JP3955037B2 - Curable resin composition for liquid crystal display element - Google Patents

Description

The present invention provides a liquid crystal display that can provide a liquid crystal display element that is less likely to contaminate the liquid crystal and that can display an image with little color unevenness, even when used as a sealant for a liquid crystal dropping method in the production of a liquid crystal display element by the dropping method. The present invention relates to a curable composition for an element, a sealing agent for a liquid crystal dropping method comprising the curable composition for a liquid crystal display element, a material for vertical conduction, and a liquid crystal display element.

Conventionally, a liquid crystal display element such as a liquid crystal display cell is formed by forming a cell by facing two transparent substrates with electrodes facing each other at a predetermined interval and sealing the periphery with a sealing agent. The liquid crystal was injected into the cell from the liquid crystal injection port, and the liquid crystal injection port was sealed using a sealing agent or a sealing agent.

In this method, first, a seal pattern provided with a liquid crystal injection port using a thermosetting sealant is formed on one of two transparent substrates with electrodes by screen printing, and prebaked at 60 to 100 ° C. Dry the solvent in the sealant. Next, alignment is performed with the two substrates facing each other with a spacer interposed therebetween, and the gap in the vicinity of the seal is adjusted by performing hot pressing at 110 to 220 ° C. for 10 to 90 minutes, and then at 110 to 220 ° C. in an oven. Heat for 10 to 120 minutes to fully cure the sealant. Next, liquid crystal was injected from the liquid crystal injection port, and finally, the liquid crystal injection port was sealed using a sealing agent to produce a liquid crystal display element.

However, according to this manufacturing method, the positional displacement, gap variation, decrease in adhesion between the sealing agent and the substrate, etc. occur due to thermal strain; residual solvent thermally expands to generate bubbles, resulting in cap variation and seal path. The seal curing time is long; the prebaking process is complicated; the usable time of the sealant is short due to the volatilization of the solvent; and it takes time to inject liquid crystal. In particular, in a large liquid crystal display device in recent years, it takes a very long time to inject liquid crystal.

On the other hand, a manufacturing method of a liquid crystal display element called a dripping method using a photocurable sealant has been studied. In the dropping method, first, a rectangular seal pattern is formed on one of the two transparent substrates with electrodes by screen printing. Next, a liquid crystal micro-droplet is applied to the entire surface of the transparent substrate in an uncured state with the sealant uncured. The other transparent substrate is immediately overlaid and cured by irradiating the seal portion with ultraviolet rays to form a liquid crystal display element. Is made. If the substrates are bonded together under reduced pressure, a liquid crystal display element can be manufactured with extremely high efficiency in a short time. In the future, this dripping method is expected to become the mainstream of liquid crystal display manufacturing methods.

As a sealing agent used in a conventional construction method, for example, Patent Document 1 discloses an adhesive mainly composed of a partial (meth) acrylate of a bisphenol A type epoxy resin. Further, Patent Document 2, Patent Document 3, Patent Document 4, Patent Document 5, Patent Document 6, and the like disclose liquid crystal sealants containing (meth) acrylate as a main component.
However, since these sealants have properties that are easily compatible with liquid crystal materials, in liquid crystal display elements assembled using these sealants, the components of the sealant are eluted in the liquid crystal, and the periphery of the sealant In this case, the alignment of the liquid crystal is disturbed, which may cause display defects such as color unevenness. In particular, in the dropping method, there is a process in which an uncured sealant is in direct contact with liquid crystal, so liquid crystal contamination due to the sealant component has been a major problem.
In particular, when a sealant that is cured by heat is used, an uncured sealant component easily elutes in the liquid crystal, which causes a problem of liquid crystal contamination.

Japanese Patent Laid-Open No. 6-160872 JP-A-1-243029 JP 7-13173 A Japanese Patent Laid-Open No. 7-13174 Japanese Patent Laid-Open No. 7-13175 Japanese Patent Laid-Open No. 7-13174

In view of the above-mentioned present situation, the present invention is a liquid crystal display that is less likely to contaminate liquid crystals and can display images with little color unevenness even when used as a sealant for liquid crystal dropping methods in the production of liquid crystal display elements by the dropping method. It aims at providing the curable composition for liquid crystal display elements from which an element is obtained, the sealing compound for liquid crystal dropping methods which consists of this curable composition for liquid crystal display elements, the material for vertical conduction, and a liquid crystal display element.

The present invention is a curable resin composition for a liquid crystal display element that is cured only by light, and has a hydrogen bonding functional group and two or more (meth) acryl groups in one molecule, and hydrogen in one molecule. Curable resin composition for liquid crystal display device containing 0.1 to 20 parts by weight of radical photopolymerization initiator with respect to 100 parts by weight of curable resin having a binding functional group amount of 3.5 × 10 ⁻³ or more. It is.
The present invention is described in detail below.

The curable resin composition for liquid crystal display elements of the present invention (hereinafter also referred to as the resin composition of the present invention) has a hydrogen-bonding functional group and two or more (meth) acryl groups in the molecule. A curable resin having a hydrogen bondable functional group amount of 3.5 × 10 ⁻³ or more is contained as a resin component.
As a result of intensive studies, the present inventors have found that a resin having a certain amount of hydrogen bonding functional groups in one molecule is not easily eluted into the liquid crystal and does not contaminate the liquid crystal. In resin compositions used for conventional sealants for liquid crystal display elements, etc., even if a resin with low polarity and easily eluted into liquid crystals is used, or even when a highly polar resin is used, it is generated in the manufacturing process. Since no consideration was given to the incorporation of low polarity resins such as by-products and unreacted resins, liquid crystal display element sealants using such a resin composition have no liquid crystals. It was easily contaminated.
In the present invention, the liquid crystal is not contaminated by using only the resin that satisfies the above-mentioned requirements as the resin component.

The lower limit of the hydrogen bondable functional group amount of the curable resin is 3.5 × 10 ⁻³ . When it is less than 3.5 × 10 ⁻³ , when the resin composition of the present invention is used as a sealant for a liquid crystal display element, the curable resin is eluted into the liquid crystal and contaminates the liquid crystal. A preferred lower limit is 4.0 × 10 ⁻³ .
In addition, in this specification, the hydrogen bondable functional group amount means a value calculated by the following formula (1).

Amount of hydrogen bonding functional group = (number of hydrogen bonding functional groups in one molecule of curable resin) / (molecular weight of curable resin) (1)

The hydrogen bonding functional group is not particularly limited as long as it is a functional group or a residue having hydrogen bonding properties. For example, —OH group, —NH ₂ group, —NHR group (R is aromatic, aliphatic, -COOH group, -CONH ₂ group, -NHOH group, etc., -NHCO- bond, -NH- bond, -CONHCO- bond, -NH-NH present in the molecule -Groups having a residue such as a bond. Of these, a hydroxyl group and / or a urethane group are preferred.

Moreover, the said curable resin has the said hydrogen bondable functional group and two or more (meth) acryl groups in 1 molecule. Thereby, the resin composition of this invention becomes a photocurable type | mold.
In addition, in this specification, a (meth) acryl group means an acryl group or a methacryl group.

Although it does not specifically limit as curable resin which has a hydrogen bondable functional group and two or more (meth) acryl groups in said 1 molecule, For example, urethane (meth) acrylate resin which has a urethane bond, an epoxy group (meta ) (Meth) acrylic acid-modified epoxy resin obtained by modification with acrylic acid, (meth) acrylate derived from OH group-containing polyol and (meth) acrylic acid leaving one or more OH groups, etc. Is mentioned.

Although it does not specifically limit as a method of obtaining the said urethane (meth) acrylate resin, For example, the method of making the (meth) acrylic acid ester monomer which has an active hydrogen group react with a diisocyanate compound; A diol compound and a diisocyanate compound are 1 by molar ratio. : A method of reacting a prepolymer having an isocyanate group at the terminal obtained by reacting at a ratio of 1 to 1: 2 with an acrylate monomer having an active hydrogen group that only reacts completely with the remaining isocyanate group; polyol And a method of reacting (meth) acrylate having an isocyanate group.

Examples of the diisocyanate compound include diphenylethane diisocyanate (MDI), tolylene diisocyanate (TDI), xylene diisocyanate (XDI), isophorone diisocyanate (IPDI), naphthylene diisocyanate (NDI), tolidine diisocyanate (TPDI), hexamethylene diisocyanate. (HDI), dicyclohexylmethane diisocyanate (HMDI), trimethylhexamethylene diisocyanate (TMHDI) and the like. Examples of commercially available (meth) acrylates having an isocyanate group include MOI manufactured by Showa Denko KK.

Although it does not specifically limit as said (meth) acrylate with active hydrogen, For example, in what has OH group, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycerin di (meth) acrylate , 2-hydroxy-3-acryloyloxypropyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxyethylphthalic acid epoxy ester, pentaerythritol triacrylate, etc., and those having a COO group, Examples include meth) acrylic acid, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, and 2-acryloyloxyethyl phthalic acid.

The diol compound is not particularly limited, and examples thereof include alkyl diol, polyether diol, and polyester diol.
The alkyl diol is not particularly limited. For example, ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, Examples include 1,4-cyclohexanediol.
The polyether diol is not particularly limited. For example, poly (ethylene oxide) diol, poly (propylene oxide) diol, poly (tetramethylene oxide) diol, bisphenol A ethylene oxide adduct, bisphenol A propylene oxide adduct Etc.
The polyester diol is not particularly limited. For example, poly (caprolactone) diol, poly (carbonate) diol, etc., acidic components such as adipic acid, succinic acid, terephthalic acid, isophthalic acid, ethylene glycol, diethylene glycol, 1, 4 -Polyester diol obtained by dehydration reaction with diol components such as butanediol.
These alkyl diols, polyether diols, and polyester diols may be used alone or in combination. Of these, bisphenol A ethylene oxide adduct and poly (caprolactone) diol are particularly preferred from the viewpoints of adhesiveness and cure shrinkage.

Examples of the epoxy resin used as a raw material for the (meth) acrylic acid-modified epoxy resin include, for example, a novolak type such as a phenol novolak type, a cresol novolak type, a biphenyl novolak type, a trisphenol novolak type, and a dicyclopentadiene novolak type. Examples of the bisphenol type include bisphenol A type, bisphenol F type, 2,2′-diallyl bisphenol type, bisphenol S type, hydrogenated bisphenol type, and polyoxypropylene bisphenol A type.

Among the epoxy resins that are commercially available as raw materials for the (meth) acrylic acid-modified epoxy resin, for example, as a phenol novolak type, Epicron N-740, Epicron N-770, Epicron N-775 (or more, Dainippon Ink Chemical Co., Ltd.), Epicoat 152, Epicoat 154 (above, Japan Epoxy Resin Co., Ltd.), and the like. Examples of the cresol novolak type include Epicron N-660, Epicron N-665, Epicron N-670, and Epicron N. -673, Epicron N-680, Epicron N-695, Epicron N-665-EXP, Epicron N-672-EXP (above, manufactured by Dainippon Ink and Chemicals, Inc.) and the like.

The (meth) acrylated product of the epoxy resin can be obtained, for example, by reacting an epoxy resin and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method. By appropriately changing the blending amount of the epoxy resin and (meth) acrylic acid, it is possible to obtain an epoxy resin having a desired acrylation rate.

Examples of (meth) acrylate derived from the polyol containing OH group and (meth) acrylic acid in a state where one or more OH groups are left include glycerin di (meth) acrylate and the like.

The resin composition of the present invention may further contain a cationically polymerizable compound having a hydrogen bonding functional group as a resin component.
In the present specification, the cationic polymerizable compound means a compound having a cationic polymerizable group that undergoes a polymerization reaction or a crosslinking reaction in a chain reaction in the presence of an acid such as a protonic acid or a Lewis acid. Examples of the cationic polymerizable group include an epoxy group, an oxetane group, a styryl group, and a vinyloxy group. Among these, an epoxy group and an oxetane group are preferable from the viewpoints of adhesiveness and rapid curing. The cationic polymerizable compound preferably has two or more of these cationic polymerizable groups in one molecule. By having two or more cationically polymerizable groups in one molecule, the amount of residual unreacted compound after the polymerization reaction or cross-linking reaction is extremely reduced, and contamination of the liquid crystal due to the amount of residual unreacted compound can be suppressed. However, the number of cationically polymerizable groups contained in one molecule is more preferably 6 or less. If it exceeds 6, curing shrinkage increases, which may cause a decrease in adhesive strength.

The cationic polymerizable compound has a hydrogen bonding functional group. Examples of the hydrogen bonding functional group include the same ones as described above. By having such a hydrogen bonding functional group, the cationically polymerizable compound is not easily eluted into the liquid crystal even when it comes into contact with the liquid crystal before curing, and does not contaminate the liquid crystal. Especially, it is preferable to have a hydroxyl group or a urethane group from an adhesive point.

The cationically polymerizable compound preferably has a weight average molecular weight of 300 or more. If it is less than 300, it may be eluted and contaminated in the liquid crystal. Although the upper limit of a weight average molecular weight is not specifically limited, When it exceeds 50,000, adjustment of the viscosity of a resin composition may become difficult.

The resin composition of the present invention contains a radical photopolymerization initiator.
Although it does not specifically limit as said radical photopolymerization initiator, What has a reactive double bond and a photoreaction start part is suitable. When such a radical photopolymerization initiator is used, sufficient reactivity can be imparted when blended with the curable resin, and it is incorporated into the cured product via a chemical bond, so that it elutes into the liquid crystal. And will not contaminate the liquid crystal. Of these, benzoin (ether) compounds having a reactive double bond and a hydrogen bonding functional group are preferred. Examples of the hydrogen bonding functional group include a hydroxyl group and a urethane bond.
The benzoin (ether) compounds represent benzoins and benzoin ethers.

Examples of the reactive double bond include functional groups such as an allyl group, a vinyl ether group, and a (meth) acryl group, and a (meth) acryl residue is preferable because of its high reactivity. By having such a reactive double bond, the weather resistance of the resin composition of the present invention is improved.

The said benzoin (ether) type compound should just have any one of a hydroxyl group and a urethane bond, and may have both. If the benzoin (ether) compound has neither a hydroxyl group nor a urethane bond, it may elute into the liquid crystal.

In the benzoin (ether) compound, the reactive double bond and the hydroxyl group and / or the urethane bond may be located at any part of the benzoin (ether) skeleton, and are represented by the following general formula (1). Those having a molecular skeleton are preferred. If a compound having such a molecular skeleton is used as a radical photopolymerization initiator, the amount of residue is reduced and the amount of outgas can be reduced.

In the formula, R represents hydrogen or a residual aliphatic hydrocarbon chain having 4 or less carbon atoms. When R is a residual aliphatic hydrocarbon chain having more than 4 carbon atoms, the storage stability when a radical photopolymerization initiator is added increases, but the reactivity may decrease due to steric hindrance of the substituent.

Examples of benzoin (ether) compounds having a molecular skeleton represented by general formula (1) include compounds represented by the following general formula (2).

In the formula, R represents hydrogen or an aliphatic hydrocarbon residue having 4 or less carbon atoms, X represents a residue of a bifunctional isocyanate derivative having 13 or less carbon atoms, and Y represents an aliphatic hydrocarbon residue having 4 or less carbon atoms. This represents a residue having an atomic ratio of carbon and oxygen constituting a group or residue of 3 or less. When X is a residue of a bifunctional isocyanate derivative having more than 13 carbon atoms, it may be easily dissolved in the liquid crystal, and Y may be an aliphatic hydrocarbon group having more than 4 carbon atoms or an atomic ratio of carbon to oxygen of 3 If the residue exceeds 50, it may be easily dissolved in the liquid crystal.

Other examples of the photo radical polymerization initiator include benzophenone, 2,2-diethoxyacetophenone, benzyl, benzoyl isopropyl ether, benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, and thioxanthone. These radical photopolymerization initiators may be used alone or in combination of two or more.

The minimum of the addition amount of the said radical photopolymerization initiator in the curable composition for liquid crystal display elements of this invention is 0.1 weight part with respect to 100 weight part of said curable resins, and an upper limit is 20 weight part. If the amount is less than 0.1 parts by weight, the ability to initiate photopolymerization is insufficient and the effect is not obtained. If the amount exceeds 20 parts by weight, a large amount of unreacted photoradical polymerization initiator remains and is eluted in the liquid crystal. Contaminates the liquid crystal. The lower limit is more preferably 0.5 parts by weight, the more preferable upper limit is 10 parts by weight, and the still more preferable upper limit is 5 parts by weight.

When the resin composition of the present invention contains a cationically polymerizable compound having a hydrogen bonding functional group as a resin component, it is preferable to further contain a cationic polymerization initiator. The cationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation. For example, an iron-allene complex compound, an aromatic diazonium salt, an aromatic iodonium salt, an aromatic sulfonium salt , Pyridinium, aluminum complex / silanol salt, halogenated alkyl-substituted triazine derivative, trifluoromethanesulfonic acid-N-imide ester derivative, benzenesulfonic acid-N-imide ester derivative, methanesulfonic acid-N-imide ester derivative, tribromomethyl And phenylsulfone derivatives. Among these cationic polymerization initiators, those commercially available include, for example, Optomer-SP-151, Optomer-SP-170, Optomer-SP-171 (manufactured by Asahi Denka Kogyo Co., Ltd.), UVE-1014 (General Electronics Co., Ltd.), Irgacure-261 (Ciba Geigy Co., Ltd.), Sun-Aid SI-60L, Sun-Aid SI-80L, UVI-6990 (manufactured by Union Carbide), BBI-103, MPI-103, TPS-103, DTS- 103, NAT-103, NDS-103 (manufactured by Midori Chemical Co., Ltd.), Sun-Aid SI-100L (manufactured by Sanshin Chemical Industry Co., Ltd.), CI-2064, CI-2639, CI-2624, CI-2481 (and above, Japan) Soda Co., Ltd.), RHODORSIL PHOTOINITIATOR 2074 And CD-1012 (manufactured by Sartomer) and the like. These cationic polymerizable initiators may be used alone or in combination of two or more.

The preferable lower limit of the addition amount of the photocationic polymerization initiator in the curable composition for liquid crystal display elements of the present invention is 0.1 part by weight with respect to 100 parts by weight of the cationically polymerizable compound, and the preferable upper limit is 10 parts by weight. is there. If the amount is less than 0.1 parts by weight, the ability to start photopolymerization is insufficient and the effect cannot be obtained. If the amount exceeds 10 parts by weight, no improvement in curability is observed.

The resin composition of the present invention may contain a silane coupling agent. The silane coupling agent has a role as an adhesion aid for improving the adhesion to the transparent substrate mainly when the resin composition of the present invention is used as a sealing agent or a material for vertical conduction.
The silane coupling agent is not particularly limited, but is excellent in the effect of improving adhesion to a substrate and the like, and can be prevented from flowing into the liquid crystal material by chemically bonding with a curable resin. Propyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-isocyanatopropyltrimethoxysilane and the like are preferably used. These silane coupling agents may be used alone or in combination of two or more.

The resin composition of the present invention may contain a filler for the purpose of improving adhesiveness due to the stress dispersion effect, improving the linear expansion coefficient, and the like. The filler is not particularly limited. For example, silica, diatomaceous earth, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, magnesium carbonate, barium sulfate, gypsum, calcium silicate , Talc, glass beads, sericite activated clay, bentonite, aluminum nitride, silicon nitride, and other inorganic fillers.

It does not specifically limit as a method to manufacture the resin composition of this invention, The method etc. which mix the said curable resin, radical photopolymerization initiator, etc. by a conventionally well-known method are mentioned. At this time, in order to remove ionic impurities, it may be brought into contact with an ion-adsorbing solid such as a layered silicate mineral.

The resin composition of the present invention has a hydrogen bonding functional group and two or more (meth) acryl groups in one molecule, and the amount of the hydrogen bonding functional group in one molecule is 3.5 × 10 ⁻³ or more. The liquid crystal display element is produced by a dripping method as a sealing agent for liquid crystal display elements or as a material for vertical conduction because there is almost no contamination of liquid crystal due to elution of resin components. Even when used in the liquid crystal display device, a liquid crystal display element capable of displaying an image with less color unevenness and hardly contaminating the liquid crystal can be obtained.
The sealing agent for a liquid crystal dropping method comprising the curable resin composition for a liquid crystal display element of the present invention is also one aspect of the present invention.

A material for vertical conduction can be produced by blending conductive fine particles with the curable resin composition for a liquid crystal display element of the present invention and / or the sealing agent for a liquid crystal dropping method of the present invention. By using such a material for vertical conduction, the electrodes of the transparent substrate can be conductively connected without contaminating the liquid crystal.
The material for vertical conduction containing the curable resin composition for a liquid crystal display element of the present invention and / or the sealing agent for a liquid crystal dropping method of the present invention and conductive fine particles is also one aspect of the present invention.

The conductive fine particles are not particularly limited, and metal balls, those obtained by forming a conductive metal layer on the surface of resin fine particles, and the like can be used. Among them, the one in which the conductive metal layer is formed on the surface of the resin fine particles is preferable because the conductive connection is possible without damaging the transparent substrate due to the excellent elasticity of the resin fine particles.

The liquid crystal display element using the sealing agent for liquid crystal dropping method of the present invention and / or the material for vertical conduction of the present invention is also one aspect of the present invention.

According to the present invention, a liquid crystal display element capable of displaying an image with little color unevenness is obtained even when used as a sealant for a liquid crystal dropping method in the production of a liquid crystal display element by a dropping method. A curable composition for liquid crystal display elements, a sealing agent for liquid crystal dropping method comprising the curable composition for liquid crystal display elements, a material for vertical conduction, and a liquid crystal display element can be provided.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples.

Example 1
1360 parts by weight of solid bisphenol A diglycidyl ether (Dainippon Ink & Chemicals "850CRP"), 2 parts by weight of p-methoxyphenol as a polymerization inhibitor, 2 parts by weight of triethylamine as a reaction catalyst, and 576 parts by weight of acrylic acid, The mixture was refluxed and stirred at 110 ° C. for 5 hours. In order to adsorb ionic impurities in the reaction product, 100 parts by weight of the obtained resin was filtered through a column packed with 10 parts by weight of a natural combination of quartz and kaolin (“Siritin V85” manufactured by Hoffman Mineral Co.). As a result, an acrylic acid-modified bisphenol A epoxy resin was obtained.
The amount of the hydrogen bonding functional group of the obtained acrylic acid-modified bisphenol A epoxy resin was calculated to be 4.1 × 10 ⁻³ .

Next, 60 parts by weight of the acrylic acid-modified bisphenol A epoxy resin obtained, 2 parts by weight of 2,2-diethoxyacetophenone as a radical photopolymerization initiator, 22 parts by weight of silica particles (average particle size 1.5 μm), γ- 1 part by weight of glycidoxypropyltrimethoxysilane was sufficiently mixed using a three roll so as to be a uniform liquid, to obtain a curable resin composition for a liquid crystal display element.

The obtained curable resin composition for a liquid crystal display element is used as a sealant for a liquid crystal dropping method, and the liquid crystal display element sealant is placed on one of two transparent substrates with a transparent electrode with a dispenser so as to draw a rectangular frame. Applied. Subsequently, fine droplets of liquid crystal (manufactured by Chisso Co., Ltd., JC-5004LA) are dropped onto the entire surface of the transparent substrate, and the other transparent substrate is immediately overlaid, and a high-pressure mercury lamp is used as a seal portion to apply ultraviolet light at 50 mW / cm. ^A liquid crystal display cell was produced by irradiating at ² for 60 seconds.
When the obtained liquid crystal display cell was visually observed for color unevenness generated in the liquid crystal around the seal portion before and after being left at 60 ° C. and 95% RH for 500 hours, no color unevenness was observed.

(Comparative Example 1)
As a curable resin, 30 parts by weight of acrylic acid-modified bisphenol A epoxy resin prepared in Example 1 and 30 parts by weight of ethylene oxide-modified bisphenol A diacrylate (“NK Ester A-BPE-4” manufactured by Shin-Nakamura Chemical Co., Ltd.) A curable resin composition for a liquid crystal display element was obtained by the same method as in Example 1 except that the mixed resin was used, and a liquid crystal display cell was produced using this as a sealant for the liquid crystal dropping method.
It was 2.1 * 10 < ^-3 > when the amount of hydrogen bondable functional groups of this mixed resin was computed.
When the obtained liquid crystal display cell was visually observed for color unevenness generated in the liquid crystal around the seal portion before and after being left at 60 ° C. and 95% RH for 500 hours, color unevenness was partially recognized.

According to the present invention, a liquid crystal display element capable of displaying an image with little color unevenness is obtained even when used as a sealant for a liquid crystal dropping method in the production of a liquid crystal display element by a dropping method. A curable composition for liquid crystal display elements, a sealing agent for liquid crystal dropping method comprising the curable composition for liquid crystal display elements, a material for vertical conduction, and a liquid crystal display element can be provided.

Claims (5)

A curable resin composition for a liquid crystal display element that is cured only by light,
100 parts by weight of a curable resin having a hydrogen bonding functional group and two or more (meth) acryl groups in one molecule, and the amount of the hydrogen bonding functional group in one molecule is 3.5 × 10 ⁻³ or more In contrast, a curable resin composition for a liquid crystal display element, comprising 0.1 to 20 parts by weight of a radical photopolymerization initiator. The curable resin composition for a liquid crystal display element according to claim 1, wherein the hydrogen bonding functional group is a hydroxyl group and / or a urethane group. A sealant for a liquid crystal dropping method comprising the curable resin composition for a liquid crystal display element according to claim 1. A material for vertical conduction comprising the curable resin composition for a liquid crystal display element according to claim 1 or 2 and / or the sealing agent for liquid crystal dropping method according to claim 3 and conductive fine particles. A liquid crystal display element comprising the sealing agent for liquid crystal dropping method according to claim 3 and / or the material for vertical conduction according to claim 4.