KR102149717B1 - Resin composition for electronic device - Google Patents

Abstract

The present invention is a resin composition for an electronic device that imparts a cured product having a low moisture permeability, (A) a partial (meth)acrylated epoxy resin of a bifunctional or higher epoxy resin, (B) a monofunctional epoxy compound, (C) an amine-based curing agent And (D) a resin composition for electronic devices containing a polymerization initiator.

Description

Resin composition for electronic device

The present invention relates to a resin composition for electronic devices.

Electronic devices such as organic electroluminescence, electronic paper, solar cells, and liquid crystal displays are sealed (sealed) with a resin composition mainly for the purpose of preventing adverse effects due to moisture.

As such a resin composition, a radical polymerization reactive resin based on an epoxy acrylate compound is widely used (see, for example, Patent Document 1).

Japanese Patent Publication No. 2007-297470

However, the cured product of the resin composition described in Patent Document 1 was not sufficiently low in moisture permeability. An object of the present invention is to provide a resin composition for electronic devices that provides a cured product with low moisture permeability.

The present invention includes the following aspects.

[1] A resin composition for an electronic device containing (A) a partial (meth)acrylated epoxy resin of a bifunctional or higher epoxy resin, (B) a monofunctional epoxy compound, (C) an amine-based curing agent, and (D) a polymerization initiator.

[2] The resin composition for electronic devices according to [1], in which (B) is a compound represented by the following formula (1).

X ¹ -G (1)

[In the formula, G is a glycidyloxy group or a methylglycidyloxy group, X ¹ is an optionally substituted aryl group, an optionally substituted aryl-(OR ¹ ) _n1 group (where R ¹ is an alkylene group, n1 is an integer of 1 to 6), an optionally substituted aryl-R ² group (here, R ² is an alkylene group), optionally substituted heteroaryl group, optionally substituted heteroaryl-(OR ³ ) _n2 group (Here, R ³ is an alkylene group, and n2 is an integer of 1 to 6), or a heteroaryl-R ⁴ group which may be substituted (here, R ⁴ is an alkylene group).]

[3] The resin composition for an electronic device according to [1] or [2], wherein the epoxy equivalent of (B) is 80 to 2,000 g/eq.

[4] (A) is bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F no Rock type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy resin and triphenolmethane skeleton The resin composition of any of [1] to [3], which is a partial (meth)acrylated epoxy resin of at least one epoxy resin selected from the group consisting of phenol novolak type epoxy resins.

[5] The resin composition for an electronic device according to any of [1] to [4], wherein (B) is 1 to 40 parts by mass with respect to 100 parts by mass in total of (A) and (B).

[6] The resin composition for electronic devices in any of [1] to [5], which is a sealing agent for a liquid crystal dropping method.

According to the present invention, there is provided a resin composition for an electronic device that provides a cured product having a low moisture permeability.

Hereinafter, the present invention will be described in detail. In addition, in this specification, (meth)acryl means methacryl and/or acrylic, and (meth)acrylate means methacrylate and/or acrylate. "It may be substituted" means "which is substituted or unsubstituted". (A) Part of a bifunctional or higher epoxy resin (meth)acrylated epoxy resin may be simply described as (A). The same applies to (B), (C) and (D).

[Resin composition for electronic devices]

The resin composition for an electronic device (hereinafter, also simply referred to as ``resin composition'') includes (A) a partial (meth)acrylated epoxy resin of a bifunctional or higher epoxy resin, (B) a monofunctional epoxy compound, (C) an amine-based curing agent, and (D) It contains a polymerization initiator.

<(A) Part of a bifunctional or higher epoxy resin (meth)acrylated epoxy resin>

(A) Partial (meth)acrylated epoxy resin of bifunctional or higher epoxy resin means a resin in which some epoxy groups in the epoxy resin react with (meth)acrylic acid, that is, both epoxy groups and (meth)acrylic groups in the resin It means a resin having.

(A) can be obtained by reaction of a bifunctional or more functional epoxy resin and (meth)acrylic acid. The number of functionalities of the bifunctional or higher epoxy resin is not particularly limited, but it is preferably 2 to 4.

Bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin, bisphenol A novolak type epoxy resin , Bisphenol F novolak type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy resin, tree And phenol novolak type epoxy resins having a phenol methane skeleton. In addition, diglycidyl ether products of difunctional phenols, diglycidyl ether products of difunctional alcohols, their halides, hydrogenated products, and the like can also be used. Moreover, as a trifunctional and tetrafunctional epoxy resin, the epoxy resin described in Japanese Patent Laid-Open No. 2012-077202 can be mentioned.

The bifunctional or more epoxy resin may be one or a combination of two or more.

As for (A), it is preferable that it is 10 to 90 mol%, and it is more preferable that it is 40 to 60 mol% with respect to the total number of moles of (meth)acrylic group and epoxy group in resin. (A) contains a compound each containing an epoxy group and one or more (meth)acrylic groups in one molecule. In addition, (A) is a compound having two or more epoxy groups per molecule and not having a (meth)acrylic group, corresponding to an unreacted epoxy compound in a bifunctional or higher epoxy resin as a raw material, and all of the epoxy compounds. A compound having two or more (meth)acrylic groups in one molecule and not having an epoxy group may be included in which the epoxy group corresponds to the compound reacted with (meth)acrylic acid.

In the production of (A), the reaction amount of the bifunctional or higher epoxy resin and (meth)acrylic acid is not particularly limited as long as it is an amount that becomes a predetermined equivalent ratio. In the reaction of a bifunctional or higher epoxy resin with (meth)acrylic acid, a catalyst (e.g., benzyldimethylamine, triethylamine, benzyltrimethylammonium chloride, triphenylphosphine, triphenylstyrene, etc.), and a polymerization inhibitor ( For example, metoquinone, hydroquinone, methylhydroquinone, phenothiazine, dibutylhydroxytoluene, etc.) can be used. The reaction temperature between the bifunctional or higher epoxy resin and (meth)acrylic acid can be, for example, 80 to 110°C. Thereby, a part of the epoxy group of the bifunctional or higher epoxy resin can be (meth)acrylated.

(A), which is a partial (meth)acrylated epoxy resin obtained by reacting a bisphenol A type epoxy resin with (meth)acrylic acid, is obtained, for example, as follows.

First, a bisphenol A type epoxy resin and (meth)acrylic acid are reacted in the presence of a basic catalyst, preferably a trivalent organic phosphoric acid compound and/or an amine compound. The reaction ratio at this time is a ratio of 10 to 90 equivalent% of (meth)acrylic acid with respect to 1 equivalent of the epoxy group. Subsequently, the reaction product is purified by removing the basic catalyst by treatment such as filtration, centrifugation and/or water washing. As the basic catalyst, a known basic catalyst used for the reaction of an epoxy resin and (meth)acrylic acid can be used. Further, a polymer-supported basic catalyst in which a basic catalyst is supported on the polymer may be used.

(A) may be 1 type or a combination of 2 or more types.

<(B) monofunctional epoxy compound>

(B) The monofunctional epoxy compound is a component that reduces the moisture permeability of the cured product of the resin composition. When instead of (B), a bifunctional or higher polyfunctional epoxy compound and/or a monofunctional acrylic compound are used, the moisture permeability cannot be effectively reduced.

(B) is not particularly limited as long as it is a compound having one epoxy group in the molecule, and includes an aromatic monofunctional epoxy compound and an aliphatic monofunctional epoxy compound, and an aromatic monofunctional epoxy compound is preferable. However, (B) is other than a monofunctional epoxy compound contained in (A) (that is, a compound containing one epoxy group per molecule and one or more (meth)acrylic groups.).

<<aromatic monofunctional epoxy compound>>

The aromatic monofunctional epoxy compound is not particularly limited as long as it is a monofunctional epoxy compound having an aromatic group and/or a heteroaromatic group in the molecule, but a compound represented by the following formula (1) is preferable.

X ¹ -G (1)

[In the formula, G is a glycidyloxy group or a methylglycidyloxy group, X ¹ is an optionally substituted aryl group, an optionally substituted aryl-(OR ¹ ) _n1 group (where R ¹ is an alkylene group, n1 is an integer of 1 to 6), an optionally substituted aryl-R ² group (here, R ² is an alkylene group), optionally substituted heteroaryl group, optionally substituted heteroaryl-(OR ³ ) _n2 group (Here, R ³ is an alkylene group, and n2 is an integer of 1 to 6), or a heteroaryl-R ⁴ group which may be substituted (here, R ⁴ is an alkylene group).

The aryl group preferably has 6 to 20 carbon atoms, and includes a phenyl group, a biphenylyl group, a naphthyl group, a terphenylyl group, an anthracenyl group, and a fluorenyl group. From the viewpoint of further lowering the moisture permeability of the cured product, the aryl group for X ¹ is preferably a phenyl group, a biphenylyl group, and a naphthyl group, and particularly preferably a phenyl group.

The heteroaryl group has a total number of 5 to 30 atoms, is a monocyclic or polycyclic heterocyclic group containing at least one hetero atom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in addition to carbon atoms, and 5 to 20 carbon atoms It is preferable to be. Heteroaryl group is a phthalimidyl group, imidazolyl group, xanthenyl group, thioxanthenyl group, thienyl group, dibenzofuryl group, chromaenyl group, isothiochromenyl group, phenoxatiinyl group, pyrrolyl group, pyrazolyl group , Pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolizinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolidinyl group, isoquinolyl group, quinolyl group, phthala Genyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, carbazolyl group, β-carbolinyl group, phenanthridinyl group, acridinyl group, perimidinyl group, phenane Trolinyl group, phenadinyl group, isothiazolyl group, phenothiazinyl group, isoxazolyl group, furazanyl group, furanyl group, etc. are mentioned.

Substituents of the aryl group and heteroaryl group include an alkyl group, a hydroxyalkyl group, an alkoxy group, an aryloxy group (preferably a phenoxy group), an arylalkyl group (preferably 1-methyl-1-phenylethyl group), arylalkyloxy group. Group consisting of a group (preferably a benzyloxy group), a formyl group, an acyl group (preferably a benzoyl group), a cyano group, a nitro group, a sulfo group, an amide group (preferably a NH ₂ CO group), a halogen atom, etc. At least one type selected from is mentioned.

The alkyl group preferably has 1 to 20 carbon atoms, and is linear or branched, and is a methyl group, ethyl group, propyl group, i-propyl group, butyl group, i-butyl group, sec-butyl group, tert-butyl group, etc. Can be mentioned. The hydroxyalkyl group is an alkyl group substituted with a hydroxy group, and the alkyl moiety in the hydroxyalkyl group is as described above. The alkyl moiety in the alkoxy group is as described above. The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

When X ¹ has a substituent, from the viewpoint of further lowering the moisture permeability of the cured product, the substituent is one selected from the group consisting of an alkyl group, a hydroxyalkyl group, an aryloxy group, an arylalkyloxy group, formyl group, acyl group, and halogen atom. The above is preferable.

The alkylene group preferably has 1 to 6 carbon atoms, is linear or branched, and is a methylene group, ethylene group, ethylidene group (ethane-1,1-diyl group), trimethylene group, propylene group (propane- 1,2-diyl group), propylidene group (propane-1,1-diyl group), isopropylidene group (propane-2,2-diyl group), tetramethylene group, butylidene group (butane-1,1 -Diyl group), isobutylidene group (2-methylpropane-1,1-diyl group), pentamethylene group, 2-methylpentane-1,5-diyl group, and hexamethylene group.

R ¹ and R ³ are preferably an ethylene group, a trimethylene group and a propylene group. n1 and n2 are preferably an integer of 1 to 4, and 1 is particularly preferable. R ² and R ⁴ are preferably an ethylene group and an ethylidene group.

It is preferable that X ¹ is an optionally substituted aryl group, an optionally substituted aryl-(OR ¹ ) _n1 group, or an optionally substituted heteroaryl-R ⁴ group. Moreover, when X ¹ is an aryl group which may be substituted, it is more preferable that it is an aryl group unsubstituted or substituted with the above-described preferable substituent.

The aromatic monofunctional epoxy compound may be one or a combination of two or more.

<< aliphatic monofunctional epoxy compound >>

The aliphatic monofunctional epoxy compound is not particularly limited as long as it is a monofunctional epoxy compound having an aliphatic group in a molecule and not having an aromatic ring and/or a hetero aromatic ring. That is, in the aliphatic monofunctional epoxy compound, neither an aromatic ring nor a hetero aromatic ring exists in the molecule. The aliphatic monofunctional epoxy compound is preferably a monofunctional epoxy compound represented by the following formula (2).

X ² -G (2)

[In the formula, G is as defined by formula (1), and X ² is an optionally substituted alkyl group, an optionally substituted alkyl-(OR ⁵ ) _n3 group (here, R ⁵ is an alkylene group, and n3 is 1 To 6), optionally substituted alkenyl group, optionally substituted alkenyl-(OR ⁶ ) _n4 group (here, R ⁶ is an alkylene group, n4 is an integer of 1 to 6), optionally substituted alkyne A nil group or an optionally substituted alkynyl-(OR ⁷ ) _n5 group (here, R ⁷ is an alkylene group, and n5 is an integer of 1 to 6)

The alkyl group is as described above. The alkenyl group is preferably 2 to 20 carbon atoms, linear or branched, vinyl group, allyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 2-pentenyl group, 3-pente A nil group, a 4-pentenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, etc. are mentioned. The alkynyl group preferably has 2 to 20 carbon atoms, and is linear or branched, and is an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 2-pentynyl group, a 3-pentynyl group, and a 4- A pentynyl group, a 2-hexynyl group, a 3-hexynyl group, a 4-hexynyl group, a 5-hexynyl group, etc. are mentioned. The substituents of the alkyl group, alkenyl group, and alkynyl group include one or more selected from the group consisting of formyl group, acyl group, cyano group, nitro group, sulfo group, amide group, and halogen.

R ⁵ , R ⁶ and R ⁷ have the same meaning as R ¹ , and the preferred range is also the same. n3, n4 and n5 have the same meaning as n1, and the preferred range is also the same.

It is preferable that X ² is an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted alkynyl group.

The aliphatic monofunctional epoxy compound may be one or a combination of two or more.

<<preferred mode>>

It is preferable that (B) contains only one or more selected from the group consisting of (b1) to (b18) disclosed in Examples.

From the viewpoint of further lowering the moisture permeability of the cured product, the epoxy equivalent of (B) is preferably 80 to 2,000 g/eq, and more preferably 100 to 1,000 g/eq.

(B) may be 1 type or a combination of 2 or more types.

<(C) Amine curing agent>

(C) The amine curing agent has a primary amino group, a secondary amino group or a tertiary amino group, and the primary amino group and the secondary amino group have active hydrogens derived from these amino groups. (C) is activated by heat, reacts with an epoxy group in the resin composition, and cures the resin composition.

Although the amine-based curing agent is not particularly limited, a polyaddition type curing agent and a catalytic curing agent are mentioned. Examples of the polyaddition type curing agent include aromatic amines, organic acid dihydrazide compounds, amine adducts, dicyandiamide, polyamine compounds, and epoxy-modified polyamines, and examples of the catalytic curing agent include imidazole, derivatives of imidazole, tertiary Amine, tertiary amine salt polyaminourea, and the like. Amine-based curing agent is VDH (1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin), ADH (adipic acid dihydrazide), UDH (7,11-octadecadiene-1,18- Organic acid dihydrazides such as dicarbohydrazide) and LDH (octadecane-1,18-dicarboxylic acid dihydrazide); Polyamine compounds sold by ADEKA as Adeka Hardener EH5030S; An amine adduct marketed as Azicure PN-23, Azicure PN-30, Azicure MY-24, Azicure MY-H, etc. from Ajinomoto Fine Techno is preferable.

(C) may be 1 type or a combination of 2 or more types.

<(D) polymerization initiator>

(D) The polymerization initiator is a component that serves as a radical generating source in photoradical polymerization and/or thermal radical polymerization of the (meth)acryloyl group contained in (A). As (D), one or more types selected from the group consisting of a photo radical polymerization initiator and a thermal radical polymerization initiator can be mentioned. By using a photoradical polymerization initiator, the resin composition can be cured with light and heat. By using a thermal radical polymerization initiator, it can be set as a curable composition which hardens a resin composition by heat.

<<Optical radical polymerization initiator>>

Photo radical polymerization initiators include benzoins, acetophenones, benzophenones, thioxanthones, α-acyloxime esters, phenylglyoxylates, benzyls, azo compounds, diphenylsulfide compounds, acylphos And pinoxide compounds, benzoin ethers and anthraquinones. It is preferable that the photoradical polymerization initiator has a low solubility in liquid crystal and has a reactive group in which the decomposition product does not gasify upon irradiation with light.

As a photo-radical polymerization initiator, reacting a compound containing at least two epoxy groups, a compound obtained by reacting dimethylaminobenzoic acid, a compound containing at least two epoxy groups, and hydroxythioxanthone described in WO2012/077720 A polymerization initiator which is a mixture of the compounds obtained by making them is preferable. Here, the compound having at least two epoxy groups is preferably a bifunctional or higher epoxy resin as described above.

<<Thermal radical polymerization initiator>>

The thermal radical polymerization initiator generates radicals by heating and initiates a polymerization reaction. The thermal radical polymerization initiator is not particularly limited, and examples include organic peroxides and azo compounds. The thermal radical polymerization initiator may be one or a combination of two or more.

(D) may be 1 type or a combination of 2 or more types.

<Additional ingredients>

The resin composition, in accordance with various properties required for use for electronic devices, within the range of not impairing the effects of the present invention, (E) photosensitizer, (F) additional curing component (however, (A) and (B)) Excluding), (G) a filler and (H) may include one or more additional components selected from the group consisting of a silane coupling agent.

<<(E) Photosensitizer>>

The resin composition may further contain (E) a photosensitizer in order to increase the sensitivity to light at the time of photocuring. From the viewpoint of curability, examples of (E) include carbonyl compounds, organic sulfur compounds and sulfides, redox compounds, azo compounds, diazo compounds, halogen compounds, and photoreducing dyes. Specific examples of the photosensitizer include acridone derivatives such as N-methylacridone and N-butylacridone; Other examples include α,α-diethoxyacetophenone, benzyl, fluorenone, xanthone, and uranyl compounds. In addition, even those listed as examples of the photoradical polymerization initiator may function as a photosensitizer.

(E) may be 1 type or a combination of 2 or more types.

<<(F) Additional hardening component (except (A) and (B))>>

(F) includes, for example, a compound having a conventional ethylenically unsaturated group and/or an epoxy group used as a subject of a composition for electronic devices (preferably a liquid crystal sealing agent).

The compound having an ethylenically unsaturated group includes a (meth)acrylate compound, an aliphatic acrylamide compound, an alicyclic acrylamide compound, an acrylamide compound containing an aromatic, and an N-substituted acrylamide compound.

The functionality of the (meth)acrylate compound may be monofunctional, bifunctional, or trifunctional or more polyfunctional.

Examples of the monofunctional (meth)acrylate compound include aliphatic (meth)acrylate, aromatic ring-containing (meth)acrylate, etc., and from the viewpoint of securing the viscosity and flexibility of the resin composition, hydroxyethyl (meth) Acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isooctyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate )Acrylate, cyclohexyloxyethyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, isomiristyl (meth)acrylate, lauryl (meth) )Acrylate, tert-butyl (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, paracumylphenoxyethylene glycol (meth)acrylate, ethoxylated phenyl (meth)acrylate, and glycidyl ( At least one compound selected from the group consisting of meth)acrylates is preferred.

As a bifunctional (meth)acrylate compound, from the viewpoint of securing the viscosity and flexibility of the resin composition, tricyclodecanedimethanoldi(meth)acrylate, dimethyloldicyclopentanedi(meth)acrylate, EO modified 1, 6-hexanedioldi(meth)acrylate, EO-modified bisphenol A di(meth)acrylate, PO-modified bisphenol A di(meth)acrylate, polyester di(meth)acrylate (e.g., ARONIX M-6100 , Doa Kosei Co., Ltd.), polyethylene glycol di(meth)acrylate (e.g., 4G, manufactured by Shinnakamura Chemical Co., Ltd.) and silicone di(meth)acrylate (e.g., EBECRYL 350, manufactured by Daicel Allnex Corporation) ) Is preferably at least one compound selected from the group consisting of. Among them, (meth)acrylate having no hydroxyl group and having a bisphenol A skeleton is preferred, and as the (meth)acrylate, light acrylate BP-4EAL (EO addition of bisphenol A) from Kyoesha Chemical Co., Ltd. Water diacrylate), BP-4PA (PO adduct diacrylate of bisphenol A) and the like are commercially available. Here, "EO" means ethylene oxide, and "PO" means propylene oxide.

As a trifunctional or polyfunctional (meth)acrylate compound, from the viewpoint of securing the viscosity and flexibility of the resin composition, EO-modified glycerol tri(meth)acrylate (trifunctional), PO-modified glycerol tri(meth)acrylate ( Trifunctional), pentaerythritol tri(meth)acrylate (trifunctional), dipentaerythritol hexa(meth)acrylate (6-functional) and pentaerythritol tetra(meth)acrylate (tetrafunctional) At least one compound selected is preferred.

Examples of the compound having an epoxy group include those described above as a bifunctional or higher epoxy resin.

(F) may be 1 type or a combination of 2 or more types.

In addition, the resin composition may contain only (A), (B) and, in some cases, (C), a component having an epoxy group and/or an ethylenically unsaturated group contained in the resin composition. In this case, the resin composition does not contain (F) (i.e., an additional cured component other than (A) and (B)). Specifically, the component having an epoxy group and an ethylenically unsaturated group may contain only part of (A), and the component having an epoxy group and not having an ethylenically unsaturated group includes only part of (A) and (B), or ( A part of A) may contain only a part of (B) and (C), and/or a component which does not have an epoxy group and has an ethylenically unsaturated group may contain only a part of (A). In addition, when the component having an epoxy group and/or an ethylenically unsaturated group contains (C), it is the case where (C) has an epoxy group.

<<(G) filler>>

(G) is added for the purpose of improving the adhesion reliability of the resin composition by controlling the viscosity of the resin composition, improving the strength of the cured product obtained by curing the resin composition, or suppressing linear expansion. (G) is not particularly limited, and known inorganic fillers and organic fillers used for a composition containing an epoxy resin may be mentioned. As an inorganic filler, calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, titanium oxide, alumina, zinc oxide, silicon dioxide, kaolin, talc, glass beads, sericite activated clay, bentonite, aluminum nitride, and silicon nitride I can. Examples of the organic filler include polymethyl methacrylate, polystyrene, a copolymer obtained by copolymerizing a monomer constituting these with other monomers, polyester fine particles, polyurethane fine particles and rubber fine particles, and in particular inorganic fillers such as silicon dioxide And talc are preferred.

(G) may be 1 type or a combination of 2 or more types.

<<(H) Silane coupling agent>>

(H) is added for the purpose of further improving the adhesion to the liquid crystal display substrate. The silane coupling agent is not particularly limited, and includes γ-aminopropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-isocyanate propyltrimethoxysilane, and 3-glycidoxypropyltrimethoxysilane. I can.

(H) may be 1 type or a combination of 2 or more types.

(Furtherance)

The content of (B) in the resin composition is preferably 1 to 40 parts by mass, more preferably 2 to 35 parts by mass, and particularly 2.5 to 15 parts by mass per 100 parts by mass of the total of (A) and (B). desirable. When the content of (B) in the resin composition is within the above range, the effect of reducing the moisture permeability of the cured product according to (B) can be sufficiently exhibited.

The content of (C) in the resin composition is preferably 1 to 40 parts by mass, and more preferably 3 to 35 parts by mass with respect to 100 parts by mass in total of (A) and (B). However, when (C) contains only a polyaddition type curing agent, the content of (C) in the resin composition is, relative to the sum of the epoxy groups of (A) and (B), the amount of active hydrogen in (C) is 0.6 to 1.2 It is preferable that it is an amount which doubles, and it is more preferable that it is an amount which becomes 0.7 to 1.1 times. With respect to the total of the epoxy groups (A) and (B), if the amount of active hydrogen in (C) is 1.2 times or less, the amount of amino groups in the cured product of the resin composition can be reduced. Thereby, the solubility of the cured product of the resin composition in water is further reduced, and the moisture permeability of the cured product can be further reduced. Further, if the amount of active hydrogen in (C) is 0.6 times or more with respect to the total of the epoxy groups of (A) and (B), the curing reaction can be efficiently promoted.

The content of (D) in the resin composition is preferably 0.1 to 25 parts by mass, and more preferably 0.5 to 15 parts by mass with respect to 100 parts by mass in total of (A) and (B).

When the resin composition contains (E), the content of (E) is preferably 0.5 to 40 parts by mass, and more preferably 1 to 20 parts by mass with respect to 100 parts by mass of (D).

When the resin composition contains (F), the content of (F) is preferably 1 to 30 parts by mass, and more preferably 2 to 20 parts by mass based on 100 parts by mass in total of (A) and (B). .

When the resin composition contains (G), the content of (G) is preferably 2 to 40 parts by mass, more preferably 3 to 30 parts by mass based on 100 parts by mass in total of (A) and (B). .

When the resin composition contains (H), the content of (H) is preferably 0.1 to 10 parts by mass, more preferably 0.3 to 2 parts by mass based on 100 parts by mass in total of (A) and (B). .

It is preferable that it is 40 mass% or more, and, as for the content rate of (A) and (B) in a resin composition, it is especially preferable that it is 60 mass% or more. In addition, the content rate of (A), (B), (C) and (D) in the resin composition is preferably 40% by mass to 100% by mass, more preferably 50% by mass to 97% by mass, and 60 It is particularly preferably from mass% to 95 mass%.

[Preparation of resin composition]

The resin composition can be produced by mixing (A) to (D) as essential components and other components as optional components.

[Hardening method]

The resin composition can be cured by a method including heating or a method including heating and irradiation with active energy rays. When both heating and irradiation with active energy rays are performed, heating can be performed before, simultaneously, and/or after irradiation with active energy rays, and is preferably performed after. The active energy ray is preferably ultraviolet ray or visible ray. The irradiation amount of the active energy ray is preferably 50 to 10,000 mJ/cm ² , more preferably 100 to 6,000 mJ/cm ² . The heating temperature is preferably 50 to 200°C, particularly preferably 80 to 150°C. The heating time is preferably 10 minutes to 5 hours, and particularly preferably 30 minutes to 3 hours.

[purpose]

The resin composition can be used as a sealing agent for protecting an electronic device from moisture. Examples of the electronic device include organic electroluminescence, electronic paper, solar cells, and liquid crystal displays. In particular, it is preferable to use a resin composition as a sealing agent for liquid crystal dropping methods. Thereby, the moisture permeability is low, and it can be used as a sealing agent with high reliability of liquid crystal display characteristics. About the sealing agent for a liquid crystal dropping method using an epoxy resin, JP 2012-077202 A can be referred, for example.

Example

Hereinafter, the present invention will be specifically described by way of examples, but the present invention is not limited to these examples. In addition, (A) and (D) used in Examples and Comparative Examples were prepared as follows.

[(A): Preparation of partially methacrylated bisphenol A type epoxy resin]

Bisphenol A type epoxy resin (EXA-850CRP, manufactured by DIC Corporation) 340.0 g, methacrylic acid (manufactured by Tokyo Kasei Kogyo) 90.4 g, triphenylphosphine (manufactured by Tokyo Kasei Kogyo Corporation) 0.5 g and 100 mg of BHT (dibutylhydroxytoluene) was mixed and stirred at 100°C for 6 hours. 418.0 g of partially methacrylated bisphenol A type epoxy resins a1 of a pale yellow transparent viscous product were obtained.

[(D): Preparation of polymerization initiator]

The polymerization initiators used in Examples and Comparative Examples were prepared as follows.

<Preparation of polymerization initiator d1>

Denacol EX-830 (diglycidyl ether of PEG400 manufactured by Nagase Chemtex Co., Ltd.) 26.8 g (0.10 equivalent/epoxy group), 4-dimethylaminobenzoic acid 16.5 g (1.0 equivalent), benzyltrimethylammonium chloride 3.7 g (0.20 Equivalent) and 25.0 g of MIBK (methyl isobutyl ketone) were added to the flask, followed by stirring at 110°C for 24 hours. The reaction mixture was cooled to room temperature, dissolved in 50 g of chloroform, and washed 6 times with 100 ml of water. The organic solvent was distilled off under reduced pressure to obtain 35.3 g of a polymerization initiator d1.

<Preparation of polymerization initiator d2>

Denacol EX-830 (diglycidyl ether of PEG400 manufactured by Nagase Chemtex Co., Ltd.) 26.8 g (0.10 equivalent/epoxy group), 2-hydroxy-9H-thioxanthene-9-one 22.8 g (1.0 equivalent) , 3.7g (0.20 equivalent) of benzyltrimethylammonium chloride, and 40.0g of MIBK were added to the flask, followed by stirring at 110°C for 72 hours. The reaction mixture was cooled to room temperature, dissolved in 50 g of chloroform, and washed 6 times with 100 ml of water. The organic solvent was distilled off under reduced pressure to obtain 36.2 g of a polymerization initiator d2.

[(B): monofunctional epoxy compound]

The structural formula of (B) used in the examples and the product name or manufacturing method are as follows.

b1: EX-141: phenylglycidyl ether (manufactured by Nagase Chemtex Co., Ltd.)

b2: OPP-G: 2-phenylphenol glycidyl ether (manufactured by Sanko Corporation)

b3: EX-146: 4-tert-butylphenylglycidyl ether (manufactured by Nagase Chemtex Co., Ltd.)

<Preparation of monofunctional epoxy compound b4>

200 g of 1-naphthol, 1283 g of epichlorohydrin, and 125 g of dimethyl sulfoxide were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 208 g of a 48% aqueous sodium hydroxide solution was added dropwise over 2 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Then, the reaction mixture was cooled to room temperature, 1000 g of toluene was added, followed by washing 5 times with 1.5 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 253 g of monofunctional epoxy compounds b4.

<Production of monofunctional epoxy compound b5>

200 g of 4-?-cumylphenol, 871 g of epichlorohydrin, and 85 g of dimethyl sulfoxide were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 141 g of a 48% aqueous sodium hydroxide solution was added dropwise over 2 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Then, the reaction mixture was cooled to room temperature, 1000 g of toluene was added, followed by washing 5 times with 1.5 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 250 g of monofunctional epoxy compounds b5.

<Preparation of monofunctional epoxy compound b6>

100 g of 4-methoxyphenol, 745 g of epichlorohydrin, and 15 g of benzyltrimethylammonium chloride were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50 DEG C while stirring under a reduced pressure of 50 torr, and 121 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Then, the reaction mixture was cooled to room temperature, 500 g of toluene was added and washed 5 times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 103 g of monofunctional epoxy compounds b6.

<Preparation of monofunctional epoxy compound b7>

100 g of 4-hydroxybenzaldehyde, 757 g of epichlorohydrin, and 15 g of benzyltrimethylammonium chloride were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, condenser, Dean-Stark trap, dropping funnel, and stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 123 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Subsequently, the reaction mixture was cooled to room temperature, 500 g of toluene was added, and washed 4 times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 111 g of a monofunctional epoxy compound b7.

<Preparation of monofunctional epoxy compound b8>

25 g of 4-hydroxybenzonitrile, 194 g of epichlorohydrin, and 4 g of benzyltrimethylammonium chloride were placed in a 0.5 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 32 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Then, the reaction mixture was cooled to room temperature, 150 g of toluene was added, and washed 4 times with 0.3 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 36 g of monofunctional epoxy compounds b8.

<Production of monofunctional epoxy compound b9>

100 g of 4-fluorophenol, 850 g of epichlorohydrin, and 17 g of benzyltrimethylammonium chloride were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 138 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After completion of the addition, stirring was continued over 5 hours. Subsequently, the reaction mixture was cooled to room temperature, 500 g of toluene was added, and washed 4 times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 130 g of monofunctional epoxy compounds b9.

<Preparation of monofunctional epoxy compound b10>

25 g of 4-phenoxyphenol, 124 g of epichlorohydrin, and 3 g of benzyltrimethylammonium chloride were placed in a 0.5 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 20 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Then, the reaction mixture was cooled to room temperature, 150 g of toluene was added, and washed 4 times with 0.3 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 32 g of a monofunctional epoxy compound b10.

<Preparation of monofunctional epoxy compound b11>

100 g of 2-phenoxyethanol, 670 g of epichlorohydrin, and 13 g of benzyltrimethylammonium chloride were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 20 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 3 hours. Then, the reaction mixture was cooled to room temperature, 500 g of toluene was added, followed by washing three times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 70 g of a monofunctional epoxy compound b11.

<Preparation of monofunctional epoxy compound b12>

(1) Synthesis of hydroxyethyl adduct

100 g of 2-phenylphenol, 62 g of ethylene carbonate, 300 g of N,N-dimethylformamide, and 97 g of potassium carbonate were placed in a flask, followed by stirring at 100° C. for 24 hours. It cooled to room temperature, 500 g of toluene was added, and it washed 5 times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain a 2-phenylphenol-hydroxyethyl adduct.

(2) Synthesis of epoxy resin

100 g of the obtained 2-phenylphenol-hydroxyethyl adduct, 432 g of epichlorohydrin, and 9 g of benzyltrimethylammonium chloride were added to a 1 L three-neck round bottom flask equipped with a thermometer, condenser, Dean-Stark trap, dropping funnel, and stirrer. Put in. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 70 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 3 hours. Subsequently, the reaction mixture was cooled to room temperature, 500 g of toluene was added, and washed 4 times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 121 g of a monofunctional epoxy compound b12.

<Preparation of monofunctional epoxy compound b13>

25 g of 4-hydroxybenzophenone, 117 g of epichlorohydrin, and 2 g of benzyltrimethylammonium chloride were placed in a 0.5 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50° C. while stirring under a reduced pressure of 50 torr, and 19 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 12 hours. Then, the reaction mixture was cooled to room temperature, 200 g of toluene was added, followed by washing four times with 0.3 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 26 g of monofunctional epoxy compounds b13.

<Preparation of monofunctional epoxy compound b14>

100 g of 4-(benzyloxy)phenol, 462 g of epichlorohydrin, and 9 g of benzyltrimethylammonium chloride were placed in a 1 L 3-neck round bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer. Then, the mixture was heated to about 50 DEG C while stirring under a reduced pressure of 50 torr, and 75 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 12 hours. Then, the reaction mixture was cooled to room temperature, 400 g of toluene was added, and washed three times with 1.0 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 82 g of monofunctional epoxy compounds b14.

b15: Glycidyl methyl ether (manufactured by Tokyo Kasei Kogyo Co., Ltd.)

b16: Butyl glycidyl ether (manufactured by Tokyo Kasei Kogyo Co., Ltd.)

b17: furfuryl glycidyl ether (manufactured by Across Organics)

<Preparation of monofunctional epoxy compound b18>

100 g of 2-(4-hydroxyphenyl)ethanol, 402 g of epichlorohydrin, and 65 g of dimethylsulfoxide were placed in a 2 L 3-neck round bottom flask equipped with a thermometer, condenser, Dean-Stark trap, dropping funnel, and stirrer. . Then, the mixture was heated to about 50 DEG C while stirring under a reduced pressure of 50 torr, and 60 g of a 48% aqueous sodium hydroxide solution was added dropwise over 3 hours. Stirring was continued while returning epichlorohydrin to the reaction system in the water/epichlorohydrin mixture flowing out by azeotrope. After the addition was completed, stirring was continued over 2 hours. Then, the reaction mixture was cooled to room temperature, 200 g of toluene and 200 g of 3-methyl-2-butanone were added, followed by washing three times with 0.5 L of water. Magnesium sulfate was added to the organic phase, and after drying, the solid content was separated by filtration by filtration or the like, and the obtained organic layer was removed by distillation under reduced pressure to obtain 108 g of monofunctional epoxy compounds b18.

[Others: bifunctional epoxy compounds and monofunctional (meth)acrylate compounds]

The bifunctional epoxy compound and monofunctional (meth)acrylate compound used in the comparative examples are as follows.

b'1: EXA-850CRP: Bisphenol A type epoxy resin (manufactured by DIC Corporation)

b'2: Phenyl methacrylate (manufactured by Tokyo Kasei Kogyo Co., Ltd.)

[Examples 1 to 22 and Comparative Examples 1 to 4]

Partially methacrylated bisphenol A type epoxy resin a1, monofunctional epoxy compounds, respectively, or bifunctional epoxy compounds or monofunctional (meth)acrylate compounds, photopolymerization initiators d1 and d2, amine curing agent c1 (polyamine compound, EH -5030S (manufactured by ADEKA Co., Ltd.)) was sufficiently kneaded in the amount (parts by mass) shown in Table 1 below to obtain resin compositions of Examples 1 to 22 and Comparative Examples 1 to 4.

Each compound prepared in Synthesis Example and Comparative Synthesis Example, and each of these resin compositions were evaluated by the following tests.

[Exam conditions]

(1) Epoxy equivalent (WPE) measurement

It measured under the conditions described in JISK7236:2001.

(2) moisture permeability

The resin composition was sandwiched by a PET (polyethylene terephthalate) film having a diameter of 3.6mm to 3.8mm and a thickness of 0.28mm to 0.32mm and a thickness of 0.1mm, and both sides were 1500mJ with an ultraviolet irradiation illuminance of 100mW/cm ² Irradiation was performed with light energy of /cm ² , and heat curing was performed in a hot air oven at 120° C. for 1 hour to obtain a sample for measuring moisture permeability. The moisture permeability measurement was calculated from the change in weight by the moisture permeable cup method in accordance with JIS K0208:1976, using a constant temperature and humidity tank of 65°C/95%. The unit of moisture permeability is g/(m ² ·24h).

The results of the above evaluation are shown in Tables 1 and 2 below, together with the blending compositions of the resin compositions of Examples 1 to 22 and Comparative Examples 1 to 4. In addition, except in Example 4, the amount of (C) in which the amount of active hydrogen in (C) is 1 times the total of the epoxy groups in (A) and (B) was employed. In addition, in Example 4, the amount of (C) in which the amount of active hydrogen in (C) becomes 0.83 times the total of the epoxy groups of (A) and (B) was adopted.

All of the resin compositions of Examples were resin compositions which impart a cured product with low moisture permeability.

By comparison of Examples 3, 6 and 9, when X ¹ is an unsubstituted aryl group, the lower the epoxy equivalent of (B), the more the moisture permeability was lowered. According to the comparison of Examples 19 and 20, it can be said that the case where X ² is an unsubstituted alkyl group is also the same. This is considered to be a factor because the epoxy equivalent is small, so that the number of bonds increases and the crosslinking becomes dense.

As a result of the comparison between Examples 6 to 10 and Example 11, when the content of (B) increased with respect to 100 parts by mass in total of (A) and (B), the moisture permeability of the cured product decreased. However, if the content of (B) was 10 parts by mass or more with respect to 100 parts by mass in total of (A) and (B), the effect of lowering the moisture permeability of the cured product was saturated.

As a result of the comparison between Example 3 and Example 4, even when the amount of active hydrogen in (C) was small relative to the total of the epoxy groups of (A) and (B), there was an effect of lowering the moisture permeability of the cured product.

By comparison of Examples 3, 7, 9, 10 to 14, 17 to 18, and 22, when X ¹ is an aryl group which may be substituted, if it is an aryl group which is unsubstituted or substituted with a preferable substituent, the moisture permeability of the cured product is more Fell down.

By comparison of Examples 7 and 22, compared with the case where X ¹ is an aryl group substituted with an alkyl group, in the case of an aryl group substituted with a hydroxyalkyl group, the moisture permeability of the cured product was further lowered.

By comparison of Examples 3 and 15, and Examples 8 and 16, the cyclic structure of the aromatic group compared to the resin composition containing the epoxy compound in which the cyclic structure of the aromatic group and the glycidyloxy group were bonded through an oxyalkylene group. In the resin composition containing the epoxy compound and the glycidyloxy group directly bonded, the moisture permeability of the cured product was further lowered.

By comparison of Examples 19 to 21, even if the carbon atom bonded to glycidyloxy is an aliphatic carbon atom, the resin composition containing the aromatic epoxy compound having an aromatic group further lowered the moisture permeability of the cured product.

In Comparative Example 1, since the resin composition did not contain (B), the moisture permeability of the cured product was high.

In Comparative Example 2, since the resin composition contained a bifunctional epoxy compound instead of a monofunctional epoxy compound, the reduction in the moisture permeability of the cured product was not sufficient.

In Comparative Examples 3 and 4, the resin composition contains a monofunctional (meth)acrylate compound instead of a monofunctional epoxy compound. In Comparative Examples 3 and 4, the decrease in the moisture permeability of the cured product was not sufficient with respect to Examples 2 and 3 to 4 in which the same amount of the monofunctional epoxy compound was used.

The resin composition is a resin composition for electronic devices that provides a cured product with low moisture permeability. Therefore, the resin composition has high industrial applicability as a sealing agent for electronic devices requiring low moisture permeability, particularly a sealing agent for a liquid crystal dropping method.

Claims (9)

As a resin composition for electronic devices containing (A) a partial (meth)acrylated epoxy resin of a bifunctional or higher epoxy resin, (B) a monofunctional epoxy compound, (C) an amine curing agent and (D) a polymerization initiator, (B) Is a compound represented by the following formula (1) and/or a compound represented by the following formula (2).
X ¹ -G (1)
[In the formula,
G is a glycidyloxy group or a methylglycidyloxy group,
X ¹ is an optionally substituted aryl group, an optionally substituted aryl-(OR ¹ ) _n1 group (here, R ¹ is an alkylene group and n1 is an integer of 1 to 6), optionally substituted aryl-R ² group (Here, R ² is an alkylene group), an optionally substituted heteroaryl group, an optionally substituted heteroaryl-(OR ³ ) _n2 group (here, R ³ is an alkylene group, and n2 is an integer of 1 to 6) , Or a heteroaryl-R ⁴ group which may be substituted (here, R ⁴ is an alkylene group), wherein:
Substituents of the aryl group and the heteroaryl group are alkyl, hydroxyalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxy, formyl, acyl, cyano, nitro, sulfo, and halogen atoms. It is selected from the group consisting of.]
X ² -G (2)
[In equation (2),
G is as defined by formula (1),
X ² is an optionally substituted alkyl group, an optionally substituted alkyl-(OR ⁵ ) _n3 group (here, R ⁵ is an alkylene group and n3 is an integer of 1 to 6), an alkenyl group which may be substituted, or even if substituted _Alkenyl- (OR ⁶ ) _n4 group (here, R ⁶ is an alkylene group and n4 is an integer of 1 to 6), an alkynyl group which may be substituted, or an alkynyl-(OR ⁷ ) _n5 group which may be substituted (Where, R ⁷ is an alkylene group, n5 is an integer of 1 to 6), wherein,
The substituents of the alkyl group, the alkenyl group and the alkynyl group are selected from the group consisting of a formyl group, an acyl group, a cyano group, a nitro group, a sulfo group, and a halogen atom.] The resin composition for an electronic device according to claim 1, wherein the epoxy equivalent of (B) is 80 to 2,000 g/eq. The method according to claim 1 or 2, wherein (A) is a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol S type epoxy resin, a phenol novolak type epoxy resin, a cresol novolak type epoxy resin, and a bisphenol A novolac. Type epoxy resin, bisphenol F novolak type epoxy resin, alicyclic epoxy resin, aliphatic chain type epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy A resin composition which is a partial (meth)acrylated epoxy resin of at least one epoxy resin selected from the group consisting of a resin and a phenol novolak type epoxy resin having a triphenolmethane skeleton. The resin composition for an electronic device according to claim 1 or 2, wherein (B) is 1 to 40 parts by mass per 100 parts by mass in total of (A) and (B). The resin composition for electronic devices according to claim 3, wherein (B) is 1 to 40 parts by mass with respect to 100 parts by mass in total of (A) and (B). The resin composition for electronic devices according to claim 1 or 2, which is a sealing agent for a liquid crystal dropping method. The resin composition for electronic devices according to claim 3, which is a sealing agent for a liquid crystal dropping method. The resin composition for electronic devices according to claim 4, which is a sealing agent for a liquid crystal dropping method. The resin composition for electronic devices according to claim 5, which is a sealing agent for a liquid crystal dropping method.