WO2019230709A1 - Produit d'étanchéité d'élément d'affichage à cristaux liquides, produit à conduction verticale, et élément d'affichage à cristaux liquides - Google Patents

Produit d'étanchéité d'élément d'affichage à cristaux liquides, produit à conduction verticale, et élément d'affichage à cristaux liquides Download PDF

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Publication number
WO2019230709A1
WO2019230709A1 PCT/JP2019/021056 JP2019021056W WO2019230709A1 WO 2019230709 A1 WO2019230709 A1 WO 2019230709A1 JP 2019021056 W JP2019021056 W JP 2019021056W WO 2019230709 A1 WO2019230709 A1 WO 2019230709A1
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Prior art keywords
liquid crystal
meth
crystal display
group
formula
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PCT/JP2019/021056
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English (en)
Japanese (ja)
Inventor
駿介 高橋
幸平 竹田
秀幸 林
誠実 新土
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積水化学工業株式会社
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Priority to JP2019547542A priority Critical patent/JP6676833B1/ja
Publication of WO2019230709A1 publication Critical patent/WO2019230709A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • 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
    • 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 adhesiveness, moisture permeation prevention, and low liquid crystal contamination. 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 sealing agent as disclosed in Patent Document 1 and Patent Document 2 is used from the viewpoint of shortening tact time and optimizing the amount of liquid crystal used.
  • a liquid crystal dropping method called a dropping method is used.
  • the dropping method first, a frame-like seal pattern is formed on one of the two substrates with electrodes by dispensing. Next, liquid crystal microdrops are dropped into the sealing frame of the substrate in a state where the sealing agent is uncured, and the other substrate is superposed under vacuum to cure the sealing agent, thereby producing a liquid crystal display element.
  • this dripping method has become the mainstream method for manufacturing liquid crystal display elements.
  • liquid crystal display elements are increasingly required to have moisture resistance reliability when driving in high-temperature and high-humidity environments, and the sealant prevents water from entering from the outside.
  • the sealant prevents water from entering from the outside.
  • the line width of the sealing agent applied along with the narrow frame design has become narrower, and it has been difficult to obtain a sealing agent that is excellent in both adhesion and moisture permeation prevention properties even when it is thinned.
  • the present invention is a sealing agent for a liquid crystal display element containing a curable resin and a radical polymerization initiator, and the curable resin has (A) a hydrogen bonding functional group value of 0.0030 mol / g or more. , (Meth) acrylic compounds having a molecular weight of 500 or more and 1200 or less, having no epoxy group, and having 3 or more aromatic rings in one molecule, and / or (B) a hydrogen bonding functional group value of 0
  • this invention of another aspect is a sealing agent for liquid crystal display elements containing curable resin and a radical polymerization initiator, Comprising:
  • the said curable resin is represented by following formula (1), In 1 molecule
  • a liquid crystal display element sealing agent comprising a compound having three or more aromatic rings and / or a compound represented by the following formula (3) and having three or more aromatic rings in one molecule.
  • R 1 independently represents a hydrogen atom or a methyl group
  • R 2 represents a divalent aromatic group represented by the following formula (2-1) or (2-2).
  • R 3 represents a divalent aliphatic group having 2 to 15 carbon atoms or a divalent aromatic group that is the same as or different from R 2, and n is 1 to 3 inclusive.
  • R 4 represents a linear or branched alkylene group having 1 to 4 carbon atoms, and p is 0 or more and 3 or less.
  • q is 0 or more and 3 or less.
  • * represents a bonding position.
  • some or all of the hydrogen atoms may be substituted.
  • R 5 represents a hydrogen atom or a methyl group
  • R 6 represents a divalent aromatic group represented by the following Formulas (4-1) and (4-2)
  • R 7 Represents a divalent aliphatic group having 1 to 20 carbon atoms or a divalent aromatic group that is the same as or different from R 6, and m is 1 to 3 inclusive.
  • R 8 represents a linear or branched alkylene group having 1 to 4 carbon atoms, and p is 0 or more and 3 or less.
  • q is 0 or more and 3 or less.
  • * represents a bonding position.
  • some or all of the hydrogen atoms may be substituted.
  • the hydrogen bonding functional group value is 0.0030 mol / g or more, the molecular weight is 500 or more and 1200 or less, has no epoxy group, and has 3 or more aromatic rings in one molecule.
  • the (meth) acrylic compound is also referred to as “(meth) acrylic compound according to the present invention”.
  • the modified epoxy resin is also referred to as “partial (meth) acryl-modified epoxy resin according to the present invention”.
  • the present inventors use a compound having a hydrogen bonding functional group value and a molecular weight within a specific range and having a specific structure, thereby providing adhesion, moisture permeability prevention, and The present inventors have found that a sealing agent for liquid crystal display elements excellent in low liquid crystal contamination can be obtained, and have completed the present invention.
  • liquid crystals with high polarity are often used in response to the increase in viewing angle of liquid crystal display elements.
  • the sealing agent for liquid crystal display elements of the present invention has such high polarity.
  • the liquid crystal is excellent in low liquid crystal contamination.
  • the sealing agent for liquid crystal display elements of this invention contains curable resin.
  • the said curable resin contains the (meth) acryl compound concerning this invention and / or the partial (meth) acryl modified epoxy resin concerning this invention.
  • the sealing agent for a liquid crystal display element of the present invention has adhesiveness, moisture permeation prevention, and It is excellent in low liquid crystal contamination.
  • the “(meth) acryl” means acryl or methacryl
  • the “(meth) acryl compound” means a compound having a (meth) acryloyl group
  • the “partially (meth) acryl-modified epoxy resin” is obtained by reacting a part of an epoxy compound having two or more epoxy groups in one molecule with (meth) acrylic acid. It means a compound having at least one epoxy group and one or more (meth) acryloyl groups.
  • the lower limit of the hydrogen bondable functional group value of the (meth) acrylic compound according to the present invention and the partially (meth) acrylic-modified epoxy resin according to the present invention is 0.0030 mol / g.
  • the sealing agent for liquid crystal display elements of the present invention is excellent in low liquid crystal contamination with respect to highly polarized liquid crystals.
  • the minimum with the preferable hydrogen bondable functional group value is 0.040 mol / g.
  • the “hydrogen-bonding functional group value” is a value obtained by dividing the number of hydrogen-bonding functional groups in one molecule of the compound by the weight average molecular weight of the compound.
  • the number of hydrogen bonding functional groups is the hydrogen bonding property in one molecule of the component (main component) having the largest content ratio. It means the number of functional groups.
  • the above “weight average molecular weight” is a value obtained by gel conversion chromatography (GPC) using tetrahydrofuran as a solvent and calculated in terms of polystyrene. Examples of the column used when measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko).
  • a hydroxyl group As said hydrogen bondable functional group, a hydroxyl group, an amino group, a carboxy group, a thiol group etc. are mentioned, for example. Of these, a hydroxyl group is preferred.
  • the (meth) acrylic compound according to the present invention and the partially (meth) acrylic-modified epoxy resin according to the present invention have a molecular weight lower limit of 500 and an upper limit of 1200.
  • the sealing agent for liquid crystal display elements of the present invention is excellent in low liquid crystal contamination.
  • the sealing agent for liquid crystal display elements of the present invention has excellent coating properties.
  • the preferable lower limit of the molecular weight is 600, and the preferable upper limit is 1100.
  • the “molecular weight” is a molecular weight obtained from the structural formula for a compound whose molecular structure is specified, but for a compound having a wide distribution of polymerization degree and a compound whose modification site is unspecified, Sometimes expressed using weight average molecular weight.
  • the (meth) acryl compound according to the present invention and the partial (meth) acryl-modified epoxy resin according to the present invention have three or more aromatic rings in one molecule.
  • the sealing agent for liquid crystal display elements of the present invention Is excellent in moisture permeation-preventing property even when applied in a thin line.
  • the (meth) acrylic compound according to the present invention and the partial (meth) acrylic-modified epoxy resin according to the present invention preferably have 10 or less aromatic rings in one molecule. .
  • the aromatic ring examples include a benzene ring, a naphthalene ring, and an anthracene ring. Of these, a benzene ring is preferred.
  • denaturation epoxy resin concerning this invention have three or more conjugated 6-membered rings in 1 molecule. For example, a benzene ring is counted as one conjugated six-membered ring, a naphthalene ring is counted as two conjugated six-membered rings, and an anthracene ring is counted as three conjugated six-membered rings.
  • the number of aromatic rings and conjugated 6-membered rings in one molecule is the component with the largest content (main component) in the case of a compound having a molecular weight distribution, that is, a compound containing a plurality of components having different molecular weights.
  • the number of aromatic rings or conjugated six-membered rings in one molecule is the component with the largest content (main component) in the case of a compound having a molecular weight distribution, that is, a compound containing a plurality of components having different molecular weights.
  • (meth) acrylic compound according to the present invention specifically, a compound represented by the above formula (1) is preferable.
  • the compound represented by the above formula (1) can be suitably produced by the following method. That is, first, a diepoxy compound having three or more aromatic rings in one molecule by reacting a diglycidyl ether or resorcinol diglycidyl ether having a bisphenol skeleton with a compound having two aromatic hydroxyl groups in one molecule. Get. Subsequently, all the epoxy groups of the diepoxy compound having three or more aromatic rings in one molecule thus obtained are reacted with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method, whereby the above formula ( The compound represented by 1) can be obtained.
  • R 3 in the above formula (1) a divalent aromatic group different from R 2
  • the diglycidyl ether having the bisphenol skeleton or the resorcinol diglycidyl ether and two aromatic groups in one molecule What has a different bivalent aromatic group should just be used about the compound which has a hydroxyl group.
  • the hydrogen bonding functional group value is reduced to 0. It becomes difficult to set it to 030 mol / g or more. Therefore, a commercially available epoxy (meth) acrylate using such a compound does not become a (meth) acrylic compound according to the present invention.
  • Examples of the diglycidyl ether having a bisphenol skeleton include bisphenol A diglycidyl ether, bisphenol B diglycidyl ether, bisphenol E diglycidyl ether, and bisphenol F diglycidyl ether.
  • Examples of the compound having two aromatic hydroxyl groups in one molecule include bisphenol A, bisphenol B, bisphenol E, bisphenol F, resorcinol, catechol, hydroquinone, 4,4'-dihydroxybiphenyl, and the like.
  • the partially (meth) acryl-modified epoxy resin according to the present invention is preferably a compound represented by the above formula (3).
  • the compound represented by the above formula (3) can be preferably produced by the following method. That is, the diglycidyl ether having the bisphenol skeleton or the resorcinol diglycidyl ether is reacted with the compound having two aromatic hydroxyl groups in one molecule, and the diepoxy having three or more aromatic rings in one molecule. A compound is obtained. By reacting one epoxy group of a diepoxy compound having three or more aromatic rings in one molecule thus obtained with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method, the above formula (3) Can be obtained.
  • R 7 in the above formula (3) a divalent aromatic group different from R 6 , the diglycidyl ether having the bisphenol skeleton or the resorcinol diglycidyl ether, and two aromatic groups in one molecule
  • What has a different bivalent aromatic group should just be used about the compound which has a hydroxyl group.
  • the hydrogen bonding functional group value is reduced to 0. It becomes difficult to set it to 030 mol / g or more. Therefore, a commercially available partial (meth) acryl-modified epoxy resin using such a compound does not become a partial (meth) acryl-modified epoxy resin according to the present invention.
  • the curable resin may contain other curable resins as long as the object of the present invention is not impaired. You may contain.
  • the (meth) acrylic compound according to the present invention represented by the above formula (1) and / or the partial (meth) acrylic according to the present invention in 100 parts by weight of the curable resin.
  • the preferable lower limit of the content of the modified epoxy resin is 5 parts by weight, and the preferable upper limit is 80 parts by weight.
  • the obtained sealing agent for liquid crystal display elements has adhesiveness and moisture permeation prevention. And low liquid crystal contamination.
  • the minimum with more preferable content of the (meth) acrylic compound concerning this invention and / or the partial (meth) acryl modified epoxy resin concerning this invention is 10 weight part, and a more preferable upper limit is 50 weight part.
  • the compound (henceforth "other epoxy compound”) which has epoxy groups other than the partial (meth) acryl modified epoxy resin concerning this invention is used suitably.
  • Examples of the other epoxy compounds include bisphenol A type epoxy resin, bisphenol S type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, and naphthalene.
  • epoxy compound as other partial (meth) acryl modification epoxy resins other than the partial (meth) acryl modification epoxy resin concerning this invention, some epoxy groups of these epoxy compounds are (meth).
  • a compound obtained by reacting with acrylic acid can also be used.
  • the curable resin may also contain other (meth) acrylic compounds other than the (meth) acrylic compound according to the present invention and the partially (meth) acrylic-modified epoxy resin according to the present invention as the other curable resin.
  • the other (meth) acrylic compounds include (meth) acrylic acid ester compounds, epoxy (meth) acrylates, urethane (meth) acrylates, and the like. Of these, epoxy (meth) acrylate is preferable.
  • the other (meth) acrylic compounds preferably have two or more (meth) acryloyl groups in the molecule from the viewpoint of reactivity.
  • 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.
  • 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, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri ( (Meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerin tri (meth) acrylate, propylene oxide-added glycerin tri (meth) acrylate, pentaerythritol tri (meth) acrylate, Tris (meth) acryloyloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra Meth) acrylate, dipentaerythritol pen
  • epoxy (meth) acrylate what is obtained by making the other epoxy compound mentioned above and (meth) acrylic acid react in presence of a basic catalyst according to a conventional method etc. are mentioned, for example.
  • 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), and hydrogenation.
  • 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.
  • isocyanate compound a chain-extended isocyanate compound obtained by a reaction between a polyol and an excess of an isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
  • 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.
  • urethane (meth) acrylates examples include, for example, urethane (meth) acrylate manufactured by Toagosei Co., Ltd., urethane (meth) acrylate manufactured by Daicel Ornex, and urethane (meth) manufactured by Negami Kogyo Co., Ltd. Examples thereof include acrylate, urethane (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., urethane (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd., and the like. Examples of the urethane (meth) acrylate manufactured by Toagosei include M-1100, M-1200, M-1210, and M-1600.
  • the urethane (meth) acrylate manufactured by the Daicel Orunekusu Inc. for example, EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260 etc. Can be mentioned.
  • Examples of the urethane (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd. include AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, and UA-306T. It is done.
  • the sealing agent for liquid crystal display elements of the present invention contains a radical polymerization initiator.
  • the radical polymerization initiator 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.
  • Specific examples of the photo radical polymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, and 2- (dimethylamino).
  • thermal radical polymerization initiator what is comprised with an azo compound, an organic peroxide, etc. is mentioned, for example.
  • an initiator composed of an azo compound hereinafter also referred to as “azo initiator”
  • an initiator composed of a polymer azo compound hereinafter referred to as “polymer azo”.
  • azo initiator an initiator composed of an azo compound
  • polymer azo an initiator composed of a polymer azo compound
  • Also referred to as “initiator” is more preferred.
  • the said thermal radical polymerization initiator may be used independently, and 2 or more types may be used in combination.
  • the “polymer azo compound” means a compound having an azo group and generating a radical capable of curing a (meth) acryloyl group by heat and having a number average molecular weight of 300 or more. To do.
  • 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 initiators include VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (all manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.). Can be mentioned.
  • Examples of the azo initiator that is not a polymer 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.
  • the content of the radical polymerization initiator is preferably 0.01 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the radical polymerization initiator is within this range, the obtained sealing agent for liquid crystal display elements is excellent in storage stability and curability while suppressing liquid crystal contamination.
  • the minimum with more preferable content of the said radical polymerization initiator is 0.1 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 thermosetting agent.
  • the thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Of these, 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 organic acid hydrazide include 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 Ajinomoto Fine Techno Co., and organic acid hydrazides manufactured by Nippon Finechem Co., Ltd.
  • Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
  • Examples of the organic acid hydrazide manufactured by Ajinomoto Fine Techno Co. include Amicure VDH, Amicure VDH-J, Amicure UDH, Amicure UDH-J, and the like.
  • Examples of the organic acid hydrazide manufactured by Nippon Finechem include MDH.
  • 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 upper limit with more preferable content of the said thermosetting agent is 30 weight part.
  • the sealing agent for liquid crystal display elements of the present invention may contain a filler for the purpose of improving the viscosity, further improving the adhesion due to the stress dispersion effect, improving the linear expansion coefficient, improving the moisture resistance of the cured product, and the like. preferable.
  • an inorganic filler or an organic filler can be used as the filler.
  • the inorganic filler 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.
  • the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles. The said filler may be used independently and 2 or more types may be used in combination.
  • the preferable lower limit of the content of the filler in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight.
  • the minimum with more preferable content of the said filler is 20 weight part, and a more preferable upper limit is 60 weight part.
  • the sealing agent for liquid crystal display elements of the present invention may contain 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-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are preferably used. These 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.
  • a preferable upper limit is 10 weight part.
  • 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.
  • the sealing compound for liquid crystal display elements of this invention can be used suitably as a light shielding sealing agent.
  • Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Of these, titanium black is preferable.
  • 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.
  • a shading agent 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
  • the sealing agent for a liquid crystal display element of the present invention can be used. Photocurability can be further increased.
  • 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 titanium black preferably has an optical density (OD value) per ⁇ m of 3 or more, more preferably 4 or more. The higher the light-shielding property of the titanium black, the better.
  • the OD value of the titanium black is not particularly limited, but is usually 5 or less.
  • 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 sufficient light-shielding properties, and therefore 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 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 is further added with a stress relaxation agent, reactive diluent, thixotropic agent, spacer, curing accelerator, antifoaming agent, leveling agent, polymerization inhibitor, etc., if necessary.
  • An agent may be contained.
  • Examples of the method for producing the liquid crystal display element sealing agent of the present invention include a curable resin and a radical using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll. Examples thereof include a method of mixing a polymerization initiator and an additive such as a silane coupling agent added as necessary.
  • a vertical conducting material can be produced by blending conductive fine particles with the liquid crystal display element sealant of the present invention.
  • the 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 a metal ball, a resin fine particle formed with a conductive metal layer on the surface, or the like can be used.
  • 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.
  • the sealing agent for a liquid crystal display element of the present invention is excellent in low liquid crystal contamination even when the liquid crystal display element of the present invention uses a liquid crystal with high polarity.
  • Specific examples of the highly polar liquid crystal include those using a liquid crystal molecule having a polar group.
  • Examples of the polar group include a fluoro group, a chloro group, and a cyano group.
  • the liquid crystal display element of this invention the liquid crystal display element of a narrow frame design is preferable.
  • the width of the frame portion around the liquid crystal display unit is preferably 2 mm or less.
  • the coating width of the sealing agent for liquid crystal display elements of the present invention when producing the liquid crystal display element of the present invention is preferably 1 mm or less.
  • the sealing agent for liquid crystal display elements of this invention can be used suitably for manufacture of the liquid crystal display element by a liquid crystal dropping method.
  • Examples of the method for producing the liquid crystal display element of the present invention by the liquid crystal dropping method include the following methods. First, the liquid crystal display element sealant of the present invention is applied to the substrate by screen printing, dispenser application, or the like to form a frame-shaped seal pattern. Next, in a state where the sealant for the liquid crystal display element of the present invention is uncured, a droplet of liquid crystal is dropped on the entire surface of the frame of the seal pattern, and another substrate is immediately superimposed.
  • a liquid crystal display element can be obtained by a method in which the seal pattern portion is irradiated with light such as ultraviolet rays to perform photocuring of the sealant.
  • a step of heating and curing the sealing agent may be performed.
  • the sealing compound for liquid crystal display elements which is excellent in adhesiveness, moisture-permeation prevention property, and low liquid-crystal contamination can be provided.
  • the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.
  • the curable resin A is a compound represented by the above formula (1) (R 1 is a hydrogen atom, R 2 and R 3 are represented by the formula (2-1). group (R 4 is a methylene group, p is 0), n was confirmed to contain 1) as a main component.
  • the resulting curable resin A had a weight average molecular weight of 1100 and a hydrogen bondable functional group (hydroxyl group) value of 0.0036 mol / g.
  • the curable resin B is a compound represented by the above formula (1) (R 1 is a hydrogen atom, R 2 and R 3 are represented by the formula (2-2). It was confirmed that the group (q is 0) and n is 1) as a main component.
  • the obtained curable resin B had a weight average molecular weight of 700 and a hydrogen bondable functional group (hydroxyl group) value of 0.0057 mol / g.
  • a curable resin C was obtained by filtering the obtained reaction product through a column.
  • the curable resin C is a compound represented by the above formula (1) (R 1 is a hydrogen atom, R 2 is a group represented by the formula (2-1) (R It was confirmed that 4 is a methylene group, p is 0), R 3 is a group represented by the formula (2-2) (q is 0), and n is 1) as a main component.
  • the resulting curable resin C had a weight average molecular weight of 1100 and a hydrogen bondable functional group (hydroxyl group) value of 0.0036 mol / g.
  • the curable resin D is a compound represented by the above formula (3) (R 5 is a hydrogen atom, R 6 and R 7 are represented by the formula (4-1). group (R 8 is a methylene group, p is 0), m is confirmed to contain 1) as a main component.
  • the resulting curable resin D had a weight average molecular weight of 900 and a hydrogen bondable functional group (hydroxyl group) value of 0.0033 mol / g.
  • the curable resin E is a compound represented by the above formula (3) (R 5 is a hydrogen atom, R 6 is a group represented by the formula (4-1) (R It was confirmed that 8 is a methylene group, p is 0), R 7 is a group represented by the formula (4-2) (q is 0), and m is 1) as a main component.
  • the obtained curable resin E had a weight average molecular weight of 800 and a hydrogen bondable functional group (hydroxyl group) value of 0.0038 mol / g.
  • curable resin F ethylene oxide-modified bisphenol A dimethacrylate (manufactured by Hitachi Chemical Co., Ltd., “Fancryl FA-321M”, 2 aromatic rings in molecule, weight average molecular weight 900, no hydrogen bonding functional group) is used. It was.
  • the curable resin G is a group represented by the formula (1) in which R 1 is a hydrogen atom and R 2 is a group represented by the formula (2-2) (q is 0), It was confirmed that a compound corresponding to the compound in which n is 0 was contained as a main component.
  • the obtained curable resin G had a weight average molecular weight of 400 and a hydrogen bondable functional group (hydroxyl group) value of 0.0050 mol / g.
  • (Curable resin H) 780 parts by weight of bisphenol F diglycidyl ether, 216 parts by weight of acrylic acid, 2 parts by weight of triethylamine as a reaction catalyst, and 2 parts by weight of p-methoxyphenol as a polymerization inhibitor are added to the reaction flask, and stirred at 90 ° C. for 5 hours. And reacted. The obtained reaction product was filtered through a column to obtain a curable resin H.
  • the curable resin H is a group represented by the formula (3) wherein R 5 is a hydrogen atom and R 6 is a group represented by the formula (4-1) (R 8 is a methylene group).
  • the resulting curable resin H had a weight average molecular weight of 400 and a hydrogen bondable functional group (hydroxyl group) value of 0.0025 mol / g).
  • a curable resin J was obtained by filtering the obtained reaction product through a column.
  • the curable resin J is a compound represented by the above formula (1) (R 1 is a hydrogen atom, R 2 is a group represented by the formula (2-2) (q 0), R 3 is a hexamethylene group, and n is 1).
  • the resulting curable resin J had a weight average molecular weight of 800 and a hydrogen bondable functional group (hydroxyl group) value of 0.0050 mol / g.
  • One part by weight of spacer particles (Sekisui Chemical Co., Ltd., “Micropearl SP-2050”) having an average particle diameter of 5 ⁇ m is used for 100 parts by weight of each sealing agent for liquid crystal display elements obtained in Examples and Comparative Examples. It was uniformly dispersed by a stirrer. A very small amount of the sealant in which the spacer particles are dispersed was taken in the center of a glass substrate (20 mm ⁇ 50 mm ⁇ thickness 0.7 mm), and the same type of glass substrate was overlaid thereon.
  • the sealing agent for liquid crystal display elements was spread and irradiated with 3000 mJ / cm 2 of ultraviolet rays using a metal halide lamp, and then the sealing agent was cured by heating at 120 ° C. for 1 hour to obtain an adhesion test piece.
  • the adhesive strength was measured using the tension gauge. When the adhesive strength is 3.5 kg / cm 2 or more, “ ⁇ ”, when it is 3.0 kg / cm 2 or more and less than 3.5 kg / cm 2 ,“ ⁇ ”, 2.5 kg / cm 2 or more 3 " ⁇ " the case was less than .0kg / cm 2, was evaluated adhesive where the adhesive strength is less than 2.5 kg / cm 2 as " ⁇ ".
  • the moisture permeability was measured by putting in a humidity oven.
  • the case of m 2 ⁇ 24 hr or more was evaluated as “x” to evaluate moisture permeability.
  • a seal pattern was formed on one of the two rubbed alignment films and the substrate with a transparent electrode by applying each liquid crystal display element sealant obtained in Examples and Comparative Examples with a dispenser so as to draw a square frame. .
  • a sealant for a liquid crystal display element was spotted on the inner side of the formed seal pattern.
  • fine droplets of a liquid crystal containing liquid crystal molecules having a cyano group as a polar group (“4-pentyl-4-biphenylcarbonitrile” manufactured by Tokyo Chemical Industry Co., Ltd.) are applied to the entire surface of the sealing agent frame of the substrate with a transparent electrode. Then, the other substrate was superposed in a vacuum.
  • the outer frame seal portion was irradiated with 3000 mJ / cm 2 ultraviolet rays using a metal halide lamp.
  • the masked sealant for the liquid crystal display element was masked so as not to be irradiated with ultraviolet rays.
  • the liquid crystal display element was obtained by heating at 120 degreeC for 1 hour, and hardening the sealing compound for liquid crystal display elements.
  • contamination property was judged by the nonuniformity around the dotted sealing agent. Low liquid crystal contamination is indicated by “ ⁇ ” when there is no unevenness, “ ⁇ ” when there is slight unevenness, “ ⁇ ” when there is slight unevenness, and “ ⁇ ” when there is considerable unevenness. evaluated.
  • the sealing compound for liquid crystal display elements which is excellent in adhesiveness, moisture-permeation prevention property, and low liquid-crystal contamination can be provided.
  • 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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  • Crystallography & Structural Chemistry (AREA)
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Abstract

La présente invention concerne un produit d'étanchéité pour un élément d'affichage à cristaux liquides, le produit d'étanchéité présentant une excellente adhérence, une excellente prévention de la pénétration d'humidité et une excellente résistance à la contamination de cristaux liquides. L'invention concerne également un produit à conduction verticale et un élément d'affichage à cristaux liquides qui sont obtenus en utilisant le produit d'étanchéité destiné à un élément d'affichage à cristaux liquides. La présente invention concerne : (A) un produit d'étanchéité pour un élément d'affichage à cristaux liquides, le produit d'étanchéité contenant une résine durcissable et un initiateur de polymérisation radicalaire, la résine durcissable étant un composé (méth)acrylique ayant une valeur de groupe fonctionnel de liaison à l'hydrogène d'au moins 0,0030 mol/g et un poids moléculaire de 500 à 1 200, n'ayant pas de groupe époxy, et ayant au moins trois cycles aromatiques par molécule ; et/ou (B) un produit d'étanchéité pour un élément d'affichage à cristaux liquides, le produit d'étanchéité contenant une résine époxyde (méth)acrylique modifiée partielle qui a une valeur de groupe fonctionnel de liaison à l'hydrogène d'au moins 0,0030 mol/g et un poids moléculaire de 500 à 1 200, et ayant au moins trois cycles aromatiques par molécule.
PCT/JP2019/021056 2018-06-01 2019-05-28 Produit d'étanchéité d'élément d'affichage à cristaux liquides, produit à conduction verticale, et élément d'affichage à cristaux liquides WO2019230709A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004104683A1 (fr) * 2003-05-21 2004-12-02 Nippon Kayaku Kabushiki Kaisha Agent de scellement pour cristal liquide et cellule d'affichage a cristaux liquides contenant celui-ci
JP2005308813A (ja) * 2004-04-16 2005-11-04 Sekisui Chem Co Ltd 液晶表示素子用硬化性樹脂組成物
KR20070038358A (ko) * 2005-10-05 2007-04-10 주식회사 두산 액정표시소자용 실란트 조성물 및 이를 이용한 씰제
WO2008102550A1 (fr) * 2007-02-20 2008-08-28 Mitsui Chemicals, Inc. Composition de résine durcissable pour sceller un cristal liquide, et procédé de fabrication d'un panneau d'affichage à cristaux liquides utilisant cette composition
WO2017082000A1 (fr) * 2015-11-09 2017-05-18 積水化学工業株式会社 Produit d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
JP2017218490A (ja) * 2016-06-06 2017-12-14 日華化学株式会社 コーティング剤、樹脂硬化膜及び積層体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004104683A1 (fr) * 2003-05-21 2004-12-02 Nippon Kayaku Kabushiki Kaisha Agent de scellement pour cristal liquide et cellule d'affichage a cristaux liquides contenant celui-ci
JP2005308813A (ja) * 2004-04-16 2005-11-04 Sekisui Chem Co Ltd 液晶表示素子用硬化性樹脂組成物
KR20070038358A (ko) * 2005-10-05 2007-04-10 주식회사 두산 액정표시소자용 실란트 조성물 및 이를 이용한 씰제
WO2008102550A1 (fr) * 2007-02-20 2008-08-28 Mitsui Chemicals, Inc. Composition de résine durcissable pour sceller un cristal liquide, et procédé de fabrication d'un panneau d'affichage à cristaux liquides utilisant cette composition
WO2017082000A1 (fr) * 2015-11-09 2017-05-18 積水化学工業株式会社 Produit d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
JP2017218490A (ja) * 2016-06-06 2017-12-14 日華化学株式会社 コーティング剤、樹脂硬化膜及び積層体

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