Bichalcogenophene Imide-Based Homopolymers: Chalcogen-Atom Effects on the Optoelectronic Property and Device Performance in Organic Thin-Film Transistors

Shi, Shengbin1,2; Tang, Linjing1,2; Guo, Han1,2; Uddin, Mohammad Afsar3; Wang, Hang1,2; Yang, Kun1,2; Liu, Bin1,2; Wang, Yingfeng1,2; Sun, Huiliang1,2; Woo, Han Young3; Guo, Xugang1,2

2019-10-08

10.1021/acs.macromol.9b01173

MACROMOLECULES   影响因子和分区

0024-9297

1520-5835

Driven by the exceptional success of 2,2'-bithiophene-3,3'-dicarboximide imide (BTI) for enabling high-performance polymer semiconductors, herein two BTI analogues 2,2'-bifuran-3,3'-dicarboximide (BFI) and 2,2'biselenophene-3,3'-dicarboximide (BSeI) are designed and synthesized. The strong electron-withdrawing imide group enables BFI and BSeI with high electron deficiency, differing from typical fiiran- and selenophene-based building blocks, which are electron-rich. Hence, n-type polymers can be derived based on these two new imides. To investigate the effects of chalcogenatom substitution on the physicochemical properties and device performance of these imide-bridged materials, two homopolymers PBFI and PBSeI are synthesized together with the previously reported PBTI as control. Structures, optoelectronic properties, and charge transport characteristics of PBFI and PBSeI are studied and compared to those of the thiophene-based analogue PBTI in depth. The optical band gap (E-g(opt)) of the dibrominated bichalcogenophene imide and corresponding homopolymer becomes narrowed gradually as the chalcogen-atom size increases. Among all polymers, PBSeI shows the smallest E-g(opt) of 1.78 eV. In addition, the lowest unoccupied molecular orbital (LUMO) energy level (E-LUMO) of the monomer and its homopolymer is also lowered. Such lowering of E(g)(opt)s and E(LUMO)s by simple chalcogen substitution should have profound implications for device applications. The organic thin-film transistors based on PBFI, PBTI, and PBSeI show n-type performance with the highest electron mobility of 0.085, 1.53, and 0.82 cm(2) V-1 s(-1), respectively, indicating that increasing chalcogen-atom size doesn't necessarily improve electron transport. It was found that chalcogen atoms largely affect the packing of polymer chains, which leads to PBTI and PBSeI with a higher crystallinity compared with PBFI. The results demonstrate that in addition to the well-known BTI, BSeI should also be a highly promising unit for constructing n-type polymers, and this study provides an important foundation for further development of high-performance organic semiconductors considering the significance of imide-functionalized building blocks in the field of organic electronics.

SCI ; EI

英语

NI期刊

第一 ; 通讯

NRF of Korea[2016M1A2A2940911] ; NRF of Korea[2015M1A2A2057506]

Polymer Science

Polymer Science

WOS:000489678400019

AMER CHEMICAL SOC

20194107512639

Amines ; Atoms ; Crystallinity ; Electron transport properties ; Energy gap ; Molecular orbitals ; Organic polymers ; Physicochemical properties ; Thin film circuits ; Thin film transistors ; Thin films

Semiconductor Devices and Integrated Circuits:714.2 ; Organic Compounds:804.1 ; Organic Polymers:815.1.1 ; Atomic and Molecular Physics:931.3

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol SUSTech, Dept Mat Sci & Engn, 1088 Xueyuan Rd, Shenzhen 518055, Guangdong, Peoples R China
2.Southern Univ Sci & Technol SUSTech, Shenzhen Key Lab Printed Organ Elect, 1088 Xueyuan Rd, Shenzhen 518055, Guangdong, Peoples R China
3.Korea Univ, Coll Sci, Dept Chem, 145 Anam Ro, Seoul 02841, South Korea

Shi, Shengbin,Tang, Linjing,Guo, Han,et al. Bichalcogenophene Imide-Based Homopolymers: Chalcogen-Atom Effects on the Optoelectronic Property and Device Performance in Organic Thin-Film Transistors[J]. MACROMOLECULES,2019,52(19):7301-7312.

Shi, Shengbin.,Tang, Linjing.,Guo, Han.,Uddin, Mohammad Afsar.,Wang, Hang.,...&Guo, Xugang.(2019).Bichalcogenophene Imide-Based Homopolymers: Chalcogen-Atom Effects on the Optoelectronic Property and Device Performance in Organic Thin-Film Transistors.MACROMOLECULES,52(19),7301-7312.

Shi, Shengbin,et al."Bichalcogenophene Imide-Based Homopolymers: Chalcogen-Atom Effects on the Optoelectronic Property and Device Performance in Organic Thin-Film Transistors".MACROMOLECULES 52.19(2019):7301-7312.