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WO2008004455A1 - Agent d'etanchéite pour cristaux liquides et cellules d'affichage à cristaux liquides utilisant cet agent - Google Patents

Agent d'etanchéite pour cristaux liquides et cellules d'affichage à cristaux liquides utilisant cet agent Download PDF

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Publication number
WO2008004455A1
WO2008004455A1 PCT/JP2007/062699 JP2007062699W WO2008004455A1 WO 2008004455 A1 WO2008004455 A1 WO 2008004455A1 JP 2007062699 W JP2007062699 W JP 2007062699W WO 2008004455 A1 WO2008004455 A1 WO 2008004455A1
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WIPO (PCT)
Prior art keywords
liquid crystal
epoxy resin
crystal sealant
weight
curing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2007/062699
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English (en)
Japanese (ja)
Inventor
Toyohumi Asano
Masahiro Kida
Tsutomu Namiki
Naoyuki Ochi
Hideyuki Ota
Masahiro Imaizumi
Masahiro Hirano
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.)
Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Priority to CN2007800253041A priority Critical patent/CN101484844B/zh
Priority to KR1020087030926A priority patent/KR101333720B1/ko
Publication of WO2008004455A1 publication Critical patent/WO2008004455A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • 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 liquid crystal sealant and a liquid crystal display cell using the same. More specifically, the present invention relates to a liquid crystal sealing agent suitable for manufacturing a liquid crystal display cell by a liquid crystal dropping method and a liquid crystal display cell manufactured using the same.
  • liquid crystal dropping method With the recent increase in the size of liquid crystal display cells, a so-called liquid crystal dropping method with higher mass productivity has become widespread as a method for manufacturing liquid crystal display cells.
  • a liquid crystal display cell in which the liquid crystal is sealed is manufactured by dropping the liquid crystal inside the weir of the liquid crystal sealant formed on one substrate and then bonding the other substrate.
  • the liquid crystal sealant component elutes into the liquid crystal and contaminates the display area of the liquid crystal. Therefore, there is a need for a liquid crystal sealant with low contamination due to the viewpoint of improving the reliability of liquid crystal display cells.
  • thermosetting method the sealant has a low viscosity when heated, so it is difficult to maintain the seal shape, and the liquid crystal is easily contaminated because the uncured liquid crystal sealant and the liquid crystal are in contact with heat. There is.
  • the liquid crystal sealant used in the photocuring method there are two types, a force thione polymerization type and a radical polymerization type, depending on the type of the photopolymerization initiator.
  • the cationic polymerization type liquid crystal sealant has a drawback that it is inferior in reliability because the cationic component generated during photocuring contaminates the liquid crystal and lowers the specific resistance of the liquid crystal.
  • the radical polymerization type liquid crystal sealant V has a large cure shrinkage upon photocuring, there is a problem that the adhesive strength is insufficient.
  • the light shielding part where the liquid crystal sealant is not exposed to light by the metal wiring part of the array substrate of the liquid crystal display cell or the black matrix part of the color filter substrate. Because of this, the shading part The problem arises that the minutes become uncured.
  • thermosetting method and the photocuring method have their respective problems, and the photothermosetting combined method is in widespread use as a practical curing system.
  • the photothermal curing combined method is characterized in that a liquid crystal sealant sandwiched between substrates is first cured by light irradiation and then heated to be secondarily cured (see Patent Document 1).
  • Advantages of thermosetting include significantly improved adhesive strength and moisture resistance reliability, and can be cured by thermosetting even if there is a light-shielding part.
  • the change in viscosity during use at room temperature is small and that the pot life is good.
  • it is generally 130 ° C.
  • a cured resin used in a photothermographic combination liquid crystal sealant is a cured resin having both a thermosetting epoxy group and a photocurable (meth) attalyloyl group reactive group. It is common to use a system. As such a cured resin system, a mixed resin system of an epoxy resin and an epoxy (meth) acrylate resin, or an epoxy resin that has been partially (meth) atta loyalized is used. In addition, the cured resin system further requires a photopolymerization initiator component for photocuring the (meth) attalyloyl group and a curing agent component for thermally curing the epoxy group.
  • hydrazide compounds such as adipic acid dihydrazide, sebacic acid dihydrazide, isophthalic acid dihydrazide, Amicure VDH (manufactured by Ajinomoto Finetech Co., Ltd .; dihydrazides having a valine hydantoin skeleton) are generally used.
  • the hydrazide compound is suitable not only for reacting with an epoxy group by heating but also for reacting with a (meth) atalyloyl group, so that it is suitable for curing a light shielding part, but causes a change with time such as viscosity at room temperature.
  • the selection of the curing agent is an important factor that greatly affects the workability of the liquid crystal sealant, such as liquid crystal contamination and pot life.
  • the hydrazides sealants using adipic acid dihydrazide, sebacic acid dihydrazide, dodecanoic acid dihydrazide, isophthalic acid dihydrazide and the like are relatively excellent in storage stability, but have low temperature curability due to their high melting point.
  • Amicure VDH a low-melting hydrazide compound, has excellent low-temperature curability. The stability is not good.
  • the liquid crystal dropping method using only heat curing without using photocuring is easily realized because of the difficulty in maintaining the shape of the seal and the contamination of the liquid crystal as described above.
  • the shape can be maintained and contamination can be reduced by increasing the reaction viscosity at a relatively low temperature when the temperature of thermosetting is increased.
  • a low-temperature curing accelerator but imidazoles, amine adducts, tertiary amines, triphenyl which are usually used as accelerators for epoxy resin.
  • thermosetting liquid crystal dropping method including a curing system using a curing accelerator.
  • the industrial advantage of performing the liquid crystal dripping method only by thermal curing is that no expensive photomask and UV lamp that protect the liquid crystal and alignment film are required during UV curing. The power cost required for lighting can be reduced.
  • Patent Document 2 discloses a curing system of epoxy resin and dihydrazide curing agent! No mention is made of the possibility that polycarboxylic acids can be applied to liquid crystal sealants, which have been shown to be effective as curing accelerators.
  • Patent Document 1 Japanese Patent No. 2846842
  • Patent Document 2 Japanese Patent Laid-Open No. 62-172014
  • the present invention firstly provides a liquid crystal sealant having excellent low-temperature curability, and at the same time having low liquid crystal contamination and a long pot life. Secondly, it is to provide a liquid crystal sealant effective for the thermosetting liquid crystal dropping method. Means for solving the problem
  • Curable resin (b) is a mixture of epoxy resin and (meth) acrylic epoxy resin, liquid crystal sealant according to (1),
  • liquid crystal sealing agent according to (1) or (2), wherein the polyvalent carboxylic acid (c) is dodecanedioic acid or decanedioic acid,
  • T1 to T3 are each independently hydrogen or the following formula (2)
  • a seal pattern is formed using the liquid crystal sealant described in A method of manufacturing a liquid crystal display cell, wherein the liquid crystal is dropped on the substrate or the counter substrate, the counter substrate is bonded together, and then the liquid crystal sealant is cured,
  • the liquid crystal sealant of the present invention is particularly excellent in low-temperature curability, and at the same time, has good workability for application to a substrate, low adhesion to the liquid crystal and long pot life, adhesion, and adhesive strength.
  • the liquid crystal sealant used in the present invention contains a dihydrazide compound (a) as a curing agent.
  • Dihydrazides in this case refer to those having two hydrazide groups in the molecule. Specific examples thereof include oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, adipic acid dihydrazide, and adipic acid dihydrazide.
  • dihydrazide When dihydrazide is used as a curing agent, it is preferable to uniformly disperse the particle size by vigorously.
  • dihydrazides adipic acid dihydrazide, isophthalic acid dihydrazide, and 1,3-bis (hydrazinocarbonoethyl) 5-isopropylhydantoin (Amicure VDH) are particularly preferred from the viewpoint of liquid crystal contamination. That flat
  • the average particle size is preferably 3 m or less, more preferably 2 m or less, because if the particle size is too large, it becomes a cause of defects such as failure to form a gap when the upper and lower glass substrates are bonded together when manufacturing a narrow gap liquid crystal cell. is there.
  • the maximum particle size is preferably 8 m or less, more preferably 5 m or less.
  • the particle size of the curing agent was measured with a laser diffraction / scattering particle size distribution analyzer (dry type) (manufactured by Seishin Enterprise Co., Ltd .; LMS-30).
  • the curing agent for the liquid crystal dropping method liquid crystal sealant when heated after light irradiation, the liquid crystal sealant starts a reaction uniformly and quickly without contaminating the liquid crystal, and when used, there is little change in viscosity at room temperature. It is important that the pot life is good.
  • solid dispersion type latent thermosetting agents if the particle size is uneven and there is a large particle size, or if the dispersion is insufficient and uneven, the curing is not performed uniformly and the cause of the cell gap failure Or the liquid crystal panel is contaminated, resulting in poor display on the liquid crystal panel.
  • a dihydrazide compound used in the present invention that has been finely pulverized to an average particle size of 3 m or less as measured by a laser diffraction / scattering particle size distribution analyzer. More preferably, the average particle size is 2 ⁇ m or less, and the lower limit of the average particle size is about 0.1 ⁇ m. Similarly, the maximum particle size is preferably 8 m or less, more preferably 5 m or less.
  • a sealant using a dihydrazide compound has a very good pot life at room temperature, but exhibits moderate curability even at 120 ° C for 1 hour. Dihydrazide compounds have almost no solubility in liquid crystals!
  • the amount of the dihydrazide compound (a) used as a curing agent is preferably 1 part by weight or more and 20 parts by weight or less with respect to 100 parts by weight of the curable resin (b).
  • the curable resin of the present invention includes one or more curable resins selected from epoxy resins, (meth) acrylic epoxy resins and partial (meth) acrylic epoxy resins.
  • epoxy resin a mixture of epoxy resin and (meth) acrylic epoxy resin, (meth) acrylic epoxy resin, partial (meth) acrylic epoxy resin, and so on.
  • the curable resin used in the present invention preferably has low contamination and solubility in liquid crystals.
  • suitable epoxy resins include bisphenol S type epoxy resin and resorcin diglycidyl ether in large quantities.
  • Body, Ethylene oxide added bisphenol Examples include, but are not limited to, diglycidyl ether of s.
  • (Meta) Atalloy Roi epoxy resin partial (Meth) Atalloy Roi epoxy resin is obtained by the reaction of epoxy resin and (meth) acrylic acid.
  • the epoxy resin used as a raw material is not particularly limited, but a bifunctional or higher functional epoxy resin is preferred.
  • bisphenol A type epoxy resin bisphenol F type epoxy resin, bisphenol S Epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, bisphenol A novolac epoxy resin, bisphenol F novolac epoxy resin, alicyclic epoxy resin, aliphatic chain Epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy resin, phenol novolac type epoxy resin having triphenol methane skeleton, other bifunctional phenol Diglycidyl ethers, bifunctional alcohols Diglycidyl ethers of, and their halides, hydrogenated product and be mentioned up.
  • the ratio of the epoxy group to the (meth) attaylyl group is not limited and is appropriately selected from the viewpoint of process compatibility and liquid crystal contamination.
  • a monomer and Z or oligomer of (meth) acrylic acid ester may be used for the control of reactivity and viscosity.
  • Such monomers and oligomers include, for example, a reaction product of dipentaerythritol and (meth) acrylic acid, a reaction product of dipentaerythritol's force prolatatone and (meth) acrylic acid, etc. Low, not particularly limited.
  • the amount of the curable resin (b) used in the present invention is within a range that does not affect the workability and physical properties of the obtained liquid crystal sealant, and is usually 25% in the liquid crystal sealant. About 80% by weight, preferably 25-75% by weight.
  • a radical reaction type photopolymerization initiator is used in order to impart photocurability.
  • a radical reaction type photopolymerization initiator has relatively little effect on the characteristics of liquid crystal! /, Has sensitivity near i-line (365nm) and low liquid crystal contamination! Any initiator can be used.
  • Used radical reaction type photopolymerization initiator Examples include benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, jetylthioxanthone, benzophenone, 2-ethylanthraquinone, 2-hydroxy-2-methylpropiophenone, 2-methyl- [4 (methylthio) phene.
  • the amount used is usually about 0.1 to 5% by weight in the liquid crystal sealant.
  • a polyvalent carboxylic acid (c) is blended as a curing accelerator for improving low-temperature curability.
  • the polyvalent carboxylic acid include aromatic carboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid and benzophenone tetracarboxylic acid, aliphatic carboxylic acids such as decanedioic acid and dodecanedioic acid, And polyvalent carboxylic acids having an isocyanuric ring skeleton represented by the general formula (1).
  • polyvalent carboxylic acid having an isocyanuric ring skeleton represented by the general formula (1) include tris (2-carboxymethyl) isocyanurate (the following formula (5)), tris (2 carboxyethyl) ) Isocyanurate (following formula (3)), tris (2-carboxypropyl) isocyanurate (following formula (4)), and bis (2 carboxyethyl) isocyanurate (following formula (6)).
  • decanedioic acid, dodecanedioic acid, and polyvalent carboxylic acid having an isocyanuric ring skeleton are preferable from the viewpoint of stability over time and liquid crystal contamination.
  • the addition amount of the curing accelerator is 0.1 parts by weight or more per 100 parts by weight of the curable resin (b), 1 0 parts by weight or less is preferable.
  • An inorganic filler may be blended in the liquid crystal sealant of the present invention for the purpose of improving adhesiveness, moisture resistance and the like.
  • the inorganic filler that can be used is not particularly limited. Specifically, spherical silica, fused silica, crystalline silica, titanium oxide, titanium black, silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, and barium sulfate.
  • Calcium sulfate my strength, talc, clay, alumina, magnesium oxide, zirconium oxide, aluminum hydroxide, magnesium hydroxide, calcium silicate, aluminum silicate, lithium aluminum silicate, zirconium silicate, barium titanate, glass fiber, Carbon fiber, disulfurium molybdenum, asbestos and the like, preferably spherical silica, fused silica, crystalline silica, titanium oxide, titanium black, silicon nitride, boron nitride, calcium carbonate, barium sulfate, calcium sulfate, my strength, Talc, Kure , Alumina, aluminum hydroxide, silicate calcium ⁇ beam, aluminum silicate. Two or more of these inorganic fillers may be used in combination.
  • the average particle size of the inorganic filler used in the present invention is preferably 3 ⁇ m or less. If the average particle size is larger than 3 m, there may be a problem in forming a gap when the upper and lower glass substrates are bonded together during the production of the liquid crystal cell. Usually the lower limit of the average particle size of inorganic fillers. It is about 01 / z m.
  • the content of the inorganic filler used in the present invention in the liquid crystal sealant is usually 2 to 60% by weight, preferably 5 to 50% by weight.
  • the filler content is lower than 2% by weight, the adhesion strength to the glass substrate is lowered, and the moisture resistance reliability is inferior.
  • the filler content is more than 60% by weight, the filler content is too large, and there is a risk that the gap of the liquid crystal cell cannot be formed.
  • an organic filler may be further added to the liquid crystal sealant of the present invention within the range without affecting the properties of the liquid crystal sealant.
  • organic fillers include polymer beads and core shell type rubber fillers. These fillers may be used in combination of two or more.
  • the liquid crystal sealant of the present invention has a silane coupling in order to improve its adhesive strength. It is preferable to contain an agent.
  • silane coupling agents that can be used include 3-dallyglycidoxypropinoremethinoresimethoxymethoxysilane, 2- (3,4 epoxyepoxycyclohexylene) ethyltrimethoxysilane, N-phenyl-1- ⁇ -aminopropyl.
  • Trimethoxysilane ⁇ — (2 —aminoethyl) 3 aminopropylmethyldimethoxysilane, ⁇ — (2 aminoethyl) 3-aminopropylmethyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-mercapto Propyltrimethoxysilane, vinyltrimethoxysilane, ⁇ — (2- (vinylbenzylamino) ethyl) 3-aminopropyltrimethoxysilane hydrochloride, 3-methacryloxypropyl trimethoxysilane, 3-chloropropylmethyldimethoxysilane , 3-silane mouth propyltrimethoxysilane, etc.
  • Examples include pulling agents. These silane coupling agents may be used in combination of two or more. Of these, in order to obtain better adhesive strength, the silane coupling agent is preferably a silane coupling agent having an amino group. By using a silane coupling agent, an adhesive strength is improved and a liquid crystal sealant having excellent moisture resistance reliability can be obtained.
  • the amount used is usually about 0.1 to 15% by weight in the liquid crystal sealant.
  • the liquid crystal sealant according to the present invention may further contain an organic solvent and additives such as a pigment, a leveling agent, and an antifoaming agent, if necessary.
  • liquid crystal sealant of the present invention In order to obtain the liquid crystal sealant of the present invention, a filler component and a thermosetting agent are first mixed with a resin component dissolved and mixed in a known mixing device such as a three-roll, sand mill, ball mill, or planetary mixer.
  • the liquid crystal sealant of the present invention can be produced by mixing more uniformly. In order to remove impurities after mixing is completed, it is preferable to perform filtration.
  • the substrate is composed of a combination of substrate substrates having at least one of light, such as glass, quartz, plastic, silicon, etc., which has optical transparency.
  • the manufacturing method is, for example, that after adding a spacer (gap control material) such as a glass fiber to the liquid crystal sealant of the present invention, a dispenser is placed on one of the pair of substrates.
  • the liquid crystal sealing agent After applying the liquid crystal sealing agent in the shape of a weir by means of a pressure etc., a liquid crystal is dropped inside the liquid crystal sealing agent weir and the other glass substrate is superposed in a vacuum to form a gap. After forming the gap, the liquid crystal seal is irradiated with ultraviolet rays by an ultraviolet irradiator and photocured.
  • the amount of ultraviolet irradiation is usually 200 mjZcm 2 to 6000 mjZcm 2 , preferably 500 mj / cm 2 to 4000 mjZcm 2 .
  • the liquid crystal display cell of the present invention can be obtained by curing at 90 to 140 ° C. for 1 to 2 hours.
  • the liquid crystal display cell of the present invention can be obtained by curing at 90 to 140 ° C. for 1 to 2 hours without ultraviolet irradiation.
  • the spacer include glass fiber, silica beads, and polymer beads. Its diameter varies depending on the purpose. 1S is usually 2 to 8 m, preferably 4 to 7 m. The amount used is usually about 0.1 to 4 parts by weight, preferably about 0.5 to 2 parts by weight per 100 parts by weight of the liquid crystal sealant of the present invention.
  • the liquid crystal sealant of the present invention is extremely low in contamination with liquid crystals throughout the production process, and is easy to apply to the substrate, adherence, adhesion strength, pot life at room temperature, low temperature Excellent curability.
  • the liquid crystal display cell of the present invention thus obtained is excellent in adhesion and moisture resistance reliability with no display failure due to liquid crystal contamination.
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; bisphenol F epoxy resin epoxy acrylate) 75 parts by weight, epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy) Equivalent 233gZeq, Ethylene oxide-added bisphenol S-type epoxy resin) 25 parts by weight, photopolymerization initiator KAYACURE RPI-4 (manufactured by Nippon Yakuhin Co., Ltd .; 2 isocyanatoethyl metatalylate and 2-hydroxy 1- [4 — (2Hydroxyethoxy) phenol] Reaction product with 2 methylpropane 1-on) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3-glycidoxy pill trimethoxysilane) 1.
  • Nanotech Alumina SPC Cho Kasei Co., Ltd .; spherical alumina, average particle size 50 nm
  • butadiene 'alkyl methacrylate' styrene copolymer Rohm and Haas
  • Paraloid EXL-2655 3 parts by weight are uniformly mixed in a bead mill, and then isophthalic acid dihydrazide finely pulverized product (manufactured by Otsuka Chemical Co., Ltd .; IDH-S is average particle size 1.5 mm in a jet mill.
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; Epoxy acrylate of bisphenol F epoxy resin) 75 parts by weight, epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy) Equivalent 233gZeq, 25 parts by weight of ethylene oxide-added bisphenol S-type epoxy resin) KAYACURE RPI-4 (manufactured by Nippon Yakuhin Co., Ltd .; 2-Isocyanatoethyl methacrylate and 2-hydroxy 1- [4 -— (2-Hydroxyethoxy) phenol] 2 Reaction product with methylpropane 1-one) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3-glycidoxyp mouth pill tri (Methoxysilane) 1.5 parts by weight was mixed to obtain a resin solution.
  • Nano Tech Alumina SPC Cho Kasei Co., Ltd .; spherical alumina, average particle size 50 nm
  • isophtalic acid dihydrazide finely pulverized product Otsuka Chemical Co., Ltd .; IDH-S with jet mill average particle size 1.5 m, maximum particle size 5 m 7.
  • liquid crystal sealant of the present invention was obtained by kneading 3 parts by weight with a three-necked mixture.
  • the viscosity (25 ° C) of the liquid crystal sealant was 340 Pa ⁇ s (25 ° C, R-type viscometer (manufactured by Toki Sangyo Co., Ltd.)).
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; bisphenol F epoxy resin acrylate) 75 parts by weight, epoxy resin RE- 203 ( Nippon Kayaku Co., Ltd .; epoxy equivalent 233gZeq, ethylene oxide added bisphenol S type epoxy resin) 25 parts by weight, photopolymerization initiator KAYACURE RPI-4 (manufactured by Nippon Iyaku Co., Ltd .; 2 isocyanatoethyl metatali Reaction product of 2-hydroxy 1- [4- (2-hydroxyethoxy) phenol] 2 methylpropane 1-one) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3 -Glycidoxip oral trimethylsilane) 1.
  • Nano Tech Alumina SPC Cho Kasei Co., Ltd .; spherical alumina, average particle size 50 nm
  • isophtalic acid dihydrazide finely pulverized product Otsuka Chemical Co., Ltd .; IDH-S with jet mill average particle size 1.5 m, maximum particle size 5 m 7.
  • liquid crystal sealant 55 parts by weight, tris (2-carboxypropyl) isocyanurate pulverized product (manufactured by Shikoku Kasei Kogyo Co., Ltd .: C3-CIC acid with Jet Mill average particle size 1.5 m, maximum particle size 5 Finely pulverized to ⁇ m) 3 parts by weight were mixed and kneaded with three rolls to obtain the liquid crystal sealant of the present invention.
  • the liquid crystal sealant had a viscosity (25 ° C) of 380 Pa's (25 ° C, R-type viscometer (manufactured by Toki Sangyo Co., Ltd.)).
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; Bisphenol F epoxy acrylate resin epoxy acrylate) 75 parts by weight, Epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy equivalent 233gZeq, Ethylene oxide-added bisphenol S-type epoxy resin) 25 parts by weight, photopolymerization initiator KAYACURE RPI-4 (manufactured by Nippon Kayaku Co., Ltd .; 2-isocyanatoethyl methacrylate and 2-hydroxy 1- [4- (2-Hydroxyethoxy) phenol] Reaction product with 2 methylpropane 1-one) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3-glycidoxy pill trimethoxysilane) 1.
  • Nano Tech Alumina SPC Cho Kasei Co., Ltd .; spherical alumina, average particle size 50 nm) 17.5 parts by weight, butadiene 'alkyl methacrylate' styrene copolymer (Rohm and Haas Co., Ltd .; Paraloid EXL) — 2655) 3 parts by weight were mixed evenly with a bead mill, and then adipic acid dihydrazide finely pulverized product (Otsuka Chemical Co., Ltd .; ADH-S averaged with a jet mill) Particle size: 1.5 m, finely pulverized to a maximum particle size of 5 ⁇ m) 7 parts by weight, dodecanedioic acid pulverized product (Ube Industries, Ltd .: average particle size of dodecanedioic acid by jet mill 1.5 / ⁇ ⁇ , finely pulverized to a
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; epoxy phenolic bisphenol F epoxy resin) 75 parts by weight, epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy) Equivalent 233gZeq, 25 parts by weight of ethylene oxide-added bisphenol S-type epoxy resin) KAYACURE RPI-4 (manufactured by Nippon Yakuhin Co., Ltd .; 2-Isocyanatoethyl methacrylate and 2-hydroxy 1- [4 -— (2-Hydroxyethoxy) phenol] 2 Reaction product with methylpropane 1-one) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3-glycidoxyp mouth pill tri (Methoxysilane) 1.5 parts by weight was mixed to obtain a resin solution.
  • Nano Tech Alumina SPC (Chi Kasei Co., Ltd .; spherical alumina, average particle size 50 nm) 17.5 parts by weight, butadiene 'alkyl methacrylate' styrene copolymer (Rohm and Haas Co., Ltd .; Paraloid EXL) — 2655) 3 parts by weight were mixed uniformly with a bead mill, and then adipic acid dihydrazide finely pulverized product (manufactured by Otsuka Igaku Co., Ltd .; ADH-S with a jet mill average particle size of 1.5 m, maximum particle size of 5 7 parts by weight, tris (2-carboxyethyl) isocyanurate pulverized product (manufactured by Shikoku Kasei Kogyo Co., Ltd .: average particle size of 1.5 m, maximum particle size of 5 ⁇ m with CIC acid in a jet mill) 1 part by weight
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; bisphenol F epoxy resin epoxy acrylate) 75 parts by weight, epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy) Equivalent 233gZeq, Ethylene oxide added bisphenol S-type epoxy resin) 25 parts by weight, photopolymerization initiator KAYACURE RPI—4 Manufactured by Yakuhin Co., Ltd .; 2-isocyanatoethyl methacrylate and 2-hydroxy 1- [4- (2-hydroxyethoxy) phenol] 2 methylpropane 1-one reaction product) 5 parts by weight, silane Coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3-glycidoxip pill trimethoxysilane) 1.
  • Nano Tech Alumina SPC Cho Kasei Co., Ltd .; spherical alumina, average particle size 50 nm
  • 3 parts by weight were mixed uniformly with a bead mill, and then adipic acid dihydrazide finely pulverized product (manufactured by Otsuka Igaku Co., Ltd .; ADH-S with a jet mill average particle size 1.5 m, maximum particle size 5 7 parts by weight, tris (2-carboxyl pill) isocyanurate pulverized product (manufactured by Shikoku Kasei Kogyo Co., Ltd .: C3-CIC acid in jet mill with an average particle size of 1.5 m, maximum size
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; Bisphenol F epoxy acrylate resin epoxy acrylate) 75 parts by weight, Epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy equivalent 233gZeq, Ethylene oxide-added bisphenol S-type epoxy resin 25 parts by weight, photopolymerization initiator KAYACURE RPI-4 (manufactured by Nippon Kayaku Co., Ltd .; 2 isocyanatoethyl metatalylate and 2 hydroxy 1- [4— (2 Hydroxyethoxy) phenyl] 2) Reaction product with methylpropane 1-on) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3 -glycidoxyl pill trimethoxysilane) 1.5 A weight part was mixed and the resin liquid was obtained.
  • silane coupling agent Silaace S-510 (manufactured by Chi
  • Nano Tech Alumina SPC Cho Kasei Co., Ltd .; spherical alumina, average particle size 50 nm
  • butadiene 'alkyl methacrylate' styrene copolymer (Rohm and Haas Co., Ltd .; Paraloid EXL) — 2655) 3 parts by weight
  • isophthalic acid dihydrazide (Otsuka Chemical Co., Ltd .; IDH—S average particle size 1.5 / ⁇ ⁇ , maximum particle size with a jet mill.
  • the material was finely pulverized to 5 m) 7.
  • the viscosity (25 ° C) of the liquid crystal sealant is 320 Pa's (25 ° C, R-type viscometer (manufactured by Toki Sangyo Co., Ltd.)).
  • Epoxy acrylate resin KAYARAD R-94220 (Nippon Kayaku Co., Ltd .; Bisphenol F epoxy acrylate resin epoxy acrylate) 75 parts by weight, Epoxy resin RE- 203 (Nippon Kayaku Co., Ltd .; epoxy equivalent 233gZeq, Ethylene oxide-added bisphenol S-type epoxy resin 25 parts by weight, photopolymerization initiator KAYACURE RPI-4 (manufactured by Nippon Kayaku Co., Ltd .; 2 isocyanatoethyl metatalylate and 2 hydroxy 1- [4— (2 Hydroxyethoxy) phenyl] 2) Reaction product with methylpropane 1-on) 5 parts by weight, silane coupling agent Silaace S-510 (manufactured by Chisso Corporation; 3 -glycidoxyl pill trimethoxysilane) 1.5 A weight part was mixed and the resin liquid was obtained.
  • silane coupling agent Silaace S-510 (manufactured by Chi
  • Nano Tech Alumina SPC (Chi Kasei Co., Ltd .; spherical alumina, average particle size 50 nm) 17.5 parts by weight, butadiene 'alkyl methacrylate' styrene copolymer (Rohm and Haas Co., Ltd .; Paraloid EXL) — 2655) 3 parts by weight were mixed uniformly with a bead mill, and then adipic acid dihydrazide finely pulverized product (manufactured by Otsuka Igaku Co., Ltd .; ADH-S with a jet mill average particle size of 1.5 m, maximum particle size of 5 7 parts by weight were kneaded with three rolls to obtain the liquid crystal sealant of the present invention.
  • the viscosity (25 ° C) of the liquid crystal sealant was 300 Pa's (25 ° C, R-type viscometer (manufactured by Toki Sangyo Co., Ltd.)).
  • Table 1 shows the composition table of the liquid crystal sealants described in Examples 1 to 6 and Comparative Examples 1 and 2.
  • liquid crystal sealant 0.5 g was placed in a sample bottle and liquid crystal (MLC, MLC-6866-100) lg was prepared, and then placed in a 120 ° C. oven for 1 hour. Immediately after removing from the oven The amount of the sealant component eluted by gas chromatography after removing the liquid crystal from the sample bottle
  • An alignment film solution (PIA-5540-05A; manufactured by Chisso Corporation) was applied to a substrate with a transparent electrode, baked, and rubbed. A seal pattern and a dummy seal pattern are formed with a dispenser so that the line width after bonding the liquid crystal sealants of Examples and Comparative Examples to 1 mm on this substrate, and then liquid crystal (JC-5015LA; manufactured by Chisso Corporation) Were dropped in the frame of the seal pattern. Furthermore, an in-plane spacer (NATOCOSPACEA KSEB-525F; manufactured by NATCO Corporation; sprayed the gap width after bonding, heat-fixed, and bonded in a vacuum using a bonding device.
  • NATOCOSPACEA KSEB-525F manufactured by NATCO Corporation
  • the sealant part was irradiated with 3j / cm 2 (30 seconds with lOOmWZcm 2 ) with a metal halide lamp (manufactured by Usio Electric Co., Ltd.). Furthermore, it was put into a 120 ° C oven and heat-cured for 1 hour to prepare a liquid crystal test cell for evaluation.
  • An alignment film solution (PIA-5540-05A; manufactured by Chisso Corporation) was applied to a substrate with a transparent electrode, baked, and rubbed.
  • the sticker pattern and dummy seal were dispensed with a dispenser so that the line width after laminating the liquid crystal sealants of Examples and Comparative Examples on this substrate was lmm.
  • a fine droplet of liquid crystal (JC-5015LA; manufactured by Chisso Corporation) was dropped into the frame of the seal pattern.
  • an in-plane spacer (NATOCOSPACEA KSEB-525F; manufactured by NATCO Corporation; sprayed the gap width after bonding, heat-fixed, and bonded in a vacuum using a bonding device. After bonding to the liquid crystal dripped substrate and forming a gap by opening it to the atmosphere, it was put into a 120 ° C oven as it was without UV curing and cured by heating for 1 hour to prepare a liquid crystal test cell for evaluation.
  • Table 5 shows the results of observation of the seal shape and liquid crystal alignment disorder of the prepared liquid crystal cell for evaluation using a polarizing microscope. The evaluation was based on the following four levels.
  • the liquid crystal sealants of Examples and Comparative Examples according to the present invention are both liquid crystal sealants with low liquid crystal contamination.
  • Table 4 it can be seen that the liquid crystal sealants of the examples have higher adhesive strength than the comparative examples even at low temperature curing (100 ° C. ⁇ 1 hour), and are excellent in low temperature curing properties. It can also be seen that the pot life is no inferior to the comparative example.
  • Table 5 shows that the liquid crystal sealant of the example can form cells by the thermosetting liquid crystal dropping method, which is impossible with the liquid crystal sealant of the comparative example, and there is little contamination near the seal.

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

Abstract

[PROBLEMS] Fournir un agent d'étanchéité pour cristaux liquides qui présente une excellente aptitude au durcissement à de faibles températures, qui est moins susceptible de contaminer un cristal liquide, et qui possède une longue durée de vie, une bonne aptitude au façonnage sous forme de revêtement sur un substrat, une bonne propriété de stratification, et une bonne force d'adhérence, et fournir également un agent d'étanchéité pour cristaux liquides qui est utile dans le remplissage par goutte unique d'un cristal liquide thermodurcissable. [MEANS FOR SOLVING PROBLEMS] Agent d'étanchéité pour cristaux liquides comprenant (a) un composé de dihydrazide, (b) un ou plusieurs éléments choisis parmi une résine époxy, une résine époxy (méth)acrylée et une résine époxy partiellement (méth)acrylée en tant que constituant de résine durcissable, et (c) un acide polycarboxylique en tant qu'agent accélérateur du durcissement.
PCT/JP2007/062699 2006-07-05 2007-06-25 Agent d'etanchéite pour cristaux liquides et cellules d'affichage à cristaux liquides utilisant cet agent Ceased WO2008004455A1 (fr)

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CN2007800253041A CN101484844B (zh) 2006-07-05 2007-06-25 液晶密封剂及使用该密封剂制成的液晶显示单元
KR1020087030926A KR101333720B1 (ko) 2006-07-05 2007-06-25 액정 씰링제 및 이를 이용한 액정 표시 셀

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JP2006185558A JP5268235B2 (ja) 2006-07-05 2006-07-05 液晶シール剤およびそれを用いた液晶表示セル

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KR20160018361A (ko) 2014-08-08 2016-02-17 닛뽄 가야쿠 가부시키가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀, 그리고 액정 표시 셀의 제조 방법
KR20160070700A (ko) 2014-12-10 2016-06-20 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
KR20170012039A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
KR20170012041A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
KR20170012040A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
KR20170012038A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀

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TWI396006B (zh) 2010-04-29 2013-05-11 Au Optronics Corp 液晶顯示面板
JP5645765B2 (ja) * 2011-07-03 2014-12-24 日本化薬株式会社 液晶シール剤及びそれを用いた液晶表示セル
JP5395872B2 (ja) * 2011-10-20 2014-01-22 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
KR101283474B1 (ko) * 2011-12-23 2013-07-12 금호석유화학 주식회사 액정 표시 소자용 흑색 실란트 조성물
JP6465740B2 (ja) * 2015-05-11 2019-02-06 日本化薬株式会社 液晶シール剤及びそれを用いた液晶表示セル
JP6338745B1 (ja) 2016-12-27 2018-06-06 日本化薬株式会社 光硬化性樹脂組成物及び電子部品用封止剤
KR20200015487A (ko) 2017-06-06 2020-02-12 닛뽄 가야쿠 가부시키가이샤 광경화성 조성물 및 전자 부품용 접착제
KR20190032222A (ko) 2017-09-19 2019-03-27 닛뽄 가야쿠 가부시키가이샤 디스플레이용 접착제
JP2019108432A (ja) 2017-12-15 2019-07-04 日本化薬株式会社 ディスプレイ用封止剤
KR20200012739A (ko) 2018-07-27 2020-02-05 닛뽄 가야쿠 가부시키가이샤 전자 부품용 봉지제, 전자 부품 및 액정 표시 셀
JP7591897B2 (ja) * 2020-09-24 2024-11-29 株式会社タムラ製作所 感光性樹脂組成物及び感光性樹脂組成物の硬化膜を備えたプリント配線板

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KR20160070700A (ko) 2014-12-10 2016-06-20 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
KR20170012039A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
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KR20170012040A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀
KR20170012038A (ko) 2015-07-21 2017-02-02 니폰 가야꾸 가부시끼가이샤 액정 시일제 및 그것을 이용한 액정 표시 셀

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KR20090026771A (ko) 2009-03-13
TWI420204B (zh) 2013-12-21
JP5268235B2 (ja) 2013-08-21
JP2008015155A (ja) 2008-01-24
KR101333720B1 (ko) 2013-11-28

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