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WO2010002195A2 - Composition adhésive, plaque de polarisation et dispositif d'affichage à cristaux liquides - Google Patents

Composition adhésive, plaque de polarisation et dispositif d'affichage à cristaux liquides Download PDF

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Publication number
WO2010002195A2
WO2010002195A2 PCT/KR2009/003601 KR2009003601W WO2010002195A2 WO 2010002195 A2 WO2010002195 A2 WO 2010002195A2 KR 2009003601 W KR2009003601 W KR 2009003601W WO 2010002195 A2 WO2010002195 A2 WO 2010002195A2
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WO
WIPO (PCT)
Prior art keywords
formula
meth
acrylate
compound
sensitive adhesive
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/KR2009/003601
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English (en)
Korean (ko)
Other versions
WO2010002195A9 (fr
WO2010002195A3 (fr
Inventor
장기석
박민수
한인천
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
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Filing date
Publication date
Priority claimed from KR1020090021100A external-priority patent/KR20100003689A/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN200980125811.1A priority Critical patent/CN102083931B/zh
Priority to JP2011516148A priority patent/JP5582543B2/ja
Priority to US13/002,027 priority patent/US20110111140A1/en
Publication of WO2010002195A2 publication Critical patent/WO2010002195A2/fr
Publication of WO2010002195A3 publication Critical patent/WO2010002195A3/fr
Publication of WO2010002195A9 publication Critical patent/WO2010002195A9/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
    • 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
    • G02F1/133528—Polarisers
    • 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
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements

Definitions

  • the present invention relates to an adhesive composition, a polarizing plate and a liquid crystal display device.
  • a liquid crystal display is a device that displays a screen by inserting a liquid crystal between two glass substrates.
  • the molecular arrangement of the liquid crystal is changed, and accordingly, the transmittance of light passing through the liquid crystal is changed to display an image.
  • Such a liquid crystal display device is a display device that is currently in the spotlight in various fields because of the advantages of low power consumption and flatness.
  • a liquid crystal cell and a polarizing plate including a transparent substrate on which a liquid crystal and an electrode layer are formed are required, and an adhesive or pressure-sensitive adhesive for bonding them is required.
  • a functional film such as a retardation plate, a wide viewing angle compensation plate, or a brightness enhancement film may be additionally attached to the polarizing plate included in the liquid crystal display device.
  • each functional film constituting the multilayer polarizing plate is made of a material having a different molecular structure and composition, thereby exhibiting different physical properties. Accordingly, in particular, high temperature and / or high humidity conditions have a problem of poor dimensional stability depending on the difference in shrinkage and expansion behavior of the respective materials. Therefore, when the polarizing plate is fixed by an adhesive or the like, there is a problem that stress is concentrated under high temperature and / or high humidity conditions, birefringence occurs, and light leakage occurs.
  • Representative methods for solving such problems include a method of optimizing a design such as an adhesive for fixing a polarizing plate. For example, a method of softly designing an adhesive so as to easily deform with respect to external stress to impart stress relaxation characteristics or very hard design to suppress shrinkage of a polarizing plate according to an external environment is used.
  • Japanese Patent Application Laid-open No. Hei 10-279907 discloses a method of improving light leakage phenomenon by blending a relatively large molecular weight acrylic resin and a relatively small molecular weight acrylic resin to impart stress relaxation characteristics to the pressure-sensitive adhesive.
  • Korean Patent Laid-Open Publication No. 2003-0069461 discloses a method for compensating birefringence by blending a material exhibiting positive birefringence under a residual stress in an adhesive.
  • An object of this invention is to provide an adhesive composition, a polarizing plate, and a liquid crystal display device.
  • the present invention provides a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an acrylic resin having a weight average molecular weight of 800,000 to 2 million, and an optically anisotropic compound present in a liquid phase at room temperature.
  • the present invention is another means for solving the above problems, a polarizing film or a polarizing element;
  • the present invention provides another liquid crystal display device including a liquid crystal panel in which the polarizing plate according to the present invention is attached to one side or both sides of a liquid crystal cell.
  • a pressure-sensitive adhesive composition exhibiting excellent durability under high temperature or high humidity conditions, and excellent workability such as cutting property and re-peelability, and which can effectively suppress light leakage phenomenon generated in a liquid crystal display device, and its hardness
  • a polarizing plate and a liquid crystal display including a package are provided.
  • the present invention the acrylic resin having a weight average molecular weight of 800,000 to 2 million; And it relates to a pressure-sensitive adhesive composition comprising an optically anisotropic compound present in the liquid phase at room temperature.
  • the acrylic resin used in the present invention is designed to have a weight average molecular weight in the range of 800,000 to 2 million. If the weight average molecular weight of the acrylic resin contained in the pressure-sensitive adhesive composition is less than 800,000, there may be a problem in durability reliability due to the decrease in cohesion force, and in excess of 2 million, the stress relaxation property is lowered and the light leakage inhibitory effect may be lowered. There is.
  • acrylic resin which can be used by this invention is not specifically limited.
  • (meth) acrylic acid ester monomer 90 parts by weight to 99.9 parts by weight; And 0.1 to 10 parts by weight of the crosslinkable monomer.
  • acrylic resin containing an aromatic substituent can be used depending on a case.
  • Acrylic resin containing an aromatic substituent can be manufactured by copolymerizing an aromatic ring containing monomer with the above-mentioned conventional acrylic monomer.
  • acrylic monomers exhibit negative birefringence under residual stress, and when applied to optical parts such as polarizing plates, there is a fear of causing light leakage.
  • the aromatic ring-containing monomer is a compound that exhibits positive birefringence under residual stress, and can be optically compensated by appropriately copolymerizing it with an acrylic monomer.
  • the acrylic resin includes an aromatic substituent, for example, 55 parts by weight to 94.9 parts by weight of (meth) acrylic acid ester monomer; 5 parts by weight to 35 parts by weight of an aromatic ring-containing monomer; And 0.1 to 10 parts by weight of the crosslinkable monomer.
  • an aromatic substituent for example, 55 parts by weight to 94.9 parts by weight of (meth) acrylic acid ester monomer; 5 parts by weight to 35 parts by weight of an aromatic ring-containing monomer; And 0.1 to 10 parts by weight of the crosslinkable monomer.
  • the type of the (meth) acrylic acid ester monomer is not particularly limited, and alkyl (meth) acrylate can be used, for example.
  • alkyl (meth) acrylate can be used, for example.
  • T g glass transition temperature
  • adhesion may be difficult to be controlled, and thus (meth) having an alkyl group having 1 to 14 carbon atoms.
  • Preference is given to using acrylic ester monomers.
  • Examples of such monomers include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth ) Acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, n-octyl (meth) acrylate, iso Octyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate, isobornyl (meth) acrylate and tetradecyl (meth) acrylate.
  • the (meth) acrylic acid ester monomer as described above is included in the monomer mixture in an amount of 90 parts by weight to 99.9 parts by weight based on the content of the crosslinkable monomer; Or it is preferably included in the monomer mixture in an amount of 55 parts by weight to 94.9 parts by weight relative to the content of the crosslinkable functional group or the aromatic ring-containing monomer. If the content of the (meth) acrylic acid ester monomer is too small, there is a risk that the balance of adhesive physical properties is lowered. If the content of the (meth) acrylic acid ester monomer is too small, the negative birefringence may be too large under residual stress, resulting in light leakage.
  • the content of the (meth) acrylic acid ester monomer is only one example of the present invention, and in the present invention, whether or not an aromatic substituent is included in the polymer and its kind;
  • the physical properties of the monomers can be appropriately controlled in consideration of the content of the optically anisotropic compound and the kind thereof.
  • the kind of the aromatic ring-containing monomer included in the monomer mixture of the present invention is also not particularly limited, and for example, a (meth) acrylate monomer containing an aromatic ring can be used. More specific examples of such monomers include compounds represented by the following general formula (1).
  • R 1 represents hydrogen or alkyl
  • A represents alkylene, alkenylene or alkynylene
  • n represents an integer of 0 to 3
  • Q is a single bond, -O-, -S-, alkyl Lene, alkenylene or alkynylene
  • P represents an aromatic ring.
  • single bond means a case where both groups of atoms are directly bonded to each other without a separate atom.
  • R 1 may be preferably hydrogen or alkyl having 1 to 4 carbon atoms, more preferably hydrogen, methyl or ethyl.
  • A may be alkylene having 1 to 12, preferably 1 to 8 carbon atoms, more preferably methylene, ethylene, hexylene or octylene.
  • alkenylene or alkynylene may be alkenylene or alkynylene having 2 to 12, preferably 2 to 8, more preferably 2 to 4 carbon atoms, specifically, ethenylene , Ethynylene, propenylene or propynylene.
  • n is preferably an integer of 0 to 2, more preferably 0 or 1.
  • Q may preferably be a single bond, -O- or S-.
  • P is a substituent derived from an aromatic compound, preferably an aromatic ring having 6 to 20 carbon atoms, more preferably phenyl, biphenyl, naphthyl or anthracenyl, more preferably Preferably phenyl.
  • the aromatic ring may be optionally substituted with one or more substituents, and specific examples of the substituents may be halogen or alkyl, preferably halogen or alkyl having 1 to 12 carbon atoms, more preferably. Include, but are not limited to, chlorine, bromine, methyl, ethyl, propyl, butyl, nonyl or dodecyl.
  • the compound of Formula 1 include phenoxy ethyl (meth) acrylate, benzyl (meth) acrylate, 2-phenylthio-1-ethyl (meth) acrylate, 6- (4,6-dibro) Mo-2-isopropylphenoxy) -1-hexyl (meth) acrylate, 6- (4,6-dibromo-2-sec-butyl phenoxy) -1-hexyl (meth) acrylate, 2, 6-dibromo-4-nonylphenyl (meth) acrylate, 2,6-dibromo-4-dodecylphenyl (meth) acrylate, 2- (1-naphthyloxy) -1-ethyl (meth ) Acrylate, 2- (2-naphthyloxy) -1-ethyl (meth) acrylate, 6- (1-naphthyloxy) -1-hexyl (meth)
  • the aromatic ring-containing monomer may be included in the monomer mixture in an amount of 5 parts by weight to 35 parts by weight based on the content of the (meth) acrylic acid ester monomer or the crosslinkable monomer.
  • the content is less than 5 parts by weight, the optical compensation effect due to the addition of the monomer may be insignificant.
  • the content is more than 35 parts by weight, physical properties such as adhesive properties or re-peelability may be lowered, or in some cases, optical compensation effects. May rather deteriorate.
  • the content of the monomer is only one example of the present invention, and in the present invention, the content of the monomer can be appropriately controlled in consideration of the content and type of the optically anisotropic compound.
  • the crosslinkable monomer included in the monomer mixture may impart cohesive force to the pressure-sensitive adhesive by reacting with the polyfunctional crosslinking agent described below, and impart a crosslinkable functional group capable of adjusting the adhesive force, durability, and the like to the polymer.
  • crosslinkable monomers include hydroxy group-containing monomers, carboxyl group-containing monomers and nitrogen-containing monomers.
  • Examples of the hydroxy group-containing monomers above include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) Acrylate, 8-hydroxyoctyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate or 2-hydroxypropylene glycol (meth) acrylate, and examples of the carboxyl group-containing monomer are acrylic acid.
  • Methacrylic acid 2- (meth) acryloyloxy acetic acid, 3- (meth) acryloyloxy propyl acid, 4- (meth) acryloyloxy butyl acid, acrylic acid duplex, itaconic acid, maleic acid and Maleic anhydride, and examples of the nitrogen-containing monomer include (meth) acrylamide, N-vinyl pyrrolidone or N-vinylcaprolactam, but are not limited thereto. In the present invention, a mixture of one or more of the above can be used.
  • the crosslinkable monomer may be included in the monomer mixture in an amount of 0.1 parts by weight to 10 parts by weight based on the content of the aforementioned (meth) acrylic acid ester monomer or an aromatic ring-containing monomer. If the content is less than 0.1 part by weight, the durability reliability of the pressure-sensitive adhesive may be lowered. If it exceeds 10 parts by weight, the adhesiveness and / or peeling force may be lowered.
  • the monomer mixture may further include a monomer represented by the following formula (2).
  • Such monomers may be added for the purpose of controlling the glass transition temperature of the pressure-sensitive adhesive and providing other functionalities.
  • R 2 to R 4 each independently represent hydrogen or alkyl, and R 5 represents cyano; Phenyl unsubstituted or substituted with alkyl; Acetyloxy; Or COR 6 , wherein R 6 represents amino or glycidyloxy unsubstituted or substituted with alkyl or alkoxyalkyl.
  • Alkyl or alkoxy in the definition of R 2 to R 6 in the formula may mean alkyl or alkoxy having 1 to 12 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 12 carbon atoms, and specifically methyl , Ethyl, methoxy, ethoxy, propoxy or butoxy.
  • the monomer of the formula (2) include nitrogen-containing monomers such as (meth) acrylonitrile, (meth) acrylamide, N-methyl (meth) acrylamide or N-butoxy methyl (meth) acrylamide; Styrene-based monomers such as styrene or methyl styrene; Epoxy group-containing monomers such as glycidyl (meth) acrylate; Or carboxylic acid vinyl esters such as vinyl acetate, or the like, or two or more kinds thereof, but are not limited thereto.
  • Such monomers may be included in the monomer mixture in an amount of 20 parts by weight or less relative to the content of the aforementioned (meth) acrylic acid ester monomer or crosslinkable monomer. When the content exceeds 20 parts by weight, there is a fear that the flexibility and peeling strength of the pressure-sensitive adhesive is lowered.
  • a method of preparing a polymer using the monomer mixture as described above is not particularly limited, and may be prepared through a general polymerization method such as solution polymerization, photopolymerization, bulk polymerization, suspension polymerization or emulsion polymerization.
  • a solution polymerization method it is particularly preferable to use a solution polymerization method, and solution polymerization is preferably performed at a polymerization temperature of 50 ° C to 140 ° C by mixing an initiator in a state where each monomer is uniformly mixed.
  • Initiators which can be used at this time include azo polymerization initiators such as azobis isobutyronitrile or azobiscyclohexane carbonitrile; And / or conventional initiators such as peroxides such as benzoyl peroxide or acetyl peroxide.
  • azo polymerization initiators such as azobis isobutyronitrile or azobiscyclohexane carbonitrile
  • initiators such as peroxides such as benzoyl peroxide or acetyl peroxide.
  • the adhesive composition of this invention exists in a liquid state at normal temperature, and contains the compound which has optical anisotropy.
  • an optically anisotropic compound having a melting point below room temperature and present in a liquid phase at room temperature and including a mesogen core in a molecular structure can be used.
  • room temperature means a temperature as it is, not a temperature rising or temperature decreasing state, for example, about 15 ° C to 30 ° C, preferably about 20 ° C to 30 ° C, and more preferably about 25 ° C. It can mean the temperature of.
  • mesogen is a component that is typically included in a liquid crystal compound to form a rigid part.
  • two or more benzene rings may be directly connected to each other, in some cases may be connected via another atom or group of atoms.
  • the term benzene ring used above is a concept containing not only benzene but its derivative (s).
  • the mesogen core may refer to a structure including three or more core structures preferably selected from biphenyl, toluene and benzene rings.
  • Such a mesogen core can align the compound in a certain direction with respect to external stimuli such as shrinkage of the polarizing plate, for example, and can exhibit positive birefringence properties as a whole. Accordingly, the optically anisotropic compound according to the present invention can exhibit an effect of optically compensating negative birefringence caused by, for example, shrinkage of the polarizing plate.
  • the said optically anisotropic compound used by this invention can also exhibit the effect of providing moderate softness
  • the optically anisotropic compound as described above has high crystallinity, poor compatibility with the polymer, and precipitates as crystals or phase separation occurs even when a very small amount is used.
  • the refractive index may be in the range of 1.49 to 1.60, preferably 1.50 to 1.55.
  • the pressure-sensitive adhesive has an excellent transmittance and has an effect of suppressing generation of haze.
  • the refractive index can be measured using an Abbe refractometer, and specifically, can be measured by irradiating sodium D-ray at 25 ° C.
  • optically anisotropic compound that can be used in the present invention is not particularly limited as long as it satisfies the above-described physical properties, and may be, for example, a compound represented by the following Chemical Formula 3.
  • Z is C-W or N
  • R 7 is hydrogen, alkyl, alkenyl, alkynyl or — (R 8 O) q R 9 ;
  • R 8 is alkylene, R 9 is alkyl, q is an integer from 1 to 5;
  • l, m, n and o are each independently an integer of 0 to 2, and l + m + n + o is an integer of 2 or more;
  • G 1 , G 2 , and G 3 are each independently a single bond, -O-, -R 8 O-, -NR 8- , -S-, -SO-, -SO 2- , alkylene, alkenylene, Alkynylene or -UTV-;
  • U and T are each independently a single bond, -S-, -NR 8- , -O (CH 2 ) p- , carbonyl or -O-,
  • V is a single bond, -O-, carbonyl,- NR 8- , -S-,-(CH 2 ) p- , -O (CH 2 ) p- , or-(CH 2 ) p O-, and p is an integer from 0 to 5.
  • alkyl or alkylene may be alkyl or alkylene 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
  • alkenyl, alkenylene, Alkynyl or alkynylene may be alkenyl, alkenylene, alkynyl or alkynylene having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms.
  • alkyl, alkylene, alkenyl, alkenylene, alkynyl or alkynylene is hydroxy; Cyano; Halogen, preferably chlorine or bromine; Alkyl having 1 to 12 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms; Alkoxy having 1 to 12, preferably 1 to 8, more preferably 1 to 4 carbon atoms; Alkynyl having 2 to 12 carbon atoms, preferably 2 to 8 carbon atoms, more preferably 2 to 4 carbon atoms; Or alkenyl having 2 to 12 carbon atoms, preferably 2 to 8 carbon atoms, and more preferably 2 to 4 carbon atoms.
  • single bond means a case where both groups of atoms are directly bonded to each other without a separate atom.
  • l, m, n and o preferably l, m and o is 1, n is 0, or l and o is 1, m and n may be 0 have.
  • E and F may preferably be silyl substituted with hydrogen, cyano, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or alkyl group of 1 to 8 carbon atoms, and Preferably, it may be hydrogen, cyano, propyl, hexyl or hexyl dimethyl silyl.
  • R 7 may be alkyl of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms.
  • G 2 and G 3 is preferably each independently a single bond, alkylene having 1 to 4 carbon atoms, alkenylene having 2 to 4 carbon atoms or alkynylene having 2 to 4 carbon atoms, And more preferably each independently may be a single bond, ethenylene, propenylene, ethynylene or protinylene.
  • E and F are hydrogen, cyano, ethyl, propyl, isopropyl, pentyl, hexyl, ethoxy, propoxy, pentoxy, hexyloxy, trimethyl silyl, trihexyl silyl or hexyl dimethyl silyl,
  • Z is CW or N
  • W is hydrogen, -R 7 or -OR 7 ,
  • R 7 is alkyl having 1 to 12 carbons or alkenyl having 2 to 12 carbons
  • G 2 and G 3 may each independently be a single bond, ethenylene, propenylene, ethynylene or protinylene.
  • the compound of Formula 4 is more preferably,
  • E and F are hydrogen, cyano, ethyl, propyl, isopropyl, pentyl, hexyl, ethoxy, propoxy, pentoxy, hexyloxy, trimethyl silyl, trihexyl silyl or hexyl dimethyl silyl,
  • W is hydrogen, -R 7 or -OR 7 , R 7 is alkyl of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms,
  • G 2 and G 3 may each independently be a single bond, ethenylene, propenylene, ethynylene or protinylene.
  • E is hydrogen
  • F is hydrogen, cyano, ethyl, propyl, isopropyl, pentyl, hexyl, ethoxy, propoxy, pentoxy, hexyloxy, trimethyl silyl, trihexyl silyl or hexyl dimethyl silyl,
  • W is hydrogen, -R 7 or -OR 7 , R 7 is alkyl of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms,
  • G 2 and G 3 may each independently be a single bond, ethenylene, propenylene, ethynylene or protinylene.
  • the compound of Formula 4 is more preferably,
  • W is hydrogen, -R 7 or -OR 7 , R 7 is alkyl of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms,
  • G 2 and G 3 may each independently be a single bond, ethenylene, propenylene, ethynylene or protinylene.
  • the optically anisotropic compound also preferably has one or more substituents in the meta position of mesogen.
  • the term "meta position of mesogen" as used above means at least one meta position of the benzene rings constituting the mesogen core, and preferably the meta position of the benzene ring existing at the terminal of the benzene rings constituting the mesogen core. Means.
  • the kind of the substituent present in the meta position of the mesogen is not particularly limited, and may include, for example, one or more selected from the group consisting of alkyl, alkenyl and alkynyl.
  • Q 1 , Q 2 , Q 14 , Q 15 and W may each independently be a substituent as described above or a preferable substituent among the aforementioned substituents, and more preferably alkyl, alkenyl or alkynyl of the substituents. It may be a substituent containing.
  • one or more of the compounds represented by the following Chemical Formulas 4 to 24 may be specifically used as the optically anisotropic compound of Chemical Formula 3.
  • the optically anisotropic compound as described above is preferably included in an amount of 5 parts by weight to 30 parts by weight with respect to 100 parts by weight of the acrylic resin. If the content is less than 5 parts by weight, there is a fear that the optical compensation effect is lowered, if it exceeds 30 parts by weight, there is a fear that the problem of compatibility with the adhesive resin decreases.
  • the content of the optically anisotropic compound is only one example of the present invention, in the present invention, in consideration of the type of optically anisotropic compound used, the desired optical compensation and stress relaxation effect, the content of the optically anisotropic compound It can be adjusted appropriately.
  • the pressure-sensitive adhesive composition of the present invention may further include 0.01 to 10 parts by weight of the crosslinking agent based on 100 parts by weight of the acrylic resin.
  • a crosslinking agent may impart cohesion to the pressure-sensitive adhesive through a reaction with an acrylic resin.
  • crosslinking agent used at this time is not specifically limited,
  • general crosslinking agents such as an isocyanate type compound, an epoxy type compound, an aziridine type compound, and a metal chelate type compound, can be used.
  • isocyanate compound examples include tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoborone diisocyanate, tetramethylxylene diisocyanate, naphthalene diisocyanate and the above.
  • Trimethylol propane Trimethylol propane
  • the epoxy compound include ethylene glycol diglycidyl ether, triglycidyl ether, trimethylolpropane triglycidyl ether, N, N, N'N'-tetraglycidyl ethylenediamine and glycerin diglycidyl ether.
  • aziridine compound include N, N-toluene-2,4-bis (1-aziridinecarboxamide), N, N'-diphenylmethane-4,4'-bis (1-aziridinecarbox Mid), triethylene melamine, bisisoprotaloyl-1- (2-methylaziridine), and tri-1-aziridinylphosphine oxide.
  • the metal chelate compound a compound in which a polyvalent metal such as aluminum, iron, zinc, tin, titanium, antimony, magnesium, and / or vanadium is coordinated with acetyl acetone, ethyl acetoacetate, or the like may be used. It is not limited to this.
  • the crosslinking agent is preferably included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the acrylic resin described above. If the content is less than 0.01 part by weight, the cohesive force of the pressure-sensitive adhesive may be lowered. If the content is more than 10 parts by weight, the durability may be lowered such as delamination or lifting.
  • the pressure-sensitive adhesive composition of the present invention may further include 0.005 parts by weight to 5 middle parts of a silane coupling agent, based on 100 parts by weight of the acrylic resin, in addition to the aforementioned components.
  • the silane coupling agent may contribute to the improvement of adhesion reliability when the pressure-sensitive adhesive is left for a long time under high temperature or high humidity conditions, and in particular, may improve the adhesion stability at the time of adhesion with the glass substrate to improve heat resistance and moisture resistance.
  • the silane coupling agent is preferably included in an amount of 0.005 parts by weight to 5 parts by weight, and more preferably 0.05 part by weight to 1 part by weight based on 100 parts by weight of the acrylic resin. If the content is less than 0.005 parts by weight, the effect of increasing the adhesion may be insignificant. If the content is more than 5 parts by weight, the durability may be lowered, such as bubble or peeling phenomenon.
  • the pressure-sensitive adhesive composition of the present invention may further include 1 part by weight to 100 parts by weight of a tackifying resin with respect to 100 parts by weight of the acrylic resin from the viewpoint of controlling the adhesive performance.
  • a tackifying resin is not specifically limited, For example, (hydrogenated) hydrocarbon type resin, (hydrogenated) rosin resin, (hydrogenated) rosin ester resin, (hydrogenated) terpene resin, (hydrogenated) terpene phenol resin, One kind or a mixture of two or more kinds of a polymeric rosin resin or a polymeric rosin ester resin can be used. If the content of the tackifying resin is less than 1 part by weight, the effect of addition may be insignificant. If it exceeds 100 parts by weight, the compatibility and / or cohesion improvement effect may be lowered.
  • the pressure-sensitive adhesive composition of the present invention may also include an initiator such as a thermal initiator or a photoinitiator in a range that does not affect the effect of the invention; Epoxy resins; Curing agent; Ultraviolet stabilizers; Antioxidants; Colorant; Adjuvant; Fillers; Antifoam; Surfactants; Photopolymerizable compounds such as polyfunctional acrylates; And one or more additives selected from the group consisting of plasticizers.
  • the present invention also provides a polarizing film or polarizing element; And a pressure-sensitive adhesive layer formed on one or both surfaces of the polarizing film or the polarizing element and containing a cured product of the pressure-sensitive adhesive composition according to the present invention.
  • the kind of polarizing film or polarizing element which comprises the polarizing plate (or adhesive polarizing plate) of this invention is not specifically limited.
  • stretching polarizing components such as an iodine or a dichroic dye, can be used for the film which consists of polyvinyl alcohol-type resin as said polarizing film or element, for example.
  • polyvinyl alcohol-based resin polyvinyl alcohol, polyvinyl formal, polyvinyl acetal or saponified product of ethylene vinyl acetate copolymer may be used.
  • the thickness of the polarizing film or element is not particularly limited, and may be formed in a conventional thickness.
  • the pressure-sensitive adhesive polarizing plate of the present invention also comprises a cellulose-based film such as triacetyl cellulose on one side or both sides of the polarizing film or element; Polyester film such as polycarbonate film or polyethylene terephthalate film; Polyether sulfone-based film; And / or a protective film such as a polyethylene film, a polypropylene film, or a polyolefin film having a cyclo or norbornene structure or a polyolefin film such as an ethylene propylene copolymer.
  • the thickness of the protective film is not particularly limited, and may be formed to a conventional thickness.
  • the method of forming the adhesive layer on the polarizing film or the device as described above is not particularly limited, and for example, the pressure-sensitive adhesive composition or the coating liquid containing the above by the conventional means such as a bar coater on the film or device.
  • a method of coating, drying and aging, or a method of applying the pressure-sensitive adhesive to the surface of the peelable substrate and drying it, and then transferring the adhesive layer onto a polarizing film or an element using the peelable substrate and then curing and curing may be used. have.
  • the crosslinking agent is preferably controlled from the viewpoint of uniform coating to prevent the crosslinking reaction of the functional group from proceeding when the pressure-sensitive adhesive layer is formed.
  • the crosslinking agent may form a crosslinked structure in the drying and aging process after the coating operation to improve cohesion, and improve adhesive properties and cuttability of the product.
  • the pressure-sensitive adhesive layer forming process is also preferably carried out after sufficiently removing the bubble-inducing components such as volatile components or reaction residues in the pressure-sensitive adhesive composition or coating solution. That is, if the crosslinking density or molecular weight is too low to decrease the elastic modulus, there is a fear that small bubbles existing between the glass plate and the pressure-sensitive adhesive layer in the high temperature state become large to form scatterers therein.
  • the polarizing plate of the present invention may further include at least one functional layer selected from the group consisting of a protective layer, a reflective layer, an antiglare layer, a retardation plate, a wide viewing angle compensation film, and a brightness enhancing film.
  • the present invention also relates to a liquid crystal display device comprising a liquid crystal panel in which the aforementioned polarizing plate according to the present invention is bonded to one side or both sides of a liquid crystal cell.
  • the type of liquid crystal cell constituting the liquid crystal display device of the present invention as described above is not particularly limited, such as TN (Twisted Neumatic), STN (Super Twisted Neumatic), IPS (In Plane Switching) or VA (Vertical Alignment) method It includes all common liquid crystal cells.
  • the kind and other manufacturing method of the other structure contained in the liquid crystal display device of this invention are not specifically limited, either, The general structure of this field can be employ
  • n-BA n-butyl acrylate
  • BzA benzyl acrylate
  • 2-hydroxyethyl methacryl in a 1 L reactor equipped with a refrigeration system for easy control of nitrogen gas and refrigeration.
  • a mixture of monomers containing 2 parts by weight of rate (2-HEMA) was added.
  • 120 parts by weight of ethyl acetate (EAc) was added as a solvent, and purged with nitrogen gas for 60 minutes to remove oxygen.
  • the optically anisotropic compound (A) was prepared through the process as shown in the above scheme. Specifically, Compound (1) was dissolved in a DMF solvent, and 1.2 equivalents of Compound (2) and 1.5 equivalents of K 2 CO 3 were combined based on Compound (1), followed by stirring at 100 ° C. for 4 hours. . The reaction was then worked up using ether and water and purified by silica gel to give compound 3 (yield: 87%).
  • Compound (12) was dissolved in butanone, and 1.2 equivalent of hexyl bromide and 1.2 equivalent of K 2 CO 3 were further added to 1.0 equivalent of Compound (12), followed by stirring at 80 ° C. for about 5 hours. Then work up with ether and purify with silica gel to give compound (13) in about 90% yield. Subsequently, Compound (13) is dissolved in a benzene solvent with 1.0 equivalent of Compound (14) relative to 1.0 equivalent of Compound (13), NiCl 2 (pph 3 ) 2 is added as a catalyst, and the mixture is stirred at room temperature for about 2 hours. It was. Then work-up with water and ether and purification with silica gel gave compound (15) in about 70% yield.
  • Compound (16) was dissolved in THF, and 1.0 equivalent of tert-butyldimethylsilyl chloride (TBSCl) and 1.2 equivalent of imidazole were added to 1.0 equivalent of Compound (16), followed by 5 hours at 80 ° C. Stirred. The resulting salt was then filtered off and purified by silica gel to yield compound (17) in about 80% yield.
  • Compound (17) was dissolved in butanone, and 1.2 equivalent of hexyl bromide and 1.2 equivalent of K 2 CO 3 were further added to 1.0 equivalent of Compound (17), followed by stirring at 80 ° C for about 10 hours. Then work up with ether and purify with silica gel.
  • the purified product was dissolved in THF and deprotected by combining 1.1 equivalent of Tetra-n-butylammonium fluoride (TBAF) relative to 1.0 equivalent of the purified product. Thereafter, the mixture was stirred at room temperature for about 1 hour, worked up with ether, and then purified by silica gel to obtain compound (18). Subsequently, Compound (18) was dissolved in 1.0 equivalent of Compound (19) to 1.0 equivalent of Compound (18) and CH 2 Cl 2 , 1.2 equivalents of EDC and 0.1 equivalent of DMAP were combined, followed by stirring at room temperature for about 10 hours. It was. Then work up with CH 2 Cl 2 and purify with silica gel to give compound 20 in about 85% yield.
  • TBAF Tetra-n-butylammonium fluoride
  • Compound (21) was dissolved in butanone, 1.2 equivalents of butyl bromide and 1.2 equivalents of K 2 CO 3 were combined with 1.0 equivalent of Compound (21), followed by stirring at 80 ° C for about 5 hours. Work-up with ether and water and purification with silica gel gave compound 22 in about 95% yield.
  • Compound (22) was then dissolved in 1.0 equivalent of trimethylsilyl acetylene, 0.1 equivalent of CuI, 0.03 equivalent of PdCl 2 (PPh 3 ) 2 and 4.0 equivalent of triethylamine and benzene relative to compound (22), at 60 ° C. Stir for about 10 hours.
  • Examples 2 to 28 were prepared in the same manner as in Example 1, except that compositions of acrylic resins, optically anisotropic compounds, and the like were changed as shown in Tables 2 to 5 below.
  • Comparative Examples 1 to 4 were prepared in the same manner as in Example 1, except that the composition of the pressure-sensitive adhesive composition was changed as in Table 6 below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)

Abstract

L'invention concerne une composition adhésive, une plaque de polarisation et un dispositif d'affichage à cristaux liquides. La composition adhésive selon l'invention possède une durabilité et une fiabilité excellentes dans des conditions de température ou d'humidité élevées, une ouvrabilité améliorée lors des processus de découpe ou de pelage répété et elle permet, en particulier, de supprimer de manière efficace les infiltrations de lumière dans un dispositif d'affichage à cristaux liquides. La plaque de polarisation contient un matériau durci à partir de la composition adhésive.
PCT/KR2009/003601 2008-07-01 2009-07-01 Composition adhésive, plaque de polarisation et dispositif d'affichage à cristaux liquides Ceased WO2010002195A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN200980125811.1A CN102083931B (zh) 2008-07-01 2009-07-01 压敏粘合剂组合物、偏振片和液晶显示器
JP2011516148A JP5582543B2 (ja) 2008-07-01 2009-07-01 粘着剤組成物、偏光板及び液晶表示装置
US13/002,027 US20110111140A1 (en) 2008-07-01 2009-07-01 Adhesive composition, polarizing plate, and liquid crystal display

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2008-0063383 2008-07-01
KR20080063383 2008-07-01
KR1020090021100A KR20100003689A (ko) 2008-07-01 2009-03-12 점착제 조성물, 이를 포함하는 편광판 및 액정표시장치
KR10-2009-0021100 2009-03-12

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WO2010002195A9 WO2010002195A9 (fr) 2010-07-29

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CN101921184A (zh) * 2010-06-04 2010-12-22 深圳市有为化学技术有限公司 多官能团型芳香酮类化合物及含有该化合物的光引发剂
CN103184019A (zh) * 2011-12-29 2013-07-03 第一毛织株式会社 用于偏振板的粘合剂、包括粘合剂层的偏振板和光学元件

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JPH09302070A (ja) * 1996-05-20 1997-11-25 Sumitomo Metal Ind Ltd 熱硬化性エポキシ樹脂組成物とその用途および硬化剤
JP4227680B2 (ja) * 1998-06-05 2009-02-18 新日本石油株式会社 液晶フィルムおよびその製造方法
KR100431441B1 (ko) * 2000-12-21 2004-05-14 주식회사 엘지화학 편광판용 아크릴계 점착제 조성물 및 이를 적용한 편광판
JP2002194303A (ja) * 2000-12-27 2002-07-10 Sumitomo Chem Co Ltd 表面離型性粘着フィルム
WO2003095579A1 (fr) * 2002-05-13 2003-11-20 Jsr Corporation Composition et procede pour la fixation termporaire de solides
TWI309726B (en) * 2002-12-16 2009-05-11 Fujifilm Corp Optical compensating sheet, production method thereof, optical film, and polarizing plate and liquid crystal display device using the same
TWI488933B (zh) * 2008-02-01 2015-06-21 Lg Chemical Ltd 含有光學各向異性化合物之丙烯酸系壓感性黏著劑組合物、偏光板、及含彼之液晶顯示裝置
KR101133064B1 (ko) * 2008-04-25 2012-04-04 주식회사 엘지화학 아크릴계 점착제 조성물, 이를 포함하는 편광판 및액정표시장치

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101921184A (zh) * 2010-06-04 2010-12-22 深圳市有为化学技术有限公司 多官能团型芳香酮类化合物及含有该化合物的光引发剂
CN103184019A (zh) * 2011-12-29 2013-07-03 第一毛织株式会社 用于偏振板的粘合剂、包括粘合剂层的偏振板和光学元件
US9097855B2 (en) 2011-12-29 2015-08-04 Cheil Industries, Inc. Adhesive, polarizing plate including an adhesive layer prepared from the adhesive, and optical member including the polarizing plate
TWI506109B (zh) * 2011-12-29 2015-11-01 Cheil Ind Inc 用於偏振板的黏合劑、包括黏合劑層的偏振板和光學元件

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WO2010002195A3 (fr) 2010-04-22

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