Synthesis of asymmetric biphenyl derivatives for optoelectronic applications

• Published in: Optical materials Vol. 35; no. 12; pp. 2095 - 2101
• Main Authors: Zhu, Cai-Cai, Guo, Kun-Ping, Liu, Wang-Bo, He, Yan-Bo, Li, Zhi-Mei, Gao, Xi-Cun, Deng, Feng-Jie, Wei, Bin
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier B.V 01.10.2013; Elsevier
• Subjects: Applied sciences; Asymmetry; Back propagation; Backbone; Biphenyl derivatives; Carbazole; Derivatives; Electronics; Emittance; Exact sciences and technology; Fluorescence; Optoelectronic devices; Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices; Suzuki coupling; Synthesis; Tetraphenylsilane; Transport; Triphenylamine; Ullmann coupling; Suzuki coupling; Ullmann coupling; Biphenyl derivatives; Triphenylamine; Carbazole; Tetraphenylsilane; Fluorescence spectrum; Fluorescence; Multiple layer; Quantum yield; Light emitting diode; Cyclic voltammetry; Optical properties; Visible radiation; Biphenyl; Oxidation; Blue light; Organic compounds
• ISSN: 0925-3467; 1873-1252
• DOI: 10.1016/j.optmat.2013.05.027

•Ten compounds with biphenyl as backbone was asymmetrically modified.•These compounds emit intense pure-blue with high quantum yields up to 80%.•The cyclic voltammograms are completely reversible.•These compounds are useful for blue-emitting, hole-transport and host materials. We report the synthesis and optical properties of a series of ten organic compounds with biphenyl as the backbone and asymmetrically modified by triphenylamines, carbazoles and tetraphenylsilanes (BP 1-10). BP 1-10 were synthesized mainly by Ullmann coupling reaction and Suzuki cross-coupling reaction and characterized by EA, NMR, MS, UV–Vis, DSC, TGA, fluorescence spectra and cyclic voltammetry. They exhibit reversible electrochemical behavior with low oxidation potentials and emit intense pure-blue light with high fluorescence quantum yields (up to 80%). BP 1 was fabricated into multi-layered light-emitting diodes as blue-emitting, host and hole transport materials. Based on the performance of BP 1 and the similarity in chemical structure to those compounds reported in literature, these compounds are expected to be good and versatile hole transport, host and blue emitting materials.