N-Doping improves charge transport and morphology in the organic non-fullerene acceptor O-IDTBR
Abstract
Molecular doping has been shown to improve the performance of various organic (opto)electronic devices. When compared to p-doped systems, research into n-doped organic small-molecules is relatively limited, primarily due to the lack of suitable dopants and the often encountered unfavourable microstructural effects. These factors have prevented the use of n-doping in a wider range of existing materials, such as non-fullerene acceptors (NFAs), that have already shown great promise for a range of (opto)electronic applications. Here, we show that several different molecular n-dopants, namely [1,2-b:2',1'-d]benzo[i][2.5]benzodiazocine potassium triflate adduct (DMBI-BDZC), tetra-n-butylammonium fluoride (TBAF) and 4-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine (N-DMBI), can be used to n-dope the molecular semiconductor O-IDTBR, a promising NFA, and increase the electron field-effect mobility to >1 cm2 V-1 s-1. By combining complementary experimental techniques with computer simulations of doping and charge carrier dynamics, we show that improved charge transport arises from synergistic effects of n-type doping and morphological changes. Specifically, a new, previously unreported dopant-induced packing orientation results in one of the highest electron mobility values reported to-date for an NFA molecule. Overall, this work highlights the importance of dopant–semiconductor interactions and their impact on morphology, showing that dopant-induced molecular packing motifs may be generic and a key element of the chargemore »
- Authors:
-
- Univ. of Kentucky, Lexington, KY (United States); King Abdullah University of Science and Technology (Saudi Arabia)
- Brookhaven National Lab. (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)
- Max Planck Inst. for Polymer Research, Mainz (Germany)
- National Technical University of Athens (Greece)
- King Abdullah University of Science and Technology (Saudi Arabia)
- Imperial College, London (United Kingdom)
- Univ. of Oxford (United Kingdom)
- Publication Date:
- Research Org.:
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1776539
- Report Number(s):
- BNL-221238-2021-JAAM
Journal ID: ISSN 2050-7526
- Grant/Contract Number:
- SC0012704
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Materials Chemistry C
- Additional Journal Information:
- Journal Volume: 9; Journal Issue: 13; Journal ID: ISSN 2050-7526
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Paterson, Alexandra F., Li, Ruipeng, Markina, Anastasia, Tsetseris, Leonidas, MacPhee, Sky, Faber, Hendrik, Emwas, Abdul-Hamid, Panidi, Julianna, Bristow, Helen, Wadsworth, Andrew, Baran, Derya, Andrienko, Denis, Heeney, Martin, McCulloch, Iain, and Anthopoulos, Thomas D. N-Doping improves charge transport and morphology in the organic non-fullerene acceptor O-IDTBR. United States: N. p., 2021.
Web. doi:10.1039/d0tc05861k.
Paterson, Alexandra F., Li, Ruipeng, Markina, Anastasia, Tsetseris, Leonidas, MacPhee, Sky, Faber, Hendrik, Emwas, Abdul-Hamid, Panidi, Julianna, Bristow, Helen, Wadsworth, Andrew, Baran, Derya, Andrienko, Denis, Heeney, Martin, McCulloch, Iain, & Anthopoulos, Thomas D. N-Doping improves charge transport and morphology in the organic non-fullerene acceptor O-IDTBR. United States. https://doi.org/10.1039/d0tc05861k
Paterson, Alexandra F., Li, Ruipeng, Markina, Anastasia, Tsetseris, Leonidas, MacPhee, Sky, Faber, Hendrik, Emwas, Abdul-Hamid, Panidi, Julianna, Bristow, Helen, Wadsworth, Andrew, Baran, Derya, Andrienko, Denis, Heeney, Martin, McCulloch, Iain, and Anthopoulos, Thomas D. Wed .
"N-Doping improves charge transport and morphology in the organic non-fullerene acceptor O-IDTBR". United States. https://doi.org/10.1039/d0tc05861k. https://www.osti.gov/servlets/purl/1776539.
@article{osti_1776539,
title = {N-Doping improves charge transport and morphology in the organic non-fullerene acceptor O-IDTBR},
author = {Paterson, Alexandra F. and Li, Ruipeng and Markina, Anastasia and Tsetseris, Leonidas and MacPhee, Sky and Faber, Hendrik and Emwas, Abdul-Hamid and Panidi, Julianna and Bristow, Helen and Wadsworth, Andrew and Baran, Derya and Andrienko, Denis and Heeney, Martin and McCulloch, Iain and Anthopoulos, Thomas D.},
abstractNote = {Molecular doping has been shown to improve the performance of various organic (opto)electronic devices. When compared to p-doped systems, research into n-doped organic small-molecules is relatively limited, primarily due to the lack of suitable dopants and the often encountered unfavourable microstructural effects. These factors have prevented the use of n-doping in a wider range of existing materials, such as non-fullerene acceptors (NFAs), that have already shown great promise for a range of (opto)electronic applications. Here, we show that several different molecular n-dopants, namely [1,2-b:2',1'-d]benzo[i][2.5]benzodiazocine potassium triflate adduct (DMBI-BDZC), tetra-n-butylammonium fluoride (TBAF) and 4-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine (N-DMBI), can be used to n-dope the molecular semiconductor O-IDTBR, a promising NFA, and increase the electron field-effect mobility to >1 cm2 V-1 s-1. By combining complementary experimental techniques with computer simulations of doping and charge carrier dynamics, we show that improved charge transport arises from synergistic effects of n-type doping and morphological changes. Specifically, a new, previously unreported dopant-induced packing orientation results in one of the highest electron mobility values reported to-date for an NFA molecule. Overall, this work highlights the importance of dopant–semiconductor interactions and their impact on morphology, showing that dopant-induced molecular packing motifs may be generic and a key element of the charge transport enhancement observed in doped organics.},
doi = {10.1039/d0tc05861k},
journal = {Journal of Materials Chemistry C},
number = 13,
volume = 9,
place = {United States},
year = {Wed Mar 10 00:00:00 EST 2021},
month = {Wed Mar 10 00:00:00 EST 2021}
}
Works referenced in this record:
Controlling Molecular Doping in Organic Semiconductors
journal, September 2017
- Jacobs, Ian E.; Moulé, Adam J.
- Advanced Materials, Vol. 29, Issue 42
Doping: A Key Enabler for Organic Transistors
journal, August 2018
- Xu, Yong; Sun, Huabin; Liu, Ao
- Advanced Materials, Vol. 30, Issue 46
Contact Resistance in Organic Field‐Effect Transistors: Conquering the Barrier
journal, September 2019
- Waldrip, Matthew; Jurchescu, Oana D.; Gundlach, David J.
- Advanced Functional Materials, Vol. 30, Issue 20
The Impact of Molecular p-Doping on Charge Transport in High-Mobility Small-Molecule/Polymer Blend Organic Transistors
journal, December 2017
- Paterson, Alexandra F.; Lin, Yen-Hung; Mottram, Alexander D.
- Advanced Electronic Materials, Vol. 4, Issue 10
Doped Organic Transistors
journal, October 2016
- Lüssem, Björn; Keum, Chang-Min; Kasemann, Daniel
- Chemical Reviews, Vol. 116, Issue 22
Molecular Electrical Doping of Organic Semiconductors: Fundamental Mechanisms and Emerging Dopant Design Rules
journal, February 2016
- Salzmann, Ingo; Heimel, Georg; Oehzelt, Martin
- Accounts of Chemical Research, Vol. 49, Issue 3
Doping of Organic Semiconductors: Impact of Dopant Strength and Electronic Coupling
journal, June 2013
- Méndez, Henry; Heimel, Georg; Opitz, Andreas
- Angewandte Chemie International Edition, Vol. 52, Issue 30
Doping of organic semiconductors
journal, December 2012
- Lüssem, B.; Riede, M.; Leo, K.
- physica status solidi (a), Vol. 210, Issue 1
Addition of the Lewis Acid Zn(C 6 F 5 ) 2 Enables Organic Transistors with a Maximum Hole Mobility in Excess of 20 cm 2 V −1 s −1
journal, May 2019
- Paterson, Alexandra F.; Tsetseris, Leonidas; Li, Ruipeng
- Advanced Materials, Vol. 31, Issue 27
Remarkable Enhancement of the Hole Mobility in Several Organic Small-Molecules, Polymers, and Small-Molecule:Polymer Blend Transistors by Simple Admixing of the Lewis Acid p-Dopant B(C 6 F 5 ) 3
journal, October 2017
- Panidi, Julianna; Paterson, Alexandra F.; Khim, Dongyoon
- Advanced Science, Vol. 5, Issue 1
Anion-induced N-doping of naphthalenediimide polymer semiconductor in organic thin-film transistors
journal, April 2018
- Han, Yang; Fei, Zhuping; Lin, Yen-Hung
- npj Flexible Electronics, Vol. 2, Issue 1
Introducing a Nonvolatile N‐Type Dopant Drastically Improves Electron Transport in Polymer and Small‐Molecule Organic Transistors
journal, June 2019
- Panidi, Julianna; Kainth, Jaspreet; Paterson, Alexandra F.
- Advanced Functional Materials, Vol. 29, Issue 34
Use of a 1 H -Benzoimidazole Derivative as an n -Type Dopant and To Enable Air-Stable Solution-Processed n -Channel Organic Thin-Film Transistors
journal, July 2010
- Wei, Peng; Oh, Joon Hak; Dong, Guifang
- Journal of the American Chemical Society, Vol. 132, Issue 26
A New Acceptor for Highly Efficient Organic Solar Cells
journal, April 2019
- Gao, Feng
- Joule, Vol. 3, Issue 4
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
Impact of Nonfullerene Acceptor Side Chain Variation on Transistor Mobility
journal, July 2019
- Bristow, Helen; Thorley, Karl J.; White, Andrew J. P.
- Advanced Electronic Materials, Vol. 5, Issue 10
Recent Progress in High-Mobility Organic Transistors: A Reality Check
journal, July 2018
- Paterson, Alexandra F.; Singh, Saumya; Fallon, Kealan J.
- Advanced Materials, Vol. 30, Issue 36
Systematic Study of Widely Applicable N-Doping Strategy for High-Performance Solution-Processed Field-Effect Transistors
journal, September 2016
- Kim, Jihong; Khim, Dongyoon; Baeg, Kang-Jun
- Advanced Functional Materials, Vol. 26, Issue 43
High Conductivity and Electron-Transfer Validation in an n-Type Fluoride-Anion-Doped Polymer for Thermoelectrics in Air
journal, July 2017
- Zhao, Xingang; Madan, Deepa; Cheng, Yan
- Advanced Materials, Vol. 29, Issue 34
Hybrid Modulation-Doping of Solution-Processed Ultrathin Layers of ZnO Using Molecular Dopants
journal, October 2015
- Schießl, Stefan P.; Faber, Hendrik; Lin, Yen-Hung
- Advanced Materials, Vol. 28, Issue 20
Enhanced Efficiency and Long-Term Stability of Perovskite Solar Cells by Synergistic Effect of Nonhygroscopic Doping in Conjugated Polymer-Based Hole-Transporting Layer
journal, December 2017
- Koh, Chang Woo; Heo, Jin Hyuck; Uddin, Mohammad Afsar
- ACS Applied Materials & Interfaces, Vol. 9, Issue 50
Toward high-efficiency, hysteresis-less, stable perovskite solar cells: unusual doping of a hole-transporting material using a fluorine-containing hydrophobic Lewis acid
journal, January 2018
- Luo, Junsheng; Xia, Jianxing; Yang, Hua
- Energy & Environmental Science, Vol. 11, Issue 8
Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics
journal, January 2018
- Kiefer, David; Giovannitti, Alexander; Sun, Hengda
- ACS Energy Letters, Vol. 3, Issue 2
Critical assessment of charge mobility extraction in FETs
journal, December 2017
- Choi, Hyun Ho; Cho, Kilwon; Frisbie, C. Daniel
- Nature Materials, Vol. 17, Issue 1
Remarkable Mobility Increase and Threshold Voltage Reduction in Organic Field-Effect Transistors by Overlaying Discontinuous Nano-Patches of Charge-Transfer Doping Layer on Top of Semiconducting Film
journal, November 2012
- Kim, Jong H.; Yun, Sun Woo; An, Byeong-Kwan
- Advanced Materials, Vol. 25, Issue 5
Charge transport in polymeric transistors
journal, March 2007
- Salleo, Alberto
- Materials Today, Vol. 10, Issue 3
Device Physics of Contact Issues for the Overestimation and Underestimation of Carrier Mobility in Field-Effect Transistors
journal, September 2017
- Liu, Chuan; Li, Gongtan; Di Pietro, Riccardo
- Physical Review Applied, Vol. 8, Issue 3
Calculating the trap density of states in organic field-effect transistors from experiment: A comparison of different methods
journal, January 2010
- Kalb, Wolfgang L.; Batlogg, Bertram
- Physical Review B, Vol. 81, Issue 3
Impact of the Gate Dielectric on Contact Resistance in High‐Mobility Organic Transistors
journal, March 2019
- Paterson, Alexandra F.; Mottram, Alexander D.; Faber, Hendrik
- Advanced Electronic Materials, Vol. 5, Issue 5
Polymer:Nonfullerene Bulk Heterojunction Solar Cells with Exceptionally Low Recombination Rates
journal, September 2017
- Gasparini, Nicola; Salvador, Michael; Heumueller, Thomas
- Advanced Energy Materials, Vol. 7, Issue 22
Deep Energetic Trap States in Organic Photovoltaic Devices
journal, November 2011
- Shuttle, Christopher G.; Treat, Neil D.; Douglas, Jessica D.
- Advanced Energy Materials, Vol. 2, Issue 1
Grain Boundary Induced Bias Instability in Soluble Acene-Based Thin-Film Transistors
journal, September 2016
- Nguyen, Ky V.; Payne, Marcia M.; Anthony, John E.
- Scientific Reports, Vol. 6, Issue 1
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
Rational Design of Organic Semiconductors for Texture Control and Self-Patterning on Halogenated Surfaces
journal, May 2014
- Ward, Jeremy W.; Li, Ruipeng; Obaid, Abdulmalik
- Advanced Functional Materials, Vol. 24, Issue 32
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
An Efficient, “Burn in” Free Organic Solar Cell Employing a Nonfullerene Electron Acceptor
journal, June 2017
- Cha, Hyojung; Wu, Jiaying; Wadsworth, Andrew
- Advanced Materials, Vol. 29, Issue 33
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
Carrier Transport and Recombination in Efficient “All-Small-Molecule” Solar Cells with the Nonfullerene Acceptor IDTBR
journal, April 2018
- Liang, Ru-Ze; Babics, Maxime; Savikhin, Victoria
- Advanced Energy Materials, Vol. 8, Issue 19
Mechanistic Study on the Solution-Phase n-Doping of 1,3-Dimethyl-2-aryl-2,3-dihydro-1 H -benzoimidazole Derivatives
journal, September 2013
- Naab, Benjamin D.; Guo, Song; Olthof, Selina
- Journal of the American Chemical Society, Vol. 135, Issue 40
Polaron Confinement in n-Doped P(NDI2OD-T2) Unveiled by Vibrational Spectroscopy
journal, December 2018
- Denti, Ilaria; Cimò, Simone; Brambilla, Luigi
- Chemistry of Materials, Vol. 31, Issue 17
Enhanced π–π Interactions of Nonfullerene Acceptors by Volatilizable Solid Additives in Efficient Polymer Solar Cells
journal, February 2019
- Yu, Runnan; Yao, Huifeng; Chen, Zhenyu
- Advanced Materials, Vol. 31, Issue 18
Dopant-Induced Ordering of Amorphous Regions in Regiorandom P3HT
journal, August 2019
- Yee, Patrick Y.; Scholes, D. Tyler; Schwartz, Benjamin J.
- The Journal of Physical Chemistry Letters, Vol. 10, Issue 17
Long-Range Embedding of Molecular Ions and Excitations in a Polarizable Molecular Environment
journal, August 2016
- Poelking, Carl; Andrienko, Denis
- Journal of Chemical Theory and Computation, Vol. 12, Issue 9
Microscopic Simulations of Charge Transport in Disordered Organic Semiconductors
journal, August 2011
- Rühle, Victor; Lukyanov, Alexander; May, Falk
- Journal of Chemical Theory and Computation, Vol. 7, Issue 10
A window to trap-free charge transport in organic semiconducting thin films
journal, September 2019
- Kotadiya, Naresh B.; Mondal, Anirban; Blom, Paul W. M.
- Nature Materials, Vol. 18, Issue 11
Electron Trapping in Conjugated Polymers
journal, December 2018
- Abbaszadeh, Davood; Kunz, Alexander; Kotadiya, Naresh B.
- Chemistry of Materials, Vol. 31, Issue 17
NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations
journal, September 2010
- Valiev, M.; Bylaska, E. J.; Govind, N.
- Computer Physics Communications, Vol. 181, Issue 9, p. 1477-1489
Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993
- Becke, Axel D.
- The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
journal, November 1994
- Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.
- The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
journal, April 2010
- Grimme, Stefan; Antony, Jens; Ehrlich, Stephan
- The Journal of Chemical Physics, Vol. 132, Issue 15
Density-functional based determination of intermolecular charge transfer properties for large-scale morphologies
journal, January 2010
- Baumeier, Björn; Kirkpatrick, James; Andrienko, Denis
- Physical Chemistry Chemical Physics, Vol. 12, Issue 36
Characterization of Charge-Carrier Transport in Semicrystalline Polymers: Electronic Couplings, Site Energies, and Charge-Carrier Dynamics in Poly(bithiophene- alt -thienothiophene) [PBTTT]
journal, January 2013
- Poelking, Carl; Cho, Eunkyung; Malafeev, Alexander
- The Journal of Physical Chemistry C, Vol. 117, Issue 4
GROMACS 4: Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation
journal, February 2008
- Hess, Berk; Kutzner, Carsten; van der Spoel, David
- Journal of Chemical Theory and Computation, Vol. 4, Issue 3
GROMACS 4.5: a high-throughput and highly parallel open source molecular simulation toolkit
journal, February 2013
- Pronk, Sander; Páll, Szilárd; Schulz, Roland
- Bioinformatics, Vol. 29, Issue 7
17.1% Efficient Single‐Junction Organic Solar Cells Enabled by n‐Type Doping of the Bulk‐Heterojunction
journal, February 2020
- Lin, Yuanbao; Firdaus, Yuliar; Nugraha, Mohamad Insan
- Advanced Science, Vol. 7, Issue 7