Esterification of Indoline-Based Small-Molecule Donors for Efficient Co-evaporated Organic Photovoltaics

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§ Key Laboratory of Physics and Technology for Advanced Batteries (Ministry of Education), College of Physics, Jilin University, Changchun 130012, P.R. China
Research Center for Organic Electronics (ROEL) and Department of Organic Device Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan
State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, P.R. China
Energy Technology Research Institute and Research Center for Photovoltaic Technology, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki 305-8568, Japan
Nagahama Institute of Bio-Science and Technology, Nagahama, Shiga 526-0829, Japan
*Tel.: +86-431-85155126. E-mail: [email protected] (X.-F. Wang).
Cite this: J. Phys. Chem. C 2014, 118, 27, 14785–14794
Publication Date (Web):June 26, 2014
https://doi.org/10.1021/jp5030608
Copyright © 2014 American Chemical Society
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Abstract

In this study, we attempted to develop a protocol for fabricating efficient solid-state organic photovoltaics based on materials used currently for dye-sensitized solar cells. Three typical indoline dyes, namely, D131, D102, and D149, were employed as electron donors in conjunction with C70 fullerene in solution-processed planar-heterojunction (PHJ) organic solar cells (OSCs). The PHJ cells based on these dyes exhibited similar external quantum efficiencies over the entire spectral range, resulting in identical short-circuit photocurrents. The open-circuit voltages of the PHJ cells were consistent with the highest occupied molecular orbital level of the corresponding indoline dye. The D102-based PHJ cell exhibited the highest power conversion efficiency, of up to 3.1%. The efficiency was limited by the light-harvesting capability of the solar cell, given that the short diffusion length (∼5 nm) of D102 limited the thickness of the active layer; the diffusion length was determined through an optical simulation. The methyl ester of D102 (D102-Me) was synthesized to reduce the degree of intermolecular hydrogen bonding between the dye molecules. D102-Me was found to be more suited for use in OSCs fabricated by the thermal evaporation method. PHJ cells based on solution-processed and thermally evaporated active layers of D102-Me exhibited similar photovoltaic performances. However, in the case of D102, the device with the thermally evaporated layer exhibited lower performance than that of the device with the solution-processed layer, owing to the decomposition of D102 during the evaporation process. D102-Me was then co-evaporated with C70 in bulk-heterojunction OSCs. A power conversion efficiency as high as 5.1% could be achieved by optimizing this active layer; the D102-Me/C70 blend ratio in the optimized layer was 1:9, and the thickness of the layer was 70 nm.

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1H and 13C NMR data of D102-Me and D131-Me. The HOMO levels of indoline dyes measured by UV photoelectron spectroscopy in air. The electronic absorption of D102-Me prepared by different methods. The TGA results of D102 and D102-Me both in air and in high vacuum. The absorption spectra of thin films of indoline dyes and fullerene with the thickness used in fabrication of PHJ cells. The photovoltaic performance of D131-Me-based PHJ and BHJ cells. This material is available free of charge via the Internet at http://pubs.acs.org.

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