Asymmetric Siloxane Functional Side Chains Enable High-Performance Donor Copolymers for Photovoltaic Applications

Tang, Ziye; Xu, Xiaopeng; Li, Ruipeng; Yu, Liyang; Meng, Lei; Wang, Yuliang; Li, Ying; Peng, Qiang

doi:10.1021/acsami.9b20204

Asymmetric Siloxane Functional Side Chains Enable High-Performance Donor Copolymers for Photovoltaic Applications

Journal Article · Mon Mar 09 00:00:00 EDT 2020 · ACS Applied Materials and Interfaces

DOI:https://doi.org/10.1021/acsami.9b20204· OSTI ID:1659696

Tang, Ziye ^[1]; Xu, Xiaopeng ^[1]; Li, Ruipeng ^[2]; Yu, Liyang ^[1]; Meng, Lei ^[3]; Wang, Yuliang ^[1]; Li, Ying ^[1]; ^[1]

Sichuan Univ., Chengdu (China)
Brookhaven National Lab. (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)
Chinese Academy of Sciences (CAS), Beijing (China)

Herein, three benzodithiophene–benzotriazole alternated wide band gap copolymers attaching symmetric or asymmetric conjugated side chains, namely, PDBTFBTA-2T, PBDTFTBA-TSi, and PBDTFBTA-2Si, were developed for efficient nonfullerene polymer solar cells. The symmetry effect of the side chains was investigated in detail on the overall properties of these donor polymers. The results demonstrated that the introduced siloxane functional groups showed less effect on the absorption and frontier orbital levels of the prepared polymers but had a significant effect on the miscibility between these polymer donors and the nonfullerene acceptor. When increasing the content of siloxane functional groups, the miscibility of the polymer donors and Y6 would be improved, leading to the decreased domain size and more mixed domains. Interestingly, the active blend based on PBDTFTBA-TSi with asymmetric side chains exhibited more balanced miscibility, carrier mobility, and phase separation, benefiting exciton diffusion and dissociation. Therefore, a champion power conversion efficiency (PCE) of 14.18% was achieved finally in PBDTFTBA-TSi devices, which was 20.6 and 19.0% higher than the symmetric counterparts of PBTFBTA-2T devices (PCE = 11.76%) and PBDTFBTA-2Si devices (PCE = 11.92%), respectively. This work highlights that the asymmetric side-chain engineering based on siloxane functional groups is a promising design strategy for high-performance polymer donor semiconductors.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)

Sponsoring Organization:: Foundation of State Key Laboratory of Polymer Materials Engineering; National Natural Science Foundation of China (NSFC); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012704

OSTI ID:: 1659696

Report Number(s):: BNL--216360-2020-JAAM

Journal Information:: ACS Applied Materials and Interfaces, Journal Name: ACS Applied Materials and Interfaces Journal Issue: 15 Vol. 12; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (50)

Effect of Spacer Length of Siloxane-Terminated Side Chains on Charge Transport in Isoindigo-Based Polymer Semiconductor Thin Films Mei, Jianguo; Wu, Hung-Chin; Diao, Ying Advanced Functional Materials, Vol. 25, Issue 23 https://doi.org/10.1002/adfm.201500684	journal	May 2015
Fluorobenzotriazole (FTAZ)-Based Polymer Donor Enables Organic Solar Cells Exceeding 12% Efficiency Liao, Zhihui; Xie, Yuanpeng; Chen, Lie Advanced Functional Materials, Vol. 29, Issue 10 https://doi.org/10.1002/adfm.201808828	journal	January 2019
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
Side Chain Engineering on Medium Bandgap Copolymers to Suppress Triplet Formation for High-Efficiency Polymer Solar Cells Xue, Lingwei; Yang, Yankang; Xu, Jianqiu Advanced Materials, Vol. 29, Issue 40 https://doi.org/10.1002/adma.201703344	journal	August 2017
All-Polymer Solar Cells Based on a Conjugated Polymer Containing Siloxane-Functionalized Side Chains with Efficiency over 10% Fan, Baobing; Ying, Lei; Zhu, Peng Advanced Materials, Vol. 29, Issue 47 https://doi.org/10.1002/adma.201703906	journal	November 2017
Realizing Over 13% Efficiency in Green-Solvent-Processed Nonfullerene Organic Solar Cells Enabled by 1,3,4-Thiadiazole-Based Wide-Bandgap Copolymers Xu, Xiaopeng; Yu, Ting; Bi, Zhaozhao Advanced Materials, Vol. 30, Issue 3 https://doi.org/10.1002/adma.201703973	journal	December 2017
Stirring Up Acceptor Phase and Controlling Morphology via Choosing Appropriate Rigid Aryl Rings as Lever Arms in Symmetry-Breaking Benzodithiophene for High-Performance Fullerene and Fullerene-Free Polymer Solar Cells Liu, Deyu; Wang, Junyi; Gu, Chunyang Advanced Materials, Vol. 30, Issue 8 https://doi.org/10.1002/adma.201705870	journal	January 2018
Highly Efficient Nonfullerene Polymer Solar Cells Enabled by a Copper(I) Coordination Strategy Employing a 1,3,4-Oxadiazole-Containing Wide-Bandgap Copolymer Donor Xu, Xiaopeng; Li, Zuojia; Bi, Zhaozhao Advanced Materials, Vol. 30, Issue 28 https://doi.org/10.1002/adma.201800737	journal	May 2018
Single‐Junction Polymer Solar Cells with 16.35% Efficiency Enabled by a Platinum(II) Complexation Strategy Xu, Xiaopeng; Feng, Kui; Bi, Zhaozhao Advanced Materials, Vol. 31, Issue 29 https://doi.org/10.1002/adma.201901872	journal	May 2019
16.67% Rigid and 14.06% Flexible Organic Solar Cells Enabled by Ternary Heterojunction Strategy Yan, Tingting; Song, Wei; Huang, Jiaming Advanced Materials, Vol. 31, Issue 39 https://doi.org/10.1002/adma.201902210	journal	August 2019
Improved Charge Transport and Reduced Nonradiative Energy Loss Enable Over 16% Efficiency in Ternary Polymer Solar Cells Yu, Runnan; Yao, Huifeng; Cui, Yong Advanced Materials, Vol. 31, Issue 36 https://doi.org/10.1002/adma.201902302	journal	June 2019
Effect of Alkylsilyl Side-Chain Structure on Photovoltaic Properties of Conjugated Polymer Donors Bin, Haijun; Yang, Yankang; Peng, Zhengxing Advanced Energy Materials, Vol. 8, Issue 8 https://doi.org/10.1002/aenm.201702324	journal	December 2017
High-Performance Thick-Film All-Polymer Solar Cells Created Via Ternary Blending of a Novel Wide-Bandgap Electron-Donating Copolymer Fan, Baobing; Zhu, Peng; Xin, Jingming Advanced Energy Materials, Vol. 8, Issue 14 https://doi.org/10.1002/aenm.201703085	journal	February 2018
Effects of Different Unsaturated-Linker-Containing Donors on Electronic Properties of Benzobisthiadiazole-Based Copolymers Zhang, Chen; Chen, Zhihui; Yang, Changan Macromolecular Chemistry and Physics, Vol. 219, Issue 2 https://doi.org/10.1002/macp.201700474	journal	December 2017
Modifying the morphology via employing rigid phenyl side chains achieves efficient nonfullerene polymer solar cells Zhong, Yaqian; Liu, Deyu; Zhang, Kaili Journal of Polymer Science Part A: Polymer Chemistry, Vol. 56, Issue 24 https://doi.org/10.1002/pola.29264	journal	October 2018
Highly Efficient Non-Fullerene Polymer Solar Cells Enabled by Wide Bandgap Copolymers With Conjugated Selenyl Side Chains Li, Zuojia; Xu, Xiaopeng; Zhang, Guangjun Solar RRL, Vol. 2, Issue 10 https://doi.org/10.1002/solr.201800186	journal	August 2018
Achieving over 16% efficiency for single-junction organic solar cells Fan, Baobing; Zhang, Difei; Li, Meijing Science China Chemistry, Vol. 62, Issue 6 https://doi.org/10.1007/s11426-019-9457-5	journal	March 2019
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
Narrow band-gap copolymers with two acceptors of benzo[1,2-c;3,4-c′]bis[1,2,5]thiadiazole and Benzo[c][1,2,5] thiadiazole: Synthesis, characteristics and application in field-effect transistors Zhang, Chen; Chen, Zhihui; Zeng, Weixuan Dyes and Pigments, Vol. 130 https://doi.org/10.1016/j.dyepig.2016.03.037	journal	July 2016
Overcoming the trade-off between Voc and Jsc: Asymmetric chloro-substituted two-dimensional benzo[1,2-b:4,5-b′]dithiophene-based polymer solar cells Chao, Pengjie; Liu, Longzhu; Qu, Jianfei Dyes and Pigments, Vol. 162 https://doi.org/10.1016/j.dyepig.2018.10.071	journal	March 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
Naphthobistriazole-based wide bandgap donor polymers for efficient non-fullerene organic solar cells: Significant fine-tuning absorption and energy level by backbone fluorination Tang, Dongsheng; Wan, Jiahui; Xu, Xiaopeng Nano Energy, Vol. 53 https://doi.org/10.1016/j.nanoen.2018.08.059	journal	November 2018
Crystalline Medium-Bandgap Light-Harvesting Donor Material Based on β- Naphthalene Asymmetric-Modified Benzodithiophene Moiety toward Efficient Polymer Solar Cells Li, Yonghai; Liu, Deyu; Wang, Junyi Chemistry of Materials, Vol. 29, Issue 19 https://doi.org/10.1021/acs.chemmater.7b02495	journal	September 2017
Molecular Design of Benzodithiophene-Based Organic Photovoltaic Materials Yao, Huifeng; Ye, Long; Zhang, Hao Chemical Reviews, Vol. 116, Issue 12 https://doi.org/10.1021/acs.chemrev.6b00176	journal	June 2016
Chlorinated Wide-Bandgap Donor Polymer Enabling Annealing Free Nonfullerene Solar Cells with the Efficiency of 11.5% Liu, Zhitian; Gao, Yerun; Dong, Jun The Journal of Physical Chemistry Letters, Vol. 9, Issue 24 https://doi.org/10.1021/acs.jpclett.8b03247	journal	November 2018
A Balanced Face-On to Edge-On Texture Ratio in Naphthalene Diimide-Based Polymers with Hybrid Siloxane Chains Directs Highly Efficient Electron Transport Kim, Yiho; Long, Dang Xuan; Lee, Junghoon Macromolecules, Vol. 48, Issue 15 https://doi.org/10.1021/acs.macromol.5b01012	journal	July 2015
Conjugated Donor–Acceptor Polymers Entailing Pechmann Dye-Derived Acceptor with Siloxane-Terminated Side Chains Exhibiting Balanced Ambipolar Semiconducting Behavior Yang, Si-Fen; Liu, Zi-Tong; Cai, Zheng-Xu Macromolecules, Vol. 49, Issue 16 https://doi.org/10.1021/acs.macromol.6b01440	journal	August 2016
Complementary Semiconducting Polymer Blends: Influence of Side Chains of Matrix Polymers Zhao, Xikang; Xue, Guobiao; Qu, Ge Macromolecules, Vol. 50, Issue 16 https://doi.org/10.1021/acs.macromol.7b01354	journal	August 2017
Multichloro-Substitution Strategy: Facing Low Photon Energy Loss in Nonfullerene Solar Cells Chao, Pengjie; Liu, Longzhu; Zhou, Jiadong ACS Applied Energy Materials, Vol. 1, Issue 11 https://doi.org/10.1021/acsaem.8b01447	journal	October 2018
Dithienothiapyran: An Excellent Donor Block for Building High-Performance Copolymers in Nonfullerene Polymer Solar Cells Deng, Min; Xu, Xiaopeng; Lee, Young Woong ACS Applied Materials & Interfaces, Vol. 11, Issue 3 https://doi.org/10.1021/acsami.8b18493	journal	December 2018
Impact of the Siloxane-Terminated Side Chain on Photovoltaic Performances of the Dithienylbenzodithiophene–Difluorobenzotriazole-Based Wide Band Gap Polymer Donor in Non-Fullerene Polymer Solar Cells Jiang, Haiying; Pan, Feilong; Zhang, Lianjie ACS Applied Materials & Interfaces, Vol. 11, Issue 32 https://doi.org/10.1021/acsami.9b08722	journal	July 2019
Siloxane-Terminated Side Chain Engineering of Acceptor Polymers Leading to Over 7% Power Conversion Efficiencies in All-Polymer Solar Cells Feng, Shizhen; Liu, Chang; Xu, Xiaofeng ACS Macro Letters, Vol. 6, Issue 11 https://doi.org/10.1021/acsmacrolett.7b00738	journal	November 2017
Comparison of the Photovoltaic Characteristics and Nanostructure of Fullerenes Blended with Conjugated Polymers with Siloxane-Terminated and Branched Aliphatic Side Chains Kim, Do Hwan; Ayzner, Alexander L.; Appleton, Anthony L. Chemistry of Materials, Vol. 25, Issue 3 https://doi.org/10.1021/cm303572d	journal	January 2013
Siloxane-Terminated Solubilizing Side Chains: Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors Mei, Jianguo; Kim, Do Hwan; Ayzner, Alexander L. Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja209328m	journal	December 2011
Solution-Processable Ambipolar Diketopyrrolopyrrole–Selenophene Polymer with Unprecedentedly High Hole and Electron Mobilities Lee, Junghoon; Han, A-Reum; Kim, Jonggi Journal of the American Chemical Society, Vol. 134, Issue 51 https://doi.org/10.1021/ja308927g	journal	December 2012
Boosting the Ambipolar Performance of Solution-Processable Polymer Semiconductors via Hybrid Side-Chain Engineering Lee, Junghoon; Han, A-Reum; Yu, Hojeong Journal of the American Chemical Society, Vol. 135, Issue 25 https://doi.org/10.1021/ja403949g	journal	June 2013
Non-Fullerene Polymer Solar Cells Based on Alkylthio and Fluorine Substituted 2D-Conjugated Polymers Reach 9.5% Efficiency Bin, Haijun; Zhang, Zhi-Guo; Gao, Liang Journal of the American Chemical Society, Vol. 138, Issue 13 https://doi.org/10.1021/jacs.6b01744	journal	March 2016
11.4% Efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor Bin, Haijun; Gao, Liang; Zhang, Zhi-Guo Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13651	journal	December 2016
Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages Cui, Yong; Yao, Huifeng; Zhang, Jianqi Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10351-5	journal	June 2019
An ultra-narrow bandgap derived from thienoisoindigo polymers: structural influence on reducing the bandgap and self-organization Hasegawa, Tsukasa; Ashizawa, Minoru; Hiyoshi, Junya Polymer Chemistry, Vol. 7, Issue 5 https://doi.org/10.1039/c5py01870f	journal	January 2016
Low band gap conjugated polymers combining siloxane-terminated side chains and alkyl side chains: side-chain engineering achieving a large active layer processing window for PCE > 10% in polymer solar cells Liu, Xuncheng; Nian, Li; Gao, Ke Journal of Materials Chemistry A, Vol. 5, Issue 33 https://doi.org/10.1039/c7ta05583h	journal	January 2017
Efficient fullerene-free solar cells with wide optical band gap polymers based on fluorinated benzotriazole and asymmetric benzodithiophene Liu, Zhe; Liu, Deyu; Zhang, Kaili J. Mater. Chem. A, Vol. 5, Issue 41 https://doi.org/10.1039/c7ta07390a	journal	January 2017
A trifluoromethyl substituted wide bandgap conjugated polymer for non-fullerene polymer solar cells with 10.4% efficiency Li, Wanbin; Li, Guangda; Guo, Xia Journal of Materials Chemistry A, Vol. 6, Issue 15 https://doi.org/10.1039/c7ta11059f	journal	January 2018
An effective strategy for controlling the morphology of high-performance non-fullerene polymer solar cells without post-treatment: employing bare rigid aryl rings as lever arms in new asymmetric benzodithiophene Liu, Deyu; Zhang, Kaili; Zhong, Yaqian Journal of Materials Chemistry A, Vol. 6, Issue 37 https://doi.org/10.1039/c8ta07134a	journal	January 2018
Nonhalogen solvent-processed polymer solar cells based on chlorine and trialkylsilyl substituted conjugated polymers achieve 12.8% efficiency Su, Wenyan; Li, Guangwei; Fan, Qunping Journal of Materials Chemistry A, Vol. 7, Issue 5 https://doi.org/10.1039/c8ta10662b	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
Design of asymmetric benzodithiophene based wide band-gap conjugated polymers toward efficient polymer solar cells promoted by a low boiling point additive Li, Yonghai; Duan, Linrui; Liu, Deyu Journal of Materials Chemistry C, Vol. 6, Issue 11 https://doi.org/10.1039/c8tc00148k	journal	January 2018
A monothiophene unit incorporating both fluoro and ester substitution enabling high-performance donor polymers for non-fullerene solar cells with 16.4% efficiency Sun, Huiliang; Liu, Tao; Yu, Jianwei Energy & Environmental Science, Vol. 12, Issue 11 https://doi.org/10.1039/c9ee01890e	journal	January 2019
Furan-flanked diketopyrrolopyrrole-based chalcogenophene copolymers with siloxane hybrid side chains for organic field-effect transistors Lee, Sang Myeon; Lee, Hae Rang; Dutta, Gitish K. Polymer Chemistry, Vol. 10, Issue 22 https://doi.org/10.1039/c9py00448c	journal	January 2019
The influence of siloxane side-chains on the photovoltaic performance of a conjugated polymer Heintges, Gaël H. L.; Hendriks, Koen H.; Colberts, Fallon J. M. RSC Advances, Vol. 9, Issue 16 https://doi.org/10.1039/c9ra00816k	journal	January 2019

Similar Records

Siloxane-functional small molecule acceptor for high-performance organic solar cells with 16.6% efficiency

Journal Article · Fri Mar 25 20:00:00 EDT 2022 · Chemical Engineering Journal · OSTI ID:1981560

Alkyl Chain Length Effects of Polymer Donors on the Morphology and Device Performance of Polymer Solar Cells with Different Acceptors

Journal Article · Mon Jul 08 20:00:00 EDT 2019 · Advanced Energy Materials · OSTI ID:1532584

19.32% Efficiency Polymer Solar Cells Enabled by Fine-Tuning Stacking Modes of Y-Type Molecule Acceptors: Synergistic Bromine and Fluorine Substitution of the End Groups

Journal Article · Thu Dec 14 19:00:00 EST 2023 · Advanced Materials · OSTI ID:2446646

Related Subjects

36 MATERIALS SCIENCE
charge transport properties
crystallinity
miscibility polymer solar cells
siloxane functional groups

Asymmetric Siloxane Functional Side Chains Enable High-Performance Donor Copolymers for Photovoltaic Applications

Citation Formats

References (50)

Similar Records

Related Subjects