Synthesis and properties of N,N,N′,N′-tetrasubstituted 1,3-bis(5aminothien-2-yl)azulenes and their application as a hole-injecting material in organic light-emitting devices

被引：29
|
作者：
Oda, Mitsunori [1 ]
Thanh, Nguyen Chung [2 ]
Ikai, Masamichi
Fujikawa, Hisayoshi [3 ]
Nakajima, Keita [2 ,3 ]
Kuroda, Shigeyasu [2 ]
机构：
[1] Shinshu Univ, Fac Sci, Dept Chem, Matsumoto, Nagano 3908621, Japan
[2] Toyama Univ, Fac Engn, Dept Appl Chem, Toyama 9308555, Japan
[3] Toyota Cent Res & Dev Labs Inc, Nagakute, Aichi 4801192, Japan
来源：
TETRAHEDRON | 2007年 / 63卷 / 43期
关键词：
azulenes; thiophenes; amination; organic light-emitting device; hole-injecting material;
D O I：
10.1016/j.tet.2007.08.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two title compounds, N,N,N',N'-tetraphenyl-1,3-bis(5-aminothien-2-yl)azulene (3a) and 1,3-bis{5-(9-carbazolyl)thien-2-yl}azulene (3b), were synthesized from 1,3-di(2-thienyl)azulene (4) by a two-step sequence involving bromination and subsequent Pd-catalyzed amination. These compounds were characterized by spectroscopic analyses and the structure of 3a was determined by X-ray crystallographic analysis. Their HOMO energy levels were estimated using their electrochemical oxidation potentials, and these compounds were used as a hole-injecting material in organic light-emitting devices. The device with 3a showed greater durability than that with copper phthalocyanine. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10608 / 10614
页数：7
相关论文
共 50 条
  • [1] Synthesis of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices
    Thanh, Nguyen Chung
    Ikai, Masamichi
    Kajioka, Takanori
    Fujikawa, Hisayoshi
    Taga, Yasunori
    Zhang, Yanmei
    Ogawa, Satoshi
    Shimada, Hiroko
    Miyahara, Yosuke
    Kuroda, Shigeyasu
    Oda, Mitsunori
    TETRAHEDRON, 2006, 62 (48) : 11227 - 11239
  • [2] Application of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes to hole-injecting materials for durable organic EL devices without color fade
    Oda, M
    Thanh, NC
    Ikai, M
    Kajioka, T
    Fujikawa, H
    Taga, Y
    Ogawa, S
    Shimada, H
    Kuroda, S
    CHEMISTRY LETTERS, 2005, 34 (06) : 754 - 755
  • [3] Electron blocking and hole injection:: The role of N,N′-bis(naphthalen-1-y)-N,N′-bis(phenyl)benzidine in organic light-emitting devices
    Zhang, ST
    Wang, ZJ
    Zhao, JM
    Zhan, YQ
    Wu, Y
    Zhou, YC
    Ding, XM
    Hou, XY
    APPLIED PHYSICS LETTERS, 2004, 84 (15) : 2916 - 2918
  • [4] Influence of the thickness of N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl) benzidine layer on the performance of organic light-emitting diodes
    Bo Jiao
    Zhaoxin Wu
    Xingwei Yan
    Xun Hou
    Applied Physics A, 2010, 98
  • [5] Influence of the thickness of N,N'-Bis(naphthalene-1-yl)-N,N'-bis(phenyl) benzidine layer on the performance of organic light-emitting diodes
    Jiao, Bo
    Wu, Zhaoxin
    Yan, Xingwei
    Hou, Xun
    APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING, 2010, 98 (01): : 239 - 243
  • [6] Organic Light-Emitting Devices Consisting of N-Triarylamine-Based Hole Injecting/Transporting Materials
    Cho, Ho Young
    Park, Lee Soon
    Han, Yoon Soo
    Kwon, Younghwan
    Ham, Jae-Yong
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2009, 498 : 314 - 322
  • [7] Organic light emitting diodes using NaCl:N,N′-bis(naphthalene-1-yl)-N,N′-bis(phenyl)benzidine composite as a hole injection buffer layer
    Kim, Jeongho
    Kim, Myungseop
    Kim, Jeong Won
    Yi, Yeonjin
    Kang, Heon
    JOURNAL OF APPLIED PHYSICS, 2010, 108 (10)
  • [8] Synthesis and characteristics of poly[N,N′-diphenyl-N,N′-bis(4-aminobiphenyl)-(1,1′-biphenyl)-4,4′-diamine pyromellitimide] as a hole injecting and transporting layer for hybrid organic light-emitting device
    Kim, Y
    Han, K
    Ha, CS
    MACROMOLECULES, 2002, 35 (23) : 8759 - 8767
  • [9] Bis[μ-1,3-bis(4,5-dihydroimidazol-2-yl)-benzene-κ2N,N′]bis[dichloridozinc(II)] N:N′-dimethylformamide disolvate
    Cheng, Lin
    Zhang, Ya-Wen
    Sun, Yan-Yan
    Zhang, Gong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : M1236 - U211
  • [10] Study on the performance of organic light-emitting diode with N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine doped in polystyrene as hole transporting layer
    Deng, Jing
    Xie, Guangzhong
    Yu, Junsheng
    Suo, Fan
    Li, Weizhi
    Jiang, Yadong
    ADVANCED OPTICAL MANUFACTURING TECHNOLOGIES, PTS 1 AND 2, 2007, 6722
12345