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Newly developed fused-ring electron acceptors (FREAs) have proven to be an effective class of materials for extending the absorption window and boosting the efficiency of organic photovoltaics (OPVs). While numerous acceptors have been developed, there is surprisingly little structural diversity among high performance FREAs in literature. Of the high efficiency electron acceptors reported, the vast majority utilize derivatives of 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (INCN) as the acceptor moiety. It has been postulated that the high electron mobility exhibited by FREA molecules with INCN end groups is a result of close π–π stacking between the neighboring planar INCN groups, forming an effective charge transport pathway between molecules. To explore this as a design rationale for electron acceptors, we synthesized a new fused-ring electron acceptor, IDTCF, which has methyl substituents out of plane to the conjugated acceptor backbone. These methyl groups hinder packing and expand the π–π stacking distance by ∼1 Å, but have little impact on the optical or electrochemical properties of the individual FREA molecule. The extra steric hindrance from the out of plane methyl substituents restricts packing and results in large amounts of geminate recombination, thus degrading the device performance. Our results show that intermolecular interactions (especially π–π stacking between end groups) play a crucial role in performance of FREAs. We demonstrated that the planarity of the acceptor unit is of paramount importance as even minor deviations in end group distance are enough to disrupt crystallinity and cripple device performance. 

Donor polymer fluorination has proven to be an effective method to improve the power conversion efficiency of fullerene-based polymer solar cells (PSCs). However, this fluorine effect has not been well-studied in systems containing new, non-fullerene acceptors (NFAs). Here, we investigate the impact of donor polymer fluorination in NFA-based solar cells by fabricating devices with either a fluorinated conjugated polymer (FTAZ) or its non-fluorinated counterpart (HTAZ) as the donor polymer and a small molecule NFA (ITIC) as the acceptor. We found that, similar to fullerene-based devices, fluorination leads to an increased open circuit voltage ( V oc ) from the lowered HOMO level and improved fill factor (FF) from the higher charge carrier mobility. More importantly, donor polymer fluorination in this NFA-based system also led to a large increase in short circuit current ( J sc ), which stems from the improved charge transport and extraction in the fluorinated device. This study demonstrates that fluorination is also advantageous in NFA-based PSCs and may improve performance to a higher extent than in fullerene-based PSCs. In the context of other recent reports on demonstrating higher photovoltaic device efficiencies with fluorinated materials, fluorination appears to be a valuable strategy in the design and synthesis of future donors and acceptors for PSCs.