WO2015152030A1 - Agent de scellement pour procédés de dépôt en gouttes de cristaux liquides, matériau verticalement conducteur, et élément d'affichage à cristaux liquides - Google Patents

Agent de scellement pour procédés de dépôt en gouttes de cristaux liquides, matériau verticalement conducteur, et élément d'affichage à cristaux liquides Download PDF

Info

Publication number
WO2015152030A1
WO2015152030A1 PCT/JP2015/059565 JP2015059565W WO2015152030A1 WO 2015152030 A1 WO2015152030 A1 WO 2015152030A1 JP 2015059565 W JP2015059565 W JP 2015059565W WO 2015152030 A1 WO2015152030 A1 WO 2015152030A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
meth
acrylate
crystal dropping
group
Prior art date
Application number
PCT/JP2015/059565
Other languages
English (en)
Japanese (ja)
Inventor
慶枝 松井
Original Assignee
積水化学工業株式会社
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 積水化学工業株式会社 filed Critical 積水化学工業株式会社
Priority to KR1020167007211A priority Critical patent/KR20160137944A/ko
Priority to CN201580003348.9A priority patent/CN105849632A/zh
Priority to JP2015518702A priority patent/JP6408983B2/ja
Publication of WO2015152030A1 publication Critical patent/WO2015152030A1/fr

Links

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
    • 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
    • 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
    • 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
    • G02F1/1341—Filling or closing of cells
    • G02F1/13415—Drop filling process
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes

Definitions

  • the present invention relates to a sealing agent for a liquid crystal dropping method, which is excellent in photocurability and can suppress liquid crystal contamination. Moreover, this invention relates to the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal dropping methods.
  • a liquid crystal dropping method called a dropping method using a photothermal combined curing type sealing agent containing a polymerization initiator and a thermosetting agent is used.
  • a rectangular seal pattern is formed on one of two transparent substrates with electrodes by dispensing.
  • a liquid crystal micro-droplet is dropped on the entire surface of the transparent substrate frame in a state where the sealant is uncured, and the other transparent substrate is immediately overlaid, and the seal portion is irradiated with light such as ultraviolet rays for temporary curing. . Thereafter, heating is performed at the time of liquid crystal annealing to perform main curing, and a liquid crystal display element is manufactured. If the substrates are bonded together under reduced pressure, a liquid crystal display element can be manufactured with extremely high efficiency, and this dripping method is currently the mainstream method for manufacturing liquid crystal display elements.
  • the position of the seal portion is arranged under the black matrix (hereinafter also referred to as a narrow frame design).
  • the sealant is placed directly under the black matrix, so when the dripping method is used, the light irradiated when photocuring the sealant is blocked, and the light does not reach the inside of the sealant. There was a problem that the curing was insufficient. If the sealant is insufficiently cured in this manner, the uncured sealant component is eluted in the liquid crystal, and the curing reaction by the eluted sealant component proceeds in the liquid crystal, resulting in liquid crystal contamination. there were.
  • Patent Document 3 discloses that a highly sensitive photopolymerization initiator is blended with a sealant.
  • liquid crystal contamination could not be sufficiently suppressed only by blending a highly sensitive photopolymerization initiator.
  • An object of this invention is to provide the sealing compound for liquid crystal dropping methods which is excellent in photocurability and can suppress liquid-crystal contamination. Moreover, an object of this invention is to provide the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal dropping methods.
  • the present invention is a liquid crystal dropping method sealing agent containing a curable resin and a radical photopolymerization initiator, wherein the curable resin has a dielectric constant of 10 or more, and the radical photopolymerization initiator is polar It is a sealing agent for liquid crystal dropping method which is an oxime ester compound having a group.
  • the present invention is described in detail below.
  • the present inventor uses a combination of a curable resin having a dielectric constant of 10 or more and an oxime ester compound having a polar group to provide a liquid crystal drop excellent in photocurability and capable of suppressing liquid crystal contamination.
  • the inventors have found that a sealing agent for a construction method can be obtained, and have completed the present invention.
  • the sealing agent for liquid crystal dropping method of the present invention contains a curable resin.
  • the curable resin has a dielectric constant of 10 or more.
  • the sealing agent is excellent in photocurability, and a uniform cured product can be obtained.
  • the preferable lower limit of the dielectric constant of the curable resin is 11, and the more preferable lower limit is 12. The higher the dielectric constant of the curable resin is, the better, but the practical upper limit is 20.
  • the dielectric constant of the said curable resin is the dielectric constant of each compound which comprises the said curable resin.
  • the weight fraction in the curable resin can be measured by measuring the complex dielectric constant under the conditions of 25 ° C. and 1 MHz using an impedance analyzer (for example, “1260 type” manufactured by Solartron), and is defined by the real part. .
  • an epoxy (meth) acrylate or a partial (meth) acryl-modified epoxy resin described later is preferably used.
  • the epoxy resin used as a raw material for the epoxy (meth) acrylate and the partial (meth) acryl-modified epoxy resin include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, resorcinol type epoxy resin, Biphenyl type epoxy resin, diphenyl ether type epoxy resin and the like can be mentioned.
  • the sealing agent for liquid crystal dropping method of the present invention contains two or more compounds as the curable resin
  • the average dielectric constant of the curable resin containing two or more compounds is preferably 10 or more. From the viewpoint of further suppressing elution into the resin, it is more preferable that the dielectric constant of all the compounds constituting the curable resin is 10 or more.
  • the content of the curable resin having a dielectric constant of 10 or more in the curable resin is preferably 50% by weight or more, and 80% by weight. More preferably, it is 100% by weight.
  • the curable resin preferably contains a compound having a (meth) acryloyl group, and more preferably contains a compound having 2 to 3 (meth) acryloyl groups in one molecule because of high reactivity. .
  • Examples of the compound having the (meth) acryloyl group include an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid and an epoxy resin, a partial (meth) acryl-modified epoxy resin, and (meth) acrylic acid. And an ester compound obtained by reacting a compound having a hydroxyl group with urethane, and a urethane (meth) acrylate obtained by reacting a (meth) acrylic acid derivative having a hydroxyl group with isocyanate.
  • the “(meth) acryloyl group” means an acryloyl group or a methacryloyl group
  • the “(meth) acryl” means acryl or methacryl
  • the “(meth) acrylate” "Means acrylate or methacrylate.
  • epoxy (meth) acrylate means a compound obtained by reacting all epoxy groups in the epoxy resin with (meth) acrylic acid, and the “partial (meth) acrylate” is one molecule.
  • Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy resin and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
  • Examples of the epoxy resin used as a raw material for synthesizing the epoxy (meth) acrylate include, for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and 2,2′-diallyl bisphenol A type epoxy resin.
  • Hydrogenated bisphenol type epoxy resin propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol Novolac epoxy resin, ortho-cresol novolac epoxy resin, dicyclopentadiene novolac epoxy resin, biphenyl novolac epoxy resin, naphtha Emissions phenol novolak type epoxy resin, glycidyl amine type epoxy resin, alkyl polyol type epoxy resin, rubber-modified epoxy resins, glycidyl ester compounds.
  • Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
  • Examples of commercially available naphthalene type epoxy resins include Epicron HP4032, Epicron EXA-4700 (both manufactured by DIC) and the like.
  • Examples of commercially available phenol novolac epoxy resins include Epicron N-770 (manufactured by DIC).
  • Examples of the ortho-cresol novolac type epoxy resin that are commercially available include epiclone N-670-EXP-S (manufactured by DIC).
  • Examples of commercially available biphenyl novolac epoxy resins include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.).
  • Examples of commercially available naphthalenephenol novolac epoxy resins include ESN-165S (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • Examples of commercially available glycidylamine type epoxy resins include jER630 (manufactured by Mitsubishi Chemical), Epicron 430 (manufactured by DIC), and TETRAD-X (manufactured by Mitsubishi Gas Chemical).
  • alkyl polyol type epoxy resins examples include ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epiklon 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX. -611 (manufactured by Nagase ChemteX Corporation).
  • Examples of commercially available rubber-modified epoxy resins include YR-450, YR-207 (both manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epolide PB (manufactured by Daicel), and the like.
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation).
  • Other commercially available epoxy resins 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, and jER1032. (All manufactured by Mitsubishi Chemical), EXA-7120 (manufactured by DIC), TEPIC (manufactured by Nissan Chemical) and the like.
  • Examples of commercially available epoxy (meth) acrylates include, for example, EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRY3603 EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy Ester 200PA, epoxy ester 80MFA Epoxy ester 3002M, Epoxy ester 3002A, Epoxy ester 1600A, Epoxy ester 3000M, Epoxy ester 3000A, Epoxy ester 200EA, Epoxy ester 400EA (all manufactured by Kyoeisha Chemical Co., Ltd.), Denacol acrylate DA-141, Den
  • the partial (meth) acryl-modified epoxy resin can be obtained, for example, by reacting an epoxy group of a part of an epoxy resin having two or more epoxy groups with (meth) acrylic acid.
  • an epoxy resin used as the raw material of the said partial (meth) acryl modified epoxy resin what was mentioned as a raw material for synthesize
  • Examples of commercially available partial (meth) acrylic-modified epoxy resins include UVACURE 1561 (manufactured by Daicel Ornex).
  • ester compounds obtained by reacting the above (meth) acrylic acid with a compound having a hydroxyl group examples of monofunctional compounds include methyl (meth) acrylate, ethyl (meth) acrylate, and n-propyl (meth) acrylate.
  • bifunctional ester compound examples include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth).
  • ester compound having three or more functions examples include trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, and caprolactone.
  • Examples of the urethane (meth) acrylate obtained by reacting the above isocyanate with a (meth) acrylic acid derivative having a hydroxyl group include, for example, a (meth) acrylic acid derivative having a hydroxyl group with respect to 1 equivalent of a compound having two isocyanate groups. Two equivalents can be obtained by reacting in the presence of a catalytic amount of a tin-based compound.
  • isocyanate examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4′-diisocyanate (MDI), and hydrogenated MDI.
  • Polymeric MDI 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylene diisocyanate, Examples include 1,6,11-undecane triisocyanate.
  • strand obtained by reaction of polyols, such as ethylene glycol, propylene glycol, glycerol, sorbitol, trimethylol propane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, and excess isocyanate, for example.
  • polyols such as ethylene glycol, propylene glycol, glycerol, sorbitol, trimethylol propane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, and excess isocyanate, for example.
  • Extended isocyanate compounds can also be used.
  • Examples of the (meth) acrylic acid derivative having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
  • Hydroxyalkyl (meth) acrylates such as dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol, etc.
  • Acrylate mono (meth) acrylate or di (meth) acrylate of trivalent alcohol such as trimethylolethane, trimethylolpropane, glycerin, and epoxy (meth) acrylate such as bisphenol A type epoxy acrylate, etc. And the like.
  • Examples of commercially available urethane (meth) acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700 , Art resin N-1255, Art Resin UN-330, Art Resin UN-3320HB, Art Resin UN-1200TPK, Art Resin SH-500B (all manufactured by Negami Industrial Co., Ltd.), U-122P, U-108A, U-340P,
  • the curable resin preferably has a hydrogen bondable unit such as —OH group, —NH— group, —NH 2 group, etc. from the viewpoint of suppressing liquid crystal contamination.
  • the sealing agent for liquid crystal dropping method of the present invention contains a photo radical polymerization initiator.
  • the photo radical polymerization initiator is an oxime ester compound having a polar group.
  • the sealing agent for liquid crystal dropping method of the present invention is excellent in photocurability by using an oxime ester compound having a polar group in combination with a curable resin having a dielectric constant of 10 or more as the photoradical polymerization initiator. , Liquid crystal contamination can be suppressed.
  • the polar group of the oxime ester compound having a polar group is preferably at least one selected from the group consisting of —OH group, —COOH group, —SH group, —CONH 2 group, and —NH 2 group. .
  • the —OH group is more preferable because the compatibility with the liquid crystal becomes low.
  • the oxime ester compound having a polar group is preferably a compound represented by the following formula (1).
  • X represents an alkylene group having 1 to 6 carbon atoms.
  • examples of the alkylene group having 1 to 6 carbon atoms represented by X include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, a 1-ethylethylene group, Examples thereof include an n-pentylene group and an n-hexylene group. Of these, an ethylene group is preferable.
  • the content of the oxime ester compound having a polar group is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the oxime ester compound having a polar group is less than 0.1 parts by weight, the photocuring reaction of the obtained liquid crystal dropping method sealing agent may not sufficiently proceed. If the content of the oxime ester compound having a polar group exceeds 10 parts by weight, the resulting liquid crystal dropping method sealing agent may be inferior in weather resistance and storage stability, or liquid crystal contamination may occur.
  • the minimum with more preferable content of the oxime ester compound which has the said polar group is 0.5 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for liquid crystal dropping method of the present invention may contain other photoradical polymerization initiator as the photoradical polymerization initiator in addition to the oxime ester compound having the polar group. From the viewpoint of achieving both the effect of suppressing liquid crystal contamination, it is preferable that no other radical photopolymerization initiator is contained.
  • the sealing agent for liquid crystal dropping method of the present invention preferably contains a sensitizer.
  • the liquid crystal dropping method sealing agent of the present invention can provide a liquid crystal dropping method sealing agent with high sensitivity and more excellent photocurability.
  • the sensitizer preferably has a sufficient light absorption band in the ultraviolet / visible region, at least selected from the group consisting of a benzophenone skeleton, an anthracene skeleton, an anthraquinone skeleton, a coumarin skeleton, a thioxanthone skeleton, and a phthalocyanine skeleton. It is preferable to contain a compound having one kind of skeleton, and it is more preferred to contain a compound having at least one kind of skeleton selected from the group consisting of an anthracene skeleton, an anthraquinone skeleton, and a thioxanthone skeleton.
  • Examples of the compound having a benzophenone skeleton include benzophenone, 2,4-dichlorobenzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, and the like.
  • Examples of the compound having an anthracene skeleton include 9,10-dibutoxyanthracene, 9,10-diproxyanthraquinone, and 9,10-ethoxyanthraquinone.
  • Examples of the compound having an anthraquinone skeleton include 2-ethylanthraquinone, 1-methylanthraquinone, 1,4-dihydroxyanthraquinone, 2- (2-hydroxyethoxy) -anthraquinone and the like.
  • Examples of the compound having a coumarin skeleton include 7-diethylamino-4-methylcoumarin.
  • Examples of the compound having a thioxanthone skeleton include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propylthioxanthone, and the like.
  • the compound having a phthalocyanine skeleton examples include phthalocyanine.
  • the resulting sealant for liquid crystal dropping method is particularly excellent in light-curing part curability, so that 4,4′-bis (dimethylamino) benzophenone and 4,4′-bis At least one of (diethylamino) benzophenone is preferred.
  • the content of the sensitizer is such that a preferred lower limit is 2 parts by weight and a preferred upper limit is 50 parts by weight with respect to 100 parts by weight of the photopolymerization initiator. If the content of the sensitizer is less than 2 parts by weight, the effect of further improving the photocurability of the obtained liquid crystal dropping method sealing agent may not be sufficiently exhibited. When the content of the sensitizer exceeds 50 parts by weight, liquid crystal contamination may occur.
  • the minimum with more preferable content of the said sensitizer is 5 weight part, and a more preferable upper limit is 40 weight part.
  • the sealing agent for liquid crystal dropping method of the present invention may contain a thermal radical polymerization initiator.
  • a thermal radical polymerization initiator what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
  • an initiator made of a polymer azo compound (hereinafter also referred to as “polymer azo initiator”) is preferable.
  • the polymer azo compound means a compound having an azo group and generating a radical by heat and having a number average molecular weight of 300 or more.
  • the preferable lower limit of the number average molecular weight of the polymeric azo initiator is 1000, and the preferable upper limit is 300,000.
  • the number average molecular weight of the polymer azo initiator is less than 1000, the polymer azo initiator may adversely affect the liquid crystal.
  • the number average molecular weight of the polymeric azo initiator exceeds 300,000, mixing with the curable resin may be difficult.
  • the more preferable lower limit of the number average molecular weight of the polymeric azo initiator is 5000, the more preferable upper limit is 100,000, the still more preferable lower limit is 10,000, and the still more preferable upper limit is 90,000.
  • the said number average molecular weight is a value calculated
  • GPC gel permeation chromatography
  • Examples of the column for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko KK).
  • polymer azo initiator examples include those having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
  • polymer azo initiator having a structure in which a plurality of units such as polyalkylene oxide are bonded via the azo group those having a polyethylene oxide structure are preferable.
  • Examples of such a polymer azo initiator include polycondensates of 4,4′-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4′-azobis (4-cyanopentanoic acid) Examples thereof include polycondensates of polydimethylsiloxane having a terminal amino group, such as VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (all of which are Wako Pure Chemical Industries, Ltd.) Manufactured) and the like.
  • Examples of azo compounds that are not a polymer include V-65 and V-501 (both manufactured by Wako Pure Chemical Industries, Ltd.).
  • organic peroxide examples include ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
  • the content of the thermal radical polymerization initiator is preferably 0.05 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the thermosetting reaction of the obtained liquid crystal dropping method sealing agent may not sufficiently proceed.
  • content of the said thermal radical polymerization initiator exceeds 10 weight part, the sealing compound for liquid crystal dropping methods obtained may cause liquid crystal contamination.
  • the minimum with more preferable content of the said thermal radical polymerization initiator is 0.1 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for liquid crystal dropping method of the present invention may contain a thermosetting agent.
  • thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Of these, organic acid hydrazide is preferably used.
  • organic acid hydrazide examples include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
  • organic acid hydrazides examples include, for example, SDH, ADH (all manufactured by Otsuka Chemical Co., Ltd.), Amicure VDH, Amicure VDH-J, Amicure UDH, Amicure UDH-J (all Ajinomoto Fine Techno Co., Ltd.) Manufactured) and the like.
  • the content of the thermosetting agent is preferably 1 part by weight with respect to 100 parts by weight of the curable resin, and 50 parts by weight with respect to the preferable upper limit.
  • the content of the thermosetting agent is less than 1 part by weight, the resulting sealing agent for liquid crystal dropping method may not be sufficiently cured.
  • content of the said thermosetting agent exceeds 50 weight part, the viscosity of the sealing compound for liquid crystal dropping methods obtained will become high, and applicability
  • the upper limit with more preferable content of the said thermosetting agent is 30 weight part.
  • the sealing agent for liquid crystal dropping method of the present invention may contain a filler for the purpose of improving the viscosity, improving the adhesiveness due to the stress dispersion effect, improving the coefficient of linear expansion, and further improving the moisture resistance of the cured product. preferable.
  • the filler examples include talc, asbestos, silica, diatomaceous earth, smectite, bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide, water Inorganic fillers such as aluminum oxide, glass beads, silicon nitride, barium sulfate, gypsum, calcium silicate, sericite, activated clay, aluminum nitride, and organic materials such as polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles A filler is mentioned. These fillers may be used alone or in combination of two or more.
  • the minimum with preferable content of the said filler in 100 weight part of whole sealing compound for liquid crystal dropping methods of this invention is 10 weight part, and a preferable upper limit is 70 weight part.
  • a preferable upper limit is 70 weight part.
  • content of the filler is less than 10 parts by weight, effects such as improvement of adhesiveness may not be sufficiently exhibited.
  • content of the said filler exceeds 70 weight part, the sealing compound for liquid crystal dropping methods obtained may have a viscosity too high, and may become inferior to applicability
  • the minimum with more preferable content of the said filler is 20 weight part, and a more preferable upper limit is 60 weight part.
  • the sealing agent for liquid crystal dropping method of the present invention preferably contains a silane coupling agent.
  • the silane coupling agent mainly has a role as an adhesion assistant for favorably bonding the sealing agent and the substrate.
  • silane coupling agent since it is excellent in the effect which improves adhesiveness with a board
  • -Aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are preferably used.
  • These silane coupling agents may be used alone or in combination of two or more.
  • the minimum with preferable content of the said silane coupling agent in 100 weight part of sealing agents for liquid crystal dropping methods of this invention is 0.1 weight part, and a preferable upper limit is 10 weight part.
  • a preferable upper limit is 10 weight part.
  • content of the silane coupling agent is less than 0.1 parts by weight, effects such as improvement of adhesiveness may not be sufficiently exhibited.
  • content of the said silane coupling agent exceeds 10 weight part, the sealing compound for liquid crystal dropping methods obtained may cause liquid-crystal contamination.
  • the minimum with more preferable content of the said silane coupling agent is 0.3 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for liquid crystal dropping method of the present invention may contain a light shielding agent.
  • the sealing compound for liquid crystal dropping methods of this invention can be used suitably as a light shielding sealing agent.
  • the light-shielding agent examples include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Of these, titanium black is preferred because of its high insulating properties.
  • the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
  • the liquid crystal display device manufactured using the sealing agent for liquid crystal dropping method of the present invention containing the above-described titanium black as a light-shielding agent has a sufficient light-shielding property, and thus has a high contrast without light leakage. A liquid crystal display element having excellent image display quality can be realized.
  • titanium black examples include 12S, 13M, 13M-C, 13R-N, 14M-C (all manufactured by Mitsubishi Materials Corporation), Tilak D (manufactured by Ako Kasei Co., Ltd.), and the like. Can be mentioned.
  • the preferable lower limit of the specific surface area of the titanium black is 13 m 2 / g, the preferable upper limit is 30 m 2 / g, the more preferable lower limit is 15 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
  • the preferred lower limit of the volume resistance of the titanium black is 0.5 ⁇ ⁇ cm, the preferred upper limit is 3 ⁇ ⁇ cm, the more preferred lower limit is 1 ⁇ ⁇ cm, and the more preferred upper limit is 2.5 ⁇ ⁇ cm.
  • the primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more than the distance between the substrates of the liquid crystal display element, but the preferred lower limit is 1 nm and the preferred upper limit is 5 ⁇ m.
  • the primary particle diameter of the light-shielding agent is less than 1 nm, the viscosity and thixotropy of the obtained liquid crystal dropping method sealing agent are greatly increased, and workability may be deteriorated.
  • the primary particle diameter of the light-shielding agent exceeds 5 ⁇ m, the coating property of the obtained liquid crystal dropping method sealing agent on the substrate may be deteriorated.
  • the more preferable lower limit of the primary particle diameter of the light shielding agent is 5 nm, the more preferable upper limit is 200 nm, the still more preferable lower limit is 10 nm, and the still more preferable upper limit is 100 nm.
  • the primary particle size of the light shielding agent can be measured by using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS) and dispersing the light shielding agent in a solvent (water, organic solvent, etc.).
  • the preferable lower limit of the content of the light shielding agent in 100 parts by weight of the sealing agent for liquid crystal dropping method of the present invention is 5 parts by weight, and the preferable upper limit is 80 parts by weight. If the content of the light shielding agent is less than 5 parts by weight, sufficient light shielding properties may not be obtained. When the content of the light-shielding agent exceeds 80 parts by weight, the adhesion of the obtained sealing agent for liquid crystal dropping method to the substrate and the strength after curing may be lowered, or the drawing property may be lowered.
  • the more preferable lower limit of the content of the light shielding agent is 10 parts by weight, the more preferable upper limit is 70 parts by weight, the still more preferable lower limit is 30 parts by weight, and the still more preferable upper limit is 60 parts by weight.
  • a method for producing the sealing agent for liquid crystal dropping method of the present invention for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
  • a vertical conduction material can be produced by blending conductive fine particles with the sealant for the liquid crystal dropping method of the present invention.
  • Such a vertical conduction material containing the sealing agent for liquid crystal dropping method of the present invention and conductive fine particles is also one aspect of the present invention.
  • the conductive fine particles a metal ball, a resin fine particle formed with a conductive metal layer on the surface, or the like can be used.
  • the one in which the conductive metal layer is formed on the surface of the resin fine particles is preferable because the conductive connection is possible without damaging the transparent substrate due to the excellent elasticity of the resin fine particles.
  • the liquid crystal display element using the sealing agent for liquid crystal dropping method of the present invention or the vertical conduction material of the present invention is also one aspect of the present invention.
  • the sealing agent for the liquid crystal dropping method of the present invention is applied to one of two transparent substrates such as a glass substrate with electrodes such as an ITO thin film or a polyethylene terephthalate substrate.
  • the process of forming a rectangular seal pattern by screen printing, dispenser application, etc., the liquid crystal drop method sealing agent of the present invention is uncured, and liquid crystal microdrops are dropped on the entire surface of the transparent substrate and applied immediately.
  • a step of superimposing another substrate on the substrate, a step of irradiating the seal pattern portion of the sealant for the liquid crystal dropping method of the present invention with light such as ultraviolet rays, and the step of pre-curing the sealant, and a pre-cured sealant The method etc. which have the process of heating this and making it harden
  • the sealing compound for liquid crystal dropping methods which can be excellent in photocurability and can suppress liquid crystal contamination can be provided.
  • the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal dropping methods can be provided.
  • Example 1 As curable resin, 40 parts by weight of bisphenol A type epoxy acrylate (manufactured by Daicel Ornex Co., Ltd., “EBECRYL 3700”, dielectric constant 14), and partially acrylic modified bisphenol A type epoxy resin (manufactured by Daicel Ornex Co., Ltd., “UVACURE 1561”) Dielectric constant 13) 20 parts by weight, 1 part by weight of a compound represented by the following formula (2) (produced by ADEKA, “NCI-930”) as a radical photopolymerization initiator, and adipic acid dihydrazide as a thermosetting agent 3 parts by weight (manufactured by Otsuka Chemical Co., Ltd., “ADH”), 15 parts by weight of silica (manufactured by Admatechs, “Admafine SO-C2”) as a filler, and talc (manufactured by Nippon Talc Co., Ltd., “Nanoace D600” ]) 5 parts
  • Examples 2 to 11, Comparative Examples 1 to 5 According to the blending ratios described in Tables 1 and 2, each material was mixed using a planetary stirrer (manufactured by Shinky Co., Ltd., “Awatori Netaro”) in the same manner as in Example 1, and then 3 more The sealing agents for the liquid crystal dropping method of Examples 2 to 11 and Comparative Examples 1 to 5 were prepared by mixing using a roll.
  • the “compound represented by the formula (3)” described in Tables 1 and 2 is a compound represented by the following formula (3)
  • the “compound represented by the formula (4)” It is a compound represented by following formula (4).
  • the partial acrylic modified phenol novolac type epoxy resins in Tables 1 and 2 were prepared by the following method. That is, 190 g of phenol novolac type epoxy resin (manufactured by DIC, “N-770”) was dissolved in 500 mL of toluene, and 0.1 g of triphenylphosphine was added to this solution to obtain a uniform solution. After 35 g of acrylic acid was added dropwise to the obtained solution under reflux stirring over 2 hours, the mixture was further stirred under reflux for 6 hours. By removing toluene, a partially acrylic-modified phenol novolac epoxy resin (dielectric constant 9) in which 50 mol% of the epoxy group of the phenol novolac epoxy resin was modified to an acrylic group was obtained.
  • Liquid crystal contamination 1 part by weight of spacer fine particles (“Micropearl SI-H050” manufactured by Sekisui Chemical Co., Ltd.) is dispersed in 100 parts by weight of each liquid crystal dropping method sealant obtained in the examples and comparative examples, and two rubbed orientations are obtained. It applied with a dispenser so that the line width of a sealing agent might be set to 1 mm to one of a film
  • liquid crystal Chisso, “JC-5004LA”
  • a metal halide lamp was used to irradiate 100 mW / cm 2 of ultraviolet rays for 30 seconds to cure the sealant, and further heated at 120 ° C. for 1 hour to obtain a liquid crystal display element.
  • liquid crystal alignment disorder near the sealant was confirmed by observation with an optical microscope.
  • the liquid crystal alignment disorder is judged from the color unevenness of the display part. Depending on the degree of the color unevenness, “ ⁇ ” indicates that there is no color unevenness, “ ⁇ ” indicates that the color unevenness is slight, and “color unevenness”.
  • the liquid crystal contamination property was evaluated as “ ⁇ ” when there was a slight amount of color, and “X” when there was considerable color unevenness.
  • liquid crystal display elements with the evaluations “ ⁇ ” and “O” are at a level where there is no problem in practical use, and “ ⁇ ” is a level at which the display design of the liquid crystal display element may cause a problem. "Is a level that can not be put into practical use.
  • the sealing compound for liquid crystal dropping methods which can be excellent in photocurability and can suppress liquid crystal contamination can be provided.
  • the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal dropping methods can be provided.

Landscapes

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

Abstract

Un objectif de la présente invention est de fournir un agent de scellement pour des procédés de dépôt en gouttes de cristaux liquides, qui a une excellente aptitude au photodurcissement et est apte à supprimer la contamination de cristaux liquides. Un autre objectif de la présente invention est de fournir : un matériau verticalement conducteur qui est obtenu à l'aide de l'agent de scellement pour des procédés de dépôt en gouttes de cristaux liquides ; et un élément d'affichage à cristaux liquides. La présente invention concerne un agent de scellement pour procédés de dépôt en gouttes de cristaux liquides, qui contient une résine durcissable et un initiateur de polymérisation radicalaire. La résine durcissable a une constante diélectrique de 10 ou plus. Le initiateur de photopolymérisation radicalaire est un composé d'ester d'oxime ayant un groupe polaire.
PCT/JP2015/059565 2014-03-31 2015-03-27 Agent de scellement pour procédés de dépôt en gouttes de cristaux liquides, matériau verticalement conducteur, et élément d'affichage à cristaux liquides WO2015152030A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020167007211A KR20160137944A (ko) 2014-03-31 2015-03-27 액정 적하 공법용 시일제, 상하 도통 재료 및 액정 표시 소자
CN201580003348.9A CN105849632A (zh) 2014-03-31 2015-03-27 液晶滴下工艺用密封剂、上下导通材料、及液晶显示元件
JP2015518702A JP6408983B2 (ja) 2014-03-31 2015-03-27 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014074800 2014-03-31
JP2014-074800 2014-03-31

Publications (1)

Publication Number Publication Date
WO2015152030A1 true WO2015152030A1 (fr) 2015-10-08

Family

ID=54240356

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/059565 WO2015152030A1 (fr) 2014-03-31 2015-03-27 Agent de scellement pour procédés de dépôt en gouttes de cristaux liquides, matériau verticalement conducteur, et élément d'affichage à cristaux liquides

Country Status (5)

Country Link
JP (1) JP6408983B2 (fr)
KR (1) KR20160137944A (fr)
CN (1) CN105849632A (fr)
TW (1) TW201546151A (fr)
WO (1) WO2015152030A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017061255A1 (fr) * 2015-10-09 2017-04-13 積水化学工業株式会社 Agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
WO2017130786A1 (fr) * 2016-01-26 2017-08-03 積水化学工業株式会社 Agent de scellement pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
JP2017142316A (ja) * 2016-02-09 2017-08-17 三菱電機株式会社 液晶パネルの製造方法
JPWO2021177316A1 (fr) * 2020-03-03 2021-09-10

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013146748A1 (fr) * 2012-03-30 2013-10-03 積水化学工業株式会社 Agent de scellement pour processus de dépôt en gouttes de cristaux liquides, matériau conducteur vertical, et élément d'affichage à cristaux liquides
JP5337318B1 (ja) * 2012-11-22 2013-11-06 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5337294B1 (ja) * 2012-12-03 2013-11-06 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP2013228716A (ja) * 2012-03-30 2013-11-07 Sekisui Chem Co Ltd 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5340503B1 (ja) * 2012-05-16 2013-11-13 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
WO2014136667A1 (fr) * 2013-03-06 2014-09-12 積水化学工業株式会社 Agent de scellement pour des procédés de dépôt en gouttes de cristaux liquides, matériau conducteur vertical, et élément d'affichage à cristaux liquides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN102439089B (zh) 2010-06-28 2015-05-06 株式会社艾迪科 固化性树脂组合物
CN103026292B (zh) * 2011-04-05 2014-03-05 积水化学工业株式会社 液晶显示元件用遮光密封剂、上下导通材料及液晶显示元件

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013146748A1 (fr) * 2012-03-30 2013-10-03 積水化学工業株式会社 Agent de scellement pour processus de dépôt en gouttes de cristaux liquides, matériau conducteur vertical, et élément d'affichage à cristaux liquides
JP2013228716A (ja) * 2012-03-30 2013-11-07 Sekisui Chem Co Ltd 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5340503B1 (ja) * 2012-05-16 2013-11-13 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5337318B1 (ja) * 2012-11-22 2013-11-06 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5337294B1 (ja) * 2012-12-03 2013-11-06 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
WO2014136667A1 (fr) * 2013-03-06 2014-09-12 積水化学工業株式会社 Agent de scellement pour des procédés de dépôt en gouttes de cristaux liquides, matériau conducteur vertical, et élément d'affichage à cristaux liquides

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6126756B1 (ja) * 2015-10-09 2017-05-10 積水化学工業株式会社 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
WO2017061255A1 (fr) * 2015-10-09 2017-04-13 積水化学工業株式会社 Agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
CN107250904A (zh) * 2015-10-09 2017-10-13 积水化学工业株式会社 液晶显示元件用密封剂、上下导通材料及液晶显示元件
TWI707945B (zh) * 2015-10-09 2020-10-21 日商積水化學工業股份有限公司 液晶顯示元件用密封劑、上下導通材料、及液晶顯示元件
CN107710060B (zh) * 2016-01-26 2021-11-12 积水化学工业株式会社 液晶显示元件用密封剂、上下导通材料及液晶显示元件
WO2017130786A1 (fr) * 2016-01-26 2017-08-03 積水化学工業株式会社 Agent de scellement pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
CN107710060A (zh) * 2016-01-26 2018-02-16 积水化学工业株式会社 液晶显示元件用密封剂、上下导通材料及液晶显示元件
JPWO2017130786A1 (ja) * 2016-01-26 2018-11-15 積水化学工業株式会社 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP7048314B2 (ja) 2016-01-26 2022-04-05 積水化学工業株式会社 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP2017142316A (ja) * 2016-02-09 2017-08-17 三菱電機株式会社 液晶パネルの製造方法
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
JPWO2021177316A1 (fr) * 2020-03-03 2021-09-10
JP7084550B2 (ja) 2020-03-03 2022-06-14 積水化学工業株式会社 液晶表示素子用シール剤、上下導通材料、表示素子

Also Published As

Publication number Publication date
KR20160137944A (ko) 2016-12-02
TW201546151A (zh) 2015-12-16
JP6408983B2 (ja) 2018-10-17
CN105849632A (zh) 2016-08-10
JPWO2015152030A1 (ja) 2017-04-13

Similar Documents

Publication Publication Date Title
JP5736096B1 (ja) 液晶滴下工法用シール剤
JP5759638B1 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6434901B2 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6454217B2 (ja) 変性ジアルキルアミノ安息香酸系化合物、変性チオキサントン誘導体、光硬化性樹脂組成物、液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6539160B2 (ja) 液晶表示素子用シール剤及び上下導通材料
JP6408983B2 (ja) 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5340502B2 (ja) 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP6460797B2 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6216260B2 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6126756B1 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6046868B1 (ja) 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
WO2016194871A1 (fr) Agent de scellement pour éléments d'affichage à cristaux liquides, matériau à conduction verticale et élément d'affichage à cristaux liquides
JP5337318B1 (ja) 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP6378970B2 (ja) 硬化性樹脂組成物、液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6609164B2 (ja) 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP5337294B1 (ja) 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP6609396B1 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
WO2017119260A1 (fr) Agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
JP6031215B1 (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
WO2016190398A1 (fr) Agent de scellement pour procédés de dépôt de cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides
TW202208587A (zh) 液晶顯示元件用密封劑、上下導通材料及液晶顯示元件
TW202003623A (zh) 液晶顯示元件用密封劑、上下導通材料、及液晶顯示元件
JP2017003989A (ja) 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
WO2017119407A1 (fr) Produit d'étanchéité destiné à un élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2015518702

Country of ref document: JP

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15772635

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20167007211

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase
122 Ep: pct application non-entry in european phase

Ref document number: 15772635

Country of ref document: EP

Kind code of ref document: A1