Synthesis and Properties of Novel Luminescent Compounds Containing Triphenylamine and Bipyridine Units

Chemical Research in Chinese Universities ›› 2012, Vol. 28 ›› Issue (2): 313-318 .

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Synthesis and Properties of Novel Luminescent Compounds Containing Triphenylamine and Bipyridine Units

Lü Hai-jun^1,2, LI Xiang-gao¹, WANG Shi-rong¹, GAO Wen-zheng¹, WANG Sha-sha¹

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. China

Received:2011-03-08 Revised:2011-05-24 Online:2012-03-25 Published:2012-03-08
Supported by:
Supported by the National High-Tech Research and Development Program of China(No.2008AA03A315) and the Natural Science Foundation of Tianjin City, China(No.08JCZDJC16900).

Abstract

Abstract: Blue luminescent compounds T1―T4 containing triphenylamine donors, bipyridine acceptors and olefinic linkers were synthesized and characterized by 1H NMR, 13C NMR and high resolution mass spectrometry(HRMS). Four compounds T1―T4 exhibit excellent solubility in common solvents and good film forming properties. Quantum chemical calculations show that compounds T1―T4 have asymmetric linear structures and the proper highest occupied molecular orbital(HOMO) levels. The UV-Vis absorption and fluorescence emission spectra of the four compounds in dilute chloroform solutions and on the solid films were measured. It reveals that compounds T1―T4 exhibit similar spectral behavior, suggesting that these compounds can form amorphous state in solid films. The calculated absorption and emission spectra of compounds T1―T4 are in good agreement with experimentally determined ones. Compounds T1―T4 have absolute fluorescence quantum yield above 17% in dilute chloroform solutions. Four compounds possess high glass-transition temperature(T_g) exceeding 97 °C and the maximum T_g is 155.28 °C for compound T3. Cyclic voltammetry measurements show that these compounds have proper HOMO levels in a range of –5.01― –5.13 eV for hole injection. The properties of compounds T1―T4 indicate that these compounds are candidates for the application in organic light-emitting devices(OLEDs) as hole-transporting materials(HTMs).

Key words: Luminescent compound, Triphenylamine, Bipyridine, Hole-transporting material

Lü Hai-jun, LI Xiang-gao, WANG Shi-rong, GAO Wen-zheng, WANG Sha-sha. Synthesis and Properties of Novel Luminescent Compounds Containing Triphenylamine and Bipyridine Units[J]. Chemical Research in Chinese Universities, 2012, 28(2): 313-318 .

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Synthesis and Properties of Novel Luminescent Compounds Containing Triphenylamine and Bipyridine Units

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