Sequential Doping of Ladder-Type Conjugated Polymers for Thermally Stable n-Type Organic Conductors
Abstract
Doping of organic semiconductors is a powerful tool to optimize the performance of various organic (opto)electronic and bioelectronic devices. Despite recent advances, the low thermal stability of the electronic properties of doped polymers still represents a significant obstacle to implementing these materials into practical applications. Hence, the development of conducting doped polymers with excellent long-term stability at elevated temperatures is highly desirable. Here, we report on the sequential doping of the ladder-type polymer poly(benzimidazobenzophenanthroline) (BBL) with a benzimidazole-based dopant (i.e., N-DMBI). By combining electrical, UV–vis/infrared, X-ray diffraction, and electron paramagnetic resonance measurements, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and microstructure of the sequentially doped polymer films as a function of the thermal annealing temperature. Importantly, we observed that the electrical conductivity of N-DMBI-doped BBL remains unchanged even after 20 h of heating at 190 °C. This finding is remarkable and of particular interest for organic thermoelectrics.
- Authors:
-
[1];
[2];
[2];
[2];
[4];
[2];
[3];
[2]
- Linköping Univ., Norrköping (Sweden); Paris Univ., Cergy (France)
- Linköping Univ., Norrköping (Sweden)
- Chalmers Univ. of Technology, Goteborg (Sweden)
- SLAC National Accelerator Lab., Menlo Park, CA (United States)
- Publication Date:
- Research Org.:
- SLAC National Accelerator Lab., Menlo Park, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1768776
- Grant/Contract Number:
- AC02-76SF00515; 2016-03979; SFO-Mat-LiU No 2009 00971; Dnr KAW 2014.0041; 18-313; 19-310; 204-0256
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Applied Materials and Interfaces
- Additional Journal Information:
- Journal Volume: 12; Journal Issue: 47; Journal ID: ISSN 1944-8244
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; conjugated polymers; sequential doping; n-doping; organic thermoelectrics; ladder-type polymers; thermal stability; impurities; thin films; electrical conductivity; doping; annealing (metallurgy)
Citation Formats
Wang, Suhao, Ruoko, Tero-Petri, Wang, Gang, Riera-Galindo, Sergi, Hultmark, Sandra, Puttisong, Yuttapoom, Moro, Fabrizio, Yan, Hongping, Chen, Weimin M., Berggren, Magnus, Müller, Christian, and Fabiano, Simone. Sequential Doping of Ladder-Type Conjugated Polymers for Thermally Stable n-Type Organic Conductors. United States: N. p., 2020.
Web. doi:10.1021/acsami.0c16254.
Wang, Suhao, Ruoko, Tero-Petri, Wang, Gang, Riera-Galindo, Sergi, Hultmark, Sandra, Puttisong, Yuttapoom, Moro, Fabrizio, Yan, Hongping, Chen, Weimin M., Berggren, Magnus, Müller, Christian, & Fabiano, Simone. Sequential Doping of Ladder-Type Conjugated Polymers for Thermally Stable n-Type Organic Conductors. United States. https://doi.org/10.1021/acsami.0c16254
Wang, Suhao, Ruoko, Tero-Petri, Wang, Gang, Riera-Galindo, Sergi, Hultmark, Sandra, Puttisong, Yuttapoom, Moro, Fabrizio, Yan, Hongping, Chen, Weimin M., Berggren, Magnus, Müller, Christian, and Fabiano, Simone. Thu .
"Sequential Doping of Ladder-Type Conjugated Polymers for Thermally Stable n-Type Organic Conductors". United States. https://doi.org/10.1021/acsami.0c16254. https://www.osti.gov/servlets/purl/1768776.
@article{osti_1768776,
title = {Sequential Doping of Ladder-Type Conjugated Polymers for Thermally Stable n-Type Organic Conductors},
author = {Wang, Suhao and Ruoko, Tero-Petri and Wang, Gang and Riera-Galindo, Sergi and Hultmark, Sandra and Puttisong, Yuttapoom and Moro, Fabrizio and Yan, Hongping and Chen, Weimin M. and Berggren, Magnus and Müller, Christian and Fabiano, Simone},
abstractNote = {Doping of organic semiconductors is a powerful tool to optimize the performance of various organic (opto)electronic and bioelectronic devices. Despite recent advances, the low thermal stability of the electronic properties of doped polymers still represents a significant obstacle to implementing these materials into practical applications. Hence, the development of conducting doped polymers with excellent long-term stability at elevated temperatures is highly desirable. Here, we report on the sequential doping of the ladder-type polymer poly(benzimidazobenzophenanthroline) (BBL) with a benzimidazole-based dopant (i.e., N-DMBI). By combining electrical, UV–vis/infrared, X-ray diffraction, and electron paramagnetic resonance measurements, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and microstructure of the sequentially doped polymer films as a function of the thermal annealing temperature. Importantly, we observed that the electrical conductivity of N-DMBI-doped BBL remains unchanged even after 20 h of heating at 190 °C. This finding is remarkable and of particular interest for organic thermoelectrics.},
doi = {10.1021/acsami.0c16254},
journal = {ACS Applied Materials and Interfaces},
number = 47,
volume = 12,
place = {United States},
year = {Thu Nov 12 00:00:00 EST 2020},
month = {Thu Nov 12 00:00:00 EST 2020}
}
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Works referenced in this record:
Influence of PEDOT:PSS crystallinity and composition on electrochemical transistor performance and long-term stability
journal, September 2018
- Kim, Seong-Min; Kim, Chang-Hyun; Kim, Youngseok
- Nature Communications, Vol. 9, Issue 1
Thermoelectric Performance of n‐Type Poly(Ni‐tetrathiooxalate) as a Counterpart to Poly(Ni‐ethenetetrathiolate): NiTTO versus NiETT
journal, March 2019
- Wolfe, Rylan M. W.; Menon, Akanksha K.; Marder, Seth R.
- Advanced Electronic Materials, Vol. 5, Issue 11
On the Glass Transition of Polymer Semiconductors and Its Impact on Polymer Solar Cell Stability
journal, March 2015
- Müller, Christian
- Chemistry of Materials, Vol. 27, Issue 8
Air Stable Organic Salt As an n-Type Dopant for Efficient and Stable Organic Light-Emitting Diodes
journal, March 2015
- Bin, Zhengyang; Duan, Lian; Qiu, Yong
- ACS Applied Materials & Interfaces, Vol. 7, Issue 12
Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation
journal, August 2018
- Nava, Diego; Shin, Younghun; Massetti, Matteo
- ACS Applied Energy Materials, Vol. 1, Issue 9
The electrochemical doping reactions of the conducting ladder polymer benzimidazobenzophenanthroline (BBL)
journal, January 1988
- Wilbourn, K.; Murray, Royce W.
- Macromolecules, Vol. 21, Issue 1
Highly stretchable polymer semiconductor films through the nanoconfinement effect
journal, January 2017
- Xu, Jie; Wang, Sihong; Wang, Ging-Ji Nathan
- Science, Vol. 355, Issue 6320
Moderate doping leads to high performance of semiconductor/insulator polymer blend transistors
journal, March 2013
- Lu, Guanghao; Blakesley, James; Himmelberger, Scott
- Nature Communications, Vol. 4, Issue 1
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
Biofuel powered glucose detection in bodily fluids with an n-type conjugated polymer
journal, December 2019
- Ohayon, David; Nikiforidis, Georgios; Savva, Achilleas
- Nature Materials, Vol. 19, Issue 4
A Universal Method to Produce Low-Work Function Electrodes for Organic Electronics
journal, April 2012
- Zhou, Y.; Fuentes-Hernandez, C.; Shim, J.
- Science, Vol. 336, Issue 6079, p. 327-332
Macroscopic and high-throughput printing of aligned nanostructured polymer semiconductors for MHz large-area electronics
journal, September 2015
- Bucella, Sadir G.; Luzio, Alessandro; Gann, Eliot
- Nature Communications, Vol. 6, Issue 1
Correcting for contact geometry in Seebeck coefficient measurements of thin film devices
journal, October 2014
- Reenen, Stephan van; Kemerink, Martijn
- Organic Electronics, Vol. 15, Issue 10
Quantitative Measurements of the Temperature-Dependent Microscopic and Macroscopic Dynamics of a Molecular Dopant in a Conjugated Polymer
journal, July 2017
- Li, Jun; Koshnick, Correy; Diallo, Souleymane O.
- Macromolecules, Vol. 50, Issue 14
Controlling Molecular Doping in Organic Semiconductors
journal, September 2017
- Jacobs, Ian E.; Moulé, Adam J.
- Advanced Materials, Vol. 29, Issue 42
Sequential Doping Reveals the Importance of Amorphous Chain Rigidity in Charge Transport of Semi-Crystalline Polymers
journal, September 2017
- Chew, Annabel R.; Ghosh, Raja; Shang, Zhengrong
- The Journal of Physical Chemistry Letters, Vol. 8, Issue 20
Thermoelectric Properties of Solution-Processed n-Doped Ladder-Type Conducting Polymers
journal, October 2016
- Wang, Suhao; Sun, Hengda; Ail, Ujwala
- Advanced Materials, Vol. 28, Issue 48
Enhancing Molecular n-Type Doping of Donor-Acceptor Copolymers by Tailoring Side Chains
journal, January 2018
- Liu, Jian; Qiu, Li; Alessandri, Riccardo
- Advanced Materials, Vol. 30, Issue 7
Engineered films for display technologies
journal, January 2004
- MacDonald, William A.
- Journal of Materials Chemistry, Vol. 14, Issue 1
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
Self-Assembly, Molecular Packing, and Electron Transport in n-Type Polymer Semiconductor Nanobelts
journal, July 2008
- Briseno, Alejandro L.; Mannsfeld, Stefan C. B.; Shamberger, Patrick J.
- Chemistry of Materials, Vol. 20, Issue 14
Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives
journal, September 2019
- Riera-Galindo, Sergi; Orbelli Biroli, Alessio; Forni, Alessandra
- ACS Applied Materials & Interfaces, Vol. 11, Issue 41
Doped Organic Transistors
journal, October 2016
- Lüssem, Björn; Keum, Chang-Min; Kasemann, Daniel
- Chemical Reviews, Vol. 116, Issue 22
High-performance, air-stable, n-type thermoelectric films from a water-dispersed nickel-ethenetetrathiolate complex and ethylene glycol
journal, January 2020
- Ueda, Kazuki; Yamada, Yuto; Terao, Toshiki
- Journal of Materials Chemistry A, Vol. 8, Issue 25
Parallel programming of an ionic floating-gate memory array for scalable neuromorphic computing
journal, April 2019
- Fuller, Elliot J.; Keene, Scott T.; Melianas, Armantas
- Science, Vol. 364, Issue 6440
Complementary Logic Circuits Based on High-Performance n-Type Organic Electrochemical Transistors
journal, January 2018
- Sun, Hengda; Vagin, Mikhail; Wang, Suhao
- Advanced Materials, Vol. 30, Issue 9
Ground-state electron transfer in all-polymer donor–acceptor heterojunctions
journal, March 2020
- Xu, Kai; Sun, Hengda; Ruoko, Tero-Petri
- Nature Materials, Vol. 19, Issue 7
The effect of thermal annealing on dopant site choice in conjugated polymers
journal, June 2016
- Li, Jun; Rochester, Christopher W.; Jacobs, Ian E.
- Organic Electronics, Vol. 33
Impact of the Doping Method on Conductivity and Thermopower in Semiconducting Polythiophenes
journal, October 2014
- Glaudell, Anne M.; Cochran, Justin E.; Patel, Shrayesh N.
- Advanced Energy Materials, Vol. 5, Issue 4
Molecular Doping Enhances Photoconductivity in Polymer Bulk Heterojunction Solar Cells
journal, September 2013
- Zhang, Yuan; Zhou, Huiqiong; Seifter, Jason
- Advanced Materials, Vol. 25, Issue 48
Organic electrochemical transistors
journal, January 2018
- Rivnay, Jonathan; Inal, Sahika; Salleo, Alberto
- Nature Reviews Materials, Vol. 3, Issue 2
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
All-printed large-scale integrated circuits based on organic electrochemical transistors
journal, November 2019
- Andersson Ersman, Peter; Lassnig, Roman; Strandberg, Jan
- Nature Communications, Vol. 10, Issue 1
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
High Electron Mobility in Ladder Polymer Field-Effect Transistors
journal, November 2003
- Babel, Amit; Jenekhe, Samson A.
- Journal of the American Chemical Society, Vol. 125, Issue 45, p. 13656-13657
Doping Engineering Enables Highly Conductive and Thermally Stable n-Type Organic Thermoelectrics with High Power Factor
journal, August 2019
- Liu, Jian; Garman, Matt P.; Dong, Jingjin
- ACS Applied Energy Materials, Vol. 2, Issue 9
Stretchable, Large-area Organic Electronics
journal, May 2010
- Sekitani, Tsuyoshi; Someya, Takao
- Advanced Materials, Vol. 22, Issue 20, p. 2228-2246
A Chemically Doped Naphthalenediimide-Bithiazole Polymer for n-Type Organic Thermoelectrics
journal, June 2018
- Wang, Suhao; Sun, Hengda; Erdmann, Tim
- Advanced Materials, Vol. 30, Issue 31
2D coherent charge transport in highly ordered conducting polymers doped by solid state diffusion
journal, May 2016
- Kang, Keehoon; Watanabe, Shun; Broch, Katharina
- Nature Materials, Vol. 15, Issue 8
Direct metabolite detection with an n-type accumulation mode organic electrochemical transistor
journal, June 2018
- Pappa, Anna Maria; Ohayon, David; Giovannitti, Alexander
- Science Advances, Vol. 4, Issue 6
Morphology controls the thermoelectric power factor of a doped semiconducting polymer
journal, June 2017
- Patel, Shrayesh N.; Glaudell, Anne M.; Peterson, Kelly A.
- Science Advances, Vol. 3, Issue 6
Polar Side Chains Enhance Processability, Electrical Conductivity, and Thermal Stability of a Molecularly p-Doped Polythiophene
journal, April 2017
- Kroon, Renee; Kiefer, David; Stegerer, Dominik
- Advanced Materials, Vol. 29, Issue 24
π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications †
journal, February 2011
- Facchetti, Antonio
- Chemistry of Materials, Vol. 23, Issue 3
Tetraaminoethylenes
journal, May 1965
- Winberg, H. E.; Carnahan, J. E.; Coffman, D. D.
- Journal of the American Chemical Society, Vol. 87, Issue 9