WO2018207730A1 - 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 - Google Patents
液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 Download PDFInfo
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- WO2018207730A1 WO2018207730A1 PCT/JP2018/017622 JP2018017622W WO2018207730A1 WO 2018207730 A1 WO2018207730 A1 WO 2018207730A1 JP 2018017622 W JP2018017622 W JP 2018017622W WO 2018207730 A1 WO2018207730 A1 WO 2018207730A1
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- liquid crystal
- crystal display
- meth
- acrylate
- display element
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- 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 sealant for a liquid crystal display element that is excellent in impact resistance, flexibility, and moisture permeation prevention. Moreover, this invention relates to the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements.
- a liquid crystal dropping method called a dropping method using a photothermal combined curing type sealing agent containing a polymerization initiator and a thermosetting agent is used.
- a frame-like seal pattern is formed on one of the two substrates with electrodes by dispensing.
- liquid crystal microdrops are dropped into the sealing frame of the substrate in a state where the sealing agent is uncured, the other substrate is superposed under vacuum, and the sealing portion is irradiated with light such as ultraviolet rays to perform temporary curing. Thereafter, heating is performed to perform main curing, and a liquid crystal display element is manufactured.
- this dripping method has become the mainstream method for manufacturing liquid crystal display elements.
- liquid crystal display elements are required to have impact resistance, and the sealing agent does not cause peeling of the panel even if it receives external impact due to dropping of the liquid crystal display element, etc. Therefore, there is a demand for higher flexibility and adhesiveness (particularly in the case of a narrow frame design, adhesion to an alignment film).
- the liquid crystal display element is also required to have moisture resistance reliability in driving in a high temperature and high humidity environment. In order to improve the moisture resistance reliability of the liquid crystal display element, it is necessary to improve the adhesion of the sealing agent to the substrate and the alignment film and to improve the moisture permeation preventive property of the sealing agent.
- a method for improving the moisture permeation preventive property of the sealing agent for example, a method of blending a filler such as talc can be considered.
- a filler such as talc
- the cured product may be inferior in flexibility and become brittle or inferior in impact resistance. With the agent, it was difficult to achieve both impact resistance, flexibility and moisture permeation prevention.
- An object of this invention is to provide the sealing compound for liquid crystal display elements which is excellent in impact resistance, a softness
- flexibility, and moisture-permeable prevention property. Another object of the present invention is to provide a vertical conduction material and a liquid crystal display element using the sealing agent for a liquid crystal display element.
- the present invention contains a curable resin, a polymerization initiator and / or a thermosetting agent, and an inorganic filler having a hydrophobic group on the surface, and the content of the inorganic filler having a hydrophobic group on the surface is 15% by weight. %, And the cured product has a storage elastic modulus at 25 ° C. of 2.0 GPa or less.
- the present invention is described in detail below.
- the inventor of the present invention has a flexible sealing agent in which the storage elastic modulus at 25 ° C. of the cured product is not more than a specific value, so that the inorganic filler having a hydrophobic group on the surface has a specific content ratio or more. It was considered to blend. As a result, it has been found that a sealing agent for liquid crystal display elements that is excellent in all of impact resistance, flexibility, and moisture permeation prevention properties can be obtained, and the present invention has been completed.
- the sealing agent for liquid crystal display elements of this invention contains the inorganic filler which has a hydrophobic group on the surface.
- the sealing compound for liquid crystal display elements of this invention will be excellent in moisture-permeable prevention property.
- the inorganic filler which has the said hydrophobic group on the surface also has the effect of improving the applicability
- the inorganic filler which has the said hydrophobic group on the surface also has the effect of improving the impact resistance of the sealing compound for liquid crystal display elements of this invention.
- the reason why the impact resistance of the sealant is improved by containing the inorganic filler having the hydrophobic group on the surface is as follows. That is, when the inorganic filler has a hydrophobic group on the surface, the inorganic filler is easily dispersed in the curable resin. As a result, it is considered that the cured product of the sealant, which is caused by the aggregation of the inorganic filler, is suppressed from becoming brittle or the flexibility is reduced.
- the effect of improving the impact resistance of the sealant is obtained when a compound having a polymerizable functional group and a cyclic lactone ring-opening structure is used as a curable resin in combination with an inorganic filler having an alkyl group on the surface. Particularly suitable.
- the inorganic filler having a hydrophobic group on the surface has base particles and a hydrophobic group on the surface of the base particles.
- the base particles include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, and titanium oxide.
- Inorganic particles such as calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate. Of these, silica is preferable.
- the sealing agent for liquid crystal display elements of the present invention uses a combination of a compound having a polymerizable functional group and a cyclic lactone ring-opening structure as a curable resin and an inorganic filler having an alkyl group on the surface. It is preferable.
- the inorganic filler which has the said hydrophobic group on the surface can be obtained by the method of surface-treating the said base material particle with a surface treating agent.
- the surface treatment agent examples include epoxine silane, amino silane, (meth) acryl silane, vinyl silane, methyl chlorosilane, and dimethyl polysiloxane.
- the “(meth) acryl” means acryl or methacryl.
- Examples of the method for surface-treating the substrate particles with the surface treatment agent include, for example, a method of spraying a mixed solution of water and the surface treatment agent on the fluidized substrate particles, alcohol, toluene, and the like. Examples include a method in which the base particles are added to the organic solvent, the surface treatment agent and water are further added, and then the water and the organic solvent are evaporated and dried by an evaporator.
- the minimum with a preferable average particle diameter of the inorganic filler which has the said hydrophobic group on the surface is 0.1 micrometer, and a preferable upper limit is 3 micrometers.
- the average particle size of the inorganic filler having the hydrophobic group on the surface is within this range, the obtained sealing agent for liquid crystal display elements does not deteriorate applicability, etc., impact resistance, flexibility and moisture permeation prevention It will be excellent due to the effect of balancing the properties.
- the minimum with a more preferable average particle diameter of the inorganic filler which has the said hydrophobic group on the surface is 0.4 micrometer, and a more preferable upper limit is 1 micrometer.
- the average particle size of the inorganic filler having the hydrophobic group on the surface is the average value of the particle size (major axis) of 10 particles observed at a magnification of 5000 using a scanning electron microscope. means.
- the minimum of the content rate of the inorganic filler which has the said hydrophobic group on the surface is 15 weight%.
- the content of the inorganic filler having the hydrophobic group on the surface is 15% by weight or more, the obtained sealing agent for liquid crystal display elements is excellent in moisture permeation preventive property and coating property.
- a preferable lower limit of the content of the inorganic filler having the hydrophobic group on the surface is 20% by weight, and a more preferable lower limit is 30% by weight.
- a preferable upper limit of the content ratio of the inorganic filler having the hydrophobic group on the surface is 70% by weight, and a more preferable upper limit is 50% by weight.
- the sealing agent for liquid crystal display elements of the present invention may contain other fillers in addition to the inorganic filler having the hydrophobic group on the surface thereof within the range not impairing the object of the present invention.
- the other filler include inorganic particles mentioned as inorganic filler base particles having the hydrophobic group on the surface, organic particles such as polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles. Is mentioned.
- the sealing agent for liquid crystal display elements of this invention contains curable resin.
- a method for setting the storage elastic modulus of the cured product at 25 ° C. to 2.0 GPa or less a method using a compound having a polymerizable functional group and a flexible skeleton as the curable resin. Is preferred.
- Examples of the polymerizable functional group possessed by the compound having a polymerizable functional group and a flexible skeleton include a (meth) acryloyl group and an epoxy group. Of these, a (meth) acryloyl group is preferable.
- the compound having a polymerizable functional group and a flexible skeleton preferably has two or more of the polymerizable functional groups in one molecule.
- the “(meth) acryloyl” means acryloyl or methacryloyl.
- Examples of the flexible skeleton of the compound having a polymerizable functional group and a flexible skeleton include a ring-opening structure of a cyclic lactone, a polyalkylene oxide structure, a rubber structure derived from a conjugated diene, and a polysiloxane structure. Of these, a ring-opening structure of a cyclic lactone is preferable.
- the sealing agent for liquid crystal display elements of the present invention uses a combination of a compound having a polymerizable functional group and a cyclic lactone ring-opening structure as a curable resin and an inorganic filler having an alkyl group on the surface. It is preferable.
- the compound having a polymerizable functional group and a flexible skeleton include, for example, caprolactone-modified bisphenol A type epoxy (meth) acrylate, caprolactone-modified bisphenol F type epoxy (meth) acrylate, and caprolactone-modified bisphenol E type epoxy ( (Meth) acrylate, ethylene oxide modified bisphenol A type epoxy (meth) acrylate, ethylene oxide modified bisphenol F type epoxy (meth) acrylate, ethylene oxide modified bisphenol E type epoxy (meth) acrylate, propylene oxide modified bisphenol A type epoxy (meth) Acrylate, propylene oxide modified bisphenol F type epoxy (meth) acrylate, propylene oxide modified bisphenol E type Xyl (meth) acrylate, terminal amino group-containing butadiene-acrylonitrile (ATBN) modified epoxy (meth) acrylate, terminal carboxyl group-containing butadiene-acrylonitrile (CTBN) modified epoxy (meth) acrylate, (
- caprolactone-modified bisphenol A type epoxy (meth) acrylate is preferable.
- the “(meth) acrylate” means acrylate or methacrylate
- the “epoxy (meth) acrylate” means that all epoxy groups in the epoxy compound react with (meth) acrylic acid. Represents the compound.
- the preferable lower limit of the content of the compound having the polymerizable functional group and the flexible skeleton in 100 parts by weight of the entire curable resin is 30 parts by weight, and the preferable upper limit is 90 parts by weight.
- the storage modulus at 25 ° C. of the cured liquid crystal display element sealant obtained can be easily within the above range. It becomes.
- a more preferable lower limit of the content of the compound having a polymerizable functional group and a flexible skeleton is 50 parts by weight, and a more preferable upper limit is 70 parts by weight.
- the curable resin has the polymerizable functional group and a flexible skeleton for the purpose of adjusting the storage elastic modulus of the cured product at 25 ° C., and improving impact resistance and low liquid crystal contamination. It is preferable to contain other curable resins other than the compound.
- other curable resin other epoxy compounds other than the compound which has the said polymerizable functional group and a flexible skeleton, and another (meth) acryl compound are used suitably.
- the “(meth) acrylic compound” means a compound having a (meth) acryloyl group.
- Examples of the other epoxy compounds include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2,2′-diallyl bisphenol A type epoxy resin, and hydrogenated bisphenol type.
- the said curable resin may contain the compound which has an epoxy group and a (meth) acryloyl group in 1 molecule as said other epoxy compound.
- examples of such a compound include a partial (meth) acryl-modified epoxy resin obtained by reacting a part of an epoxy group having two or more epoxy groups with (meth) acrylic acid.
- Examples of the other (meth) acrylic compounds include epoxy (meth) acrylates, (meth) acrylic acid ester compounds, urethane (meth) acrylates, and the like. Of these, epoxy (meth) acrylate is preferable.
- the other (meth) acrylic compounds are preferably those having two or more (meth) acryloyl groups in the molecule because of their high reactivity.
- Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
- Examples of the monofunctional compounds among the (meth) acrylic acid ester compounds include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, and isobutyl (meth) acrylate.
- Examples of the bifunctional compound among the (meth) acrylic acid ester compounds include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexane.
- those having three or more functions include, for example, trimethylolpropane tri (meth) acrylate, glycerin tri (meth) acrylate, pentaerythritol tri (meth) acrylate, and tris (meth).
- examples include acryloyloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.
- the urethane (meth) acrylate can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound in the presence of a catalytic amount of a tin-based compound.
- isocyanate compound examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene 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) thiophosphate, tetramethylxylylene diene Isocyanate, 1,6,11-undecane triisocyanate and the like.
- MDI diphenylmethane-4,4′-diisocyanate
- XDI
- Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono (meth) acrylate, mono (meth) acrylate of divalent alcohol, mono (meth) acrylate or di (meth) acrylate of trivalent alcohol. And epoxy (meth) acrylate.
- Examples of the hydroxyalkyl mono (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Can be mentioned.
- Examples of the divalent alcohol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
- Examples of the trivalent alcohol include trimethylolethane, trimethylolpropane, and glycerin.
- Examples of the epoxy (meth) acrylate include bisphenol A type epoxy acrylate.
- the sealing agent for liquid crystal display elements of the present invention has a molar ratio of (meth) acryloyl group to epoxy group ((meth) acryloyl group: epoxy group) in the curable resin of 50:50 to 95: 5. It is preferable to do.
- the sealing agent for liquid crystal display elements of this invention contains a polymerization initiator and / or a thermosetting agent.
- the polymerization initiator include radical polymerization initiators and cationic polymerization initiators.
- radical polymerization initiator examples include a photo radical polymerization initiator that generates radicals by light irradiation, a thermal radical polymerization initiator that generates radicals by heating, and the like.
- photo radical polymerization initiator examples include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthones, and the like.
- Examples of commercially available photo radical polymerization initiators include, for example, photo radical polymerization initiators manufactured by BASF, photo radical polymerization initiators manufactured by Light Chemical Co., and photo radical polymerization initiators manufactured by Tokyo Chemical Industry Co., Ltd. Etc.
- Examples of the photo radical polymerization initiator manufactured by BASF include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, and Lucyrin TPO.
- Examples of the radical photopolymerization initiator manufactured by Light Chemical Company include KR-02.
- Examples of the photo radical polymerization initiator manufactured by Tokyo Chemical Industry Co., Ltd. include benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
- thermal radical polymerization initiator what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
- a polymer azo initiator composed of a polymer azo compound is preferable.
- the polymer azo compound means a compound having an azo group and generating a radical capable of curing a (meth) acryloyloxy group by heat and having a number average molecular weight of 300 or more.
- the preferable lower limit of the number average molecular weight of the polymer azo compound is 1000, and the preferable upper limit is 300,000.
- the more preferable lower limit of the number average molecular weight of the polymer azo compound is 5000, the more preferable upper limit is 100,000, the still more preferable lower limit is 10,000, and the still more preferable upper limit is 90,000.
- the said number average molecular weight is a value calculated
- Examples of the polymer azo compound include those having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
- the polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via the azo group those having a polyethylene oxide structure are preferable.
- Specific examples of the polymer azo compound include, for example, a polycondensate of 4,4′-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4′-azobis (4-cyanopentanoic acid). And a polycondensate of polydimethylsiloxane having a terminal amino group.
- Examples of commercially available polymer azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.). It is done. Examples of commercially available azo compounds that are not polymers include V-65 and V-501 (both manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.).
- organic peroxide examples include ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
- a photocationic polymerization initiator can be suitably used as the cationic polymerization initiator.
- the cationic photopolymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be of an ionic photoacid generation type or a nonionic photoacid generation type. It may be.
- Examples of the photocationic polymerization initiator include onium salts such as aromatic diazonium salts, aromatic halonium salts, and aromatic sulfonium salts, organometallic complexes such as iron-allene complexes, titanocene complexes, and arylsilanol-aluminum complexes. Is mentioned.
- photocationic polymerization initiators examples include Adekaoptomer SP-150 and Adekaoptomer SP-170 (both manufactured by ADEKA).
- the said polymerization initiator may be used independently and 2 or more types may be used in combination.
- the content of the polymerization initiator is preferably 0.1 parts by weight and preferably 30 parts by weight with respect to 100 parts by weight of the curable resin.
- the content of the polymerization initiator is 0.1 parts by weight or more, the obtained sealing agent for liquid crystal display elements is more excellent in curability.
- the content of the polymerization initiator is 30 parts by weight or less, the obtained sealing agent for liquid crystal display elements is more excellent in storage stability.
- a more preferable lower limit of the content of the polymerization initiator is 1 part by weight, a more preferable upper limit is 10 parts by weight, and a still more preferable upper limit is 5 parts by weight.
- thermosetting agent examples include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Among these, solid organic acid hydrazide is preferably used.
- the said thermosetting agent may be used independently and 2 or more types may be used in combination.
- Examples of the solid organic acid hydrazide include 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin, sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
- Examples of commercially available organic acid hydrazides include organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd., organic acid hydrazides manufactured by Nippon Finechem Co., Ltd., organic acid hydrazides manufactured by Ajinomoto Fine Techno Co., and the like. Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd.
- Examples of the organic acid hydrazide manufactured by Nippon Finechem Co., Ltd. include MDH. Examples of the organic acid hydrazide manufactured by Ajinomoto Fine Techno Co. include Amicure VDH, Amicure VDH-J, Amicure UDH (all manufactured by Ajinomoto Fine Techno Co., Ltd.), and the like.
- the content of the thermosetting agent is preferably 1 part by weight with respect to 100 parts by weight of the curable resin, and 50 parts by weight with respect to the preferable upper limit.
- the content of the thermosetting agent is 1 part by weight or more, the obtained sealing agent for liquid crystal display elements is more excellent in thermosetting.
- the content of the thermosetting agent is 50 parts by weight or less, the obtained sealing agent for liquid crystal display elements is more excellent in applicability.
- the upper limit with more preferable content of the said thermosetting agent is 30 weight part.
- the sealing compound for liquid crystal display elements of this invention contains a silane coupling agent.
- the silane coupling agent mainly has a role as an adhesion assistant for favorably bonding the sealing agent and the substrate.
- silane coupling agent for example, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane and the like are preferably used. It is done. These silane coupling agents are excellent in the effect of improving the adhesion to a substrate or the like, and can suppress the outflow of the curable resin into the liquid crystal by chemically bonding with the curable resin.
- the said silane coupling agent may be used independently and 2 or more types may be used in combination.
- the minimum with preferable content of the said silane coupling agent in 100 weight part of sealing compounds for liquid crystal display elements of this invention is 0.1 weight part, and a preferable upper limit is 10 weight part.
- the content of the silane coupling agent is within this range, the obtained sealing agent for liquid crystal display elements is excellent in adhesiveness while suppressing the occurrence of liquid crystal contamination.
- the minimum with more preferable content of the said silane coupling agent is 0.3 weight part, and a more preferable upper limit is 5 weight part.
- the sealing agent for liquid crystal display elements of the present invention may contain a light shielding agent in addition to the inorganic filler.
- a light shielding agent By containing the said light shielding agent, the sealing compound for liquid crystal display elements of this invention can be used suitably as a light shielding sealing agent.
- the light-shielding agent examples include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Of these, titanium black is preferable.
- the said light-shielding agent may be used independently and 2 or more types may be used in combination.
- Titanium black is a substance having higher transmittance for light in the vicinity of the ultraviolet region, particularly for light with a wavelength of 370 nm to 450 nm, compared to the average transmittance for light with a wavelength of 300 nm to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby providing a light shielding property to the sealing agent for liquid crystal display elements of the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region.
- the light shielding agent contained in the liquid crystal display element sealant of the present invention is preferably a highly insulating material, and titanium black is also preferred as the highly insulating light shielding agent.
- the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
- the liquid crystal display element produced using the sealing agent for liquid crystal display elements of the present invention containing the above-described titanium black as a light-shielding agent has a sufficient light-shielding property, and thus has high contrast without light leakage. A liquid crystal display element having excellent image display quality can be realized.
- Examples of commercially available titanium black include titanium black manufactured by Mitsubishi Materials Corporation and titanium black manufactured by Ako Kasei Co., Ltd. Examples of the titanium black manufactured by Mitsubishi Materials include 12S, 13M, 13M-C, 13R-N, and 14M-C. Examples of the titanium black manufactured by Ako Kasei Co., Ltd. include Tilac D.
- the preferable lower limit of the specific surface area of the titanium black is 13 m 2 / g, the preferable upper limit is 30 m 2 / g, the more preferable lower limit is 15 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
- the preferred lower limit of the volume resistance of the titanium black is 0.5 ⁇ ⁇ cm, the preferred upper limit is 3 ⁇ ⁇ cm, the more preferred lower limit is 1 ⁇ ⁇ cm, and the more preferred upper limit is 2.5 ⁇ ⁇ cm.
- the primary particle diameter of the said light-shielding agent will not be specifically limited if it is below the distance between the board
- the more preferable lower limit of the primary particle diameter of the light shielding agent is 5 nm
- the more preferable upper limit is 200 nm
- the still more preferable lower limit is 10 nm
- the still more preferable upper limit is 100 nm.
- the primary particle size of the light shielding agent can be measured by using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS) and dispersing the light shielding agent in a solvent (water, organic solvent, etc.).
- the preferable lower limit of the content of the light-shielding agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 5 parts by weight, and the preferable upper limit is 80 parts by weight.
- the content of the light-shielding agent is within this range, the effect of improving the light-shielding property while suppressing deterioration of the adhesiveness, strength after curing, and drawing property of the obtained sealing agent for liquid crystal display elements is excellent. It will be a thing.
- the more preferable lower limit of the content of the light shielding agent is 10 parts by weight, the more preferable upper limit is 70 parts by weight, the still more preferable lower limit is 30 parts by weight, and the still more preferable upper limit is 60 parts by weight.
- the sealing agent for liquid crystal display elements of the present invention may further contain additives such as reactive diluents, spacers, curing accelerators, antifoaming agents, leveling agents, polymerization inhibitors, and other coupling agents as necessary. You may contain.
- the sealing agent for liquid crystal display elements of the present invention for example, using a mixer, a curable resin, a polymerization initiator and / or a thermosetting agent, an inorganic filler having a hydrophobic group on the surface, and And a method of mixing an additive such as a silane coupling agent added as necessary.
- the mixer include a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll.
- cured material is 2.0 GPa. Since the storage elastic modulus at 25 ° C. of the cured product is 2.0 GPa or less, the sealing agent for liquid crystal display elements of the present invention has excellent flexibility and adhesiveness (particularly, adhesion to an alignment film). Thus, it is possible to prevent peeling of the panel when the obtained liquid crystal display element receives an impact due to dropping or the like.
- cured material is 1.8 GPa. Moreover, from a viewpoint of adhesiveness when the adherend is bonded, a preferable lower limit of the storage elastic modulus at 25 ° C.
- the cured product for measuring the storage elastic modulus was irradiated with 100 mW / cm 2 ultraviolet rays (wavelength 365 nm) for 30 seconds using a metal halide lamp as a sealing agent, and then cured by heating at 120 ° C. for 1 hour. Things are used.
- the storage elastic modulus was measured using a dynamic viscoelasticity measuring apparatus (for example, “DVA-200” manufactured by IT Measurement Control Co., Ltd.) with a test piece width of 5 mm, a thickness of 0.35 mm, a grip width of 25 mm, and a temperature rise. It can be measured under conditions of a speed of 10 ° C./min and a frequency of 10 Hz.
- the sealant for a liquid crystal display element of the present invention has a moisture permeability of 25 g / m 2 ⁇ 24 hr in an environment of 60 ° C. and 90% RH of a cured product having a thickness of 0.7 ⁇ m, measured according to JIS Z 0208.
- the following is preferable.
- the moisture permeability is 25 g / m 2 ⁇ 24 hr or less, the obtained liquid crystal display element is more excellent in moisture resistance reliability.
- the cured product for measuring the moisture permeability is a cured product that is irradiated with 100 mW / cm 2 ultraviolet rays (wavelength 365 nm) for 30 seconds using a metal halide lamp and then heated at 120 ° C. for 1 hour to be cured. Is used.
- the preferable upper limit of the thixotropic index is 1.8.
- the thixotropic index is 1.8 or less, the workability when applying the liquid crystal display element sealing agent of the present invention to a substrate is improved.
- a more preferable upper limit of the thixotropic index is 1.7.
- the preferable lower limit of the thixotropic index is 1.1.
- the thixotropic index is obtained by dividing the viscosity measured under the conditions of 25 ° C. and 0.5 rpm using an E-type viscometer by the viscosity measured under the conditions of 25 ° C. and 5.0 rpm. Mean value.
- a vertical conduction material can be produced by blending conductive fine particles with the sealing agent for liquid crystal display elements of the present invention.
- Such a vertical conduction material containing the sealing agent for liquid crystal display elements of the present invention and conductive fine particles is also one aspect of the present invention.
- the conductive fine particles are not particularly limited, and metal balls, those obtained by forming a conductive metal layer on the surface of resin fine particles, and the like can be used. Among them, the one in which the conductive metal layer is formed on the surface of the resin fine particles is preferable because the conductive connection is possible without damaging the transparent substrate due to the excellent elasticity of the resin fine particles.
- the liquid crystal display element using the sealing agent for liquid crystal display elements of this invention or the vertical conduction material of this invention is also one of this invention.
- a liquid crystal dropping method is preferably used. Specific examples include a method having the following steps. First, a step of forming a frame-shaped seal pattern by applying the liquid crystal display element sealing agent of the present invention to one of two transparent substrates having electrodes such as an ITO thin film by screen printing, dispenser coating or the like is performed. Next, a step of applying liquid crystal microdroplets onto the entire surface of the frame of the seal pattern and superimposing the other transparent substrate under vacuum is performed. Thereafter, a liquid crystal display element can be obtained by a method of irradiating the seal pattern portion with light such as ultraviolet rays to temporarily cure the sealing agent and a method of heating and temporarily curing the temporarily cured sealing agent. it can.
- the sealing compound for liquid crystal display elements which is excellent in impact resistance, a softness
- the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.
- Examples 1 to 6, Comparative Examples 1 to 4 According to the mixing ratios described in Tables 1 and 2, after mixing each material using a planetary stirrer (“Shinky Co., Ltd.,“ Awatori Netaro ”), by further mixing using three rolls Sealants for liquid crystal display elements of Examples 1 to 6 and Comparative Examples 1 to 4 were prepared. About each obtained sealing compound for liquid crystal display elements, 100 mW / cm ⁇ 2 > ultraviolet-ray (wavelength 365nm) was irradiated for 30 second using the metal halide lamp, Then, hardened
- a planetary stirrer (“Shinky Co., Ltd.,“ Awatori Netaro ”).
- the sealing compound for liquid crystal display elements which is excellent in impact resistance, a softness
- the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.
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Abstract
Description
滴下工法では、まず、2枚の電極付き基板の一方に、ディスペンスにより枠状のシールパターンを形成する。次いで、シール剤が未硬化の状態で液晶の微小滴を基板のシール枠内に滴下し、真空下で他方の基板を重ね合わせ、シール部に紫外線等の光を照射して仮硬化を行う。その後、加熱して本硬化を行い、液晶表示素子を作製する。現在この滴下工法が液晶表示素子の製造方法の主流となっている。
このような狭額縁設計に伴い、液晶表示素子において画素領域からシール剤までの距離が近くなっており、シール剤が配向膜上に配置されることが多くなっている。
以下に本発明を詳述する。
更に、上記疎水性基を表面に有する無機フィラーは、本発明の液晶表示素子用シール剤の耐衝撃性を向上させる効果も有する。上記疎水性基を表面に有する無機フィラーを含有することでシール剤の耐衝撃性が向上する理由としては、以下のことが考えられる。即ち、無機フィラーを疎水性基を表面に有するものとすることにより、該無機フィラーが硬化性樹脂中に分散しやすくなる。その結果、無機フィラーの凝集により生じる、シール剤の硬化物が脆くなったり、柔軟性が低下したりすることが抑制されているものと考えられる。このシール剤の耐衝撃性が向上する効果は、硬化性樹脂として重合性官能基と環状ラクトンの開環構造とを有する化合物と、アルキル基を表面に有する無機フィラーとを組み合わせて用いた場合に特に好適に発揮される。
上記基材粒子としては、例えば、シリカ、タルク、ガラスビーズ、石綿、石膏、珪藻土、スメクタイト、ベントナイト、モンモリロナイト、セリサイト、活性白土、アルミナ、酸化亜鉛、酸化鉄、酸化マグネシウム、酸化錫、酸化チタン、炭酸カルシウム、炭酸マグネシウム、水酸化マグネシウム、水酸化アルミニウム、窒化アルミニウム、窒化珪素、硫酸バリウム、珪酸カルシウム等の無機粒子が挙げられる。なかでも、シリカが好ましい。
上述したように、本発明の液晶表示素子用シール剤は、硬化性樹脂として重合性官能基と環状ラクトンの開環構造とを有する化合物と、アルキル基を表面に有する無機フィラーとを組み合わせて用いることが好ましい。
なお、本明細書において、上記「(メタ)アクリル」とは、アクリル又はメタクリルを意味する。
なお、本明細書において上記疎水性基を表面に有する無機フィラーの平均粒子径は、走査型電子顕微鏡を用いて、5000倍の倍率で観察した粒子10個の粒子径(長径)の平均値を意味する。
また、塗布性等の観点から、上記疎水性基を表面に有する無機フィラーの含有割合の好ましい上限は70重量%、より好ましい上限は50重量%である。
上記その他のフィラーとしては、例えば、上記疎水性基を表面に有する無機フィラーの基材粒子として挙げた無機粒子や、ポリエステル微粒子、ポリウレタン微粒子、ビニル重合体微粒子、アクリル重合体微粒子等の有機粒子等が挙げられる。
本発明の液晶表示素子用シール剤において、硬化物の25℃における貯蔵弾性率を2.0GPa以下とする方法としては、上記硬化性樹脂として重合性官能基と柔軟骨格とを有する化合物を用いる方法が好適である。
なお、本明細書において上記「(メタ)アクリロイル」は、アクリロイル又はメタクリロイルを意味する。
上述したように、本発明の液晶表示素子用シール剤は、硬化性樹脂として重合性官能基と環状ラクトンの開環構造とを有する化合物と、アルキル基を表面に有する無機フィラーとを組み合わせて用いることが好ましい。
なお、本明細書において上記「(メタ)アクリレート」とは、アクリレート又はメタクリレートを意味し、上記「エポキシ(メタ)アクリレート」とは、エポキシ化合物中の全てのエポキシ基を(メタ)アクリル酸と反応させた化合物のことを表す。
なお、本明細書において、上記「(メタ)アクリル化合物」とは、(メタ)アクリロイル基を有する化合物を意味する。
上記ヒドロキシアルキルモノ(メタ)アクリレートとしては、例えば、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、4-ヒドロキシブチル(メタ)アクリレート等が挙げられる。
上記二価のアルコールとしては、例えば、エチレングリコール、プロピレングリコール、1,3-プロパンジオール、1,3-ブタンジオール、1,4-ブタンジオール、ポリエチレングリコール等が挙げられる。
上記三価のアルコールとしては、例えば、トリメチロールエタン、トリメチロールプロパン、グリセリン等が挙げられる。
上記エポキシ(メタ)アクリレートとしては、例えば、ビスフェノールA型エポキシアクリレート等が挙げられる。
上記重合開始剤としては、例えば、ラジカル重合開始剤、カチオン重合開始剤等が挙げられる。
上記BASF社製の光ラジカル重合開始剤としては、例えば、IRGACURE184、IRGACURE369、IRGACURE379、IRGACURE651、IRGACURE819、IRGACURE907、IRGACURE2959、IRGACURE OXE01、ルシリンTPO等が挙げられる。
上記ライトケミカル社製の光ラジカル重合開始剤としては、例えば、KR-02等が挙げられる。
上記東京化成工業社製の光ラジカル重合開始剤としては、例えば、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル等が挙げられる。
なお、本明細書において高分子アゾ化合物とは、アゾ基を有し、熱によって(メタ)アクリロイルオキシ基を硬化させることができるラジカルを生成する、数平均分子量が300以上の化合物を意味する。
なお、本明細書において、上記数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)で溶媒としてテトラヒドロフランを用いて測定を行い、ポリスチレン換算により求められる値である。GPCによってポリスチレン換算による数平均分子量を測定する際のカラムとしては、例えば、Shodex LF-804(昭和電工社製)等が挙げられる。
上記アゾ基を介してポリアルキレンオキサイド等のユニットが複数結合した構造を有する高分子アゾ化合物としては、ポリエチレンオキサイド構造を有するものが好ましい。
上記高分子アゾ化合物としては、具体的には例えば、4,4’-アゾビス(4-シアノペンタン酸)とポリアルキレングリコールの重縮合物や、4,4’-アゾビス(4-シアノペンタン酸)と末端アミノ基を有するポリジメチルシロキサンの重縮合物等が挙げられる。
上記高分子アゾ化合物のうち市販されているものとしては、例えば、VPE-0201、VPE-0401、VPE-0601、VPS-0501、VPS-1001(いずれも富士フイルム和光純薬社製)等が挙げられる。
また、高分子ではないアゾ化合物として市販されているものとしては、例えば、V-65、V-501(いずれも富士フイルム和光純薬社製)等が挙げられる。
上記光カチオン重合開始剤としては、例えば、芳香族ジアゾニウム塩、芳香族ハロニウム塩、芳香族スルホニウム塩等のオニウム塩類、鉄-アレン錯体、チタノセン錯体、アリールシラノール-アルミニウム錯体等の有機金属錯体類等が挙げられる。
上記熱硬化剤は、単独で用いられてもよいし、2種以上が組み合わせて用いられてもよい。
上記有機酸ヒドラジドのうち市販されているものとしては、例えば、大塚化学社製の有機酸ヒドラジド、日本ファインケム社製の有機酸ヒドラジド、味の素ファインテクノ社製の有機酸ヒドラジド等が挙げられる。
上記大塚化学社製の有機酸ヒドラジドとしては、例えば、SDH、ADH等が挙げられる。
上記日本ファインケム社製の有機酸ヒドラジドとしては、例えば、MDH等が挙げられる。
上記味の素ファインテクノ社製の有機酸ヒドラジドとしては、例えば、アミキュアVDH、アミキュアVDH-J、アミキュアUDH(いずれも味の素ファインテクノ社製)等が挙げられる。
上記シランカップリング剤は、単独で用いられてもよいし、2種以上が組み合わせて用いられてもよい。
上記遮光剤は、単独で用いられてもよいし、2種以上が組み合わせて用いられてもよい。
また、遮光剤として上記チタンブラックを含有する本発明の液晶表示素子用シール剤を用いて製造した液晶表示素子は、充分な遮光性を有するため、光の漏れ出しがなく高いコントラストを有し、優れた画像表示品質を有する液晶表示素子を実現することができる。
上記三菱マテリアル社製のチタンブラックとしては、例えば、12S、13M、13M-C、13R-N、14M-C等が挙げられる。
上記赤穂化成社製のチタンブラックとしては、例えば、ティラックD等が挙げられる。
また、上記チタンブラックの体積抵抗の好ましい下限は0.5Ω・cm、好ましい上限は3Ω・cmであり、より好ましい下限は1Ω・cm、より好ましい上限は2.5Ω・cmである。
なお、上記遮光剤の一次粒子径は、NICOMP 380ZLS(PARTICLE SIZING SYSTEMS社製)を用いて、上記遮光剤を溶媒(水、有機溶媒等)に分散させて測定することができる。
上記混合機としては、例えば、ホモディスパー、ホモミキサー、万能ミキサー、プラネタリーミキサー、ニーダー、3本ロール等が挙げられる。
また、被着体を貼り合わせた際の接着性等の観点から、上記硬化物の25℃における貯蔵弾性率の好ましい下限は1MPa、より好ましい下限は0.01GPaである。
なお、上記貯蔵弾性率を測定する硬化物としては、シール剤にメタルハライドランプを用いて100mW/cm2の紫外線(波長365nm)を30秒照射した後、120℃で1時間加熱して硬化させたものが用いられる。
また、上記貯蔵弾性率は、動的粘弾性測定装置(例えば、IT計測制御社製、「DVA-200」等)を用いて、試験片幅5mm、厚み0.35mm、掴み幅25mm、昇温速度10℃/分、周波数10Hzの条件で測定することができる。
なお、上記透湿度を測定する硬化物としては、シール剤にメタルハライドランプを用いて100mW/cm2の紫外線(波長365nm)を30秒照射した後、120℃で1時間加熱して硬化させたものが用いられる。
また、上記チクソトロピックインデックスの好ましい下限は1.1である。
なお、本明細書において上記チクソトロピックインデックスとは、E型粘度計を用いて、25℃、0.5rpmの条件で測定した粘度を、25℃、5.0rpmの条件で測定した粘度で除した値を意味する。
本発明の液晶表示素子を製造する方法としては、液晶滴下工法が好適に用いられ、具体的には例えば、以下の各工程を有する方法等が挙げられる。
まず、ITO薄膜等の電極を有する2枚の透明基板の一方に、本発明の液晶表示素子用シール剤をスクリーン印刷、ディスペンサー塗布等により塗布して枠状のシールパターンを形成する工程を行う。次いで、液晶の微小滴をシールパターンの枠内全面に滴下塗布し、真空下で他方の透明基板を重ね合わせる工程を行う。その後、シールパターン部分に紫外線等の光を照射してシール剤を仮硬化させる工程、及び、仮硬化させたシール剤を加熱して本硬化させる工程を行う方法により、液晶表示素子を得ることができる。
表1、2に記載された配合比に従い、各材料を、遊星式撹拌機(シンキー社製、「あわとり練太郎」)を用いて混合した後、更に3本ロールを用いて混合することにより実施例1~6、比較例1~4の液晶表示素子用シール剤を調製した。
得られた各液晶表示素子用シール剤について、メタルハライドランプを用いて100mW/cm2の紫外線(波長365nm)を30秒照射した後、120℃で1時間加熱することにより硬化物を得た。得られた硬化物について、動的粘弾性測定装置(IT計測制御社製、「DVA-200」)を用いて、試験片幅5mm、厚み0.35mm、掴み幅25mm、昇温速度10℃/分周波数5HZの条件で25℃における貯蔵弾性率を測定した。結果を表1、2に示した。
実施例及び比較例で得られた各液晶表示素子用シール剤について以下の評価を行った。結果を表1、2に示した。
実施例及び比較例で得られた各液晶表示素子用シール剤を、平滑な離型フィルム上にコーターを用いて塗布した。次いで、塗布したシール剤にメタルハライドランプを用いて100mW/cm2の紫外線(波長365nm)を30秒照射した後、120℃で1時間加熱することによって透湿度測定用フィルム(厚さ0.7μm)を得た。JIS Z 0208の防湿包装材料の透湿度試験方法(カップ法)に準じた方法で透湿度試験用カップを作製し、得られた透湿度測定用フィルムを取り付け、60℃、90%RHの恒温恒湿オーブンに投入して透湿度を測定した。
実施例及び比較例で得られた各液晶表示素子用シール剤100重量部にスペーサー微粒子(積水化学工業社製、「ミクロパールSI-H050」)1重量部を分散させた。次いで、2枚のラビング済み配向膜及び透明電極付き基板(長さ75mm、幅75mm、厚み0.7mm)の一方に、表示部が45mm×55mmとなるように、スペーサー微粒子を分散させたシール剤を線幅0.7mmでディスペンサー塗布した。続いて液晶(チッソ社製、「JC-5004LA」)の微小滴をシール剤の枠内全面に滴下塗布し、すぐにもう一方の基板を貼り合わせ、シール剤部分にメタルハライドランプを用いて100mW/cm2の紫外線(波長365nm)を30秒照射した後、120℃で1時間加熱することにより、液晶表示素子を得た。実施例及び比較例で得られた各液晶表示素子用シール剤について、液晶表示素子をそれぞれ10セルずつ作製した。
得られた各液晶表示素子について、2mの高さから落下させる落下試験を行った。落下試験後、全てのセルに剥がれや割れによる液晶漏れがなかった場合を「◎」、1セル以上4セル未満の液晶表示素子に液晶漏れがあった場合を「○」、4セル以上7セル未満の液晶表示素子に液晶漏れがあった場合を「△」、7セル以上の液晶表示素子に液晶漏れがあった場合を「×」として耐衝撃性を評価した。
Claims (4)
- 硬化性樹脂と、重合開始剤及び/又は熱硬化剤と、疎水性基を表面に有する無機フィラーとを含有し、
前記疎水性基を表面に有する無機フィラーの含有割合が15重量%以上であり、
硬化物の25℃における貯蔵弾性率が2.0GPa以下である
ことを特徴とする液晶表示素子用シール剤。 - JIS Z 0208に準拠して測定される、厚さ0.7μmの硬化物の60℃、90%RHの環境下における透湿度が25g/m2・24hr以下である請求項1記載の液晶表示素子用シール剤。
- 請求項1又は2記載の液晶表示素子用シール剤と導電性微粒子とを含有する上下導通材料。
- 請求項1若しくは2記載の液晶表示素子用シール剤又は請求項3記載の上下導通材料を用いてなる液晶表示素子。
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WO2020175443A1 (ja) * | 2019-02-25 | 2020-09-03 | 積水化学工業株式会社 | 表示素子用シール剤、上下導通材料、及び、表示素子 |
JP2020187302A (ja) * | 2019-05-16 | 2020-11-19 | 積水化学工業株式会社 | 液晶表示素子の製造方法 |
JPWO2020116267A1 (ja) * | 2018-12-07 | 2021-02-15 | 積水化学工業株式会社 | 液晶表示素子用シール剤、硬化物、上下導通材料、及び、液晶表示素子 |
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JP2020187302A (ja) * | 2019-05-16 | 2020-11-19 | 積水化学工業株式会社 | 液晶表示素子の製造方法 |
WO2022196764A1 (ja) * | 2021-03-19 | 2022-09-22 | 三井化学株式会社 | 液晶シール剤、液晶表示パネルの製造方法および液晶表示パネル |
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CN110168441A (zh) | 2019-08-23 |
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