Enhancing Performance of Fused-Ring Electron Acceptor Using Pyrrole Instead of Thiophene.

Selecting suitable outermost aromatic rings of the central cores is of particular importance for the design of fused-ring electron acceptors (FREAs) because the direct electronic communication between the outermost aromatic rings and termini exerts a strong impact on the optoelectronic properties of FREAs. In most cases, the outermost rings of the FREA cores are thiophene. This work reported the first example of using pyrrole as the outermost rings of the core. Fused hexacyclic electron acceptor, P6IC, using pyrrole in place of the often-used thiophene as the outermost rings of the central core was synthesized. Compared with its structural analogue F6IC with thiophene as the outermost rings, P6IC exhibits a remarkably upshifted highest occupied molecular orbital energy level (P6IC: -5.43 eV, F6IC: -5.71 eV), a slightly upshifted lowest unoccupied molecular orbital energy level (P6IC: -3.94 eV, F6IC: -4.00 eV), 54 nm red-shifted absorption, a narrower band gap (P6IC: 1.30 eV, F6IC: 1.37 eV), and an enhanced mobility (P6IC: 8.8 × 10 cm V s, F6IC: 7.4 × 10 cm V s). Organic photovoltaic cells using PTB7-Th/P6IC as a photoactive layer exhibit an efficiency of 12.2%, far surpassing that based on PTB7-Th/F6IC active layer (5.57%). The semitransparent devices using PTB7-Th/P6IC as the active layer yield efficiency of 10.2% with an average visible transmittance (AVT) of 17.0%, far surpassing that based on PTB7-Th/F6IC (5.26% with an AVT of 18.4%).