Active energy ray curable composition and its cured product

Abstract

To provide an active energy ray curable composition excellent in low viscosity and storage stability and capable of forming a cured material having high elongation rate and metal adhesion.SOLUTION: An active energy ray curable composition comprises a (meth)acrylate having an alicyclic skeleton (A), a N-substituted (meth)acrylamide (B), a (meth)acrylate having no phosphoric acid group (H), a (meth)acrylate having a phosphoric acid group (F) and a photopolymerization initiator (G), wherein the (H) is at least one kind selected from the group consisting of a monofunctional (meth)acrylate having a linear or branched alkyl group having 10 to 18 carbon atoms, and a bifunctional (meth)acrylate and a monofunctional urethane (meth)acrylate and, based on a total weight of (A), (B), (H) and (F), (A) is 5 to 50 wt.%, (B) is 10 to 50 wt.%, (H) is 10 to 45 wt.%, (F) is 0.5 to 7.5 wt.%, and (G) is 2 to 20 wt.%.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to an active energy ray curable composition. [Background technology]

[0002] Conventionally, cured products of active energy ray curable compositions have been used as materials for displays such as organic EL displays (see, for example, Patent Documents 1 and 2). In recent years, there has been active development of so-called flexible displays that can be folded, and consequently, display materials are required to have bending resistance that prevents damage when folded and prevents delamination between components. However, conventional cured products of active energy ray curable compositions have insufficient bending resistance. To achieve sufficient bending resistance, it was necessary to achieve both excellent elongation and excellent adhesion to the substrate at a high level.

[0003] On the other hand, active energy ray curable compositions, which have low viscosity at room temperature, are applicable to a wide range of coating methods and are particularly advantageous when used as materials for electronic components, optical components, and other applications requiring highly precise coating. As a curable composition with low viscosity and good elongation of the cured product, Patent Document 3 proposes a radiation-curable ink composition comprising 5 to 30% by mass of monofunctional urethane (meth)acrylate and 5 to 30% by mass of monofunctional nitrogen-containing monomer containing nitrogen atoms in a cyclic skeleton. However, this composition lacks sufficient adhesion to metal materials, which are often used in electronic and optical components, and its storage stability is also not sufficient. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2013-133427 [Patent Document 2] Japanese Patent Publication No. 2012-194212 [Patent Document 3] Japanese Patent Publication No. 2020-70338 [Overview of the project] [Problems that the invention aims to solve]

[0005] The present invention has been made in view of the above-mentioned problems, and the object of the present invention is to provide an active energy ray curable resin composition that has low viscosity and excellent storage stability, and can form a cured product having high elongation and metal adhesion. [Means for solving the problem]

[0006] The present inventors have diligently studied to achieve the above objectives and have arrived at the present invention. That is, the present invention is an active energy ray curable composition containing an alicyclic (meth)acrylate (A), an N-substituted (meth)acrylamide (B), a (meth)acrylate (H) without a phosphate group, a (meth)acrylate (F) having a phosphate group, and a photopolymerization initiator (G), wherein the (meth)acrylate (H) is a monofunctional (meth)acrylate (C), a bifunctional (meth)acrylate (D), and a monofunctional (meth)acrylate (D) having a linear or branched alkyl group with 10 to 18 carbon atoms. An active energy ray curable composition comprising at least one selected from the group consisting of uretan (meth)acrylate (E), wherein the content of (A) is 5 to 50% by weight, the content of (B) is 10 to 50% by weight, the content of (H) is 10 to 45% by weight, the content of (F) is 0.5 to 7.5% by weight, and the content of (G) is 2 to 20% by weight, based on the total weight of (A), (B), (H), and (F); and a cured product obtained by curing the active energy ray curable composition. [Effects of the Invention]

[0007] The active energy ray curable resin composition of the present invention has low viscosity and excellent storage stability, and can form cured products with high elongation and metal adhesion. [Modes for carrying out the invention]

[0008] The active energy ray curable composition of the present invention is an active energy ray curable composition containing an alicyclic skeleton (meth)acrylate (A), an N-substituted (meth)acrylamide (B), a phosphate-free (meth)acrylate (H), a phosphate-containing (meth)acrylate (F), and a photopolymerization initiator (G), wherein the (meth)acrylate (H) is at least one selected from the group consisting of monofunctional (meth)acrylate (C), bifunctional (meth)acrylate (D), and monofunctional urethane (meth)acrylate (E), all having a linear or branched alkyl group with 10 to 18 carbon atoms.

[0009] In this invention, "(meth)acrylate" means "methacrylate or acrylate," "(meth)acrylic" means "methacrylic or acrylic," and "(meth)acryloyl" means "methacryloyl or acryloyl." Also,

[0010] The essential components of the active energy ray curable composition of the present invention, namely (meth)acrylate (A), N-substituted (meth)acrylamide (B), (meth)acrylate (H) without a phosphate group, (meth)acrylate (F) with a phosphate group, and photopolymerization initiator (G), are described below in order.

[0011] The chemical structure of the (meth)acrylate (A) having an alicyclic skeleton is not particularly limited as long as it has an alicyclic skeleton. Examples of the (meth)acrylate (A) having an alicyclic skeleton include monofunctional (meth)acrylate (A1) and bifunctional (meth)acrylate (A2) having an alicyclic skeleton.

[0012] Examples of monofunctional (meth)acrylates (A1) having an alicyclic skeleton include isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and adamantyl (meth)acrylate. Examples of bifunctional (meth)acrylates (A2) having an alicyclic skeleton include cyclohexanemethanol di(meth)acrylate, ethoxylated cyclohexanemethanol di(meth)acrylate, tricyclodecanedimethyl di(meth)acrylate, and 1,3-adamantyldiol di(meth)acrylate. In the present invention, these alicyclic (meth)acrylate (A) materials may be used individually or in combination of two or more.

[0013] Of these alicyclic (meth)acrylates (A), monofunctional (meth)acrylates (A1) having an alicyclic structure are preferred from the viewpoint of elongation of the cured product and strength of the cured product, and more preferably isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, and 1-ethylcyclohexyl (meth)acrylate.

[0014] In the present invention, N-substituted (meth)acrylamide (B) means a (meth)acrylamide in which one or two hydrogen atoms of the amino group are replaced with substituents such as hydrocarbon groups. Examples of N-substituted (meth)acrylamides include chain amides having an N-(meth)acryloyl group (B1) and cyclic amides having an N-(meth)acryloyl group (B2).

[0015] Examples of the chain amide (B1) having an N-(meth)acryloyl group include N-alkyl(meth)acrylamide (B11), N,N-dialkyl(meth)acrylamide (B12), N-hydroxyalkyl(meth)acrylamide (B13), N-alkoxyalkyl(meth)acrylamide (B14), and N-alkoxy-N-alkyl(meth)acrylamide (B15).

[0016] Examples of N-alkyl(meth)acrylamide (B11) include N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-dodecyl(meth)acrylamide, and N-octadecyl(meth)acrylamide.

[0017] Examples of N,N-dialkyl(meth)acrylamide (B12) include N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-dipropyl(meth)acrylamide, N,N-diisopropyl(meth)acrylamide, N,N-dibutyl(meth)acrylamide, N,N-diisobutyl(meth)acrylamide, N,N-di-tert-butyl(meth)acrylamide, N,N-diheptyl(meth)acrylamide, N,N-dioctyl(meth)acrylamide, N,N-di-tert-octyl(meth)acrylamide, N,N-didodecyl(meth)acrylamide, and N,N-dioctadecyl(meth)acrylamide. The two alkyl groups of N,N-dialkyl(meth)acrylamide (B12) may be the same or different, and the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 8, and particularly preferably 1 to 4 from the viewpoint of curability.

[0018] Examples of N-hydroxyalkyl(meth)acrylamide (B13) include N-hydroxymethyl(meth)acrylamide, N-hydroxyethyl(meth)acrylamide, and N-(3-hydroxypropyl)(meth)acrylamide. From the viewpoint of curability, the number of carbon atoms in the alkyl group of N-hydroxyalkyl(meth)acrylamide (B13) is preferably 1 to 20, more preferably 1 to 8, and particularly preferably 1 to 4.

[0019] Examples of N-alkoxyalkyl(meth)acrylamide (B14) include N-methoxymethyl(meth)acrylamide, N-ethoxymethyl(meth)acrylamide, N-propoxymethyl(meth)acrylamide, N-butoxymethyl(meth)acrylamide, N-methoxyethyl(meth)acrylamide, N-ethoxyethyl(meth)acrylamide, N-butoxyethyl(meth)acrylamide, N-methoxypropyl(meth)acrylamide, N-ethoxypropyl(meth)acrylamide, N-methoxybutyl(meth)acrylamide, and N-ethoxybutyl(meth)acrylamide. From the viewpoint of curability, the number of carbon atoms in the alkoxyalkyl group of N-alkoxyalkyl(meth)acrylamide (B14) is preferably 2 to 20, more preferably 2 to 8, and particularly preferably 2 to 6. From the viewpoint of curability, the number of carbon atoms in the alkyl group of the alkoxyalkyl group is preferably 1 to 4, more preferably 1 to 3, and particularly preferably 1 to 2.

[0020] Examples of N-alkoxy-N-alkyl(meth)acrylamide (B15) include N-methyl-N-methoxy(meth)acrylamide, N-methyl-N-ethoxy(meth)acrylamide, N-methyl-N-propoxy(meth)acrylamide, and N-methyl-N-butoxy Examples include cy(meth)acrylamide, N-ethyl-N-methoxy(meth)acrylamide, N-ethyl-N-ethoxy(meth)acrylamide, N-ethyl-N-butoxy(meth)acrylamide, N-propyl-N-methoxy(meth)acrylamide, N-propyl-N-ethoxy(meth)acrylamide, N-butyl-N-methoxy(meth)acrylamide, and N-butyl-N-ethoxy(meth)acrylamide.

[0021] Examples of cyclic amides (B2) having an N-(meth)acryloyl group include N-(meth)acryloylmorpholine, N-(meth)acryloylthiomorpholine, N-(meth)acryloylpiperidine, N-(meth)acryloylpyrrolidine, and N-(meth)acryloylpiperidine. The number of carbon atoms in the cyclic amide having an N-(meth)acryloyl group is preferably 7 to 20, more preferably 7 to 18, and particularly preferably 7 to 16, from the viewpoint of curability. In the present invention, these N-substituted (meth)acrylamides (B) may be used individually or in combination of two or more.

[0022] Of these N-substituted (meth)acrylamides (B), those preferred from the viewpoint of viscosity, curability and elongation of the cured product are N,N-dialkyl(meth)acrylamide (B12), N-alkoxyalkyl(meth)acrylamide (B14), and cyclic amides (B2) having an N-(meth)acryloyl group. More preferably, these are N,N-dialkyl(meth)acrylamide (B12) and cyclic amides (B2) having an N-(meth)acryloyl group. Particularly preferred are N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, and N-(meth)acryloylmorpholine.

[0023] The (meth)acrylate (H) without a phosphate group is at least one selected from the group consisting of monofunctional (meth)acrylate (C), bifunctional (meth)acrylate (D), and monofunctional urethane (meth)acrylate (E), which have a linear or branched alkyl group having 10 to 18 carbon atoms. If (meth)acrylate (H) is not included, the elongation of the cured product will be insufficient.

[0024] Monofunctional (meth)acrylates (C) having linear or branched alkyl groups with 10 to 18 carbon atoms include decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, stearyl (meth)acrylate, and isostearyl (meth)acrylate. These (meth)acrylates can be easily produced by direct esterification or transesterification reactions with natural or synthetic alcohols such as (meth)acrylic acid or methyl (meth)acrylate. When natural alcohols are used, the alkyl groups are linear and have an even number of carbon atoms. When synthetic alcohols are used, for example, when using Dovanol (manufactured by Mitsubishi Petrochemical Co., Ltd.), the alkyl groups are a mixture of linear and branched, and the number of carbon atoms is a mixture of odd and even. When using Diadol (manufactured by Mitsubishi Chemical Corporation), the alkyl groups are a mixture of linear and branched, and the number of carbon atoms is only odd. In the present invention, these monofunctional (meth)acrylates (C) having linear or branched alkyl groups with 10 to 18 carbon atoms may be used individually or in combination of two or more.

[0025] Among these monofunctional (meth)acrylates (C) having linear or branched alkyl groups with 10 to 18 carbon atoms, lauryl (meth)acrylate, isodecyl (meth)acrylate, and isostearyl (meth)acrylate are preferred from the viewpoint of elongation of the cured product, strength of the cured product, and adhesion to the substrate.

[0026] Examples of bifunctional (meth)acrylates (D) include polyalkylene glycol (alkylene group with 2-4 carbon atoms) di(meth)acrylate (D1), di(meth)acrylate (D2) of a 4-25 molar adduct of an alkylene oxide (alkylene group with 2-4 carbon atoms) of a divalent phenol compound, diesters of (meth)acrylic acid with a 1-15 molar adduct of an alkylene oxide (alkylene group with 2-4 carbon atoms) of a polyhydric (preferably 2-8 hydric) alcohol with 2-30 carbon atoms, diesters of (meth)acrylic acid with diglycidyl ether and diesters of (meth)acrylic acid, and di(meth)acrylates of ethylene oxide adducts of fluorene.

[0027] Examples of polyalkylene glycol (alkylene group with 2-4 carbon atoms) di(meth)acrylate (D1) include polyethylene glycol di(meth)acrylate (number average molecular weight 400-1000), polypropylene glycol di(meth)acrylate (number average molecular weight 400-800), and polytetramethylene glycol di(meth)acrylate (number average molecular weight 200-800).

[0028] Examples of di(meth)acrylates (D2) of 4-25 molar adducts of alkylene oxide (alkylene group with 2-4 carbon atoms) of divalent phenol compounds include di(meth)acrylates of alkylene oxide adducts of divalent phenol compounds [monocyclic phenols (catechol, resorcinol, hydroquinone, etc.), condensed polycyclic phenols (dihydroxynaphthalene, etc.), bisphenol compounds (bisphenol A, bisphenol F, and bisphenol S, etc.)], such as the di(meth)acrylate of the ethylene oxide (hereinafter referred to as EO) adduct of catechol, the di(meth)acrylate of the propylene oxide (hereinafter referred to as PO) adduct of dihydroxynaphthalene, and the di(meth)acrylate of the EO adduct of bisphenol A.

[0029] In the present invention, these bifunctional (meth)acrylates (D) may be used individually or in combination of two or more.

[0030] In the present invention, the bifunctional (meth)acrylate (D) is preferably a bifunctional (meth)acrylate having a homopolymer glass transition temperature (Tg) of 0°C or lower, from the viewpoint of the elongation of the cured product. The lower limit of the homopolymer Tg is preferably -60°C from the viewpoint of the strength of the cured product.

[0031] Here, the glass transition temperature of the homopolymer is the temperature at which the loss tangent (tanδ) shows its maximum value when the dynamic viscoelasticity of the polymer obtained by homopolymerizing the (meth)acrylate monomer using the method described below is measured using the method described below.

[0032] <Creating a test piece> (1) As a photoradical polymerization initiator, 1-hydroxycyclohexyl phenyl ketone [trade name "Irgacure 184", manufactured by BASF] was added at a concentration of 3% by weight relative to the (meth)acrylate, and the mixture was stirred until homogeneous to prepare a test piece sample. (2) Two pieces of 1mm thick silicone rubber sheet [product name: Silicone Rubber Sheet, manufactured by AS ONE Corporation] cut to 10mm wide x 150mm long were attached to both ends of a glass plate [product name: GLASS PLATE, manufactured by AS ONE Corporation, 200mm high x 200mm wide x 5mm thick]. Approximately 5g of the test piece sample created was placed between the silicone rubber sheets, and a PET film [product name: Lumirror S, manufactured by Toray Industries, Inc.] was placed on top to prevent air from entering, and then the glass plate was placed on top of that. (3)(2) is subjected to ultraviolet irradiation at 25°C using a UV irradiation device (e.g., Fusion UV Systems Japan VPS / I600, lamp: D bulb) at an illuminance of 1500 mW / cm2 (UV-A) and 1000 mJ / cm². 2 The material was then irradiated, and (2) was flipped over and cured from the opposite side with 1000 mJ / cm2. (4) The hardened sample from (3) was cut into pieces with a length of 40 mm, a width of 5 mm, and a thickness of 1 mm to be used as test pieces.

[0033] <Method for measuring dynamic viscoelasticity> Using this test piece, measurements are taken under the following conditions using a dynamic viscoelasticity measuring device (e.g., Rheogel-E4000, manufactured by UBM). Measurement mode: Temperature-dependent, Measurement temperature range: -80℃ to 200℃, Frequency: 10Hz, Heating rate: 4℃ / min, Distortion waveform: Sine wave, Measurement fixture: Tension The temperature at which the ratio (tanδ) of the loss modulus E'' to the storage modulus E' in the obtained spectrum is maximized is defined as the glass transition temperature (Tg).

[0034] As a method for adjusting the glass transition temperature of the (meth)acrylate (A) homopolymer having the alicyclic skeleton to be greater than 0°C and less than or equal to 200°C, the glass transition temperature can be increased by, for example, increasing the number of cyclic portions, such as bicyclic or tricyclic structures.

[0035] Of these bifunctional (meth)acrylates (D), (D1) and (D2) are preferred from the viewpoint of the elongation and viscosity of the cured product, (D1) is more preferred, and polyethylene glycol di(meth)acrylate (number average molecular weight 400 to 1000), polypropylene glycol di(meth)acrylate (number average molecular weight 400 to 700), and polytetramethylene glycol di(meth)acrylate (number average molecular weight 400 to 700).

[0036] In the present invention, monofunctional urethane (meth)acrylate (E) refers to a monomer having one (meth)acryloyl group and at least one urethane group in its molecule. From the viewpoint of viscosity, a monomer having one (meth)acryloyl group and one urethane group is preferred. Examples of monofunctional urethane (meth)acrylate (E) include reaction products of a monofunctional (meth)acrylate (a) having a hydroxyl group and an organic monoisocyanate compound (b).

[0037] Examples of monofunctional (meth)acrylates (a) having a hydroxyl group include hydroxyalkyl (meth)acrylates (2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 1,4-cyclohexanedimethanol monoacrylate, etc.). Monofunctional (meth)acrylate (a) having a hydroxyl group may be used alone or in combination of two or more types.

[0038] Of these monofunctional (meth)acrylates (a) having hydroxyl groups, 2-hydroxyethyl (meth)acrylate and 4-hydroxybutyl (meth)acrylate are preferred from the viewpoint of viscosity.

[0039] Examples of organic monoisocyanate compounds (b) include aliphatic monoisocyanate compounds (b1), alicyclic monoisocyanate compounds (b2), and aromatic monoisocyanate compounds (b3). Examples of aliphatic monoisocyanate compounds (b1) include methyl isocyanate, ethyl isocyanate, propyl isocyanate, isopropyl isocyanate, butyl isocyanate, hexyl acrylate, octyl isocyanate, lauryl isocyanate, tetradecyl isocyanate, hexadecyl isocyanate, and octadecyl isocyanate. Examples of alicyclic monoisocyanate compounds (b2) include cyclohexyl isocyanates. Examples of aromatic monoisocyanate compounds (b3) include phenyl isocyanate and torylene isocyanate. Organic monoisocyanate compound (b) may be used alone or in combination of two or more types.

[0040] Of these organic monoisocyanate compounds (b), (b1) and (b2) are preferred from the viewpoint of elongation and viscosity of the cured product, (b1) is more preferred, and methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, and hexyl isocyanate are particularly preferred.

[0041] As the monofunctional urethane (meth)acrylate (E), a reaction product obtained by urethane-forming a monofunctional (meth)acrylate (a) having a hydroxyl group and an organic monoisocyanate compound (b) using a known method can be used. Alternatively, commercially available products can be used, such as Viscoat #216 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Etermer EM2080 (manufactured by Choko Material Industry Co., Ltd.), and Genomer 1122 (manufactured by RAHN).

[0042] The (meth)acrylate (F) having a phosphate group is not limited as long as it is a phosphate ester having a (meth)acryloyl group, and examples include those with 1 to 3 (meth)acryloyl functional groups. It is possible to use commercially available products, such as 2-methacryloyloxyethyl acid phosphate (Unichemical, Fosmer M), acid phosphopolyoxyethylene glycol monomethacrylate (Unichemical, Fosmer PE), acid phosphopolyoxypropylene glycol monomethacrylate (Unichemical, Fosmer PP), 2-acryloyloxyethyl acid phosphate (Kyoeisha Chemical, Light Acrylate P-1A(N)), 2-methacryloyloxyethyl acid phosphate (Kyoeisha Chemical, Light Ester P-1M), bis(2-methacryloyloxyethyl) acid phosphate (Kyoeisha Chemical, Light Ester P-2M), and bis(2-methacryloyloxyethyl) acid phosphate (Nippon Kayaku, KAYAMER). Examples include PM-2) and the reaction product of a 6-hexanolide addition polymer of 2-hydroxyethyl methacrylate and phosphoric acid anhydride (manufactured by Nippon Kayaku Co., Ltd., KAYAMER PM-21). In the present invention, these phosphate-containing (meth)acrylates (F) may be used individually or in combination of two or more.

[0043] Of these, from the viewpoint of metal adhesion, (meth)acrylate having phosphate groups with 1 to 2 functional groups of (meth)acryloyl groups is preferred, and more preferably is the reaction product of a 6-hexanolide addition polymer of 2-(meth)acryloyloxyethyl acid phosphate, bis{2-(meth)acryloyloxyethyl} acid phosphate, and 2-hydroxyethyl methacrylate with phosphoric anhydride.

[0044] The photopolymerization initiator (G) is not limited as long as it generates radicals and ions, etc., upon irradiation with active energy rays to cause a monomer polymerization reaction, and a photopolymerization initiator that generates radicals upon irradiation with active energy rays is preferably used. Preferred photopolymerization initiators (G) include acylphosphine oxide compounds (G1), α-hydroxyalkylphenone compounds (G2), α-aminoalkylphenone compounds (G3), ketal compounds (G4), benzoylformate compounds (G5), thioxanthone compounds (G6), benzophenone compounds (G7), and oxime ester compounds (G8).

[0045] Examples of acylphosphine oxide compounds (G1) include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0046] Examples of α-hydroxyalkylphenone compounds (G2) include 1-hydroxycyclohexylphenyl ketone and 2-hydroxy-2-methyl-1-phenylpropan-1-one.

[0047] Examples of α-aminoalkylphenone compounds (G3) include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-butan-1-one, and 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-butan-1-one.

[0048] Examples of ketal compounds (G4) include benzyldimethyl ketal.

[0049] Examples of benzoylformate compounds (G5) include methylbenzoylformate.

[0050] Examples of thioxanthone compounds (G6) include 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone.

[0051] Examples of benzophenone compounds (G7) include benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 4,4'-bismethylaminobenzophenone.

[0052] Examples of oxime ester compounds (G8) include 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyl oxime) and 1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazole-3-yl]-ethanone-1-(O-acetyl oxime). In the present invention, these photopolymerization initiators (G) may be used individually or in combination of two or more.

[0053] Of these photopolymerization initiators (G), those preferred from the viewpoint of curability and transmittance of the cured product are acylphosphine oxide compounds (G1) and α-hydroxyalkylphenone compounds (G2), more preferably acylphosphine oxide compounds (G1), and particularly preferably bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0054] The content of (meth)acrylate (A) having an alicyclic skeleton in the present invention is 5 to 50% by weight, preferably 15 to 50% by weight, more preferably 15 to 40% by weight, and particularly preferably 20 to 40% by weight, based on the total weight of (A), (B), (H), and (F). If the weight percentage of (A) is less than 5% by weight, the elongation of the cured product will be insufficient, and if it exceeds 50% by weight, the elongation of the cured product will also be insufficient.

[0055] The content of N-substituted (meth)acrylamide (B) in the present invention is 10 to 50% by weight, preferably 10 to 45% by weight, more preferably 20 to 45% by weight, and particularly preferably 20 to 40% by weight, based on the total weight of (A), (B), (H), and (F). If the weight percentage of (B) is less than 10% by weight, the curing properties will be insufficient, and if it exceeds 50% by weight, the elongation of the cured product will be insufficient.

[0056] The content of (meth)acrylate (H) in the present invention is 10 to 45% by weight based on the total content of (A), (B), (H), and (F), preferably 10 to 40% by weight, more preferably 10 to 35% by weight, and particularly preferably 10 to 30% by weight. If the weight percentage of (H) is less than 10% by weight, the elongation of the cured product will be insufficient, and if it exceeds 45% by weight, the adhesion will be insufficient.

[0057] The content of (meth)acrylate (F) having a phosphate group in the present invention is 0.5 to 7.5% by weight, preferably 1 to 7.5% by weight, and more preferably 1 to 6% by weight, based on the total weight of (A), (B), (H), and (F). If the weight percentage of (F) is less than 0.5% by weight, the adhesion to the substrate will be insufficient, and if it exceeds 7.5% by weight, the storage stability may be insufficient.

[0058] The content of the photopolymerization initiator (G) in the present invention is 2 to 20% by weight, preferably 2 to 15% by weight, and more preferably 5 to 12% by weight, based on the total weight of (A), (B), (H), and (F). If the weight percentage of (G) is less than 2% by weight, the curing performance will be insufficient, and if it exceeds 20% by weight, the transmittance of the cured product will be insufficient.

[0059] The active energy ray curable composition of the present invention may contain other monomers (Q) other than the alicyclic skeleton (meth)acrylate (A), N-substituted (meth)acrylamide (B), monofunctional (meth)acrylate (C), bifunctional (meth)acrylate (D), monofunctional urethane (meth)acrylate (E), and (meth)acrylate (F) having a phosphate group, to the extent that they do not impair the effects of the present invention. Other monomers (Q) include monofunctional (meth)acrylates (excluding those falling under (A), (C), (E), and (F) above), bifunctional (meth)acrylates (excluding those falling under (D) above), and trifunctional or more (meth)acrylates. The content of other monomers (Q) is 0 to 20% by weight, preferably 0 to 10% by weight, based on the total weight of (A), (B), (H), and (F) above. Furthermore, in the present invention, if monomers having cationic polymerizable groups such as vinyl ether groups and N-vinyl groups are used, the storage stability of the active energy ray curable composition may be insufficient, so it is preferable not to use them.

[0060] Monofunctional (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate, hexyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, 2-ethylhexyldiglycol (meth)acrylate, 2-ethylhexylcarbitol (meth)acrylate, 2,2,2-tetrafluoroethyl( Examples include meth)acrylate, 1H,1H,2H,2H-perfluorodecyl(meth)acrylate, 4-butylphenyl(meth)acrylate, phenyl(meth)acrylate, 2,4,5-tetramethylphenyl(meth)acrylate, phenoxymethyl(meth)acrylate, phenoxyethyl(meth)acrylate, trimethoxysilylpropyl(meth)acrylate, trimethoxysilylpropyl(meth)acrylate, trimethylsilylpropyl(meth)acrylate, trifluoroethyl(meth)acrylate, and perfluorooctylethyl(meth)acrylate.

[0061] Examples of (meth)acrylates with three or more functions include trifunctional (meth)acrylate monomers and (meth)acrylate monomers with four or more functions.

[0062] Trifunctional (meth)acrylate monomers include trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane modified tri(meth)acrylate with 3-4 carbon atoms alkylene oxide, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, trimethylolpropane tri((meth)acryloyloxypropyl) ether, sorbitol tri(meth)acrylate, tri(meth)acrylate of pentaerythritol alkylene oxide adducts of 1-30 molars, and ethoxylated glycerin. Examples include re(meth)acrylate.

[0063] Examples of (meth)acrylate monomers with four or more functions include pentaerythritol tetra(meth)acrylate, sorbitol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol propionic acid tetra(meth)acrylate, tetra(meth)acrylate of 1 to 11 molar adducts of 3-4 carbon atoms of pentaerythritol, sorbitol penta(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, sorbitol hexa(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0064] The active energy ray curable composition of the present invention may contain various additives as needed, as long as they do not inhibit the effects of the present invention. Examples of additives include leveling agents, charge regulators, light stabilizers, UV absorbers, surface treatment agents, antioxidants, anti-aging agents, crosslinking accelerators, plasticizers, preservatives, pH adjusters, defoamers, and humectants.

[0065] The method for producing the active energy ray-curable composition of the present invention is not particularly limited. For example, the above components can be mixed by stirring them in a suitable container such as a glass beaker, can, or plastic cup using a stirring rod, spatula, etc., or by uniformly mixing them using a known mixing device (such as a mechanical stirrer or magnetic stirrer, a mixing device equipped with a stirring spring such as a paddle, a dissolver, a ball mill, or a planetary mixer). The active energy ray curable composition of the present invention is preferably liquid at room temperature, and its viscosity can be measured using an E-type viscometer [such as the "VISCOMETER TV-25L" manufactured by Toki Sangyo Co., Ltd.] and a B-type viscometer.

[0066] To obtain a cured product of an active energy ray-curable composition, the active energy ray-curable ink composition is applied to a substrate by a known method, and then cured by irradiation with active energy rays. Examples of active energy rays in this invention include ultraviolet rays and electron beams. The active energy rays used for curing the active energy ray-curable composition of the present invention can be adjusted by selecting a photopolymerization initiator. When the aforementioned photopolymerization initiator (G) is used, photocuring is possible by irradiation with active energy rays having a wavelength of 200 to 700 nm, and it is preferable that curing is possible by irradiation with light (ultraviolet light) having a wavelength of 200 to 400 nm.

[0067] As light sources that emit ultraviolet light, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and high-power metal halide lamps can be used (Latest Trends in UV / EB Curing Technology, edited by Radtech Research Group, CMC Publishing, p. 138, 2006), as well as LEDs. Among these, LEDs consume less power and generate less ozone compared to other light sources, resulting in lower running costs and a smaller environmental impact. When curing with an LED light source, an LED light source ultraviolet irradiation device [for example, LED light source ultraviolet irradiation device "FJ100 150×20 365, phoseon", manufactured by TECHNOLOGY Co., Ltd.] can be used. The amount of ultraviolet light irradiated when curing the active energy ray-curable composition of the present invention is preferably 10 to 10,000 mJ / cm² from the viewpoint of curability and flexibility of the cured product. 2 More preferably 50 to 5,000 mJ / cm² 2 That is the case. When irradiating with the aforementioned electron beam, a known electron beam irradiation device can be used. The electron beam irradiation dose is preferably 1 to 10 Mrad from the viewpoint of curability and suppression of deterioration of the cured product.

[0068] The material to which the active energy ray-curable composition of the present invention is applied can be appropriately selected according to the application, and organic materials such as plastics, or inorganic materials such as metals and glass can be used. Examples of metals include steel, hot-dip galvanized steel, electro-galvanized steel, tinplate, tin-free steel, various other plated or alloy-plated steels, stainless steel, aluminum, gold, platinum, silver, and copper. Furthermore, various surface treatments such as phosphate treatment, chromate treatment, organic phosphate treatment, organic chromate treatment, and heavy metal substitution treatment may be applied. Examples of plastic materials include polyester resins {polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), etc.}, acrylic resins (triacetylcellulose, polycarbonate resin and methyl methacrylate copolymers, etc.), acrylonitrile-butadiene-styrene copolymer (ABS) resin, styrene resin, polysulfone resin, polyethersulfone resin, polycarbonate resin, vinyl chloride resin, polymethacrylimide resin, and polyolefin resins (polyethylene, polypropylene and cycloolefin polymers, etc.). Examples of inorganic materials include glass and ceramics. Of these, the active energy ray curable composition of the present invention exhibits particularly excellent adhesion to metals.

[0069] As a method for applying the active energy ray-curable composition of the present invention to a substrate, known coating methods such as spin coating, roll coating, and spray coating, as well as known printing methods such as lithographic printing, cardboard printing, metal printing, offset printing, screen printing, and gravure printing, can be applied. Furthermore, since the composition of the present invention has low viscosity at room temperature, it can also be applied to inkjet coating methods (inkjet printing) that continuously eject fine droplets. Inkjet printing allows for precise and high-speed printing with relatively simple equipment, making it ideally suited for the manufacture of display components such as liquid crystal displays and organic EL displays, as well as other electronic and optical components.

[0070] The cured product of the active energy ray curable composition of the present invention has high elongation and metal adhesion, making it useful as a material for various electronic and optical components, including display components. In particular, it can be suitably used for bonding and sealing applications of display components such as organic EL displays, electronic components such as image sensors, and semiconductor packages. It can also be widely used for various coatings, inks (UV printing inks and UV inkjet printing inks, etc.), and paints. [Examples]

[0071] The present invention will be further described below with reference to examples and comparative examples, but the present invention is not limited thereto.

[0072] <Preparation of Active Energy Ray Curable Compositions> (Example 1) The active energy ray curable composition of Example 1 was prepared by uniformly mixing 27.5 parts by weight of isobornyl acrylate (A-1), 44.0 parts by weight of N-acryloylmorpholine (B-1), 7.5 parts by weight of lauryl acrylate (C-1), 10.0 parts by weight of A-600 (D-1), 10.0 parts by weight of Viscoat #216 (E-1), and 1.0 part by weight of KAYAMER PM-2 (F-1), and then adding 10.0 parts by weight of Irgacure 819 (G-1) and mixing uniformly.

[0073] (Examples 2-23 and Comparative Examples 1-7) Active energy ray curable compositions for Examples 2-23 and Comparative Examples 1-7 were prepared in the same manner as in Example 1, except that the raw materials used had the formulations shown in Table 1 or Table 2.

[0074] [Table 1]

[0075] [Table 2]

[0076] The raw materials used in Table 1 or Table 2 are as follows: (A-1): Isobornyl acrylate [Product name: Light Acrylate IBXA, manufactured by Kyoeisha Chemical Co., Ltd.] (A-2): Dicyclopentanyl acrylate [Product name: FA-513AS, manufactured by Hitachi Chemical Co., Ltd.] (A-3): t-Butylcyclohexyl acrylate [Trade name: TBCHA, manufactured by KJ Chemicals] (A-4): Trimethylcyclohexyl acrylate [Product name: SR-420, manufactured by Arkema] (A-5): 1-Ethylcyclohexyl acrylate [manufactured by Tokyo Chemical Industry Co., Ltd.] (B-1): N-Acryloylmorpholine [Trade name: ACMO, manufactured by KJ Chemicals] (B-2): N,N-Diethylacrylamide [Product name: DEAA, manufactured by KJ Chemicals] (B-3): N,N-dimethylacrylamide [Product name: DMAA, manufactured by KJ Chemicals] (C-1): Lauryl acrylate [Product name: LA, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (Tg of homopolymer: -30°C) (C-2): Isodecyl acrylate [Product name: IDAA, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (Tg of homopolymer: -60℃) (C-3): Isostearyl acrylate [Trade name: ISTA, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (Tg of homopolymer: -15℃) (D-1): Polyethylene glycol (number average molecular weight 600) diacrylate [product name: NK Ester A-600, manufactured by Shin Nakamura Chemical Industry Co., Ltd.] (homopolymer Tg: -42℃) (D-2): Polyethylene glycol (number average molecular weight 1000) diacrylate [product name: NK Ester A-1000, manufactured by Shin Nakamura Chemical Industry Co., Ltd.] (homopolymer Tg: -60℃) (D-3): Polypropylene glycol (number average molecular weight 700) diacrylate [product name: NK Ester APG-700, manufactured by Shin Nakamura Chemical Industry Co., Ltd.] (Tg of homopolymer: -32℃) (D-4): Polytetramethylene glycol (number average molecular weight 650) diacrylate [product name: NK Ester A-PTMG65, manufactured by Shin Nakamura Chemical Industry Co., Ltd.] (Tg of homopolymer: -30℃) (E-1):2-[(butylamino)carbonyl]oxyethyl acrylate [Product name: Viscoat #216, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (F-1): Bis(2-methacryloyloxyethyl) acid phosphate [Product name: KAYAMER PM-2, manufactured by Nippon Kayaku Co., Ltd.] (F-2): Reaction product of 6-hexanolide addition polymerization of 2-hydroxyethyl methacrylate and phosphoric anhydride [Product name: KAYAMER PM-21, manufactured by Nippon Kayaku Co., Ltd.] (F-3): 2-Acryloyloxyethyl acid phosphate [Product name: Light Acrylate P-1A(N), manufactured by Kyoeisha Chemical Co., Ltd.] (F-4): Acid phosphopolyoxypropylene glycol monomethacrylate [Product name: Fosmar PP, manufactured by Unichemical Co., Ltd.] (G-1): Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide [Trade name: Irgacure 819, manufactured by BASF] (G-2): (2,4,6-trimethylbenzoyl)-phenylphosphine oxide [Trade name: Irgacure TPO, manufactured by BASF] (Q-1): Neopentyl glycol diacrylate [Product name: Light Acrylate NP-A, manufactured by Kyoeisha Chemical Co., Ltd.] (Q-2): 2-(2-vinyloxyethoxy)ethyl acrylate [Product name: VEEA, manufactured by Nippon Shokubai Co., Ltd.]

[0077] The initial viscosity, coating curability, total light transmittance of the cured product, elongation of the cured product, metal adhesion, and storage stability (viscosity change, total light transmittance) of each active energy ray curable composition obtained in Examples 1 to 23 and Comparative Examples 1 to 7 were measured or evaluated using the following test methods, and the results are shown in Table 1 or Table 2.

[0078] (1) Measurement of initial viscosity The active energy ray-curable compositions obtained in Examples 1 to 23 and Comparative Examples 1 to 7 were temperature-conditioned at 25°C for 30 minutes, and the viscosity (mPa·s) was measured under the following conditions using an E-type viscometer ["VISCOMETER TV-25L" manufactured by Toki Sangyo Co., Ltd.]. In the present invention, the viscosity needs to be 20.0 mPa·s or less. [Measurement conditions] Cone rotor: Standard cone rotor (1°34’×R24) Measurement temperature: 25°C Measurement range: M Rotation speed: 50 rpm

[0079] (2) Evaluation of film curing properties Each of the active energy ray-curable compositions obtained in Examples 1 to 23 and Comparative Examples 1 to 7 was applied to a surface-treated PET (polyethylene terephthalate) film with a thickness of 100 μm ["Cosmo Shine A4300" manufactured by Toyobo Co., Ltd.] using an applicator so that the film thickness became 10 μm. Subsequently, using an LED light source ultraviolet irradiation device [model number "FJ100 150×20 385", manufactured by phoseon TECHNOLOGY Co., Ltd., irradiation wavelength 385 nm], exposure was performed under a nitrogen atmosphere at an irradiation intensity of 200 mW / cm 2 The exposure amount was 1000 mJ / cm 2 The curing properties of the cured film immediately after light irradiation and 10 seconds after light irradiation were confirmed by touching to check the presence or absence of tack. When there was tack, exposure was performed again at an irradiation intensity of 200 mW / cm 2 (the total exposure amount of the first and second exposures: 2000 mJ / cm 2 ), and the curing properties of the cured film immediately after light irradiation and 10 seconds after light irradiation were confirmed by touching to check the presence or absence of tack. The film curing properties were evaluated according to the following criteria. The film curing properties need to be 2 or more, and preferably 3. [Evaluation criteria] 3: Tack disappeared at an exposure amount of 1000 mJ / cm 2 2: Total exposure amount 2000 mJ / cm 2 ​And the tucks disappeared. 1: Total exposure 2000 mJ / cm² 2 But it has pleats.

[0080] (3) Evaluation of storage stability (viscosity change after storage at 60°C for 500 hours) Each of the active energy ray-curable compositions obtained in Examples 1-23 and Comparative Examples 1-7 was placed in a light-shielding plastic container with a lid, stored in a constant temperature bath at 60°C for 500 hours, then temperature-controlled at 25°C for 1 hour, and the viscosity was measured under the same conditions as in "(1) Measurement of initial viscosity" above. Next, the viscosity change rate (%) was calculated using the following formula (1) and evaluated according to the following criteria. Viscosity change rate (%) = (YX) / X × 100 ... (1) X: Initial viscosity (unit: mPa·s) Y: Viscosity after storage at 60°C for 500 hours (unit: mPa·s) [Evaluation Criteria] 5: Viscosity change rate is less than 1% 4: Viscosity change rate is 1% or more but less than 5% 3: Viscosity change rate is 5% or more but less than 10% 2: Viscosity change rate is 10% or more but less than 15% 1: Viscosity change rate of 15% or more The viscosity change rate must be at or above evaluation criterion 4.

[0081] (4) Evaluation of the total light transmittance of the cured product Each of the active energy ray-curable compositions obtained in Examples 1-23 and Comparative Examples 1-7 was applied to a surface-treated 100 μm thick PET (polyethylene terephthalate) film [Cosmoshine A4300, manufactured by Toyobo Co., Ltd.] using an applicator to a film thickness of 10 μm. Subsequently, an LED light source ultraviolet irradiation device [model number "FJ100 150×20 385", manufactured by Phoseon Technology Co., Ltd., irradiation wavelength 385 nm] was used to irradiate the film at an intensity of 200 mW / cm² under a nitrogen atmosphere. 2 The samples were exposed to light and prepared for evaluation. The exposure dose was 2000 mJ / cm². 2 That was the case. The prepared evaluation samples were temperature-controlled at 25°C for 30 minutes, and the total light transmittance (%) was measured using a total light transmittance measuring device [product name "haze-garddual", manufactured by BYK gardner Co., Ltd.] in accordance with JIS-K7105. In this invention, a transmittance of 90% or higher is required.

[0082] (5) Evaluation of the elongation rate of the cured product <Preparation of test specimens> A PET film [product name: Lumirror S, manufactured by Toray Industries, Inc.] was attached to a glass plate [product name: GLASS PLATE, manufactured by AS ONE Corporation, 200 mm x 200 mm x 5 mm thick], and an active energy ray curable composition was applied using an applicator to achieve a cured film thickness of 100 μm. The mixture was then irradiated with ultraviolet light at a rate of 2000 mJ / cm² under a nitrogen atmosphere using an ultraviolet irradiation device [model number "VPS / I600", manufactured by Fusion UV Systems Co., Ltd.]. 2 A PET film coated with a cured product of an active energy ray-curable composition was obtained by irradiation. The PET film coated with the above cured product was punched out into a dumbbell shape (size 3) in accordance with JIS K 6251:2017, and then the PET film was peeled off to obtain test specimens for measurement. <Tensile Test> The obtained test specimens were left to stand at 25°C and 50% RH for 5 hours, and then a tensile test was performed using an Autograph [model number "AG-IS" (manufactured by Shimadzu Corporation)] in accordance with JIS K 6251:2017, and the elongation was measured. [Measurement conditions] Chuck spacing: 60mm Distance between gauge lines: 20mm Tensile speed: 10 mm / min Next, the growth rate (%) was calculated using the following formula (2). Elongation (%) = (Gauge length at fracture - Gauge length) / (Gauge length) × 100 ... (2)

[0083] (6) Evaluation of metal adhesion (to stainless steel sheet) Each of the active energy ray-curable compositions obtained in Examples 1-23 and Comparative Examples 1-7 was applied to a stainless steel (SUS316) sheet (film thickness 1 mm) using an applicator to a film thickness of 10 μm. Subsequently, an LED light source ultraviolet irradiation device [model number "FJ100 150×20 385", manufactured by Phoseon Technology Co., Ltd., irradiation wavelength 385 nm] was used to irradiate the sheet at an intensity of 200 mW / cm². 2 The samples were exposed to light and prepared for evaluation. The exposure dose was 2000 mJ / cm². 2 The obtained evaluation samples were left to stand for 24 hours in an environment of 23°C and 50% relative humidity. Then, the cured coating on the substrate was cross-cut into a 2mm x 2mm grid (100 squares), cellophane adhesive tape was applied to it, and peeled off at a 90-degree angle. The state of peeling of the cured material from the substrate was visually observed. Two grids were created for each sample for evaluation, and the average number of squares in which the cured material remained attached to the substrate without peeling is shown in Table 1. An average number of attached squares must be 80 or more, preferably 90 or more, and even more preferably 100.

[0084] (7) Evaluation of metal adhesion (to copper plate) A sample for evaluation was prepared in the same manner as in "(5) Evaluation of substrate adhesion (against stainless steel plate)" above, except that the substrate was changed from a stainless steel plate to a copper plate (film thickness 1 mm). In the same manner as above, 90-degree peeling was performed on two grid boards, and the average number of squares in which the hardened material remained adhered to the substrate is shown in Table 1. The average number of adhered squares must be 80 or more, preferably 90 or more, and even more preferably 100.

[0085] (8) Evaluation of storage stability (transmittance after storage at 60°C for 300 hours) Each of the active energy ray-curable compositions obtained in Examples 1-23 and Comparative Examples 1-7 was placed in a light-shielding plastic container with a lid and stored in a constant temperature bath at 60°C for 300 hours. After that, evaluation samples were prepared in the same manner as in "Evaluation of Total Light Transmittance of Cured Products" described above, and the total light transmittance was measured. In the present invention, it is necessary for the total light transmittance to be 90% or higher, and it is preferable that the change from the initial total light transmittance is small.

[0086] As shown in Table 1 or Table 2, the active energy ray curable compositions of Examples 1 to 23 of the present invention exhibit low viscosity and excellent storage stability, and their cured products have excellent ductility and metal adhesion. Furthermore, the permeability and storage stability of the cured products were also good. On the other hand, Comparative Examples 1 and 7 lacked sufficient coating curability and metal adhesion could not be evaluated due to tack on the surface of the cured coating; Comparative Example 2 had too high a viscosity and did not meet the standards; Comparative Example 3 lacked sufficient total light transmittance, elongation, and storage stability of the cured product; Comparative Example 4 lacked metal adhesion; Comparative Example 5 did not meet the viscosity standards and also lacked storage stability; and Comparative Example 6 lacked sufficient elongation of the cured product. [Industrial applicability]

[0087] The active energy ray curable resin composition of the present invention has low viscosity and excellent storage stability, and its cured product has high transparency, high elongation, and metal adhesion, making it useful as a material for various electronic components and optical components, including display components such as flexible displays. In particular, it can be suitably used for bonding and sealing applications of display components such as organic ELs, electronic components such as image sensors, and semiconductor packages. It can also be widely used for various coatings, inks (UV printing inks and UV inkjet printing inks, etc.), and paints.

Claims

1. An active energy ray curable composition comprising an alicyclic (meth)acrylate (A), an N-substituted (meth)acrylamide (B), a (meth)acrylate (H) without a phosphate group, a (meth)acrylate (F) having a phosphate group, and a photopolymerization initiator (G), wherein the (meth)acrylate (H) is at least one selected from the group consisting of monofunctional (meth)acrylate (C), difunctional (meth)acrylate (D), and monofunctional urethane (meth)acrylate (E) having a linear or branched alkyl group having 10 to 18 carbon atoms, and the monofunctional (meth)acrylate (F) has a phosphate group. An active energy ray curable composition containing rate (C) as an essential component, wherein the monofunctional (meth)acrylate (C) contains at least one selected from the group consisting of lauryl (meth)acrylate, isodecyl (meth)acrylate, and isostearyl (meth)acrylate, and based on the total weight of (A), (B), (H), and (F), the content of (A) is 5 to 50% by weight, the content of (B) is 10 to 50% by weight, the content of (H) is 10 to 45% by weight, the content of (F) is 0.5 to 7.5% by weight, and the content of (G) is 2 to 20% by weight.

2. The active energy ray curable composition according to claim 1, wherein the (meth)acrylate (A) having an alicyclic skeleton contains at least one selected from the group consisting of isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, and 1-ethylcyclohexyl acrylate.

3. The active energy ray curable composition according to claim 1 or 2, wherein the N-substituted (meth)acrylamide (B) contains at least one selected from the group consisting of N-(meth)acryloylmorpholine, N,N-diethyl(meth)acrylamide, and N,N-dimethyl(meth)acrylamide.

4. The active energy ray curable composition according to any one of claims 1 to 3, comprising the aforementioned bifunctional (meth)acrylate (D) as an essential component.

5. The active energy ray curable composition according to any one of claims 1 to 4, wherein the difunctional (meth)acrylate (D) is a difunctional (meth)acrylate having a homopolymer glass transition temperature (Tg) of 0°C or less.

6. A cured product obtained by curing an active energy ray curable composition according to any one of claims 1 to 5.

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