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 |
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Authors: | Nguyen Chung Thanh Takanori Kajioka Yasunori Taga Satoshi Ogawa Yosuke Miyahara Mitsunori Oda |
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Affiliation: | a Department of Applied Chemistry, Faculty of Engineering, University of Toyama, Gofuku 3190, Toyama 930-8555, Japan b Toyota Central R&D Labs., Inc., Nagakute, Aichi 480-1192, Japan c Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan |
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Abstract: | After a preliminary search of the reaction conditions for the Suzuki-Miyaura cross-coupling of haloazulenes with arylboronic acids, the title compounds were synthesized either by the direct coupling reaction between 1,3-dihaloazulene and the corresponding N,N-disubstituted 4-aminophenylboronic acids or by a two-step sequence involving the cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Application of the title diamines to a hole-injecting material in organic electroluminescent devices was carried out to provide their prominent characteristics as a novel durable, non-cyanine and non-polyamine substance without color fade. The diamine derivatives, extended by an ethynyl unit between the azulenyl core and the 4-aminophenyl moiety, were also synthesized and found, unfortunately, unsuitable for vacuum deposition in preparing a multilayer composite. |
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Keywords: | Azulenes Suzuki-Miyaura reaction Amination Organic electroluminescent device Hole-injecting material |
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