Q. B.;Wang, L. X.; Guo, Y. H.;Weng, J. N.; Yan, F.; Tian,B.; Tong, B. H. J. Mater. Chem. 2012, 22, 6878. doi: 10.1039/c2jm15160j
(45) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003,103, 893. doi: 10.1021/cr020033s
(46) Leng,W. N.; Zhou, Y. M.; Xu, Q. H.; Liu, J. Z. Polymer 2001,42, 9253. doi: 10.1016/S0032-3861(01)00464-5
(47) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.;Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003,125, 1700. doi: 10.1021/ja0289189
(48) Becker, R. S.; Lenolele, C.; Zein, A. J. Phys. Chem. 1987, 91,3509. doi: 10.1021/j100297a011
(49) Laskar, I. R.; Chen, T. M. Chem. Mater. 2004, 16, 111. doi: 10.1021/cm030410x
(50) Brooks, J.; Babayan, Y.; Lamansky, S.; Djurovich, P. I.; Tsyba,I.; Bau, R.; Thompson, M. E. Inorg. Chem. 2002, 41, 3055. doi: 10.1021/ic0255508
(51) Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razaq, F.; Lee,H. E.; Adachi, C.; Burrows, P. E.; Forrest, S. R.; Thompson, M.E. J. Am. Chem. Soc. 2001, 123, 4304. doi: 10.1021/ja003693s
(52) Tabbe, M. J.; Spitzer,W. A.; Victor, F.; Mikker, S. C.; Lee, C.C.; Sattelberg, T. R.; McKinnet, E.; Tang, J. C. J. Med. Chem.1997, 40, 3937. doi: 10.1021/jm970423k
(53) Huang,W. S.; Lin, J. T.; Chien, C. H.; Tao, Y. T.; Sun, S. S.;Wen, Y. S. Chem. Mater. 2004, 16, 2480. doi: 10.1021/cm0498943
(54) Ruan, J.W.; Fu, L.W.; Huang, Z. S. Chem. J. Chin. Univ. 2004,25, 870. [阮继武, 符立梧, 黄志纾. 高等学校化学学报,2004, 25, 870.]
(55) Anthopoulos, T. D.; Frampton, M. J.; Namdas, E. B.; Burn, P.L.; Samuel, I. D.W. Adv. Mater. 2004, 16, 557. doi: 10.1002/adma.200306095
(56) Frampton, M. J.; Namdas, E. B.; Lo, S. C.; Bun, P. L.; Samuel,I. D.W. J. Mater. Chem. 2004, 14, 2881. doi: 10.1039/b400160e
(57) Malinauskas, T.; Daskeviciene, M.; Kazlauskas, K.; Su, H. C.;Grazulevicius, J. V.; Jursenas, S.;Wu, C. C.; Getautis, V.Tetrahedron 2011, 67, 1852. doi: 10.1016/j.tet.2011.01.026
(58) Li, X. H.; Zhao, X. D.; Lü, K. L.; Zhang, A. Q. Chin. J. Inorg. Chem. 2011, 27, 303. [李襄宏, 赵鑫帝, 吕康乐, 张爱清. 无机化学学报, 2011, 27, 303.]
(59) Zhou, G. J.;Wong,W. Y.; Yao, B.; Xie, Z.;Wang, L. Angew. Chem. Int. Edit. 2007, 46, 1194.
(60) Ding, J. Q.; Lü, J. H.; Cheng, Y. X.; Xie, Z. Y.;Wang, L. X.;Jing, X. B.;Wang, F. S. Adv. Funct. Mater. 2008, 18, 2754. doi: 10.1002/adfm.200800259
(61) Guo, Y. H.;Wang, L. X.;Weng, J. N.; Yan, F.; Mei, Q. B.;Huang,W. Chin. Sci. Bull. 2011, 56, 2548. [郭远辉, 王玲霞,翁洁娜, 颜芳, 梅群波, 黄维. 科学通报, 2011, 56, 2548.]doi: 10.1360/972011-91
(62) Sandee, A. J.;Williams, C. K.; Evans, N. R.; Davies, J. E.;Boothby, C. E. J. Am. Chem. Soc. 2004, 126, 7041. doi: 10.1021/ja039445o
(63) Zhang, K.; Chen, Z.; Yang, C. L.; Gong, S. L.; Qin, J. G.; Cao,Y. Macromol. Rapid Commun. 2006, 27, 1926. doi: 10.1002/marc.200600525
(64) 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. doi: 10.1002/chem.200501095
(65) Liu, S. J.; Zhao, Q.; Deng, Y.; Xia, Y. J.; Lian, J.; Fan, Q. L.;Wang, L. H.; Huang,W. J. Phys. Chem. C 2007, 111, 1166. doi: 10.1021/jp064819w
(66) Tokito, S.; Suzuki, M.; Sato, F.; Kamachi, M.; Shirane, K.Organic Electronics 2003, 4, 105. doi: 10.1016/j.orgel.2003.08.005
(67) Jiang, J. X.; Jiang, C. Y.; Yang,W.; Zhen, H. Y.; Huang, F.; Cao,Y. Macromolecules 2005, 38, 4072. doi: 10.1021/ma0474473
(68) Yang, X. H.;Wu, F. L.; Neher, D.; Chien, C. H.; Shu, C. F.Chem. Mater. 2008, 20, 1629. doi: 10.1021/cm702789c
(69) Deng, J. Y.; Liu, Y.;Wang, Y. F.; Tan, H.; Zhang, Z. Y.; Lei, G.T.; Yu, J. T.; Zhu, M. X.; Zhu,W. G.; Cao, Y. European Polymer Journal 2011, 47, 1836. doi: 10.1016/j.eurpolymj.2011.06.015
(70) Tan, H.; Yu, J. T.; Nie, K. X.; Chen, J. H.; Deng, X. P.; Zhang,Z. Y.; Lei, G. T.; Zhu, M. X.; Liu, Y.; Zhu,W. G. Polymer 2011,52, 4792. doi: 10.1016/j.polymer.2011.07.058

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