High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains

Bin, Haijun; Yao, Jia; Yang, Yankang; Angunawela, Indunil; Sun, Chenkai; Gao, Liang; Ye, Long; Qiu, Beibei; Xue, Lingwei; Zhu, Chenhui; Yang, Chunhe; Zhang, Zhi‐Guo; Ade, Harald; Li, Yongfang

doi:10.1002/adma.201706361

Title: High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains

Journal Article · Mon May 21 00:00:00 EDT 2018 · Advanced Materials

DOI:https://doi.org/10.1002/adma.201706361· OSTI ID:1438077

Bin, Haijun ^[1]; Yao, Jia ^[2]; Yang, Yankang ^[1]; Angunawela, Indunil ^[3]; Sun, Chenkai ^[4]; Gao, Liang ^[4]; Ye, Long ^[3]; Qiu, Beibei ^[4]; Xue, Lingwei ^[4]; Zhu, Chenhui ^[5]; Yang, Chunhe ^[6]; Zhang, Zhi‐Guo ^[4]; Ade, Harald ^[3];

^[7]

CAS Research/Education Center for Excellence in Molecular Sciences CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China, School of Chemical Science University of Chinese Academy of Sciences Beijing 100049 China
CAS Research/Education Center for Excellence in Molecular Sciences CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China, Department of Chemistry School of Science Beijing JiaoTong University Beijing 100044 China
Department of Physics and Organic and Carbon Electronics Lab (ORaCEL) North Carolina State University Raleigh NC 27695 USA
CAS Research/Education Center for Excellence in Molecular Sciences CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China
Advanced Light Source Lawrence Berkeley National Laboratory Berkeley CA 94720 USA
Department of Chemistry School of Science Beijing JiaoTong University Beijing 100044 China
CAS Research/Education Center for Excellence in Molecular Sciences CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China, School of Chemical Science University of Chinese Academy of Sciences Beijing 100049 China, Laboratory of Advanced Optoelectronic Materials College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou Jiangsu 215123 China

Abstract Two medium‐bandgap p‐type organic small molecules H21 and H22 with an alkylsily‐thienyl conjugated side chain on benzo[1,2‐ b :4,5‐ b ′]dithiophene central units are synthesized and used as donors in all‐small‐molecule organic solar cells (SM‐OSCs) with a narrow‐bandgap n‐type small molecule 2,2′‐((2Z,2′Z)‐((4,4,9,9‐tetrahexyl‐4,9‐dihydro‐ s ‐indaceno[1,2‐ b :5,6‐ b ′]dithiophene‐2,7‐diyl)bis(methanylylidene))bis(3‐oxo‐2,3‐dihydro‐1H‐indene‐2,1‐diylidene))dimalononitrile (IDIC) as the acceptor. In comparison to H21 with 3‐ethyl rhodanine as the terminal group, H22 with cyanoacetic acid esters as the terminal group shows blueshifted absorption, higher charge‐carrier mobility and better 3D charge pathway in blend films. The power conversion efficiency (PCE) of the SM‐OSCs based on H22:IDIC reaches 10.29% with a higher open‐circuit voltage of 0.942 V and a higher fill factor of 71.15%. The PCE of 10.29% is among the top efficiencies of nonfullerene SM‐OSCs reported in the literature to date.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

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

OSTI ID:: 1438077

Journal Information:: Advanced Materials, Journal Name: Advanced Materials Vol. 30 Journal Issue: 27; ISSN 0935-9648

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

Country of Publication:: Germany

Language:: English

Citation Metrics:

Cited by: 137 works

Citation information provided by
Web of Science

References (64)

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
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
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
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
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
A High-Mobility Electron-Transport Polymer with Broad Absorption and Its Use in Field-Effect Transistors and All-Polymer Solar Cells Zhan, Xiaowei; Tan, Zhan'ao; Domercq, Benoit Journal of the American Chemical Society, Vol. 129, Issue 23, p. 7246-7247 https://doi.org/10.1021/ja071760d	journal	June 2007
Organic photovoltaics: technology and market Brabec, Christoph J. Solar Energy Materials and Solar Cells, Vol. 83, Issue 2-3, p. 273-292 https://doi.org/10.1016/j.solmat.2004.02.030	journal	June 2004
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
Designing Efficient Non-Fullerene Acceptors by Tailoring Extended Fused-Rings with Electron-Deficient Groups Lin, Yuze; Zhan, Xiaowei Advanced Energy Materials, Vol. 5, Issue 20 https://doi.org/10.1002/aenm.201501063	journal	September 2015
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
Efficient fullerene-free organic solar cells based on fused-ring oligomer molecules Lin, Yuze; Wang, Jiayu; Li, Tengfei Journal of Materials Chemistry A, Vol. 4, Issue 4 https://doi.org/10.1039/C5TA10424F	journal	January 2016
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
Solution-Processable Organic Molecule Photovoltaic Materials with Bithienyl-benzodithiophene Central Unit and Indenedione End Groups Shen, Suling; Jiang, Pei; He, Chang Chemistry of Materials, Vol. 25, Issue 11 https://doi.org/10.1021/cm400782q	journal	May 2013
Effect of Alkylsilyl Side-Chain Structure on Photovoltaic Properties of Conjugated Polymer Donors Bin, Haijun; Yang, Yankang; Peng, Zhengxing Advanced Energy Materials, Vol. 8, Issue 8 https://doi.org/10.1002/aenm.201702324	journal	December 2017
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
All-Polymer Solar Cells from Perylene Diimide Based Copolymers: Material Design and Phase Separation Control Zhou, Erjun; Cong, Junzi; Wei, Qingshuo Angewandte Chemie International Edition, Vol. 50, Issue 12, p. 2799-2803 https://doi.org/10.1002/anie.201005408	journal	February 2011
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
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
Solution Processable Rhodanine-Based Small Molecule Organic Photovoltaic Cells with a Power Conversion Efficiency of 6.1% Li, Zhi; He, Guangrui; Wan, Xiangjian Advanced Energy Materials, Vol. 2, Issue 1 https://doi.org/10.1002/aenm.201100572	journal	November 2011
Highly efficient and thermally stable fullerene-free organic solar cells based on a small molecule donor and acceptor Badgujar, Sachin; Song, Chang Eun; Oh, Sora Journal of Materials Chemistry A, Vol. 4, Issue 42 https://doi.org/10.1039/C6TA06367E	journal	January 2016
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
All-Small-Molecule Nonfullerene Organic Solar Cells with High Fill Factor and High Efficiency over 10% Qiu, Beibei; Xue, Lingwei; Yang, Yankang Chemistry of Materials, Vol. 29, Issue 17 https://doi.org/10.1021/acs.chemmater.7b02536	journal	August 2017
All-small-molecule organic solar cells based on an electron donor incorporating binary electron-deficient units Feng, Guitao; Xu, Yunhua; Zhang, Jianqi Journal of Materials Chemistry A, Vol. 4, Issue 16 https://doi.org/10.1039/C5TA10430K	journal	January 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
Small Molecules Based on Benzo[1,2-b:4,5-b′]dithiophene Unit for High-Performance Solution-Processed Organic Solar Cells Zhou, Jiaoyan; Wan, Xiangjian; Liu, Yongsheng Journal of the American Chemical Society, Vol. 134, Issue 39 https://doi.org/10.1021/ja306865z	journal	September 2012
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
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
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
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
Efficient Solution-Processed Small-Molecule Solar Cells with Inverted Structure Kyaw, Aung Ko Ko; Wang, Dong Hwan; Gupta, Vinay Advanced Materials, Vol. 25, Issue 17 https://doi.org/10.1002/adma.201300295	journal	March 2013
Fluorination-enabled optimal morphology leads to over 11% efficiency for inverted small-molecule organic solar cells Deng, Dan; Zhang, Yajie; Zhang, Jianqi Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13740	journal	December 2016
High-Performance Organic Solar Cells Based on a Small Molecule with Alkylthio-Thienyl-Conjugated Side Chains without Extra Treatments Cui, Chaohua; Guo, Xia; Min, Jie Advanced Materials, Vol. 27, Issue 45 https://doi.org/10.1002/adma.201503815	journal	October 2015
Indene−C₆₀ Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells He, Youjun; Chen, Hsiang-Yu; Hou, Jianhui Journal of the American Chemical Society, Vol. 132, Issue 4, p. 1377-1382 https://doi.org/10.1021/ja908602j	journal	February 2010
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
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
Understanding Energy Loss in Organic Solar Cells: Toward a New Efficiency Regime Menke, S. Matthew; Ran, Niva A.; Bazan, Guillermo C. Joule, Vol. 2, Issue 1 https://doi.org/10.1016/j.joule.2017.09.020	journal	January 2018
Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices Chen, Junwu; Cao, Yong Accounts of Chemical Research, Vol. 42, Issue 11 https://doi.org/10.1021/ar900061z	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
Solution-processed small-molecule solar cells with 6.7% efficiency Sun, Yanming; Welch, Gregory C.; Leong, Wei Lin Nature Materials, Vol. 11, Issue 1, p. 44-48 https://doi.org/10.1038/nmat3160	journal	November 2011
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
High performance all-small-molecule solar cells: engineering the nanomorphology via processing additives Min, Jie; Kwon, Oh Kyu; Cui, Chaohua Journal of Materials Chemistry A, Vol. 4, Issue 37 https://doi.org/10.1039/C6TA05303C	journal	January 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
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
Intensity Dependence of Current–Voltage Characteristics and Recombination in High-Efficiency Solution-Processed Small-Molecule Solar Cells Kyaw, Aung Ko Ko; Wang, Dong Hwan; Gupta, Vinay ACS Nano, Vol. 7, Issue 5 https://doi.org/10.1021/nn401267s	journal	April 2013
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
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
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
Small-molecule solar cells with efficiency over 9% Zhang, Qian; Kan, Bin; Liu, Feng Nature Photonics, Vol. 9, Issue 1 https://doi.org/10.1038/nphoton.2014.269	journal	November 2014
Efficient Charge Transfer and Fine-Tuned Energy Level Alignment in a THF-Processed Fullerene-Free Organic Solar Cell with 11.3% Efficiency Zheng, Zhong; Awartani, Omar M.; Gautam, Bhoj Advanced Materials, Vol. 29, Issue 5 https://doi.org/10.1002/adma.201604241	journal	November 2016
Fullerene-free small molecule organic solar cells with a high open circuit voltage of 1.15 V Ni, Wang; Li, Miaomiao; Kan, Bin Chemical Communications, Vol. 52, Issue 3 https://doi.org/10.1039/C5CC07973J	journal	January 2016
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
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
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
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
Additive-Assisted Control over Phase-Separated Nanostructures by Manipulating Alkylthienyl Position at Donor Backbone for Solution-Processed, Non-Fullerene, All-Small-Molecule Solar Cells Huang, Jianhua; Wang, Xue; Zhang, Xin ACS Applied Materials & Interfaces, Vol. 6, Issue 6 https://doi.org/10.1021/am406050j	journal	March 2014
Efficient Vacuum-Deposited Organic Solar Cells Based on a New Low-Bandgap Oligothiophene and Fullerene C60 Schulze, K.; Uhrich, C.; Schüppel, R. Advanced Materials, Vol. 18, Issue 21 https://doi.org/10.1002/adma.200600658	journal	November 2006
New Wide Band Gap Donor for Efficient Fullerene-Free All-Small-Molecule Organic Solar Cells Yang, Liyan; Zhang, Shaoqing; He, Chang Journal of the American Chemical Society, Vol. 139, Issue 5 https://doi.org/10.1021/jacs.6b11612	journal	January 2017
Effect of Temperature and Illumination on the Electrical Characteristics of Polymer–Fullerene Bulk-Heterojunction Solar Cells Riedel, I.; Parisi, J.; Dyakonov, V. Advanced Functional Materials, Vol. 14, Issue 1 https://doi.org/10.1002/adfm.200304399	journal	January 2004
Surface Plasmonic Effects of Metallic Nanoparticles on the Performance of Polymer Bulk Heterojunction Solar Cells Wu, Jyh-Lih; Chen, Fang-Chung; Hsiao, Yu-Sheng ACS Nano, Vol. 5, Issue 2 https://doi.org/10.1021/nn102295p	journal	January 2011
Photoinduced Electron Transfer from a Conducting Polymer to Buckminsterfullerene Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J. Science, Vol. 258, Issue 5087, p. 1474-1476 https://doi.org/10.1126/science.258.5087.1474	journal	November 1992
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
Semiconducting polymer‐buckminsterfullerene heterojunctions: Diodes, photodiodes, and photovoltaic cells Sariciftci, N. S.; Braun, D.; Zhang, C. Applied Physics Letters, Vol. 62, Issue 6 https://doi.org/10.1063/1.108863	journal	February 1993

Similar Records

Simplified synthetic routes for low cost and high photovoltaic performance n-type organic semiconductor acceptors

Journal Article · Thu Jan 31 00:00:00 EST 2019 · Nature Communications · OSTI ID:1438077

Li, Xiaojun; Pan, Fei; Sun, Chenkai; +10 more

Naphthodithiophene‐Based Nonfullerene Acceptor for High‐Performance Organic Photovoltaics: Effect of Extended Conjugation

Journal Article · Thu Nov 23 00:00:00 EST 2017 · Advanced Materials · OSTI ID:1438077

Zhu, Jingshuai; Ke, Zhifan; Zhang, Qianqian; +8 more

Printed Nonfullerene Organic Solar Cells with the Highest Efficiency of 9.5%

Journal Article · Mon Jan 22 00:00:00 EST 2018 · Advanced Energy Materials · OSTI ID:1438077

Lin, Yuanbao; Jin, Yingzhi; Dong, Sheng; +9 more

Title: High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains

Citation Formats

References (64)

Similar Records

Related Subjects