Abstract
The solubility of a direct arylation polycondensation (DArP) synthesized conjugated polymer, i.e., poly(3,6-bis(furan-2-yl)-2,5-bis(4-tetradecyloctadecyl)-pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-1,2-bis(3,4-difluorothien-2-yl)ethene) (PFuDPP-4FTVT), in various organic solvents was studied. The polymer is soluble in 3-methylcyclohexanone (3-MC), a green solvent from peppermint oil, besides other solvents such as anisole, cyclopentyl methyl ether (CPME) and o-dichlorobenzene (o-DCB), etc. Based on the Hansen solubility parameters (HSP) analysis, 3-MC is identified as a “marginal solvent” of PFuDPP-4FTVT. The morphology of the spin-coated films with 3-MC as the solvent strongly correlated with the solution preparation conditions. With a 3-MC solution aged for 3 h at 70 °C, n-channel organic thin-film transistors (OTFTs) with electron mobility (μe) above 1 cm2·V−1·s−1 and current on/off ratio (Ion/Ioff) higher than 105 were fabricated by spin-coating. This is the first report on high mobility conjugated polymers for OTFTs processible with naturally occurred green solvent.
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Huang, F.; Bo, Z. S.; Geng, Y. H.; Wang, X. H.; Wang, L. X.; Ma, Y. G.; Hou, J. H.; Hu, W. P.; Pei, J.; Dong, H. L.; Wang, S.; Li, Z.; Shuai, Z. G.; Li, Y. F.; Cao, Y. Study on optoelectronic polymers: an overview and outlook. Acta Polymerica Sinica (in Chinese) 2019, 50, 988–1046.
Kim, M.; Ryu, S. U.; Park, S. A.; Choi, K.; Kim, T.; Chung, D.; Park, T. Donor-acceptor-conjugated polymer for high-performance organic field-effect transistors: a progress report. Adv. Funct. Mater. 2019, 30, 1904545.
Zhou, Y.; Zhang, W.; Yu, G. Recent structural evolution of lactam- and imide-functionalized polymers applied in organic field-effect transistors and organic solar cells. Chem. Sci. 2021, 12, 6844–6878.
Chen, J.; Yang, J.; Guo, Y.; Liu, Y. Acceptor modulation strategies for improving the electron transport in high-performance organic field-effect transistors. Adv. Mater. 2022, 34, e2104325.
Liu, Q.; Bottle, S. E.; Sonar, P. Developments of diketopyrrolopyrrole-dye-based organic semiconductors for a wide range of applications in electronics. Adv. Mater. 2020, 32, e1903882.
Yang, Y.; Liu, Z.; Zhang, G.; Zhang, X.; Zhang, D. The effects of side chains on the charge mobilities and functionalities of semiconducting conjugated polymers beyond solubilities. Adv. Mater. 2019, 31, e1903104.
Nielsen, C. B.; Turbiez, M.; McCulloch, I. Recent advances in the development of semiconducting DPP-containing polymers for transistor applications. Adv. Mater. 2013, 25, 1859–1880.
Shen, T.; Li, W.; Zhao, Y.; Liu, Y.; Wang, Y. An all-C−H-activation strategy to rapidly synthesize high-mobility well-balanced ambipolar semiconducting polymers. Matter 2022, 5, 1953–1968.
Kang, I.; Yun, H. J.; Chung, D. S.; Kwon, S. K.; Kim, Y. H. Record high hole mobility in polymer semiconductors via side-chain engineering. J. Am. Chem. Soc. 2013, 135, 14896–14899.
Yao, J.; Yu, C.; Liu, Z.; Luo, H.; Yang, Y.; Zhang, G.; Zhang, D. Significant improvement of semiconducting performance of the diketopyrrolopyrrole-quaterthiophene conjugated polymer through side-chain engineering via hydrogen-bonding. J. Am. Chem. Soc. 2016, 138, 173–185.
Wang, Z.; Gao, M.; He, C.; Shi, W.; Deng, Y.; Han, Y.; Ye, L.; Geng, Y. Unraveling the molar mass dependence of shearing-induced aggregation structure of a high-mobility polymer semiconductor. Adv. Mater. 2022, 34, e2108255.
Zhang, A.; Xiao, C.; Wu, Y.; Li, C.; Ji, Y.; Li, L.; Hu, W.; Wang, Z.; Ma, W.; Li, W. Effect of fluorination on molecular orientation of conjugated polymers in high performance field-effect transistors. Macromolecules 2016, 49, 6431–6438.
Back, J. Y.; Yu, H.; Song, I.; Kang, I.; Ahn, H.; Shin, T. J.; Kwon, S. K.; Oh, J. H.; Kim, Y. H. Investigation of structure-property relationships in diketopyrrolopyrrole-based polymer semiconductors via side-chain engineering. Chem. Mater. 2015, 27, 1732–1739.
Lv, S. Y.; Li, Q. Y.; Li, B. W.; Wang, J. Y.; Mu, Y. B.; Li, L.; Pei, J.; Wan, X. B. Thiazole-flanked thiazoloisoindigo as a monomer for balanced ambipolar polymeric field-effect transistors. Chinese J. Polym. Sci. 2022, 40, 1131–1140.
Capello, C.; Fischer, U.; Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007, 9, 927–934.
Campana, F.; Kim, C.; Marrocchi, A.; Vaccaro, L. Green solvent-processed organic electronic devices. J. Mater. Chem. C 2020, 8, 15027–15047.
Ran, Y.; Guo, Y.; Liu, Y. Organostannane-free polycondensation and eco-friendly processing strategy for the design of semiconducting polymers in transistors. Mater. Horiz. 2020, 7, 1955–1970.
Choi, H. H.; Baek, J. Y.; Song, E.; Kang, B.; Cho, K.; Kwon, S.-K.; Kim, Y. H. A pseudo-regular alternating conjugated copolymer using an asymmetric monomer: a high-mobility organic transistor in nonchlorinated solvents. Adv. Mater. 2015, 27, 3626–3631.
Ji, Y.; Xiao, C.; Wang, Q.; Zhang, J.; Li, C.; Wu, Y.; Wei, Z.; Zhan, X.; Hu, W.; Wang, Z.; Janssen, R. A. J.; Li, W. Asymmetric diketopyrrolopyrrole conjugated polymers for field-effect transistors and polymer solar cells processed from a nonchlorinated solvent. Adv. Mater. 2016, 28, 943–950.
Yun, H. J.; Lee, G. B.; Chung, D. S.; Kim, Y. H.; Kwon, S. K. Novel diketopyrroloppyrrole random copolymers: high charge-carrier mobility from environmentally benign processing. Adv. Mater. 2014, 26, 6612–6616.
Ding, S.; Ni, Z.; Hu, M.; Qiu, G.; Li, J.; Ye, J.; Zhang, X.; Liu, F.; Dong, H.; Hu, W. An asymmetric furan/thieno[3,2-b]thiophene diketopyrrolopyrrole building block for annealing-free green-solvent processable organic thin-film transistors. Macromol. Rapid Commun. 2018, 39, e1800225.
Wang, Z.; Song, X.; Jiang, Y.; Zhang, J.; Yu, X.; Deng, Y.; Han, Y.; Hu, W.; Geng, Y. A simple structure conjugated polymer for high mobility organic thin film transistors processed from nonchlorinated solvent. Adv. Sci. 2019, 6, 1902412.
Wang, Z.; Shi, Y.; Deng, Y.; Han, Y.; Geng, Y. Toward high mobility green solvent-processable conjugated polymers: a systematic study on chalcogen effect in poly(diketopyrrolopyrrole-alt-terchalcogenophene)s. Adv. Funct. Mater. 2021, 31, 2104881.
Ding, Y.; Zhao, F.; Kim, S.; Wang, X.; Lu, H.; Zhang, G.; Cho, K.; Qiu, L. Azaisoindigo-based polymers with a linear hybrid siloxane-based side chain for high-performance semiconductors processable with nonchlorinated solvents. ACS Appl. Mater. Interfaces 2020, 12, 41832–41841.
Ding, Y.; Jiang, L.; Du, Y.; Kim, S.; Wang, X.; Lu, H.; Zhang, G.; Cho, K.; Qiu, L. Linear hybrid siloxane-based side chains for highly soluble isoindigo-based conjugated polymers. Chem. Commun. 2020, 56, 11867–11870.
Prat, D.; Wells, A.; Hayler, J.; Sneddon, H.; McElroy, C. R.; Abou-Shehada, S.; Dunn, P. J. CHEM21 selection guide of classical- and less classical-solvents. Green Chem. 2016, 18, 288–296.
Alder, C. M.; Hayler, J. D.; Henderson, R. K.; Redman, A. M.; Shukla, L.; Shuster, L. E.; Sneddon, H. F. Updating and further expanding GSK’s solvent sustainability guide. Green Chem. 2016, 18, 3879–3890.
Prat, D.; Pardigon, O.; Flemming, H.-W.; Letestu, S.; Ducandas, V.; Isnard, P.; Guntrum, E.; Senac, T.; Ruisseau, S.; Cruciani, P.; Hosek, P. Sanofi’s solvent selection guide: a step toward more sustainable processes. Org. Process Res. Dev. 2013, 17, 1517–1525.
Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jennings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M. A.; Perry, D. A.; Stefaniak, M. Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation. Green Chem. 2008, 10, 31–36.
Chen, M. S.; Lee, O. P.; Niskala, J. R.; Yiu, A. T.; Tassone, C. J.; Schmidt, K.; Beaujuge, P. M.; Onishi, S. S.; Toney, M. F.; Zettl, A.; Fréchet, J. M. J. Enhanced solid-state order and field-effect hole mobility through control of nanoscale polymer aggregation. J. Am. Chem. Soc. 2013, 135, 19229–19236.
Sonar, P.; Chang, J.; Kim, J. H.; Ong, K. H.; Gann, E.; Manzhos, S.; Wu, J.; McNeill, C. R. High-mobility ambipolar organic thin-film transistor processed from a nonchlorinated solvent. ACS Appl. Mater. Interfaces 2016, 8, 24325–24330.
Lee, S. M.; Lee, H. R.; Han, A. R.; Lee, J.; Oh, J. H.; Yang, C. High-performance furan-containing conjugated polymer for environmentally benign solution processing. ACS Appl. Mater. Interfaces 2017, 9, 15652–15661.
Sui, Y.; Wang, Z.; Bai, J.; Shi, Y.; Zhang, X.; Deng, Y.; Han, Y.; Geng, Y. Diketopyrrolopyrrole-based conjugated polymers synthesized by direct arylation polycondensation for anisole-processed high mobility organic thin-film transistors. J. Mater. Chem. C 2022, 10, 2616–2622.
Li, C.; Misovich, M. V.; Pardo, M.; Fang, Z.; Laskin, A.; Chen, J.; Rudich, Y. Secondary organic aerosol formation from atmospheric reactions of anisole and associated health effects. Chemosphere 2022, 308, 136421.
Snyder, R.; Hedli, C. C. An overview of benzene metabolism. Environ. Health Perspect 1996, 104, 1165–1171.
Mohaddese M.; Nastaran K. Chemical composition and antimicrobial activity of peppermint (mentha piperita L.) essential oil. Songklanakarin J. Sci. Technol. 2014, 36, 83–87.
Newberne, P; Doull, J; Feron, V. J.; Goodman, J. I.; Munro, I. C.; Portoghese, P. S.; Waddell, W. J.; Wagner, B. M.; Weil, C. S.; Adams, T. B.; Hallagan, J. B. GRAS flavoring substances 19. Food Technol. 2000, 54, 66–84.
Lee, J.; Kim, G. W.; Kim, M.; Park, S. A.; Park, T. Nonaromatic green-solvent-processable, dopant-free, and lead-capturable hole transport polymers in perovskite solar cells with high efficiency. Adv. Energy Mater. 2020, 10, 1902662.
Machui, F.; Abbott, S.; Waller, D.; Koppe, M.; Brabec, C. J. Determination of Solubility Parameters for organic semiconductor formulations. Macromol. Chem. Phys. 2011, 212, 2159–2165.
Kim, N. K.; Shin, E. S.; Noh, Y. Y.; Kim, D. Y. A selection rule of solvent for highly aligned diketopyrrolopyrrole-based conjugated polymer film for high performance organic field-effect transistors. Org. Electron. 2018, 55, 6–14.
Dereje, M. M.; Ji, D.; Kang, S.H.; Yang, C.; Noh, Y. Y. Effect of pre-aggregation in conjugated polymer solution on performance of diketopyrrolopyrrole-based organic field-effect transistors. Dyes Pigments 2017, 145, 270–276.
Gaikwad, A. M.; Khan, Y.; Ostfeld, A. E.; Pandya, S.; Abraham, S.; Arias, A. C. Identifying orthogonal solvents for solution processed organic transistors. Org. Electron. 2016, 30, 18–29.
Li, H.; Liu, X.; Jin, T.; Zhao, K.; Zhang, Q.; He, C.; Yang, H.; Chen, Y.; Huang, J.; Yu, X.; Han, Y. Optimizing the intercrystallite connection of a donor-acceptor conjugated semiconductor polymer by controlling the crystallization rate via temperature. Macromol. Rapid Commun. 2022, 43, e2200084.
Zhao, K.; Zhang, Q.; Chen, L.; Zhang, T.; Han, Y. Nucleation and growth of P(NDI2OD-T2) nanowires via side chain ordering and backbone planarization. Macromolecules 2021, 54, 2143–2154.
Hansen, C. M. in Hansen Solubility Parameters: A User’s Handbook. CRC Press: Boca Raton, 2007, p. 75.
Panzer, F.; Bassler, H.; Kohler, A. Temperature induced order-disorder transition in solutions of conjugated polymers probed by optical spectroscopy. J. Phys. Chem. Lett. 2017, 8, 114–125.
Schroeder, B. C.; Chiu, Y. C.; Gu, X.; Zhou, Y.; Xu, J.; Lopez, J.; Lu, C.; Toney, M. F.; Bao, Z. Non-conjugated flexible linkers in semiconducting polymers: a pathway to improved processability without compromising device performance. Adv. Electron. Mater. 2016, 2, 1600104.
Zhou, Y.; Fuentes-Hernandez, C.; Shim, J.; Meyer, J.; Giordano, A. J.; Li, H.; Winget, P.; Papadopoulos, T.; Cheun, H.; Kim, J.; Fenoll, M.; Dindar, A.; Haske, W.; Najafabadi, E.; Khan, T. M.; Sojoudi, H.; Barlow, S.; Graham, S.; Bredas, J. L.; Marder, S. R.; Kahn, A.; Kippelen, B. A universal method to produce low-work function electrodes for organic electronics. Science 2012, 336, 327–332.
Dong, H.; Jiang, S.; Jiang, L.; Liu, Y.; Li, H.; Hu, W.; Wang, E.; Yan, S.; Wei, Z.; Xu, W.; Gong, X. Nanowire crystals of a rigid rod conjugated polymer. J. Am. Chem. Soc. 2009, 131, 17315–17320.
Yao, Y.; Dong, H.; Liu, F.; Russell, T. P.; Hu, W. Approaching intra- and interchain charge transport of conjugated polymers facilely by topochemical polymerized single crystals. Adv. Mater. 2017, 29, 1701251.
Yao, Z. F.; Li, Q. Y.; Wu, H. T.; Ding, Y. F.; Wang, Z. Y.; Lu, Y.; Wang, J. Y.; Pei, J. Building crystal structures of conjugated polymers through X-ray diffraction and molecular modeling. SmartMat 2021, 2, 378–387.
Rivnay, J.; Noriega, R.; Kline, R. J.; Salleo, A.; Toney, M. F. Quantitative analysis of lattice disorder and crystallite size in organic semiconductor thin films. Phys. Rev. B 2011, 84, 045203.
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This work was financially supported by the National Natural Science Foundation of China (Nos. 51933008 and 52121002) and the Fundamental Research Funds for the Central Universities.
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3-Methylcyclohexanone Processed n-Channel Organic Thin-Film Transistors Based on A Conjugated Polymer Synthesized by Direct Arylation
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Yan, DS., Zhang, XW., Wang, ZL. et al. 3-Methylcyclohexanone Processed n-Channel Organic Thin-Film Transistors Based on A Conjugated Polymer Synthesized by Direct Arylation Polycondensation. Chin J Polym Sci 41, 824–831 (2023). https://doi.org/10.1007/s10118-023-2937-z
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DOI: https://doi.org/10.1007/s10118-023-2937-z