Photocurable acrylic resin composition and cured product thereof

Abstract

The present invention relates to a photocurable acrylic resin composition comprising: a first (meth)acrylic compound represented by chemical formula 1 (see the specification); a second (meth)acrylic compound represented by chemical formula 2 (see the specification); a third (meth)acrylic compound represented by chemical formula 3 (see the specification); and a photopolymerization initiator. The photocurable acrylic resin composition can effectively block moisture and oxygen, thereby securing the performance and lifespan of an organic light-emitting device, and further exhibits excellent processability and a low dielectric constant, and therefore may be used to encapsulate an organic light-emitting device.

Description

Photocurable acrylic resin composition and cured product thereof

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2024-0179106 filed on December 5, 2024, and all contents disclosed in the document of said Korean Patent Application are incorporated herein as part of this specification.

[0003] Technology field

[0004] The present invention relates to a photocurable acrylic resin composition and a cured product thereof.

[0005]

[0006] Research on organic electroluminescent (EL) devices has continued since Bernanose’s observation of organic thin-film luminescence in the 1950s, leading to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic electroluminescent device with a stacked structure divided into a hole layer and a functional layer for the emissive layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, development has progressed by introducing distinct organic layers within the device, leading to the development of specialized materials used for this purpose.

[0007] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0008] Organic layer materials, electrodes, etc., constituting organic electroluminescent devices have a problem in that their light-emitting characteristics and lifespan deteriorate due to external moisture or oxygen. Therefore, a protective layer is required to protect the organic layer materials and electrodes, etc. To effectively block external moisture or oxygen, such a protective layer is typically formed from one or more organic layers, inorganic layers, or a stacked structure thereof.

[0009] Meanwhile, capacitive touch panels utilizing organic electroluminescent devices have recently been widely adopted. These capacitive touch panels detect touch based on changes in capacitance when a conductor comes into contact with the panel; however, in the case of materials with high dielectric constant, significant polarization occurs when an external electric field is applied, which tends to reduce touch sensitivity.

[0010] Therefore, there is a need to develop a composition for encapsulating organic light-emitting diodes that has low dielectric constant characteristics and excellent touch sensitivity of the touch panel.

[0011] Prior art literature

[0012] Republic of Korea Registered Patent Publication No. 10-2190637

[0013]

[0014] The present invention aims to provide a photocurable acrylic resin composition and a cured product thereof that can be used for encapsulating organic light-emitting diodes by having low dielectric constant characteristics to ensure excellent touch sensitivity of the touch panel, as well as effectively blocking moisture or oxygen entering the organic light-emitting diode to secure the performance and lifespan of the organic light-emitting diode.

[0015]

[0016] To solve the above-mentioned problem, the present invention provides a photocurable acrylic resin composition comprising: a first (meth)acrylic compound represented by the following chemical formula 1; a second (meth)acrylic compound represented by the following chemical formula 2; a third (meth)acrylic compound represented by the following chemical formula 3; and a photopolymerization initiator.

[0017] [Chemical Formula 1]

[0018]

[0019] [Chemical Formula 2]

[0020]

[0021] [Chemical Formula 3]

[0022]

[0023] In the above chemical formulas 1 to 3,

[0024] R1, R4, and R5 are each independently hydrogen, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C1 to C60 alkoxy group, or a hydroxyl group, and

[0025] R2 and R3 are each independently substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and

[0026] R6 and R7 are each independently (meth)acryloyl groups, and

[0027] L1 is a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, and

[0028] L2 and L3 are each independently substituted or unsubstituted alkylene groups having 1 to 60 carbon atoms, and

[0029] X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and

[0030] m and n are each independently integers from 1 to 4.

[0031] In the above chemical formulas 1 to 3,

[0032] R1, R4, and R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group, and

[0033] R2 and R3 are each independently an alkyl group having 5 to 20 carbon atoms, and

[0034] R6 and R7 are each independently (meth)acryloyl groups, and

[0035] L1 is an alkylene group having 10 to 25 carbon atoms, and

[0036] L2 and L3 are each independently an alkylene group having 1 to 10 carbon atoms, and

[0037] X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and

[0038] m and n can each independently be integers from 1 to 4.

[0039] In the above chemical formulas 1 to 3,

[0040] R1, R4, and R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group, and

[0041] R2 is an alkyl group having 5 to 11 carbon atoms, and

[0042] R3 is an alkyl group having 12 to 20 carbon atoms, and

[0043] R6 and R7 are each independently (meth)acryloyl groups, and

[0044] L1 is an alkylene group having 10 to 25 carbon atoms, and

[0045] L2 and L3 are each independently an alkylene group having 1 to 10 carbon atoms, and

[0046] X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and

[0047] m and n can each independently be integers from 1 to 4.

[0048] The above photopolymerization initiator may be one or more selected from the group consisting of triazine-based, acetophenone-based, benzophenone-based, thioxantone-based, benzoin-based, phosphorus-based, and oxime-based.

[0049] The above photocurable acrylic resin composition may have a dielectric constant of 2.8 or less at a frequency in the range of 100 kHz to 1 MHz.

[0050] The above photocurable acrylic resin composition may have a viscosity of 50 cPs or less at 25 ℃ and a surface tension of 20 N / m to 40 N / m.

[0051] The content of the first (meth)acrylic compound is 30% to 80% by weight based on the total weight of the photocurable acrylic resin composition, the content of the second (meth)acrylic compound is 10% to 60% by weight based on the total weight of the photocurable acrylic resin composition, the content of the third (meth)acrylic compound is 1% to 40% by weight based on the total weight of the photocurable acrylic resin composition, and the content of the photopolymerization initiator may be 0.01% to 5% by weight based on 100% by weight of the entire photocurable acrylic resin composition.

[0052] In addition, to solve the above-mentioned problem, the present invention provides a cured product of the above-mentioned photocurable acrylic resin composition.

[0053]

[0054] The photocurable acrylic resin composition according to the present invention can effectively block moisture or oxygen entering the organic light-emitting device to ensure the performance and lifespan of the organic light-emitting device, and also has excellent processability and low dielectric constant characteristics to ensure excellent touch sensitivity of the touch panel, so it can be used for encapsulating organic light-emitting devices.

[0055]

[0056] The advantages and features of the present invention and the methods for achieving them will become clear by referring to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below but may be implemented in various different forms. These embodiments are provided merely to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the present invention, and the present invention is defined only by the scope of the claims.

[0057] The terms used herein are for describing the embodiments and are not intended to limit the invention. In this specification, the singular form includes the plural form unless specifically stated otherwise in the text. As used herein, "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0058] In the present invention, the term "(meth)acryl compound" may mean an acryl compound and / or a methacryl compound.

[0059] In the present invention, the term "alkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of a linear or branched structure.The above alkyl group is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1-ethylpropyl group, a 2-ethylpropyl group, an n-hexyl group, a 1-methyl-2-ethylpropyl group, a 1-ethyl-2-methylpropyl group, It may mean, but is not limited to, 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2-methylpentyl group, and 3-methylpentyl group.

[0060] In the present invention, the term "cycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of a ring structure. The cycloalkyl group may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclononyl group, and an adamantyl group, but is not limited thereto.

[0061] In the present invention, the term "alkenyl group" may refer to a monovalent functional group derived from a hydrocarbon containing one or more carbon double bonds at the middle or end of an alkyl group.

[0062] As used in this specification, the term "alkoxy group" means an alkyl group to which an oxygen radical is bonded.

[0063] As used herein, the term "(meth)acryloyl group" may mean an acryloyl group compound and / or a methacryloyl group.

[0064] As used in this specification, the term "alkylene group" means an alkanediyl group connected to a saturated hydrocarbon without a double bond, and means having two linkers.

[0065] Additionally, unless explicitly stated otherwise, in the terms “substituted or unsubstituted” as used herein, “substituted” refers to a deuterium, halogen, amino group, nitrile group, nitro group, alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, alkylamine group having 1 to 20 carbon atoms, alkylthiophene group having 1 to 20 carbon atoms, arylthiophene group having 6 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms substituted with deuterium, arylalkenyl group having 8 to 20 carbon atoms, silane group, boron group, and a carbon 2 group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P. This means that it can be substituted with one or more substituents selected from the heterocyclic groups of 20, but is not necessarily limited to these substituents.

[0066] Unless otherwise defined, all terms used herein (including technical and scientific terms) may be used in a meaning commonly understood by those skilled in the art to which the present invention pertains. Additionally, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0067]

[0068] The present invention will be described in detail below.

[0069] The present invention provides a photocurable acrylic resin composition. The photocurable acrylic resin composition comprises a first (meth)acrylic compound represented by the following chemical formula 1;

[0070] A second (meth)acrylic compound represented by the following chemical formula 2;

[0071] A third (meth)acrylic compound represented by the following chemical formula 3; and

[0072] Includes a photopolymerization initiator;

[0073] [Chemical Formula 1]

[0074]

[0075] [Chemical Formula 2]

[0076]

[0077] [Chemical Formula 3]

[0078]

[0079] In the above chemical formulas 1 to 3,

[0080] R1, R4, and R5 are each independently hydrogen, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C1 to C60 alkoxy group, or a hydroxyl group, and

[0081] R2 and R3 are each independently substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and

[0082] R6 and R7 are each independently (meth)acryloyl groups, and

[0083] L1 is a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, and

[0084] L2 and L3 are each independently substituted or unsubstituted alkylene groups having 1 to 60 carbon atoms, and

[0085] X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and

[0086] m and n are each independently integers from 1 to 4.

[0087] The photocurable acrylic resin composition according to the present invention can effectively block moisture or oxygen entering the organic light-emitting device, thereby ensuring the performance and lifespan of the organic light-emitting device. Furthermore, it has excellent processability and low dielectric constant characteristics to ensure excellent touch sensitivity of the touch panel, so it can be used for encapsulating organic light-emitting devices.

[0088]

[0089] In one embodiment, the first (meth)acrylic compound may be a monofunctional (meth)acrylic monomer comprising one branched-chain alkyl group and one (meth)acrylate group within the molecule. In this way, a lower dielectric constant can be achieved when a monofunctional (meth)acrylic monomer comprising one branched-chain alkyl group and one (meth)acrylate group within the molecule is included. This can be explained by the fact that the dielectric constant is lowered because the intermolecular volume increases due to the effect of widening the intermolecular spacing.

[0090] In one embodiment, in the above formula 1, R1 is hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group, and R2 and R3 may each independently be an alkyl group having 5 to 20 carbon atoms.

[0091] In one embodiment, R1 may be hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group, R2 may be an alkyl group having 5 to 14 carbon atoms, and R3 may be an alkyl group having 12 to 20 carbon atoms.

[0092] In one embodiment, the first (meth)acrylic compound may be one or more selected from the group consisting of 2-decyl-1-tetradecanyl acrylate, 2-tetradecyl-1-octadecanyl acrylate, and 2-dodecyl-1-hexadecanyl acrylate, as specific examples.

[0093] In one embodiment, the content of the first (meth)acrylic compound may be 30% to 80% by weight, 40% to 70% by weight, or 45% to 65% by weight based on the total weight of the photocurable acrylic resin composition. When the first (meth)acrylic compound is included in an amount within the aforementioned range, excellent processability and low dielectric constant characteristics may be achieved.

[0094]

[0095] In one embodiment, the second (meth)acrylic compound may be a polyfunctional (meth)acrylic monomer comprising two or more (meth)acrylate groups. The second (meth)acrylic compound may, for example, have 2 to 6 (meth)acrylate groups or 3 to 5 (meth)acrylate groups.

[0096] In one embodiment, in the above formula 2, L1 is an alkylene group having 10 to 25 carbon atoms, and R4 and R5 may each independently be hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group.

[0097] In one embodiment, the second (meth)acrylic compound is, as specific examples, 1,10-decanediol di(meth)acrylate, 1,9-decanediol di(meth)acrylate, 1,11-undecanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, 1,13-tridecanediol di(meth)acrylate, 1,14-tetradecanediol di(meth)acrylate, 1,15-pentadecanediol di(meth)acrylate, 1,16-hexadecanediol di(meth)acrylate, 1,17-heptadecanediol di(meth)acrylate, 1,18-octadecanediol di(meth)acrylate, 1,19-nonadecanediol di(meth)acrylate, and It may be one or more selected from the group consisting of 1,20-icosandiol di(meth)acrylate.

[0098] In one embodiment, the content of the second (meth)acrylic compound may be 10% to 60% by weight, 15% to 50% by weight, or 20% to 40% by weight based on the total weight of the photocurable acrylic resin composition. When the second (meth)acrylic compound is included in an amount within the aforementioned range, excellent processability and low dielectric constant characteristics may be achieved.

[0099]

[0100] In one embodiment, the third (meth)acrylic compound may be a polyfunctional (meth)acrylic monomer comprising two (meth)acrylate groups and an aromatic ring within the molecule.

[0101] In one embodiment, in the above formula 3, R6 and R7 are each independently (meth)acryloyl groups, L2 and L3 are each independently alkylene groups having 1 to 10 carbon atoms, X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and m and n may each be independently integers from 1 to 4.

[0102] In the above chemical formula 3, the sum of m and n can be 2 to 5.

[0103] In one embodiment, the third (meth)acrylic compound may be one or more selected from the group consisting of bisphenol-A ethylene oxide diacrylate, bisphenol-A ethylene oxide dimethacrylate, bisphenol-A ethoxylate diacrylate, bisphenol-A ethoxylate dimethacrylate, bisphenol-A polyethoxylate diacrylate, and bisphenol-A diacrylate, as specific examples.

[0104] In one embodiment, the content of the third (meth)acrylic compound may be 1% to 40% by weight, 5% to 30% by weight, or 10% to 20% by weight based on the total weight of the photocurable acrylic resin composition. When the third (meth)acrylic compound is included in an amount within the aforementioned range, excellent processability and low dielectric constant characteristics may be achieved.

[0105]

[0106] In one embodiment, the photocurable acrylic resin composition according to the present invention comprises a photopolymerization initiator capable of curing a monomer included in the composition through UV irradiation or the like.

[0107] In one embodiment, the photopolymerization initiator may be one or more selected from the group consisting of triazine-based, acetophenone-based, benzophenone-based, thioxantone-based, benzoin-based, phosphorus-based, and oxime-based.

[0108] The above triazine-based photopolymerization initiators are, for example, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, It may include one or more selected from 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl(piperonyl)-6-triazine, and 2,4-(trichloromethyl(4'-methoxystyryl)-6-triazine.

[0109] The above acetophenone-based photopolymerization initiator may include, for example, one or more selected from 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyl trichloroacetophenone, pt-butyl dichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.

[0110] The above benzophenone-based photopolymerization initiator may include, for example, one or more selected from benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

[0111] The above thioxantone-based photopolymerization initiator may include, for example, one or more selected from thioxantone, 2-methyl thioxantone, isopropyl thioxantone, 2,4-diethyl thioxantone, 2,4-diisopropyl thioxantone, and 2-chlorothioxantone.

[0112] The above benzoin-based photopolymerization initiator may include, for example, one or more selected from benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0113] The above phosphorus-based photopolymerization initiator may include, for example, one or more selected from phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, bisbenzoylphenyl phosphine oxide, and benzoyldiphenyl phosphine oxide.

[0114] The above oxime-based photopolymerization initiator may include, for example, one or more selected from 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione and 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethanolone.

[0115] In one embodiment, the photopolymerization initiator can be selected as appropriate considering the desired light wavelength range and process, etc.

[0116] The content of the above photopolymerization initiator may be, for example, 0.01 to 5 parts by weight, 0.01 to 3 parts by weight, or 0.1 to 2 parts by weight with respect to 100 parts by weight of the total photocurable acrylic resin composition. When the photopolymerization initiator is included in an amount within the aforementioned range, the curing efficiency can be increased without increasing viscosity.

[0117]

[0118] In one embodiment, the photocurable acrylic resin composition may have a dielectric constant of 2.8 or less, 2.55 or less, 2 to 2.55, 2 to 2.52, or 2 to 2.5 at a frequency in the range of 100 kHz to 1 MHz. When a photocurable acrylic resin composition having low dielectric constant characteristics within the aforementioned range is applied to a touch panel, it has the effect of providing excellent touch sensitivity.

[0119] In one embodiment, the photocurable acrylic resin composition may have a viscosity at 25°C of 50 cPs or less, 10 cPs to 40 cPs, 10 cPs to 30 cPs, 10 cPs to 25 cPs, or 10 cPs to 22 cPs. The photocurable acrylic resin composition may have excellent workability by having a viscosity within the aforementioned range. Specifically, having a viscosity within the above range can improve both printing performance and curing performance. For reference, if the viscosity is too high, it is difficult to eject from the inkjet nozzle, making inkjet printing difficult, and if the viscosity is too low, flowability increases, making it difficult to form a film of appropriate thickness.

[0120] In one embodiment, the photocurable acrylic resin composition may have a surface tension of 20 N / m to 40 N / m, 30 N / m to 40 N / m, or 30 N / m to 35 N / m. The photocurable acrylic resin composition may have excellent workability by having a surface tension within the aforementioned range. Specifically, having a surface tension within the above range may provide ink characteristics that allow for smooth ejection from an inkjet device. For reference, if the surface tension of the ink is high, a phenomenon of ink droplet scattering occurs, and if the surface tension is low, the spreadability or dispersibility of the solution may increase upon collision with a substrate. The surface tension can be measured by various known methods, and for example, it can be measured by the Ring Method under conditions of 25 ℃.

[0121] In one embodiment, the transmittance of the photocurable acrylic resin composition may be 97% or more, 98% or more, 99% or more, or 99% to 99.9%. High visibility can be achieved by having a transmittance within the aforementioned range.

[0122] In one embodiment, the photocurable acrylic resin composition according to the present invention may further include additives commonly used in the art. For example, the additives may include one or more selected from the group consisting of surfactants, curing accelerators, and antioxidants.

[0123]

[0124] According to the present invention, a cured product of the photocurable acrylic resin composition is provided. Specifically, the cured product may be a cured product obtained by applying the photocurable acrylic resin composition onto a substrate and curing it through light irradiation.

[0125] Here, the specific description of the above-mentioned photocurable acrylic resin composition may be the same as described above.

[0126] The above description is not particularly limited in type, and as long as it is transparent and capable of functioning as a support, its material or thickness is not limited. Here, "transparent" may mean that the visible light transmittance is 70% or higher.

[0127] The above-mentioned material may be a commonly known material. For example, the above-mentioned material may be glass, plastic, silicone, metal, etc.

[0128] The above-mentioned substrate may be a transparent substrate. The above-mentioned transparent substrate may include, for example, one or more selected from glass, polyimide, polyetheretherketone, polyethersulfone, polyetherimide, polycarbonate, and polyethylene terephthalate.

[0129] Various known methods can be used to apply a photocurable acrylic resin composition onto the above substrate, and coating can be performed using various coating devices such as an inkjet printer, a roll coater, a spin coater, a die coater, a comma coater, and a reverse comma coater.

[0130] As for the light used for irradiating the above-mentioned photocurable acrylic resin composition, any light that promotes the polymerization reaction of the photocurable composition may be used, such as infrared, visible light, ultraviolet, X-ray, electron beam, α-ray, β-ray, γ-ray, etc., but ultraviolet light is preferred due to its excellent handling properties. For irradiating with ultraviolet light, for example, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a xenon lamp, a carbon arc, a metal halide lamp, sunlight, a laser, etc., may be used.

[0131] The cured product of the above-mentioned photocurable acrylic resin composition can be used for encapsulating organic light-emitting diodes. The photocurable acrylic resin composition can not only ensure the performance and lifespan of the organic light-emitting diode by effectively blocking moisture or oxygen entering the organic light-emitting diode, but also possess excellent processability and low dielectric constant characteristics to ensure excellent touch sensitivity of the touch panel.

[0132]

[0133] The present invention will be described in detail below through examples, but the following examples are merely illustrative of the invention and the invention is not limited by the following examples.

[0134]

[0135] [Examples and Comparative Examples]

[0136] Examples 1 to 5 and Comparative Examples 1 to 7: Preparation of Photocurable Acrylic Resin Compositions

[0137] A photocurable acrylic resin composition was prepared according to the composition of Table 1 below. Here, the content was based on weight percent. In addition, a photopolymerization initiator (BAPO, Sigma-Aldrich) was included in an amount of 1 weight part per 100 weight parts of the total photocurable acrylic resin composition.

[0138] TDMABPAEDADTD-MAISTATotal Example 1 201565-100 Example 2 351055-100 Example 3 301555-100 Example 4 252055-100 Example 5 401545-100 Comparative Example 1 2015-65100 Comparative Example 2 3510-55100 Comparative Example 3 3015-55100 Comparative Example 4 2520-55100 Comparative Example 5 4015-45100 Comparative Example 6 6535--100 Comparative Example 7 2575-100

[0139] TDMA: 1,14-Tetradecanediol dimethacrylate (CAS No.: 168473-14-1)BPAEDA: Tetrahydrofurfuryl acrylate (CAS No.: 2399-48-6)

[0140] DTD-MA: 2-decyl-1-tetradecanyl acrylate (CAS No.: 64401-02-1)

[0141] ISTA: Isostearyl acrylate (CAS No.: 93841-48-6)

[0142]

[0143] [Experimental Example]

[0144] Experimental Example 1: Measurement of Permittivity

[0145] The dielectric constant of the photocurable acrylic resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 7 was measured, and the results are shown in Table 2 below.

[0146] Specifically, the dielectric constant evaluation was performed by coating and curing the composition according to each of the above examples and comparative examples to a thickness of 5.0 μm on the lower electrode, then depositing the upper electrode to a thickness of 1,000 Å to prepare a specimen, and then measuring the prepared specimen with a KEYSIGHT E4980A and calculating the dielectric constant.

[0147]

[0148] Experimental Example 2: Viscosity Measurement

[0149] The viscosity of the photocurable acrylic resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 7 was measured, and the results are shown in Table 2 below.

[0150] Specifically, for each of the above examples and comparative examples, the viscosity was measured using a Brookfield viscometer at 25°C under 50 rpm conditions.

[0151]

[0152] Experimental Example 3: Measurement of Surface Tension

[0153] Surface tension was measured for the photocurable acrylic resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 7 above, and the results are shown in Table 2 below.

[0154] Specifically, for each of the above examples and comparative examples, the surface tension was measured at 25°C using a surface tension meter (equipment name: KRUSS K20) with the Du Nouy Ring method.

[0155]

[0156] Experimental Example 4: Measurement of Light Transmittance

[0157] For the photocurable acrylic resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 7 above, the light transmittance was measured, and the results are shown in Table 2 below.

[0158] Specifically, the light transmittance was measured by preparing a thin film sample with a thickness of 20 μm by curing in an N2 atmosphere using the composition according to each of the above examples and comparative examples, and by measuring the value at a wavelength of 550 nm using a haze meter (PerkinElmer Lambda365) for the sample.

[0159]

[0160] Dielectric Constant (F / m) Viscosity (cPs) Surface Tension (N / m) Light Transmittance (%) Example 1 2.4 3 20.5 3 0.8 99.5 Example 2 2.4 4 19.9 3 0.2 99.5 Example 3 2.4 6 20.5 3 0.7 99.5 Example 4 2.4 8 21.9 3 0.6 99.5 Example 5 2.5 22 0.1 3 0.3 99.5 Comparative Example 1 2.6 12 3.8 29.2 99.5 Comparative Example 2 2.5 9 23.0 29.1 99.5 Comparative Example 3 2.6 5 23.4 29.1 99.5 Comparative Example 4 2.6 6 25.5 29.2 99.5 Comparative Example 5 2.7 12 2.9 29.1 99.5 Comparative Example 62.7733.831.399.5 Comparative Example 72.7227.931.589.2

[0161] Referring to Table 2 above, it can be confirmed that the photocurable acrylic resin composition according to the present invention has low dielectric constant characteristics, has appropriate viscosity and surface tension, has excellent workability, and has high light transmittance, making it transparent and highly visible, and can be used for substrate protection.

[0162] On the other hand, Comparative Examples 1 to 5 used ISTA, a monofunctional acrylic compound that does not satisfy Formula 1, as the first (meth)acrylic compound, and it was confirmed that the low dielectric constant properties were reduced and the viscosity was increased.

[0163] In addition, Comparative Example 6 is a case that does not include the first (meth)acrylic compound, and it was confirmed that the low dielectric constant properties were reduced and the surface tension and viscosity were increased.

[0164] In addition, Comparative Example 7 is a case that does not include the second (meth)acrylic compound, and it was confirmed that the low dielectric constant properties were reduced, the viscosity increased, and the light transmittance decreased.

[0165]

[0166] Although embodiments of the present invention have been described above, those skilled in the art will understand that the present invention may be implemented in other specific forms without altering its technical concept or essential features. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. A first (meth)acrylic compound represented by the following chemical formula 1; A second (meth)acrylic compound represented by the following chemical formula 2; A third (meth)acrylic compound represented by the following chemical formula 3; and Photocurable acrylic resin composition comprising a photopolymerization initiator: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 1 to 3, R1, R4, and R5 are each independently hydrogen, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C1 to C60 alkoxy group, or a hydroxyl group, and R2 and R3 are each independently substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and R6 and R7 are each independently (meth)acryloyl groups, and L1 is a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, and L2 and L3 are each independently substituted or unsubstituted alkylene groups having 1 to 60 carbon atoms, and X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and m and n are each independently integers from 1 to 4.

2. In Paragraph 1, In the above chemical formulas 1 to 3, R1, R4, and R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group, and R2 and R3 are each independently an alkyl group having 5 to 20 carbon atoms, and R6 and R7 are each independently (meth)acryloyl groups, and L1 is an alkylene group having 10 to 25 carbon atoms, and L2 and L3 are each independently alkylene groups having 1 to 10 carbon atoms, and X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and A photocurable acrylic resin composition in which m and n are each independently integers from 1 to 4.

3. In Paragraph 1, In the above chemical formulas 1 to 3, R1, R4, and R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or a hydroxyl group, and R2 is an alkyl group having 5 to 11 carbon atoms, and R3 is an alkyl group having 12 to 20 carbon atoms, and R6 and R7 are each independently (meth)acryloyl groups, and L1 is an alkylene group having 10 to 25 carbon atoms, and L2 and L3 are each independently alkylene groups having 1 to 10 carbon atoms, and X1 and X2 are each independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and A photocurable acrylic resin composition in which m and n are each independently integers from 1 to 4.

4. In Paragraph 1, A photocurable acrylic resin composition in which the above photopolymerization initiator is one or more selected from the group consisting of triazine-based, acetophenone-based, benzophenone-based, thioxanthone-based, benzoin-based, phosphorus-based, and oxime-based materials.

5. In Paragraph 1, The above photocurable acrylic resin composition is a photocurable acrylic resin composition having a dielectric constant of 2.8 or less at a frequency in the range of 100 kHz to 1 MHz.

6. In Paragraph 1, The above photocurable acrylic resin composition has a viscosity of 50 cPs or less at 25 ℃ and a surface tension of 20 N / m to 40 N / m.

7. In Paragraph 1, The content of the first (meth)acrylic compound is 30% to 80% by weight based on the total weight of the photocurable acrylic resin composition, and The content of the second (meth)acrylic compound is 10% to 60% by weight based on the total weight of the photocurable acrylic resin composition, and The content of the third (meth)acrylic compound is 1% to 40% by weight based on the total weight of the photocurable acrylic resin composition, and A photocurable acrylic resin composition in which the content of the photopolymerization initiator is 0.01 to 5 parts by weight per 100 parts by weight of the total photocurable acrylic resin composition.

8. Cured product of the photocurable acrylic resin composition according to paragraph 1.

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