WO2011118191A1 - Agent d'étanchéité pour cristaux liquides, procédé de fabrication de panneau d'affichage à cristaux liquides mettant en œuvre cet agent d'étanchéité, et panneau d'affichage à cristaux liquides - Google Patents

Agent d'étanchéité pour cristaux liquides, procédé de fabrication de panneau d'affichage à cristaux liquides mettant en œuvre cet agent d'étanchéité, et panneau d'affichage à cristaux liquides Download PDF

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Publication number
WO2011118191A1
WO2011118191A1 PCT/JP2011/001645 JP2011001645W WO2011118191A1 WO 2011118191 A1 WO2011118191 A1 WO 2011118191A1 JP 2011001645 W JP2011001645 W JP 2011001645W WO 2011118191 A1 WO2011118191 A1 WO 2011118191A1
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WIPO (PCT)
Prior art keywords
liquid crystal
epoxy resin
meth
substrate
modified
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PCT/JP2011/001645
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English (en)
Japanese (ja)
Inventor
溝部祐司
水田康司
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三井化学株式会社
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Priority to KR1020127025037A priority Critical patent/KR20120125552A/ko
Priority to JP2012506821A priority patent/JPWO2011118191A1/ja
Priority to CN2011800157534A priority patent/CN102812396A/zh
Publication of WO2011118191A1 publication Critical patent/WO2011118191A1/fr

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Classifications

    • 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
    • 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
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
    • C08G59/1461—Unsaturated monoacids
    • C08G59/1466—Acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/10—Epoxy resins modified by unsaturated 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

Definitions

  • the present invention relates to a liquid crystal sealant, a method for producing a liquid crystal display panel using the same, and a liquid crystal display panel.
  • liquid crystal display panels have been widely used as image display panels for various electronic devices such as mobile phones and personal computers.
  • the liquid crystal display panel has a structure in which a liquid crystal material (hereinafter simply referred to as “liquid crystal”) is sandwiched between two transparent substrates having electrodes provided on the surface, and the periphery thereof is sealed with a liquid crystal sealant. It is.
  • liquid crystal sealant has a small influence on the reliability of the liquid crystal display panel because it is in direct contact with the liquid crystal although the amount used is small. Therefore, in order to achieve high image quality of the liquid crystal display panel, liquid crystal sealants are currently required to have advanced and diverse characteristics.
  • liquid crystal display panels are mainly manufactured by a liquid crystal injection method.
  • the liquid crystal injection method is (1) after applying a liquid crystal sealant on one transparent substrate to form a frame, and (2) drying the liquid crystal sealant by precuring the substrate. And (3) forming a frame (cell) of liquid crystal sealant between the substrates by bonding the two substrates together by heating and pressing, and (4) emptying the substrates.
  • This is a method of manufacturing a liquid crystal display panel by injecting an appropriate amount of liquid crystal into a cell and then sealing the liquid crystal injection port.
  • liquid crystal dropping method has been studied as a method for manufacturing a liquid crystal display panel, which is expected to improve productivity.
  • a liquid crystal sealant is applied on a transparent substrate to form a frame for filling the liquid crystal
  • a minute liquid crystal is dropped into the frame
  • liquid crystal In this method, two substrates are stacked under high vacuum while the sealant is in an uncured state, and then (4) the liquid crystal sealant is cured to produce a panel.
  • a light and thermosetting liquid crystal sealant is used, and in the step (3), after the liquid crystal sealant is pre-cured by irradiating light such as ultraviolet rays, it is post-cured by heating. Has been done.
  • liquid crystal sealing agent for the liquid crystal dropping method
  • a liquid epoxy resin Patent Document 1
  • this epoxy resin is soluble in liquid crystals even at room temperature, and becomes a factor that degrades the display characteristics of the liquid crystal display panel.
  • a liquid crystal sealant using a crystalline epoxy resin such as an ether type epoxy resin as a resin that is difficult to dissolve in a liquid crystal for example, Patent Document 2
  • a liquid crystal containing an acrylic acid-modified phenol novolac epoxy resin and a urethane-modified partial acrylic modified product Sealing agents for example, Patent Document 3
  • Patent Documents 2 and 3 have low solubility in liquid crystals at room temperature to some extent. However, since the resin easily dissolves in the liquid crystal under high temperature and high humidity conditions, the display characteristics of the liquid crystal display panel may be deteriorated. In particular, in the liquid crystal dropping method, since the uncured liquid crystal sealant comes into contact with the liquid crystal, the components of the liquid crystal sealant are easily dissolved in the liquid crystal, which is likely to deteriorate the display characteristics of the liquid crystal display panel.
  • the present invention has been made in view of the above circumstances, and an object thereof is to provide a liquid crystal sealant having excellent display reliability without changing display characteristics even under high temperature and high humidity conditions.
  • the present inventors react a part of the epoxy group of the epoxy resin with (meth) acrylic acid to introduce a hydroxyl group (which has low compatibility with the liquid crystal) into the resin. Attention was focused on a method for suppressing the dissolution in the water. And it has been found that the solubility of the resin in the liquid crystal is greatly influenced not only by the absolute number of hydroxyl groups contained in the resin but also by the ratio (balance) of the number of hydroxyl groups to the number of unreacted epoxy groups. It was.
  • the ratio of the number of hydroxyl groups to the number of unreacted epoxy groups is increased; specifically, the range of hydrogen-bonding functional groups is set to a certain range, and the equivalent of (meth) acrylic groups / epoxy groups It was found that dissolution in liquid crystal can be suppressed by setting the equivalent weight to a certain value or more.
  • the present invention has been made based on such findings.
  • the first of the present invention relates to a liquid crystal sealant.
  • a (meth) acryl-modified epoxy resin obtained by reacting an epoxy resin containing two or more epoxy groups in the molecule with (meth) acrylic acid; a thermosetting agent; and a photopolymerization initiator.
  • the (meth) acryl-modified epoxy resin has a hydrogen-bonding functional group containing a hydroxyl group generated by a reaction between the epoxy resin containing two or more epoxy groups in the molecule and the (meth) acrylic acid,
  • the (meth) acryl-modified epoxy resin has an (meth) acryl group equivalent / epoxy group equivalent of more than 9, and the hydrogen bondable functional group value is 3 ⁇ 10 ⁇ 3 to 5 ⁇ 10 ⁇ 3 mol / Liquid crystal sealing agent which is g.
  • the epoxy resin containing two or more epoxy groups in the molecule is a bifunctional epoxy resin selected from the group consisting of a biphenyl type epoxy resin, a naphthalene type epoxy resin, and a bisphenol type epoxy resin.
  • Liquid crystal sealing agent as described in 2.
  • the liquid crystal sealant according to [2], wherein the bifunctional epoxy resin is a bisphenol A type epoxy resin or a bisphenol F type epoxy resin.
  • the bifunctional epoxy resin is a bisphenol A type epoxy resin or a bisphenol F type epoxy resin.
  • Liquid crystal sealing agent of description [5]
  • the photopolymerization initiator is at least one compound selected from the group consisting of alkylphenone compounds, acylphosphine oxide compounds, titanocene compounds, and oxime ester compounds.
  • the liquid crystal sealing agent in any one of.
  • the liquid crystal sealant according to any one of [1] to [7] which is used for manufacturing a liquid crystal display panel by a liquid crystal dropping method.
  • the second aspect of the present invention relates to a method for manufacturing a liquid crystal display panel using a liquid crystal sealant.
  • a step of forming a seal pattern on one substrate using the liquid crystal sealant according to any one of [1] to [8], and a seal pattern region of the one substrate when the seal pattern is uncured A step of dropping a liquid crystal on the other substrate which is paired with the one substrate, a step of superimposing the one substrate on the other substrate, and photocuring the seal pattern, followed by thermosetting
  • thermosetting A method of manufacturing a liquid crystal display panel.
  • liquid crystal sealant excellent in display reliability can be provided.
  • liquid crystal sealant of the present invention comprises (A-1) a (meth) acryl-modified epoxy resin, (B) a thermosetting agent, and (C) a photopolymerization initiator. ) Solid epoxy resin, (D) acrylic resin, and (E) filler may be further included.
  • Epoxy resin (A-1) (Meth) acryl-modified epoxy resin
  • the (meth) acryl-modified epoxy resin in the present invention is preferably an epoxy resin and (meth) acrylic acid, for example, in the presence of a basic catalyst. It is a (meth) acryl-modified epoxy resin obtained by reacting.
  • the raw material epoxy resin may be a bifunctional or higher functional epoxy resin having two or more epoxy groups in the molecule, such as bisphenol A type, bisphenol F type, 2,2′-diallyl bisphenol A type, bisphenol AD type, And bisphenol type epoxy resins such as hydrogenated bisphenol type; novolak type epoxy resins such as phenol novolak type, cresol novolak type, biphenyl novolak type, and trisphenol novolak type; biphenyl type epoxy resin; naphthalene type epoxy resin and the like.
  • bisphenol A type bisphenol F type
  • 2,2′-diallyl bisphenol A type bisphenol AD type
  • bisphenol type epoxy resins such as hydrogenated bisphenol type
  • novolak type epoxy resins such as phenol novolak type, cresol novolak type, biphenyl novolak type, and trisphenol novolak type
  • biphenyl type epoxy resin naphthalene type epoxy resin and the like.
  • a (meth) acryl-modified epoxy resin obtained by (meth) acryl modification of a trifunctional or tetrafunctional polyfunctional epoxy resin is preferably a bifunctional epoxy resin because it has a high crosslinking density and is likely to have a low adhesive strength. .
  • the bifunctional epoxy resin is preferably a biphenyl type epoxy resin, a naphthalene type epoxy resin, or a bisphenol type epoxy resin, and bisphenol type epoxy resins such as bisphenol A type and bisphenol F type are particularly preferable from the viewpoint of production efficiency. This is because the bisphenol type epoxy resin has advantages such as excellent applicability as compared with the biphenyl ether type epoxy resin.
  • the raw material epoxy resin may be one kind or a combination of two or more kinds. Moreover, it is preferable that the epoxy resin used as a raw material is highly purified by a molecular distillation method, a washing method, or the like.
  • the reaction between the raw epoxy resin and (meth) acrylic acid is carried out so that the (meth) acryl-modified epoxy resin to be obtained has a (meth) acrylic group equivalent / epoxy group equivalent within a predetermined range. Is preferred.
  • the reaction between the raw epoxy resin and (meth) acrylic acid is carried out so that the (meth) acryl-modified epoxy resin to be obtained has a (meth) acrylic group equivalent / epoxy group equivalent of more than 9. It is preferable to carry out so that it may become 9.5 or more.
  • the equivalent of (meth) acryl groups in the (meth) acryl-modified epoxy resin is “average number of (meth) acryl groups contained in one molecule of (meth) acryl-modified epoxy resin / (meth) acryl-modified epoxy”. It is expressed as “weight average molecular weight (Mw) of resin”.
  • the equivalent of the epoxy group in the (meth) acryl-modified epoxy resin is “average number of epoxy groups contained in one molecule of (meth) acryl-modified epoxy resin / weight average molecular weight of (meth) acryl-modified epoxy resin (Mw ) ". That is, the equivalent of (meth) acrylic group / equivalent of epoxy group is the same as the average number of (meth) acrylic groups / average number of epoxy groups.
  • (Meth) acrylic group equivalent / epoxy group equivalent is less than 9 (meth) acryl-modified epoxy resin has a small number of hydroxyl groups (generated by reaction) with respect to the number of unreacted epoxy groups; Alternatively, since the ratio of the reaction product (epoxy resin containing a hydroxyl group) to the unreacted product (epoxy resin containing no hydroxyl group) is small, it is difficult to obtain an effect of suppressing dissolution in the liquid crystal material.
  • the raw epoxy resin is a bifunctional epoxy resin.
  • the bifunctional epoxy resin and (meth) acrylic acid are reacted, 1) both of the two epoxy groups are not yet present. Unreacted material remaining in the reaction, 2) partial (meth) acrylate obtained by modifying one epoxy group with (meth) acrylic acid, and 3) both of the two epoxy groups modified with (meth) acrylic acid Three types of all (meth) acrylates are produced.
  • bifunctional epoxy resin and (meth) acrylic acid are reacted so that the number of (meth) acryl groups / the number of epoxy groups is 1, dissolution in liquid crystal is remarkable. 1) Unreacted product It has been confirmed that about 25 mol% remains.
  • the (meth) acryl-modified epoxy resin used in the present invention preferably has a relatively flexible skeleton and may have low crystallinity.
  • a sealing agent containing a (meth) acryl-modified epoxy resin tends to have a relatively low viscosity and is easily dissolved in a liquid crystal.
  • Such a (meth) acryl-modified epoxy resin may have a weight average molecular weight of, for example, about 310 to 500.
  • the weight average molecular weight Mw of the (meth) acryl-modified epoxy resin can be measured, for example, by gel permeation chromatography (GPC).
  • (meth) acryl-modified epoxy resins having a ratio of (meth) acrylic group equivalent / epoxy group equivalent of less than 9 have a low content of (meth) acrylic groups, and thus have low photocurability. Therefore, the temporary curing of the liquid crystal sealant with light tends to be insufficient, and it may be difficult to suppress elution into the liquid crystal.
  • (Meth) acrylic-modified epoxy resin has hydrogen bondable functional groups such as hydroxyl group, urethane bond, amide group, carboxyl group.
  • hydrogen-bonding functional groups include at least a hydroxyl group produced by the reaction of the epoxy group of the epoxy resin with (meth) acrylic acid, which is a raw material for the (meth) acryl-modified epoxy resin ( A hydroxyl group, a urethane bond, a carboxyl group, an amide group and the like contained in (meth) acrylic acid and epoxy resin are also included. Since a resin having a hydrogen bonding functional group has low compatibility with a liquid crystal material that is hydrophobic, dissolution in the liquid crystal material is suppressed.
  • the hydrogen bondable functional group value of the (meth) acryl-modified epoxy resin is preferably 3 ⁇ 10 ⁇ 3 to 5 ⁇ 10 ⁇ 3 mol / g, and 3.5 ⁇ 10 ⁇ 3 to 4.5 ⁇ 10 ⁇ . More preferably, it is 3 mol / g.
  • the hydrogen bondable functional group value is less than 3 ⁇ 10 ⁇ 3 mol / g, the number of hydrogen bondable functional groups contained in one molecule of (meth) acryl-modified epoxy resin is small, so that the dissolution in the liquid crystal is suppressed. This is because it is difficult to obtain the effect, and if it exceeds 5 ⁇ 10 ⁇ 3 mol / g, the moisture resistance of the cured product of the (meth) acryl-modified epoxy resin tends to be lowered.
  • the hydrogen bonding functional group value (mol / g) of the (meth) acryl-modified epoxy resin is “the number of hydrogen bonding functional groups contained in one molecule of the (meth) acryl-modified epoxy resin” / “(meth) acryl modification”. It is expressed as “weight average molecular weight (Mw) of epoxy resin”.
  • Mw weight average molecular weight of epoxy resin.
  • the hydrogen bonding functional group value of a (meth) acryl-modified epoxy resin having only a hydroxyl group obtained by reacting (meth) acrylic acid with an epoxy resin is reacted (meth). It can be determined by dividing the number of moles of acrylic acid by the weight average molecular weight (Mw) of the (meth) acryl-modified epoxy resin.
  • the hydrogen bonding functional group value of the (meth) acryl-modified epoxy resin can be adjusted, for example, by adjusting the number of moles of (meth) acrylic acid to be reacted with the raw material epoxy resin; the raw material (meth) acrylic acid or epoxy resin It can be controlled by adjusting the amount of the hydrogen-bonding functional group possessed by.
  • the hydroxyl value of the (meth) acryl-modified epoxy resin obtained by reacting an epoxy resin as a raw material with (meth) acrylic acid is preferably 3 ⁇ 10 ⁇ 3 to 5 ⁇ 10 ⁇ 3 mol / g. .
  • the content of the (meth) acryl-modified epoxy resin is preferably 10 to 70 parts by mass and more preferably 20 to 50 parts by mass with respect to 100 parts by mass of the liquid crystal sealant.
  • the (meth) acryl-modified epoxy resin since the (meth) acryl-modified epoxy resin has an epoxy group and a (meth) acryl group in the molecule, it can have both photocuring properties and thermosetting properties. Furthermore, even if the (meth) acryl-modified epoxy resin is an amorphous epoxy resin, since the ratio of the number of hydroxyl groups to the number of epoxy groups is large, dissolution in liquid crystals can be highly suppressed.
  • the liquid crystal sealing agent of the present invention may contain a solid epoxy resin having a softening point of 40 ° C or higher and 150 ° C or lower as necessary. Such a solid epoxy resin has low solubility and diffusibility in liquid crystal, and not only good display characteristics of the resulting liquid crystal panel, but also can improve the moisture resistance of the cured product.
  • Such a solid epoxy resin can be an aromatic epoxy resin having a weight average molecular weight of 500 to 10,000, preferably 1000 to 5,000.
  • the weight average molecular weight of the solid epoxy resin can be measured in the same manner as described above.
  • aromatic epoxy resins examples include aromatic diols represented by bisphenol A, bisphenol S, bisphenol F, bisphenol AD, and the like, and diols obtained by modifying them with ethylene glycol, propylene glycol, alkylene glycol, and epichlorohydrin.
  • Aromatic polyvalent glycidyl ether compounds obtained by the reaction with phenol; novolak resins derived from phenol or cresol and formaldehyde, polyphenols typified by polyalkenylphenol and copolymers thereof, and obtained by the reaction of epichlorohydrin
  • novolak-type polyvalent glycidyl ether compounds; glycidyl ether compounds of xylylene phenol resin, and the like are included.
  • the above aromatic epoxy resins include, among others, cresol novolac type epoxy resins, phenol novolac type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, triphenolmethane type epoxy resins, triphenolethane type epoxy resins, trisphenol type epoxy resins.
  • Resin, dicyclopentadiene type epoxy resin, diphenyl ether type epoxy resin, and biphenyl type epoxy resin are preferable. Furthermore, you may mix and use these.
  • the content of the solid epoxy resin is preferably 1 to 20 parts by mass and more preferably 3 to 10 parts by mass with respect to 100 parts by mass of the liquid crystal sealant. If the content of the solid epoxy resin is too large, the viscosity of the liquid crystal sealing agent may increase and the coating property may decrease. If the content of the solid epoxy resin is too small, the moisture resistance of the cured product of the liquid crystal sealing agent may decrease. It may be insufficient.
  • thermosetting agent Even if it is mixed with an epoxy resin, the thermosetting agent does not cure the epoxy resin under normal storage conditions (room temperature, under visible light, etc.). A curing agent to be cured.
  • the liquid crystal sealing agent containing a thermosetting agent is excellent in storage stability and thermosetting.
  • the thermosetting agent used in the present invention may be a known one, but from the viewpoint of enhancing the viscosity stability of the liquid crystal sealant and maintaining moisture resistance, the melting point is 50 ° C., although depending on the thermosetting temperature.
  • a thermosetting agent having a melting point of 250 ° C. or lower is preferable, a thermosetting agent having a melting point of 100 ° C. or higher and 200 ° C. or lower is more preferable, and a thermosetting agent having a melting point of 150 ° C. or higher and 200 ° C. or lower is further preferable.
  • thermosetting agents include organic acid dihydrazide compounds, imidazole compounds, dicyandiamide compounds, and polyamine compounds.
  • organic acid dihydrazide compounds include adipic acid dihydrazide (melting point 181 ° C.), 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin (melting point 120 ° C.), 7,11-octadecadien-1 , 18-dicarbohydrazide (melting point 160 ° C.), dodecanedioic acid dihydrazide (melting point 190 ° C.), sebacic acid dihydrazide (melting point 189 ° C.), and the like.
  • imidazole compounds include 2,4-diamino-6- [2′-ethylimidazolyl- (1 ′)]-ethyltriazine (melting point 215-225 ° C.) and 2-phenylimidazole (melting point 137-147 ° C. ) Etc. are included.
  • Examples of the dicyandiamide compound include dicyandiamide (melting point: 209 ° C.).
  • the polyamine-based compound is a thermal latent curing agent having a polymer structure obtained by reacting an amine and an epoxy.
  • ADEKA Hardener EH4339S softening point 120 to 130 ° C.
  • Adeka Hardener EH4357S softening point 73 to 83 ° C. manufactured by ADEKA Corporation is included. These may be used alone or in combination.
  • thermosetting agent is preferably adjusted so that the active hydrogen equivalent is 0.8 to 1.2 equivalents relative to the epoxy equivalent.
  • a liquid crystal sealant containing a thermosetting agent can be a so-called one-part curable resin composition.
  • the one-component curable resin composition is excellent in workability because it is not necessary to mix the main agent and the curing agent when used.
  • the photopolymerization initiator is an initiator for photocuring reaction of (A-1) (meth) acryl-modified epoxy resin or (D) acrylic resin described later.
  • A-1 (meth) acryl-modified epoxy resin or (D) acrylic resin described later.
  • the sealant can be temporarily cured by photocuring when manufacturing a liquid crystal panel, and the work process becomes easy.
  • photopolymerization initiators can be used. Examples include alkylphenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin compounds, acetophenone compounds, benzophenone compounds, thioxanthone compounds, ⁇ -acyloxime ester compounds, Examples include phenyl glyoxylate compounds, benzyl compounds, azo compounds, diphenyl sulfide compounds, organic dye compounds, iron-phthalocyanine compounds, benzoin ether compounds, anthraquinone compounds, and the like.
  • alkylphenone compounds include benzyl dimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one (IRGACURE 651); 2-methyl-2-morpholino (4-thiomethylphenyl) propane ⁇ -aminoalkylphenones such as 1-one (IIRGACURE 907); ⁇ -hydroxyalkylphenones such as 1-hydroxy-cyclohexyl-phenyl-ketone (IRGACURE 184) and the like.
  • acylphosphine oxide compound include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide.
  • the titanocene-based compound includes bis ( ⁇ 5-2,4-cyclopentadien-1-yl) -bis (2,6-difluoro-3- (1H-pyrrol-1-yl) -phenyl) titanium and the like.
  • oxime ester compounds include 1.2-octanedione-1- [4- (phenylthio) -2- (0-benzoyloxime)] (IRGACURE OXE 01).
  • the content of the photopolymerization initiator is the sum of (A-1) (meth) acrylic-modified epoxy resin, (A-2) solid epoxy resin, (B) thermosetting agent, and (D) acrylic resin described below (below) 0.3 to 5.0 parts by mass with respect to 100 parts by mass) (also referred to as “resin unit”).
  • A-1 (meth) acrylic-modified epoxy resin
  • A-2) solid epoxy resin solid epoxy resin
  • thermosetting agent thermosetting agent
  • the liquid-crystal sealing compound of this invention may contain the acrylic resin as needed.
  • acrylic resins include diacrylates and / or dimethacrylates such as polyethylene glycol, propylene glycol, polypropylene glycol; diacrylates and / or dimethacrylates of tris (2-hydroxyethyl) isocyanurate; 4 per mole of neopentyl glycol.
  • Diacrylate and / or dimethacrylate of diol obtained by adding at least 1 mole of ethylene oxide or propylene oxide; Diacrylate and / or diacrylate of diol obtained by adding 2 mole of ethylene oxide or propylene oxide to 1 mole of bisphenol A Methacrylate: Diol or triol obtained by adding 3 mol or more of ethylene oxide or propylene oxide to 1 mol of trimethylolpropane.
  • the content of the acrylic resin is preferably 5 to 40 parts by mass, more preferably 10 to 30 parts by mass with respect to 100 parts by mass of the liquid crystal sealant, although it depends on the required photocuring degree. preferable.
  • the liquid crystal sealing agent of the present invention may further contain a filler. By adding the filler, it is possible to control the viscosity of the liquid crystal sealant, the strength of the cured product, the linear expansion, and the like.
  • the filler is not particularly limited, but examples include calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, zirconium silicate, iron oxide, titanium oxide, aluminum oxide (alumina), zinc oxide, silicon dioxide, titanium.
  • Inorganic fillers such as potassium acid, kaolin, talc, glass beads, sericite activated clay, bentonite, aluminum nitride and silicon nitride are included, preferably silicon dioxide and talc.
  • the shape of the filler is not particularly limited, and may be a regular shape such as a spherical shape, a plate shape, or a needle shape, or an irregular shape.
  • the filler preferably has an average primary particle size of 1.5 ⁇ m or less and a specific surface area of 0.5 m 2 / g to 20 m 2 / g.
  • the average primary particle diameter of the filler can be measured by a laser diffraction method described in JIS Z8825-1.
  • the specific surface area can be measured by the BET method described in JIS Z8830.
  • the filler filling amount is the sum of (A-1) (meth) acrylic-modified epoxy resin, (A-2) solid epoxy resin, (B) thermosetting agent, and (D) acrylic resin (hereinafter referred to as “resin unit”). It is preferably 1 to 50 parts by mass, more preferably 10 to 30 parts by mass with respect to 100 parts by mass.
  • the liquid crystal sealant of the present invention may contain thermoplastic resin particles (also referred to as “epoxy-modified particles”) modified with an epoxy resin as necessary.
  • the thermoplastic resin particles are obtained by suspension polymerization of a resin containing an epoxy group and a double bond group with a monomer capable of radical polymerization.
  • the thermoplastic resin particles are preferably added when making a liquid crystal sealing agent for a liquid crystal injection method. This is because the shrinkage stress generated in the cured product by heating can be relaxed.
  • the resin containing an epoxy group and a double bond group examples include a resin obtained by reacting a bisphenol F type epoxy resin and methacrylic acid in the presence of a tertiary amine.
  • examples of radically polymerizable monomers include butyl acrylate, glycidyl methacrylate, and divinylbenzene.
  • the average particle diameter of the thermoplastic resin particles is usually in the range of 0.05 to 5 ⁇ m, more preferably 0.07 to 3 ⁇ m, since the gap of the liquid crystal cell is mainly 5 ⁇ m or less.
  • thermoplastic resin particles are preferably 1 to 30 parts by mass with respect to 100 parts by mass of the resin unit.
  • the liquid crystal sealing agent of the present invention includes a thermal radical polymerization initiator, a coupling agent such as a silane coupling agent, an ion trapping agent, an ion exchange agent, a leveling agent, a pigment, a dye, if necessary.
  • a coupling agent such as a silane coupling agent, an ion trapping agent, an ion exchange agent, a leveling agent, a pigment, a dye, if necessary.
  • An additive such as a plasticizer and an antifoaming agent may be further included.
  • a spacer or the like may be blended in order to adjust the gap of the liquid crystal panel.
  • the liquid crystal sealant of the present invention contains (A-1) (meth) acryl-modified epoxy resin, (B) thermosetting agent, and (C) photopolymerization initiator, photocuring and thermosetting are used in combination. It is preferably used for a liquid crystal sealant for a liquid crystal dropping method.
  • the liquid crystal sealing agent for the liquid crystal dropping method preferably further contains (A-2) a solid epoxy resin and (D) an acrylic resin, and more preferably (E) a filler.
  • the viscosity of the liquid crystal sealant of the present invention at 25 ° C. and 2.5 rpm using an E-type viscometer is preferably 30 to 350 Pa ⁇ s. This is because the liquid crystal sealant having a viscosity in the above range is excellent in coating properties.
  • the liquid crystal display panel of the present invention is a display substrate, a counter substrate that is paired with the display substrate, a frame-shaped sealing member interposed between the display substrate and the counter substrate, and a display substrate. And a liquid crystal layer filled in a space surrounded by a sealing member between the substrate and the substrate.
  • the cured product of the liquid crystal sealant of the present invention can be used as a seal member.
  • the display substrate and the counter substrate are both transparent substrates.
  • the material of the transparent substrate can be glass or plastic such as polycarbonate, polyethylene terephthalate, polyethersulfone and PMMA.
  • a matrix-like TFT, a color filter, a black matrix, or the like can be disposed on the surface of the display substrate or the counter substrate.
  • An alignment film is further formed on the surface of the display substrate or the counter substrate.
  • the alignment film includes a known organic alignment agent or inorganic alignment agent.
  • Such a liquid crystal display panel can be manufactured using the liquid crystal sealant of the present invention.
  • the liquid crystal display panel manufacturing method includes a liquid crystal dropping method and a liquid crystal injection method.
  • the manufacturing method of the liquid crystal display panel by the liquid crystal dropping method is a1) a first step of forming a seal pattern of the liquid crystal sealant of the present invention on one substrate; a2) a second step of dropping liquid crystal in a region surrounded by the seal pattern of the substrate or a region of the other substrate facing the region surrounded by the seal pattern in an uncured state of the seal pattern; a3) a third step of superimposing one substrate and the other substrate via a seal pattern; a4) a fourth step of curing the seal pattern.
  • the state in which the seal pattern is uncured means a state in which the curing reaction of the liquid crystal sealant has not progressed to the gel point. Therefore, in the step a2), the seal pattern may be semi-cured by light irradiation or heating in order to suppress dissolution of the liquid crystal sealant in the liquid crystal.
  • One substrate and the other substrate are a display substrate or a counter substrate, respectively.
  • step a4) only curing by heating may be performed, but it is preferable to perform curing (main curing) by heating after curing by light irradiation (temporary curing). This is because the liquid crystal sealant can be cured instantaneously by light curing to suppress dissolution in the liquid crystal.
  • the photocuring time is, for example, about 10 minutes although it depends on the composition of the liquid crystal sealant.
  • the light irradiation energy may be energy that can cure (A-1) (meth) acryl-modified epoxy resin, (D) acrylic resin, or the like.
  • the light is preferably ultraviolet light.
  • the thermosetting temperature is 120 ° C., for example, although it depends on the composition of the liquid crystal sealant, and the thermosetting time is about 2 hours.
  • liquid crystal dropping method since the contact time between the uncured liquid crystal sealing agent and the liquid crystal is relatively long, liquid crystal contamination is likely to occur.
  • the liquid crystal sealant of the present invention since the liquid crystal sealant of the present invention has low solubility in liquid crystals, the liquid crystal display panel obtained by the liquid crystal dropping method using the liquid crystal sealant of the present invention is excellent in display reliability.
  • the manufacturing method of the liquid crystal display panel by the liquid crystal injection method is b1) a first step of forming a seal pattern of the liquid crystal sealant of the present invention on one substrate; b2) a second step of superimposing one substrate and the other substrate via a seal pattern; b3) a third step of thermosetting the seal pattern to obtain a liquid crystal injection cell having an injection port for injecting liquid crystal; b4) a fourth step of injecting the liquid crystal into the liquid crystal injection cell through the injection port; b5) a fifth step of sealing the inlet.
  • a liquid crystal injection cell is prepared. First, two transparent substrates (for example, glass plates) are prepared. Then, a seal pattern is formed on one substrate with a liquid crystal sealant. After the other substrate is superimposed on the surface of the substrate where the seal pattern is formed, the seal pattern may be cured. At this time, it is necessary to provide an injection port for injecting liquid crystal in a part of the liquid crystal injection cell, but the injection port may be provided with a part of the opening when drawing the seal pattern. Moreover, after forming the seal pattern, the seal pattern at a desired location may be removed to provide an injection port.
  • thermosetting conditions in step b3) are, for example, about 2 to 5 hours at 150 ° C., depending on the composition of the liquid crystal sealant.
  • the step b4) can be performed according to a known method in which the inside of the liquid crystal injection cell obtained in the steps b1) to b3) is evacuated and the liquid crystal is sucked from the injection port of the liquid crystal injection cell. Good.
  • the liquid crystal sealant may be cured after being sealed in the injection port of the liquid crystal injection cell.
  • the time for which the uncured liquid crystal sealant and the liquid crystal contact is relatively short.
  • the liquid crystal may be injected even if the liquid crystal sealing agent of the liquid crystal injection cell is not sufficiently cured. Since the liquid crystal sealant of the present invention has low solubility in liquid crystal, it is difficult to contaminate the liquid crystal even in such a case. Therefore, a liquid crystal display panel excellent in display reliability can be obtained also by a liquid crystal injection method using the liquid crystal sealant of the present invention.
  • the number of epoxy groups contained in the raw material bisphenol F type epoxy resin is 1 mol.
  • the molecular weight of bisphenol F type epoxy is 320, and the molecular weight of methacrylic acid-modified bisphenol F type epoxy resin at both ends is 492.
  • the number of epoxy groups contained in the raw material bisphenol F-type epoxy resin is 1 mol as described above.
  • the number of epoxy groups contained in the novolac type epoxy resin as a raw material is 1.0 mol.
  • the number of epoxy groups contained in the starting glycidol is 0.15 mol.
  • the hydrogen bondable functional group value of the urethane-modified partially acrylated product is divided by the average molecular weight of the urethane-modified partially acrylated product by the number of urethane bonds (hydrogen bondable functional groups) contained in one molecule of the urethane-modified partially acrylated product. As a result, it was 3.0 ⁇ 10 ⁇ 3 (mol / g).
  • the number of epoxy groups contained in the raw material bisphenol A type epoxy resin is 1 mol.
  • the number of epoxy groups contained in the raw material bisphenol A type epoxy resin is 1 mol.
  • Table 1 shows the physical properties of the (meth) acryl-modified epoxy resins obtained in Synthesis Examples 1 to 6.
  • Example 1 43 parts by weight of methacrylic acid-modified bisphenol F type epoxy resin (95% partially methacrylic product) obtained in Synthesis Example 1, 4 parts by weight of solid epoxy resin (manufactured by JER: Epicoat 1004, softening point 97 ° C.), 20 parts by weight of acrylic resin (polyethylene glycol diacrylate, light acrylate 14EG-A manufactured by Kyoeisha Chemical), 9 parts by weight of adipic acid dihydrazide (manufactured by Nippon Kasei Co., Ltd., ADH, melting point: 177 to 184 ° C.), photopolymerization started 2 parts by weight of alkylphenone polymerization initiator (manufactured by Ciba Specialty Chemicals: IRGACURE651), 13 parts by weight of silica particles: S-100 (manufactured by Nippon Shokubai Chemical), (meth) acrylic acid ester monomer and 7 parts by weight of thermoplastic resin particles obtained by copolymer
  • thermosetting agent instead of adipic acid dihydrazide (Nippon Kasei Co., Ltd., ADH), 9 parts by weight of 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin (Ajinomoto Amicure VDH, melting point 120 ° C. ) was used in the same manner as in Example 1 except that a sealing agent was obtained.
  • Example 3 A sealing agent was obtained in the same manner as in Example 1 except that no solid epoxy resin was used.
  • thermosetting agent 9 parts by weight of 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin (Ajinomoto Amicure VDH) was used instead of adipic acid dihydrazide (Nippon Kasei Co., Ltd., ADH).
  • a sealing agent was obtained in the same manner as in Comparative Example 1 except for the above.
  • Viscosity stability The sealing agents obtained in Examples and Comparative Examples were collected so that the weight of the sealing agent in the dispensing syringe was 10 g, and then subjected to defoaming treatment. About 2 g of them, initial viscosity was measured at room temperature (23 degreeC) using the E-type viscosity meter. Next, after the sample was stored at 23 ° C. and 50% RH for 1 week, the viscosity was measured again under the same conditions. At this time, the rate of increase in viscosity after storage for 1 week with respect to the initial viscosity was determined.
  • NI point of liquid crystal (nematic-isotropic phase transition temperature) 0.1 g (uncured) sealing agent obtained in Examples and Comparative Examples and 1 g of liquid crystal (MLC-11900-000, manufactured by Merck & Co., Inc.) were put into a vial and heated at 120 ° C. for 1 hour. As a result, a liquid crystal mixture was obtained. Next, this liquid crystal mixture was taken out, and its NI point was measured by DTA (differential thermal analysis) at a heating rate of 5 ° C./min.
  • the NI point of the liquid crystal changes greatly if the liquid crystal contains a small amount of impurities. For this reason, the smaller the amount of change of the NI point of the liquid crystal mixture after heating with respect to the NI point of the liquid crystal (before heating), the smaller the dissolution of the sealant component in the liquid crystal.
  • the change of the NI point of the liquid crystal mixture with respect to the NI point of the liquid crystal (original) was less than 5 ° C .: ⁇ (excellent);
  • a liquid crystal material (MLC-119000-000: manufactured by Merck & Co., Inc.) corresponding to the panel internal volume after bonding was precisely dropped into the main seal frame using a dispenser.
  • a pair of glass substrates was bonded together under reduced pressure, and then bonded to the atmosphere. Then, the two bonded glass substrates were held in a light shielding box for 3 minutes, then irradiated with 2000 mJ / cm 2 of ultraviolet light, and further heated at 100 ° C. for 1 hour.
  • the obtained liquid crystal display panel was visually observed for color unevenness generated in the liquid crystal around the seal portion before and after storage in a thermostatic chamber at 70 ° C. and 95% RH for 500 hours. Those in which color unevenness was not confirmed were evaluated as ⁇ (excellent); those confirmed were evaluated as x (inferior).
  • the taken out liquid crystal display panel is driven with an applied voltage of 5 V using a DC power supply device, and the liquid crystal display function in the vicinity of the liquid crystal sealant is functioning normally from the beginning of driving.
  • the display characteristics of the liquid crystal display panel were evaluated. The display characteristics are ⁇ (excellent) when the liquid crystal display function can be exhibited normally until sealing, and ⁇ (slightly inferior) when an abnormality in the liquid crystal display function is confirmed at less than 0.3 mm near the sealing.
  • x inferior
  • Adhesiveness In the above 4), the flat tensile strength of the sample of the liquid crystal display panel after being stored in a thermostat was measured at a tensile speed of 2 m / min using a tensile tester (manufactured by Intesco). Adhesiveness was evaluated as follows. Adhesive strength of 15 MPa or more: ⁇ (excellent) Adhesive strength is 7 MPa or more and less than 15 MPa: ⁇ (slightly inferior) Adhesive strength is less than 7 MPa: x (inferior)
  • the sealing agents of Examples 1 to 3 using a (meth) acryl-modified epoxy resin having a (meth) acrylic group equivalent weight / epoxy group equivalent ratio of 19 were (meth) acrylic.
  • the NI point of liquid crystal and the liquid crystal display characteristics are much better than the sealing agents of Comparative Examples 1 to 5 using a (meth) acryl-modified epoxy resin in which the ratio of group equivalent / epoxy group equivalent is 9 or less.
  • the (meth) acryl-modified epoxy resin contained in the sealing agents of Examples 1 to 3 is more hydroxyl group to the unreacted epoxy group than the (meth) acryl-modified epoxy resin contained in the sealing agents of Comparative Examples 1 to 5. Since the content ratio of is high, it is considered that the solubility in the liquid crystal was remarkably suppressed.
  • the (meth) acryl-modified epoxy resins contained in the sealing agents of Examples 1 to 3 have a higher content of methacryl groups than the (meth) acryl-modified epoxy resins of Comparative Examples 1 to 5, and thus are UV curable. It turns out that it is also favorable.
  • the liquid crystal sealing agent of the present invention contains many hydroxyl groups, dissolution in liquid crystals is suppressed even at high temperatures and high humidity. For this reason, when the hardened

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Abstract

L'invention a pour objectif de fournir un agent d'étanchéité pour cristaux liquides dont les propriétés d'affichage ne varient pas y compris dans des conditions de température et humidité élevées, et qui présente une excellente fiabilité d'affichage. L'agent d'étanchéité pour cristaux liquides de l'invention contient : une résine époxy modifiée (méth)acrylique obtenue par réaction d'une résine époxy contenant au moins deux groupes époxy dans une molécule, et d'un acide (méth)acrylique; un agent durcissant; et un initiateur de photopolymérisation. Ladite résine époxy modifiée (méth)acrylique contient un groupe hydroxy produit par réaction de ladite résine époxy contenant au moins deux groupes époxy dans une molécule, et dudit acide (méth)acrylique. En outre, le rapport équivalent de groupe (méth)acrylique / équivalent de groupe époxy de ladite résine époxy modifiée (méth)acrylique, dépasse 9. La valeur de groupe fonctionnel capable de liaison à l'hydrogène contenant ledit groupe hydroxy, est de 3×10-3 à 5×10-3mol/g.
PCT/JP2011/001645 2010-03-26 2011-03-18 Agent d'étanchéité pour cristaux liquides, procédé de fabrication de panneau d'affichage à cristaux liquides mettant en œuvre cet agent d'étanchéité, et panneau d'affichage à cristaux liquides WO2011118191A1 (fr)

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JP2017197731A (ja) * 2014-03-31 2017-11-02 協立化学産業株式会社 硬化後柔軟性に優れる硬化性樹脂、（メタ）アクリル化硬化性樹脂、及び液晶シール剤組成物
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WO2021246479A1 (fr) * 2020-06-04 2021-12-09 積水化学工業株式会社 Composé dihydrazide, composition de résine durcissable, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale et élément d'affichage à cristaux liquides

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JP7425612B2 (ja) * 2019-04-10 2024-01-31 シチズン時計株式会社 熱硬化性樹脂組成物、時計部品、夜光カプセルおよび夜光カプセルの製造方法
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JP2014185202A (ja) * 2013-03-22 2014-10-02 Nippon Kayaku Co Ltd 活性エネルギー線硬化型樹脂組成物、及びそれを用いた表示素子用着色スペーサー及び／またはブラックマトリックス
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JP2017197731A (ja) * 2014-03-31 2017-11-02 協立化学産業株式会社 硬化後柔軟性に優れる硬化性樹脂、（メタ）アクリル化硬化性樹脂、及び液晶シール剤組成物
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JP2020506254A (ja) * 2017-01-12 2020-02-27 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ 熱硬化性シーラント組成物
JP2019143038A (ja) * 2018-02-20 2019-08-29 ヘンケルジャパン株式会社 Ｕｖ熱硬化型接着剤組成物
CN111712764A (zh) * 2018-02-20 2020-09-25 汉高股份有限及两合公司 热固化和uv固化粘合剂组合物
JP7146409B2 (ja) 2018-02-20 2022-10-04 ヘンケルジャパン株式会社 Ｕｖ熱硬化型接着剤組成物
WO2021246479A1 (fr) * 2020-06-04 2021-12-09 積水化学工業株式会社 Composé dihydrazide, composition de résine durcissable, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau à conduction verticale et élément d'affichage à cristaux liquides
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