Synthesis and characterization of new selenophene-based conjugated polymers for organic photovoltaic cells

Abstract

Three new polymers poly(3,4'''-didodecyl) hexaselenophene) (P6S), poly(5,5'-bis(4,4'-didodecyl-2,2'-biselenophene-5-yl)-2,2'-biselenophene) (HHP6S), and poly(5,5'-bis(3',4-didodecyl-2,2'-biselenophene-5-yl)-2,2'-biselenophene) (TTP6S) that have the same selenophene-based polymer backbone but different side chain patterns were designed and synthesized. The weight-averaged molecular weights (Mw) of P6S, HHP6S, and TTP6S were found to be 19,100, 24,100, and 19,700 with polydispersity indices of 2.77, 1.48, and 1.41, respectively. The UVvisible absorption maxima of P6S, HHP6S, and TTP6S are at 524, 489, and 513 nm, respectively, in solution and at 569, 517, and 606 nm, respectively, in the film state. The polymers P6S, HHP6S, and TTP6S exhibit low band gaps of 1.74, 1.95, and 1.58 eV, respectively. The field-effect mobilities of P6S, HHP6S, and TTP6S were measured to be 1.3 x 10-4, 3.9 x 10-6, and 3.2 x 10-4 cm2 V-1 s-1, respectively. A photovoltaic device with a TTP6S/[6,6]-phenyl C71-butyric acid methyl ester (1:3, w/w) blend film active layer was found to exhibit an open circuit voltage (VOC) of 0.71 V, a short circuit current (JSC) of 5.72 mA cm-2, a fill factor of 0.41, and a power conversion efficiency (PCE) of 1.67% under AM 1.5 G (100 mW cm-2) illumination. TTP6S has the most planar backbone of the tested polymers, which results in strong pp interchain interactions and strong aggregation, leading to broad absorption, high mobility, a low band gap, and the highest PCE. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 50: 551-561, 2012