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Title: Enhanced hindrance from phenyl outer side chains on nonfullerene acceptor enables unprecedented simultaneous enhancement in organic solar cell performances with 16.7% efficiency

Abstract

Inner side-chain engineering on Y6 has been a proven successful in improving short-circuit current density (JSC) through fine-tuning aggregated structures of acceptors. However, it fails in tuning the lowest unoccupied molecular orbital level (LUMO) and open-circuit voltage (VOC). In this paper, we turn to focus on engineering the outer side chains on the flanking thienothiophene units with 4-hexylphenyl (PhC6) and 6-phenylhexyl (C6Ph) chains. Use of PhC6 enhances the steric effect between the attached phenyl and the ending group, which in combination with the additional conjugation effect provided by the linking phenyl leads to upshifted energy levels and increased VOC as a result. Again, substitution with the bulkier PhC6 unprecedentedly improves film-morphology with reduced paracrystalline disorder and long period and increased root-mean-square composition variations as well, leading to increased electron and hole mobilities and suppressed monomolecular recombination with JSC and fill-factor (FF) simultaneously enhanced. The PM6:BTP-PhC6-based devices yield a higher efficiency value of 16.7% than the PM6:BTP-C6Ph-based one (15.5%). Furthermore, this study shows a conceptual advance in materials design towards reducing the conflict between VOC and JSC in binary blended organic solar cells, which can be achieved by introducing bulkier chains to twist the backbone and simultaneously enhance the packing order.

Authors:
 [1];  [2]; ORCiD logo [3];  [4];  [2];  [4];  [2];  [2];  [5];  [2]; ORCiD logo [5];  [3];  [6]; ORCiD logo [7]
  1. Chang'an Univ., Xi'an (China); Hong Kong Univ. of Science and Technology, Hong Kong (China)
  2. Hong Kong Univ. of Science and Technology, Hong Kong (China)
  3. North Carolina State Univ., Raleigh, NC (United States)
  4. Chang'an Univ., Xi'an (China); Chinese Academy of Sciences (CAS), Beijing (China)
  5. Hong Kong Univ. of Science and Technology, Hong Kong (China); Hong Kong Univ. of Science and Technology-Shenzhen Research Inst., Shenzhen (China)
  6. Chang'an Univ., Xi'an (China)
  7. Chinese Academy of Sciences (CAS), Beijing (China); Inner Mongolia Normal Univ., Huhehot (China)
Publication Date:
Research Org.:
Hong Kong Univ. of Science and Technology, Hong Kong (China)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1635335
Alternate Identifier(s):
OSTI ID: 1635438
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Nano Energy
Additional Journal Information:
Journal Volume: 76; Journal Issue: C; Journal ID: ISSN 2211-2855
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY; fullerene-free; side-chain engineering; organic solar cell; isomerization; aggregated structure

Citation Formats

Chai, Gaoda, Chang, Yuan, Peng, Zhengxing, Jia, Yanyan, Zou, Xinhui, Yu, Dian, Yu, Han, Chen, Yuzhong, Chow, Philip C. Y., Wong, Kam Sing, Zhang, Jianquan, Ade, Harald, Yang, Liwei, and Zhan, Chuanlang. Enhanced hindrance from phenyl outer side chains on nonfullerene acceptor enables unprecedented simultaneous enhancement in organic solar cell performances with 16.7% efficiency. United States: N. p., 2020. Web. doi:10.1016/j.nanoen.2020.105087.
Chai, Gaoda, Chang, Yuan, Peng, Zhengxing, Jia, Yanyan, Zou, Xinhui, Yu, Dian, Yu, Han, Chen, Yuzhong, Chow, Philip C. Y., Wong, Kam Sing, Zhang, Jianquan, Ade, Harald, Yang, Liwei, & Zhan, Chuanlang. Enhanced hindrance from phenyl outer side chains on nonfullerene acceptor enables unprecedented simultaneous enhancement in organic solar cell performances with 16.7% efficiency. United States. https://doi.org/10.1016/j.nanoen.2020.105087
Chai, Gaoda, Chang, Yuan, Peng, Zhengxing, Jia, Yanyan, Zou, Xinhui, Yu, Dian, Yu, Han, Chen, Yuzhong, Chow, Philip C. Y., Wong, Kam Sing, Zhang, Jianquan, Ade, Harald, Yang, Liwei, and Zhan, Chuanlang. Sun . "Enhanced hindrance from phenyl outer side chains on nonfullerene acceptor enables unprecedented simultaneous enhancement in organic solar cell performances with 16.7% efficiency". United States. https://doi.org/10.1016/j.nanoen.2020.105087. https://www.osti.gov/servlets/purl/1635335.
@article{osti_1635335,
title = {Enhanced hindrance from phenyl outer side chains on nonfullerene acceptor enables unprecedented simultaneous enhancement in organic solar cell performances with 16.7% efficiency},
author = {Chai, Gaoda and Chang, Yuan and Peng, Zhengxing and Jia, Yanyan and Zou, Xinhui and Yu, Dian and Yu, Han and Chen, Yuzhong and Chow, Philip C. Y. and Wong, Kam Sing and Zhang, Jianquan and Ade, Harald and Yang, Liwei and Zhan, Chuanlang},
abstractNote = {Inner side-chain engineering on Y6 has been a proven successful in improving short-circuit current density (JSC) through fine-tuning aggregated structures of acceptors. However, it fails in tuning the lowest unoccupied molecular orbital level (LUMO) and open-circuit voltage (VOC). In this paper, we turn to focus on engineering the outer side chains on the flanking thienothiophene units with 4-hexylphenyl (PhC6) and 6-phenylhexyl (C6Ph) chains. Use of PhC6 enhances the steric effect between the attached phenyl and the ending group, which in combination with the additional conjugation effect provided by the linking phenyl leads to upshifted energy levels and increased VOC as a result. Again, substitution with the bulkier PhC6 unprecedentedly improves film-morphology with reduced paracrystalline disorder and long period and increased root-mean-square composition variations as well, leading to increased electron and hole mobilities and suppressed monomolecular recombination with JSC and fill-factor (FF) simultaneously enhanced. The PM6:BTP-PhC6-based devices yield a higher efficiency value of 16.7% than the PM6:BTP-C6Ph-based one (15.5%). Furthermore, this study shows a conceptual advance in materials design towards reducing the conflict between VOC and JSC in binary blended organic solar cells, which can be achieved by introducing bulkier chains to twist the backbone and simultaneously enhance the packing order.},
doi = {10.1016/j.nanoen.2020.105087},
journal = {Nano Energy},
number = C,
volume = 76,
place = {United States},
year = {Sun Jun 21 00:00:00 EDT 2020},
month = {Sun Jun 21 00:00:00 EDT 2020}
}

Works referenced in this record:

Organic solar cells based on non-fullerene acceptors
journal, January 2018

  • Hou, Jianhui; Inganäs, Olle; Friend, Richard H.
  • Nature Materials, Vol. 17, Issue 2
  • DOI: 10.1038/nmat5063

Nonfullerene Acceptor Molecules for Bulk Heterojunction Organic Solar Cells
journal, February 2018


Nonfullerene All-Small-Molecule Organic Solar Cells
journal, May 2019


Critical review of the molecular design progress in non-fullerene electron acceptors towards commercially viable organic solar cells
journal, January 2019

  • Wadsworth, Andrew; Moser, Maximilian; Marks, Adam
  • Chemical Society Reviews, Vol. 48, Issue 6
  • DOI: 10.1039/C7CS00892A

Achieving Over 15% Efficiency in Organic Photovoltaic Cells via Copolymer Design
journal, February 2019


Achieving over 16% efficiency for single-junction organic solar cells
journal, March 2019


16.7%-efficiency ternary blended organic photovoltaic cells with PCBM as the acceptor additive to increase the open-circuit voltage and phase purity
journal, January 2019

  • Pan, Ming-Ao; Lau, Tsz-Ki; Tang, Yabing
  • Journal of Materials Chemistry A, Vol. 7, Issue 36
  • DOI: 10.1039/C9TA06929A

Single‐Junction Polymer Solar Cells with 16.35% Efficiency Enabled by a Platinum(II) Complexation Strategy
journal, May 2019


A 16.4% efficiency organic photovoltaic cell enabled using two donor polymers with their side-chains oriented differently by a ternary strategy
journal, January 2020

  • Chang, Yuan; Lau, Tsz-Ki; Chow, Philip C. Y.
  • Journal of Materials Chemistry A, Vol. 8, Issue 7
  • DOI: 10.1039/C9TA13293G

High-Performance Electron Acceptor with Thienyl Side Chains for Organic Photovoltaics
journal, March 2016

  • Lin, Yuze; Zhao, Fuwen; He, Qiao
  • Journal of the American Chemical Society, Vol. 138, Issue 14
  • DOI: 10.1021/jacs.6b02004

Fused-Ring Acceptors with Asymmetric Side Chains for High-Performance Thick-Film Organic Solar Cells
journal, September 2017


Effects of Short‐Axis Alkoxy Substituents on Molecular Self‐Assembly and Photovoltaic Performance of Indacenodithiophene‐Based Acceptors
journal, October 2019

  • Li, Xiaojun; Huang, He; Angunawela, Indunil
  • Advanced Functional Materials, Vol. 30, Issue 3
  • DOI: 10.1002/adfm.201906855

A Highly Crystalline Fused-Ring n-Type Small Molecule for Non-Fullerene Acceptor Based Organic Solar Cells and Field-Effect Transistors
journal, July 2018

  • Song, Xin; Gasparini, Nicola; Nahid, Masrur Morshed
  • Advanced Functional Materials, Vol. 28, Issue 35
  • DOI: 10.1002/adfm.201802895

Effect of Isomerization on High-Performance Nonfullerene Electron Acceptors
journal, June 2018

  • Wang, Jiayu; Zhang, Junxiang; Xiao, Yiqun
  • Journal of the American Chemical Society, Vol. 140, Issue 29
  • DOI: 10.1021/jacs.8b04027

Dithienopicenocarbazole-Based Acceptors for Efficient Organic Solar Cells with Optoelectronic Response Over 1000 nm and an Extremely Low Energy Loss
journal, February 2018

  • Yao, Zhaoyang; Liao, Xunfan; Gao, Ke
  • Journal of the American Chemical Society, Vol. 140, Issue 6
  • DOI: 10.1021/jacs.7b13239

Nonfullerene Acceptors with Enhanced Solubility and Ordered Packing for High-Efficiency Polymer Solar Cells
journal, July 2018


Side-Chain Engineering of Nonfullerene Acceptors for Near-Infrared Organic Photodetectors and Photovoltaics
journal, May 2019


Nonfullerene Polymer Solar Cells Based on a Main-Chain Twisted Low-Bandgap Acceptor with Power Conversion Efficiency of 13.2%
journal, May 2018


Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core
journal, April 2019


Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages
journal, June 2019


Semitransparent solar cells with over 12% efficiency based on a new low bandgap fluorinated small molecule acceptor
journal, January 2019

  • Luo, Mei; Zhao, Chunyan; Yuan, Jun
  • Materials Chemistry Frontiers, Vol. 3, Issue 11
  • DOI: 10.1039/C9QM00499H

High Efficiency Polymer Solar Cells with Efficient Hole Transfer at Zero Highest Occupied Molecular Orbital Offset between Methylated Polymer Donor and Brominated Acceptor
journal, January 2020

  • Sun, Chenkai; Qin, Shucheng; Wang, Rui
  • Journal of the American Chemical Society, Vol. 142, Issue 3
  • DOI: 10.1021/jacs.9b09939

Bromination: An Alternative Strategy for Non‐Fullerene Small Molecule Acceptors
journal, February 2020


Subtle Polymer Donor and Molecular Acceptor Design Enable Efficient Polymer Solar Cells with a Very Small Energy Loss
journal, December 2019

  • Xu, Xiaopeng; Feng, Kui; Lee, Young Woong
  • Advanced Functional Materials, Vol. 30, Issue 9
  • DOI: 10.1002/adfm.201907570

Simultaneous enhanced efficiency and thermal stability in organic solar cells from a polymer acceptor additive
journal, March 2020


Over 17% efficiency ternary organic solar cells enabled by two non-fullerene acceptors working in an alloy-like model
journal, January 2020

  • Zhan, Lingling; Li, Shuixing; Lau, Tsz-Ki
  • Energy & Environmental Science, Vol. 13, Issue 2
  • DOI: 10.1039/C9EE03710A

An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells
journal, January 2015


Enhancing Indacenodithiophene Acceptor Crystallinity via Substituent Manipulation Increases Organic Solar Cell Efficiency
journal, November 2017


Side-Chain Isomerization on an n-type Organic Semiconductor ITIC Acceptor Makes 11.77% High Efficiency Polymer Solar Cells
journal, November 2016

  • Yang, Yankang; Zhang, Zhi-Guo; Bin, Haijun
  • Journal of the American Chemical Society, Vol. 138, Issue 45
  • DOI: 10.1021/jacs.6b09110

Eco‐Compatible Solvent‐Processed Organic Photovoltaic Cells with Over 16% Efficiency
journal, August 2019


Alkyl Chain Tuning of Small Molecule Acceptors for Efficient Organic Solar Cells
journal, December 2019


Exploiting Noncovalently Conformational Locking as a Design Strategy for High Performance Fused-Ring Electron Acceptor Used in Polymer Solar Cells
journal, February 2017

  • Liu, Yahui; Zhang, Zhe; Feng, Shiyu
  • Journal of the American Chemical Society, Vol. 139, Issue 9
  • DOI: 10.1021/jacs.7b00566

Conformation Locking on Fused-Ring Electron Acceptor for High-Performance Nonfullerene Organic Solar Cells
journal, January 2018

  • Zhang, Zhuohan; Yu, Jiangsheng; Yin, Xinxing
  • Advanced Functional Materials, Vol. 28, Issue 11
  • DOI: 10.1002/adfm.201705095

High‐Efficiency As‐Cast Organic Solar Cells Based on Acceptors with Steric Hindrance Induced Planar Terminal Group
journal, July 2019


Impact of the Bonding Sites at the Inner or Outer π-Bridged Positions for Non-Fullerene Acceptors
journal, May 2019

  • Ming, Shouli; Zhang, Cai’e; Jiang, Pengcheng
  • ACS Applied Materials & Interfaces, Vol. 11, Issue 21
  • DOI: 10.1021/acsami.9b02964

n-Type Water/Alcohol-Soluble Naphthalene Diimide-Based Conjugated Polymers for High-Performance Polymer Solar Cells
journal, February 2016

  • Wu, Zhihong; Sun, Chen; Dong, Sheng
  • Journal of the American Chemical Society, Vol. 138, Issue 6
  • DOI: 10.1021/jacs.5b12664

Electrical characteristics and efficiency of single-layer organic light-emitting diodes
journal, November 1998


Competition between recombination and extraction of free charges determines the fill factor of organic solar cells
journal, May 2015

  • Bartesaghi, Davide; Pérez, Irene del Carmen; Kniepert, Juliane
  • Nature Communications, Vol. 6, Issue 1
  • DOI: 10.1038/ncomms8083

Recombination and loss analysis in polythiophene based bulk heterojunction photodetectors
journal, November 2002

  • Schilinsky, Pavel; Waldauf, Christoph; Brabec, Christoph J.
  • Applied Physics Letters, Vol. 81, Issue 20
  • DOI: 10.1063/1.1521244

Integrated Molecular, Interfacial, and Device Engineering towards High-Performance Non-Fullerene Based Organic Solar Cells
journal, June 2014

  • Zang, Yue; Li, Chang-Zhi; Chueh, Chu-Chen
  • Advanced Materials, Vol. 26, Issue 32, p. 5708-5714
  • DOI: 10.1002/adma.201401992

Burn-in Free Nonfullerene-Based Organic Solar Cells
journal, July 2017

  • Gasparini, Nicola; Salvador, Michael; Strohm, Sebastian
  • Advanced Energy Materials, Vol. 7, Issue 19
  • DOI: 10.1002/aenm.201700770

A SAXS/WAXS/GISAXS Beamline with Multilayer Monochromator
journal, October 2010


Quantitative analysis of lattice disorder and crystallite size in organic semiconductor thin films
journal, July 2011


Soft x-ray scattering facility at the Advanced Light Source with real-time data processing and analysis
journal, April 2012

  • Gann, E.; Young, A. T.; Collins, B. A.
  • Review of Scientific Instruments, Vol. 83, Issue 4
  • DOI: 10.1063/1.3701831