TW200906869A - Active energy ray curable composition and optical material - Google Patents

Abstract

The present invention provides an active energy ray curable composition excellent in operability and an optical material obtained by using the composition. A cured product obtained therefrom has a high refractive index and a high light transmittance and is excellent in heat resistance. The active energy ray curable composition of the present invention is characterized in that it comprises an di(meta)acrylate (A) represented by the following general formula (1) and an ethylenically unsaturated compound (B) other than component (A), wherein R1 and R3 independently of each other represent a hydrogen atom or a methyl group, R2 and R4 independently of each other represent an alkylene group, R5 represents a hydrogen atom and a methyl group, R6 represents a hydrogen atom, a halogen atom or a methyl group, R7 and R8 independently of each other represent a halogen atom or a methyl group, m1 and m2 independently of each other represent an integer of 0 to 4, and m3 and m4 independently of each other represent an integer of 0 to 2.

Description

200906869 IX. Description of the Invention: [Technical Field of the Invention] The present invention relates to an active energy ray-curable composition and an optical material. [Prior Art] Conventionally, a lens sheet such as a Fresnel lens or a lenticular lens is produced by a method such as a press method or a casting method. However, since the pressurization method of the former is manufactured by circulation of heating, pressurization, and cooling, there is a problem that productivity is poor. Further, the latter casting method is because the monomer is allowed to flow into the mold to be polymerized, so that the production time is long and many molds are required, which increases the manufacturing cost. On the other hand, the active energy ray-curable composition has excellent rapid productivity and is excellent in productivity. Therefore, in order to solve the above problems, a Fresnel lens for projection television or a lens sheet for a liquid crystal display is used for manufacturing a lens sheet. There are various proposals for the active energy ray-curable composition (for example, Patent Documents 1 to 6). However, the conventional active energy ray-curable composition is insufficient in terms of refractive index and transparency. In order to improve this point, there is a review of bisphenol-type di(meth)acrylate and a single ring having an aromatic ring. A composition of (meth) acrylate (for example, Patent Documents 7 and 8). [Patent Document 1] Japanese Laid-Open Patent Publication No. JP-A No. Hei 6 No. Hei. [Patent Document 5] Japanese Laid-Open Patent Publication No. JP-A-63-136-A Japanese Laid-Open Patent Publication No. Hei 9-8 73 No. 3 (Patent Document 8) Japanese Patent No. 3 3 9744 8 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION However, the active energy ray-curable composition, It is insufficient for applications such as projection televisions where thinning is required and high refractive index and transparency are required. Further, the (meth) acrylate used for optical use is often high in viscosity and crystallized at room temperature, and has troublesome handling properties. Further, it is insufficient in applications requiring heat resistance such as a vehicle display device for a car navigation system. The present inventors have found that the obtained cured product is excellent in workability at room temperature, and the obtained cured product is an active energy ray-curable composition having a high refractive index and a high light transmittance and excellent heat resistance. Review. In order to solve the above problems, the inventors of the present invention conducted various reviews and found that a composition containing two specific (meth) acrylates is rapidly hardened by active energy rays, and the cured product is hardened. The present invention has been completed by having a high refractive index, excellent light transmittance, and excellent heat resistance. That is, the above problem is solved by the following paragraphs described in <1 > &<9>. The preferred embodiments of <2>~<8> and <10> are described below. <1> An active energy ray-curable composition comprising: a di(meth)acrylate (A) represented by the following formula (1); and a non-component (A): 200906869 ethylenic unsaturation Compound (B),

[In the formula (1), R1 and R3 each independently represent a hydrogen atom or a methyl group, R2 and R4 each independently represent an alkylene group, R5 represents a hydrogen atom or a methyl group, and R6 represents a hydrogen atom, a dentate atom or a methyl group. R7 and R8 each independently represent a halogen atom or a methyl group, and ^^ and m2 each independently represent an integer of 〇~4, and m3 and m4 each independently represent an integer of 0 to 2]. The active energy ray-curable composition according to the above-mentioned item (1), which contains 10 to 90% by weight (A) based on the total amount of the component (A) and the component (B). And the active energy ray-curable composition according to the above-mentioned <1>, wherein the component (A) is the above-mentioned (A) component. R5 in the formula (1) is a methyl group, R6 is a hydrogen atom, and m3 and m4 are a di(meth)acrylate of oxime '4&gt; as in any of the above &lt;1&gt; to the above &lt;3&gt; The active energy ray-curable composition according to the above aspect, wherein the component (A) is a diacrylate in which both R1 and R3 are a hydrogen atom in the formula (1) '&lt;5&gt; as described above &lt;1&gt; to the above &lt;4&gt; An active energy ray-curable composition according to any one of the above, wherein the component (B) is a compound H2C represented by the following formula (2)

R 11 (2) 200906869 [In the formula (2), R9 represents a hydrogen atom or a methyl group, Ri 〇 represents an alkylene group, Rii represents a phenyl group or an alkyl group having a phenyl group having 10 or less carbon atoms, and η represents 〇 〜 4 Integer]. The active energy ray-curable composition according to the above-mentioned <5>, wherein the (Β) component is a compound of η = 0 in the above formula (2), and <7> is as described above &lt;1&gt; The active energy ray-curable composition according to any one of the above-mentioned items, wherein the photopolymerization initiator (C) is further contained, and &lt;8&gt; An active energy ray-curable composition, wherein the cured product obtained from the composition has a refractive index at 150 ° C of 1.56 or more and 1.62 or less, &lt;9&gt; an optical material The composition according to any one of the above <1> to <8> is cured. &lt;1〇&gt; The optical material described in the above <9> is a lens sheet. Advantageous Effects of Invention The composition of the present invention is excellent in workability at room temperature, and the obtained cured product is high in refractive index, and also has excellent light transmittance and excellent heat resistance. [Embodiment] The best shape Kumamoto for carrying out the invention The present invention relates to an active energy ray-curable composition (hereinafter also referred to as "the composition of the present invention"), which contains a di(meth)acrylate (A) represented by the following formula (1) (hereinafter referred to as (A) (Component) and the ethylenically unsaturated compound (B) other than (A) (hereinafter also referred to as (B) component). Further, in the present specification, acrylate or methacrylate is represented by (200906869 methyl) acrylate. Each component will be described below. 1. (A) component

The component (A) is a di(meth)acrylate represented by the following formula (1).

(1) [In the formula (1), R1 and R3 each independently represent a hydrogen atom or a methyl group, R2 and R4 each independently represent an alkylene group, R5 represents a hydrogen atom or a methyl group, and R6 represents a hydrogen atom, a halogen atom or The methyl group, R7 and R8 each independently represent a halogen atom or a methyl group, and (1) and ^ each independently represent an integer of 0 to 4, and m3 and m4 each independently represent an integer of 〇2 to 2]. R1 and R3 are preferably each a hydrogen atom because the composition is excellent in systemic hardenability.

f乍 is an alkylene group of R2 and R4, preferably a lower alkylene group S' having a carbon number of 1 to 6 is more preferably a lower alkylene group having a carbon number of 1 to 4, specifically, a sub-group @' ί Ethyl, propyl and butyl groups. Among these, it is preferred that /|4-» -t r _ S Θ be easily obtained as a raw material, and the obtained cured product has excellent refractive index. R θ 圭 is a methyl group because a low-colored cured product can be obtained. When m3 and/or 1X14 is 2, a plurality of R7 and/or R8 present may be the same or different. The halogen atom in R6 to R8 may, for example, be a fluorine atom, a chlorine atom or a -10-200906869 bromine atom or an iodine atom. More preferably, it is a bromine atom. R6, m3, and m4 are those in which the composition is excellent in curability, and a compound in which R6 is a hydrogen atom and m3 and m4 are 0 is preferable. The m> and m2' are preferably 0 to 3 because the obtained cured product has excellent refractive index. The component (A) is more preferably a di(meth)acrylate in which R5 in the formula (1) is a methyl group, R6 is a hydrogen atom, and m3 and m4 are 0, since the composition is excellent in hardenability, and the cured product is Low coloring. Specific examples of the component (A) include bis(4-propenyloxyphenyl)phenylmethane, bis(4-methylpropenyloxyphenyl)phenylmethane, and bis(4-propenefluorene). Oxyethoxyphenyl)phenylmethane, bis(4-methylpropenyloxyethoxyphenyl)phenylmethane, bis(4-propenyloxydiethoxyphenyl)phenylmethane , bis(4-methylpropenyloxydiethoxyphenyl)phenylmethane, bis(4-propenyloxytriethoxyphenyl)phenylmethane, bis(4-methylpropene oxime) Triethoxyphenyl)phenylmethane, bis(4-propenyloxyphenyl)methylphenylmethane, bis(4-methylpropenyloxyphenyl)methylphenylmethane, bis ( 4-propenyloxyethoxyphenyl)methylphenylmethane, bis(4-methacryloxyethoxyphenyl)methylphenylmethane, bis(4-propenyloxydiethyl) Oxyphenyl)methylphenylmethane, bis(4-methylpropenyloxydiethoxyphenyl)methylphenylmethane, bis(4-propenyloxytriethoxyphenyl)methyl Phenylphenylmethane and bis(4-methacryloxyloxytriethoxy) Phenyl)methylphenylmethane, etc. Among these, eutectic is excellent, and bis(4-propenyloxyethoxyphenyl)methylphenylmethane is more preferable. 200906869 (A) One type can be used, or two or more types can be used. 2 . f B ) Component (B) The component is an ethylenically unsaturated compound other than the component (A). In addition, the ethylenically unsaturated compound is a compound which has one or more ethylenically unsaturated groups, and the (B) component is a compound which has one ethylenic unsaturated group ( A saturated compound ") and a compound of two or more ethylenically unsaturated groups (hereinafter referred to as "polyfunctional unsaturated compound"). In general, the purpose of blending the monofunctional unsaturated compound is to treat the composition into a liquid or to reduce the viscosity, to improve the coating property, etc., and the purpose of blending the polyfunctional unsaturated compound is to improve the hardness of the cured product of the composition, etc. As the component (B), various ethylenically unsaturated compounds of compounds other than (A) can be used. Specific examples of the component (B) include monoethylenically unsaturated compounds, and examples thereof include phenoxyethyl (meth)acrylate, carbitol (meth)acrylate, and N-vinylcaprolactone. , propylene decylmorpholine, glycidyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 1,4-butanediol mono(methyl) Acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, tribromophenyl (meth)acrylate, and tribromophenoxyethyl (meth)acrylate. Examples of the polyfunctional unsaturated compound include 1,6-hexanediol di(meth)acrylate, decanediol diacrylate, polyethylene glycol di(meth)acrylate, and 2,2-bis ( 4-(Methyl)acryloxyethoxyethoxyphenyl)-propane, 2,2-bis(4-(methyl)propenyloxydiethoxyphenyl)-propane, 2,2-double (4-(methyl) 200906869 propylene decyloxytriethoxyphenyl)-propane, ethylene glycol di(meth) acrylate, trimethylolpropane tri(meth) acrylate, pentaerythritol tetra (a) Base) bis(meth) acrylate of acrylate, bisphenol A type epoxy resin, various polyurethane poly(meth) acrylates, polyester poly(meth) acrylate, etc. A compound having an aromatic group and having one (meth)acryl fluorenyl group (hereinafter referred to as "aromatic monofunctional (meth) acrylate") has a high refractive index due to a cured product which can impart a composition. Further, since the composition can be made into a liquid which can be easily handled, it is preferable. The aromatic monofunctional (meth) acrylate may, for example, be benzyl (meth) acrylate, phenoxyethyl (meth) acrylate or a (meth) acrylate represented by the following formula (2). The aromatic monofunctional (meth) acrylate is more preferably a (meth) acrylate represented by the formula (2) in order to make the cured product of the composition a higher refractive index.

In the formula (2), R9 represents a hydrogen atom or a methyl group, R1Q represents an alkylene group, R11 represents a phenyl group or an alkyl group having a phenyl group having 10 or less carbon atoms, and η represents an integer of 0 to 4]. The alkylene group of R1() is preferably a lower alkylene group having 1 to 6 carbon atoms, more preferably a lower alkylene group having 1 to 4 carbon atoms, and specific examples thereof include a methylene group and an ethyl group. Propyl and butyl groups. Among these, it is preferred that Ethylethyl-13-200906869' is excellent in the refractive index of the obtained cured product because the raw material is easily obtained. Examples of the alkyl group having a phenyl group having a carbon number of 1 Torr or less in R11 include a benzyl group and a p-cumylphenyl group.具体. Specific examples of the (meth) acrylate represented by the formula (2) include, for example, a phenylphenol (meth) acrylate or an ethylene oxide adduct of a phenylphenol (meth). Acrylate, propylene oxide adduct of phenylphenol, (meth) acrylate, 4-α-cumyl phenyl acrylate, 4-α-cumylphenol ethylene oxide adduct (meth) acrylate such as acrylate and 4-α-cumylphenol epoxy propylene adduct. The (Β) component is more preferably a compound of the above formula (2) wherein R11 is a phenyl group, that is, a (meth) acrylate having a biphenyl group. The (meth) acrylate having a biphenyl group has a neighboring body, an intermediate body, and a counter body. However, from the viewpoint of easy handling at room temperature and easy availability, it is preferably a neighbor. The (Β) component is preferably a compound represented by the following formula (3).

In the formula (3), R9, the ruler 1 () and the η system are synonymous with the above formula (2). Specific examples of the compound represented by the above formula (3) include o-phenylphenyl (meth)acrylate and (meth)acrylate of an ethylene oxide adduct of o-phenylphenol. Further, among these, phenyl (meth)acrylate phthalate-14-200906869 phenyl ester having η = 0 is particularly preferable because the viscosity of the composition can be lowered and the obtained hardening is high refractive index. (B) The component may be used alone or in combination of two or more. Component of the present invention The composition of the present invention is cured by irradiation with an active energy ray. Examples of the active energy ray in this case include electron beams and visible light ultraviolet rays. Among these, it is preferably visible light or ultraviolet light, and does not require a special device and is simple. When it is a visible light ray or ultraviolet curable composition, a photopolymerization initiator is blended in the group. Further, when it is an electron beam hardening type group, it is not necessary to blend a photopolymerization initiator. Specific examples of the photopolymerization initiator (hereinafter referred to as component (c)) include benzoin acetophenone, 2,2-di, such as benzoin, benzoin methyl ether, and benzoin propyl ether. Methoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 1,1-dichloroacetophenone, hydroxycyclohexyl phenyl ketone, yl-methylthio)phenyl _2_morpholinyl-propane-ketone and N,N_: acetophenones such as aminoacetophenone; anthraquinones such as 2-methylhydrazine, hydrazine-chlorinated hydrazine and hydrazine; , 4_dimethylthioxanthone, 2,4-diethylthio, 2-chlorothioxanthone, and thioxanthone such as 2,4-diisopropylthioxanthone; And ketals such as benzyl dimethyl ketal; dibenzoyl benzophenone, 4,4,-dichlorobenzophenone, 4,4, bisdiethylamine ketone, Michlerone and 4-benzylidenyl-4,-methyldiphenyl sulfide benzophenone; and 2,4,6-trimethylbenzimidyldiphenylphosphine oxide. The composition of the product, the line and the product of the product can be classified as follows; -2-benzene 2-methylmethyl 2-pentanone acetophenone, the base compound -15- 200906869 (C) ingredients can be used alone, It is also possible to use two or more types. In the component (C), a photosensitizer may be used as needed. Examples of the photosensitizer include ethyl N,N-dimethylaminobenzoate, hydrazine, isoamyl dimethylamino benzoate, triethylamine and triethanolamine. The preferred blending ratio of the component (C) is preferably 〇·〇 5 to 12 parts by weight, more preferably 〇.1, for a total of 1 part by weight of the (Α) component and the (Β) component. ~ 5 parts by weight. In addition to the above components, pigments, dyes, antifoaming agents, leveling agents, inorganic materials, organic materials, and the like may be blended as needed. Further, an antioxidant, a light stabilizer, an ultraviolet absorber, a polymerization inhibitor, or the like may be added in a small amount as needed. The composition of the present invention may be further cured, and may be heated after irradiation with an active energy ray by a composition of a grazing/ Φ ii thermal polymerization initiator. As the thermal polymerization initiator, various compounds can be used, and an organic peroxide and an azo initiator are preferred. Specific examples of the organic peroxide include 1, bis-bis(t-butylperoxy) 2-methylcyclohexane, hydrazine, and bis (trihexylperoxy)_3,3,5_ Trimethylcyclohexan, 1,1-bis(trihexylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane 1,1-bis(t-butylperoxy)cyclohexane, 2,2-bis(4,4-dibutylperoxycyclohexyl)propane, 1,1-bis (t-butylperoxy) Cyclododecane, third hexylperoxyisopropylmonocarbonate, tert-butylperoxymaleic acid, tert-butylperoxy-3,5,5-trimethylhexanoate, third Butyl peroxylaurate, 2,5-dimethyl-2,5-di(m-tolylperoxy)hexane, tert-butylperoxyisopropyl monocarbonate, tert-butyl Oxygen 2-ethylhex-16- 200906869 monomonocarbonate, third hexylperoxybenzoate, 2,5-di-methyl-2,5-bis(benzhydrylperoxy)hexane, Tert-butyl peroxyacetate, 2,2-bis(t-butylperoxy)butane, tert-butylperoxybenzoate, n-butyl-4,4-bis(t-butyl Peroxy) valerate, di-tert-butyl Oxalisophthalate, α,α'-bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2'5_methyl-2,5-di(t-butyl Peroxy)hexane, tert-butyl cumyl peroxide 'di-tert-butyl peroxide, methane hydroperoxide, 2,5-dimethyl-2,5-di (third Base peroxy)hexyne-3, diisopropylbenzene hydroperoxide f ' &quot; , tert-butyltrimethyldecyl peroxide, 1,1,3,3-tetramethylbutyl hydrogen Peroxide, suspicion of hydroperoxide, third hexyl hydroperoxide and second butyl hydroperoxide. Specific examples of the azo compound include 1,1'-azobis(cyclohexane-b-carbonitrile), 2-(aminomercaptoazo)isobutyronitrile, and 2-phenylazo- The oxime of 4-methoxy-2,4-dimethylvaleronitrile, azodioctane octane, and azobisbutane may be used singly or in combination of two or more. Further, the organic peroxide can be subjected to a redox reaction by being combined with a reducing agent. 4. Composition for active energy ray-curable optical material The present invention is indispensable for the components (A) and (B) described above. The ratio of the component (A) to the component (B) is preferably from 1 to 9% by weight based on the total amount of the component (A) and the component (B), and the component is from 9 to 10 The % by weight is more preferably 4% to 9% by weight of the component (A) and 60 to 10% by weight of the component (B). When the ratio of the component (A) is 1% by weight or more, the desired refractive index of 200906869 is preferable. On the other hand, the ratio of the component (A) is 90% by weight or less. It is preferable to make the composition solid at room temperature and to be excellent in workability. In the case of the composition of the present invention, the total amount of the component (A) and the component (B) is preferably from 40 to 99% by weight, more preferably from 60 to 99% by weight, based on the total amount of the composition. Good for 8〇~999% by weight. When used in optical applications, it is preferably from 80 to 99.9% by weight. The composition of the present invention can be produced by stirring and mixing the above components (A) and (B) with other components as needed according to a usual method. When the component (A) or the component (B) is a solid, the heating may be carried out after stirring and mixing, and the heating temperature is preferably 50 to 1 0 t. The composition of the present invention is hardened by irradiation with an active energy ray. Here, as the active energy ray, an electron beam, a visible ray, an ultraviolet ray, or the like can be given. Among these, it is preferably visible light or ultraviolet light because a special device is not required and is simple. As the ultraviolet irradiation device, a high pressure mercury lamp or the like can be given. The irradiation amount of the active energy ray, the irradiation time, and the like can be appropriately set depending on the composition and use to be used. The composition of the present invention is preferably cured by ultraviolet rays from the viewpoint of convenience and low cost. In the ultraviolet irradiation, an ultrahigh pressure mercury lamp, a high pressure mercury lamp, a low pressure mercury lamp, a metal halide lamp, a carbon arc, a xenon lamp, or the like which is generally used in the curing of the ultraviolet curable composition can be used. Preferably, a high-pressure mercury lamp or a metal halide lamp having a wavelength of 3 65 nm as a center is used. When the irradiation amount of ultraviolet rays is 200 mJ/cm 2 or more, 200906869 is more suitable for curing, and more preferably 300 to 2,000 mJ/cm 2 . The refractive index (25 ton) of the cured product obtained by the hardening of the composition of the present invention is preferably 1.5 or more and more preferably 丨.6 〇 or more. Further, the upper limit of the refractive index (25 t ) is not particularly limited, but is preferably i · 62 or less. According to the active-strand hardening type composition of the present invention, a cured product having a high refractive index can be obtained. Further, the cured product is also excellent in transparency. The light transmittance of the 5 5 Onm of the cured product is preferably 8 〇 % or more, more preferably 8 5 % or more, and particularly preferably 90% or more. Further, the upper limit of the light transmittance is not particularly limited, but is preferably 100% or less. Thus, the cured product of the composition of the present invention is suitable for optical materials because of its high refractive index and transparency. That is, the composition of the present invention can be applied to an active energy ray-curable resin composition for an optical material. The composition of the present invention can be used for the production of various optical materials such as a Fresnel lens, a lens for a lenticular lens and a prism sheet, and a plastic lens, and the like, and can be used for a coating agent, an adhesive, a lens itself, and the like. More specifically, the lens sheet ′ can be used for a video projector, a projection television, and a liquid crystal display. The active energy ray-curable composition of the present invention is particularly preferably a coating agent or a lens sheet which can be used as such an optical material. Further, the method for producing an optical material of the present invention comprises the steps of applying or injecting the composition of the present invention, and subjecting the composition to irradiation with an active energy ray to cure. As a method of using the composition of the present invention, a usual method can be followed. Specifically, the composition -19-200906869 can be applied to a plastic film substrate by using a coating bar or the like, and the active energy ray is irradiated to be hardened. When a plurality of plastic substrates are bonded to each other and laminated, a film or a sheet substrate may be laminated on the applied composition, and then irradiated with an active energy ray to be irradiated. An example of manufacturing a lens sheet using the composition of the present invention will be described. In the case of producing a lens sheet having a relatively small film thickness, the composition of the present invention is applied onto a mold called a die having a desired lens shape, and a layer of the composition is provided, and a transparent substrate is adhered to the layer. Next, the active energy ray is irradiated from the side of the transparent substrate to harden the composition, and then peeled off from the mold. On the other hand, when a lens sheet having a relatively large film thickness is produced, a composition of the present invention is poured (injected) between a mold having a desired lens shape and a transparent substrate. Next, the active energy ray is irradiated from the side of the transparent substrate to harden the composition, and then the mold is released from the mold. The transparent substrate is preferably a resin substrate, and specific examples thereof include a sheet of a methacrylic resin, a polycarbonate resin, a methyl methacrylate-styrene resin, and a styrene resin. The material of the mold is not particularly limited, and examples thereof include metals such as brass and nickel, and resins such as epoxy resins. From the viewpoint of a long life of the mold, it is preferably made of metal. Next, an example in which a plastic lens is produced by using the composition of the present invention will be described. For example, a composition in which the composition of the present invention is injected into a mirror-honed mold having at least one surface and transparent is irradiated with an active energy ray to be cured. The method of modeling and so on. Examples of the mold in this case include glass, plastic -20-200906869, or two mirror-honed dies which are combined, and plasticized vinyl chloride and ethylene-vinyl acetate copolymer. A gasket made of a thermoplastic resin, a combination of two molds and a lock mold, and the like. The irradiation of the active energy ray in this case can be carried out on one or both sides of the mold. Further, irradiation and heating of the active energy ray may be combined. EXAMPLES Hereinafter, the present invention will be more specifically described by way of examples and comparative examples. In the following, "parts" means parts by weight. 〇Examples and Comparative Examples The components shown in Table 1 were stirred and mixed according to a usual method, and in a dryer maintained at 80 ° C in advance, it was heated for 15 minutes to dissolve the solid photopolymerization initiator to prepare ultraviolet rays. Hardened composition. The obtained composition was applied to the tantalum film at a film thickness of 3 Ο μη at room temperature using a bar coater. The high-pressure mercury lamp having a conveyor belt speed of 10 m/min, a lamp height of 10 cm, and an output of 80 W/cm was subjected to ultraviolet irradiation twice to harden. The obtained hardened material was evaluated in accordance with the following method. Their results are shown in Table 1. (1) Workability When manufacturing a cured product, the ease of handling of the composition was evaluated. Think of a liquid at room temperature as a cockroach and a solid or paste as X. (2) Refractive index The refractive index (25 ° C) of the cured product of the sodium D line was measured by an Abe refractometer DR-M2 manufactured by AT AGO. (3) Light transmittance -21- 200906869 The light transmittance of the cured product at 550 nm was measured by V-55 0 manufactured by JASCO Corporation. (4) Heat resistance The dynamic viscoelasticity of the cured product was measured under the following conditions using DMS 6100 manufactured by Seiko Instruments Co., Ltd., and the obtained tanSmax was evaluated as the glass transition temperature. • Frequency 10 Hz, temperature rise rate 2 ° C / min, measurement temperature range -50 to 250 ° C. [Table 1] Composition (parts) Evaluation result (Α) (Β) (C) Operational refractive index light transmission and heat resistance ΡΕΒΗΡ 〇-ΡΡΑ ΤΟ-1463 Μ-211Β ΡΟΑ THFA Irgl84 Pass rate CC) Example 1 85 One — — — 15 5 〇 1.5902 93 134 Same as 2 20 80 — One — — 5 〇 1.6122 94 90 Same as 3 50 50 — — — — 5 〇1.6134 95 108 Same as 4 50 — 50 — — — 5 〇1.6072 95 91 Same as 5 50 — — 50 — 5 〇 1.5677 92 84 Comparative Example 1 100 — — — — — 5 X — — — 2 — Same as 2 — — 50 50 — — 5 〇1.5791 94 60 Same as 3 — 1 85 — 15 5 〇 1.5551 95 73 Furthermore, the abbreviations in Table 1 mean the following. • PEB HP: bis(4_acryloxyethoxyphenyl)methylphenylmethane [In the formula (1), 'R1, r3, R5 and R6 are hydrogen atoms, and R2 and R4 are exoethyl' mi And a compound wherein 1 is 1, and m3 and rn4 are 0] • o_PPA: o-phenylphenyl decenoate [in the formula (3), R9 is a hydrogen atom, and Rio is a compound having an ethyl group and η is 0] - 22 - 200906869 • TO- 1 463 : 1 modified acrylate of moor o-phenylphenol ethylene oxide, Aronix ΤΟ-1 463 manufactured by East Asian Synthetic Co., Ltd. [In the formula (3), R9 is a hydrogen atom, R10 a compound which is ethyl and η is 1]

• Μ-2 1 1Β: 4 modified bisphenol oxirane modified diacrylate, Aronix M-211B manufactured by East Asia Synthetic Co., Ltd. • POA: phenoxyethyl acrylate • THFA: tetrahydroanthracene Ester • Irgl84 : 1-hydroxycyclohexyl phenyl ketone, made by Ciba Specialty Chemicals, ·

Irgacure 184 As is apparent from Table 1, the composition of the present invention is excellent in handleability, and the cured product has a refractive index of high refractive index, good light transmittance, and excellent heat resistance. On the other hand, the composition using only the component (A) (Comparative Example 1) had a high viscosity at room temperature, so that workability was poor, and a cured product could not be obtained at room temperature. Further, in the composition containing the component (B) and not containing the component (A) (Comparative Example 2 and Comparative Example 3), the obtained cured product had insufficient refractive index and insufficient heat resistance. 〇Application example (manufacture of lens sheet) Using the composition obtained in the example, flowing into a mold having a lens shape, and then using a PET (polyethylene terephthalate) film as a transparent substrate Cosmoshine 4300, film thickness 50μιη] to hold. From the side of the transparent substrate, an ultraviolet ray having a conveyor belt was used, and a high-pressure mercury lamp was used as a light source, and ultraviolet rays of a UV-A irradiation amount of 800 mJ/cm 2 were irradiated to cure the composition. -23 - 200906869 The cured product after hardening is peeled off from the mold. As a result, the composition of the example is easily peeled off, and a lens sheet having a desired shape can be obtained. Further, in the compositions of Examples 1 to 5, a lens excellent in optical properties such as the above can be obtained. Industrial Applicability The composition of the present invention is applicable to a Fresnel lens and a lenticular lens used in video projectors, projection televisions, liquid crystal displays, and the like as a composition for an active energy ray-curable optical material. An optical member that requires a high refractive index and a high light transmittance, as represented by a lens sheet, a plastic lens, etc. 〇 [Simple description of the drawing] None. [Main component symbol description] None. -twenty four-

Claims (1)

200906869 X. Patent application scope: 1. An active energy ray-curable composition comprising: a di(meth)acrylate (A) represented by the following formula (1), and a component other than the component (A) Ethylene unsaturated compound (B), H2〇Xg. i£〇H2 [In the formula (1), R1 and R3 each independently represent a hydrogen atom or a methyl group, R2 and R4 each independently represent an alkylene group, R5 represents a hydrogen atom or a methyl group, and R6 represents a hydrogen atom, a halogen atom or a methyl group. R7 and R8 each independently represent a halogen atom or a methyl group, and 1^ and m2 each independently represent an integer of 〇~4, and «13 and HU each independently represent an integer of 0 to 2]. 2. The active energy ray-curable composition according to claim 1, wherein the (A) component and the component (B) are contained in an amount of 10 to 90% by weight of (human) component and 9 〇~10% by weight of the component (8). 3. The active energy ray-curable composition according to claim 1, wherein the (A) component is a methyl group in the formula (1), R6 is a hydrogen atom, and m3 and m4 are bismuth ( Methyl) acrylate. 4. The active energy ray-curable composition according to claim 1, wherein the component (A) is a diacrylate wherein R1 and R3 are each a hydrogen atom in the formula (1). 5. The active energy ray-curable composition of claim 1, wherein the component (B) is a compound represented by the following formula (2), In the formula (2), R9 represents a hydrogen atom or a methyl group, R1() represents an alkylene group, R11 represents a phenyl group or an alkyl group having a phenyl group having 10 or less carbon atoms, and η represents an integer of 0 to 4]. 6. The active energy ray-curable composition of claim 5, wherein the (Β) component is a compound of the formula (2) wherein η = 0. 7. The active energy ray-curable composition of claim 1, wherein the photopolymerization initiator (C) is further contained. 8. The active energy ray-curable composition according to claim 1, wherein the cured product obtained from the composition has a refractive index at 1.5 ° C of 1.56 or more and 1.62 or less. An optical material obtained by hardening a composition of any one of claims 1 to 8. 1 〇. The optical material of claim 9 is a lens sheet. -26- 200906869 VII. Designation of the representative representative: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: No. 0. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention.