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WO2019054778A1 - Composition adhésive, lame polarisante et élément optique - Google Patents

Composition adhésive, lame polarisante et élément optique Download PDF

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Publication number
WO2019054778A1
WO2019054778A1 PCT/KR2018/010771 KR2018010771W WO2019054778A1 WO 2019054778 A1 WO2019054778 A1 WO 2019054778A1 KR 2018010771 W KR2018010771 W KR 2018010771W WO 2019054778 A1 WO2019054778 A1 WO 2019054778A1
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WO
WIPO (PCT)
Prior art keywords
weight
resin
parts
meth
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2018/010771
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English (en)
Korean (ko)
Inventor
노승주
윤하송
김우연
손현희
김장순
서광수
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180107807A external-priority patent/KR102159496B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to JP2020514204A priority Critical patent/JP7033654B2/ja
Priority to US16/647,232 priority patent/US11384265B2/en
Priority to CN201880058186.2A priority patent/CN111094484B/zh
Publication of WO2019054778A1 publication Critical patent/WO2019054778A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09J133/06—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
    • C09J133/08—Homopolymers or copolymers of acrylic acid 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
    • 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
    • C09J133/06—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
    • C09J133/10—Homopolymers or copolymers of methacrylic acid 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the present application relates to a pressure-sensitive adhesive composition, a polarizing plate and an optical member.
  • &quot liquid crystal display device
  • LCD device &quot including an optical functional film such as a polarizing film, a retardation film or a brightness enhancement film and a liquid crystal panel
  • a pressure-sensitive adhesive may be used to adhere the optically functional film to the panel.
  • the pressure-sensitive adhesive When the pressure-sensitive adhesive is used for the above-described use, there may be a case where the pressure-sensitive adhesive is transferred from the release-type substrate, or the pressure-sensitive adhesive is adhered to the object to be adhered or peeled for reuse therefrom.
  • the static electricity generated in this process may cause malfunction of the device.
  • the pressure-sensitive adhesive is prepared by drying a solvent in a pressure-sensitive adhesive composition applied on a release-type substrate, and then transferring the solvent. In this process, bubbles or irregularities in thickness of the pressure-sensitive adhesive layer may occur.
  • Another object of the present invention is to provide a solvent-free pressure-sensitive adhesive composition capable of preventing the generation of static electricity because the surface resistance is low when the pressure-sensitive adhesive layer is formed.
  • the present application relates to an adhesive polarizer.
  • the polarizing plate may include a polarizing film and an adhesive layer formed on at least one surface of the polarizing film.
  • the adhesive layer may be formed by photo-curing the composition for non-use of the formulation described below. That is, the adhesive layer may be a cured product of the solvent-free photo-curable composition.
  • Photocuring can be accomplished, for example, by electromagnetic waves such as microwaves, infrared (IR), ultraviolet (UV), X-rays or gamma rays, as well as alpha-particle beams, proton beams, For example, by irradiation of a particle beam such as a neutron beam and an electron beam.
  • the conditions for photo-curing the composition are not particularly limited.
  • the polarizing film may be a functional film capable of extracting only light vibrating in one direction from incident light while vibrating in various directions.
  • the kind of usable polarizing film is not particularly limited.
  • a general polarizing film known in this field can be used without limitation, such as a polyvinyl alcohol polarizing film in which a dichroic dye is adsorbed and oriented on a polyvinyl alcohol film.
  • the polyvinyl alcohol-based resin used for the polarizing film can be obtained by, for example, gelling a polyvinyl acetate-based resin.
  • the polyvinyl acetate-based resin which can be used may include a homopolymer of vinyl acetate, as well as a copolymer of vinyl acetate and other monomers copolymerizable therewith.
  • the monomer copolymerizable with vinyl acetate include monomers such as unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and acrylamides having an ammonium group, or a mixture of two or more thereof. no.
  • the degree of gelation of the polyvinyl alcohol-based resin may be generally from 85 mol% to 100 mol%, preferably 98 mol% or more.
  • the polyvinyl alcohol resin may be further modified. For example, polyvinyl formal or polyvinyl acetal modified with aldehydes may be used.
  • the degree of polymerization of the polyvinyl alcohol-based resin may be about 1,000 to 10,000, preferably about 1,500 to 5,000.
  • the polarizing film is formed by a process of stretching a polyvinyl alcohol resin film (uniaxially stretching), a process of dyeing a polyvinyl alcohol resin film with a dichroic dye and adsorbing the dichroic dye, a process of adsorbing a dichroic dye A process of treating a polyvinyl alcohol resin film with a boric acid aqueous solution and a process of washing with a boric acid aqueous solution after washing.
  • the dichroic dye iodine and dichroic organic dyes may be used.
  • the method of forming the pressure-sensitive adhesive layer on the optical member such as the polarizing film is not particularly limited.
  • a pressure-sensitive adhesive composition for forming a pressure-sensitive adhesive layer mentioned below may be cured by applying a pressure-sensitive adhesive composition using a bar coater or the like, or the pressure-sensitive adhesive composition may be coated on the surface of a releasable substrate And a method of transferring it.
  • the composition of the present application is more suitable for the latter method in that the generation of static electricity can be suppressed when the release agent is removed.
  • the adhesive layer may be a photo-curable material of the solventless formulation. That is, the composition used to form the adhesive layer is a solventless formulation and may be a composition comprising a photocurable component.
  • the term " solventless formulation composition " means that the composition does not contain a solvent, for example, an organic solvent or an aqueous solvent.
  • the term " photocurable composition " in the present application means a composition that can be cured by radical polymerization according to light irradiation.
  • the photocurable composition may include a resin having a carbon-carbon unsaturated double bond in the molecule so that polymerization can be carried out by a radical reaction according to light irradiation.
  • the drying process for the solvent can be omitted, so that the process efficiency can be enhanced, and bubbles due to the solvent can be avoided and the durability deterioration of the adhesive polarizing plate can be avoided.
  • the solventless photocurable composition is advantageous in securing adhesion.
  • a thermosetting composition such as an isocyanate reaction type composition is required to be separately aged for stabilizing physical properties after curing, but the photo-curing composition has an advantage that it can be commercialized immediately after curing without aging.
  • the use of the solvent-free photo-curable composition has an advantage of being able to avoid the problem of shrinkage or deterioration of the polarizer that occurs during thermal curing.
  • non-solvent-formable photocurable composition of the present application may contain two or more photocurable resins (or polymers) having different molecular weights and having carbon-carbon unsaturated double bonds in each molecule.
  • the composition may further include a first resin having a weight average molecular weight (Mw) in a range of 1,000,000 to 3,500,000, and a second resin having a weight average molecular weight lower than that of the first resin.
  • Mw weight average molecular weight
  • the weight average molecular weight in the present application may mean a value converted to a standard polystyrene measured by GPC (Gel Permeation Chromatograph) as described in Examples described later.
  • the second resin having a relatively small molecular weight may be present in a state of being appropriately dispersed in the composition containing the second resin and / or the cured product thereof, because the second resin has better dispersibility than the first resin. Due to the characteristics of the second resin, the migration of the antistatic agent onto the surface of the pressure-sensitive adhesive layer can be facilitated, and the effect of reducing the surface resistance of the pressure-sensitive adhesive layer can be greatly improved even with a small amount of the antistatic agent.
  • the second resin may include a (meth) acrylic acid ester monomer and a polymerization unit derived from a monomer represented by the following formula (1).
  • the term "polymerized unit" in the present application may mean a state in which the predetermined monomer is polymerized in the main chain or side chain of a resin, a polymer or a polymerization reaction product formed by polymerization of a predetermined monomer which is one impression.
  • Q is hydrogen or an alkyl group
  • U is alkylene having 1 to 4 carbon atoms
  • m is a number within the range of 1 to 15
  • Z is hydrogen, an alkyl group or an aryl group.
  • m may be any number, for example, in the range of 1 to 15, in the range of 1 to 13, or in the range of 1 to 11. When the above range is satisfied, appropriate conductivity can be given to the pressure-sensitive adhesive.
  • alkyl group in the present application may mean an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, unless otherwise specified.
  • the alkyl group may be straight-chain, branched or cyclic.
  • the alkyl group may be substituted by one or more substituents, or may be unsubstituted.
  • the alkylene group may be an alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms.
  • the alkylene group may be straight-chain, branched or cyclic.
  • the alkylene group may be optionally substituted by one or more substituents.
  • aryl group in the present application includes a benzene ring, or two or more benzene rings are linked, or two or more benzene rings may share one or more carbon atoms, May refer to a monovalent residue derived from a compound or a derivative thereof having a structure represented by the following formula:
  • the aryl group may be, for example, an aryl group having 6 to 25 carbon atoms, 6 to 22 carbon atoms, 6 to 16 carbon atoms, or 6 to 13 carbon atoms.
  • aryl group examples include a phenyl group, a phenylethyl group, a phenylpropyl group, a benzyl group, a tolyl group, a xylyl group and a naphthyl group.
  • Examples of the compound of the formula (1) include, for example, ethoxyethoxyethyl (meth) acrylate, alkoxy dialkylene glycol (meth) acrylic acid ester, alkoxytrialkylene glycol (meth) acrylic acid ester, alkoxy tetraalkylene glycol (Meth) acrylic acid esters, aryloxy dialkylene glycol (meth) acrylic acid esters, aryloxytrialkylene glycol (meth) acrylic acid esters, aryloxytetraalkylene glycol (meth) acrylic acid esters or polyalkylene glycol monoalkyl ethers ) Acrylate esters, but are not limited thereto.
  • the kind of the (meth) acrylic acid ester monomer contained in the second resin is not particularly limited.
  • alkyl (meth) acrylates having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms and 1 to 4 carbon atoms may be used have.
  • Examples of such monomers include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, (Meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, pentyl (Meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate or lauryl (meth) acrylate may be used.
  • the second resin may include 50 to 90 parts by weight of a (meth) acrylic acid ester monomer and 10 to 50 parts by weight of a monomer represented by the formula (1).
  • the amount of the monomer represented by the above formula (1) is less than 10 parts by weight, the antistatic property is insignificant.
  • compatibility with the first resin is deteriorated and inter-resin phase separation may occur.
  • " part by weight " may mean a relative weight ratio between the components.
  • the relative weight ratio of the two monomers in the mixture is 50 parts by weight (meth) To 90 parts by weight: 10 to 50 parts by weight of the monomer represented by the formula (1).
  • the weight average molecular weight of the second resin may be less than 1,000,000.
  • the antistatic function of the pressure-sensitive adhesive composition can be further improved because it functions as a kind of plasticizer. More specifically, the molecular weight of the second resin may be less than 950,000, less than 900,000, less than 850,000, less than 800,000, less than 750,000, less than 700,000, less than 650,000, less than 600,000, less than 550,000, less than 500,000, less than 450,000, have. When considering the function as a plasticizer, it is more preferable that it is 800,000 or less.
  • the molecular weight lower limit of the second resin may be 50,000 or more, 100,000 or more, 150,000 or more, 200,000 or more, or 250,000 or more. When the molecular weight of the second resin is less than 50,000, the cohesive force of the pressure-sensitive adhesive film is significantly lowered and the durability may be poor.
  • the composition may comprise from 40 parts by weight to 95 parts by weight of the first resin and from 5 parts by weight to 60 parts by weight of the second resin.
  • the amount of the second resin is less than 5 parts by weight, it is difficult to obtain a desired level of antistatic performance.
  • the amount of the second resin is more than 60 parts by weight, the characteristics of the first resin are greatly impaired and durability may be poor.
  • the content of the first resin having a larger molecular weight is equal to or greater than the content of the second resin in the relative content of the first resin and the second resin.
  • the composition may comprise 50 to 95 parts by weight of the first resin and 5 to 50 parts by weight of the second resin.
  • the first resin may comprise polymerized units of a (meth) acrylic acid ester monomer.
  • the first resin may be a polymer of a (meth) acrylic acid ester monomer or a mixture thereof.
  • the (meth) acrylic acid ester monomer one or more monomers mentioned in relation to the second resin may be used.
  • the first resin may further comprise polymerized units of a compound capable of hydrogen bonding.
  • a compound capable of hydrogen bonding When the first resin has a polymerized unit of a hydrogen-bondable compound, adhesion of the pressure-sensitive adhesive layer or durability of the pressure-sensitive adhesive layer can be improved through hydrogen bonding.
  • the kind of the hydrogen-bondable compound is not particularly limited, and for example, one or more compounds including a hydroxyl group, a carboxyl group, a urethane group, an amine group, or an amide group may be used.
  • the hydrogen-bondable compound includes 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) Hydroxyalkyl (meth) acrylates such as hexyl (meth) acrylate or 8-hydroxyoctyl (meth) acrylate; (Meth) acrylates such as poly (alkylene glycol) (meth) acrylates such as poly (ethylene glycol) (meth) acrylate or poly (propylene glycol) , Carboxyl group-containing copolymerizable monomers such as 3- (meth) acryloyloxypropyl acid, 4- (meth) acryloyloxybutyl acid, acrylic acid doublet, itaconic acid, maleic acid or maleic anhydride; (Meth) acrylamide or N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N- (Meth)
  • the first resin when the first resin contains a compound capable of hydrogen bonding as a polymerized unit, the first resin may contain 30 parts by weight or less of polymerizable units capable of hydrogen bonding.
  • the first resin may include at least 70 parts by weight of a (meth) acrylic acid ester monomer and at most 30 parts by weight of a compound capable of hydrogen bonding. If the content of the hydrogen-bondable compound exceeds 30 parts by weight, the attractive force between the hydrogen bondable compound and the surface of the adherend substrate may be greater than that attributed to the adherend substrate surface, thereby deteriorating the adhesive property.
  • the content of the hydrogen-bondable compound that can be used in forming the first resin is 25 parts by weight or less, 20 parts by weight or less, 15 parts by weight or less, Or less.
  • the lower limit is 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, 5 parts by weight or more, 6 parts by weight or more, 7 parts by weight or more, 8 parts by weight or more, 10 parts by weight or more.
  • the pressure sensitive adhesive composition may comprise a polyfunctional (meth) acrylate. If the compound has two or more (meth) acryloyl groups in the molecule, the specific type of the polyfunctional (meth) acrylate contained in the composition is not particularly limited.
  • the composition may further comprise a photocurable oligomer.
  • a photocurable oligomer urethane acrylate obtained by reacting a polyol and a polyisocyanate compound can be used.
  • the oligomer may be measured by GPC and may have a weight average molecular weight (Mw) in the range of 1,000 to 50,000 calculated on the basis of polystyrene.
  • the second crosslinking agent may be a bifunctional urethane acrylate oligomer having two acrylate groups at the terminals thereof.
  • the photocurable oligomer may be used in an amount of 15 parts by weight or less based on 100 parts by weight of the total amount of the first resin and the second resin. For example, it may be used in an amount of 0.01 or more, 0.1 or more, 0.5 or more, or 1.0 or more, and 10 or less parts or 5 parts or less.
  • the pressure-sensitive adhesive composition may further include a photoinitiator.
  • a photoinitiator known compounds can be used. For example, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl- 1-propanone), 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methyl- Methyl-1-propanone, methylbenzoylformate, oxy-phenyl-acetic acid -2- [2-oxo-2-phenyl-acetoxy-ethoxy] - Ethyl-oxy-phenyl-acetic acid-2- [2-hydroxy-ethoxy] -ethyl ester, oxy- phenyl-acetic acid-2- [2-hydroxy-ethoxy] -ethyl ester, alpha-dimethoxy-alpha-phenylacetophenone, 2-benzyl- 2- (dimethylamino) - (4-morpholinyl) phenyl] -1-butan
  • a commercialized photoinitiator product may be used, for example, an alpha-hydroxy ketone based compound (e.g., IRGACURE 184, IRGACURE 500, IRGACURE 2959, DAROCUR 1173, Ciba Specialty Chemicals); Phenylglyoxylate-based compounds (ex IRGACURE 754, DAROCUR MBF; Ciba Specialty Chemicals); Benzyldimethylketal compounds (ex IRGACURE 651; Ciba Specialty Chemicals); a-aminoketone-based compounds (ex IRGACURE 369, IRGACURE 907, IRGACURE 1300, Ciba Specialty Chemicals); Monoacylphosphine based compounds (MAPO) (ex.
  • an alpha-hydroxy ketone based compound e.g., IRGACURE 184, IRGACURE 500, IRGACURE 2959, DAROCUR 1173, Ciba Specialty Chemicals
  • DAROCUR TPO Ciba Specialty Chemicals
  • Bisacylphosphine compounds BAPO
  • BAPO bisacylphosphine compounds
  • Phosphine oxide-based compounds ex IRGACURE 2100; Ciba Specialty Chemicals
  • Metallocene compounds ex IRGACURE 784; Ciba Specialty Chemicals
  • Or iodonium salt can be used.
  • the initiator may be used in an amount of 5 parts by weight or less based on 100 parts by weight of the total amount of the first resin and the second resin. Specifically, the initiator may be used in an amount of 0.001 parts by weight or more, or 0.01 parts by weight or more, and 3 parts by weight or less, or 2 parts by weight or less. When an initiator is used in this range, suitable photo-curing can be achieved.
  • the adhesive composition of the present application may contain an antistatic agent.
  • an antistatic agent known antistatic agents can be used without limitation.
  • the adhesive composition of the present application may contain up to 5 parts by weight of an antistatic agent, based on 100 parts by weight of the total amount of the first resin and the second resin.
  • the antistatic agent may be used in an amount of 5 parts by weight or less, 4 parts by weight or less, 3 parts by weight or less, or 2 parts by weight or less.
  • the polymerization unit derived from the compound represented by the general formula (1) contained in the second resin is excellent in affinity with the antistatic agent.
  • the second resin having a relatively low molecular weight has excellent dispersibility. Therefore, the second resin having a low molecular weight and the antistatic agent can have a uniform surface distribution in the composition of the present application and / or the cured product thereof, thereby effectively lowering the surface resistance of the adhesive layer.
  • the lower limit of the antistatic agent content may be 0.1 parts by weight or more, 0.2 parts by weight or more, 0.3 parts by weight or more, 0.4 parts by weight or more, or 0.5 parts by weight or more, though not particularly limited.
  • an ionic compound may be used as the antistatic agent.
  • an ionic compound for example, a metal salt or an organic salt may be used.
  • the metal salt ionic compound may include, for example, an alkali metal cation or an alkaline earth metal cation. Cations, the lithium ions (Li +), sodium ion (Na +), potassium ion (K +), rubidium ions (Rb +), cesium ion (Cs +), beryllium ion (Be 2 +), magnesium ion ( Mg 2 +), calcium ions (Ca 2 +), strontium ion (Sr 2 +) and barium ion (Ba 2 +) there is iljong or two kinds or more of the like can be illustrated, for example, a lithium ion, a sodium ion, Potassium ion, magnesium ion, calcium ion and barium ion, or ion stability and mobility.
  • anion contained in the metal salt is PF 6 -, AsF -, NO 2 -, fluoride (F -), chloride (Cl -), bromide (Br -), iodide (I -), perchlorate (ClO 4 - ), hydroxide (OH -), carbonate (CO 3 2-), nitrate (NO 3 -), trifluoromethane sulfonate (CF 3 SO 3 -), sulfonate (SO 4 -), hexafluoro with phosphate (PF 6 -), methyl benzene sulfonate (CH 3 (C 6 H 4 ) SO 3 -), p- toluenesulfonate (CH 3 C 6 H 4 SO 3 -), tetraborate (B 4 O 7 2 -), carboxymethyl sulfonate (COOH (C 6 H 4) SO 3 -), sulfonate as a triple (CF 3 SO 2 -,
  • the anion contained in the metal salt may be an anion or bifluorosulfonylimide represented by the following formula (2), or the like.
  • A is a nitrogen atom or a carbon atom
  • B is a carbon atom or a sulfur atom
  • R f is a perfluoroalkyl group
  • m is 1 or 2
  • n is 2 or 3.
  • B when B is carbon, m is 1, and when B is sulfur, m is 2, and when A is nitrogen, n is 2 and when A is carbon, n may be 3.
  • the anion or bis (fluorosulfonyl) imide of formula (2) exhibits a high electronegativity due to the perfluoroalkyl group (R f ) or the fluorine group and also forms a weak bond with the cation, including a unique resonance structure And at the same time has hydrophobicity. Therefore, the ionic compound exhibits excellent compatibility with other components of the composition such as a polymer, and can give a high antistatic property even in a small amount.
  • R f in Formula 2 may be a perfluoroalkyl group having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, wherein the perfluoroalkyl group may be a straight chain, And may have a cyclic structure.
  • the anion of the formula (2) may be a sulfonylimide-based, sulfonylimide-based, carbonylimide-based or carbonylimide-based anion.
  • tris trifluoromethanesulfonylmethide bistrifluoromethanesulfonyl A perfluorobutanesulfonylimide, bispentafluoroethanesulfonylimide, tris trifluoromethanecarbonylmide, bis perfluorobutanecarbonylimide or bispentafluoroethanecarbonyl, bispentafluoroethanesulfonylimide, bis It can be used more than one kind of imide.
  • organic salt ionic compound examples include N, N-dimethyl N-propylammonium, N, N, N-trimethyl-N-propylammonium, N-methyl- N, N-dibutylammonium, N, N-tributylammonium, N-ethyl-N, N, Quaternary ammonium such as N-methyl-N, N, N-trioctylammonium or N-ethyl-N, N, N-trioctylammonium, phosphonium, pyridinium, imidazolium ), Pyrolidinium, piperidinium or the like may be used together with the anion component.
  • the antistatic agent may simultaneously contain the metal salt and the organic salt, if necessary.
  • the pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer may further include additives such as an epoxy resin, a curing agent, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, a defoamer, a surfactant or a plasticizer.
  • additives such as an epoxy resin, a curing agent, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, a defoamer, a surfactant or a plasticizer.
  • the specific kind or content of the additive is not particularly limited.
  • the adhesive layer having the above-described constitution can have a surface resistance value and a peeling force suitable for use.
  • the adhesive layer has a surface resistance value of 1 x 10 < 10 > OMEGA / & squ & and the peeling force measured at a speed of 300 mm / min and a 90 DEG angle with respect to the glass substrate is in the range of 300 to 700 gf / inch .
  • the present application is also directed to a display device.
  • the display device is an LCD
  • the device may include a liquid crystal panel and the adhesive polarizer attached to one or both surfaces of the liquid crystal panel.
  • the liquid crystal panel may include, for example, a first substrate sequentially formed, a pixel electrode, a first alignment film, a liquid crystal layer, a second alignment film, a common electrode, and a second substrate.
  • the first substrate and the second substrate may be glass substrates.
  • the optical member may be attached to the glass substrate via a pressure-sensitive adhesive layer.
  • the apparatus may further include a light source on the opposite side of the viewing side of the liquid crystal panel.
  • a light source on the opposite side of the viewing side of the liquid crystal panel.
  • an active driving circuit including TFT (Thin Film Transistor), wiring and the like may be formed as a driving element electrically connected to the transparent pixel electrode.
  • the pixel electrode includes, for example, ITO (Indium Tin Oxide) or the like and can function as an electrode for each pixel.
  • the first or second alignment film may include, for example, a material such as polyimide, but is not limited thereto.
  • liquid crystal panel in the apparatus examples include passive matrix type panels such as TN (twisted nematic) type, STN (super twisted nematic) type, F (ferroelectic) type or PD (polymer dispersed) type;
  • An active matrix type panel such as a two terminal or a three terminal type;
  • a known panel such as an in-plane switching (IPS) panel and a vertical alignment (VA) panel may be used.
  • IPS in-plane switching
  • VA vertical alignment
  • the present application relates to a pressure sensitive adhesive composition.
  • the specific composition of the pressure-sensitive adhesive composition is the same as that described above, and can be used for a purpose of being attached to one surface of a polarizing plate.
  • a pressure-sensitive adhesive composition a pressure-sensitive adhesive composition, a polarizing plate, and a liquid crystal device excellent in durability and antistatic property can be provided.
  • Weight average molecular weight The molecular weight and the molecular weight distribution (PDI) of the polymer were measured using GPC (Gel Permeation Chromatograph), and the GPC measurement conditions were as follows. The calibration curve was prepared using standard polystyrene (Aglient system), and the measurement result was converted into weight average molecular weight (Mw).
  • Aglient GPC Aglient 1200 series, U.S.
  • the surface resistance of the adhesive layer was measured using a Hiresta-UX surface resistance meter, and the measurement conditions were as follows.
  • Adhesive layer was cut to 8 x 13 cm on soda-lime glass and placed in a chamber at 60 °C / 90% RH. After 500 hours, Respectively.
  • Two optical members including a pressure-sensitive adhesive layer and a polarizing plate described below were laminated so as to be orthogonal to each other on a soda-lime glass, and they were laminated in an autoclave under the conditions of 40 DEG C, 4 bar and 20 minutes And made a trial version.
  • the prepared test plate was allowed to stand at 80 DEG C for 500 hours and the degree of light leakage was visually observed and evaluated according to the following criteria.
  • Peel strength The adhesive film was cut to a width of 1 inch, adhered to soda-lime glass, allowed to stand at room temperature for 1 hour, and peel strength was measured. At this time, the normal temperature is a temperature within a range of 18 to 30 ⁇ ⁇ at which no artificially warmed or reduced temperature is observed.
  • the first production of the resin (A) BA (n- butyl acrylate) 85 parts by weight of DMAA (dimethyl acrylamide) 5 parts by weight, and HBA (hydroxy butyl acrylate) 10 parts by weight, a weight average molecular weight by bulk polymerization at 50 °C CONDITIONS To obtain a first resin having 2,500,000.
  • Second Resin 60 parts by weight of BA (n-butyl acrylate) and 40 parts by weight of EOEOEA (2- (2-ethoxyethoxy) ethyl acrylate) were bulk polymerized to obtain a second resin having a weight average molecular weight of 300,000.
  • a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1, except that the resin content was changed as shown in Table 1 below.
  • An adhesive layer was prepared in the same manner as in Example 1, except that 100 parts by weight of one kind of resin having the structure shown in Table 1 below was used.
  • An adhesive layer was prepared in the same manner as in Example 1, except that 100 parts by weight of one kind of resin having the structure shown in Table 1 below was used.
  • An adhesive layer was prepared in the same manner as in Example 1, except that 100 parts by weight of one kind of resin having the structure shown in Table 1 below was used.
  • a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1, except that two resins having the same compositions as those shown in Table 1 below were used.
  • a pressure-sensitive adhesive layer was formed in the same manner as in Example 1, except that two kinds of resins having the same compositions as shown in Table 1 below were used.
  • Comparative Example 3 in which the antistatic agent is contained in an excessively large amount in order to lower the surface resistance, the antistatic agent bleeds out, resulting in poor high temperature / high humidity durability and adhesion.
  • Comparative Example 4 containing an excessive amount of EOEOA lowered the surface resistance, but the compatibility between resins was lowered and the high temperature / high humidity durability and adhesive strength were poor.
  • Comparative Example 5 in which the weight average molecular weight of the second resin is 1,000,000, the antistatic function by the second resin is insufficient and both the durability and the adhesive strength are not good.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention porte sur une composition adhésive sans solvant photodurcissable, une lame polarisante du type adhésive et un dispositif d'affichage. Selon la présente invention, une composition adhésive, une lame polarisante et un dispositif d'affichage à cristaux liquides, chacun de ceux-ci présentant une excellente durabilité et d'excellentes performances antistatiques, peuvent être fournis.
PCT/KR2018/010771 2017-09-15 2018-09-13 Composition adhésive, lame polarisante et élément optique Ceased WO2019054778A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2020514204A JP7033654B2 (ja) 2017-09-15 2018-09-13 粘着剤組成物、偏光板及び光学部材
US16/647,232 US11384265B2 (en) 2017-09-15 2018-09-13 Pressure-sensitive adhesive composition, polarizing plate, and optical member
CN201880058186.2A CN111094484B (zh) 2017-09-15 2018-09-13 压敏粘合组合物、偏光板和光学构件

Applications Claiming Priority (4)

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KR10-2017-0118726 2017-09-15
KR20170118726 2017-09-15
KR10-2018-0107807 2018-09-10
KR1020180107807A KR102159496B1 (ko) 2017-09-15 2018-09-10 점착제 조성물, 편광판, 및 광학부재

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WO2019054778A1 true WO2019054778A1 (fr) 2019-03-21

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110007687A (ko) * 2009-07-17 2011-01-25 공주대학교 산학협력단 무용제 자외선 경화형 아크릴 점착제 조성물 및 그 제조방법
KR20110029761A (ko) * 2009-09-16 2011-03-23 주식회사 엘지화학 양면 점착 테이프, 그 제조 방법 및 터치 패널
KR20120109750A (ko) * 2011-03-25 2012-10-09 한국생산기술연구원 성능이 개선된 자기점착성 보호필름 및 이를 부착한 물품
KR20160074425A (ko) * 2014-12-18 2016-06-28 주식회사 엘지화학 점착제 조성물
KR20170085095A (ko) * 2015-01-21 2017-07-21 가부시키가이샤 데라오카 세이사쿠쇼 점착 시트 및 그 제조 방법, 및 그것을 사용한 광학 부재의 제조 방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110007687A (ko) * 2009-07-17 2011-01-25 공주대학교 산학협력단 무용제 자외선 경화형 아크릴 점착제 조성물 및 그 제조방법
KR20110029761A (ko) * 2009-09-16 2011-03-23 주식회사 엘지화학 양면 점착 테이프, 그 제조 방법 및 터치 패널
KR20120109750A (ko) * 2011-03-25 2012-10-09 한국생산기술연구원 성능이 개선된 자기점착성 보호필름 및 이를 부착한 물품
KR20160074425A (ko) * 2014-12-18 2016-06-28 주식회사 엘지화학 점착제 조성물
KR20170085095A (ko) * 2015-01-21 2017-07-21 가부시키가이샤 데라오카 세이사쿠쇼 점착 시트 및 그 제조 방법, 및 그것을 사용한 광학 부재의 제조 방법

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