Improving Charge Transport and Environmental Stability of Carbohydrate‐Bearing Semiconducting Polymers in Organic Field‐Effect Transistors

Mooney, Madison; Pandolfi, Lauren; Wang, Yunfei; Zhu, Chenhui; Garg, Garima; Kraft, Ulrike; Gu, Xiaodan; Rondeau‐Gagné, Simon

doi:10.1002/aelm.202400537

Improving Charge Transport and Environmental Stability of Carbohydrate‐Bearing Semiconducting Polymers in Organic Field‐Effect Transistors

Journal Article · Fri Oct 04 00:00:00 EDT 2024 · Advanced Electronic Materials

DOI:https://doi.org/10.1002/aelm.202400537· OSTI ID:2564476

Mooney, Madison ^[1]; Pandolfi, Lauren ^[1]; Wang, Yunfei ^[2]; Zhu, Chenhui ^[3]; Garg, Garima ^[1]; Kraft, Ulrike ^[4]; Gu, Xiaodan ^[2]; ^[1]

Department of Chemistry and Biochemistry University of Windsor Windsor Ontario N9B 3P4 Canada
School of Polymer Science and Engineering The University of Southern Mississippi Hattiesburg MS 39406 USA
Advanced Light Source Lawrence Berkeley National Laboratory Berkeley CA 94720 USA
Organic Bioelectronics Research Group Max Planck Institute for Polymer Research 55182 Mainz Germany

Abstract

Semiconducting polymers offer synthetic tunability, good mechanical properties, and biocompatibility, enabling the development of soft technologies previously inaccessible. Side‐chain engineering is a versatile approach for optimizing these semiconducting materials, but minor modifications can significantly impact material properties and device performance. Carbohydrate side chains have been previously introduced to improve the solubility of semiconducting polymers in greener solvents. Despite this achievement, these materials exhibit suboptimal performance and stability in field‐effect transistors. In this work, structure–property relationships are explored to enhance the device performance of carbohydrate‐bearing semiconducting polymers. Toward this objective, a series of isoindigo‐based polymers with carbohydrate side chains of varied carbon‐spacer lengths is developed. Material and device characterizations reveal the effects of side chain composition on solid‐state packing and device performance. With this new design, charge mobility is improved by up to three orders of magnitude compared to the previous studies. Processing–property relationships are also established by modulating annealing conditions and evaluating device stability upon air exposure. Notably, incidental oxygen‐doping effects lead to increased charge mobility after 10 days of exposure to ambient air, correlated with decreased contact resistance. Bias stress stability is also evaluated. This work highlights the importance of understanding structure–property relationships toward the optimization of device performance.

View Journal Article

Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; AC02-05CH11231

OSTI ID:: 2564476

Alternate ID(s):: OSTI ID: 2479512

Journal Information:: Advanced Electronic Materials, Journal Name: Advanced Electronic Materials Journal Issue: 6 Vol. 11; ISSN 2199-160X

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United States

Language:: English

References (63)

Recent Advances in the Bias Stress Stability of Organic Transistors Park, Sangsik; Kim, Seung Hyun; Choi, Hyun Ho Advanced Functional Materials, Vol. 30, Issue 20 https://doi.org/10.1002/adfm.201904590	journal	October 2019
Solvent‐Assisted Re‐annealing of Polymer Films for Solution‐Processable Organic Field‐Effect Transistors Di, Chong‐an; Lu, Kun; Zhang, Lei Advanced Materials, Vol. 22, Issue 11 https://doi.org/10.1002/adma.200902813	journal	March 2010
Recent Progress in High-Mobility Organic Transistors: A Reality Check Paterson, Alexandra F.; Singh, Saumya; Fallon, Kealan J. Advanced Materials, Vol. 30, Issue 36 https://doi.org/10.1002/adma.201801079	journal	July 2018
Performance Improvements in Conjugated Polymer Devices by Removal of Water-Induced Traps Nikolka, Mark; Schweicher, Guillaume; Armitage, John Advanced Materials, Vol. 30, Issue 36 https://doi.org/10.1002/adma.201801874	journal	July 2018
Environmental Effects on the Performance of Small‐Molecule Organic Thin‐Film Transistors Jagoo, Zafrullah; McNeil, L. E. Advanced Materials Interfaces, Vol. 11, Issue 14 https://doi.org/10.1002/admi.202301088	journal	March 2024
Contact Doping and Ultrathin Gate Dielectrics for Nanoscale Organic Thin-Film Transistors Ante, Frederik; Kälblein, Daniel; Zschieschang, Ute Small, Vol. 7, Issue 9 https://doi.org/10.1002/smll.201002254	journal	April 2011
Recent Progress of Textile-Based Wearable Electronics: A Comprehensive Review of Materials, Devices, and Applications Heo, Jae Sang; Eom, Jimi; Kim, Yong-Hoon Small, Vol. 14, Issue 3 https://doi.org/10.1002/smll.201703034	journal	December 2017
Recent Advances in Isoindigo‐Inspired Organic Semiconductors Randell, Nicholas M.; Kelly, Timothy L. The Chemical Record, Vol. 19, Issue 6 https://doi.org/10.1002/tcr.201800135	journal	October 2018
Organic Semiconductors in Sensor Applications Bernards, Daniel A.; Malliaras, George G.; Owens, Róisín M. Materials Science https://doi.org/10.1007/978-3-540-76314-7	book	January 2008
Recent advances on π-conjugated polymers as active elements in high performance organic field-effect transistors Luo, Lixing; Huang, Wanning; Yang, Canglei Frontiers of Physics, Vol. 16, Issue 3 https://doi.org/10.1007/s11467-020-1045-6	journal	March 2021
Review on thermochromic materials: development, characterization, and applications Hakami, Abdullatif; Srinivasan, Sesha S.; Biswas, Prasanta K. Journal of Coatings Technology and Research, Vol. 19, Issue 2 https://doi.org/10.1007/s11998-021-00558-x	journal	January 2022
Insight into High-Performance Conjugated Polymers for Organic Field-Effect Transistors Yang, Jie; Zhao, Zhiyuan; Wang, Shuai Chem, Vol. 4, Issue 12 https://doi.org/10.1016/j.chempr.2018.08.005	journal	December 2018
O2 and organic semiconductors: Electronic effects Nayak, Pabitra K.; Rosenberg, Ron; Barnea-Nehoshtan, Lee Organic Electronics, Vol. 14, Issue 3 https://doi.org/10.1016/j.orgel.2013.01.020	journal	March 2013
Detailed analysis and contact properties of low-voltage organic thin-film transistors based on dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DNTT) and its didecyl and diphenyl derivatives Kraft, Ulrike; Takimiya, Kazuo; Kang, Myeong Jin Organic Electronics, Vol. 35 https://doi.org/10.1016/j.orgel.2016.04.038	journal	August 2016
Smart Packaging: Opportunities and Challenges Schaefer, Dirk; Cheung, Wai M. Procedia CIRP, Vol. 72 https://doi.org/10.1016/j.procir.2018.03.240	journal	January 2018
Benzothiadiazole-based donor–acceptor nanoparticles with solvatochromic and thermoresponsive properties Nakabayashi, Kazuhiro; Takahashi, Tomoki; Sugawara, Ryo Reactive and Functional Polymers, Vol. 131 https://doi.org/10.1016/j.reactfunctpolym.2018.08.011	journal	October 2018
Highly-sensitive organic field effect transistor sensors for dual detection of humidity and NO2 Zhu, Yangyang; Zhang, Yiqun; Yu, Jiajia Sensors and Actuators B: Chemical, Vol. 374 https://doi.org/10.1016/j.snb.2022.132815	journal	January 2023
Highly aligned and crystalline poly(3-hexylthiophene) thin films by off-center spin coating for high performance organic field-effect transistors Chaudhary, Vivek; Pandey, Rajiv K.; Prakash, Rajiv Synthetic Metals, Vol. 258 https://doi.org/10.1016/j.synthmet.2019.116221	journal	December 2019
Self-Driving Laboratory for Polymer Electronics Vriza, Aikaterini; Chan, Henry; Xu, Jie Chemistry of Materials, Vol. 35, Issue 8 https://doi.org/10.1021/acs.chemmater.2c03593	journal	March 2023
Breaking the Bimolecular Crystal: The Effect of Side-Chain Length on Oligothiophene/Fullerene Intercalation Burnett, Edmund K.; Cherniawski, Benjamin P.; Rosa, Stephen J. Chemistry of Materials, Vol. 30, Issue 8 https://doi.org/10.1021/acs.chemmater.7b04702	journal	March 2018
Doping Approaches for Organic Semiconductors Scaccabarozzi, Alberto D.; Basu, Aniruddha; Aniés, Filip Chemical Reviews, Vol. 122, Issue 4 https://doi.org/10.1021/acs.chemrev.1c00581	journal	November 2021
Self-Healing Polymers for Electronics and Energy Devices Zhou, Yao; Li, Li; Han, Zhubing Chemical Reviews, Vol. 123, Issue 2 https://doi.org/10.1021/acs.chemrev.2c00231	journal	October 2022
Doped Organic Transistors Lüssem, Björn; Keum, Chang-Min; Kasemann, Daniel Chemical Reviews, Vol. 116, Issue 22 https://doi.org/10.1021/acs.chemrev.6b00329	journal	October 2016
Side-Chain Engineering of Conjugated Polymers for High-Performance Organic Field-Effect Transistors Luo, Nan; Ren, Peng; Feng, Yu The Journal of Physical Chemistry Letters, Vol. 13, Issue 4 https://doi.org/10.1021/acs.jpclett.1c03909	journal	January 2022
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties Ocheje, Michael U.; Charron, Brynn P.; Cheng, Yu-Hsuan Macromolecules, Vol. 51, Issue 4 https://doi.org/10.1021/acs.macromol.7b02393	journal	February 2018
Carbohydrate-Containing Conjugated Polymers: Solvent-Resistant Materials for Greener Organic Electronics Mooney, Madison; Wang, Yunfei; Iakovidis, Ekaterini ACS Applied Electronic Materials, Vol. 4, Issue 4 https://doi.org/10.1021/acsaelm.1c00932	journal	December 2021
Building a Versatile Platform for the Detection of Protein–Protein Interactions Based on Organic Field-Effect Transistors Yousefi, Nastaran; Caba, Cody; Hu, Anita ACS Applied Electronic Materials, Vol. 4, Issue 10 https://doi.org/10.1021/acsaelm.2c00983	journal	September 2022
Materials Design Strategies for Solvent-Resistant Organic Electronics Mooney, Madison; Crep, Chloe; Rondeau-Gagné, Simon ACS Applied Electronic Materials, Vol. 4, Issue 12 https://doi.org/10.1021/acsaelm.2c01228	journal	November 2022
Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains Mooney, Madison; Wang, Yunfei; Nyayachavadi, Audithya ACS Applied Materials & Interfaces, Vol. 13, Issue 21 https://doi.org/10.1021/acsami.1c02860	journal	May 2021
Structure–Property Relationships of Semiconducting Polymers for Flexible and Durable Polymer Field-Effect Transistors Kim, Min Je; Jung, A-Ra; Lee, Myeongjae ACS Applied Materials & Interfaces, Vol. 9, Issue 46 https://doi.org/10.1021/acsami.7b12435	journal	November 2017
Asymmetric Side-Chain Engineering of Isoindigo-Based Polymers for Improved Stretchability and Applications in Field-Effect Transistors Lin, Yan-Cheng; Chen, Fei-Hao; Chiang, Yun-Chi ACS Applied Materials & Interfaces, Vol. 11, Issue 37 https://doi.org/10.1021/acsami.9b10943	journal	August 2019
Asymmetric Siloxane Functional Side Chains Enable High-Performance Donor Copolymers for Photovoltaic Applications Tang, Ziye; Xu, Xiaopeng; Li, Ruipeng ACS Applied Materials & Interfaces, Vol. 12, Issue 15 https://doi.org/10.1021/acsami.9b20204	journal	March 2020
Understanding Comparable Charge Transport Between Edge-on and Face-on Polymers in a Thiazolothiazole Polymer System Saito, Masahiko; Koganezawa, Tomoyuki; Osaka, Itaru ACS Applied Polymer Materials, Vol. 1, Issue 6 https://doi.org/10.1021/acsapm.8b00111	journal	April 2019
Systematic Investigation of Isoindigo-Based Polymeric Field-Effect Transistors: Design Strategy and Impact of Polymer Symmetry and Backbone Curvature Lei, Ting; Cao, Yue; Zhou, Xu Chemistry of Materials, Vol. 24, Issue 10 https://doi.org/10.1021/cm300117x	journal	May 2012
Roles of Flexible Chains in Organic Semiconducting Materials Lei, Ting; Wang, Jie-Yu; Pei, Jian Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm4018776	journal	July 2013
The Rise of Organic Bioelectronics Rivnay, Jonathan; Owens, Róisín M.; Malliaras, George G. Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm4022003	journal	September 2013
Advances in Charge Carrier Mobilities of Semiconducting Polymers Used in Organic Transistors Holliday, Sarah; Donaghey, Jenny E.; McCulloch, Iain Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm402421p	journal	September 2013
Low-Voltage Organic Transistors Based on Tetraceno[2,3- b ]thiophene: Contact Resistance and Air Stability Kraft, Ulrike; Anthony, John E.; Ripaud, Emilie Chemistry of Materials, Vol. 27, Issue 3 https://doi.org/10.1021/cm5043183	journal	January 2015
Investigation of Structure–Property Relationships in Diketopyrrolopyrrole-Based Polymer Semiconductors via Side-Chain Engineering Back, Jang Yeol; Yu, Hojeong; Song, Inho Chemistry of Materials, Vol. 27, Issue 5 https://doi.org/10.1021/cm504545e	journal	February 2015
Understanding Odd−Even Effects in Organic Self-Assembled Monolayers Tao, Feng; Bernasek, Steven L. Chemical Reviews, Vol. 107, Issue 5 https://doi.org/10.1021/cr050258d	journal	May 2007
Interaction of Oxygen with Conjugated Polymers: Charge Transfer Complex Formation with Poly(3-alkylthiophenes) Abdou, Mohamed S. A.; Orfino, Francesco P.; Son, Yongkeun Journal of the American Chemical Society, Vol. 119, Issue 19 https://doi.org/10.1021/ja964229j	journal	May 1997
High operational and environmental stability of high-mobility conjugated polymer field-effect transistors through the use of molecular additives Nikolka, Mark; Nasrallah, Iyad; Rose, Bradley Nature Materials, Vol. 16, Issue 3 https://doi.org/10.1038/nmat4785	journal	December 2016
Dynamic self-stabilization in the electronic and nanomechanical properties of an organic polymer semiconductor Dobryden, Illia; Korolkov, Vladimir V.; Lemaur, Vincent Nature Communications, Vol. 13, Issue 1 https://doi.org/10.1038/s41467-022-30801-x	journal	June 2022
The role of chemical design in the performance of organic semiconductors Bronstein, Hugo; Nielsen, Christian B.; Schroeder, Bob C. Nature Reviews Chemistry, Vol. 4, Issue 2 https://doi.org/10.1038/s41570-019-0152-9	journal	January 2020
Realizing the full potential of conjugated polymers: innovation in polymer synthesis Morin, Pierre-Olivier; Bura, Thomas; Leclerc, Mario Materials Horizons, Vol. 3, Issue 1 https://doi.org/10.1039/C5MH00164A	journal	January 2016
Effect of the alkyl spacer length on the electrical performance of diketopyrrolopyrrole-thiophene vinylene thiophene polymer semiconductors Yu, Hojeong; Park, Kwang Hun; Song, Inho Journal of Materials Chemistry C, Vol. 3, Issue 44 https://doi.org/10.1039/C5TC02565F	journal	January 2015
Charge carrier traps in organic semiconductors: a review on the underlying physics and impact on electronic devices Haneef, Hamna F.; Zeidell, Andrew M.; Jurchescu, Oana D. Journal of Materials Chemistry C, Vol. 8, Issue 3 https://doi.org/10.1039/C9TC05695E	journal	January 2020
n-Type organic semiconducting polymers: stability limitations, design considerations and applications Griggs, Sophie; Marks, Adam; Bristow, Helen Journal of Materials Chemistry C, Vol. 9, Issue 26 https://doi.org/10.1039/D1TC02048J	journal	January 2021
Improving molecular alignment and charge percolation in semiconducting polymer films with highly localized electronic states through tailored thermal annealing Luzio, Alessandro; Martin, Jaime; Cheng, Christina H. Journal of Materials Chemistry C, Vol. 9, Issue 44 https://doi.org/10.1039/D1TC03907E	journal	January 2021
Asymmetric side-chain engineering in semiconducting polymers: a platform for greener processing and post-functionalization of organic electronics Mooney, Madison; Nyayachavadi, Audithya; Awada, Angela Polymer Chemistry, Vol. 14, Issue 5 https://doi.org/10.1039/D2PY01244H	journal	January 2023
Semiconducting polymers: the Third Generation Heeger, Alan J. Chemical Society Reviews, Vol. 39, Issue 7 https://doi.org/10.1039/b914956m	journal	January 2010
Inkjet printing of organic electronics – comparison of deposition techniques and state-of-the-art developments Teichler, Anke; Perelaer, Jolke; Schubert, Ulrich S. Journal of Materials Chemistry C, Vol. 1, Issue 10 https://doi.org/10.1039/c2tc00255h	journal	January 2013
Transfer printing methods for the fabrication of flexible organic electronics Hines, D. R.; Ballarotto, V. W.; Williams, E. D. Journal of Applied Physics, Vol. 101, Issue 2 https://doi.org/10.1063/1.2403836	journal	January 2007
High performance organic thin film transistor with phenyltrimethoxysilane-modified dielectrics Yuan, Guang Cai; Xu, Zheng; Gong, Cheng Applied Physics Letters, Vol. 94, Issue 15 https://doi.org/10.1063/1.3115828	journal	April 2009
Charge transport and trapping in organic field effect transistors exposed to polar analytes Duarte, Davianne; Sharma, Deepak; Cobb, Brian Applied Physics Letters, Vol. 98, Issue 13 https://doi.org/10.1063/1.3569592	journal	March 2011
Tutorial: Organic field-effect transistors: Materials, structure and operation Lamport, Zachary A.; Haneef, Hamna F.; Anand, Sajant Journal of Applied Physics, Vol. 124, Issue 7 https://doi.org/10.1063/1.5042255	journal	August 2018
Side-chain engineering as a powerful tool to tune the properties of polymeric field-effect transistors Lv, Siyu; Li, Liang; Mu, Youbing Polymer Reviews, Vol. 61, Issue 3 https://doi.org/10.1080/15583724.2020.1855195	journal	December 2020
Stretchable electronics: recent progress in the preparation of stretchable and self-healing semiconducting conjugated polymers Ocheje, Michael U.; Charron, Brynn P.; Nyayachavadi, Audithya Flexible and Printed Electronics, Vol. 2, Issue 4 https://doi.org/10.1088/2058-8585/aa9c9b	journal	December 2017
Progress and Challenges in Commercialization of Organic Electronics Loo, Yueh-Lin; McCulloch, Iain MRS Bulletin, Vol. 33, Issue 07, p. 653-662 https://doi.org/10.1557/mrs2008.149	journal	July 2008
Flexible Electronics: Status, Challenges and Opportunities Corzo, Daniel; Tostado-Blázquez, Guillermo; Baran, Derya Frontiers in Electronics, Vol. 1 https://doi.org/10.3389/felec.2020.594003	journal	September 2020
Recent Progress in Conjugated Conducting and Semiconducting Polymers for Energy Devices Heydari Gharahcheshmeh, Meysam; Gleason, Karen K. Energies, Vol. 15, Issue 10 https://doi.org/10.3390/en15103661	journal	May 2022
E-Skin: The Dawn of a New Era of On-Body Monitoring Systems Bunea, Alina-Cristina; Dediu, Violeta; Laszlo, Edwin Alexandru Micromachines, Vol. 12, Issue 9 https://doi.org/10.3390/mi12091091	journal	September 2021
Effects of Charge Traps on Hysteresis in Organic Field-Effect Transistors and Their Charge Trap Cause Analysis through Causal Inference Techniques Kim, Somi; Yoo, Hochen; Choi, Jaeyoung Sensors, Vol. 23, Issue 4 https://doi.org/10.3390/s23042265	journal	February 2023

Similar Records

Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains

Journal Article · Wed May 19 00:00:00 EDT 2021 · ACS Applied Materials and Interfaces · OSTI ID:1865533

Improving Charge Transport and Environmental Stability of Carbohydrate‐Bearing Semiconducting Polymers in Organic Field‐Effect Transistors

Citation Formats

References (63)

Similar Records

Related Subjects