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

Abstract

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.

Authors:
 [1];  [2];  [1];  [3];  [4];  [4];  [3];  [4];  [4];  [5];  [6];  [4];  [3]; ORCiD logo [7]
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  1. 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
  2. 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
  3. Department of Physics and Organic and Carbon Electronics Lab (ORaCEL) North Carolina State University Raleigh NC 27695 USA
  4. 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
  5. Advanced Light Source Lawrence Berkeley National Laboratory Berkeley CA 94720 USA
  6. Department of Chemistry School of Science Beijing JiaoTong University Beijing 100044 China
  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, Laboratory of Advanced Optoelectronic Materials College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou Jiangsu 215123 China
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1438077
Grant/Contract Number:  
DE‐AC02‐05CH11231
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Advanced Materials
Additional Journal Information:
Journal Name: Advanced Materials Journal Volume: 30 Journal Issue: 27; Journal ID: ISSN 0935-9648
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

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, and Li, Yongfang. High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains. Germany: N. p., 2018. Web. doi:10.1002/adma.201706361.
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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. High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains. Germany. https://doi.org/10.1002/adma.201706361
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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, and Li, Yongfang. Mon . "High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains". Germany. https://doi.org/10.1002/adma.201706361.
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@article{osti_1438077,
title = {High‐Efficiency All‐Small‐Molecule Organic Solar Cells Based on an Organic Molecule Donor with Alkylsilyl‐Thienyl Conjugated Side Chains},
author = {Bin, Haijun and Yao, Jia and Yang, Yankang and Angunawela, Indunil and Sun, Chenkai and Gao, Liang and Ye, Long and Qiu, Beibei and Xue, Lingwei and Zhu, Chenhui and Yang, Chunhe and Zhang, Zhi‐Guo and Ade, Harald and Li, Yongfang},
abstractNote = {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.},
doi = {10.1002/adma.201706361},
journal = {Advanced Materials},
number = 27,
volume = 30,
place = {Germany},
year = {Mon May 21 00:00:00 EDT 2018},
month = {Mon May 21 00:00:00 EDT 2018}
}
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Journal Article:
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https://doi.org/10.1002/adma.201706361
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Works referenced in this record:

A High-Performing Solution-Processed Small Molecule:Perylene Diimide Bulk Heterojunction Solar Cell
journal, June 2013

  • Sharenko, Alexander; Proctor, Christopher M.; van der Poll, Thomas S.
  • Advanced Materials, Vol. 25, Issue 32
  • DOI: 10.1002/adma.201301167

High-Performance Electron Acceptor with Thienyl Side Chains for Organic Photovoltaics
journal, March 2016

  • Lin, Yuze; Zhao, Fuwen; He, Qiao
  • Journal of the American Chemical Society, Vol. 138, Issue 14
  • DOI: 10.1021/jacs.6b02004

Single-Junction Binary-Blend Nonfullerene Polymer Solar Cells with 12.1% Efficiency
journal, March 2017

Fullerene derivative acceptors for high performance polymer solar cells
journal, January 2011

  • He, Youjun; Li, Yongfang
  • Phys. Chem. Chem. Phys., Vol. 13, Issue 6
  • DOI: 10.1039/C0CP01178A

A High-Mobility Electron-Transport Polymer with Broad Absorption and Its Use in Field-Effect Transistors and All-Polymer Solar Cells
journal, June 2007

  • Zhan, Xiaowei; Tan, Zhan'ao; Domercq, Benoit
  • Journal of the American Chemical Society, Vol. 129, Issue 23, p. 7246-7247
  • DOI: 10.1021/ja071760d

Organic photovoltaics: technology and market
journal, June 2004

A Rhodanine Flanked Nonfullerene Acceptor for Solution-Processed Organic Photovoltaics
journal, January 2015

  • Holliday, Sarah; Ashraf, Raja Shahid; Nielsen, Christian B.
  • Journal of the American Chemical Society, Vol. 137, Issue 2
  • DOI: 10.1021/ja5110602

Designing Efficient Non-Fullerene Acceptors by Tailoring Extended Fused-Rings with Electron-Deficient Groups
journal, September 2015

High-efficiency and air-stable P3HT-based polymer solar cells with a new non-fullerene acceptor
journal, June 2016

  • Holliday, Sarah; Ashraf, Raja Shahid; Wadsworth, Andrew
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms11585

Efficient fullerene-free organic solar cells based on fused-ring oligomer molecules
journal, January 2016

  • Lin, Yuze; Wang, Jiayu; Li, Tengfei
  • Journal of Materials Chemistry A, Vol. 4, Issue 4
  • DOI: 10.1039/C5TA10424F

Molecular Design toward Highly Efficient Photovoltaic Polymers Based on Two-Dimensional Conjugated Benzodithiophene
journal, April 2014

  • Ye, Long; Zhang, Shaoqing; Huo, Lijun
  • Accounts of Chemical Research, Vol. 47, Issue 5
  • DOI: 10.1021/ar5000743

Solution-Processable Organic Molecule Photovoltaic Materials with Bithienyl-benzodithiophene Central Unit and Indenedione End Groups
journal, May 2013

  • Shen, Suling; Jiang, Pei; He, Chang
  • Chemistry of Materials, Vol. 25, Issue 11
  • DOI: 10.1021/cm400782q

Effect of Alkylsilyl Side-Chain Structure on Photovoltaic Properties of Conjugated Polymer Donors
journal, December 2017

  • Bin, Haijun; Yang, Yankang; Peng, Zhengxing
  • Advanced Energy Materials, Vol. 8, Issue 8
  • DOI: 10.1002/aenm.201702324

A SAXS/WAXS/GISAXS Beamline with Multilayer Monochromator
journal, October 2010

All-Polymer Solar Cells from Perylene Diimide Based Copolymers: Material Design and Phase Separation Control
journal, February 2011

  • Zhou, Erjun; Cong, Junzi; Wei, Qingshuo
  • Angewandte Chemie International Edition, Vol. 50, Issue 12, p. 2799-2803
  • DOI: 10.1002/anie.201005408

Side-Chain Isomerization on an n-type Organic Semiconductor ITIC Acceptor Makes 11.77% High Efficiency Polymer Solar Cells
journal, November 2016

  • Yang, Yankang; Zhang, Zhi-Guo; Bin, Haijun
  • Journal of the American Chemical Society, Vol. 138, Issue 45
  • DOI: 10.1021/jacs.6b09110

Design and Synthesis of a Low Bandgap Small Molecule Acceptor for Efficient Polymer Solar Cells
journal, July 2016

Solution Processable Rhodanine-Based Small Molecule Organic Photovoltaic Cells with a Power Conversion Efficiency of 6.1%
journal, November 2011

  • Li, Zhi; He, Guangrui; Wan, Xiangjian
  • Advanced Energy Materials, Vol. 2, Issue 1
  • DOI: 10.1002/aenm.201100572

Highly efficient and thermally stable fullerene-free organic solar cells based on a small molecule donor and acceptor
journal, January 2016

  • Badgujar, Sachin; Song, Chang Eun; Oh, Sora
  • Journal of Materials Chemistry A, Vol. 4, Issue 42
  • DOI: 10.1039/C6TA06367E

An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells
journal, January 2015

All-Small-Molecule Nonfullerene Organic Solar Cells with High Fill Factor and High Efficiency over 10%
journal, August 2017

All-small-molecule organic solar cells based on an electron donor incorporating binary electron-deficient units
journal, January 2016

  • Feng, Guitao; Xu, Yunhua; Zhang, Jianqi
  • Journal of Materials Chemistry A, Vol. 4, Issue 16
  • DOI: 10.1039/C5TA10430K

Efficient organic solar cells processed from hydrocarbon solvents
journal, January 2016

Small Molecules Based on Benzo[1,2-b:4,5-b′]dithiophene Unit for High-Performance Solution-Processed Organic Solar Cells
journal, September 2012

  • Zhou, Jiaoyan; Wan, Xiangjian; Liu, Yongsheng
  • Journal of the American Chemical Society, Vol. 134, Issue 39
  • DOI: 10.1021/ja306865z

Energy-Level Modulation of Small-Molecule Electron Acceptors to Achieve over 12% Efficiency in Polymer Solar Cells
journal, September 2016

Solution-processed organic tandem solar cells with power conversion efficiencies >12%
journal, December 2016

A Thieno[3,4- b ]thiophene-Based Non-fullerene Electron Acceptor for High-Performance Bulk-Heterojunction Organic Solar Cells
journal, November 2016

  • Liu, Feng; Zhou, Zichun; Zhang, Cheng
  • Journal of the American Chemical Society, Vol. 138, Issue 48
  • DOI: 10.1021/jacs.6b08523

Non-fullerene acceptors for organic photovoltaics: an emerging horizon
journal, January 2014

Efficient Solution-Processed Small-Molecule Solar Cells with Inverted Structure
journal, March 2013

  • Kyaw, Aung Ko Ko; Wang, Dong Hwan; Gupta, Vinay
  • Advanced Materials, Vol. 25, Issue 17
  • DOI: 10.1002/adma.201300295

Fluorination-enabled optimal morphology leads to over 11% efficiency for inverted small-molecule organic solar cells
journal, December 2016

  • Deng, Dan; Zhang, Yajie; Zhang, Jianqi
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms13740

Indene−C60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells
journal, February 2010

  • He, Youjun; Chen, Hsiang-Yu; Hou, Jianhui
  • Journal of the American Chemical Society, Vol. 132, Issue 4, p. 1377-1382
  • DOI: 10.1021/ja908602j

Efficient Nonfullerene Polymer Solar Cells Enabled by a Novel Wide Bandgap Small Molecular Acceptor
journal, March 2017

High-performance fullerene-free polymer solar cells with 6.31% efficiency
journal, January 2015

  • Lin, Yuze; Zhang, Zhi-Guo; Bai, Huitao
  • Energy & Environmental Science, Vol. 8, Issue 2
  • DOI: 10.1039/C4EE03424D

Understanding Energy Loss in Organic Solar Cells: Toward a New Efficiency Regime
journal, January 2018

Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices
journal, November 2009

  • Chen, Junwu; Cao, Yong
  • Accounts of Chemical Research, Vol. 42, Issue 11
  • DOI: 10.1021/ar900061z

Fused Nonacyclic Electron Acceptors for Efficient Polymer Solar Cells
journal, January 2017

  • Dai, Shuixing; Zhao, Fuwen; Zhang, Qianqian
  • Journal of the American Chemical Society, Vol. 139, Issue 3
  • DOI: 10.1021/jacs.6b12755

Solution-processed small-molecule solar cells with 6.7% efficiency
journal, November 2011

  • Sun, Yanming; Welch, Gregory C.; Leong, Wei Lin
  • Nature Materials, Vol. 11, Issue 1, p. 44-48
  • DOI: 10.1038/nmat3160

Deep Absorbing Porphyrin Small Molecule for High-Performance Organic Solar Cells with Very Low Energy Losses
journal, June 2015

  • Gao, Ke; Li, Lisheng; Lai, Tianqi
  • Journal of the American Chemical Society, Vol. 137, Issue 23
  • DOI: 10.1021/jacs.5b03740

High performance all-small-molecule solar cells: engineering the nanomorphology via processing additives
journal, January 2016

  • Min, Jie; Kwon, Oh Kyu; Cui, Chaohua
  • Journal of Materials Chemistry A, Vol. 4, Issue 37
  • DOI: 10.1039/C6TA05303C

Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions
journal, December 1995

A New Nonfullerene Electron Acceptor with a Ladder Type Backbone for High-Performance Organic Solar Cells
journal, November 2016

  • Qiu, Nailiang; Zhang, Huijing; Wan, Xiangjian
  • Advanced Materials, Vol. 29, Issue 6
  • DOI: 10.1002/adma.201604964

Reducing the efficiency–stability–cost gap of organic photovoltaics with highly efficient and stable small molecule acceptor ternary solar cells
journal, November 2016

  • Baran, Derya; Ashraf, Raja Shahid; Hanifi, David A.
  • Nature Materials, Vol. 16, Issue 3
  • DOI: 10.1038/nmat4797

11.4% Efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor
journal, December 2016

  • Bin, Haijun; Gao, Liang; Zhang, Zhi-Guo
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms13651

A Facile Planar Fused-Ring Electron Acceptor for As-Cast Polymer Solar Cells with 8.71% Efficiency
journal, February 2016

  • Lin, Yuze; He, Qiao; Zhao, Fuwen
  • Journal of the American Chemical Society, Vol. 138, Issue 9
  • DOI: 10.1021/jacs.6b00853

Non-Fullerene Polymer Solar Cells Based on Alkylthio and Fluorine Substituted 2D-Conjugated Polymers Reach 9.5% Efficiency
journal, March 2016

  • Bin, Haijun; Zhang, Zhi-Guo; Gao, Liang
  • Journal of the American Chemical Society, Vol. 138, Issue 13
  • DOI: 10.1021/jacs.6b01744

Polymer solar cells
journal, February 2012

Small-molecule solar cells with efficiency over 9%
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
journal, November 2016

  • Zheng, Zhong; Awartani, Omar M.; Gautam, Bhoj
  • Advanced Materials, Vol. 29, Issue 5
  • DOI: 10.1002/adma.201604241

Fullerene-free small molecule organic solar cells with a high open circuit voltage of 1.15 V
journal, January 2016

  • Ni, Wang; Li, Miaomiao; Kan, Bin
  • Chemical Communications, Vol. 52, Issue 3
  • DOI: 10.1039/C5CC07973J

Fullerene-Free Polymer Solar Cells with over 11% Efficiency and Excellent Thermal Stability
journal, April 2016

  • Zhao, Wenchao; Qian, Deping; Zhang, Shaoqing
  • Advanced Materials, Vol. 28, Issue 23
  • DOI: 10.1002/adma.201600281

A Series of Simple Oligomer-like Small Molecules Based on Oligothiophenes for Solution-Processed Solar Cells with High Efficiency
journal, March 2015

  • Kan, Bin; Li, Miaomiao; Zhang, Qian
  • Journal of the American Chemical Society, Vol. 137, Issue 11
  • DOI: 10.1021/jacs.5b00305

Small-Molecule Acceptor Based on the Heptacyclic Benzodi(cyclopentadithiophene) Unit for Highly Efficient Nonfullerene Organic Solar Cells
journal, March 2017

  • Kan, Bin; Feng, Huanran; Wan, Xiangjian
  • Journal of the American Chemical Society, Vol. 139, Issue 13
  • DOI: 10.1021/jacs.7b01170

An All-Small-Molecule Organic Solar Cell with High Efficiency Nonfullerene Acceptor
journal, February 2015

  • Kwon, Oh Kyu; Park, Jung-Hwa; Kim, Dong Won
  • Advanced Materials, Vol. 27, Issue 11
  • DOI: 10.1002/adma.201405429

Efficient Vacuum-Deposited Organic Solar Cells Based on a New Low-Bandgap Oligothiophene and Fullerene C60
journal, November 2006

New Wide Band Gap Donor for Efficient Fullerene-Free All-Small-Molecule Organic Solar Cells
journal, January 2017

  • Yang, Liyan; Zhang, Shaoqing; He, Chang
  • Journal of the American Chemical Society, Vol. 139, Issue 5
  • DOI: 10.1021/jacs.6b11612

Effect of Temperature and Illumination on the Electrical Characteristics of Polymer–Fullerene Bulk-Heterojunction Solar Cells
journal, January 2004

  • Riedel, I.; Parisi, J.; Dyakonov, V.
  • Advanced Functional Materials, Vol. 14, Issue 1
  • DOI: 10.1002/adfm.200304399

Surface Plasmonic Effects of Metallic Nanoparticles on the Performance of Polymer Bulk Heterojunction Solar Cells
journal, January 2011

  • Wu, Jyh-Lih; Chen, Fang-Chung; Hsiao, Yu-Sheng
  • ACS Nano, Vol. 5, Issue 2
  • DOI: 10.1021/nn102295p

Photoinduced Electron Transfer from a Conducting Polymer to Buckminsterfullerene
journal, November 1992

9.73% Efficiency Nonfullerene All Organic Small Molecule Solar Cells with Absorption-Complementary Donor and Acceptor
journal, March 2017

  • Bin, Haijun; Yang, Yankang; Zhang, Zhi-Guo
  • Journal of the American Chemical Society, Vol. 139, Issue 14
  • DOI: 10.1021/jacs.6b12826

Semiconducting polymer‐buckminsterfullerene heterojunctions: Diodes, photodiodes, and photovoltaic cells
journal, February 1993

  • Sariciftci, N. S.; Braun, D.; Zhang, C.
  • Applied Physics Letters, Vol. 62, Issue 6
  • DOI: 10.1063/1.108863
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