

FOLLOWUS
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
xzhao@dhu.edu.cn (X.Z.)
qhzhang@dhu.edu.cn (Q.H.Z.)
Received:05 August 2020,
Revised:2020-9-28,
Accepted:05 October 2020,
Online First:10 November 2020,
Published:01 January 2021
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Zuo, H. T.; Gan, F.; Dong, J.; Zhang, P.; Zhao, X.; Zhang, Q. H. Highly transparent and colorless polyimide film with low dielectric constant by introducing , meta,-substituted structure and trifluoromethyl groups. Chinese J. Polym. Sci. 2021, 39, 455–464
Hong-Tao Zuo, Feng Gan, Jie Dong, et al. Highly Transparent and Colorless Polyimide Film with Low Dielectric Constant by Introducing
Zuo, H. T.; Gan, F.; Dong, J.; Zhang, P.; Zhao, X.; Zhang, Q. H. Highly transparent and colorless polyimide film with low dielectric constant by introducing , meta,-substituted structure and trifluoromethyl groups. Chinese J. Polym. Sci. 2021, 39, 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
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.
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.9b04118 http://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/C8TC00998H http://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.2007.04.039 http://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.2014.10.030 http://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/s10118-020-2366-1 http://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-C http://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/ma60076a011 http://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/s41467-019-09054-8 http://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.201501046 http://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: 10.1109/50.989001 http://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.2015.03.013 http://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.2018.01.006 http://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.2017.09.010 http://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.2012.05.047 http://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.2015.09.019 http://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/C8PY00004B http://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.2019.01.004 http://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/s00289-017-1927-0 http://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.2006.03.002 http://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.2009.04.032 http://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.9b00136 http://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.2018.11.175 http://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.9b00963 http://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.2004.03.040 http://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.5b01798 http://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/ma802305q http://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.2016.04.011 http://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/s10118-019-2225-0 http://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/C6QM00027D http://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.2018.08.043 http://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.2018.12.045 http://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: 10.1063/1.1677067 http://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/ma971801y http://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: 10.1080/15685551.2013.840473 http://doi.org/10.1080/15685551.2013.840473 .
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