Synthesis and photovoltaic properties of conjugated copolymers based on benzimidazole and various thiophene

Abstract

A new accepter unit, dimethyl-2H-benzimidazole, was prepared and used for the synthesis of the conjugated polymers containing electron donor–acceptor pair for organic photovoltaics (OPVs). Dimethyl-2H-benzimidazole unit was designed to substitute the BT unit of poly(N-9′-heptadecanyl-2,7-carbazole-alt-5,5-(4′,7′-di-2-thienyl-2′,1′,3′-benzothiadiazole)) (PCDTBT). A series of new semiconducting polymers with 2,2-dimethyl-2H-benzimidazole, 9-heptadecanyl-9H-carbazole, and thiophene (or bithiophene) units was synthesized using Stille polymerization to generate PCDTMBIs (or PCBBTMBIs). In dimethyl-2H-benzimidazole, the sulfur at 2-position of BT unit was replaced with dialkyl substituted carbon, while keeping the 1,2-quinoid form, to improve the solubility of the polymers. The absorption spectra of PCDTMBIs with thiophene units exhibit two maximum peaks at about 430 and 613–645 nm in solution. The solutions of PCBBTMBIs show two absorption peaks at about 445–456 and 630–645 nm which is red-shifted about 20 nm when compared with PCDTMBIs caused by the introduction of bithiophene units. In most efficient polymer PCBBTMBI3, the device annealed at 100 °C for 10 min demonstrated a VOC value of 0.60 V, a JSC value of 4.31 mA/cm2, and a FF of 0.35, leading to the power conversion efficiency (PCE) of 0.91%, under white light illumination (AM 1.5 G and 100 mW/cm2). © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011