Dicyanovinyl-Substituted Oligothiophenes: Structure-Property Relationships and Application in Vacuum-Processed Small Molecule Organic Solar Cells

Efficient synthesis of a series of terminally dicyanovinyl (DCV)‐substituted oligothiophenes, DCVnT 1–6, without solubilizing side chains synthesized via a novel convergent approach and their application as electron donors in vacuum‐processed m‐i‐p‐type planar and p‐i‐n‐type bulk heterojunction orga...

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Published in:Advanced functional materials 2011-03, Vol.21 (5), p.897-910
Main Authors: Fitzner, Roland, Reinold, Egon, Mishra, Amaresh, Mena-Osteritz, Elena, Ziehlke, Hannah, Körner, Christian, Leo, Karl, Riede, Moritz, Weil, Matthias, Tsaryova, Olga, Weiß, André, Uhrich, Christian, Pfeiffer, Martin, Bäuerle, Peter
Format: Article
Language:English
Subjects:
Absorption spectra
bulk-heterojunction solar cells
Devices
dicyanovinylene acceptors
Heterojunctions
Illumination
molecular packing
Oligomers
oligothiophenes
Photovoltaic cells
Solar cells
structure-property relationships
Sunlight
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Summary:Efficient synthesis of a series of terminally dicyanovinyl (DCV)‐substituted oligothiophenes, DCVnT 1–6, without solubilizing side chains synthesized via a novel convergent approach and their application as electron donors in vacuum‐processed m‐i‐p‐type planar and p‐i‐n‐type bulk heterojunction organic solar cells is described. Purification of the products via gradient sublimation yields thermally highly stable organic semiconducting materials in single crystalline quality which allows for X‐ray structure analysis. Important insights into the packing features and intermolecular interactions of these promising solar cell materials are provided. Optical absorption spectra and electrochemical properties of the oligomers are investigated and valuable structure–property relationships deduced. Photovoltaic devices incorporating DCVnTs 4–6 showed power conversion efficiencies up to 2.8% for planar and 5.2% for bulk heterojunction organic solar cells under full sun illumination (mismatch corrected simulated AM 1.5G sunlight). The 5.2% efficiency shown here represents one of the highest values ever reported for organic vacuum‐deposited single heterojunction solar cells. A series of A‐D‐A‐type oligothiophenes have been developed as efficient donor materials for application in vacuum‐processed organic solar cells. Due to their promising optoelectronic properties and molecular packing in the bulk, these oligomers show high power conversion efficiencies up to 2.8% in planar heterojunction and record efficiencies of 5.2% in bulk heterojunction solar cells prepared by vacuum deposition.
ISSN:1616-301X
1616-3028
1616-3028
DOI:10.1002/adfm.201001639