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

Title: Chemical and Morphological Control of Interfacial Self-Doping for Efficient Organic Electronics

Abstract

Solution-based processing of materials for electrical doping of organic semiconductor interfaces is attractive for boosting the efficiency of organic electronic devices with multilayer structures. In order to simplify this process, self-doping perylene diimide (PDI)-based ionene polymers are synthesized, in which the semiconductor PDI components are embedded together with electrolyte dopants in the polymer backbone. Functionality contained within the PDI monomers suppresses their aggregation, affording self-doping interlayers with controllable thickness when processed from solution into organic photovoltaic devices (OPVs). Optimal results for interfacial self-doping lead to increased power conversion efficiencies (PCEs) of the fullerene-based OPVs, from 2.62% to 10.64%, and of the nonfullerene-based OPVs, from 3.34% to 10.59%. These PDI–ionene interlayers enable chemical and morphological control of interfacial doping and conductivity, demonstrating that the conductive channels are crucial for charge transport in doped organic semiconductor films. Using these novel interlayers with efficient doping and high conductivity, both fullerene- and nonfullerene-based OPVs are achieved with PCEs exceeding 9% over interlayer thicknesses ranging from ≈3 to 40 nm.

Authors:
 [1];  [2];  [3];  [2];  [4];  [2]; ORCiD logo [1]
  1. Univ. of Massachusetts, Amherst, MA (United States). Polymer Science and Engineering Dept.; Beijing Univ. of Chemical Technology (China). Beijing Advanced Innovation Center for Soft Matter
  2. Univ. of Massachusetts, Amherst, MA (United States). Polymer Science and Engineering Dept.
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Sciences Division
  4. SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)
Publication Date:
Research Org.:
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); US Department of the Navy, Office of Naval Research (ONR); National Science Foundation (NSF)
OSTI Identifier:
1470752
Alternate Identifier(s):
OSTI ID: 1423702
Grant/Contract Number:  
N00014-17-1-2244; NSF‐CHE1506839; AC02-76SF00515
Resource Type:
Accepted Manuscript
Journal Name:
Advanced Materials
Additional Journal Information:
Journal Volume: 30; Journal Issue: 15; Journal ID: ISSN 0935-9648
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; conductivity; morphology characterizations; organic semiconductors; organic solar cells; self-doping

Citation Formats

Liu, Yao, Cole, Marcus D., Jiang, Yufeng, Kim, Paul Y., Nordlund, Dennis, Emrick, Todd, and Russell, Thomas P. Chemical and Morphological Control of Interfacial Self-Doping for Efficient Organic Electronics. United States: N. p., 2018. Web. doi:10.1002/adma.201705976.
Liu, Yao, Cole, Marcus D., Jiang, Yufeng, Kim, Paul Y., Nordlund, Dennis, Emrick, Todd, & Russell, Thomas P. Chemical and Morphological Control of Interfacial Self-Doping for Efficient Organic Electronics. United States. https://doi.org/10.1002/adma.201705976
Liu, Yao, Cole, Marcus D., Jiang, Yufeng, Kim, Paul Y., Nordlund, Dennis, Emrick, Todd, and Russell, Thomas P. Mon . "Chemical and Morphological Control of Interfacial Self-Doping for Efficient Organic Electronics". United States. https://doi.org/10.1002/adma.201705976. https://www.osti.gov/servlets/purl/1470752.
@article{osti_1470752,
title = {Chemical and Morphological Control of Interfacial Self-Doping for Efficient Organic Electronics},
author = {Liu, Yao and Cole, Marcus D. and Jiang, Yufeng and Kim, Paul Y. and Nordlund, Dennis and Emrick, Todd and Russell, Thomas P.},
abstractNote = {Solution-based processing of materials for electrical doping of organic semiconductor interfaces is attractive for boosting the efficiency of organic electronic devices with multilayer structures. In order to simplify this process, self-doping perylene diimide (PDI)-based ionene polymers are synthesized, in which the semiconductor PDI components are embedded together with electrolyte dopants in the polymer backbone. Functionality contained within the PDI monomers suppresses their aggregation, affording self-doping interlayers with controllable thickness when processed from solution into organic photovoltaic devices (OPVs). Optimal results for interfacial self-doping lead to increased power conversion efficiencies (PCEs) of the fullerene-based OPVs, from 2.62% to 10.64%, and of the nonfullerene-based OPVs, from 3.34% to 10.59%. These PDI–ionene interlayers enable chemical and morphological control of interfacial doping and conductivity, demonstrating that the conductive channels are crucial for charge transport in doped organic semiconductor films. Using these novel interlayers with efficient doping and high conductivity, both fullerene- and nonfullerene-based OPVs are achieved with PCEs exceeding 9% over interlayer thicknesses ranging from ≈3 to 40 nm.},
doi = {10.1002/adma.201705976},
journal = {Advanced Materials},
number = 15,
volume = 30,
place = {United States},
year = {Mon Mar 05 00:00:00 EST 2018},
month = {Mon Mar 05 00:00:00 EST 2018}
}

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

Citation Metrics:
Cited by: 58 works
Citation information provided by
Web of Science

Figures / Tables:

Figure 1 Figure 1: Chemical structures of the POI-based ionene interlayers and the photoactive layers used to prepare the OPV devices in this work (ITO: indium tin oxide; PED OT:PSS: poly(ethylenedioxythiophene) poly(styrene sulfonate )) .

Save / Share:

Works referenced in this record:

Low-Bandgap Near-IR Conjugated Polymers/Molecules for Organic Electronics
journal, August 2015


Molecular Design of Benzodithiophene-Based Organic Photovoltaic Materials
journal, June 2016


Bulk Heterojunction versus Diffused Bilayer: The Role of Device Geometry in Solution p-Doped Polymer-Based Solar Cells
journal, July 2012

  • Loiudice, Anna; Rizzo, Aurora; Biasiucci, Mariano
  • The Journal of Physical Chemistry Letters, Vol. 3, Issue 14
  • DOI: 10.1021/jz300754p

Contact engineering in organic field-effect transistors
journal, March 2015


Triarylamine: Versatile Platform for Organic, Dye-Sensitized, and Perovskite Solar Cells
journal, November 2016


Interface design for high-efficiency non-fullerene polymer solar cells
journal, January 2017

  • Sun, Chen; Wu, Zhihong; Hu, Zhanhao
  • Energy & Environmental Science, Vol. 10, Issue 8
  • DOI: 10.1039/C7EE00601B

Water/alcohol soluble conjugated polymers as highly efficient electron transporting/injection layer in optoelectronic devices
journal, January 2010

  • Huang, Fei; Wu, Hongbin; Cao, Yong
  • Chemical Society Reviews, Vol. 39, Issue 7
  • DOI: 10.1039/b907991m

Doping of organic semiconductors
journal, December 2012


Simultaneous cross-linking and p-doping of a polymeric semiconductor film by immersion into a phosphomolybdic acid solution for use in organic solar cells
journal, January 2016

  • Aizawa, Naoya; Fuentes-Hernandez, Canek; Kolesov, Vladimir A.
  • Chemical Communications, Vol. 52, Issue 19
  • DOI: 10.1039/C6CC01022A

A Self-Doping, O2-Stable, n-Type Interfacial Layer for Organic Electronics
journal, March 2012

  • Reilly, Thomas H.; Hains, Alexander W.; Chen, Hsiang-Yu
  • Advanced Energy Materials, Vol. 2, Issue 4
  • DOI: 10.1002/aenm.201100446

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

Contact Doping with Sub-Monolayers of Strong Polyelectrolytes for Organic Photovoltaics
journal, May 2014

  • Mor, Gopal K.; Jones, David; Le, Thinh P.
  • Advanced Energy Materials, Vol. 4, Issue 13
  • DOI: 10.1002/aenm.201400439

Single-junction polymer solar cells with high efficiency and photovoltage
journal, February 2015


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

  • Chueh, Chu-Chen; Li, Chang-Zhi; Jen, Alex K. -Y.
  • Energy & Environmental Science, Vol. 8, Issue 4
  • DOI: 10.1039/C4EE03824J

Quaternisation-polymerized N-type polyelectrolytes: synthesis, characterisation and application in high-performance polymer solar cells
journal, January 2017

  • Hu, Zhicheng; Xu, Rongguo; Dong, Sheng
  • Materials Horizons, Vol. 4, Issue 1
  • DOI: 10.1039/C6MH00434B

Ion Motion in Conjugated Polyelectrolyte Electron Transporting Layers
journal, September 2007

  • Hoven, Corey; Yang, Renqiang; Garcia, Andres
  • Journal of the American Chemical Society, Vol. 129, Issue 36
  • DOI: 10.1021/ja072612q

Doped polymer semiconductors with ultrahigh and ultralow work functions for ohmic contacts
journal, November 2016

  • Tang, Cindy G.; Ang, Mervin C. Y.; Choo, Kim-Kian
  • Nature, Vol. 539, Issue 7630
  • DOI: 10.1038/nature20133

Measurement of Small Molecular Dopant F4TCNQ and C 60 F 36 Diffusion in Organic Bilayer Architectures
journal, December 2015

  • Li, Jun; Rochester, Chris W.; Jacobs, Ian E.
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 51
  • DOI: 10.1021/acsami.5b09216

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

Power Factor Enhancement in Solution-Processed Organic n-Type Thermoelectrics Through Molecular Design
journal, March 2014

  • Russ, Boris; Robb, Maxwell J.; Brunetti, Fulvio G.
  • Advanced Materials, Vol. 26, Issue 21
  • DOI: 10.1002/adma.201306116

Highly Efficient Organic Devices Based on Electrically Doped Transport Layers
journal, April 2007

  • Walzer, K.; Maennig, B.; Pfeiffer, M.
  • Chemical Reviews, Vol. 107, Issue 4
  • DOI: 10.1021/cr050156n

A Universal Method to Produce Low-Work Function Electrodes for Organic Electronics
journal, April 2012


Doped Organic Semiconductors: Trap-Filling, Impurity Saturation, and Reserve Regimes
journal, March 2015

  • Tietze, Max L.; Pahner, Paul; Schmidt, Kathleen
  • Advanced Functional Materials, Vol. 25, Issue 18
  • DOI: 10.1002/adfm.201404549

Conjugated Polymer Zwitterions: Efficient Interlayer Materials in Organic Electronics
journal, October 2016


Recent Advances in Bulk Heterojunction Polymer Solar Cells
journal, August 2015


Electron injection into organic semiconductor devices from high work function cathodes
journal, August 2008

  • Hoven, C. V.; Yang, R.; Garcia, A.
  • Proceedings of the National Academy of Sciences, Vol. 105, Issue 35
  • DOI: 10.1073/pnas.0806494105

Molecular Electrical Doping of Organic Semiconductors: Fundamental Mechanisms and Emerging Dopant Design Rules
journal, February 2016


Fulleropyrrolidine interlayers: Tailoring electrodes to raise organic solar cell efficiency
journal, September 2014


Perylene Diimide-Based Ionene and Zwitterionic Polymers: Synthesis and Solution Photophysical Properties
journal, September 2017


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

Solution-based electrical doping of semiconducting polymer films over a limited depth
journal, December 2016

  • Kolesov, Vladimir A.; Fuentes-Hernandez, Canek; Chou, Wen-Fang
  • Nature Materials, Vol. 16, Issue 4
  • DOI: 10.1038/nmat4818

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


Charge Transport in Electrically Doped Amorphous Organic Semiconductors
journal, April 2015

  • Yoo, Seung-Jun; Kim, Jang-Joo
  • Macromolecular Rapid Communications, Vol. 36, Issue 11
  • DOI: 10.1002/marc.201500026

Doped Organic Transistors
journal, October 2016


N-Doped Zwitterionic Fullerenes as Interlayers in Organic and Perovskite Photovoltaic Devices
journal, April 2017


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

Electron transporting semiconducting polymers in organic electronics
journal, January 2011

  • Zhao, Xingang; Zhan, Xiaowei
  • Chemical Society Reviews, Vol. 40, Issue 7
  • DOI: 10.1039/c0cs00194e

Enhanced Charge-Carrier Injection and Collection Via Lamination of Doped Polymer Layers p-Doped with a Solution-Processible Molybdenum Complex
journal, December 2013

  • Dai, An; Zhou, Yinhua; Shu, Andrew L.
  • Advanced Functional Materials, Vol. 24, Issue 15
  • DOI: 10.1002/adfm.201303232

Use of a High Electron-Affinity Molybdenum Dithiolene Complex to p-Dope Hole-Transport Layers
journal, September 2009

  • Qi, Yabing; Sajoto, Tissa; Barlow, Stephen
  • Journal of the American Chemical Society, Vol. 131, Issue 35
  • DOI: 10.1021/ja904939g

Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics
journal, November 2011

  • Wang, Chengliang; Dong, Huanli; Hu, Wenping
  • Chemical Reviews, Vol. 112, Issue 4
  • DOI: 10.1021/cr100380z

Ultralow Doping in Organic Semiconductors: Evidence of Trap Filling
journal, October 2012


Self-Doped, n-Type Perylene Diimide Derivatives as Electron Transporting Layers for High-Efficiency Polymer Solar Cells
journal, April 2017

  • Wang, Zhenfeng; Zheng, Nannan; Zhang, Wenqiang
  • Advanced Energy Materials, Vol. 7, Issue 15
  • DOI: 10.1002/aenm.201700232

Highly Efficient Organic Devices Based on Electrically Doped Transport Layers
journal, July 2007


Fused nonacyclic electron acceptors for efficient polymer solar cells
text, January 2017

  • Qidan, Ling,; Qianqian, Zhang,; Wei, You,
  • American Chemical Society
  • DOI: 10.17615/9yfc-2e87

Works referencing / citing this record:

Tailoring and Modifying an Organic Electron Acceptor toward the Cathode Interlayer for Highly Efficient Organic Solar Cells
journal, November 2019


Efficient n-Dopants and Their Roles in Organic Electronics
journal, July 2018

  • Bin, Zhengyang; Liu, Ziyang; Qiu, Yong
  • Advanced Optical Materials, Vol. 6, Issue 18
  • DOI: 10.1002/adom.201800536

Controlled Design of a Robust Hierarchically Porous and Hollow Carbon Fiber Textile for High‐Performance Freestanding Electrodes
journal, September 2019


Zwitterions for Organic/Perovskite Solar Cells, Light-Emitting Devices, and Lithium Ion Batteries: Recent Progress and Perspectives
journal, January 2019

  • Islam, Amjad; Li, Jianguo; Pervaiz, Muhammad
  • Advanced Energy Materials, Vol. 9, Issue 10
  • DOI: 10.1002/aenm.201803354

Transforming Ionene Polymers into Efficient Cathode Interlayers with Pendent Fullerenes
journal, March 2019


Transforming Ionene Polymers into Efficient Cathode Interlayers with Pendent Fullerenes
journal, March 2019

  • Liu, Yao; Sheri, Madhu; Cole, Marcus D.
  • Angewandte Chemie International Edition, Vol. 58, Issue 17
  • DOI: 10.1002/anie.201901536

Solution‐Processable Conductive Organics via Anion‐Induced n‐Doping and Their Applications in Organic and Perovskite Solar Cells
journal, April 2019

  • Yan, Kangrong; Li, Chang‐Zhi
  • Macromolecular Chemistry and Physics, Vol. 220, Issue 10
  • DOI: 10.1002/macp.201900084

Perylene derivatives for solar cells and energy harvesting: a review of materials, challenges and advances
journal, August 2019

  • Macedo, Andreia Gerniski; Christopholi, Leticia Patricio; Gavim, Anderson E. X.
  • Journal of Materials Science: Materials in Electronics, Vol. 30, Issue 17
  • DOI: 10.1007/s10854-019-02019-z

Allylamine PECVD Modification of PDMS as Simple Method to Obtain Conductive Flexible Polypyrrole Thin Films
journal, December 2019


Allylamine PECVD Modification of PDMS as Simple Method to Obtain Conductive Flexible Polypyrrole Thin Films
journal, December 2019


Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.