Citation: Chong-Yu HUANG, Shi-Yu FENG, Wei-Guo HUANG. Pendant Group Effect of Polymeric Dielectrics on the Performance of Organic Thin Film Transistors[J]. Chinese Journal of Structural Chemistry, ;2021, 40(11): 1541-1549. doi: 10.14102/j.cnki.0254-5861.2011-3167 shu

Pendant Group Effect of Polymeric Dielectrics on the Performance of Organic Thin Film Transistors

Chong-Yu HUANG ^{a, b, c} ,
Shi-Yu FENG ^{a, b, c} ,
Wei-Guo HUANG ^{a, b, c,,}

a.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China, Fuzhou 350002, China

Corresponding author: Wei-Guo HUANG, whuang@fjirsm.ac.cn
Received Date: 2 March 2021
Accepted Date: 13 April 2021

Fund Project: the start-up funding from FJIRSM-CAS, and National Natural Science foundation of China 51803214

Figures(5)

Polymer dielectric is superior to its inorganic counterparts due to not only the low cost and intrinsic flexibility, but also the readily tunable dielectric constant, surface charge trap density, charge ejection and releasing ability and dipole moment, and all these properties play decisive roles in regulating the characteristic and performances of organic thin film transistors (OTFT). However, systematical studies on the relationship between structure and properties of polymeric dielectrics are rare. To this end, a series of polymeric dielectrics with well-defined linkages (ester or amide bonds) and predesigned pendant groups (alkyl- and aromatic-groups) are synthesized in high yields. Detailed studies show that the polyamide dielectrics exhibit higher dielectric constant, surface charge trapping density, and better charge storage capability than corresponding polyester dielectrics. Further, increasing the π electron delocalization of the pendant groups generally benefits the charge storage property and transistor memory behavior. Theoretical calculation reveals that the hydrogen bonding between the linkage groups and the energy alignment between polymeric dielectric and semiconductor are responsible for the observed performance differences of OTFT with different polymeric dielectrics. These results may shine light on the design of polymeric dielectrics for OTFTs with different applications.
- polymer dielectric,
- organic thin film transistor,
- hydrogen bonding,
- π-electron delocalization,
- noncovalent interaction
1. [1]
  Ortiz, R. P.; Facchetti, A.; Marks, T. J. High-k organic, inorganic, and hybrid dielectrics for low-voltage organic field-effect transistors. Chem. Rev. 2010, 110, 205–239. doi: 10.1021/cr9001275
2. [2]
  Wang, B.; Huang, W.; Chi, L.; Al-Hashimi, M.; Marks, T. J.; Facchetti, A. High-k gate dielectrics for emerging flexible and stretchable electronics. Chem. Rev. 2018, 118, 5690–5754. doi: 10.1021/acs.chemrev.8b00045
3. [3]
  Magliulo, M.; Manoli, K.; Macchia, E.; Palazzo, G.; Torsi, L. Tailoring functional interlayers in organic field-effect transistor biosensors. Adv. Mater. 2015, 27, 7528–7551. doi: 10.1002/adma.201403477
4. [4]
  Lee, W.; Kim, D.; Rivnay, J.; Matsuhisa, N.; Lonjaret, T.; Yokota, T.; Yawo, H.; Sekino, M.; Malliaras, G. G.; Someya, T. Integration of organic electrochemical and field-effect transistors for ultraflexible, high temporal resolution electrophysiology arrays. Adv. Mater. 2016, 28, 9722–9728. doi: 10.1002/adma.201602237
5. [5]
  Li, Y.; Huang, X.; Hu, Z.; Jiang, P.; Li, S.; Tanaka, T. Large dielectric constant and high thermal conductivity in poly(vinylidene fluoride)/barium titanate/silicon carbide three-phase nanocomposites. ACS Appl. Mater. Interfaces 2011, 3, 4396–4403. doi: 10.1021/am2010459
6. [6]
  Byun, H. R.; You, E. A.; Ha, Y. G. Multifunctional hybrid multilayer gate dielectrics with tunable surface energy for ultralow-power organic and amorphous oxide thin-film transistors. ACS Appl. Mater. Interfaces 2017, 9, 7347–7354. doi: 10.1021/acsami.6b15798
7. [7]
  Everaerts, K.; Emery, J. D.; Jariwala, D.; Karmel, H. J.; Sangwan, V. K.; Prabhumirashi, P. L.; Geier, M. L.; McMorrow, J. J.; Bedzyk, M. J.; Facchetti, A.; Hersam, M. C.; Marks, T. J. Ambient-processable high capacitance hafnia-organic self-assembled nanodielectrics. J. Am. Chem. Soc. 2013, 135, 8926–8939. doi: 10.1021/ja4019429
8. [8]
  Wang, Y.; Huang, X.; Li, T.; Li, L.; Guo, X.; Jiang, P. Polymer-based gate dielectrics for organic field-effect transistors. Chem. Mater. 2019, 31, 2212–2240. doi: 10.1021/acs.chemmater.8b03904
9. [9]
  Yi, H. T.; Payne, M. M.; Anthony, J. E.; Podzorov, V. Ultra-flexible solution-processed organic field-effect transistors. Nat. Commun. 2012, 3, 1259. doi: 10.1038/ncomms2263
10. [10]
  Wu, Y. L.; Lin, J. J.; Ma, C. M. Fabrication of an organic thin-film transistor by direct deposit of a pentacene layer onto a silicon substrate. J. Phys. Chem. Solids 2008, 69, 730–733. doi: 10.1016/j.jpcs.2007.07.089
11. [11]
  Jang, J.; Nam, S.; Chung, D. S.; Kim, S. H.; Yun, W. M.; Park, C. E. High t_g cyclic olefin copolymer gate dielectrics for N, N΄-ditridecyl perylene diimide based field-effect transistors: improving performance and stability with thermal treatment. Adv. Funct. Mater. 2010, 20, 2611–2618. doi: 10.1002/adfm.201000383
12. [12]
  Nugraha, M. I.; Häusermann, R.; Watanabe, S.; Matsui, H.; Sytnyk, M.; Heiss, W.; Takeya, J.; Loi, M. A. Broadening of distribution of trap states in PbS quantum dot field-effect transistors with high-k dielectrics. ACS Appl. Mater. Interfaces 2017, 9, 4719–4724. doi: 10.1021/acsami.6b14934
13. [13]
  Veres, J.; Ogier, S. D.; Leeming, S. W.; Cupertino, D. C.; Mohialdin Khaffaf, S. Low-k insulators as the choice of dielectrics in organic field-effect transistors. Adv. Funct. Mater. 2003, 13, 199–204. doi: 10.1002/adfm.200390030
14. [14]
  Xia, Y.; Cho, J. H.; Lee, J.; Ruden, P. P.; Frisbie, C. D. Comparison of the mobility-carrier density relation in polymer and single-crystal organic transistors employing vacuum and liquid gate dielectrics. Adv. Mater. 2009, 21, 2174–2179. doi: 10.1002/adma.200803437
15. [15]
  Sun, X.; Liu, Y.; Di, C. A.; Wen, Y.; Guo, Y.; Zhang, L.; Zhao, Y.; Yu, G. Interfacial heterogeneity of surface energy in organic field-effect transistors. Adv. Mater. 2011, 23, 1009–1014. doi: 10.1002/adma.201004187
16. [16]
  Kim, C.; Facchetti, A.; Marks, T. J. Polymer gate dielectric surface viscoelasticity modulates pentacene transistor performance. Science 2007, 318, 76–80. doi: 10.1126/science.1146458
17. [17]
  Orgiu, E.; Locci, S.; Fraboni, B.; Scavetta, E.; Lugli, P.; Bonfiglio, A. Analysis of the hysteresis in organic thin-film transistors with polymeric gate dielectric. Org. Electron. 2011, 12, 477–485. doi: 10.1016/j.orgel.2010.12.014
18. [18]
  Yang, H.; Kim, S. H.; Yang, L.; Yang, S. Y.; Park, C. E. Pentacene nanostructures on surface-hydrophobicity-controlled polymer/SiO₂ bilayer gate-dielectrics. Adv. Mater. 2007, 19, 2868–2872. doi: 10.1002/adma.200700560
19. [19]
  Alameddine, B.; Rice, A. H.; Luscombe, C.; Jenny, T. A. Synthesis of arylamine tribenzopentaphenes and investigation of their hole mobility. ChemistryOpen 2015, 4, 453–456. doi: 10.1002/open.201500064
20. [20]
  Baeg, K. J.; Noh, Y. Y.; Ghim, J.; Lim, B.; Kim, D. Y. Polarity effects of polymer gate electrets on non-volatile organic field-effect transistor memory. Adv. Funct. Mater. 2008, 18, 3678–3685. doi: 10.1002/adfm.200800378
21. [21]
  Kumar, R.; Goswami, M.; Sumpter, B. G.; Novikov, V. N.; Sokolov, A. P. Effects of backbone rigidity on the local structure and dynamics in polymer melts and glasses. Phys. Chem. Chem. Phys. 2013, 15, 4604–4609. doi: 10.1039/c3cp43737j
22. [22]
  Zhang, H. C.; Deng, R. N.; Wang, J.; Li, X.; Chen, Y. M.; Liu, K. W.; Taubert, C.; Cheng, S. Z. D.; Zhu, Y. Crystalline organic pigment-based field-effect transistors. ACS Appl. Mater. Interfaces 2017, 9, 21891–21899. doi: 10.1021/acsami.7b03170
23. [23]
  Zhang, H. C.; Li, R.; Deng, Z. F.; Cui, S. W.; Wang, Y. H.; Zheng, M.; Yang, W. J. π-Conjugated oligomers based on aminobenzodifuranone and diketopyrrolopyrrole. Dyes Pigm. 2020, 181, 108552. doi: 10.1016/j.dyepig.2020.108552
24. [24]
  Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras-García, J.; Cohen, A. J.; Yang, W. Revealing noncovalent interactions. J. Am. Chem. Soc. 2010, 132, 6498–6506. doi: 10.1021/ja100936w
25. [25]
  Wu, P.; Chaudret, R.; Hu, X.; Yang, W. Noncovalent interaction analysis in fluctuating environments. J. Chem. Theory. Comput. 2013, 9, 2226–2234. doi: 10.1021/ct4001087
26. [26]
  Contreras-García, J.; Yang, W.; Johnson, E. R. Analysis of hydrogen-bond interaction potentials from the electron density: integration of noncovalent interaction regions. J. Phys. Chem. A 2011, 115, 12983–12990. doi: 10.1021/jp204278k
27. [27]
  Emamian, S.; Lu, T.; Kruse, H.; Emamian, H. Exploring nature and predicting strength of hydrogen bonds: a correlation analysis between atoms-in-molecules descriptors, binding energies, and energy components of symmetry-adapted perturbation theory. J. Comput. Chem. 2019, 40, 2868–2881. doi: 10.1002/jcc.26068
28. [28]
  Ji, D.; Li, T.; Liu, J.; Amirjalayer, S.; Zhong, M.; Zhang, Z. Y.; Huang, X.; Wei, Z.; Dong, H.; Hu, W.; Fuchs, H. Band-like transport in small-molecule thin films toward high mobility and ultrahigh detectivity phototransistor arrays. Nat. Commun. 2019, 10, 12. doi: 10.1038/s41467-018-07943-y
29. [29]
  Wu, X.; Feng, S.; Shen, J.; Huang, W.; Li, C.; Li, C.; Sui, Y.; Huang, W. Nonvolatile transistor memory based on a high-k dielectric polymer blend for multilevel data storage, encryption, and protection. Chem. Mater. 2020, 32, 3641–3650. doi: 10.1021/acs.chemmater.0c01271
30. [30]
  Tsai, T. D.; Chang, J. W.; Wen, T. C.; Guo, T. F. Manipulating the hysteresis in poly(vinyl alcohol)-dielectric organic field-effect transistors toward memory elements. Adv. Funct. Mater. 2013, 23, 4206–4214. doi: 10.1002/adfm.201203694
31. [31]
  Weigend, F.; Ahlrichs, R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys. Chem. Chem. Phys. 2005, 7, 3297–3305. doi: 10.1039/b508541a
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