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Preparation of polymers having hole and electron transport units by Friedel–Crafts reaction
Authors:Takashi Washizu  Yuanfu Pei  Jaekook Ha  Martin Vacha  Kuniko Tani  Kenji Ogino  Hisaya Sato
Affiliation:1. Graduate School of Bio‐Applications and Systems Engineering, Tokyo University of Agriculture and Technology, 2‐24‐16 Naka‐machi, Koganei, Tokyo 184‐8588, Japan;2. LCD R&D Center, Samsung Electronics Co., Yongin, Gyeonggi‐Do 449‐711, Korea;3. Department of Organic and Polymeric Materials, Tokyo Institute of Technology, Ookayama 2‐12‐1‐S8, Meguro‐ku, Tokyo 152‐8552, Japan;4. Graduate School of Bio‐Applications and Systems Engineering, Tokyo University of Agriculture and Technology, 2‐24‐16 Naka‐machi, Koganei, Tokyo 184‐8588, JapanGraduate School of Bio‐Applications and Systems Engineering, Tokyo University of Agricultureand Technology, 2‐24‐16 Naka‐machi, Koganei, Tokyo 184‐8588, Japan
Abstract:Polymers having 2,5‐diphenyl‐1,3,4‐oxadiazole (BCO) or anthracene (BCA) as an electron transport unit and N,N′‐diphenyl‐N,N′‐bis(4‐butylphenyl)‐benzidine (BTPD) as a hole transport unit were prepared by condensation polymerization using Friedel–Crafts reaction. It was found that BCO was less reactive than BCA. The low reactivity of the BCO monomer can be explained by the oxygen atom in the oxadiazole unit, which acts as a Lewis base and reduces the activity of the catalyst. The redox behavior measured by cyclic voltammetry showed for both BTPD‐BCO and BTPD‐BCA almost the same oxidation potential. In addition, the BTPD‐BCO also exhibited a reduction peak. Hole and electron drifts mobility of the polymers were measured by the time‐of‐flight method. The hole drift mobility of both BTPD‐BCO and BTPD‐BCA was 7.4 × 10?5 cm2 V?1 s?1. The electron drift mobilities of BTPD‐BCO and BTPD‐BCA were 6.5 × 10?5 cm2 V?1 s?1 and 5.2 × 10?6 cm2 V?1 s?1, respectively. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 3083–3089, 2007
Keywords:anthracene  charge transport  electrochemistry  high performance polymers  oxadiazole  redox polymers  tetraphenylbenzidine
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