Alkyl Chain End Group Engineering of Small Molecule Acceptors for Non-Fullerene Organic Solar Cells

Qu, Jianfei; Mu, Zhao; Lai, Hanjian; Chen, Hui; Liu, Tao; Zhang, Shuai; Chen, Wei; He, Feng

doi:10.1021/acsaem.8b00851

Title: Alkyl Chain End Group Engineering of Small Molecule Acceptors for Non-Fullerene Organic Solar Cells

Journal Article · Fri Aug 31 00:00:00 EDT 2018 · ACS Applied Energy Materials

DOI:https://doi.org/10.1021/acsaem.8b00851· OSTI ID:1483636

Qu, Jianfei ^[1]; Mu, Zhao ^[1]; Lai, Hanjian ^[1]; Chen, Hui ^[1]; Liu, Tao ^[1]; Zhang, Shuai ^[1];

^[2];

^[1]

Southern Univ. of Science and Technology, Shenzhen (People’s Republic of China)
Argonne National Lab. (ANL), Lemont, IL (United States); The Univ. of Chicago, Chicago, IL (United States)

Alkyl chain engineering is widely used to prepare high-performance donor materials. However, relatively few studies have been focused on the alkyl chain optimization of acceptor materials. Herein, a series of new A-D-A (acceptor-donor-acceptor) type small molecule acceptors (ITBTR-C2, ITBTR-C4, ITBTR-C6, and ITBTR-C8) with indacenodithieno[3,2-b]thiophene (IDTT) as the core, benzothiadiazole (BT) as the π bridge, and ethyl-, butyl-, hexyl-, and octyl-substituted 2-(1,1-dicyanomethylene) rhodanine as the end groups, respectively, are successfully synthesized to systematically investigate the alkyl substituent effects on the physical, chemical, and electronic properties of A-D-A type small molecule acceptors. All molecules exhibit a strong and broad absorption from 600 to 800 nm as well as similar HOMO and LUMO energy levels. ITBTR-C6 with hexyl substitution showed the highest electron mobility and better phase separation morphology after blending with a donor polymer (PBDB-T). Therefore, inverted bulk heterojunction organic solar cells based on ITBTR-C6:PBDB-T blends exhibit the highest power conversion efficiency (PCE) of 8.26% with an open-circuit voltage (V_OC) of 0.89 V, a high short-circuit current density (J_SC) of 15.80 mA/cm2, and a fill factor (FF) of 58.21%, while the PCEs of ITBTR-C2-, ITBTR-C4-, and ITBTR-C8-based devices are 7.04%, 7.43%, and 7.93%, respectively. After solvent vapor and thermal annealing, both the J_SC and FF values of the ITBTR-C6-based device further increased, leading to a PCE of 9.29%. Furthermore, the results demonstrate that the alkyl chain substitution of A-D-A type small molecule acceptors is critical, and an appropriate adjustment of the alkyl chains can effectively enhance device performance.

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Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Natural Science Foundation of China (NSFC); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1483636

Journal Information:: ACS Applied Energy Materials, Vol. 1, Issue 9; ISSN 2574-0962

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 17 works

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References (53)

Polymer solar cells Li, Gang; Zhu, Rui; Yang, Yang Nature Photonics, Vol. 6, Issue 3 https://doi.org/10.1038/nphoton.2012.11	journal	February 2012
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
Conjugated Polymer-Based Organic Solar Cells Günes, Serap; Neugebauer, Helmut; Sariciftci, Niyazi Serdar Chemical Reviews, Vol. 107, Issue 4, p. 1324-1338 https://doi.org/10.1021/cr050149z	journal	April 2007
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
Efficient photodiodes from interpenetrating polymer networks Halls, J. J. M.; Walsh, C. A.; Greenham, N. C. Nature, Vol. 376, Issue 6540, p. 498-500 https://doi.org/10.1038/376498a0	journal	August 1995
Molecular Design of Benzodithiophene-Based Organic Photovoltaic Materials Yao, Huifeng; Ye, Long; Zhang, Hao Chemical Reviews, Vol. 116, Issue 12 https://doi.org/10.1021/acs.chemrev.6b00176	journal	June 2016
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
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
Solution-processed organic tandem solar cells with power conversion efficiencies >12% Li, Miaomiao; Gao, Ke; Wan, Xiangjian Nature Photonics, Vol. 11, Issue 2 https://doi.org/10.1038/nphoton.2016.240	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
Preparation and Characterization of Fulleroid and Methanofullerene Derivatives Hummelen, Jan C.; Knight, Brian W.; LePeq, F. The Journal of Organic Chemistry, Vol. 60, Issue 3 https://doi.org/10.1021/jo00108a012	journal	February 1995
A Rhodanine Flanked Nonfullerene Acceptor for Solution-Processed Organic Photovoltaics Holliday, Sarah; Ashraf, Raja Shahid; Nielsen, Christian B. Journal of the American Chemical Society, Vol. 137, Issue 2 https://doi.org/10.1021/ja5110602	journal	January 2015
Electron-Accepting Conjugated Materials Based on 2-Vinyl-4,5-dicyanoimidazoles for Application in Organic Electronics Shin, Richard Y. C.; Sonar, Prashant; Siew, Pei Sann The Journal of Organic Chemistry, Vol. 74, Issue 9 https://doi.org/10.1021/jo802720m	journal	May 2009
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
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
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
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
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
A Thieno[3,4- b ]thiophene-Based Non-fullerene Electron Acceptor for High-Performance Bulk-Heterojunction Organic Solar Cells Liu, Feng; Zhou, Zichun; Zhang, Cheng Journal of the American Chemical Society, Vol. 138, Issue 48 https://doi.org/10.1021/jacs.6b08523	journal	November 2016
Side-Chain Isomerization on an n-type Organic Semiconductor ITIC Acceptor Makes 11.77% High Efficiency Polymer Solar Cells Yang, Yankang; Zhang, Zhi-Guo; Bin, Haijun Journal of the American Chemical Society, Vol. 138, Issue 45 https://doi.org/10.1021/jacs.6b09110	journal	November 2016
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
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
High-Performance As-Cast Nonfullerene Polymer Solar Cells with Thicker Active Layer and Large Area Exceeding 11% Power Conversion Efficiency Fan, Qunping; Wang, Yan; Zhang, Maojie Advanced Materials, Vol. 30, Issue 6 https://doi.org/10.1002/adma.201704546	journal	December 2017
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
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
9.73% Efficiency Nonfullerene All Organic Small Molecule Solar Cells with Absorption-Complementary Donor and Acceptor Bin, Haijun; Yang, Yankang; Zhang, Zhi-Guo Journal of the American Chemical Society, Vol. 139, Issue 14 https://doi.org/10.1021/jacs.6b12826	journal	March 2017
Improved Domain Size and Purity Enables Efficient All-Small-Molecule Ternary Solar Cells Zhang, Hao; Wang, Xiaohui; Yang, Liyan Advanced Materials, Vol. 29, Issue 42 https://doi.org/10.1002/adma.201703777	journal	September 2017
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
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
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
Ternary organic solar cells offer 14% power conversion efficiency Xiao, Zuo; Jia, Xue; Ding, Liming Science Bulletin, Vol. 62, Issue 23 https://doi.org/10.1016/j.scib.2017.11.003	journal	December 2017
Synergistic effect of fluorination on both donor and acceptor materials for high performance non-fullerene polymer solar cells with 13.5% efficiency Fan, Qunping; Su, Wenyan; Wang, Yan Science China Chemistry, Vol. 61, Issue 5 https://doi.org/10.1007/s11426-017-9199-1	journal	January 2018
Chlorine substituted 2D-conjugated polymer for high-performance polymer solar cells with 13.1% efficiency via toluene processing Fan, Qunping; Zhu, Qinglian; Xu, Zhuo Nano Energy, Vol. 48 https://doi.org/10.1016/j.nanoen.2018.04.002	journal	June 2018
Dithieno[3,2- b :2′,3′- d ]pyrrol Fused Nonfullerene Acceptors Enabling Over 13% Efficiency for Organic Solar Cells Sun, Jia; Ma, Xiaoling; Zhang, Zhuohan Advanced Materials, Vol. 30, Issue 16 https://doi.org/10.1002/adma.201707150	journal	March 2018
Thermostable single-junction organic solar cells with a power conversion efficiency of 14.62% Li, Hui; Xiao, Zuo; Ding, Liming Science Bulletin, Vol. 63, Issue 6 https://doi.org/10.1016/j.scib.2018.02.015	journal	March 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
Haptacyclic Carbazole-Based Ladder-Type Nonfullerene Acceptor with Side-Chain Optimization for Efficient Organic Photovoltaics Hsiao, Yu-Tang; Li, Chia-Hua; Chang, Shao-Ling ACS Applied Materials & Interfaces, Vol. 9, Issue 48 https://doi.org/10.1021/acsami.7b12612	journal	November 2017
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
Efficient Nonfullerene Polymer Solar Cells Enabled by a Novel Wide Bandgap Small Molecular Acceptor Zhang, Guangjun; Yang, Guofang; Yan, He Advanced Materials, Vol. 29, Issue 18 https://doi.org/10.1002/adma.201606054	journal	March 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
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
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
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
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
Environmentally Friendly Solvent-Processed Organic Solar Cells that are Highly Efficient and Adaptable for the Blade-Coating Method Zhao, Wenchao; Zhang, Shaoqing; Zhang, Yun Advanced Materials, Vol. 30, Issue 4 https://doi.org/10.1002/adma.201704837	journal	December 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
Enhancing Indacenodithiophene Acceptor Crystallinity via Substituent Manipulation Increases Organic Solar Cell Efficiency Aldrich, Thomas J.; Swick, Steven M.; Melkonyan, Ferdinand S. Chemistry of Materials, Vol. 29, Issue 24 https://doi.org/10.1021/acs.chemmater.7b04616	journal	November 2017
Fused-Ring Acceptors with Asymmetric Side Chains for High-Performance Thick-Film Organic Solar Cells Feng, Shiyu; Zhang, Cai'e; Liu, Yahui Advanced Materials, Vol. 29, Issue 42 https://doi.org/10.1002/adma.201703527	journal	September 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
Improved Charge Transport and Absorption Coefficient in Indacenodithieno[3,2-b]thiophene-based Ladder-Type Polymer Leading to Highly Efficient Polymer Solar Cells Xu, Yun-Xiang; Chueh, Chu-Chen; Yip, Hin-Lap Advanced Materials, Vol. 24, Issue 47 https://doi.org/10.1002/adma.201203246	journal	September 2012
Highly efficient new indoline dye having strong electron-withdrawing group for zinc oxide dye-sensitized solar cell Higashijima, Shinji; Miura, Hidetoshi; Fujita, Tomoki Tetrahedron, Vol. 67, Issue 34 https://doi.org/10.1016/j.tet.2011.06.016	journal	August 2011
Design, Application, and Morphology Study of a New Photovoltaic Polymer with Strong Aggregation in Solution State Qian, Deping; Ye, Long; Zhang, Maojie Macromolecules, Vol. 45, Issue 24 https://doi.org/10.1021/ma301900h	journal	December 2012

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