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Title: A Highly Crystalline Fused‐Ring n‐Type Small Molecule for Non‐Fullerene Acceptor Based Organic Solar Cells and Field‐Effect Transistors

Abstract

Abstract N‐type organic small molecules (SMs) are attracting attention in the organic electronics field, due to their easy purification procedures with high yield. However, only a few reports show SMs that perform well in both organic field‐effect transistors (OFETs) and organic solar cells (OSCs). Here, the synthesis and characterization of an n‐type small molecule with an indacenodithieno[3,2‐b]thiophene (IDTT) core unit and linear alkylated side chain (C 16 ) (IDTTIC) are reported. Compared to the state‐of‐the‐art n‐type molecule IDTIC, IDTTIC exhibits smaller optical bandgap and higher absorption coefficient, which is due to the enhanced intramolecular effect. After mixing with the polymer donor PBDB‐T, IDTIC‐based solar cells deliver a power conversion efficiency of only 5.67%. In stark contrast, the OSC performance of IDTTIC improves significantly to 11.2%. It is found that the superior photovoltaic properties of PBDB‐T:IDTTIC blends are mainly due to reduced trap‐assisted recombination and enhanced molecular packing coherence length and higher domain purity when compared to IDTIC. Moreover, a significantly higher electron mobility of 0.50 cm 2 V −1 s −1 for IDTTIC in OFET devices than for IDTIC (0.15 cm 2 V −1 s −1 ) is obtained. These superior performances in OSCs and OFETs demonstrate that SMs withmore » extended π‐conjugation of the backbone possess a great potential for application in organic electronic devices.« less

Authors:
ORCiD logo [1];  [1];  [2];  [1];  [1];  [1];  [3];  [3];  [1];  [2];  [4]; ORCiD logo [1]
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  1. KAUST Solar Center (KSC) Division of Physical Sciences and Engineering King Abdullah University of Science and Technology (KAUST) Thuwal 23955‐6900 Saudi Arabia
  2. Department of Physics Organic and Carbon Electronics Lab (ORaCEL) North Carolina State University Raleigh NC 27695 USA
  3. Advanced Light Source Lawrence Berkeley National Laboratory Berkeley CA 94720 USA
  4. KAUST Solar Center (KSC) Division of Physical Sciences and Engineering King Abdullah University of Science and Technology (KAUST) Thuwal 23955‐6900 Saudi Arabia, Department of Chemistry and Centre for Plastic Electronics Imperial College London London SW7 2AZ UK
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1460113
Grant/Contract Number:  
DE‐AC02‐05CH11231
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Advanced Functional Materials
Additional Journal Information:
Journal Name: Advanced Functional Materials Journal Volume: 28 Journal Issue: 35; Journal ID: ISSN 1616-301X
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Song, Xin, Gasparini, Nicola, Nahid, Masrur Morshed, Chen, Hu, Macphee, Sky Marie, Zhang, Weimin, Norman, Victoria, Zhu, Chenhui, Bryant, Daniel, Ade, Harald, McCulloch, Iain, and Baran, Derya. A Highly Crystalline Fused‐Ring n‐Type Small Molecule for Non‐Fullerene Acceptor Based Organic Solar Cells and Field‐Effect Transistors. Germany: N. p., 2018. Web. doi:10.1002/adfm.201802895.
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Song, Xin, Gasparini, Nicola, Nahid, Masrur Morshed, Chen, Hu, Macphee, Sky Marie, Zhang, Weimin, Norman, Victoria, Zhu, Chenhui, Bryant, Daniel, Ade, Harald, McCulloch, Iain, & Baran, Derya. A Highly Crystalline Fused‐Ring n‐Type Small Molecule for Non‐Fullerene Acceptor Based Organic Solar Cells and Field‐Effect Transistors. Germany. https://doi.org/10.1002/adfm.201802895
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Song, Xin, Gasparini, Nicola, Nahid, Masrur Morshed, Chen, Hu, Macphee, Sky Marie, Zhang, Weimin, Norman, Victoria, Zhu, Chenhui, Bryant, Daniel, Ade, Harald, McCulloch, Iain, and Baran, Derya. Fri . "A Highly Crystalline Fused‐Ring n‐Type Small Molecule for Non‐Fullerene Acceptor Based Organic Solar Cells and Field‐Effect Transistors". Germany. https://doi.org/10.1002/adfm.201802895.
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@article{osti_1460113,
title = {A Highly Crystalline Fused‐Ring n‐Type Small Molecule for Non‐Fullerene Acceptor Based Organic Solar Cells and Field‐Effect Transistors},
author = {Song, Xin and Gasparini, Nicola and Nahid, Masrur Morshed and Chen, Hu and Macphee, Sky Marie and Zhang, Weimin and Norman, Victoria and Zhu, Chenhui and Bryant, Daniel and Ade, Harald and McCulloch, Iain and Baran, Derya},
abstractNote = {Abstract N‐type organic small molecules (SMs) are attracting attention in the organic electronics field, due to their easy purification procedures with high yield. However, only a few reports show SMs that perform well in both organic field‐effect transistors (OFETs) and organic solar cells (OSCs). Here, the synthesis and characterization of an n‐type small molecule with an indacenodithieno[3,2‐b]thiophene (IDTT) core unit and linear alkylated side chain (C 16 ) (IDTTIC) are reported. Compared to the state‐of‐the‐art n‐type molecule IDTIC, IDTTIC exhibits smaller optical bandgap and higher absorption coefficient, which is due to the enhanced intramolecular effect. After mixing with the polymer donor PBDB‐T, IDTIC‐based solar cells deliver a power conversion efficiency of only 5.67%. In stark contrast, the OSC performance of IDTTIC improves significantly to 11.2%. It is found that the superior photovoltaic properties of PBDB‐T:IDTTIC blends are mainly due to reduced trap‐assisted recombination and enhanced molecular packing coherence length and higher domain purity when compared to IDTIC. Moreover, a significantly higher electron mobility of 0.50 cm 2 V −1 s −1 for IDTTIC in OFET devices than for IDTIC (0.15 cm 2 V −1 s −1 ) is obtained. These superior performances in OSCs and OFETs demonstrate that SMs with extended π‐conjugation of the backbone possess a great potential for application in organic electronic devices.},
doi = {10.1002/adfm.201802895},
journal = {Advanced Functional Materials},
number = 35,
volume = 28,
place = {Germany},
year = {Fri Jul 13 00:00:00 EDT 2018},
month = {Fri Jul 13 00:00:00 EDT 2018}
}
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https://doi.org/10.1002/adfm.201802895
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Works referenced in this record:

The Physics of Small Molecule Acceptors for Efficient and Stable Bulk Heterojunction Solar Cells
journal, January 2018

  • Gasparini, Nicola; Wadsworth, Andrew; Moser, Maximilian
  • Advanced Energy Materials, Vol. 8, Issue 12
  • DOI: 10.1002/aenm.201703298

A Novel Alkylated Indacenodithieno[3,2-b]thiophene-Based Polymer for High-Performance Field-Effect Transistors
journal, October 2015

Origins of polarization-dependent anisotropic X-ray scattering from organic thin films
journal, January 2016

  • Gann, Eliot; Collins, Brian A.; Tang, Maolong
  • Journal of Synchrotron Radiation, Vol. 23, Issue 1
  • DOI: 10.1107/S1600577515019074

Over 14% Efficiency in Polymer Solar Cells Enabled by a Chlorinated Polymer Donor
journal, March 2018

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

A high-mobility electron-transporting polymer for printed transistors
journal, January 2009

  • Yan, He; Chen, Zhihua; Zheng, Yan
  • Nature, Vol. 457, Issue 7230, p. 679-686
  • DOI: 10.1038/nature07727

Design of Diketopyrrolopyrrole (DPP)-Based Small Molecules for Organic-Solar-Cell Applications
journal, November 2016

  • Tang, Ailing; Zhan, Chuanlang; Yao, Jiannian
  • Advanced Materials, Vol. 29, Issue 2
  • DOI: 10.1002/adma.201600013

Experimental determination of the rate law for charge carrier decay in a polythiophene: Fullerene solar cell
journal, March 2008

  • Shuttle, C. G.; O’Regan, B.; Ballantyne, A. M.
  • Applied Physics Letters, Vol. 92, Issue 9
  • DOI: 10.1063/1.2891871

Reduced voltage losses yield 10% efficient fullerene free organic solar cells with >1 V open circuit voltages
journal, January 2016

  • Baran, D.; Kirchartz, T.; Wheeler, S.
  • Energy & Environmental Science, Vol. 9, Issue 12
  • DOI: 10.1039/C6EE02598F

Enhancing Performance of Nonfullerene Acceptors via Side-Chain Conjugation Strategy
journal, July 2017

Halogenated conjugated molecules for ambipolar field-effect transistors and non-fullerene organic solar cells
journal, January 2017

  • Yang, Fan; Li, Cheng; Lai, Wenbin
  • Materials Chemistry Frontiers, Vol. 1, Issue 7
  • DOI: 10.1039/C7QM00025A

High-performance ternary organic solar cells with thick active layer exceeding 11% efficiency
journal, January 2017

  • Gasparini, Nicola; Lucera, Luca; Salvador, Michael
  • Energy & Environmental Science, Vol. 10, Issue 4
  • DOI: 10.1039/C6EE03599J

High-efficiency and air-stable P3HT-based polymer solar cells with a new non-fullerene acceptor
journal, June 2016

  • Holliday, Sarah; Ashraf, Raja Shahid; Wadsworth, Andrew
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms11585

Morphological characterization of fullerene and fullerene-free organic photovoltaics by combined real and reciprocal space techniques
journal, May 2017

  • Mukherjee, Subhrangsu; Herzing, Andrew A.; Zhao, Donglin
  • Journal of Materials Research, Vol. 32, Issue 10
  • DOI: 10.1557/jmr.2017.131

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

Control of Mesoscale Morphology and Photovoltaic Performance in Diketopyrrolopyrrole-Based Small Band Gap Terpolymers
journal, October 2016

  • Ye, Long; Jiao, Xuechen; Zhang, Shaoqing
  • Advanced Energy Materials, Vol. 7, Issue 3
  • DOI: 10.1002/aenm.201601138

Imide- and Amide-Functionalized Polymer Semiconductors
journal, September 2014

  • Guo, Xugang; Facchetti, Antonio; Marks, Tobin J.
  • Chemical Reviews, Vol. 114, Issue 18
  • DOI: 10.1021/cr500225d

Quantitative relations between interaction parameter, miscibility and function in organic solar cells
journal, February 2018

Efficient organic solar cells processed from hydrocarbon solvents
journal, January 2016

Indacenodithiophene Semiconducting Polymers for High-Performance, Air-Stable Transistors
journal, August 2010

  • Zhang, Weimin; Smith, Jeremy; Watkins, Scott E.
  • Journal of the American Chemical Society, Vol. 132, Issue 33
  • DOI: 10.1021/ja1049324

Design of a Highly Crystalline Low-Band Gap Fused-Ring Electron Acceptor for High-Efficiency Solar Cells with Low Energy Loss
journal, September 2017

Nonfullerene Polymer Solar Cells with 8.5% Efficiency Enabled by a New Highly Twisted Electron Acceptor Dimer
journal, October 2015

  • Hwang, Ye-Jin; Li, Haiyan; Courtright, Brett A. E.
  • Advanced Materials, Vol. 28, Issue 1
  • DOI: 10.1002/adma.201503801

Constructing a Strongly Absorbing Low-Bandgap Polymer Acceptor for High-Performance All-Polymer Solar Cells
journal, September 2017

  • Zhang, Zhi-Guo; Yang, Yankang; Yao, Jia
  • Angewandte Chemie International Edition, Vol. 56, Issue 43
  • DOI: 10.1002/anie.201707678

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

Effect of traps on the performance of bulk heterojunction organic solar cells
journal, December 2007

  • Mandoc, M. M.; Kooistra, F. B.; Hummelen, J. C.
  • Applied Physics Letters, Vol. 91, Issue 26
  • DOI: 10.1063/1.2821368

Non-Fullerene Electron Acceptors for Use in Organic Solar Cells
journal, October 2015

  • Nielsen, Christian B.; Holliday, Sarah; Chen, Hung-Yang
  • Accounts of Chemical Research, Vol. 48, Issue 11
  • DOI: 10.1021/acs.accounts.5b00199

Two-Dimensional π-Expanded Quinoidal Terthiophenes Terminated with Dicyanomethylenes as n-Type Semiconductors for High-Performance Organic Thin-Film Transistors
journal, November 2014

  • Zhang, Cheng; Zang, Yaping; Gann, Eliot
  • Journal of the American Chemical Society, Vol. 136, Issue 46
  • DOI: 10.1021/ja510003y

Quantitative Morphology-Performance Correlations in Organic Solar Cells: Insights from Soft X-Ray Scattering
journal, May 2017

  • Jiao, Xuechen; Ye, Long; Ade, Harald
  • Advanced Energy Materials, Vol. 7, Issue 18
  • DOI: 10.1002/aenm.201700084

Energy-Level Modulation of Small-Molecule Electron Acceptors to Achieve over 12% Efficiency in Polymer Solar Cells
journal, September 2016

Ladder-Type Dithienonaphthalene-Based Small-Molecule Acceptors for Efficient Nonfullerene Organic Solar Cells
journal, September 2017

Molecular Optimization Enables over 13% Efficiency in Organic Solar Cells
journal, May 2017

  • Zhao, Wenchao; Li, Sunsun; Yao, Huifeng
  • Journal of the American Chemical Society, Vol. 139, Issue 21
  • DOI: 10.1021/jacs.7b02677

The Influence of Solvent Additive on Polymer Solar Cells Employing Fullerene and Non-Fullerene Acceptors
journal, November 2017

  • Song, Xin; Gasparini, Nicola; Baran, Derya
  • Advanced Electronic Materials, Vol. 4, Issue 10
  • DOI: 10.1002/aelm.201700358

Fused Nonacyclic Electron Acceptors for Efficient Polymer Solar Cells
journal, January 2017

  • Dai, Shuixing; Zhao, Fuwen; Zhang, Qianqian
  • Journal of the American Chemical Society, Vol. 139, Issue 3
  • DOI: 10.1021/jacs.6b12755

Characterization of the dominating bulk recombination in bulk-heterojunction blends using photoinduced absorption
journal, May 2016

  • Sandén, S.; Wilson, N. M.; Sandberg, O. J.
  • Applied Physics Letters, Vol. 108, Issue 19
  • DOI: 10.1063/1.4949016

Covalently Bound Clusters of Alpha-Substituted PDI—Rival Electron Acceptors to Fullerene for Organic Solar Cells
journal, June 2016

  • Wu, Qinghe; Zhao, Donglin; Schneider, Alexander M.
  • Journal of the American Chemical Society, Vol. 138, Issue 23
  • DOI: 10.1021/jacs.6b03562

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin-Film Transistors and All-Polymer Solar Cells
journal, November 2017

  • Wang, Yingfeng; Yan, Zhenglong; Guo, Han
  • Angewandte Chemie International Edition, Vol. 56, Issue 48
  • DOI: 10.1002/anie.201708421

Reducing the efficiency–stability–cost gap of organic photovoltaics with highly efficient and stable small molecule acceptor ternary solar cells
journal, November 2016

  • Baran, Derya; Ashraf, Raja Shahid; Hanifi, David A.
  • Nature Materials, Vol. 16, Issue 3
  • DOI: 10.1038/nmat4797

Organic Electronics: Does a Plot of the HOMO–LUMO Wave Functions Provide Useful Information?
journal, January 2017

11.4% Efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor
journal, December 2016

  • Bin, Haijun; Gao, Liang; Zhang, Zhi-Guo
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms13651

Fine-Tuned Photoactive and Interconnection Layers for Achieving over 13% Efficiency in a Fullerene-Free Tandem Organic Solar Cell
journal, May 2017

  • Cui, Yong; Yao, Huifeng; Gao, Bowei
  • Journal of the American Chemical Society, Vol. 139, Issue 21
  • DOI: 10.1021/jacs.7b01493

A Facile Planar Fused-Ring Electron Acceptor for As-Cast Polymer Solar Cells with 8.71% Efficiency
journal, February 2016

  • Lin, Yuze; He, Qiao; Zhao, Fuwen
  • Journal of the American Chemical Society, Vol. 138, Issue 9
  • DOI: 10.1021/jacs.6b00853

Solution-Processed Molecular Bis(Naphthalene Diimide) Derivatives with High Electron Mobility
journal, August 2011

  • Polander, Lauren E.; Tiwari, Shree P.; Pandey, Laxman
  • Chemistry of Materials, Vol. 23, Issue 15
  • DOI: 10.1021/cm201729s

Designing ternary blend bulk heterojunction solar cells with reduced carrier recombination and a fill factor of 77%
journal, August 2016

Fullerene-Free Polymer Solar Cells with over 11% Efficiency and Excellent Thermal Stability
journal, April 2016

  • Zhao, Wenchao; Qian, Deping; Zhang, Shaoqing
  • Advanced Materials, Vol. 28, Issue 23
  • DOI: 10.1002/adma.201600281

Small-Molecule Acceptor Based on the Heptacyclic Benzodi(cyclopentadithiophene) Unit for Highly Efficient Nonfullerene Organic Solar Cells
journal, March 2017

  • Kan, Bin; Feng, Huanran; Wan, Xiangjian
  • Journal of the American Chemical Society, Vol. 139, Issue 13
  • DOI: 10.1021/jacs.7b01170

Unconventional Molecular Weight Dependence of Charge Transport in the High Mobility n-type Semiconducting Polymer P(NDI2OD-T2)
journal, January 2017

  • Nahid, Masrur M.; Matsidik, Rukiya; Welford, Adam
  • Advanced Functional Materials, Vol. 27, Issue 9
  • DOI: 10.1002/adfm.201604744

New M- and V-shaped perylene diimide small molecules for high-performance nonfullerene polymer solar cells
journal, January 2016

  • Park, Gi Eun; Kim, Hyung Jong; Choi, Suna
  • Chemical Communications, Vol. 52, Issue 57
  • DOI: 10.1039/C6CC04229E

Breaking 10% Efficiency in Semitransparent Solar Cells with Fused-Undecacyclic Electron Acceptor
journal, December 2017

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