DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Benzodithiophene Hole‐Transporting Materials for Efficient Tin‐Based Perovskite Solar Cells

Abstract

Abstract Developing efficient interfacial hole transporting materials (HTMs) is crucial for achieving high‐performance Pb‐free Sn‐based halide perovskite solar cells (PSCs). Here, a new series of benzodithiophene (BDT)‐based organic small molecules containing tetra‐ and di‐triphenyl amine donors prepared via a straightforward and scalable synthetic route is reported. The thermal, optical, and electrochemical properties of two BDT‐based molecules are shown to be structurally and energetically suitable to serve as HTMs for Sn‐based PSCs. It is reported here that ethylenediammonium/formamidinium tin iodide solar cells using BDT‐based HTMs deliver a champion power conversion efficiency up to 7.59%, outperforming analogous reference solar cells using traditional and expensive HTMs. Thus, these BDT‐based molecules are promising candidates as HTMs for the fabrication of high‐performance Sn‐based PSCs.

Authors:
 [1];  [2];  [1];  [1];  [1];  [2];  [1];  [2];  [1]; ORCiD logo [2]
  1. Department of Chemistry and Research Center of New Generation Light Driven Photovoltaic Modules National Central University Taoyuan 32001 Taiwan
  2. Department of Chemistry and the Center for Light Energy Activated Redox Processes (LEAP) Northwestern University Evanston IL 60208 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1560270
Grant/Contract Number:  
DE‐SC0001059
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Advanced Functional Materials
Additional Journal Information:
Journal Name: Advanced Functional Materials Journal Volume: 29 Journal Issue: 45; Journal ID: ISSN 1616-301X
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Vegiraju, Sureshraju, Ke, Weijun, Priyanka, Pragya, Ni, Jen‐Shyang, Wu, Yi‐Ching, Spanopoulos, Ioannis, Yau, Shueh Lin, Marks, Tobin J., Chen, Ming‐Chou, and Kanatzidis, Mercouri G. Benzodithiophene Hole‐Transporting Materials for Efficient Tin‐Based Perovskite Solar Cells. Germany: N. p., 2019. Web. doi:10.1002/adfm.201905393.
Vegiraju, Sureshraju, Ke, Weijun, Priyanka, Pragya, Ni, Jen‐Shyang, Wu, Yi‐Ching, Spanopoulos, Ioannis, Yau, Shueh Lin, Marks, Tobin J., Chen, Ming‐Chou, & Kanatzidis, Mercouri G. Benzodithiophene Hole‐Transporting Materials for Efficient Tin‐Based Perovskite Solar Cells. Germany. https://doi.org/10.1002/adfm.201905393
Vegiraju, Sureshraju, Ke, Weijun, Priyanka, Pragya, Ni, Jen‐Shyang, Wu, Yi‐Ching, Spanopoulos, Ioannis, Yau, Shueh Lin, Marks, Tobin J., Chen, Ming‐Chou, and Kanatzidis, Mercouri G. Wed . "Benzodithiophene Hole‐Transporting Materials for Efficient Tin‐Based Perovskite Solar Cells". Germany. https://doi.org/10.1002/adfm.201905393.
@article{osti_1560270,
title = {Benzodithiophene Hole‐Transporting Materials for Efficient Tin‐Based Perovskite Solar Cells},
author = {Vegiraju, Sureshraju and Ke, Weijun and Priyanka, Pragya and Ni, Jen‐Shyang and Wu, Yi‐Ching and Spanopoulos, Ioannis and Yau, Shueh Lin and Marks, Tobin J. and Chen, Ming‐Chou and Kanatzidis, Mercouri G.},
abstractNote = {Abstract Developing efficient interfacial hole transporting materials (HTMs) is crucial for achieving high‐performance Pb‐free Sn‐based halide perovskite solar cells (PSCs). Here, a new series of benzodithiophene (BDT)‐based organic small molecules containing tetra‐ and di‐triphenyl amine donors prepared via a straightforward and scalable synthetic route is reported. The thermal, optical, and electrochemical properties of two BDT‐based molecules are shown to be structurally and energetically suitable to serve as HTMs for Sn‐based PSCs. It is reported here that ethylenediammonium/formamidinium tin iodide solar cells using BDT‐based HTMs deliver a champion power conversion efficiency up to 7.59%, outperforming analogous reference solar cells using traditional and expensive HTMs. Thus, these BDT‐based molecules are promising candidates as HTMs for the fabrication of high‐performance Sn‐based PSCs.},
doi = {10.1002/adfm.201905393},
journal = {Advanced Functional Materials},
number = 45,
volume = 29,
place = {Germany},
year = {Wed Sep 04 00:00:00 EDT 2019},
month = {Wed Sep 04 00:00:00 EDT 2019}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1002/adfm.201905393

Citation Metrics:
Cited by: 35 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Design of benzodithiophene-diketopyrrolopyrrole based donor–acceptor copolymers for efficient organic field effect transistors and polymer solar cells
journal, January 2012

  • Yuan, Jianyu; Huang, Xiaodong; Zhang, Fengjiao
  • Journal of Materials Chemistry, Vol. 22, Issue 42
  • DOI: 10.1039/c2jm34004f

The Renaissance of Halide Perovskites and Their Evolution as Emerging Semiconductors
journal, September 2015


Lead-Free Inverted Planar Formamidinium Tin Triiodide Perovskite Solar Cells Achieving Power Conversion Efficiencies up to 6.22%
journal, August 2016


Enhanced photovoltaic performance and stability with a new type of hollow 3D perovskite {en}FASnI 3
journal, August 2017

  • Ke, Weijun; Stoumpos, Constantinos C.; Zhu, Menghua
  • Science Advances, Vol. 3, Issue 8
  • DOI: 10.1126/sciadv.1701293

All-solid-state dye-sensitized solar cells with high efficiency
journal, May 2012

  • Chung, In; Lee, Byunghong; He, Jiaqing
  • Nature, Vol. 485, Issue 7399, p. 486-489
  • DOI: 10.1038/nature11067

Solution-Processed and High-Performance Organic Solar Cells Using Small Molecules with a Benzodithiophene Unit
journal, May 2013

  • Zhou, Jiaoyan; Zuo, Yi; Wan, Xiangjian
  • Journal of the American Chemical Society, Vol. 135, Issue 23
  • DOI: 10.1021/ja403318y

Unusual defect physics in CH 3 NH 3 PbI 3 perovskite solar cell absorber
journal, February 2014

  • Yin, Wan-Jian; Shi, Tingting; Yan, Yanfa
  • Applied Physics Letters, Vol. 104, Issue 6
  • DOI: 10.1063/1.4864778

Amorphous oxide alloys as interfacial layers with broadly tunable electronic structures for organic photovoltaic cells
journal, June 2015

  • Zhou, Nanjia; Kim, Myung-Gil; Loser, Stephen
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 26
  • DOI: 10.1073/pnas.1508578112

Two-Dimensional Hybrid Halide Perovskites: Principles and Promises
journal, November 2018

  • Mao, Lingling; Stoumpos, Constantinos C.; Kanatzidis, Mercouri G.
  • Journal of the American Chemical Society, Vol. 141, Issue 3
  • DOI: 10.1021/jacs.8b10851

The rapid evolution of highly efficient perovskite solar cells
journal, January 2017

  • Correa-Baena, Juan-Pablo; Abate, Antonio; Saliba, Michael
  • Energy & Environmental Science, Vol. 10, Issue 3
  • DOI: 10.1039/C6EE03397K

Effect of multi-armed triphenylamine-based hole transporting materials for high performance perovskite solar cells
journal, January 2016

  • Park, Sungmin; Heo, Jin Hyuck; Yun, Jae Hoon
  • Chemical Science, Vol. 7, Issue 8
  • DOI: 10.1039/C6SC00876C

High-performance photovoltaic perovskite layers fabricated through intramolecular exchange
journal, May 2015


“Unleaded” Perovskites: Status Quo and Future Prospects of Tin‐Based Perovskite Solar Cells
journal, September 2018

  • Ke, Weijun; Stoumpos, Constantinos C.; Kanatzidis, Mercouri G.
  • Advanced Materials, Vol. 31, Issue 47
  • DOI: 10.1002/adma.201803230

Hole transporting materials for perovskite solar cells: a chemical approach
journal, January 2018

  • Urieta-Mora, Javier; García-Benito, Inés; Molina-Ontoria, Agustín
  • Chemical Society Reviews, Vol. 47, Issue 23
  • DOI: 10.1039/C8CS00262B

Prospects for low-toxicity lead-free perovskite solar cells
journal, February 2019


Dopant-Free Hole Transporting Polymers for High Efficiency, Environmentally Stable Perovskite Solar Cells
journal, June 2016

  • Liao, Hsueh-Chung; Tam, Teck Lip Dexter; Guo, Peijun
  • Advanced Energy Materials, Vol. 6, Issue 16
  • DOI: 10.1002/aenm.201600502

Halide Perovskites: Poor Man's High-Performance Semiconductors
journal, May 2016

  • Stoumpos, Constantinos C.; Kanatzidis, Mercouri G.
  • Advanced Materials, Vol. 28, Issue 28
  • DOI: 10.1002/adma.201600265

Efficient Hybrid Solar Cells Based on Meso-Superstructured Organometal Halide Perovskites
journal, October 2012


Triazatruxene-Based Hole Transporting Materials for Highly Efficient Perovskite Solar Cells
journal, December 2015

  • Rakstys, Kasparas; Abate, Antonio; Dar, M. Ibrahim
  • Journal of the American Chemical Society, Vol. 137, Issue 51
  • DOI: 10.1021/jacs.5b11076

Efficient Lead-Free Solar Cells Based on Hollow {en}MASnI 3 Perovskites
journal, October 2017

  • Ke, Weijun; Stoumpos, Constantinos C.; Spanopoulos, Ioannis
  • Journal of the American Chemical Society, Vol. 139, Issue 41
  • DOI: 10.1021/jacs.7b09018

Antioxidant Grain Passivation for Air-Stable Tin-Based Perovskite Solar Cells
journal, December 2018

  • Tai, Qidong; Guo, Xuyun; Tang, Guanqi
  • Angewandte Chemie International Edition, Vol. 58, Issue 3
  • DOI: 10.1002/anie.201811539

o -Methoxy Substituents in Spiro-OMeTAD for Efficient Inorganic–Organic Hybrid Perovskite Solar Cells
journal, May 2014

  • Jeon, Nam Joong; Lee, Hag Geun; Kim, Young Chan
  • Journal of the American Chemical Society, Vol. 136, Issue 22
  • DOI: 10.1021/ja502824c

High-Performance Solar Cells using a Solution-Processed Small Molecule Containing Benzodithiophene Unit
journal, October 2011


Anomalous Hysteresis in Perovskite Solar Cells
journal, April 2014

  • Snaith, Henry J.; Abate, Antonio; Ball, James M.
  • The Journal of Physical Chemistry Letters, Vol. 5, Issue 9
  • DOI: 10.1021/jz500113x

Lead-free solid-state organic–inorganic halide perovskite solar cells
journal, May 2014

  • Hao, Feng; Stoumpos, Constantinos C.; Cao, Duyen Hanh
  • Nature Photonics, Vol. 8, Issue 6
  • DOI: 10.1038/nphoton.2014.82

Compositional engineering of perovskite materials for high-performance solar cells
journal, January 2015

  • Jeon, Nam Joong; Noh, Jun Hong; Yang, Woon Seok
  • Nature, Vol. 517, Issue 7535
  • DOI: 10.1038/nature14133

Solution-Processed Organic Solar Cells Based on Dialkylthiol-Substituted Benzodithiophene Unit with Efficiency near 10%
journal, October 2014

  • Kan, Bin; Zhang, Qian; Li, Miaomiao
  • Journal of the American Chemical Society, Vol. 136, Issue 44
  • DOI: 10.1021/ja509703k

Benzotrithiophene-Based Hole-Transporting Materials for 18.2 % Perovskite Solar Cells
journal, April 2016

  • Molina-Ontoria, Agustín; Zimmermann, Iwan; Garcia-Benito, Inés
  • Angewandte Chemie International Edition, Vol. 55, Issue 21
  • DOI: 10.1002/anie.201511877

Semiconducting Tin and Lead Iodide Perovskites with Organic Cations: Phase Transitions, High Mobilities, and Near-Infrared Photoluminescent Properties
journal, July 2013

  • Stoumpos, Constantinos C.; Malliakas, Christos D.; Kanatzidis, Mercouri G.
  • Inorganic Chemistry, Vol. 52, Issue 15, p. 9019-9038
  • DOI: 10.1021/ic401215x

Progress on lead-free metal halide perovskites for photovoltaic applications: a review
journal, March 2017

  • Hoefler, Sebastian F.; Trimmel, Gregor; Rath, Thomas
  • Monatshefte für Chemie - Chemical Monthly, Vol. 148, Issue 5
  • DOI: 10.1007/s00706-017-1933-9

Small Molecules Based on Benzo[1,2-b:4,5-b′]dithiophene Unit for High-Performance Solution-Processed Organic Solar Cells
journal, September 2012

  • Zhou, Jiaoyan; Wan, Xiangjian; Liu, Yongsheng
  • Journal of the American Chemical Society, Vol. 134, Issue 39
  • DOI: 10.1021/ja306865z

Efficient Inorganic–Organic Hybrid Perovskite Solar Cells Based on Pyrene Arylamine Derivatives as Hole-Transporting Materials
journal, December 2013

  • Jeon, Nam Joong; Lee, Jaemin; Noh, Jun Hong
  • Journal of the American Chemical Society, Vol. 135, Issue 51, p. 19087-19090
  • DOI: 10.1021/ja410659k

Diammonium Cations in the FASnI 3 Perovskite Structure Lead to Lower Dark Currents and More Efficient Solar Cells
journal, May 2018


Star-shaped hole transport materials with indeno[1,2-b] thiophene or fluorene on a triazine core for efficient perovskite solar cells
journal, January 2016

  • Lim, Kimin; Kang, Moon-Sung; Myung, Yoon
  • Journal of Materials Chemistry A, Vol. 4, Issue 4
  • DOI: 10.1039/C5TA07369C

Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)
journal, June 2015

  • Youn, Jangdae; Vegiraju, Sureshraju; Emery, Jonathan D.
  • Advanced Electronic Materials, Vol. 1, Issue 8
  • DOI: 10.1002/aelm.201500098

Lead Iodide Perovskite Sensitized All-Solid-State Submicron Thin Film Mesoscopic Solar Cell with Efficiency Exceeding 9%
journal, August 2012

  • Kim, Hui-Seon; Lee, Chang-Ryul; Im, Jeong-Hyeok
  • Scientific Reports, Vol. 2, Issue 1
  • DOI: 10.1038/srep00591

Dopant-Free Tetrakis-Triphenylamine Hole Transporting Material for Efficient Tin-Based Perovskite Solar Cells
journal, December 2017

  • Ke, Weijun; Priyanka, Pragya; Vegiraju, Sureshraju
  • Journal of the American Chemical Society, Vol. 140, Issue 1
  • DOI: 10.1021/jacs.7b10898

TiO 2 –ZnS Cascade Electron Transport Layer for Efficient Formamidinium Tin Iodide Perovskite Solar Cells
journal, November 2016

  • Ke, Weijun; Stoumpos, Constantinos C.; Logsdon, Jenna Leigh
  • Journal of the American Chemical Society, Vol. 138, Issue 45
  • DOI: 10.1021/jacs.6b08790

Perovskites: The Emergence of a New Era for Low-Cost, High-Efficiency Solar Cells
journal, October 2013

  • Snaith, Henry J.
  • The Journal of Physical Chemistry Letters, Vol. 4, Issue 21, p. 3623-3630
  • DOI: 10.1021/jz4020162

Effects of organic cations on the defect physics of tin halide perovskites
journal, January 2017

  • Shi, Tingting; Zhang, Hai-Shan; Meng, Weiwei
  • Journal of Materials Chemistry A, Vol. 5, Issue 29
  • DOI: 10.1039/C7TA02662E

Low-Temperature Solution-Processed Tin Oxide as an Alternative Electron Transporting Layer for Efficient Perovskite Solar Cells
journal, May 2015

  • Ke, Weijun; Fang, Guojia; Liu, Qin
  • Journal of the American Chemical Society, Vol. 137, Issue 21
  • DOI: 10.1021/jacs.5b01994

Lead-free organic–inorganic tin halide perovskites for photovoltaic applications
journal, January 2014

  • Noel, Nakita K.; Stranks, Samuel D.; Abate, Antonio
  • Energy Environ. Sci., Vol. 7, Issue 9
  • DOI: 10.1039/C4EE01076K

p-Type semiconducting nickel oxide as an efficiency-enhancing anode interfacial layer in polymer bulk-heterojunction solar cells
journal, February 2008

  • Irwin, M. D.; Buchholz, D. B.; Hains, A. W.
  • Proceedings of the National Academy of Sciences, Vol. 105, Issue 8, p. 2783-2787
  • DOI: 10.1073/pnas.0711990105