Functionalized Phenanthrene Imide-Based Polymers for n-Type Organic Thin-Film Transistors

Yang，Jie1; Li，Jianfeng1; Zhang，Xiage1; Yang，Wanli1; Jeong，Sang Young3; Huang，Enmin1; Liu，Bin1; Woo，Han Young3; Chen，Zhicai1,2; Guo，Xugang1,4

2024-04-22

10.1002/anie.202319627

Angewandte Chemie - International Edition   影响因子和分区

1433-7851

1521-3773

High-performing n-type polymers are crucial for the advance of organic electronics field, however strong electron-deficient building blocks with optimized physicochemical properties for constructing them are still limited. The imide-functionalized polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugated framework, high electron deficiency and good solubility serve as promising candidates for developing high-performance n-type polymers. Among the PAHs, phenanthrene (PhA) features a well-delocalized aromatic π-system with multiple modifiable active sites. However, the PhA-based imides are seldom studied, mainly attributed to the synthetic challenge. Herein, we report two functionalized PhAs, CPOI and CPCNI, by simultaneously incorporating imide with carbonyl or dicyanomethylene onto PhA. Notably, the dicyanomethylene-modified CPCNI exhibits a well stabilized LUMO energy level (−3.84 eV), attributed to the synergetic inductive effect from imide and cyano groups. Subsequently, based on CPOI and CPCNI, two polymers PCPOI-Tz and PCPCNI-Tz were developed. Applied to organic thin-film transistors, owing to the strong electron-deficiency of CPCNI, polymer PCPCNI-Tz shows an improved electron mobility and largely decreased threshold voltage compared with PCPOI-Tz. This work affords two structurally novel electron-deficient building blocks and highlights the effectiveness of dual functionalization of PhAs with strong electron-withdrawing groups for devising n-type polymers.

Electron-Deficient Building Blocks Imide-Functionalized Polymers n-Type Polymers Organic Thin-Film Transistors Polycyclic Aromatic Hydrocarbons

SCI ; EI

英语

第一 ; 通讯

CHEMISTRY

2-s2.0-85188358689

Scopus

1.Department Materials Science and Engineering,Southern University of Science and Technology (SUSTech) No. 1088,Shenzhen,Xueyuan Road, Guangdong,518055,China
2.Department State Key Laboratory of Marine Resource Utilization in South China Sea,College of Materials Science and Engineering,Hainan University,Haikou,Hainan,570228,China
3.Research Institute for Natural Sciences,Department of Chemistry,Korea University,Anamro 145,Seoul,02841,South Korea
4.Guangdong,Provincial Key Laboratory of Functional Oxide Materials and Devices,Southern University of Science and Technology (SUSTech) No. 1088,Shenzhen,Xueyuan Road, Guangdong,518055,China

Yang，Jie,Li，Jianfeng,Zhang，Xiage,et al. Functionalized Phenanthrene Imide-Based Polymers for n-Type Organic Thin-Film Transistors[J]. Angewandte Chemie - International Edition,2024,63(17).

Yang，Jie.,Li，Jianfeng.,Zhang，Xiage.,Yang，Wanli.,Jeong，Sang Young.,...&Guo，Xugang.(2024).Functionalized Phenanthrene Imide-Based Polymers for n-Type Organic Thin-Film Transistors.Angewandte Chemie - International Edition,63(17).

Yang，Jie,et al."Functionalized Phenanthrene Imide-Based Polymers for n-Type Organic Thin-Film Transistors".Angewandte Chemie - International Edition 63.17(2024).