Issue 24, 2005
From the journal:

Journal of Materials Chemistry

New 9-fluorene-type trispirocyclic compounds for thermally stable hole transport materials in OLEDs

Makoto Kimura,*a   Seiichi Kuwano,a   Yasuhiko Sawaki,a   Hisayoshi Fujikawa,b   Koji Noda,b   Yasunori Taga*b  and  Katsuhiko Takagi*a  

* Corresponding authors

a Department of Applied Chemistry and Crystalline Materials Science, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Japan
E-mail: ktakagi@apchem.nagoya-u.ac.jp

b Toyota Central Research and Development Laboratories, Inc., Nagakute, Aichi, Japan

Abstract

A novel trispirocyclic hydrocarbon having three 9-fluorene moieties around the core of truxene (5) was prepared readily via coupling of truxenone with 2-bromobiphenyl; 5 was a high melting (>500 °C) solid. For the application of 5 to an effective hole transport material (HTM) in the OLED, a triphenylamine derivative carrying six diphenylamino groups at the 2- and 7-positions of each 9-fluorene moiety (6) was designed in order to get high thermal stability as an improved material of the TPD type HTM. The synthesis of 6 was easily achieved using 4,4′-bis(diphenylamino)-2-bromobiphenyl (9). The trispirocyclic 6 was found to show a glass transition temperature as high as 170 °C. It effects the formation of its stable cation radical upon electrooxidation in solution, and amorphous thin films in solid. A multi-layered EL device for 6 as an HTM using Alq3 as an electron transporting emitter showed good EL characteristics such as the maximum luminance of 37 000 cd m−2 at 14 V. Thus, the hexakis(diphenylamino)substituted trispirocycle 6 (TX-F6S) can be used as an efficient and thermally stable HTM in OLEDs.

Graphical abstract: New 9-fluorene-type trispirocyclic compounds for thermally stable hole transport materials in OLEDs

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Article information

DOI
https://doi.org/10.1039/B502268A
Article type
Paper
Submitted
14 Feb 2005
Accepted
19 Apr 2005
First published
04 May 2005

J. Mater. Chem., 2005,15, 2393-2398

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New 9-fluorene-type trispirocyclic compounds for thermally stable hole transport materials in OLEDs

M. Kimura, S. Kuwano, Y. Sawaki, H. Fujikawa, K. Noda, Y. Taga and K. Takagi, J. Mater. Chem., 2005, 15, 2393 DOI: 10.1039/B502268A

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