Alkoxy-Substituted Anthra[1,2‑c:5,6‑c′]bis([1,2,5]thiadiazole) (ATz): A New Electron-Acceptor Unit in the Semiconducting Polymers for Organic Electronics

• Published in: Macromolecules 2018-07, Vol.51 (14), p.5473-5484
• Main Authors: Mori, Hiroki, Nishinaga, Shuhei, Takahashi, Ryosuke, Nishihara, Yasushi
• Format: Article
• Language: English
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/acs.macromol.8b01230

A new type of thiadiazole-based acceptor unit and its donor–acceptor copolymers were synthesized and characterized to develop the high-performance semiconducting polymers for organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). We successfully synthesized an anthra­[1,2-c:5,6-c′]­bis­([1,2,5]­thiadiazole) (ATz) core and ATz-quaterthiophene copolymers. These copolymers possess a wide energy gap of ca. 1.8 eV and a deeper HOMO energy levels around −5.4 eV than that of typical thiadiazole–oligothiophene copolymers. Such weak electron-accepting nature may be due to the decreased electron affinity of the ATz core by an existence of alkoxy groups with strong electron-donating ability. The ATz copolymers exhibited good semiconducting properties with hole mobility of up to 0.03 cm2 V–1 s–1 and photovoltaic response with PCE of up to 5.7%, despite the unfavorable molecular orders, thin-film structure, and/or amorphous structure.