WO2011118192A1 - Agent d'étanchéité à cristaux liquides, procédé de fabrication d'un panneau d'affichage à cristaux liquides au moyen de celui-ci et panneau d'affichage à cristaux liquides - Google Patents

Agent d'étanchéité à cristaux liquides, procédé de fabrication d'un panneau d'affichage à cristaux liquides au moyen de celui-ci et panneau d'affichage à cristaux liquides Download PDF

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Publication number
WO2011118192A1
WO2011118192A1 PCT/JP2011/001646 JP2011001646W WO2011118192A1 WO 2011118192 A1 WO2011118192 A1 WO 2011118192A1 JP 2011001646 W JP2011001646 W JP 2011001646W WO 2011118192 A1 WO2011118192 A1 WO 2011118192A1
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WIPO (PCT)
Prior art keywords
liquid crystal
substrate
group
display panel
weight
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PCT/JP2011/001646
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English (en)
Japanese (ja)
Inventor
溝部祐司
水田康司
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三井化学株式会社
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Priority to KR1020117030068A priority Critical patent/KR101343156B1/ko
Priority to CN201180002917.XA priority patent/CN102472929B/zh
Priority to JP2011522321A priority patent/JP4815027B1/ja
Publication of WO2011118192A1 publication Critical patent/WO2011118192A1/fr
Priority to HK12111066.2A priority patent/HK1170312A1/xx

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/10—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
    • C08G59/18—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
    • C08G59/40—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 characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5046—Amines heterocyclic
    • C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
    • C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
    • 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
    • C08G59/68—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 characterised by the catalysts used
    • C08G59/686—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 characterised by the catalysts used containing nitrogen
    • 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
    • C09K2003/1034—Materials or components characterised by specific properties
    • C09K2003/1059—Heat-curable materials
    • 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 liquid crystal sealant, a method for producing a liquid crystal display panel using the same, and a liquid crystal display panel.
  • liquid crystal display panels have been widely used as image display panels for various electronic devices such as mobile phones and personal computers.
  • the liquid crystal display panel has a structure in which a liquid crystal material (hereinafter simply referred to as “liquid crystal”) is sandwiched between two transparent substrates having electrodes provided on the surface, and the periphery thereof is sealed with a liquid crystal sealant. It is.
  • liquid crystal sealant has a small influence on the reliability of the liquid crystal display panel because it is in direct contact with the liquid crystal although the amount used is small. Therefore, in order to achieve high image quality of the liquid crystal display panel, liquid crystal sealants are currently required to have advanced and diverse characteristics.
  • liquid crystal display panels are mainly manufactured by a liquid crystal injection method.
  • the liquid crystal injection method is (1) after applying a liquid crystal sealant on one transparent substrate to form a frame, and (2) drying the liquid crystal sealant by precuring the substrate.
  • the other substrate is bonded, (3) the two substrates are heated and pressed, and the substrates are bonded together to form a frame (cell) of the liquid crystal sealant between the substrates, and (4) empty
  • This is a method of manufacturing a liquid crystal display panel by injecting an appropriate amount of liquid crystal into a cell and then sealing the liquid crystal injection port.
  • liquid crystal dropping method has been studied as a method for manufacturing a liquid crystal display panel, which is expected to improve productivity.
  • a liquid crystal sealant is applied on a transparent substrate to form a frame for filling the liquid crystal
  • a minute liquid crystal is dropped into the frame
  • liquid crystal In this method, two substrates are stacked under high vacuum while the sealant is in an uncured state, and then (4) the liquid crystal sealant is cured to produce a panel.
  • a light and thermosetting liquid crystal sealant is used, and in the step (3), after the liquid crystal sealant is pre-cured by irradiating light such as ultraviolet rays, it is post-cured by heating. Has been done.
  • liquid crystal sealant for the liquid crystal dropping method a liquid crystal sealant using a crystalline epoxy resin that is difficult to dissolve in liquid crystal has been proposed (for example, Patent Document 1). Further, a liquid crystal sealant using isophthalic acid dihydrazide as a thermosetting agent has been proposed (for example, Patent Document 2). According to this, isophthalic acid dihydrazide has low compatibility with liquid crystals, and can cure a resin at a low temperature and in a short time. In addition, liquid crystal sealing agents using imidazole compounds as thermosetting agents have been proposed (for example, Patent Documents 3 and 4).
  • liquid crystal sealing agent for a liquid crystal injection method including a specific latent curing agent and an imidazole curing accelerator having a phenyl group at the 2-position and a melting point of 170 ° C. or higher has been proposed (for example, Patent Document 5).
  • Patent Document 1 has a certain decrease in solubility in liquid crystal at room temperature. However, since the resin easily dissolves in the liquid crystal under high temperature and high humidity conditions, the display characteristics of the liquid crystal display panel may be deteriorated. Further, although the liquid crystal sealing agents of Patent Documents 2 to 5 are cured in a short time to some extent, their curability at low temperatures is not a sufficient level. For this reason, there exists a possibility that the uncured component of the liquid crystal sealant may be dissolved in the liquid crystal and deteriorate the display characteristics of the liquid crystal display panel.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a liquid crystal sealant that is hardly soluble in liquid crystals, can be cured at a low temperature in a short time, and has excellent display reliability.
  • the present inventors paid attention to the fact that an epoxy resin can be cured at a low temperature in a short time in the presence of an imidazole-based curing catalyst.
  • the imidazole-based curing catalyst is not only easily dissolved in the liquid crystal due to its chemical structure, but also because the curing catalyst is not incorporated into the crosslinked structure of the resin, it remains in the cured resin and is easily eluted into the liquid crystal. There was a bug. Accordingly, the present inventors have found that elution into the liquid crystal can be suppressed by introducing a certain amount or more of hydroxyl groups into the imidazole-based curing catalyst to reduce the compatibility with the liquid crystal.
  • the present inventors have increased the catalytic activity of the imidazole-based curing catalyst (lowering the melting point) and used it in combination with other thermosetting agents, so that even with a small amount of the curing catalyst, the resin can be made at low temperature and short. It has been found that it can be cured in time. The present invention has been made based on such findings.
  • the first of the present invention relates to the following liquid crystal sealant.
  • a curable resin containing an epoxy resin, a thermosetting agent, and 0.1 to 10 parts by weight of a curing catalyst with respect to a total of 100 parts by weight of the curable resin, the curing catalyst Is a liquid crystal sealant which is an imidazole-based curing catalyst having a melting point represented by formula (1) of 150 ° C. or lower.
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, a phenyl group or a benzyl group; 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms, and at least one of R 1 to R 4 is a lower hydroxyalkyl group. It is a group.
  • thermosetting agent is at least one selected from the group consisting of a dihydrazide compound, a polyamine compound, and a phenol compound.
  • thermosetting agent is at least one selected from the group consisting of a dihydrazide compound, a polyamine compound, and a phenol compound.
  • a photopolymerization initiator is further included, and the curable resin further includes at least one of an acrylic resin and an epoxy resin having a (meth) acryl group and an epoxy group in the molecule. 4] The liquid crystal sealing agent in any one of.
  • the second of the present invention relates to a method for producing a liquid crystal display panel and a liquid crystal display panel obtained thereby.
  • a method for manufacturing a liquid crystal display panel comprising: a step of superimposing the seal pattern on the surface, and a step of thermosetting the seal pattern.
  • thermosetting temperature 80 to 100 ° C.
  • a display substrate, a counter substrate paired with the display substrate, a frame-shaped sealing member interposed between the display substrate and the counter substrate, and between the display substrate and the counter substrate A liquid crystal layer filled in a space surrounded by the sealing member, wherein the sealing member is a cured liquid crystal sealing agent according to any one of [1] to [6] A liquid crystal display panel.
  • the liquid crystal sealant excellent in display reliability can be provided because the liquid crystal is less contaminated and can be cured at a low temperature and in a short time.
  • the liquid crystal sealant of the present invention contains at least (A-1) a curable resin containing an epoxy resin, (A-2) a thermosetting agent, and (A-3) a specific imidazole-based curing catalyst.
  • the curable resin may further contain (B) (meth) acryl-modified epoxy resin and (C) acrylic resin as necessary.
  • the liquid crystal sealing agent of the present invention may further contain (D) a photopolymerization initiator and (E) a filler, if necessary.
  • Epoxy Resin The epoxy resin used in the present invention is not particularly limited as long as it is a bifunctional or higher functional epoxy resin, and is not limited to bisphenol A type, bisphenol F type, bisphenol S type, 2,2′-diallyl bisphenol.
  • Bisphenol type epoxy resins such as A type, bisphenol AD type and hydrogenated bisphenol type; diphenyl ether type epoxy resin; phenol novolak type, cresol novolak type, biphenyl novolak type, bisphenol novolak type, naphthol novolak type, trisphenol novolak type, di Novolak type epoxy resins such as cyclopentadiene novolac type; biphenyl type epoxy resin; naphthyl type epoxy resin; triphenol methane type, triphenol ethane type, triphenol propane type, etc.
  • E Nord alkane type epoxy resins include alicyclic epoxy resins and the like.
  • bifunctional epoxy resins are preferable, and bisphenol type epoxy resins such as bisphenol A type and bisphenol F type are more preferable. This is because these bisphenol-type epoxy resins have advantages such as excellent coating stability because they have lower crystallinity than diphenyl ether-type epoxy resins and the like.
  • the weight average molecular weight (Mw) of the epoxy resin is preferably 400 to 3000, and more preferably 600 to 2000.
  • the weight average molecular weight of the epoxy resin can be measured, for example, by gel permeation chromatography (GPC) using polystyrene as a standard.
  • the epoxy resin may be used alone, or two or more types of epoxy resins having different types and molecular weights may be used in combination.
  • thermosetting agent Even when mixed with an epoxy resin, the thermosetting agent does not cure the epoxy resin under normal storage conditions (room temperature, under visible light, etc.). It is a latent curing agent that cures the resin.
  • the thermosetting agent in the present invention is incorporated as a crosslinking group in the cured resin.
  • thermosetting agent known ones are used. In order to increase the viscosity stability of the liquid crystal sealing agent, a thermosetting agent having a melting point of 50 ° C. or more and 250 ° C. or less is preferable, and a low thermosetting temperature (about 80 to 100 ° C.). However, in order to cure the resin, a thermosetting agent having a melting point of 50 ° C. or higher and 150 ° C. or lower is more preferable.
  • thermosetting agents include organic acid dihydrazide compounds, polyamine compounds, dicyandiamide compounds, phenol compounds, and the like.
  • organic acid dihydrazide compounds include adipic acid dihydrazide (melting point 181 ° C.), 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin (melting point 120 ° C.), 7,11-octadecadien-1 , 18-dicarbohydrazide (melting point 160 ° C.), dodecanedioic acid dihydrazide (melting point 190 ° C.), sebacic acid dihydrazide (melting point 189 ° C.), and the like.
  • the polyamine-based compound is a thermal latent curing agent having a polymer structure obtained by reacting an amine and an epoxy.
  • ADEKA Hardener EH4339S softening point 120 to 130 ° C.
  • Adeka Hardener EH4357S softening point 73 to 83 ° C.
  • ADEKA Corporation Adeka Hardener EH4357S manufactured by ADEKA Corporation is included.
  • the dicyandiamide compound include dicyandiamide (melting point: 209 ° C.).
  • phenolic compounds include phenol novolac resins, cresol novolac resins, and zylock type novolac resins.
  • organic acid dihydrazide compounds are preferable from the viewpoint of obtaining high curing characteristics when used in combination with an imidazole curing catalyst described later. These may be used alone or in combination.
  • thermosetting agent is 1 to 20 with respect to 100 parts by weight of the total of the curable resin (the total of (A-1) epoxy resin, (B) (meth) acryl-modified epoxy resin and (C) acrylic resin). Part by weight, more preferably 3 to 15 parts by weight.
  • a liquid crystal sealant containing a thermosetting agent can be a so-called one-part curable resin composition.
  • the one-component curable resin composition is excellent in workability because it is not necessary to mix the main agent and the curing agent when used.
  • R 1 and R 2 are each independently a hydrogen atom, a lower alkyl group, a lower hydroxyalkyl group, a phenyl group or a benzyl group.
  • R 3 and R 4 are each independently a hydrogen atom, a lower alkyl group or a lower hydroxyalkyl group. At least one of R 1 to R 4 is a lower hydroxyalkyl group.
  • the imidazole-based curing catalyst having a lower hydroxyalkyl group contains a hydroxyl group and thus is difficult to dissolve in the liquid crystal.
  • the lower alkyl group is an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group or a propyl group, preferably a methyl group or an ethyl group.
  • the lower hydroxyalkyl group is a hydroxyalkyl group having 1 to 4 carbon atoms such as a hydroxymethyl group or a hydroxyethyl group, preferably a hydroxymethyl group.
  • the lower hydroxyalkyl group may contain a plurality of hydroxyl groups.
  • the number of hydroxyl groups contained in the imidazole-based curing catalyst is not particularly limited. However, when the number of hydroxyl groups is 2 or more, the water resistance may be decreased. Preferably there is.
  • the melting point of the imidazole-based curing catalyst represented by the formula (1) depends on the thermosetting temperature, but when thermosetting at a lower temperature (for example, about 80 to 100 ° C.), it is preferably 150 ° C. or less. It is more preferably 120 ° C. or less, further preferably 60 to 120 ° C., and particularly preferably 80 to 100 ° C. If the melting point of the imidazole-based curing catalyst is too low, the imidazole-based curing catalyst dissolves at room temperature, so that the resin curing reaction proceeds, and the storage stability of the liquid crystal sealant at room temperature becomes poor.
  • the catalyst function of the imidazole-based curing catalyst may not be sufficiently exhibited at the heat curing temperature.
  • the melting point of the imidazole-based curing catalyst can be lowered by, for example, a structure that does not contain an aromatic ring.
  • R 2 is preferably a group other than a phenyl group or a benzyl group, that is, a hydrogen atom, a lower alkyl group, or a lower hydroxyalkyl group, and more preferably a lower hydroxyalkyl group.
  • Examples of the imidazole-based curing catalyst represented by the formula (1) include 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-hydroxymethylimidazole, 1 -Benzyl-5-hydroxymethylimidazole, 1,2-dihydroxyethylimidazole and the like are included.
  • examples of the imidazole curing catalyst having a melting point of 150 ° C. or lower include 2-hydroxymethylimidazole.
  • the content of the imidazole-based curing catalyst represented by the formula (1) is the total of the curable resins ((A-1) epoxy resin, (B) (meth) acryl-modified epoxy resin and (C) acrylic resin) It is preferably 0.1 parts by weight or more and less than 10 parts by weight with respect to 100 parts by weight, more preferably 0.5 parts by weight or more and 8 parts by weight or less, and 1 part by weight or more and 5 parts by weight or less. Is more preferable.
  • the content of the imidazole curing catalyst represented by the formula (1) is less than 0.1 parts by weight, it is difficult to obtain the effect of adding the curing catalyst, and when it is 10 parts by weight or more, the curing catalyst is dissolved in the liquid crystal. This is because not only is it easy to take out, but the pot life is shortened.
  • the imidazole-based curing catalyst represented by the formula (1) activates the epoxy resin. For this reason, an epoxy resin can be hardened in a short time (before it melt
  • the liquid crystal sealing agent of the present invention may contain a (meth) acryl-modified epoxy resin as necessary.
  • the (meth) acryl-modified epoxy resin includes a resin obtained by reacting a bifunctional or higher functional epoxy resin with (meth) acrylic acid, for example, under a basic catalyst.
  • the bifunctional or higher functional epoxy resin as the raw material may be the same as the above-described epoxy resin.
  • bifunctional epoxy resin such as bisphenol A type epoxy resin and bisphenol F type epoxy resin is used as a raw material
  • (meth) acrylic acid is reacted at a ratio of approximately 1: 1 epoxy group and (meth) acrylic acid.
  • the resin obtained is preferable.
  • the liquid crystal sealant containing the epoxy group can have both photocuring property and thermosetting property.
  • the liquid crystal sealant contains (C) acrylic resin described later
  • the (meth) acryl-modified epoxy resin can enhance the compatibility between the (C) acrylic resin and the (A-1) epoxy resin. Therefore, a cured product having a high glass transition temperature (Tg) and excellent adhesiveness can be obtained.
  • the liquid-crystal sealing compound of this invention may contain the acrylic resin as needed.
  • acrylic resins include diacrylates and / or dimethacrylates such as polyethylene glycol, propylene glycol, polypropylene glycol; diacrylates and / or dimethacrylates of tris (2-hydroxyethyl) isocyanurate; 4 per mole of neopentyl glycol.
  • Diacrylate and / or dimethacrylate of diol obtained by adding at least 1 mole of ethylene oxide or propylene oxide; Diacrylate and / or diacrylate of diol obtained by adding 2 mole of ethylene oxide or propylene oxide to 1 mole of bisphenol A Methacrylate: Diol or triol obtained by adding 3 mol or more of ethylene oxide or propylene oxide to 1 mol of trimethylolpropane.
  • the photopolymerization initiator is a polymerization initiator for photocuring
  • B (meth) acryl-modified epoxy resin or (C) acrylic resin.
  • the sealant can be temporarily cured by photocuring when manufacturing a liquid crystal panel, and the work process becomes easy.
  • photopolymerization initiators can be used. Examples include alkylphenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin compounds, acetophenone compounds, benzophenone compounds, thioxanthone compounds, ⁇ -acyloxime ester compounds, Examples include phenyl glyoxylate compounds, benzyl compounds, azo compounds, diphenyl sulfide compounds, organic dye compounds, iron-phthalocyanine compounds, benzoin ether compounds, anthraquinone compounds, and the like.
  • alkylphenone compounds include benzyl dimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one (IRGACURE 651); 2-methyl-2-morpholino (4-thiomethylphenyl) propane ⁇ -aminoalkylphenones such as 1-one (IIRGACURE 907); ⁇ -hydroxyalkylphenones such as 1-hydroxy-cyclohexyl-phenyl-ketone (IRGACURE 184) and the like.
  • acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and the like, and titanocene compounds include bis ( ⁇ 5-2,4-cyclopentadien-1-yl.
  • oxime ester compounds include 1.2-octanedione-1 -[4- (phenylthio)-, 2- (O-benzoyloxime)] (IRGACURE OXE 01) and the like are included.
  • the content of the photopolymerization initiator includes (A-1) epoxy resin, (A-2) thermosetting agent, (A-3) imidazole-based curing catalyst, (B) (meth) acryl-modified epoxy resin, and ( C) It is preferably 0.3 to 5.0 parts by weight with respect to 100 parts by weight of the total acrylic resin (hereinafter also referred to as “resin unit”).
  • resin unit the total acrylic resin
  • the liquid crystal sealing agent of the present invention may further contain a filler. By adding the filler, it is possible to control the viscosity of the liquid crystal sealant, the strength of the cured product, the linear expansion, and the like.
  • the filler is not particularly limited, but examples include calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, zirconium silicate, iron oxide, titanium oxide, aluminum oxide (alumina), zinc oxide, silicon dioxide, titanium.
  • Inorganic fillers such as potassium acid, kaolin, talc, glass beads, sericite activated clay, bentonite, aluminum nitride and silicon nitride are included, preferably silicon dioxide and talc.
  • the shape of the filler is not particularly limited, and may be a regular shape such as a spherical shape, a plate shape, or a needle shape, or an irregular shape.
  • the filler preferably has an average primary particle size of 1.5 ⁇ m or less and a specific surface area of 1 m 2 / g to 500 m 2 / g.
  • the average primary particle diameter of the filler can be measured by a laser diffraction method described in JIS Z8825-1.
  • the specific surface area can be measured by the BET method described in JIS Z8830.
  • the filling amount of the filler is preferably 1 to 50 parts by weight and more preferably 10 to 30 parts by weight with respect to 100 parts by weight of the resin unit.
  • the liquid crystal sealant of the present invention may contain thermoplastic resin particles (also referred to as “epoxy-modified particles”) modified with an epoxy resin as necessary.
  • the thermoplastic resin particles are obtained by suspension polymerization of a resin containing an epoxy group and a double bond group with a monomer capable of radical polymerization.
  • the thermoplastic resin particles are preferably added when making a liquid crystal sealing agent for a liquid crystal injection method. This is because the shrinkage stress generated in the cured product by heating can be relaxed.
  • thermoplastic resin particles are preferably 1 to 30 parts by weight with respect to 100 parts by weight of the resin unit.
  • the average particle diameter of the thermoplastic resin particles is usually in the range of 0.05 to 5 ⁇ m, more preferably 0.07 to 3 ⁇ m, since the gap of the liquid crystal cell is mainly 5 ⁇ m or less.
  • the liquid crystal sealing agent of the present invention may further include a thermal radical polymerization initiator, a coupling agent such as a silane coupling agent, an ion trapping agent, an ion exchange agent, a leveling agent, a pigment, if necessary. Additives such as dyes, plasticizers and antifoaming agents may be included. Further, a spacer or the like may be blended in order to adjust the gap of the liquid crystal panel.
  • the liquid crystal sealant of the present invention can be used for either a liquid crystal injection method or a liquid crystal dropping method.
  • the liquid crystal sealing agent of the present invention is preferably used in a liquid crystal dropping method because it is difficult to dissolve in liquid crystals and can be cured at a low temperature in a short time.
  • Curing in the liquid crystal dropping method may be only thermosetting or a combination of photocuring and thermosetting.
  • the photocuring and heat can be cured from the viewpoint that the liquid crystal is hardly deteriorated by heating and can be cured quickly. It is preferable to use in combination with curing.
  • liquid crystal sealing agent for liquid crystal dropping method using both photocuring and thermosetting (B) (meth) acryl-modified epoxy resin or (C) acrylic resin and (D) a photopolymerization initiator are preferably further included, and (E) a filler is preferably further included.
  • (A-1) epoxy resin Preferably, 1 to 20 parts by weight, more preferably 3 to 10 parts by weight of (A-1) epoxy resin, and preferably 30 to 80 parts by weight, more preferably 40 to 40 parts by weight with respect to 100 parts by weight of the liquid crystal sealant.
  • 70 parts by weight of (B) (meth) acryl-modified epoxy resin and preferably 1 to 40 parts by weight, more preferably 3 to 20 parts by weight of (C) acrylic resin are included.
  • the viscosity of the liquid crystal sealant of the present invention at 25 ° C. and 2.5 rpm using an E-type viscometer is preferably 30 to 350 Pa ⁇ s. This is because a liquid crystal sealant having a viscosity in the above range is excellent in coating stability.
  • the liquid crystal display panel of the present invention is a display substrate, a counter substrate that is paired with the display substrate, a frame-shaped sealing member interposed between the display substrate and the counter substrate, and a display substrate. And a liquid crystal layer filled in a space surrounded by a sealing member between the substrate and the substrate.
  • the cured product of the liquid crystal sealant of the present invention can be used as a seal member.
  • the display substrate and the counter substrate are both transparent substrates.
  • the material of the transparent substrate can be glass or plastic such as polycarbonate, polyethylene terephthalate, polyethersulfone and PMMA.
  • a matrix-like TFT, a color filter, a black matrix, or the like can be disposed on the surface of the display substrate or the counter substrate.
  • An alignment film is further formed on the surface of the display substrate or the counter substrate.
  • the alignment film includes a known organic alignment agent or inorganic alignment agent.
  • Such a liquid crystal display panel can be manufactured using the liquid crystal sealant of the present invention.
  • the liquid crystal display panel manufacturing method includes a liquid crystal dropping method and a liquid crystal injection method.
  • the manufacturing method of the liquid crystal display panel by the liquid crystal dropping method is a1) a first step of forming a seal pattern of the liquid crystal sealant of the present invention on one substrate; a2) a second step of dropping liquid crystal into a region surrounded by the seal pattern of the substrate or a region of the other substrate facing the region surrounded by the seal pattern in a state where the seal pattern is uncured; , a3) a third step of superimposing one substrate and the other substrate via a seal pattern; a4) a fourth step of curing the seal pattern.
  • the state in which the seal pattern is uncured means a state in which the curing reaction of the liquid crystal sealant has not progressed to the gel point. Therefore, in the step a2), the seal pattern may be semi-cured by light irradiation or heating in order to suppress dissolution of the liquid crystal sealant in the liquid crystal.
  • One substrate and the other substrate are a display substrate or a counter substrate, respectively.
  • step a4) only curing by heating may be performed, but it is preferable to perform curing by heating (main curing) after curing by light irradiation (temporary curing). This is because the liquid crystal sealant can be instantly cured by temporary curing by light irradiation to suppress dissolution in the liquid crystal.
  • Irradiation energy, (B) (meth) may as long as capable of curing the acrylic-modified epoxy resin and (C) an acrylic resin, 1000 ⁇ 3000mJ / cm 2, preferably about 2000 mJ / cm 2 about It is.
  • the light is preferably ultraviolet light.
  • the thermosetting temperature depends on the composition of the liquid crystal sealant, it is as low as possible, for example, about 120 ° C., preferably 80 to 100 ° C. from the viewpoint of reducing the deterioration of the liquid crystal, and the thermosetting time is 1 to About 2 hours.
  • liquid crystal dropping method since the contact time between the uncured liquid crystal sealant and the liquid crystal is relatively long, liquid crystal contamination tends to occur.
  • the liquid crystal sealant of the present invention since the liquid crystal sealant of the present invention has low solubility in liquid crystals, the liquid crystal display panel obtained by the liquid crystal dropping method using the liquid crystal sealant of the present invention is excellent in display reliability.
  • the manufacturing method of the liquid crystal display panel by the liquid crystal injection method is b1) a first step of forming a seal pattern of the liquid crystal sealant of the present invention on one substrate; b2) a second step of superimposing one substrate and the other substrate via a seal pattern; b3) a third step of thermosetting the seal pattern to obtain a liquid crystal injection cell having an injection port for injecting liquid crystal; b4) a fourth step of injecting the liquid crystal into the liquid crystal injection cell through the injection port; b5) a fifth step of sealing the inlet.
  • a liquid crystal injection cell is prepared. First, two transparent substrates (for example, glass plates) are prepared. Then, a seal pattern is formed on one substrate with a liquid crystal sealant. After the other substrate is superimposed on the surface of the substrate where the seal pattern is formed, the seal pattern may be cured. At this time, it is necessary to provide an injection port for injecting liquid crystal in a part of the liquid crystal injection cell, but the injection port may be provided with a part of the opening when drawing the seal pattern. Moreover, after forming the seal pattern, the seal pattern at a desired location may be removed to provide an injection port.
  • thermosetting conditions in step b3) are, for example, about 2 to 5 hours at 150 ° C., depending on the composition of the liquid crystal sealant.
  • the step b4) can be performed according to a known method in which the inside of the liquid crystal injection cell obtained in the steps b1) to b3) is evacuated and the liquid crystal is sucked from the injection port of the liquid crystal injection cell. Good.
  • the liquid crystal sealant may be cured after being sealed in the injection port of the liquid crystal injection cell.
  • the time for which the uncured liquid crystal sealant and the liquid crystal contact is relatively short.
  • the liquid crystal may be injected even if the liquid crystal sealing agent of the liquid crystal injection cell is not sufficiently cured. Since the liquid crystal sealant of the present invention has low solubility in liquid crystal, it is difficult to contaminate the liquid crystal even in such a case. Therefore, a liquid crystal display panel excellent in display reliability can be obtained also by a liquid crystal injection method using the liquid crystal sealant of the present invention.
  • A-1) Epoxy resin Bisphenol A type epoxy resin (Epicoat 828EL: JER, epoxy equivalent 190 g / eq)
  • Hydroxyl-containing type 1 2-hydroxymethylimidazole (molecular weight 98.1, melting point 115 ° C.)
  • Hydroxyl-containing type 2 2-phenyl-4,5-dihydroxymethylimidazole (molecular weight 204, solid, melting point> 230 ° C. (decomposition))
  • Hydroxyl-free type 1 2-methylimidazole (molecular weight 82, solid, melting point 137-145 ° C)
  • Hydroxyl-free type 2 2-ethyl-4-methylimidazole (molecular weight 110, liquid, melting point 41 ° C.)
  • (B) (Meth) acryl-modified epoxy resin An acrylic-modified bisphenol F-type epoxy resin (50% partially acrylate) synthesized as follows was used. In a 500 ml four-necked flask equipped with a stirrer, a gas introduction tube, a thermometer and a cooling tube, 160 g of bisphenol F type epoxy resin (Epototo YDF-8170C: manufactured by Tohto Kasei Co., Ltd., epoxy equivalent 160 g / eq), 36 g of acrylic An acid and 0.2 g of triethanolamine were charged, respectively, and heated and stirred at 110 ° C. for 5 hours under a dry air stream to obtain an acrylic-modified bisphenol F type epoxy resin. The obtained acrylic modified bisphenol F type epoxy resin washed 40 times with ultra pure water was used.
  • E Filler Silicon dioxide S-100 (manufactured by Nippon Shokubai Chemical Co., Ltd.)
  • F Thermoplastic resin particles Fine particle polymer F325 (manufactured by Zeon Kasei Co., Ltd., primary particle diameter 0.5 ⁇ m)
  • G Other components Silane coupling agent KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd.)
  • Example 1 10 parts by weight of (A-1) bisphenol A type epoxy resin, 5 parts by weight of (A-2) Amicure VDH, 3 parts by weight of (A-3) 2-hydroxymethylimidazole, 70 parts by weight of (B) acrylic Modified bisphenol F type epoxy resin, 20 parts by weight of (C) acrylic resin, 1 part by weight of (D) Irgacure 184, 15 parts by weight of (E) silicon dioxide S-100, 20 parts by weight of (F) fine particle polymer F325 And 0.5 part by weight of (G) KBM-403 curable resin composition was sufficiently kneaded with a Dalton mixer using three rolls to obtain a sealant. The viscosity of the sealant at 25 ° C. by an E-type viscometer (1.0 rpm) was 300 Pa ⁇ s.
  • Example 4 (C) without using acrylic resin and (D) Irgacure 184, (A-1) bisphenol A type epoxy resin, (A-2) Amicure VDH, (A-3) 2-hydroxymethylimidazole, and (B) A sealing agent was obtained in the same manner as in Example 1 except that the blending amount of the acrylic-modified bisphenol F type epoxy resin was changed as shown in Table 1.
  • Table 1 shows the blending amounts of (A-1) bisphenol A type epoxy resin, (A-3) 2-hydroxymethylimidazole, and (B) acrylic modified bisphenol F type epoxy resin without using (C) acrylic resin.
  • a sealant was obtained in the same manner as in Example 1 except that the changes were made as shown.
  • Example 6 A sealant was obtained in the same manner as in Example 1 except that the blending amounts of (A) epoxy resin and (A-3) 2-hydroxymethylimidazole were changed as shown in Table 1.
  • Viscosity stability The sealing agents obtained in Examples and Comparative Examples were collected so that the weight of the sealing agent in the dispensing syringe was 10 g, and then subjected to defoaming treatment. About 2 g of them, initial viscosity was measured at room temperature (23 degreeC) using the E-type viscosity meter. Next, after the sample was stored at 23 ° C. and 50% RH for 1 week, the viscosity was measured again under the same conditions. At this time, the rate of increase in viscosity after storage for 1 week with respect to the initial viscosity was determined. Thereby, the viscosity stability was evaluated according to the following criteria. Viscosity increase rate is 1.5 times or less: ⁇ (excellent) Viscosity increase rate exceeds 1.5 times and is 2.0 times or less: ⁇ (slightly inferior) Viscosity increase rate exceeds 2.0 times: x (inferior)
  • Liquid crystal leak resistance 1 part by weight of a spherical spacer (average particle size: 5 ⁇ m) is added to the sealing agents obtained in the examples and comparative examples, and defoaming treatment is performed. Obtained.
  • the obtained sealing agent was filled in a syringe for dispensing under a yellow lamp. Furthermore, using a dispensing device (manufactured by Hitachi Plant Technology), a rectangular seal pattern of 35 mm ⁇ 40 mm square at a drawing speed of 100 mm / s on a 360 mm ⁇ 470 mm glass substrate for liquid crystal display panel (manufactured by Nippon Electric Glass Co., Ltd.) 50 pieces (cross-sectional area 3500 ⁇ m 2 ) were produced. Further, a seal pattern was formed on the outer circumference of each of the 50 seal patterns under the same conditions to form a double frame seal line.
  • a dispensing device manufactured by Hitachi Plant Technology
  • a liquid crystal material (MLC-11900-000: manufactured by Merck & Co., Inc.) corresponding to the panel internal volume after bonding was precisely dropped into the seal pattern of the obtained substrate with a dispensing device (Hitachi Plant Technology Co., Ltd.).
  • the glass substrate paired with the substrate was bonded under a reduced pressure of 5 Pa using a vacuum bonding apparatus (manufactured by Shin-Etsu Engineering Co., Ltd.).
  • the bonded glass substrate was held in a light shielding box for 3 minutes, then irradiated with 2000 mJ of ultraviolet light to be temporarily cured, and then heated at 100 ° C. for 60 minutes to be cured.
  • the seal pattern linearity of the obtained liquid crystal display panel that is, the seal linearity was evaluated by the following method.
  • the discharge pressure was 0.3 MPa
  • the cross-sectional area was 3000 ⁇ m 2
  • the coating speed was 100 mm / s.
  • the shape of the obtained seal pattern was evaluated as follows. 50 frame molds with no seal breakage or seal fading: ⁇ (Excellent) 48-49 frame molds with no seal breakage or seal fading: ⁇ (somewhat inferior) Less than 48 frame molds with no seal breakage or seal fading: ⁇ (Inferior)
  • liquid crystal sealant is dispensed onto a 40 mm x 45 mm glass substrate (EHC, RT-DM88-PIN) provided with a transparent electrode and an alignment film (shot master: manufactured by Musashi Engineering). Then, a rectangular seal pattern (cross-sectional area 3500 ⁇ m 2 ) (main seal) of 35 mm ⁇ 40 mm was formed, and a similar seal pattern was also formed on the outer periphery thereof.
  • a liquid crystal material (MLC-11900-000: manufactured by Merck & Co., Inc.) corresponding to the panel internal volume after bonding is precisely dropped into the frame of the main seal using a dispenser, and the paired glass substrates are reduced under reduced pressure. After pasting together, it was released to the atmosphere and pasted. The bonded glass substrate was held in a light shielding box for 3 minutes, and then irradiated with ultraviolet rays at 2000 mJ / cm 2 and heated at 100 ° C. for 1 hour.
  • MLC-11900-000 manufactured by Merck & Co., Inc.
  • the obtained liquid crystal display panel was visually observed for color unevenness generated in the liquid crystal around the seal portion before and after storage in a thermostatic chamber at 70 ° C. and 95% RH for 500 hours.
  • the case where color unevenness was not confirmed was evaluated as ⁇ (excellent); the case where slight unevenness was confirmed was evaluated as ⁇ (inferior);
  • the liquid crystal display panel taken out after storage in the thermostatic chamber is driven with an applied voltage of 5 V using a DC power supply device, and whether or not the liquid crystal display function in the vicinity of the liquid crystal sealant functions normally from the initial stage of driving,
  • the panel display characteristics were evaluated as follows.
  • the liquid crystal display function can be demonstrated until sealing. ⁇ (Good) Abnormal display function is confirmed in the vicinity of the seal when it is less than 0.3 mm: ⁇ (slightly inferior) Abnormality of the display function is confirmed beyond 0.3 mm in the vicinity of the seal: ⁇ (remarkably inferior)
  • Adhesiveness In the above 4), the plane tensile strength of the liquid crystal display panel sample after storage in a thermostatic chamber was measured at a pulling rate of 2 mm / min using a tensile tester (manufactured by Intesco). Adhesiveness was evaluated as follows. Adhesive strength of 15 MPa or more: ⁇ (excellent) Adhesive strength is 7 MPa or more and less than 15 MPa: ⁇ (slightly inferior) Adhesive strength is less than 7 MPa: x (inferior)
  • the sealants of Examples 1 to 6 containing an imidazole-based curing catalyst containing a hydroxyl group are all cured at a low temperature and in a short time and are difficult to dissolve in liquid crystals. It can be seen that leakage and display characteristics are good.
  • the sealant of Example 1 containing a curing catalyst having a low melting point is more easily melted near the heat curing temperature than the sealant of Comparative Example 6 containing a curing catalyst having a high melting point, and therefore has excellent curability and liquid crystal It is suggested that there is little dissolution. That is, since the sealing agent of Comparative Example 6 contains a curing catalyst having a melting point higher than 150 ° C., the resin is not sufficiently cured, is dissolved in liquid crystal, and is considered to have low adhesion.
  • the sealing agent of Comparative Example 3 that does not contain an imidazole-based curing catalyst does not cause the curing catalyst itself to dissolve in the liquid crystal, but because the resin is not sufficiently cured, it causes dissolution in the liquid crystal and further adhesion. Is also suggested to be low. Furthermore, it can be seen that the sealant of Comparative Example 4 has slightly low display characteristics. This is presumably because the imidazole-based curing catalyst is partially dissolved in the liquid crystal even though it is difficult to dissolve in the liquid crystal due to the inclusion of a hydroxyl group.
  • the sealing agent of Comparative Example 5 containing an imidazole-based curing catalyst containing a hydroxyl group and no thermosetting agent has low display characteristics and low adhesion of the liquid crystal display panel. This is considered to be because a tough crosslinked body cannot be formed.
  • the liquid crystal sealing agent of the present invention contains many hydroxyl groups, dissolution in liquid crystals is suppressed even at high temperatures and high humidity. For this reason, when the hardened

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Abstract

La présente invention se rapporte à un agent d'étanchéité à cristaux liquides qui est difficile à dissoudre par des cristaux liquides, qui peut durcir aux basses températures et en peu de temps et qui présente une excellente fiabilité d'affichage. L'agent d'étanchéité à cristaux liquides comprend une résine durcissable qui comprend une résine époxy, un agent thermodurcissable et un catalyseur de durcissement en une quantité comprise entre 0,1 et 10 parties en poids par rapport à 100 parties en poids au total de la résine durcissable susmentionnée. Le catalyseur de durcissement susmentionné est un catalyseur de durcissement à imidazole ayant un point de fusion indiqué par la formule (1) à la température maximale de 150 °C. [Dans la formule (1), R1 et R2 représentent chacun de façon indépendante un atome d'hydrogène, un groupe alkyle inférieur, un groupe hydroxyalkyle inférieur, un groupe phényle ou un groupe benzyle; R3 et R4 représentent chacun de façon indépendante un atome d'hydrogène, un groupe alkyle inférieur ou un groupe hydroxyalkyle inférieur; et R1 et/ou R2 et/ou R3 et/ou R4 est un groupe hydroxyalkyle inférieur].
PCT/JP2011/001646 2010-03-25 2011-03-18 Agent d'étanchéité à cristaux liquides, procédé de fabrication d'un panneau d'affichage à cristaux liquides au moyen de celui-ci et panneau d'affichage à cristaux liquides WO2011118192A1 (fr)

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CN201180002917.XA CN102472929B (zh) 2010-03-25 2011-03-18 液晶密封剂、使用其的液晶显示面板的制造方法及液晶显示面板
JP2011522321A JP4815027B1 (ja) 2010-03-25 2011-03-18 液晶シール剤、それを用いた液晶表示パネルの製造方法、および液晶表示パネル
HK12111066.2A HK1170312A1 (en) 2010-03-25 2012-11-02 Liquid crystal sealing agent, method for producing liquid crystal display panel using same, and liquid crystal display panel

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JP2017102291A (ja) * 2015-12-02 2017-06-08 協立化学産業株式会社 液晶表示素子用シール剤

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WO2013094734A1 (fr) * 2011-12-22 2013-06-27 日産化学工業株式会社 Procédé de fabrication d'un élément d'écran à cristaux liquides pour commutation dans le plan
KR101623670B1 (ko) * 2012-01-18 2016-05-23 미쓰이 가가쿠 가부시키가이샤 조성물, 조성물로 이루어지는 표시 디바이스 단면 시일제, 표시 디바이스 및 그의 제조 방법
CN103173159B (zh) * 2013-03-13 2015-08-05 北京京东方光电科技有限公司 封框胶组合物及其制备方法和显示装置
WO2016067582A1 (fr) * 2014-10-30 2016-05-06 三井化学株式会社 Procédé de production de panneau d'affichage à cristaux liquides, panneau d'affichage à cristaux liquides et composition d'agent d'étanchéité pour cristaux liquides
KR102204964B1 (ko) 2018-04-17 2021-01-19 주식회사 엘지화학 반도체 회로 접속용 접착제 조성물 및 이를 포함한 접착 필름
JP7145329B2 (ja) * 2019-05-17 2022-09-30 三井化学株式会社 液晶滴下工法用封止剤、これを用いた液晶表示パネル、およびその製造方法

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