Thiophene fused azacoronenes: regioselective synthesis, self organization, charge transport, and its incorporation in conjugated polymers

US9136483B1 · kind B1 · utility

Assignee

• The Regents of the University of California · US

Inventors

• Yi Liu · Fremont, US
• Bo He · Albany, US

Key dates

• Filing date: Apr 16, 2015
• Grant date: Sep 15, 2015
• Expiry date: Apr 16, 2035

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P70/50
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A regioselective synthesis of an azacoronene fused with two peripheral thiophene groups has been realized through a concise synthetic route. The resulting thienoazacoronene (TAC) derivatives show high degree of self-organization in solution, in single crystals, in the bulk, and in spuncast thin films. Spuncast thin film field-effect transistors of the TACs exhibited mobilities up to 0.028 cm2V−1 S−1, which is among the top field effect mobilities for solution processed discotic materials. Organic photovoltaic devices using TAC-containing conjugated polymers as the donor material exhibited a high open-circuit voltage of 0.89 V, which was ascribable to TAC's low-lying highest occupied molecular orbital energy level.