CN113896926A - Antistatic polyimide film and application thereof - Google Patents
Antistatic polyimide film and application thereof Download PDFInfo
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- CN113896926A CN113896926A CN202111157326.1A CN202111157326A CN113896926A CN 113896926 A CN113896926 A CN 113896926A CN 202111157326 A CN202111157326 A CN 202111157326A CN 113896926 A CN113896926 A CN 113896926A
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- polyimide
- antistatic
- polyimide film
- polysiloxane
- layer
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 134
- 239000004642 Polyimide Substances 0.000 claims abstract description 83
- 239000000758 substrate Substances 0.000 claims abstract description 55
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 50
- -1 polysiloxane Polymers 0.000 claims abstract description 46
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 44
- 239000002041 carbon nanotube Substances 0.000 claims abstract description 29
- 229910021393 carbon nanotube Inorganic materials 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 18
- ZPSUIVIDQHHIFH-UHFFFAOYSA-N 3-(trifluoromethyl)-4-[2-(trifluoromethyl)phenyl]benzene-1,2-diamine Chemical group FC(F)(F)C1=C(N)C(N)=CC=C1C1=CC=CC=C1C(F)(F)F ZPSUIVIDQHHIFH-UHFFFAOYSA-N 0.000 claims description 17
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000004984 aromatic diamines Chemical class 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 3
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 claims description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 3
- FWOLORXQTIGHFX-UHFFFAOYSA-N 4-(4-amino-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluoroaniline Chemical group FC1=C(F)C(N)=C(F)C(F)=C1C1=C(F)C(F)=C(N)C(F)=C1F FWOLORXQTIGHFX-UHFFFAOYSA-N 0.000 claims description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 claims description 2
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 2
- 238000002834 transmittance Methods 0.000 abstract description 12
- 238000010438 heat treatment Methods 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000001035 drying Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000006185 dispersion Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 238000005406 washing Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 9
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000002048 multi walled nanotube Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000006258 conductive agent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/001—Macromolecular compounds containing organic and inorganic sequences, e.g. organic polymers grafted onto silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D187/00—Coating compositions based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C09D187/005—Block or graft polymers not provided for in groups C09D101/00 - C09D185/04
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/58—Structural electrical arrangements for semiconductor devices not otherwise provided for, e.g. in combination with batteries
- H01L23/60—Protection against electrostatic charges or discharges, e.g. Faraday shields
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Abstract
The invention provides an antistatic polyimide film and application thereof, wherein the polyimide film comprises: the polyimide film comprises a polyimide base layer and an antistatic layer positioned on the polyimide base layer; the polyimide substrate layer is made of polyimide; the antistatic layer is composed of polysiloxane grafted with carbon nanotubes. The polyimide film disclosed by the invention has an antistatic property while keeping high light transmittance.
Description
Technical Field
The invention relates to the technical field of high polymer materials, in particular to an antistatic polyimide film and application thereof.
Background
An Organic Light Emitting Diode (OLED) is a photoelectric technology for realizing multi-color display by using an organic semiconductor material to generate reversible color change under current driving. OLEDs have advantages of being thin, light, high in brightness, wide in viewing angle, fast in response, flexible, and the like, and are considered as a new generation display technology with the greatest development prospects. With the development of OLEDs in these years, OLEDs are used in display fields such as mobile phones, computers, televisions, and in-vehicle displays, and since the OLEDs are thinner and have a severe requirement for static electricity, protective films suitable for OLED displays are lacking in the market.
At present, the research on the antistatic protective film at home and abroad mainly focuses on thermoplastic resin materials such as Polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC) and the like, and the materials have the biggest defect of being incapable of resisting high temperature and generally being capable of melting at about 160 ℃. Polyimide films are widely used as protective films for OLED displays because of good mechanical properties, dielectric properties and thermal stability, but the current research results are unsatisfactory for obtaining antistatic polyimide films by using proper fillers and adopting proper film forming technology.
The application with Chinese patent publication No. CN105504811A discloses a long-acting antistatic polyimide film, which is prepared by carrying out polymerization reaction on aromatic diamine and tetracarboxylic dianhydride to obtain imidized substance of polyamic acid, adding an antistatic agent, and carrying out tape casting; the polyimide film prepared by the method has the surface resistivity of 105-107And the antistatic effect can be achieved for a long time between omega. In addition, chinese patent application publication No. CN102120826A discloses a method for preparing an antistatic polyimide film, which comprises preparing a polyamic acid conductive agent composite solution with uniform phase dispersion by in-situ polymerization using diamine, dianhydride, a conductive agent and a coupling agent as raw materials, and performing thermal imidization treatment to obtain the antistatic polyimide film. The antistatic materials of the two invention patents are added in a traditional blending mode, particles are easy to agglomerate in a solution and are not uniformly dispersed, and the mechanical property and the light transmittance of the prepared polyimide film are obviously reduced.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides an antistatic polyimide film and application thereof.
The invention provides an antistatic polyimide film, which comprises: the polyimide film comprises a polyimide base layer and an antistatic layer positioned on the polyimide base layer;
the polyimide substrate layer is made of polyimide; the antistatic layer is composed of polysiloxane grafted with carbon nanotubes.
Preferably, the polyimide is obtained by performing polycondensation reaction on monomers comprising aromatic diamine, alicyclic dianhydride and aromatic diacid chloride;
preferably, the aromatic diamine is at least one of 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 4' -diaminodiphenyl ether, or 4, 4' -diaminooctafluorobiphenyl;
preferably, the alicyclic dianhydride is at least one of 1, 2, 3, 4-cyclobutanetetracarboxylic dianhydride, 1, 2, 4, 5-cyclopentanetetracarboxylic dianhydride, bicyclo [2.2.1] hepta-2, 3, 5, 6-tetracarboxylic dianhydride or bicyclo [2.2.2] hepta-2, 3, 5, 6-tetracarboxylic dianhydride;
preferably, the aromatic diacid chloride is at least one of terephthaloyl chloride or isophthaloyl chloride.
Preferably, the aromatic diacid chloride is used in an amount of 10 to 30 mole percent of the aromatic diamine.
Preferably, the monomer further comprises an aromatic dianhydride;
preferably, the aromatic dianhydride is at least one of 4, 4'- (hexafluoroisopropylidene) diphthalic anhydride, 4, 4' -oxydiphthalic anhydride, 3', 4, 4' -benzophenone tetracarboxylic dianhydride, and 3, 3', 4, 4' -biphenyl tetracarboxylic dianhydride.
Preferably, the polysiloxane grafted with the carbon nanotubes is obtained by grafting the carbon nanotubes with the polysiloxane.
Preferably, the polysiloxane is obtained after the trialkoxysilane is condensed;
preferably, the trialkoxysilane is at least one of 3-chloropropyltriethoxysilane, methyltrimethoxysilane, aminopropyltriethoxysilane, or vinyltriethoxysilane.
Preferably, the carbon nanotubes are acid-activated carbon nanotubes;
preferably, the carbon nanotubes are used in an amount of 0.1 to 5 wt% of the polysiloxane.
Preferably, the polyimide substrate layer is obtained by film-forming polyimide;
preferably, the thickness of the polyimide substrate layer is 10 to 100 μm.
Preferably, the antistatic layer is obtained by coating polysiloxane grafted with carbon nanotubes on the polyimide-based bottom layer and forming a film;
preferably, the thickness of the antistatic layer is 0.1 to 10 μm.
An application of the antistatic polyimide film in an OLED display.
In the invention, the antistatic layer composed of polysiloxane grafted with carbon nano tubes is formed on the surface of the polyimide base layer with high light transmittance, so that the surface resistance of the obtained polyimide film is 10 on the basis of keeping the high light transmittance of the polyimide base layer7Omega or more.
Detailed Description
Hereinafter, the technical solution of the present invention will be described in detail by specific examples, but these examples should be explicitly proposed for illustration, but should not be construed as limiting the scope of the present invention.
The invention provides an antistatic polyimide film, which comprises: a polyimide base layer and an antistatic layer on the polyimide base layer.
The polyimide substrate layer is made of polyimide, and the polyimide is preferably obtained by performing a polycondensation reaction of monomers including aromatic diamine, alicyclic dianhydride, and aromatic diacid chloride. The polyimide synthesized by the raw materials is actually in a polyamide-imide structure, and when a polyimide substrate layer is formed, the light transmittance of more than 90 percent in a 400-700nm interval can be obtained, and the ultralow yellow index is less than 3.
The antistatic layer is composed of polysiloxane grafted with carbon nanotubes. Since the carbon nanotubes are uniformly dispersed in the polysiloxane grafted with the carbon nanotubes, the carbon nanotubes can be uniformly dispersed in the polysiloxane when the polysiloxane is coated on the polyimide substrateWhen forming a film, an antistatic layer having a high light transmittance can be formed, thus imparting the polyimide film 107A surface resistance of Ω or more, while not hindering the optical performance of the polyimide substrate layer.
In fact, the polysiloxane grafted with carbon nanotubes of the present invention utilizes the surface hydroxyl groups of the carbon nanotubes to be activated under the acid-washing condition, and the hydroxyl groups can generate Si — O bonds with the polysiloxane at a high temperature to form the polysiloxane grafted with carbon nanotubes, and the principle of the process can be shown as follows:
in order to more clearly describe the antistatic polyimide film of the present invention in detail, the following description will be given with reference to specific examples.
Example 1
The antistatic polyimide film comprises a polyimide substrate layer and an antistatic layer positioned on the polyimide substrate layer, and is prepared by the following method:
(1) under the protection of nitrogen, 2, 2' -bis (trifluoromethyl) diaminobiphenyl is added into N, N-dimethylacetamide and stirred to be completely dissolved, then 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are sequentially added, the solid content is adjusted to be 15 wt%, 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are stirred to react for 10 hours at the temperature of 10:3:5:2, then isoquinoline and acetic anhydride with the molar weight being 2 times of that of 2, 2' -bis (trifluoromethyl) diaminobiphenyl are added, the reaction is continued for 1 hour at room temperature, the temperature is increased to 80 ℃, and then the reaction is stirred for 1 hour, dripping the obtained reaction solution into excessive methanol to separate out a precipitate, filtering, washing with a large amount of methanol, crushing the obtained precipitate, and performing vacuum drying at 80 ℃ for 5 hours to obtain polyimide;
adding the polyimide into N, N-dimethylacetamide to be completely dissolved to obtain a polyimide solution with the solid content of 10%, casting the obtained polyimide solution on a glass substrate, placing the glass substrate in an oven, heating to 100 ℃, drying for 0.5h, continuously heating to 200 ℃, drying for 0.5h, heating to 280 ℃, drying for 1h, cooling to room temperature, and separating a membrane from the glass substrate to obtain a polyimide film, namely the polyimide substrate layer (the thickness of the polyimide substrate layer is 30 mu m, the light transmittance is 91.3% under the condition of 400-700nm, and the yellowness index YI is 2.4);
(2) dissolving 3-chloropropyltriethoxysilane in an ethanol-deionized water mixed solution with the volume ratio of 1:1, adding dilute hydrochloric acid (0.1mol/L) to adjust the pH value to 3.5-5.5, heating to 80 ℃, stirring for reaction for 5 hours, and evaporating to remove the solvent to obtain polysiloxane; then adding the multi-walled carbon nanotube into concentrated nitric acid according to the mass-volume ratio of 1g:10mL, carrying out ultrasonic heating reflux reaction for 6h, filtering, washing with water until the filtrate is neutral, drying in vacuum, and grinding to obtain a hydroxylated carbon nanotube (CNT-OH);
adding the polysiloxane into an ethanol-deionized water mixed solution with the volume ratio of 3:1, completely dissolving, adding the hydroxylated carbon nanotube (CNT-OH), uniformly stirring and dispersing, wherein the addition amount of the hydroxylated carbon nanotube is 2 wt% of that of the polysiloxane, heating to 80 ℃, reacting for 5 hours, and evaporating to remove the solvent to obtain the polysiloxane grafted with the carbon nanotube;
(3) and adding the polysiloxane grafted with the carbon nano tube into ethanol for uniform dispersion to obtain a dispersion liquid with the solid content of 20 wt%, coating the dispersion liquid on one surface of the polyimide substrate layer, carrying out heat treatment at 90 ℃ for 10min, and forming an antistatic layer (the thickness of the antistatic layer is 3 mu m) on the polyimide substrate layer to obtain the polyimide film.
Example 2
The antistatic polyimide film comprises a polyimide substrate layer and an antistatic layer positioned on the polyimide substrate layer, and is prepared by the following method:
(1) under the protection of nitrogen, 2, 2' -bis (trifluoromethyl) diaminobiphenyl is added into N, N-dimethylacetamide and stirred to be completely dissolved, then 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are sequentially added, the solid content is adjusted to be 15 wt%, 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are stirred to react for 10 hours at the temperature of 10:3:5:2, then isoquinoline and acetic anhydride with the molar weight being 2 times of that of 2, 2' -bis (trifluoromethyl) diaminobiphenyl are added, the reaction is continued for 1 hour at room temperature, the temperature is increased to 80 ℃, and then the reaction is stirred for 1 hour, dripping the obtained reaction solution into excessive methanol to separate out a precipitate, filtering, washing with a large amount of methanol, crushing the obtained precipitate, and performing vacuum drying at 80 ℃ for 5 hours to obtain polyimide;
adding the polyimide into N, N-dimethylacetamide to be completely dissolved to obtain a polyimide solution with the solid content of 10%, casting the obtained polyimide solution on a glass substrate, placing the glass substrate in an oven, heating to 100 ℃, drying for 0.5h, continuously heating to 200 ℃, drying for 0.5h, heating to 280 ℃, drying for 1h, cooling to room temperature, and separating a membrane from the glass substrate to obtain a polyimide film, namely the polyimide substrate layer (the thickness of the polyimide substrate layer is 30 mu m, the light transmittance is 91.3% under the condition of 400-700nm, and the yellowness index YI is 2.4);
(2) dissolving aminopropyltriethoxysilane in an ethanol-deionized water mixed solution with the volume ratio of 1:1, adding dilute hydrochloric acid (0.1mol/L) to adjust the pH value to 3.5-5.5, heating to 80 ℃, stirring for reaction for 5 hours, and evaporating to remove the solvent to obtain polysiloxane; then adding the multi-walled carbon nanotube into concentrated nitric acid according to the mass-volume ratio of 1g:10mL, carrying out ultrasonic heating reflux reaction for 6h, filtering, washing with water until the filtrate is neutral, drying in vacuum, and grinding to obtain a hydroxylated carbon nanotube (CNT-OH);
adding the polysiloxane into an ethanol-deionized water mixed solution with the volume ratio of 3:1, completely dissolving, adding the hydroxylated carbon nanotube (CNT-OH), uniformly stirring and dispersing, wherein the addition amount of the hydroxylated carbon nanotube is 5 wt% of that of the polysiloxane, heating to 80 ℃, reacting for 5 hours, and evaporating to remove the solvent to obtain the polysiloxane grafted with the carbon nanotube;
(3) and adding the polysiloxane grafted with the carbon nano tube into ethanol for uniform dispersion to obtain a dispersion liquid with the solid content of 20 wt%, coating the dispersion liquid on one surface of the polyimide substrate layer, carrying out heat treatment at 90 ℃ for 10min, and forming an antistatic layer (the thickness of the antistatic layer is 3 mu m) on the polyimide substrate layer to obtain the polyimide film.
Example 3
The antistatic polyimide film comprises a polyimide substrate layer and an antistatic layer positioned on the polyimide substrate layer, and is prepared by the following method:
(1) under the protection of nitrogen, 2, 2' -bis (trifluoromethyl) diaminobiphenyl is added into N, N-dimethylacetamide and stirred to be completely dissolved, then 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are sequentially added, the solid content is adjusted to be 15 wt%, 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are stirred to react for 10 hours at the temperature of 10:3:5:2, then isoquinoline and acetic anhydride with the molar weight being 2 times of that of 2, 2' -bis (trifluoromethyl) diaminobiphenyl are added, the reaction is continued for 1 hour at room temperature, the temperature is increased to 80 ℃, and then the reaction is stirred for 1 hour, dripping the obtained reaction solution into excessive methanol to separate out a precipitate, filtering, washing with a large amount of methanol, crushing the obtained precipitate, and performing vacuum drying at 80 ℃ for 5 hours to obtain polyimide;
adding the polyimide into N, N-dimethylacetamide to be completely dissolved to obtain a polyimide solution with the solid content of 10%, casting the obtained polyimide solution on a glass substrate, placing the glass substrate in an oven, heating to 100 ℃, drying for 0.5h, continuously heating to 200 ℃, drying for 0.5h, heating to 280 ℃, drying for 1h, cooling to room temperature, and separating a membrane from the glass substrate to obtain a polyimide film, namely the polyimide substrate layer (the thickness of the polyimide substrate layer is 30 mu m, the light transmittance is 91.3% under the condition of 400-700nm, and the yellowness index YI is 2.4);
(2) dissolving vinyl triethoxysilane in an ethanol-deionized water mixed solution with a volume ratio of 1:1, adding dilute hydrochloric acid (0.1mol/L) to adjust the pH value to 3.5-5.5, heating to 80 ℃, stirring for reaction for 5 hours, and evaporating to remove the solvent to obtain polysiloxane; then adding the multi-walled carbon nanotube into concentrated nitric acid according to the mass-volume ratio of 1g:10mL, carrying out ultrasonic heating reflux reaction for 6h, filtering, washing with water until the filtrate is neutral, drying in vacuum, and grinding to obtain a hydroxylated carbon nanotube (CNT-OH);
adding the polysiloxane into an ethanol-deionized water mixed solution with the volume ratio of 3:1, completely dissolving, adding the hydroxylated carbon nanotube (CNT-OH), uniformly stirring and dispersing, wherein the addition amount of the hydroxylated carbon nanotube is 0.1 wt% of that of the polysiloxane, heating to 80 ℃, reacting for 5 hours, and evaporating to remove the solvent to obtain the polysiloxane grafted with the carbon nanotube;
(3) and adding the polysiloxane grafted with the carbon nano tube into ethanol for uniform dispersion to obtain a dispersion liquid with the solid content of 20 wt%, coating the dispersion liquid on one surface of the polyimide substrate layer, carrying out heat treatment at 90 ℃ for 10min, and forming an antistatic layer (the thickness of the antistatic layer is 3 mu m) on the polyimide substrate layer to obtain the polyimide film.
Example 4
The antistatic polyimide film comprises a polyimide substrate layer and an antistatic layer positioned on the polyimide substrate layer, and is prepared by the following method:
(1) under the protection of nitrogen, 2, 2' -bis (trifluoromethyl) diaminobiphenyl is added into N, N-dimethylacetamide and stirred to be completely dissolved, then 1, 2, 4, 5-cyclopentane tetracarboxylic dianhydride, 4' -oxydiphthalic anhydride and phthaloyl chloride are sequentially added, the solid content is adjusted to be 15 wt%, 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are stirred for reaction for 10 hours at 30 ℃, then isoquinoline and acetic anhydride with 2 times of molar weight of 2, 2' -bis (trifluoromethyl) diaminobiphenyl are added, the reaction is continued for 1 hour at room temperature, the temperature is increased to 80 ℃, and then the reaction is stirred for 1 hour, dripping the obtained reaction solution into excessive methanol to separate out a precipitate, filtering, washing with a large amount of methanol, crushing the obtained precipitate, and performing vacuum drying at 80 ℃ for 5 hours to obtain polyimide;
adding the polyimide into N, N-dimethylacetamide to be completely dissolved to obtain a polyimide solution with the solid content of 10%, casting the obtained polyimide solution on a glass substrate, placing the glass substrate in an oven, heating to 100 ℃, drying for 0.5h, continuously heating to 200 ℃, drying for 0.5h, heating to 280 ℃, drying for 1h, cooling to room temperature, and separating a membrane from the glass substrate to obtain a polyimide film, namely the polyimide substrate layer (the thickness of the polyimide substrate layer is 30 mu m, the light transmittance is 90.5% under the condition of 400-700nm, and the yellowness index YI is 2.6);
(2) dissolving 3-chloropropyltriethoxysilane in an ethanol-deionized water mixed solution with the volume ratio of 1:1, adding dilute hydrochloric acid (0.1mol/L) to adjust the pH value to 3.5-5.5, heating to 80 ℃, stirring for reaction for 5 hours, and evaporating to remove the solvent to obtain polysiloxane; then adding the multi-walled carbon nanotube into concentrated nitric acid according to the mass-volume ratio of 1g:10mL, carrying out ultrasonic heating reflux reaction for 6h, filtering, washing with water until the filtrate is neutral, drying in vacuum, and grinding to obtain a hydroxylated carbon nanotube (CNT-OH);
adding the polysiloxane into an ethanol-deionized water mixed solution with the volume ratio of 3:1, completely dissolving, adding the hydroxylated carbon nanotube (CNT-OH), uniformly stirring and dispersing, wherein the addition amount of the hydroxylated carbon nanotube is 2 wt% of that of the polysiloxane, heating to 80 ℃, reacting for 5 hours, and evaporating to remove the solvent to obtain the polysiloxane grafted with the carbon nanotube;
(3) and adding the polysiloxane grafted with the carbon nano tube into ethanol for uniform dispersion to obtain a dispersion liquid with the solid content of 20 wt%, coating the dispersion liquid on one surface of the polyimide substrate layer, carrying out heat treatment at 90 ℃ for 10min, and forming an antistatic layer (the thickness of the antistatic layer is 3 mu m) on the polyimide substrate layer to obtain the polyimide film.
Comparative example 1
The antistatic polyimide film comprises a polyimide substrate layer and an antistatic layer positioned on the polyimide substrate layer, and is prepared by the following method:
(1) under the protection of nitrogen, 2, 2' -bis (trifluoromethyl) diaminobiphenyl is added into N, N-dimethylacetamide and stirred to be completely dissolved, then 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are sequentially added, the solid content is adjusted to be 15 wt%, 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 1, 2, 3, 4-cyclobutane tetracarboxylic dianhydride, 4' -hexafluoroisopropyl phthalic anhydride and phthaloyl chloride are stirred to react for 10 hours at the temperature of 10:3:5:2, then isoquinoline and acetic anhydride with the molar weight being 2 times of that of 2, 2' -bis (trifluoromethyl) diaminobiphenyl are added, the reaction is continued for 1 hour at room temperature, the temperature is increased to 80 ℃, and then the reaction is stirred for 1 hour, dripping the obtained reaction solution into excessive methanol to separate out a precipitate, filtering, washing with a large amount of methanol, crushing the obtained precipitate, and performing vacuum drying at 80 ℃ for 5 hours to obtain polyimide;
adding the polyimide into N, N-dimethylacetamide to be completely dissolved to obtain a polyimide solution with the solid content of 10%, casting the obtained polyimide solution on a glass substrate, placing the glass substrate in an oven, heating to 100 ℃, drying for 0.5h, continuously heating to 200 ℃, drying for 0.5h, heating to 280 ℃, drying for 1h, cooling to room temperature, and separating a membrane from the glass substrate to obtain a polyimide film, namely the polyimide substrate layer (the thickness of the polyimide substrate layer is 30 mu m, the light transmittance is 91.3% under the condition of 400-700nm, and the yellowness index YI is 2.4);
(2) dissolving 3-chloropropyltriethoxysilane in an ethanol-deionized water mixed solution with the volume ratio of 1:1, adding dilute hydrochloric acid (0.1mol/L) to adjust the pH value to 3.5-5.5, heating to 80 ℃, stirring for reaction for 5 hours, and evaporating to remove the solvent to obtain polysiloxane; then adding the multi-walled carbon nanotube into concentrated nitric acid according to the mass-volume ratio of 1g:10mL, carrying out ultrasonic heating reflux reaction for 6h, filtering, washing with water until the filtrate is neutral, drying in vacuum, and grinding to obtain a hydroxylated carbon nanotube (CNT-OH);
(3) and adding the polysiloxane and the hydroxylated carbon nano tube with 2 wt% of the polysiloxane into ethanol for uniform dispersion to obtain a dispersion liquid with the solid content of 20 wt%, coating the dispersion liquid on one surface of the polyimide substrate layer, and carrying out heat treatment at 90 ℃ for 10min to form an antistatic layer (the thickness of the antistatic layer is 3 mu m) on the polyimide substrate layer, thus obtaining the polyimide film.
The polyimide films obtained in the examples and comparative examples were subjected to the following performance tests, the results of which are shown in Table 1 below, the surface resistivity was measured with reference to GBT 1410-2006 standard,
TABLE 1 Performance test results of polyimide films obtained in examples and comparative examples
As can be seen from the above table, the polyimide film according to the example of the present invention has high light transmittance while having excellent antistatic property.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (10)
1. An antistatic polyimide film, comprising: the polyimide film comprises a polyimide base layer and an antistatic layer positioned on the polyimide base layer;
the polyimide substrate layer is made of polyimide; the antistatic layer is composed of polysiloxane grafted with carbon nanotubes.
2. The antistatic polyimide film according to claim 1, wherein the polyimide is obtained by polycondensation of monomers comprising an aromatic diamine, an alicyclic dianhydride and an aromatic diacid chloride;
preferably, the aromatic diamine is at least one of 2, 2' -bis (trifluoromethyl) diaminobiphenyl, 4' -diaminodiphenyl ether, or 4, 4' -diaminooctafluorobiphenyl;
preferably, the alicyclic dianhydride is at least one of 1, 2, 3, 4-cyclobutanetetracarboxylic dianhydride, 1, 2, 4, 5-cyclopentanetetracarboxylic dianhydride, bicyclo [2.2.1] hepta-2, 3, 5, 6-tetracarboxylic dianhydride or bicyclo [2.2.2] hepta-2, 3, 5, 6-tetracarboxylic dianhydride;
preferably, the aromatic diacid chloride is at least one of terephthaloyl chloride or isophthaloyl chloride.
3. The antistatic polyimide film of claim 2 wherein said aromatic diacid chloride is used in an amount of 10 to 30 mole percent of the aromatic diamine.
4. The antistatic polyimide film of any one of claims 1-3 wherein said monomers further comprise an aromatic dianhydride;
preferably, the aromatic dianhydride is at least one of 4, 4'- (hexafluoroisopropylidene) diphthalic anhydride, 4, 4' -oxydiphthalic anhydride, 3', 4, 4' -benzophenone tetracarboxylic dianhydride, and 3, 3', 4, 4' -biphenyl tetracarboxylic dianhydride.
5. The antistatic polyimide film according to any one of claims 1 to 4, wherein the polysiloxane grafted with carbon nanotubes is obtained by graft reaction of carbon nanotubes with polysiloxane.
6. The antistatic polyimide film according to claim 5, wherein the polysiloxane is obtained by polycondensation of trialkoxysilane;
preferably, the trialkoxysilane is at least one of 3-chloropropyltriethoxysilane, methyltrimethoxysilane, aminopropyltriethoxysilane, or vinyltriethoxysilane.
7. The antistatic polyimide film of claim 5 or 6 wherein the carbon nanotubes are acid activated carbon nanotubes;
preferably, the carbon nanotubes are used in an amount of 0.1 to 5 wt% of the polysiloxane.
8. The antistatic polyimide film according to any one of claims 1 to 7, wherein the polyimide substrate layer is obtained by film-forming a polyimide;
preferably, the thickness of the polyimide substrate layer is 10 to 100 μm.
9. The antistatic polyimide film according to any one of claims 1 to 8, wherein the antistatic layer is obtained by coating polysiloxane grafted with carbon nanotubes on the polyimide-based base layer and forming a film;
preferably, the thickness of the antistatic layer is 0.1 to 10 μm.
10. Use of the antistatic polyimide film of any one of claims 1-9 in an OLED display.
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CN115583834A (en) * | 2022-09-30 | 2023-01-10 | 浙江中科玖源新材料有限公司 | High-performance aramid fiber-based graphite film and preparation method thereof |
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CN113429785A (en) * | 2021-06-16 | 2021-09-24 | 浙江中科玖源新材料有限公司 | Low-birefringence polyimide film and preparation method thereof |
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