4H-1,2,6-Thiadiazine-containing donor–acceptor conjugated polymers: synthesis, optoelectronic characterization and their use in organic solar cells

Abstract

π-Conjugated donor–acceptor (D–A) polymers containing electron withdrawing non-S-oxidized 4H-1,2,6-thiadiazines and electron donating (het)aryl-substituted indacenodithiophenes (IDTs) were prepared and used in organic solar cell (OSC) devices with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the fullerene acceptor. The non-S-oxidized 4H-1,2,6-thiadiazine containing polymers were wide bandgap absorbers (Eoptg 1.80–1.95 eV) with low-lying highest occupied molecular orbital energy levels (EHOMO −5.5 to −6.1 eV) affording high open circuit voltages (Vocs 0.82–0.96 V) for polymer:fullerene bulk heterojunction (BHJ) OSCs. Owing to enhanced short circuit currents (Jscs) and fill factors (FFs), the 1,2,6-thiadiazin-4(H)-one-based polymers had significantly higher performances (up to 3.83%) vs. the N-(perfluorophenyl)-1,2,6-thiadiazin-4(H)-imine based-polymers (up to 1.37%).