Enhance the performance of organic solar cells by nonfused ring electron acceptors bearing a pendent perylenediimide group

Huang, Hao; Chen, Qiaoling; Guo, Qingxin; Wang, Liwen; Wu, Baohua; Xu, Xinjun; Ma, Wei; Tang, Zheng; Li, Cuihong; Bo, Zhishan

doi:10.1016/j.dyepig.2022.111033

Enhance the performance of organic solar cells by nonfused ring electron acceptors bearing a pendent perylenediimide group

Journal Article · Tue Dec 20 00:00:00 EST 2022 · Dyes and Pigments

DOI:https://doi.org/10.1016/j.dyepig.2022.111033· OSTI ID:2422679

Huang, Hao ^[1]; Chen, Qiaoling ^[1]; Guo, Qingxin ^[1]; Wang, Liwen ^[1]; Wu, Baohua ^[2]; Xu, Xinjun ^[1]; Ma, Wei ^[2]; Tang, Zheng ^[3]; Li, Cuihong ^[4]; Bo, Zhishan ^[5]

Beijing Normal University, Beijing (China)
Xi'an Jiaotong Univ. (China)
Donghua University (China)
Beijing Normal University, Beijing (China); Nankai Univ., Tianjin (China)
Beijing Normal University, Beijing (China); Qingdao Univ. (China)

A new nonfused ring electron acceptor PDI-DO-2F is designed and synthesized by attaching perylenediimide (PDI) unit as a pendent group to the central donor core. Compared with the control molecule DO-2F, the introduction of PDI lateral substituent can greatly enhance the solubility and decrease the crystallinity of the resulted acceptor. The PBDB-T:PDI-DO-2F blend film exhibits a much better morphology with higher and more balanced carrier mobility in contrast to PBDB-T:DO-2F one. PDI-DO-2F based organic solar cells (OSCs) give a power conversion efficiency (PCE) of 11.78%, higher than DO-2F based ones (9.82%). Furthermore, PDI-DO-2F based OSCs shows a ΔE_non-rad value of 0.23 eV, which is significantly lower than the DO-2F based ones (0.28 eV). More importantly, the addition of PDI-DO-2F as the third component to the PBDB-T:DO-2F binary system can optimize the morphology of blend films and improve the shelf stability of devices. Finally, the PBDB-T:DO-2F:PDI-DO-2F based ternary OSCs achieve a higher PCE of 13.82%.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)

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

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 2422679

Journal Information:: Dyes and Pigments, Journal Name: Dyes and Pigments Vol. 210; ISSN 0143-7208

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (69)

An Electron Acceptor with Broad Visible-NIR Absorption and Unique Solid State Packing for As-Cast High Performance Binary Organic Solar Cells Shi, Xueliang; Liao, Xunfan; Gao, Ke Advanced Functional Materials, Vol. 28, Issue 33 https://doi.org/10.1002/adfm.201802324	journal	June 2018
Perylene Diimide‐Based Nonfullerene Polymer Solar Cells with over 11% Efficiency Fabricated by Smart Molecular Design and Supramolecular Morphology Optimization Zhang, Guangjun; Feng, Jirui; Xu, Xiaopeng Advanced Functional Materials, Vol. 29, Issue 50 https://doi.org/10.1002/adfm.201906587	journal	September 2019
Isomerization of Asymmetric Ladder‐Type Heteroheptacene‐Based Small‐Molecule Acceptors Improving Molecular Packing: Efficient Nonfullerene Organic Solar Cells with Excellent Fill Factors Luo, Zhenghui; Liu, Tao; Oh, Jiyeon Advanced Functional Materials, Vol. 32, Issue 34 https://doi.org/10.1002/adfm.202203200	journal	June 2022
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
The Role of Demixing and Crystallization Kinetics on the Stability of Non‐Fullerene Organic Solar Cells Hu, Huawei; Ghasemi, Masoud; Peng, Zhengxing Advanced Materials, Vol. 32, Issue 49 https://doi.org/10.1002/adma.202005348	journal	November 2020
Efficient Electron Transport Layer Free Small‐Molecule Organic Solar Cells with Superior Device Stability Bin, Haijun; Wang, Junke; Li, Junyu Advanced Materials, Vol. 33, Issue 14 https://doi.org/10.1002/adma.202008429	journal	March 2021
Single‐Junction Organic Photovoltaic Cell with 19% Efficiency Cui, Yong; Xu, Ye; Yao, Huifeng Advanced Materials, Vol. 33, Issue 41 https://doi.org/10.1002/adma.202102420	journal	August 2021
Achieving 19% Power Conversion Efficiency in Planar‐Mixed Heterojunction Organic Solar Cells Using a Pseudosymmetric Electron Acceptor Gao, Wei; Qi, Feng; Peng, Zhengxing Advanced Materials, Vol. 34, Issue 32 https://doi.org/10.1002/adma.202202089	journal	July 2022
Binary Organic Solar Cells Breaking 19% via Manipulating the Vertical Component Distribution Wei, Yanan; Chen, Zhihao; Lu, Guanyu Advanced Materials, Vol. 34, Issue 33 https://doi.org/10.1002/adma.202204718	journal	July 2022
Factors Influencing the Efficiency of Current Collection in Large Area, Monolithic Organic Solar Cells Jin, Hui; Pivrikas, Almantas; Lee, Kwan H. Advanced Energy Materials, Vol. 2, Issue 11 https://doi.org/10.1002/aenm.201200254	journal	July 2012
Simple Nonfused Ring Electron Acceptors with 3D Network Packing Structure Boosting the Efficiency of Organic Solar Cells to 15.44% Wang, Xiaodong; Lu, Hao; Liu, Yahui Advanced Energy Materials, Vol. 11, Issue 45 https://doi.org/10.1002/aenm.202102591	journal	October 2021
The Crystalline Behavior and Device Function of Nonfullerene Acceptors in Organic Solar Cells Xu, Jinqiu; Lin, Francis; Zhu, Lei Advanced Energy Materials, Vol. 12, Issue 34 https://doi.org/10.1002/aenm.202201338	journal	July 2022
2D Outer Side Chain‐Incorporated Y Acceptors for Highly Efficient Organic Solar Cells with Nonhalogenated Solvent and Annealing‐Free Process Park, Jin Su; Sun, Cheng; Han, Yunghee Advanced Energy and Sustainability Research, Vol. 3, Issue 9 https://doi.org/10.1002/aesr.202200070	journal	July 2022
An Electron Acceptor with Porphyrin and Perylene Bisimides for Efficient Non-Fullerene Solar Cells Zhang, Andong; Li, Cheng; Yang, Fan Angewandte Chemie International Edition, Vol. 56, Issue 10 https://doi.org/10.1002/anie.201612090	journal	January 2017
A Fully Non‐fused Ring Acceptor with Planar Backbone and Near‐IR Absorption for High Performance Polymer Solar Cells Chen, Ya‐Nan; Li, Miao; Wang, Yunzhi Angewandte Chemie International Edition, Vol. 59, Issue 50 https://doi.org/10.1002/anie.202010856	journal	October 2020
High‐Performance Noncovalently Fused‐Ring Electron Acceptors for Organic Solar Cells Enabled by Noncovalent Intramolecular Interactions and End‐Group Engineering Zhang, Xin; Qin, Linqing; Yu, Jianwei Angewandte Chemie International Edition, Vol. 60, Issue 22 https://doi.org/10.1002/anie.202100390	journal	April 2021
Simple Non‐Fused Electron Acceptors Leading to Efficient Organic Photovoltaics Wen, Tian‐Jiao; Liu, Zhi‐Xi; Chen, Zeng Angewandte Chemie International Edition, Vol. 60, Issue 23 https://doi.org/10.1002/anie.202101867	journal	May 2021
Built‐In Potential and Operational Stability of Nonfullerene Organic Solar Cells Han, Jiayin; Wang, Yiwen; Zhu, Furong Energy Technology, Vol. 8, Issue 12 https://doi.org/10.1002/ente.202000245	journal	June 2020
Controlling Molecular Weight to Achieve High-Efficient Polymer Solar Cells With Unprecedented Fill Factor of 79% Based on Non-Fullerene Small Molecule Acceptor Xiong, Wentao; Qi, Feng; Liu, Tao Solar RRL, Vol. 2, Issue 9 https://doi.org/10.1002/solr.201800129	journal	June 2018
Ternary Strategy Enabling High‐Performance Organic Solar Cells with Optimized Film Morphology and Reduced Nonradiative Energy Loss Li, Miao; Zhou, Yuanyuan; Zhang, Ming Solar RRL, Vol. 5, Issue 12 https://doi.org/10.1002/solr.202100806	journal	November 2021
Recent progress in organic solar cells (Part I material science) Liu, Yahui; Liu, Bowen; Ma, Chang-Qi Science China Chemistry, Vol. 65, Issue 2 https://doi.org/10.1007/s11426-021-1180-6	journal	December 2021
Recent progress in organic solar cells (Part II device engineering) Liu, Yahui; Liu, Bowen; Ma, Chang-Qi Science China Chemistry, Vol. 65, Issue 8 https://doi.org/10.1007/s11426-022-1256-8	journal	May 2022
The design of highly efficient polymer solar cells with outstanding short-circuit current density based on small band gap electron acceptor Ma, Danyang; Feng, Shiyu; Zhang, Zhe Dyes and Pigments, Vol. 150 https://doi.org/10.1016/j.dyepig.2017.12.017	journal	March 2018
Quenching to the Percolation Threshold in Organic Solar Cells Ye, Long; Li, Sunsun; Liu, Xiaoyu Joule, Vol. 3, Issue 2 https://doi.org/10.1016/j.joule.2018.11.006	journal	February 2019
Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core Yuan, Jun; Zhang, Yunqiang; Zhou, Liuyang Joule, Vol. 3, Issue 4 https://doi.org/10.1016/j.joule.2019.01.004	journal	April 2019
The performance-stability conundrum of BTP-based organic solar cells Qin, Yunpeng; Balar, Nrup; Peng, Zhengxing Joule, Vol. 5, Issue 8 https://doi.org/10.1016/j.joule.2021.06.006	journal	August 2021
Developement of highly efficient large area organic photovoltaic module: Effects of nonfullerene acceptor Park, So Hyun; Park, Sungmin; Lee, Seungjin Nano Energy, Vol. 77 https://doi.org/10.1016/j.nanoen.2020.105147	journal	November 2020
Tuning the Mechanical Properties of a Polymer Semiconductor by Modulating Hydrogen Bonding Interactions Zheng, Yu; Ashizawa, Minoru; Zhang, Song Chemistry of Materials, Vol. 32, Issue 13 https://doi.org/10.1021/acs.chemmater.0c01437	journal	June 2020
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
Isomerization of Noncovalently Conformational Lock in Nonfused Electron Acceptor toward Efficient Organic Solar Cells Yu, Kexin; Pan, Mingao; Xu, Xiaopeng ACS Applied Energy Materials, Vol. 5, Issue 8 https://doi.org/10.1021/acsaem.2c01945	journal	July 2022
Noncovalently Fused-Ring Electron Acceptors with C _{2 v} Symmetry for Regulating the Morphology of Organic Solar Cells Hou, Ran; Li, Miao; Ma, Xueqing ACS Applied Materials & Interfaces, Vol. 12, Issue 41 https://doi.org/10.1021/acsami.0c13993	journal	September 2020
P3HT-Based Organic Solar Cells with a Photoresponse to 1000 nm Enabled by Narrow Band Gap Nonfullerene Acceptors with High HOMO Levels Liang, Ziqi; Cheng, Xiafei; Jiang, Yu ACS Applied Materials & Interfaces, Vol. 13, Issue 51 https://doi.org/10.1021/acsami.1c21089	journal	December 2021
Designing High-Performance Nonfused Ring Electron Acceptors via Synergistically Adjusting Side Chains and Electron-Withdrawing End-Groups Zhang, Yan; Zhang, Cai’e; Zhang, Andong ACS Applied Materials & Interfaces, Vol. 14, Issue 18 https://doi.org/10.1021/acsami.2c01190	journal	April 2022
Naphthodithiophene-Based Conjugated Polymer with Linear, Planar Backbone Conformation and Strong Intermolecular Packing for Efficient Organic Solar Cells Lee, Jaewon; Ko, Hyomin; Song, Eunjoo ACS Applied Materials & Interfaces, Vol. 7, Issue 38 https://doi.org/10.1021/acsami.5b04884	journal	September 2015
4-Alkyl-3,5-difluorophenyl-Substituted Benzodithiophene-Based Wide Band Gap Polymers for High-Efficiency Polymer Solar Cells Li, Guangwu; Gong, Xue; Zhang, Jicheng ACS Applied Materials & Interfaces, Vol. 8, Issue 6 https://doi.org/10.1021/acsami.5b08769	journal	September 2015
1,8-Naphthalimide-Based Planar Small Molecular Acceptor for Organic Solar Cells Zhang, Jicheng; Zhang, Xuejuan; Xiao, Hongmei ACS Applied Materials & Interfaces, Vol. 8, Issue 8 https://doi.org/10.1021/acsami.5b10211	journal	February 2016
Regulating the Packing of Non-Fullerene Acceptors via Multiple Noncovalent Interactions for Enhancing the Performance of Organic Solar Cells Feng, Shiyu; Li, Miao; Tang, Ningning ACS Applied Materials & Interfaces, Vol. 12, Issue 4 https://doi.org/10.1021/acsami.9b18076	journal	January 2020
The Role of Solvent Additive Processing in High Performance Small Molecule Solar Cells Perez, Louis A.; Rogers, James T.; Brady, Michael A. Chemistry of Materials, Vol. 26, Issue 22 https://doi.org/10.1021/cm5031987	journal	November 2014
Universal Correlation between Fibril Width and Quantum Efficiency in Diketopyrrolopyrrole-Based Polymer Solar Cells Li, Weiwei; Hendriks, Koen H.; Furlan, Alice Journal of the American Chemical Society, Vol. 135, Issue 50 https://doi.org/10.1021/ja4101003	journal	December 2013
A Planar Copolymer for High Efficiency Polymer Solar Cells Qin, Ruiping; Li, Weiwei; Li, Cuihong Journal of the American Chemical Society, Vol. 131, Issue 41 https://doi.org/10.1021/ja9057986	journal	October 2009
Non-Fullerene-Acceptor-Based Bulk-Heterojunction Organic Solar Cells with Efficiency over 7% Sun, Dan; Meng, Dong; Cai, Yunhao Journal of the American Chemical Society, Vol. 137, Issue 34 https://doi.org/10.1021/jacs.5b06414	journal	August 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
Exploiting Noncovalently Conformational Locking as a Design Strategy for High Performance Fused-Ring Electron Acceptor Used in Polymer Solar Cells Liu, Yahui; Zhang, Zhe; Feng, Shiyu Journal of the American Chemical Society, Vol. 139, Issue 9 https://doi.org/10.1021/jacs.7b00566	journal	February 2017
Ring-Fusion of Perylene Diimide Acceptor Enabling Efficient Nonfullerene Organic Solar Cells with a Small Voltage Loss Zhang, Jianquan; Li, Yunke; Huang, Jiachen Journal of the American Chemical Society, Vol. 139, Issue 45 https://doi.org/10.1021/jacs.7b09998	journal	November 2017
Morphology and Phase Segregation of Spin-Casted Films of Polyfluorene/PCBM Blends Nilsson, Svante; Bernasik, Andrzej; Budkowski, Andrzej Macromolecules, Vol. 40, Issue 23 https://doi.org/10.1021/ma070712a	journal	November 2007
2,7-Carbazole-1,4-phenylene Copolymers with Polar Side Chains for Cathode Modifications in Polymer Light-Emitting Diodes Xu, Xiaofeng; Han, Bing; Chen, Junwu Macromolecules, Vol. 44, Issue 11 https://doi.org/10.1021/ma200191p	journal	May 2011
Organic solar cells based on non-fullerene acceptors Hou, Jianhui; Inganäs, Olle; Friend, Richard H. Nature Materials, Vol. 17, Issue 2 https://doi.org/10.1038/nmat5063	journal	January 2018
Simple non-fused electron acceptors for efficient and stable organic solar cells Yu, Zhi-Peng; Liu, Zhi-Xi; Chen, Fang-Xiao Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10098-z	journal	May 2019
Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells Huang, Hao; Guo, Qingxin; Feng, Shiyu Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-11001-6	journal	July 2019
Completely non-fused electron acceptor with 3D-interpenetrated crystalline structure enables efficient and stable organic solar cell Ma, Lijiao; Zhang, Shaoqing; Zhu, Jincheng Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-25394-w	journal	August 2021
Increasing donor-acceptor spacing for reduced voltage loss in organic solar cells Wang, Jing; Jiang, Xudong; Wu, Hongbo Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-26995-1	journal	November 2021
High-efficiency small-molecule ternary solar cells with a hierarchical morphology enabled by synergizing fullerene and non-fullerene acceptors Zhou, Zichun; Xu, Shengjie; Song, Jingnan Nature Energy, Vol. 3, Issue 11 https://doi.org/10.1038/s41560-018-0234-9	journal	September 2018
Wide-gap non-fullerene acceptor enabling high-performance organic photovoltaic cells for indoor applications Cui, Yong; Wang, Yuming; Bergqvist, Jonas Nature Energy, Vol. 4, Issue 9 https://doi.org/10.1038/s41560-019-0448-5	journal	August 2019
A molecular interaction–diffusion framework for predicting organic solar cell stability Ghasemi, Masoud; Balar, Nrup; Peng, Zhengxing Nature Materials, Vol. 20, Issue 4 https://doi.org/10.1038/s41563-020-00872-6	journal	January 2021
Single-junction organic solar cells with over 19% efficiency enabled by a refined double-fibril network morphology Zhu, Lei; Zhang, Ming; Xu, Jinqiu Nature Materials, Vol. 21, Issue 6 https://doi.org/10.1038/s41563-022-01244-y	journal	May 2022
Balancing the H- and J-aggregation in DTS(PTTh ₂ ) ₂ /PC ₇₀ BM to yield a high photovoltaic efficiency Zhao, Qiaoqiao; Liu, Jiangang; Wang, Haiyang Journal of Materials Chemistry C, Vol. 3, Issue 31 https://doi.org/10.1039/C5TC01205H	journal	January 2015
Ternary solar cells with a mixed face-on and edge-on orientation enable an unprecedented efficiency of 12.1% Kumari, Tanya; Lee, Sang Myeon; Kang, So-Huei Energy & Environmental Science, Vol. 10, Issue 1 https://doi.org/10.1039/C6EE02851A	journal	January 2017
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
Ternary nonfullerene polymer solar cells with efficiency >13.7% by integrating the advantages of the materials and two binary cells Ma, Xiaoling; Gao, Wei; Yu, Jiangsheng Energy & Environmental Science, Vol. 11, Issue 8 https://doi.org/10.1039/C8EE01107A	journal	January 2018
Relating open-circuit voltage losses to the active layer morphology and contact selectivity in organic solar cells Tang, Zheng; Wang, Jing; Melianas, Armantas Journal of Materials Chemistry A, Vol. 6, Issue 26 https://doi.org/10.1039/C8TA01195H	journal	January 2018
Multi-component non-fullerene acceptors with tunable bandgap structures for efficient organic solar cells Gao, Bowei; Yao, Huifeng; Hou, Junxian Journal of Materials Chemistry A, Vol. 6, Issue 46 https://doi.org/10.1039/C8TA09830A	journal	January 2018
Dihydropyreno[1,2- b :6,7- b ′]dithiophene based electron acceptors for high efficiency as-cast organic solar cells Jiang, Pengcheng; Lu, Hao; Jia, Qing-Qing Journal of Materials Chemistry A, Vol. 7, Issue 11 https://doi.org/10.1039/C9TA00614A	journal	January 2019
High-efficiency ternary nonfullerene organic solar cells with record long-term thermal stability Zhang, Cai'e; Ming, Shouli; Wu, Hongbo Journal of Materials Chemistry A, Vol. 8, Issue 43 https://doi.org/10.1039/D0TA07887E	journal	January 2020
Manipulating the D:A interfacial energetics and intermolecular packing for 19.2% efficiency organic photovoltaics He, Chengliang; Pan, Youwen; Ouyang, Yanni Energy & Environmental Science, Vol. 15, Issue 6 https://doi.org/10.1039/D2EE00595F	journal	January 2022
Fourier-transform photocurrent spectroscopy of microcrystalline silicon for solar cells Vanecek, M.; Poruba, A. Applied Physics Letters, Vol. 80, Issue 5 https://doi.org/10.1063/1.1446207	journal	February 2002
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
Heteroheptacene-based acceptors with thieno[3,2-b]pyrrole yield high-performance polymer solar cells Luo, Zhenghui; Ma, Ruijie; Yu, Jianwei National Science Review, Vol. 9, Issue 7 https://doi.org/10.1093/nsr/nwac076	journal	April 2022
Relating the open-circuit voltage to interface molecular properties of donor:acceptor bulk heterojunction solar cells Vandewal, Koen; Tvingstedt, Kristofer; Gadisa, Abay Physical Review B, Vol. 81, Issue 12 https://doi.org/10.1103/PhysRevB.81.125204	journal	March 2010
Designing a High-Performance A-D-A Fused-Ring Electron Acceptor via Noncovalently Conformational Locking and Tailoring Its End Groups Feng, Shiyu; Lu, Hao Acta Physico-Chimica Sinica, Vol. 35, Issue 4 https://doi.org/10.3866/PKU.WHXB201805161	journal	January 2019

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14 SOLAR ENERGY
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Enhance the performance of organic solar cells by nonfused ring electron acceptors bearing a pendent perylenediimide group

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