Fluorinated Colorless Polyimides with High Heat-resistance and Low Birefringence

Bing-Yu Zou; Lu-Hao Qiu; Huan-Yu Lei; Jin-Ming Liu; Wei-Feng Peng; Hong-Qin Zhao; Feng Bao; Ming-Jun Huang

doi:10.1007/s10118-023-3011-6

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Fluorinated Colorless Polyimides with High Heat-resistance and Low Birefringence

RESEARCH ARTICLE | Updated：2023-09-21

- Fluorinated Colorless Polyimides with High Heat-resistance and Low Birefringence
- Chinese Journal of Polymer Science Vol. 41, Issue 10, Pages: 1599-1608(2023)
- Affiliations：
  
  a.South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, Guangzhou 510640, China
  b.Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China University of Technology, Guangzhou 510640, China
- Author bio：
  
  fbao@scut.edu.cn (F.B.)
  huangmj25@scut.edu.cn (M.J.H.)
- Funds：
- DOI：10.1007/s10118-023-3011-6
  CLC：
- Received：23 April 2023，
  
  Revised：2023-5-24，
  
  Accepted：31 May 2023，
  
  Online First：24 July 2023，
  
  Published：01 October 2023
- Accepted：
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Zou, B. Y.; Qiu, L. H.; Lei, H. Y.; Liu, J. M.; Peng, W. F.; Zhao, H. Q.; Bao, F.; Huang, M. J. Fluorinated colorless polyimides with high heat-resistance and low birefringence. Chinese J. Polym. Sci. 2023, 41, 1599–1608

Bing-Yu Zou, Lu-Hao Qiu, Huan-Yu Lei, et al. Fluorinated Colorless Polyimides with High Heat-resistance and Low Birefringence[J]. Chinese Journal of Polymer Science, 2023, 41(10): 1599-1608.
Zou, B. Y.; Qiu, L. H.; Lei, H. Y.; Liu, J. M.; Peng, W. F.; Zhao, H. Q.; Bao, F.; Huang, M. J. Fluorinated colorless polyimides with high heat-resistance and low birefringence. Chinese J. Polym. Sci. 2023, 41, 1599–1608 DOI： 10.1007/s10118-023-3011-6.

Bing-Yu Zou, Lu-Hao Qiu, Huan-Yu Lei, et al. Fluorinated Colorless Polyimides with High Heat-resistance and Low Birefringence[J]. Chinese Journal of Polymer Science, 2023, 41(10): 1599-1608. DOI： 10.1007/s10118-023-3011-6.

摘要

We designed and synthesized a series of fluorinated colorless polyimides (CPI) through one-step polymerization of 2

5-substituted m-phenylenediamine diamine and CHDA dianhydride. Excellent combination of high heat-resistance

high transparency and low birefringence was achieved in these CPIs with simple chemical structures.

Abstract

The development of optical films with high transparency

high thermal resistance and low birefringence remains a challenge in the flexible display industry. In this work

we designed and synthesized a series of fluorinated colorless polyimides (CPIs) materials using 2

5-substituted

-phenylenediamine diamine monomers and 1

5-cyclohexanetetracarboxylic dianhydride (CHDA). We systematically studied the effects of fluorinated group substitutions on the thermal

mechanical

optical and dielectric properties of CPI films. The introduction of alicyclic CHDA dianhydride affords high transparency and low yellowness

while the 2

5-substituted

-phenylenediamine diamines offer the CPIs with quite low birefringence as well as high glass transition temperatures. A particular CHDA/

3FBDA film with simple chemical structure stands out

exhibiting well-balanced overall properties.

关键词

Keywords

references

Tominaka,S.;Nishizeko,H.;Mizuno,J.Osaka,T.Bendablefuelcells:on-chipfuelcellonaflexiblepolymersubstrate. Energy Environ. Sci. 2009 , 2 ,1074−1077..

Sheraw,C.D.;Zhou,L.;Huang,J.R.;Gundlach,D.J.;Jackson,T.N.;Kane,M.G.;Hill,I.G.;Hammond,M.S.;Campi,J.;Greening,B.K.;Francl,J.West,J.Organicthin-filmtransistor-drivenpolymer-dispersedliquidcrystaldisplaysonflexiblepolymericsubstrates. Appl. Phys. Lett. 2002 , 80 ,1088−1090..

Villani,F.;Vacca,P.;Nenna,G.;Valentino,O.;Burrasca,G.;Fasolino,T.;Minarini,C.;dellaSala,D.InkjetprintedpolymerlayeronflexiblesubstrateforOLEDapplications. J. Phys. Chem. C 2009 , 113 ,13398−13402..

Li,H.;Ma,Y.Huang,Y.Materialinnovationandmechanicsdesignforsubstratesandencapsulationofflexibleelectronics:areview. Mater. Horiz. 2021 , 8 ,383−400..

Sroog,C.Polyimides. Prog. Polym. Sci. 1991 , 16 ,561−694..

Ding,M.Isomericpolyimides. Prog. Polym. Sci. 2007 , 32 ,623−668..

Liaw,D.J.;Wang,K.L.;Huang,Y.C.;Lee,K.R.;Lai,J.Y.;Ha,C.S.Advancedpolyimidematerials:syntheses,physicalpropertiesandapplications. Prog. Polym. Sci. 2012 , 37 ,907−974..

Dhara,MG.Banerjee,S.Fluorinatedhigh-performancepolymers:poly(aryleneether)sandaromaticpolyimidescontainingtrifluoromethylgroups. Prog. Polym. Sci. 2010 , 35 ,1022−1077..

Yi,C.;Li,W.;Shi,S.;He,K.;Ma,P.;Chen,M.;Yang,C.High-temperature-resistantandcolorlesspolyimide:preparations,properties,andapplications. Sol. Energy. 2020 , 195 ,340−354..

Ni,H.J.;Liu,J.G.;Wang,Z.H.;Yang,S.Y.Areviewoncolorlessandopticallytransparentpolyimidefilms:chemistry,processandengineeringapplications. J. Ind. Eng. Chem. 2015 , 28 ,16−27..

Zhuang,Y.;Seong,J.G.;Lee,Y.M.Polyimidescontainingaliphatic/alicyclicsegmentsinthemainchains. Prog. Polym. Sci. 2019 , 92 ,35−88..

Ding,M. Polyimides: relationship between chemistry, structure, and performance and their materials .2 nd Ed.Beijing,SciencePress, 2012 ..

Abadie,M.J.M. High performance polymers-polyimides based- from chemistry to applications .Rijeka:IntechOpen; 2012 ..

Liu,Y.Y.;Wang,Y.K.;Wu,D.Y.Syntheticstrategiesforhighlytransparentandcolorlesspolyimidefilm. J. Appl. Polym. Sci. 2022 , 139 ,e52604..

Hu,X.;Yan,J.;Wang,Y.;Mu,H.;Wang,Z.;Cheng,H.;Zhao,F.;Wang,Z.Colorlesspolyimidesderivedfrom2R,5R,7S,10S-naphthanetetracarboxylicdianhydride. Polym. Chem. 2017 , 8 ,6165−6172..

Ozawa,H.;Ishiguro,E.;Kyoya,Y.;Kikuchi,Y.;Matsumoto,T.Colorlesspolyimidesderivedfromanalicyclictetracarboxylicdianhydride,CpODA. Polymers 2021 , 13 ,2824..

Peng,W.;Lei,H.;Qiu,L.;Bao,F.;Huang,M.Perfluorocyclobutyl-containingtransparentpolyimideswithlowdielectricconstantandlowdielectricloss. Polym. Chem. 2022 , 13 ,3949−3955..

Matsuura,T.;Hasuda,Y.;Nishi,S.;Yamada,N.Polyimidederivedfrom2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl.1.Synthesisandcharacterizationofpolyimidespreparedwith2,2'-bis(3,4-dicarboxyphenyl)hexafluoropropanedianhydrideorpyromelliticdianhydride. Macromolecules 1991 , 24 ,5001−5005..

Peng,W.F.;Lei,H.Y.;Zhang,X.X.;Qiu,L.H.;Huang,M.J.Fluorinesubstitutioneffectonthematerialpropertiesintransparentaromaticpolyimides. Chinese J. Polym. Sci. 2022 , 40 ,781−788..

Zuo,H.T.;Gan,F.;Dong,J.;Zhang,P.;Zhao,X.;Zhang,Q.H.Highlytransparentandcolorlesspolyimidefilmwithlowdielectricconstantbyintroducingmeta-substitutedstructureandtrifluoromethylgroups. Chinese J. Polym. Sci. 2021 , 39 ,455−464..

Lin,S.H.;Li,F.M.;Cheng,S.Z.D.;Harris,F.W.Organo-solublepolyimides:Synthesisandpolymerizationof2,2'-bis(trifluoromethyl)-4,4',5,5'-biphenyltetracarboxylicdianhydride. Macromolecules 1998 , 31 ,2080−2086..

Feiring,A.E.;Auman,B.C.;Wonchoba,E.R.Synthesisandpropertiesoffluorinatedpolyimidesfromnovel2,2'-bis(fluoroalkoxy)benzidines. Macromolecules 1993 , 26 ,2779−2784..

Song,G.;Chen,C.;Wang,X.;Yao,J.Synthesisandpropertiesofpolyimidesderivedfrom2,2'-dichloro-4,4',5,5'-biphenyl-tetracarboxylicdianhydride. Polymer 2019 , 183 ,121862..

Li,F.M.;Ge,J.J.;Honigfort,P.S.;Fang,S.;Chen,J.C.;Harris,F.W.;Cheng,S.Z.D.Dianhydridearchitecturaleffectsontherelaxationbehaviorsandthermalandopticalpropertiesoforgano-solublearomaticpolyimidefilms. Polymer 1999 , 40 ,4987−5002..

Hougham,G.;Tesoro,G.;Shaw,J.Synthesisandpropertiesofhighlyfluorinatedpolyimides. Macromolecules 1994 , 27 ,3642−3649..

Xiao,P.;He,X.;Zheng,F.;Lu,Q.Super-heatresistant,transparentandlowdielectricpolyimidesbasedonspirocyclicbisbenzoxazolediamineswith T g > 450°C. Polym. Chem. 2022 , 13 ,3660−3669..

Zhang,M.;Miao,J.;Xu,Y.;Wang,Z.;Yan,J.Colorlesspolyimidesfromfluorinatedladderdiaminescontainingnorbornylbenzocyclobutenesegments. Macromolecules 2022 ,DOI:10.1021/acs.macromol.2c00894..

Lei,H.;Bao,F.;Peng,W.;Qiu,L.;Zou,B.;Huang,M.Torsioneffectoftheimideringontheperformanceoftransparentpolyimidefilmswithmethyl-substitutedphenylenediamine. Polym. Chem. 2022 , 13 ,6606−6613..

Liu,H.;Zhai,L.;Bai,L.;He,M.;Wang,C.;Mo,S.Fan,L.Synthesisandcharacterizationofopticallytransparentsemi-aromaticpolyimidefilmswithlowfluorinecontent. Polymer 2019 , 163 ,106−114..

Tapaswi,P.K.;Ha,C.S.Recenttrendsontransparentcolorlesspolyimideswithbalancedthermalandopticalproperties:designandsynthesis. Macromol. Chem. Phys. 2019 , 220 ,1800313..

Hasegawa,M.Developmentofsolution-processable,opticallytransparentpolyimideswithultra-lowlinearcoefficientsofthermalexpansion. Polymers 2017 , 9 ,520..

Liu,J.;Nakamura,Y.;Shibasaki,Y.;Ando,S.;Ueda,M.Synthesisandcharacterizationofhighlyrefractivepolyimidesfrom4,4'-thiobis( p -phenylenesulfanyl)anilineandvariousaromatictetracarboxylicdianhydrides. J. Polym. Sci., Part A: Polym. Chem. 2007 , 45 ,5606−5617..

Uchiyama,A.;Ono,Y.;Ikeda,Y.;Shuto,H.;Yahata,K.Copolycarbonateopticalfilmsdevelopedusingbirefringencedispersioncontrol. Polym. J. 2012 , 44 ,995−1008..

Bao,F.;Lei,H.;Zou,B.;Peng,W.;Qiu,L.;Ye,F.;Song,Y.;Qi,F.;Qiu,X.;Huang,M.Colorlesspolyimidesderivedfromrigidtrifluoromethyl-substitutedtriphenylenediamines. Polymer 2023 , 273 ..

Li,F.M.;Kim,K.H.;Savitski,E.P.;Chen,J.C.;Harris,F.W.;Cheng,S.Z.D.Molecularweightandfilmthicknesseffectsonlinearopticalanisotropyof6FDA-PFMBpolyimides. Polymer 1997 , 38 ,3223−3227..

Ge,J.J.;Li,B.F.;Harris,F.W.;Cheng,S.Z.D.Novelpolymerwideviewinganglecompensationfilmsforliquidcrystaldisplays(LCDs). Chinese J. Polym. Sci. 2003 , 21 ,223−230..

Li,X.;Wang,M.;Mushtaq,N.;Chen,G.;Li,G.;Fang,X.;Zhang,A.Colorlesspolyimidefilmswithlowbirefringenceandretardation:synthesisandcharacterization. Polymer 2023 , 265 ,125579..

Ando,S.;Sawada,T.;Sasaki,S.Arod-likefluorinatedpolyimideasanin-planebirefringentopticalmaterial.2.Controlofopticalretardationusingspontaneousmolecularorientation. Polym. Adv. Technol. 1999 , 10 ,169−178..

Jung,Y.;Jeong,B.;Yang,Y.;Kim,T.;Kwon,S.Correlationofstressandopticalpropertiesinhighlytransparentpolyimidesforfutureflexibledisplay. Macromol. Res. 2017 , 25 ,971−975..

Nakabayashi,K.;Imai,T.;Fu,M.C.;Ando,S.;Higashihara,T.;Ueda,M.Poly(phenylenethioether)swithfluorene-basedcardostructuretowardhightransparency,highrefractiveindex,andlowbirefringence. Macromolecules 2016 , 49 ,5849−5856..

Min,X.;Wu,T.;Han,X.;An,M.;Yu,W.;Li,L.Zero-zerobirefringencecelluloseacetate-basedopticalfilmsbybenzoylation. ACS Appl. Polym. Mater. 2022 , 4 ,6255−6264..

Wen,P.;He,R.;Li,X.D.;Lee,M.H.Synthesesandcharacterizationsofhighrefractiveindexandlowbirefringencepolyimidescontainingspirobifluoreneinthesidechain. Polymer 2017 , 117 ,76−83..

Liu,Y.;Guo,J.;Wang,J.;Zhu,X.;Qi,D.;Li,W.;Shen,K.Anovelfamilyofopticallytransparentfluorinatedhyperbranchedpolyimideswithlonglinearbackbonesandbulkysubstituents. Eur. Polym. J. 2020 , 125 ,109526..

Sun,Q.;Feng,Y.;Guo,J.;Wang,C.Achievingbothlowthermalexpansionandlowbirefringenceforpolyimidesbyregulatingchainstructures. Eur. Polym. J. 2023 , 189 ,111986..

Matsuura,T.;Ishizawa,M.;Hasuda,Y.;Nishi,S.Polyimidesderivedfrom2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl.2.Synthesisandcharacterizationofpolyimidespreparedfromfluorinatedbenzenetetracarboxylicdianhydrides. Macromolecules 1992 , 25 ,3540−3545..

Bao,F.;Qi,F.;Lei,H.;Luo,F.;Cai,Y.;Dai,X.;Dong,Z.;Qiu,X.Near-zerothermalexpansionandhighheat-resistancepolyimidefilmsbasedonasymmetricandrigidpyrazinestructure. ACS Appl. Polym. Mater. 2022 , 5 ,672−679..

Li,D.;Wang,C.;Yan,X.;Ma,S.;Lu,R.;Qian,G.;Zhou,H.Heat-resistantcolorlesspolyimidesfrombenzimidazolediamines:Synthesisandproperties. Polymer 2022 , 254 ,125078..

Hasegawa,M.;Fujii,M.;Ishii,J.;Yamaguchi,S.;Takezawa,E.;Kagayama,T.Ishikawa,A.Colorlesspolyimidesderivedfrom1 S ,2 S ,4 R ,5 R -cyclohexanetetracarboxylicdianhydride,self-orientationbehaviorduringsolutioncasting,andtheiroptoelectronicapplications. Polymer 2014 , 55 ,4693−4708..

Wang,Z.H.;Chen,X.;Yang,H.X.;Zhao,J.;Yang,S.Y.Thein-planeorientationandthermalmechanicalpropertiesofthechemicallyimidizedpolyimidefilms. Chinese J. Polym. Sci. 2019 , 37 ,268−278..

Yin,Q.;Qin,Y.;Lv,J.;Wang,X.;Luo,L.;Liu,X.Reducingintermolecularfrictionwork:preparationofpolyimidefilmswithultralowdielectriclossfromMHztoTHzfrequency. Ind. Eng. Chem. Res. 2022 , 61 ,17894−17903..

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