Bis(benzoselenadiazol)ethane: A π‐Extended Acceptor‐Dimeric Unit for Ambipolar Polymer Transistors with Hole and Electron Mobilities Exceeding 10 cm2 V−1 s−1

• Published in: Angewandte Chemie International Edition 2024-04, Vol.63 (17), p.e202400061-n/a
• Main Authors: Liu, Di, Zhao, Yinghan, Zhang, Jianqi, Wei, Zhixiang, Liu, Yunqi, Wang, Yang
• Format: Article
• Language: English
• Subjects: Acceptor Dimers; Acceptor-Acceptor Backbone; Ambipolar Polymers; Organic Thin-Film Transistors; Selenium Substitution
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202400061

The lack of ambipolar polymers with balanced hole (μh) and electron mobilities (μe) >10 cm2 V−1 s−1 is the main bottleneck for developing organic integrated circuits. Herein, we show the design and synthesis of a π‐extended selenium‐containing acceptor‐dimeric unit, namely benzo[c][1,2,5]selenadiazol‐4‐yl)ethane (BBSeE), to address this dilemma. In comparison to its sulfur‐counterpart, BBSeE demonstrates enlarged co‐planarity, selective noncovalent interactions, polarized Se−N bond, and higher electron affinity. The successful stannylation of BBSeE offers a great opportunity to access acceptor‐acceptor copolymer pN‐BBSeE, which shows a narrower band gap, lower‐lying lowest unoccupied molecular orbital level (−4.05 eV), and a higher degree of backbone planarity. Consequently, the pN‐BBSeE‐based organic transistors display an ideally balanced ambipolar transporting property with μh and μe of 10.65 and 10.72 cm2 V−1 s−1, respectively. To the best of our knowledge, the simultaneous μh/μe values >10.0 cm2 V−1 s−1 are the best performances ever reported for ambipolar polymers. In addition, pN‐BBSeE shows an excellent shelf‐storage stability, retaining over 85 % of the initial mobility values after two months storage. Our study demonstrates the π‐extended acceptor‐dimeric BBSeE is a promising acceptor building block for constructing high‐performance ambipolar polymers applied in next‐generation organic integrated circuit. A selenium‐containing π‐extended acceptor‐dimeric unit, namely BBSeE, is designed and synthesized for constructing ambipolar polymer pN‐BBSeE, featuring narrower band gap, high planarity, and low‐lying LUMO. pN‐BBSeE demonstrates ideally balanced ambipolar TFT performances with hole and electron mobility values up to 10.65 and 10.72 cm2 V−1 s−1, respectively, which is among the best ambipolar polymers reported so far.