KR102011345B1 - New compound, photo-curable composition containing the same, and cured product thereof - Google Patents

Abstract

(상기 화학식 1에서 X, Y, R₁, R₂ 및 R₃에 대한 정의는 청구항 1항에서의 정의와 동일하다.)The present invention relates to an organic electronic device encapsulated with a novel compound, a composition comprising the same, and an encapsulant including a cured product thereof, wherein the novel compound is represented by the following Chemical Formula 1.
[Formula 1]

(Definitions for X, Y, R ₁ , R ₂ and R ₃ in Chemical Formula 1 are the same as those in Claim 1).

Description

New compound, photocurable composition comprising the same and cured product thereof New compound, photo-curable composition containing the same, and cured product

The present invention relates to novel compounds, photocurable compositions comprising the same and cured products thereof.

Halogen lamps, which are widely used at the time of light irradiation, emit light of many unnecessary wavelengths that are not necessary for polymerization, and thus the efficiency of visible light irradiator decreases, and the problem of long time light irradiation continues. In addition, in order to reduce the light irradiation time, a visible light irradiator having a higher power density should be used, and a high cycle is emitted by the light irradiator and the life cycle of the light irradiator is shortened.

As an alternative that can effectively reduce this problem, a light emitter using a light emitting diode (LED) lamp has been recently developed. LED lamps can selectively emit only light in the wavelength range necessary for polymerization, and have been evaluated as a device that can effectively solve the problems presented above.

Although the irradiation light of such an LED lamp has a long wavelength up to almost 400 nm band, since photopolymerization does not occur effectively in the wavelength band with only the photoinitiator, a photosensitizer or the like is used to increase the polymerization efficiency.

In general, polynuclear aromatic hydrocarbon-based photosensitizers such as dibutoxy antracene (dibutoxy antracene) (Korean Patent No. 10-1293803) have excellent sensitivity and are mainly used with photoinitiators.

On the other hand, phenothiazine has the advantage of higher solubility in reactive monomers or oligomers than polyaromatic hydrocarbon-based photosensitizers, but until now does not effectively absorb wavelengths near 400 nm, In the case of increased absorption, a wide absorption band was generated in the visible light region, making it difficult to use as a photosensitizer.

The present inventors have repeatedly studied to solve the conventional problems, and as a result, by selectively improving only the absorption in the irradiated light wavelength range to improve the degree of polymerization and transmittance, while maintaining the solubility in the reactive monomers or oligomers, which is an existing advantage, The present invention has been completed by devising a novel compound having excellent compatibility.

Republic of Korea Patent No. 10-1293803 (2013.07.31.)

In order to solve the above problems, an object of the present invention is to provide a novel compound having a good solubility in reactive monomers and oligomers while being able to selectively improve only the absorption in the irradiated light wavelength band to improve the degree of polymerization and transmittance. .

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

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

One aspect of the present invention for achieving the above object relates to a compound represented by the following formula (1).

[Formula 1]

(In Formula 1,

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

R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 30 carbon atoms An alkyl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof;

R ₃ is a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 30 30 heteroaryl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or a combination thereof.)

In one embodiment, the compound wherein the X and Y are a direct bond, O or S independently of each other, X and Y are not all direct bonds; R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms Groups or structures in which these are combined; R ₃ is 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 heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 30 carbon atoms 30 aryl groups, or a combination thereof.

In one embodiment, the compound wherein the X and Y are a direct bond, O or S independently of each other, X and Y are not all direct bonds; R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms Groups or structures in which these are combined; R ₃ is a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C15 20 aryl groups, or a combination thereof.

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

In addition, another aspect of the present invention relates to a photocurable composition comprising a compound represented by the following formula (1).

[Formula 1]

(In Formula 1,

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

R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 30 carbon atoms An alkyl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof;

R ₃ is a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 30 30 heteroaryl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or a combination thereof.)

In another aspect, the compound may be used for light absorption.

In another aspect, the photocurable composition may be photocured by generating a cation, a radical or a cation and a radical by light irradiation.

In another aspect, the photocurable composition may further include a photopolymerizable monomer and a photoinitiator having two or more photocurable unsaturated groups.

In another aspect, the photoinitiator may be a cationic photoinitiator.

In another embodiment, the photoinitiator is a benzoin derivative, acetophenone derivative, anthraquinone derivative, thioxanthone derivative, ketal derivative, benzophenone derivative, α-aminoacetophenone derivative, acylphosphine oxide derivative and oxime ester It may be any one or two or more selected from derivatives and the like.

Further, another aspect of the present invention relates to an organic electronic device encapsulated with an encapsulant including a cured product of the photocurable composition described above.

Phenothiazine-based compounds according to the present invention have the advantage that the absorption of the wavelength in the unnecessary visible light region other than the irradiated light wavelength band can be selectively improved only by the absorption in the irradiated light wavelength band to improve the degree of polymerization and transmittance. have. In addition, there is an advantage that the solubility in the reactive monomer or oligomer can be improved to improve the compatibility.

In addition, the composition comprising the compound according to the present invention can implement a photocurability improved with high sensitivity, it can significantly improve the transparency and heat resistance of the cured product.

In addition, when the composition containing the compound according to the present invention is shaped into a film or sheet, the surface can be more uniform, and foreign matters can be significantly reduced.

In addition, the composition comprising the compound of the present invention may be formed of a film or sheet to encapsulate the organic electronic device, thereby providing a highly reliable organic electronic device with remarkably improved life characteristics and durability.

Hereinafter, a novel compound according to the present invention, a photocurable composition including the same, and a cured product thereof will be described in detail.

In this case, unless there is another definition in the technical terms and scientific terms used, it has the meaning that is commonly understood by those of ordinary skill in the art, unnecessarily obscure the subject matter of the present invention in the following description Description of known functions and configurations that may be omitted.

In the present invention, "substituted or substituted" means one or more hydrogen atoms of the functional group in the compound is halogen (-F, -Cl, -Br or -I), alkyl group having 1 to 30 carbon atoms unless otherwise specified herein , 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 It means substituted with one or more substituents selected from the group consisting of a hydroxy group, an amine group, a carboxylic acid group and an aldehyde group, and the like, provided that the carbon number of the functional group described in Formula 1 may not include the carbon number of the substituent.

Substituents including the "alkyl", "alkoxy", "thioxy" and other "alkyl" moieties described in the present invention include all linear or pulverized forms. According to one aspect of the present invention, short-chain alkyl, alkoxy, thioxy and the like having 7 or less carbon atoms are preferable, but long chains having 8 or more carbon atoms are also an aspect of the present invention.

In addition, "aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and each ring preferably contains 4 to 7, preferably 5 or 6 ring atoms, or It includes a fused ring system, and includes 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, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. Not limited to this, "heteroaryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, at least one selected from B, N, O, S, P (= O), Si and P, etc. It may be a monocyclic or polycyclic aromatic hydrocarbon radical containing 3 to 8 ring atoms comprising heteroatoms, each ring being suitably containing 3 to 7, preferably 5 or 6 ring atoms Or it includes a fused ring system, and includes a form in which a plurality of heteroaryl is connected by a single bond. Specific examples include furyl, thiophenyl, pyrrolyl, pyranyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, tria Monocyclic heteroaryl such as zolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl; And benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindoleyl, indolyl, indazolyl, benzothiadia Polycyclic heteroaryls such as zolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolizinyl, quinoxalinyl, carbazolyl, phenanthridinyl, and benzodioxolyl; And the like, but are not limited thereto.

In addition, "cycloalkyl" described in the present invention means a fully saturated and partially unsaturated hydrocarbon ring of 3 to 9 carbon atoms, including the case where aryl or heteroaryl is fused.

In addition, the "ring" described in the present invention is a ring formed by linking adjacent substituents to each other. According to one embodiment of the present invention, the ring preferably forms a phenyl group.

Phenothiazine has the advantage of higher solubility in reactive monomers or oligomers than polyaromatic hydrocarbon-based photosensitizers, but until now it does not effectively absorb wavelengths near 400 nm, or absorbs through some substitutions. In the case of increasing the high absorption band in the visible light region has a disadvantage that it is difficult to use as a photosensitizer. Accordingly, the present inventors seek to provide a novel compound that can solve the above-mentioned disadvantages while maintaining the advantages of phenothiazine.

In detail, the phenothiazine-based compound according to an embodiment of the present invention is a compound represented by the following Chemical Formula 1.

[Formula 1]

(In Formula 1,

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

R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 30 carbon atoms An alkyl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof;

R ₃ is a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 30 30 heteroaryl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or a combination thereof.)

The compound represented by the formula (1) has an advantage in that the absorption in the unnecessary visible light region other than the irradiation light wavelength band has almost no absorption, and can be selectively improved only by the absorption rate in the irradiation light wavelength band to improve the degree of polymerization and transmittance. In addition, there is an advantage that the solubility in the reactive monomer or oligomer can be improved to improve the compatibility.

In a more specific example, in the compound represented by Formula 1, X and Y are a direct bond, O or S independently of each other, X and Y are not all direct bonds; R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms Groups or structures in which these are combined; R ₃ is 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 heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 30 carbon atoms An aryl group of 30 or a combination thereof.

In a more specific example, in the compound represented by Formula 1, X and Y are each independently a direct bond, O or S, X and Y are not all direct bonds; R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms Groups or structures in which these are combined; R ₃ is a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C15 An aryl group of 20 or a combination thereof.

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

In addition, the present invention provides a photocurable composition comprising a compound represented by the above formula (1). The photocurable composition including the compound represented by Formula 1 may realize improved photocuring properties with high sensitivity, and may significantly improve transparency and heat resistance of the cured product. In addition, the compound represented by Formula 1 has excellent solubility in reactive monomers or oligomers, so that when the photocurable composition is shaped into a film or sheet, the surface may be more uniform, and the material may be significantly reduced. .

Specifically, the photocurable composition according to an aspect of the present invention may include a compound represented by the following Chemical Formula 1, and as an example, may be used as a photocurable composition or an encapsulant composition.

[Formula 1]

(In Formula 1,

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

R ₁ and R ₂ are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 30 carbon atoms An alkyl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof;

R ₃ is a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 30 30 heteroaryl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or a combination thereof.)

As such, the photocurable composition according to the present invention may ensure excellent sensitivity and transmission characteristics by including the compound represented by the formula (1). In this case, the compound represented by Formula 1 according to the present invention may be to perform the role of a photosensitizer, more specifically, the compound may be used for light absorption.

In this case, the amount of the compound represented by Formula 1 is not limited, but may be included as 0.01 to 20% by weight, specifically 0.01 to 10% by weight, more specifically 0.1 based on the total weight of the photocurable composition It is preferably included in 5% by weight.

The photocurable composition according to an embodiment of the present invention may be photocured by light irradiation, and specifically, may be photocured by generating cations, radicals or cations and radicals by light irradiation.

In more detail, the photocurable composition according to an embodiment of the present invention may further include a photopolymerizable monomer and photoinitiator having two or more photocurable unsaturated groups.

In this case, the photopolymerizable monomer is not limited and may be cured by thermal curing or cured by irradiating active energy rays. At this time, non-limiting examples of the functional group of the photopolymerizable monomer are oxazoline group, carbamate group, hydroxy group, thiol group, carboxyl group, epoxy group, oxetane group, isocyanate group, glycidyl group, acrylic group, methacryl group, Acroyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, etc. are mentioned.

The categories of active energy rays include microwaves, infrared rays (IR), ultraviolet rays (UV), X-rays and gamma rays, as well as alpha-particle beams, proton beams, and neutron beams. Particle beams, such as beams or electron beams, may be included, and typically may be ultraviolet rays or electron beams.

Specifically, the photopolymerizable monomer according to an embodiment of the present invention may be selected from an acrylate compound including an acrylooxy group or a methacryloyloxy group. In this case, the photopolymerizable monomer is mixed with the compound according to the present invention and then photocured by radicals, and more specifically, in terms of providing a cured product having excellent lightness and improved light transmittance. 1,3-butanedioldi (meth) acrylate, 1,6-hexanedioldi (meth) acrylate, 1,9-nonanedioldi (meth) acrylate, 1,10-decanedioldi (meth) acrylic Ethylene, 1, 3- butylene glycol di (meth) acrylate, phenoxyethyl (meth) acrylate, 2-methacryloyl oxyethyl acetate phosphate, ethylene glycol di (meth) acrylate, diethylene glycol di (Meth) acrylate, triethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, tetraethylene glycol di (Meth) acrylate, cyclohexane dimethanol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polyethylene glycol (200) di (meth) acrylate, polyethylene glycol (400) di (meth) acrylate, Polyethylene glycol (600) di (meth) acrylate, glycerin di (meth) acrylate, 2-hydroxy-3-acrylooxypropyl methacrylate, dimethylol tricyclodecanedi (meth) acrylate, trimethylol Propane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, trimethyl propane tri (meth) acrylate, tri ( 2-hydroxyethyl) isocyanurate triacrylate, tri (2-hydroxyethyl) isocyanurate, pentaritritol triacrylate, ethoxylate trimes All propane tri (meth) acrylate, proxyate trimethylol propane tri (meth) acrylate, pentathritol tetra (meth) acrylate, ditrimethylol proanthera (meth) acrylate, dipentatritol penta (meth) ) Acrylate, an epoxide pentaryl tritol tetra (meth) acrylate, a triethyl propane triacrylate, pentaacrylate ester, etc. are mentioned. In this case, the acrylate compound also includes an acrylate instead of (meth) acrylate.

Specifically, the photopolymerizable monomer according to an embodiment of the present invention may be selected from an unsaturated epoxy compound including an epoxy group and an unsaturated oxetane compound including an oxetane group. At this time, the photopolymerizable monomer is mixed with the compound according to the present invention and then photocured by cation, in terms of providing a hardened product having high strength with excellent curing degree, more specifically 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 [(3-ethyloxetan-3-yl) methoxymethyl] benzene, 1 , 4-bis [(3-ethyloxetan-3-yl) methoxy] benzene, 1,3-bis [(3-ethyloxetan-3-yl) methoxy] benzene, 1,2-bis [( 3-ethyloxetan-3-yl) methoxy] benzene, 4,4'-bis [(3-ethyloxetan-3-yl) methoxy] biphenyl, 2,2'-bis [(3-ethyl Oxetan-3-yl) methoxy] biphenyl, 3,3 ', 5,5'-tetramethyl-4,4'-bis [(3-ethyloxetan-3-yl) methoxy] biphenyl, 2,7-bis [(3-ethyloxetan-3-yl) methoxy] naphthalene, bis [4-{(3-ethyloxetan-3-yl) methoxy} phenyl] methane, bis [2- { (3-ethyloxetan-3-yl) methoxy} phenyl] methane, 2,2-bis [4-{(3-ethyloxetan-3-yl) methoxy} phenyl] propane, 3 (4), 8 (9) -bis [(3-ethyloxetan-3-yl) methoxymethyl] -tricyclo [5.2.1.0 2,6] decane, 2,3-bis [(3-ethyloxetane-3- Yl) methoxymethyl] norbornane, 1,1,1-tris [(3-ethyloxetan-3-yl) methoxymethyl] propane, 1-butoxy-2,2-bis [(3-in Thioxetan-3-yl) methoxymethyl] butane, 1,2-bis [{2- (3-ethyloxetan-3-yl) methoxy} ethylthio] ethane, bis [{4- (3-ethyl Oxetan-3-yl) methylthio} phenyl] sulfide, bis [{1-ethyl (3-oxetanyl)} methyl] ether and 1,6-bis [(3-ethyloxetan-3-yl) Unsaturated oxetane compounds such as methoxy] -2,2,3,3,4,4,5,5-octafluorohexane; Etc. can be mentioned.

At this time, the amount of the photopolymerizable monomer is not limited, but may be included in 50 to 99% by weight based on the total weight of the photocurable composition, specifically 60 to 99% by weight, more specifically 70 to 99% by weight It is good to be included in%.

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, a cationic photoinitiator that produces a cationic species or Lewis acid by irradiation of the active energy ray or a radical by irradiation of the active energy ray. It can be a photoinitiator that produces

The cationic photoinitiator may be an onium salt having a weak nucleophilic anion, and examples thereof include a halonium salt, an iodosil salt, a sulfonium salt, a sulfoxnium salt, or a diazonium salt. Non-limiting examples of commercial cationic photoinitiators include UVI-6974, UVI-6976, UVI-6970, UVI-6960, UVI-6990 (DOW Corp.), CD1010, CD-1011, CD-1012 (Sato Saromer Corp.), Adekaoptomer SP-150, SP-151, SP-170, SP-171 (Asahi Denka Kogyo Co., Ltd.), Irgacure 261 (Ciba Specialty Chemicals), CI-2481, CI-2624, CI-2639, CI-2064 (Nippon Soda Co, Ltd.), and DTS-102, DTS-103, NAT-103, NDS- 103, TPS-103, MDS-103, MPI-103, BBI-103 (Midori Chemical Co, Ltd.), etc. are mentioned.

In addition, the photoinitiator may be selected from benzoin derivatives, acetophenone derivatives, anthraquinone derivatives, thioxanthone derivatives, ketal derivatives, benzophenone derivatives, α-aminoacetophenone derivatives, acylphosphine oxide derivatives and oxime ester derivatives. . In this case, 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-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone and 1-chloroanthraquinone; Thioxanthone derivatives, such as 2, 4- dimethyl thioxanthone, 2, 4- diisopropyl thioxanthone, and 2-chloro thioxanthone; Ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; Benzophenone derivatives such as benzophenone, 4- (1-t-butyldioxy-1-methylethyl) benzophenone, 3,3 ', 4,4'-tetrakis (t-butyldioxycarbonyl) benzophenone ; 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one , 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, N, N-dimethylaminoacetophenone (as a commercial item Α-aminoacetophenone derivatives such as Irugacure (registered trademark) 907, Irugacure 369, Irugacure 379, etc. manufactured by Chiba Specialty Chemical Co., Ltd .; 2,4,6-trimethylbenzoyldiphenylhospinoxite, bis (2,4,6-trimethylbenzoyl) -phenylphosphineoxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl Acyl phosphine oxide derivatives, such as a pentyl phosphine oxide (A commercially available product, Lucilin TPO by BASF Corporation, Irugacure 819 by Chiba Specialty Chemicals, etc.); 2- (acetyloxyiminomethyl) thioxanthene-9-one, (1,2-octanedione, 1- [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)), and the like. It is preferred to use one or two or more mixtures selected from oxime ester derivatives.

In this case, the amount of the photoinitiator is not limited, but may be included in 0.5 to 20% by weight based on the total weight of the photocurable composition, specifically 1 to 15% by weight, more specifically 1 to 10% by weight It is good to be included.

In addition, the photocurable composition according to an embodiment of the present invention in terms of achieving a superior degree of curing, the second photosensitizer, adhesive aid, surfactant, ultraviolet light absorber, light stabilizer, heat stabilizer, antioxidant, moisture absorbent , Additives such as a softening agent, a plasticizer, a lubricant, a flame retardant, an antistatic agent, an antifoaming agent, and a leveling agent may be further included.

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

The adhesion aid may be of at least two 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.). Silane compounds having different substituents. Non-limiting examples thereof include N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl ) -3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1,3-dimethyl-butylidene) propyl Amine, N-phenyl-3-aminopropyltrimethoxysilane, N- (vinylbenzyl) -2-aminoethyl-3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and the like. have.

The surfactant may be a polyether silicone oil having a surfactant activity, and non-limiting examples thereof include trade names KF-101, KF-102, KF-105, KF-351, KF-352, KF-618, and KF. -945, KF-2001, KF-2004, X-22-163A, X-22-163B, X-22-167B, X-22-169AS, X-22-2000, X-22-4741, X-22 -4741 (above, Shin-Etsu Chemical Co., Ltd.), brand names BYK-307, BYK-325, BYK-333 (above, the product made by Vik Chemi Japan), etc. are mentioned.

According to the use of the photocurable composition, the ultraviolet absorber may serve to absorb ultraviolet rays from sunlight or the like and convert them into harmless thermal energy in the molecule to prevent the active species of the photodegradation from being excited. At this time, one non-limiting example of the ultraviolet absorber is one or more kinds of inorganic ultraviolet absorbers such as benzophenone-based, benzotriazole-based, acrylonitrile-based, metal complex salt, hindered amine-based, ultrafine titanium oxide or ultrafine zinc oxide Or two or more kinds of mixtures may be used.

The light stabilizer may play a role of capturing active species of photodegradation initiation and preventing photooxidation. In this case, a non-limiting example of the light stabilizer may be a known compound such as a hindered amine compound or a hindered piperidine compound.

Non-limiting examples of the heat stabilizer include tris (2,4-di-tert-butylphenyl) phosphite, bis [2,4-bis (1,1-dimethylethyl) -6-methylphenyl] ethylester phosphorous acid, Tetrakis (2,4-di-tert-butylphenyl) [1,1-biphenyl] -4,4'-diylbisphosphonate and bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite Phosphorus thermal stabilizers such as these; Lactone-based heat stabilizers such as reaction products of 8-hydroxy-5,7-di-tert-butyl-furan-2-one and o-xylene; and one or more of these or a mixture of two or more thereof. 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 encapsulant when the photocurable composition is used as the encapsulant. Non-limiting examples of the moisture adsorbent include metal oxides, sulfates, organic metal oxides, clay, talc, acicular silica, plate silica, porous silica, zeolite, titania or zirconia, and specific examples thereof are magnesium oxide Metal oxides such as calcium oxide, strontium oxide, barium oxide or aluminum oxide; Sulfates such as magnesium sulfate, sodium sulfate or nickel sulfate; Organic metal oxides, such as aluminum oxide octylate, are mentioned.

In this case, the additive may be included in each of 0.01 to 10 parts by weight based on the total weight of the composition, specifically, it is preferably included in 0.05 to 5 parts by weight, more specifically 0.1 to 5 parts by weight, but is not limited thereto. to be.

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

The shape of the encapsulant is not particularly limited, but may be preferably in the form of a sheet or film. In this case, the film thickness of the encapsulant sheet or film may be appropriately adjusted in consideration of support efficiency and breakage potential of devices such as cells of organic electronic devices, weight reduction or workability of the device, and the like. May be prepared to have a thickness of 5 to 2,000 μm, and more specifically, may be prepared to have a thickness of 5 to 1,000 μm.

The cured product according to the present invention, that is, the encapsulant may be prepared using the photocurable composition of the combination according to the present invention as described above, thereby providing a cured product having excellent hygroscopicity and excellent moisture resistance as well as achieving excellent degree of curing. In addition, the encapsulant according to the present invention can ensure improved heat resistance and excellent surface properties (eg, surface hardness, adhesion, crack resistance, thermal shock resistance, etc.).

In addition, according to the present invention, even when applied for the protection of the device in a large-area device can be laminated on the device without causing bubbles, etc., and effectively protect the device from external components, for example, moisture, etc. after the sealing process can do.

The encapsulant according to an embodiment of the present invention may have a multilayer structure in which two or more organic layers including the photocurable composition are laminated. In this case, each organic layer of the multilayer structure may have different elastic modulus, light transmittance, and water vapor transmission rate.

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

Light transmittance (@ 400nm) of the encapsulation material according to an embodiment of the present invention may be specifically 85 to 99%, more specifically 90 to 99%.

The encapsulant 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 that has been subjected to a release treatment, and the type of such substrate may be used without limitation in the art.

The encapsulant according to an embodiment of the present invention may be applied to encapsulation and protection of various objects. In particular, the encapsulant may be effective for protecting an object including an element sensitive to oxygen or moisture. Examples of the object to which the encapsulant may be applied include an organic electronic device such as a photovoltaic device, a rectifier, a transmitter, or an organic light emitting diode (OLED). Of course, solar cells or secondary batteries, etc. can also be applied.

Hereinafter, a novel compound, a photocurable composition comprising the same, and a cured product thereof according to the present invention will be described in more detail with reference to Examples. However, the following examples are only one reference for describing the present invention in detail, and the present invention is not limited thereto and may be implemented in various forms.

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

[ Example  1] Preparation of Compound 1

Under a nitrogen atmosphere, 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) (1,4,7,10,13,16-hexaoxacyclooctadecane) 0.53 g, 1,2-dichlorobenzene 100ml were mixed and stirred at 180 ° C for 48 hours.

After completion of the reaction, the reaction solution was cooled, filtered under reduced pressure, and the filtrate was washed with distilled water two to three times. Then, the organic solvent was removed using a rotary concentrator, and then purified through column chromatography to obtain 2.9 g of Compound 1. Got.

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), 6.83 (t, J = 9.0 Hz, 2H), 6.21 (d, J = 6.0 Hz, 1H), 6.16 (s, 1H), 3.91 (s, 1H), 2.73 (m, 2H), 1.14 (t, J = 9.0 Hz, 3H).

[ Example  2] Preparation of Compound 2

Under a nitrogen atmosphere, 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, 0.53 g of 18-crown-6 and 100 ml of 1,2-dichlorobenzene were mixed and then stirred at 180 ° C. for 48 hours.

After completion of the reaction, the reaction solution was cooled, 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 concentrator, and then purified by column chromatography to obtain 2.97 g of Compound 2. Got.

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 ( m, 4H), 6.12 (d, J = 6.0 Hz, 1H), 6.08 (s, 1H), 3.92 (s, 3H), 3.81 (s, 3H), 2.73 (m, 2H), 1.14 (t, J = 9.0 Hz, 3H).

[ Example  3] Preparation of Compound 3

Under a nitrogen atmosphere, 2.59 g of 2- (ethylthio) -10H-phenothiazine, 3.06 g of iodobenzene, 4.15 g of anhydrous potassium carbonate, copper powder 1.82 g, 18-crown-6 0.53 g, 1,2 -100 ml of dichlorobenzene was mixed and stirred at 150 ° C. for 24 hours.

After completion of the reaction, the reaction solution was cooled, 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 concentrator, and then purified through column chromatography to obtain 2.85 g of Compound 3. Got.

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 (d, J = 6.0 Hz, 1H), 5.15 (s, 1H), 2.72 (m, 2H), 1.12 (t, J = 9.0 Hz, 3H).

[ Example  4] Preparation of Compound 4

Under nitrogen atmosphere, 2.59 g of 2- (ethylthio) -10H-phenothiazine, 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, 1,2-dichlorobenzene 100 ml were mixed and stirred at 180 ° C. for 48 hours.

After completion of the reaction, the reaction solution was cooled, 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 concentrator, and then purified by column chromatography to obtain 2.71 g of Compound 4. -1 was obtained.

Next, 1.3 g of compound 4-1 was dissolved in 30 ml of dimethylformamide (DMF) under a nitrogen atmosphere, cooled to 0 ° C., and 0.74 g of N-bromosuccinimide (NBS) was added to room temperature (about 25 Agitation) for 8 hours. Upon completion of the reaction, the mixture was neutralized to pH 7 with dilute potassium hydroxide and extracted with methylene chloride (MC). The product was purified via column chromatography to give 1.32 g of compound 4-2.

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

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, 1H), 6.39 (d, J = 9.0 Hz, 1H), 6.10 (d, J = 9.0 Hz, 1H), 6.03 (d, J = 9.0 Hz, 1H), 4.03 (t, J = 6.5 Hz, 2H) , 3.85 (t, J = 6.5 Hz, 2H), 1.82 (m, 2H), 1.69 (m, 2H), 1.53 (m, 2H), 1.44 (m, 2H), 1.02 (t, J = 7.5 Hz, 3H), 0.95 (t, J = 7.5 Hz, 3H).

[Example 5] Preparation of a cationic photo-curable composition

45.85 g of photopolymerizable monomers (3,4-epoxycyclohexylmethyl-3,4'-epoxycyclohexanecarboxylate, UVR-6110, Dow chemical), cationic photoinitiator (CD-1012, Sartomer) 2.0 g, Example 1 1.0 g of the compound, 1.0 g of the adhesion aid (KBM-403) and 0.15 g of the surfactant (BYK-307) were sequentially mixed, and stirred at room temperature (23 ° C.) for 3 hours to prepare a cationic photocurable composition.

[Example 6-8] Preparation of a cationic photo-curable composition

A cationic photocurable composition was prepared by the same composition and method as Example 5, except that 1.0 g of the compound of Example 2, Example 3, or Example 4 was used instead of the compound of Example 1.

Example 9 Preparation of the cationic photo-curing composition

45.85 g of photopolymerizable monomer (UVR-6110, Dow chemical), 2.0 g of photoinitiator (CD-1012, Sartomer), 0.5 g of compound of Example 1, 0.5 g of photosensitizer (UVS-1331, Kawasaki Kasei chemical), adhesion 1.0 g of the preparation (KBM-403) and 0.15 g of the surfactant (BYK-307) were sequentially mixed and stirred at room temperature for 3 hours to prepare a cationic photocurable photocurable composition.

[Examples 10 to 12 Preparation of the cationic photo-curing composition

A cationic photocurable composition was prepared in the same composition and method as in Example 9, except that 0.5 g of each of the compounds of Examples 2, 3, and 4 was used instead of the compound of Example 1.

Example 13 Preparation of radical photo-curable composition

10.37 g of phenoxyethyl acrylate, 55.34 g of tripropylene glycol diacrylate, 8.30 g of triethyl propane triacrylate, 0.83 g of the compound of Example 1, 1.66 g of a photoinitiator (Irgacure TPO, BASF), an adhesion aid (KBM- 503) 1.0g and 0.15g of surfactant (BYK-307) were sequentially mixed and stirred at room temperature for 3 hours to prepare a radical photocurable composition.

[Examples 14 to 16 Preparation of a radical photo-curable composition

Radical photocurable compositions were prepared in the same composition and method 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.

Example 17 Preparation of radical photo-curable composition

10.37 g of phenoxyethyl acrylate, 55.34 g of tripropylene glycol diacrylate, 8.30 g of triethyl propane triacrylate, 0.83 g of the compound of Example 1, 0.43 g of the compound of Example 1, and a photosensitizer (UVS- 1331, Kawasaki Kasei chemical) 0.4g, (Irgacure TPO, BASF) 1.66g, a mixture of adhesive aid (KBM-503) 1.0g and 0.15g surfactant (BYK-307) was sequentially mixed and stirred for 3 hours at room temperature Radical photocurable compositions were prepared.

[Examples 18 to 20 Preparation of a radical photo-curable composition

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

Comparative Example 1 Preparation of Cationic Photocurable Composition

A cationic photocurable composition was prepared by the same composition and method as Example 5, except that 1.0 g of a photosensitizer (UVS-1331, Kawasaki Kasei chemical) was used instead of the compound of Example 1.

Comparative Example 2 Preparation of Radical Photocurable Composition

A radical photocurable composition was prepared in the same composition and method 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 photocurable composition prepared by the above method was coated on a polyimide film substrate by inkjet method, and then 1000mJ UV irradiation was performed for 1 second with a 1000mW LED exposure machine having a wavelength of 395nm in a nitrogen atmosphere to form a film having a thickness of 5 μm, and then physical properties thereof were measured. .

1) Hardness Measurement

Encapsulation substrate having a thickness of 5 μm by coating the polyimide substrate film by inkjet method using the photocurable compositions prepared in Examples and Comparative Examples and irradiating 1000mJ UV light for 1 second with a 1000mW LED exposure machine having a wavelength of 395nm in a nitrogen atmosphere. Was prepared. Each film produced was cut to 5 cm wide and 5 cm long. Then, using the FT-IR (infrared spectrometer), the absorption spectra of the film before curing and the film after curing were measured, and then the degree of curing was calculated by the following Equation 1.

(Equation 1)

Hardness (%) = 100- (Wf / Wi ⅹ 100)

[Equation 1, wherein Wi is the peak area (absorption) of the functional group of the photopolymerizable monomer included in the composition before curing, the Wf is the peak area (absorption) of the functional group of the photopolymerizable monomer included in the film after curing. Means.]

2) Surface hardness measurement

An encapsulant substrate having a thickness of 5 μm was prepared by coating the glass on the glass by an inkjet method using the photocurable compositions prepared in Examples and Comparative Examples, and then irradiating 1000mJ UV light for 1 second with a 1000mW LED exposure machine having a wavelength of 395nm in a nitrogen atmosphere. . The surface hardness of the prepared substrate was measured with a pencil hardness tester at 200 g weight.

3) Light transmittance measurement

An encapsulant substrate having a thickness of 5 μm was prepared by coating the glass on the glass by an inkjet method using the photocurable compositions prepared in Examples and Comparative Examples, and then irradiating 1000mJ UV light for 1 second with a 1000mW LED exposure machine having a wavelength of 395nm in a nitrogen atmosphere. . The prepared substrate was measured for light transmittance using a UV-VIS spectrophotometer (@ 400nm).

4) Outgassing Measurement

An encapsulant substrate having a thickness of 5 μm was prepared by coating the glass on the glass by an inkjet method using the photocurable compositions prepared in Examples and Comparative Examples, and then irradiating 1000mJ UV light for 1 second with a 1000mW LED exposure machine having a wavelength of 395nm in a nitrogen atmosphere. . TVOC generated by heat treatment for 10 minutes at 100 ℃ prepared substrate was measured using 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.

Curing degree
(Curing Rate) Surface hardness
Light transmittance
(@ 400nm) Outgasing
Example 5 93% 3H 97% 151 ppm Example 6 90% 2H 96% 182ppm Example 7 92% 3H 97% 168 ppm Example 8 85% 2H 96% 485 ppm 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% 855 ppm

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

As shown in Table 1 and Table 2, in the case of the film using the cationic photocurable composition and the radical photocurable composition according to the present invention, not only has excellent hardness and significantly lower outgassing properties due to the high degree of curing, but also polycyclic In the light transmittance of 400 nm, which is the biggest problem of the polynuclear aromatic hydrocarbon-based photosensitizer, the characteristics were excellent. In addition, even when used in combination with the photosensitizer prepared in the present invention and the existing photosensitizer, it was confirmed that it has excellent characteristics. This means that according to the curing conditions (exposure wavelength and exposure amount, etc.) of the various compositions, only the adjustment of the mixing ratio of the photosensitizer and the existing photosensitizer of the present invention can produce a film having various characteristics that meet the user's purpose.

Although the present invention has been described through the specific matters and the limited embodiments as described above, it is provided only to help a more general understanding of the present invention, and the present invention is not limited to the above embodiments, and the present invention belongs to Those skilled in the art can make various modifications and variations from this description.

Therefore, the spirit of the present invention should not be limited to the described embodiments, and all the things that are equivalent to or equivalent to the claims as well as the following claims will belong to the scope of the present invention. .

Claims (11)

delete delete delete Compounds selected from the following structures:

A photocurable composition comprising the compound of claim 4. The method of claim 5,
The compound is used for light absorption, photocurable composition. The method of claim 5,
The photocurable composition is a cation by light irradiation; Radicals; Or cations and radicals; Will be generated and photocured, photocurable composition. The method of claim 5,
The photocurable composition further comprises a photopolymerizable monomer having a two or more photocurable unsaturated groups and a photoinitiator, photocurable composition. The method of claim 8,
The photoinitiator is a cationic photoinitiator, photocurable composition. The method of claim 8,
The photoinitiator is any one or two selected from benzoin derivatives, acetophenone derivatives, anthraquinone derivatives, thioxanthone derivatives, ketal derivatives, benzophenone derivatives, α-aminoacetophenone derivatives, acylphosphine oxide derivatives and oxime ester derivatives The photocurable composition which is the above. An organic electronic device encapsulated with an encapsulant comprising a cured product of the photocurable composition of any one of claims 5 to 10.