Chem. Mater., 20 (7), 25322537, 2008. 10.1021/cm7035458
Web Release Date: March 11, 2008

Copyright © 2008 American Chemical Society

Solution-Processible Bipolar Triphenylamine-Benzimidazole Derivatives for Highly Efficient Single-Layer Organic Light-Emitting Diodes

Ziyi Ge, Teruaki Hayakawa, Shinji Ando, Mitsuru Ueda, Toshiyuki Akiike, Hidetoshi Miyamoto, Toru Kajita, and Masa-aki Kakimoto*

Department of Organic & Polymeric Materials, Tokyo Institute of Technology, Ookayama 2-12-1, Meguro-ku, Tokyo 152-8552, Japan, and Display Research Laboratories, JSR Corporation, 100 Kawajiri-cho, Yokkaichi, Mie 510-8552, Japan

Received December 12, 2007

Revised Manuscript Received January 20, 2008

Abstract:

Two solution-processible bipolar molecules, tris(3′-(1-phenyl-1H-benzimidazol-2-yl)biphenyl-4-yl)amine (TBBI) and tris(2-methyl-3′-(1-phenyl-1H-benzimidazol-2-yl)biphenyl-4-yl)amine (Me-TBBI), bearing both hole-transporting triphenylamine and electron-transporting benzimidazole moieties were newly prepared. TBBI and Me-TBBI possess excellent thermal stability with high glass-transition temperature (Tg) of 148 and 144 °C, and the decomposition temperatures (Td) of 552 and 515 °C in nitrogen, respectively. They exhibit good solubility in common solvents due to the metastructured and star-shaped configuration allowing a solution processing. TBBI and Me-TBBI were employed to fabricate phosphorescent organic light-emitting diodes (OLEDs) as the host materials doped with the guest of Ir(ppy)3 by spin coating with a single-layer structure. The solution-processed Me-TBBI device exhibited an improved performance relative to TBBI arising from the complete charge localization of HOMO and LUMO and an increase in the singlet–triplet (S0T1) energy gap. The performance of spin-coated Me-TBBI device (16400 cd m−2, 27.4 cd A−1, 4.5 lm W−1) is outstanding with respect to other work for fully solution-processed OLEDs with the similar single-layer structure.

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