2,3-Diphenylthieno[3,4-b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells

Afraj, Shakil N.; Zheng, Ding; Velusamy, Arulmozhi; Ke, Weijun; Cuthriell, Shelby; Zhang, Xiaohua; Chen, Yao; Lin, Chenjian; Ni, Jen-Shyang; Wasielewski, Michael R.; Huang, Wei; Yu, Junsheng; Pan, Chun-Huang; Schaller, Richard D.; Chen, Ming-Chou; Kanatzidis, Mercouri G.; Facchetti, Antonio; Marks, Tobin J.

doi:10.1021/acsenergylett.2c00684

2,3-Diphenylthieno[3,4-b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells

Journal Article · Tue May 31 00:00:00 EDT 2022 · ACS Energy Letters

DOI:https://doi.org/10.1021/acsenergylett.2c00684· OSTI ID:1924243

Afraj, Shakil N. ^[1]; ^[2]; Velusamy, Arulmozhi ^[1]; Ke, Weijun ^[3]; Cuthriell, Shelby ^[3]; Zhang, Xiaohua ^[4]; ^[3]; ^[3]; ^[5]; ^[3]; ^[3]; ^[4]; Pan, Chun-Huang ^[1]; ^[6]; ^[1]; ^[3]; ^[3]; ^[3]

National Central Univ., Taoyuan (Taiwan)
Univ. of Electronic Science and Technology of China, Chengdu (China); Northwestern Univ., Evanston, IL (United States)
Northwestern Univ., Evanston, IL (United States)
Univ. of Electronic Science and Technology of China, Chengdu (China)
National Kaohsiung University of Science and Technology (Taiwan)
Northwestern Univ., Evanston, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States). Center for Nanoscale Materials

High-performance and durable perovskite solar cells (PSCs) have advanced rapidly, enabled in part by the development of superior interfacial hole-transporting layers (HTLs). Here, in this study, a new series of 2,3-diphenylthieno[3,4-b]pyrazine (DPTP)-based small molecules containing bis- and tetrakis-triphenyl amino donors (1–3) was synthesized from simple, low-cost, and readily available starting materials. The matched energy levels, ideal surface topographies, high hole mobilities of 8.57 × 10^–4 cm² V^–1 S^–1, and stable chemical structures of DPTP-4D (3) make it an effective hole-transporting material, delivering a PCE of 20.18% with high environmental, thermal, and light-soaking stability when compared to the reference HTL materials, doped Spiro-OMeTAD and PTAA in PSC n-i-p planar devices. Overall, these DPTP-based molecules are promising HTM candidates for the fabrication of stable PSCs.

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); US Department of the Navy, Office of Naval Research (ONR); Northwestern University; National Science Foundation (NSF); W.M. Keck Foundation; State of Illinois; Ministry of Science and Technology of Taiwan (MOST); National Central University; National Key Research and Development Program of China; National Natural Science Foundation of China (NSFC)

Grant/Contract Number:: AC02-06CH11357; FG02-99ER14999

OSTI ID:: 1924243

Journal Information:: ACS Energy Letters, Journal Name: ACS Energy Letters Journal Issue: 6 Vol. 7; ISSN 2380-8195

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (62)

Polymer Solar Cells Based on a Low-Bandgap Fluorene Copolymer and a Fullerene Derivative with Photocurrent Extended to 850 nm Zhang, F.; Perzon, E.; Wang, X. Advanced Functional Materials, Vol. 15, Issue 5 https://doi.org/10.1002/adfm.200400416	journal	April 2005
Boosting the Efficiency of SnO ₂ ‐Triple Cation Perovskite System Beyond 20% Using Nonhalogenated Antisolvent Lee, Hock Beng; Jeon, Mi‐Kyung; Kumar, Neetesh Advanced Functional Materials, Vol. 29, Issue 32 https://doi.org/10.1002/adfm.201903213	journal	June 2019
Benzodithiophene Hole‐Transporting Materials for Efficient Tin‐Based Perovskite Solar Cells Vegiraju, Sureshraju; Ke, Weijun; Priyanka, Pragya Advanced Functional Materials, Vol. 29, Issue 45 https://doi.org/10.1002/adfm.201905393	journal	September 2019
Highly Stable and Efficient Perovskite Solar Cells with 22.0% Efficiency Based on Inorganic–Organic Dopant‐Free Double Hole Transporting Layers Liu, Chang; Zhang, Luozheng; Li, Yan Advanced Functional Materials, Vol. 30, Issue 28 https://doi.org/10.1002/adfm.201908462	journal	May 2020
Organic Ionic Plastic Crystals as Hole Transporting Layer for Stable and Efficient Perovskite Solar Cells Sonigara, Keval K.; Shao, Zhipeng; Prasad, Jyoti Advanced Functional Materials, Vol. 30, Issue 28 https://doi.org/10.1002/adfm.202001460	journal	May 2020
Heteroalkyl‐Substitution in Molecular Organic Semiconductors: Chalcogen Effect on Crystallography, Conformational Lock, and Charge Transport Afraj, Shakil N.; Lin, Chia‐Chi; Velusamy, Arulmozhi Advanced Functional Materials, Vol. 32, Issue 27 https://doi.org/10.1002/adfm.202200880	journal	March 2022
The Unusual Effect of Bandgap Lowering by C60 on a Conjugated Polymer Sonmez, G.; Shen, C. K. F.; Rubin, Y. Advanced Materials, Vol. 17, Issue 7 https://doi.org/10.1002/adma.200306494	journal	April 2005
Halide Perovskites: Poor Man's High-Performance Semiconductors Stoumpos, Constantinos C.; Kanatzidis, Mercouri G. Advanced Materials, Vol. 28, Issue 28 https://doi.org/10.1002/adma.201600265	journal	May 2016
Dopant‐Free Small‐Molecule Hole‐Transporting Material for Inverted Perovskite Solar Cells with Efficiency Exceeding 21% Wang, Yang; Chen, Wei; Wang, Lei Advanced Materials, Vol. 31, Issue 35 https://doi.org/10.1002/adma.201902781	journal	July 2019
Dopant‐Free Organic Hole‐Transporting Material for Efficient and Stable Inverted All‐Inorganic and Hybrid Perovskite Solar Cells Jiang, Kui; Wang, Jing; Wu, Fei Advanced Materials, Vol. 32, Issue 16 https://doi.org/10.1002/adma.201908011	journal	March 2020
Recent Advances in Spiro-MeOTAD Hole Transport Material and Its Applications in Organic-Inorganic Halide Perovskite Solar Cells Hawash, Zafer; Ono, Luis K.; Qi, Yabing Advanced Materials Interfaces, Vol. 5, Issue 1 https://doi.org/10.1002/admi.201700623	journal	October 2017
Dopant‐Free Crossconjugated Hole‐Transporting Polymers for Highly Efficient Perovskite Solar Cells Sun, Xianglang; Deng, Xiang; Li, Zhen Advanced Science, Vol. 7, Issue 13 https://doi.org/10.1002/advs.201903331	journal	May 2020
Recent Progress on Hole-Transporting Materials for Emerging Organometal Halide Perovskite Solar Cells Yu, Ze; Sun, Licheng Advanced Energy Materials, Vol. 5, Issue 12 https://doi.org/10.1002/aenm.201500213	journal	April 2015
New Generation Hole Transporting Materials for Perovskite Solar Cells: Amide-Based Small-Molecules with Nonconjugated Backbones Petrus, Michiel L.; Schutt, Kelly; Sirtl, Maximilian T. Advanced Energy Materials, Vol. 8, Issue 32 https://doi.org/10.1002/aenm.201801605	journal	October 2018
Relating Frontier Orbital Energies from Voltammetry and Photoelectron Spectroscopy to the Open-Circuit Voltage of Organic Solar Cells Willems, Robin E. M.; Weijtens, Christ H. L.; de Vries, Xander Advanced Energy Materials, Vol. 9, Issue 10 https://doi.org/10.1002/aenm.201803677	journal	January 2019
High‐Performance and Stable Perovskite Solar Cells Based on Dopant‐Free Arylamine‐Substituted Copper(II) Phthalocyanine Hole‐Transporting Materials Feng, Yaomiao; Hu, Qikun; Rezaee, Ehsan Advanced Energy Materials https://doi.org/10.1002/aenm.201901019	journal	May 2019
Rational Design of Dopant‐Free Coplanar D‐π‐D Hole‐Transporting Materials for High‐Performance Perovskite Solar Cells with Fill Factor Exceeding 80% Chen, Yatong; Xu, Xiuwen; Cai, Ning Advanced Energy Materials, Vol. 9, Issue 39 https://doi.org/10.1002/aenm.201901268	journal	August 2019
Development of Dopant‐Free Organic Hole Transporting Materials for Perovskite Solar Cells Pham, Hong Duc; Yang, Terry Chien‐Jen; Jain, Sagar M. Advanced Energy Materials, Vol. 10, Issue 13 https://doi.org/10.1002/aenm.201903326	journal	April 2020
Dopant‐Free Hole‐Transporting Material with Enhanced Intermolecular Interaction for Efficient and Stable n‐i‐p Perovskite Solar Cells Wang, Jing; Wu, Xin; Liu, Yizhe Advanced Energy Materials, Vol. 11, Issue 29 https://doi.org/10.1002/aenm.202100967	journal	June 2021
A Red, Green, and Blue (RGB) Polymeric Electrochromic Device (PECD): The Dawning of the PECD Era Sonmez, Gursel; Shen, Clifton K. F.; Rubin, Yves Angewandte Chemie International Edition, Vol. 43, Issue 12 https://doi.org/10.1002/anie.200352910	journal	March 2004
Benzotrithiophene-Based Hole-Transporting Materials for 18.2 % Perovskite Solar Cells Molina-Ontoria, Agustín; Zimmermann, Iwan; Garcia-Benito, Inés Angewandte Chemie International Edition, Vol. 55, Issue 21 https://doi.org/10.1002/anie.201511877	journal	April 2016
Hole-Transport Materials for Perovskite Solar Cells Calió, Laura; Kazim, Samrana; Grätzel, Michael Angewandte Chemie International Edition, Vol. 55, Issue 47 https://doi.org/10.1002/anie.201601757	journal	October 2016
Semi‐Locked Tetrathienylethene as a Building Block for Hole‐Transporting Materials: Toward Efficient and Stable Perovskite Solar Cells Shen, Chao; Wu, Yongzhen; Zhang, Hao Angewandte Chemie International Edition, Vol. 58, Issue 12 https://doi.org/10.1002/anie.201811593	journal	March 2019
Dopant‐Free Squaraine‐Based Polymeric Hole‐Transporting Materials with Comprehensive Passivation Effects for Efficient All‐Inorganic Perovskite Solar Cells Xiao, Qi; Tian, Jingjing; Xue, Qifan Angewandte Chemie International Edition, Vol. 58, Issue 49 https://doi.org/10.1002/anie.201907331	journal	December 2019
Intramolecular Noncovalent Interaction‐Enabled Dopant‐Free Hole‐Transporting Materials for High‐Performance Inverted Perovskite Solar Cells Yang, Kun; Liao, Qiaogan; Huang, Jun Angewandte Chemie International Edition, Vol. 61, Issue 2 https://doi.org/10.1002/anie.202113749	journal	December 2021
Stable Perovskite Solar Cells Using Molecularly Engineered Functionalized Oligothiophenes as Low‐Cost Hole‐Transporting Materials Joseph, Vellaichamy; Sutanto, Albertus Adrian; Igci, Cansu Small, Vol. 17, Issue 26 https://doi.org/10.1002/smll.202100783	journal	June 2021
Optical absorption spectra and energy band gap in praseodymium borophosphate glasses Sharma, Y. K.; Mathur, S. C.; Dube, D. C. Journal of Materials Science Letters, Vol. 14, Issue 1 https://doi.org/10.1007/BF02565291	journal	January 1995
Optical characterization of a new donor–acceptor type conjugated polymer derived from 3,4-diphenylthiophene Manjunatha, M. G.; Adhikari, Airody Vasudeva; Hegde, Pramod Kumar Journal of Materials Science, Vol. 44, Issue 22 https://doi.org/10.1007/s10853-009-3838-4	journal	November 2009
Isomeric Carbazole-Based Hole-Transporting Materials: Role of the Linkage Position on the Photovoltaic Performance of Perovskite Solar Cells Sutanto, Albertus Adrian; Joseph, Vellaichamy; Igci, Cansu Chemistry of Materials, Vol. 33, Issue 9 https://doi.org/10.1021/acs.chemmater.1c00335	journal	April 2021
Organic–Inorganic Perovskites: Structural Versatility for Functional Materials Design Saparov, Bayrammurad; Mitzi, David B. Chemical Reviews, Vol. 116, Issue 7 https://doi.org/10.1021/acs.chemrev.5b00715	journal	March 2016
Molecularly Engineered Cyclopenta[2,1-b;3,4-b′]dithiophene-Based Hole-Transporting Materials for High-Performance Perovskite Solar Cells with Efficiency over 19% Lin, Yan-Duo; Lee, Kun-Mu; Chang, Sheng Hsiung ACS Applied Energy Materials, Vol. 4, Issue 5 https://doi.org/10.1021/acsaem.1c00328	journal	April 2021
Asymmetric Benzotrithiophene-Based Hole Transporting Materials Provide High-Efficiency Perovskite Solar Cells Budiawan, Widhya; Lai, Kuan-Wen; Karuppuswamy, Priyadharsini ACS Applied Materials & Interfaces https://doi.org/10.1021/acsami.0c02204	journal	June 2020
Tetraphenylbutadiene-Based Symmetric 3D Hole-Transporting Materials for Perovskite Solar Cells: A Trial Trade-off between Charge Mobility and Film Morphology Chen, Jian; Xia, Jianxing; Gao, Wei-Jie ACS Applied Materials & Interfaces, Vol. 12, Issue 18 https://doi.org/10.1021/acsami.0c02751	journal	April 2020
Additive-free, Cost-Effective Hole-Transporting Materials for Perovskite Solar Cells Based on Vinyl Triarylamines Nishimura, Hidetaka; Okada, Iku; Tanabe, Taro ACS Applied Materials & Interfaces, Vol. 12, Issue 29 https://doi.org/10.1021/acsami.0c06055	journal	June 2020
Carbazole-Based Spiro[fluorene-9,9′-xanthene] as an Efficient Hole-Transporting Material for Perovskite Solar Cells Lee, Do Yoon; Sivakumar, Gangala ACS Applied Materials & Interfaces, Vol. 12, Issue 25 https://doi.org/10.1021/acsami.0c06318	journal	June 2020
D–A–D-Typed Hole Transport Materials for Efficient Perovskite Solar Cells: Tuning Photovoltaic Properties via the Acceptor Group Xu, Peng; Liu, Peng; Li, Yuanyuan ACS Applied Materials & Interfaces, Vol. 10, Issue 23 https://doi.org/10.1021/acsami.8b04003	journal	May 2018
Solvent Engineering of a Dopant-Free Spiro-OMeTAD Hole-Transport Layer for Centimeter-Scale Perovskite Solar Cells with High Efficiency and Thermal Stability Hu, Min; Wu, Xuelian; Tan, Wen Liang ACS Applied Materials & Interfaces, Vol. 12, Issue 7 https://doi.org/10.1021/acsami.9b21177	journal	January 2020
Carbazole-Terminated Isomeric Hole-Transporting Materials for Perovskite Solar Cells Rakstys, Kasparas; Paek, Sanghyun; Drevilkauskaite, Aida ACS Applied Materials & Interfaces, Vol. 12, Issue 17 https://doi.org/10.1021/acsami.9b23495	journal	April 2020
Impact of Peripheral Groups on Phenothiazine-Based Hole-Transporting Materials for Perovskite Solar Cells Zhang, Fei; Wang, Shirong; Zhu, Hongwei ACS Energy Letters, Vol. 3, Issue 5 https://doi.org/10.1021/acsenergylett.8b00395	journal	April 2018
Dopant-Free Tetrakis-Triphenylamine Hole Transporting Material for Efficient Tin-Based Perovskite Solar Cells Ke, Weijun; Priyanka, Pragya; Vegiraju, Sureshraju Journal of the American Chemical Society, Vol. 140, Issue 1 https://doi.org/10.1021/jacs.7b10898	journal	December 2017
Two-Dimensional Hybrid Halide Perovskites: Principles and Promises Mao, Lingling; Stoumpos, Constantinos C.; Kanatzidis, Mercouri G. Journal of the American Chemical Society, Vol. 141, Issue 3 https://doi.org/10.1021/jacs.8b10851	journal	November 2018
Perovskites: The Emergence of a New Era for Low-Cost, High-Efficiency Solar Cells Snaith, Henry J. The Journal of Physical Chemistry Letters, Vol. 4, Issue 21, p. 3623-3630 https://doi.org/10.1021/jz4020162	journal	October 2013
Raman Spectra of Poly(2,3-R,R-thieno[3,4-b]pyrazine). A New Low-Band-Gap Polymer Kastner, J.; Kuzmany, H.; Vegh, D. Macromolecules, Vol. 28, Issue 8 https://doi.org/10.1021/ma00112a044	journal	April 1995
A Second Look at Polythieno[3,4-b]pyrazines: Chemical vs Electrochemical Polymerization and Its Effect on Band Gap Kenning, Don D.; Rasmussen, Seth C. Macromolecules, Vol. 36, Issue 17 https://doi.org/10.1021/ma034831b	journal	July 2003
Poly(2,3-dihexylthieno[3,4- b ]pyrazine) via GRIM Polymerization: Simple Preparation of a Solution Processable, Low-Band-Gap Conjugated Polymer Wen, Li; Duck, Benjamin C.; Dastoor, Paul C. Macromolecules, Vol. 41, Issue 13 https://doi.org/10.1021/ma801057s	journal	July 2008
All-solid-state dye-sensitized solar cells with high efficiency Chung, In; Lee, Byunghong; He, Jiaqing Nature, Vol. 485, Issue 7399, p. 486-489 https://doi.org/10.1038/nature11067	journal	May 2012
Sequential deposition as a route to high-performance perovskite-sensitized solar cells Burschka, Julian; Pellet, Norman; Moon, Soo-Jin Nature, Vol. 499, Issue 7458, p. 316-319 https://doi.org/10.1038/nature12340	journal	July 2013
Efficient planar heterojunction perovskite solar cells by vapour deposition Liu, Mingzhen; Johnston, Michael B.; Snaith, Henry J. Nature, Vol. 501, Issue 7467, p. 395-398 https://doi.org/10.1038/nature12509	journal	September 2013
Compositional engineering of perovskite materials for high-performance solar cells Jeon, Nam Joong; Noh, Jun Hong; Yang, Woon Seok Nature, Vol. 517, Issue 7535 https://doi.org/10.1038/nature14133	journal	January 2015
The light and shade of perovskite solar cells Grätzel, Michael Nature Materials, Vol. 13, Issue 9 https://doi.org/10.1038/nmat4065	journal	August 2014
Polymer solar cells with enhanced fill factors Guo, Xugang; Zhou, Nanjia; Lou, Sylvia J. Nature Photonics, Vol. 7, Issue 10 https://doi.org/10.1038/nphoton.2013.207	journal	August 2013
Efficient inorganic–organic hybrid heterojunction solar cells containing perovskite compound and polymeric hole conductors Heo, Jin Hyuck; Im, Sang Hyuk; Noh, Jun Hong Nature Photonics, Vol. 7, Issue 6, p. 486-491 https://doi.org/10.1038/nphoton.2013.80	journal	May 2013
A decade of perovskite photovoltaics Zhang, Changjun Nature Energy, Vol. 4, Issue 1, p. 1-1 https://doi.org/10.1038/s41560-018-0323-9	journal	January 2019
Lead Iodide Perovskite Sensitized All-Solid-State Submicron Thin Film Mesoscopic Solar Cell with Efficiency Exceeding 9% Kim, Hui-Seon; Lee, Chang-Ryul; Im, Jeong-Hyeok Scientific Reports, Vol. 2, Issue 1 https://doi.org/10.1038/srep00591	journal	August 2012
Review of recent progress in chemical stability of perovskite solar cells Niu, Guangda; Guo, Xudong; Wang, Liduo Journal of Materials Chemistry A, Vol. 3, Issue 17, p. 8970-8980 https://doi.org/10.1039/C4TA04994B	journal	December 2014
Halide perovskite materials for solar cells: a theoretical review Yin, Wan-Jian; Yang, Ji-Hui; Kang, Joongoo Journal of Materials Chemistry A, Vol. 3, Issue 17 https://doi.org/10.1039/C4TA05033A	journal	January 2015
The first thieno[3,4- b ]pyrazine based small molecular acceptor with a linear A ₂ –A ₁ –D–A ₁ –A ₂ skeleton for fullerene-free organic solar cells with a high V _oc of 1.05 V Li, Jianfeng; Yang, Jing; Hu, Junyi Chemical Communications, Vol. 54, Issue 76 https://doi.org/10.1039/C8CC06198J	journal	January 2018
Perovskite precursor solution chemistry: from fundamentals to photovoltaic applications Jung, Minsu; Ji, Sang-Geun; Kim, Gwisu Chemical Society Reviews, Vol. 48, Issue 7 https://doi.org/10.1039/C8CS00656C	journal	January 2019
Efficiency vs. stability: dopant-free hole transporting materials towards stabilized perovskite solar cells Rakstys, Kasparas; Igci, Cansu; Nazeeruddin, Mohammad Khaja Chemical Science, Vol. 10, Issue 28 https://doi.org/10.1039/C9SC01184F	journal	January 2019
Poly(2,3-dihexylthieno[3,4-b]pyrazine). A new processable low band-gap polyheterocycle Pomerantz, Martin; Chaloner-Gill, Benjamin; Harding, Larry O. Journal of the Chemical Society, Chemical Communications, Issue 22 https://doi.org/10.1039/c39920001672	journal	January 1992
Efficient Hybrid Solar Cells Based on Meso-Superstructured Organometal Halide Perovskites Lee, M. M.; Teuscher, J.; Miyasaka, T. Science, Vol. 338, Issue 6107, p. 643-647 https://doi.org/10.1126/science.1228604	journal	October 2012
High-performance photovoltaic perovskite layers fabricated through intramolecular exchange Yang, W. S.; Noh, J. H.; Jeon, N. J. Science, Vol. 348, Issue 6240 https://doi.org/10.1126/science.aaa9272	journal	May 2015

Similar Records

De Novo Design of Spiro-Type Hole-Transporting Material: Anisotropic Regulation Toward Efficient and Stable Perovskite Solar Cells

Journal Article · Sat Mar 23 00:00:00 EDT 2024 · Research · OSTI ID:2426884

Thermally Stable Perovskite Solar Cells by Systematic Molecular Design of the Hole-Transport Layer

Journal Article · Mon Jan 07 23:00:00 EST 2019 · ACS Energy Letters · OSTI ID:1491373

Related Subjects

14 SOLAR ENERGY
band-gap
energy levels
high-efficiency
materials
mobility
perovskites
polymerization
power conversion efficiency
spectra

2,3-Diphenylthieno[3,4-b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells

Citation Formats

References (62)

Similar Records

Related Subjects