Abstract

Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained.

Highlights

  • Organic photovoltaics are gathering a tremendous amount of attention in the scientific community

  • In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained

  • Solar cells with power conversion efficiencies (PCEs) of up to 2.6% could be realized in the inverted architecture and maximum PCEs of 2.35% were reached with solar cells prepared in normal architecture

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Summary

Introduction

Organic photovoltaics are gathering a tremendous amount of attention in the scientific community. Fullerene-free organic solar cells have sparked interest amongst researchers since novel donor and acceptor structures have extended the range of possible combinations to tune the device performance to an optimum. By combining the right conjugated polymer donor and non-fullerene acceptor (NFA) partners, power conversion efficiencies (PCEs) have reached values of up to 15.6% in singlejunction solar cells [1,2,3] and 17% in tandem devices [4], while the quest for suitable materials on both sides is still ongoing. It is possible to prepare NFAs in large quantities and good purity, but even more importantly, they can be tailored more than fullerenes to match the energy levels with the donor in order to improve the device performance [5,6,7,8,9,10,11]. ITIC-based systems, in particular those with fluorinated ITIC derivatives, have been successfully used to obtain devices with PCEs of up to 14% [1, 13, 14]

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