Benzimidazolone-Dioxazine Pigments-Based Conjugated Polymers for Organic Field-Effect Transistor
Abstract
Molecules based on benzimidazolone-dioxazine are known as blue/violet pigments and have been commercialized for decades. However, unfavorable solubility limits the application of these structures as building blocks of conjugated polymers despite their low band gaps. Herein, a series of donor–acceptor conjugated polymers containing soluble benzimidazolone-dioxazine structures as the acceptors and oligothiophene as donors are synthesized and investigated. With increasing numbers of thiophene rings, the steric hindrance diminishes and high molecular weight polymers can be achieved, leading to an improved performance in organic field effect transistor devices. The hole mobility of polymers with three to six thiophene units is in the order of 10-1 cm2 V-1 s -1. Among all the polymers, polymer P3 with three thiophene units between benzimidazolone-dioxazine structures shows the best hole mobility of 0.4 cm2 V-1 s -1. Grazing-incidence wide-angle X-ray scattering results reveal that the high mobility of organic field-effect transistors (OFETs) can be accredited by matched donor–acceptor packing in the solid thin films.
- Authors:
-
[1]
- University of Akron, OH (United States)
- National Yang Ming Chiao Tung University, Hsinchu (Taiwan)
- Publication Date:
- Research Org.:
- Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS); Univ. of Akron, OH (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Science Foundation (NSF)
- OSTI Identifier:
- 1981422
- Grant/Contract Number:
- AC02-06CH11357; DMR-1554851
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Macromolecular Rapid Communications
- Additional Journal Information:
- Journal Volume: 44; Journal Issue: 1; Journal ID: ISSN 1022-1336
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; benzimidazolone-dioxazine; conjugated polymers; organic field effect transistors; pigments
Citation Formats
Tung, Wei‐Yao, Pu, Cheng, Huang, Yi‐Fan, Xie, Wei, Cheng, Chung‐Fu, Lai, Yun‐Yu, Li, Xiang, Lin, Heng‐Yi, Lai, Yueh‐Ting, Chen, Kun, Wang, Chien‐Lung, and Zhu, Yu. Benzimidazolone-Dioxazine Pigments-Based Conjugated Polymers for Organic Field-Effect Transistor. United States: N. p., 2022.
Web. doi:10.1002/marc.202200297.
Tung, Wei‐Yao, Pu, Cheng, Huang, Yi‐Fan, Xie, Wei, Cheng, Chung‐Fu, Lai, Yun‐Yu, Li, Xiang, Lin, Heng‐Yi, Lai, Yueh‐Ting, Chen, Kun, Wang, Chien‐Lung, & Zhu, Yu. Benzimidazolone-Dioxazine Pigments-Based Conjugated Polymers for Organic Field-Effect Transistor. United States. https://doi.org/10.1002/marc.202200297
Tung, Wei‐Yao, Pu, Cheng, Huang, Yi‐Fan, Xie, Wei, Cheng, Chung‐Fu, Lai, Yun‐Yu, Li, Xiang, Lin, Heng‐Yi, Lai, Yueh‐Ting, Chen, Kun, Wang, Chien‐Lung, and Zhu, Yu. Fri .
"Benzimidazolone-Dioxazine Pigments-Based Conjugated Polymers for Organic Field-Effect Transistor". United States. https://doi.org/10.1002/marc.202200297. https://www.osti.gov/servlets/purl/1981422.
@article{osti_1981422,
title = {Benzimidazolone-Dioxazine Pigments-Based Conjugated Polymers for Organic Field-Effect Transistor},
author = {Tung, Wei‐Yao and Pu, Cheng and Huang, Yi‐Fan and Xie, Wei and Cheng, Chung‐Fu and Lai, Yun‐Yu and Li, Xiang and Lin, Heng‐Yi and Lai, Yueh‐Ting and Chen, Kun and Wang, Chien‐Lung and Zhu, Yu},
abstractNote = {Molecules based on benzimidazolone-dioxazine are known as blue/violet pigments and have been commercialized for decades. However, unfavorable solubility limits the application of these structures as building blocks of conjugated polymers despite their low band gaps. Herein, a series of donor–acceptor conjugated polymers containing soluble benzimidazolone-dioxazine structures as the acceptors and oligothiophene as donors are synthesized and investigated. With increasing numbers of thiophene rings, the steric hindrance diminishes and high molecular weight polymers can be achieved, leading to an improved performance in organic field effect transistor devices. The hole mobility of polymers with three to six thiophene units is in the order of 10-1 cm2 V-1 s -1. Among all the polymers, polymer P3 with three thiophene units between benzimidazolone-dioxazine structures shows the best hole mobility of 0.4 cm2 V-1 s -1. Grazing-incidence wide-angle X-ray scattering results reveal that the high mobility of organic field-effect transistors (OFETs) can be accredited by matched donor–acceptor packing in the solid thin films.},
doi = {10.1002/marc.202200297},
journal = {Macromolecular Rapid Communications},
number = 1,
volume = 44,
place = {United States},
year = {Fri May 27 00:00:00 EDT 2022},
month = {Fri May 27 00:00:00 EDT 2022}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Annealing-Free High-Mobility Diketopyrrolopyrrole−Quaterthiophene Copolymer for Solution-Processed Organic Thin Film Transistors
journal, February 2011
- Li, Yuning; Sonar, Prashant; Singh, Samarendra P.
- Journal of the American Chemical Society, Vol. 133, Issue 7
Electropolymerized Porous Conjugated Polymer Film as an Electrode for a Stable, High Energy Density Thin Film Asymmetric Supercapacitor
journal, June 2019
- Chen, Xiaoyi; Tung, Wei-Yao; Yang, Kun
- ACS Applied Polymer Materials, Vol. 1, Issue 7
Donor–acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells
journal, January 2015
- Wu, Jhong-Sian; Cheng, Sheng-Wen; Cheng, Yen-Ju
- Chemical Society Reviews, Vol. 44, Issue 5
High Performance Nonvolatile Transistor Memories Utilizing Functional Polyimide-Based Supramolecular Electrets
journal, April 2016
- Tung, Wei-Yao; Li, Meng-Hsien; Wu, Hung-Chin
- Chemistry - An Asian Journal, Vol. 11, Issue 10
Insight into High-Performance Conjugated Polymers for Organic Field-Effect Transistors
journal, December 2018
- Yang, Jie; Zhao, Zhiyuan; Wang, Shuai
- Chem, Vol. 4, Issue 12
Controlling the Field-Effect Mobility of Regioregular Polythiophene by Changing the Molecular Weight
journal, September 2003
- Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.
- Advanced Materials, Vol. 15, Issue 18
Improved Performance in Diketopyrrolopyrrole-Based Transistors with Bilayer Gate Dielectrics
journal, February 2014
- Ha, Tae-Jun; Sonar, Prashant; Dodabalapur, Ananth
- ACS Applied Materials & Interfaces, Vol. 6, Issue 5
Materials and Applications for Large Area Electronics: Solution-Based Approaches
journal, January 2010
- Arias, Ana Claudia; MacKenzie, J. Devin; McCulloch, Iain
- Chemical Reviews, Vol. 110, Issue 1
Furan substituted diketopyrrolopyrrole and thienylenevinylene based low band gap copolymer for high mobility organic thin film transistors
journal, January 2012
- Sonar, Prashant; Zhuo, Jing-Mei; Zhao, Li-Hong
- Journal of Materials Chemistry, Vol. 22, Issue 33
Conjugated polymer with dynamic and thermoreversible hydrogen bonding on the backbone
journal, August 2020
- Zhang, Haichang; Tung, Wei-Yao; Li, Xiang
- Polymer, Vol. 203
Design of High-Mobility Diketopyrrolopyrrole-Based π-Conjugated Copolymers for Organic Thin-Film Transistors
journal, May 2015
- Yi, Zhengran; Wang, Shuai; Liu, Yunqi
- Advanced Materials, Vol. 27, Issue 24
Regioregular poly(3-hexyl)selenophene: a low band gap organic hole transporting polymer
journal, January 2007
- Heeney, Martin; Zhang, Weimin; Crouch, David J.
- Chemical Communications, Issue 47
Crystalline Organic Pigment-Based Field-Effect Transistors
journal, June 2017
- Zhang, Haichang; Deng, Ruonan; Wang, Jing
- ACS Applied Materials & Interfaces, Vol. 9, Issue 26
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
A general relationship between disorder, aggregation and charge transport in conjugated polymers
journal, August 2013
- Noriega, Rodrigo; Rivnay, Jonathan; Vandewal, Koen
- Nature Materials, Vol. 12, Issue 11
High-Field-Effect Mobility of Low-Crystallinity Conjugated Polymers with Localized Aggregates
journal, May 2016
- Son, Sung Y.; Kim, Yebyeol; Lee, Junwoo
- Journal of the American Chemical Society, Vol. 138, Issue 26
Patternable Conjugated Polymers with Latent Hydrogen-Bonding on the Main Chain
journal, December 2014
- Yang, Kun; He, Tianda; Chen, Xiaoyi
- Macromolecules, Vol. 47, Issue 24
A Low Band Gap Conjugated Polymer for Supercapacitor Devices
journal, October 2006
- Marchioni, Filippo; Yang, Jian; Walker, Wesley
- The Journal of Physical Chemistry B, Vol. 110, Issue 44
Improving polymer transistor performance via morphology control
journal, January 2010
- Tsao, Hoi Nok; Müllen, Klaus
- Chemical Society Reviews, Vol. 39, Issue 7
Poly(2,5-bis(2-octyldodecyl)-3,6-di(furan-2-yl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione-co-thieno[3,2-b]thiophene): a high performance polymer semiconductor for both organic thin film transistors and organic photovoltaics
journal, January 2012
- Li, Yuning; Sonar, Prashant; Singh, Samarendra P.
- Physical Chemistry Chemical Physics, Vol. 14, Issue 19
Hole mobility of 3.56 cm 2 V −1 s −1 accomplished using more extended dithienothiophene with furan flanked diketopyrrolopyrrole polymer
journal, January 2015
- Sonar, Prashant; Chang, Jingjing; Shi, Zugui
- Journal of Materials Chemistry C, Vol. 3, Issue 36
Efficient organic solar cells processed from hydrocarbon solvents
journal, January 2016
- Zhao, Jingbo; Li, Yunke; Yang, Guofang
- Nature Energy, Vol. 1, Issue 2
Charge Transport in Organic and Polymeric Semiconductors for Flexible and Stretchable Devices
journal, December 2015
- Yao, Yifan; Dong, Huanli; Hu, Wenping
- Advanced Materials, Vol. 28, Issue 22
Multilevel Nonvolatile Flexible Organic Field-Effect Transistor Memories Employing Polyimide Electrets with Different Charge-Transfer Effects
journal, April 2014
- Yu, An-Dih; Tung, Wei-Yao; Chiu, Yu-Cheng
- Macromolecular Rapid Communications, Vol. 35, Issue 11
Flexible suspended gate organic thin-film transistors for ultra-sensitive pressure detection
journal, March 2015
- Zang, Yaping; Zhang, Fengjiao; Huang, Dazhen
- Nature Communications, Vol. 6, Issue 1
Light absorption of poly(3-hexylthiophene) single crystals
journal, January 2014
- Rahimi, Khosrow; Botiz, Ioan; Agumba, John O.
- RSC Adv., Vol. 4, Issue 22
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon
journal, January 2014
- Sirringhaus, Henning
- Advanced Materials, Vol. 26, Issue 9
Intrinsically stretchable and healable semiconducting polymer for organic transistors
journal, November 2016
- Oh, Jin Young; Rondeau-Gagné, Simon; Chiu, Yu-Cheng
- Nature, Vol. 539, Issue 7629
Polymers Based on Benzodipyrrolidone and Naphthodipyrrolidone with Latent Hydrogen‐Bonding on the Main Chain
journal, April 2017
- Zhang, Haichang; Yang, Kun; Chen, Yu‐Ming
- Macromolecular Chemistry and Physics, Vol. 218, Issue 13
Ternary non-fullerene polymer solar cells with 13.51% efficiency and a record-high fill factor of 78.13%
journal, January 2018
- Nian, Li; Kan, Yuanyuan; Wang, Haitao
- Energy & Environmental Science, Vol. 11, Issue 12
Conjugated polymers containing diketopyrrolopyrrole units in the main chain
journal, January 2010
- Tieke, Bernd; Rabindranath, A. Raman; Zhang, Kai
- Beilstein Journal of Organic Chemistry, Vol. 6
Red Emitting Diphenylpyrrolopyrrole (DPP)-Based Polymers Prepared by Stille and Heck Coupling
journal, December 2006
- Zhu, Yu; Heim, Ingo; Tieke, Bernd
- Macromolecular Chemistry and Physics, Vol. 207, Issue 23
Developments of Diketopyrrolopyrrole‐Dye‐Based Organic Semiconductors for a Wide Range of Applications in Electronics
journal, December 2019
- Liu, Qian; Bottle, Steven E.; Sonar, Prashant
- Advanced Materials, Vol. 32, Issue 4
Charge Transport in Organic Semiconductors
journal, April 2007
- Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A.
- Chemical Reviews, Vol. 107, Issue 4
Orienting Semi-Conducting π-Conjugated Polymers
journal, December 2013
- Brinkmann, Martin; Hartmann, Lucia; Biniek, Laure
- Macromolecular Rapid Communications, Vol. 35, Issue 1
Investigation of Structure–Property Relationships in Diketopyrrolopyrrole-Based Polymer Semiconductors via Side-Chain Engineering
journal, February 2015
- Back, Jang Yeol; Yu, Hojeong; Song, Inho
- Chemistry of Materials, Vol. 27, Issue 5
Design, Synthesis, and Structure–Property Relationships of Isoindigo-Based Conjugated Polymers
journal, February 2014
- Lei, Ting; Wang, Jie-Yu; Pei, Jian
- Accounts of Chemical Research, Vol. 47, Issue 4
Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state
journal, January 2019
- Yang, Kun; Li, Xiang; Huang, Yi-Fan
- Polymer, Vol. 160
Polymer and Organic Nonvolatile Memory Devices †
journal, February 2011
- Heremans, Paul; Gelinck, Gerwin H.; Müller, Robert
- Chemistry of Materials, Vol. 23, Issue 3
Ultralow-power organic complementary circuits
journal, February 2007
- Klauk, Hagen; Zschieschang, Ute; Pflaum, Jens
- Nature, Vol. 445, Issue 7129
Structural and electrochemical properties of polythiophene
journal, August 2011
- Senthilkumar, B.; Thenamirtham, P.; Kalai Selvan, R.
- Applied Surface Science, Vol. 257, Issue 21
Tetrathiafulvalenes as π-Electron Donors for Intramolecular Charge-Transfer Materials
journal, January 1999
- Bryce, Martin R.
- Advanced Materials, Vol. 11, Issue 1
Designing π-conjugated polymers for organic electronics
journal, December 2013
- Guo, Xin; Baumgarten, Martin; Müllen, Klaus
- Progress in Polymer Science, Vol. 38, Issue 12
Highly Luminescent 1,4-Diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole- (DPP-) Based Conjugated Polymers Prepared Upon Suzuki Coupling
journal, September 2007
- Zhu, Y.; Rabindranath, A. R.; Beyerlein, T.
- Macromolecules, Vol. 40, Issue 19
Hydrogen-Bonding-Mediated Solid-State Self-Assembled Isoepindolidiones (isoEpi) Crystal for Organic Field-Effect Transistor
journal, February 2018
- Zhang, Haichang; Liu, Kewei; Wu, Kuan-Yi
- The Journal of Physical Chemistry C, Vol. 122, Issue 11
Red Emitting N-Functionalized Poly(1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole) (Poly-DPP): A Deeply Colored Polymer with Unusually Large Stokes Shift
journal, October 2006
- Rabindranath, A. R.; Zhu, Y.; Heim, I.
- Macromolecules, Vol. 39, Issue 24
Linear-type carbazoledioxazine-based organic semiconductors: the effect of backbone planarity on the molecular orientation and charge transport properties
journal, January 2018
- Otsuka, Rikuo; Wang, Yang; Mori, Takehiko
- RSC Advances, Vol. 8, Issue 18
Donor–Acceptor‐Conjugated Polymer for High‐Performance Organic Field‐Effect Transistors: A Progress Report
journal, August 2019
- Kim, Minjun; Ryu, Seung Un; Park, Sang Ah
- Advanced Functional Materials, Vol. 30, Issue 20
Higher Molecular Weight Leads to Improved Photoresponsivity, Charge Transport and Interfacial Ordering in a Narrow Bandgap Semiconducting Polymer
journal, September 2010
- Tong, Minghong; Cho, Shinuk; Rogers, James T.
- Advanced Functional Materials, Vol. 20, Issue 22, p. 3959-3965
Hydrogen-Bonded Semiconducting Pigments for Air-Stable Field-Effect Transistors
journal, December 2012
- Głowacki, Eric Daniel; Irimia-Vladu, Mihai; Kaltenbrunner, Martin
- Advanced Materials, Vol. 25, Issue 11
Naphthodipyrrolidone (NDP) based conjugated polymers with high electron mobility and ambipolar transport properties
journal, January 2017
- Zhang, Haichang; Zhang, Shuo; Mao, Yifan
- Polymer Chemistry, Vol. 8, Issue 21
Organic Semiconductors based on Dyes and Color Pigments
journal, March 2016
- Gsänger, Marcel; Bialas, David; Huang, Lizhen
- Advanced Materials, Vol. 28, Issue 19