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Synthesis of π-Conjugated Polymers Containing Fluorinated Arylene Units via Direct Arylation: Efficient Synthetic Method of Materials for OLEDs

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† Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan
‡ Advanced Materials Research Laboratory, Sumitomo Chemical Co., Ltd., 6 Kitahara, Tsukuba 300-3294, Japan
§ Nagoya Municipal Industrial Research Institute, 3-4-41, Rokuban, Atsuta-ku, Nagoya 456-0058, Japan
*E-mail: (J.K.) [email protected]; (T.K.) [email protected]
Cite this: Macromolecules 2012, 45, 10, 4128–4133
Publication Date (Web):May 8, 2012
https://doi.org/10.1021/ma3004899
Copyright © 2012 American Chemical Society
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Abstract

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Polycondensation via direct arylation of tetrafluorobenzene or octafluorobiphenyl was investigated for the synthesis of π-conjugated polymers consisting of fluorinated arylene units. The optimization of reaction conditions revealed that a combination of Pd(OAc)2 and PtBu2Me-HBF4 is the most efficient catalytic system for the polycondensation reactions. The polycondensation reactions produced four types of π-conjugated polymers having low highest occupied molecular orbital (HOMO) levels due to the strong electron-withdrawing nature of the fluorine substituents. Owing to the low HOMO levels, the synthesized polymers served as an efficient hole-blocking layer (HBL) in OLEDs.

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