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 (Ion/Ioff) of 105-107. 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 cm2 V-1 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.
| Original language | English |
|---|---|
| Pages (from-to) | 35924-35934 |
| Number of pages | 11 |
| Journal | ACS Applied Materials and Interfaces |
| Volume | 11 |
| Issue number | 39 |
| DOIs | |
| Publication status | Published - 2019 Oct 2 |
Keywords
- dithienylbenzodiimide
- fluorination
- imide functionalization
- n-type polymer semiconductors
- organic thin-film transistors
ASJC Scopus subject areas
- Materials Science(all)
Cite this
Fluorine-Substituted Dithienylbenzodiimide-Based n-Type Polymer Semiconductors for Organic Thin-Film Transistors. / Feng, Kui; Zhang, Xianhe; Wu, Ziang; Shi, Yongqiang; Su, Mengyao; Yang, Kun; Wang, Yang; Sun, Huiliang; Min, Jie; Zhang, Yujie; Cheng, Xing; Woo, Han Young; Guo, Xugang.
In: ACS Applied Materials and Interfaces, Vol. 11, No. 39, 02.10.2019, p. 35924-35934.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Fluorine-Substituted Dithienylbenzodiimide-Based n-Type Polymer Semiconductors for Organic Thin-Film Transistors
AU - Feng, Kui
AU - Zhang, Xianhe
AU - Wu, Ziang
AU - Shi, Yongqiang
AU - Su, Mengyao
AU - Yang, Kun
AU - Wang, Yang
AU - Sun, Huiliang
AU - Min, Jie
AU - Zhang, Yujie
AU - Cheng, Xing
AU - Woo, Han Young
AU - Guo, Xugang
PY - 2019/10/2
Y1 - 2019/10/2
N2 - 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 (Ion/Ioff) of 105-107. 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 cm2 V-1 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.
AB - 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 (Ion/Ioff) of 105-107. 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 cm2 V-1 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.
KW - dithienylbenzodiimide
KW - fluorination
KW - imide functionalization
KW - n-type polymer semiconductors
KW - organic thin-film transistors
UR - http://www.scopus.com/inward/record.url?scp=85072849338&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85072849338&partnerID=8YFLogxK
U2 - 10.1021/acsami.9b13138
DO - 10.1021/acsami.9b13138
M3 - Article
C2 - 31525945
AN - SCOPUS:85072849338
VL - 11
SP - 35924
EP - 35934
JO - ACS applied materials & interfaces
JF - ACS applied materials & interfaces
SN - 1944-8244
IS - 39
ER -