WO2016006875A1 - Plaque de polarisation ultramince, et dispositif d'affichage à cristaux liquides muni de cette plaque - Google Patents

Plaque de polarisation ultramince, et dispositif d'affichage à cristaux liquides muni de cette plaque Download PDF

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Publication number
WO2016006875A1
WO2016006875A1 PCT/KR2015/006856 KR2015006856W WO2016006875A1 WO 2016006875 A1 WO2016006875 A1 WO 2016006875A1 KR 2015006856 W KR2015006856 W KR 2015006856W WO 2016006875 A1 WO2016006875 A1 WO 2016006875A1
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Prior art keywords
group
ultra
formula
polarizing plate
acrylic copolymer
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English (en)
Korean (ko)
Inventor
최한영
김대철
박진영
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the present invention relates to an ultra-thin polarizing plate and a liquid crystal display device having the same, and more particularly, to an ultra-thin polarizing plate and a liquid crystal display device having the same excellent antistatic properties and excellent durability and optical properties even under severe conditions of high temperature and high humidity. It is about.
  • Liquid crystal display devices are used in various applications such as notebooks, mobile phones, liquid crystal TVs, etc., and generally include liquid crystal cells and polarizing plates containing liquid crystals, and as adhesive layers or adhesive layers for bonding them. It is composed.
  • polarizers used in liquid crystal displays generally have a polarizer having a thickness of about 30 ⁇ m in which an iodine-based compound or a dichroic polarizer is adsorbed on a polyvinyl alcohol (PVA) resin film arranged in a predetermined direction.
  • Polarizing film ' and on both sides of the polarizer, first and second polarizer protective films each having a thickness of about 80 ⁇ m represented by triacetyl cellulose (TAC) are laminated through an adhesive,
  • TAC triacetyl cellulose
  • One side of the polarizer protective film has a multi-layered structure in which the pressure-sensitive adhesive layer is laminated with the liquid crystal cell.
  • each constituent film of the polarizing plate is made of a material having a different molecular structure and composition, they have different physical and chemical properties.
  • the polarizer which is a double PVA stretched film, contracts or swells under high temperature and humidity, so that the constituent films of the polarizing plate bend or fall easily, and there is a problem in that bubbles are generated.
  • the ultra-thin polarizing plate is in direct contact with the iodine polarizer and the pressure-sensitive adhesive, so that the iodine ion to the pressure-sensitive adhesive is increased by increasing the degree of freedom of iodine due to a decrease in the crosslinking density due to the penetration of moisture under durability conditions, particularly moisture and heat resistance conditions. There is a concern that the optical characteristics may be degraded due to bleed-out.
  • the present invention is to solve the above problems, one object of the present invention is to provide an ultra-thin polarizing plate that can exhibit excellent durability and optical properties even under the conditions of excellent antistatic properties and high temperature and high humidity.
  • Another object of the present invention is to provide a liquid crystal display device having the ultra-thin polarizing plate on at least one side of a liquid crystal cell.
  • a protective film is attached to one surface of the polarizer, the pressure-sensitive adhesive layer is formed on the other surface of the surface is attached to the protective film, the pressure-sensitive adhesive composition comprising an acrylic copolymer in which the ionic functional group is fixed It provides an ultra-thin polarizing plate formed with.
  • the acrylic copolymer in which the ionic functional group is immobilized may be prepared by copolymerization of an ionic monomer with another acrylic monomer.
  • the acrylic copolymer in which the ionic functional group is immobilized may be prepared by preparing an acrylic copolymer including a tertiary amine group, followed by ammoniumation of the tertiary amine.
  • the acrylic copolymer in which the ionic functional group is immobilized prepares an acrylic copolymer containing at least one functional group selected from the group consisting of an acid anhydride group, an epoxy group and an isocyanate group, and then a hydroxy group and a thiol. It can be prepared by reacting with an ionic compound containing a group, a carboxyl group or an amino group.
  • the acrylic copolymer in which the ionic functional group is immobilized is prepared using a crosslinking reaction in which ammonium is produced by the reaction of an acrylic copolymer including a tertiary amine group and an acrylic copolymer including a leaving group. It can manufacture.
  • the pressure-sensitive adhesive composition is characterized in that it further comprises an antistatic agent not immobilized on the acrylic copolymer.
  • the present invention provides a liquid crystal display device having the ultra-thin polarizing plate on at least one side of the liquid crystal cell.
  • the ultra-thin polarizing plate formed of the pressure-sensitive adhesive composition comprising an acrylic copolymer in which the ionic functional group is immobilized according to the present invention can suppress the loss of iodine anions in the polarizer and thus exhibit excellent optical properties even under severe conditions of high temperature and high humidity, and also excellent durability. It can exhibit an antistatic performance.
  • a protective film is attached to one surface of the polarizer, an adhesive layer is formed on the other surface of the surface to which the protective film is attached, and the pressure-sensitive adhesive layer includes an acrylic copolymer in which an ionic functional group is immobilized. It relates to an ultra-thin polarizing plate formed of a composition.
  • the ultra-thin polarizing plate refers to a direct bonding of the polarizer and the pressure-sensitive adhesive layer without a separate protective film to implement a slimmer liquid crystal display device.
  • the polarizer is a dichroic dye is adsorbed orientation to the stretched polyvinyl alcohol-based resin film, iodine may be used as the dichroic dye.
  • the polyvinyl alcohol-based resin constituting the polarizer can be obtained by saponifying a polyvinyl acetate-based resin.
  • a polyvinyl acetate-based resin As said polyvinyl acetate type resin, the copolymer etc. of vinyl acetate and the other monomer copolymerizable with this besides the polyvinyl acetate which is a homopolymer of vinyl acetate are mentioned.
  • an unsaturated carboxylic acid type, unsaturated sulfonic acid type, an olefin type, a vinyl ether type, an acrylamide type monomer which has an ammonium group, etc. are mentioned.
  • the polyvinyl alcohol-based resin may be modified, for example, polyvinyl formal or polyvinyl acetal modified with aldehydes may be used.
  • the saponification degree of the polyvinyl alcohol-based resin is usually 85 to 100 mol%, preferably 98 mol% or more.
  • the degree of polymerization of the polyvinyl alcohol-based resin is usually 1,000 to 10,000, preferably 1,500 to 5,000.
  • What formed such a polyvinyl alcohol-type resin into a film is used as a raw film of a polarizer.
  • the film formation method of polyvinyl alcohol-type resin is not specifically limited, A well-known method can be used.
  • the film thickness of the raw film is not particularly limited, and may be, for example, 10 to 150 ⁇ m.
  • the polarizer is manufactured through a process of uniaxially stretching a polyvinyl alcohol-based film in an aqueous solution, a process of dyeing with a dichroic dye and adsorbing, a process of treating with an aqueous solution of boric acid, and washing with water and drying.
  • the process of uniaxially stretching the polyvinyl alcohol-based film may be performed before dyeing, may be simultaneously performed with dyeing, or may be performed after dyeing.
  • the uniaxial stretching is performed after dyeing, it may be performed before boric acid treatment, or may be performed during boric acid treatment.
  • rolls or heat rolls with different circumferential speeds can be used.
  • uniaxial stretching may be dry stretching extending
  • the draw ratio is usually 4 to 8 times.
  • the method of immersing a polyvinyl alcohol-type film in the aqueous solution containing a dichroic dye can be used, for example. Iodine may be used as the dichroic dye.
  • the polyvinyl alcohol-based film is preferably swelled by dipping in water before dyeing.
  • a dyeing process can use the method of immersing and dyeing a polyvinyl alcohol-type film in the aqueous solution for dyeing containing iodine and potassium iodide normally.
  • the content of iodine in the aqueous solution for dyeing is 0.01 to 1 part by weight based on 100 parts by weight of water (distilled water), and the content of potassium iodide is 0.5 to 20 parts by weight based on 100 parts by weight of water.
  • the temperature of the aqueous solution for dyeing is usually 20 to 40 ° C.
  • the immersion time (dyeing time) is usually 20 to 1,800 seconds.
  • Boric acid treatment of the dyed polyvinyl alcohol-based film can be carried out by immersing in a boric acid-containing aqueous solution.
  • the content of boric acid in the aqueous solution containing boric acid is 2 to 15 parts by weight, preferably 5 to 12 parts by weight with respect to 100 parts by weight of water.
  • the boric acid-containing aqueous solution preferably contains potassium iodide, and its content is usually 0.1 to 15 parts by weight, preferably 5 to 12 parts by weight with respect to 100 parts by weight of water.
  • the temperature of the boric acid-containing aqueous solution is usually 50 ° C or higher, preferably 50 to 85 ° C, more preferably 60 to 80 ° C, and the immersion time is usually 60 to 1,200 seconds, preferably 150 to 600 seconds, more preferably 200 to 400 seconds.
  • the polyvinyl alcohol-based film is usually washed with water and dried.
  • Water washing treatment can be performed by immersing the boric acid-treated polyvinyl alcohol-based film in water.
  • cleaning process is 5-40 degreeC normally, and immersion time is 1-120 second normally.
  • a polarizer can be obtained by drying after washing with water. Drying process can be normally performed using a hot air dryer or a far-infrared heater.
  • the drying treatment temperature is usually 30 to 100 ° C, preferably 50 to 80 ° C, and the drying time is usually 60 to 600 seconds, preferably 120 to 600 seconds.
  • the thickness of the polarizer is not particularly limited, but may be, for example, 5 to 80 ⁇ m.
  • the protective film is formed only on the other side of the surface on which the pressure-sensitive adhesive layer of the polarizer is formed, and is not used as a base material when the pressure-sensitive adhesive layer is formed.
  • the type of the protective film is not particularly limited as long as it is excellent in transparency, mechanical strength, thermal stability, moisture shielding, isotropy, and the like, and examples thereof include polyester-based films such as polyethylene terephthalate, polyethylene isophthalate, and polybutylene terephthalate; Cellulose films such as diacetyl cellulose and triacetyl cellulose; Polycarbonate film; Acrylic films such as polymethyl (meth) acrylate and polyethyl (meth) acrylate; Styrene films such as polystyrene and acrylonitrile-styrene copolymers; Polyolefin-based films such as polyethylene, polypropylene, cyclo-based or norbornene-structured polyolefin and ethylene propylene copolymer; Polyimide film; Polyether sulfone-based film; Conventional films such as sulfone films may be used, but are not limited thereto.
  • polyester-based films such as polyethylene
  • a surface treatment layer such as a hard coating layer, an antireflection layer, and an antiglare layer may be further stacked on the protective film.
  • the hard coating layer is for preventing damage to the surface of the polarizing plate, and for example, may be formed from an acrylic or silicone resin having excellent adhesion or hardness.
  • the anti-reflection layer is for preventing reflection of external light on the surface of the polarizing plate and may be formed by a known method.
  • the anti-glare layer is to prevent the visibility of the light generated by the external light shining on the surface of the polarizing plate, for example, sandblasting method, embossing method, roughening method, or UV-curable resin to the transparent fine particles It can be formed by the method of applying and curing the mixed composition.
  • the thickness of the protective film is not particularly limited, but may be 10 to 200 ⁇ m, preferably 10 to 150 ⁇ m.
  • the pressure-sensitive adhesive layer is directly bonded to the polarizer without a separate protective film, it is possible to implement a thinner and lighter weight of the polarizing plate.
  • it is formed of a pressure-sensitive adhesive composition comprising an antistatic agent immobilized on an acrylic copolymer to allow the polarizing plate according to the present invention to exhibit excellent durability even under severe conditions of high temperature and high humidity.
  • the KI ion salt used during the manufacturing process of the polarizer undergoes an ion exchange reaction with the ionic antistatic agent MX included in the pressure sensitive adhesive layer under moisture and heat conditions, so that the KI in the polarizer moves to the pressure sensitive adhesive layer, and the MX of the pressure sensitive adhesive layer Is moved to the polarizer layer, resulting in a decrease in the concentration of I in the polarizer, and a decrease in the degree of polarization of the polarizer occurs by the decrease in the concentration of I.
  • the antistatic agent in which the antistatic agent in the pressure-sensitive adhesive layer is immobilized on the acrylic copolymer In order to suppress the fall of the concentration of I in the polarizer, by using the antistatic agent in which the antistatic agent in the pressure-sensitive adhesive layer is immobilized on the acrylic copolymer, the ion exchange reaction can be prevented from progressing and the decrease in the concentration of I ions in the polarizer can be suppressed. . Further, in addition to the immobilized antistatic agent, even if it contains an additional unimmobilized antistatic agent, due to the ionic interaction of the immobilized ionic antistatic agent and the unimmobilized ionic antistatic agent, It is possible to suppress bleed-out.
  • the pressure-sensitive adhesive composition used in the present invention includes an acrylic copolymer in which an ionic functional group is immobilized.
  • the said acryl-type copolymer contains the (meth) acrylate monomer which has a C1-C12 alkyl group, and the polymerizable monomer which has a crosslinkable functional group.
  • the (meth) acrylate means acrylate and methacrylate.
  • (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms examples include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, and 2-ethyl.
  • the polymerizable monomer having a crosslinkable functional group is a component for reinforcing the cohesive force or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding and imparting durability and cutting properties, for example, a monomer having a hydroxy group, a monomer having a carboxyl group, and a monomer having an amide group.
  • the monomer etc. which have a tertiary amine group are mentioned, These can be used individually or in mixture of 2 or more types.
  • Monovalent acids such as (meth) acrylic acid and a crotonic acid; Diacids such as maleic acid, itaconic acid and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; Succinic anhydride ring-opening adduct of 2-hydroxyalkyl (meth) acrylate with 2-3 carbon atoms of an alkyl group, Succinic anhydride ring opening adduct of hydroxyalkylene glycol (meth) acrylate with 2-4 carbon atoms of an alkylene group And a compound obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth) acrylate having 2 to 3 carbon atoms of an alkyl group, and among these, (meth) acrylic acid is preferable.
  • (meth) acrylic acid is preferable.
  • Examples of the monomer having an amide group include (meth) acrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (meth) acrylamide, 6 -Hydroxyhexyl (meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide, 2-hydroxyethylhexyl (meth) acrylamide, etc. are mentioned, Among these, (meth) acrylamide is preferable.
  • Monomers having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) acrylate, and N, N- (dimethylamino) propyl (meth ) Acrylates and the like.
  • the content is less than 0.05 parts by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. If the content is more than 10 parts by weight, the adhesive strength is lowered by a high gel fraction may cause problems in durability.
  • the acrylic copolymer in which the ionic functional group is immobilized can be prepared, for example, by one of the following methods.
  • any compound containing a photocurable double bond and an ionic functional group in the molecule may be used, but cationically curable ions having a photocurable group in a cation moiety, such as compounds of Formulas 1 and 2 below
  • Anionic curable ionic materials including photocurable groups in the anion moiety, such as the active material and the compound of Formula 3 may be used.
  • a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms which can be used in the preparation of the above-described acrylic copolymer may be used.
  • the acryl-based copolymer including the tertiary amine group may be prepared by copolymerization of a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a monomer simultaneously containing an unsaturated double bond and a tertiary amine group in a molecule thereof.
  • a compound represented by the following formulas 4 to 6 can be used as the monomer containing the unsaturated double bond and the tertiary amine group at the same time in a molecule.
  • the ammoniumation reaction of the acrylic copolymer including the tertiary amine group may be performed by adding a compound containing a good leaving group.
  • a compound containing a good leaving group include iodine methane, dimethyl sulfonate, trifluoromethyl (methyl) sulfonate, and halogenated benzyl compounds.
  • the acrylic copolymer containing at least one functional group selected from the group consisting of an acid anhydride group, an epoxy group and an isocyanate group includes a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, an unsaturated double bond, an acid anhydride group, an epoxy group and One or more functional groups selected from the group consisting of isocyanate groups can be prepared by copolymerization of monomers simultaneously containing in the molecule.
  • the monomer containing the unsaturated double bond and the acid anhydride group in the molecule at the same time it may be used a compound of the formula (7-8).
  • the monomer containing the unsaturated double bond and the epoxy group in the molecule at the same time it may be used a compound of formula 9 to 10.
  • a compound of formula 11 may be used as the monomer containing the unsaturated double bond and the isocyanate group in the molecule at the same time.
  • the acryl-based copolymer including the tertiary amine group may be prepared by copolymerization of a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a monomer simultaneously containing an unsaturated double bond and a tertiary amine group in a molecule thereof.
  • the compounds of the formulas (4) to (6) can be used as the monomer containing the unsaturated double bond and the tertiary amine group at the same time in the molecule.
  • the acrylic copolymer including the leaving group may be prepared by copolymerization of a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a monomer containing an unsaturated double bond and a leaving group in the molecule at the same time.
  • the monomer containing the unsaturated double bond and the leaving group in the molecule at the same time it may be used a compound of the formula (18) to 19.
  • X is halide, methanesulfonate, trifluoromethanesulfonate, benzenesulfonate or p-toluenesulfonate.
  • the acrylic copolymer including the tertiary amine group and the acrylic copolymer including the leaving group are cross-linked during curing after formation of the pressure-sensitive adhesive layer to introduce ionic functional groups.
  • the acrylic copolymer in which the ionic functional group is immobilized may further include a polymerizable monomer having the aforementioned crosslinkable functional group in addition to the monomers.
  • other polymerizable monomers may be further included in a range that does not lower the adhesion, for example, 10 wt% or less with respect to the total amount.
  • the production method of the copolymer is not particularly limited, and may be prepared using a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable.
  • a solvent, a polymerization initiator, a chain transfer agent for molecular weight control, and the like, which are usually used in the polymerization may be used.
  • the acrylic copolymer preferably has a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 50,000 to 2,000,000, more preferably 400,000 to 2,000,000. If the weight average molecular weight is less than 50,000, there is a lack of cohesion between copolymers may cause problems in adhesion durability, if the weight average molecular weight is more than 2,000,000 may require a large amount of dilution solvent to ensure fairness during coating.
  • Mw polystyrene equivalent
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention may further include an antistatic agent that is not immobilized on the acrylic copolymer.
  • an organic cation such as ammonium, phosphonium or sulfonium or an alkali metal cation may be used as the cation.
  • the organic cation include quaternary ammonium salts in which four alkyl groups such as tetrabutylammonium are substituted, 1-ethylpyridinium, 1-butylpyridinium, 1-hexylpyridinium, and 1-butyl-3-methylpyridinium.
  • pyridinium has an alkyl group substituted in N, such as pyridinium, 1-methyl-3-butylimidazonium, and 1-methyl-3-hexylimidazonium.
  • Cations such as substituted imidazonium salts, quaternary phosphonium salts having four alkyl groups such as tetrabutyl phosphonium, and tertiary sulfonium salts having three alkyl groups such as tributyl sulfonium.
  • the alkali metal may be lithium, sodium, potassium or cesium, with lithium, sodium or potassium being preferred. These can be used individually or in combination of 2 or more types.
  • OTf trifluoromethane sulfonate
  • OTs - toluene-4-sulfonate
  • OMs sulfonate
  • a sulfonylimide compound is preferable, and may be a compound of Formula 20 below.
  • M is an alkali metal
  • R is a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms.
  • the compound of Formula 20 has a high electronegativity of the fluorine atoms of the anion has a large stabilizing effect of the anion present in the nitrogen atom, improves the hydrophobicity of the antistatic agent, excellent compatibility with the acrylic copolymer and no surface transition, It is preferable at the point which gives antistatic property with durability.
  • the compound of Formula 20 is bis (fluorosulfonyl) imide potassium (KN (FSO 2 ) 2 ), bis (fluorosulfonyl) imide sodium (NaN (FSO 2 ) 2 ), bis (fluoro Sulfonyl) imide lithium (LiN (FSO 2 ) 2 ), bis (trifluoromethylsulfonyl) imide potassium (KN (CF 3 SO 2 ) 2 ), bis (trifluoromethylsulfonyl) imide sodium (NaN (CF 3 SO 2 ) 2 ) or bis (trifluoromethylsulfonyl) imide lithium (LiN (CF 3 SO 2 ) 2 ) and the like.
  • the content of the antistatic agent is not particularly limited as long as it is within the range of the function thereof, for example, may be included in 0.1 to 3 parts by weight relative to 100 parts by weight of the acrylic copolymer, preferably 0.5 to 1 part by weight.
  • the emission of iodine ion from a polarizer can be suppressed effectively, and the optical characteristic and durability of a polarizer can be improved remarkably.
  • the decrease in adhesion durability due to the bleed-out of the antistatic agent from the pressure-sensitive adhesive layer to the glass It can cause problems.
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention may further include a crosslinking agent and a silane coupling agent.
  • the said crosslinking agent is a component for strengthening the cohesion force of an adhesive by crosslinking a copolymer suitably,
  • the kind is not specifically limited.
  • an isocyanate type compound, an epoxy type compound, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • isocyanate compound tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalene Diisocyanate compounds such as diisocyanate; Diisocyanate obtained from 2 moles of an adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate obtained by self-condensing 3 moles of the diisocyanate compound, and 3 moles of the diisocyanate compound And polyfunctional isocyanate compounds containing three functional groups such as biuret, triphenylmethanetriisocyanate, and methylenebistriisocyanate, in which the remaining 1
  • Examples of the epoxy compound include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and polypropylene glycol.
  • melamine type compound can be used individually or in mixture of 2 or more types together with an isocyanate type compound and an epoxy type compound.
  • Hexamethylol melamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine, etc. are mentioned as a melamine type compound.
  • the crosslinking agent is preferably included in an amount of 0.1 to 15 parts by weight, and more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer based on the solid content. If the content is less than 0.1 part by weight, the cohesion force becomes small due to insufficient crosslinking degree, which may cause deterioration of durability and damage of cutting property. When the content is more than 15 parts by weight, problems may be caused in reducing residual stress due to excessive crosslinking reaction.
  • the silane coupling agent is added to improve the adhesion between the pressure-sensitive adhesive and the substrate, the kind is not particularly limited as long as it is within the range of the function, for example amino group, epoxy group, acetoacetyl group, Alkoxysilane containing functional groups, such as a polyalkylene glycol group, an acryl group, and an alkyl group, can be used.
  • the content of the silane coupling agent is not particularly limited, but is preferably included in an amount of 0.1 to 2.0 parts by weight, and more preferably 0.1 to 0.5 parts by weight based on 100 parts by weight of the acrylic copolymer based on the solid content.
  • the content is less than 0.1 parts by weight, peeling is likely to occur in the heat and moisture resistant conditions, and when it is more than 2.0 parts by weight, the peeling may occur in the heat resistant conditions.
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention in addition to the components described above, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc. required according to the use, tackifying resin, antioxidant, leveling agent, surface Additives such as lubricants, dyes, pigments, antifoaming agents, fillers, light stabilizers may be further included.
  • the pressure-sensitive adhesive composition comprising the above-described components is applied to the other surface of the surface to which the protective film of the polarizer is bonded to form a pressure-sensitive adhesive layer.
  • the coating method is not particularly limited as long as it is a method commonly used in the art, and for example, the surface of the polarizer protective film is bonded by a mayer bar coating method, gravure coating method, die coating method, dip coating method, spraying method, or the like.
  • coating to another surface is mentioned.
  • the thickness of the pressure-sensitive adhesive layer formed by the above method is not particularly limited, and may be, for example, 3 to 100 ⁇ m, and preferably 10 to 100 ⁇ m.
  • the ultra-thin polarizing plate of the present invention can be applied to any conventional liquid crystal display device, and specifically, a liquid crystal display device including a liquid crystal panel in which the polarizing plate on which the pressure-sensitive adhesive layer is laminated is bonded to at least one surface of a liquid crystal cell can be configured.
  • one embodiment of the present invention relates to a liquid crystal display device provided with the ultra-thin polarizing plate on at least one side of a liquid crystal cell.
  • n-butyl acrylate BA
  • MA methyl acrylate
  • 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to reflux and to facilitate temperature control.
  • 2 parts by weight of acrylic acid, 3 parts by weight of the compound of Formula 1 and 80 parts by weight of ethyl acetate solvent were added. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 62 °C.
  • AIBN azobisisobutyronitrile
  • n-butyl acrylate BA
  • MA methyl acrylate
  • 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to reflux and to facilitate temperature control.
  • Part by weight 2 parts by weight of acrylic acid, 3 parts by weight of the compound of Formula 4 and 80 parts by weight of ethyl acetate solvent were added. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 62 °C.
  • AIBN azobisisobutyronitrile
  • n-butyl acrylate BA
  • MA methyl acrylate
  • 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to reflux and to facilitate temperature control.
  • 5 parts by weight of the compound of Formula 9 and 80 parts by weight of ethyl acetate solvent were added.
  • purging nitrogen gas for 1 hour to remove oxygen it was maintained at 62 °C.
  • 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 6 hours to prepare an acrylic copolymer having a weight average molecular weight of 1.5 million or more.
  • AIBN azobisisobutyronitrile
  • n-butyl acrylate (BA) 95 parts by weight of n-butyl acrylate (BA), 5 parts by weight of the compound of Formula 7 and 100 parts by weight of ethyl acetate solvent were added to a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to reflux and to facilitate temperature control. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 62 °C. After homogenizing the mixture, 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 6 hours to prepare an acrylic copolymer having a weight average molecular weight of 1 million or more.
  • AIBN azobisisobutyronitrile
  • n-butyl acrylate (BA) 95 parts by weight of n-butyl acrylate (BA), 5 parts by weight of the compound of Formula 11 and 100 parts by weight of ethyl acetate solvent were added to a 1 L reactor equipped with a refrigeration device to allow nitrogen gas to reflux and to facilitate temperature control. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 62 °C. After homogenizing the mixture, 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 6 hours to prepare an acrylic copolymer having a weight average molecular weight of 1 million or more.
  • AIBN azobisisobutyronitrile
  • n-butyl acrylate BA
  • 2-hydroxyethyl acrylate 8 parts by weight of the compound of Formula 9
  • a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to be refluxed and to facilitate temperature control.
  • Part and 100 parts by weight of an ethyl acetate solvent were added.
  • 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 6 hours to prepare an acrylic copolymer having a weight average molecular weight of 1 million or more.
  • n-butyl acrylate BA
  • MA methyl acrylate
  • 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to reflux and to facilitate temperature control.
  • AIBN azobisisobutyronitrile
  • n-butyl acrylate BA
  • MA methyl acrylate
  • 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to facilitate nitrogen temperature reflux and temperature control.
  • 2 parts by weight of acrylic acid and 80 parts by weight of ethyl acetate solvent were added.
  • 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 6 hours to prepare an acrylic copolymer having a weight average molecular weight of 1.5 million or more.
  • Antistatic Agent B1 KFSI (bis (fluorosulfonyl) imide potassium)
  • Antistatic Agent B2 1-hexyl-4-methylpyridinium hexafluorophosphate
  • Crosslinking agent Coronate L (COR-L, Japan Polyurethane Industry)
  • Silane coupling agent KBM-403 (Shin-Etsu Corporation)
  • the polyvinyl alcohol resin film having a thickness of 75 ⁇ m and an average polymerization degree of about 2,400 and a saponification degree of 99.9 mol% or more were stretched about 1.5 times while immersing in 30 ° C pure water for 2 minutes. Then, the solution was stretched by about 2.0 times while immersing for 3 minutes in a dye bath containing an aqueous solution having a weight ratio of 0.01 / 1.0 / 100 of iodine / potassium iodide / water and having a temperature of 30 ° C. Then, the film was stretched about 2.0 times while immersing for 1 minute at 53 ° C.
  • An adhesive composition was prepared by adding 3 parts by weight of acetoacetyl group-modified polyvinyl alcohol resin (Cosenol Z200, Nippon Synthetic Chemical Co., Ltd.) and 0.3 parts by weight of glyoxalic crosslinking agent (SPM-01, Nippon Kyosoy) to 100 parts by weight of water. Then, 50 parts by weight of copper sulfate was added to 100 parts by weight of the adhesive composition to prepare an adhesive layer-forming composition.
  • acetoacetyl group-modified polyvinyl alcohol resin Cosenol Z200, Nippon Synthetic Chemical Co., Ltd.
  • SPM-01 glyoxalic crosslinking agent
  • Example 2 After applying the adhesive layer forming composition prepared in Example 1-2 to one side of the polarizer prepared in Example 1-1 so that the dry film thickness is 0.1 ⁇ m, a saponified acetylcellulose-based film (30cm ⁇ 20cm ) was bonded. The conjugate was dried at a temperature of 60 ° C. for 3 minutes to prepare a polarizing plate.
  • the pressure-sensitive adhesive composition prepared in Preparation Example 1 was applied on the other side of the polarizer with a protective film prepared in Example 1-3 so that the thickness after drying was 25 ⁇ m, and dried at 100 ° C. for 1 minute to form an adhesive layer. To prepare an ultra-thin polarizing plate.
  • the pressure-sensitive adhesive layer of the ultra-thin polarizing plate was bonded to the Corning glass and subjected to autoclave treatment, and then the bubbles and the peeling phenomenon were observed after standing at 80 ° C. for 300 hours.
  • the surface resistivity was measured 10 times at each of three points of the pressure-sensitive adhesive layer of the ultra-thin polarizing plate using a surface resistance measuring instrument (MCP-HT450, manufactured by Mitsubishi Chemical Co., Ltd.), and expressed as the average value (unit: ⁇ / ⁇ ).
  • ⁇ The surface resistivity of less than 5X10 10 1X10 10 or more
  • ⁇ surface resistivity of 5X10 10 or more but less than 1X10 11
  • the polarization degree was measured after leaving at 60 degreeC and 90RH% for 300 hours.
  • ⁇ : polarization degree is more than 95%
  • the ultra-thin polarizing plates of Examples 1 to 9 formed of a pressure-sensitive adhesive composition comprising an acrylic copolymer in which an ionic functional group according to the present invention is immobilized is an adhesive including an acrylic copolymer containing no ionic functional group.
  • the antistatic property and the heat resistance as well as the moisture resistance optical durability were remarkably excellent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention a trait : à une plaque de polarisation ultramince où un film protecteur est fixé à une surface d'un polariseur, une couche adhésive collante est formée sur la surface qui n'est pas celle à laquelle le film protecteur est fixé, et cette couche adhésive collante est constituée d'une composition adhésive collante qui contient un copolymère acrylique ayant un groupe fonctionnel ionique fixé dessus ; ainsi qu'à un dispositif d'affichage à cristaux liquides muni de cette plaque. La plaque de polarisation ultramince selon l'invention peut présenter d'excellentes propriétés antistatiques, ainsi que des caractéristiques optiques et une durabilité remarquables même dans des conditions difficiles telles qu'une température élevée et une forte humidité.
PCT/KR2015/006856 2014-07-11 2015-07-03 Plaque de polarisation ultramince, et dispositif d'affichage à cristaux liquides muni de cette plaque Ceased WO2016006875A1 (fr)

Applications Claiming Priority (2)

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KR10-2014-0087697 2014-07-11
KR1020140087697A KR20160007272A (ko) 2014-07-11 2014-07-11 초박형 편광판 및 이를 구비하는 액정표시장치

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KR102315005B1 (ko) * 2018-12-26 2021-10-19 동우 화인켐 주식회사 하드코팅 조성물 및 이를 이용한 하드코팅 필름
KR102609172B1 (ko) * 2021-01-13 2023-12-01 삼성에스디아이 주식회사 편광판용 점착 필름, 이를 포함하는 편광판 및 이를 포함하는 광학표시장치

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005325180A (ja) * 2004-05-12 2005-11-24 Denki Kagaku Kogyo Kk 粘着剤組成物及び粘着シート
KR20090016241A (ko) * 2007-08-10 2009-02-13 동우 화인켐 주식회사 점착제 조성물 및 이를 포함하는 편광판
KR20090101762A (ko) * 2008-03-24 2009-09-29 동우 화인켐 주식회사 초박형 편광판 및 이를 구비한 액정표시장치
KR20120132397A (ko) * 2011-05-26 2012-12-05 닛토덴코 가부시키가이샤 점착제층이 부착된 편광 필름 및 화상 표시 장치
KR101314401B1 (ko) * 2010-02-26 2013-10-04 주식회사 엘지화학 편광판

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005325180A (ja) * 2004-05-12 2005-11-24 Denki Kagaku Kogyo Kk 粘着剤組成物及び粘着シート
KR20090016241A (ko) * 2007-08-10 2009-02-13 동우 화인켐 주식회사 점착제 조성물 및 이를 포함하는 편광판
KR20090101762A (ko) * 2008-03-24 2009-09-29 동우 화인켐 주식회사 초박형 편광판 및 이를 구비한 액정표시장치
KR101314401B1 (ko) * 2010-02-26 2013-10-04 주식회사 엘지화학 편광판
KR20120132397A (ko) * 2011-05-26 2012-12-05 닛토덴코 가부시키가이샤 점착제층이 부착된 편광 필름 및 화상 표시 장치

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TW201606016A (zh) 2016-02-16

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