A Fused Ring Electron Acceptor with Decacyclic Core Enables over 13.5% Efficiency for Organic Solar Cells

He, Dan; Zhao, Fuwen; Xin, Jingming; Rech, Jeromy James; Wei, Zhixiang; Ma, Wei; You, Wei; Li, Bao; Jiang, Li; Li, Yongfang; Wang, Chunru

doi:10.1002/aenm.201802050

A Fused Ring Electron Acceptor with Decacyclic Core Enables over 13.5% Efficiency for Organic Solar Cells

Journal Article · Fri Sep 14 00:00:00 EDT 2018 · Advanced Energy Materials

DOI:https://doi.org/10.1002/aenm.201802050· OSTI ID:1471127

He, Dan ^[1]; Zhao, Fuwen ^[1]; Xin, Jingming ^[2]; Rech, Jeromy James ^[3]; Wei, Zhixiang ^[4]; Ma, Wei ^[2]; You, Wei ^[3]; Li, Bao ^[5]; Jiang, Li ^[1]; Li, Yongfang ^[1]; ^[1]

Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China
State Key Laboratory for Mechanical Behavior of Materials Xi'an Jiaotong University Xi'an 710049 China
Department of Chemistry University of North Carolina at Chapel Hill Chapel Hill NC 27599‐3290 USA
Key Laboratory of Nanosystem and Hierarchical Fabrication National Center for Nanoscience and Technology Beijing 100190 China
School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China

Abstract

Extending π‐conjugation of donor units in fused ring electron acceptors (FREAs) promises to reinforce intramolecular charge transfer for smaller bandgaps, and enhances intermolecular interactions for higher charge mobility. Despite these advantages, power conversion efficiencies (PCEs) of FREAs with a large planar donor core are still below 12%. Herein, a fused decacyclic donor unit, IDC, is developed, and the FREA, IDCIC, whose optical bandgap is 1.45 eV, is synthesized. The FTAZ:IDCIC‐based organic solar cell (OSC) with a binary additive, chloronaphthalene and 1,8‐diiodooctane (CN&DIO), affords a remarkable PCE of 13.58%, which is among the highest efficiencies of OSCs. The binary additive plays a crucial role in the morphology of FTAZ:IDCIC‐based OSCs. The addition of DIO promotes IDCIC to aggregate and enhances domain size and domain purity in FTAZ:IDCIC blend film for its poor solubility in DIO, while the addition of chloronaphthalene (CN) inhibits the aggregation, facilitates IDCIC to diffuse into the donor, and reduces domain size and domain purity for its excellent solubility in CN. The binary additive, CN&DIO, compromises the effect of the two; thus FTAZ:IDCIC‐based OSCs with 0.25% CN&DIO obtain moderate domain size and high domain purity simultaneously, achieving the least charge recombination for the highest J _SC (21.98 mA cm ⁻² ) and fill factor (FF) (71.03%).

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1471127

Journal Information:: Advanced Energy Materials, Journal Name: Advanced Energy Materials Journal Issue: 30 Vol. 8; ISSN 1614-6832

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

Country of Publication:: Germany

Language:: English

References (54)

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
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
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
Enhancing Performance of Nonfullerene Acceptors via Side-Chain Conjugation Strategy Wang, Jiayu; Wang, Wei; Wang, Xiaohui Advanced Materials, Vol. 29, Issue 35 https://doi.org/10.1002/adma.201702125	journal	July 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
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
An Alkylated Indacenodithieno[3,2- b ]thiophene-Based Nonfullerene Acceptor with High Crystallinity Exhibiting Single Junction Solar Cell Efficiencies Greater than 13% with Low Voltage Losses Fei, Zhuping; Eisner, Flurin D.; Jiao, Xuechen Advanced Materials, Vol. 30, Issue 8 https://doi.org/10.1002/adma.201705209	journal	January 2018
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
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
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
A High-Performance D-A Copolymer Based on Dithieno[3,2-b:2′,3′-d]Pyridin-5(4H)-One Unit Compatible with Fullerene and Nonfullerene Acceptors in Solar Cells An, Mingwei; Xie, Fangyuan; Geng, Xinjian Advanced Energy Materials, Vol. 7, Issue 14 https://doi.org/10.1002/aenm.201602509	journal	April 2017
Additive-Free Organic Solar Cells with Power Conversion Efficiency over 10% Li, Hui; He, Dan; Mao, Peng Advanced Energy Materials, Vol. 7, Issue 13 https://doi.org/10.1002/aenm.201602663	journal	February 2017
Morphology Control in Organic Solar Cells Zhao, Fuwen; Wang, Chunru; Zhan, Xiaowei Advanced Energy Materials, Vol. 8, Issue 28 https://doi.org/10.1002/aenm.201703147	journal	March 2018
Effect of Isomeric Structures on Photovoltaic Performance of D-A Copolymers Xie, Fangyuan; He, Dan; Pan, Han Macromolecular Rapid Communications, Vol. 38, Issue 12 https://doi.org/10.1002/marc.201700074	journal	April 2017
Roll-to-roll fabrication of polymer solar cells Søndergaard, Roar; Hösel, Markus; Angmo, Dechan Materials Today, Vol. 15, Issue 1-2 https://doi.org/10.1016/S1369-7021(12)70019-6	journal	January 2012
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
π-Bridge-Independent 2-(Benzo[ c ][1,2,5]thiadiazol-4-ylmethylene)malononitrile-Substituted Nonfullerene Acceptors for Efficient Bulk Heterojunction Solar Cells Wang, Kai; Firdaus, Yuliar; Babics, Maxime Chemistry of Materials, Vol. 28, Issue 7 https://doi.org/10.1021/acs.chemmater.6b00131	journal	March 2016
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
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
Panchromatic Ternary Photovoltaic Cells Using a Nonfullerene Acceptor Synthesized Using C–H Functionalization Zhang, Junxiang; Yan, Cenqi; Wang, Wei Chemistry of Materials, Vol. 30, Issue 2 https://doi.org/10.1021/acs.chemmater.7b04499	journal	January 2018
Enhancing the Performance of Organic Solar Cells by Hierarchically Supramolecular Self-Assembly of Fused-Ring Electron Acceptors Liu, Yahui; Zhang, Cai’e; Hao, Dan Chemistry of Materials, Vol. 30, Issue 13 https://doi.org/10.1021/acs.chemmater.8b01319	journal	June 2018
Organic Optoelectronic Materials: Mechanisms and Applications Ostroverkhova, Oksana Chemical Reviews, Vol. 116, Issue 22 https://doi.org/10.1021/acs.chemrev.6b00127	journal	October 2016
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
Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer−Fullerene Solar Cells Price, Samuel C.; Stuart, Andrew C.; Yang, Liqiang Journal of the American Chemical Society, Vol. 133, Issue 12 https://doi.org/10.1021/ja1112595	journal	March 2011
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
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
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
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
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
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
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 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
Polymer power Shrotriya, Vishal Nature Photonics, Vol. 3, Issue 8 https://doi.org/10.1038/nphoton.2009.130	journal	August 2009
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
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
Rhodanine dye-based small molecule acceptors for organic photovoltaic cells Kim, Yujeong; Song, Chang Eun; Moon, Sang-Jin Chem. Commun., Vol. 50, Issue 60 https://doi.org/10.1039/C4CC01695E	journal	January 2014
Donor–acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells Wu, Jhong-Sian; Cheng, Sheng-Wen; Cheng, Yen-Ju Chemical Society Reviews, Vol. 44, Issue 5 https://doi.org/10.1039/C4CS00250D	journal	January 2015
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
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
Single crystalline indene-C ₆₀ bisadduct: isolation and application in polymer solar cells Zhao, Fuwen; Meng, Xiangyue; Feng, Yongqiang Journal of Materials Chemistry A, Vol. 3, Issue 29 https://doi.org/10.1039/C5TA04040J	journal	January 2015
Development of isomer-free fullerene bisadducts for efficient polymer solar cells Xiao, Zuo; Geng, Xinjian; He, Dan Energy & Environmental Science, Vol. 9, Issue 6 https://doi.org/10.1039/C6EE01026A	journal	January 2016
A pentacyclic building block containing an azepine-2,7-dione moiety for polymer solar cells He, Dan; Qian, Liu; Ding, Liming Polymer Chemistry, Vol. 7, Issue 13 https://doi.org/10.1039/C6PY00082G	journal	January 2016
The effect of fluorination on the photovoltaic performance of the D–A copolymers containing naphtho[2,3-c]thiophene-4,9-dione and bithiophene moieties He, Dan; Geng, Xinjian; Ding, Liming Polymer Chemistry, Vol. 7, Issue 31 https://doi.org/10.1039/C6PY00883F	journal	January 2016
Non-fullerene acceptor with low energy loss and high external quantum efficiency: towards high performance polymer solar cells Li, Yongxi; Liu, Xiaodong; Wu, Fu-Peng Journal of Materials Chemistry A, Vol. 4, Issue 16 https://doi.org/10.1039/C6TA00612D	journal	January 2016
Non-fullerene small molecule acceptors based on perylene diimides Liu, Zhitian; Wu, Yao; Zhang, Qi Journal of Materials Chemistry A, Vol. 4, Issue 45 https://doi.org/10.1039/C6TA06978A	journal	January 2016
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
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
A–D–A small molecule acceptors with ladder-type arenes for organic solar cells He, Dan; Zhao, Fuwen; Jiang, Li Journal of Materials Chemistry A, Vol. 6, Issue 19 https://doi.org/10.1039/C8TA02534G	journal	January 2018
Functional fullerenes for organic photovoltaics Li, Chang-Zhi; Yip, Hin-Lap; Jen, Alex K. -Y. Journal of Materials Chemistry, Vol. 22, Issue 10 https://doi.org/10.1039/c2jm15126j	journal	January 2012
Indan-1,3-dione electron-acceptor small molecules for solution-processable solar cells: a structure–property correlation Winzenberg, Kevin N.; Kemppinen, Peter; Scholes, Fiona H. Chemical Communications, Vol. 49, Issue 56 https://doi.org/10.1039/c3cc42293c	journal	January 2013
Soft x-ray scattering facility at the Advanced Light Source with real-time data processing and analysis Gann, E.; Young, A. T.; Collins, B. A. Review of Scientific Instruments, Vol. 83, Issue 4 https://doi.org/10.1063/1.3701831	journal	April 2012
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
Recombination in polymer-fullerene bulk heterojunction solar cells Cowan, Sarah R.; Roy, Anshuman; Heeger, Alan J. Physical Review B, Vol. 82, Issue 24 https://doi.org/10.1103/PhysRevB.82.245207	journal	December 2010

Similar Records

Blade‐Cast Nonfullerene Organic Solar Cells in Air with Excellent Morphology, Efficiency, and Stability

Journal Article · Mon Apr 16 20:00:00 EDT 2018 · Advanced Materials · OSTI ID:1433419

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

Journal Article · Sun Jan 21 19:00:00 EST 2018 · Advanced Energy Materials · OSTI ID:1417715

A Fused Ring Electron Acceptor with Decacyclic Core Enables over 13.5% Efficiency for Organic Solar Cells

Citation Formats

References (54)

Similar Records

Related Subjects