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
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