5 years ago

Significant Influence of the Methoxyl Substitution Position on Optoelectronic Properties and Molecular Packing of Small-Molecule Electron Acceptors for Photovoltaic Cells

Significant Influence of the Methoxyl Substitution Position on Optoelectronic Properties and Molecular Packing of Small-Molecule Electron Acceptors for Photovoltaic Cells
Shaoqing Zhang, Long Ye, Sunsun Li, Harald Ade, Jianhui Hou, Wenchao Zhao
Molecular engineering of nonfullerene electron acceptors is of great importance for the development of organic photovoltaics. In this study, a series of methoxyl-modified dithieno[2,3-d:2′,3′-d′]-s-indaceno[1,2-b:5,6-b′]dithiophene-based small-molecule acceptor (SMA) isomers are synthesized and characterized to determine the effect of substitution position of the terminal group in these acceptor–donor–acceptor-type SMAs. Minor changes in the substitution position are demonstrated to greatly influence the optoelectronic properties and molecular packing of the isomers. Note that SMAs with planar molecular backbones show more ordered molecular packing and smaller π–π stacking distances, thus dramatically higher electron mobilities relative to their counterparts with distorted end-groups. By utilizing polymer poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophen)-co-(1,3-di(5-thiophene-2-yl)-5,7-bis(2-ethylhexyl)benzo[1,2-c:4,5-c′]dithiophene-4,8-dione)] (PBDB-T) as an electron donor, an optimum power conversion efficiency (PCE) of 11.9% is achieved in the device based on PBDB-T:IT-OM-2, which is among the top efficiencies reported as of yet. Moreover, the PCE stays above 10% as the film thickness increases to 250 nm, which is very advantageous for large-area printing. Overall, the intrinsic molecular properties as well as the morphologies of blends can be effectively modulated by manipulating the substituent position on the terminal groups, and the structure–property relationships gleaned from this study will aid in designing more efficient SMAs for versatile applications. Through substitution position manipulations of methoxyl on terminal groups in ITIC-based small-molecule acceptors (SMAs), relations between the chemical structure and optoelectronic properties of these SMAs are systematically investigated. Benefiting from the planar backbone and strong intermolecular interactions of a 5-methoxyl-substituted SMA (IT-OM-2), an efficiency of 11.9% is achieved, which is among the top efficiencies reported so far.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/aenm.201700183

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