KR101803660B1 - Acrylate-based compound having high refractive index, photo-curing composition and optical film manufactured by the photosensitive composition - Google Patents

Abstract

The present invention relates to an acrylate-based compound, a photocuring composition including the same, and an optical film manufactured by using the same, wherein the acrylate-based compound is represented by chemical formula 1. An objective of the present invention is to provide an acrylate-based compound having a high refractive index, being excellent in optical characteristics when applied to an optical film, and capable of improving stability against external impact.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a photo-curable composition, an acrylate-based compound, and an optical film prepared using the same. BACKGROUND ART [0002]

The present invention relates to an acrylate-based compound, a photo-curable composition containing the same, and an optical film produced using the same, and is a photo-curable composition having a high refractive index suitable for producing an optical film, And to a manufactured optical film.

Acrylates having a high refractive index are widely used in optical products such as optical lenses, optical films, and optical media. BACKGROUND ART [0002] Optical films are used in display products such as liquid crystal displays and plasma display panels, and prism sheets among optical films are mainly used for improving the brightness of light provided to liquid crystal panels.

An important optical parameter of the material constituting the prism pattern of the prism sheet is the refractive index. The higher the refractive index, the better the performance of the prism sheet. A prism sheet having a high refractive index is disclosed in Korean Patent Publication No. 2001-0012340 (published on Feb. 15, 2001) and Korean Patent Publication No. 2005-0010760 ). These patents disclose optical products made from a polymerizable composition comprising a brominated monomer having a high refractive index. However, a compound including a halogen element such as bromine or chlorine has an advantage that the refractive index of the material can be increased, but there is a problem that when the composition is cured to produce a film, the yellowing is severe. The yellowing phenomenon itself not only deteriorates the performance of the optical film but also adversely affects the color reproducibility of the display device.

Since most of the acrylates developed for high refractive index contain halogen elements, there is a problem that they are toxic and a large amount of corrosive gas is generated when they are burned. In addition, since the acrylate itself having a high refractive index has a high viscosity or a solid state in many cases, the viscosity of the coating liquid containing the acrylate itself is high, which makes the coating process difficult. Therefore, there is a need to prepare a non-halogen liquid high refractive index acrylate.

In addition, when the prism sheet is applied to a touch screen display as an optical product, it is necessary that the prism pattern of the prism sheet has excellent stability against impact such as external pressing.

An object of the present invention is to provide an acrylate-based compound having a high refractive index and being excellent in optical properties when applied to an optical film and capable of improving stability against external impact.

Another object of the present invention is to provide a photocurable composition comprising the acrylate-based compound.

It is still another object of the present invention to provide an optical film formed of the photo-curable composition, which can be applied to a display device to improve the brightness of a display device.

The acrylate compound for one purpose of the present invention is represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

x represents a natural number of 1 to 6,

y represents a natural number of 1 to 6,

R represents a hydrogen atom or a methyl group,

Ar represents any one of the following formulas (1-a) to (1-d)

[Chemical Formula 1-a] [Chemical Formula 1-b]

[Chemical Formula 1-c] [Chemical Formula 1-d]

Z in the formulas (1-b) and (1-c) represents NH, S, O or Se,

At least one of the hydrogen atoms of Ar may be substituted with an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms.

In one embodiment, the acrylate-based compound may be represented by the following general formula (2) or (3).

[Chemical Formula 2] < EMI ID =

In one embodiment, the acrylate-based compound may have a liquid-phase refractive index of 1.5 to 1.8.

Another object of the present invention is to provide a photocurable composition comprising an acrylate compound, an acrylic monomer and a photoinitiator represented by the above formula (1).

In one embodiment, the amount of the acrylate compound may be 3 to 85 wt%, the amount of the acrylic monomer may be 5 to 82 wt%, and the amount of the photoinitiator may be 0.5 to 15 wt% based on the total weight of the photocurable composition.

The optical film for another purpose of the present invention is prepared by using a photocurable composition containing an acrylate-based compound represented by the general formula (1). At this time, the optical film may be a prism sheet including a prism pattern.

According to the acrylate-based compound of the present invention described above, the photo-curing composition containing the same, and the optical film produced using the acrylate-based compound, the acrylate-based compound contains a thioalkylene group, It is possible to impart a high elastic force to the optical film produced by using the film. Accordingly, even if an external impact is applied to the optical film, excellent stability is exhibited. The optical film produced using the high-refractive-index acrylic monomer according to the present invention can be applied to a display device, thereby improving the brightness of the display device.

1 is a view for explaining an optical device to which an optical film according to an embodiment of the present invention is applied.
FIG. 2 is a view for explaining a restoring force performance test performed in the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. The present invention is capable of various modifications and various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. It is to be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but on the contrary, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. Like reference numerals are used for like elements in describing each drawing.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the term "comprises" or "having ", etc. is intended to specify that there is a feature, step, operation, element, part or combination thereof described in the specification, , &Quot; an ", " an ", " an "

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

Acrylate compound

The acrylate compound according to the present invention is represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1, x represents a natural number of 1 to 6, y represents a natural number of 1 to 6, R represents a hydrogen atom or a methyl group, and Ar represents any one of the following Chemical Formulas 1-a to 1-d .

[Chemical Formula 1-a] [Chemical Formula 1-b]

[Chemical Formula 1-c] [Chemical Formula 1-d]

Z in the above formulas 1-b and 1-c represents NH, S, O or Se, and at least any one of the hydrogen atoms of Ar is substituted with an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms .

The alkyl group as a substituent of Ar at this time includes not only a straight chain but also a branched form, and examples of the aryl group having 6 to 12 carbon atoms include a phenyl group and a naphthalenyl group. Examples of the aryl group as a substituent of Ar include dibenzofuran, dibenzothiophene, bipheneyl, carbazole, diphenyl sulfide, diphenyl ether ( Diphenyl ether, 9,9-diphenyl fluorene, and the like.

In the above formula (1), Ar may have a molecular weight of 120-450.

When the molecular weight of Ar is less than 120, the refractive index of liquid phase of the acrylate compound may be low. When the molecular weight of Ar exceeds 450, the acrylate compound exists in a solid state having low solubility with other monomers, It is possible to cause defects such as the formation of particles during production of a film by using a base compound.

In one embodiment, the acrylate-based compound may be represented by the following general formula (2) or (3).

[Chemical Formula 2] < EMI ID =

The acrylate compound according to the present invention may have a liquid refractive index of 1.5 to 1.8. At this time, the liquid refractive index measurement condition is 550 nm at 25 캜.

The acrylate compound according to the present invention is a non-halogen compound containing no halogen element, and has a liquid refractive index of 1.5 or more, and can be controlled to a viscosity suitable for molding when used as a composition.

Photo-curing composition

The photocurable composition according to the present invention includes an acrylate-based compound, an acrylic monomer, and a photoinitiator.

(1) Acrylate compound

The acrylate-based compound contained in the photo-curing composition is the compound represented by Formula 1, which is substantially the same as the acrylate-based compound according to the present invention described above. Therefore, redundant detailed description will be omitted.

The content of the acrylate compound may be 3 to 85% by weight based on the total weight of the photocurable composition. When the content of the acrylate compound is less than 3% by weight, the effect of the acrylate compound is only insignificant. When the content of the acrylate compound is more than 85% by weight, Film formation during photocuring may be difficult. Preferably, the content of the acrylate compound may be 3 to 80% by weight based on the total weight of the photocurable composition.

(2) Acrylic monomers

The acrylic monomer may be an organic photo-curable acrylic compound having an average liquid refractive index of 1.5 to 1.8 as measured at 550 nm at 25 ° C.

Examples of the acrylic monomer include acrylic acid esters such as 2-phenoxyethyl acrylate, 2-phenoxyethyl (meth) acrylate, 3-phenoxypropyl acrylate, 3-phenoxypropyl (meth) (Meth) acrylate, 5-phenoxypentyl (meth) acrylate, 6-phenoxyhexyl acrylate, 6-phenoxyhexyl Phenoxyhexyl acrylate, 7-phenoxyheptyl acrylate, 7-phenoxyheptyl (meth) acrylate, 8-phenoxyoctyl acrylate, 8-phenoxyoctyl (meth) acrylate, (Meth) acrylate, 2- (phenylthio) ethyl (meth) acrylate, 10-phenoxydecyl (meth) acrylate, 3- (phenylthio) propyl acrylate, 3- (phenylthio) propyl (meth) acrylate, 4- (Phenylthio) butyl acrylate, 4- (phenylthio) butyl (meth) acrylate, 5- (phenylthio) pentyl acrylate, 5- (Phenylthio) heptyl (meth) acrylate, 8- (phenylthio) octyl acrylate, 8 (phenylthio) octyl acrylate, (Meth) acrylate, 10- (phenylthio) decyl acrylate, 10- (phenylthio) decyl acrylate, 2- (naphthalene-2-yloxy) ethyl acrylate, 2- (naphthalene-2-yloxy) ethyl (meth) acrylate, 3- (Meth) acrylate, 4- (naphthalene-2-yloxy) butyl (meth) acrylate, 4- (Naphthalene-2-yloxy) pentyl acrylate, 5- (naphthalene-2-yloxy) pentyl (meth) acrylate, 6- (Naphthalene-2-yloxy) heptyl (meth) acrylate, 8- (naphthalene-2-yloxy) heptyl (Naphthalene-2-yloxy) octyl acrylate, 9- (naphthalene-2-yloxy) nonyl acrylate, 9- (Naphthalene-2-ylthio) decyl acrylate, 10- (naphthalene-2-yloxy) decyl (meth) acrylate, 2- (Naphthalene-2-ylthio) propyl (meth) acrylate, 4 (naphthalene-2-ylthio) - (naphthalene-2-ylthio) butyl acrylate (Naphthalene-2-ylthio) pentyl (meth) acrylate, 6 (naphthalene-2-ylthio) (Meth) acrylate, 7- (naphthalene-2-ylthio) heptyl, acrylate, 7- (naphthalene-2-ylthio) hexyl acrylate, 6- (Naphthalene-2-ylthio) octyl (meth) acrylate, 8- (naphthalene- (Naphthalene-2-ylthio) decyl acrylate, 10- (naphthalene-2-ylthio) decyl acrylate, Acrylate, 2 - ([1,1'-biphenyl] -4-yloxy) ethyl (meth) acrylate, 2- ([1,1'-biphenyl] -4-yloxy) propyl acrylate, 3 - ([ ([1,1'-biphenyl] -4-yloxy) butyl (meth) acrylate, 4 - Acrylate, 5 - ([1,1'-biphenyl] -4-yloxy) pentyl acrylate, 5- ([1,1'-biphenyl] -4-yloxy) hexyl (meth) acrylate, 7- ([1,1'-biphenyl] -4-yloxy) heptyl acrylate, 7 - ([ ([1,1'-biphenyl] -4-yloxy) octyl (meth) acrylate, 9 - Biphenyl] -4-yloxy) nonyl acrylate, 10 - ([1,1'-biphenyl] (1, 1'-biphenyl) -4-yloxy) decyl acrylate, 10 - - ylthio) ethyl < / RTI > ([1,1'-biphenyl] -4-ylthio) ethyl (meth) acrylate, 3- 4 - ylthio) propyl (meth) acrylate, 4 - ([1,1'-biphenyl] ([1,1'-biphenyl] -4-ylthio) pentyl acrylate, 5 - ([ Biphenyl] -4-ylthio) pentyl (meth) acrylate, 6 - ([ ([1,1'-biphenyl] -4-ylthio) heptyl acrylate, 7 - ([1,1'-biphenyl] Octyl acrylate, 8 - ([1,1'-biphenyl] -4-ylthio) heptyl (meth) acrylate, ([1,1'-biphenyl] -4-ylthio) nonyl acrylate, 9 - ([1,1'-biphenyl] -4-ylthio) nonyl (Meth) acrylate Biphenyl] -4-ylthio) decyl (meth) acrylate, 2 - [(1,1'- (Meth) acrylate, 2-hydroxy-2- (naphthalene-2-yloxy) ethyl acrylate, 2-hydroxy-2-phenoxyethyl Acrylate, 2 - ([1,1'-biphenyl] -4-yloxy) ethyl acrylate, 2- ([ 2- (2-phenoxyethoxy) ethyl (meth) acrylate, 2- (2-phenoxyethoxy) ethyl Acrylate, 2 - (([1,1'-biphenyl] -4-yloxy) methoxy) ethylacrylate, Acrylate, 2 - ((naphthalene-2-yloxy) methoxy) ethyl acrylate, 2 - ((1,1'-biphenyl) -4-yloxy) methoxy) ethyl (Naphthalene-2-yloxy (Meth) acrylate, 2 - ((phenylthio) methoxy) ethyl acrylate, 2 - ((phenylthio) methoxy) ethyl (Meth) acrylate, 2 - ((naphthalene-2-ylthio) methoxy) ethyl Bis (4-phenylene)) bis (oxy) bis (ethane-2,1-diyl) diacrylate, 2,2 ' Bis (ethane-2,1-diyl) bis (2-methylacrylate), 3,3'- (4,4'- (Propane-3,1-diyl) diacrylate, 3,3 '' - (4,4'-diene) bis Bis (propane-3,1-diyl) bis (2-methylacrylate), 2,2 ` Bis (ethane-2,1-diyl) diacrylate, 2, 3-bis (4,4'- 2 '- (4,4'- (9H-fluorene-9, (9-diyl) bis (4,1-phenylene)) bis (sulfanediyl) bis (ethane-2,1-diyl) bis (2-methylacrylate), 3,3 ' (4,4-phenylene)) bis (propanediyl) bis (propane-3,1-diyl) diacrylate, 3,3 ' Bis (propane-3,1-diyl) bis (2-methylacrylate), 2,2-bis Bis (4,1-phenylene)) bis (4,1-phenylene)) bis (oxy) bis (4, 4 '- (9H-fluorene-9,9-diyl) bis (4, Bis (ethane-2,1-diyl) bis (2-methylacrylate), 3,3 '- (4-phenylene) Bis (4, 1-phenylene)) bis (oxy) bis (4, (4,4'- (9H-fluorene-9,9-diyl) bis (4,1-diyl) diacrylate, 3,3 ' Rhen)) Bis (oxy) Bee (4,4'-bis (4,1-phenylene)) bis (oxy) bis (propane-3,1-diyl) bis (2-methylacrylate), 2,2 ' Bis (ethane-2,1-diyl) bis (4-phenylene)) bis (oxy) bis Diacrylate, 2,2'- (4,4'- (4,4'- (9H-fluorene-9,9-diyl) bis (4,1- phenylene)) bis (sulfanediyl) bis (Meth) acrylate, 3,3 '- (4,4'- (4,4'- (9H) Bis (propane-3,1-diyl) bis (4,1-phenylene)) bis (4,1- Acrylate, 3,3'- (4,4'- (4,4'- (9H-fluorene-9,9-diyl) bis (4,1- phenylene)) bis (sulfanediyl) bis (1-phenylene)) bis (oxy) bis (propane-3,1-diyl) bis (2-methylacrylate), 2,2 ' Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (4,1-phenylene)) bis Rate, 2,2` Bis (ethane-2,1-diyl) bis (4,1-phenylene)) bis (oxy) bis Bis (oxy) bis (ethane-2, -1 diyl) bis (2-methylacrylate). (2,2'- (4,4'- (9H-fluorene-9,9-diyl) bis (4,1- phenylene)) bis (sulfanediyl) bis 1-diyl)) bis (oxy) bis (ethane-2,1-diyl) diacrylate, 2,2'- (4,4'- (9H- Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl)) bis (4,1-phenylene) Bis (ethane-2,1-diyl) diacrylate, 2,2 '- (4,4'-bis Bis (ethane-2,1-diyl) bis (2-methylacrylate), 2,2 '- (4,4'-oxybis (4,4'-phenylene) bis (sulfanediyl)) bis (ethane-2,1-diyl) diacrylate, 2,2 '- (4,4'- Bis (4,1-phenylene) bis (oxy) bis (ethane-2,1-diyl) bis (2-methylacrylate), 2,2 ' (Ethane-2,1-diyl) diacrylate, 2,2 '- (4,4'-thiobis ) Bis (ethane-2,1-diyl) diacrylate, bis (2-methylacrylate), and 2,2 '- (4,4'-thiobis (2-methylacrylate), 2,2 '- (4,4'-thiobis (4,1-phenylene) bis (sulfanediyl) Bis (propane-3,1-diyl) bis (oxy) bis (ethane-2, , 1-diyl) diacrylate, 2,2 '- (3,3' - (4,4'-oxybis (4,1-phenylene) bis (oxy) Bis (2-methyl acrylate), 2,2 '- (3,3' - (4,4'-thiobis (4,1- Bis (oxy) bis (ethane-2,1-diyl) diacrylate, 2,2 '- (3,3' - (Oxy) bis (ethane-2,1-diyl) bis (2-ethylhexyl) bis (4,1'- Methyl acrylate), 2,2 '- (3,3' - (4,4'-oxybis (4,1-phenylene) bis (sulfanediyl) (3,3 '- (4,4'-oxybis (4,1-di-tert-butyldimethylsilyloxy) Bis (propane-3,1-diyl) bis (oxy) bis (ethane-2,1-diyl) bis (2-methylacrylate), 2,2 '- Bis (propane-3,1-diyl)) bis (oxy) bis (ethane-2,1 Bis (ethane-2,1-diyl) diacrylate, 2,2 '- (4,4' Diyl) diacrylate, 2,2 '- (4,4' - (propane-2,2-diyl) bis (4,1- ) Bis (2-methylacrylate), 2,2 '- (4,4' - (propane-2,2-diyl) bis (4,1- Bis (ethane-bis- (2,6-di-tert-butylphenol) diacrylate, 2,2 ' (2,2 '- (4,4' - (propene-2,2-diyl) bis (4,1-phenylacrylate) Bis (ethane-2,1-diyl) diacrylate, 2,2 '- (2,2' - (4, Bis (ethoxy) bis (ethane-2,1-diyl)) bis (4-fluorophenyl) (2,2 '- (4,4' - (propane-2,2-diyl) bis (4,1-phenylen)) bis (2-methyl acrylate) Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl)) bis Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (4,1- (2,2 '- (2,2' - (4,4 '- (propene-2,2-diyl) bis (4,1- phenylene)) (Oxy) bis (ethane-2,1-diyl)) bis (oxy) bis (ethane-2,1-diyl) Bis (ethoxy) -2 '- (2,2' - (2,2 '- (4,4' , 1-diyl)) bis (oxy) ratio (2,2 '- (2,2' - ((ethane-2,1-diyl)) bis Bis (ethane-2,1-diyl)) bis (oxy) bis (ethane-2, , 1-diyl)) bis (oxy) bis (ethane-2,1-diyl) diacrylate, 2,2 '- (2,2' Bis (ethane-2,1-diyl) bis (4,1-phenylene)) bis (ethane-2,1-diyl)) bis Oxy) bis (ethane-2,1-diyl) bis (2-methylacrylate, 2,2 '- (2,2' - (2,2 '- (4,4'- Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (2,2 '- (2,2' - (4,4'-oxybis (4,1-phenylene) bis (oxy)) bis Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (oxy) bis , 2 '- (4,4'-thiobis (4,1-phenylen) Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl)) bis (ethane- (2,2 '- (2,2' - (4,4'-thiobis (4,1-phenylene) bis (oxy) ), 2,2 '- (2,2' - (2,2 ') - bis (ethane-2,1-diyl) bis Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (oxy) bis (2,2 '- (2,2' - (4,4'-thiobis (4,1-phenylene) bis Bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (ethane-2,1-diyl) bis (Meth) acrylate, polyester urethane diacrylate, tripropylene glycol diacrylate, urethane acrylate, epoxy acrylate, phenylthioethyl (methyl) acrylate, isobornyl (Methyl) acrylate, phenoxyethoxyethyl (meth) acrylate, phenoxybenzyl acrylate, phenoxyethoxyethyl (meth) acrylate, , 2-naphthyloxyethyl (methyl) acrylate, 2-naphthyloxyethyl (methyl) acrylate, 2-1- Naphthylthioethyl (meth) acrylate or 2-2-naphthylthioethyl (methyl) acrylate, trimethylolpropane triacrylate, and the like. These may be used alone or in combination of two or more.

The content of the acrylic monomer may be 5 to 82% by weight based on the total weight of the photocurable composition.

(3) Photo initiators

The photoinitiator is a compound which reacts with light, and may include a photopolymerization initiator and / or a radical polymerization initiator.

Examples of the photopolymerization initiator include an acetophenone-based compound, a phosphine oxide-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, and a triazine-based compound.

Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.

Examples of the phosphine oxide-based compound include diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide and bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide.

Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

Examples of the thioxanthone compound include thioxanthone, 2-crothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, Propyl thioxanthone, 2-chlorothioxanthone, and the like. Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho 1-yl) -4,6 -Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) (Piperonyl) -6-triazine, and 2-4-trichloromethyl (4'-methoxystyryl) -6-triazine.

The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.

The radical polymerization initiator may be a peroxide compound, an azobis compound, or the like. Examples of the peroxide compound include ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, and acetylacetone peroxide; Diacyl peroxides such as isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, o-methylbenzoyl peroxide, and bis-3,5,5-trimethylhexanoyl peroxide; Hydroperoxides such as 2,4,4-trimethylpentyl-2-hydroperoxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide, and t-butyl hydroperoxide; Dicumyl peroxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexane, 1,3-bis (t-butyloxyisopropyl) Dialkyl peroxides such as esters; Alkyl peresters such as 2,4,4-trimethylpentyl peroxyphenoxyacetate,? -Cumyl peroxyneodecanoate, t-butyl peroxybenzoate and di-t-butyl peroxytrimethyl adipate; Di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, bis-4-t-butylcyclohexyl peroxydicarbonate, diisopropyl peroxydicarbonate, acetylcyclohexylsulfonyl peroxide, t And percarbonates such as butyl peroxyaryl carbonate. Examples of the azobis compound include 1,1'-azobiscyclohexane-1-carbonitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2, -azobis Azoisobutyrate), 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), α, α'-azobis (isobutylnitrile) and 4,4'-azobis - cyanobalenoic acid), and the like.

The photoinitiator may further include a photosensitizer that generates a chemical reaction by absorbing light to be excited and transferring the energy. Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .

The content of the photoinitiator may be 0.5 to 15% by weight based on the total weight of the photocurable composition. When the content of the photoinitiator is in the range of 0.5 to 15% by weight, photocuring can be sufficiently performed when light is supplied to the photo-curing composition, thereby improving the reliability of the production of the optical film and minimizing the amount of the photo-initiator remaining unreacted. It is possible to prevent the transmittance of the optical film from deteriorating. Preferably, the content of the photoinitiator may be 0.5 to 15% by weight based on the total weight of the photocurable composition.

(4) Other additives

The photocurable composition according to the present invention may further comprise other additives in addition to the above-described acrylate compound, acrylic monomer and photoinitiator.

Examples of the other additives include surfactants, ultraviolet absorbers, and radical stabilizers. These may be used alone or in combination of two or more.

Examples of the surfactant include Megaface F-444, Megaface F-554, and BYK-333. Examples of the ultraviolet absorber include Hostavin 3206 and Tinuvin 400. Examples of the radical stabilizer include Irgacure 1010, Tinuvin 292, and the like. These may be used alone or in combination of two or more.

When the composition further contains the other additives, the content of the other additives may be 0.2 wt% to 5 wt% based on the total weight of the photocurable composition. If it is less than 0.2% by weight, the effect may be insignificant. If it is more than 5% by weight, film formation may be prevented.

Optical film

1 is a view for explaining an optical device to which an optical film according to an embodiment of the present invention is applied.

The optical device includes an optical film produced using the photo-curable composition described above. For example, the optical device may be a backlight unit that generates light in a liquid crystal display device.

1, the optical device 100 includes a light source 110, a light guide plate 120, a reflection plate 130, a diffusion sheet 140, a first prism sheet 150a, a second prism sheet 150b, Sheet 160 as shown in FIG.

The light source 110 first emits light and the light source 110 may be a light emitting diode (LED), a cold cathode fluorescent lamp (CCFL), or the like.

The light guide plate 120 guides the light generated by the light source 110 in a specific direction and emits the light. More specifically, when the light incident on the light guide plate 120 travels while causing total reflection on the exit surface or the reflection surface of the light guide plate 120 and enters the exit surface or the reflection surface at an incident angle smaller than the critical angle, .

The reflection plate 130 is disposed below the reflection plane of the light guide plate 120 and reflects the light emitted from the reflection plane. The light reflected by the reflection plate 130 is incident again on the light guide plate 120.

The diffusion sheet 140 can diffuse the light emitted through the exit surface of the light guide plate 120 to make the brightness uniform and widen the viewing angle.

The first and second prism sheets 150a and 150b refract the light diffused by the diffusion sheet 140 and condense the light to vertically enter the liquid crystal display panel (not shown), thereby increasing the brightness in the front direction It plays a role. A prism pattern having a triangular prism-shaped pattern extending in the X-axis direction may be formed on the first prism sheet 150a. On the upper portion of the second prism sheet 150b, a Y- A prism pattern having a pattern in the form of a triangular prism extending in the direction of the prism is formed. First and second prism sheets 150a and 150b are made of the photocurable composition according to the present invention described above.

The photocurable composition may contain 3 to 85% by weight of the acrylate compound represented by Formula 1, 5 to 82% by weight of the acrylic monomer, and 0.5 to 15% by weight of the photoinitiator. Alternatively, when the photo-curable composition further contains other additives, the photoacid generator may contain 3 to 80% by weight of the acrylate-based compound represented by Formula 1, 5 to 82% by weight of the acrylic monomer, 0.5 to 10% And 0.2 to 5% by weight of an additive.

Hereinafter, the first prism sheet 150a will be described, but the second prism sheet 150b is also substantially the same.

The first prism sheet 150a includes a base film and a prism pattern, which are located on top of the base film and have a triangular prism shape. Both the base film and the prism pattern are formed of the photo-curable composition described above, or the base film is formed of a transparent material that transmits light, and a prism pattern formed thereon may be formed of the photo-curable composition described above. At this time, the base film may be a polyethylene terephthalate (PET) film. The first prism sheet 150a itself or a prism pattern included therein may be formed by injecting a photocurable composition into a mold having a prism shape and pressing the mold. In the pressing process, the photocurable composition can be photocured.

Alternatively, the prism pattern may be formed by applying the photocurable composition on a base substrate to a desired thickness, for example, a thickness of 0.5 to 100 탆, using a spin, slit coat method, roll coating method, screen printing method, applicator method, , And then curing by irradiation with light. At this time, the light amount may be 100 to 2000 mJ. As the light source used for exposure, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, an argon gas laser, or the like can be used. In some cases, X-rays and electron beams can also be used. The first and second prism sheets 150a and 150b including the prism pattern thus manufactured have high refractive index and excellent transparency.

The protective sheet 160 is located above the second prism sheet 150b and can prevent scratches or the like from being generated in the second prism sheet 150b. The protective sheet 160 may be omitted in some cases.

According to the above description, the first and second prism sheets 150a and 150b are manufactured using the photocurable composition containing the acrylate compound represented by Formula 1 according to the present invention, Can be implemented. By combining such an optical device with a display device such as a liquid crystal display device, there is an advantage that display quality of an image displayed by the display device can be improved.

Hereinafter, the present invention will be described with reference to specific examples and comparative examples.

Example 1: Preparation of Compound 1

100 g of dibenzofuran (Alfa aesar), 35 g of p-Formaldehyde (manufactured by Daeshin Kim), 300 g of acetic acid (manufactured by Daeshin Fine Chemical Co., Ltd.), 30 g of Hydrochloric acid (36% ), 120 g of sulfonic acid was added dropwise at room temperature for 30 minutes, and then the mixture was heated to 70 ° C. and stirred for 6 hours. After the reaction was completed, 300 mL of toluene (toluene, manufactured by DaeHwa Kim) was added to the reaction mixture, the lower layer was removed, 300 mL of water was added again, and the mixture was stirred for 10 minutes and then the lower layer was removed.

52 g of 2-mercaptoethanol was added to the toluene solution thus obtained, and the mixture was stirred at 80 ° C for 4 hours. After cooling to room temperature, 300 mL of water was added, and the mixture was stirred for 10 minutes to remove the lower layer. To the toluene solution, 70 g of triethylamine (manufactured by Daehwa Kagaku) was added, and after cooling to 5 ° C, 60 g of acryloyl chloride (Aldrich) was added dropwise for 30 minutes, and the temperature was raised to room temperature. Lt; / RTI >

The resulting salt was removed by filtration, and the filtrate was stirred with 300 mL of water for 10 minutes, and then the lower layer was removed. The toluene layer was distilled under reduced pressure to remove the solvent, and the residue was separated into a silica column to prepare Compound 1. Compound 1 thus prepared was identified by the analytical instrument having the structure of Formula 2 above.

Example 2: Preparation of compound 2

Compound 2 according to Example 2 of the present invention was prepared in substantially the same manner as in the preparation of Compound 1 except that 92 g of biphenyl was used instead of dibenzofuran. Compound 2 thus prepared was identified by the analytical instrument having the structure of Formula 3 above.

Comparative Example 1: Preparation of Comparative Compound 1

100 g of dibenzofuran (Alfa aesar), 35 g of p-Formaldehyde (manufactured by Daeshin Kim), 300 g of acetic acid (manufactured by Daeshin Fine Chemical Co., Ltd.), 30 g of Hydrochloric acid (36% ), 120 g of sulfonic acid was added dropwise at room temperature for 30 minutes, and then the mixture was heated to 70 ° C. and stirred for 6 hours. After the reaction was completed, 300 mL of toluene (manufactured by DaeHwa Kim) was added to the reaction mixture, and then 300 mL of water was added to the reaction mixture. To the obtained toluene solution, 110 g of sodium acrylate (Aldrich) was added, and the mixture was stirred at 100 ° C. for 8 hours, cooled to room temperature, and the resulting salt was removed by filtration. The filtrate was stirred with 300 mL of water for 10 minutes, . The toluene layer was distilled under reduced pressure to remove the solvent, and the residue was separated into a silica column to prepare Comparative Compound 1. The comparative compound 1 thus prepared was confirmed to have a structure represented by the following formula (5) through analytical instruments.

[Chemical Formula 5]

Comparative Example 2: Preparation of Comparative Compound 2

Comparative Compound 2 was prepared in substantially the same manner as in the preparation of Comparative Compound 1 except that 92 g of biphenyl was used instead of dibenzofuran. The comparative compound 2 thus prepared was confirmed to have a structure represented by the following formula (6) through an analytical instrument.

[Chemical Formula 6]

Characteristic evaluation: liquid refractive index measurement

The refractive indexes of the compounds 1 and 2 and Comparative Compounds 1 and 2 according to the present invention thus prepared were measured at 25 ° C using an Abbe refractive index meter (trade name: NAR-1T) manufactured by ATAGO. The results are shown in Table 1 below.

division Refractive index Compound 1 1.608 Compound 2 1.602 Comparative compound 1 1.615 Comparative compound 2 1.608

Referring to Table 1, it can be seen that each of Compound 1 according to Example 1 of the present invention and Compound 2 according to Example 2 has a value substantially similar to the liquid refractive index of Comparative Compound 1 or 2. That is, even if the compound has the structure of the compound 1 or the compound 2 according to the present invention, it can be confirmed that the refractive index can be at least 1.6 or more without lowering the refractive index.

Preparation of photocurable composition and preparation of optical film

Photocurable compositions according to the following Table 2 were prepared.

Photocurable
Composition 1 Photocurable
Composition 2 Comparative Composition 1 Comparative Composition 2 Monomer 2
compound
82 g (3)
compound
82 g 4
compound
82 g 5
compound
82 g 1,10-Decanediacrylate (Aldrich) 10 g 10 g 10 g 10 g 1,1,1-Trimethylolpropane Triacrylate (Aldrich) 4.5 g 4.5 g 4.5 g 4.5 g Megaface F-444 0.5 0.5 0.5 0.5 Darocur TPO (BASF) 3 g 3 g 3 g 3 g

Each of the photocurable composition and the comparative composition was slit coated on PET (SKC) to a thickness of 100 μm, and then light cured by irradiation with light using a 150 W metal halide lamp for 10 minutes. Thus, Film Samples 1 and 2 and Comparative Samples 1 and 2 were obtained.

Characteristic evaluation: luminance and resilience

Using the thus prepared film samples 1 and 2 and comparative samples 1 and 2, the luminance was measured using an LED as a white light source. The luminance was measured using a CS-2000 manufactured by Konicaminolta.

In order to confirm the restoring force, a prism pattern was prepared by using the photocurable composition and the comparative composition shown in Table 2 as shown in FIG. 2. Then, the weights of the restored patterns were compared by raising and pulling the weights thereon. The beads were dropped on the patterned prism sheet to compare the restored heights. The prism patterns 1 and 2 were prepared from the photocurable compositions 1 and 2, respectively, and the comparative patterns 1 and 2 were prepared from the comparative compositions 1 and 2, respectively.

The results are shown in Table 3.

White LED Prism pattern 1 Prism pattern 2 Comparison pattern 1 Comparison pattern 2 Luminance
(cd / m ² ) 60 207 195 212 204 The pattern is restored
Weight of weight (g) - 300 350 100 150 The height at which the pattern is restored by dropping the iron ball (cm) - 15 18 4 8

Referring to Table 3, in the case of having the prism patterns 1 or 2, the difference in luminance is not largely different from the case of including the comparison pattern 1 or 2, but the weight of the weight to be restored as the factor for evaluating the restoring force It can be seen that there is a remarkably large difference in the height to be restored. That is, the weight of the restored weight for the prism patterns 1 or 2 is remarkably heavy compared to the comparative patterns 1 and 2, the height restored by using the 36 g iron ball, and the prism pattern 1 or 2 is the comparative pattern 1 2 < / RTI >

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the present invention as defined by the following claims. It can be understood that it is possible.

100: Optical device
150a, 150b: first and second prism sheets

Claims (7)

An acrylate-based compound represented by the following formula (1);
[Chemical Formula 1]

In Formula 1,
x represents a natural number of 1 to 6,
y represents a natural number of 1 to 6,
R represents a hydrogen atom or a methyl group,
Ar represents any one of the following formulas (1-b) to (1-d)
[Chemical Formula 1-b]

[Chemical Formula 1-c] [Chemical Formula 1-d]

Z in the formulas (1-b) and (1-c) represents NH, S, O or Se,
At least one of the hydrogen atoms of Ar may be substituted with an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms.
The method according to claim 1,
The acrylate-based compound
An acrylate-based compound represented by the following formula (2);
(2)

The method according to claim 1,
Wherein the liquid-phase refractive index is 1.5 to 1.8.
An acrylate-based compound according to any one of claims 1 to 3;
Acrylic monomers; And
A photocurable composition comprising a photoinitiator.
5. The method of claim 4,
And 3 to 85% by weight of the acrylate compound,
And 5 to 82% by weight of the acrylic monomer,
And 0.5 to 15% by weight of the photoinitiator.
Photocurable composition.
An optical film produced by curing the photocurable composition of claim 4.
The method according to claim 6,
Wherein the optical film is a prism sheet including a prism pattern.

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