Modulation of End Groups for Low‐Bandgap Nonfullerene Acceptors Enabling High‐Performance Organic Solar Cells

Chen, Yuzhong; Liu, Tao; Hu, Huawei; Ma, Tingxuan; Lai, Joshua Yuk Lin; Zhang, Jianquan; Ade, Harald; Yan, He

doi:10.1002/aenm.201801203

Modulation of End Groups for Low‐Bandgap Nonfullerene Acceptors Enabling High‐Performance Organic Solar Cells

Journal Article · Mon Aug 06 00:00:00 EDT 2018 · Advanced Energy Materials

DOI:https://doi.org/10.1002/aenm.201801203· OSTI ID:1463199

^[1]; Liu, Tao ^[1]; Hu, Huawei ^[2]; Ma, Tingxuan ^[1]; Lai, Joshua Yuk Lin ^[1]; Zhang, Jianquan ^[1]; Ade, Harald ^[2]; Yan, He ^[1]

HKUST‐Shenzhen Research Institute No. 9 Yuexing 1st Road, Hi‐tech Park Nanshan Shenzhen 518057 China, Department of Chemistry and Energy Institute Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration &, Reconstruction The Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong
Department of Physics and Organic and Carbon Electronics Lab (ORaCEL) North Carolina State University Raleigh NC 27695 USA

Abstract

The field of nonfullerene organic solar cells (OSCs) has seen an impressive progress, largely due to advances in high‐performance small molecule acceptors (SMAs). As a large portion of the solar energy is located in the near‐infrared region, it is important to develop ultralow‐bandgap SMAs that have extended absorption in the spectral range of 800–1000 nm to maximize light absorption and efficiencies. In this work, three low‐bandgap SMAs, namely, IXIC, IXIC‐2Cl, and IXIC‐4Cl, are designed and synthesized with same fused terthieno[3,2‐ b ]thiophene donor unit and different end groups (EGs). The three SMAs all have low optical bandgap ( E _g ) of 1.35, 1.30, and 1.25 eV, respectively. The chlorination on EGs can lower the energy level and broaden absorption range of the SMAs. As a result, the V _oc of the devices is reduced but the J _sc is significantly increased. In addition, the addition of chlorine atoms can enhance π–π stacking and crystallinity of the SMAs, which result in high fill factors. Overall, the optimum EGs are monochlorine‐substituted IC and OSCs based on PBDB‐T:IXIC‐2Cl that can achieve remarkable power conversion efficiencies (PCEs) of 12.2%, which is one of the highest PCEs for nonfullerene organic solar cells based on low‐bandgap SMAs.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1463199

Journal Information:: Advanced Energy Materials, Journal Name: Advanced Energy Materials Journal Issue: 27 Vol. 8; ISSN 1614-6832

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

Country of Publication:: Germany

Language:: English

References (46)

Side Group Engineering of Small Molecular Acceptors for High-Performance Fullerene-Free Polymer Solar Cells: Thiophene Being Superior to Selenophene Gao, Wei; An, Qiaoshi; Ming, Ruijie Advanced Functional Materials, Vol. 27, Issue 34 https://doi.org/10.1002/adfm.201702194	journal	July 2017
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
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
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
A New Nonfullerene Electron Acceptor with a Ladder Type Backbone for High-Performance Organic Solar Cells Qiu, Nailiang; Zhang, Huijing; Wan, Xiangjian Advanced Materials, Vol. 29, Issue 6 https://doi.org/10.1002/adma.201604964	journal	November 2016
Single-Junction Binary-Blend Nonfullerene Polymer Solar Cells with 12.1% Efficiency Zhao, Fuwen; Dai, Shuixing; Wu, Yang Advanced Materials, Vol. 29, Issue 18 https://doi.org/10.1002/adma.201700144	journal	March 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
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
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
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
A Twisted Thieno[3,4- b ]thiophene-Based Electron Acceptor Featuring a 14-π-Electron Indenoindene Core for High-Performance Organic Photovoltaics Xu, Sheng jie; Zhou, Zichun; Liu, Wuyue Advanced Materials, Vol. 29, Issue 43 https://doi.org/10.1002/adma.201704510	journal	October 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
Fine-Tuning the Energy Levels of a Nonfullerene Small-Molecule Acceptor to Achieve a High Short-Circuit Current and a Power Conversion Efficiency over 12% in Organic Solar Cells Kan, Bin; Zhang, Jiangbin; Liu, Feng Advanced Materials, Vol. 30, Issue 3 https://doi.org/10.1002/adma.201704904	journal	December 2017
Fused Tris(thienothiophene)-Based Electron Acceptor with Strong Near-Infrared Absorption for High-Performance As-Cast Solar Cells Li, Tengfei; Dai, Shuixing; Ke, Zhifan Advanced Materials, Vol. 30, Issue 10 https://doi.org/10.1002/adma.201705969	journal	January 2018
Fine-Tuning of Molecular Packing and Energy Level through Methyl Substitution Enabling Excellent Small Molecule Acceptors for Nonfullerene Polymer Solar Cells with Efficiency up to 12.54% Luo, Zhenghui; Bin, Haijun; Liu, Tao Advanced Materials, Vol. 30, Issue 9 https://doi.org/10.1002/adma.201706124	journal	January 2018
Enhancing the Performance of Polymer Solar Cells via Core Engineering of NIR-Absorbing Electron Acceptors Dai, Shuixing; Li, Tengfei; Wang, Wei Advanced Materials, Vol. 30, Issue 15 https://doi.org/10.1002/adma.201706571	journal	March 2018
A High-Efficiency Organic Solar Cell Enabled by the Strong Intramolecular Electron Push-Pull Effect of the Nonfullerene Acceptor Li, Wanning; Ye, Long; Li, Sunsun Advanced Materials, Vol. 30, Issue 16 https://doi.org/10.1002/adma.201707170	journal	March 2018
Nonfullerene Tandem Organic Solar Cells with High Performance of 14.11% Zhang, Yamin; Kan, Bin; Sun, Yanna Advanced Materials, Vol. 30, Issue 18 https://doi.org/10.1002/adma.201707508	journal	March 2018
Asymmetrical Ladder-Type Donor-Induced Polar Small Molecule Acceptor to Promote Fill Factors Approaching 77% for High-Performance Nonfullerene Polymer Solar Cells Gao, Wei; Zhang, Miao; Liu, Tao Advanced Materials, Vol. 30, Issue 26 https://doi.org/10.1002/adma.201800052	journal	May 2018
Over 14% Efficiency in Polymer Solar Cells Enabled by a Chlorinated Polymer Donor Zhang, Shaoqing; Qin, Yunpeng; Zhu, Jie Advanced Materials, Vol. 30, Issue 20 https://doi.org/10.1002/adma.201800868	journal	March 2018
Structure Evolution of Oligomer Fused-Ring Electron Acceptors toward High Efficiency of As-Cast Polymer Solar Cells Lin, Yuze; Li, Tengfei; Zhao, Fuwen Advanced Energy Materials, Vol. 6, Issue 18 https://doi.org/10.1002/aenm.201600854	journal	July 2016
Significant Influence of the Methoxyl Substitution Position on Optoelectronic Properties and Molecular Packing of Small-Molecule Electron Acceptors for Photovoltaic Cells Li, Sunsun; Ye, Long; Zhao, Wenchao Advanced Energy Materials, Vol. 7, Issue 17 https://doi.org/10.1002/aenm.201700183	journal	May 2017
Terthieno[3,2- b ]Thiophene (6T) Based Low Bandgap Fused-Ring Electron Acceptor for Highly Efficient Solar Cells with a High Short-Circuit Current Density and Low Open-Circuit Voltage Loss Shi, Xueliang; Chen, Jingde; Gao, Ke Advanced Energy Materials, Vol. 8, Issue 12 https://doi.org/10.1002/aenm.201702831	journal	January 2018
A Halogenation Strategy for over 12% Efficiency Nonfullerene Organic Solar Cells Wang, Yanbo; Zhang, Yamin; Qiu, Nailiang Advanced Energy Materials, Vol. 8, Issue 15 https://doi.org/10.1002/aenm.201702870	journal	January 2018
A Novel Thiophene-Fused Ending Group Enabling an Excellent Small Molecule Acceptor for High-Performance Fullerene-Free Polymer Solar Cells with 11.8% Efficiency Xie, Dongjun; Liu, Tao; Gao, Wei Solar RRL, Vol. 1, Issue 6 https://doi.org/10.1002/solr.201700044	journal	May 2017
Non-Fullerene Electron Acceptors for Use in Organic Solar Cells Nielsen, Christian B.; Holliday, Sarah; Chen, Hung-Yang Accounts of Chemical Research, Vol. 48, Issue 11 https://doi.org/10.1021/acs.accounts.5b00199	journal	October 2015
Oligomer Molecules for Efficient Organic Photovoltaics Lin, Yuze; Zhan, Xiaowei Accounts of Chemical Research, Vol. 49, Issue 2 https://doi.org/10.1021/acs.accounts.5b00363	journal	November 2015
An A-D-A Type Small-Molecule Electron Acceptor with End-Extended Conjugation for High Performance Organic Solar Cells Feng, Huanran; Qiu, Nailiang; Wang, Xian Chemistry of Materials, Vol. 29, Issue 18 https://doi.org/10.1021/acs.chemmater.7b02811	journal	September 2017
Ladder-Type Dithienonaphthalene-Based Small-Molecule Acceptors for Efficient Nonfullerene Organic Solar Cells Ma, Yunlong; Zhang, Meiqi; Yan, Yu Chemistry of Materials, Vol. 29, Issue 18 https://doi.org/10.1021/acs.chemmater.7b02887	journal	September 2017
Synthesis and Photovoltaic Properties of a Series of Narrow Bandgap Organic Semiconductor Acceptors with Their Absorption Edge Reaching 900 nm Li, Xiaojun; Huang, He; Bin, Haijun Chemistry of Materials, Vol. 29, Issue 23 https://doi.org/10.1021/acs.chemmater.7b03928	journal	November 2017
Breaking 10% Efficiency in Semitransparent Solar Cells with Fused-Undecacyclic Electron Acceptor Jia, Boyu; Dai, Shuixing; Ke, Zhifan Chemistry of Materials, Vol. 30, Issue 1 https://doi.org/10.1021/acs.chemmater.7b04251	journal	December 2017
Recent Advances in Bulk Heterojunction Polymer Solar Cells Lu, Luyao; Zheng, Tianyue; Wu, Qinghe Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00098	journal	August 2015
Nonfullerene Acceptor Molecules for Bulk Heterojunction Organic Solar Cells Zhang, Guangye; Zhao, Jingbo; Chow, Philip C. Y. Chemical Reviews, Vol. 118, Issue 7 https://doi.org/10.1021/acs.chemrev.7b00535	journal	February 2018
Synthesis of Conjugated Polymers for Organic Solar Cell Applications Cheng, Yen-Ju; Yang, Sheng-Hsiung; Hsu, Chain-Shu Chemical Reviews, Vol. 109, Issue 11 https://doi.org/10.1021/cr900182s	journal	November 2009
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
Small-Molecule Acceptor Based on the Heptacyclic Benzodi(cyclopentadithiophene) Unit for Highly Efficient Nonfullerene Organic Solar Cells Kan, Bin; Feng, Huanran; Wan, Xiangjian Journal of the American Chemical Society, Vol. 139, Issue 13 https://doi.org/10.1021/jacs.7b01170	journal	March 2017
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
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 Efficiency Near-Infrared and Semitransparent Non-Fullerene Acceptor Organic Photovoltaic Cells Li, Yongxi; Lin, Jiu-Dong; Che, Xiaozhou Journal of the American Chemical Society, Vol. 139, Issue 47 https://doi.org/10.1021/jacs.7b11278	journal	November 2017
Non-fullerene acceptors for organic solar cells Yan, Cenqi; Barlow, Stephen; Wang, Zhaohui Nature Reviews Materials, Vol. 3, Issue 3 https://doi.org/10.1038/natrevmats.2018.3	journal	February 2018
Organic solar cells based on non-fullerene acceptors Hou, Jianhui; Inganäs, Olle; Friend, Richard H. Nature Materials, Vol. 17, Issue 2 https://doi.org/10.1038/nmat5063	journal	January 2018
Next-generation organic photovoltaics based on non-fullerene acceptors Cheng, Pei; Li, Gang; Zhan, Xiaowei Nature Photonics, Vol. 12, Issue 3 https://doi.org/10.1038/s41566-018-0104-9	journal	February 2018
A near-infrared non-fullerene electron acceptor for high performance polymer solar cells Li, Yongxi; Zhong, Lian; Gautam, Bhoj Energy & Environmental Science, Vol. 10, Issue 7 https://doi.org/10.1039/C7EE00844A	journal	January 2017
Halogenated conjugated molecules for ambipolar field-effect transistors and non-fullerene organic solar cells Yang, Fan; Li, Cheng; Lai, Wenbin Materials Chemistry Frontiers, Vol. 1, Issue 7 https://doi.org/10.1039/C7QM00025A	journal	January 2017
Indacenodithiophene: a promising building block for high performance polymer solar cells Li, Yongxi; Gu, Minchao; Pan, Zhe Journal of Materials Chemistry A, Vol. 5, Issue 22 https://doi.org/10.1039/C7TA02562A	journal	January 2017
New small-molecule acceptors based on hexacyclic naphthalene(cyclopentadithiophene) for efficient non-fullerene organic solar cells Yi, Yuan-Qiu-Qiang; Feng, Huanran; Chang, Meijia Journal of Materials Chemistry A, Vol. 5, Issue 33 https://doi.org/10.1039/C7TA05809H	journal	January 2017

Similar Records

Benzotriazole‐Based Nonfused Ring Acceptors for Efficient and Thermally Stable Organic Solar Cells

Journal Article · Fri Aug 05 00:00:00 EDT 2022 · Macromolecular Rapid Communications · OSTI ID:2422649

Single‐Junction Binary‐Blend Nonfullerene Polymer Solar Cells with 12.1% Efficiency

Journal Article · Thu Mar 09 23:00:00 EST 2017 · Advanced Materials · OSTI ID:1400823

Electron‐Deficient and Quinoid Central Unit Engineering for Unfused Ring‐Based A ₁ –D–A ₂ –D–A ₁ ‐Type Acceptor Enables High Performance Nonfullerene Polymer Solar Cells with High V _oc and PCE Simultaneously

Journal Article · Wed May 06 00:00:00 EDT 2020 · Small · OSTI ID:1617525

Modulation of End Groups for Low‐Bandgap Nonfullerene Acceptors Enabling High‐Performance Organic Solar Cells

Citation Formats

References (46)

Similar Records

Related Subjects