Fullerene-free small molecule organic solar cells with a high open circuit voltage of 1.15 V

Ni, Wang; Li, Miaomiao; Kan, Bin; Liu, Feng; Wan, Xiangjian; Zhang, Qian; Zhang, Hongtao; Russell, Thomas P.; Chen, Yongsheng

doi:10.1039/c5cc07973j

Fullerene-free small molecule organic solar cells with a high open circuit voltage of 1.15 V

Journal Article · Thu Oct 29 00:00:00 EDT 2015 · ChemComm

DOI:https://doi.org/10.1039/c5cc07973j· OSTI ID:1370268

^[1]; Li, Miaomiao ^[1]; Kan, Bin ^[1]; Liu, Feng ^[2]; Wan, Xiangjian ^[1]; Zhang, Qian ^[1]; Zhang, Hongtao ^[1]; Russell, Thomas P. ^[3]; Chen, Yongsheng ^[1]

Nankai Univ., Tianjin (China)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of Massachusetts, Amherst, MA (United States)

In this work, a new small molecule named DTBTF with thiobarbituric acid as a terminal group was designed and synthesized as an acceptor for organic photovoltaic applications. DTBTF exhibits strong absorption in the visible region, and a relatively high lying LUMO energy level (-3.62 eV). All-small-molecule organic solar cells based on DR3TSBDT:DTBTF blend films show a considerable PCE of 3.84% with a high V_oc of 1.15 V.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Polymer-Based Materials for Harvesting Solar Energy (PHaSE)

Sponsoring Organization:: Ministry of Science and Technology of the People’s Republic of China (MOST); National Natural Science Foundation of China (NSFC); Tianjin City; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001087

OSTI ID:: 1370268

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 3 Vol. 52; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

The Energy of Charge‐Transfer States in Electron Donor–Acceptor Blends: Insight into the Energy Losses in Organic Solar Cells Veldman, Dirk; Meskers, Stefan C. J.; Janssen, René A. J. Advanced Functional Materials, Vol. 19, Issue 12 https://doi.org/10.1002/adfm.200900090	journal	June 2009
Polymer-Fullerene Bulk-Heterojunction Solar Cells Dennler, Gilles; Scharber, Markus C.; Brabec, Christoph J. Advanced Materials, Vol. 21, Issue 13, p. 1323-1338 https://doi.org/10.1002/adma.200801283	journal	April 2009
Non-Basic High-Performance Molecules for Solution-Processed Organic Solar Cells van der Poll, Thomas S.; Love, John A.; Nguyen, Thuc-Quyen Advanced Materials, Vol. 24, Issue 27 https://doi.org/10.1002/adma.201201127	journal	June 2012
A High-Performing Solution-Processed Small Molecule:Perylene Diimide Bulk Heterojunction Solar Cell Sharenko, Alexander; Proctor, Christopher M.; van der Poll, Thomas S. Advanced Materials, Vol. 25, Issue 32 https://doi.org/10.1002/adma.201301167	journal	June 2013
An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells Lin, Yuze; Wang, Jiayu; Zhang, Zhi-Guo Advanced Materials, Vol. 27, Issue 7 https://doi.org/10.1002/adma.201404317	journal	January 2015
Single-Junction Polymer Solar Cells Exceeding 10% Power Conversion Efficiency Chen, Jing-De; Cui, Chaohua; Li, Yan-Qing Advanced Materials, Vol. 27, Issue 6 https://doi.org/10.1002/adma.201404535	journal	November 2014
An All-Small-Molecule Organic Solar Cell with High Efficiency Nonfullerene Acceptor Kwon, Oh Kyu; Park, Jung-Hwa; Kim, Dong Won Advanced Materials, Vol. 27, Issue 11 https://doi.org/10.1002/adma.201405429	journal	February 2015
A New Fullerene-Free Bulk-Heterojunction System for Efficient High-Voltage and High-Fill Factor Solution-Processed Organic Photovoltaics Tang, Zheng; Liu, Bo; Melianas, Armantas Advanced Materials, Vol. 27, Issue 11 https://doi.org/10.1002/adma.201405485	journal	February 2015
Fine-Tuning the 3D Structure of Nonfullerene Electron Acceptors Toward High-Performance Polymer Solar Cells Li, Haiyan; Hwang, Ye-Jin; Courtright, Brett A. E. Advanced Materials, Vol. 27, Issue 21 https://doi.org/10.1002/adma.201500577	journal	April 2015
Fluoro-Substituted n-Type Conjugated Polymers for Additive-Free All-Polymer Bulk Heterojunction Solar Cells with High Power Conversion Efficiency of 6.71% Jung, Jae Woong; Jo, Jea Woong; Chueh, Chu-Chen Advanced Materials, Vol. 27, Issue 21 https://doi.org/10.1002/adma.201501214	journal	April 2015
7.7% Efficient All-Polymer Solar Cells Hwang, Ye-Jin; Courtright, Brett A. E.; Ferreira, Amy S. Advanced Materials, Vol. 27, Issue 31 https://doi.org/10.1002/adma.201501604	journal	July 2015
Efficiency Improvement of Solution-Processed Dithienopyrrole-Based A-D-A Oligothiophene Bulk-Heterojunction Solar Cells by Solvent Vapor Annealing Wessendorf, Cordula D.; Schulz, Gisela L.; Mishra, Amaresh Advanced Energy Materials, Vol. 4, Issue 14 https://doi.org/10.1002/aenm.201400266	journal	May 2014
Realizing over 10% efficiency in polymer solar cell by device optimization Zhang, Shaoqing; Ye, Long; Zhao, Wenchao Science China Chemistry, Vol. 58, Issue 2 https://doi.org/10.1007/s11426-014-5273-x	journal	January 2015
Fluorene-centered perylene monoimides as potential non-fullerene acceptor in organic solar cells Zhang, Youdi; Xiao, Yi; Xie, Yuanpeng Organic Electronics, Vol. 21 https://doi.org/10.1016/j.orgel.2015.03.017	journal	June 2015
Charge carrier recombination in organic solar cells Proctor, Christopher M.; Kuik, Martijn; Nguyen, Thuc-Quyen Progress in Polymer Science, Vol. 38, Issue 12 https://doi.org/10.1016/j.progpolymsci.2013.08.008	journal	December 2013
Fabrication and processing of polymer solar cells: A review of printing and coating techniques Krebs, Frederik C. Solar Energy Materials and Solar Cells, Vol. 93, Issue 4, p. 394-412 https://doi.org/10.1016/j.solmat.2008.10.004	journal	April 2009
Synthesis of a perylene bisimide with acetonaphthopyrazine dicarbonitrile terminal moieties for photovoltaic applications Mikroyannidis, John A.; Suresh, P.; Sharma, G. D. Synthetic Metals, Vol. 160, Issue 9-10 https://doi.org/10.1016/j.synthmet.2010.02.003	journal	May 2010
Single-Junction Polymer Solar Cells with Over 10% Efficiency by a Novel Two-Dimensional Donor–Acceptor Conjugated Copolymer Liu, Chang; Yi, Chao; Wang, Kai ACS Applied Materials & Interfaces, Vol. 7, Issue 8 https://doi.org/10.1021/am509047g	journal	February 2015
Molecular Design of Photovoltaic Materials for Polymer Solar Cells: Toward Suitable Electronic Energy Levels and Broad Absorption Li, Yongfang Accounts of Chemical Research, Vol. 45, Issue 5 https://doi.org/10.1021/ar2002446	journal	January 2012
High Performance Photovoltaic Applications Using Solution-Processed Small Molecules Chen, Yongsheng; Wan, Xiangjian; Long, Guankui Accounts of Chemical Research, Vol. 46, Issue 11 https://doi.org/10.1021/ar400088c	journal	July 2013
Design and Synthesis of Molecular Donors for Solution-Processed High-Efficiency Organic Solar Cells Coughlin, Jessica E.; Henson, Zachary B.; Welch, Gregory C. Accounts of Chemical Research, Vol. 47, Issue 1 https://doi.org/10.1021/ar400136b	journal	August 2013
Molecular Design toward Highly Efficient Photovoltaic Polymers Based on Two-Dimensional Conjugated Benzodithiophene Ye, Long; Zhang, Shaoqing; Huo, Lijun Accounts of Chemical Research, Vol. 47, Issue 5 https://doi.org/10.1021/ar5000743	journal	April 2014
Small-Molecule, Nonfullerene Acceptors for Polymer Bulk Heterojunction Organic Photovoltaics Anthony, John E. Chemistry of Materials, Vol. 23, Issue 3, p. 583-590 https://doi.org/10.1021/cm1023019	journal	February 2011
Fluorine Substituents Reduce Charge Recombination and Drive Structure and Morphology Development in Polymer Solar Cells Stuart, Andrew C.; Tumbleston, John R.; Zhou, Huaxing Journal of the American Chemical Society, Vol. 135, Issue 5 https://doi.org/10.1021/ja309289u	journal	January 2013
Efficient Organic Solar Cells with Helical Perylene Diimide Electron Acceptors Zhong, Yu; Trinh, M. Tuan; Chen, Rongsheng Journal of the American Chemical Society, Vol. 136, Issue 43 https://doi.org/10.1021/ja5092613	journal	October 2014
Solution-Processed Organic Solar Cells Based on Dialkylthiol-Substituted Benzodithiophene Unit with Efficiency near 10% Kan, Bin; Zhang, Qian; Li, Miaomiao Journal of the American Chemical Society, Vol. 136, Issue 44 https://doi.org/10.1021/ja509703k	journal	October 2014
High Quantum Efficiencies in Polymer Solar Cells at Energy Losses below 0.6 eV Li, Weiwei; Hendriks, Koen H.; Furlan, Alice Journal of the American Chemical Society, Vol. 137, Issue 6 https://doi.org/10.1021/ja5131897	journal	February 2015
A Series of Simple Oligomer-like Small Molecules Based on Oligothiophenes for Solution-Processed Solar Cells with High Efficiency Kan, Bin; Li, Miaomiao; Zhang, Qian Journal of the American Chemical Society, Vol. 137, Issue 11 https://doi.org/10.1021/jacs.5b00305	journal	March 2015
Deep Absorbing Porphyrin Small Molecule for High-Performance Organic Solar Cells with Very Low Energy Losses Gao, Ke; Li, Lisheng; Lai, Tianqi Journal of the American Chemical Society, Vol. 137, Issue 23 https://doi.org/10.1021/jacs.5b03740	journal	June 2015
Non-Fullerene-Acceptor-Based Bulk-Heterojunction Organic Solar Cells with Efficiency over 7% Sun, Dan; Meng, Dong; Cai, Yunhao Journal of the American Chemical Society, Vol. 137, Issue 34 https://doi.org/10.1021/jacs.5b06414	journal	August 2015
Rational Design of High Performance Conjugated Polymers for Organic Solar Cells Zhou, Huaxing; Yang, Liqiang; You, Wei Macromolecules, Vol. 45, Issue 2 https://doi.org/10.1021/ma201648t	journal	January 2012
Nanoscale Morphology of High-Performance Polymer Solar Cells Yang, Xiaoniu; Loos, Joachim; Veenstra, Sjoerd C. Nano Letters, Vol. 5, Issue 4, p. 579-583 https://doi.org/10.1021/nl048120i	journal	April 2005
Single-junction polymer solar cells with high efficiency and photovoltage He, Zhicai; Xiao, Biao; Liu, Feng Nature Photonics, Vol. 9, Issue 3 https://doi.org/10.1038/nphoton.2015.6	journal	February 2015
Efficient bulk heterojunction devices based on phenylenevinylene small molecule and perylene–pyrene bisimide Sharma, G. D.; Suresh, P.; Mikroyannidis, John A. J. Mater. Chem., Vol. 20, Issue 3 https://doi.org/10.1039/B918527E	journal	January 2010
Fullerene derivative acceptors for high performance polymer solar cells He, Youjun; Li, Yongfang Phys. Chem. Chem. Phys., Vol. 13, Issue 6 https://doi.org/10.1039/C0CP01178A	journal	January 2011
Recent advances of non-fullerene, small molecular acceptors for solution processed bulk heterojunction solar cells Eftaiha, Ala'a F.; Sun, Jon-Paul; Hill, Ian G. J. Mater. Chem. A, Vol. 2, Issue 5 https://doi.org/10.1039/C3TA14236A	journal	January 2014
A–D–A small molecules for solution-processed organic photovoltaic cells Ni, Wang; Wan, Xiangjian; Li, Miaomiao Chemical Communications, Vol. 51, Issue 24 https://doi.org/10.1039/C4CC09758K	journal	January 2015
High-efficiency non-fullerene organic solar cells enabled by a difluorobenzothiadiazole-based donor polymer combined with a properly matched small molecule acceptor Zhao, Jingbo; Li, Yunke; Lin, Haoran Energy & Environmental Science, Vol. 8, Issue 2 https://doi.org/10.1039/C4EE02990A	journal	January 2015
Non-fullerene acceptors for organic photovoltaics: an emerging horizon Lin, Yuze; Zhan, Xiaowei Materials Horizons, Vol. 1, Issue 5 https://doi.org/10.1039/C4MH00042K	journal	January 2014
Key components to the recent performance increases of solution processed non-fullerene small molecule acceptors McAfee, Seth M.; Topple, Jessica M.; Hill, Ian G. Journal of Materials Chemistry A, Vol. 3, Issue 32 https://doi.org/10.1039/C5TA04310G	journal	January 2015
Semiconducting polymers: the Third Generation Heeger, Alan J. Chemical Society Reviews, Vol. 39, Issue 7 https://doi.org/10.1039/b914956m	journal	January 2010
Organic non-fullerene acceptors for organic photovoltaics Sonar, Prashant; Fong Lim, Jacelyn Pui; Chan, Khai Leok Energy & Environmental Science, Vol. 4, Issue 5, p. 1558-1574 https://doi.org/10.1039/c0ee00668h	journal	January 2011
Small molecule semiconductors for high-efficiency organic photovoltaics Lin, Yuze; Li, Yongfang; Zhan, Xiaowei Chemical Society Reviews, Vol. 41, Issue 11 https://doi.org/10.1039/c2cs15313k	journal	January 2012
Perylene diimides: a thickness-insensitive cathode interlayer for high performance polymer solar cells Zhang, Zhi-Guo; Qi, Boyuan; Jin, Zhiwen Energy & Environmental Science, Vol. 7, Issue 6, p. 1966-1973 https://doi.org/10.1039/c4ee00022f	journal	January 2014

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