WO2020036234A1 - Composition for moistureproof sealing material - Google Patents

Abstract

The purpose of the present invention is to provide a composition for moistureproof sealing materials which has excellent photocurability and gives cured objects excellent in terms of moistureproofness and stretachability. A composition for moistureproof sealing materials which comprises (a) at least one isocyanuric-acid-based epoxy compound selected from the group consisting of compounds represented by formula [1] and compounds represented by formula [2], (b) a polyfunctional epoxy compound having no isocyanuric acid skeleton, (c) a polyfunctional oxetane compound, and (d) a polymerization initiator which generates an acid or a base upon irradiation with actinic rays. (In formula [1], R¹ represents a hydrogen atom or a methyl group and L¹ represents a C_2-7 alkylene group; the R¹ moieties may be the same or different and the L¹ moieties may be the same or different.) (In formula [2], R² represents a hydrogen atom or a methyl group, L² represents a C_1-5 alkylene group, A represents an (n+1)-valent aliphatic hydrocarbon group optionally containing an ether bond, and n is an integer of 2-5; the R² moieties may be the same or different, the L² moieties may be the same or different, the A moieties may be the same or different, and the n's may be the same or different.)

Description

Composition for moisture-proof sealing material

The present invention relates to a composition for a moisture-proof sealing material, a cured product obtained therefrom, and an organic EL display mounted with the cured product.

In recent years, flat panel displays (FPDs) using various display elements have been developed and manufactured in the electric and electronic industries. Many of these displays have a display element sealed in a cell made of a flat panel such as glass or plastic. Typical examples thereof include a liquid crystal display (LCD), an electroluminescence display (ELD), and electronic paper.

Among these, EL displays, especially organic EL displays, are excellent in terms of high brightness, high efficiency, high-speed response, and the like in addition to the high viewing angle and high contrast unique to natural light emission. Attracting attention. Further, since the electrodes and the light-emitting layer are very thin, the possibility of forming them on a plastic base material for use as a flexible display or large-scale flat lighting is also being studied.

The organic EL element is composed of an electron injected into the light emitting layer directly from the electron injection electrode or through the electron transport layer, and a hole injected directly into the light emitting layer from the hole injection electrode or through the hole transport layer. Light emission is generated by recombination with the hydrogen. Very active and chemically unstable alloys are used for the electrodes of the organic EL device based on such a light emitting mechanism. Therefore, it is susceptible to corrosion and oxidation by moisture and oxygen from the outside, and a non-light-emitting portion called a dark spot is formed and markedly increased, and luminance decreases with time. Further, since an organic material is used for the light emitting layer and the charge transport layer of the organic EL element, the organic layer is easily deteriorated by moisture and oxygen, and similarly, there is a problem that a dark spot is formed and the luminance is reduced.

Therefore, in order to make a practical organic EL element, it is necessary to effectively seal the element so that moisture and oxygen do not enter the organic material and the electrode material. As a method for sealing the FPD, there is a method using a thermosetting epoxy resin which has been conventionally used for sealing the LCD. However, such a thermosetting epoxy resin is used at a high temperature of 150 to 180 ° C. for about 2 hours. There was a problem that it was necessary to heat and productivity did not increase. Further, the organic EL element is excellent in high brightness, high efficiency, high-speed response and the like, but has low heat resistance, and usually has a heat resistance temperature of about 80 to 100 ° C. For this reason, there has been a problem that even when a thermosetting epoxy resin is used, the sealing of the organic EL display cannot be sufficiently cured by heating.

In order to solve these problems, development of a photocurable sealing material that can be cured at low temperature and at high speed has been attempted. As the photocurable sealing material, there are usually a photoradical curable sealing material and a photocationically curable sealing material.
An acrylic resin is mainly used as the photo-radical-curable sealing material.
On the other hand, an epoxy resin is mainly used as a photocationically curable sealing material (for example, Patent Documents 1 and 2).

Japanese Patent Application Laid-Open No. H11-224771 JP 2014-105286 A

While the acrylic resin has an advantage that various acrylate monomers and oligomers can be used, there is still a problem that the moisture resistance is generally insufficient, and the curing shrinkage is large and the adhesiveness is insufficient. No material has satisfactory performance.
The epoxy resin generally has relatively good adhesiveness, but has poor photocurability such as photosensitivity and rapid curability, and has a problem in that it is generally hard and brittle.
Furthermore, in recent years, flexible displays such as rollable and foldable have been actively developed, so that not only a photocuring property but also a mechanical property after curing, particularly a sealing material having high stretchability has been demanded.
However, in the technique described in Patent Document 1 described above, a high molecular weight polymer cannot be obtained due to chain transfer by a hydroxyl group of a compound having a hydroxyl group, which is blended to improve photocationic curability, and mechanical properties are improved. Can not expect.

Accordingly, an object of the present invention is to provide a composition for a moisture-proof sealing material which is excellent in photocurability and further provides a cured product excellent in moisture-proof property and stretchability.

The present inventors have conducted intensive studies to solve the above problems, and as a result, among various epoxy resins, an isocyanuric acid-based epoxy compound having a specific structure, and a specific polyfunctional epoxy compound and a polyfunctional oxetane compound. It has been found that a cured product made of a composition containing the compound has moisture-proof properties, stretchability, and high adhesion to a substrate or an electrode, and is excellent as a moisture-proof sealing material for an organic EL device or the like, and has led to the present invention.
That is, the present invention provides, as a first aspect, (a) at least one isocyanuric acid-based epoxy compound selected from the group consisting of a compound represented by Formula [1] and a compound represented by Formula [2]; A composition for a moisture-proof seal material, comprising: b) a polyfunctional epoxy compound having no isocyanuric acid skeleton, (c) a polyfunctional oxetane compound, and (d) a polymerization initiator that generates an acid or a base by active energy rays.

(Wherein, R ¹ represents a hydrogen atom or a methyl group, and L ¹ represents an alkylene group having 2 to 7 carbon atoms. Here, each R ¹ may be the same or different. , Each L ¹ may be the same or different.)

(Wherein, R ² represents a hydrogen atom or a methyl group, L ² represents an alkylene group having 1 to 5 carbon atoms, and A represents an aliphatic group which may contain a (n + 1) -valent ether bond. Represents a hydrocarbon group, and n represents an integer of 2 to 5. Here, each R ² may be the same or different, and each L ² may be the same or different. And each A may be the same or different, and each n may be the same or different.)
As a second viewpoint, the (b) polyfunctional epoxy compound having no isocyanuric acid skeleton is a bisphenol A epoxy resin, a bisphenol F epoxy resin, a hydrogenated bisphenol A epoxy resin, a hydrogenated bisphenol F epoxy resin, Bisphenol A novolak type epoxy resin, bisphenol F novolak type epoxy resin, and at least one selected from the group consisting of alicyclic polyglycidyl ether type epoxy resin, the composition for a moisture-proof sealing material according to the first aspect,
As a third viewpoint, the polyfunctional epoxy compound (b) having no isocyanuric acid skeleton is bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, Bisphenol A novolak polyglycidyl ether, and at least one selected from the group consisting of dicyclopentadiene dimethanol diglycidyl ether, the composition for a moisture-proof sealing material according to the second aspect,
As a fourth aspect, the composition for a moisture-proof sealing material according to the third aspect, wherein (b) the polyfunctional epoxy compound having no isocyanuric acid skeleton is bisphenol F diglycidyl ether.
As a fifth aspect, for the moisture-proof sealing material according to any one of the first to fourth aspects, the polymerization initiator (d) that generates an acid or a base by an active energy ray is a photoacid generator. Regarding the composition,
As a sixth aspect, the composition for a moisture-proof sealing material according to any one of the first to fifth aspects, wherein the (a) isocyanuric acid-based epoxy compound is a compound represented by the formula [1]. With regard to
As a seventh aspect, the moisture permeability of the cured product measured by the cup method condition B (temperature 40 ° C., relative humidity 90%) of the moisture permeability test method of the moisture-proof packaging material according to JIS Z 0208 (1976) is represented by the following formula: 100μm or less 20g ^/ m 2 · 24h with terms relates moisture sealant composition according to any one of the first aspect to the sixth aspect,
As an eighth aspect, the composition for a moisture-proof seal material according to any one of the first to seventh aspects, which is a composition for an organic EL display moisture-proof seal material,
As a ninth aspect, a cured product obtained by curing the moisture-proof sealing material composition according to any one of the first to eighth aspects,
As a tenth aspect, the present invention relates to an organic EL display on which the cured product according to the ninth aspect is mounted.

Epoxy resin is excellent in heat resistance, insulation resistance and adhesion. Among them, the isocyanuric acid-based epoxy compound, which is a feature of the present invention, has excellent adhesion to various substrates and the like due to its structure containing many polar elements, and has between the isocyanuric acid skeleton and the epoxy ring. Because of its structure containing an alkylene group or an alkylene group and an ester bond, it is excellent in stretchability. Therefore, by curing with a polyfunctional epoxy compound and a polyfunctional oxetane compound not containing a cyanuric acid skeleton, adhesion and moisture resistance are improved. And a sealing material having excellent stretchability.
Further, since the epoxy ring and the oxetane ring have high reactivity in the presence of an acid or a base, the use of a polymerization initiator that generates an acid or a base by an active energy ray enables the activation energy such as light without heating. The reaction proceeds by irradiation with a ray.
Therefore, according to the present invention, it is possible to provide a composition for a moisture-proof sealing material which is excellent in photocurability and further provides a cured product excellent in moistureproofness and stretchability.
Further, according to the present invention, a cured product which is cured by an active energy ray and has excellent moisture-proof properties and stretchability can be obtained. Therefore, a device having low heat resistance such as an organic EL display and susceptible to deterioration by moisture or oxygen is used. A cured product (moisture-proof sealing material) useful as a moisture-proof sealing material can be provided.

FIG. 1 is a schematic view of a glass substrate on which a silver electrode used for ion migration evaluation is formed. FIG. 2 is a schematic view showing a process of preparing a test piece used for ion migration evaluation.

<Composition for moisture-proof sealing material>
The composition for a moisture-proof seal material of the present invention is, for example, a composition for a moisture-proof seal material used for forming a moisture-proof seal material for effectively sealing an organic EL element in an organic EL display, (A) an isocyanuric acid epoxy compound selected from the compound represented by the formula [1] and the compound represented by the formula [2], (b) a polyfunctional epoxy compound having no isocyanuric acid skeleton, (c) A moisture-proof seal material composition comprising a polyfunctional oxetane compound and (d) a polymerization initiator that generates an acid or a base by an active energy ray.

[Component (a)]
<Epoxy compound represented by formula [1]>
In the above formula [1], R ¹ represents a hydrogen atom or a methyl group, and L ¹ represents an alkylene group having 2 to 7 carbon atoms. Here, each R ¹ may be the same or different, and each L ¹ may be the same or different.
Examples of the alkylene group having 2 to 7 carbon atoms represented by L ¹ include ethylene, trimethylene, 1-methylethylene, tetramethylene, 1-methyltrimethylene, 1,1-dimethylethylene, and pentane. Methylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1,1-dimethyltrimethylene group, 1,2-dimethyltrimethylene group, 2,2-dimethyltrimethylene group, 1-ethyltrimethylene group , Hexamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 1,1-dimethyltetramethylene, 1,2-dimethyltetramethylene, 2,2-dimethyltetramethylene Methylene group, 1-ethyltetramethylene group, 1,1,2-trimethyltrimethylene group, 1,2,2-trimethyl And a 1-ethyl-1-methyltrimethylene group, a 1-ethyl-2-methyltrimethylene group, a cyclohexane-1,4-diyl group, and a heptamethylene group. Especially, a trimethylene group and a hexamethylene group are preferable.

The compound represented by the above formula [1] can be prepared by using, for example, an isocyanuric acid and an olefin compound having a leaving group X as a starting material, which are conventionally known (for example, WO 2010/092947 pamphlet, JP 2012-25688 A). Epoxides) can be produced.
Specifically, after reacting isocyanuric acid with an olefin compound represented by CH ₂ ＣＲCR ₁ -L ₁ -X to produce an olefin-substituted isocyanurate having an unsaturated bond (intermediate), By reacting the (intermediate) with a peroxide, the epoxy compound represented by the above formula [1] can be produced. As an example, a synthesis scheme is shown below.
The leaving group X is not particularly limited as long as it is a group that reacts with the NH group of isocyanuric acid. Examples thereof include a hydroxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a toluenesulfonyloxy group, and a nitrobenzenesulfonyl group. Examples include an oxy group, an acetoxy group, a trifluoroacetoxy group, a halogen atom and the like.

In the above formula, R ¹ and L ¹ represent the same meaning as described above.

Examples of the epoxy compound include tris (3,4-epoxybutyl) isocyanurate, tris (4,5-epoxypentyl) isocyanurate, tris (5,6-epoxyhexyl) isocyanurate, tris (6,7- Epoxyheptyl) isocyanurate, tris (7,8-epoxyoctyl) isocyanurate, tris (8,9-epoxynonyl) isocyanurate and the like.
As the epoxy compound, a commercially available product can be suitably used, and examples thereof include TEPIC (registered trademark) -VL and FL (both manufactured by Nissan Chemical Industries, Ltd.). These epoxy compounds can be used alone or as a mixture of two or more.

<Compound represented by Formula [2]>
In the formula [2], R ² represents a hydrogen atom or a methyl group, L ² represents an alkylene group having 1 to 5 carbon atoms, and A may contain a (n + 1) -valent ether bond. It represents a good aliphatic hydrocarbon group, and n represents an integer of 2 to 5. Here, each R ² may be the same or different, each L ² may be the same or different, each A may be the same or different, Each n may be the same or different.
The alkylene group having 1 to 5 carbon atoms which L ² represents, for example, methylene group, ethylene group, trimethylene group, methylethylene group, tetramethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 1 1,1-dimethylethylene group, pentamethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1,1-dimethyltrimethylene group, 1,2-dimethyltrimethylene group, 2,2-dimethyltrimethylene And a 1-ethyltrimethylene group. Among them, an ethylene group is preferred.

Examples of the aliphatic hydrocarbon group which may contain an (n + 1) -valent ether bond represented by A include, for example, those derived by removing (n + 1) hydrogen atoms from an aliphatic hydrocarbon having 1 to 10 carbon atoms. And (n + 1) -valent groups. Further, these groups may contain an ether bond (—O—) between any carbon-carbon bonds. Examples of the aliphatic hydrocarbon having 1 to 10 carbon atoms include methane, ethane, propane, cyclopropane, butane, isobutane, cyclobutane, pentane, isopentane, neopentane, cyclopentane, hexane, isohexane, neohexane and biisopropyl. , Cyclohexane, heptane, octane, 2-ethylhexane, nonane, decane, adamantane and the like.
Specifically, for example, glycerin, diglycerin, triglycerin, 2-hydroxy-1,4-butanediol, trimethylolmethane, 1,1,1-trimethylolethane, 1,1,1-trimethylolpropane, Examples thereof include (n + 1) -valent groups derived from a polyol selected from the group consisting of ditrimethylolpropane, pentaerythritol, and dipentaerythritol by removing a hydroxy group. Among them, a trivalent group derived from 1,1,1-trimethylolpropane by removing a hydroxy group is preferable.

The compound represented by the above formula [2] is conventionally known from, for example, tris (carboxyalkyl) isocyanurate and an olefin compound having an ether bond and a group Y that reacts with a carboxyl group as a starting material (for example, International Publication WO 2012/2012). / 128325 pamphlet), etc.).

Specifically, an olefin-substituted isocyanate having an unsaturated bond is reacted by reacting tris (carboxyalkyl) isocyanurate with an olefin compound represented by (CH ₂ ＣＲCR ² —CH ₂ —O) _n —AY. After producing the nurate (intermediate), the compound (intermediate) is reacted with a peroxide to produce the epoxy compound represented by the above formula [2]. As an example, a synthesis scheme is shown below.
The group Y is not particularly limited as long as it reacts with the carboxyl group of isocyanuric acid, and examples thereof include a hydroxy group and a halogen atom.

In the above formula, R ² , L ² and A represent the same meaning as described above.

Examples of the epoxy compound include 1,3,5-tris (2- (2,2-bis (glycidyloxymethyl) butoxycarbonyl) ethyl) isocyanurate and 1,3,5-tris (2- (2,2 2-bis (glycidyloxymethyl) -3- (glycidyloxy) propoxycarbonyl) ethyl) isocyanurate, 1,3,5-tris (2- (1- (glycidyloxymethyl) -2- (glycidyloxy) ethoxycarbonyl) ) Ethyl) isocyanurate and the like. Among them, 1,3,5-tris (2- (2,2-bis (glycidyloxymethyl) butoxycarbonyl) ethyl) isocyanurate is preferable.
As the epoxy compound, commercially available products can be suitably used, and examples thereof include TEPIC (registered trademark) -UC (manufactured by Nissan Chemical Industries, Ltd.). These epoxy compounds can be used alone or as a mixture of two or more.

The composition for a moisture-proof sealing material of the present invention uses an isocyanuric acid-based epoxy compound, particularly, a semiconductor substrate such as a metal or ceramic, a semiconductor element and a lead electrode to be joined to the semiconductor element, and a cured semiconductor sealing resin. A moisture-proof sealing material having excellent adhesion can be formed.
In the isocyanuric acid epoxy compound of the present invention, L ¹ in the formula [1] represents an alkylene group having 2 to 7 carbon atoms, and L ² in the formula [2] represents a carbon atom having ² to 7 carbon atoms. Since A represents an alkylene group of 1 to 5 and A represents an aliphatic hydrocarbon group which may contain an (n + 1) -valent ether bond, the composition for a moisture-proof sealing material of the present invention is, for example, a compound represented by the formula A cured product excellent in stretchability can be formed as compared with a composition containing a compound in which L ^{1 in} [1] represents a methylene group.

[(B) Polyfunctional epoxy compound having no isocyanuric acid skeleton]
The polyfunctional epoxy compound having no isocyanuric acid skeleton is not particularly limited as long as it contains two or more epoxy groups in one molecule, and a commercially available product can be used. For example, 1,2,7,8-diepoxyoctane, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,6-dimethylol perfluorohexane diglycidyl ether, (poly ) Ethylene glycol diglycidyl ether, (poly) propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, glycerol triglycidyl ether, diglycerol polyglycidyl ether, trimethylolethane triglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol Diglycidyl ether, pentaerythritol tetraglycidyl ether, pentaerythritol polyglycidyl ether, sorbitol polyglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, dicyclopentadiene dimethanol diglycidyl ether, dibromophenyl glycidyl ether, 2,6-diglycidylphenyl glycidyl ether, resorcinol diglycidyl ether, bis (2.7 -Diglycidyloxynaphthalen-1-yl) methane, 1,1,2,2-tetrakis (4-glycidyloxyphenyl) ethane, 1,1,3-tris (4-glycidyloxyphenyl) propane, bisphenol A diglycidyl Ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, tetrabromobisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl Ether, bisphenol hexafluoroacetone diglycidyl ether, bis (2,3-epoxycyclopentyl) ether, 1,2-bis (3,4-epoxycyclohexylmethoxy) ethane, ethylene glycol bis (3,4-epoxycyclohexanecarboxylate) 3,4-epoxycyclohexanecarboxylate (3,4-epoxycyclohexyl) methyl, 4,5-epoxy-2-methylcyclohexanecarboxylate 4,5-epoxy-2-methylcyclohexylmethyl, adipate bis (3,4 -Epoxycyclohexylmethyl), 1,2-epoxy-4- (epoxyethyl) cyclohexane, 4- (spiro [3,4-epoxycyclohexane-1,5 '-[1,3] dioxane] -2'-yl) -1,2-epoxycyclohexyl Diglycidyl adipate, diglycidyl phthalate, diglycidyl tetrahydrophthalate, diglycidyl 1,2-cyclohexanedicarboxylate, N, N-diglycidyl-4-glycidyloxyaniline, N, N, N ′, N′-tetraglycidyl-m -Xylylenediamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, 4,4'-methylenebis (N, N-diglycidylaniline), 2- (4,4-dimethylpentane-2- Yl) -2,2-bis (glycidyloxymethyl) butyl-5,7,7-trimethyloctanoate, bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol A epoxy resin, hydrogenated bisphenol F epoxy Resin, bisphenol S type epoxy resin, alicyclic epoxy Resin, trisphenolmethane epoxy resin, tetraphenolethane epoxy resin, alicyclic polyglycidyl ether epoxy resin, phenol novolak epoxy resin, cresol novolak epoxy resin, naphthalene novolak epoxy resin, anthracene novolak epoxy resin, Biphenylene novolak epoxy resin, xylylene novolak epoxy resin, bisphenol A novolak epoxy resin, bisphenol F novolak epoxy resin, triphenolmethane novolak epoxy resin, tetrakisphenol novolak epoxy resin, dicyclopentadiene novolak epoxy resin, etc. But are not limited to these.

Among them, bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol A epoxy resin, hydrogenated bisphenol F epoxy resin, bisphenol A novolak epoxy resin, bisphenol F novolak epoxy resin, and alicyclic polyglycidyl At least one polyfunctional epoxy compound selected from the group consisting of ether type epoxy resins is preferable, and bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, bisphenol A At least one polyfunctional epoxy compound selected from the group consisting of novolak polyglycidyl ether and dicyclopentadiene dimethanol diglycidyl ether Still more preferably, bisphenol F diglycidyl ether are particularly preferred.
As the epoxy compound, commercially available products can be suitably used. For example, jER (registered trademark) 825, 827, 828, 828EL, 828US, 828XA, 834, 819, 806, 806H, 807, 4004P, 152, 157S70, 630, 630LSD, 871, 1750, YX8000, YX8034, YL980, YL983U, YX7105, YX7110B80, YX7400 Manufactured by Mitsubishi Chemical Corporation], Adeka Resin (registered trademark), EP-4100HF, EP-4901HF, EP-4000S, EP-4000L, EP-4003S, EP-4010S, EP-4010L, EP-4088S, EP-4088L, EP-330 E, EP-3300S, EP-3950S, EP-3950L, EP-3980S, EPR-4030, EP-49-23 (all manufactured by ADEKA Corporation), EPICLON (registered trademark) EXA- 850CRP, EXA-830CRP, EXA-830LVP, EXA-835LV, HP-4032D, HP-7200L, HP-7200, HP-7200H, HP-7200HH, HP-7200HHH, HP- 4700, HP-4770, HP-5000, HP-6000, EXA-4850-150, EXA-4850-1000, and EXA-4816 (all manufactured by DIC Corporation).
These epoxy compounds can be used alone or as a mixture of two or more.
By combining such a polyfunctional epoxy compound having no isocyanuric acid skeleton with an isocyanuric acid-based epoxy compound, a skeleton serving as a sufficient barrier against moisture can be obtained, so that a moisture-proof sealing material having high moisture permeability is formed. An epoxy resin composition is obtained.

In the present invention, the amount of the polyfunctional epoxy compound (b) having no isocyanuric acid skeleton is, for example, 100 to 1,000 parts by mass, preferably 100 parts by mass, based on 100 parts by mass of the (a) isocyanuric acid-based epoxy compound. It is preferably used in an amount of 200 to 900 parts by mass, more preferably 250 to 500 parts by mass.

[(C) Polyfunctional oxetane compound]
The polyfunctional oxetane compound is not particularly limited as long as it contains two or more oxetanyl groups in one molecule, and a commercially available product can be used.
Examples of the polyfunctional oxetane compound include bis ((oxetane-3-yl) methyl) ether, bis ((3-methyloxetane-3-yl) methyl) ether, and bis ((3-ethyloxetane-3-yl) Methyl) ether (DOX), 1,2-bis ((3-ethyloxetan-3-yl) methoxy) ethane, 1,2-bis ((3-ethyloxetan-3-yl) methoxy) propane, 1,3 -Bis ((3-ethyloxetane-3-yl) methoxy) propane, 1,4-bis ((3-ethyloxetane-3-yl) methoxy) butane, 1,6-bis ((3-ethyloxetane-3 -Yl) methoxy) hexane, 1,1,1-tris ((3-ethyloxetane-3-yl) methoxymethyl) propane, 1,2-bis ((3-ethyloxetane- -Yl) methoxy) benzene, 1,3-bis ((3-ethyloxetane-3-yl) methoxy) benzene, 1,4-bis ((3-ethyloxetane-3-yl) methoxy) benzene, 1,4 -Bis ((3-ethyloxetane-3-yl) methoxymethyl) benzene (XDO), 2,2'-bis ((3-ethyloxetane-3-yl) methoxy) biphenyl, 4,4'-bis (( 3-ethyloxetane-3-yl) methoxy) biphenyl, 4,4'-bis ((3-ethyloxetane-3-yl) methoxymethyl) biphenyl, bis ((3-ethyloxetane-3-yl) methyl) iso Phthalate and the like are mentioned, and bis ((3-ethyloxetane-3-yl) methyl) ether is particularly preferable.
As the polyfunctional oxetane compound, commercially available products can be suitably used. Examples thereof include Alonoxetane (registered trademark) OXT-121 and 221 (all manufactured by Toagosei Co., Ltd.) and Eternacoll (registered trademark) OXBP. And OXIPA [all manufactured by Ube Industries, Ltd.] and the like.
These polyfunctional oxetane compounds can be used alone or in combination of two or more.
By using a polyfunctional oxetane compound, a composition for a moisture-proof sealing material having excellent curability in a short time can be obtained.

In the present invention, the amount of the (c) polyfunctional oxetane compound to be used is, for example, 1 to 100 parts by mass, preferably 100 parts by mass, based on 100 parts by mass of the (a) isocyanuric acid-based epoxy compound and (b) the polyfunctional epoxy compound in total. Is preferably used in an amount of 2 to 50 parts by mass, more preferably 5 to 25 parts by mass.

[(D) Polymerization initiator generating acid or base by active energy ray]
As a polymerization initiator, it is sufficient that an acid or a base is generated by an active energy ray such as light to initiate polymerization of (a) an isocyanuric acid-based epoxy compound, (b) a polyfunctional epoxy compound, and (c) a polyfunctional oxetane compound. . Accordingly, the moisture-proof sealing material composition of the present invention does not immediately cure even when the components (a) to (d) are mixed, so that the storage stability is excellent and a sufficient working time can be obtained.

As the polymerization initiator that generates acid, a photoacid generator can be used. The photoacid generator is not particularly limited as long as it generates an acid (Lewis acid or Bronsted acid) directly or indirectly by light irradiation. Further, the curable composition containing the photoacid generator is cured by light irradiation without heating, and thus can be suitably used as a moisture-proof sealing material for an organic EL display substrate having low heat resistance.

Specific examples of the photoacid generator include onium salts such as iodonium salts, sulfonium salts, phosphonium salts, selenium salts, metallocene complex compounds, iron arene complex compounds, disulfone compounds, sulfonic acid derivative compounds, triazine compounds, acetophenone derivatives And a diazomethane compound.

Examples of the iodonium salt include diphenyliodonium, 4,4′-dichlorodiphenyliodonium, 4,4′-dimethoxydiphenyliodonium, 4,4′-di-tert-butyldiphenyliodonium, and 4-methylphenyl (4- ( 2-methylpropyl) phenyl) iodonium, 3,3'-dinitrophenyliodonium, 4- (1-ethoxycarbonylethoxy) phenyl (2,4,6-trimethylphenyl) iodonium, 4-methoxyphenyl (phenyl) iodonium and the like Of iodonium, chloride, bromide, mesylate, tosylate, trifluoromethanesulfonate, tetrafluoroborate, tetrakis (pentafluorophenyl) borate, hexafluorophosphate, hexafluoroarsene DOO, diaryliodonium salts such as hexafluoroantimonate, and the like.

Examples of the sulfonium salt include triphenylsulfonium, diphenyl (4-tert-butylphenyl) sulfonium, tris (4-tert-butylphenyl) sulfonium, diphenyl (4-methoxyphenyl) sulfonium, and tris (4-methylphenyl) Sulfonium, tris (4-methoxyphenyl) sulfonium, tris (4-ethoxyphenyl) sulfonium, diphenyl (4- (phenylthio) phenyl) sulfonium, tris (4- (phenylthio) phenyl) sulfonium, tris (4- (4-acetyl) Chloride, bromide, trifluoromethanesulfonate, tetrafluoroborate, tetrakis (pentafluorophenyl) borate, hexyl of sulfonium such as phenylthio) phenyl) sulfonium Hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate, triarylsulfonium salts, such as tris (trifluoromethylsulfonyl) methanide and the like.

Examples of the phosphonium salt include chloride, bromide, and tetrafluorophosphonium such as tetraphenylphosphonium, ethyltriphenylphosphonium, tetra (p-methoxyphenyl) phosphonium, ethyltri (p-methoxyphenyl) phosphonium, and benzyltriphenylphosphonium. And arylphosphonium salts such as borate, hexafluorophosphate and hexafluoroantimonate.

<< Examples of the selenium salt include, for example, triarylselenium salts such as triphenylselenium hexafluorophosphate.

{Examples of the iron arene complex compound include bis (η5-cyclopentadienyl) (η6-isopropylbenzene) iron (II) hexafluorophosphate.

The photoacid generator is commercially available, for example, CPI (registered trademark) -100P, 101A, 200K, 210S, 310B, 310FG, 410S, and IK-1 Co., Ltd.], IRGACURE (registered trademark) 250, 270, 290, GSID 26-1 [all manufactured by BASF Japan Co., Ltd.], WPAG-145, 149, 170, 199, 336, same 367, 370, 469, 638, 699, WPI-113, 116, 169, 170, 124 [all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] and the like can be preferably used. .
These photoacid generators can be used alone or in combination of two or more.
Among these, a sulfonium salt compound or an iodonium salt compound is preferable as a polymerization initiator. For example, compounds having an anionic species such as tetrakis (pentafluorophenyl) borate, hexafluorophosphate, and hexafluoroantimonate exhibiting strong acidity, and particularly, a reaction. A salt compound of tetrakis (pentafluorophenyl) borate is preferred from the viewpoint that hydrogen fluoride is not sometimes produced as a by-product.

The content of the photoacid generator in the moisture-proof sealing material composition of the present invention is based on 100 parts by mass of the total of (a) the isocyanuric acid-based epoxy compound, (b) the polyfunctional epoxy compound, and (c) the polyfunctional oxetane compound. For example, it can be 0.1 to 20 parts by mass, preferably 0.1 to 10 parts by mass, more preferably 0.5 to 10 parts by mass.

光 As the polymerization initiator for generating a base, a photobase generator can be used. The photobase generator is not particularly limited as long as it generates a base (Lewis base or Bronsted base) directly or indirectly by light irradiation. Since the moisture-proof sealing material composition containing the photobase generator cures by light irradiation without heating, it can be suitably used as a moisture-proof sealing material for organic EL display substrates having low heat resistance.

Examples of the photobase generator include alkylamine photobase generators such as 9-anthrylmethyl = N, N-diethylcarbamate; 9-anthryl = N, N-dicyclohexylcarbamate; 1- (9,10-anthraquinone) -2-yl) ethyl = N, N-dicyclohexylcarbamate, dicyclohexylammonium = 2- (3-benzoylphenyl) propionate, 9-anthryl = N-cyclohexylcarbamate, 1- (9,10-anthraquinone-2-yl) ethyl = N-cyclohexylcarbamate, cyclohexylammonium = cycloalkylamine-based photobase generator such as 2- (3-benzoylphenyl) propionate, (E) -N-cyclohexyl-3- (2-hydroxyphenyl) acrylamide; 9-anthrylmethy = Piperidine-1-carboxylate, (E) -1-piperidino-3- (2-hydroxyphenyl) -2-propen-1-one, (2-nitrophenyl) methyl = 4-hydroxypiperidine-1-carboxylate , (2-nitrophenyl) methyl 4- (methacryloyloxy) piperidine-1-carboxylate and other piperidine photobase generators; guanidinium 2- (3-benzoylphenyl) propionate, 1,2-diisopropyl-3- (Bis (dimethylamino) methylene) guanidinium = 2- (3-benzoylphenyl) propionate, 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidium = n-butyltriphenylborate, 1, 5,7-triazabicyclo [4.4.0] dec-5-enium = A guanidine-based photobase generator such as-(9-oxoxanthen-2-yl) propionate; an imidazole-based photobase generator such as 1- (9,10-anthraquinone-2-yl) ethyl imidazole-1-carboxylate And the like.
The photobase generator can be obtained as a commercial product. Examples thereof include WPBG-174, 018, 041, 015, 172, 166, 140, 168, 025, 167, and 300. , 266, 158, 165, 082, and 027 [all manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.] and the like.
These photobase generators can be used alone or in combination of two or more.

The content of the photobase generator in the moisture-proof sealing material composition of the present invention is based on 100 parts by mass of (a) an isocyanuric acid-based epoxy compound, (b) a polyfunctional epoxy compound, and (c) a polyfunctional oxetane compound. For example, the amount can be 0.1 to 30 parts by mass, preferably 0.1 to 20 parts by mass, and more preferably 0.5 to 10 parts by mass.

[Other components]
Further, the moisture-proof sealing material composition of the present invention may contain a conventional additive as long as the effects of the present invention are not impaired. Such additives include, for example, solvents, surfactants, adhesion promoters, thickeners, sensitizers, defoamers, leveling agents, coating improvers, lubricants, stabilizers (antioxidants, Heat stabilizers, light stabilizers, etc.), plasticizers, dissolution promoters, fillers (such as silica), antistatic agents, silane coupling agents and the like. These additives may be used alone or in combination of two or more.

[Silane coupling agent]
The silane coupling agent is not particularly limited as long as it contains an alkoxysilyl group and other reactive functional groups in the molecule, and a commercially available product can be used.

Examples of the silane coupling agent include vinyl group-containing silane coupling agents such as trimethoxy (vinyl) silane, triethoxy (vinyl) silane, and trimethoxy (7-octenyl) silane; 2- (3,4-epoxycyclohexyl) ethyltrisilane Methoxysilane, 3-glycidyloxypropyldimethoxy (methyl) silane, 3-glycidyloxypropyltrimethoxysilane, diethoxy (3-glycidyloxypropyl) (methyl) silane, triethoxy (3-glycidyloxypropyl) silane, 8-glycidyloxy Epoxy group-containing silane coupling agents such as octyltrimethoxysilane and triethoxy (8-glycidyloxyoctyl) silane; vinylphenyl group-containing silane cups such as trimethoxy (4-vinylphenyl) silane 3-methacryloyloxypropyldimethoxy (methyl) silane, 3-methacryloyloxypropyltrimethoxysilane, diethoxy (3-methacryloyloxypropyl) methylsilane, triethoxy (3-methacryloyloxypropyl) silane, trimethoxy (8-methacryloyloxyoctyl) A) silane-containing silane coupling agent such as silane; acryl-containing silane coupling agent such as 3-acryloyloxypropyltrimethoxysilane; 3-((2-aminoethyl) amino) propyldimethoxy (methyl) silane, 3- ((2-aminoethyl) amino) propyltrimethoxysilane, 8-((2-aminoethyl) amino) octyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyl Piltriethoxysilane, N- (1,3-dimethylbutylidene) -3-triethoxysilylpropylamine, trimethoxy (3-phenylaminopropyl) silane, trimethoxy (3-((2-((vinylbenzyl) amino) Amino group-containing silane coupling agents such as ethyl) amino) propyl) silane hydrochloride; ureido group-containing silane coupling agents such as trimethoxy (3-ureidopropyl) silane and triethoxy (3-ureidopropyl) silane; triethoxy (3- Isocyanate group-containing silane coupling agents such as isocyanatopropyl) silane; isocyanurate type silane coupling agents such as tris (3-trimethoxysilylpropyl) isocyanurate and tris (3-triethoxysilylpropyl) isocyanurate; 3- Mercap Mercapto group-containing silane coupling agents such as tripropyldimethoxy (methyl) silane and 3-mercaptopropyltrimethoxysilane; and acid anhydride type silane coupling agents such as (3-trimethoxysilylpropyl) succinic anhydride. Can be
Among them, an epoxy group-containing silane coupling agent is preferable, a glycidyl group-containing silane coupling agent is more preferable, and 3-glycidyloxypropyltrimethoxysilane and triethoxy (3-glycidyloxypropyl) silane are particularly preferable.

Commercially available products can be suitably used as the silane coupling agent. For example, Shin-Etsu Silicone (registered trademark) KBM-1003, KBE-1003, KBM-1083, KBM-303, KBM-402 KBM-403, KBE-402, KBE-403, KBM-4803, KBM-1403, KBM-502, KBM-503, KBE-502, KBE-503, KBM-5803 KBM-5103, KBM-602, KBM-603, KBM-6803, KBM-903, KBE-903, KBE-9103P, KBM-573, KBM-575, KBE-585 , The same KBE-9007, the same KBM-9659, the same KBE-9659, the same KBM-802, the same KBM-803, X-12-967C [both manufactured by Shin-Etsu Chemical Co., Ltd.], and the like.

These silane coupling agents can be used alone or as a mixture of two or more.
By adding these silane coupling agents, a composition for a moisture-proof sealing material having excellent ion migration resistance can be obtained.

In the present invention, when a silane coupling agent is added, for example, 0.1% by mass of the total of (a) the isocyanuric acid-based epoxy compound, (b) the polyfunctional epoxy compound, and (c) the polyfunctional oxetane compound. It is preferably used in an amount of 1 to 10 parts by mass, preferably 0.1 to 5 parts by mass, more preferably 0.5 to 2 parts by mass.

[Method of preparing composition for moisture-proof sealing material]
The composition for a moisture-proof sealing material of the present invention can be prepared by mixing the components by a known method. The mixing is not particularly limited as long as it can be uniformly mixed. For example, the mixing is performed under heating as necessary in consideration of the viscosity, and is performed at a temperature of 10 to 100 ° C. for 0.5 to 1 hour. If necessary, defoaming and stirring are further performed to remove air bubbles in the composition.

[Organic EL display]
The composition for a moisture-proof seal material of the present invention can be used as a sealing material or an adhesive material between a shield material and a substrate or an electrode in an electric device such as an organic EL display, in particular, an organic EL element of an organic EL display. it can.
Thereby, the organic EL element can be prevented from being corroded and oxidized by moisture and oxygen from the outside, and the formation of a dark spot and a decrease in luminance can be prevented.
The method for curing the moisture-proof sealing material composition of the present invention is not particularly limited, and a known method such as irradiation with active energy rays such as light can be used. Examples of the active energy ray include an ultraviolet ray, an electron beam, and an X-ray, and an ultraviolet ray is particularly preferable. As a light source used for ultraviolet irradiation, a solar ray, a chemical lamp, a low-pressure mercury lamp, a high-pressure mercury lamp, a metal halide lamp, a xenon lamp, a UV-LED, or the like can be used.
Since the composition for a moisture-proof seal material of the present invention is cured by being applied and irradiated with an active energy ray, a heating (baking) step at a high temperature is not required for curing. Therefore, it can be suitably used for manufacturing an organic EL element having low heat resistance.

湿 The moisture-proof sealing material composition of the present invention is excellent in photocurability and can form a cured product excellent in moisture-proof property, so that various elements can be appropriately sealed. Furthermore, the moisture-proof sealing material composition of the present invention can form a cured product having excellent stretchability, and is therefore very useful as a sealing material for sealing a display element such as an organic EL element used for a flexible display.

Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples. In the examples, the devices and conditions used for sample preparation and physical property analysis are as follows.

(1) Stirring and defoaming device: Rotating / revolving mixer manufactured by Shinky Co., Ltd. Awatori Rentaro (registered trademark) ARE-310
(2) Bar coater: PM-9050MC manufactured by SMT Co., Ltd.
Bar coater: SA-203 No. manufactured by Tester Sangyo Co., Ltd. 65, wet film thickness: 148.6 μm
Coating speed: 4 m / min (3) Moisture permeability Constant temperature and humidity device: Small environmental tester SH-262 manufactured by Espec Corporation
Moisture permeable cup: Made by Imoto Manufacturing Co., Ltd.
(4) Tensile test equipment: Tabletop precision universal testing machine Autograph AGS-5kNX manufactured by Shimadzu Corporation
Gripping tool: Pneumatic flat gripping tool Gripping tooth: Rubber coated gripping tooth Peeling speed: 5 mm / min Measurement temperature: Room temperature (about 23 ° C)
(5) Ion migration evaluation evaluation apparatus: Electrochemical migration evaluation system AMI-025-U-5 manufactured by Espec Corporation
Constant temperature and humidity device: Small environmental tester SH-222 manufactured by Espec Corporation

The meanings of the abbreviations used are as follows.
ADGIC: monoallyl diglycidyl isocyanurate [MA-DGIC manufactured by Shikoku Chemicals Co., Ltd.]
TEOIC: Tris (7,8-epoxyoctyl) isocyanurate [TEPIC (registered trademark) -FL manufactured by Nissan Chemical Industries, Ltd.]
TEPEIC: Tris (4,5-epoxypentyl) isocyanurate [TEPIC (registered trademark) -VL manufactured by Nissan Chemical Industries, Ltd.]
TGIC: triglycidyl isocyanurate [TEPIC (registered trademark) -L manufactured by Nissan Chemical Industries, Ltd.)
BPAN: bisphenol A novolak type epoxy resin [jER (registered trademark) 157S70 manufactured by Mitsubishi Chemical Corporation]
BPF: bisphenol F type epoxy resin [jER (registered trademark) 807, manufactured by Mitsubishi Chemical Corporation)
DCP: dicyclopentadiene dimethanol diglycidyl ether [ADEKARESIN (registered trademark) EP-4088L manufactured by ADEKA Corporation]
DOX: 3,3 ′-(oxybis (methylene)) bis (3-ethyloxetane) [Alonoxetane (registered trademark) OXT-221 manufactured by Toagosei Co., Ltd.]
C100P: diphenyl (4- (phenylthio) phenyl) sulfonium hexafluorophosphate [CPI (registered trademark) -100P, 50% propylene carbonate solution manufactured by San Apro Co., Ltd.]
C101A: diphenyl (4- (phenylthio) phenyl) sulfonium hexafluoroantimonate (V) [CPI (registered trademark) -101A manufactured by San Apro Co., Ltd., 50% propylene carbonate solution]
C310B: Triarylsulfonium tetrakis (pentafluorophenyl) borate [CPI (registered trademark) -310B manufactured by San Apro Co., Ltd.]
GTMS: 3-glycidyloxypropyltrimethoxysilane [Shin-Etsu Silicone (registered trademark) KBM-403 manufactured by Shin-Etsu Chemical Co., Ltd.]

[Example 1]
20 parts by mass of TEPeIC as an isocyanuric acid-based epoxy compound, 70 parts by mass of BPF as a polyfunctional epoxy compound having no isocyanuric acid skeleton, 10 parts by mass of DOX as a polyfunctional oxetane compound, and 3 parts by mass of C101A (in terms of active ingredient) as a polymerization initiator are mixed. did. This mixture was stirred and defoamed (2,000 rpm for 4 minutes, followed by 1,000 rpm for 4 minutes) to prepare Composition 1.
This composition was bar-coated on a PET film [Lumirror (registered trademark) S10 manufactured by Toray Industries, Inc.]. This coating film was cured by irradiating it with UV light at 20 mW / cm ² for 50 seconds using a high-pressure mercury lamp in an air atmosphere. The cured product was peeled from the PET film to obtain a cured film having a thickness of about 100 μm.

(4) The moisture permeability and elongation at break of the obtained cured film were evaluated. The procedure of each evaluation is shown below. Table 1 shows the results.

[Moisture permeability]
The moisture permeability of the cured film was measured according to JIS Z 0208: 1976, a moisture permeability test method for a moisture-proof packaging material (cup method). To form a test body (transmission area: 28.3 cm ² ). The test specimen was placed in a thermo-hygrostat set at a temperature of 40 ° C. and a relative humidity of 90% (condition B). After a lapse of 24 hours, the specimen was taken out and the mass of the specimen was measured. The operation of placing the test sample in the thermo-hygrostat again, taking out the test sample at 24 hour intervals and weighing it was repeated until the weight increase became constant, and the moisture permeability (actual measurement) of the membrane was calculated.
In this test, the moisture permeability of the cured film produced so that the film thickness was in the range of 80 to 500 μm was measured in consideration of the influence of the difference in the film thickness of the test piece, and converted into a 100 μm thickness by the following equation. The value was used as the evaluation value.
Moisture permeability ^{[g / m 2 · 24h]} = moisture permeability (measured) × test KatamakuAtsu [μm] ÷ 100 [μm]

[Elongation at break]
The cured film was cut into a rectangle having a length of 60 mm and a width of 15 mm to prepare a test piece. The test piece was attached to a grip of a universal testing machine so as to grip 20 mm each from both ends in the longitudinal direction, and a tensile test was performed. The length I [mm] between the gauge points (between the grippers) when the fractured sections were butted so that the center lines of both fractured pieces of the test piece were on a straight line was measured. Calculated.
Elongation at break δ [%] = (I ₀ ) ÷ I ₀ × 100
(I ₀ : distance between original reference points = 20 [mm])

[Examples 2 to 4, Comparative Examples 1 and 2]
Each cured film was obtained in the same manner as in Example 1 except that each composition was changed to the description in Table 1. The compositions 5 and 6 were insufficiently cured under the same curing conditions (exposure conditions) and remained sticky on the surface of the cured product. Therefore, they were further heated (post-cured) on a hot plate at 100 ° C. for 30 minutes. Table 1 shows the moisture permeability and elongation at break of each cured film.

As shown in Table 1, the cured products obtained from the compositions of Examples 1 to 4 had lower moisture permeability and the elongation at break than the cured products obtained from the compositions of Comparative Examples 1 and 2. Was also higher. That is, it was shown that the composition of the present invention can provide a cured product having excellent moisture resistance and stretchability.
In addition, it was confirmed that the compositions of Examples 1 to 4 obtained cured products excellent in moisture resistance and stretchability only by UV exposure, and were excellent in photocurability.

[Examples 5 to 10]
Compositions 7 to 10 were prepared in the same manner as in Example 1, except that each composition was changed as described in Table 2.

操作 A cured film having a thickness of about 100 μm was prepared in the same manner as in Example 1 except that the obtained composition was used. The moisture permeability of each cured film was evaluated in the same manner as in Example 1. Table 3 shows the results.

Further, as shown in FIG. 2, a silicone rubber spacer having a thickness of 500 μm was placed on a glass substrate on which two silver electrodes having the shape shown in FIG. 1 were formed, and each composition was applied so as to cover both electrodes. did. The coated substrate was covered with a quartz glass substrate of the same size as that of the coated substrate, which had been previously subjected to a release treatment by Optool (registered trademark) DSX (manufactured by Daikin Industries, Ltd.). Using a UV-LED (wavelength: 365 nm), UV light was irradiated from the quartz glass substrate side at 100 mW / cm ² for 10 seconds to cure the applied composition. Thereafter, the quartz glass substrate and the spacer were removed to obtain a test piece in which both electrodes were sealed with a cured product having a thickness of 500 μm.

In a thermo-hygrostat set to the temperature and humidity shown in Table 3, a DC voltage shown in Table 3 was applied to both electrodes of the obtained test piece, and ion migration occurred (the resistance between both electrodes was 10%). ^{The time up to 5} Ω or less) was measured and evaluated. The results are shown in Table 3.

As shown in Table 3, the cured products (Examples 6 to 10) obtained from the compositions using the sulfonium salt compounds having tetrakis (pentafluorophenyl) borate ion as the polymerization initiator maintained low moisture permeability. As it was, it was confirmed that the ion migration resistance was excellent. It was also confirmed that the addition of the silane coupling agent further improved the ion migration resistance (Example 10).

1. Silver electrode2. Composition 3. spacer

Claims (10)

1. (A) at least one isocyanuric acid-based epoxy compound selected from the group consisting of the compound represented by the formula [1] and the compound represented by the formula [2]; (b) a polyfunctional compound having no isocyanuric acid skeleton A composition for a moisture-proof sealing material, comprising: an epoxy compound; (c) a polyfunctional oxetane compound; and (d) a polymerization initiator that generates an acid or a base by an active energy ray.
   

   

   (Wherein, R ¹ represents a hydrogen atom or a methyl group, and L ¹ represents an alkylene group having 2 to 7 carbon atoms. Here, each R ¹ may be the same or different. , Each L ¹ may be the same or different.)
   

   

   (Wherein, R ² represents a hydrogen atom or a methyl group, L ² represents an alkylene group having 1 to 5 carbon atoms, and A represents an aliphatic group which may contain a (n + 1) -valent ether bond. Represents a hydrocarbon group, and n represents an integer of 2 to 5. Here, each R ² may be the same or different, and each L ² may be the same or different. And each A may be the same or different, and each n may be the same or different.)
2. (B) The polyfunctional epoxy compound having no isocyanuric acid skeleton is a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a hydrogenated bisphenol A type epoxy resin, a hydrogenated bisphenol F type epoxy resin, a bisphenol A novolak type epoxy resin The composition for a moisture-proof sealing material according to claim 1, wherein the composition is at least one selected from the group consisting of a resin, a bisphenol F novolak type epoxy resin, and an alicyclic polyglycidyl ether type epoxy resin.
3. (B) the polyfunctional epoxy compound having no isocyanuric acid skeleton is bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, bisphenol A novolak polyglycidyl The composition for a moisture-proof sealing material according to claim 2, wherein the composition is at least one selected from the group consisting of ether and dicyclopentadiene dimethanol diglycidyl ether.
4. The composition for a moisture-proof sealing material according to claim 3, wherein the polyfunctional epoxy compound (b) having no isocyanuric acid skeleton is bisphenol F diglycidyl ether.
5. The composition for a moisture-proof sealing material according to any one of claims 1 to 4, wherein the polymerization initiator (d) that generates an acid or a base by an active energy ray is a photoacid generator.
6. The composition for a moisture-proof sealing material according to any one of claims 1 to 5, wherein the (a) isocyanuric acid-based epoxy compound is a compound represented by the formula [1].
7. The moisture permeability of the cured product measured under the cup method condition B (temperature 40 ° C., relative humidity 90%) of the moisture permeability test method of the moisture-proof packaging material according to JIS Z 0208 (1976) is 20 g / 100 μm in terms of thickness. m is 2 ^· 24h or less, according to claim 1 or moisture sealant composition according to any one of claims 6.
8. The composition for a moisture-proof seal material according to any one of claims 1 to 7, which is a composition for an organic EL display moisture-proof seal material.
9. A cured product obtained by curing the moisture-proof sealing material composition according to any one of claims 1 to 8.
10. An organic EL display on which the cured product according to claim 9 is mounted.

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