Achieving Highly Efficient Nonfullerene Organic Solar Cells with Improved Intermolecular Interaction and Open-Circuit Voltage

Yao, Huifeng; Ye, Long; Hou, Junxian; Jang, Bomee; Han, Guangchao; Cui, Yong; Su, Gregory M.; Wang, Cheng; Gao, Bowei; Yu, Runnan; Zhang, Hao; Yi, Yuanping; Woo, Han Young; Ade, Harald; Hou, Jianhui

doi:10.1002/adma.201700254

Title: Achieving Highly Efficient Nonfullerene Organic Solar Cells with Improved Intermolecular Interaction and Open-Circuit Voltage

Journal Article · Wed Mar 29 04:00:00 UTC 2017 · Advanced Materials

DOI: https://doi.org/10.1002/adma.201700254 · OSTI ID:1436630

Yao, Huifeng ^[1]; Ye, Long ^[2]; Hou, Junxian ^[3]; Jang, Bomee ^[4]; Han, Guangchao ^[1]; Cui, Yong ^[1]; Su, Gregory M. ^[5]; Wang, Cheng ^[5]; Gao, Bowei ^[1]; Yu, Runnan ^[1]; Zhang, Hao ^[1]; Yi, Yuanping ^[1]; Woo, Han Young ^[4]; Ade, Harald ^[2]; Hou, Jianhui ^[1]

Chinese Academy of Science, Beijing (P. R. China); Univ. of Chinese Academy of Science, Beijing (P. R. China)
North Carolina State Univ., Raleigh, NC (United States)
Hebei Univ. of Engineering, Handan (P. R. China)
Korea Univ., Seoul (Republic of Korea)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Here, a new acceptor–donor–acceptor-structured nonfullerene acceptor ITCC (3,9-bis(4-(1,1-dicyanomethylene)-3-methylene-2-oxo-cyclopenta[b]thiophen)-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d':2,3-d'] -s-indaceno[1,2-b:5,6-b']-dithiophene) is designed and synthesized via simple end-group modification. ITCC shows improved electron-transport properties and a high-lying lowest unoccupied molecular orbital level. A power conversion efficiency of 11.4% with an impressive V _OC of over 1 V is recorded in photovoltaic devices, suggesting that ITCC has great potential for applications in tandem organic solar cells.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1436630

Journal Information:: Advanced Materials, Journal Name: Advanced Materials Journal Issue: 21 Vol. 29; ISSN 0935-9648

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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A Novel Carbazole‐Based Nonfullerene Acceptor for High‐Efficiency Polymer Solar Cells Ouyang, Jinyang; Zeng, Guang; Xin, Yue Solar RRL, Vol. 4, Issue 3 https://doi.org/10.1002/solr.201900417	journal	November 2019
A new nonfullerene acceptor based on perylene diimides for organic solar cells Liu, Zhitian; Wu, Yao; Jiang, Huanxiang Journal of Materials Science: Materials in Electronics, Vol. 29, Issue 12 https://doi.org/10.1007/s10854-018-9094-0	journal	April 2018
Fluorination-modulated end units for high-performance non-fullerene acceptors based organic solar cells Sun, Yanna; Gao, Huan-Huan; Yi, Yuan-Qiu-Qiang Science China Materials, Vol. 62, Issue 8 https://doi.org/10.1007/s40843-019-9415-2	journal	April 2019
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
Material insights and challenges for non-fullerene organic solar cells based on small molecular acceptors Zhang, Jianquan; Tan, Huei Shuan; Guo, Xugang Nature Energy, Vol. 3, Issue 9 https://doi.org/10.1038/s41560-018-0181-5	journal	July 2018
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Enhancing the performance of the electron acceptor ITIC-Th via tailoring its end groups Li, Zeyuan; Dai, Shuixing; Xin, Jingming Materials Chemistry Frontiers, Vol. 2, Issue 3 https://doi.org/10.1039/c7qm00547d	journal	January 2018
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High performance non-fullerene polymer solar cells based on PTB7-Th as the electron donor with 10.42% efficiency Sun, Jia; Zhang, Zhuohan; Yin, Xinxing Journal of Materials Chemistry A, Vol. 6, Issue 6 https://doi.org/10.1039/c7ta10391c	journal	January 2018
Two-dimensional benzo[1,2- b :4,5- b ′]difuran-based wide bandgap conjugated polymers for efficient fullerene-free polymer solar cells Gao, Yueyue; Wang, Zhen; Zhang, Jianqi Journal of Materials Chemistry A, Vol. 6, Issue 9 https://doi.org/10.1039/c7ta10976h	journal	January 2018
Effect of π-bridge units on properties of A–π–D–π–A-type nonfullerene acceptors for organic solar cells Wang, Yan-Ling; Li, Quan-Song; Li, Ze-Sheng Physical Chemistry Chemical Physics, Vol. 20, Issue 20 https://doi.org/10.1039/c8cp02266f	journal	January 2018
Ultrafast Channel II process induced by a 3-D texture with enhanced acceptor order ranges for high-performance non-fullerene polymer solar cells Chen, Shanshan; Lee, Sang Myeon; Xu, Jianqiu Energy & Environmental Science, Vol. 11, Issue 9 https://doi.org/10.1039/c8ee01546e	journal	January 2018
Enhancement of intra- and inter-molecular π-conjugated effects for a non-fullerene acceptor to achieve high-efficiency organic solar cells with an extended photoresponse range and optimized morphology Wang, Ning; Zhan, Lingling; Li, Shuixing Materials Chemistry Frontiers, Vol. 2, Issue 11 https://doi.org/10.1039/c8qm00318a	journal	January 2018
Effects of different types of unsymmetrical squaraines on the material properties and Coulomb interactions in organic photovoltaic devices Yang, Lin; Yang, Daobin; Chen, Yao Materials Chemistry Frontiers, Vol. 2, Issue 11 https://doi.org/10.1039/c8qm00327k	journal	January 2018
Enhanced intramolecular charge transfer of unfused electron acceptors for efficient organic solar cells Qin, Ran; Yang, Weitao; Li, Shuixing Materials Chemistry Frontiers, Vol. 3, Issue 3 https://doi.org/10.1039/c8qm00609a	journal	January 2019
Designing an asymmetrical isomer to promote the LUMO energy level and molecular packing of a non-fullerene acceptor for polymer solar cells with 12.6% efficiency Gao, Wei; An, Qiaoshi; Zhong, Cheng Chemical Science, Vol. 9, Issue 42 https://doi.org/10.1039/c8sc02018c	journal	January 2018
High efficiency ternary polymer solar cells based on a fused pentacyclic electron acceptor Zhang, Cai'e; Feng, Shiyu; Liu, Yahui Journal of Materials Chemistry A, Vol. 6, Issue 16 https://doi.org/10.1039/c8ta00944a	journal	January 2018
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
Revealing the effects of molecular packing on the performances of polymer solar cells based on A–D–C–D–A type non-fullerene acceptors Li, Shuixing; Zhan, Lingling; Zhao, Wenchao Journal of Materials Chemistry A, Vol. 6, Issue 25 https://doi.org/10.1039/c8ta03753a	journal	January 2018
Nonfullerene small-molecule acceptors with perpendicular side-chains for fullerene-free solar cells Shen, Fugang; Xu, Jianzhong; Li, Xuemei Journal of Materials Chemistry A, Vol. 6, Issue 32 https://doi.org/10.1039/c8ta04718a	journal	January 2018
Carboxylate substitution position influencing polymer properties and enabling non-fullerene organic solar cells with high open circuit voltage and low voltage loss Liu, Jing; Ma, Lik-Kuen; Sheong, Fu Kit Journal of Materials Chemistry A, Vol. 6, Issue 35 https://doi.org/10.1039/c8ta04935a	journal	January 2018
Recent advances in electron acceptors with ladder-type backbone for organic solar cells Jiang, Zuo-Quan; Wang, Tong-Tong; Wu, Fu-Peng Journal of Materials Chemistry A, Vol. 6, Issue 36 https://doi.org/10.1039/c8ta05440a	journal	January 2018
Enhancing the performance of non-fullerene organic solar cells via end group engineering of fused-ring electron acceptors Yan, Cenqi; Wang, Wei; Lau, Tsz-Ki Journal of Materials Chemistry A, Vol. 6, Issue 34 https://doi.org/10.1039/c8ta05800h	journal	January 2018
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Synergistic effect of side-chain and backbone engineering in thieno[2,3- f ]benzofuran-based conjugated polymers for high performance non-fullerene organic solar cells Dou, Keke; Wang, Xunchang; Du, Zurong Journal of Materials Chemistry A, Vol. 7, Issue 3 https://doi.org/10.1039/c8ta07544a	journal	January 2019
Ultra-narrow bandgap non-fullerene organic solar cells with low voltage losses and a large photocurrent Wang, Jianqiu; Xie, Shenkun; Zhang, Dongyang Journal of Materials Chemistry A, Vol. 6, Issue 41 https://doi.org/10.1039/c8ta07954d	journal	January 2018
The influence of the π-bridging unit of fused-ring acceptors on the performance of organic solar cells Jiang, Pengcheng; Ming, Shouli; Jia, Qing-Qing Journal of Materials Chemistry A, Vol. 6, Issue 43 https://doi.org/10.1039/c8ta08410f	journal	January 2018
Asymmetric selenophene-based non-fullerene acceptors for high-performance organic solar cells Li, Chao; Xia, Tian; Song, Jiali Journal of Materials Chemistry A, Vol. 7, Issue 4 https://doi.org/10.1039/c8ta11197a	journal	January 2019
Length evolution of fused-ring electron acceptors toward optimal blend morphology in polymer solar cells incorporating asymmetric benzodithiophene-based donors Zhu, Qianqian; Liu, Deyu; Lu, Zhou Journal of Materials Chemistry A, Vol. 7, Issue 9 https://doi.org/10.1039/c8ta11363g	journal	January 2019
Highly efficient near-infrared and semitransparent polymer solar cells based on an ultra-narrow bandgap nonfullerene acceptor Chen, Juan; Li, Guangda; Zhu, Qinglian Journal of Materials Chemistry A, Vol. 7, Issue 8 https://doi.org/10.1039/c8ta11484f	journal	January 2019
A decacyclic indacenodithiophene-based non-fullerene electron acceptor with meta -alkyl-phenyl substitutions for polymer solar cells Wu, Fupeng; Zhong, Lian; Hu, Huawei Journal of Materials Chemistry A, Vol. 7, Issue 8 https://doi.org/10.1039/c8ta11972d	journal	January 2019
Molecular engineering of central fused-ring cores of non-fullerene acceptors for high-efficiency organic solar cells Wang, Hongtao; Cao, Jinru; Yu, Jiangsheng Journal of Materials Chemistry A, Vol. 7, Issue 9 https://doi.org/10.1039/c8ta12465e	journal	January 2019
Tuning the dipole moments of nonfullerene acceptors with an asymmetric terminal strategy for highly efficient organic solar cells Li, Miao; Zhou, Yuanyuan; Zhang, Jianqi Journal of Materials Chemistry A, Vol. 7, Issue 15 https://doi.org/10.1039/c8ta12530a	journal	January 2019
High-efficiency non-fullerene polymer solar cell fabricated by a simple process using new conjugated terpolymers Hoang, Mai Ha; Park, Gi Eun; Choi, Suna Journal of Materials Chemistry C, Vol. 7, Issue 1 https://doi.org/10.1039/c8tc05035j	journal	January 2019
Design of organic small molecules for photovoltaic application with high open-circuit voltage ( V _oc ) He, Xiaodong; Yin, Lunxiang; Li, Yanqin Journal of Materials Chemistry C, Vol. 7, Issue 9 https://doi.org/10.1039/c8tc06589f	journal	January 2019
The crucial role of end group planarity for fused-ring electron acceptors in organic solar cells Rech, Jeromy J.; Bauer, Nicole; Dirkes, David Materials Chemistry Frontiers, Vol. 3, Issue 8 https://doi.org/10.1039/c9qm00314b	journal	January 2019
Semitransparent solar cells with over 12% efficiency based on a new low bandgap fluorinated small molecule acceptor Luo, Mei; Zhao, Chunyan; Yuan, Jun Materials Chemistry Frontiers, Vol. 3, Issue 11 https://doi.org/10.1039/c9qm00499h	journal	January 2019
Ultra-narrow bandgap non-fullerene acceptors for organic solar cells with low energy loss Liu, Dongxue; Wang, Ting; Ke, Xin Materials Chemistry Frontiers, Vol. 3, Issue 10 https://doi.org/10.1039/c9qm00505f	journal	January 2019
Efficient as-cast thick film small-molecule organic solar cell with less fluorination on the donor Wang, Kai; Song, Xin; Guo, Xiao Materials Chemistry Frontiers, Vol. 4, Issue 1 https://doi.org/10.1039/c9qm00605b	journal	January 2020
[2,2′-Bithiophene]-4,4′-dicarboxamide: a novel building block for semiconducting polymers Zhou, Xiaocheng; Zhang, Zhifang; Hendsbee, Arthur D. RSC Advances, Vol. 9, Issue 52 https://doi.org/10.1039/c9ra06909g	journal	January 2019
Improved photovoltaic performance of a nonfullerene acceptor based on a benzo[ b ]thiophene fused end group with extended π-conjugation Yang, Kun; Liao, Qiaogan; Koh, Chang Woo Journal of Materials Chemistry A, Vol. 7, Issue 16 https://doi.org/10.1039/c9ta01111k	journal	January 2019
Asymmetric fused-ring electron acceptor with two distinct terminal groups for efficient organic solar cells Ye, Linglong; Xie, Yuanpeng; Xiao, Yiqun Journal of Materials Chemistry A, Vol. 7, Issue 14 https://doi.org/10.1039/c9ta01285k	journal	January 2019
A fused-ring non-fullerene acceptor based on a benzo[1,2- b :4,5- b ′]dithiophene central core with a thieno[3,2- b ]thiophene side-chain for highly efficient organic solar cells Jia, Yu; Zhang, Yun; Jiang, Wei Journal of Materials Chemistry A, Vol. 7, Issue 18 https://doi.org/10.1039/c9ta01888c	journal	January 2019
An efficient binary cathode interlayer for large-bandgap non-fullerene organic solar cells Yin, Qingwu; Zhang, Kai; Zhang, Long Journal of Materials Chemistry A, Vol. 7, Issue 20 https://doi.org/10.1039/c9ta02844g	journal	January 2019
Benzo[1,2- b :4,5- b ′]diselenophene-fused nonfullerene acceptors with alternative aromatic ring-based and monochlorinated end groups: a new synergistic strategy to simultaneously achieve highly efficient organic solar cells with the energy loss of 0.49 eV Wan, Shi-Sheng; Xu, Xiaopeng; Wang, Jin-Liang Journal of Materials Chemistry A, Vol. 7, Issue 19 https://doi.org/10.1039/c9ta03177d	journal	January 2019
Effects of energy-level offset between a donor and acceptor on the photovoltaic performance of non-fullerene organic solar cells Yang, Chenyi; Zhang, Jianqi; Liang, Ningning Journal of Materials Chemistry A, Vol. 7, Issue 32 https://doi.org/10.1039/c9ta04789a	journal	January 2019
Insights into constitutional isomeric effects on donor–acceptor intermolecular arrangements in non-fullerene organic solar cells Lee, Jungho; Go, Eun Min; Dharmapurikar, Satej Journal of Materials Chemistry A, Vol. 7, Issue 31 https://doi.org/10.1039/c9ta07133d	journal	January 2019
Modulating the molecular packing and distribution enables fullerene-free ternary organic solar cells with high efficiency and long shelf-life Du, Xiaoyang; Zhao, Juewen; Zhang, Hao Journal of Materials Chemistry A, Vol. 7, Issue 35 https://doi.org/10.1039/c9ta07542a	journal	January 2019
Achieving high-performance non-halogenated nonfullerene acceptor-based organic solar cells with 13.7% efficiency via a synergistic strategy of an indacenodithieno[3,2- b ]selenophene core unit and non-halogenated thiophene-based terminal group Liu, Kai-Kai; Xu, Xiaopeng; Wang, Jin-Liang Journal of Materials Chemistry A, Vol. 7, Issue 42 https://doi.org/10.1039/c9ta08328f	journal	January 2019
Impact of end groups on the performance of non-fullerene acceptors for organic solar cell applications Suman, Suman; Singh, Surya Prakash Journal of Materials Chemistry A, Vol. 7, Issue 40 https://doi.org/10.1039/c9ta08620j	journal	January 2019
A p-π* conjugated triarylborane as an alcohol-processable n-type semiconductor for organic optoelectronic devices Yu, Yingjian; Dong, Changshuai; Alahmadi, Abdullah F. Journal of Materials Chemistry C, Vol. 7, Issue 24 https://doi.org/10.1039/c9tc01562k	journal	January 2019
Boosted photovoltaic performance of indenothiophene-based molecular acceptor via fusing a thiophene Wang, Pengfei; Jiao, Xuechen; Xu, Shengjie Journal of Materials Chemistry C, Vol. 8, Issue 2 https://doi.org/10.1039/c9tc03407b	journal	January 2020
An efficient medium-bandgap nonfullerene acceptor for organic solar cells Liu, Qishi; Jin, Ke; Li, Wenting Journal of Materials Chemistry A, Vol. 8, Issue 18 https://doi.org/10.1039/d0ta02427a	journal	January 2020
A helical perylene diimide-based acceptor for non-fullerene organic solar cells: synthesis, morphology and exciton dynamics Chen, Li; Wu, Mingliang; Shao, Guangwei Royal Society Open Science, Vol. 5, Issue 5 https://doi.org/10.1098/rsos.172041	journal	May 2018
Performance optimization of tandem organic solar cells at varying incident angles based on optical analysis method Zhao, Xuenan; Xia, Ruoxi; Gu, Honggang Optics Express, Vol. 28, Issue 2 https://doi.org/10.1364/oe.382245	journal	January 2020
Polymer Solar Cells with 90% External Quantum Efficiency Featuring an Ideal Light- and Charge-Manipulation Layer J. -D., Chen,; J., Zhu,; R. -P., Xu, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/08jj-1y55	text	January 2018
The crucial role of end group planarity for fused-ring electron acceptors in organic solar cells F., Gao,; L., Ye,; D., Dirkes, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/6vb6-9k95	text	January 2019
Surpassing 10% Efficiency Benchmark for Nonfullerene Organic Solar Cells by Scalable Coating in Air from Single Nonhalogenated Solvent Y., Xiong,; W., You,; C., Wang, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/jhpv-dy32	text	January 2018
A Fused Ring Electron Acceptor with Decacyclic Core Enables over 13.5% Efficiency for Organic Solar Cells Y., Li,; J. J., Rech,; F., Zhao, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/w77e-dg58	text	January 2018
Organic solar cells based on non-fullerene acceptors. Hou, Jianhui; Inganäs, Olle; Friend, Richard Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.47720	text	January 2018
Recent Progress in Fused-Ring Based Nonfullerene Acceptors for Polymer Solar Cells Cui, Chaohua Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00404	journal	September 2018
Development of n-Type Porphyrin Acceptors for Panchromatic Light-Harvesting Fullerene-Free Organic Solar Cells Lee, Un-Hak; Hadmojo, Wisnu Tantyo; Kim, Junho Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00473	journal	October 2018

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