CN100384895C - Composition for active energy ray-curable optical material - Google Patents

Abstract

This invention provides an actinic-energy-ray-curable composition for optical materials which can give a cured article having a high refractive index, high light transmittance, and low water absorption. The actinic-energy-ray-curable composition for optical materials comprises (A) a di(meth)acrylate represented by the formula(1) and (B) a mono(meth)acrylate represented by the formula (2) and/or mono(meth)acrylate represented by the formula (3). Also provided is a process for producing an optical material which comprises applying or pouring the composition to a casting mold and then irradiating it with actinic energy rays. In formula(1): R1 and R3 each independently represents hydrogen or methyl; R2 and R4 each independently represents hydrogen, methyl, or ethyl; R5 to R8 each independently represents hydrogen, methyl, or bromine; and l and m each independently is an integer of 1 to 6. In formula(2): R9 represents hydrogen or methyl, R10 represents hydrogen or methyl.

Description

Composition for active energy ray-curable optical material

technical field

The present invention relates to a composition for active energy ray-curable optical materials, and belongs to the technical field of active energy ray-curable compositions and optical materials such as lens sheets and plastic lenses.

Background technique

Conventionally, lens sheets such as Fresnel lenses and biconvex lenses have been molded by methods such as molding and casting.

However, the former press molding method has a problem of poor productivity because it is produced in a cycle of heating, pressurizing, and cooling. In addition, in the latter casting method, in order to inject the monomer into the mold to polymerize, it takes a long time to manufacture, and a plurality of molds are required at the same time, so there is a problem of high manufacturing cost.

On the other hand, since active energy ray-curable compositions have fast curing properties and are excellent in productivity, in order to solve the above problems, various proposals have been made for active energy ray-curable compositions for lens sheet production (for example, Patent Document 1 ~6).

However, conventional active energy ray-curable compositions have deficiencies in refractive index and transparency. In order to improve this point, studies have been made of bisphenol-type di(meth)acrylate and aromatic ring-containing mono(methyl) Compositions obtained by using acrylates in combination (for example, Patent Document 7 and Patent Document 8).

Patent Document 1: JP-A-61-177215 (claims)

Patent Document 2: JP-A-61-248707 (claims)

Patent Document 3: JP-A-61-248708 (claims)

Patent Document 4: JP-A-63-163330 (Claim)

Patent Document 5: JP-A-63-167301 (Claim)

Patent Document 6: JP-A-63-199302 (claims)

Patent Document 7: JP-A-9-87336 (Claim)

Patent Document 8: Patent No. 3397448 (Claim)

Contents of the invention

However, among active energy ray-curable compositions used in optical applications, the above-mentioned compositions have shortcomings in applications requiring higher refractive index and transparency, which are required for thinning projection televisions and the like.

In addition, in active energy ray-curable compositions used for optical applications, in addition to these optical properties, dimensional stability of cured products to be obtained is also required. That is, when the water absorption rate of the cured product is high, dimensional changes due to water absorption over a long period of time may cause unevenness in optical properties, and peeling and deformation of members may occur.

The present inventors conducted intensive research to find a composition for an active energy ray-curable optical material that has a high refractive index, high light transmittance, low water absorption, and excellent dimensional stability in the obtained cured product.

The inventors of the present invention conducted various studies to solve the above-mentioned problems. As a result, they found that a composition containing two specific types of (meth)acrylates was cured quickly by active energy rays, and the cured product had a high refractive index and light transmittance. Excellent, thus completing the present invention.

Next, the present invention will be described in detail.

In this specification, acrylate or methacrylate is represented by (meth)acrylate.

The present invention relates to a composition for an active energy ray-curable optical material, which is composed of a di(meth)acrylate (A) represented by the general formula (1) described below and a compound represented by the general formula (2) described below. ) represented by a mono(meth)acrylate or/and a mono(meth)acrylate (B) represented by general formula (3) described later; the total amount of (A) component and (B) component is taken as On a standard basis, the said composition contains 10-90 mass % of (A) components and 90-10 mass % of (B) components.

Next, each component is demonstrated.

1. (A) Ingredients

(A) Component is di(meth)acrylate represented by following general formula (1).

[In formula (1), R ₁ and R ₃ independently represent a hydrogen atom or a methyl group, R ₂ and R ₄ independently represent a hydrogen atom, a methyl group or an ethyl group, and R ₅ to R ₈ independently represent a hydrogen atom atom, a methyl group or a bromine atom, and l and m each independently represent an integer of 1-6. ]

Both R ₁ and R ₃ are preferably hydrogen atoms in order to improve the curability of the composition. Both R ₂ and R ₄ are preferably hydrogen atoms in order to improve the refractive index of the obtained cured product. As R ₅ to R ₈ , it is preferable that all of R ₅ to R ₈ are hydrogen atoms, or that R ₅ is a hydrogen atom, and R ₆ is a methyl group, and R ₇ is a hydrogen atom, R ₈ is a methyl group; and R ₅ is a hydrogen atom, R ₆ is a bromine atom, and R ₇ is a hydrogen atom, R ₈ is a bromine atom.

As l and m, in order to make the refractive index of the hardened|cured material obtained excellent, 1-3 are preferable.

Specific examples of the component (A) include bis(4-methacryloyloxyethoxyphenyl)sulfide, bis(4-acryloyloxyethoxyphenyl)sulfide, bis( 4-methacryloxydiethoxyphenyl) sulfide, bis(4-acryloxydiethoxyphenyl) sulfide, bis(4-methacryloxytriethoxy Phenyl) sulfide, bis(4-acryloxytriethoxyphenyl) sulfide, bis(4-methacryloxydiethoxy-3-methylphenyl) sulfide, bis (4-acryloyloxydiethoxy-3-methylphenyl)sulfide, bis(4-methacryloyloxyethoxy-3-bromophenyl)sulfide, bis(4-propene Acyloxyethoxy-3-bromophenyl)sulfide, bis(4-methacryloyloxydiethoxy-3-bromophenyl)sulfide and bis(4-acryloyloxydiethyl Oxy-3-bromophenyl) sulfide, etc.

Among them, bis(4-acryloyloxyethoxyphenyl)sulfide, bis(4-acryloyloxydiethoxyphenyl)sulfide, bis(4 - Acryloyloxyethoxy-3-methylphenyl)sulfide and bis(4-acryloyloxydiethoxy-3-methylphenyl)sulfide.

(A) The component can be used in combination of 1 type, 2 type, or more types.

2. (B) Ingredients

The (B) component is a (meth)acrylate represented by the following general formula (2) (hereinafter referred to as (B-1) component) or/and a mono(meth)acrylate represented by the following general formula (3) The acrylate (hereinafter referred to as component (B-2)) is a component that imparts a high refractive index and low water absorption to a cured product of the composition, and makes the composition a liquid that is easy to handle.

(In formula (2), R ₉ represents a hydrogen atom or a methyl group.)

(In formula (3), R ₁₀ represents a hydrogen atom or a methyl group.)

Specific examples of component (B-1) include (meth)acrylate-o-phenylphenyl, (meth)acrylate-m-phenylphenyl, and (meth)acrylate-p-phenyl phenyl esters.

Among them, o-phenylphenyl (meth)acrylate is preferable from the viewpoint of being liquid at room temperature, easy to handle, and easy to produce.

A (meth)acrylate or a compound having an epoxy group that is different from the component (B-1) of the present invention and has a phenyl group cannot make the cured product of the composition have a high refractive index, and the cured product has a high water absorption rate. high.

As a specific example of (B-2) component, p-cumylphenol (meth)acrylate etc. are mentioned.

Unlike the component (B-2) of the present invention, a (meth)acrylate having one phenyl group cannot impart a high refractive index to a cured product of the composition.

Both (B-1) component and (B-2) component can be used in combination of 1 type, 2 type or more.

As a ratio when (B-1) component and (B-2) component are used together, it is preferable that (B-1) component is 10-90 mass %, and (B-2) component is 90-10 mass %.

3. Other ingredients

The composition of the present invention is cured by irradiating active energy rays, and examples of the active energy rays at this time include electron rays, visible light, and ultraviolet rays. Among them, visible light or ultraviolet light is preferable because it does not require special equipment and is simple.

In the case of forming a visible light or ultraviolet curable composition, a photopolymerization initiator is mixed in the composition. In addition, when forming an electron beam curable composition, it is not necessarily necessary to mix a photoinitiator.

Specific examples of photopolymerization initiators (hereinafter referred to as (C) component) include benzoins such as benzoin, benzoin methyl ether, and benzoin propyl ether; acetophenone, 2,2- Dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2 -Acetophenones such as -methyl-1-(4-(methylthio)phenyl)-2-morpholino-propan-1-one and N,N-dimethylaminoacetophenone; 2-methyl Anthraquinones such as base anthraquinone, 1-chloroanthraquinone and 2-pentyl anthraquinone; 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone and Thioxanthones such as 2,4-diisopropylthioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone, methylbenzophenone, 4,4'-Dichlorobenzophenone, 4,4'-bisdiethylaminobenzophenone, Michler's ketone and 4-benzoyl-4'-methyldiphenylsulfide benzophenones, etc.; and 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc.

(C) Components may be used alone or in combination of two or more.

In (C)component, a photosensitizer can be used together as needed. Examples of the photosensitizer include N,N-dimethylaminobenzoic acid ethyl ester, N,N-dimethylaminobenzoic acid isoamyl ester, triethylamine, triethanolamine, and the like.

The preferred mixing ratio of component (C) is relative to 100 parts by mass of the total amount of component (A) and component (B), or when an unsaturated group-containing compound described later is mixed, relative to component (A) , (B) 100 mass parts of total amounts of a component and an unsaturated group containing compound, Preferably it is 0.05-12 mass parts, More preferably, it is 0.1-5 mass parts.

In the composition of this invention, the unsaturated group containing compound other than (A) component and (B) component can be mixed as needed.

Examples of the unsaturated group-containing compound include phenoxyethyl (meth)acrylate, carbitol (meth)acrylate, N-vinylcaprolactone, acryloylmorpholine, (methyl) ) glycidyl acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1,4-butylene glycol mono(meth)acrylate, di(meth)acrylate )-1,6-hexanediol acrylate, nonanediol diacrylate, polyglycol di(meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, (meth)acrylate base) tribromophenyl acrylate, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxydiethyl oxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxytriethoxyphenyl)propane, ethylene glycol di(meth)acrylate, tribromo(meth)acrylate Phenoxyethyl ester, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, di(meth)acrylates of bisphenol A type epoxy resins, various polyurethane poly(meth)acrylates base) acrylates and polyester poly(meth)acrylates, etc.

The mixing ratio of the unsaturated group-containing compound is preferably in the range of 0 to 50% by mass in the composition.

In addition to the above-mentioned components, pigments, dyes, antifoaming agents, leveling agents, inorganic fillers, organic fillers and light stabilizers, antioxidants, ultraviolet absorbers, etc. may be mixed as needed. In addition, a small amount of antioxidants, light stabilizers, ultraviolet absorbers and polymerization inhibitors can also be added as needed.

In order to further advance curing, a thermal polymerization initiator may be mixed with the composition of the present invention, and the composition may be heated after irradiating active energy rays.

As the thermal polymerization initiator, various compounds can be used, and organic peroxides and azo-based initiators are preferable.

Specific examples of organic peroxides include 1,1-bis(tert-butylperoxy)-2-methylcyclohexane, 1,1-bis(tert-hexylperoxy)-3,3 , 5-trimethylcyclohexane, 1,1-bis(tert-hexylperoxy)cyclohexane, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Hexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(4,4-bis(butylperoxy)cyclohexyl)propane, 1,1-bis(tert- Butylperoxy)cyclododecane, tert-hexylperoxyisopropyl monocarbonate, tert-butylperoxymaleic acid, tert-butylperoxy-3,5,5-trimethylhexanoate, tert-butyl perlaurate, 2,5-dimethyl-2,5-bis(m-toluoylperoxy)hexane, tert-butylperoxyisopropyl monocarbonate, tert-butylperoxy-2- Ethylhexyl monocarbonate, tert-hexyl peroxybenzoate, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, tert-butyl peroxyacetate, 2,2- Bis(tert-butylperoxy)butane, tert-butyl peroxybenzoate, n-butyl 4,4-bis(tert-butylperoxy)valerate, bis(tert-butylperoxy)m-benzene Diacyl ester, α,α'-bis(tert-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy) ) hexane, tert-butyl cumyl peroxide, di-tert-butyl peroxide, terpane hydroperoxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne , Dicumyl hydroperoxide, tert-butyl trimethylsilyl peroxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, tert-hexyl hydroperoxide And tert-butyl hydroperoxide, etc.

Specific examples of azo compounds include 1,1'-azobis(cyclohexane-1-carbonitrile), 2-(carbamoylazo)isobutyronitrile, 2-phenylazo- 4-methoxy-2,4-dimethylvaleronitrile, azodi-tert-octane, azodi-tert-butane, etc.

These compounds may be used alone or in combination of two or more. In addition, organic peroxides can also form redox reactions by combining with reducing agents.

4. Composition for active energy ray-curable optical material

In this invention, it is essential to contain the said (A) component and (B) component.

The ratio of (A) component and (B) component is based on the total amount of (A) component and (B) component, (A) component is 10 to 90 mass % and (B) component is 90 to 10 mass % , It is preferable that (A) component is 30-90 mass %, and (B) component is 70-10 mass %. If the proportion of the component (A) is less than 10% by mass, the desired refractive index cannot be obtained; on the other hand, if the proportion of the component (A) exceeds 90% by mass, the composition sometimes becomes solid at room temperature, Operational problems arise.

The composition of this invention can be manufactured by stirring and mixing the said (A) component, (B) component, and other components added as needed according to a conventional method.

When (A) component or (C) component is solid, you may heat after stirring and mixing as needed, Preferably a heating temperature is 50-100 degreeC.

As the production method of the optical material using the composition of the present invention, conventional methods can be used, for example, coating or injecting the composition into a mold frame having a predetermined shape, and then placing a transparent substrate from above if necessary, and irradiating the active material. A method of curing the composition with energy rays, and then removing the cured product from the formwork, etc.

Examples of active energy rays include electron rays, visible light, ultraviolet rays, and the like. Among them, visible light or ultraviolet light is preferable because it does not require a special device and is simple. As an ultraviolet irradiation device, a high-pressure mercury lamp etc. are mentioned.

The irradiation dose and irradiation time of active energy rays can be appropriately set according to the composition to be used and its use.

In the composition of the present invention, a cured product having a high refractive index such that the refractive index (25° C.) is usually 1.59 or higher, preferably 1.60 or higher can be obtained. In addition, the cured product is also excellent in transparency.

As such, the cured product of the composition of the present invention has a high refractive index and transparency, and can be used in various optical materials such as Fresnel lenses, lenticular lenses, and prism sheets, as well as plastic lenses.

More specifically, as the lens sheet, applications such as video projectors, projection televisions, and liquid crystal displays are mentioned.

An example of producing a lens sheet using the composition of the present invention will be described.

When producing a lens sheet with a relatively thin film thickness, the composition of the present invention is applied to a mold frame called a stamper having the desired lens shape, a layer of the composition is placed, and a transparent substrate is bonded on the layer. .

Next, the composition was cured by irradiating active energy rays from the transparent substrate side, and then peeled off from the mold.

On the other hand, when producing a lens sheet having a relatively thick film thickness, the composition of the present invention is injected between the mold frame having the intended lens shape and the transparent substrate.

Next, active energy rays were irradiated from the transparent substrate side to cure the composition, and then the composition was peeled off from the mold.

The above-mentioned transparent substrate is preferably a resin substrate, and as specific examples, sheet-like ones such as methacrylic resin, polycarbonate resin, methyl methacrylate-styrene resin, and styrene resin can be used.

The material of the mold frame is not particularly limited, and examples thereof include metals such as brass and nickel, and resins such as epoxy resin. From the viewpoint of long mold frame life, metal molds are preferable.

Next, an example of producing a plastic lens using the composition of the present invention will be described.

For example, there may be mentioned a method in which the composition of the present invention is poured into a mirror-polished frame with at least one side transparent, cured by irradiating active energy rays, and then released from the mold.

As the mold frame in this case, two mirror-polished templates made of glass, plastic, or a combination of them, plasticized vinyl chloride and ethylene-vinyl acetate copolymer and other thermoplastic resins can be used. A mold frame formed by combining gaskets and other tools for clamping two templates together.

In this case, irradiation of active energy rays may be performed on one or both surfaces of the template. In addition, active energy ray irradiation and heating may be combined.

The composition of the present invention has excellent workability at room temperature, and the obtained cured product has a high refractive index and good light transmittance, and can be low in water absorption and excellent in dimensional stability. Therefore, the composition of the present invention can be suitably used for optical members such as lens sheets and plastic lenses that require high refractive index, high light transmittance, dimensional stability, and the like.

Detailed ways

In the composition of this invention, it is essential to contain (A) component 90-10 mass % and (B) component 90-10 mass %. As the component (A), in order to increase the refractive index of the cured product of the composition, it is preferable that R ₁ and R ₃ are both diacrylates of hydrogen atoms. As a composition, it is preferable to contain (C)component.

In addition, the present invention is a method for producing an optical material in which the above-mentioned composition is applied or injected into a mold having a predetermined shape, and then irradiated with active energy rays.

Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples.

Examples and Comparative Examples

The components shown in Table 1 were stirred and mixed according to the usual method, and the solid photopolymerization initiator was heated and dissolved in a dryer kept at 80°C for 15 minutes to prepare an ultraviolet curable composition. .

The prepared composition was coated on an OPP film with a film thickness of 30 μm using a bar coater at room temperature. Under the condition that the speed of the conveyor belt is 10m/min, a high-pressure mercury lamp with a lamp height of 10cm and a power of 80W/cm is used to irradiate it with ultraviolet rays twice to cure it.

The obtained cured product was evaluated according to the following method. These results are shown in Table 2.

(1) Operability

Ease of handling the composition when producing a cured product was evaluated. Those that were liquid at room temperature were set as ◯, and those that were solid or pasty were set as x.

(2) Refractive index

The refractive index of the hardened|cured material was measured with the Abbe refractometer DR-M2 by Atago Corporation (the measured value using the sodium D line at 25 degreeC).

(3) Light transmittance

The light transmittance of the cured product at a wavelength of 400 nm was measured with V-550 manufactured by JASCO Corporation.

(4) Water absorption

A resin plate was placed on the four corners of the glass plate to form a hollow portion with a thickness of 0.4 mm. The prepared composition was filled in the void, and then the glass plate was placed.

It was irradiated with ultraviolet rays under the same conditions as above. After curing, the glass plate was removed to obtain a thin slice of cured product having a thickness of 0.4 mm.

The obtained cured product was cut into 5 cm x 5 cm and used as a test piece.

This test piece was heated at 210° C. for 1 hour in nitrogen gas to completely dry the cured product, and then left to cool in a desiccator, and then the test piece (W1) was weighed. Next, the test piece was immersed in distilled water at 80° C. for 20 hours, and after taking it out, the water on the surface of the test piece was lightly wiped off and weighed (W2), and the water absorption rate was calculated by the following formula.

Water absorption (%)=100×(W2-W1)/W1

[Table 1]

The abbreviations in Table 1 have the following meanings.

BAEPS: bis(4-acryloyloxyethoxyphenyl) sulfide

o-PPA: o-phenylphenyl acrylate

p-PPA: p-cumylphenyl acrylate

・M-211B: bisphenol A ethylene oxide 4 mole modified diacrylate, Aronix M-211B manufactured by Toagosei Co., Ltd.

M-400: a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, Toagosei Co., Ltd. product Aronix M-400

POA: Phenoxyethyl Acrylate

・TO-1463: Acrylic ester of 1 mole adduct of o-phenylphenol ethylene oxide, Aronix TO-1463 manufactured by Toagosei Co., Ltd.

Irg184: 1-hydroxycyclohexyl phenyl ketone, Irgacure184 manufactured by Ciba Specialty Chemicals

[Table 2]

As apparent from Table 2, the composition of the present invention is excellent in workability, and its cured product has a high refractive index of 1.59 or more, and is also good in light transmittance and low in water absorption.

On the other hand, when a composition (Comparative Example 1) containing component (A) but containing only one phenyl group in the molecule and phenoxyethyl acrylate different from component (B) was used, the refractive index could not be obtained. Cured product with high and low water absorption. Moreover, since the composition (comparative example 2) using only (A) component was solid at room temperature, it was inferior in handleability, and hardened|cured material could not be obtained. In addition, in the compositions containing (B) component but not containing (A) component (Comparative Example 3 and Comparative Example 4), cured products with high refractive index and low water absorption could not be obtained. In addition, compositions having an alkylene oxide unit different from the component (B) of the present invention (Comparative Example 5 and Comparative Example 6) were excellent in optical properties such as handleability and refractive index, but could not achieve low water absorption. of solidification.

Application example (manufacture of lens sheet)

The compositions prepared in Examples 1 to 8 were used, poured into a mold having a lens shape, and sandwiched between methacrylate resin plates of transparent substrates from above.

Under the same conditions as above, the composition was cured by irradiating ultraviolet rays from the transparent substrate side.

By taking out the cured cured product from the mold and shaping it into a desired shape, a lens sheet having excellent optical properties as described above can be obtained.

The composition of the present invention, as a composition for active energy ray-curable optical materials, can be used suitably for lens sheets such as Fresnel lenses and lenticular lenses used in image projectors, projection televisions, liquid crystal displays, etc., and plastic lenses, etc. Representative optical components that require high refractive index and high light transmittance.

Claims (10)

1. A composition for an active energy ray-curable optical material, characterized in that it contains a di(meth)acrylate (A) represented by the following general formula (1) and a di(meth)acrylate represented by the following general formula (2). Mono(meth)acrylate and/or mono(meth)acrylate (B) represented by the following general formula (3), based on the total amount of (A) component and (B) component, containing 10-90% by mass of component (A) and 90-10% by mass of component (B), In formula (1), R ₁ and R ₃ each independently represent a hydrogen atom or a methyl group; R ₂ and R ₄ each independently represent a hydrogen atom, a methyl group or an ethyl group; R ₅ to R ₈ each independently represent a hydrogen atom , a methyl group or a bromine atom; 1 and m independently represent an integer of 1 to 6,

In formula (2), R represents _a hydrogen atom or a methyl group,

In formula (3), R ₁₀ represents a hydrogen atom or a methyl group. 2. The composition for active energy ray-curable optical materials according to claim 1, wherein the di(meth)acrylate (A) is that in the general formula (1) _R1 and _R3 are both A diacrylate ester of a hydrogen atom. 3. The composition for an active energy ray-curable optical material according to claim 1, further comprising a photopolymerization initiator (C). 4. The composition for active energy ray-curable optical materials according to claim 1, wherein R ₂ and R ₄ are hydrogen atoms. 5. The composition for active energy ray-curable optical materials according to claim 1, wherein the component (A) is bis(4-methacryloyloxyethoxyphenyl) sulfide, bis(4- Acryloyloxyethoxyphenyl) sulfide, bis(4-methacryloxydiethoxyphenyl)sulfide, bis(4-acryloyloxydiethoxyphenyl)sulfide , bis(4-methacryloyloxytriethoxyphenyl) sulfide, bis(4-acryloyloxytriethoxyphenyl) sulfide, bis(4-methacryloyloxydi Ethoxy-3-methylphenyl)sulfide, bis(4-acryloyloxydiethoxy-3-methylphenyl)sulfide, bis(4-methacryloyloxyethoxy -3-bromophenyl)sulfide, bis(4-acryloyloxyethoxy-3-bromophenyl)sulfide, bis(4-methacryloyloxydiethoxy-3-bromobenzene base) sulfide or bis(4-acryloyloxydiethoxy-3-bromophenyl) sulfide. 6. The composition for an active energy ray-curable optical material according to claim 1, wherein the mono(meth)acrylate represented by the general formula (2) is o-phenylphenyl(meth)acrylate. 7 . The composition for an active energy ray-curable optical material according to claim 1 , comprising 30 to 90% by mass of the component (A) and 70 to 10% by mass of the component (B). 8. A method of manufacturing an optical material, comprising: The process of coating or injecting the composition described in any one of claims 1 to 7 into a mold frame having a prescribed shape; A step of irradiating active energy rays to cure the composition after coating or injection; and After the composition is cured, the process of removing the cured product from the mold. 9 . An optical material obtained by curing the composition for an active energy ray-curable optical material according to claim 1 by irradiating active energy rays. 10. The optical material according to claim 9, which is a lens sheet or a plastic lens.