WO2022260325A1 - Composition d'apprêt, film stratifié et dispositif d'affichage - Google Patents

Composition d'apprêt, film stratifié et dispositif d'affichage Download PDF

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WO2022260325A1
WO2022260325A1 PCT/KR2022/007602 KR2022007602W WO2022260325A1 WO 2022260325 A1 WO2022260325 A1 WO 2022260325A1 KR 2022007602 W KR2022007602 W KR 2022007602W WO 2022260325 A1 WO2022260325 A1 WO 2022260325A1
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compound
formula
based compound
hard coating
acrylate
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Korean (ko)
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박준기
우석종
조형우
편승용
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에스케이씨하이테크앤마케팅(주)
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Publication of WO2022260325A1 publication Critical patent/WO2022260325A1/fr

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    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/002—Priming paints
    • 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
    • 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
    • C08J7/042—Coating with two or more layers, where at least one layer of a composition contains a polymer binder
    • 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
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • 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
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
    • C09D5/1662—Synthetic film-forming substance
    • C09D5/1668—Vinyl-type polymers
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays

Definitions

  • Embodiments relate to primer compositions, laminated films, and display devices.
  • Polyimide-based resins such as polyamide-imide (PAI) have excellent friction, heat and chemical resistance, and are used as primary electrical insulation, coatings, adhesives, resins for extrusion, heat-resistant paints, heat-resistant plates, and heat-resistant materials. It is applied to adhesives, heat-resistant fibers, and heat-resistant films.
  • PAI polyamide-imide
  • polyimide-based resins are utilized in various fields.
  • polyimide-based resin is made in the form of a powder and used as a coating agent for metal or magnet wire, etc., and is mixed with other additives depending on the use.
  • polyimide-based resin is used as a paint for decoration and anti-corrosion along with fluoropolymer, and serves to adhere the fluoropolymer to a metal substrate.
  • polyimide-based resin is used to coat kitchen utensils, and is used as a membrane used for gas separation due to its heat resistance and chemical resistance, and filters contaminants such as carbon dioxide, hydrogen sulfide and impurities in natural gas oil wells. Also used for devices.
  • One embodiment provides a primer composition having excellent optical properties, mechanical properties and bonding properties.
  • One embodiment provides a laminated film having excellent optical and mechanical properties.
  • One embodiment provides a display device having excellent optical and mechanical properties.
  • a primer composition according to embodiments may include an acrylic binder resin; trifunctional or more polyvalent aziridine-based compounds; and a solvent.
  • a laminated film according to embodiments may include a substrate; a primer layer formed from a primer composition including an acrylic binder resin, a trifunctional or higher polyvalent aziridine-based compound, and a solvent on the substrate; and a hard coating layer formed on the primer layer.
  • a display device includes a display panel; and a cover window disposed on a viewing surface of the display panel, wherein the cover window includes a primer layer formed from a primer composition including a base material, an acrylic binder resin, a trifunctional or higher polyvalent aziridine compound, and a solvent on the base material; and and a hard coating layer formed on the primer layer.
  • the primer composition according to the embodiment may include a trifunctional or higher polyvalent aziridine-based compound to improve bonding strength between the substrate and the hard coating layer and improve durability of the laminated film.
  • the polymer resin base film and the hard coating layer having antifouling and antistatic properties can be strongly bonded.
  • the hard coating layer is strongly bonded to the substrate and cannot be easily separated by external stimuli, for example, even if applied to a flexible device and repeatedly deformed Bonding between the hard coat layer and the substrate can be effectively maintained.
  • FIG. 1 is a schematic exploded view of a display device according to an exemplary embodiment.
  • FIG. 2 is a schematic perspective view of a display device according to an exemplary embodiment.
  • FIG 3 is a schematic cross-sectional view of a display device according to an exemplary embodiment.
  • one component is formed above/under another component or is connected or coupled to each other includes all forms, connections, or couplings between these components directly or indirectly through another component. .
  • the criterion for the top/bottom of each component may vary according to the direction in which the object is observed.
  • substituted means deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido group, a hydrazine group, a hydrazone group, an ester group, unless otherwise specified.
  • ketone group carboxyl group, substituted or unsubstituted C 1 -C 30 alkyl group, substituted or unsubstituted C 2 -C 30 alkenyl group, substituted or unsubstituted C 2 -C 30 alkynyl group, substituted or unsubstituted C 1 -C 30 alkoxy group, substituted or unsubstituted C 6 -C 30 alicyclic organic group, substituted or unsubstituted C 4 -C 30 heterocyclic group, substituted or unsubstituted C 6 -C 30 aryl group and substituted Alternatively, it means one substituted with one or more substituents selected from the group consisting of an unsubstituted C 4 -C 30 heteroaryl group, and two adjacent substituents may be linked to form a ring.
  • the molecular weight of the compound or polymer described herein is a relative mass based on carbon-12 and does not describe the unit, but, if necessary, the same numerical molar mass (g/mol).
  • Primer compositions according to embodiments include a binder resin, a trifunctional or higher polyvalent aziridine-based compound, and a solvent.
  • the binder resin may include an acrylic resin.
  • the acrylic resin is an oligomer or polymer having a repeating unit derived from a (meth)acrylic acid-based compound, and may be formed by polymerization of the (meth)acrylic acid-based compound.
  • the (meth)acrylic acid-based compound may include (meth)acrylic acid and derivatives thereof.
  • the (meth)acrylic acid derivative may include, for example, a (meth)acrylic acid ester-based compound.
  • “(meth)acrylic acid” includes acrylic acid and methacrylic acid.
  • the (meth)acrylic acid-based compound may include an ester compound in which (meth)acrylic acid is substituted with an alkyl group having 1 to 12 carbon atoms.
  • the (meth)acrylic acid ester compound is a (meth)acrylic acid ester substituted with an alkyl group having 1 to 12 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. It may include, preferably, the number of carbon atoms of the alkyl group substituted in the ester compound may be 1 to 8.
  • the (meth) acrylic acid compound is ethyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, (meth) acrylic acid, methyl (meth) acrylate, ethyl methacrylate, n-propyl (meth) )Acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate
  • the acrylic resin may include a polymer of the (meth)acrylic acid-based compound and a comonomer.
  • the comonomer may include an acrylic compound or a vinyl compound other than the (meth)acrylic acid compound.
  • the acrylic compound may include an ester compound (acrylic ester compound) of carboxylic acid having 4 to 12 carbon atoms and carbon number 2 and carbon number 3 connected by a double bond.
  • the acrylic ester compound is an alkyl ester of crotonic acid, an alkyl ester of isocrotonic acid, an alkyl 2-petenoate, an alkyl 2-hexenoate ( alkyl 2-hexanoate) and the like.
  • the number of carbon atoms of the carboxylic acid may be preferably 4 to 8 or 4 to 6.
  • the alkyl group of the acrylic ester compound may be linear, branched or cyclic, and may have 1 to 12 carbon atoms, preferably 1 to 8 carbon atoms.
  • vinyl compound examples include acrylamide, N,N-dimethyl(meth)acrylamide, (meth)acrylonitrile, 3-(meth)acryloylpropyltrimethoxysilane, styrene, and ⁇ -methylstyrene. , p-methylstyrene, p-methoxystyrene, and the like, which may be used alone or in combination of two or more.
  • the acrylic resin may include 50 wt% to 97 wt% of the (meth)acrylic acid-based compound and 3 wt% to 50 wt% of the comonomer, based on the total weight of the monomers.
  • the (meth)acrylic acid compound may be included in 60% to 97% by weight, 70% to 97% by weight, 80% to 97% by weight, or 90% to 97% by weight, and the comonomer is 3% by weight % to 40% by weight, 3% to 30% by weight, 3% to 20% by weight or 3% to 10% by weight.
  • the weight average molecular weight (Mw) of the acrylic resin may be 15,000 to 150,000.
  • the weight average molecular weight (MW) of the acrylic resin is 20,000 to 150,000, 30,000 to 150,000, 40,000 to 150,000, 15,000 to 100,000, 20,000 to 100,000, 30,000 to 100,000, 40,000 to 100,000, 15,000 to 80,000, 20,000 to 80,000, 30,000 to 80,000, 40,000 to 80,000, 15,000 to 60,000, 20,000 to 60,000, 30,000 to 60,000 or 40,000 to 60,000.
  • the glass transition temperature (Tg) of the acrylic resin is 50 °C to 150 °C, 60 °C to 150 °C, 70 °C to 150 °C, 80 °C to 150 °C, 50 °C to 120 °C, 60 °C to 120°C, 70°C to 120°C, 80°C to 120°C, 50°C to 100°C, 60°C to 100°C, 70°C to 100°C, 80°C to 100°C, 50°C to 90°C, 60°C to 90°C °C, 70 °C to 90 °C or 80 °C to 90 °C.
  • the acrylic resin may be formed from the (meth)acrylic acid-based compound and the acrylic ester compound, and may not include an acrylic double bond and other functional groups other than an ester group.
  • compatibility between the acrylic resin and the polyvalent aziridine-based compound to be described later may be improved, and bonding properties of the primer composition may be improved.
  • the acrylic resin may be formed from a C 1 to C 4 alkyl crotonate and a C 1 to C 8 alkyl (meth)acrylate.
  • the acrylic resin may be formed from methyl crotonate, methyl (meth)acrylate, butyl (meth)acrylate, octyl methacrylate and 2-ethylhexyl methacrylate.
  • the polyvalent aziridine-based compound may serve as a curing agent and/or a crosslinking agent of the primer composition.
  • the polyvalent aziridine-based compound may include three or more aziridinyl groups (-N(CH 2 )(CH 2 )) at the terminal of the molecular structure.
  • the aziridinyl group may improve bonding strength between the substrate and the hard coating layer by cross-linking the binder resin of the primer layer with the polymer component of the substrate and the polymer component of the hard coating layer.
  • the polyvalent aziridine-based compound may include a compound in which an aziridinylalkanoate-based moiety and a polyol-based moiety are ester-bonded.
  • the aziridinyl alkanoate-based residue may be obtained by substituting an aziridinyl group for an alkyl group of the alkanoate-based residue.
  • the diziridinyl group may be substituted on a terminal carbon atom of the alkanoate-based residue.
  • the polyol-based residue may include 2 to 10 hydroxyl groups, preferably 4 to 6 hydroxyl groups. All of the hydroxyl groups of the polyol-based residue may be ester-bonded with the aziridinylalkanoate-based residue, and in some embodiments, some of the hydroxyl groups of the polyol-based residue may remain without esterification. Preferably, when a part of the hydroxyl group remains, the hydroxyl group may be provided as a reaction site to an aziridinyl group of another polyvalent aziridine-based compound. Accordingly, the crosslinking reaction may be promoted, and bonding strength between the layers of the laminated film may be improved.
  • the polyvalent aziridine-based compound may include a compound represented by Formula I below.
  • A is a tetravalent carbon atom or a residue represented by Formula Ia
  • n, m and l are each independently an integer of 1 to 6
  • y is an integer of 3 or more
  • x+y is A It may be 4 in the case of a carbon atom and 6 in the case of a residue of the following formula (Ia).
  • n, m and l may be 1 to 4.
  • n and m can be the same. l may be greater than n and m, in which case the aziridinyl group of the compound of formula (I) may be relatively free from steric hindrance effects. Accordingly, the crosslinking ability of the compound of formula (I) can be improved.
  • k may be an integer of 1 to 6, preferably, an integer of 1 to 4.
  • the acrylic binder resin may be included in an amount of 0.1% to 20% by weight based on the total weight of the composition.
  • a primer film can be formed with a uniform thickness and strong adhesion can be realized.
  • the acrylic binder resin is 0.1% to 10% by weight, 0.1% to 5% by weight, 0.1% to 3% by weight, 0.1% to 2% by weight, 0.5% by weight based on the total weight of the composition. to 20% by weight, 0.5% to 10% by weight, 0.5% to 5% by weight, 0.5% to 3% by weight, or 0.5% to 2% by weight.
  • the polyvalent aziridine-based compound may be included in an amount of 0.01% by weight or more and less than 3% by weight based on the total weight of the composition. It is possible to improve the bonding strength between the substrate and the hard coating layer in the above content range.
  • the polyhydric aziridine-based compound may be included in an amount of 0.01 wt% to 2.5 wt%, 0.01 wt% to 2 wt%, 0.03 wt% to 2.5 wt%, or 0.03 wt% to 2 wt% based on the total weight of the composition. .
  • the polyvalent aziridine-based compound in the primer composition may be included in a smaller amount than the acrylic binder resin. In this case, bonding strength between the substrate and the hard coating layer may be improved.
  • the solvent may be included in the remaining amount of the primer composition.
  • the solvent may include an aprotic polar solvent of at least one of an ether-based compound, a ketone-based compound, and an ester-based compound, or a non-polar solvent including an aromatic hydrocarbon-based compound.
  • the ether-based compound may include an ether compound of a polyol compound, and may include, for example, propylene glycol n-propyl ether (PNP).
  • the ketone-based compound may include methyl isobutyl ketone and the like.
  • the ester-based compound may include an acetate-based compound, for example, n-butyl acetate and the like.
  • the hydrocarbon-based compound may include an aromatic hydrocarbon-based compound, and may include, for example, benzene, toluene, xylene, and the like. Two or more of the exemplified solvents may be used in combination.
  • FIGS. 1 to 3 are schematic exploded views, perspective views, and cross-sectional views of a display device according to an embodiment, respectively.
  • FIG. 3 is a cross-sectional view taken along the A-A′ direction of FIG. 2 .
  • a display device according to embodiments may include a laminated film 100 and a display panel.
  • the laminated film 100 may include a substrate 130 , a primer layer 120 formed on the substrate 130 , and a hard coating layer 110 formed on the primer layer 120 .
  • the primer layer 120 may be formed from the above-described primer composition.
  • the primer layer 120 may be directly formed on the substrate 130
  • the hard coating layer 110 may be directly formed on the primer layer 120 .
  • the substrate 130 may include a polymer film.
  • the substrate 130 may be a polyester-based resin such as polyethylene terephthalate, polyethylene isophthalate, polyethylene naphthalate, or polybutylene terephthalate; cellulosic resins such as diacetyl cellulose and triacetyl cellulose; polycarbonate-based resin; acrylic resins such as polymethyl (meth)acrylate and polyethyl (meth)acrylate; styrenic resins such as polystyrene and acrylonitrile-styrene copolymer; polyolefin-based resins such as polyethylene, polypropylene, polyolefins having a cyclo-based or norbornene structure, and ethylene-propylene copolymers; vinyl chloride-based resins; amide resins such as nylon and aromatic polyamide; imide-based resins; polyamideimide-based resins; polyethersulfone-based resins; polyurea poly
  • the polyimide-based resin may be formed by simultaneously or sequentially reacting reactants including a diamine compound and a dianhydride compound.
  • the polyimide-based resin may include a polyimide-based polymer formed by polymerization of a diamine compound and a dianhydride compound.
  • the polyimide-based resin may include an imide repeating unit derived from polymerization of a diamine compound and a dianhydride compound.
  • the polyimide-based resin may be polymerized by further including a dicarbonyl compound, and may include a polyamide-imide polymer including an amide repeating unit derived from polymerization of the diamine compound and the dicarbonyl compound.
  • the diamine compound is not particularly limited, but may be, for example, an aromatic diamine compound containing an aromatic structure.
  • the diamine compound may be a compound represented by Formula 1 below.
  • e is selected from an integer of 1 to 5, and when e is 2 or more, E may be the same as or different from each other.
  • (E) e of Formula 1 may be selected from the groups represented by Formulas 1-1a to 1-14a, but is not limited thereto.
  • (E) e of Formula 1 may be selected from the groups represented by Formulas 1-1b to 1-13b below, but is not limited thereto:
  • (E) e in Chemical Formula 1 may be a group represented by Chemical Formula 1-6b.
  • the diamine compound may include a compound having a fluorine-containing substituent.
  • the diamine compound may be composed of a compound having a fluorine-containing substituent.
  • the fluorine-containing substituent may be a fluorinated hydrocarbon group, specifically a trifluoromethyl group, but is not limited thereto.
  • the diamine compound may use one type of diamine compound. That is, the diamine compound may be composed of a single component.
  • the diamine compound is 2,2'-bis (trifluoromethyl) -4,4'-diaminobiphenyl (2,2'-bis (trifluoromethyl) -4,4 having the following structure) '-diaminobiphenyl, TFDB), but is not limited thereto.
  • the dianhydride compound Since the dianhydride compound has a low birefringence value, it may contribute to improving optical properties such as transmittance of the film including the polyimide-based resin.
  • the dianhydride compound is not particularly limited, but may be an aromatic dianhydride compound having an aromatic structure.
  • the aromatic dianhydride compound may be a compound represented by Formula 2 below.
  • G is a substituted or unsubstituted tetravalent C 6 -C 30 aliphatic ring group, a substituted or unsubstituted tetravalent C 4 -C 30 heteroaliphatic ring group, or a substituted or unsubstituted tetravalent C 6 -C 30
  • An aromatic ring group, a substituted or unsubstituted tetravalent C 4 -C 30 heteroaromatic ring group, and the aliphatic ring group, the heteroaliphatic ring group, the aromatic ring group, or the heteroaromatic ring group exists alone or , bonded to each other to form a condensed ring, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, or a substituted or unsubstituted C 2 -C 30 alkynylene group , -O-,
  • G in Formula 2 may be selected from groups represented by Formulas 2-1a to 2-9a, but is not limited thereto.
  • G in Chemical Formula 2 may be a group represented by Chemical Formula 2-8a.
  • the dianhydride compound may include a compound having a fluorine-containing substituent.
  • the dianhydride compound may be composed of a compound having a fluorine-containing substituent.
  • the fluorine-containing substituent may be a fluorinated hydrocarbon group, specifically a trifluoromethyl group, but is not limited thereto.
  • the dianhydride compound may consist of one single component or two mixed components.
  • the dianhydride compound is 2,2'-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride having the following structure (2,2'-bis- (3,4 -dicarboxyphenyl) hexafluoropropane dianhydride, 6-FDA), but is not limited thereto.
  • Polyamic acid may be produced by polymerization of the diamine compound and the dianhydride compound.
  • the polyamic acid may be converted into polyimide through a dehydration reaction.
  • the polyimide may include a repeating unit represented by Formula A below.
  • the polyimide may include a repeating unit represented by Formula A-1 below, but is not limited thereto.
  • n may be an integer from 1 to 400.
  • the dicarbonyl compound is not particularly limited, but may be, for example, a compound represented by Formula 3 below.
  • j is selected from an integer of 1 to 5, and when j is 2 or more, J may be the same as or different from each other.
  • X is a halogen atom. Specifically, X may be F, Cl, Br, I or the like. More specifically, X may be Cl, but is not limited thereto.
  • (J) j in Chemical Formula 3 may be selected from the groups represented by Chemical Formulas 3-1a to 3-14a, but is not limited thereto.
  • (J) j in Chemical Formula 3 may be selected from the groups represented by Chemical Formulas 3-1b to 3-8b, but is not limited thereto:
  • (J) j in Chemical Formula 3 may be a group represented by Chemical Formula 3-1b, a group represented by Chemical Formula 3-2b, or a group represented by 3-3b.
  • At least two dicarbonyl compounds that are different from each other may be mixed and used as the dicarbonyl compound.
  • two or more dicarbonyl compounds are used, two or more dicarbonyl compounds selected from the groups in which (J) j in Formula 3 are represented by Formulas 3-1b to 3-8b may be used. have.
  • the dicarbonyl compound may be an aromatic dicarbonyl compound including an aromatic structure.
  • the dicarbonyl compound may include a first dicarbonyl compound and/or a second dicarbonyl compound different from the first dicarbonyl compound.
  • the first dicarbonyl compound and the second dicarbonyl compound may each be an aromatic dicarbonyl compound.
  • the first dicarbonyl compound and the second dicarbonyl compound may be different aromatic dicarbonyl compounds, but are not limited thereto.
  • first dicarbonyl compound and the second dicarbonyl compound are aromatic dicarbonyl compounds, respectively, since they contain a benzene ring, surface hardness and tensile strength of the film containing the prepared polyamide-imide resin It can contribute to improving mechanical properties such as
  • the dicarbonyl compound has the following structures: terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), 1'-biphenyl-4,4'-dicarbonyldichloride ( 1,1'-biphenyl-4,4'-dicarbonyl dichloride (BPDC) or a combination thereof, but is not limited thereto.
  • TPC terephthaloyl chloride
  • IPC isophthaloyl chloride
  • 1'-biphenyl-4,4'-dicarbonyldichloride 1,1'-biphenyl-4,4'-dicarbonyl dichloride (BPDC) or a combination thereof, but is not limited thereto.
  • the first dicarbonyl compound may include BPDC
  • the second dicarbonyl compound may include TPC, but are not limited thereto.
  • the prepared film including the polyamide-imide resin may have high oxidation resistance. have.
  • the first dicarbonyl compound may include isophthaloyl chloride (IPC), and the second dicarbonyl compound may include TPC, but is not limited thereto.
  • IPC isophthaloyl chloride
  • the prepared film including the polyamide-imide resin may have high oxidation resistance. And the manufacturing cost can be reduced.
  • the diamine compound and the dicarbonyl compound may be polymerized to form a repeating unit represented by Chemical Formula B below.
  • the diamine compound and the dicarbonyl compound may be polymerized to form amide repeating units represented by Chemical Formulas B-1 and B-2.
  • x is an integer from 1 to 400.
  • y is an integer from 1 to 400.
  • the polyimide-based film may include a filler.
  • the filler may be at least one selected from the group consisting of barium sulfate, silica and calcium carbonate.
  • the polyimide-based film can improve roughness and winding properties, as well as improve running properties and scratch improvement effects during film production.
  • the particle diameter of the filler may be greater than or equal to 0.01 ⁇ m and less than 1.0 ⁇ m.
  • the particle size of the filler may be 0.05 ⁇ m to 0.9 ⁇ m or 0.1 ⁇ m to 0.8 ⁇ m, but is not limited thereto.
  • the polyimide-based film may include the filler in an amount of 0.01 wt % to 3 wt % based on the total weight of the polyimide-based film.
  • the polyimide-based film may contain the filler in an amount of 0.05 wt% to 2.5 wt%, 0.1 wt% to 2 wt%, or 0.2 wt% to 1.7 wt% based on the total weight of the polyimide-based film. It may include, but is not limited thereto.
  • the haze of the polyimide-based film may be 3% or less.
  • the haze may be 2% or less, 1.5% or less, or 1% or less, but is not limited thereto.
  • the yellow index (YI) of the polyimide-based film may be 5 or less.
  • the yellowness may be 4 or less, 3.8 or less, 2.8 or less, 2.5 or less, 2.3 or less, or 2.1 or less, but is not limited thereto.
  • the modulus of the polyimide-based film may be 5 GPa or more.
  • the modulus may be 5.2 GPa or more, 5.5 GPa or more, 6.0 GPa or more, 10 GPa or less, 5 GPa to 10 GPa, or 7 GPa to 10 GPa, but is not limited thereto.
  • transmittance of the polyimide-based film may be 80% or more.
  • the transmittance may be 85% or more, 88% or more, 89% or more, 80% to 99%, 80% to 99%, or 85% to 99%, but is not limited thereto.
  • the compressive strength of the polyimide-based film may be 0.4 kgf/ ⁇ m or more. Specifically, the compressive strength may be 0.45 kgf/ ⁇ m or more or 0.46 kgf/ ⁇ m or more, but is not limited thereto.
  • the surface hardness of the polyimide-based film may be greater than or equal to HB. Specifically, the surface hardness may be H or more or 2H or more, but is not limited thereto.
  • the polyimide-based film may have a tensile strength of 15 kgf/mm 2 or more. Specifically, the tensile strength may be 18 kgf/mm 2 or more, 20 kgf/mm 2 or more, 21 kgf/mm 2 or more, or 22 kgf/mm 2 or more, but is not limited thereto.
  • the polyimide-based film may have an elongation of 15% or more. Specifically, the elongation may be 16% or more, 17% or more, or 17.5% or more, but is not limited thereto.
  • the substrate 130 may have high oxidation resistance and secure excellent optical properties such as high light transmittance, low haze, and low yellowness (YI). Furthermore, it may have excellent modulus, elongation, tensile properties, and elastic restoring force.
  • the primer composition may be coated, dried, and cured on the substrate 130 to form the primer layer 120 .
  • the coating may be performed through a method commonly used in the art, such as die coating.
  • the drying and curing may be performed by heat treatment at a temperature of 80° C. to 160° C. for 1 minute to 20 minutes.
  • the primer layer 120 capable of strongly bonding the substrate 130 and the hard coating layer 110 can be formed.
  • the temperature condition may be 100° C. to 140° C.
  • the heat treatment time may be 3 minutes to 12 minutes.
  • the thickness of the primer layer 120 can be between 20 nm and 200 nm.
  • the thickness is 20 nm to 190 nm, 20 nm to 180 nm, 20 nm to 160 nm, 20 nm to 130 nm, 20 nm to 120 nm, 20 nm to 110 nm, 20 nm to 80 nm, 30 nm nm to 200 nm, 30 nm to 190 nm, 30 nm to 180 nm, 30 nm to 160 nm, 30 nm to 130 nm, 30 nm to 120 nm, 30 nm to 110 nm, 30 nm to 100 nm or 30 nm to may be 80 nm.
  • the primer layer 120 includes a first surface 122 and a second surface 124 .
  • the first surface 122 is a surface opposite to the hard coating layer 110 and may be provided as an interface between the primer layer 120 and the hard coating layer 110 .
  • the second surface 124 is a surface facing the base material 130 , and the second surface 124 may be positioned opposite to a surface where the primer layer 120 and the hard coating layer 110 come into contact.
  • the second surface 124 may serve as an interface between the primer layer 120 and the substrate 130 .
  • the hard coating layer 110 may be formed by being coated on the primer layer 120 .
  • the hard coating layer 110 may be bonded on the primer layer 120 .
  • the hard coating layer 110 may include a curable resin. Specifically, the hard coating layer 110 may be a curable coating layer.
  • the hard coating layer 110 may improve mechanical properties and/or optical properties of the laminated film 100 .
  • the hard coating layer 110 may include functions such as antiglare, antifouling, and antistatic.
  • the hard coating layer 110 may include an organic resin and/or an additive.
  • the organic resin may be a curable resin.
  • the organic resin may be a binder resin.
  • the organic resin may include at least one selected from the group consisting of a urethane acrylate-based compound, an acrylic ester-based compound, and an epoxy acrylate-based compound.
  • the organic resin may include a urethane acrylate-based compound and an acrylic ester-based compound.
  • the acrylic ester compound may be at least one selected from the group consisting of substituted or unsubstituted acrylates and substituted or unsubstituted methacrylates.
  • the acrylic ester-based compound may include 1 to 10 functional groups.
  • the urethane acrylate-based compound may include 2 to 15 functional groups.
  • the epoxy acrylate-based compound may include 1 to 10 functional groups.
  • acrylic ester compound examples include trimethylolpropane triacrylate (TMPTA), trimethylolpropaneethoxy triacrylate (TMPEOTA), glycerin propoxylated triacrylate (GPTA), pentaerythritol tetraacrylate (PETA), Or dipentaerythritol hexaacrylate (DPHA) and the like, but are not limited thereto.
  • TMPTA trimethylolpropane triacrylate
  • TMPEOTA trimethylolpropaneethoxy triacrylate
  • GPTA glycerin propoxylated triacrylate
  • PETA pentaerythritol tetraacrylate
  • DPHA dipentaerythritol hexaacrylate
  • the urethane acrylate-based compound includes a urethane bond as a repeating unit and may have a plurality of functional groups.
  • the urethane acrylate-based compound may be one in which a terminal of a urethane compound formed by reacting a diisocyanate compound with a polyol is substituted with an acrylate group.
  • the diisocyanate compound may include at least one of a straight-chain, branched or cyclic aliphatic diisocyanate compound having 4 to 12 carbon atoms and an aromatic diisocyanate compound having 6 to 20 carbon atoms.
  • the polyol includes 2 to 4 hydroxyl groups (-OH) and may be a straight-chain, branched or cyclic aliphatic polyol compound having 4 to 12 carbon atoms or an aromatic polyol compound having 6 to 20 carbon atoms.
  • Terminal substitution with the acrylate group may be performed by an acrylate compound having a functional group capable of reacting with an isocyanate group (-NCO).
  • an acrylate compound having a hydroxyl group or an amine group may be used, and a hydroxyalkyl acrylate compound or an aminoalkyl acrylate compound having 2 to 10 carbon atoms may be used.
  • urethane acrylate-based compound examples include a bifunctional urethane acrylate oligomer having a weight average molecular weight of 1400 to 25000, a trifunctional urethane acrylate oligomer having a weight average molecular weight of 1700 to 16000, a tetrafunctional urethane acrylate oligomer having a weight average molecular weight of 500 to 2000, 15 of hexafunctional urethane acrylate oligomers having a weight average molecular weight of 818 to 2600, 9 functional urethane acrylate oligomers having a weight average molecular weight of 2500 to 5500, 10 functional urethane acrylate oligomers having a weight average molecular weight of 3200 to 3900 or weight average molecular weights of 2300 to 20000 functional urethane acrylate oligomers and the like, but are not limited thereto.
  • the glass transition temperature (Tg) of the urethane acrylate compound is -80 ° C to 100 ° C, -80 ° C to 90 ° C, -80 ° C to 80 ° C, -80 ° C to 70 ° C, -80 °C to 60 °C, -70 °C to 100 °C, -70 °C to 90 °C, -70 °C to 80 °C, -70 °C to 70 °C, -70 °C to 60 °C, -60 °C to 100 °C, -60 °C to 90°C, -60°C to 80°C, -60°C to 70°C, -60°C to 60°C, -50°C to 100°C, -50°C to 90°C, -50°C to 80°C, -50°C to 70°C or -50°C to 60°C.
  • Examples of the epoxy acrylate-based compound include a monofunctional epoxy acrylate oligomer having a weight average molecular weight of 100 to 300, a bifunctional epoxy acrylate oligomer having a weight average molecular weight of 250 to 2000, a tetrafunctional epoxy acrylate oligomer having a weight average molecular weight of 1000 to 3000, and the like. It may include, but is not limited thereto.
  • the weight average molecular weight (Mw) of the acrylic ester compound is about 500 to about 6,000, about 500 to about 5,000, about 500 to about 4,000, 1000 to about 6,000, about 1000 to about 5,000, about 1000 to about 4,000, 1500 to about 6,000, about 1500 to about 5,000 or about 1500 to about 4,000.
  • the acrylate equivalent weight of the acrylic ester compound is about 50 g/eq to about 300 g/eq, about 50 g/eq to about 200 g/eq, or about 50 g/eq to about 150 g/eq. may be in the range of
  • the epoxy equivalent weight of the epoxy acrylate-based compound is about 50 g/eq to about 300 g/eq, about 50 g/eq to about 200 g/eq, or about 50 g/eq to about 150 g/eq. may be in the range of
  • the content of the organic resin may be 30 wt% to 100 wt% based on the total weight of the hard coating layer 110 . Specifically, the content of the organic resin may be 40% to 90% by weight or 50% to 80% by weight based on the total weight of the hard coating layer 110 .
  • the hard coating layer 110 may optionally include a filler.
  • the filler include silica, barium sulfate, zinc oxide or alumina.
  • the particle diameter of the filler may be 1 nm to 100 nm. Specifically, the particle diameter of the filler may be 5 nm to 50 nm or 10 nm to 30 nm.
  • the filler may include inorganic fillers having different particle diameter distributions.
  • the filler may include a first inorganic filler having a d50 of 20 nm to 35 nm and a second inorganic filler having a d50 of 40 nm to 130 nm.
  • the content of the filler may be about 25% by weight or more, about 30% by weight or more, or about 35% by weight or more based on the total weight of the functional layer. In addition, the content of the filler may be about 50 wt% or less, about 45 wt% or less, or about 40 wt% or less based on the total weight of the functional layer.
  • the hard coating layer 110 may not include an inorganic filler such as silica.
  • an inorganic filler such as silica.
  • bonding strength between the base layer and the hard coating layer having the above composition may be improved.
  • the hard coating layer 110 may further include a photoinitiator.
  • photoinitiator examples include 1-hydroxy-cyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-1-[4-(2-hydroxyethoxy ) Phenyl] -2-methyl-1-propanone, methylbenzoyl formate, ⁇ , ⁇ -dimethoxy- ⁇ -phenylacetophenone, 2-benzoyl-2- (dimethylamino) -1- [4- (4- Morpholinyl) phenyl] -1-butanone, 2-methyl-1- [4- (methylthio) phenyl] -2- (4-morpholinyl) -1-propanone diphenyl (2,4, 6-trimethylbenzoyl)-phosphine oxide, or bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and the like, but are not limited thereto.
  • commercial products include Irgacure 184, Irgacure 500, Irgacure 651, Irgacure 369, Irgacure 907, Darocur 1173, Darocur MBF, Irgacure 819, Darocur TPO, Irgacure 907, Esacure KIP 100F, and the like.
  • the photoinitiator may be used alone or in combination of two or more different types.
  • the hard coating layer 110 may include at least one of an antifouling additive and an antistatic agent.
  • the antifouling additive may include a fluorine-substituted acrylate-based compound.
  • the antifouling additive may include an acrylate-based compound including a perfluoroalkyl group such as (perfluorohexyl)ethyl acrylate.
  • the antistatic agent may include an ionic surfactant.
  • the ionic surfactant may include an ammonium salt or a quaternary alkylammonium salt, and the ammonium salt and quaternary alkylammonium salt may include a halide such as chloride or bromide.
  • the hard coating layer having antifouling and antistatic properties provided by the antifouling additive and the antistatic agent has adhesive strength with a substrate (in particular, a polyimide-based film). This may be low, and thus, when the laminated film is deformed or subjected to an external stimulus, the hard coat layer can be easily separated from the substrate.
  • the hard coating layer 110 may include other additives such as a surfactant, a UV absorber, a UV stabilizer, an anti-yellowing agent, a leveling agent, or a dye for improving a color value.
  • the content of the additive may be variously adjusted within a range that does not degrade the physical properties of the hard coating layer 110.
  • the content of the additive may be included in about 0.01 wt% to about 10 wt% based on the hard coating layer 110, but is not limited thereto.
  • the surfactant may be a mono- or bifunctional fluorine-based acrylate, a fluorine-based surfactant, or a silicone-based surfactant.
  • the surfactant may be included in a dispersed or cross-linked form in the hard coating layer 110 .
  • UV absorber examples include benzophenone-based compounds, benzotriazole-based compounds, and triazine-based compounds
  • UV stabilizer examples include tetramethyl piperidine.
  • the hard coating layer 110 may be formed by applying a hard coating composition on the primer layer 120, drying, and curing.
  • the hard coating composition may include the aforementioned organic resin, photoinitiator, antifouling additive, antistatic agent, other additives and/or solvent.
  • organic solvent examples include alcohol-based solvents such as methanol, ethanol, isopropyl alcohol, and butanol; alkoxy alcohol solvents such as 2-methoxyethanol, 2-ethoxyethanol, and 1-methoxy-2-propanol; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl propyl ketone, and cyclohexanone; Propylene glycol monopropyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethyl glycol monoethyl ether, diethyl glycol monopropyl ether ether solvents such as diethyl glycol monobutyl ether and diethylene glycol-2-ethylhexyl ether; aromatic solvents such as benzene, tol
  • the content of the organic solvent is not particularly limited as it can be variously adjusted within a range that does not degrade the physical properties of the coating composition, but with respect to the solid content among the components included in the hard coating composition, the solid content: organic solvent weight ratio is about 30:70 to about 99:1. When the organic solvent is within the above range, appropriate fluidity and coating properties may be obtained.
  • the hard coating composition may include 10% to 30% by weight of an organic resin, 0.1% to 5% by weight of a photoinitiator, 0.01% to 2% by weight of an antifouling additive, and 0.1% to 10% by weight of an antistatic agent.
  • an organic resin 0.1% to 5% by weight of a photoinitiator
  • an antifouling additive 0.1% to 10% by weight of an antistatic agent.
  • the hard coating composition is a bar coating method, a knife coating method, a roll coating method, a blade coating method, a die coating method, a micro gravure coating method, a comma coating method, a slot die coating method, a lip coating method, or a solution casting method It may be applied on the primer layer 120 through the like.
  • the organic solvent included in the hard coating composition may be removed through a drying process.
  • the drying process may be performed at a temperature of 40°C to 100°C, preferably 40°C to 80°C, 50°C to 100°C, or 50°C to 80°C, for about 1 minute to 20 minutes, preferably 1 minutes to 10 minutes or 1 to 5 minutes.
  • the hard coating composition layer may be cured by light and/or heat.
  • the cured hard coating layer 110 has a thickness of about 2 ⁇ m or more, or about 3 ⁇ m or more, for example, about 2 ⁇ m to about 20 ⁇ m, about 2 ⁇ m to about 15 ⁇ m, about 2 ⁇ m to about 10 ⁇ m, or about 3 ⁇ m to about 3 ⁇ m. It may have a thickness of about 10 ⁇ m.
  • the laminated film may have a cross hatch adhesion test result value measured according to JIS K 5600 of 50/100 or more, 70/100 or more, 80/100 or more, 90/100 or more, or 95/100 or more. have.
  • a display device may include a laminated film 100 and a display panel 200 .
  • the laminated film 100 may be provided as a cover window of a display device.
  • the laminated film (cover window: 100) may be disposed on the viewer side with respect to the display panel 200 to protect the display panel 200.
  • the display device when the antifouling additive and the antistatic agent are included in the hard coating layer 110, the display device may have antifouling and antistatic properties, and the above-described primer layer 120 is the hard coating layer 110 When formed between the substrate 130 and the antifouling/antistatic hard coating layer and the substrate are strongly bonded, a display device having durability even when repeatedly deformed can be provided.
  • the display panel 200 is a device capable of displaying an image and may have a flexible characteristic.
  • the display panel 200 may be, for example, a liquid crystal display panel or an organic light emitting display panel.
  • the organic light emitting display panel may include a front polarizer and an organic EL panel, but is not limited thereto.
  • the front polarizing plate may be disposed on the front surface of the organic EL panel. Specifically, the front polarizing plate may be attached to a surface of the organic EL panel on which an image is displayed.
  • the organic EL panel displays an image by self-emission in pixel units.
  • the organic EL panel may include an organic EL substrate and a driving substrate.
  • the organic EL substrate may include a plurality of organic electroluminescent units each corresponding to a pixel. Specifically, each may include a cathode, an electron transport layer, a light emitting layer, a hole transport layer, and an anode.
  • the driving substrate may be drivingly coupled to the organic EL substrate. That is, the driving substrate is coupled to apply a driving signal such as a driving current to the organic EL substrate, so that the organic EL substrate can be driven by applying a current to each of the organic electroluminescent units.
  • an adhesive layer may be included between the display panel 200 and the laminated film 100 .
  • the adhesive layer may be an optically transparent adhesive layer, and is not particularly limited.
  • a primer composition was prepared by mixing each component according to the composition shown in Table 1 below.
  • a primer composition was prepared in the same manner as in Preparation Example 1, except that the content of pentaerythritol tris(3-aziridin-1-ylpropionate) in the primer composition was adjusted as shown in Table 2 below.
  • the content of the solvent was decreased by the increase in the content of pentaerythritol tris(3-aziridin-1-ylpropionate) in the composition.
  • a hard coating composition was prepared by mixing each component in the composition shown in Table 3 below.
  • a hard coating composition was prepared in the same manner as in Preparation Example 7, except that urethane acrylate and acrylic ester were respectively changed to the compounds shown in Table 4 below.
  • Preparation Example 7 Preparation Example 8
  • Preparation Example 9 Preparation Example 10
  • Urethane Acrylate Miramer MU9800 Miramer PU340 (Miwon Specialty Chemical) Miramer PU320 (Miwon Specialty Chemical) Miramer SC2152 (Miwon Specialty Chemical) acrylic ester Miramer PS3010 Photocryl DP344 (Miwon Specialty Chemical) Miramer P261 (Miwon Specialty Chemical) Miramer PS3010 (Miwon Specialty Chemical)
  • the primer compositions of Preparation Examples 1 to 6 were applied on one surface of a transparent polyimide film (manufactured by SKC) having a thickness of about 30 to 80 ⁇ m by a die coating method. Heat treatment was performed at about 120° C. for about 6 minutes to dry the solvent and curing was performed to form a primer layer having a thickness of about 70 to 90 nm.
  • the hard coating compositions of Preparation Examples 7 to 10 were applied on the primer layer by a die coating method.
  • the applied composition was dried at about 120° C. for about 6 minutes and cured by applying a total energy of about 1 J/cm 2 through UV with a wavelength of 375 nm to form a hard coating layer having a thickness of about 5 ⁇ m.
  • a laminated film was prepared in the same manner as in Example 1, except that the thickness of the primer layer was changed as shown in Table 5 below.
  • Example 7 Example 8
  • Example 9 Example 10 coating thickness 73 nm 36 nm 120 nm 156 nm 182 nm
  • Laminated films were prepared in the same manner as in Examples 1 to 4, except that a polyethylene terephthalate film (TU94, 50 ⁇ m thick; manufactured by SKC) having a thickness of about 40 ⁇ m was used as the primer composition instead of the polyimide film.
  • a polyethylene terephthalate film (TU94, 50 ⁇ m thick; manufactured by SKC) having a thickness of about 40 ⁇ m was used as the primer composition instead of the polyimide film.
  • the hard coating composition of Preparation Example 7 was directly applied on one surface of a ⁇ m transparent polyimide film by a die coating method, and the coated composition was dried at about 120 ° C. for about 6 minutes, and a total of about 1
  • a laminated film in which a hard coating layer was laminated was prepared by curing by applying energy of J/cm 2 .
  • Adhesion tests were conducted on the laminated films of Examples and Comparative Examples according to JIS K 5600 using a cross hatch adhesion tester (Elcometer, 107-1542).
  • sheaths were formed in two directions orthogonal to each other on the surface of the sample on which the hard coating layer was formed using a cross hatch cutter to form 10 x 10 cutting units.
  • An adhesive tape (Nitto, 31B) was attached so as to cover all of the cutting units, and the tape was peeled off at a speed of about 2500 mm/min or more in the 90 ° direction.
  • the number of cut units remaining without being peeled off by the tape among the total cut units was evaluated as a ratio and shown in Table 6 below.
  • the thickness of the primer layer was 200 nm or less, it was confirmed to have excellent adhesive strength, and when the content of the trifunctional or higher polyvalent aziridine-based compound in the primer composition was less than 3% by weight, it was confirmed that the adhesive strength was improved.

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Abstract

Une composition d'apprêt, selon un mode de réalisation, comprend : une résine de liant acrylique ; un composé à base d'aziridine polyvalente au moins trifonctionnelle ; et un solvant, ce qui permet de lier fortement un substrat et une couche de revêtement dur.
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WO2015069502A1 (fr) * 2013-11-07 2015-05-14 3M Innovative Properties Company Revêtements fluoropolymères comprenant des composés aziridine et polymère non fluoré
JP2015142999A (ja) * 2013-12-25 2015-08-06 東レフィルム加工株式会社 帯電防止性離型フィルム
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KR20100096138A (ko) * 2007-11-30 2010-09-01 시카 테크놀러지 아게 접착성이 개선된 필름 하도제
KR20110130142A (ko) * 2010-05-27 2011-12-05 주식회사 대하맨텍 자외선 경화형 기능성 하드코팅제
WO2015069502A1 (fr) * 2013-11-07 2015-05-14 3M Innovative Properties Company Revêtements fluoropolymères comprenant des composés aziridine et polymère non fluoré
JP2015142999A (ja) * 2013-12-25 2015-08-06 東レフィルム加工株式会社 帯電防止性離型フィルム
KR20210031671A (ko) * 2019-09-05 2021-03-22 에스케이씨 주식회사 플렉서블 디스플레이 장치를 위한 폴리에스테르 보호 필름

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