Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing <italic style="font-style: italic">Meta</italic>-substituted Structure and Trifluoromethyl Groups

Hong-Tao Zuo; Feng Gan; Jie Dong; Peng Zhang; Xin Zhao; Qing-Hua Zhang

doi:10.1007/s10118-021-2514-2

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Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups

ARTICLE | Updated：2020-11-10

- Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups
- Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups
- Chinese Journal of Polymer Science 2021年39卷第4期页码：455-464
- Affiliations：
  
  a.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China
  b.Institute of High Energy Physics, Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  xzhao@dhu.edu.cn (X.Z.)
  qhzhang@dhu.edu.cn (Q.H.Z.)
- Funds：
  
  This work was financially supported by the Scientific Research Innovation Plan of Shanghai Education Commission (No. 2019-01-07-00-03-E00001), the National Natural Science Foundation of China (Nos. 21774019, 21975040, and 51903038), the Program of Shanghai Academic Research Leader (No. 18XD1400100), the Natural Science Foundation of Shanghai (No. 18ZR1400600) and the DHU Distinguished Young Professor Program.
- DOI：10.1007/s10118-021-2514-2
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Hong-Tao Zuo, Feng Gan, Jie Dong, 等. Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups[J]. Chinese Journal of Polymer Science, 2021,39(4):455-464.

Hong-Tao Zuo, Feng Gan, Jie Dong, et al. Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups[J]. Chinese Journal of Polymer Science, 2021,39(4):455-464.
Hong-Tao Zuo, Feng Gan, Jie Dong, 等. Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups[J]. Chinese Journal of Polymer Science, 2021,39(4):455-464. DOI： 10.1007/s10118-021-2514-2.

Hong-Tao Zuo, Feng Gan, Jie Dong, et al. Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups[J]. Chinese Journal of Polymer Science, 2021,39(4):455-464. DOI： 10.1007/s10118-021-2514-2.

摘要

Abstract

An effective design strategy for preparing highly transparent polyimide film with low dielectric constant is presented. The key to the strategy is to simultaneously introduce ,meta,-substituted structure and trifluoromethyl in polymer chains. By using this design strategy, a highly transparent polyimide film with low-,k, was synthesized from 3,5-diaminobenzotrifluoride (,m,-TFPDA) and 4,4′-(hexafluoroisopropylidene) diphthalic anhydride (6FDA) through a two-step method. The obtained ,m,-TFPDA/6FDA (CPI) film (~30 μm) possesses high optical transparency (,λ,cutoff,=334 nm,T,450nm,=85.26%, Haze=0.31) and is close to colorless (,L,*,=96.03,a,*,=−0.34,b,*,=2.12, yellow index=3.96). The intrinsic ,k, and dielectric loss value of the film are 2.27 and 0.0013 at 10 kHz, respectively. More importantly, such low dielectric performance could remain stable up to 280 °C, and the film shows a low moisture rate (~0.51%), which helps to maintain the low-,k, property stability in different humid environments. Meanwhile, the film also shows good thermal stability and mechanical properties, with a glass transition temperature (,T,g,) of 296 °C and the 5 wt% decomposition temperature (,T,d,5%,) of 522 °C under N,2,. The tensile strength and tensile modulus of the film are 85.1 MPa and 1.96 GPa, respectively. In addition, the film is soluble in common solvents, which allows simple solution processing and low-cost, continuous roll-to-roll processes. This design strategy is beneficial to improving the transparency, lightening yellow color, lowering the dielectric constant and meanwhile maintaining the comprehensive properties of polyimide films, which is mainly due to the introduced ,meta,-substituted and trifluoromethyl structures effectively inhibiting the transfer of charge transfer complex (CTC) effects and increasing the free volume of film. This design strategy could also be extended to other high-performance polymer systems.

关键词

Keywords

Polyimide filmTransparentColorlessLow dielectric constant

references

Lee, D. H.; Yun, H. D.; Jung, E. D.; Chu, J. H.; Nam, Y. S. Song, S.; Seok, S. H.; Song, M. H. Kwon, S. Y. . Ultrathin graphene intercalation in PEDOT:PSS/colorless polyimide-based transparent electrodes for enhancement of optoelectronic performance and operational stability of organic devices . ACS Appl. Mater. Interfaces , 2019 . 11 21069 -21077 . DOI:10.1021/acsami.9b04118http://doi.org/10.1021/acsami.9b04118 .

Yin, X. D.; Feng, Y. Y.; Zhao, Q.; Li, Y.; Li, S. W.; Dong, H. L.; Hu, W. P.; Feng, W. A. . A highly transparent, strong, and flexible fluorographene/fluorinated polyimide nanocomposite film with low dielectric constant . J. Mater. Chem. C , 2018 . 6 6378 -6384 . DOI:10.1039/C8TC00998Hhttp://doi.org/10.1039/C8TC00998H .

Kim, S. D.; Lee, B.; Byun, T.; Chung, I. S.; Park, J.; Shin, I.; Ahn, N. Y.; Seo, M.; Lee, Y.; Kim, Y.; Kim, W. Y.; Kwon, H.; Moon, H.; Yoo, S.; Kim, S. Y. . Poly(amide-imide) materials for transparent and flexible displays . Sci. Adv. , 2018 . 4 eaau1956 .

Li, T. L.; Hsu, S. L. C. . Preparation and properties of a high temperature, flexible and colorless ITO coated polyimide substrate . Eur. Polym. J. , 2007 . 43 3368 -3373 . DOI:10.1016/j.eurpolymj.2007.04.039http://doi.org/10.1016/j.eurpolymj.2007.04.039 .

Kang, S. B.; Kim, H. J.; Noh, Y. J.; Na, S. I.; Kim, H. K. . Face-to-face transferred multicrystalline ITO films on colorless polyimide substrates for flexible organic solar cells . Nano Energy , 2015 . 11 179 -188 . DOI:10.1016/j.nanoen.2014.10.030http://doi.org/10.1016/j.nanoen.2014.10.030 .

Bai, L.; Zhai, L.; Hea, M. H.; Wang, C. O.; Mo, S.; Fan, L. . Thermal expansion behavior of poly(amide-imide) films with ultrahigh tensile strength and ultralow CTE . Chinese J. Polym. Sci. , 2020 . 38 748 -758 . DOI:10.1007/s10118-020-2366-1http://doi.org/10.1007/s10118-020-2366-1 .

Kashiyama, Y.; He, J. H.; Machida, S.; Horie, K. . Large photoinduced refractive index change in a polyimide film by charge-transfer complex formation with a polymer-bound phenylazide fragment . Macromol. Rapid Commun. , 2001 . 22 185 -188 . DOI:10.1002/1521-3927(200102)22:3<185::AID-MARC185>3.0.CO;2-Chttp://doi.org/10.1002/1521-3927(200102)22:3<185::AID-MARC185>3.0.CO;2-C .

Ishida, H.; Wellinghoff, S. T.; Baer, E.; Koenig, J. . Spectroscopic studies of poly [N,N′-bis(phenoxyphenyl) pyromellitimide]. 1. Structures of the polyimide and three model compounds . Macromolecules , 1980 . 13 826 -834 . DOI:10.1021/ma60076a011http://doi.org/10.1021/ma60076a011 .

Zhang, Q.; Tsai, C. Y.; Li, L. J.; Liaw, D. J. . Colorless-to-colorful switching electrochromic polyimides with very high contrast ratio . Nat. Commun. , 2019 . 10 1239 DOI:10.1038/s41467-019-09054-8http://doi.org/10.1038/s41467-019-09054-8 .

Kim, M.; Ryu, T. I.; Ok, K. H.; Kwak, M. G.; Park, S.; Park, N. G.; Han, C. J.; Kim, B. S.; Ko, M. J.; Son, H. J.; Kim, J. W. . Transparent electronics: inverted layer-by-layer fabrication of an ultraflexible and transparent Ag nanowire/conductive polymer composite electrode for use in high-performance organic solar cells . Adv. Funct. Mater. , 2015 . 25 4580 -4589 . DOI:10.1002/adfm.201501046http://doi.org/10.1002/adfm.201501046 .

Jang, J. H.; Cueva, G.; Hoke, W. E.; Lemonias, P. J.; Fay, P.; Adesida, I. . Metamorphic graded bandgap InGaAs-InGaAlAs-InAlAs double heterojunction P-i-I-N photodiodes . J. Lightwave. Technol. , 2002 . 20 507 -514 . DOI:10.1109/50.989001http://doi.org/10.1109/50.989001 .

Ni, H. J.; Liu, J. G.; Wang, Z. H.; Yang, S. Y. . A review on colorless and optically transparent polyimide films: chemistry, process and engineering applications . J. Ind. Eng. Chem. , 2015 . 28 16 -27 . DOI:10.1016/j.jiec.2015.03.013http://doi.org/10.1016/j.jiec.2015.03.013 .

Mi, Z. M.; Liu, Z. X.; Yao, J. N.; Wang. C. B.; Zhou, C. J.; Wang. D. M.; Zhao, X. G.; Zhou, H. W.; Zhang, Y. M.; Chen, C. H. . Transparent and soluble polyimide films from 1,4:3,6-dianhydro-D-mannitol based dianhydride and diamines containing aromatic and semiaromatic units: preparation, characterization, thermal and mechanical properties . Polym. Degrad. Stab. , 2018 . 151 80 -89 . DOI:10.1016/j.polymdegradstab.2018.01.006http://doi.org/10.1016/j.polymdegradstab.2018.01.006 .

Li, F.; Shen, J. L.; Liu, X. F.; Cao, Z. H.; Cai, X.; Li, J. L.; Ding, K.; Liu, J. K.; Tu, G. L. . Flexible QLED and OPV based on transparent polyimide substrate with rigid alicyclic asymmetric isomer . Org. Electron. , 2017 . 51 54 -61 . DOI:10.1016/j.orgel.2017.09.010http://doi.org/10.1016/j.orgel.2017.09.010 .

Zhai, L.; Yang, S. Y.; Fan, L. . Preparation and characterization of highly transparent and colorless semi-aromatic polyimide films derived from alicyclic dianhydride and aromatic diamines . Polymer , 2012 . 53 3529 -3539 . DOI:10.1016/j.polymer.2012.05.047http://doi.org/10.1016/j.polymer.2012.05.047 .

Yeo, H.; Goh, M.; Ku, B. C.; You, N. H. . Synthesis and characterization of highly-fluorinated colorless polyimides derived from 4,4′-((perfluoro-[1,1′-biphenyl]-4,4′-diyl)bis(oxy))bis(2,6-dimethylaniline) and aromatic dianhydrides . Polymer , 2015 . 76 280 -286 . DOI:10.1016/j.polymer.2015.09.019http://doi.org/10.1016/j.polymer.2015.09.019 .

Jia, M. C.; Zhou, M. T.; Li, Y. J.; Lu, G. L.; Huang, X. Y. . Construction of semi-fluorinated polyimides with perfluorocyclobutyl aryl ether-based side chains . Polym. Chem. , 2018 . 9 920 -930 . DOI:10.1039/C8PY00004Bhttp://doi.org/10.1039/C8PY00004B .

Sato, S.; Ichikawa, M.; Suzuki, E.; Matsumoto, M.; Nagai, K. . Photoelectric properties of ABA-type triblock copolymers designed using fluorine-containing polyimide macroinitiators with polyhedral oligomeric silsesquioxane . Polym. Eng. Sci. , 2017 . 57 1207 -1213. .

Zhuang, Y. B.; Seong, J. G.; Lee, Y. M. . Polyimides containing aliphatic/alicyclic segments in the main chains . Prog. Polym. Sci. , 2019 . 92 35 -88 . DOI:10.1016/j.progpolymsci.2019.01.004http://doi.org/10.1016/j.progpolymsci.2019.01.004 .

Nawaz, H.; Akhter, Z.; Iqbal, N. . Study of physicochemical properties of meta and ortho trifluoromethyl substituted isomeric aromatic polyimides . Polym. Bull. , 2017 . 74 3889 -3906 . DOI:10.1007/s00289-017-1927-0http://doi.org/10.1007/s00289-017-1927-0 .

Lee, C. W.; Kwak, S. M.; Yoon, T. H. . Synthesis and characterization of polyimides from bis(3-aminophenyl)-2,3,5,6-tetrafluoro-4-trifluoromethylphenyl phosphine oxide (mDA7FPPO) . Polymer , 2006 . 47 4140 -4147 . DOI:10.1016/j.polymer.2006.03.002http://doi.org/10.1016/j.polymer.2006.03.002 .

Bong, S.; Yeo, H.; Ku, B. C.; Goh, M.; You, N. H. . Highly soluble polyimide based on asymmetric diamines containing trifluoromethyl group for high performance dielectric material . Macromol. Res. , 2018 . 26 85 -91. .

Wang, C. Y.; Zhao, X. Y.; Li, G.; Jiang, J. M. . High solubility and optical transparency of novel polyimides containing 3,3′,5,5′-tetramethyl pendant groups and 4-tert-butyltoluene moiety . Polym. Degrad. Stab. , 2009 . 94 1526 -1532 . DOI:10.1016/j.polymdegradstab.2009.04.032http://doi.org/10.1016/j.polymdegradstab.2009.04.032 .

Qian, C.; Bei, R. X.; Zhu, T. W.; Zheng, W. W.; Liu, S. W.; Chi, Z. G.; Aldred, M. P.; Chen, X. D.; Zhang, Y.; Xu, J. R. . Facile strategy for intrinsic Low-k dielectric polymers: molecular design based on secondary relaxation behavior . Macromolecules , 2019 . 52 4601 -4609 . DOI:10.1021/acs.macromol.9b00136http://doi.org/10.1021/acs.macromol.9b00136 .

Li, X. T.; Liu, T.; Jiao, Y. Z.; Dong, J.; Gan, F.; Zhao, X.; Zhang, Q. H. . Novel high-performance poly(benzoxazole-co-imide) resins with low dielectric constants and superior thermal stabilities derived from thermal rearrangement of ortho-hydroxy polyimide oligomers . Chem. Eng. J. , 2019 . 359 641 -651 . DOI:10.1016/j.cej.2018.11.175http://doi.org/10.1016/j.cej.2018.11.175 .

Amin, M.; Samy, H.; Küpper, J. . Robust and accurate computational estimation of the polarizability tensors of macromolecules . J. Phys. Chem. Lett. , 2019 . 10 2938 -2943 . DOI:10.1021/acs.jpclett.9b00963http://doi.org/10.1021/acs.jpclett.9b00963 .

Yu, S. Z.; Wong, T. K. S.; Hu, X.; Pita, K. . Synthesis and characterization of porous silsesquioxane dielectric films . Thin Solid Films , 2005 . 473 191 -195 . DOI:10.1016/j.tsf.2004.03.040http://doi.org/10.1016/j.tsf.2004.03.040 .

Liu, Y. W.; Qian, C.; Qu, L. J.; Wu, Y. N.; Zhang, Y.; Wu, X. H.; Zou, B. Y.; Chen, W. X.; Chen, Z. Q.; Chi, Z. G.; Liu, S. W.; Oigiviy, L. Y.; Xu, J. R. . A bulk dielectric polymer film with intrinsic ultralow dielectric constant and outstanding comprehensive properties . Chem. Mater. , 2015 . 27 6543 -6549 . DOI:10.1021/acs.chemmater.5b01798http://doi.org/10.1021/acs.chemmater.5b01798 .

Chern, Y. T.; Tsai, J. Y. . Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-bis(4-aminophenoxy)-2,6-di-tert-butylbenzene . Macromolecules , 2008 . 41 9556 -9564 . DOI:10.1021/ma802305qhttp://doi.org/10.1021/ma802305q .

Chen, W. X.; Zhou, Z. X.; Yang, T. T.; Bei, R. X.; Zhang, Y.; Liu, S. W.; Chi, Z. G.; Chen, X. D.; Xu, J. R. . Synthesis and properties of highly organosoluble and low dielectric constant polyimides containing non-polar bulky triphenyl methane moiety . React. Funct. Polym. , 2016 . 108 71 -77 . DOI:10.1016/j.reactfunctpolym.2016.04.011http://doi.org/10.1016/j.reactfunctpolym.2016.04.011 .

Liu, Y. W.; Tang, L. S.; Qu, L. J.; Liu, S. W.; Chi, Z. G.; Zhang, Y.; Xu, J. R. . Synthesis and properties of high-performance functional polyimides containing rigid nonplanar conjugated fluorene moieties . Chinese J. Polym. Sci. , 2019 . 37 416 -427 . DOI:10.1007/s10118-019-2225-0http://doi.org/10.1007/s10118-019-2225-0 .

Liu, Y. W.; Zhou, Z. X.; Qu, L. J.; Zou, B.; Chen, Z. Q.; Zhang, Y., Liu, S. W.; Chi, Z. G.; Chen, X. D.; Xu, J. R. . Exceptionally thermostable and soluble aromatic polyimides with special characteristics: intrinsic ultralow dielectric constant, static random access memory behaviors, transparency and fluorescence . Mater. Chem. Front. , 2017 . 1 326 -337 . DOI:10.1039/C6QM00027Dhttp://doi.org/10.1039/C6QM00027D .

Yang, H.; Cheng, X. P.; Cheng, X. X.; Pan, F. S.; Wu, H.; Liu, G. H.; Song, Y. M.; Cao, X. Z.; Jiang, Z. Y. . Highly water-selective membranes based on hollow covalent organic frameworks with fast transport pathways . J. Membr. Sci. , 2018 . 565 331 -341 . DOI:10.1016/j.memsci.2018.08.043http://doi.org/10.1016/j.memsci.2018.08.043 .

Liu, H.; Zhai, L.; Bai, L.; He, M. H.; Wang, C. O.; Mo, S.; Fan, L. . Synthesis and characterization of optically transparent semi-aromatic polyimide films with low fluorine content . Polymer , 2019 . 163 106 -114 . DOI:10.1016/j.polymer.2018.12.045http://doi.org/10.1016/j.polymer.2018.12.045 .

Tao, S. J. . Positronium annihilation in molecular substances . J. Chem. Phys. , 1972 . 56 5499 -5510 . DOI:10.1063/1.1677067http://doi.org/10.1063/1.1677067 .

Dlubek, G.; Stejny, J.; Alam, M. A. . Effect of cross-linking on the free-volume properties of diethylene glycol bis(allyl carbonate) polymer networks: a positron annihilation lifletime study . Macromolecules , 1998 . 31 4574 -4580 . DOI:10.1021/ma971801yhttp://doi.org/10.1021/ma971801y .

Eldrup, M. M.; Lightbody, D.; Sherwood, J. N. . The temperature dependence of positron lifetimes in solid pivalic acid . Phys. Chem. Chem. Phys. , 1981 . 63 51 -58. .

Ghaemy, M.; Berenjestanaki, F. R.; Bazzar, M. . Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains . Des. Monomers Polym. , 2014 . 17 101 -110 . DOI:10.1080/15685551.2013.840473http://doi.org/10.1080/15685551.2013.840473 .

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Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing Meta-substituted Structure and Trifluoromethyl Groups

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DOI：10.1007/s10118-021-2514-2

摘要

Abstract

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Keywords

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