A Donor Polymer Based on a Difluorinated Pentathiophene Unit Enabling Enhanced Performance for Nonfullerene Organic Solar Cells

Liu, Jing; Ma, Lik‐Kuen; Lin, Haoran; Zhang, Lin; Li, Zhengke; Law, Wai Kit; Shang, Ao; Hu, Huawei; Ma, Wei; Yan, He

doi:10.1002/smtd.201700415

Title: A Donor Polymer Based on a Difluorinated Pentathiophene Unit Enabling Enhanced Performance for Nonfullerene Organic Solar Cells

Journal Article · Sun Mar 25 00:00:00 EDT 2018 · Small Methods

DOI:https://doi.org/10.1002/smtd.201700415· OSTI ID:1429530

Liu, Jing ^[1]; Ma, Lik‐Kuen ^[2]; Lin, Haoran ^[2]; Zhang, Lin ^[3]; Li, Zhengke ^[1]; Law, Wai Kit ^[2]; Shang, Ao ^[1]; Hu, Huawei ^[1]; Ma, Wei ^[3]; Yan, He ^[1]

The Hong Kong University of Science and Technology‐Shenzhen Research Institute No. 9 Yuexing 1st RD Hi‐tech Park Nanshan Shenzhen 518057 P. R. China, Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration &, Reconstruction Hong Kong University of Science and Technology (HKUST) Clear Water Bay Kowloon Hong Kong
Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration &, Reconstruction Hong Kong University of Science and Technology (HKUST) Clear Water Bay Kowloon Hong Kong
State Key Laboratory for Mechanical Behavior of Materials Xi'an Jiaotong University Xi'an 710049 P. R. China

Abstract For oligothiophene‐based donor polymers, changing the number of thiophene rings in each repeating unit is a simple and effective approach to tune their optical and electronic properties. While bithiophene‐, terthiophene‐, and quaterthiophene‐based polymers have been widely known and studied, pentathiophene‐based ones are rarely reported. Here, the pentathiophene‐based polymer PT5T, which yields extremely poor device performance with an efficiency of only 0.37%, is synthesized. However, after the introduction of two fluorine atoms to the center thiophene unit, the resulting polymer (PT5T‐2F) yields dramatic improvement in device performance with the fill factor and the power conversion efficiency improved to 70.8% and 9.69%, respectively. The morphological study shows that the difluorinated pentathiophene building block introduces enhanced molecular aggregation and crystallinity of PT5T‐2F, which facilitates the formation of bulk heterojunction blends with higher domain purity. Most importantly, despite its high crystallinity, PT5T‐2F can still produce reasonably small domain sizes in the polymer‐based blend. The results indicate that the difluorinated pentathiophene is a promising building block to construct donor polymers for nonfullerene organic solar cells.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

Grant/Contract Number:: DE‐AC02‐05CH11231

OSTI ID:: 1429530

Journal Information:: Small Methods, Journal Name: Small Methods Vol. 2 Journal Issue: 5; ISSN 2366-9608

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 14 works

Citation information provided by
Web of Science

References (63)

Tuning Energy Levels without Negatively Affecting Morphology: A Promising Approach to Achieving Optimal Energetic Match and Efficient Nonfullerene Polymer Solar Cells Zhang, Jianquan; Jiang, Kui; Yang, Guofang Advanced Energy Materials, Vol. 7, Issue 15 https://doi.org/10.1002/aenm.201602119	journal	April 2017
High-Performance Electron Acceptor with Thienyl Side Chains for Organic Photovoltaics Lin, Yuze; Zhao, Fuwen; He, Qiao Journal of the American Chemical Society, Vol. 138, Issue 14 https://doi.org/10.1021/jacs.6b02004	journal	March 2016
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
Reduced voltage losses yield 10% efficient fullerene free organic solar cells with >1 V open circuit voltages Baran, D.; Kirchartz, T.; Wheeler, S. Energy & Environmental Science, Vol. 9, Issue 12 https://doi.org/10.1039/C6EE02598F	journal	January 2016
Fast charge separation in a non-fullerene organic solar cell with a small driving force Liu, Jing; Chen, Shangshang; Qian, Deping Nature Energy, Vol. 1, Issue 7 https://doi.org/10.1038/nenergy.2016.89	journal	June 2016
Realizing Over 13% Efficiency in Green-Solvent-Processed Nonfullerene Organic Solar Cells Enabled by 1,3,4-Thiadiazole-Based Wide-Bandgap Copolymers Xu, Xiaopeng; Yu, Ting; Bi, Zhaozhao Advanced Materials, Vol. 30, Issue 3 https://doi.org/10.1002/adma.201703973	journal	December 2017
Alkyl Side-Chain Engineering in Wide-Bandgap Copolymers Leading to Power Conversion Efficiencies over 10% Liu, Tao; Pan, Xuexue; Meng, Xiangyi Advanced Materials, Vol. 29, Issue 6 https://doi.org/10.1002/adma.201604251	journal	December 2016
High-Performance Solution-Processed Non-Fullerene Organic Solar Cells Based on Selenophene-Containing Perylene Bisimide Acceptor Meng, Dong; Sun, Dan; Zhong, Chengmei Journal of the American Chemical Society, Vol. 138, Issue 1 https://doi.org/10.1021/jacs.5b11149	journal	December 2015
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 inverted polymer solar cells employing favourable molecular orientation Vohra, Varun; Kawashima, Kazuaki; Kakara, Takeshi Nature Photonics, Vol. 9, Issue 6 https://doi.org/10.1038/nphoton.2015.84	journal	May 2015
A Star-Shaped Perylene Diimide Electron Acceptor for High-Performance Organic Solar Cells Lin, Yuze; Wang, Yifan; Wang, Jiayu Advanced Materials, Vol. 26, Issue 30 https://doi.org/10.1002/adma.201400525	journal	March 2014
High-efficiency and air-stable P3HT-based polymer solar cells with a new non-fullerene acceptor Holliday, Sarah; Ashraf, Raja Shahid; Wadsworth, Andrew Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms11585	journal	June 2016
Characterizing morphology in organic systems with resonant soft X-ray scattering Carpenter, Joshua H.; Hunt, Adrian; Ade, Harald Journal of Electron Spectroscopy and Related Phenomena, Vol. 200 https://doi.org/10.1016/j.elspec.2015.05.006	journal	April 2015
A SAXS/WAXS/GISAXS Beamline with Multilayer Monochromator Hexemer, Alexander; Bras, Wim; Glossinger, James Journal of Physics: Conference Series, Vol. 247 https://doi.org/10.1088/1742-6596/247/1/012007	journal	October 2010
Polymer solar cells with enhanced open-circuit voltage and efficiency Chen, Hsiang-Yu; Hou, Jianhui; Zhang, Shaoqing Nature Photonics, Vol. 3, Issue 11, p. 649-653 https://doi.org/10.1038/nphoton.2009.192	journal	November 2009
A Tetraphenylethylene Core-Based 3D Structure Small Molecular Acceptor Enabling Efficient Non-Fullerene Organic Solar Cells Liu, Yuhang; Mu, Cheng; Jiang, Kui Advanced Materials, Vol. 27, Issue 6 https://doi.org/10.1002/adma.201404152	journal	November 2014
Highly Fluorinated Benzobisbenzothiophenes Wang, Yongfeng; Parkin, Sean R.; Gierschner, Johannes Organic Letters, Vol. 10, Issue 15 https://doi.org/10.1021/ol8003468	journal	August 2008
Surprising Effects upon Inserting Benzene Units into a Quaterthiophene-Based D-A Polymer-Improving Non-Fullerene Organic Solar Cells via Donor Polymer Design Chen, Shangshang; Yao, Huatong; Li, Zhengke Advanced Energy Materials, Vol. 7, Issue 12 https://doi.org/10.1002/aenm.201602304	journal	January 2017
Design and Synthesis of a Low Bandgap Small Molecule Acceptor for Efficient Polymer Solar Cells Yao, Huifeng; Chen, Yu; Qin, Yunpeng Advanced Materials, Vol. 28, Issue 37 https://doi.org/10.1002/adma.201602642	journal	July 2016
High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Li, Gang; Shrotriya, Vishal; Huang, Jinsong Nature Materials, Vol. 4, Issue 11, p. 864-868 https://doi.org/10.1038/nmat1500	journal	October 2005
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
Semi-crystalline photovoltaic polymers with efficiency exceeding 9% in a ∼300 nm thick conventional single-cell device Nguyen, T. L.; Choi, H.; Ko, S. -J. Energy Environ. Sci., Vol. 7, Issue 9 https://doi.org/10.1039/C4EE01529K	journal	January 2014
Ring-Fusion of Perylene Diimide Acceptor Enabling Efficient Nonfullerene Organic Solar Cells with a Small Voltage Loss Zhang, Jianquan; Li, Yunke; Huang, Jiachen Journal of the American Chemical Society, Vol. 139, Issue 45 https://doi.org/10.1021/jacs.7b09998	journal	November 2017
Naphthodithiophene-Based Nonfullerene Acceptor for High-Performance Organic Photovoltaics: Effect of Extended Conjugation Zhu, Jingshuai; Ke, Zhifan; Zhang, Qianqian Advanced Materials, Vol. 30, Issue 2 https://doi.org/10.1002/adma.201704713	journal	November 2017
Molecular Engineering of Conjugated Polymers for Solar Cells: An Updated Report Xiao, Shengqiang; Zhang, Qianqian; You, Wei Advanced Materials, Vol. 29, Issue 20 https://doi.org/10.1002/adma.201601391	journal	December 2016
Efficient organic solar cells processed from hydrocarbon solvents Zhao, Jingbo; Li, Yunke; Yang, Guofang Nature Energy, Vol. 1, Issue 2 https://doi.org/10.1038/nenergy.2015.27	journal	January 2016
Synthesis of Fluorinated Polythienothiophene- co -benzodithiophenes and Effect of Fluorination on the Photovoltaic Properties Son, Hae Jung; Wang, Wei; Xu, Tao Journal of the American Chemical Society, Vol. 133, Issue 6 https://doi.org/10.1021/ja108601g	journal	February 2011
Ultimate efficiency of polymer/fullerene bulk heterojunction solar cells Koster, L. J. A.; Mihailetchi, V. D.; Blom, P. W. M. Applied Physics Letters, Vol. 88, Issue 9 https://doi.org/10.1063/1.2181635	journal	February 2006
High-efficiency photovoltaic cells with wide optical band gap polymers based on fluorinated phenylene-alkoxybenzothiadiazole Ko, Seo-Jin; Hoang, Quoc Viet; Song, Chang Eun Energy & Environmental Science, Vol. 10, Issue 6 https://doi.org/10.1039/C6EE03051C	journal	January 2017
Polymer solar cells with enhanced fill factors Guo, Xugang; Zhou, Nanjia; Lou, Sylvia J. Nature Photonics, Vol. 7, Issue 10 https://doi.org/10.1038/nphoton.2013.207	journal	August 2013
Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells Zhong, Yu; Trinh, M. Tuan; Chen, Rongsheng Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms9242	journal	September 2015
Three-Bladed Rylene Propellers with Three-Dimensional Network Assembly for Organic Electronics Meng, Dong; Fu, Huiting; Xiao, Chengyi Journal of the American Chemical Society, Vol. 138, Issue 32 https://doi.org/10.1021/jacs.6b04368	journal	August 2016
Terthiophene-Based D–A Polymer with an Asymmetric Arrangement of Alkyl Chains That Enables Efficient Polymer Solar Cells Hu, Huawei; Jiang, Kui; Yang, Guofang Journal of the American Chemical Society, Vol. 137, Issue 44 https://doi.org/10.1021/jacs.5b08556	journal	October 2015
Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells Liu, Yuhang; Zhao, Jingbo; Li, Zhengke Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6293	journal	November 2014
Design, Synthesis, and Photovoltaic Characterization of a Small Molecular Acceptor with an Ultra-Narrow Band Gap Yao, Huifeng; Cui, Yong; Yu, Runnan Angewandte Chemie International Edition, Vol. 56, Issue 11 https://doi.org/10.1002/anie.201610944	journal	February 2017
Reduced Intramolecular Twisting Improves the Performance of 3D Molecular Acceptors in Non-Fullerene Organic Solar Cells Lin, Haoran; Chen, Shangshang; Hu, Huawei Advanced Materials, Vol. 28, Issue 38 https://doi.org/10.1002/adma.201600997	journal	August 2016
Energy-Level Modulation of Small-Molecule Electron Acceptors to Achieve over 12% Efficiency in Polymer Solar Cells Li, Sunsun; Ye, Long; Zhao, Wenchao Advanced Materials, Vol. 28, Issue 42 https://doi.org/10.1002/adma.201602776	journal	September 2016
Implication of Fluorine Atom on Electronic Properties, Ordering Structures, and Photovoltaic Performance in Naphthobisthiadiazole-Based Semiconducting Polymers Kawashima, Kazuaki; Fukuhara, Tomohiro; Suda, Yousuke Journal of the American Chemical Society, Vol. 138, Issue 32 https://doi.org/10.1021/jacs.6b05418	journal	August 2016
Dramatic performance enhancement for large bandgap thick-film polymer solar cells introduced by a difluorinated donor unit Li, Zhengke; Lin, Haoran; Jiang, Kui Nano Energy, Vol. 15 https://doi.org/10.1016/j.nanoen.2015.05.016	journal	July 2015
Molecular Optimization Enables over 13% Efficiency in Organic Solar Cells Zhao, Wenchao; Li, Sunsun; Yao, Huifeng Journal of the American Chemical Society, Vol. 139, Issue 21 https://doi.org/10.1021/jacs.7b02677	journal	May 2017
High-performance fullerene-free polymer solar cells with 6.31% efficiency Lin, Yuze; Zhang, Zhi-Guo; Bai, Huitao Energy & Environmental Science, Vol. 8, Issue 2 https://doi.org/10.1039/C4EE03424D	journal	January 2015
Efficient Low-Bandgap Polymer Solar Cells with High Open-Circuit Voltage and Good Stability Ma, Tingxuan; Jiang, Kui; Chen, Shangshang Advanced Energy Materials, Vol. 5, Issue 20 https://doi.org/10.1002/aenm.201501282	journal	September 2015
25th Anniversary Article: Bulk Heterojunction Solar Cells: Understanding the Mechanism of Operation Heeger, Alan J. Advanced Materials, Vol. 26, Issue 1 https://doi.org/10.1002/adma.201304373	journal	December 2013
An Electron Acceptor with Porphyrin and Perylene Bisimides for Efficient Non-Fullerene Solar Cells Zhang, Andong; Li, Cheng; Yang, Fan Angewandte Chemie International Edition, Vol. 56, Issue 10 https://doi.org/10.1002/anie.201612090	journal	January 2017
Fused Nonacyclic Electron Acceptors for Efficient Polymer Solar Cells Dai, Shuixing; Zhao, Fuwen; Zhang, Qianqian Journal of the American Chemical Society, Vol. 139, Issue 3 https://doi.org/10.1021/jacs.6b12755	journal	January 2017
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
Design of a New Small‐Molecule Electron Acceptor Enables Efficient Polymer Solar Cells with High Fill Factor Li, Sunsun; Ye, Long; Zhao, Wenchao Advanced Materials, Vol. 29, Issue 46 https://doi.org/10.1002/adma.201704051	journal	October 2017
Efficient Semitransparent Organic Solar Cells with Tunable Color enabled by an Ultralow-Bandgap Nonfullerene Acceptor Cui, Yong; Yang, Chenyi; Yao, Huifeng Advanced Materials, Vol. 29, Issue 43 https://doi.org/10.1002/adma.201703080	journal	October 2017
Donor polymer design enables efficient non-fullerene organic solar cells Li, Zhengke; Jiang, Kui; Yang, Guofang Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13094	journal	October 2016
Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions Yu, G.; Gao, J.; Hummelen, J. C. Science, Vol. 270, Issue 5243, p. 1789-1791 https://doi.org/10.1126/science.270.5243.1789	journal	December 1995
Realizing Small Energy Loss of 0.55 eV, High Open-Circuit Voltage >1 V and High Efficiency >10% in Fullerene-Free Polymer Solar Cells via Energy Driver Cheng, Pei; Zhang, Mingyu; Lau, Tsz-Ki Advanced Materials, Vol. 29, Issue 11 https://doi.org/10.1002/adma.201605216	journal	January 2017
Reducing the efficiency–stability–cost gap of organic photovoltaics with highly efficient and stable small molecule acceptor ternary solar cells Baran, Derya; Ashraf, Raja Shahid; Hanifi, David A. Nature Materials, Vol. 16, Issue 3 https://doi.org/10.1038/nmat4797	journal	November 2016
11.4% Efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor Bin, Haijun; Gao, Liang; Zhang, Zhi-Guo Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13651	journal	December 2016
Fine-Tuned Photoactive and Interconnection Layers for Achieving over 13% Efficiency in a Fullerene-Free Tandem Organic Solar Cell Cui, Yong; Yao, Huifeng; Gao, Bowei Journal of the American Chemical Society, Vol. 139, Issue 21 https://doi.org/10.1021/jacs.7b01493	journal	May 2017
Achieving Highly Efficient Nonfullerene Organic Solar Cells with Improved Intermolecular Interaction and Open-Circuit Voltage Yao, Huifeng; Ye, Long; Hou, Junxian Advanced Materials, Vol. 29, Issue 21 https://doi.org/10.1002/adma.201700254	journal	March 2017
A Facile Planar Fused-Ring Electron Acceptor for As-Cast Polymer Solar Cells with 8.71% Efficiency Lin, Yuze; He, Qiao; Zhao, Fuwen Journal of the American Chemical Society, Vol. 138, Issue 9 https://doi.org/10.1021/jacs.6b00853	journal	February 2016
Non-Fullerene Polymer Solar Cells Based on Alkylthio and Fluorine Substituted 2D-Conjugated Polymers Reach 9.5% Efficiency Bin, Haijun; Zhang, Zhi-Guo; Gao, Liang Journal of the American Chemical Society, Vol. 138, Issue 13 https://doi.org/10.1021/jacs.6b01744	journal	March 2016
Interplay of Intramolecular Noncovalent Coulomb Interactions for Semicrystalline Photovoltaic Polymers Uddin, Mohammad Afsar; Lee, Tack Ho; Xu, Shuhao Chemistry of Materials, Vol. 27, Issue 17 https://doi.org/10.1021/acs.chemmater.5b02251	journal	August 2015
Fullerene-Free Polymer Solar Cells with over 11% Efficiency and Excellent Thermal Stability Zhao, Wenchao; Qian, Deping; Zhang, Shaoqing Advanced Materials, Vol. 28, Issue 23 https://doi.org/10.1002/adma.201600281	journal	April 2016
Influence of fluorination on the properties and performance of isoindigo–quaterthiophene-based polymers Hu, Huawei; Jiang, Kui; Kim, Joo-Hyun Journal of Materials Chemistry A, Vol. 4, Issue 14 https://doi.org/10.1039/C6TA00006A	journal	January 2016
Fused Hexacyclic Nonfullerene Acceptor with Strong Near-Infrared Absorption for Semitransparent Organic Solar Cells with 9.77% Efficiency Wang, Wei; Yan, Cenqi; Lau, Tsz-Ki Advanced Materials, Vol. 29, Issue 31 https://doi.org/10.1002/adma.201701308	journal	June 2017
Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure He, Zhicai; Zhong, Chengmei; Su, Shijian Nature Photonics, Vol. 6, Issue 9, p. 591-595 https://doi.org/10.1038/nphoton.2012.190	journal	August 2012
Towards rational design of organic electron acceptors for photovoltaics: a study based on perylenediimide derivatives Yan, Qifan; Zhou, Yan; Zheng, Yu-Qing Chemical Science, Vol. 4, Issue 12 https://doi.org/10.1039/c3sc51841h	journal	January 2013

Similar Records

Critical Role of Polymer Aggregation and Miscibility in Nonfullerene‐Based Organic Photovoltaics

Journal Article · Wed Jan 29 00:00:00 EST 2020 · Advanced Energy Materials · OSTI ID:1429530

Yi, Xueping; Peng, Zhengxing; Xu, Bing; +9 more

Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

Journal Article · Tue Sep 08 00:00:00 EDT 2015 · Journal of the American Chemical Society · OSTI ID:1429530

Zhou, Nanjia; Guo, Xugang; Ortiz, Rocio Ponce; +14 more

Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

Journal Article · Tue Sep 08 00:00:00 EDT 2015 · Journal of the American Chemical Society · OSTI ID:1429530

Zhou, Nanjia; Guo, Xugang; Ponce Ortiz, Rocio; +14 more

Title: A Donor Polymer Based on a Difluorinated Pentathiophene Unit Enabling Enhanced Performance for Nonfullerene Organic Solar Cells

Citation Formats

References (63)

Similar Records

Related Subjects