Thieno[3,2-b]thiophene-Substituted Benzo[1,2-b:4,5-b′]dithiophene as a Promising Building Block for Low Bandgap Semiconducting Polymers for High-Performance Single and Tandem Organic Photovoltaic Cells

Abstract

We designed and synthetized a new poly{4,8-bis((2-ethylhexyl)thieno[3,2-b]thiophene)-benzo[1,2-b:4,5-b′]dithiophene-alt-2-ethylhexyl-4,6-dibromo-3-fluorothieno[3,4-b]thiophene-2-carboxylate} (PTTBDT-FTT) comprising bis(2-ethylhexylthieno[3,2-b]thiophenylbenzo[1,2-b:4,5-b′]dithiophene (TTBDT) and 2-ethylhexyl 3-fluorothieno[3,4-b]thiophene-2-carboxylate (FTT). The optical bandgap of PTTBDT-FTT was 1.55 eV. The energy levels of the highest occupied and lowest unoccupied molecular orbitals of PTTBDT-FTT were −5.31 and −3.73 eV, respectively. Two-dimensional grazing-incidence X-ray scattering measurements showed that the film’s PTTBDT-FTT chains are predominantly arranged with a face-on orientation with respect to the substrate, with strong π–π stacking. An organic thin-film transistor fabricated using PTTBDT-FTT as the active semiconductor showed high hole mobility of 2.1 × 10–2 cm2/(V·s). Single-junction bulk heterojunction photovoltaic cells with the configuration ITO/PEDOT:PSS/PTTBDT-FTT:PC71BM/Ca/Al were...