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

Title: High-Performance Polymer Solar Cells Based on a Wide-Bandgap Polymer Containing Pyrrolo[3,4- f ]benzotriazole-5,7-dione with a Power Conversion Efficiency of 8.63%

Abstract

In article 1600032, an efficient new wide-bandgap polymer based on a novel moiety of pyrrolo[3,4-f]benzotriazole-5,7-dione (TZBI) is developed by Lei Ying, Feng Lui, Thomas P. Russel, Fei Huang, and co-workers. The new chemistry enables fine electronic structure tuning and solution-processed single-junction polymer solar cells provided a remarkable power conversion efficiency of 8.63%. Full electrical and structural characterization reveales that TZBI is a promising building block for the application in highly efficient organic photovoltaics.

Authors:
 [1];  [1];  [2];  [1];  [2];  [3];  [3];  [1];  [1]
  1. South China Univ. of Technology (SCUT), Guangzhou (China). Inst. of Polymer Optoelectronic Materials and Devices State Key Lab. of Luminescent Materials and Devices
  2. Peking Univ., Beijing (China). School of Physics, State Key Lab. for Artificial Microstructure and Mesoscopic Physics
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Sciences Division
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Natural Science Foundation of China; US Department of the Navy, Office of Naval Research (ONR)
OSTI Identifier:
1377457
Grant/Contract Number:  
AC02-05CH11231; 2014CB643501; 51303056; 21520102006; 51521002; 21490573; N00014-15-1-2244
Resource Type:
Accepted Manuscript
Journal Name:
Advanced Science
Additional Journal Information:
Journal Volume: 3; Journal Issue: 9; Journal ID: ISSN 2198-3844
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 14 SOLAR ENERGY; polymer solar cells; pyrrolo[3,4-f]benzotriazole-5,7-dione; wide-bandgap polymer

Citation Formats

Lan, Liuyuan, Chen, Zhiming, Hu, Qin, Ying, Lei, Zhu, Rui, Liu, Feng, Russell, Thomas P., Huang, Fei, and Cao, Yong. High-Performance Polymer Solar Cells Based on a Wide-Bandgap Polymer Containing Pyrrolo[3,4- f ]benzotriazole-5,7-dione with a Power Conversion Efficiency of 8.63%. United States: N. p., 2016. Web. doi:10.1002/advs.201600032.
Lan, Liuyuan, Chen, Zhiming, Hu, Qin, Ying, Lei, Zhu, Rui, Liu, Feng, Russell, Thomas P., Huang, Fei, & Cao, Yong. High-Performance Polymer Solar Cells Based on a Wide-Bandgap Polymer Containing Pyrrolo[3,4- f ]benzotriazole-5,7-dione with a Power Conversion Efficiency of 8.63%. United States. https://doi.org/10.1002/advs.201600032
Lan, Liuyuan, Chen, Zhiming, Hu, Qin, Ying, Lei, Zhu, Rui, Liu, Feng, Russell, Thomas P., Huang, Fei, and Cao, Yong. Mon . "High-Performance Polymer Solar Cells Based on a Wide-Bandgap Polymer Containing Pyrrolo[3,4- f ]benzotriazole-5,7-dione with a Power Conversion Efficiency of 8.63%". United States. https://doi.org/10.1002/advs.201600032. https://www.osti.gov/servlets/purl/1377457.
@article{osti_1377457,
title = {High-Performance Polymer Solar Cells Based on a Wide-Bandgap Polymer Containing Pyrrolo[3,4- f ]benzotriazole-5,7-dione with a Power Conversion Efficiency of 8.63%},
author = {Lan, Liuyuan and Chen, Zhiming and Hu, Qin and Ying, Lei and Zhu, Rui and Liu, Feng and Russell, Thomas P. and Huang, Fei and Cao, Yong},
abstractNote = {In article 1600032, an efficient new wide-bandgap polymer based on a novel moiety of pyrrolo[3,4-f]benzotriazole-5,7-dione (TZBI) is developed by Lei Ying, Feng Lui, Thomas P. Russel, Fei Huang, and co-workers. The new chemistry enables fine electronic structure tuning and solution-processed single-junction polymer solar cells provided a remarkable power conversion efficiency of 8.63%. Full electrical and structural characterization reveales that TZBI is a promising building block for the application in highly efficient organic photovoltaics.},
doi = {10.1002/advs.201600032},
journal = {Advanced Science},
number = 9,
volume = 3,
place = {United States},
year = {Mon Apr 25 00:00:00 EDT 2016},
month = {Mon Apr 25 00:00:00 EDT 2016}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 62 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Dithienocarbazole and Isoindigo based Amorphous Low Bandgap Conjugated Polymers for Efficient Polymer Solar Cells
journal, October 2013


Single-Junction Organic Solar Cells Based on a Novel Wide-Bandgap Polymer with Efficiency of 9.7%
journal, April 2015


Single-Junction Polymer Solar Cells with Over 10% Efficiency by a Novel Two-Dimensional Donor–Acceptor Conjugated Copolymer
journal, February 2015

  • Liu, Chang; Yi, Chao; Wang, Kai
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 8
  • DOI: 10.1021/am509047g

Naphtho[1,2-b:5,6- b ′]dithiophene Based Two-Dimensional Conjugated Polymers for Highly Efficient Thick-Film Inverted Polymer Solar Cells
journal, December 2014

  • Zhu, Xiangwei; Fang, Jin; Lu, Kun
  • Chemistry of Materials, Vol. 26, Issue 24
  • DOI: 10.1021/cm5033223

Efficient Polymer Solar Cells Based on a Low Bandgap Semi-crystalline DPP Polymer-PCBM Blends
journal, June 2012


Low Band Gap Polymers Incorporating a Dicarboxylic Imide-Derived Acceptor Moiety for Efficient Polymer Solar Cells
journal, June 2013

  • Wang, Lixin; Cai, Dongdong; Zheng, Qingdong
  • ACS Macro Letters, Vol. 2, Issue 7
  • DOI: 10.1021/mz400185k

Small-Bandgap Polymer Solar Cells with Unprecedented Short-Circuit Current Density and High Fill Factor
journal, April 2015


Replacing Alkoxy Groups with Alkylthienyl Groups: A Feasible Approach To Improve the Properties of Photovoltaic Polymers
journal, August 2011

  • Huo, Lijun; Zhang, Shaoqing; Guo, Xia
  • Angewandte Chemie International Edition, Vol. 50, Issue 41
  • DOI: 10.1002/anie.201103313

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

Molecular Design toward Highly Efficient Photovoltaic Polymers Based on Two-Dimensional Conjugated Benzodithiophene
journal, April 2014

  • Ye, Long; Zhang, Shaoqing; Huo, Lijun
  • Accounts of Chemical Research, Vol. 47, Issue 5
  • DOI: 10.1021/ar5000743

Polymer solar cells with enhanced open-circuit voltage and efficiency
journal, November 2009

  • Chen, Hsiang-Yu; Hou, Jianhui; Zhang, Shaoqing
  • Nature Photonics, Vol. 3, Issue 11, p. 649-653
  • DOI: 10.1038/nphoton.2009.192

Dithienosilole-benzothiadiazole-based ternary copolymers with a D 1 –A–D 2 –A structure for polymer solar cells
journal, January 2015

  • Huang, Xuelong; Zhang, Guichuan; Zhou, Cheng
  • Polymer Chemistry, Vol. 6, Issue 22
  • DOI: 10.1039/C5PY00201J

Polymer–Fullerene Composite Solar Cells
journal, January 2008

  • Thompson, Barry C.; Fréchet, Jean M. J.
  • Angewandte Chemie International Edition, Vol. 47, Issue 1, p. 58-77
  • DOI: 10.1002/anie.200702506

Recent trends in polymer tandem solar cells research
journal, December 2013


Recent advances in water/alcohol-soluble π-conjugated materials: new materials and growing applications in solar cells
journal, January 2013

  • Duan, Chunhui; Zhang, Kai; Zhong, Chengmei
  • Chemical Society Reviews, Vol. 42, Issue 23
  • DOI: 10.1039/c3cs60200a

Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer−Fullerene Solar Cells
journal, March 2011

  • Price, Samuel C.; Stuart, Andrew C.; Yang, Liqiang
  • Journal of the American Chemical Society, Vol. 133, Issue 12
  • DOI: 10.1021/ja1112595

Alkyl Side Chain Impact on the Charge Transport and Photovoltaic Properties of Benzodithiophene and Diketopyrrolopyrrole-Based Copolymers
journal, August 2011

  • Li, Zhao; Zhang, Yanguang; Tsang, Sai-Wing
  • The Journal of Physical Chemistry C, Vol. 115, Issue 36
  • DOI: 10.1021/jp202996p

Anthracene-Based Medium Bandgap Conjugated Polymers for High Performance Polymer Solar Cells Exceeding 8% PCE Without Additive and Annealing Process
journal, April 2015

  • Jung, Jae Woong; Liu, Feng; Russell, Thomas P.
  • Advanced Energy Materials, Vol. 5, Issue 11
  • DOI: 10.1002/aenm.201500065

Thieno[3,2- b ]thiophene-Bridged D−π–A Polymer Semiconductor Based on Benzo[1,2- b :4,5- b ′]dithiophene and Benzoxadiazole
journal, June 2013

  • Wang, Xiaochen; Jiang, Pei; Chen, Yu
  • Macromolecules, Vol. 46, Issue 12
  • DOI: 10.1021/ma4005555

Constructing the nanointerpenetrating structure of PCDTBT:PC70BM bulk heterojunction solar cells induced by aggregation of PC70BM via mixed-solvent vapor annealing
journal, January 2013

  • Liu, Jiangang; Chen, Liang; Gao, Bingrong
  • Journal of Materials Chemistry A, Vol. 1, Issue 20
  • DOI: 10.1039/c3ta10629b

A pentacyclic aromatic lactam building block for efficient polymer solar cells
journal, January 2013

  • Cao, Jiamin; Liao, Qiaogan; Du, Xiaoyan
  • Energy & Environmental Science, Vol. 6, Issue 11
  • DOI: 10.1039/c3ee41948g

A polymer tandem solar cell with 10.6% power conversion efficiency
journal, February 2013

  • You, Jingbi; Dou, Letian; Yoshimura, Ken
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms2411

A Large-Bandgap Conjugated Polymer for Versatile Photovoltaic Applications with High Performance
journal, July 2015


Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells
journal, November 2014

  • Liu, Yuhang; Zhao, Jingbo; Li, Zhengke
  • Nature Communications, Vol. 5, Issue 1
  • DOI: 10.1038/ncomms6293

Recent development of push–pull conjugated polymers for bulk-heterojunction photovoltaics: rational design and fine tailoring of molecular structures
journal, January 2012

  • Duan, Chunhui; Huang, Fei; Cao, Yong
  • Journal of Materials Chemistry, Vol. 22, Issue 21
  • DOI: 10.1039/c2jm30470h

Efficiency of bulk-heterojunction organic solar cells
journal, December 2013


Relating Chemical Structure to Device Performance via Morphology Control in Diketopyrrolopyrrole-Based Low Band Gap Polymers
journal, December 2013

  • Liu, Feng; Wang, Cheng; Baral, Jayanta K.
  • Journal of the American Chemical Society, Vol. 135, Issue 51
  • DOI: 10.1021/ja408923y

Thermally Stable, Efficient Polymer Solar Cells with Nanoscale Control of the Interpenetrating Network Morphology
journal, October 2005

  • Ma, W.; Yang, C.; Gong, X.
  • Advanced Functional Materials, Vol. 15, Issue 10, p. 1617-1622
  • DOI: 10.1002/adfm.200500211

Design and synthesis of star-burst triphenyamine-based π-conjugated molecules
journal, February 2015


Synthesis and Photovoltaic Performance of Water/Alcohol Soluble Small Phorphyrin Derivatives for Polymer Solar Cells
journal, January 2015

  • Lu, Junming; Cai, Wanqing; Zhang, Guichuan
  • Acta Chimica Sinica, Vol. 73, Issue 11
  • DOI: 10.6023/A15080546

Absolute Measurement of Domain Composition and Nanoscale Size Distribution Explains Performance in PTB7:PC 71 BM Solar Cells
journal, October 2012

  • Collins, Brian A.; Li, Zhe; Tumbleston, John R.
  • Advanced Energy Materials, Vol. 3, Issue 1
  • DOI: 10.1002/aenm.201200377

Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications
journal, December 2011

  • Beaujuge, Pierre M.; Fréchet, Jean M. J.
  • Journal of the American Chemical Society, Vol. 133, Issue 50, p. 20009-20029
  • DOI: 10.1021/ja2073643

Efficient Small Bandgap Polymer Solar Cells with High Fill Factors for 300 nm Thick Films
journal, March 2013

  • Li, Weiwei; Hendriks, Koen H.; Roelofs, W. S. Christian
  • Advanced Materials, Vol. 25, Issue 23
  • DOI: 10.1002/adma.201300017

“Solvent Annealing” Effect in Polymer Solar Cells Based on Poly(3-hexylthiophene) and Methanofullerenes
journal, July 2007

  • Li, G.; Yao, Y.; Yang, H.
  • Advanced Functional Materials, Vol. 17, Issue 10, p. 1636-1644
  • DOI: 10.1002/adfm.200600624

A high voltage solar cell using a donor–acceptor conjugated polymer based on pyrrolo[3,4-f]-2,1,3-benzothiadiazole-5,7-dione
journal, January 2014

  • Li, Hairong; Sun, Shuangyong; Mhaisalkar, Subodh
  • J. Mater. Chem. A, Vol. 2, Issue 42
  • DOI: 10.1039/C4TA01248H

Development of Large Band-Gap Conjugated Copolymers for Efficient Regular Single and Tandem Organic Solar Cells
journal, August 2013

  • Li, Kai; Li, Zuojia; Feng, Kui
  • Journal of the American Chemical Society, Vol. 135, Issue 36
  • DOI: 10.1021/ja406220a

Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions
journal, December 1995


6.5% Efficiency of Polymer Solar Cells Based on poly(3-hexylthiophene) and Indene-C60 Bisadduct by Device Optimization
journal, June 2010

  • Zhao, Guangjin; He, Youjun; Li, Yongfang
  • Advanced Materials, Vol. 22, Issue 39, p. 4355-4358
  • DOI: 10.1002/adma.201001339

Origin of the Open Circuit Voltage of Plastic Solar Cells
journal, October 2001


Single-Junction Polymer Solar Cells Exceeding 10% Power Conversion Efficiency
journal, November 2014


Sub-glass transition annealing enhances polymer solar cell performance
journal, January 2014

  • Bergqvist, Jonas; Lindqvist, Camilla; Bäcke, Olof
  • J. Mater. Chem. A, Vol. 2, Issue 17
  • DOI: 10.1039/C3TA14165A

Processable Low-Bandgap Polymers for Photovoltaic Applications
journal, February 2011

  • Boudreault, Pierre-Luc T.; Najari, Ahmed; Leclerc, Mario
  • Chemistry of Materials, Vol. 23, Issue 3
  • DOI: 10.1021/cm1021855

Linear Side Chains in Benzo[1,2- b :4,5- b ′]dithiophene–Thieno[3,4- c ]pyrrole-4,6-dione Polymers Direct Self-Assembly and Solar Cell Performance
journal, March 2013

  • Cabanetos, Clément; El Labban, Abdulrahman; Bartelt, Jonathan A.
  • Journal of the American Chemical Society, Vol. 135, Issue 12
  • DOI: 10.1021/ja400365b

Donor–acceptor conjugated polymers based on cyclic imide substituted quinoxaline or dibenzo[a,c]phenazine for polymer solar cells
journal, January 2015

  • Lan, Liuyuan; Chen, Zhiming; Li, Yunchuan
  • Polymer Chemistry, Vol. 6, Issue 43
  • DOI: 10.1039/C5PY01235J

A “zig-zag” naphthodithiophene core for increased efficiency in solution-processed small molecule solar cells
journal, January 2012

  • Loser, Stephen; Miyauchi, Hiroyuki; Hennek, Jonathan W.
  • Chemical Communications, Vol. 48, Issue 68
  • DOI: 10.1039/c2cc32646a

[1,2,5]Thiadiazolo[3,4-f]benzotriazole based narrow band gap conjugated polymers with photocurrent response up to 1.1μm
journal, October 2013


Water/alcohol soluble conjugated polymers for the interface engineering of highly efficient polymer light-emitting diodes and polymer solar cells
journal, January 2015

  • Hu, Zhicheng; Zhang, Kai; Huang, Fei
  • Chemical Communications, Vol. 51, Issue 26
  • DOI: 10.1039/C4CC09433F

Manipulating the Morphology of P3HT–PCBM Bulk Heterojunction Blends with Solvent Vapor Annealing
journal, October 2012

  • Verploegen, Eric; Miller, Chad E.; Schmidt, Kristin
  • Chemistry of Materials, Vol. 24, Issue 20
  • DOI: 10.1021/cm302312a

6.5% Efficiency of Polymer Solar Cells Based on poly(3-hexylthiophene) and Indene-C60 Bisadduct by Device Optimization
journal, June 2010

  • Zhao, Guangjin; He, Youjun; Li, Yongfang
  • Advanced Materials, Vol. 22, Issue 39, p. 4355-4358
  • DOI: 10.1002/adma.201001339

Efficient Polymer Solar Cells Based on a Low Bandgap Semi-crystalline DPP Polymer-PCBM Blends
journal, June 2012


Dithienocarbazole and Isoindigo based Amorphous Low Bandgap Conjugated Polymers for Efficient Polymer Solar Cells
journal, October 2013


A Large-Bandgap Conjugated Polymer for Versatile Photovoltaic Applications with High Performance
journal, July 2015


Molecular Design toward Highly Efficient Photovoltaic Polymers Based on Two-Dimensional Conjugated Benzodithiophene
journal, April 2014

  • Ye, Long; Zhang, Shaoqing; Huo, Lijun
  • Accounts of Chemical Research, Vol. 47, Issue 5
  • DOI: 10.1021/ar5000743

Linear Side Chains in Benzo[1,2- b :4,5- b ′]dithiophene–Thieno[3,4- c ]pyrrole-4,6-dione Polymers Direct Self-Assembly and Solar Cell Performance
journal, March 2013

  • Cabanetos, Clément; El Labban, Abdulrahman; Bartelt, Jonathan A.
  • Journal of the American Chemical Society, Vol. 135, Issue 12
  • DOI: 10.1021/ja400365b

Recent advances in water/alcohol-soluble π-conjugated materials: new materials and growing applications in solar cells
journal, January 2013

  • Duan, Chunhui; Zhang, Kai; Zhong, Chengmei
  • Chemical Society Reviews, Vol. 42, Issue 23
  • DOI: 10.1039/c3cs60200a

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

Works referencing / citing this record:

Recent Advances in Wide-Bandgap Photovoltaic Polymers
journal, March 2017


High-Performance Nonfullerene Polymer Solar Cells based on Imide-Functionalized Wide-Bandgap Polymers
journal, March 2017

  • Fan, Baobing; Zhang, Kai; Jiang, Xiao-Fang
  • Advanced Materials, Vol. 29, Issue 21
  • DOI: 10.1002/adma.201606396

All-Polymer Solar Cells Based on a Conjugated Polymer Containing Siloxane-Functionalized Side Chains with Efficiency over 10%
journal, November 2017


Highly Efficient Tandem Organic Solar Cell Enabled by Environmentally Friendly Solvent Processed Polymeric Interconnecting Layer
journal, February 2018

  • Zhang, Kai; Fan, Baobing; Xia, Ruoxi
  • Advanced Energy Materials, Vol. 8, Issue 15
  • DOI: 10.1002/aenm.201703180

Recent Progress in All‐Polymer Solar Cells Based on Wide‐Bandgap p‐Type Polymers
journal, August 2019

  • Zhu, Peng; Fan, Baobing; Ying, Lei
  • Chemistry – An Asian Journal, Vol. 14, Issue 18
  • DOI: 10.1002/asia.201900827

Imide‐Functionalized Polymer Semiconductors
journal, December 2018

  • Sun, Huiliang; Wang, Lei; Wang, Yingfeng
  • Chemistry – A European Journal, Vol. 25, Issue 1
  • DOI: 10.1002/chem.201803605

Towards a bright future: polymer solar cells with power conversion efficiencies over 10%
journal, March 2017


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


Surpassing the 10% efficiency milestone for 1-cm2 all-polymer solar cells
journal, September 2019


Fine-tuning of the chemical structure of photoactive materials for highly efficient organic photovoltaics
journal, October 2018


Structural engineering of pyrrolo[3,4- f ]benzotriazole-5,7(2 H ,6 H )-dione-based polymers for non-fullerene organic solar cells with an efficiency over 12%
journal, January 2019

  • Abdulahi, Birhan A.; Li, Xiaoming; Mone, Mariza
  • Journal of Materials Chemistry A, Vol. 7, Issue 33
  • DOI: 10.1039/c9ta06385d

Impact of linker positions for thieno[3,2-b]thiophene in wide band gap benzo[1,2-b:4,5-b′]dithiophene-based photovoltaic polymers
journal, March 2019

  • Zhang, Mingjing; Zhang, Xiaofang; Guo, Pengzhi
  • Journal of Materials Research, Vol. 34, Issue 12
  • DOI: 10.1557/jmr.2019.81