Synthesis and Structure-Property Correlations of Dicyanovinyl-Substituted Oligoselenophenes and their Application in Organic Solar Cells

• Published in: Advanced functional materials Vol. 22; no. 20; pp. 4322 - 4333
• Main Authors: Haid, Stefan, Mishra, Amaresh, Weil, Matthias, Uhrich, Christian, Pfeiffer, Martin, Bäuerle, Peter
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 23.10.2012; WILEY‐VCH Verlag
• Subjects: crystal structure; dicyanovinyl acceptor; heterojunction solar cells; oligoselenophene; structure-property relationships
• DOI: 10.1002/adfm.201201018
• ISSN: 1616-301X

The convergent synthesis of a series of acceptor–donor–acceptor (A‐D‐A) type dicaynovinyl (DCV)‐substituted oligoselenophenes DCVnS (n = 3–5) is presented. Trends in thermal and optoelectronic properties are studied, in dependence on the length of the conjugated backbone. Optical measurements reveal red‐shifted absorption spectra and electrochemical investigations show lowering of the lowest unoccupied molecular orbital (LUMO) energy levels for DCVnS compared to the corresponding thiophene analogs DCVnT. As a consequence, a lowering of the bandgap is observed. Single crystal X‐ray structure analysis of tetramer DCV4S provides important insight into the packing features and intermolecular interactions of the molecules, further corroborating the importance of the DCV acceptor groups for the molecular ordering. DCV4S and DCV5S are used as donor materials in planar heterojunction (PHJ) and bulk‐heterojunction (BHJ) organic solar cells. The devices show very high fill factors (FF), a high open circuit voltage, and power conversion efficiencies (PCE) of up to 3.4% in PHJ solar cells and slightly reduced PCEs of up to 2.6% in BHJ solar cells. In PHJ devices, the PCE for DCV4S almost doubles compared to the PCE reported for the oligothiophene analog DCV4T, while DCV5S shows an about 30% higher PCE than DCV5T. Trends in the thermal and optoelectronic properties of a series of dicyanovinyl‐substituted oligoselenophenes are studied and compared to corresponding thiophene analogs. X‐ray structure analysis corroborates the importance of the dicyanovinyl acceptor groups for the molecular ordering. These oligomers show efficiencies as high as 3.4% in vacuum‐processed planar heterojunction solar cells.