KR20190074096A - New compound, photo-curable composition containing the same, and cured product thereof - Google Patents

Abstract

The present invention relates to a novel compound, a composition comprising the same, and an organic electronic device encapsulated with an encapsulating material containing a cured product thereof. More particularly, the novel compound is represented by chemical formula 1. In the chemical formula 1, a definition of X, Y, R_1, R_2, and R_3 is the same as defined in claim 1. The composition containing a compound according to the present invention can realize photo-curability improved with high sensitivity.

Description

TECHNICAL FIELD The present invention relates to a novel compound, a photocurable composition containing the same, and a cured product thereof,

The present invention relates to a novel compound, a photocurable composition containing the same, and a cured product thereof.

Halogen lamps, which are frequently used in light irradiation, emit many unwanted wavelengths of light that are not necessary for polymerization, so that the efficiency of the visible light irradiation apparatus is lowered and the problem of long-time light irradiation is continued. Also, in order to reduce the light irradiation time, a visible ray irradiator having a more power density is used, and a vicious cycle in which the heat is emitted from the light irradiator incidentally and the life time of the light irradiator is further shortened.

Recently, a light emitting diode (LED) lamp has been developed as an alternative to effectively reduce these problems. The LED lamp is capable of selectively emitting only the light of the wavelength range necessary for polymerization, and is evaluated as a device capable of effectively solving the above-mentioned problems.

The irradiation light of such an LED lamp has a long wavelength up to almost 400 nm band region. However, since photo-polymerization is not effectively performed at the corresponding wavelength range only by the photoinitiator, a photosensitizer and the like are used together to increase the polymerization efficiency.

Generally, Polynuclear aromatic hydrocarbons such as dibutoxy antracene (Korean Patent No. 10-1293803) have excellent sensitivity and are mainly used together with photoinitiators.

On the other hand, phenothiazine has advantages of higher solubility to reactive monomers and oligomers than polycyclic aromatic hydrocarbon type photosensitizer, but up to now, it has not been able to effectively absorb wavelength near 400 nm, A wide absorption band is generated in the visible light region and it is difficult to utilize it as a photosensitizer.

As a result of repeated studies to solve the problems of the prior art, the applicant has found that it is possible to improve the degree of polymerization and the transmittance by selectively improving only the absorption rate at the wavelength of the irradiation light, while maintaining the solubility of the reactive monomers or oligomers, The present inventors have completed the present invention by devising a novel compound having excellent compatibility.

Korean Registered Patent No. 10-1293803 (July 31, 2013)

In order to solve the above problems, it is an object of the present invention to provide a novel compound capable of improving the polymerization degree and the transmittance by selectively improving only the absorption rate at the wavelength of the irradiated light, and having high solubility in the reactive monomer or oligomer .

Still another object of the present invention is to provide a photocurable composition which is excellent in sensitivity and permeability, including the novel compound, and is useful as an encapsulating material or an adhesive raw material.

Another object of the present invention is to provide an organic electronic device having a long-life characteristic and a long-term reliability including a cured product having improved heat resistance and excellent surface properties.

In order to accomplish the above object, one aspect of the present invention relates to a compound represented by the following general formula (1).

[Chemical Formula 1]

(In the formula 1,

X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;

R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocyclo An alkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof;

R ₃ represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof.

In this embodiment, the compound is a compound wherein X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds; R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 heteroaryl, substituted or unsubstituted C 6 -C 30 aryl Or a combination thereof; R ₃ is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6- 30 aryl group, or a combination thereof.

In this embodiment, the compound is a compound wherein X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds; R ₁ and R ₂ are independently selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms Or a combination thereof; R ₃ represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted C6- 20 aryl group, or a combination thereof.

In such an embodiment, the compound may be selected from the following structures.

Another embodiment of the present invention relates to a photocurable composition comprising a compound represented by the following general formula (1).

[Chemical Formula 1]

(In the formula 1,

X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;

R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocyclo An alkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof;

R ₃ represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof.

In another embodiment described above, the compound may be one used for light absorption.

In another embodiment of the present invention, the photocurable composition may be photocurable by generating a cation, a radical or a cation and a radical by light irradiation.

In another such aspect, the photocurable composition may further comprise a photopolymerizable monomer having at least two photocurable unsaturated groups and a photoinitiator.

In another embodiment described above, the photoinitiator may be a cationic photoinitiator.

In still another embodiment of the present invention, the photoinitiator is a benzoin derivative, an acetophenone derivative, an anthraquinone derivative, a thioxanthone derivative, a ketal derivative, a benzophenone derivative, an α-amino acetophenone derivative, an acylphosphine oxide derivative, Derivatives, and the like.

Still another aspect of the present invention relates to an organic electronic device encapsulated with an encapsulant comprising a cured product of the photo-curable composition described above.

The Phenothiazine compound according to the present invention has an advantage that the degree of polymerization and the degree of transparency can be improved by selectively improving the absorptance only at the wavelength of the irradiated light while the wavelength is not absorbed in the unnecessary visible light region other than the irradiated light wavelength band have. In addition, it has an advantage of being excellent in solubility in reactive monomers and oligomers and improving compatibility.

In addition, the composition containing the compound according to the present invention can realize photo-curability improved with high sensitivity, and the transparency and heat resistance of the cured product can be remarkably improved.

Further, when the composition comprising the compound according to the present invention is formed into a film or a sheet, the surface can be more uniform and the foreign matter can be remarkably reduced.

In addition, the composition containing the compound in the present invention can be formed into a film or sheet to encapsulate an organic electronic device, thereby providing a highly reliable organic electronic device with remarkably improved lifetime characteristics and durability.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, a novel compound, a photocurable composition containing the same, and a cured product thereof according to the present invention will be described in detail.

Here, unless otherwise defined, technical terms and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. In the following description, the gist of the present invention is unnecessarily blurred And a description of the known function and configuration will be omitted.

In the present invention, the term " substituted or substituted " means that at least one hydrogen atom in the functional group in the compound is a halogen (-F, -Cl, -Br or -I), an alkyl group having 1 to 30 carbon , An alkoxy group having 1 to 30 carbon atoms, a halogenated alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 6 to 30 carbon atoms , A hydroxyl group, an amine group, a carboxylic acid group, and an aldehyde group, with the proviso that the number of carbon atoms of the substituent may not be included in the number of carbon atoms of the functional group of Formula 1.

The substituents comprising the "alkyl", "alkoxy", "thioxy" and other "alkyl" moieties described in the present invention include both linear and branched forms. According to one embodiment of the present invention, short chain alkyl, alkoxy, thioxy and the like having 7 or less carbon atoms are preferable, but long chain having 8 or more carbon atoms is also an aspect of the present invention.

Furthermore, the "aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination, which may be a single or an aliphatic group containing, suitably, 4 to 7, preferably 5 or 6, ring atoms in each ring, A fused ring system, and a form in which a plurality of aryls are connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, The "heteroaryl" described in the present invention is not limited thereto. The "heteroaryl" described in the present invention is an organic radical derived from aromatic hydrocarbons by removal of one hydrogen, and at least one selected from B, N, O, S, P May be monocyclic or polycyclic aromatic hydrocarbon radicals containing from 3 to 8 ring atoms containing heteroatoms and may optionally include 3 to 7, preferably 5 or 6, ring atoms in each ring Or a fused ring system, and includes a form in which a plurality of heteroaryls are connected by a single bond. Specific examples include furyl, thiophenyl, pyrrolyl, pyranyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, tri Monocyclic heteroaryl such as, for example, pyrrolyl, pyrrolyl, pyrazinyl, pyrimidinyl and pyridazinyl; And benzofuranyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazole Polycyclic heteroaryl such as benzyl, tolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolizinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl and the like; But are not limited thereto.

The term " cycloalkyl " as used herein also means a fully saturated and partially unsaturated hydrocarbon ring of 3 to 9 carbon atoms, including the case where aryl or heteroaryl is fused.

Further, the "ring" described in the present invention is a ring formed by connecting adjacent substituents to each other, and according to one aspect of the present invention, it is preferred that said ring forms a phenyl group.

Phenothiazine has a higher solubility in reactive monomers and oligomers than polycyclic aromatic hydrocarbon type photosensitizers. However, up to now, it has not been able to effectively absorb wavelengths near 400 nm, A wide absorption band is generated in the visible light region and it is difficult to utilize it as a photosensitizer. Accordingly, the present inventors intend to provide a novel compound capable of solving the aforementioned drawback while maintaining the advantages of phenothiazine.

In detail, the phenothiazine compound according to an embodiment of the present invention is a compound represented by the following formula (1).

[Chemical Formula 1]

(In the formula 1,

X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;

R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocyclo An alkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof;

R ₃ represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof.

The compound represented by the formula (1) has an advantage that the polymerization degree and the transmittance can be improved by selectively improving the absorptivity only at the wavelength of the irradiated light while the wavelength is not absorbed in an unnecessary visible light region other than the irradiated light wavelength band. In addition, it has an advantage of being excellent in solubility in reactive monomers and oligomers and improving compatibility.

More specifically, in the compound represented by Formula 1, X and Y are independently a direct bond, O or S, and X and Y are not a direct bond; R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 heteroaryl, substituted or unsubstituted C 6 -C 30 aryl Or a combination thereof; R ₃ is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6- 30 aryl group, or a combination thereof.

As a more specific example, in the compound represented by Formula 1, X and Y are independently a direct bond, O or S, and X and Y are not a direct bond; R ₁ and R ₂ are independently selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms Or a combination thereof; R ₃ represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted C6- 20 aryl group, or a combination thereof.

More preferred examples of the compound according to an embodiment of the present invention include compounds having the following structures, but the present invention is not necessarily limited thereto.

The present invention also provides a photocurable composition comprising the compound represented by the above-mentioned general formula (1). The photo-curing composition containing the compound represented by the formula (1) can realize photo-curing properties improved with high sensitivity, and the transparency and heat resistance of the cured product can be remarkably improved. In addition, the compound represented by the general formula (1) is excellent in solubility with respect to reactive monomers or oligomers, so that the surface can be more uniformized when the photocurable composition is formed into a film or a sheet, and the material can be remarkably reduced .

Specifically, the photo-curable composition according to an embodiment of the present invention may include a compound represented by the following formula (1), and may be used, for example, as a photo-curing composition or an encapsulating composition.

[Chemical Formula 1]

(In the formula 1,

X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;

R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocyclo An alkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof;

R ₃ represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof.

As described above, the photocurable composition according to the present invention can ensure excellent sensitivity and transmission characteristics by including the compound represented by the formula (1). At this time, the compound represented by the formula (1) according to the present invention may act as a photosensitizer, and more specifically, the compound may be used for light absorption.

The amount of the compound represented by Formula 1 is not limited, but may be 0.01 to 20% by weight, more preferably 0.01 to 10% by weight, more preferably 0.1 to 10% by weight, based on the total weight of the photocurable composition. By weight to 5% by weight.

The photocurable composition according to an exemplary embodiment of the present invention may be photo-cured by light irradiation. Specifically, cation, radical or cation and radical may be generated by light irradiation to be photo-cured.

More specifically, the photocurable composition according to an example of the present invention may further comprise a photopolymerizable monomer having two or more photocurable unsaturated groups and a photoinitiator.

Here, the photopolymerizable monomer is not limited and may be cured by thermal curing or curing by irradiating an active energy ray. Examples of the functional groups of the photopolymerizable monomer include an oxazoline group, a carbamate group, a hydroxyl group, a thiol group, a carboxyl group, an epoxy group, an oxetane group, an isocyanate group, a glycidyl group, An acroyl group, a methacryloyl group, an acryloyloxy group, or a methacryloyloxy group.

The categories of active energy rays include, but are not limited to, microwaves, infrared (IR), ultraviolet (UV), X-rays and gamma rays, as well as alpha-particle beams, proton beams, neutron beams a particle beam such as a beam or an electron beam, and the like, and may be typically an ultraviolet ray or an electron beam.

The photopolymerizable monomer according to an embodiment of the present invention is preferably selected from acrylate compounds including an acryloxy group or a methacryloyloxy group. The photopolymerizable monomer is mixed with a compound according to the present invention and is photocured by a radical so as to provide a cured product having an improved light transmittance as well as an excellent curability. More specifically, (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10- Acrylate, 2-methacryloyloxyethyl stearate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, (Meth) acrylate, triethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (Meth) acrylate, polyethylene glycol (di) (meth) acrylate, cyclohexanedimethanol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polyethylene glycol Polyethylene glycol (600) di (meth) acrylate, glycerin di (meth) acrylate, 2-hydroxy-3-acryloxypropyl methacrylate, dimethylol tricyclodecanediol Acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane tri (2-hydroxyethyl) isocyanurate triacrylate, tri (2-hydroxyethyl) isocyanate, pentaerythritol triacrylate, ethoxylate trime (Meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol tetra ) Acrylate, epoxylated pentaerythritol tetra (meth) acrylate, triethylpropane triacrylate, and pentaacrylate esters. Here, the acrylate-based compound may be acrylate instead of (meth) acrylate.

The photopolymerizable monomer according to one embodiment of the present invention is preferably selected from an unsaturated oxetane-based compound containing an epoxy group and an unsaturated epoxy compound containing an oxetane group. In this regard, the photopolymerizable monomer is mixed with the compound of the present invention and then photocured by cations. Thus, in view of providing a cured product having excellent hardenability and high strength, more specifically, it is preferable to use dicyclopentadiene dioxide , Limonene dioxide, 4-vinylcyclohexene dioxide, 2,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate and bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclo Unsaturated epoxy compounds such as hexylmethyl-3,4'-epoxycyclohexanecarboxylate and bis (3,4-epoxycyclohexylmethyl) adipate dicyclopentadiene dioxide; And 3-ethyl-3 - [(3-ethyloxetan-3-yl) methoxymethyl] oxetane, 1,4-bis [ Methoxy] benzene, 1,3-bis [(3-ethyloxetan-3-yl) methoxy] benzene, 1,2-bis [ Methoxy] benzene, 4,4'-bis [(3-ethyloxetan-3-yl) methoxy] biphenyl, 2,2'-bis [ 3-yl) methoxy] biphenyl, 3,3 ', 5,5'-tetramethyl-4,4'-bis [(3-ethyloxetan- Methoxy] naphthalene, bis [4- {(3-ethyloxetan-3-yl) methoxy} phenyl] methane, bis [2- { Methoxy} phenyl] methane, 2,2-bis [4- (3-ethyloxetan- 8 (9) -bis [(3-ethyloxetan-3-yl) methoxymethyl] -tricyclo [5.2.1.0 2,6] decane, 2,3- Methoxymethyl] norbornane, 1,1,1-tris [(3-ethyloxetan-3-yl) methoxymethyl] propane, 1-butoxy-2,2-bis [ Methoxyethyl] butane, 1,2-bis [{2- (3-ethyloxetan-3-yl) methoxy} ethylthio] ethane, bis [{4- (3-oxetanyl) methyl] ether and 1,6-bis [(3-ethyloxetan-3-yl) methylthio} phenyl] sulfide, bis [ Methoxy] -2,2,3,3,4,4,5,5-octafluorohexane and the like; And the like.

The amount of the photopolymerizable monomer to be used is not limited, but may be 50 to 99% by weight based on the total weight of the photocurable composition, specifically 60 to 99% by weight, more preferably 70 to 99% %.

In addition, the photoinitiator according to an embodiment of the present invention is not limited as long as it is a known one. For example, the photoinitiator may be a cationic photoinitiator that produces a cationic species or a Lewis acid by irradiation of the active energy ray, Can be a photoinitiator.

The cationic photoinitiator may be an onium salt having a weakly nucleophilic anion, and examples thereof include a halonium salt, an iodosyl salt, a sulfonium salt, a sulfoxonium salt, and a diazonium salt. Non-limiting examples of commercial cationic photoinitiators include UVI-6974, UVI-6976, UVI-6970, UVI-6990 (DOW Corp.), CD1010, CD-1011, CD- (Sartomer Corp.), Adekaoptomer SP-150, SP-151, SP-170 and SP-171 (Asahi Denka Kogyo Co., Ltd.), Irgacure 261 (Nippon Soda Co., Ltd.) and DTS-102, DTS-103, NAT-103, NDS-1024 and CI- 103, TPS-103, MDS-103, MPI-103 and BBI-103 (Midori Chemical Co., Ltd.).

The photoinitiator may be selected from benzoin derivatives, acetophenone derivatives, anthraquinone derivatives, thioxanthone derivatives, ketal derivatives, benzophenone derivatives,? -Aminoacetophenone derivatives, acylphosphine oxide derivatives and oxime ester derivatives . At this time, non-limiting examples of the photoinitiator include benzoin derivatives such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Acetophenone derivatives such as acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone and 4- (1-t-butyldioxy-1-methylethyl) acetophenone; Anthraquinone derivatives such as 2-methyl anthraquinone, 2-amylanthraquinone, 2-t-butyl anthraquinone, and 1-chloro anthraquinone; Thioxanthone derivatives such as 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone and 2-chlorothioxanthone; Ketal such as acetophenone dimethyl ketal and benzyl dimethyl ketal; Benzophenone derivatives such as benzophenone, 4- (1-t-butyldioxy-1-methylethyl) benzophenone and 3,3 ', 4,4'-tetrakis (t-butyldioxycarbonyl) benzophenone ; Methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) , N, N-dimethylaminoacetophenone (commercially available products such as N, N-dimethylaminoethyl) -2 - [(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) Α-amino acetophenone derivatives such as Irgacure (registered trademark) 907, Irgacure 369, Irgacure 379 from Chiba Specialty Chemicals (now Ciba Japan); Bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl Acylphosphine oxide derivatives such as pentylphosphine oxide (commercially available products such as Lucylin (registered trademark) TPO from BASF, and IRGACURE 819 from Ciba Specialty Chemicals); (4-phenylthio) phenyl, 2- (O-benzoyloxime), (ethanone) Oxime ester derivatives such as 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -, 1- (O-acetyloxime) Oxime ester derivatives, and the like. However, the present invention is not limited thereto.

The amount of the photoinitiator may be in the range of 0.5 to 20% by weight based on the total weight of the photocurable composition, specifically 1 to 15% by weight, more preferably 1 to 10% by weight It should be included.

In addition, the photocurable composition according to an embodiment of the present invention may further contain a second photosensitizer, an adhesion promoter, a surfactant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, an antioxidant, , A plasticizing agent, a plasticizer, a lubricant, a flame retardant, an antistatic agent, a defoaming agent, and a leveling agent.

As an example of the additive, a non-limiting example of the second photosensitizer is 2-ethyl-9,10-dimethoxyanthracene, 9,10-dichloroanthracene (9 1-chloroanthracene, 2-methylanthracene, 9-methylanthracene, 2-t-butylanthracene, Anthracene, 1,2-benzanthracene, 1,2,3,4-dibenzanthracene, 1,2,5,6- 1,2,5,6-dibenzanthracene, 1,2,7,8-dibenzanthracene, 9,10-dimethoxydimethylanthracene (9,10-dibenzanthracene) dimethoxydimethylanthracene, 2-ethyl-9,10-dimethoxyanthracene, N-methylphenothiazine, 2-isopropylthioxanthone, ) And the like. Nonlimiting examples of commercially available second photosensitizers include Kayacure TM-DMBI, BDMK, BP-100, BMBI, DETX-S, EPA (available from Nippon Kayaku Co., Ltd.) UVS-1331, UVS-1221 (manufactured by Kawasaki Kasei Kogyo Co., Ltd.), Yubecryl P102, 103, 104 and 105 (manufactured by UCB Co., Ltd.) and the like.

The adhesion aid may be of two or more types selected from hydrolyzable groups (e.g., alkoxy, acyloxy, halogen, etc.) and organic functional groups (e.g., amino, mercapto, vinyl, epoxy, methacryloxy, acryloxy, isocyanate, etc.) May be a silane compound having a different substituent. Nonlimiting examples thereof include N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, Aminopropyltriethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1,3-dimethyl-butylidene) propyl Amine, N-phenyl-3-aminopropyltrimethoxysilane, N- (vinylbenzyl) -2-aminoethyl-3-aminopropyltrimethoxysilane and 3-glycidoxypropyltrimethoxysilane. have.

KF-101, KF-102, KF-105, KF-351, KF-352, KF-618, and KF-101 are commercially available products -945, KF-2001, KF-2004, X-22-163A, X-22-163B, X-22-167B, X-22-169AS, X-22-2000, X- -4741 (manufactured by Shin-Etsu Chemical Co., Ltd.), trade names BYK-307, BYK-325 and BYK-333 (manufactured by Beck Chemie Japan).

The ultraviolet absorber may act to absorb ultraviolet rays from sunlight or the like and convert the ultraviolet absorber into harmless thermal energy in the molecule to prevent excitation of the active species of photo-initiation initiation, depending on the use of the photo-curable composition. Examples of the ultraviolet absorber include inorganic ultraviolet absorbers such as benzophenone, benzotriazole, acrylonitrile, metal complex salt, hindered amine, ultrafine titanium oxide and ultrafine zinc oxide. Or a mixture of two or more of them may be used.

The light stabilizer can capture the active species of photo-induced initiation and prevent photo-oxidation. At this time, non-limiting examples of the light stabilizer include a known compound such as a hindered amine compound or a hindered piperidine compound.

Nonlimiting examples of the heat stabilizer include tris (2,4-di-tert-butylphenyl) phosphite, bis [2,4-bis (1,1-dimethylethyl) -6- methylphenyl] ethyl ester phosphorous acid, (2,4-di-tert-butylphenyl) [1,1-biphenyl] -4,4'-diyl bisphosphonate and bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite Phosphorus-based thermal stabilizers; And a lactone type heat stabilizer such as a reaction product of 8-hydroxy-5,7-di-tert-butyl-furan-2-one and o-xylene, Can be used.

The moisture adsorbent refers to a material capable of adsorbing or removing moisture through chemical reaction or physical reaction with moisture or moisture penetrated into the encapsulating material when the photo-curing composition is used as an encapsulating material. Specific examples of the moisture adsorbent include metal oxides, sulfates, organic metal oxides, clay, talc, needle-like silica, plate-like silica, porous silica, zeolite, titania or zirconia. , Metal oxides such as calcium oxide, strontium oxide, barium oxide or aluminum oxide; Sulfates such as magnesium sulfate, sodium sulfate or nickel sulfate; And organic metal oxides such as aluminum oxide octylate.

In this case, the additive may be contained in an amount of 0.01 to 10 parts by weight based on the total weight of the composition, specifically 0.05 to 5 parts by weight, more specifically 0.1 to 5 parts by weight, to be.

The present invention also provides an organic electronic device encapsulated with an encapsulant comprising a cured product of the photocurable composition of the combination described above.

The shape of the encapsulating material is not particularly limited, but may be preferably formed in the form of a sheet or a film. At this time, it is a matter of course that the film thickness of the sealing material sheet or film can be appropriately adjusted in consideration of the supporting efficiency and breakage possibility of elements such as cells of the organic electronic device, lightening of the apparatus, workability, May be manufactured to a thickness of 5 to 2,000 mu m, and more specifically may be manufactured to a thickness of 5 to 1,000 mu m.

The cured product, that is, the sealing material according to the present invention can be produced by using the photocurable composition of the combination according to the present invention as described above, thereby providing a cured product that not only realizes an excellent curing degree but also has a low hygroscopicity and excellent moisture resistance. Further, the encapsulant according to the present invention can secure an improved heat resistance and excellent surface properties (e.g., surface hardness, adhesiveness, crack resistance, thermal shock resistance, etc.).

According to the present invention, even when applied to protect devices in a large-area device, the device can be stacked on the device without causing bubbles or the like, and after the sealing process, the device is effectively protected from external components, can do.

The encapsulant according to an embodiment of the present invention may have a multi-layer structure in which two or more organic layers including the photo-curable composition are laminated. At this time, the organic layers of the multi-layer structure may have different elastic moduli, light transmittance, and water vapor transmittance.

The encapsulant according to an embodiment of the present invention not only exhibits excellent transparency with a light transmittance of 80 to 99% at a wavelength of 400 nm, but also can improve the overall film characteristic with an improved curing rate.

The light transmittance (400 nm) of the encapsulant according to an embodiment of the present invention may be specifically 85 to 99%, more specifically 90 to 99%.

The encapsulating material according to an embodiment of the present invention may further include a substrate. The substrate may be disposed on one side or both sides of the encapsulant. The substrate may be a substrate subjected to a releasing treatment, and the kind of substrate may be used without limitation in the art.

The encapsulant according to an embodiment of the present invention can be applied to encapsulate and protect various objects. In particular, the encapsulant may be effective in protecting an object comprising oxygen or moisture sensitive devices. Examples of objects to which the encapsulant can be applied include organic electronic devices such as a photovoltaic device, a rectifier, a transmitter or an organic light emitting diode (OLED) A solar cell, a secondary cell, or the like may also be applied.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the novel compounds according to the present invention, photocurable compositions containing them, and cured products thereof will be described in more detail by way of examples. It should be understood, however, that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the invention.

Unless otherwise defined, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. In addition, the unit of the additives not specifically described in the specification may be% by weight.

[ Example  1] Preparation of compound 1

2.59 g of 2- (ethylthio) -10H-phenothiazine, 3.51 g of 4-iodoanisole, 4.15 g of anhydrous potassium carbonate, Copper bronze 1.82 g, 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane) 0.53 g, and 1,2-diclorobenzene (100 ml) were mixed and stirred at 180 ° C for 48 hours.

After completion of the reaction, the reaction solution was cooled and filtered under reduced pressure, and the filtrate was washed with distilled water for 2 to 3 times. Then, the organic solvent was removed using a rotary evaporator and then purified by column chromatography to obtain 2.9 g of Compound 1 ≪ / RTI >

_{^{1 H NMR (acetone-d 6}} , 300 MHz), δ: 7.36 (d, J = 6.0 Hz, 2H), 7.23 (d, J = 6.0 Hz, 2H), 7.00 (d, J = 6.0 Hz, 1H) , 6.94 (d, J = 6.0 Hz, 1H), 6.89 (d, J = 6.0 Hz, 1H) (s, 1H), 3.91 (s, 1H), 2.73 (m, 2H), 1.14 (t, J = 9.0 Hz, 3H).

[ Example  2] Preparation of compound 2

2.59 g of 2- (ethylthio) -10H-phenothiazine, 3.96 g of 2,4-dimethoxy iodobenzene, 4.15 g of anhydrous potassium carbonate, 1.82 g of copper powder, 18-crown-6 (0.53 g) and 1,2-diclorobenzene (100 ml) were mixed, and the mixture was stirred at 180 ° C for 48 hours.

After completion of the reaction, the reaction solution was cooled and filtered under reduced pressure, and the filtrate was washed with distilled water two to three times. Next, the organic solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain 2.97 g of Compound 2 .

_{^{1 H NMR (acetone-d 6}} , 300 MHz), δ: 7.25 (d, J = 6.0 Hz, 1H), 6.97 (s, 1H), 6.89 (d, J = 6.0 Hz, 2H), 6.80-6.74 ( (s, 3H), 3.81 (s, 3H), 2.73 (m, 2H), 1.14 (t, J = 9.0 Hz, 3H).

[ Example  3] Preparation of Compound 3

2.59 g of 2- (ethylthio) -10H-phenothiazine, 3.06 g of iodobenzene, 4.15 g of anhydrous potassium carbonate, 1.82 g of copper powder, 0.53 g of 18-crown-6, -Dichlorobenzene (100 ml) were mixed and stirred at 150 占 폚 for 24 hours.

After completion of the reaction, the reaction solution was cooled and filtered under reduced pressure, and the filtrate was washed with distilled water for 2 to 3 times. Next, the organic solvent was removed using a rotary condenser and then purified by column chromatography to obtain 2.85 g of Compound 3 ≪ / RTI >

_{^{1 H NMR (acetone-d 6}} , 300 MHz), δ: 7.71 (t, J = 9.0 Hz, 2H), 7.57 (t, J = 9.0 Hz, 1H), 7.46 (t, J = 9.0 Hz, 2H) , 7.03 (d, J = 6.0 Hz, 1H), 6.97 (d, J = 6.0 Hz, 1H), 6.89-6.81 (m, 3H), 5.22 1H), 2.72 (m, 2H), 1.12 (t, J = 9.0 Hz, 3H).

[ Example  4] Preparation of compound 4

Phenylazine, 4.14 g of 4-butoxy iodobenzene, 4.15 g of anhydrous potassium carbonate, 1.82 g of copper powder, 18-crown- 6 (0.53 g) and 1,2-diclobulobenzene (100 ml) were mixed, and the mixture was stirred at 180 ° C for 48 hours.

After completion of the reaction, the reaction solution was cooled and filtered under reduced pressure, and the filtrate was washed with distilled water for 2 to 3 times. Then, the organic solvent was removed using a rotary evaporator and then purified by column chromatography to obtain 2.71 g of Compound 4 -1.

Subsequently, 1.3 g of the compound 4-1 was dissolved in 30 ml of dimethylformamide (DMF) in a nitrogen atmosphere, and the mixture was cooled to 0 캜. 0.74 g of N-bromosuccinimide (NBS) was added thereto, Lt; 0 > C) for 8 hours. When the reaction was completed, the mixture was neutralized to pH 7 with diluted potassium hydroxide and extracted with methylene chloride (MC). The product was purified by column chromatography to give 1.32 g of compound 4-2.

Next, the mixture was stirred a mixture of compound 4-2 1.1 g, CuI 0.024 g, 8- hydroxyquinoline (8-hydroxyquinoline) 0.038 g, potassium phosphate (K ₃ PO ₄₎ 1.1 g in a nitrogen atmosphere. 6 ml of 1-butanol was added to the stirring solution, and the mixture was stirred at 110 DEG C for 24 hours. When the reaction was completed, the reaction mixture was cooled to room temperature (about 25 ° C), the solvent was removed, and the reaction solution was extracted using MC. The product was purified by column chromatography to obtain 0.7 g of compound 4. < 1 >

^{_{1 H NMR (CDCl 3, 500}} MHz), δ: 7.24 (t, J = 9.0 Hz, 2H), 7.08-7.06 (m, 4H), 6.89 (d, J = 9.0 Hz, 1H), 6.56 (s, J = 9.0 Hz, 1H), 6.39 (d, J = 9.0 Hz, 1H), 6.10 (d, 2H, J = 7.5 Hz, 1H), 3.85 (m, 2H), 1.85 3H), 0.95 (t, J = 7.5 Hz, 3 H).

[ Example 5] Preparation of cationic photo-curable composition

45.85 g of a photopolymerizable monomer (3,4-epoxycyclohexylmethyl-3,4'-epoxycyclohexanecarboxylate, UVR-6110, Dow chemical), 2.0 g of a cationic photoinitiator (CD-1012, Sartomer) (KBM-403) and 0.15 g of a surfactant (BYK-307) were sequentially mixed and stirred at room temperature (23 캜) for 3 hours to prepare a cationic photo-curable composition.

[ Examples 6 to 8] Preparation of cationic photo-curable composition

A cationic photo-curable composition was prepared in the same manner as in Example 5 except that 1.0 g of each of the compounds of Example 2, Example 3 or Example 4 was used instead of the compound of Example 1 above.

[ Example 9] Preparation of cationic photo-curable composition

2.0 g of a photoinitiator (CD-1012, Sartomer), 0.5 g of the compound of Example 1, 0.5 g of a photosensitizer (UVS-1331, Kawasaki Kasei chemical) (KBM-403) and 0.15 g of a surfactant (BYK-307) were sequentially mixed, and the mixture was stirred at room temperature for 3 hours to prepare a cationically photo-curable photocurable composition.

[ Examples 10 to 12] Preparation of cationic photo-curable composition

A cationic photo-curable composition was prepared in the same manner as in Example 9 except that 0.5 g of each of the compounds of Example 2, Example 3 and Example 4 was used instead of the compound of Example 1 above.

[ Example 13] Preparation of radical photocurable composition

(Irgacure TPO, BASF) 1.66 g, and the adhesive preparation (KBM-1) were added to a solution prepared by dissolving 10.37 g of phenoxyethyl acrylate, 55.34 g of tripropylene glycol diacrylate, 8.30 g of triethylpropane triacrylate, 0.83 g of the compound of Example 1, 503) and 0.15 g of a surfactant (BYK-307) were sequentially mixed, and the mixture was stirred at room temperature for 3 hours to prepare a radical photocurable composition.

[ Examples 14 to 16] Preparation of radical photocurable composition

A radical photocurable composition was prepared in the same manner as in Example 13 except that 0.83 g of the compound of Example 2, Example 3 or Example 4 was used instead of the compound of Example 1, respectively.

[ Example 17] Preparation of radical photocurable composition

10.37 g of phenoxyethyl acrylate, 55.34 g of tripropylene glycol diacrylate, 8.30 g of triethylpropane triacrylate, 0.83 g of the compound of Example 1, 0.43 g of the compound of Example 1, (KBK-1331, Kawasaki Kasei chemical), 1.66 g of Irgacure TPO (BASF), 1.0 g of adhesive preparation (KBM-503) and 0.15 g of a surfactant (BYK-307) were successively mixed and stirred at room temperature for 3 hours Radical photocurable compositions were prepared.

[ Examples 18 to 20] Preparation of radical photocurable composition

A radical photocurable composition was prepared in the same manner as in Example 17 except that 0.43 g of the compound of Example 2, Example 3 or Example 4 was used instead of the photoactive compound prepared in Example 1 Respectively.

(Comparative Example 1) Preparation of cationically photo-curable composition

A cationic photo-curable composition was prepared in the same manner as in Example 5 except that 1.0 g of a photosensitizer (UVS-1331, Kawasaki Kasei chemical) was used in place of the compound of Example 1.

(Comparative Example 2) Preparation of radical photocurable composition

A radical photocurable composition was prepared in the same manner as in Example 13 except that 0.83 g of a photosensitizer (UVS-1331, Kawasaki Kasei chemical) was used instead of the compound of Example 1.

The photo-curable composition prepared by the above method was coated on a polyimide film substrate by an ink jet method and irradiated with 1000 mJ ultraviolet rays for 1 second with a 1000 mW LED exposing device having a wavelength of 395 nm in a nitrogen atmosphere to form a film having a thickness of 5 탆 and measuring the physical properties .

1) Hardening degree measurement

The polyimide base film was coated on the polyimide base film by the ink jet method using the photocurable compositions prepared in the above Examples and Comparative Examples, and then irradiated with 1000 mJ ultraviolet rays for 1 second with a 1000 mW LED exposer having a wavelength of 395 nm in a nitrogen atmosphere, . Each of the produced films was cut to a width of 5 cm and a length of 5 cm. Then, the absorption spectrum of the pre-cured film and the post-cured film was measured using an FT-IR (infrared spectroscope), and the degree of cure was calculated by the following formula 1.

(Equation 1)

Hardening degree (%) = 100- (Wf / Wi x 100)

(Wf) is a peak area (degree of absorption) of the functional group of the photopolymerizable monomer contained in the film after curing, and Wf is a peak area (degree of absorption) of the functional group of the photopolymerizable monomer contained in the composition before curing. .]

2) Surface hardness measurement

The photocurable composition prepared in the above Examples and Comparative Examples was coated on a glass by an inkjet method and irradiated with 1000 mJ ultraviolet rays for 1 second with a 1000 mW LED exposer having a wavelength of 395 nm in a nitrogen atmosphere to prepare an encapsulating substrate having a thickness of 5 탆 . The surface hardness of the prepared substrate was measured with a pencil hardness meter under the condition of 200 g weight.

3) Light transmittance measurement

The photocurable composition prepared in the above Examples and Comparative Examples was coated on a glass by an inkjet method and irradiated with 1000 mJ ultraviolet rays for 1 second with a 1000 mW LED exposer having a wavelength of 395 nm in a nitrogen atmosphere to prepare an encapsulating substrate having a thickness of 5 탆 . The prepared substrate was measured for light transmittance using a UV-VIS spectrophotometer (@ 400 nm).

4) Outgasing measurement

The photocurable composition prepared in the above Examples and Comparative Examples was coated on a glass by an inkjet method and irradiated with 1000 mJ ultraviolet rays for 1 second with a 1000 mW LED exposer having a wavelength of 395 nm in a nitrogen atmosphere to prepare an encapsulating substrate having a thickness of 5 탆 . The TVOC produced by the heat treatment at 100 ° C for 10 minutes was measured by TD-GC / MS.

The physical properties of the encapsulant film prepared by the above method were measured and shown in Tables 1 and 2 below.

Degree of hardening
(Curing Rate) Surface hardness
Light transmittance
(@ 400 nm) Outgasing
Example 5 93% 3H 97% 151 ppm Example 6 90% 2H 96% 182 ppm Example 7 92% 3H 97% 168 ppm Example 8 85% 2H 96% 485ppm Example 9 92% 3H 94% 201 ppm Example 10 90% 2H 94% 252 ppm Example 11 91% 3H 94% 221 ppm Example 12 84% 2H 93% 433 ppm Comparative Example 1 84% 2H 81% 855ppm

Degree of hardening
(Curing Rate) Surface hardness
Light transmittance
(@ 400 nm) Outgasing
Example 13 88% 2H 98% 908ppm Example 14 86% 2H 96% 952 ppm Example 15 88% 2H 98% 917 ppm Example 16 83% H 97% 1232 ppm Example 17 87% 2H 93% 941ppm Example 18 87% H 93% 987ppm Example 19 86% 2H 92% 970ppm Example 20 81% H 92% 1320ppm Comparative Example 2 78% H 84% 1500ppm

As shown in Tables 1 and 2, in the case of the film using the cationic photo-curable composition and the radical photo-curable composition according to the present invention, not only has an excellent hardness, a remarkably low outgasing characteristic due to a high degree of curing, It has excellent properties in light transmittance of 400nm which is the biggest problem of aromatic hydrocarbon (Polynuclear aromatic hydrocarbon) type photosensitizer. Also, it was confirmed that even when the photosensitizer prepared in the present invention is mixed with the conventional photosensitizer, it has excellent properties. This means that it is possible to produce films having various properties suitable for the user's purpose only by adjusting the mixing ratio of the photosensitizer of the present invention and the conventional photosensitizer according to the curing conditions (exposure wavelength and exposure amount, etc.) of various compositions.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, Various modifications and variations may be made thereto by those skilled in the art.

Accordingly, the spirit of the present invention should not be construed as being limited to the embodiments described, and all of the equivalents or equivalents of the claims, as well as the following claims, belong to the scope of the present invention .

Claims (11)

A compound represented by the following formula (1):
[Chemical Formula 1]

(In the formula 1,
X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;
R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocyclo An alkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof;
R ₃ represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof. The method according to claim 1,
The compound,
X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;
R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 heteroaryl, substituted or unsubstituted C 6 -C 30 aryl Or a combination thereof;
R ₃ is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6- Lt; / RTI > is an aryl group of 1 to 30 carbon atoms, or a combination thereof. The method according to claim 1,
The compound,
X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;
R ₁ and R ₂ are independently selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms Or a combination thereof;
R ₃ represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted C6- Lt; / RTI > or an aryl group having from 1 to 20 carbon atoms, or a combination thereof. The method according to claim 1,
The compound,
A compound selected from the following structure:

1. A photocurable composition comprising a compound represented by the following formula (1).
[Chemical Formula 1]

(In the formula 1,
X and Y are independently a direct bond, O or S, and X and Y are not both direct bonds;
R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocyclo An alkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof;
R ₃ represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof. 6. The method of claim 5,
Wherein the compound is used for light absorption. 6. The method of claim 5,
The photo-curable composition may be cured by light irradiation; Radical; Or cations and radicals; Is generated and photo-cured. 6. The method of claim 5,
Wherein the photocurable composition further comprises a photopolymerizable monomer having at least two photocurable unsaturated groups and a photoinitiator. 9. The method of claim 8,
Wherein the photoinitiator is a cationic photoinitiator. 9. The method of claim 8,
Wherein the photoinitiator is selected from the group consisting of benzoin derivatives, acetophenone derivatives, anthraquinone derivatives, thioxanthone derivatives, ketal derivatives, benzophenone derivatives,? -Amino acetophenone derivatives, acylphosphine oxide derivatives and oxime ester derivatives Or more. An organic electronic device encapsulated with an encapsulant comprising a cured product of the photo-curable composition of any one of claims 5 to 10.