Tuning the Cross-Linker Crystallinity of a Stretchable Polymer Semiconductor
Abstract
The cross-linking of conjugated polymers has been shown to be an effective strategy to improve its elastic properties to give deformable semiconductors for plastic electronics. Although there have been extensive studies of the structural requirements of the polymer host for good film ductility, no work to date has focused on the relevance of the structural design or chemistry of these cross-linker additives. In this study, urethane groups and tertiary carbon atoms are inserted into the alkyl backbone of perfluorophenyl azide-based cross-linkers to investigate the importance of cross-linker crystallinity with respect to polymer morphology and hence mechanical and electrical properties. Linear cross-linkers with hydrogen bonding from urethane groups readily phase separate and recrystallize in the polymer network to form cross-linked domains that obstruct the strain distribution of the polymer film. Branch cross-linkers with tertiary carbon on the other hand form an evenly cross-linked network in the polymer blend stemming from excellent miscibility and show a 4-fold increase in fracture strain. Furthermore, a stable hole mobility of 0.2 cm2 V–1 s–1 is achieved up to ε = 100%, and a stable hole mobility of 0.1 cm2 V–1 s–1 after 2000 cycles of ε = 25% on fully stretchable organic field-effect transistors.
- Authors:
-
[1];
[1];
[1]
- Stanford Univ., CA (United States)
- Univ. of Southern Mississippi, Hattiesburg, MI (United States)
- Publication Date:
- Research Org.:
- Univ. of Southern Mississippi, Hattiesburg, MS (United States); University of Southern Mississippi, Hattiesburg, MS (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division (MSE); US Air Force Office of Scientific Research (AFOSR); National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1599403
- Alternate Identifier(s):
- OSTI ID: 1985406
- Grant/Contract Number:
- SC0019361; FA9550-15-1-0106; FA9550-18-1-0143; ECCS-1542152
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemistry of Materials
- Additional Journal Information:
- Journal Volume: 31; Journal Issue: 17; Journal ID: ISSN 0897-4756
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Wang, Ging-Ji Nathan, Zheng, Yu, Zhang, Song, Kang, Jiheong, Wu, Hung-Chin, Gasperini, Andrea, Zhang, Hongyi, Gu, Xiaodan, and Bao, Zhenan. Tuning the Cross-Linker Crystallinity of a Stretchable Polymer Semiconductor. United States: N. p., 2018.
Web. doi:10.1021/acs.chemmater.8b04314.
Wang, Ging-Ji Nathan, Zheng, Yu, Zhang, Song, Kang, Jiheong, Wu, Hung-Chin, Gasperini, Andrea, Zhang, Hongyi, Gu, Xiaodan, & Bao, Zhenan. Tuning the Cross-Linker Crystallinity of a Stretchable Polymer Semiconductor. United States. https://doi.org/10.1021/acs.chemmater.8b04314
Wang, Ging-Ji Nathan, Zheng, Yu, Zhang, Song, Kang, Jiheong, Wu, Hung-Chin, Gasperini, Andrea, Zhang, Hongyi, Gu, Xiaodan, and Bao, Zhenan. Fri .
"Tuning the Cross-Linker Crystallinity of a Stretchable Polymer Semiconductor". United States. https://doi.org/10.1021/acs.chemmater.8b04314. https://www.osti.gov/servlets/purl/1599403.
@article{osti_1599403,
title = {Tuning the Cross-Linker Crystallinity of a Stretchable Polymer Semiconductor},
author = {Wang, Ging-Ji Nathan and Zheng, Yu and Zhang, Song and Kang, Jiheong and Wu, Hung-Chin and Gasperini, Andrea and Zhang, Hongyi and Gu, Xiaodan and Bao, Zhenan},
abstractNote = {The cross-linking of conjugated polymers has been shown to be an effective strategy to improve its elastic properties to give deformable semiconductors for plastic electronics. Although there have been extensive studies of the structural requirements of the polymer host for good film ductility, no work to date has focused on the relevance of the structural design or chemistry of these cross-linker additives. In this study, urethane groups and tertiary carbon atoms are inserted into the alkyl backbone of perfluorophenyl azide-based cross-linkers to investigate the importance of cross-linker crystallinity with respect to polymer morphology and hence mechanical and electrical properties. Linear cross-linkers with hydrogen bonding from urethane groups readily phase separate and recrystallize in the polymer network to form cross-linked domains that obstruct the strain distribution of the polymer film. Branch cross-linkers with tertiary carbon on the other hand form an evenly cross-linked network in the polymer blend stemming from excellent miscibility and show a 4-fold increase in fracture strain. Furthermore, a stable hole mobility of 0.2 cm2 V–1 s–1 is achieved up to ε = 100%, and a stable hole mobility of 0.1 cm2 V–1 s–1 after 2000 cycles of ε = 25% on fully stretchable organic field-effect transistors.},
doi = {10.1021/acs.chemmater.8b04314},
journal = {Chemistry of Materials},
number = 17,
volume = 31,
place = {United States},
year = {Fri Nov 30 00:00:00 EST 2018},
month = {Fri Nov 30 00:00:00 EST 2018}
}
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Works referenced in this record:
Effect of Nonconjugated Spacers on Mechanical Properties of Semiconducting Polymers for Stretchable Transistors
journal, September 2018
- Mun, Jaewan; Wang, Ging-Ji Nathan; Oh, Jin Young
- Advanced Functional Materials, Vol. 28, Issue 43
Nonhalogenated Solvent Processable and Printable High-Performance Polymer Semiconductor Enabled by Isomeric Nonconjugated Flexible Linkers
journal, June 2018
- Wang, Ging-Ji Nathan; Molina-Lopez, Francisco; Zhang, Hongyi
- Macromolecules, Vol. 51, Issue 13
An ABA triblock copolymer strategy for intrinsically stretchable semiconductors
journal, January 2015
- Peng, Rui; Pang, Bo; Hu, Daqing
- Journal of Materials Chemistry C, Vol. 3, Issue 15
Flexible, highly efficient all-polymer solar cells
journal, October 2015
- Kim, Taesu; Kim, Jae-Han; Kang, Tae Eui
- Nature Communications, Vol. 6, Issue 1
Mechanical Properties of Conjugated Polymers and Polymer-Fullerene Composites as a Function of Molecular Structure
journal, October 2013
- Savagatrup, Suchol; Makaram, Aditya S.; Burke, Daniel J.
- Advanced Functional Materials, Vol. 24, Issue 8
Comparison of Methods for Determining the Mechanical Properties of Semiconducting Polymer Films for Stretchable Electronics
journal, March 2017
- Rodriquez, Daniel; Kim, Jae-Han; Root, Samuel E.
- ACS Applied Materials & Interfaces, Vol. 9, Issue 10
Polythiophene Nanofibril Bundles Surface-Embedded in Elastomer: A Route to a Highly Stretchable Active Channel Layer
journal, January 2015
- Shin, Minkwan; Oh, Jin Young; Byun, Kyung-Eun
- Advanced Materials, Vol. 27, Issue 7
Exploiting π–π Stacking for Stretchable Semiconducting Polymers
journal, March 2018
- Son, Sung Yun; Kim, Jae-Han; Song, Eunjoo
- Macromolecules, Vol. 51, Issue 7
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
Tough and Water-Insensitive Self-Healing Elastomer for Robust Electronic Skin
journal, February 2018
- Kang, Jiheong; Son, Donghee; Wang, Ging-Ji Nathan
- Advanced Materials, Vol. 30, Issue 13
Molecular origin of high field-effect mobility in an indacenodithiophene–benzothiadiazole copolymer
journal, July 2013
- Zhang, Xinran; Bronstein, Hugo; Kronemeijer, Auke J.
- Nature Communications, Vol. 4, Issue 1
Correlations between Mechanical and Electrical Properties of Polythiophenes
journal, November 2010
- O’Connor, Brendan; Chan, Edwin P.; Chan, Calvin
- ACS Nano, Vol. 4, Issue 12
Probing the Viscoelastic Property of Pseudo Free-Standing Conjugated Polymeric Thin Films
journal, May 2018
- Zhang, Song; Ocheje, Michael U.; Luo, Shaochuan
- Macromolecular Rapid Communications, Vol. 39, Issue 14
Mechanical Properties of a Library of Low-Band-Gap Polymers
journal, March 2016
- Roth, Bérenger; Savagatrup, Suchol; V. de los Santos, Nathaniel
- Chemistry of Materials, Vol. 28, Issue 7
Environmentally benign fabrication processes for high-performance polymeric semiconductors
journal, January 2017
- Cho, Jangwhan; Yu, Seong Hoon; Chung, Dae Sung
- Journal of Materials Chemistry C, Vol. 5, Issue 11
Improving Miscibility of a Naphthalene Diimide-Bithiophene Copolymer with n-Type Dopants through the Incorporation of “Kinked” Monomers
journal, March 2018
- Shin, Younghun; Massetti, Matteo; Komber, Hartmut
- Advanced Electronic Materials, Vol. 4, Issue 10
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
Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding
journal, December 2015
- Yao, Jingjing; Yu, Chenmin; Liu, Zitong
- Journal of the American Chemical Society, Vol. 138, Issue 1
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
Biocompatible and totally disintegrable semiconducting polymer for ultrathin and ultralightweight transient electronics
journal, May 2017
- Lei, Ting; Guan, Ming; Liu, Jia
- Proceedings of the National Academy of Sciences, Vol. 114, Issue 20
Soft Poly(butyl acrylate) Side Chains toward Intrinsically Stretchable Polymeric Semiconductors for Field-Effect Transistor Applications
journal, June 2017
- Wen, Han-Fang; Wu, Hung-Chin; Aimi, Junko
- Macromolecules, Vol. 50, Issue 13
Skin electronics from scalable fabrication of an intrinsically stretchable transistor array
journal, February 2018
- Wang, Sihong; Xu, Jie; Wang, Weichen
- Nature, Vol. 555, Issue 7694
Morphological considerations of organic electronic films for flexible and stretchable devices
journal, February 2017
- O’Connor, Brendan T.; Awartani, Omar M.; Balar, Nrup
- MRS Bulletin, Vol. 42, Issue 02
Inducing Elasticity through Oligo-Siloxane Crosslinks for Intrinsically Stretchable Semiconducting Polymers
journal, August 2016
- Wang, Ging-Ji Nathan; Shaw, Leo; Xu, Jie
- Advanced Functional Materials, Vol. 26, Issue 40
Stretchable Polymer Semiconductors for Plastic Electronics
journal, January 2018
- Wang, Ging-Ji Nathan; Gasperini, Andrea; Bao, Zhenan
- Advanced Electronic Materials, Vol. 4, Issue 2
Deformable Organic Nanowire Field-Effect Transistors
journal, January 2018
- Lee, Yeongjun; Oh, Jin Young; Kim, Taeho Roy
- Advanced Materials, Vol. 30, Issue 7
Mechanical Properties of Organic Semiconductors for Stretchable, Highly Flexible, and Mechanically Robust Electronics
journal, March 2017
- Root, Samuel E.; Savagatrup, Suchol; Printz, Adam D.
- Chemical Reviews, Vol. 117, Issue 9
FTIR analysis of hydrogen bonding in amorphous linear aromatic polyurethanes. I. Influence of temperature
journal, June 1994
- Wang, Fu Cai; Feve, Michel; Lam, Thanh My
- Journal of Polymer Science Part B: Polymer Physics, Vol. 32, Issue 8
Mechanical Properties of Polymer–Fullerene Bulk Heterojunction Films: Role of Nanomorphology of Composite Films
journal, April 2017
- Kim, Jae-Han; Noh, Jonghyeon; Choi, Hyesun
- Chemistry of Materials, Vol. 29, Issue 9
High-performance polymer semiconducting heterostructure devices by nitrene-mediated photocrosslinking of alkyl side chains
journal, December 2009
- Png, Rui-Qi; Chia, Perq-Jon; Tang, Jie-Cong
- Nature Materials, Vol. 9, Issue 2
The rise of plastic bioelectronics
journal, December 2016
- Someya, Takao; Bao, Zhenan; Malliaras, George G.
- Nature, Vol. 540, Issue 7633
Elastomer–Polymer Semiconductor Blends for High-Performance Stretchable Charge Transport Networks
journal, February 2016
- Choi, Dalsu; Kim, Hyungchul; Persson, Nils
- Chemistry of Materials, Vol. 28, Issue 4
Electronic Muscles and Skins: A Review of Soft Sensors and Actuators
journal, August 2017
- Chen, Dustin; Pei, Qibing
- Chemical Reviews, Vol. 117, Issue 17
Melt-Processing of Complementary Semiconducting Polymer Blends for High Performance Organic Transistors
journal, December 2016
- Zhao, Yan; Zhao, Xikang; Roders, Michael
- Advanced Materials, Vol. 29, Issue 6
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties
journal, February 2018
- Ocheje, Michael U.; Charron, Brynn P.; Cheng, Yu-Hsuan
- Macromolecules, Vol. 51, Issue 4
Anisotropic Structure and Charge Transport in Highly Strain-Aligned Regioregular Poly(3-hexylthiophene)
journal, August 2011
- O'Connor, Brendan; Kline, R. Joseph; Conrad, Brad R.
- Advanced Functional Materials, Vol. 21, Issue 19
The meniscus-guided deposition of semiconducting polymers
journal, February 2018
- Gu, Xiaodan; Shaw, Leo; Gu, Kevin
- Nature Communications, Vol. 9, Issue 1
Effects of Molecular Structure and Packing Order on the Stretchability of Semicrystalline Conjugated Poly(Tetrathienoacene-diketopyrrolopyrrole) Polymers
journal, December 2016
- Lu, Chien; Lee, Wen-Ya; Gu, Xiaodan
- Advanced Electronic Materials, Vol. 3, Issue 2
Tuning Mechanical and Optoelectrical Properties of Poly(3-hexylthiophene) through Systematic Regioregularity Control
journal, June 2015
- Kim, Jin-Seong; Kim, Jae-Han; Lee, Wonho
- Macromolecules, Vol. 48, Issue 13
Effect of Broken Conjugation on the Stretchability of Semiconducting Polymers
journal, August 2016
- Savagatrup, Suchol; Zhao, Xikang; Chan, Esther
- Macromolecular Rapid Communications, Vol. 37, Issue 19
Stretchable and Transparent Organic Semiconducting Thin Film with Conjugated Polymer Nanowires Embedded in an Elastomeric Matrix
journal, October 2015
- Song, Eunjoo; Kang, Boseok; Choi, Hyun Ho
- Advanced Electronic Materials, Vol. 2, Issue 1
Intrinsically stretchable field-effect transistors
journal, February 2017
- Liang, Jiajie; Tong, Kwing; Sun, Huibin
- MRS Bulletin, Vol. 42, Issue 02
Biodegradable Polymeric Materials in Degradable Electronic Devices
journal, February 2018
- Feig, Vivian R.; Tran, Helen; Bao, Zhenan
- ACS Central Science, Vol. 4, Issue 3
Stretchable and ultraflexible organic electronics
journal, February 2017
- Lipomi, Darren J.; Bao, Zhenan
- MRS Bulletin, Vol. 42, Issue 02
Skin-Inspired Electronics: An Emerging Paradigm
journal, April 2018
- Wang, Sihong; Oh, Jin Young; Xu, Jie
- Accounts of Chemical Research, Vol. 51, Issue 5
Tough, Semiconducting Polyethylene-poly(3-hexylthiophene) Diblock Copolymers
journal, October 2007
- Müller, C.; Goffri, S.; Breiby, D. W.
- Advanced Functional Materials, Vol. 17, Issue 15
Perfluorophenyl Azides: New Applications in Surface Functionalization and Nanomaterial Synthesis
journal, November 2010
- Liu, Li-Hong; Yan, Mingdi
- Accounts of Chemical Research, Vol. 43, Issue 11
Works referencing / citing this record:
Improved thin film stability of differently formulated, printed, and crosslinked polymer layers against successive solvent printing
journal, January 2020
- Hibon, Pauline; von Seggern, Heinz; Tseng, Hsin‐Rong
- Journal of Applied Polymer Science, Vol. 137, Issue 29
Challenge and Solution of Characterizing Glass Transition Temperature for Conjugated Polymers by Differential Scanning Calorimetry
journal, August 2019
- Qian, Zhiyuan; Galuska, Luke; McNutt, William W.
- Journal of Polymer Science Part B: Polymer Physics, Vol. 57, Issue 23