WO2013005693A1 - Agent de scellement étanche pour cristaux liquides et cellule d'affichage à cristaux liquides l'utilisant - Google Patents

Agent de scellement étanche pour cristaux liquides et cellule d'affichage à cristaux liquides l'utilisant Download PDF

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Publication number
WO2013005693A1
WO2013005693A1 PCT/JP2012/066793 JP2012066793W WO2013005693A1 WO 2013005693 A1 WO2013005693 A1 WO 2013005693A1 JP 2012066793 W JP2012066793 W JP 2012066793W WO 2013005693 A1 WO2013005693 A1 WO 2013005693A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
component
epoxy resin
sealant
dropping method
Prior art date
Application number
PCT/JP2012/066793
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English (en)
Japanese (ja)
Inventor
早紀 吉田
堅太 菅原
英之 太田
大輔 今岡
Original Assignee
日本化薬株式会社
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 日本化薬株式会社 filed Critical 日本化薬株式会社
Priority to KR1020147000426A priority Critical patent/KR20140036301A/ko
Priority to CN201280032943.1A priority patent/CN103635854B/zh
Publication of WO2013005693A1 publication Critical patent/WO2013005693A1/fr

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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
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1339—Gaskets; Spacers; Sealing of cells
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
    • C09K2200/0647—Polyepoxides

Definitions

  • the present invention relates to a liquid crystal sealant for a liquid crystal dropping method that has good curability by heat. More specifically, a liquid crystal sealant for liquid crystal dropping method having good curability by heat, excellent storage stability, and excellent moisture resistance of the cured product, and liquid crystal sealed with the cured product Regarding display cells.
  • Patent Documents 1 and 2 a so-called liquid crystal dropping method with higher mass productivity has been proposed as a liquid crystal display cell manufacturing method. Specifically, it is a method of manufacturing a liquid crystal display cell in which liquid crystal is sealed by dropping a liquid crystal inside a weir of a liquid crystal sealant formed on one substrate and then bonding the other substrate.
  • the liquid crystal sealant in an uncured state comes into contact with the liquid crystal. At that time, the components of the liquid crystal sealant are dissolved (eluting) in the liquid crystal to reduce the resistance value of the liquid crystal, There is a problem that a display defect occurs.
  • a photothermal combination type liquid crystal sealant for a liquid crystal dropping method is currently used and put into practical use (Patent Documents 3 and 4).
  • the liquid crystal dropping method using the liquid crystal sealant is characterized in that the liquid crystal sealant sandwiched between the substrates is irradiated with light to be primarily cured and then heated to be secondarily cured.
  • the uncured liquid crystal sealant can be quickly cured by light, and dissolution (elution) of the liquid crystal sealant component into the liquid crystal can be suppressed.
  • the problem of insufficient adhesive strength due to curing shrinkage or the like at the time of photocuring occurs only by photocuring, but the photothermal combination type has an advantage that such problems can be solved by secondary curing by heating.
  • Patent Documents 5 and 6 disclose a method using a thermal radical initiator.
  • Patent Documents 7 to 9 disclose methods using polyvalent carboxylic acids as curing accelerators.
  • the present invention relates to a liquid crystal sealant for a liquid crystal dropping method that is cured only by heating or by combined use of light and heat, and since the reaction by heat is fast, it is extremely low in contamination with liquid crystal throughout the process and also has good storage stability.
  • the present invention proposes a liquid crystal sealing agent for a liquid crystal dropping method which is excellent and has excellent cured properties such as moisture resistance reliability.
  • the present inventors have found that a liquid crystal sealing agent for a liquid crystal dropping method containing a specific compound having a carboxy group has excellent thermal reactivity, and as a result, it is possible to suppress liquid crystal contamination. Furthermore, the present inventors have found that the storage stability and the moisture resistance reliability are excellent, and have completed the present invention. That is, the present invention relates to the following 1) to 10).
  • curing containing 1 type (s) or 2 or more types selected from an epoxy resin, a (meth) acrylated epoxy resin, and a partial (meth) acrylated epoxy resin In order to avoid complications described as “reactive resin”, it may be described as “component (a) curable resin” or simply “component (a)”.
  • component (a) curable resin In order to avoid complications described as “reactive resin”, it may be described as “component (a) curable resin” or simply “component (a)”.
  • component (meth) acryl means one or both of “acryl” and “methacryl”.
  • (meth) acryloyl” means one or both of “acryloyl” and “methacryloyl”.
  • the liquid crystal sealant for liquid crystal dropping method of the present invention has a high reaction speed at the time of thermosetting, it has sufficient curability even under wiring where light is difficult to reach in the photothermal combined liquid crystal dropping method.
  • the degree of freedom in wiring design can be ensured, and the manufacture of a highly reliable liquid crystal display panel can be facilitated. Furthermore, it can be applied to a liquid crystal dropping method in which a liquid crystal sealant is cured only by heat. .
  • the liquid crystal sealant of the present invention contains component (c) a compound having a carboxy group in the molecule and an acid value of 50 to 250 mgKOH / g, thereby achieving both thermal reactivity and storage stability. It is possible.
  • the carboxy group of this compound functions as a thermosetting accelerator. Therefore, when the oxidation is less than 50 mg, sufficient thermal reactivity cannot be obtained. Moreover, when oxidation is larger than 250 mg, the polarity of a molecule
  • the acid value is more preferably 50 to 180 mgKOH / g, still more preferably 50 to 100 mgKOH / g, and particularly preferably 60 to 100 mgKOH / g.
  • the acid value is defined as the number of mg of potassium hydroxide required to neutralize the carboxylic acid present in 1 g of component (c).
  • the component (c) preferably has a mass average molecular weight of 3000 to 10000 g / mol. If the mass average molecular weight is too small, it itself dissolves in the liquid crystal and causes display defects. On the other hand, if the mass average molecular weight is too large, the compatibility with other components is deteriorated, and the thermal reaction promoting effect is remarkably reduced.
  • the mass average molecular weight is more preferably 4000 to 8000 g / mol.
  • the content of component (c) is preferably 0.1 to 20 parts by mass, particularly 1 to 10 parts by mass, when the total amount of component (a) curable resin is 100 parts by mass. preferable. If the content is too small, sufficient thermosetting property cannot be obtained. If the content is too large, the liquid crystal sealant has a high viscosity, which is unsuitable because it imposes restrictions on the blending of other components.
  • the component (c) include compounds obtained by reacting an acid anhydride or a polyvalent carboxylic acid (including an anhydride) with an epoxy (meth) acrylate having a hydroxyl group, and one or more types of polyvalent carboxylic acid Examples thereof include compounds obtained by reacting a terminal alcoholic hydroxyl group of a polyester resin obtained by a dehydration condensation reaction with one or more polyhydric alcohols and a polyvalent carboxylic acid (including an anhydride).
  • a compound obtained by reacting an epoxy (meth) acrylate having a hydroxyl group with an acid anhydride or a polyvalent carboxylic acid (including an anhydride) can be obtained, for example, by the method described in JP-A-5-32746. It is.
  • a compound obtained by reacting bisphenol A type epoxy (meth) acrylate with an acid anhydride is preferable.
  • the terminal alcoholic hydroxyl group of the polyester resin obtained by subjecting one or more types of polycarboxylic acid and one or more types of polyhydric alcohol to dehydration condensation reaction is allowed to react with polyvalent carboxylic acid (including anhydride).
  • the obtained compound can be easily obtained from the market under the trade names (Iupika Coat GV230 and Iupika Coat GV250), for example.
  • Iupika Coat GV230 (acid value 53 mgKOH / g, mass average molecular weight 7900 g / mol) and Iupika Coat GV250 (acid value 74 mgKOH / g, mass average molecular weight 5200 g / mol) are preferably used, and Iupika Coat GV250 is particularly preferably used.
  • thermosetting agent that is the component (b) used in the liquid crystal sealing agent of the present invention is not particularly limited, and examples thereof include polyvalent amines, polyhydric phenols, hydrazide compounds, and the like. Compounds are particularly preferably used.
  • the aromatic hydrazide terephthalic acid dihydrazide, isophthalic acid dihydrazide, 2,6-naphthoic acid dihydrazide, 2,6-pyridinedihydrazide, 1,2,4-benzenetrihydrazide, 1,4,5,8-naphthoic acid examples include tetrahydrazide and pyromellitic acid tetrahydrazide.
  • aliphatic hydrazide compound examples include form hydrazide, acetohydrazide, propionic acid hydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, pimelic acid dihydrazide, 1,4- Cyclohexane dihydrazide, tartaric acid dihydrazide, malic acid dihydrazide, iminodiacetic acid dihydrazide, N, N'-hexamethylenebissemicarbazide, citric acid trihydrazide, nitriloacetic acid trihydrazide, cyclohexanetricarboxylic acid trihydrazide, 1,3-bis (hydrazinocarbono Hydantoin skeleton such as ethyl) -5-isopropylhydantoin, preferably valine hydanto
  • Examples of the compound represented by the above (1) include tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris. (3-hydrazinocarbonylpropyl) isocyanurate, bis (2-hydrazinocarbonylethyl) isocyanurate, and the like can be mentioned, but the structure of the formula (1) is not limited thereto.
  • isophthalic acid dihydrazide isophthalic acid dihydrazide, malonic acid dihydrazide, adipic acid dihydrazide, tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate and tris (3-hydrazinocarbonylpropyl) isocyanurate, particularly preferably tris (2-hydrazinocarbonylethyl) isocyanurate.
  • the content of component (b) is preferably 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, when the total amount of component (a) curable resin is 100 parts by mass. Two or more kinds may be mixed and used.
  • the liquid crystal sealing agent of the present invention comprises a curable resin composed of one or more selected from an epoxy resin, a (meth) acrylated epoxy resin, and a partial (meth) acrylated epoxy resin. contains. Examples thereof include an epoxy resin, a mixture of an epoxy resin and a (meth) acrylated epoxy resin, a (meth) acrylated epoxy resin, and a partial (meth) acrylated epoxy resin.
  • the component (a) used in the present invention preferably has low contamination and solubility for liquid crystals.
  • suitable epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F novolak type.
  • diglycidyl etherified products of bifunctional phenols diglycidyl etherified products of bifunctional alcohols, their halides, hydrogenated products, etc.
  • the (meth) acryloylated epoxy resin and the partial (meth) acryloylated epoxy resin can be obtained by a known reaction between an epoxy resin and (meth) acrylic acid.
  • epoxy resin, (meth) acrylic acid having a predetermined equivalent ratio catalyst (for example, benzyldimethylamine, triethylamine, benzyltrimethylammonium chloride, triphenylphosphine, triphenylstibine, etc.), and a polymerization inhibitor (for example, methoquinone)
  • catalyst for example, benzyldimethylamine, triethylamine, benzyltrimethylammonium chloride, triphenylphosphine, triphenylstibine, etc.
  • a polymerization inhibitor for example, methoquinone
  • hydroquinone, methylhydroquinone, phenothiazine, dibutylhydroxytoluene, etc. and an esterification reaction is carried out at 80 to 110
  • An epoxy resin more than bifunctional is preferable, for example, a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol S type epoxy resin, a phenol novolac type epoxy resin , Cresol novolac type epoxy resin, bisphenol A novolac type epoxy resin, bisphenol F novolac type 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 resins, phenol novolac type epoxy resins having a triphenolmethane skeleton, diglycidyl ethers of difunctional phenols, difunctional alcohols Diglycidyl ether compound, and their halides, hydrogenated product and the like.
  • bisphenol type epoxy resin and novolac type epoxy resin are more preferable from the viewpoint of liquid crystal contamination.
  • the ratio of the epoxy group to the (meth) acryloyl group is not limited, and is appropriately selected from the viewpoint of process compatibility and liquid crystal contamination.
  • the content of the component (a) is appropriately determined in consideration of workability and physical properties of the obtained liquid crystal sealant, and is usually about 25 to 80% by mass, preferably 25 to 75% by mass in the liquid crystal sealant. It is.
  • a silane coupling agent can be used to improve adhesive strength and moisture resistance reliability.
  • silane coupling agents include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxy Silane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyltrimethoxysilane, 3-amino Propyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl)
  • an inorganic filler can be used to improve the adhesive strength and improve the moisture resistance reliability.
  • this (e) inorganic filler fused silica, crystalline silica, silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, barium sulfate, calcium sulfate, mica, 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, molybdenum disulfide, asbestos, etc., preferably fused silica, crystalline silica, nitriding Silicon, boron nitride, calcium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, aluminum hydroxide, calcium silicate, aluminum silicate, more preferably
  • the particle size can be measured with a laser diffraction / scattering particle size distribution analyzer (dry type) (manufactured by Seishin Enterprise Co., Ltd .; LMS-30).
  • the content of the inorganic filler (e) that can be used in the liquid crystal sealant of the present invention in the liquid crystal sealant is usually 10 to 60 parts by mass when the total amount of the liquid crystal sealant of the present invention is 100 parts by mass, The amount is preferably 20 to 50 parts by mass.
  • the amount is preferably 20 to 50 parts by mass.
  • the liquid crystal sealant of the present invention may contain a component (f) a photopolymerization initiator in order to obtain a photothermal combined curing liquid crystal sealant.
  • a photopolymerization initiator is not particularly limited as long as it is a compound that generates radicals by UV or visible light irradiation and initiates a chain polymerization reaction.
  • benzyldimethyl ketal 1-hydroxycyclohexyl phenyl ketone, diethylthioxanthone, benzophenone 2-ethylanthraquinone, 2-hydroxy-2-methylpropiophenone, 2-methyl- [4- (methylthio) phenyl] -2-morpholino-1-propane, 2,4,6-trimethylbenzoyldiphenylphosphine oxide Etc.
  • 2-methacryloyloxyethyl isocyanate and 1- [4- (2-hydroxyethoxy) -phenyl]- The reaction product with 2-hydroxy-2methyl-1-propan-1-one is preferably used.
  • This compound can be obtained by the method described in International Publication No. 2006/027982.
  • the content of the component (f) photopolymerization initiator that can be used in the liquid crystal sealant of the present invention in the liquid crystal sealant is usually 0.1 to 5 when the total amount of the liquid crystal sealant of the present invention is 100 parts by mass. Parts by mass, preferably 0.2 to 3 parts by mass.
  • a monomer or oligomer of (meth) acrylic acid ester may be used as necessary.
  • Such monomers and oligomers include, for example, a reaction product of dipentaerythritol and (meth) acrylic acid, a reaction product of dipentaerythritol / caprolactone and (meth) acrylic acid, etc., but has a contamination property to liquid crystals. If it is low, it will not be restricted in particular.
  • the liquid crystal sealant of the present invention may further contain organic fillers and additives such as pigments, leveling agents, antifoaming agents, and solvents as necessary.
  • An example of a method for obtaining the liquid crystal sealant of the present invention is the following method. First, the component (a) is dissolved in an organic solvent, and then the component (c) is added and mixed by heating to dissolve the component (c). Thereafter, the organic solvent is removed by heating or the like, and if necessary, the component (f) is dissolved and mixed under heating. (B) component is added after cooling to room temperature, (d) component, (e) component, and an organic filler, an antifoamer, a leveling agent, a solvent, etc. are added as needed, and a well-known mixing apparatus, for example, 3
  • the liquid crystal sealing agent of the present invention can be produced by mixing uniformly with a roll, sand mill, ball mill or the like and filtering with a metal mesh.
  • the liquid crystal display cell of the present invention is a cell in which a pair of substrates having predetermined electrodes formed on a substrate are arranged opposite to each other at a predetermined interval, the periphery is sealed with the liquid crystal sealant of the present invention, and the liquid crystal is sealed in the gap. is there.
  • the kind of liquid crystal to be sealed is not particularly limited.
  • the substrate is composed of a combination of substrates made of at least one of glass, quartz, plastic, silicon, etc. and having light transmission properties.
  • a spacer spacer (gap control material) such as glass fiber
  • the liquid crystal sealant is applied to one of the pair of substrates using a dispenser or a screen printing device.
  • the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 ° C. for 1 to 2 hours.
  • the liquid crystal sealant part is irradiated with ultraviolet rays by an ultraviolet irradiator and photocured.
  • UV irradiation dose is preferably 500 ⁇ 6000mJ / cm 2, more preferably 1000 ⁇ 4000mJ / cm 2.
  • the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 ° C. for 1 to 2 hours.
  • the liquid crystal display cell of the present invention thus obtained is free from display defects due to liquid crystal contamination and has excellent adhesion and moisture resistance reliability.
  • the spacer include glass fiber, silica beads, and polymer beads.
  • the diameter varies depending on the purpose, but 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 0.5 to 2 parts by weight, more preferably about 0.9 to 1.5 parts by weight with respect to 100 parts by weight of the liquid crystal sealant of the present invention. is there.
  • the liquid crystal sealant of the present invention has a very good thermosetting property and quickly cures in the heating step in the liquid crystal dropping method. Accordingly, the elution of the constituent components into the liquid crystal is extremely small, and display defects of the liquid crystal display cell can be reduced. Moreover, since it is excellent also in storage stability, it is suitable for manufacture of a liquid crystal display cell. Furthermore, since the cured product is excellent in various cured product characteristics such as adhesive strength, heat resistance, and moisture resistance, it is possible to produce a liquid crystal display cell with excellent reliability by using the liquid crystal sealant of the present invention. is there. In addition, the liquid crystal display cell prepared using the liquid crystal sealant of the present invention satisfies the characteristics required for a liquid crystal display cell having a high voltage holding ratio and a low ion density.
  • Synthesis Example 1-1 The reaction solution obtained in Synthesis Example 1 was washed with water, and toluene was distilled off to obtain 395 g of the desired bisphenol A type epoxy acrylate (KAYARAD RTM R-93100).
  • Example 3 Each resin component (component (a)) was mixed and stirred at the ratio shown in Table 1 below, and then component (c) was added and dissolved by heating at 90 ° C.
  • the radical polymerization initiator (component (f)) was heated and dissolved therein, and then cooled to room temperature.
  • a silane coupling agent (component (d)), an inorganic filler (component (e)), a thermosetting agent (component) (B)) was added and stirred, and then dispersed by a three-roll mill and filtered through a metal mesh (635 mesh) to prepare a liquid crystal sealant for liquid crystal dropping method of Example 3.
  • thermosetting test After applying the liquid crystal sealing agent for each liquid crystal dropping method between polyethylene terephthalate films, it was stretched to a thickness of 100 ⁇ m using a laminator and irradiated with 3000 mJ / cm 2 of ultraviolet rays (sample 1). The resulting film was heat cured at 120 ° C. for 1 hour (Sample 2). The enthalpies of Sample 1 and Sample 2 were measured using a differential scanning calorimeter (Seiko Instruments Inc., measurement conditions: 30 ° C. to 250 ° C., heating rate 10 ° C.), and the thermal reaction rate was calculated using the following formula. did.
  • Thermal reaction rate [1 ⁇ (enthalpy of sample 1 ⁇ enthalpy of sample 2) / enthalpy of sample 1] ⁇ 100 The result was determined as follows. ⁇ : Thermal reaction rate of 90% or more ⁇ : Thermal reaction rate of less than 90% The thermal reaction rate of Example 1 was 92%, the thermal reaction rate of Example 2 was 91%, and the thermal reaction rate of Example 3 was 94%. It was.
  • a PCT test (conditions: temperature 120 ° C., humidity 100%, atmospheric pressure 2 atm, test time 12 hours) was performed using the glass substrate after curing, and the shear adhesive strength of the subsequent glass pieces was measured. Then, the adhesion retention before and after the PCT test was calculated and determined as follows. ⁇ : Adhesion retention 50% or more ⁇ : Adhesion retention 25% or more and less than 50% ⁇ : Adhesion retention 25% or less Example 1 has an adhesion retention of 69%, and Example 2 has an adhesion retention of 65%. The adhesion retention of Example 3 was 55%.
  • Comparative Example 3 containing no curing accelerator component is inferior in curability, and as a result, orientation failure occurs in the panel display characteristics.
  • the thing using the thermal radical initiator and CIC acid as a hardening accelerator has improved sclerosis
  • Examples 1 to 3 it is confirmed that other characteristics are at a usable level while improving the curability.
  • Examples 1 and 2 show very excellent results in all characteristics. From these results, it can be said that the liquid crystal sealant of the present invention is excellent in workability because of its excellent storage stability and curability, and also excellent in liquid crystal contamination, moisture-resistant adhesion, and panel display characteristics. It can be said that high reliability can be realized.
  • the liquid crystal sealant of the present invention is excellent in workability, it enables stable production of liquid crystal display cells and contributes to ensuring long-term reliability of the liquid crystal display cells.

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

Abstract

L'invention a pour but de procurer un agent de scellement étanche pour cristaux liquides pour le procédé de dépôt en gouttes de cristaux liquides, qui répond rapidement à la chaleur, provoque peu de contamination des cristaux liquides durant toutes les étapes, présente une excellente durée de conservation et confère d'excellentes propriétés de produit durci telles que la fiabilité de la résistance à l'humidité. L'agent de scellement étanche pour cristaux liquides pour le procédé de dépôt en gouttes de cristaux liquides de l'invention est caractérisé en ce qu'il comprend (a) une résine durcissable contenant un, deux ou plus choisis dans le groupe consistant en une résine époxy, une résine époxy (méth)acrylée et une résine époxy partiellement (méth)acrylée, (b) un agent de thermodurcissement et (c) un composé ayant des groupes carboxy intramoléculaires et un indice d'acide entre 50 et 250 mgKOH/g.
PCT/JP2012/066793 2011-07-03 2012-06-29 Agent de scellement étanche pour cristaux liquides et cellule d'affichage à cristaux liquides l'utilisant WO2013005693A1 (fr)

Priority Applications (2)

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KR1020147000426A KR20140036301A (ko) 2011-07-03 2012-06-29 액정 시일제 및 그것을 사용한 액정 표시 셀
CN201280032943.1A CN103635854B (zh) 2011-07-03 2012-06-29 液晶密封剂及使用其的液晶显示单元

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JP2011-147814 2011-07-03
JP2011147814A JP5645765B2 (ja) 2011-07-03 2011-07-03 液晶シール剤及びそれを用いた液晶表示セル

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KR (1) KR20140036301A (fr)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018201428A1 (fr) * 2017-05-05 2018-11-08 Henkel Ag & Co. Kgaa Composition de matériau d'étanchéité thermodurcissable et utilisation associée
FR3121790A1 (fr) 2021-04-09 2022-10-14 Valeo Systemes Thermiques Compartiment pour un équipement susceptible de dégager de la chaleur

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6535002B2 (ja) * 2014-07-17 2019-06-26 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
JP6497809B2 (ja) * 2015-07-21 2019-04-10 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
CN110136581B (zh) * 2019-04-01 2022-01-04 陈波 热塑性光学胶的贴合方法和应用及一种显示器

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