WO2022255452A1 - Agent d'étanchéité pour éléments d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé - Google Patents

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

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WO2022255452A1
WO2022255452A1 PCT/JP2022/022496 JP2022022496W WO2022255452A1 WO 2022255452 A1 WO2022255452 A1 WO 2022255452A1 JP 2022022496 W JP2022022496 W JP 2022022496W WO 2022255452 A1 WO2022255452 A1 WO 2022255452A1
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liquid crystal
meth
crystal display
acrylate
sealant
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PCT/JP2022/022496
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English (en)
Japanese (ja)
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大輝 山脇
秀幸 林
剛 大浦
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積水化学工業株式会社
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Priority to CN202280023421.9A priority Critical patent/CN117043670A/zh
Priority to KR1020247000209A priority patent/KR20240017908A/ko
Priority to JP2022537078A priority patent/JP7201881B1/ja
Publication of WO2022255452A1 publication Critical patent/WO2022255452A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0625—Polyacrylic esters or derivatives thereof

Definitions

  • the present invention relates to a sealant for liquid crystal display elements, which is excellent in visible light curability and low liquid crystal contamination, and which can suppress nozzle clogging during application.
  • the present invention also relates to a liquid crystal display element using the sealant for a liquid crystal display element.
  • a photo-heat curing type seal disclosed in Patent Document 1 and Patent Document 2
  • a liquid crystal dropping method called a dropping method using an agent is used.
  • the dripping method first, a frame-shaped seal pattern is formed on one of two electrode-attached transparent substrates by dispensing.
  • the sealant is not yet cured, liquid crystal microdroplets are dropped on the entire surface of the frame of the transparent substrate, the other transparent substrate is immediately attached, and the sealant is irradiated with light such as ultraviolet rays for temporary curing. .
  • the liquid crystal is annealed for final curing by heating, and a liquid crystal display element is produced. If the bonding of the substrates is performed under reduced pressure, the liquid crystal display element can be manufactured with extremely high efficiency.
  • Patent Document 3 discloses a camphorquinone-based compound and the like.
  • the present disclosure 1 is a sealant for liquid crystal display elements containing a curable resin and a photopolymerization initiator,
  • the gel fraction is 70% or more when irradiated with light of 100 mW/cm 2 for 30 seconds using an LED lamp having a peak top at a wavelength of 450 nm, and
  • the sealant for liquid crystal display elements has a gel fraction of less than 10% when irradiated with light of 400 lux for 48 hours using an LED lamp having a peak top at a wavelength of 580 nm.
  • a second aspect of the present disclosure is a liquid crystal display device having a cured product of the sealant for a liquid crystal display device of the first disclosure. The present invention will be described in detail below.
  • the present inventors irradiate the sealant by using an LED lamp having a peak top at a long wavelength (for example, a wavelength of 450 nm) without passing through a cut filter. It was considered to harden to produce a liquid crystal display element.
  • a sealant containing a camphorquinone-based compound is used as a photopolymerization initiator and such an LED lamp is used to fabricate a liquid crystal display element, it has become clear that liquid crystal contamination occurs.
  • the present inventors used a sealant containing a camphorquinone-based compound as a photopolymerization initiator, and produced a liquid crystal display device using an LED lamp having a peak top in the wavelength region on the longer wavelength side without a cut filter. It was thought that the cause of the liquid crystal contamination in some cases was that the sealant was not sufficiently cured due to the low reactivity of the camphorquinone compound. Therefore, the present inventors have investigated the use of a photopolymerization initiator such as a titanocene compound, which is superior in reactivity to visible light. The sealant sometimes clogged the nozzle of the device.
  • the application of a sealant using a photopolymerization initiator that is highly reactive to visible light is performed under a yellow lamp designed so that light with a wavelength of 500 nm or less is not irradiated in order to prevent the reaction of the photopolymerization initiator.
  • the present inventors considered that the cause of nozzle clogging during application of the sealant is that the photopolymerization initiator reacts even with the light from the yellow lamp. Therefore, the present inventors have found that the gel fraction when irradiated with light of 100 mW / cm 2 for 30 seconds using an LED lamp having a peak top at 450 nm is a specific value or more, and has a peak top at a wavelength of 580 nm.
  • the sealant for a liquid crystal display element of the present invention has a gel fraction of 70% or more. With a gel fraction of 70% or more when irradiated with light of 100 mW/cm 2 for 30 seconds using the 450 nm LED lamp, the sealant for a liquid crystal display element of the present invention has visible light curability and low liquid crystal contamination. It will be excellent in quality.
  • a preferred lower limit of the gel fraction is 80%, and a more preferred lower limit is 85%, when irradiated with light of 100 mW/cm 2 for 30 seconds using the 450 nm LED lamp.
  • the "gel fraction" means the degree to which the curable resin contained in the sealant is crosslinked and polymerized.
  • the filler and the like mixed at this time are gelled at the same time by being taken into the polymer.
  • the gel fraction can be calculated by the following formula.
  • Gel fraction (% by weight) ((G2-G0)/(G1-G0)) x 100
  • Specific work is as follows. A sealant is spread between two polyethylene terephthalate (PET) films to a thickness of 300 ⁇ m.
  • PET film include PET5011 (manufactured by Lintec Corporation). After irradiating light from one side of the PET film with a designated LED lamp and metal halide lamp, the two PET films are peeled off.
  • the sealant does not have tackiness, the cured sealant is peeled off from the PET film and then cut into strips of 1 cm x 2 cm. prevent it from being released from any other location.
  • the sealant is tacky, the sealant is collected on the plane of the microspatula and wrapped in a 200-mesh metal mesh so that the sealant is not released outside the lattice of the mesh.
  • the weight of the metal mesh to be used is measured as G0
  • the total weight of the sealant and the metal mesh is measured as G1. Note that G0 should be 1 g or more and less than 3 g, and (G1-G0) should be 0.2 g or more and less than 0.4 g.
  • 200 mesh is an index representing the fineness of the mesh, and indicates that the number of metal threads per inch is 200.
  • a metal mesh wrapped with a sealing agent is attached to a screw tube No. 1. 8 (manufactured by Maruem), 70 g of acetone is added to the screw tube and allowed to stand for 3 hours. The metal mesh enveloping the sealing agent present in the acetone is taken out with tweezers and a new screw tube No. 8 (manufactured by Maruem), 70 g of fresh acetone is added to the screw tube, and the tube is allowed to stand for another 2 hours. After taking out the metal mesh wrapped with the sealant with tweezers, it is dried in an oven at 80° C. under normal pressure for 2 hours.
  • FIG. 1 shows the emission spectrum of UELCL-P-450-X.
  • the illuminance of the 450 nm LED lamp is expressed in units of mW/cm 2 when the absolute value calibration wavelength is set to 450 nm using an ultraviolet thin illuminance meter UIT- ⁇ LED (manufactured by Ushio Inc.).
  • the liquid crystal display element sealing agent of the present invention has a gel fraction of 10% when irradiated with light of 400 lux for 48 hours using an LED lamp having a peak top at a wavelength of 580 nm (hereinafter also referred to as "580 nm LED lamp"). is less than When the gel fraction is less than 10% when irradiated with light of 400 lux for 48 hours using the 580 nm LED lamp, the sealant for liquid crystal display elements of the present invention can suppress nozzle clogging during application. becomes possible.
  • a preferred upper limit of the gel fraction is 7%, and a more preferred upper limit is 3%, when irradiated with light of 400 lux for 48 hours using the 580 nm LED lamp.
  • Examples of the 580 nm LED lamp include ECOHILUX HES-YF LDG32T Y22/22 (manufactured by Iris Ohyama Co., Ltd.).
  • FIG. 2 shows the emission spectrum of ECOHILUX HES-YF LDG32T ⁇ Y22/22.
  • the illuminance of the 580 nm LED lamp is expressed in units of lux (lx) when using a digital illuminance meter TM-201L (manufactured by TENMARS).
  • the sealant for liquid crystal display elements of the present invention contains a curable resin.
  • the curable resin preferably contains a (meth)acrylic compound.
  • the (meth)acrylic compound include (meth)acrylic acid ester compounds, epoxy (meth)acrylates, and urethane (meth)acrylates. Among them, epoxy (meth)acrylate is preferred.
  • the (meth)acrylic compound preferably has two or more (meth)acryloyl groups in one molecule from the viewpoint of reactivity.
  • the above “(meth)acryl” means acrylic or methacryl
  • the above “(meth)acrylic compound” means a compound having a (meth)acryloyl group
  • the above “( meth)acryloyl” means acryloyl or methacryloyl.
  • the above-mentioned “(meth)acrylate” means acrylate or methacrylate.
  • the above-mentioned “epoxy (meth)acrylate” represents a compound obtained by reacting all epoxy groups in an epoxy compound with (meth)acrylic acid.
  • monofunctional ones include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, and isobutyl (meth)acrylate.
  • t-butyl (meth)acrylate 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, iso myristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexyl ( meth)acrylate, isobornyl (meth)acrylate, bicyclopentenyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate,
  • bifunctional ones include, for example, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexane Diol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate (Meth) acrylate, polyethylene glycol di (meth) acrylate, 2-n-butyl-2-ethyl-1,3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) ) acrylate, polypropylene glycol di(meth)acrylate, neopen
  • trifunctional or higher ones 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 penta(meth)acrylate, dipentaerythritol penta(meth)acryl
  • 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.
  • epoxy compounds that are raw materials for synthesizing the epoxy (meth)acrylate include bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, bisphenol S type epoxy compounds, and 2,2′-diallylbisphenol A type epoxy compounds. , hydrogenated bisphenol type epoxy compound, propylene oxide added bisphenol A type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, sulfide type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound, naphthalene type epoxy compound, phenol Novolac-type epoxy compounds, ortho-cresol novolac-type epoxy compounds, dicyclopentadiene novolak-type epoxy compounds, biphenyl novolak-type epoxy compounds, naphthalenephenol novolak-type epoxy compounds, glycidylamine-type epoxy compounds, alkylpolyol-type epoxy compounds, rubber-modified epoxy compounds , glycidyl ester compounds, and the like.
  • bisphenol A type epoxy compounds include, for example, jER828EL, jER1004 (all manufactured by Mitsubishi Chemical Corporation), EPICLON EXA-850CRP (manufactured by DIC Corporation), and the like.
  • Examples of commercially available bisphenol F-type epoxy compounds include jER806 and jER4004 (both manufactured by Mitsubishi Chemical Corporation).
  • Examples of commercially available bisphenol S-type epoxy compounds include EPICLON EXA1514 (manufactured by DIC Corporation).
  • Examples of commercially available 2,2'-diallylbisphenol A type epoxy compounds include RE-810NM (manufactured by Nippon Kayaku Co., Ltd.).
  • Examples of commercially available hydrogenated bisphenol type epoxy compounds include EPICLON EXA7015 (manufactured by DIC Corporation).
  • Examples of commercially available propylene oxide-added bisphenol A type epoxy compounds include EP-4000S (manufactured by ADEKA).
  • Commercially available resorcinol-type epoxy compounds include, for example, EX-201 (manufactured by Nagase ChemteX Corporation).
  • commercially available biphenyl-type epoxy compounds include, for example, jER YX-4000H (manufactured by Mitsubishi Chemical Corporation).
  • Examples of commercially available sulfide-type epoxy compounds include YSLV-50TE (manufactured by Nippon Steel Chemical & Materials Co., Ltd.).
  • Examples of commercially available diphenyl ether type epoxy compounds include YSLV-80DE (manufactured by Nippon Steel Chemical & Materials Co., Ltd.). Examples of commercially available dicyclopentadiene type epoxy compounds include EP-4088S (manufactured by ADEKA). Examples of commercially available naphthalene-type epoxy compounds include EPICLON HP4032 and EPICLON EXA-4700 (both manufactured by DIC Corporation). Examples of commercially available phenolic novolac type epoxy compounds include EPICLON N-770 (manufactured by DIC Corporation). Examples of commercially available ortho-cresol novolac type epoxy compounds include EPICLON N-670-EXP-S (manufactured by DIC Corporation).
  • Examples of commercially available dicyclopentadiene novolac type epoxy compounds include EPICLON HP7200 (manufactured by DIC Corporation).
  • Commercially available biphenyl novolac type epoxy compounds include, for example, NC-3000P (manufactured by Nippon Kayaku Co., Ltd.).
  • Examples of commercially available naphthalenephenol novolac type epoxy compounds include ESN-165S (manufactured by Nippon Steel Chemical & Materials Co., Ltd.).
  • Examples of commercially available glycidylamine type epoxy compounds include jER630 (manufactured by Mitsubishi Chemical Corporation), EPICLON 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Co., Ltd.), and the like.
  • Examples of commercially available alkyl polyol type epoxy compounds include ZX-1542 (manufactured by Nippon Steel Chemical & Materials), EPICLON 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), and Denacol EX. -611 (manufactured by Nagase ChemteX Corporation) and the like.
  • Examples of commercially available rubber-modified epoxy compounds include YR-450 and YR-207 (both manufactured by Nippon Steel Chemical & Materials) and Epolead PB (manufactured by Daicel).
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation).
  • Other commercially available epoxy compounds include YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel Chemical & Materials), XAC4151 (manufactured by Asahi Kasei), jER1031, and jER1032. (all manufactured by Mitsubishi Chemical), EXA-7120 (manufactured by DIC), TEPIC (manufactured by Nissan Chemical) and the like.
  • epoxy (meth)acrylates include, for example, epoxy (meth)acrylate manufactured by Daicel Allnex, epoxy (meth)acrylate manufactured by Shin-Nakamura Chemical Industry, epoxy (meth)acrylate manufactured by Kyoeisha Chemical Co., Ltd. ( meth) acrylate, epoxy (meth) acrylate manufactured by Nagase ChemteX Corporation, and the like.
  • 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 and the like.
  • Examples of epoxy (meth)acrylates manufactured by Nagase ChemteX Co., Ltd. include Denacol acrylate DA-141, Denacol acrylate DA-314, Denacol acrylate DA-911, and the like.
  • the urethane (meth)acrylate can be obtained, for example, by reacting a polyfunctional isocyanate compound with a (meth)acrylic acid derivative having a hydroxyl group in the presence of a catalytic amount of a tin compound.
  • polyfunctional isocyanate compound examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), Hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris(isocyanatophenyl) thiophosphate, tetramethyl xylylene diisocyanate, 1,6,11-undecane triisocyanate, and the like.
  • MDI diphenylmethane-4,4'-diisocyanate
  • polyfunctional isocyanate compound a chain-extended polyfunctional isocyanate compound obtained by reacting a polyol with an excess polyfunctional isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and the like.
  • Examples of the (meth)acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono(meth)acrylates, dihydric alcohol mono(meth)acrylates, trihydric alcohol mono(meth)acrylates and di(meth)acrylates. , epoxy (meth)acrylate, and the like.
  • Examples of the hydroxyalkyl mono(meth)acrylates include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate and the like. mentioned.
  • Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
  • Examples of the trihydric alcohol include trimethylolethane, trimethylolpropane, glycerin and the like.
  • Examples of the epoxy (meth)acrylate include bisphenol A type epoxy acrylate.
  • urethane (meth) acrylates examples include urethane (meth) acrylate manufactured by Toagosei Co., Ltd., urethane (meth) acrylate manufactured by Daicel Allnex, and urethane (meth) acrylate manufactured by Negami Kogyo Co., Ltd. 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)acrylates manufactured by Toagosei Co., Ltd. examples include M-1100, M-1200, M-1210 and M-1600.
  • 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. be done.
  • the curable resin may contain an epoxy compound for the purpose of improving the adhesiveness of the obtained sealing agent for liquid crystal display elements.
  • the epoxy compound include an epoxy compound that serves as a raw material for synthesizing the epoxy (meth)acrylate described above, a partially (meth)acryl-modified epoxy compound, and the like.
  • the partially (meth)acrylic-modified epoxy compound means, for example, reacting a part of the epoxy group of an epoxy compound having two or more epoxy groups in one molecule with (meth)acrylic acid. means a compound having one or more epoxy groups and one or more (meth)acryloyl groups in one molecule, which can be obtained by
  • the curable resin contains the (meth)acrylic compound and the epoxy compound, or when the partially (meth)acryl-modified epoxy compound is contained, the (meth)acryloyl group in the curable resin and the epoxy It is preferable that the ratio of the (meth)acryloyl group in the total of the groups is 30 mol % or more and 95 mol % or less. When the ratio of the (meth)acryloyl group is within this range, the resulting sealant for liquid crystal display elements has excellent adhesion while suppressing the occurrence of liquid crystal contamination.
  • the curable resin has a hydrogen-bonding unit such as —OH group, —NH— group, or —NH 2 group, from the viewpoint of making the obtained sealing agent for liquid crystal display element more excellent in low liquid crystal contamination resistance. is preferred.
  • the curable resins may be used alone, or two or more of them may be used in combination.
  • the sealant for liquid crystal display elements of the present invention contains a photopolymerization initiator.
  • the initiator or the combination of the photopolymerization initiator and the sensitizer described below can be adjusted by adjusting the type and content ratio.
  • the gel fraction when irradiated with light of 100 mW / cm 2 for 30 seconds using the 450 nm LED lamp, and the gel fraction when irradiated with light of 400 lux for 48 hours using the 580 nm LED lamp Compounds represented by the following formulas (1-1) to (1-3) are preferred because they facilitate adjustment of the gel fractions within the respective ranges described above.
  • Camphorquinone is also preferable as the photopolymerization initiator when it is used in combination with a sensitizer described later.
  • a preferable lower limit is 0.3 parts by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the photopolymerization initiator is 0.3 parts by weight or more, the obtained sealing agent for liquid crystal display elements is excellent in visible light curability and low liquid crystal contamination resistance.
  • the content of the photopolymerization initiator is 10 parts by weight or less, the resulting sealing agent for liquid crystal display elements is excellent in low liquid crystal contamination.
  • a more preferable lower limit to the content of the photopolymerization initiator is 0.5 parts by weight, and a more preferable upper limit is 4 parts by weight.
  • the sealing compound for liquid crystal display elements of the present invention may contain a sensitizer.
  • the sensitizer in combination with the camphorquinone, the gel fraction when 100 mW/cm 2 light is irradiated for 30 seconds using the 450 nm LED lamp , and the gel fraction when irradiated with light of 400 lux for 48 hours using the 580 nm LED lamp can be easily adjusted.
  • the sensitizer when used in combination with the camphorquinone, the gel fraction when irradiated with light of 100 mW / cm 2 for 30 seconds using the 450 nm LED lamp, and 400 lux using the 580 nm LED lamp When the light is irradiated for 48 hours, it becomes easy to adjust the gel fraction to the range described above, so the compound represented by the following formula (2-1), the following formula (2-2) are preferred.
  • the content of the sensitizer has a preferred lower limit of 0.001 parts by weight and a preferred upper limit of 0.5 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the sensitizer is within this range, the obtained sealing agent for liquid crystal display elements is excellent in visible light curability and low liquid crystal contamination, and also has the effect of suppressing nozzle clogging during coating. become excellent.
  • a more preferable lower limit to the content of the sensitizer is 0.005 parts by weight, and a more preferable upper limit is 0.1 parts by weight.
  • the sealant for liquid crystal display elements of the present invention may contain a thermal polymerization initiator as long as the object of the present invention is not impaired.
  • the thermal polymerization initiator include those composed of azo compounds, organic peroxides, and the like. Among them, a polymeric azo initiator composed of a polymeric azo compound is preferable.
  • the above thermal polymerization initiators may be used alone, or two or more of them may be used in combination.
  • the term "polymeric azo compound” refers to a compound having an azo group and a number average molecular weight of 300 or more, which generates a radical capable of curing a (meth)acryloyloxy group by heat. means.
  • a preferable lower limit of the number average molecular weight of the above high-molecular azo compound is 1,000, and a preferable upper limit thereof is 300,000.
  • the lower limit of the number average molecular weight of the high-molecular azo compound is more preferably 5,000, the upper limit is 100,000, the lower limit is still more preferably 10,000, and the upper limit is still more preferably 90,000.
  • 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 one having a polyethylene oxide structure is preferable.
  • Specific examples of the high-molecular azo compound include polycondensates 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 polymeric azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.). be done.
  • Examples of non-polymeric azo compounds include V-65 and V-501 (both manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.).
  • organic peroxides examples include ketone peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, peroxyesters, diacyl peroxides and peroxydicarbonates.
  • the content of the thermal polymerization initiator has a preferable lower limit of 0.05 parts by weight and a preferable upper limit of 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the sealing agent for liquid crystal display elements of the present invention becomes excellent in thermosetting property.
  • the sealant for liquid crystal display elements of the present invention is excellent in low liquid crystal contamination and storage stability.
  • a more preferred lower limit to the content of the thermal polymerization initiator is 0.1 parts by weight, and a more preferred upper limit is 5 parts by weight.
  • the sealing compound 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. Among them, organic acid hydrazides are preferably used.
  • the thermosetting agents may be used alone, or two or more of them may be used in combination.
  • Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, and malonic acid dihydrazide.
  • 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., Ltd., and the like.
  • Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
  • Examples of the organic acid hydrazides manufactured by Ajinomoto Fine-Techno Co., Inc. include Amicure VDH, Amicure VDH-J, Amicure UDH, and Amicure UDH-J.
  • the content of the thermosetting agent has a preferable lower limit of 1 part by weight and a preferable upper limit of 50 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the thermosetting agent is within this range, the obtained sealing compound for liquid crystal display elements can be made more excellent in thermosetting properties without deteriorating the applicability and the like.
  • a more preferable upper limit of the content of the thermosetting agent is 30 parts by weight.
  • the sealant for liquid crystal display elements of the present invention preferably contains a filler for the purpose of improving viscosity, improving adhesiveness due to a stress dispersion effect, improving coefficient of linear expansion, and the like.
  • An inorganic filler or an organic filler can be used as the filler.
  • inorganic fillers 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. , calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate and the like.
  • the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, acrylic polymer fine particles, and the like.
  • the filler is preferable because it has the effect of promoting light scattering and improving the gel fraction when irradiated with light of 100 mW/cm 2 for 30 seconds using a 450 nm LED lamp.
  • organic fillers are more preferable than inorganic fillers from the viewpoint of ensuring light transmittance at the same time.
  • the above fillers may be used alone, or two or more of them may be used in combination.
  • a preferable lower limit is 10 parts by weight and a preferable upper limit is 60 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the filler is within this range, the effect of improving adhesiveness and the like is excellent without deteriorating coatability and the like.
  • a more preferable lower limit of the filler content is 20 parts by weight, and a more preferable upper limit thereof is 50 parts by weight.
  • the sealing compound for liquid crystal display elements of the present invention preferably contains a silane coupling agent.
  • the silane coupling agent mainly serves as an adhesion assistant for good adhesion between 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 adhesiveness 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 silane coupling agents may be used alone, or two or more of them may be used in combination.
  • a preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the liquid crystal display element sealing compound of the present invention is 0.1 parts by weight, and a preferable upper limit thereof is 10 parts by weight.
  • the content of the silane coupling agent is within this range, the effect of improving adhesion while suppressing the occurrence of liquid crystal contamination is more excellent.
  • a more preferable lower limit to the content of the silane coupling agent is 0.3 parts by weight, and a more preferable upper limit is 5 parts by weight.
  • the sealing agent for liquid crystal display elements of the present invention further contains additives such as reactive diluents, thixotropic agents, spacers, curing accelerators, antifoaming agents, leveling agents and polymerization inhibitors, if necessary. may
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mixer is used to mix a curable resin with light.
  • the conductive fine particles a metal ball, a resin fine particle having a conductive metal layer formed on its surface, or the like can be used.
  • the one in which a conductive metal layer is formed on the surface of the resin fine particles is preferable because the excellent elasticity of the resin fine particles enables conductive connection without damaging the transparent substrate or the like.
  • a liquid crystal display element having a cured product of the sealant for a liquid crystal display element of the present invention is also one aspect of the present invention.
  • a liquid crystal display element having a narrow frame design is preferable.
  • the width of the frame portion around the liquid crystal display section is 2 mm or less.
  • the coating width of the sealant for a liquid crystal display element of the present invention when manufacturing the liquid crystal display element of the present invention is 1 mm or less.
  • a liquid crystal dropping method is preferably used, and specific examples thereof include a method including the following steps.
  • a step is performed in which the liquid crystal liquid crystal sealing agent of the present invention is in an uncured state, and liquid crystal microdroplets are applied dropwise within the frame of the seal pattern of the substrate, and the other transparent substrate is superimposed under vacuum.
  • a liquid crystal display element can be obtained by a method of performing a step of photocuring the sealing agent by irradiating the sealing pattern portion of the sealing agent for a liquid crystal display element of the present invention with light through a cut filter or the like.
  • a step of heating the sealant to thermally cure it may be performed.
  • the sealing compound for liquid crystal display elements which is excellent in visible light curability and low liquid-crystal contamination property, and can suppress the nozzle clogging at the time of application
  • the extracted solution was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated to obtain product (A2).
  • 3 parts by weight of the obtained product (A2), 0.76 parts by weight of hydroxylammonium chloride, and 0.86 parts by weight of pyridine were added to 30 mL of ethanol and stirred under reflux for 10 hours.
  • the resulting reaction solution was poured into ice water and then filtered. After the filtrate was washed with water, it was dissolved in ethyl acetate, dried with anhydrous magnesium sulfate and concentrated to obtain the product (B2).
  • Examples 1 to 10 and Comparative Examples 1 to 6 According to the compounding ratio described in Tables 1 and 2, after mixing each material using a planetary stirrer, the liquid crystals of Examples 1 to 10 and Comparative Examples 1 to 6 were further mixed using three rolls. A sealant for display elements was prepared. Awatori Mixer (manufactured by Thinky Corporation) was used as the planetary stirrer. As a pretreatment, the resulting liquid crystal display element sealing compound was defoamed with ARV-310LED (manufactured by Thinky Corporation). Each liquid crystal display element sealant was spread between two polyethylene terephthalate (PET) films (“PET5011” manufactured by Lintec Corporation) so as to have a thickness of 300 ⁇ m.
  • PET polyethylene terephthalate
  • the two PET films were separated. If the sealant does not have tackiness, the cured sealant is peeled off from the PET film and then cut into strips of 1 cm x 2 cm. Prevented from being emitted from other places. On the other hand, when the sealant had tack, the sealant was collected on the plane of the microspatula and wrapped with a 200-mesh metal mesh so that the sealant was not released from places other than the grid of the mesh. At this time, the weight of the metal mesh used was measured as G0, and the total weight of the sealant and the metal mesh was measured as G1.
  • G0 was set to 1 g or more and less than 3 g
  • (G1-G0) was set to 0.2 g or more and less than 0.4 g.
  • a metal mesh wrapped with a sealing agent is attached to a screw tube No. 1. 8 (manufactured by Maruem), 70 g of acetone was added to the screw tube and allowed to stand for 3 hours. The metal mesh enveloping the sealing agent present in the acetone is taken out with tweezers and a new screw tube No. 8 (manufactured by Maruem), 70 g of new acetone was added to the screw tube, and the tube was allowed to stand for another 2 hours.
  • the metal mesh wrapped with the sealant was taken out with tweezers, it was dried in an oven at 80° C. under normal pressure for 2 hours. After drying, the weight of the metal mesh wrapped with the sealant was measured and designated as G2.
  • the above work was performed in a darkroom of 1 lux or less.
  • a TENMARS digital illuminance meter TM-201L (manufactured by TENMARS) was used to measure the illuminance of the work environment.
  • the gel fraction was measured by inserting the obtained values of G0 to G2 into the above formula.
  • UELCL-P-450-X manufactured by iGraphics
  • a 580 nm LED lamp was used in place of the 450 nm LED lamp, and light of 400 lux was irradiated for 48 hours, and the gel fraction of the sealing agent after light irradiation was measured in the same manner.
  • the 580 nm LED lamp ECOHILUX HES-YF LDG32T Y22/22 (manufactured by Iris Ohyama Co., Ltd.) was used.
  • a metal halide lamp was used to irradiate light of 100 mW/cm 2 for 30 seconds through a cut filter that cuts light of 340 nm or less (340 nm cut filter). was used to measure the gel fraction.
  • the liquid crystal display element sealants obtained in Examples 7, 9, and 10 were irradiated with light of 100 mW/cm 2 for 30 seconds through a 340 nm cut filter, and the gel fraction was not measured. .
  • Each obtained gel fraction is shown in Tables 1 and 2.
  • the inside of the syringe was decompressed at a pressure at which the sealant did not drip from the tip of the nozzle and the sealant did not disappear from the tip of the nozzle, and the syringe was allowed to stand still for 48 hours while being sucked back. After that, a pressure of 100 kPa was applied to the inside of the syringe, and nozzle clogging was evaluated as " ⁇ " when the sealant was ejected from the tip of the nozzle, and "x" when it was not ejected.
  • PSY-10EU-OR manufactured by Musashi Engineering Co., Ltd.
  • HN-0.3N manufactured by Musashi Engineering Co., Ltd.
  • SHOTMASTER 300 manufactured by Musashi Engineering Co., Ltd.
  • Engineering Co., Ltd. was used. This evaluation was performed under the environment of irradiating light of 400 lux using a 580 nm LED lamp.
  • ECOHILUX HES-YF LDG32T Y22/22 manufactured by Iris Ohyama
  • TM-201L manufactured by TENMARS
  • sealant was performed under an environment in which light of 1 lux or less was irradiated using a 580 nm LED lamp.
  • a 580 nm LED lamp As the 580 nm LED lamp, ECOHILUX HES-YF LDG32T Y22/22 (manufactured by Iris Ohyama Co., Ltd.) was used. Subsequently, microdroplets of the liquid crystal taken out from the sample bottle were dropped and applied to the entire surface of the frame on the substrate, and another glass substrate was superimposed in a vacuum. The vacuum was released and a 450 nm LED lamp was used to irradiate 100 mW/cm 2 light for 30 seconds.
  • UELCL-P-450-X manufactured by iGraphics
  • the sealant was thermally cured by heating at 120° C. for 1 hour to obtain a liquid crystal display element.
  • a liquid crystal property evaluation system manufactured by Toyo Technica Co., Ltd., "6254 type"
  • an AC voltage of 5 V and 1 Hz is applied to the obtained liquid crystal display element at 25° C., and the holding voltage is measured after 1 second.
  • the voltage holding ratio of the liquid crystal was calculated.
  • the voltage holding rate was 95% or more, " ⁇ ", when it was 80% or more and less than 95%, " ⁇ ", and when it was less than 80%, " ⁇ ", Low liquid crystal contamination was evaluated. did.
  • the sealing compound for liquid crystal display elements which is excellent in visible light curability and low liquid-crystal contamination property, and can suppress the nozzle clogging at the time of application

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Liquid Crystal (AREA)
  • Sealing Material Composition (AREA)

Abstract

L'objectif de la présente invention est de fournir un agent d'étanchéité pour des éléments d'affichage à cristaux liquides, l'agent d'étanchéité ayant une excellente aptitude au durcissement à la lumière visible et une faible propriété de coloration de cristaux liquides et capable de supprimer le colmatage de la buse lorsqu'il est appliqué. Un autre but de la présente invention est de fournir un élément d'affichage à cristaux liquides qui est formé à l'aide dudit agent d'étanchéité pour des éléments d'affichage à cristaux liquides. La présente invention concerne un agent d'étanchéité pour des éléments d'affichage à cristaux liquides, l'agent d'étanchéité contenant une résine durcissable et un initiateur de photopolymérisation, la fraction de gel lorsque de la lumière de 100 mW/cm2 est appliquée pendant 30 secondes à l'aide d'une lampe à DEL ayant un sommet de pic à une longueur d'onde de 450 nm étant de 70 % ou plus, et la fraction de gel lorsque la lumière de 400 lux est appliquée pendant 48 heures à l'aide d'une lampe à DEL ayant un sommet de pic à une longueur d'onde de 580 nm étant inférieure à 10 %.
PCT/JP2022/022496 2021-06-04 2022-06-02 Agent d'étanchéité pour éléments d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé WO2022255452A1 (fr)

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CN202280023421.9A CN117043670A (zh) 2021-06-04 2022-06-02 液晶显示元件用密封剂和液晶显示元件
KR1020247000209A KR20240017908A (ko) 2021-06-04 2022-06-02 액정 표시 소자용 씰제 및 액정 표시 소자
JP2022537078A JP7201881B1 (ja) 2021-06-04 2022-06-02 液晶表示素子用シール剤及び液晶表示素子

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JP2010189279A (ja) * 2009-02-16 2010-09-02 Nippon Kagaku Kogyosho:Kk オキシムエステル化合物及びこれらを用いた感光性樹脂組成物
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JP2020170120A (ja) * 2019-04-04 2020-10-15 東京応化工業株式会社 感光性樹脂組成物、パターン化された硬化膜の製造方法、及びパターン化された硬化膜
WO2021177316A1 (fr) * 2020-03-03 2021-09-10 積水化学工業株式会社 Composition de résine durcissable, agent d'étanchéité pour éléments d'affichage, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau conducteur vertical, élément d'affichage, adhésif pour composants électroniques, et composant électronique

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JP3583326B2 (ja) 1999-11-01 2004-11-04 協立化学産業株式会社 Ｌｃｄパネルの滴下工法用シール剤
US7253131B2 (en) 2001-05-16 2007-08-07 Sekisui Chemical Co., Ltd. Curing resin composition and sealants and end-sealing materials for displays
US11384169B2 (en) 2016-08-26 2022-07-12 Sharp Kabushiki Kaisha Sealant composition, liquid crystal cell, and method of producing liquid crystal cell

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JP2003313216A (ja) * 2002-04-18 2003-11-06 Henkel Loctite Corp 可視光硬化型樹脂組成物
JP2010189279A (ja) * 2009-02-16 2010-09-02 Nippon Kagaku Kogyosho:Kk オキシムエステル化合物及びこれらを用いた感光性樹脂組成物
CN106405946A (zh) * 2016-11-29 2017-02-15 深圳市华星光电技术有限公司 框胶固化方法及液晶面板制造方法
JP2020170120A (ja) * 2019-04-04 2020-10-15 東京応化工業株式会社 感光性樹脂組成物、パターン化された硬化膜の製造方法、及びパターン化された硬化膜
WO2021177316A1 (fr) * 2020-03-03 2021-09-10 積水化学工業株式会社 Composition de résine durcissable, agent d'étanchéité pour éléments d'affichage, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau conducteur vertical, élément d'affichage, adhésif pour composants électroniques, et composant électronique

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