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Title: Rational design of dipolar chromophore as an efficient dopant-free hole-transporting material for perovskite solar cells

Abstract

In this paper, an electron donor-acceptor (D-A) substituted dipolar chromophore (BTPA-TCNE) is developed to serve as an efficient dopant-free hole-transporting material (HTM) for perovskite solar cells (PVSCs). BTPA-TCNE is synthesized via a simple reaction between a triphenylamine-based Michler’s base and tetracyanoethylene. This chromophore possesses a zwitterionic resonance structure in the ground state, as evidenced by X-ray crystallography and transient absorption spectroscopies. Moreover, BTPA-TCNE shows an antiparallel molecular packing (i.e., centrosymmetric dimers) in its crystalline state, which cancels out its overall molecular dipole moment to facilitate charge transport. Finally, BTPA-TCNE can be employed as an effective dopant-free HTM to realize an efficient (PCE ≈ 17.0%) PVSC in the conventional n-i-p configuration, outperforming the control device with doped spiro-OMeTAD HTM.

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [1]
  1. Univ. of Washington, Seattle, WA (United States)
Publication Date:
Research Org.:
Univ. of Washington, Seattle, WA (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
Contributing Org.:
This work was supported by the Office of Naval Research (N00014-14-1-0246), the National Science Foundation (DMR- 1608279), the Asian Office of Aerospace R&D (FA2386-15-1- 4106), and the Department of Energy SunShot (DEEE0006710). Prof. Jen thanks the Boeing-Johnson Foundation for financial support. The authors thank Prof. Werner Kaminsky (UW) for X-ray structure refinement, Prof. Cody W. Schlenker and Dana B. Sulas (UW) for providing access to the transient-absorption spectra, and Ellen Cambron Hayes (UW) for electron spin resonance measurements.
OSTI Identifier:
1343607
Report Number(s):
DOE-UW-Jen-32
Journal ID: ISSN 0002-7863
Grant/Contract Number:  
EE0006710
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 138; Journal Issue: 36; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY; 36 MATERIALS SCIENCE

Citation Formats

Li, Zhong’an, Zhu, Zonglong, Chueh, Chu -Chen, Jo, Sae Byeok, Luo, Jingdong, Jang, Sei -Hum, and Jen, Alex K. -Y. Rational design of dipolar chromophore as an efficient dopant-free hole-transporting material for perovskite solar cells. United States: N. p., 2016. Web. doi:10.1021/jacs.6b06291.
Li, Zhong’an, Zhu, Zonglong, Chueh, Chu -Chen, Jo, Sae Byeok, Luo, Jingdong, Jang, Sei -Hum, & Jen, Alex K. -Y. Rational design of dipolar chromophore as an efficient dopant-free hole-transporting material for perovskite solar cells. United States. https://doi.org/10.1021/jacs.6b06291
Li, Zhong’an, Zhu, Zonglong, Chueh, Chu -Chen, Jo, Sae Byeok, Luo, Jingdong, Jang, Sei -Hum, and Jen, Alex K. -Y. 2016. "Rational design of dipolar chromophore as an efficient dopant-free hole-transporting material for perovskite solar cells". United States. https://doi.org/10.1021/jacs.6b06291. https://www.osti.gov/servlets/purl/1343607.
@article{osti_1343607,
title = {Rational design of dipolar chromophore as an efficient dopant-free hole-transporting material for perovskite solar cells},
author = {Li, Zhong’an and Zhu, Zonglong and Chueh, Chu -Chen and Jo, Sae Byeok and Luo, Jingdong and Jang, Sei -Hum and Jen, Alex K. -Y.},
abstractNote = {In this paper, an electron donor-acceptor (D-A) substituted dipolar chromophore (BTPA-TCNE) is developed to serve as an efficient dopant-free hole-transporting material (HTM) for perovskite solar cells (PVSCs). BTPA-TCNE is synthesized via a simple reaction between a triphenylamine-based Michler’s base and tetracyanoethylene. This chromophore possesses a zwitterionic resonance structure in the ground state, as evidenced by X-ray crystallography and transient absorption spectroscopies. Moreover, BTPA-TCNE shows an antiparallel molecular packing (i.e., centrosymmetric dimers) in its crystalline state, which cancels out its overall molecular dipole moment to facilitate charge transport. Finally, BTPA-TCNE can be employed as an effective dopant-free HTM to realize an efficient (PCE ≈ 17.0%) PVSC in the conventional n-i-p configuration, outperforming the control device with doped spiro-OMeTAD HTM.},
doi = {10.1021/jacs.6b06291},
url = {https://www.osti.gov/biblio/1343607}, journal = {Journal of the American Chemical Society},
issn = {0002-7863},
number = 36,
volume = 138,
place = {United States},
year = {Tue Aug 23 00:00:00 EDT 2016},
month = {Tue Aug 23 00:00:00 EDT 2016}
}

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Works referenced in this record:

The emergence of perovskite solar cells
journal, July 2014


Current Challenges and Prospective Research for Upscaling Hybrid Perovskite Photovoltaics
journal, February 2016


Recent Advances in the Inverted Planar Structure of Perovskite Solar Cells
journal, December 2015


A Long-Term View on Perovskite Optoelectronics
journal, January 2016


Relationships between Lead Halide Perovskite Thin-Film Fabrication, Morphology, and Performance in Solar Cells
journal, November 2015


Rational Strategies for Efficient Perovskite Solar Cells
journal, February 2016


Recent progress and perspective in solution-processed Interfacial materials for efficient and stable polymer and organometal perovskite solar cells
journal, January 2015


Perovskite Solar Cells: Influence of Hole Transporting Materials on Power Conversion Efficiency
journal, December 2015


Planar heterojunction organometal halide perovskite solar cells: roles of interfacial layers
journal, January 2016


Efficient planar heterojunction perovskite solar cells by vapour deposition
journal, September 2013


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


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


A Methoxydiphenylamine-Substituted Carbazole Twin Derivative: An Efficient Hole-Transporting Material for Perovskite Solar Cells
journal, July 2015


A molecularly engineered hole-transporting material for efficient perovskite solar cells
journal, January 2016


Air-Exposure Induced Dopant Redistribution and Energy Level Shifts in Spin-Coated Spiro-MeOTAD Films
journal, January 2015


Dopant-Free Spiro-Triphenylamine/Fluorene as Hole-Transporting Material for Perovskite Solar Cells with Enhanced Efficiency and Stability
journal, January 2016


A dopant-free spirobi[cyclopenta[2,1-b:3,4-b′]dithiophene] based hole-transport material for efficient perovskite solar cells
journal, January 2015


A dopant free linear acene derivative as a hole transport material for perovskite pigmented solar cells
journal, January 2015


Dopant-Free Hole-Transporting Material with a C 3 h Symmetrical Truxene Core for Highly Efficient Perovskite Solar Cells
journal, February 2016


Perovskite Solar Cells Employing Dopant-Free Organic Hole Transport Materials with Tunable Energy Levels
journal, November 2015


Dopant-free polymeric hole transport materials for highly efficient and stable perovskite solar cells
journal, January 2016


Integrated Perovskite/Bulk-Heterojunction toward Efficient Solar Cells
journal, December 2014


A dopant-free organic hole transport material for efficient planar heterojunction perovskite solar cells
journal, January 2015


A–D–A-type S,N-heteropentacene-based hole transport materials for dopant-free perovskite solar cells
journal, January 2015


Perovskite Solar Cells with 12.8% Efficiency by Using Conjugated Quinolizino Acridine Based Hole Transporting Material
journal, June 2014


A hydrophobic hole transporting oligothiophene for planar perovskite solar cells with improved stability
journal, January 2014


Efficient inorganic–organic hybrid heterojunction solar cells containing perovskite compound and polymeric hole conductors
journal, May 2013


Influence of Solid-State Packing of Dipolar Merocyanine Dyes on Transistor and Solar Cell Performances
journal, October 2015


Comparative Studies on Optical, Redox, and Photovoltaic Properties of a Series of D-A-D and Analogous D-A Chromophores
journal, May 2014


Tricyanofuran-based donor–acceptor type chromophores for bulk heterojunction organic solar cells
journal, March 2012


Development of New Conjugated Polymers with Donor−π-Bridge−Acceptor Side Chains for High Performance Solar Cells
journal, September 2009


Characterisation of a dipolar chromophore with third-harmonic generation applications in the near-IR
journal, January 2012


Push–Pull Type Oligo( N -annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties
journal, June 2015


Photoconduction in Amorphous Organic Solids
journal, March 2008


The synthesis of new double-donor chromophores with excellent electro-optic activity by introducing modified bridges
journal, January 2015


Proaromaticity: Organic Charge-Transfer Chromophores with Small HOMO-LUMO Gaps
journal, July 2010


Push-Pull Buta-1,2,3-trienes: Exceptionally Low Rotational Barriers of Cumulenic CC Bonds and Proacetylenic Reactivity
journal, March 2015


Subchromophore interactions in tricyanovinyl-substituted triarylamines—a combined experimental and computational study
journal, January 1999


The captodative effect
journal, May 1985


Radical stabilization energies of disubstituted methyl radicals. A detailed theoretical analysis of the captodative effect
journal, November 1988


Long-Range Balanced Electron- and Hole-Transport Lengths in Organic-Inorganic CH3NH3PbI3
journal, October 2013


Hot-carrier cooling and photoinduced refractive index changes in organic–inorganic lead halide perovskites
journal, September 2015


Band filling with free charge carriers in organometal halide perovskites
journal, August 2014


Works referencing / citing this record:

Influence of hole transport material/metal contact interface on perovskite solar cells
journal, April 2018


Semi‐Locked Tetrathienylethene as a Building Block for Hole‐Transporting Materials: Toward Efficient and Stable Perovskite Solar Cells
journal, March 2019


Fluoranthene-based dopant-free hole transporting materials for efficient perovskite solar cells
journal, January 2018


Highly efficient phenothiazine 5,5-dioxide-based hole transport materials for planar perovskite solar cells with a PCE exceeding 20%
journal, January 2019


Hole-Transporting Materials for Perovskite Solar Cells
journal, September 2018


Cost-effective dopant-free star-shaped oligo-aryl amines for high performance perovskite solar cells
journal, January 2019


Recent Progress on the Long-Term Stability of Perovskite Solar Cells
journal, February 2018


Spiro-Phenylpyrazole/Fluorene as Hole-Transporting Material for Perovskite Solar Cells
journal, August 2017


Semiconductor TiO 2 thin film as an electrolyte for fuel cells
journal, January 2019


Realizing Efficient Lead-Free Formamidinium Tin Triiodide Perovskite Solar Cells via a Sequential Deposition Route
journal, December 2017


Stability improvement under high efficiency—next stage development of perovskite solar cells
journal, April 2019


Dopant-free molecular hole transport material that mediates a 20% power conversion efficiency in a perovskite solar cell
journal, January 2019


Inorganic CsPb 1− x Sn x IBr 2 for Efficient Wide-Bandgap Perovskite Solar Cells
journal, May 2018


Materials toward the Upscaling of Perovskite Solar Cells: Progress, Challenges, and Strategies
journal, November 2018


Acceptor-donor-acceptor type planar hole-transporting materials for efficient dopant-free perovskite solar cells
journal, January 2018


Side‐Chain Engineering on Dopant‐Free Hole‐Transporting Polymers toward Highly Efficient Perovskite Solar Cells (20.19%)
journal, July 2019


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


Toward Perovskite Solar Cell Commercialization: A Perspective and Research Roadmap Based on Interfacial Engineering
journal, June 2018


Low-Cost N , N ′-Bicarbazole-Based Dopant-Free Hole-Transporting Materials for Large-Area Perovskite Solar Cells
journal, May 2018


Organic interfacial materials for perovskite-based optoelectronic devices
journal, January 2019


Inorganic p-Type Semiconductors as Hole Conductor Building Blocks for Robust Perovskite Solar Cells
journal, July 2018


Diaryl ketone-based hole-transporting materials for efficient perovskite solar cells
journal, January 2019


Less is More: Dopant-Free Hole Transporting Materials for High-Efficiency Perovskite Solar Cells
journal, January 2018


Recent advances in perovskite solar cells: efficiency, stability and lead-free perovskite
journal, January 2017


Lowering Molecular Symmetry To Improve the Morphological Properties of the Hole-Transport Layer for Stable Perovskite Solar Cells
journal, August 2018


Recent Advances in Spiro-MeOTAD Hole Transport Material and Its Applications in Organic-Inorganic Halide Perovskite Solar Cells
journal, October 2017


Immobilization of Molecular Catalysts for Enhanced Redox Catalysis
journal, February 2018


Direct C−H Arylation Meets Perovskite Solar Cells: Tin-Free Synthesis Shortcut to High-Performance Hole-Transporting Materials
journal, May 2018


Effects of thiophene substituents on hole-transporting properties of dipolar chromophores for perovskite solar cells
journal, January 2018


Saddle-like, π-conjugated, cyclooctatetrathiophene-based, hole-transporting material for perovskite solar cells
journal, January 2019


Recent Progress on the Long-Term Stability of Perovskite Solar Cells
journal, February 2018


Spiro-Phenylpyrazole/Fluorene as Hole-Transporting Material for Perovskite Solar Cells
journal, August 2017


Fluoranthene-based dopant-free hole transporting materials for efficient perovskite solar cells
journal, January 2018