WO2022005138A1 - Composition adhésive et feuille adhésive l'utilisant - Google Patents

Composition adhésive et feuille adhésive l'utilisant Download PDF

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Publication number
WO2022005138A1
WO2022005138A1 PCT/KR2021/008116 KR2021008116W WO2022005138A1 WO 2022005138 A1 WO2022005138 A1 WO 2022005138A1 KR 2021008116 W KR2021008116 W KR 2021008116W WO 2022005138 A1 WO2022005138 A1 WO 2022005138A1
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Prior art keywords
meth
pressure
sensitive adhesive
acrylic copolymer
adhesive composition
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PCT/KR2021/008116
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English (en)
Korean (ko)
Inventor
정경문
권혜림
김명진
Original Assignee
동우 화인켐 주식회사
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Publication of WO2022005138A1 publication Critical patent/WO2022005138A1/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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition and a pressure-sensitive adhesive sheet using the same, and more particularly, to a pressure-sensitive adhesive composition exhibiting low dielectric properties suitable for application to a thin image display device requiring a high frequency band or a pressure-sensitive adhesive sheet using the same.
  • an optically clear adhesive having high transparency is used for interlayer adhesion for stacking components in an image display device.
  • OCA optically clear adhesive
  • These optically transparent pressure-sensitive adhesives require high transmittance and low haze, and must satisfy physical properties such as adhesion to various substrates, heat resistance, and heat-and-moisture resistance.
  • a touch sensor is a device that detects a touch point in response to a user's contact with an image displayed on the screen with a finger or a touch pen, and is a liquid crystal display (LCD), organic light- It is manufactured in a structure that is mounted on a flat panel display device such as an emitting diode (OLED).
  • LCD liquid crystal display
  • OLED organic light- It is manufactured in a structure that is mounted on a flat panel display device such as an emitting diode (OLED).
  • OLED emitting diode
  • Korean Patent Laid-Open No. 10-2013-0106368 discloses a (meth)acrylic acid ester-based monomer having a hydrocarbon group having 1 to 12 carbon atoms, a (meth)acrylic acid ester-based monomer containing a hydroxyl group, a monomer containing an amide group, and a vinyl ester-based monomer.
  • An acrylic polymer compound obtained by copolymerizing the monomer component containing A pressure-sensitive adhesive composition comprising a crosslinking agent is disclosed.
  • the pressure-sensitive adhesive composition has a problem in that it is difficult to secure sufficiently low dielectric properties to use a high frequency band of 1 GHz or more or to be applied to a thinned image display device.
  • One object of the present invention is to provide a pressure-sensitive adhesive composition that enables faster antenna transmission and reception without lowering an antenna gain value by exhibiting a low dielectric characteristic even in a high frequency band.
  • Another object of the present invention is to provide a pressure-sensitive adhesive composition exhibiting low dielectric properties that do not affect the driving of the touch sensor even when the image display device is thinned.
  • Another object of the present invention is to provide a pressure-sensitive adhesive sheet formed by using the pressure-sensitive adhesive composition.
  • the present invention is a pressure-sensitive adhesive composition containing a (meth) acrylic copolymer, or a mixture of a (meth) acrylic copolymer and a photopolymerizable monomer,
  • the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is 16.5% or less
  • the dielectric constant at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m is less than 2.5, and the dielectric loss tangent at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing is 0.015 or less.
  • the (meth)acrylic copolymer, or a mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is a (meth)acrylic monomer having an aliphatic hydrocarbon group having 10 or more carbon atoms and an aliphatic hydrocarbon having 8 or more carbon atoms.
  • One or more of the vinyl ether monomers having a group may be included in an amount of 20 wt% or more based on 100 wt% of the total monomers.
  • the pressure-sensitive adhesive composition may contain a (meth)acrylic copolymer and a thermosetting agent.
  • thermosetting agent may include an isocyanate-based crosslinking agent.
  • thermosetting agent may be contained in an amount of 0.04 to 1 part by weight based on 100 parts by weight of the (meth)acrylic copolymer.
  • the pressure-sensitive adhesive composition may contain a mixture of a (meth)acrylic copolymer and a photopolymerizable monomer, and a photoinitiator.
  • the photoinitiator may be contained in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the total amount of the (meth)acrylic copolymer and the photopolymerizable monomer.
  • the present invention provides a pressure-sensitive adhesive sheet formed using the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition according to the present invention adjusts the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer so that the dielectric constant at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing and
  • the dielectric loss tangent to a specific value range, it is possible to exhibit low dielectric properties suitable for application to a thin image display device or requiring a high frequency band. Accordingly, when applied to an antenna, the antenna gain value is not lowered, enabling faster antenna transmission/reception, and even if the image display device is thinned, driving of the touch sensor is not affected.
  • One embodiment of the present invention is a pressure-sensitive adhesive composition containing a (meth)acrylic copolymer, or a mixture of a (meth)acrylic copolymer and a photopolymerizable monomer,
  • the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is 16.5% or less
  • the dielectric constant at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m is less than 2.5, and the dielectric loss tangent at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing is 0.015 or less.
  • the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer constitutes the (meth)acrylic copolymer, or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer. refers to the weight ratio of heteroatoms to the total atomic weight, and may be defined according to Equation 1 below.
  • the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is the (meth)acrylic copolymer, or the (meth)acrylic copolymer and the photopolymerizable monomer. It is a value expressed as a percentage by adding the value obtained by multiplying the weight ratio of heteroatoms contained in each monomer constituting the mixture by the ratio of the corresponding monomer.
  • (meth)acrylate means acrylate and/or methacrylate.
  • the heteroatom is an element other than carbon and means, for example, oxygen, sulfur or nitrogen.
  • the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is 16.5% or less, such as 0.5 to 16.5%, preferably 3 to 16.5%, as described above; More preferably 5 to 16.5%, more preferably 7 to 16.5%, still more preferably 10 to 16.5%, still more preferably 10 to 16.0%.
  • the dielectric constant at 15GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing is 2.5 or more, or , the dielectric loss tangent at 15 GHz of the 150 ⁇ m thick pressure-sensitive adhesive layer after curing may be greater than 0.015.
  • the radio wave reception efficiency of the antenna may be reduced and the touch sensor may be thinned It can be difficult.
  • the dielectric constant is a physical unit indicating the effect of a medium between charges on the electric field when an electric field acts between the charges, and may be viewed as an amount of charge that the medium can store.
  • the dielectric constant at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing is a value measured at a frequency of 15 GHz according to the method described in Experimental Examples to be described later with respect to a sample having a pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing.
  • the dielectric constant at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m may be less than 2.5, for example, greater than 1 and less than 2.5 as described above. If the dielectric constant at 15 GHz of the 150 ⁇ m-thick adhesive layer after curing is 2.5 or more, the antenna gain value can be lowered when applied to an antenna using a high frequency band such as 15 GHz, and when the image display device is thinned, the touch sensor may affect the operation of
  • the dielectric tangent is a unit representing a ratio of power loss generated when an AC voltage is applied to a dielectric, and is generally expressed as tangent delta (tangent ⁇ ).
  • the dielectric loss tangent at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing is a value measured at a frequency of 15 GHz according to the method described in Experimental Examples to be described later with respect to a sample having a pressure-sensitive adhesive layer having a thickness of 150 ⁇ m after curing.
  • the dielectric loss tangent at 15 GHz of the pressure-sensitive adhesive layer having a thickness of 150 ⁇ m may be 0.015 or less as described above, for example, more than 0 and 0.015 or less. If the dielectric loss tangent at 15 GHz of the 150 ⁇ m-thick adhesive layer after curing exceeds 0.015, the antenna gain value can be lowered when applied to an antenna using a high frequency band such as 15 GHz, and when the image display device is thinned, the touch sensor is driven may affect
  • the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer can be prepared by appropriately selecting the monomer so that the weight ratio of heteroatoms is 16.5% or less.
  • the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is a (meth)acrylic monomer having an aliphatic hydrocarbon group having 10 or more carbon atoms and a vinyl ether having an aliphatic hydrocarbon group having 8 or more carbon atoms.
  • One or more of the monomers may be included in an amount of 20% by weight or more, for example 20 to 99% by weight, preferably 20 to 90% by weight based on 100% by weight of the total monomers.
  • the content of at least one of the (meth)acrylic monomer having an aliphatic hydrocarbon group having 10 or more carbon atoms and the vinyl ether monomer having an aliphatic hydrocarbon group having 8 or more carbon atoms is less than 20% by weight, it is difficult to control the weight ratio of heteroatoms to be 16.5% or less can
  • the aliphatic hydrocarbon group having 10 or more carbon atoms is a straight or branched chain having 10 or more carbon atoms, for example, 10 to 100, preferably 10 to 50, more preferably 10 to 30. It means a saturated or unsaturated hydrocarbon, and, for example C 10 -C 100 alkyl group, C 10 -C 100 alkenyl groups, may be an alkynyl of C 10 -C 100.
  • the aliphatic hydrocarbon group having 10 or more carbon atoms includes, but is not limited to, decyl, isodecyl, undecyl, dodecyl, tridecyl, cetyl, stearyl, isostearyl, heptacosanyl, and the like.
  • the aliphatic hydrocarbon group having 8 or more carbon atoms is a straight or branched chain consisting of 8 or more carbon atoms, for example 8 to 100, preferably 8 to 50, more preferably 8 to 30. It means a saturated or unsaturated hydrocarbon group, and for example, it may be a C 8 -C 100 alkyl group, C 8 -C 100 alkenyl group, or C 8 -C 100 alkynyl group.
  • the aliphatic hydrocarbon group having 8 or more carbon atoms includes octyl, ethylhexyl, nonyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, cetyl, stearyl, isostearyl, heptacosanyl, and the like. it is not
  • the (meth)acryl monomer having an aliphatic hydrocarbon group having 10 or more carbon atoms is a compound having an aliphatic hydrocarbon group having 10 or more carbon atoms and a (meth)acrylate group as a radically polymerizable functional group.
  • the (meth)acrylic monomer having an aliphatic hydrocarbon group having 10 or more carbon atoms decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, Tridecyl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, 1-heptacosanyl (meth) acrylate, etc. may be used, and these may be used alone. It can be used alone or in combination of two or more.
  • the vinyl ether monomer having an aliphatic hydrocarbon group having 8 or more carbon atoms is a compound having an aliphatic hydrocarbon group having 8 or more carbon atoms and a vinyl ether group as a radically polymerizable functional group.
  • vinyl ether monomer having an aliphatic hydrocarbon group having 8 or more carbon atoms 2-ethylhexyl vinyl ether, dodecyl vinyl ether, etc. may be used, and these may be used alone or in combination of two or more.
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention may be a thermosetting pressure-sensitive adhesive composition containing a (meth)acrylic copolymer and a thermosetting agent.
  • the (meth)acrylic copolymer is a component that serves to control the balance of viscosity versus elasticity of the pressure-sensitive adhesive composition, and may be a (meth)acrylic copolymer having a crosslinkable functional group in a molecule.
  • the (meth)acryl copolymer can be prepared by appropriately selecting a monomer so that the weight ratio of heteroatoms is 16.5% or less as described above, and for example, (meth)acryl having an aliphatic hydrocarbon group having 10 or more carbon atoms. It may be formed from a monomer mixture including at least one of a monomer and a vinyl ether monomer having an aliphatic hydrocarbon group having 8 or more carbon atoms, and a monomer having a crosslinkable functional group.
  • the monomer having a crosslinkable functional group may be at least one of a monomer having a hydroxyl group and a monomer having a carboxy group.
  • Examples of the monomer having a carboxyl group include monoacids such as (meth)acrylic acid, crotonic acid, and 2-carboxyethyl acrylate; diacids, such as maleic acid, itaconic acid, and fumaric acid, and monoalkyl esters thereof; 3-(meth)acryloylpropionic acid; a ring-opening adduct of succinic anhydride of 2-hydroxyalkyl (meth)acrylate having an alkyl group having 2-3 carbon atoms; Ring-opening adduct of succinic anhydride of hydroxyalkylene glycol (meth)acrylate having 2-4 carbon atoms in the alkylene group; and a compound obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth)acrylate having an alkyl group having 2-3 carbon atoms.
  • (meth)acrylic acid and 2-carboxyethyl acrylate
  • the monomer having the crosslinkable functional group is preferably included in an amount of 0.5 to 20% by weight, preferably 0.5 to 10% by weight, based on 100% by weight of the total monomer used in the preparation of the (meth)acrylic copolymer.
  • content of the monomer having a crosslinkable functional group is less than 0.5 wt%, the cohesive force of the pressure-sensitive adhesive may be reduced to decrease durability, and if it exceeds 20 wt%, the dielectric constant may be increased.
  • the (meth)acrylic copolymer may be formed from a monomer mixture further including other polymerizable monomers in addition to the above monomers.
  • the other polymerizable monomer examples include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethyl (meth) ) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylic a rate, nonyl (meth)acrylate, isobornyl (meth)acrylate, etc. are mentioned, Among these, 2-ethylhexyl (meth)acrylate and isobornyl (meth)acrylate are preferable. These can be used individually or in mixture of 2 or more types.
  • the other polymerizable monomer is included in an amount of 79.5 wt% or less, for example 1 to 79.5 wt%, preferably 5 to 79.5 wt%, based on 100 wt% of the total monomer used in the preparation of the (meth)acrylic copolymer.
  • the content of the other polymerizable monomer is more than 79.5% by weight, it may be difficult to control the weight ratio of heteroatoms to be 16.5% or less.
  • the method for preparing the (meth)acrylic copolymer is not particularly limited, and it can be prepared using methods such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization commonly used in the art, and solution polymerization is preferable. .
  • a solvent, polymerization initiator, chain transfer agent for molecular weight control, etc. commonly used during polymerization may be used.
  • the (meth)acrylic copolymer has a weight average molecular weight (in terms of polystyrene, Mw) measured by gel permeation chromatography (GPC) is usually 50,000 to 2 million, preferably 400,000 to 2 million . If the weight average molecular weight is less than 50,000, the cohesive force between the copolymers may be insufficient, which may cause problems in adhesion durability, and if the weight average molecular weight is more than 2 million, a large amount of diluent solvent may be required to secure fairness during coating.
  • Mw polystyrene
  • the molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the acrylic copolymer may be 7 or less. If the molecular weight distribution is more than 7, it may be difficult to secure durability due to the monomolecular oligomer.
  • the thermosetting agent is a component capable of improving adhesion and durability, and maintaining reliability and shape of the pressure-sensitive adhesive at high temperatures, and is also referred to as a crosslinking agent.
  • a crosslinking agent an isocyanate type, an epoxy type, a peroxide type, a metal chelate type, an oxazoline type, etc. may be used, and one type or a mixture of two or more types may be used. Among these, an isocyanate type is preferable.
  • thermosetting agent is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylene di diisocyanate compounds such as isocyanate and naphthalene diisocyanate;
  • An adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate product obtained by self-condensing 3 moles of a diisocyanate compound, and a diisocyanate obtained from 2 moles of 3 moles of a diisocyanate compound
  • thermosetting agent may be included in an amount of 0.04 to 1 part by weight, for example, 0.1 to 1 part by weight based on 100 parts by weight of the (meth)acrylic copolymer. If the content of the thermosetting agent is less than 0.04 parts by weight, the cohesive force may be small due to insufficient crosslinking, which may impair the physical properties of adhesion durability and cutability. have.
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention may be a photocurable pressure-sensitive adhesive composition containing a mixture of a (meth)acrylic copolymer and a photopolymerizable monomer, and a photoinitiator.
  • the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer may be a partial polymer obtained by partially polymerizing the photopolymerizable monomer mixture for preparing the (meth)acrylic copolymer.
  • This partial polymer exhibits a syrupy shape (viscous liquid) in which a (meth)acrylic copolymer formed from a part of the photopolymerizable monomer mixture and an unreacted photopolymerizable monomer are mixed. Therefore, the partial polymer of such properties is sometimes referred to as (meth)acrylic copolymer syrup.
  • the monomer mixture may be the same as that for preparing the (meth)acrylic copolymer used in the above-described thermosetting pressure-sensitive adhesive composition.
  • a method of partially polymerizing the monomer mixture is not particularly limited, and various polymerization methods may be appropriately selected and used. For example, a photopolymerization method may be used.
  • the weight ratio of the (meth)acrylic copolymer in the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer means the ratio in which the photopolymerizable monomer is converted to the (meth)acrylic copolymer due to partial polymerization, that is, the conversion rate, and syrup It corresponds to my solids content.
  • the weight ratio of the (meth)acrylic copolymer in the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer may be appropriately adjusted to control the viscosity of the (meth)acrylic copolymer syrup.
  • the weight ratio of the (meth)acrylic copolymer in the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer may be included in an amount of 10 to 40% by weight. If the content is less than 10% by weight, the viscosity may be too low because there are many remaining photopolymerizable monomers, and if it is more than 40% by weight, the viscosity may be too high, so that it may not be easy to apply the pressure-sensitive adhesive composition.
  • the photoinitiator means an initiator that absorbs an active energy ray to generate a radical.
  • the photoinitiators include, for example, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethylaminoacetophenone, 2, 2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenylketone , 2-Methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl ) ketone, benzophenone, p-phenylbenzophenone, 4,4'-bis(diethylamino)benzophenone (EAB-F), dichlorobenzophenone, 2-methyl anthr
  • the photoinitiator may be included in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the total amount of the (meth)acrylic copolymer and the photopolymerizable monomer.
  • content of the photoinitiator is less than 0.01 parts by weight, photocuring does not proceed sufficiently, so it is difficult to implement mechanical properties or adhesion of the finally obtained pressure-sensitive adhesive sheet. .
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention in addition to the above components, a silane coupling agent, a tackifying resin in order to control the adhesive force, cohesive force, viscosity, elastic modulus, glass transition temperature, antistatic property, etc. required according to the use , antioxidants, corrosion inhibitors, leveling agents, surface lubricants, dyes, pigments, defoamers, fillers, light stabilizers, may further include additives such as antistatic agents.
  • One embodiment of the present invention relates to a pressure-sensitive adhesive sheet formed using the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive sheet may be one in which the pressure-sensitive adhesive layer is formed from the pressure-sensitive adhesive composition according to the present invention on the base film, or the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to the present invention is interposed between two base films.
  • the base film may include a polyolefin-based film, a polyester-based film, an acrylic film, a styrene-based film, an amide-based film, a polyvinyl chloride film, a polyvinylidene chloride film, a polycarbonate film, and the like, and these are silicone-based, fluorine-based, silica It may be a mold release treatment suitably made with powder or the like.
  • the thickness of the base film is preferably 30 to 80 ⁇ m. When the thickness is less than 30 ⁇ m, the base film is vulnerable to engraving defects, and when it exceeds 80 ⁇ m, handling properties may be deteriorated.
  • An adhesive layer can be formed by the method of coating an adhesive composition on one base film.
  • the coating method is not particularly limited as long as it is a method known in the art, and for example, a method such as a bar coater, air knife, gravure, reverse roll, kiss roll, spray, blade, die coater, casting, spin coating, etc. can be used. .
  • it may be formed by coating the pressure-sensitive adhesive composition on a single base film, drying it at 30 to 150° C. for 1 second to 2 hours, preferably 5 seconds to 1 hour, and heat curing.
  • the pressure-sensitive adhesive composition is applied on one base film and dried at 30 to 150° C. for 1 second to 2 hours, preferably 5 seconds to 1 hour, and then about 100 to 2000 mJ/cm 2 , preferably 200 It can be formed by photocuring by irradiating with an ultraviolet irradiation amount of 1500mJ/cm2. After drying, you may bond another base film on the said adhesive layer.
  • the pressure-sensitive adhesive layer may have a thickness of 10 to 2,000 ⁇ m, preferably 25 to 1,500 ⁇ m. If the thickness of the pressure-sensitive adhesive layer is less than 10 ⁇ m, it may be difficult to buffer an impact generated from the outside, and if it exceeds 2,000 ⁇ m, transmission may be lowered and optical performance may be deteriorated.
  • the adhesive sheet according to an embodiment of the present invention may improve adhesion by surface-treating the adhesive layer before bonding.
  • the surface treatment method is not particularly limited, and for example, the surface of the pressure-sensitive adhesive layer may be activated by a method such as corona discharge treatment, plasma treatment, ultraviolet irradiation, electron beam irradiation, or applying an anchoring agent.
  • the pressure-sensitive adhesive sheet according to an embodiment of the present invention is applicable to not only a general flat panel display and a flexible display but also a foldable display.
  • the pressure-sensitive adhesive sheet according to an embodiment of the present invention can be effectively applied to interlayer adhesion using a high frequency band or laminating components in a thin display device.
  • the adhesive sheet may be applied to bonding of various display materials such as an antenna, a display panel, a polarizer, a touch sensor, a cover window, a bezel, a polymer film, and an FPCB, and in particular, may be applied to bonding of an antenna or a touch sensor.
  • IBOA isobornyl acrylate
  • IBOA isobornyl acrylate
  • i-SA isostearylacrylate
  • 2-hydroxyethyl acrylate (2- HEA) 100 parts by weight of a monomer mixture consisting of 10% by weight and 0.04 parts by weight of Igacure 184 (BASF) as a photoinitiator were mixed in a glass container to prepare a mixture.
  • the mixture was partially polymerized by irradiating ultraviolet rays using a low pressure lamp (Sylvania BL Lamp) for several minutes to have a viscosity of about 15,000 cPs and a viscous liquid having a solid content of 42% by weight; That is, an acrylic copolymer syrup was obtained (weight ratio of heteroatoms: 15.8%).
  • a low pressure lamp Sylvania BL Lamp
  • a pressure-sensitive adhesive composition was prepared by mixing the acrylic copolymer of Preparation Examples and Comparative Preparation Examples, the acrylic copolymer syrup of Preparation Examples, a thermal curing agent and a photoinitiator in the composition shown in Table 2 below.
  • Crosslinking agent A Coronate-L, TDI (toluene diisocyanate) type, Nippon Urethane
  • Crosslinking agent B Coronate-HXR, HDI (hexamethylene diisocyanate) type, Nippon Urethane
  • the pressure-sensitive adhesive compositions of Examples 1 to 6 and Comparative Examples 1 to 3 prepared above were dried on a 50 ⁇ m-thick release film coated with a silicone release agent so that the thickness became 150 ⁇ m, and dried at 100° C. for 5 minutes. An adhesive layer was formed, and a release film was laminated thereon to prepare an adhesive sheet.
  • the pressure-sensitive adhesive composition of Example 7 prepared above is dried on a 50 ⁇ m-thick release film coated with a silicone release agent, then applied to a thickness of 150 ⁇ m, and dried at 110° C. for 5 minutes to form an adhesive layer, A release film was laminated thereon.
  • a pressure-sensitive adhesive sheet was prepared by irradiating both sides of the release film with ultraviolet light at a light amount of 1.5 J/cm 2 using a low pressure lamp (Sylvania BL Lamp) for about 6 minutes.
  • dielectric constant and dielectric loss tangent were measured using a dielectric constant measuring device (Anritsu, product name: MS46522B) at a temperature of 25° C. and a humidity of 50%.
  • a 150 ⁇ m adhesive sheet from which the release film is removed was laminated between the upper and lower 40 ⁇ m COP films (Zeonor) and cut to a size of 30mm in length ⁇ 70mm in width.
  • the cut adhesive sheet was put into a probe of a measuring device, and the dielectric constant (Dk) and dielectric loss tangent (Df) values at 15 GHz were measured.
  • Example comparative example One 2 3 4 5 6 7 8 One 2 3 permittivity 2.47 2.42 2.37 2.33 2.35 2.29 2.31 2.43 2.53 2.60 2.63 dielectric loss tangent 0.014 0.011 0.009 0.006 0.004 0.002 0.010 0.013 0.023 0.028 0.032
  • the pressure-sensitive adhesive sheets of Examples 1 to 7 in which the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer is 16.5% or less
  • the dielectric constant was less than 2.5 and the dielectric loss tangent was 0.015 or less, indicating excellent low dielectric properties. Accordingly, the adhesive sheets of Examples 1 to 7 do not lower the antenna gain value when applied to an antenna using a high frequency band, thereby enabling faster antenna transmission/reception, and touch even when the image display device is thinned. It was found that there was no effect on the operation of the sensor.
  • the pressure-sensitive adhesive sheets of Comparative Examples 1 to 3 in which the weight ratio of heteroatoms in the (meth)acrylic copolymer or the mixture of the (meth)acrylic copolymer and the photopolymerizable monomer exceeds 16.5% has a dielectric constant in the high frequency band of 15GHz It is 2.5 or more, and the dielectric loss tangent is more than 0.015, indicating that it will affect the operation of the touch sensor when the antenna gain value is lowered or the image display device is thinned when applied to an antenna using a high frequency band.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

La présente invention concerne une composition adhésive contenant un copolymère (méth)acrylique ou un mélange d'un copolymère (méth)acrylique et d'un monomère photopolymérisable, le rapport en poids des hétéroatomes dans le copolymère (méth)acrylique ou du mélange d'un copolymère (méth)acrylique et d'un monomère photopolymérisable étant régulé et la constante diélectrique et la tangente de perte diélectrique à 15 GHz d'une couche adhésive d'une épaisseur de 150 µm après durcissement étant régulées dans une plage spécifique. La composition adhésive selon la présente invention peut présenter de faibles propriétés diélectriques, appropriées pour une application à des dispositifs d'affichage d'image qui nécessitent une bande de fréquence élevée ou qui sont amincis.
PCT/KR2021/008116 2020-07-01 2021-06-28 Composition adhésive et feuille adhésive l'utilisant WO2022005138A1 (fr)

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KR102229883B1 (ko) * 2020-07-01 2021-03-18 동우 화인켐 주식회사 점착제 조성물 및 그를 이용한 점착 시트
JP7173252B2 (ja) * 2020-09-24 2022-11-16 三菱ケミカル株式会社 粘着剤組成物、粘着剤及び粘着剤層
KR20230049859A (ko) * 2021-10-07 2023-04-14 동우 화인켐 주식회사 점착 시트 및 이를 포함하는 안테나 구조체

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KR20090042880A (ko) * 2006-08-07 2009-05-04 미쓰이 가가쿠 폴리우레탄 가부시키가이샤 경화성 수지 및 경화성 조성물
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