WO2013024768A1 - Agent d'étanchéité pour élément d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé - Google Patents

Agent d'étanchéité pour élément d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé Download PDF

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WO2013024768A1
WO2013024768A1 PCT/JP2012/070223 JP2012070223W WO2013024768A1 WO 2013024768 A1 WO2013024768 A1 WO 2013024768A1 JP 2012070223 W JP2012070223 W JP 2012070223W WO 2013024768 A1 WO2013024768 A1 WO 2013024768A1
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meth
group
liquid crystal
crystal display
acrylate
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PCT/JP2012/070223
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English (en)
Japanese (ja)
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雄一 尾山
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積水化学工業株式会社
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Priority to JP2012540184A priority Critical patent/JP5281204B1/ja
Priority to KR1020137018537A priority patent/KR101953925B1/ko
Priority to CN201280011440.6A priority patent/CN103430086B/zh
Priority to KR1020137018415A priority patent/KR101357327B1/ko
Publication of WO2013024768A1 publication Critical patent/WO2013024768A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C09J163/10—Epoxy resins modified by unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
    • C08G59/1461—Unsaturated monoacids
    • C08G59/1466—Acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/265—Calcium, strontium or barium carbonate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0625—Polyacrylic esters or derivatives thereof
    • 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
    • G02F1/1339—Gaskets; Spacers; Sealing of cells

Definitions

  • the present invention relates to a sealing agent for a liquid crystal display element which is excellent in adhesion to an alignment film and hardly generates liquid crystal contamination.
  • the present invention also relates to a liquid crystal display element formed using the sealing agent for a liquid crystal display element.
  • the liquid crystal display element has a liquid crystal cell in which liquid crystal is sealed in a cell formed by applying a sealing agent to two substrates and bonding them.
  • a liquid crystal display cell two transparent substrates with electrodes are opposed at a predetermined interval, the periphery is sealed with a sealing agent to form a cell, and a liquid crystal injection port provided in a part of the cell is used in the cell. Liquid crystal is injected into the liquid crystal, and the liquid crystal injection port is sealed by using a sealing agent or a sealing agent.
  • a method of manufacturing a liquid crystal display element called a dropping method using a photo-setting / curing combination-type sealing agent as disclosed in Patent Document 1 has also been studied.
  • the dropping method first, a frame-like seal pattern is formed on one of the two transparent substrates with electrodes. Next, small droplets of liquid crystal are dropped and applied to the entire surface of the seal pattern frame of the transparent substrate in a non-cured state of the sealing agent, the other transparent substrate is superposed under reduced pressure, and ultraviolet rays are irradiated to the seal portion to perform temporary curing. . Thereafter, heating is carried out to carry out main curing to produce a liquid crystal display element.
  • the arrangement position of the sealing agent is mostly on an inorganic material such as glass or ITO, and the sealing agent is also designed in consideration of the adhesion to these inorganic materials.
  • the narrowing of the frame of liquid crystal display parts has progressed, and substrates in which a sealing agent is disposed on an alignment film are rapidly spreading. There is a problem that the adhesion to the film is insufficient.
  • the present invention is a curable resin having a (meth) acrylic group, a curing agent, surface-treated hydrotalcite, surface-treated calcium carbonate, fine particles of polyimide, fine particles of nitrile butadiene rubber, 3-alkoxysilylpropylsuccinic anhydride, Characterized by containing at least one selected from the group consisting of a compound represented by the formula (1), a compound represented by the following formula (2), and a compound represented by the following formula (3) Liquid crystal display element sealing agent.
  • R 1 represents a methyl group, a methoxy group or an ethoxy group
  • R 2 and R 3 represent a methoxy group or an ethoxy group
  • R 4 represents a methyl group, a methoxy group or an ethoxy group
  • R 5 and R 6 represent a methoxy group or an ethoxy group
  • R 7 represents a methoxy group or an ethoxy group.
  • the present inventor provides surface-treated hydrotalcite, surface-treated calcium carbonate, polyimide fine particles, nitrile butadiene rubber fine particles, a compound represented by the above formula (1), a compound represented by the above formula (2), and the above formula
  • surface-treated hydrotalcite surface-treated calcium carbonate
  • polyimide fine particles polyimide fine particles
  • nitrile butadiene rubber fine particles a compound represented by the above formula (1)
  • compound represented by the above formula (2) nitrile butadiene rubber fine particles
  • a compound represented by the above formula (1) a compound represented by the above formula (2)
  • the above formula By using at least one selected from the group consisting of compounds represented by (3), it is found that the adhesion of the obtained sealing agent for a liquid crystal display element to the alignment film can be remarkably improved, and the present invention It came to complete.
  • the sealing agent for a liquid crystal display element of the present invention is represented by surface-treated hydrotalcite, surface-treated calcium carbonate, polyimide fine particles, nitrile butadiene rubber fine particles, a compound represented by the above formula (1), and the above formula (2) It contains at least one selected from the group consisting of a compound and a compound represented by the above formula (3).
  • the sealing agent for a liquid crystal display element of the present invention has excellent adhesion to an alignment film by containing at least one selected from the group consisting of the following compounds.
  • the surface-treated hydrotalcite is obtained by surface-treating hydrotalcite.
  • Examples of the surface treatment to be applied to the hydrotalcite include fatty acid treatment and silane coupling agent treatment. Among them, hydrophobic treatment is preferred.
  • Examples of surface treatment agents used for surface treatment of the above hydrotalcite include fatty acids such as stearic acid, oleic acid and linoleic acid, dimethyldimethoxysilane, dimethyldiexisilane, methyltrimethoxysilane, methyltrimethoxysilane and the like.
  • Examples thereof include silane coupling agents such as excisilane, n-hexyltrimethoxysilane, n-hexyltriethoxysilane, and ⁇ -glycidoxypropyltrimethoxysilane.
  • fatty acid treatment is preferable because the obtained sealing agent for a liquid crystal display element is particularly excellent in adhesion to an alignment film.
  • those commercially available include, for example, DHT-4A and DHT-4A-2 (all manufactured by Kyowa Chemical Industry Co., Ltd.).
  • the preferable upper limit of the average particle diameter of the secondary aggregates of the surface-treated hydrotalcite is 5 ⁇ m.
  • the average particle diameter of the secondary aggregate of the surface-treated hydrotalcite exceeds 5 ⁇ m, cell gap control of the liquid crystal display element may be hindered when the obtained sealing agent for liquid crystal display element is used.
  • the more preferable upper limit of the average particle diameter of the secondary aggregates of the surface-treated hydrotalcite is 3 ⁇ m.
  • the said average particle diameter means the average particle diameter calculated by measuring by a laser diffraction type particle size distribution measuring apparatus in this specification.
  • the content of the surface-treated hydrotalcite is preferably 3 parts by weight with respect to 100 parts by weight of the curable resin, and 100 parts by weight with a preferable upper limit. If the content of the surface-treated hydrotalcite is less than 3 parts by weight, adhesion may not be sufficiently obtained. When the content of the surface-treated hydrotalcite exceeds 100 parts by weight, the viscosity of the obtained sealing agent may be too high.
  • the more preferable lower limit of the content of the surface-treated hydrotalcite is 5 parts by weight, and the more preferable upper limit is 50 parts by weight.
  • the surface-treated calcium carbonate is obtained by surface-treating calcium carbonate.
  • Examples of the surface treatment applied to the calcium carbonate include fatty acid treatment and silane coupling agent treatment. Among them, hydrophobic treatment is preferred.
  • Examples of surface treatment agents used for surface treatment of the calcium carbonate include fatty acids such as stearic acid, oleic acid and linoleic acid, dimethyldimethoxysilane, dimethyldiexisilane, methyltrimethoxysilane, and methyltriethoxy.
  • Silane coupling agents such as silane, n-hexyltrimethoxysilane, n-hexyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane and the like can be mentioned.
  • fatty acid treatment is preferable because the obtained sealing agent for a liquid crystal display element is particularly excellent in adhesion to an alignment film.
  • the preferable upper limit of the average particle diameter of the secondary aggregate of the surface-treated calcium carbonate is 5 ⁇ m.
  • the average particle diameter of the secondary aggregate of the surface-treated calcium carbonate exceeds 5 ⁇ m, cell gap control of the liquid crystal display element may be hindered when the obtained sealing agent for liquid crystal display element is used.
  • the more preferable upper limit of the average particle diameter of the secondary aggregate of the surface-treated calcium carbonate is 3 ⁇ m.
  • the preferable lower limit of the content of the surface-treated calcium carbonate is 3 parts by weight and the preferable upper limit is 100 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the surface-treated calcium carbonate is less than 3 parts by weight, the effect of improving the adhesion of the sealing agent to the alignment film may not be sufficiently exhibited.
  • the content of the surface-treated calcium carbonate exceeds 100 parts by weight, the viscosity of the obtained sealing agent may be too high.
  • the more preferable lower limit of the content of the surface-treated calcium carbonate is 5 parts by weight, and the more preferable upper limit is 50 parts by weight.
  • Polyimide fine particles for example, a method of subjecting a polyamic acid solution to thermal imidization treatment, a method of producing polyamic acid particles and thereafter subjecting the polyamic acid particles to thermal imidization treatment, And methods such as crushing and cutting the film.
  • polyimide fine particles examples of commercially available ones include PI powder (manufactured by Finetech Co., Ltd.).
  • the preferable upper limit of the average particle diameter of the secondary aggregates of the polyimide fine particles is 5 ⁇ m.
  • the average particle diameter of the secondary aggregate of the polyimide fine particles exceeds 5 ⁇ m, the cell gap control of the liquid crystal display element may be hindered when the obtained sealing agent for liquid crystal display element is used.
  • the more preferable upper limit of the average particle diameter of the secondary aggregate of the polyimide fine particles is 3 ⁇ m.
  • a preferable lower limit is 3 parts by weight and a preferable upper limit is 100 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the polyimide fine particles is less than 3 parts by weight, the effect of improving the adhesion of the sealing agent to the alignment film may not be sufficiently exhibited.
  • the content of the polyimide fine particles is more than 100 parts by weight, the viscosity of the obtained sealing agent may be too high.
  • the more preferable lower limit of the content of the polyimide fine particles is 5 parts by weight, and the more preferable upper limit is 50 parts by weight.
  • NBR nonitrile butadiene rubber
  • XNBR carboxyl-modified NBR
  • NBIR isoprene
  • NBR fine particles commercially available ones include Narpow VP-401, Narpow VP-501 (all manufactured by Sanyo Trading Co., Ltd.), and the like.
  • the preferable upper limit of the average particle diameter of the secondary aggregates of the NBR fine particles is 5 ⁇ m.
  • the more preferable upper limit of the average particle diameter of the secondary aggregates of the NBR fine particles is 3 ⁇ m.
  • a preferable lower limit is 3 parts by weight and a preferable upper limit is 100 parts by weight with respect to 100 parts by weight of the curable resin. If the content of the NBR fine particles is less than 3 parts by weight, the effect of improving the adhesion of the sealing agent to the alignment film may not be sufficiently exhibited. When the content of the NBR fine particles is more than 100 parts by weight, the viscosity of the obtained sealing agent may be too high.
  • the more preferable lower limit of the content of the NBR fine particles is 5 parts by weight, and the more preferable upper limit is 50 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention contains at least one selected from the group consisting of surface-treated hydrotalcite, surface-treated calcium carbonate, polyimide fine particles, and nitrile butadiene rubber fine particles, May contain only 1 type, and may contain 2 or more types.
  • the sealing agent for a liquid crystal display element of the present invention contains two or more of surface-treated hydrotalcite, surface-treated calcium carbonate, polyimide fine particles, and nitrile butadiene rubber fine particles, the total content thereof is the above
  • the preferable lower limit is 3 parts by weight and the preferable upper limit is 100 parts by weight with respect to 100 parts by weight of the curable resin.
  • 3-alkoxysilylpropylsuccinic anhydrides examples include 3-trimethoxysilypropylsuccinic anhydride, 3-triethoxysilypropylsuccinic acid, 3-methyldimethoxysilypropylsuccinic acid and 3-methylsuccinic anhydride. Diethoxysilyl silyl succinic acid etc. are mentioned.
  • 3-alkoxysilylpropylsuccinic anhydrides commercially available ones include, for example, X-12-967C (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • R 1 a methyl group, a methoxy group, or represents an ethoxy group
  • R 2 R 3 represents a methoxy group or an ethoxy group.
  • R 4 is a methyl group, a methoxy group, or represents an ethoxy group
  • R 5 represents a methoxy group or an ethoxy group.
  • R 7 represents a methoxy group or an ethoxy group.
  • a preferable lower limit is 0.2 parts by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin. If the content of the silane coupling agent according to the present invention is less than 0.2 parts by weight, adhesion may not be sufficiently obtained. When the content of the silane coupling agent according to the present invention exceeds 10 parts by weight, the obtained sealing agent becomes inferior in storage stability, or the silane coupling agent according to the present invention when producing a liquid crystal display element May be eluted into the liquid crystal to cause display unevenness.
  • a more preferable lower limit of the content of the silane coupling agent according to the present invention is 0.5 parts by weight, a more preferable upper limit is 7 parts by weight, and a still more preferable upper limit is 5 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention is represented by surface-treated hydrotalcite, surface-treated calcium carbonate, polyimide fine particles, nitrile butadiene rubber fine particles, 3-alkoxysilylpropylsuccinic anhydride, formula (1) It is sufficient to contain at least one selected from the group consisting of a compound, a compound represented by Formula (2), and a compound represented by Formula (3), surface-treated hydrotalcite, surface-treated calcium carbonate, polyimide At least one selected from the group consisting of fine particles and nitrile butadiene rubber fine particles, 3-alkoxysilylpropylsuccinic anhydride, a compound represented by the above formula (1), a compound represented by the formula (2), And at least one selected from the group consisting of compounds represented by formula (3).
  • the total content of the total content of the surface-treated hydrotalcite, surface-treated calcium carbonate, the polyimide fine particles, and the nitrile butadiene rubber fine particles is preferably a lower limit of 3 weight per 100 weight parts of the curable resin.
  • the preferable upper limit is 100 parts by weight
  • the total content of the silane coupling agent according to the present invention is preferably 0.2 parts by weight with the preferable lower limit with respect to 100 parts by weight of the curable resin. It is 10 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention contains a curable resin having a (meth) acrylic group.
  • the curable resin having the (meth) acrylic group is obtained, for example, by reacting an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, (meth) acrylic acid and an epoxy compound.
  • Epoxy (meth) acrylates, urethane (meth) acrylates obtained by reacting an isocyanate with a (meth) acrylic acid derivative having a hydroxyl group, and the like.
  • the (meth) acrylic means acrylic or methacrylic
  • the (meth) acrylate means acrylate or methacrylate.
  • the above-mentioned epoxy (meth) acrylate refers to a compound obtained by reacting all epoxy groups in the epoxy compound with (meth) acrylic acid.
  • examples of monofunctional compounds include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4 -Hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isobornyl (Meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxy ethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, tetrahydrofuran Furyl (meth)
  • ester compounds obtained by reacting the above-described (meth) acrylic acid with a compound having a hydroxyl group for example, 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, 2-n-butyl-2-ethyl 1,3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate ) Acrylate, tetra Tylene glycol di (meth) acrylate
  • ester compounds obtained by reacting a compound having a hydroxyl group with the above (meth) acrylic acid as trifunctional or higher functional ones, for example, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene Oxide-added trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanurate tri (meth) acrylate, dipentaerythritol penta (meth) Acrylate, dipentaerythritol hexa (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra ( Data) acrylate, glycerin tri (meth) acrylate,
  • the epoxy (meth) acrylate obtained by reacting the above (meth) acrylic acid and the epoxy compound is not particularly limited.
  • the epoxy resin and (meth) acrylic acid can be used in the presence of a basic catalyst according to a conventional method. What is obtained by making it react below is mentioned.
  • combining the said epoxy (meth) acrylate is not specifically limited, For example, bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, 2,2'- diallyl bisphenol A Type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy Resin, phenol novolac epoxy resin, ortho cresol novolac epoxy resin, dicyclopentadiene novolac epoxy resin, biphenyl novolac epoxy resin Naphthalene phenol novolac-type epoxy resin, glycidyl amine type epoxy resin, alkyl polyol type epoxy resin, rubber modified epoxy resin, glycidyl ester compounds, bisphenol A type episulfide resins.
  • bisphenol A epoxy resin
  • bisphenol A-type epoxy resins commercially available ones include, for example, Epicoat 828 EL, Epicoat 1004 (all manufactured by Mitsubishi Chemical Corporation), Epiclon 850-S (manufactured by DIC Corporation), and the like.
  • Epicoat 828 EL Epicoat 828 EL
  • Epicoat 1004 all manufactured by Mitsubishi Chemical Corporation
  • Epiclon 850-S manufactured by DIC Corporation
  • the like As what is marketed among the said bisphenol F-type epoxy resins, Epicoat 806, Epicoat 4004 (all are Mitsubishi Chemical Corp. make), etc. are mentioned, for example.
  • Epiclon EXA1514 made by DIC company
  • biphenyl type epoxy resins commercially available ones include, for example, Epicoat YX-4000H (manufactured by Mitsubishi Chemical Corporation).
  • sulfide type epoxy resins commercially available ones include, for example, YSLV-50TE (manufactured by Nippon Steel Chemical Co., Ltd.).
  • diphenyl ether type epoxy resins examples include YSLV-80DE (manufactured by Nippon Steel Chemical Co., Ltd.).
  • dicyclopentadiene type epoxy resins commercially available ones include, for example, EP-4088S (manufactured by Adeka).
  • naphthalene type epoxy resins commercially available ones include, for example, Epiclon HP4032, Epiclon EXA-4700 (all manufactured by DIC) and the like.
  • examples of commercially available phenol novolac epoxy resins include Epiclon N-770 (manufactured by DIC Corporation).
  • commercially available ones include, for example, Epiclon N-670-EXP-S (manufactured by DIC) and the like.
  • Epiclon HP7200 made by DIC Corporation
  • biphenyl novolac epoxy resins commercially available ones include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.) and the like.
  • examples of commercially available naphthalenephenol novolac type epoxy resins include ESN-165S (manufactured by Nippon Steel Chemical Co., Ltd.).
  • examples of commercially available glycidyl amine type epoxy resins those commercially available include, for example, Epicoat 630 (manufactured by Mitsubishi Chemical Corporation), Epiclon 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Co., Ltd.), and the like.
  • alkyl polyol type epoxy resins commercially available ones are, for example, ZX-1542 (manufactured by Nippon Steel Chemical Co., Ltd.), Epiclon 726 (manufactured by DIC Corporation), Epolight 80 MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX- 611 (manufactured by Nagase ChemteX Co., Ltd.) and the like.
  • those commercially available include, for example, YR-450, YR-207 (all manufactured by Nippon Steel Chemical Co., Ltd.), Epode PB (manufactured by Daicel Chemical Industries, Ltd.), and the like.
  • examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corp.).
  • commercially available ones include, for example, Epicoat YL-7000 (manufactured by Mitsubishi Chemical Corporation).
  • epoxy resins as other commercially available ones, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel Chemical Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Corp.), Epicoat 1031, Epicoat 1032 (all manufactured by Mitsubishi Chemical Corporation), EXA-7120 (manufactured by DIC Corporation), TEPIC (manufactured by Nissan Chemical Industries, Ltd.), and the like.
  • YDC-1312, YSLV-80XY, YSLV-90CR all manufactured by Nippon Steel Chemical Co., Ltd.
  • XAC4151 manufactured by Asahi Kasei Corp.
  • Epicoat 1031 Epicoat 1032
  • EXA-7120 manufactured by DIC Corporation
  • TEPIC manufactured by Nissan Chemical Industries, Ltd.
  • the epoxy (meth) acrylate obtained by reacting the above (meth) acrylic acid and the epoxy compound is, for example, 360 parts by weight of resorcinol type epoxy resin (manufactured by Nagase ChemteX, "EX-201") Then, 2 parts by weight of p-methoxyphenol as a polymerization inhibitor, 2 parts by weight of triethylamine as a reaction catalyst, and 210 parts by weight of acrylic acid are stirred under reflux while feeding in air at 90 ° C. You can get it.
  • epoxy (meth) acrylates that are commercially available, for example, Ebecryl 860, Ebecryl 3200, Ebecryl 3201, Ebecryl 3412, Ebecryl 3600, Ebecryl 3700, Ebecryl 3701, Ebecryl 3702, Ebecryl 3703, Ebecryl 3800, Ebecryl 6040 , Ebecryl RDX63182 (all manufactured by Daicel-Cytec), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Co., Ltd.), epoxy ester M -600A, epoxy ester 40 EM, epoxy ester 70 PA, epoxy ester 200 PA, epoxy ester 80 MFA, epoxy ester 3002 M, epoxy ester 3 02A, epoxy ester 1600 A, epoxy ester 3000 M, epoxy ester 3000 A, epoxy ester 200 EA, epoxy ester 400 EA (all from Kyo
  • the urethane (meth) acrylate obtained by reacting the above-mentioned isocyanate with a (meth) acrylic acid derivative having a hydroxyl group is, for example, a (meth) acrylic acid derivative 2 having a hydroxyl group with respect to one equivalent of a compound having two isocyanate groups.
  • An equivalent amount can be obtained by reacting in the presence of a catalytic amount of a tin-based compound.
  • isocyanate used as a raw material of urethane (meth) acrylate obtained by making the above-mentioned isocyanate react the (meth) acrylic acid derivative which has a hydroxyl group for example, isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tridiisocyanate Diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphe DOO, tetra
  • isocyanate used as the raw material of the urethane (meth) acrylate obtained by making the (meth) acrylic acid derivative which has a hydroxyl group react with the said isocyanate ethylene glycol, glycerol, sorbitol, trimethylolpropane, (poly) propylene glycol
  • chain-extended isocyanate compounds obtained by the reaction of polyols such as carbonate diols, polyether diols, polyester diols, polycaprolactone diols and the like with an excess of isocyanate.
  • a (meth) acrylic acid derivative having a hydroxyl group which is a raw material of urethane (meth) acrylate obtained by reacting a (meth) acrylic acid derivative having a hydroxyl group with the above-mentioned isocyanate
  • 2-hydroxyethyl (meth) Commercial products such as acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3- Mono (meth) acrylate of dihydric alcohol such as butanediol, 1,4-butanediol, polyethylene glycol, etc.
  • Mono (meth) acrylate or di (meth) acrylate of trihydric alcohol such as trimethylolethane, trimethylolpropane and glycerin Acrylates, epoxy acrylates such as bisphenol A-modified epoxy acrylate.
  • urethane (meth) acrylate obtained by reacting the above-mentioned isocyanate with a (meth) acrylic acid derivative having a hydroxyl group are 134 parts by weight of trimethylolpropane, 0.2 parts by weight of BHT as a polymerization inhibitor, As a reaction catalyst, 0.01 part by weight of dibutyltin dilaurate and 666 parts by weight of isophorone diisocyanate are added and reacted for 2 hours while stirring under reflux at 60 ° C. Then, 51 parts by weight of 2-hydroxyethyl acrylate is added and air is fed in It can be obtained by reacting for 2 hours with reflux stirring at 90 ° C.
  • urethane (meth) acrylates commercially available ones are, for example, M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), Ebecryl 230, Ebecryl 270, Ebecryl.
  • the curable resin having a (meth) acrylic group is preferably one having a hydrogen bonding unit such as -OH group, -NH- group, -NH 2 group or the like from the viewpoint of suppressing an adverse effect on liquid crystal.
  • Epoxy (meth) acrylate is particularly preferred in view of ease and the like.
  • the curable resin having a (meth) acrylic group is preferably one having 2 to 3 (meth) acrylic groups in the molecule in view of high reactivity.
  • the sealing agent for a liquid crystal display element of the present invention it is preferable to further add a resin having an epoxy group as a curable resin.
  • a resin having an epoxy group As what is marketed among resin which has an epoxy group, what was mentioned as an epoxy compound used as a raw material for synthesize
  • the resin having an epoxy group may be, for example, a compound having a (meth) acrylic group and an epoxy group in one molecule.
  • a compound obtained by reacting an epoxy group of a part of a compound having two or more epoxy groups with (meth) acrylic acid can be mentioned.
  • the compound etc. obtained by making the epoxy group of a part of compound which has an epoxy group react with (meth) acrylic acid can also be regarded as curable resin which has the said (meth) acryl group.
  • the compound obtained by reacting the epoxy group of a part of the compound having two or more epoxy groups with (meth) acrylic acid is, for example, an epoxy resin and (meth) acrylic acid in a basic catalyst according to a conventional method. It is obtained by reacting in the presence.
  • a phenol novolac epoxy resin N-770 (manufactured by DIC) is dissolved in 500 mL of toluene, 0.1 g of triphenylphosphine is added to this solution to make a uniform solution, and 35 g of acrylic acid in this solution Is added dropwise under reflux stirring for 2 hours, and then reflux stirring is further conducted for 6 hours, and then a partially acrylic modified phenol novolac epoxy resin in which 50 mol% of epoxy groups are reacted with acrylic acid by removing toluene Can be obtained (in this case 50% partially acrylic modified).
  • the sealing agent for a liquid crystal display element of the present invention preferably has a (meth) acrylic group and an epoxy group, and the molar ratio of the (meth) acrylic group to the epoxy group of the curable resin is 50:50 to 95: 5. It is preferable to mix
  • the sealing agent for a liquid crystal display element of the present invention contains a curing agent.
  • a photo radical polymerization initiator for reacting a (meth) acrylic group with light such as ultraviolet light
  • a thermal radical polymerization initiator for reacting a (meth) acrylic group with heat an epoxy group by UV
  • the photo cationic polymerization initiator for making it react the thermal epoxy curing agent for making an epoxy group react with heat are mentioned.
  • the photo radical polymerization initiator is not particularly limited, and commercially available ones include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, Lucirin TPO (all manufactured by BASF Japan), Soin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.), Adeka Cruz NCI 930 (manufactured by ADEKA), and the like can be mentioned.
  • the content of the photo radical polymerization initiator is not particularly limited, but a preferable lower limit is 0.1 parts by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the (meth) acrylic group-containing curable resin.
  • a preferable lower limit is 0.1 parts by weight
  • a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the (meth) acrylic group-containing curable resin.
  • the content of the photo radical polymerization initiator is less than 0.1 parts by weight, the liquid crystal display element sealing agent of the present invention may not be sufficiently cured.
  • storage stability may be lowered.
  • the heat radical polymerization initiator is not particularly limited, and includes peroxides and azo compounds.
  • Examples of commercially available products include perbutyl O, perhexyl O, and perbutyl PV (all manufactured by NOF Corporation), V -30, V-501, V-601, VPE-0201, VPE-0401, VPE-0601 (all manufactured by Wako Pure Chemical Industries, Ltd.) and the like.
  • the content of the thermal radical polymerization initiator is not particularly limited, but a preferable lower limit is 0.01 parts by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the (meth) acrylic group-containing curable resin.
  • a preferable lower limit is 0.01 parts by weight
  • a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the (meth) acrylic group-containing curable resin.
  • the content of the thermal radical polymerization initiator is less than 0.01 parts by weight, the liquid crystal display element sealing agent of the present invention may not be sufficiently cured.
  • storage stability may be reduced.
  • the photo cationic polymerization initiator is not particularly limited, and commercially available ones include, for example, Adeka Optomer SP-150, Adeka Optomer SP-170 (all manufactured by ADEKA), and the like.
  • the content of the photo cationic polymerization initiator is not particularly limited, but a preferable lower limit is 0.1 parts by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the resin having an epoxy group.
  • a preferable lower limit is 0.1 parts by weight
  • a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the resin having an epoxy group.
  • the sealant for a liquid crystal display element of the present invention may not be sufficiently cured.
  • storage stability may be reduced.
  • thermal epoxy curing agent examples include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides and the like. Among them, solid organic acid hydrazide is suitably used.
  • the solid organic acid hydrazide is not particularly limited, and examples thereof include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide and the like, and examples of commercially available ones include SDH (manufactured by Nippon Finechem Co., Ltd.) And ADH (manufactured by Otsuka Chemical Co., Ltd.). In addition, Amicure VDH, Amicure VDH-J, Amicure UDH (all manufactured by Ajinomoto Fine Techno Co., Ltd.) and the like can be used.
  • the content of the thermal epoxy curing agent is preferably 1 part by weight with respect to 100 parts by weight of the resin having an epoxy group, and 50 parts by weight with a preferable upper limit.
  • the content of the thermal epoxy curing agent is less than 1 part by weight, the sealant for a liquid crystal display element of the present invention may not be cured sufficiently.
  • the content of the thermal epoxy thermosetting agent exceeds 50 parts by weight, the viscosity of the sealing agent for a liquid crystal display element of the present invention may be high, and the coating property and the like may be impaired.
  • a more preferable upper limit of the content of the thermal epoxy curing agent is 30 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention may further contain a filler for the purpose of improving adhesion by a stress dispersion effect, improving a linear expansion coefficient, and the like.
  • the filler is not particularly limited.
  • talc asbestos, silica, diatomaceous earth, smectite, bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide
  • Inorganic fillers such as aluminum hydroxide, glass beads, silicon nitride, barium sulfate, gypsum, calcium silicate, sericite activated clay, aluminum nitride, etc., organic particles such as polyester particles, polyurethane particles, vinyl polymer particles, acrylic polymer particles, etc. Filler is mentioned.
  • the sealing agent for a liquid crystal display element of the present invention can further contain other silane coupling agents other than the silane coupling agent according to the present invention.
  • the other silane coupling agents described above are not particularly limited, and examples thereof include ⁇ -aminopropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, and ⁇ -isocyanatopropyltrimethoxysilane. It is preferably used.
  • These other silane coupling agents may be used alone or in combination of two or more.
  • the sealing agent for a liquid crystal display element of the present invention further comprises, if necessary, a reactive diluent for adjusting viscosity, a thixotropic agent for adjusting thixotropy, a spacer such as a polymer bead for adjusting panel gap, -Other known additives such as a curing accelerator such as P-chlorophenyl-1,1-dimethylurea, an antifoaming agent, a leveling agent, and a polymerization inhibitor may be contained.
  • the method for producing the sealing agent for a liquid crystal display element of the present invention is not particularly limited, and for example, (meth) acrylic using a mixer such as homodisper, homomixer, universal mixer, planetarium mixer, kneader, 3-roll etc.
  • a mixer such as homodisper, homomixer, universal mixer, planetarium mixer, kneader, 3-roll etc.
  • the liquid crystal display element which uses the sealing compound for liquid crystal display elements of this invention is also one of this invention.
  • the sealing agent for liquid crystal display element of the present invention, etc. is screen-printed, dispenser coated, etc. on one of the transparent substrates having electrodes such as ITO thin film and alignment film.
  • minute droplets of liquid crystal are dropped and applied to the entire surface of the transparent substrate frame.
  • the present invention it is possible to provide a sealing agent for a liquid crystal display element which is excellent in adhesion to an alignment film and hardly generates liquid crystal contamination. Further, according to the present invention, it is possible to provide a liquid crystal display element using the sealing agent for a liquid crystal display element.
  • Examples 1 to 54, and Comparative Examples 1 to 5 According to the compounding ratio described in Tables 1 to 10, the respective materials are mixed using a planetary stirrer ("Awatori Neritaro" manufactured by Shinky Co., Ltd.), and then mixed using three rolls. Sealing agents for liquid crystal display elements of Examples 1 to 54 and Comparative Examples 1 to 5 were prepared.
  • the obtained sealing agent for a liquid crystal display element was applied on the alignment film of a substrate having a transparent electrode and an alignment film ("SE7492” manufactured by Nissan Chemical Industries, Ltd.) in a square frame by a dispenser. Subsequently, microdroplets of liquid crystal (manufactured by Chisso Corporation, “JC-5004LA”) were dropped and applied onto the entire surface of the frame on the substrate, and the substrate having another transparent electrode and an alignment film was superposed in vacuum. After releasing the vacuum, the liquid crystal display element sealing agent was cured to obtain a liquid crystal display element. In addition, hardening of the sealing compound for liquid crystal display elements was performed by heating at 120 degreeC for 1 hour, after irradiating an ultraviolet-ray 3000 mJ / cm ⁇ 2 >.
  • N-770 partially modified products in Tables 1 to 10 were prepared by the following method. That is, 190 g of a phenol novolac epoxy resin (manufactured by DIC, “N-770”) was dissolved in 500 mL of toluene, and 0.1 g of triphenylphosphine was added to this solution to obtain a uniform solution. After 35 g of acrylic acid was added dropwise to the obtained solution under reflux and stirring over 2 hours, the mixture was further stirred under reflux for 6 hours. Partially acrylated epoxy (N-770 partially modified product) in which 50 mol% of epoxy groups were modified to acrylic groups by removing toluene was obtained.
  • N-770 phenol novolac epoxy resin
  • the present invention it is possible to provide a sealing agent for a liquid crystal display element which is excellent in adhesion to an alignment film and hardly generates liquid crystal contamination. Further, according to the present invention, it is possible to provide a liquid crystal display element using the sealing agent for a liquid crystal display element.

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Abstract

L'invention concerne un agent d'étanchéité pour élément d'affichage à cristaux liquides, présentant une adhérence supérieure sur un film orienté et n'entraînant sensiblement pas de contamination des cristaux liquides. L'invention concerne également un élément d'affichage à cristaux liquides obtenu au moyen dudit agent d'étanchéité. L'agent d'étanchéité pour élément d'affichage à cristaux liquides selon l'invention contient : une résine durcissable contenant un groupe (méth)acrylate ; un agent de durcissement ; et au moins un composé sélectionné dans le groupe constitué par une hydrotalcite traitée en surface, un carbonate de calcium traité en surface, des microparticules de polyimide, des microparticules de caoutchouc nitrile-butadiène, un anhydride de 3-alcoxysilyl-propyl-succinate, le composé représenté par la formule (1), le composé représenté par la formule (2) et le composé représenté par la formule (3). Dans la formule (1), R1 représente un groupe méthyle, un groupe méthoxy ou un groupe éthoxy et R2 et R3 représentent un groupe méthoxy ou un groupe éthoxy. Dans la formule (2), R4 représente un groupe méthyle, un groupe méthoxy ou un groupe éthoxy et R5 et R6 représentent un groupe méthoxy ou un groupe éthoxy. Dans la formule (3), R7 représente un groupe méthoxy ou un groupe éthoxy.
PCT/JP2012/070223 2011-08-17 2012-08-08 Agent d'étanchéité pour élément d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé WO2013024768A1 (fr)

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JP2012540184A JP5281204B1 (ja) 2011-08-17 2012-08-08 液晶表示素子用シール剤及び液晶表示素子
KR1020137018537A KR101953925B1 (ko) 2011-08-17 2012-08-08 액정 표시 소자용 시일제 및 액정 표시 소자
CN201280011440.6A CN103430086B (zh) 2011-08-17 2012-08-08 液晶显示元件用密封剂以及液晶显示元件
KR1020137018415A KR101357327B1 (ko) 2011-08-17 2012-08-08 액정 표시 소자용 시일제 및 액정 표시 소자

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KR102267591B1 (ko) 2018-11-20 2021-06-18 주식회사 엘지화학 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 이를 이용한 액정 배향막 및 액정표시소자
KR102267590B1 (ko) 2018-11-20 2021-06-18 주식회사 엘지화학 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 이를 이용한 액정 배향막 및 액정표시소자
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