Readily Accessible Benzo[d]thiazole Polymers for Nonfullerene Solar Cells with &gt;16% Efficiency and Potential Pitfalls

Feng, Liang-Wen; Chen, Jianhua; Mukherjee, Subhrangsu; Sangwan, Vinod K.; Huang, Wei; Chen, Yao; Zheng, Ding; Strzalka, Joseph W.; Wang, Gang; Hersam, Mark C.; DeLongchamp, Dean; Facchetti, Antonio; Marks, Tobin J.

doi:10.1021/acsenergylett.0c00691

Readily Accessible Benzo[d]thiazole Polymers for Nonfullerene Solar Cells with >16% Efficiency and Potential Pitfalls

Journal Article · Mon May 04 00:00:00 EDT 2020 · ACS Energy Letters

DOI:https://doi.org/10.1021/acsenergylett.0c00691· OSTI ID:1635203

Feng, Liang-Wen ^[1]; ^[1]; ^[2]; ^[1]; ^[1]; ^[1]; Zheng, Ding ^[1]; ^[3]; Wang, Gang ^[1]; ^[1]; DeLongchamp, Dean ^[4]; ^[5]; ^[6]

Northwestern Univ., Evanston, IL (United States)
National Inst. of Standards and Technology (NIST), Gaithersburg, MD (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)
Materials Science and Engineering Division, National Institute of Standards and Technology, Gaithersburg, Maryland 20899, United States
Department of Chemistry, Center for Light Energy-Activated Redox Processes, and the Materials Research Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States; Flexterra Corporation, 8025 Lamon Avenue, Skokie, Illinois 60077, United States
Department of Chemistry, Center for Light Energy-Activated Redox Processes, and the Materials Research Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States

Here we report facile, high-yield synthetic access to the difluoro BTA building block, 4,7-bis(5-bromo-4-(2-hexyl-decyl)-thiophen-2-yl)-5,6-difluoro-2-(pentadecan-7-yl)-benzo[d]thiazole (BTAT-2f), for use in donor (D)–acceptor 1 (A1)–D–acceptor 2 (A2) polymers [D = bithiophene; A1 = BTA-2f; A2 = benzothiadiazole (BT) derivative] for organic solar cells (OSCs). Fine tuning of polymer optical and electronic properties is achieved by incrementally varying the A2 fluorination level. Bulk-heterojunction (BHJ) PBTATBT-4f:Y6 solar cells deliver a noteworthy power conversion (PCE) efficiency of 16.08% (V_oc = 0.81 V; J_sc = 27.25 mAcm^–2; FF = 72.70%) without processing additives. In contrast, PBTATBT-2f:Y6 exhibits an irregular morphology and low PCE, ascribable to cocrystal formation-induced recombination, which is unprecedented for nonfullerene (NFA) OSCs. This result should be of guiding significance for future NFA design.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

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

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1635203

Alternate ID(s):: OSTI ID: 1690072

Journal Information:: ACS Energy Letters, Journal Name: ACS Energy Letters Journal Issue: 6 Vol. 5; ISSN 2380-8195

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (45)

Bimolecular Crystals of Fullerenes in Conjugated Polymers and the Implications of Molecular Mixing for Solar Cells Mayer, A. C.; Toney, Michael F.; Scully, Shawn R. Advanced Functional Materials, Vol. 19, Issue 8 https://doi.org/10.1002/adfm.200801684	journal	April 2009
Correlated In Situ Low-Frequency Noise and Impedance Spectroscopy Reveal Recombination Dynamics in Organic Solar Cells Using Fullerene and Non-Fullerene Acceptors Luck, Kyle A.; Sangwan, Vinod K.; Hartnett, Patrick E. Advanced Functional Materials, Vol. 27, Issue 48 https://doi.org/10.1002/adfm.201703805	journal	November 2017
Toward Additive-Free Small-Molecule Organic Solar Cells: Roles of the Donor Crystallization Pathway and Dynamics Abdelsamie, Maged; Treat, Neil D.; Zhao, Kui Advanced Materials, Vol. 27, Issue 45 https://doi.org/10.1002/adma.201503395	journal	September 2015
Organic Photovoltaics over Three Decades Inganäs, Olle Advanced Materials, Vol. 30, Issue 35 https://doi.org/10.1002/adma.201800388	journal	June 2018
17% Efficient Organic Solar Cells Based on Liquid Exfoliated WS ₂ as a Replacement for PEDOT:PSS Lin, Yuanbao; Adilbekova, Begimai; Firdaus, Yuliar Advanced Materials, Vol. 31, Issue 46 https://doi.org/10.1002/adma.201902965	journal	September 2019
Understanding the High Performance of over 15% Efficiency in Single‐Junction Bulk Heterojunction Organic Solar Cells Karki, Akchheta; Vollbrecht, Joachim; Dixon, Alana L. Advanced Materials, Vol. 31, Issue 48 https://doi.org/10.1002/adma.201903868	journal	October 2019
Achieving Fast Charge Separation and Low Nonradiative Recombination Loss by Rational Fluorination for High‐Efficiency Polymer Solar Cells Sun, Chenkai; Pan, Fei; Chen, Shanshan Advanced Materials, Vol. 31, Issue 52 https://doi.org/10.1002/adma.201905480	journal	November 2019
Phthalimide‐Based High Mobility Polymer Semiconductors for Efficient Nonfullerene Solar Cells with Power Conversion Efficiencies over 13% Yu, Jianwei; Chen, Peng; Koh, Chang Woo Advanced Science https://doi.org/10.1002/advs.201801743	journal	December 2018
Fluorinating π‐Extended Molecular Acceptors Yields Highly Connected Crystal Structures and Low Reorganization Energies for Efficient Solar Cells Swick, Steven M.; Alzola, Joaquin M.; Sangwan, Vinod K. Advanced Energy Materials, Vol. 10, Issue 23 https://doi.org/10.1002/aenm.202000635	journal	May 2020
Tetrahydroxy‐Perylene Bisimide Embedded in a Zinc Oxide Thin Film as an Electron‐Transporting Layer for High‐Performance Non‐Fullerene Organic Solar Cells Wen, Xinbo; Nowak‐Król, Agnieszka; Nagler, Oliver Angewandte Chemie International Edition, Vol. 58, Issue 37 https://doi.org/10.1002/anie.201907467	journal	August 2019
Strategy for structural elucidation of drugs and drug metabolites using (MS)n fragmentation in an electrospray ion trap Tozuka, Zenzaburo; Kaneko, Hayato; Shiraga, Toshifumi Journal of Mass Spectrometry, Vol. 38, Issue 8 https://doi.org/10.1002/jms.511	journal	January 2003
UV/Vis Spectral Study of the Self-aggregation of Pinacyanol Chloride in Ethanol–Water Solutions Khouri, Sa’ib J.; Buss, Volker Journal of Solution Chemistry, Vol. 39, Issue 1 https://doi.org/10.1007/s10953-009-9476-2	journal	November 2009
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
Riluzole, a glutamate antagonist, enhances slow wave and REM sleep in rats Stutzmann, J. M.; Lucas, M.; Blanchard, J. C. Neuroscience Letters, Vol. 88, Issue 2 https://doi.org/10.1016/0304-3940(88)90125-5	journal	May 1988
Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D–π–A dyes Ci, Zhenhua; Yu, Xiaoqiang; Bao, Ming Dyes and Pigments, Vol. 96, Issue 3 https://doi.org/10.1016/j.dyepig.2012.11.004	journal	March 2013
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
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
Fill factor in organic solar cells Gupta, Dhritiman; Mukhopadhyay, Sabyasachi; Narayan, K. S. Solar Energy Materials and Solar Cells, Vol. 94, Issue 8 https://doi.org/10.1016/j.solmat.2008.06.001	journal	August 2010
Synthesis and luminescence of red, fluorinated iridium (III) complexes containing alkenyl benzothiazole ligand Xiao, Guoyong; Lei, Peng; Chi, Haijun Synthetic Metals, Vol. 159, Issue 7-8 https://doi.org/10.1016/j.synthmet.2008.12.019	journal	April 2009
Benzo[ d ][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers Chen, Zhihua; Brown, Jennifer; Drees, Martin Chemistry of Materials, Vol. 28, Issue 17 https://doi.org/10.1021/acs.chemmater.6b02813	journal	August 2016
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
Impact of Structural Polymorphs on Charge Collection and Nongeminate Recombination in Organic Photovoltaic Devices Keivanidis, Panagiotis E.; Khan, Jafar I.; Katzenmeier, Leon The Journal of Physical Chemistry C, Vol. 122, Issue 51 https://doi.org/10.1021/acs.jpcc.8b09825	journal	November 2018
Investigation of Fluorination on Donor Moiety of Donor–Acceptor 4,7-Dithienylbenzothiadiazole-Based Conjugated Polymers toward Enhanced Photovoltaic Efficiency Li, Yonghai; Wang, Junyi; Liu, Yan ACS Applied Materials & Interfaces, Vol. 8, Issue 39 https://doi.org/10.1021/acsami.6b08233	journal	September 2016
5,6-Difluorobenzothiazole-Based Conjugated Polymers with Large Band Gaps and Deep Highest Occupied Molecular Orbital Levels Sun, Jiangman; Cai, Ping; Pan, Feilong ACS Applied Materials & Interfaces, Vol. 10, Issue 13 https://doi.org/10.1021/acsami.8b03643	journal	March 2018
Low-Frequency Carrier Kinetics in Perovskite Solar Cells Sangwan, Vinod K.; Zhu, Menghua; Clark, Sarah ACS Applied Materials & Interfaces, Vol. 11, Issue 15 https://doi.org/10.1021/acsami.9b03884	journal	March 2019
Conjugated Polymer-Based Organic Solar Cells Günes, Serap; Neugebauer, Helmut; Sariciftci, Niyazi Serdar Chemical Reviews, Vol. 107, Issue 4, p. 1324-1338 https://doi.org/10.1021/cr050149z	journal	April 2007
Hybridization of Local Exciton and Charge-Transfer States Reduces Nonradiative Voltage Losses in Organic Solar Cells Eisner, Flurin D.; Azzouzi, Mohammed; Fei, Zhuping Journal of the American Chemical Society, Vol. 141, Issue 15 https://doi.org/10.1021/jacs.9b01465	journal	March 2019
High Efficiency Polymer Solar Cells with Efficient Hole Transfer at Zero Highest Occupied Molecular Orbital Offset between Methylated Polymer Donor and Brominated Acceptor Sun, Chenkai; Qin, Shucheng; Wang, Rui Journal of the American Chemical Society, Vol. 142, Issue 3 https://doi.org/10.1021/jacs.9b09939	journal	January 2020
Bandgap and Molecular Energy Level Control of Conjugated Polymer Photovoltaic Materials Based on Benzo[1,2- b :4,5- b ′]dithiophene Hou, Jianhui; Park, Mi-Hyae; Zhang, Shaoqing Macromolecules, Vol. 41, Issue 16 https://doi.org/10.1021/ma800820r	journal	August 2008
Tuning the Properties of Polymer Bulk Heterojunction Solar Cells by Adjusting Fullerene Size to Control Intercalation Cates, Nichole C.; Gysel, Roman; Beiley, Zach Nano Letters, Vol. 9, Issue 12 https://doi.org/10.1021/nl9023808	journal	December 2009
A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO₂ films O'Regan, Brian; Grätzel, Michael Nature, Vol. 353, Issue 6346, p. 737-740 https://doi.org/10.1038/353737a0	journal	October 1991
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
Competition between recombination and extraction of free charges determines the fill factor of organic solar cells Bartesaghi, Davide; Pérez, Irene del Carmen; Kniepert, Juliane Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8083	journal	May 2015
High-performance ternary blend polymer solar cells involving both energy transfer and hole relay processes Lu, Luyao; Chen, Wei; Xu, Tao Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8327	journal	June 2015
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
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
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
New developments in non-fullerene small molecule acceptors for polymer solar cells Liang, Ningning; Jiang, Wei; Hou, Jianhui Materials Chemistry Frontiers, Vol. 1, Issue 7 https://doi.org/10.1039/C6QM00247A	journal	January 2017
How to determine optical gaps and voltage losses in organic photovoltaic materials Vandewal, K.; Benduhn, J.; Nikolis, V. C. Sustainable Energy & Fuels, Vol. 2, Issue 3 https://doi.org/10.1039/C7SE00601B	journal	January 2018
Measuring the competition between bimolecular charge recombination and charge transport in organic solar cells under operating conditions Heiber, Michael C.; Okubo, Takashi; Ko, Seo-Jin Energy & Environmental Science, Vol. 11, Issue 10 https://doi.org/10.1039/C8EE01559G	journal	January 2018
Characterization of nanostructured hybrid and organic solar cells by impedance spectroscopy Fabregat-Santiago, Francisco; Garcia-Belmonte, Germà; Mora-Seró, Iván Physical Chemistry Chemical Physics, Vol. 13, Issue 20 https://doi.org/10.1039/c0cp02249g	journal	January 2011
Enhanced photovoltaic properties in graphene/polycrystalline BiFeO ₃ /Pt heterojunction structure Zang, Yongyuan; Xie, Dan; Wu, Xiao Applied Physics Letters, Vol. 99, Issue 13 https://doi.org/10.1063/1.3644134	journal	September 2011
Balanced charge carrier mobilities in bulk heterojunction organic solar cells Abbas, Mamatimin; Tekin, Nalan Applied Physics Letters, Vol. 101, Issue 7 https://doi.org/10.1063/1.4745602	journal	August 2012
The Physics of Solar Cells Nelson, Jenny World Scientific https://doi.org/10.1142/p276	book	January 2003
The Development of the Antitumour Benzothiazole Prodrug, Phortress, as a Clinical Candidate Bradshaw, T.; Westwell, A. Current Medicinal Chemistry, Vol. 11, Issue 8 https://doi.org/10.2174/0929867043455530	journal	April 2004

Similar Records

Critical Role of Polymer Aggregation and Miscibility in Nonfullerene‐Based Organic Photovoltaics

Journal Article · Tue Jan 28 19:00:00 EST 2020 · Advanced Energy Materials · OSTI ID:1595870

Nonfullerene Acceptor Featuring Unique Self‐Regulation Effect for Organic Solar Cells with 19 % Efficiency

Journal Article · Wed Dec 13 23:00:00 EST 2023 · Angewandte Chemie (International Edition) · OSTI ID:2580576

Bandgap Narrowing in Non‐Fullerene Acceptors: Single Atom Substitution Leads to High Optoelectronic Response Beyond 1000 nm

Journal Article · Wed Jun 27 20:00:00 EDT 2018 · Advanced Energy Materials · OSTI ID:1457792

Related Subjects

14 SOLAR ENERGY

Readily Accessible Benzo[d]thiazole Polymers for Nonfullerene Solar Cells with >16% Efficiency and Potential Pitfalls

Citation Formats

References (45)

Similar Records

Related Subjects