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Synthesis and properties of N,N,N′,N′-tetrasubstituted 1,3-bis(5-aminothien-2-yl)azulenes and their application as a hole-injecting material in organic light-emitting devices |
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| Authors: | Mitsunori Oda Nguyen Chung Thanh Hisayoshi Fujikawa Shigeyasu Kuroda |
| Institution: | a Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan b Department of Applied Chemistry, Faculty of Engineering, University of Toyama, Gofuku 3190, Toyama 930-8555, Japan c Toyota Central R&D Labs., Inc., Nagakute, Aichi 480-1192, Japan |
| Abstract: | 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. |
| Keywords: | Azulenes Thiophenes Amination Organic light-emitting device Hole-injecting material |
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