Spiro‐Phenylpyrazole‐9,9′‐Thioxanthene Analogues as Hole‐Transporting Materials for Efficient Planar Perovskite Solar Cells

Wang, Yang; Zhu, Zonglong; Chueh, Chu‐Chen; Jen, Alex K. ‐Y.; Chi, Yun

doi:10.1002/aenm.201700823

Spiro‐Phenylpyrazole‐9,9′‐Thioxanthene Analogues as Hole‐Transporting Materials for Efficient Planar Perovskite Solar Cells

Journal Article · Fri Jun 09 00:00:00 EDT 2017 · Advanced Energy Materials

DOI:https://doi.org/10.1002/aenm.201700823· OSTI ID:1399053

Wang, Yang ^[1]; Zhu, Zonglong ^[2]; Chueh, Chu‐Chen ^[2]; Jen, Alex K. ‐Y. ^[3]; ^[1]

Department of Chemistry and Low Carbon Energy Research Center National Tsing Hua University Hsinchu 30013 Taiwan
Department of Materials Science and Engineering and Department of Chemistry University of Washington Seattle WA 98195‐2120 USA
Department of Materials Science and Engineering and Department of Chemistry University of Washington Seattle WA 98195‐2120 USA, Department of Biology and Chemistry City University of Hong Kong Kowloon 999077 Hong Kong

Abstract

Perovskite solar cells have emerged as a promising technique for low‐cost, light weight, and highly efficient photovoltaics. However, they still largely rely on 2,2′,7,7′‐tetrakis( N , N ‐di‐ p ‐methoxyphenylamine)‐9,9′‐spirobifluorene (Spiro‐OMeTAD) to serve as hole‐transporting materials (HTMs). Here, a series of HTMs with small molecular weight is designed, which are constructed on a spiro core involving phenylpyrazole and a second heteroaromatics, i.e., xanthene (O atom), thioxanthene (S atom), and acridine (N atom). Through varying from phenylpyrazole substituted xanthene ( PPyra‐XA ), thioxanthene ( PPyra‐TXA ), to acridine ( PPyra‐ACD ), their optical and electrochemical properties, hole mobilities, and the photovoltaic performance are optimized. As a consequence, PPyra‐TXA based device exhibits the highest power conversion efficiency (PCE) of 18.06%, outperforming that of Spiro‐OMeTAD (16.15%), which could be attributed to the enhancement of hole mobility exerted by the thioxanthene. In addition, the dopant‐free device shows PCE of 11.7%. These results open a new direction for designing spiro‐HTMs by simple modification of chemical structures.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: EE0006710

OSTI ID:: 1399053

Alternate ID(s):: OSTI ID: 1537401

Journal Information:: Advanced Energy Materials, Journal Name: Advanced Energy Materials Journal Issue: 19 Vol. 7; ISSN 1614-6832

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (45)

Dopant-Free Spiro-Triphenylamine/Fluorene as Hole-Transporting Material for Perovskite Solar Cells with Enhanced Efficiency and Stability Wang, Ya-Kun; Yuan, Zhong-Cheng; Shi, Guo-Zheng Advanced Functional Materials, Vol. 26, Issue 9 https://doi.org/10.1002/adfm.201504245	journal	January 2016
High Charge Carrier Mobilities and Lifetimes in Organolead Trihalide Perovskites Wehrenfennig, Christian; Eperon, Giles E.; Johnston, Michael B. Advanced Materials, Vol. 26, Issue 10 https://doi.org/10.1002/adma.201305172	journal	December 2013
Perovskite Solar Cells Employing Dopant-Free Organic Hole Transport Materials with Tunable Energy Levels Liu, Yongsheng; Hong, Ziruo; Chen, Qi Advanced Materials, Vol. 28, Issue 3 https://doi.org/10.1002/adma.201504293	journal	November 2015
Organic Semiconductors based on Dyes and Color Pigments Gsänger, Marcel; Bialas, David; Huang, Lizhen Advanced Materials, Vol. 28, Issue 19 https://doi.org/10.1002/adma.201505440	journal	March 2016
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
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
Highly Efficient Perovskite Solar Cells Employing an Easily Attainable Bifluorenylidene-Based Hole-Transporting Material Rakstys, Kasparas; Saliba, Michael; Gao, Peng Angewandte Chemie International Edition, Vol. 55, Issue 26 https://doi.org/10.1002/anie.201602545	journal	May 2016
Stability of Perovskite Solar Cells: A Prospective on the Substitution of the A Cation and X Anion Wang, Ze; Shi, Zejiao; Li, Taotao Angewandte Chemie International Edition, Vol. 56, Issue 5 https://doi.org/10.1002/anie.201603694	journal	November 2016
m -Methoxy Substituents in a Tetraphenylethylene-Based Hole-Transport Material for Efficient Perovskite Solar Cells Wu, Fei; Liu, Jianlin; Wang, Gang Chemistry - A European Journal, Vol. 22, Issue 46 https://doi.org/10.1002/chem.201603672	journal	October 2016
Perovskite Solar Cells: Influence of Hole Transporting Materials on Power Conversion Efficiency Ameen, Sadia; Rub, Malik Abdul; Kosa, Samia A. ChemSusChem, Vol. 9, Issue 1 https://doi.org/10.1002/cssc.201501228	journal	December 2015
Hybrid Perovskites for Photovoltaics: Charge-Carrier Recombination, Diffusion, and Radiative Efficiencies Johnston, Michael B.; Herz, Laura M. Accounts of Chemical Research, Vol. 49, Issue 1 https://doi.org/10.1021/acs.accounts.5b00411	journal	December 2015
What Is Moving in Hybrid Halide Perovskite Solar Cells? Frost, Jarvist M.; Walsh, Aron Accounts of Chemical Research, Vol. 49, Issue 3 https://doi.org/10.1021/acs.accounts.5b00431	journal	February 2016
Recent Advances in Bulk Heterojunction Polymer Solar Cells Lu, Luyao; Zheng, Tianyue; Wu, Qinghe Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00098	journal	August 2015
Efficient Inorganic–Organic Hybrid Perovskite Solar Cells Based on Pyrene Arylamine Derivatives as Hole-Transporting Materials Jeon, Nam Joong; Lee, Jaemin; Noh, Jun Hong Journal of the American Chemical Society, Vol. 135, Issue 51, p. 19087-19090 https://doi.org/10.1021/ja410659k	journal	December 2013
o -Methoxy Substituents in Spiro-OMeTAD for Efficient Inorganic–Organic Hybrid Perovskite Solar Cells Jeon, Nam Joong; Lee, Hag Geun; Kim, Young Chan Journal of the American Chemical Society, Vol. 136, Issue 22 https://doi.org/10.1021/ja502824c	journal	May 2014
Perovskite Solar Cells with 12.8% Efficiency by Using Conjugated Quinolizino Acridine Based Hole Transporting Material Qin, Peng; Paek, Sanghyun; Dar, M. Ibrahim Journal of the American Chemical Society, Vol. 136, Issue 24 https://doi.org/10.1021/ja503272q	journal	June 2014
Organometal Halide Perovskites as Visible-Light Sensitizers for Photovoltaic Cells Kojima, Akihiro; Teshima, Kenjiro; Shirai, Yasuo Journal of the American Chemical Society, Vol. 131, Issue 17, p. 6050-6051 https://doi.org/10.1021/ja809598r	journal	May 2009
Well-Defined Thiolated Nanographene as Hole-Transporting Material for Efficient and Stable Perovskite Solar Cells Cao, Jing; Liu, Yu-Min; Jing, Xiaojing Journal of the American Chemical Society, Vol. 137, Issue 34 https://doi.org/10.1021/jacs.5b06493	journal	August 2015
Hole-Transporting Materials with a Two-Dimensionally Expanded π-System around an Azulene Core for Efficient Perovskite Solar Cells Nishimura, Hidetaka; Ishida, Naoki; Shimazaki, Ai Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11008	journal	December 2015
Rational Design of Dipolar Chromophore as an Efficient Dopant-Free Hole-Transporting Material for Perovskite Solar Cells Li, Zhong’an; Zhu, Zonglong; Chueh, Chu-Chen Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b06291	journal	August 2016
A molecularly engineered hole-transporting material for efficient perovskite solar cells Saliba, Michael; Orlandi, Simonetta; Matsui, Taisuke Nature Energy, Vol. 1, Issue 2 https://doi.org/10.1038/nenergy.2015.17	journal	January 2016
Polymer-templated nucleation and crystal growth of perovskite films for solar cells with efficiency greater than 21% Bi, Dongqin; Yi, Chenyi; Luo, Jingshan Nature Energy, Vol. 1, Issue 10 https://doi.org/10.1038/nenergy.2016.142	journal	September 2016
Enhanced electron extraction using SnO2 for high-efficiency planar-structure HC(NH2)2PbI3-based perovskite solar cells Jiang, Qi; Zhang, Liuqi; Wang, Haolin Nature Energy, Vol. 2, Issue 1 https://doi.org/10.1038/nenergy.2016.177	journal	November 2016
Novel hole transporting materials based on triptycene core for high efficiency mesoscopic perovskite solar cells Krishna, Anurag; Sabba, Dharani; Li, Hairong Chem. Sci., Vol. 5, Issue 7 https://doi.org/10.1039/C4SC00814F	journal	January 2014
Novel spiro-based hole transporting materials for efficient perovskite solar cells Li, Ming-Hsien; Hsu, Che-Wei; Shen, Po-Shen Chemical Communications, Vol. 51, Issue 85 https://doi.org/10.1039/C5CC04405G	journal	January 2015
Cesium-containing triple cation perovskite solar cells: improved stability, reproducibility and high efficiency Saliba, Michael; Matsui, Taisuke; Seo, Ji-Youn Energy & Environmental Science, Vol. 9, Issue 6 https://doi.org/10.1039/C5EE03874J	journal	January 2016
A dopant-free spirobi[cyclopenta[2,1-b:3,4-b′]dithiophene] based hole-transport material for efficient perovskite solar cells Franckevičius, Marius; Mishra, Amaresh; Kreuzer, Franziska Materials Horizons, Vol. 2, Issue 6 https://doi.org/10.1039/C5MH00154D	journal	January 2015
High conductivity Ag-based metal organic complexes as dopant-free hole-transport materials for perovskite solar cells with high fill factors Hua, Yong; Xu, Bo; Liu, Peng Chemical Science, Vol. 7, Issue 4 https://doi.org/10.1039/C5SC03569D	journal	January 2016
A dopant-free organic hole transport material for efficient planar heterojunction perovskite solar cells Liu, Yongsheng; Chen, Qi; Duan, Hsin-Sheng Journal of Materials Chemistry A, Vol. 3, Issue 22 https://doi.org/10.1039/C5TA02502H	journal	January 2015
A low-cost spiro[fluorene-9,9′-xanthene]-based hole transport material for highly efficient solid-state dye-sensitized solar cells and perovskite solar cells Xu, Bo; Bi, Dongqin; Hua, Yong Energy & Environmental Science, Vol. 9, Issue 3 https://doi.org/10.1039/C6EE00056H	journal	January 2016
Highly efficient and stable planar perovskite solar cells by solution-processed tin oxide Anaraki, Elham Halvani; Kermanpur, Ahmad; Steier, Ludmilla Energy & Environmental Science, Vol. 9, Issue 10 https://doi.org/10.1039/C6EE02390H	journal	January 2016
Is Cu a stable electrode material in hybrid perovskite solar cells for a 30-year lifetime? Zhao, Jingjing; Zheng, Xiaopeng; Deng, Yehao Energy & Environmental Science, Vol. 9, Issue 12 https://doi.org/10.1039/C6EE02980A	journal	January 2016
Highly efficient perovskite solar cells with a compositionally engineered perovskite/hole transporting material interface Cho, Kyung Taek; Paek, Sanghyun; Grancini, Giulia Energy & Environmental Science, Vol. 10, Issue 2 https://doi.org/10.1039/C6EE03182J	journal	January 2017
The rapid evolution of highly efficient perovskite solar cells Correa-Baena, Juan-Pablo; Abate, Antonio; Saliba, Michael Energy & Environmental Science, Vol. 10, Issue 3 https://doi.org/10.1039/C6EE03397K	journal	January 2017
Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells Yun, Jae Hoon; Park, Sungmin; Heo, Jin Hyuck Chemical Science, Vol. 7, Issue 11 https://doi.org/10.1039/C6SC02448C	journal	January 2016
SFX as a low-cost ‘Spiro’ hole-transport material for efficient perovskite solar cells Maciejczyk, Michal; Ivaturi, Aruna; Robertson, Neil Journal of Materials Chemistry A, Vol. 4, Issue 13 https://doi.org/10.1039/C6TA00110F	journal	January 2016
A review of organic small molecule-based hole-transporting materials for meso-structured organic–inorganic perovskite solar cells Teh, Chin Hoong; Daik, Rusli; Lim, Eng Liang Journal of Materials Chemistry A, Vol. 4, Issue 41 https://doi.org/10.1039/C6TA06987H	journal	January 2016
Isomerism effect on the photovoltaic properties of benzotrithiophene-based hole-transporting materials García-Benito, Inés; Zimmermann, Iwan; Urieta-Mora, Javier Journal of Materials Chemistry A, Vol. 5, Issue 18 https://doi.org/10.1039/C7TA00997F	journal	January 2017
Long-Range Balanced Electron- and Hole-Transport Lengths in Organic-Inorganic CH₃NH₃PbI₃ Xing, G.; Mathews, N.; Sun, S. Science, Vol. 342, Issue 6156, p. 344-347 https://doi.org/10.1126/science.1243167	journal	October 2013
Electron-Hole Diffusion Lengths Exceeding 1 Micrometer in an Organometal Trihalide Perovskite Absorber Stranks, S. D.; Eperon, G. E.; Grancini, G. Science, Vol. 342, Issue 6156, p. 341-344 https://doi.org/10.1126/science.1243982	journal	October 2013
Impact of microstructure on local carrier lifetime in perovskite solar cells de Quilettes, D. W.; Vorpahl, S. M.; Stranks, S. D. Science, Vol. 348, Issue 6235 https://doi.org/10.1126/science.aaa5333	journal	April 2015
Electron-hole diffusion lengths > 175 μm in solution-grown CH ₃ NH ₃ PbI ₃ single crystals Dong, Qingfeng; Fang, Yanjun; Shao, Yuchuan Science, Vol. 347, Issue 6225 https://doi.org/10.1126/science.aaa5760	journal	January 2015
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
Incorporation of rubidium cations into perovskite solar cells improves photovoltaic performance Saliba, M.; Matsui, T.; Domanski, K. Science, Vol. 354, Issue 6309 https://doi.org/10.1126/science.aah5557	journal	September 2016

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