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WO2017061303A1 - Produit d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides - Google Patents

Produit d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides Download PDF

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Publication number
WO2017061303A1
WO2017061303A1 PCT/JP2016/078392 JP2016078392W WO2017061303A1 WO 2017061303 A1 WO2017061303 A1 WO 2017061303A1 JP 2016078392 W JP2016078392 W JP 2016078392W WO 2017061303 A1 WO2017061303 A1 WO 2017061303A1
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Prior art keywords
meth
acrylate
liquid crystal
crystal display
epoxy
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PCT/JP2016/078392
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English (en)
Japanese (ja)
Inventor
慶枝 松井
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Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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Priority to CN201680010535.4A priority Critical patent/CN107250903B/zh
Priority to JP2016561025A priority patent/JP6795400B2/ja
Priority to KR1020177023955A priority patent/KR102641044B1/ko
Publication of WO2017061303A1 publication Critical patent/WO2017061303A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08F220/00—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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—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
    • 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
    • C08G59/20—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 epoxy compounds used
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/04—Non-macromolecular organic compounds
    • C09K2200/0441—Carboxylic acids, salts, anhydrides or esters thereof

Definitions

  • the present invention relates to a sealant for a liquid crystal display element that is excellent in photocurability, adhesiveness, and moisture permeation prevention. Moreover, this invention relates to the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements.
  • Patent Document 1 and Patent Document 2 a method for manufacturing a liquid crystal display element such as a liquid crystal display cell has been disclosed in, for example, Patent Document 1 and Patent Document 2 from the conventional vacuum injection method from the viewpoint of shortening tact time and optimizing the amount of liquid crystal used.
  • a liquid crystal dropping method called a dripping method using such a photothermal combined curing type sealant has become the mainstream.
  • a rectangular seal pattern is formed on one of two transparent substrates with electrodes by dispensing.
  • a liquid crystal micro-droplet is dropped on the entire surface of the transparent substrate frame in a state where the sealant is uncured, and the other transparent substrate is immediately overlaid, and the seal portion is irradiated with light such as ultraviolet rays for temporary curing.
  • heating is performed at the time of liquid crystal annealing to perform main curing, and a liquid crystal display element is manufactured. If the substrates are bonded together under reduced pressure, a liquid crystal display element can be manufactured with extremely high efficiency.
  • liquid crystal display elements are increasingly required to have moisture resistance reliability in driving in high-temperature and high-humidity environments, and the performance of sealing agents to prevent water from entering from the outside. Is further demanded.
  • it is necessary to improve the adhesion between the sealing agent and the substrate and to make the cured product of the sealing agent excellent in moisture permeation prevention.
  • it has been difficult to achieve both adhesiveness and moisture permeation preventive properties in the sealing agent.
  • the present invention relates to an epoxy (meth) acrylate having one or more (meth) acryloyl groups in one molecule, an epoxy compound having one or more epoxy groups in one molecule, and two or more in one molecule.
  • a polyfunctional maleimide compound having a maleimide group, and the content of the epoxy (meth) acrylate in a total of 100 parts by weight of the epoxy (meth) acrylate and the epoxy compound exceeds 50 parts by weight and is 90 parts by weight or less. It is the sealing compound for liquid crystal display elements which is.
  • the present invention is described in detail below.
  • the inventor of the present invention provides a liquid crystal display element sealing agent containing a (meth) acrylic compound and an epoxy compound, further containing a polyfunctional maleimide compound, thereby preventing moisture permeation of the liquid crystal display element sealing agent.
  • the obtained sealing agent for liquid crystal display elements has a problem of insufficient photocurability and adhesiveness. Therefore, the present inventor further uses an epoxy (meth) acrylate as the (meth) acrylic compound, and by setting the content of the epoxy (meth) acrylate to a specific range, photocurability, adhesiveness, and moisture permeability.
  • the present inventors have found that a sealing agent for liquid crystal display elements having excellent prevention properties can be obtained, and have completed the present invention.
  • liquid-crystal contamination can also be suppressed by using the sealing compound for liquid crystal display elements of this invention.
  • (meth) acryl means acryl or methacryl
  • (meth) acrylate means acrylate or methacrylate
  • epoxy (meth) acrylate means epoxy. It represents a compound obtained by reacting an epoxy group in a compound with (meth) acrylic acid.
  • the sealing agent for liquid crystal display elements of this invention contains the epoxy (meth) acrylate which has a 1 or more (meth) acryloyl group in 1 molecule.
  • the “(meth) acryloyl” means acryloyl or methacryloyl.
  • the said epoxy (meth) acrylate is not limited to the compound which reacted all the epoxy groups in an epoxy compound with (meth) acrylic acid, As mentioned later, a partial (meth) acryl modified epoxy resin is also said epoxy ( Included in (meth) acrylate.
  • the epoxy (meth) acrylate is preferably one having two or more (meth) acryloyl groups in one molecule because of its high reactivity.
  • Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
  • Examples of the epoxy compound as a raw material for synthesizing the epoxy (meth) acrylate include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and 2,2′-diallyl bisphenol A type epoxy resin. , Hydrogenated bisphenol type epoxy resin, propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol Novolac epoxy resin, orthocresol novolac epoxy resin, dicyclopentadiene novolac epoxy resin, biphenyl novolac epoxy resin, naphtha Ren phenol novolak type epoxy resin, glycidyl amine type epoxy resin, alkyl polyol type epoxy resin, rubber-modified epoxy resins, glycidyl ester compounds.
  • Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
  • Examples of commercially available naphthalene type epoxy resins include Epicron HP4032, Epicron EXA-4700 (both manufactured by DIC) and the like.
  • Examples of commercially available phenol novolac epoxy resins include Epicron N-770 (manufactured by DIC).
  • Examples of the ortho-cresol novolac type epoxy resin that are commercially available include epiclone N-670-EXP-S (manufactured by DIC).
  • Examples of commercially available glycidylamine type epoxy resins include jER630 (manufactured by Mitsubishi Chemical), Epicron 430 (manufactured by DIC), and TETRAD-X (manufactured by Mitsubishi Gas Chemical).
  • Examples of commercially available alkyl polyol type epoxy resins include ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epiklon 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX-611. (Manufactured by Nagase ChemteX Corporation).
  • Examples of commercially available rubber-modified epoxy resins include YR-450, YR-207 (both manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epolide PB (manufactured by Daicel Corporation), and the like.
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation).
  • Other commercially available epoxy compounds include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by NS Also, Mitsubishi Chemical Corporation), EXA-7120 (DIC Corporation), TEPIC (Nissan Chemical Corporation) and the like.
  • Examples of commercially available epoxy (meth) acrylates include, for example, EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRY3603 EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy Ester 200PA, epoxy ester 80MFA Epoxy ester 3002M, Epoxy ester 3002A, Epoxy ester 1600A, Epoxy ester 3000M, Epoxy ester 3000A, Epoxy ester 200EA, Epoxy ester 400EA (all manufactured by Kyoeisha Chemical Co., Ltd.), Denacol acrylate DA-141, Den
  • a partial (meth) acryl-modified epoxy resin is also preferably used as the epoxy (meth) acrylate.
  • the partial (meth) acryl-modified epoxy resin can be obtained by reacting an epoxy group of a part of two or more epoxy compounds with (meth) acrylic acid.
  • the epoxy (meth) acrylate is an aliphatic compound that does not have an aromatic skeleton because the sealing agent for liquid crystal display elements obtained can be excellent in both adhesiveness and flexibility of a cured product. It is preferable to contain an epoxy (meth) acrylate.
  • the content of the epoxy (meth) acrylate in a total of 100 parts by weight of the epoxy (meth) acrylate and the epoxy compound is more than 50 parts by weight and 90 parts by weight or less.
  • the content of the epoxy (meth) acrylate is 50 parts by weight or less, the obtained sealing agent for liquid crystal display elements is inferior in photocurability and adhesiveness or causes liquid crystal contamination.
  • content of the said epoxy (meth) acrylate exceeds 90 weight part, the sealing compound for liquid crystal display elements obtained will be inferior to moisture-permeable prevention property and adhesive force.
  • the minimum with preferable content of the said epoxy (meth) acrylate is 60 weight part, and a preferable upper limit is 85 weight part.
  • the content of the said epoxy (meth) acrylate is the epoxy (meth) acrylate which does not have an epoxy group, and the said partial (meth) acryl modified epoxy resin Is represented by the following formula (I).
  • the sealing agent for liquid crystal display elements of the present invention may contain other (meth) acrylic compounds in addition to the epoxy (meth) acrylate as long as the object of the present invention is not impaired.
  • the other (meth) acrylic compounds include (meth) acrylic acid ester compounds obtained by reacting (meth) acrylic acid with a compound having a hydroxyl group, and (meth) acrylic acid derivatives having a hydroxyl group in an isocyanate compound. And urethane (meth) acrylate obtained by reacting.
  • 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
  • Examples of the urethane (meth) acrylate obtained by reacting a hydroxyl group-containing (meth) acrylic acid derivative with the isocyanate compound include, for example, (meth) acrylic having a hydroxyl group with respect to 1 equivalent of an isocyanate compound having two isocyanate groups. Two equivalents of the acid derivative can be obtained by reacting in the presence of a catalytic amount of a tin-based compound.
  • isocyanate compound used as the raw material for the urethane (meth) acrylate examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4.
  • MDI '-Diisocyanate
  • hydrogenated MDI polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanate) Phenyl) thiophosphate, tetramethylxylene diisocyanate, 1,6,11-undecanetriiso Aneto and the like.
  • Examples of the isocyanate compound that is a raw material for the urethane (meth) acrylate include, for example, polyols such as ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol. Chain-extended isocyanate compounds obtained by reaction with excess isocyanate compounds can also be used.
  • Examples of the (meth) acrylic acid derivative having a hydroxyl group as a raw material for the urethane (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxybutyl (meth). Hydroxyalkyl (meth) acrylates such as acrylate, 4-hydroxybutyl (meth) acrylate, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol, etc.
  • Mono (meth) acrylates of dihydric alcohols mono (meth) acrylates or di (meth) acrylates of trivalent alcohols such as trimethylolethane, trimethylolpropane and glycerin, and bisphenol A type epoxy alcohol Epoxy (meth) acrylate of rate, and the like.
  • Examples of commercially available urethane (meth) acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8804 , Art resin N-1255, Art Resin UN-3320HB, Art Resin UN-7100, Art Resin UN-9000A, Art Resin UN-9000H (all manufactured by Negami Industrial Co., Ltd.), U-2HA, U-2PHA, U-3HA, U- 4HA, U-6H, U-6HA, U-6LPA, U-10H, U-15HA, U
  • the sealing agent for liquid crystal display elements of the present invention contains an epoxy compound having one or more epoxy groups in one molecule.
  • said epoxy compound the thing similar to what was mentioned above as an epoxy compound used as the raw material for synthesize
  • the obtained sealing agent for liquid crystal display elements can be made excellent in both adhesiveness and flexibility of a cured product, it preferably contains an aliphatic epoxy compound having no aromatic skeleton. .
  • a partial (meth) acryl modified epoxy resin is contained in the said epoxy (meth) acrylate instead of the said epoxy compound.
  • polyfunctional maleimide compound a compound represented by the following formula (1) or a compound represented by the following formula (2) is preferably used.
  • R 1 represents an alkylene group having 2 to 3 carbon atoms, and n is an integer of 2 to 40.
  • R 2 preferably has 12 to 45 carbon atoms.
  • R 2 preferably has an aliphatic ring.
  • Specific examples of the compound represented by the above formula (2) include 1,20-bismaleimide-10,11-dioctyl-eicosane (compound represented by the following formula (3-1)), 1- Heptylenemaleimide-2-octylenemaleimide-4-octyl-5-heptylcyclohexane (compound represented by the following formula (3-2)), 1,2-dioctylenemaleimide-3-octyl-4-hexyl Examples include cyclohexane (compound represented by the following formula (3-3)) and the like, which can be synthesized by the method described in US Pat. No. 5,973,166.
  • the minimum with preferable content of the said polyfunctional maleimide compound in the total 100 weight part of the said epoxy (meth) acrylate and the said epoxy compound is 0.1 weight part, and a preferable upper limit is 15 weight part.
  • the content of the polyfunctional maleimide compound is within this range, the obtained sealing agent for liquid crystal display elements is more excellent in photocurability, adhesiveness, and moisture permeability prevention.
  • the minimum with more preferable content of the said polyfunctional maleimide compound is 1 weight part, and a more preferable upper limit is 10 weight part.
  • the polyfunctional maleimide compound can exhibit a role as a polymerization initiator, but the reactivity may be insufficient with the polyfunctional maleimide compound alone. Therefore, it is preferable that the sealing compound for liquid crystal display elements of the present invention contains a polymerization initiator.
  • radical photopolymerization initiator As said polymerization initiator, radical photopolymerization initiator, a thermal radical polymerization initiator, etc. are mentioned, It is preferable to use radical photopolymerization initiator. Furthermore, since the adhesiveness of the obtained sealing agent for liquid crystal display elements can be made better, it is more preferable to use a photoradical polymerization initiator in combination with a thermal radical polymerization initiator or a curing accelerator described later. preferable.
  • oxime ester compounds examples include 1- (4- (phenylthio) phenyl) -1,2-octanedione 2- (O-benzoyloxime), O-acetyl-1- (6- (2-methylbenzoyl) ) -9-ethyl-9H-carbazol-3-yl) ethanone oxime and the like.
  • Examples of the commercially available photo radical polymerization initiators include IRGACURE OXE01, IRGACURE OXE02, IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE PF2
  • Examples include methyl ether, benzoin ethyl ether, and benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.).
  • the content of the photo radical polymerization initiator is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to a total of 100 parts by weight of the epoxy (meth) acrylate and the epoxy compound.
  • the content of the photo radical polymerization initiator is within this range, the photocurability can be improved without deteriorating the storage stability of the obtained sealing agent for liquid crystal display elements.
  • the minimum with more preferable content of the said radical photopolymerization initiator is 0.5 weight part, and a more preferable upper limit is 5 weight part.
  • thermal radical polymerization initiator what consists of an organic peroxide, an azo compound, etc. is mentioned, for example. Of these, organic peroxides are preferable.
  • organic peroxide examples include dicumyl peroxide, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxy ester, diacyl peroxide, and peroxydicarbonate. Of these, dicumyl peroxide is preferable.
  • the azo compound a polymer azo initiator composed of a polymer azo compound is preferable.
  • the polymer azo initiator means a compound having an azo group and generating a radical capable of curing a (meth) acryloyloxy group by heat and having a number average molecular weight of 300 or more. .
  • the preferable lower limit of the number average molecular weight of the polymeric azo initiator is 1000, and the preferable upper limit is 300,000.
  • the more preferable lower limit of the number average molecular weight of the polymeric azo initiator 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
  • polymer azo initiator examples include those having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
  • polymer azo initiator 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.
  • Examples of such a polymer azo initiator include polycondensates of 4,4′-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4′-azobis (4-cyanopentanoic acid) Examples thereof include polycondensates of polydimethylsiloxane having a terminal amino group, such as VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (all of which are Wako Pure Chemical Industries, Ltd.) Manufactured) and the like.
  • Examples of azo compounds that are not polymers include V-65 and V-501 (both manufactured by Wako Pure Chemical Industries, Ltd.).
  • the content of the thermal radical polymerization initiator is preferably 0.05 parts by weight and preferably 10 parts by weight with respect to a total of 100 parts by weight of the epoxy (meth) acrylate and the epoxy compound.
  • the thermosetting property can be improved without deteriorating the storage stability of the obtained sealing agent for liquid crystal display elements.
  • the minimum with more preferable content of the said thermal 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.
  • thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Among these, solid organic acid hydrazide is preferably used.
  • Examples of the solid organic acid hydrazide include 1,3-bis (hydrazinocarboethyl-5-isopropylhydantoin), sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
  • Examples thereof include SDH, ADH (manufactured by Otsuka Chemical Co., Ltd.), MDH (manufactured by Nippon Finechem Co., Ltd.), Amicure VDH, Amicure VDH-J, Amicure UDH (all manufactured by Ajinomoto Fine Techno Co., Ltd.) and the like.
  • thermosetting agent As for content of the said thermosetting agent, a preferable minimum is 1 weight part and a preferable upper limit is 50 weight part with respect to a total of 100 weight part of the said epoxy (meth) acrylate and the said epoxy compound. When the content of the thermosetting agent is within this range, the thermosetting property can be further improved without deteriorating the applicability of the obtained sealing agent for liquid crystal display elements.
  • the upper limit with more preferable content of the said thermosetting agent is 30 weight part.
  • curing accelerator examples include amine adduct compounds, tertiary amines, and phosphines. Of these, amine adduct compounds are preferred.
  • a preferable minimum is 0.5 weight part and a preferable upper limit is 40 weight part with respect to a total of 100 weight part of the said epoxy (meth) acrylate and the said epoxy compound.
  • the content of the curing accelerator is within this range, the curability can be improved without deteriorating the storage stability of the obtained sealing agent for liquid crystal display elements.
  • the sealing compound for liquid crystal display elements of this invention contains a soft particle from a viewpoint of improving the softness
  • the flexible particles include silicone particles, vinyl particles, urethane particles, fluorine particles, and nitrile particles. Of these, silicone particles and vinyl particles are preferable.
  • a silicone rubber particle is preferable from a dispersible viewpoint to resin.
  • (Meth) acrylic particles are preferably used as the vinyl particles.
  • the (meth) acrylic particles can be obtained by polymerizing monomers as raw materials by a known method. Specifically, for example, a method in which a monomer is suspension-polymerized in the presence of a radical polymerization initiator, and a seed particle is swollen by absorbing the monomer into a non-crosslinked seed particle in the presence of a radical polymerization initiator. And a seed polymerization method.
  • Examples of the monomer that is a raw material for forming the (meth) acrylic particles include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and hexyl (meth).
  • Alkyl (meth) such as acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, etc.
  • Acrylates oxygen-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, glycerol (meth) acrylate, polyoxyethylene (meth) acrylate, glycidyl (meth) acrylate, etc.
  • (meth) nitrile and containing monomers such as acrylonitrile, trifluoromethyl (meth) acrylate, monofunctional monomer such as a fluorine-containing (meth) acrylates such as pentafluoroethyl (meth) acrylate.
  • alkyl (meth) acrylates are preferable because the Tg of the homopolymer is low and the deformation amount when a 1 g load is applied can be increased.
  • tetramethylol methane tetra (meth) acrylate tetramethylol methane tri (meth) acrylate, tetramethylol methane di (meth) acrylate, trimethylol propane tri (meth) acrylate, dipentaerythritol hexa ( (Meth) acrylate, dipentaerythritol penta (meth) acrylate, glycerol tri (meth) acrylate, glycerol di (meth) acrylate, (poly) ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, ( Poly) tetramethylene di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, isocyanuric acid
  • the preferable lower limit is 1% by weight and the preferable upper limit is 90% by weight in the whole monomer as a raw material for forming the (meth) acrylic particles.
  • the amount of the crosslinkable monomer used is 1% by weight or more, the solvent resistance is improved, and when kneaded with various sealant raw materials, problems such as swelling do not occur and the particles are easily dispersed uniformly.
  • the amount of the crosslinkable monomer used is 90% by weight or less, the recovery rate can be lowered.
  • a more preferable lower limit of the amount of the crosslinkable monomer used is 3% by weight, and a more preferable upper limit is 80% by weight.
  • styrene monomers such as styrene and ⁇ -methylstyrene
  • vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, and propyl vinyl ether, vinyl acetate, vinyl butyrate, and laurin.
  • Carboxylic acid vinyl esters such as vinyl acid and vinyl stearate, unsaturated hydrocarbons such as ethylene, propylene, isoprene and butadiene, halogen-containing monomers such as vinyl chloride, vinyl fluoride and chlorostyrene, triallyl ( Use monomers such as iso) cyanurate, triallyl trimellitate, divinylbenzene, diallylphthalate, diallylacrylamide, diallyl ether, ⁇ - (meth) acryloxypropyltrimethoxysilane, trimethoxysilylstyrene, vinyltrimethoxysilane May be.
  • core-shell (meth) acrylate copolymer fine particles are also preferably used.
  • core-shell (meth) acrylate copolymer fine particles include F351 (manufactured by Zeon Kasei Co., Ltd.).
  • vinyl particles for example, polydivinylbenzene particles, polychloroprene particles, butadiene rubber particles and the like may be used.
  • the preferable lower limit of the average particle diameter of the flexible particles is 0.01 ⁇ m, and the preferable upper limit is 10 ⁇ m.
  • the more preferable lower limit of the average particle diameter of the flexible particles is 0.1 ⁇ m, and the more preferable upper limit is 8 ⁇ m.
  • the average particle diameter of the said flexible particle means the value obtained by measuring using the laser diffraction type particle size distribution measuring apparatus about the particle
  • the laser diffraction type distribution measuring device Mastersizer 2000 (manufactured by Malvern) or the like can be used.
  • the preferable lower limit of the hardness of the flexible particles is 10, and the preferable upper limit is 50.
  • the more preferable lower limit of the hardness of the soft particles is 20, and the more preferable upper limit is 40.
  • the hardness of the said flexible particle means the durometer A hardness measured by the method based on JISK6253.
  • the preferable lower limit of the content of the flexible particles in 100 parts by weight of the sealing agent for liquid crystal display elements of the present invention is 5 parts by weight, and the preferable upper limit is 50 parts by weight.
  • grain is 10 weight part, and a more preferable upper limit is 30 weight part.
  • the sealing agent for liquid crystal display elements of the present invention preferably contains a filler for the purpose of improving the viscosity, further improving the adhesion due to the stress dispersion effect, improving the linear expansion coefficient, and the like.
  • the filler examples include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide,
  • inorganic fillers such as calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate, and organic fillers other than those contained in the flexible particles.
  • 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 content of the filler is within this range, the adhesiveness is improved without deteriorating applicability and the like.
  • 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 compound for liquid crystal display elements of this invention contains a silane coupling agent.
  • the silane coupling agent mainly serves as an adhesion assistant for better bonding the sealing agent and the substrate.
  • silane coupling agent since it is excellent in the effect which improves adhesiveness with a board
  • -Aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are preferably used.
  • 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.
  • the light-shielding agent examples include titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black.
  • the iron oxide, titanium oxide, etc. which were mentioned as said inorganic filler can also be used as said light-shielding agent.
  • titanium black is preferable.
  • Titanium black is a substance having a higher transmittance in the vicinity of the ultraviolet region, particularly for light having a wavelength of 370 to 450 nm, compared to the average transmittance for light having a wavelength of 300 to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby providing a light shielding property to the sealing agent for liquid crystal display elements of the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region.
  • the light shielding agent contained in the liquid crystal display element sealant of the present invention is preferably a highly insulating material, and titanium black is also preferred as the highly insulating light shielding agent.
  • the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
  • the liquid crystal display element produced using the sealing agent for liquid crystal display elements of the present invention containing the above-described titanium black as a light-shielding agent has 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.
  • titanium black examples include 12S, 13M, 13M-C, 13R-N, 14M-C (all manufactured by Mitsubishi Materials Corporation), Tilak D (manufactured by Ako Kasei Co., Ltd.), and the like. Can be mentioned.
  • the preferable lower limit of the specific surface area of the titanium black is 13 m 2 / g, the preferable upper limit is 30 m 2 / g, the more preferable lower limit is 15 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
  • the preferred lower limit of the volume resistance of the titanium black is 0.5 ⁇ ⁇ cm, the preferred upper limit is 3 ⁇ ⁇ cm, the more preferred lower limit is 1 ⁇ ⁇ cm, and the more preferred upper limit is 2.5 ⁇ ⁇ cm.
  • the primary particle diameter of the said light-shielding agent will not be specifically limited if it is below the distance between the board
  • the more preferable lower limit of the primary particle diameter of the light shielding agent is 5 nm
  • the more preferable upper limit is 200 nm
  • the still more preferable lower limit is 10 nm
  • the still more preferable upper limit is 100 nm.
  • the primary particle size of the light shielding agent can be measured by using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS) and dispersing the light shielding agent in a solvent (water, organic solvent, etc.).
  • the preferable lower limit of the content of the light-shielding agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 5 parts by weight, and the preferable upper limit is 80 parts by weight.
  • the content of the light-shielding agent is within this range, the liquid crystal display element sealant can exhibit better light-shielding properties without reducing the adhesion to the substrate, the strength after curing, and the drawability. it can.
  • 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 further contains additives such as a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor, if necessary. May be.
  • the sealing agent for liquid crystal display elements of the present invention for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, epoxy (meth) acrylate and And a method of mixing an epoxy compound, a polyfunctional maleimide compound, and a radical photopolymerization initiator, a silane coupling agent and the like used as necessary.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, epoxy (meth) acrylate and And a method of mixing an epoxy compound, a polyfunctional maleimide compound, and a radical photopolymerization initiator, a silane coupling agent and the like used 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.
  • Such a vertical conduction material containing the sealing agent for liquid crystal display elements of the present invention and conductive fine particles is also one aspect of the present invention.
  • the conductive fine particles 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.
  • a liquid crystal dropping method is preferably used.
  • the liquid crystal display element sealant of the present invention is applied to one of two substrates such as a glass substrate with electrodes such as an ITO thin film or a polyethylene terephthalate substrate by screen printing, dispenser application, or the like.
  • the sealing compound for liquid crystal display elements which is excellent in photocurability, adhesiveness, and moisture-permeable prevention property 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.
  • Examples 1 to 23 and Comparative Examples 1 to 4 According to the blending ratios listed in Tables 1 to 3, each material was mixed using a planetary stirrer (“Shinky Co.,“ Awatori Nertaro ”), and then mixed using three rolls. The sealants for liquid crystal display elements of Examples 1 to 23 and Comparative Examples 1 to 4 were prepared.
  • the polytetramethylene ether glycol dimaleimide acetate (“LMICURE MIA200" manufactured by DIC) described in the table as the polyfunctional maleimide compound is a compound represented by the above formula (1).
  • the “content of epoxy (meth) acrylate in 100 parts by weight of the total of epoxy (meth) acrylate and epoxy compound” in Examples 1 to 23 and Comparative Examples 2 to 4 in the table is the above formula (I).
  • the moisture permeability was measured by putting in a constant temperature and humidity oven.
  • the sealing compound for liquid crystal display elements which is excellent in photocurability, adhesiveness, and moisture-permeable prevention property 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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Abstract

L'objectif de la présente invention est de fournir un produit d'étanchéité pour éléments d'affichage à cristaux liquides, qui est excellent en termes de performance de photo-durcissement, d'adhésivité, et de performance de prévention de perméabilité à l'humidité. De plus, l'objectif de la présente invention est de fournir un matériau à conduction verticale et un élément d'affichage à cristaux liquides fabriqué à l'aide du produit d'étanchéité pour éléments d'affichage à cristaux liquides. À cet effet, la présente invention concerne un produit d'étanchéité pour éléments d'affichage à cristaux liquides qui contient : un (méth)acrylate d'époxy ayant un ou plusieurs groupes (méth)acryloyle dans une molécule unique de ce dernier ; un composé époxy ayant un ou plusieurs groupes époxy dans une molécule unique de ce dernier ; et un composé de maléimide polyfonctionnel ayant deux groupes maléimide ou plus dans une molécule unique de ce dernier, la quantité contenue du (méth)acrylate d'époxy par rapport à 100 parties en poids du total du (méth)acrylate d'époxy et du composé d'époxy étant supérieure à 50 parties en poids mais n'étant pas supérieure à 90 parties en poids.
PCT/JP2016/078392 2015-10-09 2016-09-27 Produit d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides Ceased WO2017061303A1 (fr)

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CN201680010535.4A CN107250903B (zh) 2015-10-09 2016-09-27 液晶显示元件用密封剂、上下导通材料及液晶显示元件
JP2016561025A JP6795400B2 (ja) 2015-10-09 2016-09-27 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
KR1020177023955A KR102641044B1 (ko) 2015-10-09 2016-09-27 액정 표시 소자용 시일제, 상하 도통 재료, 및 액정 표시 소자

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WO2019221026A1 (fr) * 2018-05-18 2019-11-21 積水化学工業株式会社 Agent de scellement d'élément d'affichage à cristaux liquides, élément d'affichage à cristaux liquides, et procédé de production d'élément d'affichage à cristaux liquides
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KR20180067461A (ko) 2018-06-20
CN107250903A (zh) 2017-10-13
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JP6795400B2 (ja) 2020-12-02

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