JP7382313B2 - Optical resin composition and optical lens - Google Patents

Description

The present invention relates to an optical resin composition and an optical lens obtained from the composition.

Many optical materials are known that constitute imaging optical systems such as cameras. In particular, organic optical materials such as plastic lenses are lighter than inorganic materials, less likely to break, and can be processed into various shapes, as well as having a high degree of freedom in selecting material designs with desired properties. , has become rapidly popular in various applications in recent years.

Generally, an imaging optical system such as a camera is constructed by combining a plurality of types of optical lenses having different optical properties. In particular, a method has been adopted in which chromatic aberration in an optical system is corrected by combining optical lenses with different wavelength dispersion characteristics of refractive index. Conventionally, the Abbe number νd has been mainly used as an index indicating wavelength dispersion characteristics, and attempts have been made to correct chromatic aberration by combining materials exhibiting a high Abbe number and materials exhibiting a low Abbe number.

Furthermore, as a method for correcting chromatic aberration at a higher level regarding organic optical materials, it has been proposed to use an optical material that exhibits a low Abbe number and a specific partial dispersion ratio θg,F (Patent Document 1) ).

On the other hand, Patent Document 2 describes that an organic-inorganic composite material in which inorganic fine particles are dispersed in a thermoplastic resin having a specific benzotriazole skeleton has a high refractive index and a low Abbe number. Further, Patent Document 3 describes that, regarding materials used in paints and the like, a high refractive index polymer having a benzotriazole skeleton as an ultraviolet absorbing group has excellent light resistance and does not cause bleed-out.

Japanese Patent Application Publication No. 2010-097195 Japanese Patent Application Publication No. 2010-189562 Japanese Patent Application Publication No. 2014-201735

Generally, when the Abbe number is low, the partial dispersion ratio tends to be relatively high, but a material with a low Abbe number does not necessarily exhibit a sufficiently high partial dispersion ratio. Further, in the past, materials exhibiting a low Abbe number and a high partial dispersion ratio often lacked the properties required for optical lenses, such as light transmittance, heat resistance, and light resistance. For example, an optical material containing a compound having a diphenyl sulfide skeleton disclosed in Patent Document 1 has low light resistance and heat resistance, and there is room for improvement in terms of long-term reliability.

An object of the present invention is to provide an optical resin composition capable of forming a resin material for optical members that exhibits a low Abbe number and a high partial dispersion ratio, and also has excellent light resistance, high light transmittance, and high heat resistance. Our goal is to provide the following.

One aspect of the present invention provides: (A) a first radically polymerizable component comprising at least one radically polymerizable compound represented by the following formula (a1), (a2), or (a3); The present invention relates to an optical resin composition containing a second radically polymerizable component made of a radically polymerizable compound different from the first radically polymerizable component. When the first radically polymerizable component and the second radically polymerizable component undergo radical polymerization, a resin material containing these polymers is formed. The Abbe number νd and partial dispersion ratio θg,F of the resin material are expressed by the following formula:
18≦νd≦25; and θg, F≧0.700
satisfy.

式（ａ１）中、
Ｘ^１は、水素原子、ハロゲン原子、置換基を有していてもよい炭素数１～１８の炭化水素基、置換基を有していてもよい炭素数１～１８のアルコキシカルボニルアルキル基、又は、（メタ）アクリロイル基を有する基を示し、
Ｘ^２及びＸ^３は、それぞれ独立して、水素原子、ハロゲン原子、又は、置換基を有していてもよい炭素数１～１８の炭化水素基を示し、
Ｘ^４は、水素原子、置換基を有していてもよい炭素数１～１８の炭化水素基、又は、（メタ）アクリロイル基を有する基を示し、
Ｘ^５は、水素原子、ハロゲン原子、置換基を有していてもよい炭素数１～１８の炭化水素基、又は、（メタ）アクリロイル基を有する基を示し、
Ｘ^１、Ｘ^４又はＸ^５のうち少なくとも１つが、（メタ）アクリロイル基を有する基である。

In formula (a1),
X ¹ is a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, an alkoxycarbonylalkyl group having 1 to 18 carbon atoms which may have a substituent, or , represents a group having a (meth)acryloyl group,
X ² and X ³ each independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 18 carbon atoms that may have a substituent,
X ⁴ represents a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
X ⁵ represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
At least one of X ¹ , X ⁴ or X ⁵ is a group having a (meth)acryloyl group.

式（ａ２）中、
Ｙ^１及びＹ^２は、それぞれ独立して、水素原子、水酸基、置換基を有していてもよい炭素数１～８のアルコキシ基、又は、（メタ）アクリロイル基を有する基を示し、
Ｙ^３及びＹ^４は、それぞれ独立して、水素原子、置換基を有していてもよい炭素数１～１８の炭化水素基、又は、（メタ）アクリロイル基を有する基を示し、
Ｙ^１、Ｙ^２、Ｙ^３又はＹ^４のうち少なくとも１つが、（メタ）アクリロイル基を有する基である。

In formula (a2),
Y ¹ and Y ² each independently represent a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
Y ³ and Y ⁴ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
At least one of Y ¹ , Y ² , Y ³ or Y ⁴ is a group having a (meth)acryloyl group.

式（ａ３）中、
Ｚ^１は置換基を有していてもよい炭素数１～１８の炭化水素基、置換基を有していてもよい炭素数１～１８のアルキルカルボニルオキシアルキル基、置換基を有していてもよい炭素数１～１８のアルコキシカルボニルアルキル基、又は置換基を有していてもよい炭素数１～１８のアルコキシアルキル基を示し、
Ｚ^２、Ｚ^４、Ｚ^５、Ｚ^６、Ｚ^８及びＺ^９は、それぞれ独立して、水素原子、置換基を有していてもよい炭素数１～１８の炭化水素基、又は置換基を有していてもよい炭素数１～８のアルコキシ基を示し、
Ｚ^３は水素原子、又は、（メタ）アクリロイル基を有する基を示し、
Ｚ^７は水素原子、水酸基、置換基を有していてもよい炭素数１～１８の炭化水素基、置換基を有していてもよい炭素数１～８のアルコキシ基、又は、（メタ）アクリロイル基を有する基を示し、
Ｚ^３又はＺ^７のうち少なくとも１つは、（メタ）アクリロイル基を有する基である。

In formula (a3),
Z ¹ is a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, an alkylcarbonyloxyalkyl group having 1 to 18 carbon atoms which may have a substituent, and an alkoxycarbonylalkyl group having 1 to 18 carbon atoms, or an alkoxyalkyl group having 1 to 18 carbon atoms, which may have a substituent;
Z ² , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁸ and Z ⁹ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a substituent. Indicates an optional alkoxy group having 1 to 8 carbon atoms,
Z ³ represents a hydrogen atom or a group having a (meth)acryloyl group,
Z ⁷ is a hydrogen atom, a hydroxyl group, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, an alkoxy group having 1 to 8 carbon atoms which may have a substituent, or (meth) Indicates a group having an acryloyl group,
At least one of Z ³ or Z ⁷ is a group having a (meth)acryloyl group.

As described above, the optical resin composition containing the first radically polymerizable component and the second radically polymerizable component exhibits a low Abbe number and a high partial dispersion ratio, and also has excellent light resistance, high light transmittance, and A resin material for optical members having high heat resistance can be formed.

Another aspect of the present invention relates to an optical lens made of a resin material containing a polymer formed by radical polymerization of the first radically polymerizable component and the second radically polymerizable component in the optical resin composition. This optical lens exhibits a low Abbe number and a high partial dispersion ratio, and can also have excellent light resistance, high light transmittance, and high heat resistance.

The optical resin composition according to the present invention can form a resin material for optical members that exhibits a low Abbe number and a high partial dispersion ratio, and has excellent light resistance, high light transmittance, and high heat resistance. By using a molded body of this resin material as an optical lens, chromatic aberration of the optical system can be efficiently removed.

FIG. 1 is a cross-sectional view showing one embodiment of an optical lens.

Hereinafter, several embodiments of the present invention will be described in detail.

As used herein, "(meth)acrylic" means "acrylic" and "methacrylic".

The optical resin composition according to one embodiment includes a first radically polymerizable component consisting of at least one radically polymerizable compound represented by formula (a1), (a2), or (a3); It contains a second radically polymerizable component made of a radically polymerizable compound different from the first radically polymerizable component. When the first radically polymerizable component and the second radically polymerizable component undergo radical polymerization, a solid resin material containing a polymer of these radically polymerizable components is formed. For example, when at least one of the first radically polymerizable component or the second radically polymerizable component contains a polyfunctional radically polymerizable compound having two or more radically polymerizable groups, the crosslinked polymer is A resin material (cured product) containing the resin is formed.

The Abbe number νd and the partial dispersion ratio θg,F of the resin material formed from the optical resin composition according to the present embodiment satisfy the following formula. Satisfying these equations means that the resin material exhibits a significantly high partial dispersion ratio while exhibiting a relatively low Abbe number.
18≦νd≦25
θg, F≧0.700

(A) The first radically polymerizable component is a radically polymerizable compound represented by formula (a1), a radically polymerizable compound represented by formula (a2), or a radically polymerizable compound represented by formula (a3). , or a combination of two or more selected from these. The radically polymerizable compounds represented by formulas (a1), (a2), or (a3) constituting the first radically polymerizable component each have one or more (meth)acryloyl groups. The radically polymerizable compound represented by formula (a1), (a2) or (a3) may be a monofunctional radically polymerizable compound having one (meth)acryloyl group.

The radically polymerizable compound represented by formula (a1) has a benzotriazole skeleton, and has a (meth)acryloyl group in at least one of X ¹ , X ⁴ , or X ⁵ .

Examples of the halogen atom represented by X ¹ in formula (a1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. X ¹ may be a chlorine atom.

When formula (a1) is a hydrocarbon group having 1 to 18 carbon atoms and having a substituent, the substituent may be, for example, a halogeno group, an alkoxy group or a hydroxy group. The same applies to specific examples of substituents in other compounds described below. Examples of the hydrocarbon group having 1 to 18 carbon atoms and optionally having a substituent, represented by X ¹ in formula (a1), include methyl group, ethyl group, 2-methoxyethyl group, n-propyl group. group, isopropyl group, 3-chloro-n-propyl group, n-butyl group, sec-butyl group, tert-butyl group, 4-hydroxy-n-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert -pentyl group, n-hexyl group, isohexyl group, cyclohexyl group, 6-phenyl-n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, 1,1,3,3-tetramethylbutyl group, n-dodecyl group, n-octadecyl group, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-chlorophenyl group, 4-bromophenyl group, 3,4-dichlorophenyl group, naphthyl group group, benzyl group, phenethyl group, and 1-methyl-1-phenethyl group. X ¹ may be a hydrocarbon group having 1 to 8 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, isopentyl group, neopentyl group, It may be an n-pentyl group, a tert-pentyl group, an n-hexyl group, or an n-octyl group.

Examples of the alkoxycarbonylalkyl group having 1 to 18 carbon atoms and optionally having a substituent, represented by X ¹ in formula (a1), include methoxycarbonylethyl group, ethoxycarbonylethyl group, n-octoxy Carbonylethyl group, isooctyloxycarbonylethyl group, n-dodecyloxycarbonylethyl group, methoxycarbonylpropyl group, ethoxycarbonylpropyl group, n-octoxycarbonylpropyl group, isooctyloxycarbonylpropyl group, and n-dodecyloxycarbonyl group Examples include propyl group. X ¹ may be a methoxycarbonylethyl group, an ethoxycarbonylethyl group, an n-octoxycarbonylethyl group, or an isooctyloxycarbonylethyl group. The number of carbon atoms in an alkoxycarbonylalkyl group means the total number of carbon atoms contained in the alkoxy moiety, carbonyl moiety, and alkyl moiety contained in the alkoxycarbonylalkyl group.

Examples of the group having a (meth)acryloyl group represented by X ¹ in formula (a1) include an acryloyl group, an acryloyloxy group, an acryloyloxyethyl group, a methacryloyl group, a methacryloyloxy group, and a methacryloyloxyethyl group. can be mentioned. X ¹ may be an acryloyloxyethyl group or a methacryloyloxyethyl group.

The hydrocarbon group having 1 to 18 carbon atoms and optionally having a halogen atom and a substituent, represented by X ² or X ³ in formula (a1), has a halogen atom and a substituent represented by X ¹ It has the same meaning as an optional hydrocarbon group having 1 to 18 carbon atoms.

The hydrocarbon group having 1 to 18 carbon atoms which may have a substituent and which is represented by X ⁴ in formula (a1) is a hydrocarbon group having ¹ to 18 carbon atoms which may have a substituent and which is represented by It has the same meaning as the hydrocarbon group of ~18.

Examples of the group having a (meth)acryloyl group represented by X ⁴ in formula (a1) include acryloyl group, 2-(acryloyloxy)ethylcarbamoyl group, methacryloyl group, and 2-(methacryloyloxy)ethylcarbamoyl group. Examples include groups.

The hydrocarbon group having 1 to 18 carbon atoms, which may have a halogen atom and a substituent, and which is represented by X ⁵ in formula (a1), has a halogen atom and a substituent, which is represented by X ¹ . It has the same meaning as a hydrocarbon group having 1 to 18 carbon atoms.

Examples of the group having a (meth)acryloyl group represented by X ⁵ in formula (a1) include an acryloyl group, an acryloyloxy group, an acryloyloxyethyl group, an acryloyloxyethoxy group, a methacryloyl group, a methacryloyloxy group, and a methacryloyl group. Examples include oxyethyl group and methacryloyloxyethoxy group. X ⁵ may be an acryloyloxyethoxy group or a methacryloyloxyethoxy group.

Specific examples of the radically polymerizable compound represented by formula (a1) include 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole (for example, the product name "RUVA -93'' (manufactured by Otsuka Chemical Co., Ltd. or Tokyo Kasei Co., Ltd.), 2-[2-hydroxy-3-tert-butyl-5-[2-(methacryloyloxy)ethyl]phenyl]-2H- Benzotriazole, 2-(2-hydroxy-5-methylphenyl)-5-[2-(methacryloyloxy)ethyl]-2H-benzotriazole, 2-[2-(2-hydroxy-4-octyloxyphenyl)- 2H-1,2,3-benzotriazol-5-yloxy]ethyl methacrylate, 2-[2-(2-(methacryloyloxy)ethylcarbamoyloxy)-5-[2-(methacryloyloxy)ethyl]phenyl]-2H -benzotriazole, and 2-[2-methacryloyloxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole.

The radically polymerizable compound represented by formula (a2) has a benzophenone skeleton, and has a (meth)acryloyl group in at least one of Y ¹ , Y ² , Y ³ , or Y ⁴ .

Examples of the alkoxy group having 1 to 8 carbon atoms and optionally having a substituent, represented by Y ¹ or Y ² in formula (a2), include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, 4-hydroxy-n-butoxy group, n-pentoxy group, isopentoxy group, neopentoxy group, tert-pentoxy group, n-hexyloxy group, isohexyl Examples include oxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, and 1,1,3,3-tetramethylbutoxy group. Y ¹ and Y ² each independently represent a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, n-hexyloxy group, isohexyloxy or n-octyloxy group.

Examples of the group having a (meth)acryloyl group represented by Y ¹ or Y ² in formula (a2) include acryloyl group, acryloyloxy group, acryloyloxyethyl group, acryloyloxyethoxy group, 2-(acryloyloxy ) ethylcarbamoyloxy group, methacryloyl group, methacryloyloxy group, methacryloyloxyethyl group, methacryloyloxyethoxy group, and 2-(methacryloyloxy)ethylcarbamoyloxy group. Y ¹ and Y ² may each independently be an acryloyloxy group, a 2-(acryloyloxy)ethylcarbamoyloxy group, a methacryloyloxy group, or a 2-(methacryloyloxy)ethylcarbamoyloxy group.

Examples of the hydrocarbon group having 1 to 18 carbon atoms and optionally having a substituent, represented by Y ³ or Y ⁴ in formula (a2), include a methyl group, an ethyl group, a 2-methoxyethyl group, n-propyl group, isopropyl group, 3-chloro-n-propyl group, n-butyl group, sec-butyl group, tert-butyl group, 4-hydroxy-n-butyl group, n-pentyl group, isopentyl group, neopentyl group group, tert-pentyl group, n-hexyl group, isohexyl group, cyclohexyl group, 6-phenyl-n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, 1,1,3,3-tetramethyl Butyl group, n-dodecyl group, n-octadecyl group, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-chlorophenyl group, 4-bromophenyl group, 3,4-dichlorophenyl group group, naphthyl group, benzyl group, phenethyl group, and 1-methyl-1-phenethyl group. Y ³ and Y ⁴ may each independently be a hydrocarbon group having 1 to 8 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group. group, isopentyl group, neopentyl group, n-pentyl group, tert-pentyl group, n-hexyl group, or n-octyl group.

Examples of the group having a (meth)acryloyl group represented by Y ³ or Y ⁴ in formula (a2) include an acryloyl group, a 2-(acryloyloxy)ethylcarbamoyl group, a methacryloyl group, and a 2-(methacryloyloxy) group. ) ethylcarbamoyl group, etc.

Specific examples of the radically polymerizable compound represented by formula (a2) include 2-hydroxy-4-acryloyloxybenzophenone (for example, manufactured by FINIPHARMA LIMITED) and 2-hydroxy-4-methacryloyloxybenzophenone (for example, Alfa Aesar). ), 2,2',4,4'-tetramethacryyloxybenzophenone, and 2,2',4,4'-tetra[2-(methacryyloxy)ethylcarbamoyloxy]benzophenone.

The radically polymerizable compound represented by formula (a3) has a triazine skeleton, and has a (meth)acryloyl group in at least one of Z ³ and Z ⁷ .

Examples of the hydrocarbon group having 1 to 18 carbon atoms and optionally having a substituent, represented by Z ¹ in formula (a3), include methyl group, ethyl group, 2-methoxyethyl group, n-propyl group. group, isopropyl group, 3-chloro-n-propyl group, n-butyl group, sec-butyl group, tert-butyl group, 4-hydroxy-n-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert -pentyl group, n-hexyl group, isohexyl group, cyclohexyl group, 6-phenyl-n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, 1,1,3,3-tetramethylbutyl group, n-dodecyl group, n-octadecyl group, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-chlorophenyl group, 4-bromophenyl group, 3,4-dichlorophenyl group, naphthyl group group, benzyl group, phenethyl group, and 1-methyl-1-phenethyl group. Z ¹ may be a hydrocarbon group having 1 to 8 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, isopentyl group, neopentyl group , n-pentyl group, tert-pentyl group, n-hexyl group, n-octyl group, or phenyl group.

Examples of the alkylcarbonyloxyalkyl group having 1 to 18 carbon atoms and optionally having a substituent, represented by Z ¹ in formula (a3), include methylcarbonyloxyethyl group, ethylcarbonyloxyethyl group, and Examples include (2-ethylhexyl)carbonyloxyethyl group. Z ¹ may be a (2-ethylhexyl)carbonyloxyethyl group. The number of carbon atoms in the alkylcarbonyloxyalkyl group means the total number of carbon atoms included in the two alkyl moieties and the carbonyl moiety contained in the alkylcarbonyloxyalkyl group.

Examples of the alkoxycarbonylalkyl group having 1 to 18 carbon atoms and optionally having a substituent, represented by Z ¹ in formula (a3), include methoxycarbonylethyl group, ethoxycarbonylethyl group, n-octoxy Carbonylethyl group, isooctyloxycarbonylethyl group, n-dodecyloxycarbonylethyl group, methoxycarbonylpropyl group, ethoxycarbonylpropyl group, n-octoxycarbonylpropyl group, isooctyloxycarbonylpropyl group, and n-dodecyloxycarbonyl group Examples include propyl group. Z ¹ may be a methoxycarbonylethyl group, an ethoxycarbonylethyl group, an n-octoxycarbonylethyl group, or an isooctyloxycarbonylethyl group. The number of carbon atoms in an alkoxycarbonylalkyl group means the total number of carbon atoms contained in the alkoxy moiety, carbonyl moiety, and alkyl moiety contained in the alkoxycarbonylalkyl group.

Examples of the alkoxyalkyl group having 1 to 18 carbon atoms and optionally having a substituent, represented by Z ¹ in formula (a3), include methoxymethyl group, methoxyethyl group, 3-methoxypropyl group, ethoxy Methyl group, ethoxyethyl group, 3-ethoxypropyl group, 3-(n-hexyloxy)propyl group, (2-ethylhexyloxy)-2-hydroxypropyl group, (dodecyloxy)-2-hydroxypropyl group, etc. Can be mentioned. Z ¹ may be a (2-ethylhexyloxy)-2-hydroxypropyl group. The number of carbon atoms in an alkoxyalkyl group means the total number of carbon atoms contained in the alkoxy moiety and the alkyl moiety contained in the alkoxyalkyl group.

The hydrocarbon group having 1 to 18 carbon atoms and optionally having a substituent, which is represented by Z ² , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁸ or Z ⁹ in formula (a3), ^is It has the same meaning as the hydrocarbon group having 1 to 18 carbon atoms which may have a substituent as shown.

Examples of the alkoxy group having 1 to 8 carbon atoms and optionally having a substituent represented by Z ² , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁸ or Z ⁹ in formula (a3) include methoxy; group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, 4-hydroxy-n-butoxy group, n-pentoxy group, isopentoxy group, neopentoxy group, tert -Pentoxy group, n-hexyloxy group, isohexyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, and 1,1,3,3-tetramethylbutoxy group, etc. can be mentioned. Z ² , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁸ and Z ⁹ each independently represent a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert -butoxy group, n-hexyloxy group, isohexyloxy group, or n-octyloxy group.

Examples of the group having a (meth)acryloyl group represented by Z ³ in formula (a3) include an acryloyl group, a 2-(acryloyloxy)ethylcarbamoyl group, a methacryloyl group, and a 2-(methacryloyloxy)ethylcarbamoyl group. Examples include groups.

The hydrocarbon group having 1 to 18 carbon atoms which may have a substituent and which is represented by Z ⁷ in formula (a3) is a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent and which is represented by Z ¹ It has the same meaning as the hydrocarbon group of ~18. The alkoxy group having 1 to 8 carbon atoms which may have a substituent and which is represented by Z ⁷ in formula (a3) is an alkoxy group having 1 to 8 carbon atoms which may have a substituent and which is represented by Z ² etc. It has the same meaning as the alkoxy group in ~8.

Examples of the group having a (meth)acryloyl group represented by Z ⁷ in formula (a3) include an acryloyl group, an acryloyloxy group, an acryloyloxyethyl group, an acryloyloxyethoxy group, and a 2-(acryloyloxy)ethylcarbamoyl group. Examples include oxy group, methacryloyl group, methacryloyloxy group, methacryloyloxyethyl group, methacryloyloxyethoxy group, and 2-(methacryloyloxy)ethylcarbamoyloxy group. Z ⁷ may be an acryloyloxy group, a 2-(acryloyloxy)ethylcarbamoyloxy group, a methacryloyloxy group, or a 2-(methacryloyloxy)ethylcarbamoyloxy group.

As a specific example of the radically polymerizable compound represented by formula (a3), in formula (a3), Z ¹ is an isooctyloxycarbonylethyl group, and Z ² , Z ⁴ , Z ⁵ , Z ⁷ and Z ⁸ are hydrogen A compound in which Z ³ is a 2-(acryloyloxy)ethylcarbamoyl group, Z ⁶ and Z ⁹ are phenyl groups, and in formula (a3), Z ¹ is an n-octyl group, and Z ² , Z ⁵ and Z A compound in which ⁸ is a hydrogen atom, Z ⁴ , Z ⁶ , Z ⁷ and Z ⁹ are a methyl group, and Z ³ is a 2-(methacryloyloxy)ethylcarbamoyl group, and in formula (a3), Z ¹ is n- Compounds in which Z ² , Z ⁵ and Z ⁸ are hydrogen atoms, Z ⁴ , Z ⁶ and Z ⁹ are n-butoxy groups, Z ³ is a methacryloyl group, and Z ⁷ is a methacryloyloxy group, etc. are butyl groups. Can be mentioned.

The radically polymerizable compound represented by formula (a1), (a2) or (a3) is, for example, a commercially available benzotriazole compound, benzophenone compound, or triazine compound (hereinafter referred to as "raw material compound") with a (meth)acryloyl group. can be synthesized by introducing The method for introducing the (meth)acryloyl group into the raw material compound is not particularly limited, and any conventional method can be employed. For example, a method in which a raw material compound having an active hydrogen group such as a hydroxyl group, an amino group, or a mercapto group is reacted with (meth)acryloyl chloride in the presence of a base, and a method in which the raw material compound is reacted with 2-bromoethyl methacrylate in the presence of a base. method (JP 2012-072333), a method of reacting the raw material compound with an isocyanate compound having a (meth)acryloyl group in the presence of a tin-based catalyst and/or an amine-based catalyst (Voprosy Khimii i Khimicheskoi Tekhnologii, 1983, 70, 16 -22), a radically polymerizable compound represented by formula (a1), (a2) or (a3) can be synthesized. In addition, a commercially available compound can also be used as the radically polymerizable compound represented by formula (a1), (a2) or (a3).

The optical resin composition according to this embodiment further contains (B) a second radically polymerizable component. The second radically polymerizable component includes one or more radically polymerizable compounds ( (hereinafter sometimes referred to as the "second radically polymerizable compound").

The second radically polymerizable compound has one or more radically polymerizable groups. The second radically polymerizable component may contain one or more types of polyfunctional radically polymerizable compounds. When the second radically polymerizable component contains a polyfunctional radically polymerizable compound, a crosslinked polymer is formed, and a resin material having higher heat resistance is formed. A resin material containing a crosslinked polymer can also be called a cured product of an optical resin composition. Here, the "polyfunctional radically polymerizable compound" means a compound having two or more radically polymerizable groups in the molecule. "Monofunctional radically polymerizable compound" means a compound having one radically polymerizable group in the molecule.

The radically polymerizable group of the second radically polymerizable compound can be a (meth)acrylic group, a vinyl group (excluding the vinyl group included in the (meth)acrylic group), or a combination thereof. Examples of the second radically polymerizable compound include a sulfide compound having a radically polymerizable group and a diphenyl sulfide skeleton, (meth)acrylic acid, (meth)acrylic acid ester, and other vinyl compounds.

The (meth)acrylic acid esters include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, and sec-butyl (meth)acrylate. Acrylate, tert-butyl (meth)acrylate, 2-methylbutyl (meth)acrylate, 2-ethylbutyl (meth)acrylate, 3-methylbutyl (meth)acrylate, 1,3-dimethylbutyl (meth)acrylate, pentyl (meth)acrylate , hexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, 3-ethoxypropyl acrylate , 2-ethoxybutyl acrylate, 3-ethoxybutyl acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenylethyl (meth)acrylate ) acrylate, phenoxyethyl (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, isobornyl (meth)acrylate, ethoxy O-phenylphenol (meth)acrylate , monofunctional (meth)acrylic acid esters such as cyclic trimethylolpropane formal (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, trifluoroethyl methacrylate, and glycidyl (meth)acrylate; and
Ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene Glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1 , 5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, trimethylolpropane tri(meth)acrylate ) acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate, and other polyfunctional (meth)acrylic acid esters. .

Examples of the vinyl compounds include styrene, α-methylstyrene, 2,4-dimethylstyrene, α-ethylstyrene, α-butylstyrene, α-hexylstyrene, 4-chlorostyrene, 3-chlorostyrene, and 4-bromostyrene. , 4-nitrostyrene, 4-methoxystyrene, vinyltoluene, and monofunctional vinyl compounds such as cyclohexene, as well as divinylbenzene, 4-vinylcyclohexene, and 5-vinylbicyclo[2,2,1]hept-2-ene. , diallyl diphenate, and polyfunctional vinyl compounds such as triallyltriazine.

Examples of the sulfide compound having a radically polymerizable group and a diphenyl sulfide skeleton include at least one sulfide compound represented by the following formula (b1) or (b2). A resin material formed from an optical resin composition containing these sulfide compounds can exhibit a low Abbe number and an even higher partial dispersion ratio. Furthermore, there is a tendency for the refractive index of resin materials to become high.

In formulas (b1) and (b2), R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms, and n is 0 to 10 ^R5 represents a hydrogen atom or a methyl group. Two R ⁵ 's in formula (b2) may be the same or different, or may be the same. n in formula (b1) may be 0.

The halogen atom represented by R ¹ , R ² , R ³ or R ⁴ in formula (b1) or (b2) may be, for example, a chlorine atom, a bromine atom, or an iodine atom. Examples of the alkyl group having 1 to 6 carbon atoms represented by R ¹ , R ² , R ³ or R ⁴ in formula (b1) or (b2) include methyl group, ethyl group, n-propyl group, isopropyl group. group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, and n-hexyl group. R ¹ , R ² , R ³ and R ⁴ in formula (b1) or (b2) may all be hydrogen atoms.

Examples of the sulfide compound represented by formula (b1) include bis(4-vinylthiophenyl) sulfide, bis(3-methyl-4-vinylthiophenyl) sulfide, and bis(3,5-dimethyl-4-vinyl). thiophenyl) sulfide, bis(2,3,5,6-tetramethyl-4-vinylthiophenyl) sulfide, bis(3-hexyl-4-vinylthiophenyl) sulfide, bis(3,5-dihexyl-4- vinylthiophenyl) sulfide, bis(3-chloro-4-vinylthiophenyl) sulfide, bis(3,5-dichloro-4-vinylthiophenyl) sulfide, bis(2,3,5,6-tetrachloro-4- vinylthiophenyl) sulfide, bis(3-bromo-4-vinylthiophenyl) sulfide, bis(3,5-dibromo-4-vinylthiophenyl) sulfide, and bis(2,3,5,6-tetrabromo-4 -vinylthiophenyl) sulfide. The sulfide compound represented by formula (b1) is bis(4-vinylthiophenyl) sulfide, bis(3-methyl-4-vinylthiophenyl) sulfide, or bis(3,5-dimethyl-4-vinylthiophenyl) ) sulfide or bis(4-vinylthiophenyl) sulfide.

Examples of the sulfide compound represented by formula (b2) include S,S'-(thiodi-p-phenylene)bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(2 -chlorobenzene)]bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(3-chlorobenzene)]bis(thio(meth)acrylate),S,S'-[4,4' -thiobis(2,6-dichlorobenzene)]bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(3,5-dichlorobenzene)]bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(2-bromobenzene)]bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(3-bromobenzene)]bis(thio (meth)acrylate), S,S'-[4,4'-thiobis(2,6-dibromobenzene)]bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(3 ,5-dibromobenzene)]bis(thio(meth)acrylate),S,S'-[4,4'-thiobis(2-methylbenzene)]bis(thio(meth)acrylate),S,S'-[ 4,4'-thiobis(3-methylbenzene)]bis(thio(meth)acrylate), S,S'-[4,4'-thiobis(2,6-dimethylbenzene)]bis(thio(meth)acrylate) ), S,S'-[4,4'-thiobis(3,5-dimethylbenzene)]bis(thio(meth)acrylate), and S,S'-[4,4'-thiobis(2-tert- butylbenzene)]bis(thio(meth)acrylate), and the like. The sulfide compound represented by formula (b2) is S,S'-(thiodi-p-phenylene)bis(thiomethacrylate), S,S'-[4,4'-thiobis(3,5-dibromobenzene) ] bis(thiomethacrylate), S,S'-[4,4'-thiobis(3,5-dimethylbenzene)]bis(thiomethacrylate), or S,S'-(thiodi-p-phenylene)bis(thio acrylate) or S,S'-(thiodi-p-phenylene)bis(thiomethacrylate).

The sulfide compound represented by formula (b1) is, for example, bis(4-vinylthiophenyl) sulfide in which R ¹ to R ⁴ are all hydrogen atoms and n is 0 in formula (b1), 4,4 It can be obtained by a method in which '-thiodibenzenethiol is reacted with dihaloethane and then the product is dehydrohalogenated in a polar solvent such as dimethyl sulfoxide. can. In this method, vinyl sulfide compounds having different values for n in formula (b1) can be obtained by changing reaction conditions such as the amount of dihaloethane used and the charging method. Alternatively, a method in which a mercaptan compound and a vinyl halide are reacted in the presence of a base (JP-A-3-287572), and a method in which a mercaptan compound and 2-halogenoethanol are reacted as disclosed in JP-A-2004-51488. is reacted in the presence of an alkali metal compound, and then the product is reacted with a halogenating agent to produce a dihalide, and the obtained dihalide is disclosed in JP-A No. 2003-183246. As described above, the sulfide compound represented by formula (b1) can also be obtained by a method comprising heterogeneously reacting with an aqueous alkali metal compound solution in the presence of a phase transfer catalyst in an aliphatic hydrocarbon solvent. can.

The sulfide compound represented by formula (b2) is, for example, S,S'-(thiodi-p-phenylene) in which R ¹ to R ⁴ are all hydrogen atoms and R ⁵ is a methyl group. In the case of bis(thiomethacrylate), an alkali metal salt of 4,4'-thiodibenzenethiol obtained by reacting 4,4'-thiodibenzenethiol with an alkali metal compound and methacryloyl chloride are combined with a nonpolar organic It can be obtained by a method of reaction in a solvent.

The second radically polymerizable component includes a sulfide compound represented by formula (b1) or (b2) and other radicals selected from (meth)acrylic acid, (meth)acrylic acid ester, and other vinyl compounds. It may also contain a polymerizable compound. Examples of (meth)acrylic acid, (meth)acrylic acid ester, and other vinyl compounds used in combination with the sulfide compound represented by formula (b1) or (b2) as the second radically polymerizable component are as described above. It is similar to that of .

The content of each radically polymerizable compound in the optical resin composition is adjusted so that the Abbe number νd and the partial dispersion ratio θg,F of the resin material containing these polymers satisfy the above formula. For example, when the ratio of the first radically polymerizable component is large, the Abbe number νd tends to decrease and the partial dispersion ratio θg,F tends to increase. Furthermore, when the ratio of the second radically polymerizable component is large, the partial dispersion ratio θg,F tends to decrease. More specifically, for example, by adjusting the content of each radically polymerizable compound with reference to the numerical ranges exemplified below, a resin material exhibiting an Abbe number νd and a partial dispersion ratio θg,F that satisfy the above formula can be obtained. It is possible to find a blending ratio of the optical resin composition that gives the following.

(A) The total content of the first radically polymerizable component is 3 to 80 parts by mass, 5 to 80 parts by mass, based on 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component. It may be 70 parts by weight, or 5 to 60 parts by weight.

The content of the radically polymerizable compound represented by formula (a1) is determined from the viewpoint of maintaining high light transmittance with respect to the total amount of 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component. From the viewpoint of increasing the partial dispersion ratio θg,F, it may be 60 parts by mass or less, 50 parts by mass or less, or 30 parts by mass or less, and may be 3 parts by mass or more, or 5 parts by mass or more. The content of the radically polymerizable compound represented by formula (a2) is determined from the viewpoint of maintaining high light transmittance with respect to the total amount of 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component. Therefore, the amount may be 80 parts by mass or less, and from the viewpoint of increasing the partial dispersion ratio θg,F, it may be 30 parts by mass or more. The content of the radically polymerizable compound represented by formula (a3) is determined from the viewpoint of maintaining high light transmittance with respect to the total amount of 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component. Therefore, the amount may be 70 parts by mass or less, and from the viewpoint of increasing the partial dispersion ratio θg,F, it may be 20 parts by mass or more.

(B) The total content of the second radically polymerizable component increases the partial dispersion ratio θg,F with respect to the total amount of 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component. From the viewpoint, it may be 97 parts by mass or less, 95 parts by mass or less, or 90 parts by mass or less, and from the viewpoint of maintaining high light transmittance, it may be 5 parts by mass or more, 10 parts by mass or more, or 20 parts by mass or more. It's okay.

The total content of the sulfide compounds represented by formula (b1) or (b2) is based on the light resistance of the resin material with respect to 100 parts by mass of the total amount of the first radically polymerizable component and the second radically polymerizable component. From the viewpoint of improving properties, the amount may be 95 parts by mass or less, or 90 parts by mass or less, and in order to obtain a resin material having a high refractive index (for example, 1.630 or more, or 1.650 or more), 5 parts by mass or more, or 15 parts by mass or more. Moreover, the ratio of the sulfide compound represented by formula (b1) or (b2) in the (B) second radically polymerizable compound is 15, based on the total mass of the (B) second radically polymerizable component. It may be ~100% by weight, 20-100% by weight, or 25-100% by weight. When the ratio of the sulfide compound represented by formula (b1) or (b2) is within these ranges, a resin material having a low Abbe number νd, high light transmittance, and a high refractive index can be easily obtained.

The optical resin composition according to the present embodiment may further contain a radical polymerization initiator for advancing radical polymerization of the first and second radically polymerizable components. The radical polymerization initiator can be a photoradical polymerization initiator, a thermal radical polymerization initiator, or a combination thereof.

Examples of photoradical polymerization initiators include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 1-hydroxycyclohexyl-phenylketone, 2-hydroxy-2-methyl-1 -phenyl-propan-1-one, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, 4-phenylbenzophenone, 4-phenoxybenzophenone, 4,4'-diphenylbenzophenone, and 4,4'- Examples include diphenoxybenzophenone. Only one type of photoradical polymerization initiator can be used, or two or more types can be used in combination.

The content of the photoradical polymerization initiator can be appropriately selected depending on the amount of light irradiation, additional heating temperature, and the like. The content of the photoradical polymerization initiator can also be adjusted depending on the target average molecular weight of the polymer to be formed. The content of the photoradical polymerization initiator is 0.1 to 10 parts by mass, 0.1 to 10 parts by mass, based on 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component in the optical resin composition. .2 to 8 parts by weight, or 0.3 to 7 parts by weight. If the content of the photoradical polymerization initiator is less than 0.1 part by mass, the polymerization reaction may be difficult to proceed sufficiently. If the content of the photoradical polymerization initiator exceeds 10 parts by mass, the resin material formed may be colored and the light transmittance may be reduced.

Examples of thermal radical polymerization initiators include azobisoisobutyl nitrile, benzoyl peroxide, tert-butyl peroxy pivalate, tert-butyl peroxy neohexanoate, tert-hexyl peroxy neohexanoate, tert-butyl Peroxyneodecanoate, tert-hexylperoxyneodecanoate, cumylperoxyneohexanoate, cumylperoxyneodecanoate, and 1,1,3,3,-tetramethylbutylperoxy2- Examples include ethylhexanoate. Only one type of thermal radical polymerization initiator can be used, or two or more types can be used in combination.

The content of the thermal radical polymerization initiator can be appropriately selected depending on the heating temperature, the amount of oxygen present during radical polymerization, and the like. The content of the thermal radical polymerization initiator can also be adjusted depending on the target degree of polymerization of the polymer to be formed. The content of the thermal radical polymerization initiator is 0.05 to 10 parts by mass, 0.05 to 10 parts by mass, based on 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component in the optical resin composition. .1 to 8 parts by weight, or 0.2 to 6 parts by weight. If the content of the thermal radical polymerization initiator is less than 0.05 part by mass, the polymerization reaction may be difficult to proceed sufficiently. If the content of the thermal radical polymerization initiator exceeds 10 parts by mass, the resin material formed may be colored and the light transmittance may be reduced.

As a polymerization initiator other than a radical polymerization initiator, for example, a photocationic polymerization initiator or a thermal cationic polymerization initiator can also be used.

The optical resin composition according to the present embodiment contains fine particles such as inorganic fine particles dispersed in a homogeneous phase containing the first and second radically polymerizable components to the extent that the required optical properties are maintained. It's okay. However, from the viewpoint of maintaining high light transmittance of the resin material, the content of fine particles may be 0 to 15% by mass, 0 to 10% by mass, 0 to 5% by mass, or 0 to 2% by mass. good.

The optical resin composition according to this embodiment may further contain other components as necessary. Examples include polymerization inhibitors, antioxidants, light stabilizers, plasticizers, leveling agents, antifoaming agents, UV absorbers, coupling agents, sensitizers, metal deactivators, chain transfer agents, and antiblocking agents. Examples include additives such as a mold release agent and a mold release agent. The content of these additives is 0 to 50 parts by mass, 0 to 30 parts by mass based on 100 parts by mass of the first radically polymerizable component and the second radically polymerizable component in the optical resin composition. parts, or 0 to 20 parts by mass.

The Abbe number νd of the resin material formed from the optical resin composition in this embodiment is 18≦νd≦25, and may be 18≦νd≦24, or 18≦νd≦23. The partial dispersion ratio θg,F of the resin material is 0.700 or more, and may be 0.710 or more, or 0.720 or more. When the Abbe number νd and the partial dispersion ratio θg,F are within these ranges, sufficient chromatic aberration correcting ability can be more easily imparted to the resin material. The upper limit of the partial dispersion ratio θg,F is not particularly limited, but is usually about 0.900.

In this specification, the Abbe number νd and the partial dispersion ratio θg,F mean values calculated by the following equations.
Abbe number νd=(nd-1)/(nF-nC)
Partial dispersion ratio θg, F = (ng-nF)/(nF-nC)
In the formula, ng is the refractive index at a wavelength of 435.8 nm which is the G line, nF is the refractive index at a wavelength of 486.1 nm which is the F line, nd is the refractive index at a wavelength of 587.6 nm which is the D line, and nC is the refractive index at the C line. It shows the refractive index at a certain wavelength of 656.3 nm.

When the resin material formed from the optical resin composition according to the present embodiment is subjected to a light resistance test, the difference ΔT in the change in light transmittance at a wavelength of 400 nm of the resin material before and after the light resistance test is 5%. It may be the following. If ΔT exceeds 5%, there is a possibility that the reliability of an optical system constructed using the resin material will be lowered. Although the lower limit of ΔT is not particularly limited, it is ideally 0%.

The light resistance test here uses a xenon weather meter (for example, manufactured by Suga Test Instruments Co., Ltd., model ^number : This is a test in which light is irradiated for 100 hours under the following conditions. The thickness of the sheet-like test piece (molded body) of the resin material used for the light resistance test is 190 to 210 μm. When the light transmittance of the test piece after the light fastness test at a wavelength of 400 nm is T2, and the light transmittance of the test piece before the light fastness test at a wavelength of 400 nm is T1, the difference between T1 and T2 is ΔT. Values converted to a thickness of 200 μm are used as T1 and T2.

For example, using the sulfide compound represented by the above formula (b1) or (b2) and keeping the content within the above range can contribute to setting ΔT to 5% or less.

The glass transition temperature (Tg) of the resin material formed from the optical resin composition according to this embodiment may be 100°C or higher, or 110°C or higher. Tg is one of the indicators showing heat resistance. If Tg is less than 100° C., the molded body of the resin material is likely to deform, especially in a high temperature range, which may lead to a decrease in the reliability of an optical system constructed using the resin material in a high temperature environment. Although the upper limit of Tg is not particularly limited, it is usually about 300°C. However, the resin material may not exhibit a glass transition temperature.

In this specification, Tg refers to the dynamic viscoelasticity of a resin material measured in tensile mode using a dynamic viscoelasticity measuring device (for example, manufactured by TA Instruments Japan, model number: RSA-G2). It means the temperature at the peak top of tan δ when measured under the conditions of a temperature increase rate of 10° C./min and a frequency of 1 Hz.

When the resin material formed from the optical resin composition according to the present embodiment is subjected to a boiling test, the difference Δnd in the refractive index nd at the d-line (wavelength 587.6 nm) before and after the boiling test is 0.0007 or less. , or 0.0005 or less. If Δnd exceeds 0.0007, there is a possibility that the reliability of an optical system constructed using the resin material in a high temperature and high humidity environment, that is, the moisture and heat resistance will be reduced. The lower limit of Δnd is not particularly limited, but is ideally 0.

The boiling test here is a test in which a sheet-like test piece (molded body) of a resin material with a thickness of 1.9 to 2.0 mm is immersed in a hot water bath maintained at 100° C. for 24 hours. The refractive index nd of each test piece before and after the boiling test is measured, and the difference therebetween is defined as Δnd.

The refractive index nd of the resin material formed from the optical resin composition according to this embodiment may be 1.550 or more, 1.600 or more, 1.630 or more, or 1.650 or more. When the resin material has such a high refractive index, the degree of freedom in optical design increases when applied to optical system materials such as lenses. The upper limit of the refractive index nd is not particularly limited, but is usually about 1.800.

The internal transmittance T _i of the resin material formed from the optical resin composition according to the present embodiment may be 50% or more, 60% or more, or 75% or more. If T _i is less than 50%, color reproducibility may be impaired when the resin material is applied to an imaging optical system such as a lens, and the degree of freedom in optical design may be reduced. The upper limit of the internal transmittance T _i is not particularly limited, and is ideally 100%.

The internal transmittance Ti here is a value converted to a thickness of 200 μm at a wavelength of 400 nm. The external transmittance at a wavelength of 400 nm of a test piece (molded body) with a thickness of 90 to 110 μm and a test piece with a thickness of 190 to 200 μm is measured, and the internal transmittance Ti is calculated from the following formula.
log(T _i /100)=-[{log(T ₃ )-log(T ₄ )}/(d ₄ -d ₃ )]×200
Here, d ₃ is the measured thickness of a test piece with a thickness of 90 to 110 μm, d ₄ is the measured thickness of a test piece with a thickness of 190 to 210 μm, T ₃ is the external transmittance at a wavelength of 400 nm of a test piece with a thickness of 90 to 110 μm, T ₄ is the external transmittance at a wavelength of 400 nm of a test piece with a thickness of 190 to 210 μm. External transmittance is light transmittance including surface reflection loss.

The optical resin composition according to the present embodiment can be prepared, for example, by a method of mixing the first and second polymerizable components and, if necessary, other components (polymerization initiator, additives, etc.) and stirring the mixture. It can be obtained by Each component may be mixed simultaneously or sequentially. The temperature during stirring is not particularly limited, but is usually 0 to 120°C, and may be 10 to 100°C. The stirring time may be 0.1 to 24 hours, or 0.1 to 6 hours. The temperature and stirring time during stirring are adjusted as appropriate depending on the type of polymerization initiator.

Using the optical resin composition according to this embodiment, a molded article of a resin material having an arbitrary shape can be manufactured. A molded article of a resin material is produced, for example, by radically polymerizing a first radically polymerizable component and a second radically polymerizable component in an optical resin composition filled in a mold, and then forming a resin material containing these polymers. It can be manufactured by a method including forming a molded body of a resin material, and removing the formed molded body of a resin material from a mold.

Before filling the optical resin composition into a mold, if you want to improve the viscosity of the optical resin composition for the purpose of improving operability, etc., the first radically polymerizable component is prepolymerized until the desired viscosity is achieved. The radical polymerization of the second radically polymerizable component may proceed to some extent.

The optical resin composition may be degassed and defoamed before being filled into the mold. Thereby, radical polymerization can proceed efficiently while maintaining a state in which the optical resin composition does not come into contact with air (oxygen). The method of degassing and defoaming the optical resin composition is not particularly limited, and examples include bubbling with an inert gas such as nitrogen and argon, vacuum degassing, ultrasonic degassing, hollow fiber membrane degassing, or any of these. A combination of these can be adopted.

Radical polymerization of the first radically polymerizable component and the second radically polymerizable component can proceed by thermal polymerization, photopolymerization, or a combination thereof.

The polymerization temperature and polymerization time for thermal polymerization vary depending on the type and blending ratio of the radically polymerizable component, the type and amount used of the thermal radical polymerization initiator, and the like. Generally, the polymerization temperature may be 0 to 180°C, or 20 to 150°C, and the polymerization time may be 0.1 to 30 hours, or 0.1 to 12 hours.

In the case of photopolymerization, the optical resin composition filled in the mold is irradiated with light such as ultraviolet rays. Examples of light sources used for photopolymerization include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, deuterium lamps, argon lamps, xenon lamps, LEDs, halogen lamps, excimer lasers, and helium-cadmium lasers. can be mentioned. The cumulative amount of irradiated light varies depending on the type and ratio of the radically polymerizable component, the type and amount used of the photoradical polymerization initiator, the shape and shape of the molded article, etc. Usually, the integrated light amount may be 0.01 to 100 J/cm ² or 0.1 to 50 J/cm ² .

Since the molded article of the resin material obtained from the optical resin composition according to the present embodiment exhibits a low Abbe number and a high partial dispersion ratio, it can be applied as an optical member constituting an imaging optical system such as an optical lens. This makes it possible to highly correct the chromatic aberration of the optical system. Optical Lens The optical lens formed from the optical resin composition according to the present embodiment can be used, for example, in imaging optical systems such as camera lenses for optical equipment, camera lenses for vehicles, camera lenses for smartphones, and lenses for digital cameras. can. The thickness of the optical lens can be appropriately set as desired and is not particularly limited, but is usually 1 μm to 10 mm, and may be 1 μm to 5 mm. FIG. 1 is a cross-sectional view showing one embodiment of an optical lens. The optical lens 1 shown in FIG. 1 is a molded body of a resin material formed from the optical resin composition according to the present embodiment.

Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples. However, the present invention is not limited to the following examples.

・化合物Ａ－２：２－ヒドロキシ－４－メタクリロイルオキシベンゾフェノン（下記式（ａ２－１）で表される化合物、Ａｌｆａ Ａｅｓａｒ社製）

・化合物Ａ－３：以下の製造例１で合成した下記式（ａ３－１）で表される化合物

1. Preparation of raw materials (A) First radically polymerizable component/compound A-1: 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole (formula (a1- Compound represented by 1), manufactured by Tokyo Kasei)

・Compound A-2: 2-hydroxy-4-methacryloyloxybenzophenone (compound represented by the following formula (a2-1), manufactured by Alfa Aesar)

・Compound A-3: Compound represented by the following formula (a3-1) synthesized in Production Example 1 below

[Manufacture example 1]
TINUVIN479 (manufactured by BASF, compound name: 2-[4-(4,6-bis-biphenyl-4-yl-[1,3 , 5]triazin-2-yl)-3-hydroxy-phenoxy]-propionic acid 6-methyl-heptyl ester) 70 g (0.10 mol), DMF (dehydrated grade) 70 g, tin(II) 2-ethylhexanoate 0.42 g (0.001 mol) and 0.01 g (0.0001 mol) of tert-butylxylenol were charged, and these were stirred at 60° C. for 30 minutes. Next, 15.2 g (0.11 mol) of Karenz AOI (manufactured by Showa Denko, compound name: 2-acryloyloxyethyl isocyanate) was added dropwise thereto over 10 minutes. 0.16 g (0.001 mol) of diazabicycloundecene (DBU) was further added to the reaction solution in the flask, the temperature of the reaction solution was raised to 110° C., and the reaction was allowed to proceed at 110° C. over 6 hours. Next, 120 g of toluene and 70 g of water were added, and the mixture in the flask was stirred at 85° C. for 2 hours. The organic layer taken out from the liquid mixture by liquid separation was washed twice with 100 g of water. The organic layer after washing was concentrated, and the resulting crude product was purified by column chromatography to obtain 25.5 g of compound A-3. The HPLC purity of the obtained compound A-3 was 97%. Furthermore, the yield relative to TINUVIN479 was 30%.

(B) Second radically polymerizable component/compound B-1: Bis(4-vinylthiophenyl) sulfide (radical polymerizable compound represented by formula (b1)) synthesized in Production Example 2 below
・Compound B-2: S,S'-(thiodi-p-phenylene)bis(thiomethacrylate) (radical polymerizable compound represented by formula (b2)) synthesized in Production Example 3 below
・Compound B-3: Methyl methacrylate (manufactured by Tokyo Kasei)
・Compound B-4: Styrene (manufactured by Tokyo Kasei)
・Compound B-5: Ethoxylated bisphenol A diacrylate (manufactured by Shin Nakamura Chemical Industries, product name: ABE-300)
・Compound B-6: Trimethylolpropane triacrylate (manufactured by Shin-Nakamura Chemical Industries, product name: A-TMPT)
・Compound B-7: Triethylene glycol diacrylate (manufactured by Kyoeisha Chemical, trade name: Light Acrylate 3EG-A)

[Manufacture example 2]
250.4 g (1.0 mol) of 4,4'-thiodibenzenethiol and 480.0 g (2 mol) of a 17% by mass aqueous sodium hydroxide solution were placed in a 2 L four-necked flask equipped with a stirrer, a dropping funnel, and a thermometer. .0 mol) and stirred at 60° C. for 1 hour. Next, 169.1 g (2.1 mol) of 2-chloroethanol was added dropwise at 60° C. over 1.5 hours. After the dropwise addition was completed, the reaction was allowed to proceed at 60° C. for 1.5 hours. After the reaction was completed, the reaction solution was cooled to 20° C., and the precipitated crystals were taken out by filtration. The crystals were washed twice with 400 g of water to obtain 492.5 g of a wet cake containing bis[4-(2-hydroxyethylthio)phenyl] sulfide.

492.5 g of the obtained wet cake and 1500 g of toluene were charged into a 3 L four-necked flask equipped with a stirrer, a dropping funnel, and a thermometer, and the flask was heated at 110° C. to distill water off by azeotropic distillation. . During distillation, the toluene that was distilled off azeotropically with water was separated from the water and returned to the flask. The remaining solution was cooled to 70°C, and 249.9 g (2.1 mol) of thionyl chloride was added dropwise thereto at 70°C over 2 hours. After the dropwise addition was completed, the reaction was allowed to proceed by heating at 70° C. for 2 hours. After the reaction was completed, 600 g (1.5 mol) of a 10% by mass aqueous sodium hydroxide solution was added to the reaction solution, and the resulting mixed solution was separated at 70°C. The organic layer obtained by liquid separation was cooled to 10° C. to precipitate crystals. The crystals were taken out by filtration and washed with 600 g of n-heptane. The washed crystals were dried by heating to 50° C. under reduced pressure to obtain 348.0 g (0.93 mol) of bis[4-(2-chloroethylthio)phenyl] sulfide.

Next, 348.0 g (0.93 mol) of bis[4-(2-chloroethylthio)phenyl] sulfide, 780 g of n-heptane, 14.9 g (0.046 mol) of tetrabutylammonium bromide and 48% by mass hydroxide. 232.5 g (2.8 mol) of sodium aqueous solution was charged into a 3 L four-necked flask equipped with a stirrer and a thermometer, and the mixture was heated at 75 to 85°C for 5.5 hours to allow the reaction to proceed. . After the reaction was completed, 428 g of water was added to the reaction solution in the flask, and the resulting mixed solution was separated at 60°C. The organic layer obtained by separation was washed twice with 372 g of water to obtain 1050 g of a solution of bis(4-vinylthiophenyl) sulfide in n-heptane.

1.4 g of 2,6-di-tert-butyl-4-methylphenol was added to the obtained n-heptane solution, and the n-heptane was distilled off under the conditions of 0.6 kPa and 40°C to obtain bis(4 -vinylthiophenyl) sulfide (compound B-1) 275.3 g (0.91 mol) was obtained. The HPLC purity of the obtained compound B-1 was 99%. The yield based on 4,4'-thiodibenzenethiol was 91%.

[Manufacture example 3]
In a 2 L four-necked flask equipped with a stirrer, a dropping funnel, and a thermometer, 250.4 g (1 mol) of 4,4'-thiodibenzenethiol and 800 g of monochlorobenzene were charged under a nitrogen atmosphere. While heating the inside of the flask to 60 to 65°C, 114.3 g (2.8 mol) of 98% by mass sodium hydroxide and 1.9 g (0.05 mol) of sodium borohydride were added to 546.8 g of water. 663.0 g of the dissolved aqueous solution was added dropwise over 1 hour. After the dropwise addition was completed, the reaction was allowed to proceed by heating at the same temperature for 1 hour. After the reaction was completed, the reaction solution was separated to obtain 910.6 g (aqueous layer) of an aqueous solution containing the sodium salt of 4,4'-thiodibenzenethiol.

230.0 g (2.2 mol) of methacryloyl chloride, 450 g of n-heptane, 900 g of cyclohexane, and 2.0 g of p-methoxyphenol were charged into a 3 L four-neck flask equipped with a stirrer, a dropping funnel, and a thermometer. was cooled to 5°C. Thereto, 910.6 g of the aqueous solution containing the sodium salt of 4,4'-thiodibenzenethiol cooled to 5° C. was added dropwise over 5 minutes. After the dropwise addition was completed, the reaction solution was heated at 55 to 60° C. for 1 hour to allow the reaction to proceed. After the reaction was completed, the reaction solution was separated to obtain an organic layer. The obtained organic layer was washed twice with 140 g of water. 2.0 g of p-methoxyphenol and 1.5 g of activated carbon were added to the washed organic layer, and the organic layer was stirred at 55 to 60° C. for 30 minutes. Thereafter, insoluble matter was removed by hot filtration. Crystals were precipitated by cooling the remaining organic layer to 0°C. The precipitated crystals were filtered off. The obtained crystals were washed with a mixture of 170 g of n-heptane, 340 g of cyclohexane, and 0.13 g of p-methoxyphenol, and dried under reduced pressure to obtain white S,S'-(thiodi-p-phenylene)bis. (Thiomethacrylate) (Compound B-2) 325.5 g (0.84 mol) was obtained. The HPLC purity of the obtained compound B-1 was 99%. Further, the yield based on 4,4'-thiodibenzenethiol was 84%.

2. Optical resin composition and molded article of resin material (Example 1)
Compound A-1 and compound B-4 were mixed at the mass ratio shown in Table 1, and the mixture was stirred at 60° C. for 30 minutes. After cooling to 25°C, 3 parts by mass of IRGACURE 1173 (manufactured by BASF, 2-hydroxy-2-methyl-1-phenyl-propan-1-one) was dissolved in the mixture as a photoradical polymerization initiator based on 100 parts by mass of the mixture. The resulting mixed solution (optical resin composition) was sufficiently degassed. Next, the optical resin composition was applied to a glass mold in which two glass plates of 76 x 52 mm were arranged with a gap of 200 μm, and a glass mold in which two glass plates of 76 x 52 mm were arranged with a gap of 100 μm. was filled. Radical polymerization of Compound A-1 and Compound B-4 was performed by irradiating the optical resin composition filled in the glass mold with light of 5000 mJ/cm ² (integrated illuminance at 365 nm sensor) using a high-pressure mercury lamp. A molded body of a resin material containing the polymer formed by the above was formed. The formed body was taken out from the glass mold. Thereby, sheet-like molded bodies for evaluation with a thickness of about 200 μm and a thickness of about 100 μm were obtained.

Instead of the photoradical polymerization initiator, 0.5 parts by mass of Perocta O (manufactured by NOF Co., Ltd., 1,1,3,3,-tetramethyl Butylperoxy 2-ethylhexanoate) was added as a thermal radical polymerization initiator to prepare an optical resin composition, which was thoroughly degassed. Next. The optical resin composition was filled into a gap between two circular glass molds each having a diameter of 73 mm and arranged with a gap of 2 mm. After heating the glass mold filled with the optical resin composition at 55°C for 2 hours, the temperature was raised from 55°C to 95°C over 12 hours, and by heating at 95°C for 2 hours, compound A-1 was obtained. A molded body of a resin material containing a polymer formed from Compound B-4 was formed. The formed body was taken out from the glass mold. As a result, a disk-shaped molded article for evaluation with a thickness of about 2 mm was obtained.

(Examples 2 to 16, Comparative Examples 1 to 3)
An optical resin composition was prepared in the same manner as in Example 1 except that each raw material was used in the ratio shown in Table 1, and three types of molded bodies for evaluation were produced using this.

3. Evaluation <Refractive index nd, Abbe number νd, partial dispersion ratio θg, F>
G-line (wavelength 435.8 nm), F-line (wavelength 486.1 nm), d-line (wavelength 587.6 nm), and C-line (wavelength The refractive indexes ng, nd, nF, and nC at 656.3 nm) were measured at 25° C. using a Carl Zeiss Jena refractometer PR-2 (V block method). From the obtained refractive index, the Abbe number and θg, F were calculated using the following formulas.
Abbe number νd=(nd-1)/(nF-nC)
Partial dispersion ratio θg, F = (ng-nF)/(nF-nC)

<Heat resistance>
The temperature change in dynamic viscoelasticity of a test piece (molded body) for evaluation with a thickness of approximately 200 μm was measured using a dynamic viscoelasticity measuring device (manufactured by TA Instruments Japan, model number: RSA-G2). The measurement was carried out under the conditions of tensile mode, temperature increase rate of 10° C./min, and frequency of 1 Hz. The temperature at the peak top of tan δ was recorded as the glass transition temperature Tg of the molded article. The heat resistance of the molded product was determined based on the Tg value based on the following criteria.
AA: Tg≧110℃
A: 100≦Tg<110℃
C: Tg<100℃

<Moisture heat resistance>
A test piece (molded body) for evaluation with a thickness of about 2 mm was subjected to a boiling test in which it was immersed in a hot water bath maintained at 100° C. for 24 hours. The refractive index nd of the test piece before and after the boiling test was measured, and the difference Δnd between them was determined. Based on the value of Δnd, the heat-and-moisture resistance of the molded article was determined based on the following criteria.
AA: Δnd≦0.0005
A: 0.0005<Δnd≦0.0007
C:Δnd>0.0007

<Internal transmittance>
The transmittance at a wavelength of 400 nm of a test piece (molded body) for evaluation with a thickness of approximately 200 μm and a test piece (molded body) for evaluation with a thickness of approximately 100 μm was measured using a spectrophotometer (manufactured by Hitachi, Ltd., model number: UH- 4150). The measured value obtained here is the external transmittance including surface reflection loss. Using the obtained measurement value and the actually measured thickness of each test piece, the internal transmittance T _i at a wavelength of 400 nm converted to a thickness of 200 μm was calculated from the following formula.
log(T _i /100)=-[{log(T ₃ )-log(T ₄ )}/(d ₄ -d ₃ )]×200
_d3 : Measured thickness of a molded body approximately 100 μm thick _d4 : Measured thickness of a molded body approximately 200 μm thick _T3 : External transmittance at a wavelength of 400 nm of a molded body approximately 100 μm thick _T4 : Measured thickness of a molded body approximately 200 μm thick External transmittance at wavelength 400nm

The internal transmittance of the molded body was determined based on the value of the internal transmittance Ti based on the following criteria.
AA: T _i ≧75%
A: 60%≦T _i <75%
B: 50%≦T _i <60%
C: T _i <50%

<Light resistance>
A test piece (molded body) for evaluation with a thickness of about 200 μm was measured using a xenon weather meter (manufactured by Suga Test Instruments Co., Ltd., model ^number : A light resistance test was conducted in which light was irradiated for 100 hours at a black panel temperature of 63°C. The transmittance at a wavelength of 400 nm of each molded article before and after the light resistance test was measured using a spectrophotometer (manufactured by Hitachi, Ltd., model number: UH-4150). Using these values and the actually measured thickness of the molded body, the transmittance converted to a thickness of 200 μm was calculated using the Lambert-Beer equation. The difference ΔT in transmittance at a wavelength of 400 nm before and after the light resistance test was determined, and the light resistance was determined based on the value based on the following criteria.
A: ΔT=0 to 5%
C:ΔT>5%

1...Optical lens.

Claims (7)

(A) a first radically polymerizable component consisting of at least one radically polymerizable compound represented by the following formula (a1), (a2) or (a3);
(B) a second radically polymerizable component comprising at least one radically polymerizable compound different from the first radically polymerizable component;
An optical resin composition containing,
The second radically polymerizable component is a sulfide compound having a radically polymerizable group and a diphenyl sulfide skeleton, a (meth)acrylic acid ester, and a vinyl group containing a vinyl group (excluding the vinyl group contained in the ( meth)acrylic group). type compound, or a combination thereof, the (meth)acrylic acid ester and the vinyl compound are compounds excluding the sulfide compound,
The vinyl compound is styrene, α-methylstyrene, 2,4-dimethylstyrene, α-ethylstyrene, α-butylstyrene, α-hexylstyrene, 4-chlorostyrene, 3-chlorostyrene, 4-bromostyrene, selected from 4-nitrostyrene, 4-methoxystyrene, vinyltoluene, and divinylbenzene,
When the first radically polymerizable component and the second radically polymerizable component undergo radical polymerization, a resin material containing these polymers is formed,
The Abbe number νd and partial dispersion ratio θg,F of the resin material are expressed by the following formula:
18≦νd≦25; and θg, F≧0.700
An optical resin composition that satisfies the following.
[In formula (a1),
X ¹ is a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, an alkoxycarbonylalkyl group having 1 to 18 carbon atoms which may have a substituent, or , represents a group having a (meth)acryloyl group,
X ² and X ³ each independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 18 carbon atoms that may have a substituent,
X ⁴ represents a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
X ⁵ represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
At least one of X ¹ , X ⁴ or X ⁵ is a group having a (meth)acryloyl group. ]
[In formula (a2),
Y ¹ and Y ² each independently represent a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
Y ³ and Y ⁴ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a group having a (meth)acryloyl group,
At least one of Y ¹ , Y ² , Y ³ or Y ⁴ is a group having a (meth)acryloyl group. ]
[In formula (a3),
Z ¹ is a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, an alkylcarbonyloxyalkyl group having 1 to 18 carbon atoms which may have a substituent, and an alkoxycarbonylalkyl group having 1 to 18 carbon atoms, or an alkoxyalkyl group having 1 to 18 carbon atoms, which may have a substituent;
Z ² , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁸ and Z ⁹ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a substituent. Indicates an optional alkoxy group having 1 to 8 carbon atoms,
Z ³ represents a hydrogen atom or a group having a (meth)acryloyl group,
Z ⁷ is a hydrogen atom, a hydroxyl group, a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, an alkoxy group having 1 to 8 carbon atoms which may have a substituent, or (meth) Indicates a group having an acryloyl group,
At least one of Z ³ or Z ⁷ is a group having a (meth)acryloyl group. ] A sheet-like molded article of the resin material with a thickness of 190 to 210 μm was subjected to a light resistance test in which it was irradiated with light for 100 hours under the conditions of an integrated illuminance of 60 W/m ² in the wavelength range of 300 to 400 nm and a black panel temperature of 63 ° C. The optical resin composition according to claim 1, wherein the difference ΔT in transmittance at a wavelength of 400 nm of the molded article before and after the light resistance test is 5% or less when provided. The optical resin composition according to claim 1 or 2, wherein the resin material has a glass transition temperature of 100°C or higher. When a sheet-like molded body of the resin material with a thickness of 1.9 to 2.0 mm was subjected to a boiling test in which it was immersed in a water bath maintained at 100°C for 24 hours, the d-line (wavelength 587 The optical resin composition according to any one of claims 1 to 3, wherein a difference Δnd in refractive index nd before and after the boiling test at a wavelength of 0.6 nm) is 0.0007 or less. (B) The optical resin according to any one of claims 1 to 4, wherein the second radically polymerizable component contains at least one kind of the sulfide compound represented by the following formula (b1) or (b2). Composition.
[In formulas (b1) and (b2), R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, and n is 0 to represents an integer of 10, R ⁵ represents a hydrogen atom or a methyl group, and two R ^5s in formula (b2) may be the same or different. ] The optical resin composition according to any one of claims 1 to 5, wherein the optical resin composition may contain fine particles. Consisting of a resin material containing a polymer formed by radical polymerization of the first radically polymerizable component and the second radically polymerizable component in the optical resin composition according to any one of claims 1 to 6. optical lens.

Images