Molecular packing modulation enabling optimized blend morphology and efficient all small molecule organic solar cells

Duan, YW; Xu, Xiaopeng; Yu, Liyang; Li, Ying; Li, Ruipeng; Peng, Qiang

doi:10.1016/j.dyepig.2021.109387

Molecular packing modulation enabling optimized blend morphology and efficient all small molecule organic solar cells

Journal Article · Sat Apr 17 00:00:00 EDT 2021 · Dyes and Pigments

DOI:https://doi.org/10.1016/j.dyepig.2021.109387· OSTI ID:1788064

Duan, YW ^[1]; Xu, Xiaopeng ^[1]; Yu, Liyang ^[1]; Li, Ying ^[1]; Li, Ruipeng ^[2]; Peng, Qiang ^[1]

Sichuan Univ., Chengdu (China)
Brookhaven National Lab. (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)

The molecular planarity of a small molecule donor is one of the key factors affecting its molecular packing behavior, the morphology of the related active blend and thus the photovoltaic properties of all small molecule organic solar cells (ASM-OSCs). Here, a series of new benzodithiophene (BDT)-based A-π-D-π-A type small molecules were developed, namely SD1, SD2 and SD3, by combining the chemical modification of side chain (sulfuration), π-bridge (alkoxy groups introducing) and end group (different type or different alkyl chain). The sulfuration of the BDT side chains and introducing alkoxy group to the π-bridge could induce intermolecular S^…S and intramolecular S^…O non-covalent interactions for higher planarity of these small molecules. The rhodanine and cyanoacetate end groups showed less effect on the optical and electronic properties but significantly affected the molecular packing behavior and blend morphology. From SD1:Y6-T to SD2:Y6-T and SD3:Y6-T, the face-to-face packing was gradually reduced, while the face-to-edge packing was increased, which resulted in lowered exciton dissociation efficiency, further decreased the device performance. SD1:Y6-T blend exhibited more favorable face-to-face packing and ideal morphology for efficient charge dissociation and transport, contributing to a champion PCE of 10.12%. This work provided a deep insight of the donor and acceptor packing behavior effect on the photovoltaic property by molecular design.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

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

Grant/Contract Number:: SC0012704

OSTI ID:: 1788064

Report Number(s):: BNL--221651-2021-JAAM

Journal Information:: Dyes and Pigments, Journal Name: Dyes and Pigments Vol. 191; ISSN 0143-7208

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (62)

Subtle Polymer Donor and Molecular Acceptor Design Enable Efficient Polymer Solar Cells with a Very Small Energy Loss Xu, Xiaopeng; Feng, Kui; Lee, Young Woong Advanced Functional Materials, Vol. 30, Issue 9 https://doi.org/10.1002/adfm.201907570	journal	December 2019
Moving Alkyl‐Chain Branching Point Induced a Hierarchical Morphology for Efficient All‐Small‐Molecule Organic Solar Cells Zhou, Ruimin; Jiang, Zhaoyan; Shi, Yanan Advanced Functional Materials, Vol. 30, Issue 51 https://doi.org/10.1002/adfm.202005426	journal	September 2020
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
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 Advanced Materials, Vol. 30, Issue 27 https://doi.org/10.1002/adma.201706361	journal	May 2018
13.7% Efficiency Small‐Molecule Solar Cells Enabled by a Combination of Material and Morphology Optimization Yue, Qihui; Wu, Hao; Zhou, Zichun Advanced Materials, Vol. 31, Issue 51 https://doi.org/10.1002/adma.201904283	journal	November 2019
Highly Efficient All‐Small‐Molecule Organic Solar Cells with Appropriate Active Layer Morphology by Side Chain Engineering of Donor Molecules and Thermal Annealing Qiu, Beibei; Chen, Zeng; Qin, Shucheng Advanced Materials, Vol. 32, Issue 21 https://doi.org/10.1002/adma.201908373	journal	April 2020
Solution-Processed Organic Solar Cells with 9.8% Efficiency Based on a New Small Molecule Containing a 2D Fluorinated Benzodithiophene Central Unit Wang, Zhenguo; Xu, Xiaopeng; Li, Zuojia Advanced Electronic Materials, Vol. 2, Issue 6 https://doi.org/10.1002/aelm.201600061	journal	April 2016
High-Performance Small Molecule via Tailoring Intermolecular Interactions and its Application in Large-Area Organic Photovoltaic Modules Badgujar, Sachin; Lee, Gang-Young; Park, Taiho Advanced Energy Materials, Vol. 6, Issue 12 https://doi.org/10.1002/aenm.201600228	journal	April 2016
Simultaneous Enhancement of Three Parameters of P3HT‐Based Organic Solar Cells with One Oxygen Atom Wu, Jianfei; Xu, Yunxiao; Yang, Zhou Advanced Energy Materials, Vol. 9, Issue 6 https://doi.org/10.1002/aenm.201803012	journal	December 2018
Efficient Organic Solar Cell with 16.88% Efficiency Enabled by Refined Acceptor Crystallization and Morphology with Improved Charge Transfer and Transport Properties Zhu, Lei; Zhang, Ming; Zhou, Guanqing Advanced Energy Materials, Vol. 10, Issue 18 https://doi.org/10.1002/aenm.201904234	journal	March 2020
Precise Control of Phase Separation Enables 12% Efficiency in All Small Molecule Solar Cells Bin, Haijun; Angunawela, Indunil; Qiu, Beibei Advanced Energy Materials, Vol. 10, Issue 34 https://doi.org/10.1002/aenm.202001589	journal	August 2020
Emerging Approaches in Enhancing the Efficiency and Stability in Non‐Fullerene Organic Solar Cells Zhao, Fuwen; Zhang, Huotian; Zhang, Rui Advanced Energy Materials, Vol. 10, Issue 47 https://doi.org/10.1002/aenm.202002746	journal	November 2020
13.34 % Efficiency Non‐Fullerene All‐Small‐Molecule Organic Solar Cells Enabled by Modulating the Crystallinity of Donors via a Fluorination Strategy Ge, Jinfeng; Xie, Lingchao; Peng, Ruixiang Angewandte Chemie International Edition, Vol. 59, Issue 7 https://doi.org/10.1002/anie.201910297	journal	February 2020
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
17.1 %‐Efficient Eco‐Compatible Organic Solar Cells from a Dissymmetric 3D Network Acceptor Chen, Hui; Lai, Hanjian; Chen, Ziyi Angewandte Chemie International Edition, Vol. 60, Issue 6 https://doi.org/10.1002/anie.202013053	journal	December 2020
Developing Wide Bandgap Polymers Based on Sole Benzodithiophene Units for Efficient Polymer Solar Cells Xu, Xiaopeng; Lee, Young Woong; Woo, Han Young Chemistry – A European Journal, Vol. 26, Issue 49 https://doi.org/10.1002/chem.202000951	journal	July 2020
Recent Advances in Wide Bandgap Polymer Donors and Their Applications in Organic Solar Cells Xu, Xiaopeng; Yu, Liyang; Peng, Qiang Chinese Journal of Chemistry, Vol. 39, Issue 2 https://doi.org/10.1002/cjoc.202000451	journal	January 2021
Weak Makes It Powerful: The Role of Cognate Small Molecules as an Alloy Donor in 2D/1A Ternary Fullerene Solar Cells for Finely Tuned Hierarchical Morphology in Thick Active Layers Fan, Qunping; Liu, Tao; Zhang, Ming Small Methods, Vol. 4, Issue 3 https://doi.org/10.1002/smtd.201900766	journal	January 2020
Improving Molecular Planarity by Changing Alky Chain Position Enables 12.3% Efficiency All‐Small‐Molecule Organic Solar Cells with Enhanced Carrier Lifetime and Reduced Recombination Dong, Xiyue; Yang, Ke; Tang, Hua Solar RRL, Vol. 4, Issue 1 https://doi.org/10.1002/solr.201900326	journal	October 2019
Improving open-circuit voltage by a chlorinated polymer donor endows binary organic solar cells efficiencies over 17% Ma, Ruijie; Liu, Tao; Luo, Zhenghui Science China Chemistry, Vol. 63, Issue 3 https://doi.org/10.1007/s11426-019-9669-3	journal	February 2020
High-efficiency all-small-molecule organic solar cells based on an organic molecule donor with an asymmetric thieno[2,3-f] benzofuran unit Sun, Rui; Wu, Yao; Guo, Jing Science China Chemistry, Vol. 63, Issue 9 https://doi.org/10.1007/s11426-020-9753-x	journal	May 2020
15.3% efficiency all-small-molecule organic solar cells enabled by symmetric phenyl substitution Qin, Jinzhao; An, Cunbin; Zhang, Jianqi Science China Materials, Vol. 63, Issue 7 https://doi.org/10.1007/s40843-020-1269-9	journal	March 2020
The recent progress of wide bandgap donor polymers towards non-fullerene organic solar cells Xu, Xiaopeng; Zhang, Guangjun; Li, Ying Chinese Chemical Letters, Vol. 30, Issue 4 https://doi.org/10.1016/j.cclet.2019.02.030	journal	April 2019
Fused ring non-fullerene acceptors with benzothiophene dioxide end groups and their side chain effect investigations Deng, Min; Xu, Xiaopeng; Yu, Liyang Dyes and Pigments, Vol. 180 https://doi.org/10.1016/j.dyepig.2020.108452	journal	September 2020
14.46% Efficiency small molecule organic photovoltaics enabled by the well trade-off between phase separation and photon harvesting Xu, Chunyu; Chen, Haiyan; Zhao, Zijin Journal of Energy Chemistry, Vol. 57 https://doi.org/10.1016/j.jechem.2020.09.025	journal	June 2021
All-Small-Molecule Organic Solar Cells with an Ordered Liquid Crystalline Donor Chen, Haiyan; Hu, Dingqin; Yang, Qianguang Joule, Vol. 3, Issue 12 https://doi.org/10.1016/j.joule.2019.09.009	journal	December 2019
Fine-Tuning Energy Levels via Asymmetric End Groups Enables Polymer Solar Cells with Efficiencies over 17% Luo, Zhenghui; Ma, Ruijie; Liu, Tao Joule, Vol. 4, Issue 6 https://doi.org/10.1016/j.joule.2020.03.023	journal	June 2020
Benzodithiophene-Based Small-Molecule Donors for Next-Generation All-Small-Molecule Organic Photovoltaics Tang, Hua; Yan, Cenqi; Huang, Jiaming Matter, Vol. 3, Issue 5 https://doi.org/10.1016/j.matt.2020.09.001	journal	November 2020
Synergistic effect of halogenation on molecular energy level and photovoltaic performance modulations of highly efficient small molecular materials Ji, Zhenkai; Xu, Xiaopeng; Zhang, Guangjun Nano Energy, Vol. 40 https://doi.org/10.1016/j.nanoen.2017.08.027	journal	October 2017
Over 15% efficiency all-small-molecule organic solar cells enabled by a C-shaped small molecule donor with tailorable asymmetric backbone Wang, Xunchang; Wang, Jianxiao; Han, Jianhua Nano Energy, Vol. 81 https://doi.org/10.1016/j.nanoen.2020.105612	journal	March 2021
A new small molecule donor for efficient and stable all small molecule organic solar cells Wang, Wei; Chen, Bingcai; Jiao, Xuechen Organic Electronics, Vol. 70 https://doi.org/10.1016/j.orgel.2019.03.011	journal	July 2019
18% Efficiency organic solar cells Liu, Qishi; Jiang, Yufan; Jin, Ke Science Bulletin, Vol. 65, Issue 4 https://doi.org/10.1016/j.scib.2020.01.001	journal	February 2020
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 and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks Huang, Hui; Yang, Lei; Facchetti, Antonio Chemical Reviews, Vol. 117, Issue 15 https://doi.org/10.1021/acs.chemrev.7b00084	journal	July 2017
Modulation of Donor Alkyl Terminal Chains with the Shifting Branching Point Leads to the Optimized Morphology and Efficient All-Small-Molecule Organic Solar Cells Wu, Qiong; Deng, Dan; Zhou, Ruimin ACS Applied Materials & Interfaces, Vol. 12, Issue 22 https://doi.org/10.1021/acsami.0c03977	journal	May 2020
Side-Chain Engineering of Benzodithiophene-Bridged Dimeric Porphyrin Donors for All-Small-Molecule Organic Solar Cells Piradi, Venkatesh; Zhang, Guangjun; Li, Tengfei ACS Applied Materials & Interfaces, Vol. 12, Issue 37 https://doi.org/10.1021/acsami.0c11410	journal	August 2020
Effect of Side-Chain Modification on the Active Layer Morphology and Photovoltaic Performance of Liquid Crystalline Molecular Materials Subbiah, Jegadesan; Lee, Calvin J.; Mitchell, Valerie D. ACS Applied Materials & Interfaces, Vol. 13, Issue 1 https://doi.org/10.1021/acsami.0c20389	journal	December 2020
Effective Molecular Engineering Approach for Employing a Halogen-Free Solvent for the Fabrication of Solution-Processed Small-Molecule Solar Cells Abbas, Zaheer; Shin, Jawon; Atla, Raju ACS Applied Materials & Interfaces, Vol. 10, Issue 45 https://doi.org/10.1021/acsami.8b14888	journal	October 2018
Simple-Structured NIR-Absorbing Small-Molecule Acceptors with a Thiazolothiazole Core: Multiple Noncovalent Conformational Locks and D–A Effect for Efficient OSCs Peng, Wenhong; Zhang, Guangjun; Zhu, Mengbing ACS Applied Materials & Interfaces, Vol. 11, Issue 51 https://doi.org/10.1021/acsami.9b16686	journal	November 2019
Improved Efficiency in All-Small-Molecule Organic Solar Cells with Ternary Blend of Nonfullerene Acceptor and Chlorinated and Nonchlorinated Donors Ge, Jinfeng; Wei, Qiang; Peng, Ruixiang ACS Applied Materials & Interfaces, Vol. 11, Issue 47 https://doi.org/10.1021/acsami.9b16900	journal	November 2019
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
New Phase for Organic Solar Cell Research: Emergence of Y-Series Electron Acceptors and Their Perspectives Li, Shuixing; Li, Chang-Zhi; Shi, Minmin ACS Energy Letters, Vol. 5, Issue 5 https://doi.org/10.1021/acsenergylett.0c00537	journal	April 2020
Low-Bandgap Non-fullerene Acceptors Enabling High-Performance Organic Solar Cells Liu, Wei; Xu, Xiang; Yuan, Jun ACS Energy Letters, Vol. 6, Issue 2 https://doi.org/10.1021/acsenergylett.0c02384	journal	January 2021
Nonfullerene All-Small-Molecule Organic Solar Cells Huo, Yong; Zhang, Hao-Li; Zhan, Xiaowei ACS Energy Letters, Vol. 4, Issue 6 https://doi.org/10.1021/acsenergylett.9b00528	journal	May 2019
Solution-Processed and High-Performance Organic Solar Cells Using Small Molecules with a Benzodithiophene Unit Zhou, Jiaoyan; Zuo, Yi; Wan, Xiangjian Journal of the American Chemical Society, Vol. 135, Issue 23 https://doi.org/10.1021/ja403318y	journal	May 2013
Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions Jackson, Nicholas E.; Savoie, Brett M.; Kohlstedt, Kevin L. Journal of the American Chemical Society, Vol. 135, Issue 28 https://doi.org/10.1021/ja403667s	journal	May 2013
n-Type Molecular Photovoltaic Materials: Design Strategies and Device Applications Yue, Qihui; Liu, Wuyue; Zhu, Xiaozhang Journal of the American Chemical Society, Vol. 142, Issue 27 https://doi.org/10.1021/jacs.0c04084	journal	May 2020
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
Bis(methylthio)tetracenes: Synthesis, Crystal-Packing Structures, and OFET Properties Kimoto, Takakazu; Tanaka, Kenro; Kawahata, Masatoshi The Journal of Organic Chemistry, Vol. 76, Issue 12 https://doi.org/10.1021/jo200696a	journal	June 2011
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
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
Single-layered organic photovoltaics with double cascading charge transport pathways: 18% efficiencies Zhang, Ming; Zhu, Lei; Zhou, Guanqing Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-020-20580-8	journal	January 2021
Highly efficient halogen-free solvent processed small-molecule organic solar cells enabled by material design and device engineering Wan, Jiahui; Xu, Xiaopeng; Zhang, Guangjun Energy & Environmental Science, Vol. 10, Issue 8 https://doi.org/10.1039/C7EE00805H	journal	January 2017
Terminal group engineering for small-molecule donors boosts the performance of nonfullerene organic solar cells Duan, Tainan; Tang, Hua; Liang, Ru-Ze Journal of Materials Chemistry A, Vol. 7, Issue 6 https://doi.org/10.1039/C8TA11420J	journal	January 2019
A novel wide-bandgap small molecule donor for high efficiency all-small-molecule organic solar cells with small non-radiative energy losses Wang, Yulong; Wang, Yang; Zhu, Lei Energy & Environmental Science, Vol. 13, Issue 5 https://doi.org/10.1039/C9EE04199K	journal	January 2020
Designing high performance conjugated materials for photovoltaic cells with the aid of intramolecular noncovalent interactions Liu, Yahui; Song, Jinsheng; Bo, Zhishan Chemical Communications, Vol. 57, Issue 3 https://doi.org/10.1039/D0CC07086F	journal	January 2021
15.34% efficiency all-small-molecule organic solar cells with an improved fill factor enabled by a fullerene additive Hu, Dingqin; Yang, Qianguang; Chen, Haiyan Energy & Environmental Science, Vol. 13, Issue 7 https://doi.org/10.1039/D0EE00714E	journal	January 2020
Highly efficient non-fullerene organic solar cells enabled by a delayed processing method using a non-halogenated solvent Xu, Xiaopeng; Yu, Liyang; Yan, He Energy & Environmental Science, Vol. 13, Issue 11 https://doi.org/10.1039/D0EE02034F	journal	January 2020
Fine-tuning of side-chain orientations on nonfullerene acceptors enables organic solar cells with 17.7% efficiency Chai, Gaoda; Chang, Yuan; Zhang, Jianquan Energy & Environmental Science, Vol. 14, Issue 6 https://doi.org/10.1039/D0EE03506H	journal	January 2021
Over 14% efficiency nonfullerene all-small-molecule organic solar cells enabled by improving the ordering of molecular donors via side-chain engineering Gao, Jing; Ge, Jinfeng; Peng, Ruixiang Journal of Materials Chemistry A, Vol. 8, Issue 15 https://doi.org/10.1039/D0TA01893G	journal	January 2020
Small molecule donors with different conjugated π linking bridges: Synthesis and photovoltaic properties Dong, Xiyue; Hu, Dingqin; Chen, Pengyu Journal of Semiconductors, Vol. 41, Issue 12 https://doi.org/10.1088/1674-4926/41/12/122201	journal	December 2020
Effects of Alkoxy and Fluorine Atom Substitution of Donor Molecules on the Morphology and Photovoltaic Performance of All Small Molecule Organic Solar Cells Qiu, Beibei; Chen, Shanshan; Xue, Lingwei Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00413	journal	September 2018

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Related Subjects

36 MATERIALS SCIENCE
All-small-molecule organic solar cells
Molecular packing
Non-covalent bond interaction
Non-fullerene acceptor
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Molecular packing modulation enabling optimized blend morphology and efficient all small molecule organic solar cells

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