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Fluorine-Substituted Dithienylbenzodiimide-Based n-Type Polymer Semiconductors for Organic Thin-Film Transistors

Authors
Feng, KuiZhang, XianheWu, ZiangShi, YongqiangSu, MengyaoYang, KunWan, YangSun, HuiliangMin, JieZhang, YujieCheng, XingWoo, Han YoungGuo, Xugang
Issue Date
2-10월-2019
Publisher
AMER CHEMICAL SOC
Keywords
fluorination; imide functionalization; dithienylbenzodiimide; n-type polymer semiconductors; organic thin-film transistors
Citation
ACS APPLIED MATERIALS & INTERFACES, v.11, no.39, pp.35924 - 35934
Indexed
SCIE
SCOPUS
Journal Title
ACS APPLIED MATERIALS & INTERFACES
Volume
11
Number
39
Start Page
35924
End Page
35934
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/62548
DOI
10.1021/acsami.9b13138
ISSN
1944-8244
Abstract
Imide functionalization is one of the most effective approaches to develop electron-deficient building blocks for constructing n-type organic semiconductors. Driven by the attractive properties of imide-functionalized dithienylbenzodiimide (TBDI) and the promising device performance of TBDI-based polymers, a novel acceptor with increased electron affinity, fluorinated dithienylbenzodiimide (TFBDI), was designed with the hydrogen replaced by fluorine on the benzene core, and the synthetic challenges associated with this highly electron-deficient fluorinated imide building block are successfully overcome. TFBDI showed suppressed frontier molecular orbital energy levels as compared with TBDI. Copolymerizing this new electron-withdrawing TBDI with various donor co-units afforded a series of n-type polymer semiconductors TFBDI-T, TFBDI-Se, and TFBDI-BSe. All these TFBDI-based polymers exhibited a lower-lying lowest unoccupied molecular orbital (LUMO) energy level than the polymer analogue without fluorine. When applied in organic thin-film transistors, three polymers showed unipolar electron transport with large on-current/off-current ratios (I-on/I-off) of 10(5)-10(7). Among them, the selenophene-based polymer TFBDI-Se with the deepest-positioned LUMO and optimal chain stacking exhibited the highest electron mobility of 0.30 cm(2) s(-1). This result demonstrates that the new TFBDI is a highly attractive electron-deficient unit for enabling n-type polymer semiconductors, and the fluorination of imide-functionalized arenes offers an effective approach to develop more electron-deficient building blocks in organic electronics.
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