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WO2019013194A1 - Agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale et élément d'affichage à cristaux liquides - Google Patents

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

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Publication number
WO2019013194A1
WO2019013194A1 PCT/JP2018/025999 JP2018025999W WO2019013194A1 WO 2019013194 A1 WO2019013194 A1 WO 2019013194A1 JP 2018025999 W JP2018025999 W JP 2018025999W WO 2019013194 A1 WO2019013194 A1 WO 2019013194A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
meth
compound
crystal display
acrylate
Prior art date
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Ceased
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PCT/JP2018/025999
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English (en)
Japanese (ja)
Inventor
洋 小林
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
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Sekisui Chemical Co Ltd
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Filing date
Publication date
Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to KR1020197015190A priority Critical patent/KR102612646B1/ko
Priority to JP2018540897A priority patent/JP7156946B2/ja
Priority to CN201880007538.1A priority patent/CN110226120A/zh
Publication of WO2019013194A1 publication Critical patent/WO2019013194A1/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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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 sealing agent for a liquid crystal display element which is excellent in curability to long wavelength light and can suppress the generation of foreign matter. Further, the present invention relates to a vertical conduction material and a liquid crystal display element formed by using the sealing agent for the liquid crystal display element.
  • a photo-thermal combination curing seal as disclosed in Patent Document 1 and Patent Document 2 from the viewpoint of shortening tact time and optimizing the amount of liquid crystal used.
  • a liquid crystal dropping method called a dropping method using an agent is used.
  • the dropping method first, a frame-like seal pattern is formed on one of the two transparent substrates with electrodes by dispensing. Next, while the sealing agent is in an uncured state, minute droplets of liquid crystal are dropped over the entire surface of the frame of the transparent substrate, the other transparent substrate is immediately bonded, and light such as ultraviolet light is irradiated on the sealing portion to perform temporary curing. .
  • liquid crystal display element is manufactured. If bonding of the substrates is performed under reduced pressure, the liquid crystal display element can be manufactured with extremely high efficiency, and the dropping method is currently the mainstream of the manufacturing method of the liquid crystal display element.
  • narrowing the frame of the liquid crystal display portion is mentioned, and for example, the position of the seal portion is disposed under the black matrix (hereinafter, also referred to as narrow frame design).
  • the sealing agent is disposed immediately below the black matrix in the narrow frame design, when the dropping method is performed, the light irradiated when the sealing agent is photocured is blocked, and the light does not reach the inside of the sealing agent. There is a problem that curing becomes insufficient. As described above, when the curing of the sealing agent is insufficient, the uncured sealing agent component is eluted into the liquid crystal, and the curing reaction by the eluted sealing agent component proceeds in the liquid crystal, thereby causing liquid crystal contamination. there were.
  • irradiation of ultraviolet light is performed as a method of photocuring the sealing agent, but in the liquid crystal dropping method, since the sealing agent is hardened after dropping the liquid crystal, the liquid crystal is deteriorated by irradiating the ultraviolet light.
  • a photopolymerization initiator which is excellent in the reactivity to the long wavelength light and to photocure it with the long wavelength light through a cut filter or the like.
  • a photopolymerization initiator when such a photopolymerization initiator is used, there is a problem that the sealing agent is partially cured by a slight light before the photocuring step, and foreign matter is generated.
  • the present invention contains a curable resin, a photopolymerization initiator and a maleimide compound, and the photopolymerization initiator has a light absorption coefficient at a wavelength of 430 nm of 0.8 ⁇ 10 2 mL / g ⁇ cm or more. It is a sealing agent.
  • the present invention will be described in detail below.
  • the present inventors have surprisingly found that, even if a photopolymerization initiator excellent in reactivity with long wavelength light is used by blending a maleimide compound in the sealing agent, the sealing agent is partially formed before the light curing step. It has been found that it is possible to obtain a sealing agent for a liquid crystal display element capable of suppressing the generation of foreign matter due to curing to complete the present invention.
  • the sealing agent for a liquid crystal display element of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator has an absorption coefficient of at least 0.8 ⁇ 10 2 mL / g ⁇ cm at a wavelength of 430 nm.
  • the photopolymerization initiator having an absorption coefficient of 0.8 ⁇ 10 2 mL / g ⁇ cm or more at a wavelength of 430 nm is also referred to as “the photopolymerization initiator according to the present invention”.
  • the photopolymerization initiator according to the present invention has a light absorption coefficient at a wavelength of 430 nm of 0.8 ⁇ 10 2 mL / g ⁇ cm or more, so that the sealing agent for a liquid crystal display element of the present invention is curable to long wavelength light. Excellent.
  • the preferable lower limit of the absorption coefficient at a wavelength of 430 nm of the photopolymerization initiator according to the present invention is 1.0 ⁇ 10 2 mL / g ⁇ cm.
  • the preferable upper limit of the light absorption coefficient in wavelength 430nm of the photoinitiator concerning this invention is 1.0 * 10 ⁇ 4 > mL / g * cm.
  • the said absorption coefficient can be measured using a spectrophotometer, after melt
  • the solvent is not particularly limited as long as it can dissolve the compound to be measured and does not absorb light at the absorption wavelength to be measured, and examples thereof include acetonitrile and methanol.
  • the photopolymerization initiator according to the present invention is preferably a compound having a structure represented by the following formula (1) because it is excellent in the reactivity to light of long wavelength, and it is preferable to use one compound per molecule. It is more preferable that the compound has a structure represented by (1), and a compound represented by the following formula (2-1) and / or a compound represented by the following formula (2-2) preferable.
  • * is a bonding position
  • R is a structure derived from a monofunctional epoxy compound.
  • m is an integer of 1 to 5.
  • the monofunctional epoxy compound preferably has an aromatic ring having at least one or more substituents having one or more carbon atoms or an aliphatic ring having at least one or more substituents having one or more carbon atoms.
  • the aromatic ring or the aliphatic ring include aromatic rings such as benzene ring, naphthalene ring, anthracene ring, cyclobutane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cyclooctane ring, norbornene ring, tricyclodecane ring, etc. That in which at least one or more hydrogen atoms in an aliphatic ring is substituted by a C 1 or more substituent is mentioned.
  • the substituent having one or more carbon atoms may be linear or branched.
  • the number of carbon atoms is preferably 6 or more, and more preferably 10 or more.
  • the number of carbon atoms is 4 or more.
  • carbon number of the C1 or more substituent which the said aromatic ring or the said aliphatic ring has is a number used as the molecular weight of the said monofunctional epoxy compound becomes 300 or less mentioned later.
  • an alkyl group is preferable.
  • Examples of the monofunctional epoxy compound include alkylphenyl glycidyl ether, toluene sulfonate having a glycidyl group, 2-epoxy-4-vinylcyclohexane, 3,4-epoxycyclohexylmethyl methacrylate and the like.
  • Examples of the alkylphenyl glycidyl ether include o-methylphenyl glycidyl ether, m-methylphenyl glycidyl ether, p-methylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether and the like.
  • monofunctional epoxy compounds manufactured by Nagase ChemteX Corp. for example, monofunctional epoxy compounds manufactured by Nagase ChemteX Corp., monofunctional epoxy compounds manufactured by ADEKA, monofunctional epoxy compounds manufactured by Mitsubishi Chemical Co., Ltd., Tokyo Chemical Industry Co., Ltd. Examples thereof include monofunctional epoxy compounds manufactured by Co., and monofunctional epoxy compounds manufactured by Daicel. Examples of the monofunctional epoxy compound manufactured by Nagase ChemteX Corp. include Denacol EX-146. Examples of the monofunctional epoxy compound manufactured by ADEKA include ED-509S, ED-509E, ED-529 and the like. Examples of monofunctional epoxy compounds manufactured by Mitsubishi Chemical Corporation include YED-122. Examples of monofunctional epoxy compounds manufactured by Tokyo Chemical Industry Co., Ltd. include glycidyl 2-methoxyphenyl ether, 1-methyl-1,2-epoxycyclohexane and the like. Examples of the monofunctional epoxy compound manufactured by Daicel Corporation include Celoxide 2000, Cyclomer M100 and the like.
  • the molecular weight of the monofunctional epoxy compound is preferably 300 or less from the viewpoint of the compatibility of the photopolymerization initiator according to the present invention with the curable resin.
  • the compound represented by the above formula (2-1) or the compound represented by the above formula (2-2) is highly recovered when the ratio of the raw material thioxanthone derivative to the above monofunctional epoxy compound is within this range. It can be manufactured at a rate.
  • a trivalent organic phosphoric acid compound and / or an amine compound are preferable.
  • Specific examples of the above basic catalyst include triphenylphosphine, triethylamine, trypromylamine, tetramethylethylenediamine, dimethyllaurylamine, triethylbenzylammonium chloride, trimethylcetyl ammonium bromide, tetrabutyl ammonium bromide, trimethylbutyl phosphonium bromide. And tetrabutylphosphonium bromide and the like.
  • triphenyl phosphine is preferable.
  • the above basic catalyst can also be supported on a polymer and used as a polymer-supported basic catalyst.
  • Examples of the photopolymerization initiator according to the present invention other than the compound having a structure represented by the above formula (1) include, for example, bis (2,4,6-trimethylbenzoyl) phenyl phosphine oxide and the like. .
  • the preferable lower limit of the content of the photopolymerization initiator according to the present invention is 0.1 parts by weight and the preferable upper limit is 20 parts by weight with respect to 100 parts by weight in total of the curable resin and the maleimide compound.
  • the content of the photopolymerization initiator according to the present invention is 0.1 parts by weight or more, the obtained sealing agent for a liquid crystal display element is excellent in the curability to long wavelength light.
  • the content of the photopolymerization initiator according to the present invention is 20 parts by weight or less, the obtained sealing agent for a liquid crystal display element is more excellent in the effect of suppressing the generation of foreign matter.
  • the lower limit of the content of the photopolymerization initiator according to the present invention is more preferably 0.2 parts by weight, still more preferably 0.3 parts by weight, still more preferably 0.5 parts by weight, particularly preferably 1 part by weight It is.
  • the upper limit of the content of the photopolymerization initiator according to the present invention is more preferably 10 parts by weight, still more preferably 5 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention may contain a thermal polymerization initiator as long as the object of the present invention is not impaired.
  • a thermal polymerization initiator what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
  • a polymeric azo initiator comprising a polymeric azo compound is preferred.
  • polymer azo compound refers to a compound having a number average molecular weight of 300 or more which has an azo group and generates a radical capable of curing a (meth) acryloyloxy group by heat. means.
  • the preferable lower limit of the number average molecular weight of the above-mentioned high molecular weight azo compound is 1000, and the preferable upper limit is 300,000.
  • the number average molecular weight of the high molecular weight azo compound is in this range, it can be easily mixed with the curable resin while suppressing liquid crystal contamination.
  • a more preferable lower limit of the number average molecular weight of the above-mentioned high molecular weight azo compound is 5,000, a more preferable upper limit is 100,000, a further preferable lower limit is 10,000, and a still more preferable upper limit is 90,000.
  • the above-mentioned number average molecular weight is a value obtained by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent and measuring in terms of polystyrene.
  • GPC gel permeation chromatography
  • Shodex LF-804 made by Showa Denko
  • said high molecular weight azo compound what has the structure which multiple units, such as a polyalkylene oxide and polydimethylsiloxane, couple
  • a polymeric azo compound having a structure in which a plurality of units such as a polyalkylene oxide is bonded via the above azo group one having a polyethylene oxide structure is preferable.
  • Specific examples of the high molecular weight azo compound include polycondensates of 4,4'-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4'-azobis (4-cyanopentanoic acid) And polydimethylsiloxanes having a terminal amino group, and the like.
  • VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 all are Fujifilm Wako Pure Chemical Industries, Ltd. make
  • V-65, V-501 all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
  • organic peroxide examples include ketone peroxide, peroxy ketal, hydroperoxide, dialkyl peroxide, peroxy ester, diacyl peroxide, peroxy dicarbonate and the like.
  • a preferable lower limit is 0.05 parts by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight in total of the curable resin and the maleimide compound.
  • the sealing agent for a liquid crystal display element of the present invention is more excellent in thermosetting.
  • the sealing agent for a liquid crystal display element of the present invention is excellent in low liquid crystal contamination and storage stability.
  • the more preferable lower limit of the content of the thermal polymerization initiator is 0.1 parts by weight, and the more preferable upper limit is 5 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention contains a curable resin. As described later, in the present invention, the maleimide compound is not included in the curable resin.
  • the said curable resin contains a (meth) acrylic compound.
  • a (meth) acrylic acid ester compound an epoxy (meth) acrylate, urethane (meth) acrylate etc. are mentioned, for example.
  • epoxy (meth) acrylate is preferable.
  • the said (meth) acrylic compound has 2 or more of (meth) acryloyl groups in a molecule
  • numerator from the height of the reactivity is preferable.
  • the above “(meth) acrylic” means acrylic or methacrylic
  • the above “(meth) acrylic compound” means a compound having a (meth) acryloyl group
  • the above “((meth) acrylic compound” "Meth) acryloyl” means acryloyl or methacryloyl.
  • the above-mentioned “(meth) acrylate” means an acrylate or a methacrylate.
  • the above-mentioned “epoxy (meth) acrylate” represents the compound which made all the epoxy groups in an epoxy compound react with (meth) acrylic acid.
  • methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate is mentioned, for example , T-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, iso Myristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxy 2)
  • epoxy (meth) acrylate what is obtained by reacting an epoxy compound and (meth) acrylic acid in presence of a basic catalyst according to a conventional method etc. are mentioned, for example.
  • epoxy compound used as a raw material for synthesizing the above-mentioned epoxy (meta) acrylate for example, bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, 2,2'-diallyl bisphenol A type epoxy compound Hydrogenated bisphenol epoxy compound, propylene oxide-added bisphenol A epoxy compound, resorcinol epoxy compound, biphenyl epoxy compound, sulfide epoxy compound, diphenyl ether epoxy compound, dicyclopentadiene epoxy compound, naphthalene epoxy compound, phenol Novolak type epoxy compound, ortho cresol novolac type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenyl Novolac-type epoxy compounds, naphthalene phenol novolac-type epoxy compounds, glycidyl amine type epoxy compounds, alkyl polyol type epoxy compound, a rubber-modified epoxy compounds, glycidyl ester compounds.
  • biphenyl type epoxy compounds commercially available ones include, for example, jER YX-4000H (manufactured by Mitsubishi Chemical Corporation).
  • examples of commercially available sulfide-type epoxy compounds include YSLV-50TE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • Examples of commercially available diphenyl ether type epoxy compounds include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • commercially available ones include, for example, EP-4088S (manufactured by Adeka).
  • Examples of commercially available naphthalene type epoxy compounds include Epiclon HP4032 and Epiclon EXA-4700 (all manufactured by DIC Corporation).
  • Examples of the commercially available phenol novolac epoxy compounds include Epiclon N-770 (manufactured by DIC Corporation).
  • Examples of commercially available ortho-cresol novolac epoxy compounds include Epiclon N-670-EXP-S (manufactured by DIC Corporation).
  • Epiclon HP7200 made by DIC Corporation
  • biphenyl novolac epoxy compounds commercially available ones include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.) and the like.
  • examples of commercially available naphthalenephenol novolac epoxy compounds include ESN-165S (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • commercially available ones include jER630 (manufactured by Mitsubishi Chemical Corporation), Epiclon 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Co., Ltd.), and the like.
  • alkyl polyol type epoxy compounds commercially available ones are, for example, ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epiclon 726 (manufactured by DIC Corporation), Epolight 80 MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX-611. (Made by Nagase ChemteX) etc. are mentioned.
  • commercially available ones include YR-450, YR-207 (all manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), and Eporide PB (manufactured by Daicel Co., Ltd.).
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corp.).
  • Denacol EX-147 manufactured by Nagase ChemteX Corp.
  • YDC-1312, YSLV-80XY, YSLV-90CR all are manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.
  • XAC4151 manufactured by Asahi Kasei Corp.
  • jER1031, jER1032 any one
  • Mitsubishi Chemical Corporation EXA-7120 (manufactured by DIC Corporation), TEPIC (manufactured by Nissan Chemical Industries, Ltd.), and the like.
  • epoxy (meth) acrylates for example, epoxy (meth) acrylate manufactured by Daicel Ornex, epoxy (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., epoxy manufactured by Kyoeisha Chemical Examples thereof include meta) acrylates and epoxy (meth) acrylates manufactured by Nagase ChemteX Corporation. Examples of the epoxy (meth) acrylates manufactured by Daicel Ornex Co., Ltd.
  • 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 and the like. Examples of epoxy (meth) acrylates manufactured by Kyoeisha Chemical Co., Ltd.
  • epoxy ester M-600A examples 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 3000 M, epoxy ester 3000 A, epoxy ester 200 EA, epoxy ester 400 EA, etc. may be mentioned.
  • Examples of the epoxy (meth) acrylate manufactured by Nagase ChemteX Corporation examples include Denacol acrylate DA-141, Denacol acrylate DA-314, Denacol acrylate DA-911 and the like.
  • the urethane (meth) acrylate is obtained, for example, by reacting 2 equivalents of a (meth) acrylic acid derivative having a hydroxyl group with 1 equivalent of an isocyanate compound having two isocyanate groups in the presence of a catalytic amount of a tin-based compound be able to.
  • isocyanate compound examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), and hydrogenation.
  • MDI polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethyl xylylene And isocyanate, 1,6,11-undecanetriisocyanate, etc.
  • a chain-extended isocyanate compound obtained by the reaction of a polyol and an excess of an isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and the like.
  • the (meth) acrylic acid derivative having a hydroxyl group for example, hydroxyalkyl mono (meth) acrylate, mono (meth) acrylate of dihydric alcohol, mono (meth) acrylate or di (meth) acrylate of trihydric alcohol And epoxy (meth) acrylates.
  • hydroxyalkyl mono (meth) acrylate examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate and the like. It 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 trimethylol ethane, trimethylol propane and glycerin.
  • As said epoxy (meth) acrylate, bisphenol-A epoxy acrylate etc. are mentioned, for example.
  • urethane (meta) acrylates for example, urethane (meta) acrylate by Toagosei Co., Ltd., urethane (meta) acrylate by Daicel Ornex, urethane (meta) 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.
  • urethane (meth) acrylate manufactured by the above-mentioned Daicel Ornex Co., Ltd., for example, EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYLL4852, EBECRYLL5129, EBECRYLL747. It can be mentioned.
  • urethane (meth) acrylates manufactured by Shin-Nakamura Chemical Co., Ltd. include U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, U-6LPA, U-10H, and the like.
  • urethane (meth) acrylates manufactured by Kyoeisha Chemical Co., Ltd. include AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T, etc.
  • the said curable resin contains an epoxy compound further in order to improve the adhesiveness of the sealing compound for liquid crystal display elements obtained.
  • combining the epoxy (meth) acrylate mentioned above, a partial (meth) acryl modified epoxy compound, etc. are mentioned, for example.
  • the above-mentioned partial (meth) acrylic-modified epoxy compound means a compound having one or more epoxy group and one or more (meth) acryloyl group in one molecule, for example, two in one molecule. It can obtain by making the epoxy group of a part of the epoxy compound which has the above epoxy group react with (meth) acrylic acid.
  • the sealing compound for a liquid crystal display element of the present invention contains the above-mentioned epoxy compound
  • the ratio of (meth) acryloyl group in the total of (meth) acryloyl group and epoxy group in the above curable resin is 30 mol% or more It is preferable to make it less than mol%.
  • the ratio of the (meth) acryloyl group is 30 mol% or more, the obtained sealing agent for a liquid crystal display element is excellent in low liquid crystal contamination.
  • the sealing agent for liquid crystal display elements obtained by the ratio of the said (meth) acryloyl group being 95 mol% or less will become excellent by adhesiveness.
  • the curable resin preferably has a hydrogen bonding unit such as -OH group, -NH- group, and -NH 2 group.
  • the sealing agent for a liquid crystal display element of the present invention contains a maleimide compound.
  • the sealing agent for a liquid crystal display element of the present invention can suppress the generation of foreign matter even when using the photopolymerization initiator according to the present invention.
  • the maleimide compound is not included in the curable resin.
  • the preferred lower limit of the molecular weight of the maleimide compound is 400.
  • the obtained sealing agent for a liquid crystal display element is excellent due to the effect of achieving both the improvement of the curability to long wavelength light and the suppression of the generation of foreign matter.
  • a more preferable lower limit of the molecular weight of the maleimide compound is 500.
  • the upper limit of the molecular weight of the maleimide compound is preferably 1,500, and more preferably 1,000.
  • the above maleimide compound is preferably a polyfunctional maleimide compound having two or more maleimide groups in one molecule from the viewpoint of reactivity.
  • polyfunctional maleimide compound a compound represented by the following formula (3) or a compound represented by the following formula (4) is suitably used.
  • R 1 represents an alkylene group having a carbon number of 2 to 3
  • n is an integer of 2 to 40.
  • R 2 represents a divalent aliphatic group having 1 to 40 carbon atoms.
  • the carbon number of R 2 is preferably 12 to 36. Further, R 2 preferably has an aliphatic ring.
  • Specific examples of the compound represented by the above formula (4) include 1,4-bis (maleimide) butane, 1,20-bismaleimide-10,11-dioctyl-eicosane (following formula (5-1) ), 1-heptylenemaleimide-2-octylenemaleimide-4-octyl-5-heptylcyclohexane (compound represented by the following formula (5-2)), 1,2-dioc Examples include lenmaleimide-3-octyl-4-hexylcyclohexane (compound represented by the following formula (5-3)) and the like.
  • the compound represented by the above formula (4) can be synthesized, for example, by the method described in US Pat. No. 5,973,166.
  • maleimide compounds as a monofunctional maleimide compound having one maleimide group in one molecule, for example, N-biotinyl-N '-(3-maleimidopropionyl) -3,6-dioxaoctane-1, 8-diamine and the like can be mentioned.
  • the preferable lower limit of the content of the maleimide compound in a total of 100 parts by weight of the curable resin and the maleimide compound is 2 parts by weight, and the preferable upper limit is 50 parts by weight.
  • the content of the maleimide compound is 2 parts by weight or more, the obtained sealing agent for a liquid crystal display element is excellent in the effect of suppressing the generation of foreign matter.
  • the content of the maleimide compound is 50 parts by weight or less, the obtained sealing agent for a liquid crystal display element is more excellent in photocurability.
  • a more preferable lower limit of the content of the maleimide compound is 3 parts by weight, a still more preferable lower limit is 5 parts by weight, and a particularly preferable lower limit is 10 parts by weight.
  • the upper limit of the content of the maleimide compound is preferably 45 parts by weight, more preferably 40 parts by weight, still more preferably 35 parts by weight, particularly preferably 30 parts by weight, and most preferably 25 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention may contain a thermosetting agent.
  • a thermosetting agent an organic acid hydrazide, an imidazole derivative, an amine compound, a polyhydric phenol type compound, an acid anhydride etc. are mentioned, for example.
  • organic acid hydrazides are preferably used.
  • Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide and the like.
  • the organic acid hydrazide by Otsuka Chemical Co., Ltd. As what is marketed among the said organic acid hydrazide, the organic acid hydrazide by Otsuka Chemical Co., Ltd., the organic acid hydrazide by Ajinomoto Fine Techno Co., Ltd., etc. are mentioned, for example.
  • Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
  • Examples of the organic acid hydrazide manufactured by Ajinomoto Fine Techno Co., Ltd. include Amicure VDH, Amicure VDH-J, Amicure UDH, Amicure UDH-J and the like.
  • the preferable lower limit is 1 part by weight and the preferable upper limit is 50 parts by weight with respect to 100 parts by weight in total of the curable resin and the maleimide compound.
  • the thermosetting property can be further improved without deteriorating the coating property and the like of the obtained sealing agent for a liquid crystal display element.
  • a more preferable upper limit of the content of the thermosetting agent is 30 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention preferably contains a filler for the purpose of improving viscosity, improving adhesion due to a stress dispersion effect, improving linear expansion coefficient, and the like.
  • 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 And 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, and acrylic polymer fine particles. The above fillers may be used alone or in combination of two or more.
  • the preferable lower limit of the content of the filler in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight.
  • the content of the above-mentioned filler is in this range, the effect of improving the adhesiveness and the like becomes excellent without deteriorating the coatability and the like.
  • the more preferable lower limit of the content of the filler is 20 parts by weight, and the more preferable upper limit is 60 parts by weight.
  • the sealing agent for a liquid crystal display element of the present invention preferably contains a silane coupling agent.
  • the above-mentioned silane coupling agent mainly serves as an adhesion aiding agent for favorably bonding the sealing agent and the substrate and the like.
  • silane coupling agent for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are suitably used. These are excellent in the effect of improving the adhesion to a substrate or the like, and can suppress the outflow of the curable resin into the liquid crystal by chemically bonding with the curable resin.
  • the preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the liquid crystal display element sealing agent of the present invention is 0.1 parts by weight, and the preferable upper limit is 10 parts by weight.
  • the content of the silane coupling agent is in this range, the occurrence of liquid crystal contamination is suppressed, and the adhesive property is improved.
  • a more preferable lower limit of the content of the silane coupling agent is 0.3 parts by weight, and a more preferable upper limit is 5 parts by weight.
  • the sealant for a liquid crystal display element of the present invention further contains, as necessary, additives such as a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor. May be
  • a curable resin and a curable resin using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a 3-roll mill.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a 3-roll mill.
  • the method etc. which mix the photoinitiator concerning this invention, a maleimide compound, and the silane coupling agent etc. which are added as needed are mentioned.
  • a vertical conduction material can be manufactured by mix
  • a vertical conduction material containing such a sealing agent for a liquid crystal display element of the present invention and conductive fine particles is also one of the present invention.
  • electroconductive fine particle what formed the conductive metal layer in the surface of a metal ball and resin fine particles etc. can be used.
  • those in which a conductive metal layer is formed on the surface of resin fine particles are preferable because the excellent elasticity of the resin fine particles allows conductive connection without damaging the transparent substrate and the like.
  • a liquid crystal display device using the sealing agent for a liquid crystal display device of the present invention or the vertical conduction material of the present invention is also one of the present invention.
  • a liquid crystal dropping method is suitably used, and specifically, for example, a method having the following respective steps can be mentioned.
  • the sealing agent for a liquid crystal display element of the present invention is applied by screen printing, dispenser coating, or the like to one of two substrates such as a glass substrate with an electrode such as ITO thin film and a polyethylene terephthalate substrate.
  • the process of forming a pattern is performed.
  • a step of applying minute droplets of liquid crystal to the inside of the frame of the seal pattern of the substrate by a drop in a state where the sealing agent for a liquid crystal display element of the present invention is uncured is dropped, and another substrate is superposed under vacuum.
  • the seal pattern portion of the sealing agent for a liquid crystal display element of the present invention is irradiated with light through a 420 nm cut filter or the like to perform a step of photocuring the sealing agent with long wavelength light. You can get In addition to the step of photocuring the sealing agent, the step of heating and thermally curing the sealing agent may be performed.
  • the sealing compound for liquid crystal display elements which is excellent in the sclerosis
  • PS-PPh 3 a basic catalyst in which triphenylphosphine is supported on polystyrene (PS) manufactured by Biotage Japan Ltd.
  • PS-PPh 3 a basic catalyst in which triphenylphosphine is supported on polystyrene (PS) manufactured by Biotage Japan Ltd.
  • a basic catalyst comprising 69 parts by weight of 2-hydroxy-9H-thioxanthen-9-one and 62 parts by weight of p-tert-butylphenyl glycidyl ether ("ED-509S" manufactured by ADEKA Corporation) as a monofunctional epoxy compound
  • ED-509S p-tert-butylphenyl glycidyl ether
  • a basic catalyst 5.2 parts by weight of PS-PPh 3 (a basic catalyst in which triphenylphosphine is supported on polystyrene (PS) manufactured by Biotage Japan Ltd.) was used.
  • Examples 1 to 9 and Comparative Examples 1 to 3 According to the compounding ratio described in Tables 1 and 2, after mixing each material using a planetary stirrer ("Awatori Neritaro" manufactured by Shinky Co., Ltd.), mixing is further performed using three rolls. Sealing agents for liquid crystal display devices of Examples 1 to 9 and Comparative Examples 1 to 3 were prepared.
  • a spectrophotometer the Hitachi High-Tech Science company make, "U-3900" The extinction coefficient at a wavelength of 430 nm was measured using this.
  • a light of 100 mW / cm 2 was irradiated to the sealant portion of the bonded glass substrate for 10 seconds using a metal halide lamp.
  • Light irradiation performed two patterns, the case without a 420 nm cut filter, and the case with a 420 nm cut filter.
  • Evaluation of curability by performing FT-IR measurement of the sealing agent using an infrared spectrometer (manufactured by BIORAD, "FTS 3000") and measuring the amount of change of the (meth) acryloyl group-derived peak before and after light irradiation Did.
  • the sealing compound for liquid crystal display elements which is excellent in the sclerosis

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Mathematical Physics (AREA)
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  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
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  • Polymerisation Methods In General (AREA)
  • Epoxy Resins (AREA)

Abstract

Un objet de la présente invention est de fournir un agent d'étanchéité pour éléments d'affichage à cristaux liquides, qui est apte à supprimer la génération de substances étrangères, tout en présentant une excellente aptitude au durcissement à la lumière ayant une grande longueur d'onde. Un autre objet de la présente invention est de fournir : un matériau à conduction verticale qui est obtenu à l'aide de cet agent d'étanchéité pour éléments d'affichage à cristaux liquides ; ainsi qu'un élément d'affichage à cristaux liquides. La présente invention concerne un agent d'étanchéité pour éléments d'affichage à cristaux liquides, qui contient une résine durcissable, un initiateur de photopolymérisation et un composé maléimide, et l'initiateur de photopolymérisation ayant un coefficient d'absorption supérieur ou égal à 0,8 × 102 mL/g·cm à la longueur d'onde de 430 nm.
PCT/JP2018/025999 2017-07-14 2018-07-10 Agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale et élément d'affichage à cristaux liquides Ceased WO2019013194A1 (fr)

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KR1020197015190A KR102612646B1 (ko) 2017-07-14 2018-07-10 액정 표시 소자용 시일제, 상하 도통 재료, 및 액정 표시 소자
JP2018540897A JP7156946B2 (ja) 2017-07-14 2018-07-10 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
CN201880007538.1A CN110226120A (zh) 2017-07-14 2018-07-10 液晶显示元件用密封剂、上下导通材料和液晶显示元件

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