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WO2020085081A1 - Agent d'étanchéité pour élément d'affichage, produit durci, matériau conducteur vertical et élément d'affichage - Google Patents

Agent d'étanchéité pour élément d'affichage, produit durci, matériau conducteur vertical et élément d'affichage Download PDF

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Publication number
WO2020085081A1
WO2020085081A1 PCT/JP2019/039618 JP2019039618W WO2020085081A1 WO 2020085081 A1 WO2020085081 A1 WO 2020085081A1 JP 2019039618 W JP2019039618 W JP 2019039618W WO 2020085081 A1 WO2020085081 A1 WO 2020085081A1
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WO
WIPO (PCT)
Prior art keywords
meth
display element
acrylate
sealant
examples
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2019/039618
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English (en)
Japanese (ja)
Inventor
慶枝 松井
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Chemical Co Ltd
Original Assignee
Sekisui Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to KR1020217008519A priority Critical patent/KR102798870B1/ko
Priority to JP2019556375A priority patent/JP6792088B2/ja
Priority to CN201980065563.XA priority patent/CN112840267B/zh
Publication of WO2020085081A1 publication Critical patent/WO2020085081A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/064—Polymers containing more than one epoxy group per molecule
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4246—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof polymers with carboxylic terminal groups
    • C08G59/4253—Rubbers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1339—Gaskets; Spacers; Sealing of cells

Definitions

  • the present invention relates to a sealant for a display element, which is capable of obtaining a display element having excellent wet heat resistance and impact resistance.
  • the present invention also relates to a cured product of the display element sealant, and a vertical conduction material and a display element using the display element sealant.
  • liquid crystal display elements organic EL display elements, and the like have been widely used as display elements having features such as thinness, light weight, and low power consumption.
  • the liquid crystal, the light emitting layer and the like are usually sealed with a sealant made of a curable resin composition.
  • a sealant made of a curable resin composition.
  • a liquid crystal display element a liquid crystal display element using a photo-thermosetting curable sealant as disclosed in Patent Documents 1 and 2 is used from the viewpoint of shortening the tact time and optimizing the amount of liquid crystal used. It is disclosed.
  • display elements are required to have impact resistance that does not cause panel peeling or the like even when an impact is applied from the outside due to a drop or the like. Further, the display element is required to have a high level of reliability in driving under a high temperature and high humidity environment, which is compatible with a pressure cooker test (PCT) under the conditions of 121 ° C., 100% RH and 2 atm.
  • PCT pressure cooker test
  • the sealant has excellent resistance to moist heat.
  • a sealant that can improve the impact resistance of a display element and is excellent in wet heat resistance.
  • the present invention contains a curable resin and a polymerization initiator and / or a thermosetting agent, and has a storage elastic modulus at 25 ° C. of less than 0.8 GPa and a storage elastic modulus at 121 ° C. of 0.
  • the present inventor has excellent moisture and heat resistance by controlling the storage elastic modulus at 25 ° C. of the cured product to be less than a specific value and the storage elastic modulus at 121 ° C. of the cured product to be a specific value or more. Moreover, they have found that it is possible to obtain a display element sealant capable of obtaining a display element having excellent impact resistance, and have completed the present invention.
  • the sealant for a display element of the present invention the effect of being able to obtain a display element having excellent wet heat resistance and excellent impact resistance is that the sealant for a display element of the present invention is on the alignment film of a liquid crystal display element. It is particularly remarkable when arranged.
  • the display element sealant of the present invention has a storage elastic modulus at 25 ° C. of less than 0.8 GPa.
  • the sealant for a display element of the present invention makes it possible to obtain a display element having excellent impact resistance. Even when it is arranged on the film, it is possible to prevent the panel from peeling off due to an external impact.
  • a preferable upper limit of the storage elastic modulus at 25 ° C. of the cured product is 0.75 GPa, and a more preferable upper limit thereof is 0.7 GPa. Further, from the viewpoint of the adhesiveness when the adherends are stuck together, the preferable lower limit of the storage elastic modulus at 25 ° C.
  • the cured product for measuring the storage elastic modulus there is used a cured product obtained by irradiating the sealing agent with ultraviolet rays of 100 mW / cm 2 for 30 seconds and then heating at 120 ° C. for 1 hour.
  • the storage elastic modulus can be measured using a dynamic viscoelasticity measuring device under the conditions of a test piece width of 5 mm, a thickness of 0.35 mm, a gripping width of 25 mm, a temperature rising rate of 10 ° C./min, and a frequency of 10 Hz. .
  • the storage elastic modulus at 25 ° C. of the cured product can be obtained as a value at 25 ° C.
  • the storage elastic modulus at 121 ° C. of the cured product described below is It can be obtained as a value at 121 ° C. when the temperature of the product is raised from 0 ° C. to 200 ° C.
  • Examples of the dynamic viscoelasticity measuring device include DVA-200 (manufactured by IT measurement control company).
  • the lower limit of the storage elastic modulus at 121 ° C. of the cured product of the sealant for a display element of the present invention is 0.01 GPa.
  • the sealant for a display element of the present invention has excellent wet heat resistance.
  • a preferable lower limit of the storage elastic modulus at 121 ° C. of the cured product is 0.02 GPa, and a more preferable lower limit thereof is 0.03 GPa.
  • the display element sealant of the present invention contains a curable resin.
  • a compound having an epoxy group and a rubber structure as the curable resin hereinafter, It is preferable to use a "rubber structure-containing epoxy compound" and adjust the content ratio.
  • the "rubber structure” means a vulcanized rubber structure formed by adding sulfur to raw rubber, a synthetic rubber structure formed by a double bond formed in a molecular main chain by addition polymerization, and a peroxide.
  • the rubber structure is preferably a structure having an unsaturated bond in the main chain or a structure having a polysiloxane skeleton in the main chain.
  • the structure having an unsaturated bond in the main chain include a structure having a skeleton formed by polymerization of a conjugated diene in the main chain.
  • the skeleton formed by polymerization of the conjugated diene include a polybutadiene skeleton, a polyisoprene skeleton, a styrene-butadiene skeleton, a polyisobutylene skeleton, a polychloroprene skeleton, and the like.
  • the rubber structure is more preferably a structure having a polybutadiene skeleton, a polyisoprene skeleton, or a polysiloxane skeleton.
  • the preferred lower limit of the molecular weight of the epoxy compound having a rubber structure is 100, and the preferred upper limit is 10,000.
  • the more preferable lower limit of the molecular weight of the epoxy compound having a rubber structure is 200, and the more preferable upper limit thereof is 5000.
  • the "molecular weight” is a molecular weight obtained from the structural formula for a compound having a specified molecular structure, but for a compound having a wide distribution of the degree of polymerization and a compound having an unspecified modification site, It may be expressed using a weight average molecular weight.
  • the "weight average molecular weight” is a value obtained by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent and polystyrene conversion.
  • GPC gel permeation chromatography
  • Examples of the column used when measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (Showa Denko KK).
  • the epoxy compound having a rubber structure examples include terminal amino group-containing butadiene-acrylonitrile (ATBN) modified epoxy resin, terminal carboxyl group-containing butadiene-acrylonitrile (CTBN) modified epoxy resin, and acrylonitrile-butadiene rubber (NBR).
  • ATBN terminal amino group-containing butadiene-acrylonitrile
  • CBN terminal carboxyl group-containing butadiene-acrylonitrile
  • NBR acrylonitrile-butadiene rubber
  • Modified epoxy resin epoxy modified isoprene rubber, epoxy modified butadiene rubber, epoxy modified chloroprene rubber, epoxy modified silicone rubber and the like can be mentioned.
  • the epoxy compound having a rubber structure may be used alone or in combination of two or more kinds.
  • the preferable lower limit of the content of the epoxy compound having the rubber structure in the total 100 parts by weight of the curable resin is 3 parts by weight, and the preferable upper limit is 30 parts by weight.
  • the content of the epoxy compound having the rubber structure is in this range, it becomes easy to set the storage elastic moduli at 25 ° C. and 121 ° C. of the cured product of the obtained display element sealing agent to the ranges described above.
  • the more preferable lower limit of the content of the epoxy compound having a rubber structure is 5 parts by weight, and the more preferable upper limit thereof is 25 parts by weight.
  • the curable resin has a rubber structure for the purpose of adjusting the storage elastic modulus, further improving the adhesiveness when adherends are adhered and the low liquid crystal contamination when used in a liquid crystal display device. It is preferable to contain other curable resin other than the epoxy compound.
  • an epoxy compound other than the epoxy compound having the rubber structure or a (meth) acrylic compound is preferably used as the other curable resin.
  • the “(meth) acryl” means acryl or methacryl
  • the “(meth) acryl compound” means a compound having a (meth) acryloyl group.
  • Examples of the above other epoxy compounds include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2,2′-diallyl bisphenol A type epoxy resin, hydrogenated bisphenol type epoxy resin 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 type epoxy resin, Orthocresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, naphthalenepheno Novolak type epoxy resins, glycidyl amine type epoxy resin, alkyl polyol type epoxy resins, glycidyl ester compounds.
  • Examples of commercially available bisphenol A type epoxy resins include jER828EL, jER1004 (both manufactured by Mitsubishi Chemical Co., Ltd.), Epicron 850CRP (manufactured by DIC Co.) and the like.
  • Examples of commercially available bisphenol F type epoxy resins include jER806 and jER4004 (both manufactured by Mitsubishi Chemical Corporation).
  • Examples of commercially available bisphenol E type epoxy resins include R710 (manufactured by Printec Co., Ltd.) and the like.
  • Examples of commercially available bisphenol S-type epoxy resins include Epiclon EXA1514 (manufactured by DIC) and the like.
  • Examples of commercially available 2,2′-diallyl bisphenol A type epoxy resins include RE-810NM (manufactured by Nippon Kayaku Co., Ltd.) and the like.
  • Examples of commercially available hydrogenated bisphenol type epoxy resins include Epiclon EXA7015 (manufactured by DIC) and the like.
  • Examples of commercially available propylene oxide-added bisphenol A type epoxy resins include EP-4000S (manufactured by ADEKA).
  • Examples of commercially available resorcinol type epoxy resins include EX-201 (manufactured by Nagase Chemtex).
  • Examples of commercially available biphenyl type epoxy resins include jER YX-4000H (manufactured by Mitsubishi Chemical Corporation) and the like.
  • Examples of commercially available sulfide type epoxy resins include YSLV-50TE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and the like.
  • Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and the like.
  • Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA) and the like.
  • Examples of commercially available naphthalene type epoxy resins include Epiclon HP4032 and Epiclon EXA-4700 (both manufactured by DIC).
  • Examples of commercially available phenol novolac type epoxy resins include Epicron N-770 (manufactured by DIC).
  • Examples of commercially available ortho-cresol novolac type epoxy resins include Epiclon N-670-EXP-S (manufactured by DIC).
  • Examples of commercially available dicyclopentadiene novolac type epoxy resins include Epiclon HP7200 (manufactured by DIC).
  • Examples of commercially available biphenyl novolac type epoxy resins include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.) and the like.
  • Examples of commercially available naphthalenephenol novolac type epoxy resins include ESN-165S (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and the like.
  • Examples of commercially available glycidyl amine type epoxy resins include jER630 (manufactured by Mitsubishi Chemical Corporation), Epicron 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Company) and the like.
  • alkyl polyol type epoxy resins commercially available products include, for example, ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epicron 726 (manufactured by DIC Co., Ltd.), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), and Denacol EX-611. (Manufactured by Nagase Chemtex) and the like.
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase Chemtex) and the like.
  • epoxy compounds include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Co., Ltd.), jER1031, jER1032 (any of them). And Mitsubishi Chemical Co., Ltd.), EXA-7120 (manufactured by DIC), TEPIC (manufactured by Nissan Chemical Co., Ltd.) and the like.
  • the curable resin may contain, as the other epoxy compound, a compound having an epoxy group and a (meth) acryloyl group in one molecule.
  • a compound having an epoxy group and a (meth) acryloyl group in one molecule examples include a partial (meth) acrylic modified epoxy resin obtained by reacting a partial epoxy group of an epoxy compound having two or more epoxy groups in one molecule with (meth) acrylic acid. Can be mentioned.
  • examples of commercially available products include UVACURE1561 and KRM8287 (both manufactured by Daicel Ornex Co., Ltd.).
  • Examples of the (meth) acrylic compound include epoxy (meth) acrylate, (meth) acrylic acid ester compound, and urethane (meth) acrylate. Of these, epoxy (meth) acrylate is preferable. Further, the above-mentioned other (meth) acrylic compounds are preferably those having two or more (meth) acryloyl groups in the molecule because of their high reactivity.
  • said "(meth) acrylate” means an acrylate or a methacrylate, and said "epoxy (meth) acrylate” reacts all the epoxy groups in an epoxy compound with (meth) acrylic acid. It represents the compound.
  • the epoxy (meth) acrylate can be synthesized by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
  • epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate the same epoxy compounds as those having the rubber structure and other epoxy compounds can be used.
  • epoxy (meth) acrylates include, for example, epoxy (meth) acrylate manufactured by Daicel Ornex Co., epoxy (meth) acrylate manufactured by Shin-Nakamura Chemical Co., and epoxy (meth) manufactured by Kyoeisha Chemical Co., Ltd. Examples thereof include (meth) acrylate and epoxy (meth) acrylate manufactured by Nagase Chemtex.
  • the epoxy (meth) acrylate manufactured by the Daicel Orunekusu Inc. for example, EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3708, EBECRYL3800, EBECRYL6040, EBECRYL RDX63182 and the like.
  • Examples of the epoxy (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd. include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020.
  • Examples of the epoxy (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd. include 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, etc. are mentioned.
  • Examples of the epoxy (meth) acrylate manufactured by Nagase Chemtex include Denacol acrylate DA-141, Denacol acrylate DA-314, Denacol acrylate DA-911, and the like.
  • Examples of 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, isobutyl (meth) acrylate.
  • bifunctional compounds of the (meth) acrylic acid ester compound include, for example, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexane.
  • trifunctional or higher functional compounds of the (meth) acrylic acid ester compound examples include trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, and 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
  • the urethane (meth) acrylate can be obtained, for example, by reacting an isocyanate compound with a (meth) acrylic acid derivative having a hydroxyl group in the presence of a catalytic amount of a tin compound.
  • isocyanate compound examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4′-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethyl xylylene diisocyanate Examples thereof include isocyanate and 1,6,11-undecane triisocyanate.
  • MDI diphenylmethane-4,4′-diisocyanate
  • a chain-extended isocyanate compound obtained by reacting a polyol with an excess isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol and polycaprolactone diol.
  • Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono (meth) acrylate, monohydric alcohol mono (meth) acrylate, trihydric alcohol mono (meth) acrylate or di (meth) acrylate. , Epoxy (meth) acrylate and the like.
  • Examples of the hydroxyalkyl mono (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Can be mentioned.
  • Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol and the like.
  • Examples of the trihydric alcohol include trimethylolethane, trimethylolpropane, and glycerin.
  • Examples of the epoxy (meth) acrylate include bisphenol A type epoxy acrylate.
  • urethane (meth) acrylates examples include, for example, urethane (meth) acrylate manufactured by Toagosei Co., Ltd., urethane (meth) acrylate manufactured by Daicel Ornex Co., and urethane (meth) 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) acrylate manufactured by Toagosei Co., Ltd.
  • the urethane (meth) acrylate manufactured by the Daicel Orunekusu Inc. for example, EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260 etc. Can be mentioned.
  • Examples of the urethane (meth) acrylate manufactured by Negami Kogyo Co., Ltd. include Art Resin UN-330, Art Resin SH-500B, Art Resin UN-1200TPK, Art Resin UN-1255, Art Resin UN-3320HB, Art Resin UN-. 7100, Art Resin UN-9000A, Art Resin UN-9000H and the like.
  • urethane (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd. include AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T.
  • the above curable resins may be used alone or in combination of two or more.
  • the content ratio of the (meth) acryloyl group in the total of the (meth) acryloyl group and the epoxy group in the curable resin is preferably 50 mol% or more and 95 mol% or less.
  • the display element sealing agent of the present invention contains a polymerization initiator and / or a thermosetting agent.
  • a polymerization initiator examples include radical polymerization initiators and cationic polymerization initiators.
  • radical polymerization initiator examples include a photoradical polymerization initiator that generates a radical upon irradiation with light and a thermal radical polymerization initiator that generates a radical upon heating.
  • photoradical polymerization initiator examples include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthone compounds, and the like.
  • Specific examples of the above radical photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 1,2- (dimethylamino).
  • thermal radical polymerization initiator examples include those composed of azo compounds, organic peroxides and the like. Among them, a polymer azo initiator composed of a polymer azo compound is preferable.
  • the polymer azo compound means a compound having an azo group and having a number average molecular weight of 300 or more, which produces a radical capable of curing a (meth) acryloyloxy group by heat.
  • the preferable lower limit of the number average molecular weight of the high molecular weight azo compound is 1,000, and the preferable upper limit thereof is 300,000.
  • the more preferable lower limit of the number average molecular weight of the high molecular weight azo compound is 5000, the more preferable upper limit thereof is 100,000, the still more preferable lower limit thereof is 10,000, and the still more preferable upper limit thereof is 90,000.
  • the said number average molecular weight is a value calculated
  • GPC gel permeation chromatography
  • Examples of the polymer azo compound include those having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
  • the polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via the azo group those having a polyethylene oxide structure are preferable.
  • Specific examples of the polymer azo compound include polycondensates of 4,4′-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4′-azobis (4-cyanopentanoic acid). And a polycondensation product of polydimethylsiloxane having a terminal amino group.
  • Examples of commercially available high-molecular azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (all manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.).
  • Examples of commercially available azo compounds which are not polymers include V-65 and V-501 (both manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.).
  • organic peroxide examples include ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, peroxydicarbonate and the like.
  • a photocationic polymerization initiator can be preferably used.
  • the photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by irradiation with light, and may be an ionic photoacid generating type or a nonionic photoacid generating type. May be Examples of the above-mentioned photocationic polymerization initiator include onium salts such as aromatic diazonium salts, aromatic halonium salts and aromatic sulfonium salts, iron-allene complexes, titanocene complexes, arylsilanol-aluminum complexes and other organometallic complexes. Is mentioned.
  • photocationic polymerization initiators examples include ADEKA OPTOMER SP-150 and ADEKA OPTOMER SP-170 (both manufactured by ADEKA).
  • the above polymerization initiators may be used alone or in combination of two or more kinds.
  • the content of the polymerization initiator has a preferable lower limit of 0.1 part by weight and a preferable upper limit of 30 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the above-mentioned polymerization initiator is 0.1 parts by weight or more, the obtained sealing agent for a display element is more excellent in curability.
  • the content of the above-mentioned polymerization initiator is 30 parts by weight or less, the resulting display element sealant becomes more excellent in storage stability.
  • the more preferable lower limit of the content of the polymerization initiator is 1 part by weight, the more preferable upper limit thereof is 10 parts by weight, and the still more preferable upper limit thereof is 5 parts by weight.
  • thermosetting agent examples include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Among them, solid organic acid hydrazide is preferably used.
  • the above thermosetting agents may be used alone or in combination of two or more.
  • Examples of the solid organic acid hydrazide include 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin, sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide and the like.
  • Examples of commercially available organic acid hydrazides include organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd., organic acid hydrazides manufactured by Nippon Finechem Co., Ltd., and organic acid hydrazides manufactured by Ajinomoto Fine-Techno Inc., and the like. Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd.
  • Examples of the organic acid hydrazide manufactured by Nippon Finechem Co., Ltd. include MDH and the like.
  • Examples of the organic acid hydrazides manufactured by Ajinomoto Fine-Techno Co., Inc. include Amicure VDH, Amicure VDH-J, Amicure UDH and the like.
  • the content of the thermosetting agent is preferably 1 part by weight and 50 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the thermosetting agent is 1 part by weight or more, the resulting display element sealing agent is more excellent in thermosetting property.
  • the content of the thermosetting agent is 50 parts by weight or less, the obtained display element sealing agent becomes more excellent in coating property.
  • a more preferable upper limit of the content of the thermosetting agent is 30 parts by weight.
  • the sealant for a display element of the present invention preferably contains a filler for the purpose of adjusting viscosity, improving adhesiveness due to stress dispersion effect, improving linear expansion coefficient, and improving moisture resistance of a cured product.
  • An inorganic filler or an organic filler can be used as the filler.
  • the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, 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 preferable lower limit of the content of the filler in 100 parts by weight of the display element sealant of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight.
  • the more preferable lower limit of the content of the filler is 20 parts by weight, and the more preferable upper limit thereof is 60 parts by weight.
  • the display element sealing agent of the present invention preferably contains a silane coupling agent.
  • the above-mentioned silane coupling agent mainly has a role as an adhesion aid for favorably adhering the sealant to the substrate and the like.
  • silane coupling agent for example, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, etc. are preferably used.
  • silane coupling agents are excellent in the effect of improving the adhesiveness to the substrate, etc., and when the obtained display element sealing agent is used in a liquid crystal display element, suppress the outflow of the curable resin into the liquid crystal. You can
  • the silane coupling agent may be used alone or in combination of two or more kinds.
  • the preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the display element sealant of the present invention is 0.1 part by weight, and the preferable upper limit is 10 parts by weight.
  • the content of the silane coupling agent is in this range, the resulting display element sealant becomes more excellent in adhesiveness, and when the obtained display element sealant is used in a liquid crystal display element, liquid crystal contamination is prevented. The generation can be suppressed.
  • the more preferable lower limit of the content of the silane coupling agent is 0.3 parts by weight, and the more preferable upper limit thereof is 5 parts by weight.
  • the display element sealing agent of the present invention may contain the above-mentioned light shielding agent.
  • the display element sealant of the present invention can be suitably used as a light-shielding sealant.
  • the light-shielding agent examples include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, resin-coated carbon black, and the like. Of these, titanium black is preferable.
  • the light shielding agents may be used alone or in combination of two or more.
  • the titanium black is a substance having a higher transmittance in the vicinity of the ultraviolet region, particularly in the light having a wavelength of 370 nm to 450 nm, as compared with the average transmittance to light having a wavelength of 300 nm to 800 nm. That is, the titanium black has a property of imparting a light-shielding property to the sealant for a display element of the present invention by sufficiently shielding light having a wavelength in the visible light region, while transmitting light having a wavelength near the ultraviolet region. It is a light-shielding agent.
  • the light-shielding agent contained in the sealant for a display element of the present invention is preferably a substance having a high insulating property, and titanium black is also suitable as a light-shielding agent having a high insulating property.
  • the titanium black exhibits sufficient effects 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, or oxide. It is also possible to use surface-treated titanium black such as one coated with an inorganic component such as zirconium or magnesium oxide. Among them, those treated with an organic component are preferable because the insulating property can be further improved. Further, since the display element manufactured by using the sealant for a display element of the present invention containing the above-mentioned titanium black as a light shielding agent has a sufficient light shielding property, it has a high contrast without light leakage and is excellent. A display element having image display quality can be realized.
  • an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, or oxide. It is also possible to use surface-treated titanium black such as one coated with an inorganic component such as zirconium or magnesium oxide. Among them, those treated with an organic component are preferable because the
  • Examples of commercially available titanium blacks include titanium black manufactured by Mitsubishi Materials and titanium black manufactured by Ako Kasei. Examples of the titanium black manufactured by Mitsubishi Materials include 12S, 13M, 13M-C, 13R-N, 14M-C and the like. Examples of the titanium black manufactured by Ako Kasei Co., Ltd. include Tilak D.
  • the preferable lower limit of the specific surface area of the titanium black is 13 m 2 / g, the preferable upper limit thereof is 30 m 2 / g, the more preferable lower limit thereof is 15 m 2 / g, and the more preferable upper limit thereof is 25 m 2 / g.
  • the preferred lower limit of 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 light-shielding agent is not particularly limited as long as it is equal to or less than the distance between the substrates of the display element, but a preferable lower limit is 1 nm and a preferable upper limit is 5000 nm.
  • a preferable lower limit is 1 nm and a preferable upper limit is 5000 nm.
  • the primary particle size of the light-shielding agent can be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
  • the preferable lower limit of the content of the light-shielding agent in 100 parts by weight of the display element sealant of the present invention is 5 parts by weight, and the preferable upper limit thereof is 80 parts by weight.
  • the content of the light-shielding agent is in this range, the adhesiveness of the resulting display element sealant, the strength after curing, and the effect of improving the light-shielding property while suppressing the deterioration of the drawing property are more excellent.
  • the more preferable lower limit of the content of the light-shielding agent is 10 parts by weight, the more preferable upper limit thereof is 70 parts by weight, the further preferable lower limit thereof is 30 parts by weight, and the further preferable upper limit thereof is 60 parts by weight.
  • the sealant for a display element of the present invention further contains additives such as a reactive diluent, a spacer, a curing accelerator, a defoaming agent, a leveling agent, a polymerization inhibitor, and other coupling agents, if necessary. You may.
  • the sealing agent for a display element of the present invention for example, a curable resin, a polymerization initiator and / or a thermosetting agent, and a silane coupling agent to be added as necessary, using a mixer.
  • a mixer include a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and three rolls.
  • the sealant for a display element of the present invention can be cured by light irradiation and / or heating.
  • a cured product of the display element sealing agent of the present invention is also one aspect of the present invention.
  • a vertical conduction material By mixing conductive fine particles with the display element sealant of the present invention, a vertical conduction material can be manufactured.
  • a vertical conduction material containing such a display element sealant of the present invention and conductive fine particles is also one aspect of the present invention.
  • the conductive fine particles are not particularly limited, and metal balls, resin fine particles having a conductive metal layer formed on their surfaces, or the like can be used. Of these, a resin fine particle having a conductive metal layer formed on the surface thereof is preferable because conductive elasticity can be achieved without damaging the transparent substrate or the like due to the excellent elasticity of the resin fine particle.
  • a display element having the cured product of the display element sealant of the present invention or the cured product of the vertical conduction material of the present invention is also one aspect of the present invention.
  • a liquid crystal display element is suitable as the display element of the present invention.
  • a liquid crystal dropping method is preferably used, and specific examples thereof include a method including the following steps. First, a step of forming a frame-shaped seal pattern by applying the display element sealant of the present invention to one of two transparent substrates having electrodes such as ITO thin films by screen printing, dispenser application, or the like.
  • a step of applying minute droplets of liquid crystal to the entire surface of the frame of the seal pattern and applying the other transparent substrate under vacuum is performed.
  • a liquid crystal display element can be obtained by a method of performing a step of irradiating the seal pattern portion with light such as ultraviolet rays to temporarily cure the sealant, and a step of heating the provisionally cured sealant to perform main curing. it can.
  • a display element sealant capable of obtaining a display element having excellent wet heat resistance and impact resistance. Further, according to the present invention, it is possible to provide a cured product of the display element sealant, and a vertical conduction material and a display element using the display element sealant.
  • Examples 1 to 5, Comparative Examples 1 to 4 According to the compounding ratios shown in Table 1, the respective materials were mixed using a planetary stirrer and then further mixed using a three-roll mill to display the display elements of Examples 1 to 5 and Comparative Examples 1 to 4.
  • a sealant was prepared.
  • As the planetary stirrer Awatori Kentaro (manufactured by Shinky Co.) was used.
  • Each of the obtained sealants for display elements was irradiated with 100 mW / cm 2 ultraviolet rays (wavelength 365 nm) for 30 seconds using a metal halide lamp, and then heated at 120 ° C. for 1 hour to obtain a cured product.
  • the obtained cured product was stored at 25 ° C. and 121 ° C.
  • Spacer particles 1 part by weight of spacer particles was uniformly dispersed in 100 parts by weight of the sealing agent for each display element obtained in Examples and Comparative Examples.
  • the spacer particles Micropearl Micropearl SI-H050 (manufactured by Sekisui Chemical Co., Ltd.) was used. Fill the syringe for dispensing with the sealant in which the spacer particles are dispersed, perform defoaming treatment, and then apply with a dispenser to draw a rectangular frame on the alignment film of the alignment film and the transparent substrate with the ITO thin film. did.
  • PSY-10E (manufactured by Musashi Engineering Co., Ltd.) was used as the syringe, and SHOTMASTER 300 (manufactured by Musashi Engineering Co., Ltd.) was used as the dispenser. Subsequently, minute droplets of liquid crystal were dropped and applied on the entire surface of the frame of the sealant, and another transparent substrate was immediately attached. As the liquid crystal, JC-5004LA (manufactured by Chisso Corporation) was used. Immediately after bonding the transparent substrate, the sealant portion was irradiated with 100 mW / cm 2 ultraviolet rays (wavelength 365 nm) for 30 seconds using a metal halide lamp, and then heated at 120 ° C.
  • liquid crystal display element for 1 hour to obtain a liquid crystal display element.
  • the obtained liquid crystal display device was exposed to PCT conditions (121 ° C., 100% RH, 2 atm) for 24 hours. After the PCT condition, the liquid crystal display element was visually observed to confirm the occurrence of display unevenness and air bubbles. When neither display unevenness nor air bubbles was found, " ⁇ " was given. Moisture and heat resistance was evaluated by setting “ ⁇ ” when one generation was confirmed and “ ⁇ ” when both display unevenness and bubbles were confirmed.
  • a display element sealant capable of obtaining a display element having excellent wet heat resistance and impact resistance. Further, according to the present invention, it is possible to provide a cured product of the display element sealant, and a vertical conduction material and a display element using the display element sealant.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Nonlinear Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
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  • General Physics & Mathematics (AREA)
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  • Sealing Material Composition (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)

Abstract

Le but de la présente invention est de fournir un agent d'étanchéité pour un élément d'affichage qui peut fournir un élément d'affichage ayant une excellente résistance à la chaleur humide et une excellente résistance au choc. Un autre but de la présente invention est de fournir un produit durci de l'agent d'étanchéité pour un élément d'affichage, et un matériau conducteur vertical et un élément d'affichage utilisant l'agent d'étanchéité pour un élément d'affichage. L'agent d'étanchéité pour un élément d'affichage de la présente invention comprend une résine durcissable et un initiateur de polymérisation et/ou un agent thermodurcissable, le produit durci a un module de conservation à 25°C inférieur à 0,8 GPa, et le produit durci a un module de conservation à 121°C de 0,01 GPa ou plus.
PCT/JP2019/039618 2018-10-23 2019-10-08 Agent d'étanchéité pour élément d'affichage, produit durci, matériau conducteur vertical et élément d'affichage Ceased WO2020085081A1 (fr)

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KR1020217008519A KR102798870B1 (ko) 2018-10-23 2019-10-08 표시 소자용 시일제, 경화물, 상하 도통 재료, 및, 표시 소자
JP2019556375A JP6792088B2 (ja) 2018-10-23 2019-10-08 液晶滴下工法用シール剤、硬化物、上下導通材料、及び、液晶表示素子
CN201980065563.XA CN112840267B (zh) 2018-10-23 2019-10-08 显示元件用密封剂、固化物、上下导通材料及显示元件

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WO2022196764A1 (fr) * 2021-03-19 2022-09-22 三井化学株式会社 Agent d'étanchéité à cristaux liquides, procédé de production d'un écran d'affichage à cristaux liquides et écran d'affichage à cristaux liquides

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KR100906926B1 (ko) 2001-05-16 2009-07-10 세키스이가가쿠 고교가부시키가이샤 경화성 수지 조성물, 표시 소자용 시일제 및 표시 소자용주입구 밀봉제
KR101849892B1 (ko) * 2014-03-31 2018-04-17 교리쯔 가가꾸 산교 가부시키가이샤 경화 후 유연성이 우수한 경화성 수지, (메트)아크릴화 경화성 수지 및 액정 밀봉제 조성물
KR102106760B1 (ko) * 2016-12-27 2020-05-06 세키스이가가쿠 고교가부시키가이샤 액정 표시 소자용 시일제, 상하 도통 재료 및 액정 표시 소자

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JP2022083550A (ja) * 2020-11-25 2022-06-06 協立化学産業株式会社 封止用組成物
JP7430911B2 (ja) 2020-11-25 2024-02-14 協立化学産業株式会社 封止用組成物
WO2022196764A1 (fr) * 2021-03-19 2022-09-22 三井化学株式会社 Agent d'étanchéité à cristaux liquides, procédé de production d'un écran d'affichage à cristaux liquides et écran d'affichage à cristaux liquides
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JP7536999B2 (ja) 2021-03-19 2024-08-20 三井化学株式会社 液晶シール剤、液晶表示パネルの製造方法および液晶表示パネル

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KR102798870B1 (ko) 2025-04-21
CN112840267B (zh) 2024-07-12
JP6792088B2 (ja) 2020-11-25
CN112840267A (zh) 2021-05-25

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