JP2019101301A - Cured product, optical element, optical instrument, and method of producing optical element - Google Patents

Abstract

To provide an optical composition capable of forming a cured product and an optical element with a characteristic of a high chromatic aberration correction function that hardly crystallizes.SOLUTION: The cured product is obtained by polymerizing compounds represented by general formula (1) with compounds represented by general formula (2), where the content of the compounds represented by general formula (2) is 0.1-50.0 mass% of the total content of the compounds represented by general formula (1).SELECTED DRAWING: None

Description

  The present invention relates to a cured product, an optical element and an optical device, and more particularly to a cured product, an optical element and an optical device having high secondary dispersion characteristics.

Generally, the refractive index of an optical material made of a glass material (glass material), an organic resin or the like gradually increases as the wavelength becomes shorter. The Abbe number (dispersion characteristic) (ν _d ), the second-order dispersion characteristic (θg, F), and the like can be given as an index indicating the wavelength dispersion of the refractive index. The Abbe number and θg and F values are values specific to the respective optical materials, but in many cases, they are within a certain range. FIG. 2 is a view showing the relationship between the secondary dispersion characteristics of the conventional optical material (glass material and organic material) and the Abbe number.

  In the refractive optical system, it is possible to reduce the chromatic aberration by appropriately combining glass materials having different dispersion characteristics. For example, in an objective lens such as a telescope, a chromatic aberration appearing on the optical axis is corrected by using a glass material having a small dispersion as a positive lens and a glass material having a large dispersion as a negative lens in combination. However, when the lens configuration and the number of lenses are limited or when the glass material to be used is limited, it may be very difficult to sufficiently correct the chromatic aberration. As one of the methods for solving such problems, there is a method of utilizing a glass material having anomalous dispersion characteristics, and design of optical elements using this method is carried out.

  In addition, when manufacturing an optical element excellent in chromatic aberration correction function and having an aspheric shape or the like, a method such as molding a resin on a glass material such as spherical glass is used rather than using only the glass material as a material. . This method is excellent in mass productivity, moldability, and freedom of shape. However, as shown in FIG. 2, the optical characteristics of the conventional organic material fall within a limited fixed range (second-order dispersion characteristics [θg, F] of 0.700 or less), and the unique dispersion characteristics Very little organic material is shown.

  Furthermore, many of the organic materials exhibiting unique dispersion characteristics are compounds in which a conjugated system is formed by a double bond, a benzene ring, or the like, which has high rigidity and orientation, and is easily crystallized. When an optical element such as a lens is produced using an organic material exhibiting such a unique dispersion characteristic, non-uniform portions may occur due to the crystallization of the organic material.

  Patent Document 1 proposes an optical element having a molded product obtained by polymerizing a sulfone (meth) acrylate having secondary dispersion characteristics (high θg, F characteristics) higher than general-purpose organic materials.

  Patent Document 2 proposes an optical element having a molded body obtained by polymerizing a compound in which a branched chain substituent is introduced into the same molecular skeleton as Patent Document 1 in order to reduce birefringence. .

JP, 2012-167019, A JP, 2014-43565, A

  However, although the organic materials disclosed in Patent Document 1 have high θg and F values, they are easily oriented due to their molecular structure, and easily become crystals. Further, the material shown in Patent Document 2 also has a branched structure in the side chain because of the same molecular skeleton as the organic material shown in Patent Document 1 although the values of θg and F are high, It is easy to become.

The present invention has been made in view of the background art described above, and is a cured product having high refractive index dispersion characteristics (Abbe number (ν _d )) and secondary dispersion characteristics (θg, F) and which is difficult to crystallize And provide an optical element using the cured product.

  In the cured product of the present invention, at least the compound represented by the following general formula (1) and / or the compound represented by the general formula (3) and the compound represented by the following general formula (2) are polymerized It is a cured product, and the compound represented by the general formula (2) is contained in an amount of 0.1 to 50.0% by mass of the total amount of the compounds represented by the general formula (1) and the general formula (3). Do.

(In the general formula (1), X and Y are O or S, and may be the same or different. R ₁ and R ₂ each represent a carbon atom bonded to X and Y, respectively. The substituent may have the same or different molecular weight of 15 or more and less than 170. Z ₁ and Z ₂ may be any one of hydrogen, carbon, oxygen, sulfur, nitrogen or halogen, which is bonded to a benzene ring The substituents having a molecular weight of 1 or more and less than 200 as atoms may be the same or different.
At least one of R ₁ , R ₂ , Z ₁ and Z ₂ has a polymerizable functional group, a and b are 1 or 2, and when a and / or b are 2, Z ₁ and Z ₂ May be the same or different. )

(In the general formula (2), R ₅ and R ₆ are heterocyclic compounds and may be the same or different. The substituent on the heterocycle is a substituent having a molecular weight of 1 or more and less than 200. In the case where there are a plurality of substituents on the hetero ring, the substituents may be the same or different, and the total molecular weight of the substituents is 2 or more and 200 or more. Less than a substituent))

(In the general formula (3), Q is O or S and may be the same or different. R ₃ and R ₄ each have a molecular weight such that the bonding atom to S and Q is a carbon atom 15 or more and less than 170 substituents, which may be the same or different, and each of Z ₃ is a molecular weight of 1 or more in which hydrogen, carbon, oxygen, sulfur, nitrogen or halogen is a bonding atom to a benzene ring It is a substituent less than 200. At least one of R ₃ , R ₄ and Z ₃ has a polymerizable functional group, and c is 1 or 2.)

  The optical element of the present invention is a base material and an optical element in which a resin is provided on the base material, and the resin is the above-mentioned cured product.

  The optical element of the present invention is an optical element in which a resin is provided between two base materials, and the resin is the above-mentioned cured product.

  An optical apparatus of the present invention is characterized by having the above-described optical element.

  The method for producing an optical element of the present invention is characterized by comprising the steps of: providing the above-mentioned cured product on a substrate or between substrates; and forming the cured product.

According to the present invention, there is provided a cured product having high refractive index dispersion characteristics (Abbe number (ν _d )) and secondary dispersion characteristics (θg, F) and capable of suppressing crystallization of an organic material as compared with the prior art. be able to.

It is the schematic which shows the example of the optical element of this invention. It is a graph which shows the relationship between the secondary dispersion characteristic of the conventional optical material, and an Abbe number.

  Hereinafter, the present invention will be described in detail.

(Composition for optics)
First, the optical composition of the present embodiment will be described. In the present specification, the optical composition is a raw material before curing the cured resin.

  The optical composition according to the present embodiment comprises at least a compound represented by the following general formula (1) and / or a compound represented by the following general formula (3), and a compound represented by the following general formula (2) Have. In the optical composition according to the present embodiment, the compound represented by the general formula (2) is 0.1 to 50.0% by mass of the total amount of the compounds represented by the general formula (1) and the general formula (3) It is characterized by containing.

(In the general formula (1), X and Y are O or S, and may be the same or different. R ₁ and R ₂ each represent a carbon atom bonded to X and Y, respectively. The substituent may have the same or different molecular weight of 15 or more and less than 170. Z ₁ and Z ₂ may be any one of hydrogen, carbon, oxygen, sulfur, nitrogen or halogen, which is bonded to a benzene ring The substituents having a molecular weight of 1 or more and less than 200 as atoms may be the same or different.
At least one of R ₁ , R ₂ , Z ₁ and Z ₂ has a polymerizable functional group, a and b are 1 or 2, and when a and / or b are 2, Z ₁ and Z ₂ May be the same or different. )

(In the general formula (2), R ₅ and R ₆ are heterocyclic compounds and may be the same or different. The substituent on the heterocycle is a substituent having a molecular weight of 1 or more and less than 200. In the case where there are a plurality of substituents on the hetero ring, the substituents may be the same or different, and the total molecular weight of the substituents is 2 or more and 200 or more. Less than a substituent))

(In the general formula (3), Q is O or S and may be the same or different. R ₃ and R ₄ each have a molecular weight such that the bonding atom to S and Q is a carbon atom 15 or more and less than 170 substituents, which may be the same or different, and each of Z ₃ is a molecular weight of 1 or more in which hydrogen, carbon, oxygen, sulfur, nitrogen or halogen is a bonding atom to a benzene ring It is a substituent less than 200. At least one of R ₃ , R ₄ and Z ₃ has a polymerizable functional group, and c is 1 or 2.)

  Hereinafter, a case where the optical composition of the present embodiment includes at least a compound represented by General Formula (1) and a compound represented by General Formula (2) will be described.

  In the compound represented by the general formula (1), if X and Y are electron donating elements, the dispersion characteristics and the secondary dispersion characteristics are not particularly limited because they are characteristics within a range effective in optical design. However, in consideration of environmental resistance performance and easiness of synthesis of the compound, X and Y are O (oxygen atom) or S (sulfur atom), and they may be the same or different. However, X and Y are preferably the same in consideration of the ease of synthesis of the compound. More preferably, X and Y are each O.

R ₁ and R ₂ are not particularly limited as long as they do not reduce the optical properties of the cured product, and are preferably substituents in which the bonding atom to X and Y is a carbon atom. As the molecular weight of R ₁ and R ₂ increases, the optical performance decreases, and crystallization becomes impossible in the purification step during production, making it difficult to improve the purity as an optical material. Therefore, R ₁ and R ₂ are substituents having a molecular weight of 15 or more and less than 170, and may be the same or different. Specifically, R ₁ and R _{2 each} represent a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a 2-hydroxyethyl group, a 2-mercaptoethyl group, a 3-hydroxypropyl group, 2- Hydroxypropyl, 3-mercaptopropyl, 2-mercaptopropyl, 4-hydroxybutyl, 3-hydroxybutyl, 2-hydroxybutyl, 4-mercaptobutyl, 3-mercaptobutyl, 2-mercaptobutyl Group, allyl group, glycidyl group, isocyanatomethyl group, 2-isocyanatoethyl group, 3-isocyanatopropyl group, 4-isocyanatobutyl group, (meth) acryloyl group, 2- (meth) acryloyloxyethyl group, 2-methyl-2- (meth) acryloyloxyethyl group, 1-methyl-2- (2) T) Acryloyloxyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl-3- (meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxypropyl group, 2- (2-) And (meth) acryloyloxypropyl group, 4- (meth) acryloyloxybutyl group, 3- (meth) acryloyloxybutyl group, 2- (meth) acryloyloxybutyl group and the like.

When a substituent having a molecular weight of 15 or more and less than 170 is selected as R ₁ and R ₂ , in order to maintain the optical performance of the cured product, the purity of the general formula (1) or the residual solvent is high. It is preferable to control. Further, R ₁ and R ₂ may be methyl group, 2-hydroxyethyl group, 2-mercaptoethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, 3-mercaptopropyl group, considering the difficulty in production. 2-mercaptopropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxybutyl group, 4-mercaptobutyl group, 3-mercaptobutyl group, 2-mercaptobutyl group, (meth) acryloyl group, 2- (Meth) acryloyloxyethyl group, 2-methyl-2- (meth) acryloyloxyethyl group, 1-methyl-2- (meth) acryloyloxyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl- 3- (Meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxy Propyl group, a 2- (meth) acryloyloxy propyl, 4- (meth) acryloyloxy-butyl group, 3- (meth) acryloyloxy-butyl group, 2- (meth) acryloyloxy-butyl group.

Z ₁ and Z ₂ are not particularly limited as long as they do not reduce the optical properties of the cured product, and are preferably substituents having hydrogen, carbon, oxygen, sulfur, nitrogen or halogen as a bonding atom to the benzene ring It may be the same or different. As the molecular weight of Z ₁ and Z ₂ increases, the optical performance decreases, and crystallization becomes impossible in the purification step during production, and it becomes difficult to improve the purity as an optical material. Therefore, Z ₁ and Z ₂ are substituents having a molecular weight of 1 or more and less than 200. When a substituent having a large molecular weight of 1 to less than 200 is selected, in order to maintain the optical performance of the cured product, it is preferable to control the purity of the general formula (1) and the residual solvent to a high degree. Z ₁ and Z ₂ may be a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoro group in view of the difficulty in production. Methyl group, methoxy group, ethoxy group, isopropoxy group, chloromethyloxy group, dichloromethyloxy group, trichloromethyloxy group, fluoromethyloxy group, difluoromethyloxy group, trifluoromethyloxy group, methylthio group, ethylthio group, A propylthio group, a dimethylamino group, a diethylamino group, a dipropylamino group, a 2- (meth) acryloyloxyethoxy group, a 3- (meth) acryloyloxypropoxy group, a 4- (meth) acryloyloxybutoxy group, and the general formula (4) The structure etc. represented by) is preferred There.

  In the general formula (4), m is not particularly limited as long as the molecular weight of the substituent of the general formula (4) does not exceed 200, but m is preferably 0 in consideration of easiness in production.

W is hydrogen or a methyl group, and V is not particularly limited as long as the molecular weight of the substituent of the general formula (4) does not exceed 200. However, in consideration of the easiness of synthesis and easiness of raising the purity, V is selected from the groups shown below.
* -O-**,
* -S-**,
* -O-C _n H _2n -O-**,
_{* -S-C n H 2n -O} - **,
* -O-C _n H _2n -S-**,
_{* -S-C n H 2n -S} - **,

* Represents a bond with an alkylene moiety, ** represents a bond with a (meth) acryloyl group, and n is one of integers selected from 2 to 5. If the molecular weight of Z in the structure represented by C _n H _2n in V does not exceed 200, substitution of a halogen atom, an alkyl group, an aromatic group, a reactive functional group, etc. on a carbon atom There may be a base. The structure shown below is preferable as the above-mentioned V in consideration of easiness of synthesis and dispersion characteristics and secondary dispersion characteristics of a cured product.
* -O-**,
* -S-**,
_{* -O-CH 2 CH 2 -O} - **,
_{* -O-CH 2 CH 2 CH} 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -O-CH 2 CH (CH} 3) CH 2 -O - **,
_{* -O-CH (CH 3)} CH 2 CH (CH 3) -O - **,
_{* -O-C (CH 3)} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 C} (CH 3) 2 -O - **,
_{* -S-CH 2 CH 2 -O} - **,
_{* -S-CH 2 CH 2 CH} 2 -O - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -S-CH 2 CH (CH} 3) CH 2 -O - **,
_{* -S-CH (CH 3)} CH 2 CH (CH 3) -O - **,
_{* -S-C (CH 3)} 2 CH 2 CH 2 -O - **,
_{* -S-CH 2 CH 2 C} (CH 3) 2 -O - **,
_{* -O-CH 2 CH 2 -S} - **,
_{* -O-CH 2 CH 2 CH} 2 -S - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -S - **,
_{* -O-CH 2 CH (CH} 3) CH 2 -S - **,
_{* -O-CH (CH 3)} CH 2 CH (CH 3) -S - **,
_{* -O-C (CH 3)} 2 CH 2 CH 2 -S - **,
_{* -O-CH 2 CH 2 C} (CH 3) 2 -S - **,
_{* -S-CH 2 CH 2 -S} - **,
_{* -S-CH 2 CH 2 CH} 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -S - **,
_{* -S-CH 2 CH (CH} 3) CH 2 -S - **,
_{* -S-CH (CH 3)} CH 2 CH (CH 3) -S - **,
_{* -S-C (CH 3)} 2 CH 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 C} (CH 3) 2 -S - **,

As V, the structure shown below is more preferable in consideration of the easiness of synthesis.
* -O-**,
* -S-**,
_{* -O-CH 2 CH 2 -O} - **,
_{* -O-CH 2 CH 2 CH} 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -O-CH 2 CH (CH} 3) CH 2 -O - **,
_{* -O-CH (CH 3)} CH 2 CH (CH 3) -O - **,
_{* -S-CH 2 CH 2 -O} - **,
_{* -S-CH 2 CH 2 CH} 2 -O - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -S-CH 2 CH (CH} 3) CH 2 -O - **,
_{* -S-CH (CH 3)} CH 2 CH (CH 3) -O - **,
_{* -O-CH 2 CH 2 -S} - **,
_{* -O-CH 2 CH 2 CH} 2 -S - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -S - **,
_{* -O-CH 2 CH (CH} 3) CH 2 -S - **,
_{* -O-CH (CH 3)} CH 2 CH (CH 3) -S - **,
_{* -S-CH 2 CH 2 -S} - **,
_{* -S-CH 2 CH 2 CH} 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -S - **,
_{* -S-CH 2 CH (CH} 3) CH 2 -S - **,
_{* -S-CH (CH 3)} CH 2 CH (CH 3) -S - **,

Considering the ease of synthesis of the compound represented by the general formula (1), particularly the ease of purification, V preferably has a structure shown below.
* -O-**,
* -S-**,
_{* -O-CH 2 CH 2 -O} - **,
_{* -O-CH 2 CH 2 CH} 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -O-CH 2 CH (CH} 3) CH 2 -O - **,
_{* -O-CH (CH 3)} CH 2 CH (CH 3) -O - **,
_{* -S-CH 2 CH 2 -S} - **,
_{* -S-CH 2 CH 2 CH} 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -S - **,
_{* -S-CH 2 CH (CH} 3) CH 2 -S - **,
_{* -S-CH (CH 3)} CH 2 CH (CH 3) -S - **,

In view of the production cost, the odor of the reagent, the storage stability of the compound, etc., V is more preferably a structure shown below.
* -O-**,
* -S-**,
_{* -O-CH 2 CH 2 -O} - **,
_{* -O-CH 2 CH 2 CH} 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -S-CH 2 CH 2 -S} - **,
_{* -S-CH 2 CH 2 CH} 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -S - **,

Z ₁ and Z ₂ are preferably a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a methoxy group, an ethoxy group, an isopropoxy group, a methylthio group, an ethylthio group, a propylthio group, and a dimethylthio group in view of the difficulty in production. Amino group, diethylamino group, dipropylamino group, 2- (meth) acryloyloxyethoxy group, 3- (meth) acryloyloxypropoxy group, 4- (meth) acryloyloxybutoxy group, and general formula (4) Or any one of the substituents.

Z ₁ and Z ₂ are each more preferably a hydrogen atom, a methyl group, a methoxy group, a methylthio group, a dimethylamino group, a 2- (meth) acryloyloxyethoxy group, 3- (meth), in consideration of the degree of difficulty in production. It is an acryloyloxy propoxy group, 4- (meth) acryloyl oxy butoxy group, and any one of the substituent represented by General formula (4).

  Next, among the optical composition according to the present embodiment, an optical composition containing at least a compound represented by General Formula (1) and a compound represented by General Formula (3) will be described.

In the compound represented by the general formula (3), Q is O or S, and R ₃ and R ₄ are substituents having a molecular weight of 15 or more and less than 170, wherein the bonding atom to S and Q is a carbon atom Each may be the same or different. Z ₃ is a substituent having a molecular weight of 1 or more and less than 200 in which hydrogen, carbon, oxygen, sulfur, nitrogen or halogen is a bonding atom to a benzene ring, and at least one of R ₃ , R ₄ and Z ₃ is polymerizable And c is 1 or 2.

R ₃ and R ₄ are not particularly limited as long as they do not reduce the optical properties of the cured product, and preferably a substituent in which a bonding atom to Q or S is a carbon atom. R ₃ and R _4, the optical performance is lowered when the molecular weight becomes large, can no longer be crystallized in the purification process during manufacturing, it is difficult to improve to a purity as an optical material. Therefore, R ₃ and R ₄ are substituents having a molecular weight of 15 or more and less than 170, and may be the same or different. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, 2-hydroxyethyl group, 2-mercaptoethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, 3-mercapto Propyl group, 2-mercaptopropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxybutyl group, 4-mercaptobutyl group, 3-mercaptobutyl group, 2-mercaptobutyl group, allyl group, glycidyl group , Isocyanate methyl group, 2-isocyanatoethyl group, 3-isocyanatopropyl group, 4-isocyanatobutyl group, (meth) acryloyl group, 2- (meth) acryloyloxyethyl group, 2-methyl-2- ( Meta) acryloyloxyethyl group, 1-methyl-2- (meth) acryloyl Xyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl-3- (meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxypropyl group, 2- (meth) acryloyloxy A propyl group, 4- (meth) acryloyloxybutyl group, 3- (meth) acryloyloxybutyl group, and 2- (meth) acryloyloxybutyl group are preferable.

When R ₃ and R ₄ are substituents having a molecular weight of 15 or more and less than 170 and a substituent having a large molecular weight is selected, the purity of the general formula (3) or the residual solvent is high to maintain the optical performance of the cured product. It is preferable to control the R ₃ and R ₄ may be methyl group, 2-hydroxyethyl group, 2-mercaptoethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, 3-mercaptopropyl group, considering the difficulty in production. -Mercaptopropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxybutyl group, 4-mercaptobutyl group, 3-mercaptobutyl group, 2-mercaptobutyl group, (meth) acryloyl group, 2- (2-) Meta) acryloyloxyethyl group, 2-methyl-2- (meth) acryloyloxyethyl group, 1-methyl-2- (meth) acryloyloxyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl-3 -(Meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxy group Propyl group, 2- (meth) acryloyloxy propyl, 4- a (meth) acryloyloxy-butyl group, 3- (meth) acryloyloxy-butyl group, and more preferably a 2- (meth) acryloyloxy-butyl group.

Z ₃ is not particularly limited as long as it does not reduce the optical properties of the cured product, and is a substituent having a molecular weight of 1 or more and less than 200, which has hydrogen, carbon, oxygen, sulfur, nitrogen or halogen as a bonding atom to a benzene ring, Each may be the same or different. As Z ₃ increases in optical performance when molecular weight increases, and can not be crystallized in the purification step at the time of production, and it becomes difficult to improve the purity as an optical material, substituents with a molecular weight of 1 or more and less than 200 It is. When a substituent having a molecular weight of 1 or more and less than 200 is selected, in order to maintain the optical performance of the cured product, it is desirable to highly control the purity of the general formula (1) and the residual solvent. In view of the difficulty in production, Z ₃ is a hydrogen atom, methyl group, ethyl group, isopropyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, methoxy , Ethoxy, isopropoxy, chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, methylthio, ethylthio, propylthio, dimethyl Amino group, diethylamino group, dipropylamino group, 2- (meth) ac It is preferable to use a functional group represented by a lyoloyloxy ethoxy group, a 3- (meth) acryloyloxypropoxy group, a 4- (meth) acryloyloxybutoxy group, and the general formula (4).

Z ₃ is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a methoxy group, an ethoxy group, an isopropoxy group, a methylthio group, an ethylthio group, a propylthio group, a dimethylamino group, a diethylamino group, in view of the difficulty in production. Using a dipropylamino group, 2- (meth) acryloyloxyethoxy group, 3- (meth) acryloyloxypropoxy group, 4- (meth) acryloyloxybutoxy group, or a substituent represented by the general formula (4) Is more preferred.

Z ₃ is a hydrogen atom, a methyl group, a methoxy group, a methylthio group, a dimethylamino group, a 2- (meth) acryloyloxyethoxy group, a 3- (meth) acryloyloxypropoxy group, 4 in view of the difficulty in production It is further preferable to use a-(meth) acryloyloxybutoxy group or a substituent represented by the above general formula (4).

In the compound represented by the general formula (2), R ₅ and R ₆ are preferably one selected from the following formulas (5) to (20), and R ₅ and R ₆ are the same even though they are the same. May be

Z ₄ is a substituent having a molecular weight of 1 or more and less than 200, and may be the same or different. d is an integer in the range of 1 to 5 in the structural formula, and when d is an integer of 2 to 5, the substituents may be the same or different, and the sum of molecular weights of Z4 Is 2 or more and less than 200. Specifically, Z ₄ is not particularly limited as long as it does reduce the optical properties of the cured product, there preferably hydrogen, carbon, oxygen, sulfur, nitrogen, or halogen substituents to be bonded atoms between the benzene ring May be the same or different. Z ₄ is a hydrogen atom, chloro group, bromo group, fluoro group, methyl group, ethyl group, isopropyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, fluoromethyl group, in view of production difficulty Difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, isopropoxy group, chloromethyloxy group, dichloromethyloxy group, trichloromethyloxy group, fluoromethyloxy group, difluoromethyloxy group, trifluoromethyloxy group, Methylthio, ethylthio, propylthio, dimethylamino, diethylamino, dipropylamino, 2- (meth) acryloyloxyethoxy, 3- (meth) acryloyloxypropoxy, 4- (meth) acryloyloxybutoxy , (Meth) acryloyl Roxymethyl group, 2- (meth) acryloyloxyethoxymethyl group, 3- (meth) acryloyloxypropoxymethyl group, 4- (meth) acryloyloxybutoxymethyl group, 3- (meth) acryloyloxy-2-methylpropoxymethyl group (Meth) acryloyloxy-1-ethyl group, 2- (meth) acryloyloxyethoxy-1-ethyl group, 3- (meth) acryloyloxypropoxy-1-ethyl group, 4- (meth) acryloyloxybutoxy-1 -Ethyl group and 3- (meth) acryloyloxy-2-methylpropoxy-1-ethyl group are preferable.

Z ₄ is a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a dimethylamino group, a diethylamino group, a 2- (meth) acryloyloxyethoxy group, (meth) in view of the difficulty in production Acryloyloxymethyl, 2- (meth) acryloyloxyethoxymethyl, 3- (meth) acryloyloxypropoxymethyl, 4- (meth) acryloyloxybutoxymethyl, 3- (meth) acryloyloxy-2-methylpropoxy Methyl group, (meth) acryloyloxy-1-ethyl group, 2- (meth) acryloyloxyethoxy-1-ethyl group, 3- (meth) acryloyloxypropoxy-1-ethyl group, 4- (meth) acryloyloxybutoxy -1-ethyl group, 3- (meth) acryloyloxy- More preferably, it is a 2-methylpropoxy-1-ethyl group.

Z ₄ is a hydrogen atom, a methyl group, a methoxy group, a methylthio group, a dimethylamino group, a 2- (meth) acryloyloxyethoxy group, a (meth) acryloyloxymethyl group, (meth) in consideration of the degree of difficulty in production More preferably, it is an acryloyloxy-1-ethyl group.

R ₇ may be the same or different and is preferably a methyl group, an ethyl group, a propyl group, an acetyl group or the like.

  Next, the effect of incorporating the compound represented by the general formula (2) into the compound represented by the general formula (1) and / or the general formula (3) in the optical composition of the invention of the present embodiment will be described. In general, an optical composition stored in a storage bottle is added with a polymerization inhibitor in order to suppress the polymerization of the polymerizable material. However, when the polymerizable material crystallizes, the polymerization inhibitor can not be present in the vicinity of the molecules of the polymerizable material in the crystalline state, and the polymerizable material becomes more likely to be polymerized. On the other hand, since the polymerization in the crystalline state is different from the polymerization in the liquid state, the polymerization for each crystal unit is performed, so the risk of the entire storage bottle being polymerized is low. When the polymerizable material is polymerized in a crystalline state, the polymer has low solubility in the optical composition and causes scattering in a cured product obtained by polymerizing the optical composition. Moreover, since it is identified as a foreign substance, it is one of the factors that lower the quality of the appearance of the optical composition.

  In addition, when crystallization of the material progresses in the optical composition in the state of the mixture to which various additives are added, a nonuniform portion in which the polymerization inhibitor and the additive are collected is generated in the optical composition. It becomes one of the factors that lower the quality of the appearance of the optical composition. Furthermore, if an uneven part occurs, additional steps such as re-stirring are required, which causes a problem in process control.

  As a typical method of suppressing crystallization of a polymerizable material, a method of adding a material having high solvency, addition of a molecule which is difficult to crystallize and whose molecular structure is similar to the molecule of the polymerizable material of which crystallization is desired to be suppressed And the method of inhibiting the orientation of the molecule | numerator of the polymeric material which advances at the time of crystallization. In the former, it is necessary to add a large amount of high solvency material to obtain the effect. In this method, although crystallization of the polymerizable material can be suppressed, a change in optical properties of a cured product obtained by curing the optical composition can be a problem. In the latter case, as disclosed in JP-A-2014-198814, a general method is to add a more difficult-to-crystallizable molecule whose molecular structure is similar to the molecule of the polymerizable material whose crystallization is to be suppressed. . As a molecule that has a similar molecular structure and is more difficult to crystallize, specifically, it is desirable to suppress addition or crystallization of a long flexible substituent of a carbon chain to the backbone of the molecule of the base polymerizable material A change to a substituent having a carbon chain longer than the molecule may, for example, be mentioned.

  However, an optical composition containing a compound having a similar structure to a polymerizable material having a flexible substituent added or a change to a substituent having a long carbon chain has dispersion characteristics and secondary dispersion characteristics. There is a concern that the Therefore, in the present embodiment, the compound represented by General Formula (2) is contained in the compound represented by General Formula (1) and / or General Formula (3). When the content of the compound represented by the general formula (2) is too small, the effect of suppressing crystallization is small, and when the content is too large, the cured product of the optical composition becomes brittle. For this reason, it is preferable to contain the compound represented by General formula (2) 0.1-50.0 mass% of the total amount of the compound represented by General formula (1) and General formula (3). More preferably, in consideration of the brittleness of the cured product of the optical composition of the present embodiment, the compound represented by the general formula (2) is a total of the compounds represented by the general formula (1) and the general formula (3) 0.1 to 20.0% by mass of the amount. More preferably, in view of the performance of the optical element formed by curing and molding the optical composition of the present embodiment and the brittleness of the molded article, compounds of the general formula (1) and the general formula (3) It is 5.0 to 20.0 mass% of the total amount.

  The compound represented by the general formula (2) not only has the same diphenyl sulfone skeleton as that of the general formula (1) or the general formula (3) but also contains a heterocycle. Therefore, the compound represented by the general formula (2) can effectively inhibit the crystallization due to the orientation of the general formula (1) due to the effect of the noncovalent electron pair of the hetero atom. Moreover, since the molecular weight of General formula (2) is comparable with General formula (1) or General formula (3), crystallization can be suppressed, without raising the viscosity of the composition for optics extremely. Furthermore, since the optical performance is also improved by the effect of the heterocycle, crystallization can be suppressed without adverse effects such as viscosity increase by the addition, and further improvement of the optical performance can be expected.

  Although the manufacturing method of the compound represented by General formula (1) or General formula (3) was manufactured referring to Unexamined-Japanese-Patent No. 2012-167019, it does not specifically limit about the manufacturing method, What kind of manufacturing method employ | adopts It is possible.

  Although the manufacturing method of the compound represented by General formula (2) was manufactured by the Suzuki coupling which referred Unexamined-Japanese-Patent No. 2012-167019 similarly to General formula (1), it does not specifically limit about the manufacturing method, Any manufacturing method can be employed.

(Cured product)
The hardened | cured material of this embodiment is demonstrated.

The cured product of the present embodiment is a cured product in which the polymerizable functional group of the optical composition of the present embodiment is polymerized. The cured product of this embodiment is
It is a cured product in which at least a compound represented by the following general formula (1) and / or a compound represented by the general formula (3) and a compound represented by the following general formula (2) are polymerized. n The compound represented by General formula (2) is characterized by containing 0.1-50.0 mass% of the total amount of the compound represented by General formula (1) and General formula (3).

  The hardened | cured material of this embodiment is divided roughly into the aspect of following (A)-(D).

  (A) A cured product obtained by polymerizing a compound represented by the general formula (1) and / or the general formula (3) and a compound represented by the general formula (2).

  (B) Copolymerized with a compound represented by the general formula (1) and / or the general formula (3), a compound represented by the general formula (2), and another copolymerizable polymerizable material Cured product.

  (C) A compound represented by the general formula (1) and / or the general formula (3) and a compound represented by the general formula (2) are dispersed in another copolymerizable polymerizable material, and these are copolymerized Cured product.

  (D) A cured product obtained by dispersing the compound represented by the general formula (1) and / or the general formula (3) and the compound represented by the general formula (2) in another matrix polymer.

(Method for producing cured product)
The method for producing a cured product of the present embodiment comprises an optical composition containing at least a compound represented by the general formula (1) or a compound represented by the general formula (3), and a compound represented by the general formula (2) It has the process of preparing a thing. The optical resin composition contains the compound represented by Formula (2) in an amount of 0.1 to 50.0% by mass of the compound represented by Formula (1) or Formula (3). Next, a cured product is manufactured through the steps of polymerizing and curing the prepared optical composition.

  When the cured product of this embodiment is the cured product of the aspect of (A), the cured product is represented by the compound represented by the general formula (1) and / or the general formula (3), and the general formula (2) Manufactured by polymerizing an optical composition containing a compound of formula (I) and a polymerization initiator. The composition for optics may further contain, if necessary, a polymerization inhibitor, a photosensitizer, a light stabilizer, a heat stabilizer, an antioxidant, a mold release agent, a fungicide and the like. .

  Examples of the polymerization initiator include, but are not limited to, those that generate active species such as radical species and cationic species by light irradiation, and those that generate active species such as radical species by heat.

  As a polymerization initiator which generates radical species by light irradiation, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2- Methyl-1-phenyl-propan-1-one, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 4-phenylbenzophenone, 4-phenoxybenzophenone, 4,4'-diphenylbenzophenone, 4,4 ' -Diphenoxy benzophenone etc. is mentioned, However, It is not limited to these.

  Moreover, as a polymerization initiator which generate | occur | produces cationic seed | species by light irradiation, iodonium (4-methylphenyl) [4- (2-methylpropyl) phenyl] hexafluorophosphate is mentioned as a suitable polymerization initiator, It is not limited.

  Furthermore, as a polymerization initiator which generates radical species by heat, an azo compound such as azobis isobutyl nitrile (AIBN), benzoyl peroxide, tert-butyl peroxypivalate, tert-butyl peroxy neohexanoate, tert Peroxides such as hexyl peroxy neohexanoate, tert-butyl peroxy neodecanoate, tert-hexyl peroxy neodecanoate, cumylperoxy neohexanoate, cumylperoxy neodecanoate These include, but are not limited to.

  The addition amount of the polymerization initiator contained in the optical composition is relative to the total mass of the compound represented by the general formula (1) and / or the general formula (3) and the compound represented by the general formula (2) The range of 0.01 mass% or more and 10.00 mass% or less is preferable. The polymerization initiator may be used alone or in combination of two or more. The addition ratio of the polymerization initiator to the total amount of the compound represented by the general formula (1) and / or the general formula (3) and the compound represented by the general formula (2) is the light irradiation amount, further, You may select suitably according to additional heating temperature. Also, it may be adjusted according to the target average molecular weight of the resulting polymer.

  Examples of polymerization inhibitors include hydroquinones such as hydroquinone, hydroquinone monomethyl ether, hydroquinone monoethyl ether, hydroquinone monopropyl ether, hydroquinone monobutyl ether, hydroquinone monopentyl ether, hydroquinone monohexyl ether, hydroquinone monooctyl ether, hydroquinone monooctyl ether, hydroquinone monoheptyl ether, etc. And a phenolic polymerization inhibitor having a substituent such as 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate. However, hydroquinone-based polymerization inhibitors such as hydroquinone and benzoquinone-based polymerization inhibitors such as benzoquinone are not preferable because they may turn yellow upon UV irradiation.

  Examples of the polymerization inhibitor include, but are not limited to, those described above as the polymerization inhibitor at the time of reaction and storage. The addition amount is preferably in the range of 0.01% by mass to 1.00% by mass with respect to the composition for optics. Further, only one polymerization inhibitor may be used, or two or more polymerization inhibitors may be used in combination. Specifically, in consideration of the low coloring, it is preferable to use a combination of hydroquinone polymerization inhibitors.

  Photosensitizers include benzophenone, 4,4-diethylaminobenzophenone, 1-hydroxycyclohexyl phenyl ketone, isoamyl p-dimethylaminobenzoate, methyl 4-dimethylaminobenzoate, benzoin, benzoin ethyl ether, benzoin isobutyl ether, benzoin isopropyl Ether, 2,2-diethoxyacetophenone, methyl o-benzoylbenzoate, 2-hydroxy-2-methyl-1-phenylpropan-1-one, acyl phosphine oxide and the like can be mentioned. The amount of addition is preferably in the range of 0.01% by mass or more and 10.00% by mass or less with respect to the optical composition.

  The light stabilizer is not particularly limited as long as it does not greatly affect the optical properties of the cured product, and 2- (2H-benzotriazol-2-yl) -p-cresol, 2- (2H-benzotriazole) 2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol, 2- [5-chloro (2H) -benzotriazol-2-yl] -4-methyl-6- (tert-butyl) ) Phenol, 2- (2H-benzotriazol-2-yl) -4,6-di-tert-pentylphenol, 2- (2H-benzotriazol-2-yl) -4- (1,1,3,3) -Tetramethylbutyl) phenol, 2,2'-Methylenebis [6- (2H-benzotriazol-2-yl)]-4- (1,1,3,3-tetramethylbutyl) phenol, 2- ( Benzotriazole compounds such as H-benzotriazol-2-yl) -6-dodecyl-4-methylphenol, ethyl 2-cyano-3,3-diphenylacrylate, 2-cyano-3,3-diphenylacrylic acid Examples include cyanoacrylate compounds such as 2-ethylhexyl, triazine compounds, and benzophenone compounds such as octabenzone and 2,2'-4,4'-tetrahydrobenzophenone. In some cases, the above-mentioned light stabilizer plays a role of a photosensitizer, in which case the photosensitizer may not be added. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  The heat-resistant stabilizer is not particularly limited as long as it does not greatly affect the optical properties of the cured product, and pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl)] propionate, Octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 3,5-bis (1,1-dimethylethyl) -4-hydroxybenzenepropanoic acid having 7 carbon atoms having a side chain -9 alkyl esters, 4,6-bis (octylthiomethyl) -o-cresol, 4,6-bis (dodecylthiomethyl) -o-cresol, ethylene bis (oxyethylene) bis [3- (5-tert) -Butyl-4-hydroxy-m-tolyl)] propionate, hexamethylene bis [3- (3,5-di-tert-butyl) Hindered phenol compounds such as -4-hydroxyphenyl)] propionate, phosphorus compounds such as tris (2,4-di-tert-butylphenyl) phosphite, dioctadecyl-3,3'-thiodipropio And sulfur-based compounds such as nitrate. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  The antioxidant is not particularly limited as long as it does not greatly affect the optical properties of the cured product, and bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,7) Examples thereof include hindered amine compounds such as 2,6,6-pentamethyl-4-piperidyl) [[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] butyl malonate. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  When the cured product of this embodiment is the cured product of the aspect of (B), the cured product is represented by the compound represented by the general formula (1) and / or the general formula (3) and the general formula (2) The compound is produced by polymerizing an optical composition comprising a polymerizable material copolymerizable with the compound. The content of the compound represented by the general formula (1) or the general formula (3) and the compound represented by the general formula (2) in the optical composition is desirably 1.0% by weight or more and 99% by weight or less. In order to make the dispersion characteristics and the second-order dispersion characteristics of the cured product in a range useful for optical design, the inclusion of the compound represented by General Formula (1) or General Formula (3) and the compound represented by General Formula (2) The amount is preferably 50% by weight or more and 99% by weight or less. The composition for optics may further contain, if necessary, a polymerization inhibitor, a photosensitizer, a light stabilizer, a heat stabilizer, an antioxidant, a mold release agent, a fungicide and the like. .

  Examples of the copolymerizable polymerizable material include, but are not particularly limited to, (meth) acrylic monomers. For example, 1,3-adamantane diol dimethacrylate, 1,3-adamantane dimethanol dimethacrylate, tricyclodecane dimethanol diacrylate, pentaerythritol tetraacrylate, propoxylated neopentyl glycol diacrylate, dipropylene glycol diacrylate, ethoxylated Bisphenol A dimethacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, stearyl acrylate, tetrahydrofurfuryl acrylate, 2-phenoxyethyl acrylate, isodecyl acrylate, isobonyl acrylate, Isobonyl methacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol di Crylates, diethylene glycol diacrylate, 1,6-hexanediol diacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, triethylene glycol dimethacrylate, ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, diethylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, tripropylene glycol dimethacrylate, dipropylene glycol dimethacrylate, trimethylolpropane trimethacrylate, 9,9-bis [4- (2 -Acrylyloxyethoxy) phenyl] fluorene, 9,9-bis [4- (2-) Tacryloyloxyethoxy) phenyl] fluorene, 9,9-bis [4- (2-acryloyloxy) phenyl] fluorene, 9,9-bis [4- (2-methacryloyloxy) phenyl] fluorene, benzyl acrylate, benzyl methacrylate , Butoxyethyl acrylate, butoxymethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxymethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, phenyl methacrylate, ethylene glycol diacrylate, ethylene Glycol dimethacrylate, diethylene glycol diacrylate, diethylene Glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate Ethylene glycol bisglycidyl acrylate, ethylene glycol bisglycidyl methacrylate, bisphenol A diacrylate, bisphenol A dimethacrylate, 2,2-bis (4-acryloxyethoxyphenyl) propane, 2,2-bis (4-methacryloxyethoxyphenyl) ) Propane, 2,2-bis (4-acryloxydiethoxy group) Nyl) propane, 2,2-bis (4-methacryloxydiethoxyphenyl) propane, bisphenol F diacrylate, bisphenol F dimethacrylate, 1,1-bis (4-acryloxyethoxyphenyl) methane, 1,1-bis (4-methacryloxyethoxyphenyl) methane, 1,1-bis (4-acryloxydiethoxyphenyl) methane, 1,1-bis (4-methacryloxydiethoxyphenyl) methane, 1,1-bis (4-) Acryloxyethoxyphenyl) sulfone, 1,1-bis (4-methacryloxyethoxyphenyl) sulfone, 1,1-bis (4-acryloxydiethoxyphenyl) sulfone, 1,1-bis (4-methacryloxydiethoxy) Phenyl) sulfone, dimethylol tricyclodecane diacrylate, tri Tyrolpropane triacrylate, trimethylolpropane trimethacrylate, glycerol diacrylate, glycerol dimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, methylthioacrylate, methylthiomethacrylate, phenylthioacrylate, benzylthiomethacrylate, xylylene (Meth) acrylate compounds such as thiol diacrylate, xylylene dithiol dimethacrylate, mercaptoethyl sulfide diacrylate, mercaptoethyl sulfide dimethacrylate, allyl glycidyl ether, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl carbonate, diaryl carbonate And allyl compounds such as ethylene glycol bisallyl carbonate, vinyl compounds such as styrene, chlorostyrene, methylstyrene, bromostyrene, dibromostyrene, divinylbenzene, 3,9-divinyl spirobi (m-dioxane), and diisopropenylbenzene. However, it is not limited to these.

  The addition amount of the copolymerizable polymerizable material is preferably in the range of 0.10% by mass or more and 80.00% by mass or less with respect to the mass of the composition for optics. It is preferably 0.10% by mass or more and 30.00% by mass or less, considering that the dispersion property and the secondary dispersion property of the cured product fall within a useful range in optical design.

  As the polymerization initiator contained in the optical composition for producing the cured product of this embodiment, the polymerization initiator shown in the embodiment of (A) can be used. The addition amount thereof is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the total mass of the polymerizable components. The polymerization initiator may be used alone or in combination of two or more. The addition ratio of the polymerization initiator may be appropriately selected according to the light irradiation amount, and further, the additional heating temperature. Also, it may be adjusted according to the target average molecular weight of the resulting polymer.

  As a polymerization inhibitor contained in the composition for optics for manufacturing the hardened | cured material of this embodiment, the polymerization inhibitor shown in the aspect of (A) can be used. The amount of addition is preferably in the range of 0.01% by mass or more and 10.00% by mass or less with respect to the optical composition.

  When ultraviolet light or the like is irradiated to initiate polymerization, a known photosensitizer or the like can also be used. As a photosensitizer, the photosensitizer shown in the aspect of (A) can be used. The addition amount of the photosensitizer is preferably in the range of 0.01% by mass or more and 10.00% by mass or less based on the optical composition.

  As a light resistance stabilizer contained in the composition for optics for manufacturing the hardened | cured material of this embodiment, the light resistance stabilizer shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  As a heat-resistant stabilizer contained in the composition for optics for manufacturing the hardened | cured material of this embodiment, the heat-resistant stabilizer shown in the aspect of (A) is mentioned. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass of the composition for optics.

  As the antioxidant contained in the optical composition for producing the cured product of the present embodiment, the antioxidant shown in the embodiment of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  When the cured product of this embodiment is the cured product of the aspect of (C), the cured product is a compound represented by the general formula (1) or the general formula (3) and a compound represented by the general formula (2) It is produced by polymerizing an optical composition dispersed in a copolymerizable polymerizable material. The content of the copolymerizable polymerizable material contained in the optical composition is desirably 1.0% by mass or more and 99.0% by mass or less. It is necessary to consider the dispersion characteristics and secondary dispersion characteristics of the resulting cured product, and the compatibility between the compound represented by the general formula (1) and the compound represented by the general formula (2) and the polymerizable material. Therefore, the content of the compound represented by the general formula (1) and the general formula (3) and the compound represented by the general formula (2) is preferably 1.0% by mass or more and 50.0% by mass or less.

  The composition for optics may further contain, if necessary, a polymerization inhibitor, a photosensitizer, a light stabilizer, a heat stabilizer, an antioxidant, a mold release agent, a fungicide and the like. .

  The polymerizable material is not particularly limited as long as the dispersion property and the secondary dispersion property of the cured product fall within a useful range in optical design. Specifically, the (meth) acrylic monomers, allyl compounds, vinyl compounds, diisopropenyl benzene compounds, epoxy compounds, thiirane compounds, etc. shown in the aspect of (B) may be used as the polymerizable material in this aspect. Although it can, it is not limited to these.

  As the polymerization initiator contained in the optical composition for producing the cured product of this embodiment, the polymerization initiator shown in the embodiment of (A) can be used. The addition amount thereof is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the polymerizable component. The polymerization initiator may be used alone or in combination of two or more. The addition ratio of the polymerization initiator may be appropriately selected according to the light irradiation amount, and further, the additional heating temperature. Also, it may be adjusted according to the target average molecular weight of the resulting polymer.

  As a polymerization inhibitor contained in the composition for optics of this embodiment, the polymerization inhibitor shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  When ultraviolet light or the like is irradiated to initiate polymerization, a known photosensitizer or the like can also be used. As a typical photosensitizer, the photosensitizer shown in the embodiment of (A) can be used. The addition amount of the photosensitizer contained in the optical composition for producing the cured product of the present embodiment is in the range of 0.01% by mass to 10.00% by mass with respect to the optical composition. Is preferred.

  As a light resistance stabilizer contained in the composition for optics for manufacturing the hardened | cured material of this embodiment, the light resistance stabilizer shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  As a heat-resistant stabilizer contained in the optical composition for manufacturing the hardened | cured material of this embodiment, the heat-resistant stabilizer shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  As the antioxidant contained in the optical composition for producing the cured product of the present embodiment, the antioxidant shown in the embodiment of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  In the case of the cured product of the embodiment (D), the cured product is a compound represented by the general formula (1) and the general formula (3), a compound represented by the general formula (2), and a copolymer thereof with these compounds It is produced by polymerizing an optical composition comprising a possible matrix polymer. The content of the matrix polymer compound contained in the optical composition is desirably 1.0% by mass or more and 99.0% by mass or less. It is necessary to consider the dispersion characteristics and secondary dispersion characteristics of the resulting cured product, and the compatibility between the compounds represented by the general formulas (1) and (3) and the compounds represented by the general formula (2) and the matrix polymer. is there. In consideration of these, the content of the matrix polymer is preferably 1.0% by mass or more and 50.0% by mass or less. The composition for optics may further contain, if necessary, a polymerization inhibitor, a photosensitizer, a light stabilizer, a heat stabilizer, an antioxidant, a mold release agent, a fungicide and the like. .

  Examples of matrix polymers include (meth) acrylic polymers; allyl polymers; ethylene homopolymers, ethylene and propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, etc. Random or block copolymer with a kind or more of α-olefin, ethylene and vinyl acetate, acrylic acid, methacrylic acid, methyl acrylate, methyl acrylate, methyl methacrylate, methyl methacrylate, methyl methacrylate or random copolymer of one or more kinds, propylene Homopolymers, random or block copolymers of propylene and one or more α-olefins such as 1-butene other than propylene, 1-pentene, 1-hexene, 4-methyl-1-pentene, etc. -Polyolefins such as butene homopolymers, ionomer resins, and mixtures of these polymers Resins; hydrocarbon resins such as petroleum resins and terpene resins; polyester resins such as polyethylene terephthalate, polybutylene terephthalate and polyethylene naphthalate; nylon 6, nylon 66, nylon 11, nylon 12, nylon 610, nylon 6/66 Polyamide resins such as nylon 66/610 and nylon MXD; acrylic resins such as polymethyl methacrylate; polystyrene, styrene-acrylonitrile copolymer, styrene-acrylonitrile-butadiene copolymer, styrene such as polyacrylonitrile, acrylonitrile resin; Polyvinyl alcohol resins such as polyvinyl alcohol and ethylene-vinyl alcohol copolymer; polycarbonate resin; polyketone resin; polymethylene oxide resin; polysulfone resin Polyimide resins; but polyamideimide resins are not limited thereto. These resins may be used alone or in combination of two or more. Further, these matrix polymers are appropriately selected in consideration of the compatibility with the compound represented by the general formula (1) and the compound represented by the general formula (2), the dispersion characteristics of the cured product and the secondary dispersion characteristics.

  As the polymerization initiator contained in the optical composition for producing the cured product of this embodiment, the polymerization initiator shown in the embodiment of (A) can be used. The addition amount thereof is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the polymerizable component. The polymerization initiator may be used alone or in combination of two or more. The addition ratio of the polymerization initiator may be appropriately selected according to the light irradiation amount, and further, the additional heating temperature. Also, it may be adjusted according to the target average molecular weight of the resulting polymer.

  As a polymerization inhibitor contained in the composition for optics for manufacturing the hardened | cured material of this embodiment, the polymerization inhibitor shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  When ultraviolet light or the like is irradiated to initiate polymerization, a known photosensitizer or the like can also be used. As a typical photosensitizer, the photosensitizer shown in the embodiment of (A) can be used. The addition amount of the photosensitizer contained in the optical composition for producing the cured product of the present embodiment is in the range of 0.01% by mass to 10.00% by mass with respect to the optical composition. Is preferred.

  As a light resistance stabilizer contained in the composition for optics for manufacturing the hardened | cured material of this embodiment, the light resistance stabilizer shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  As a heat-resistant stabilizer contained in the optical composition for manufacturing the hardened | cured material of this embodiment, the heat-resistant stabilizer shown in the aspect of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  As the antioxidant contained in the optical composition for producing the cured product of the present embodiment, the antioxidant shown in the embodiment of (A) can be used. The addition amount is preferably in the range of 0.01% by mass to 10.00% by mass with respect to the composition for optics.

  The mixing method with various additives, general purpose monomers, and matrix polymer is not particularly limited as long as it can be uniformly mixed, and after mixing all materials in a solvent etc., the method of removing the solvent, heating and melting the materials It is a method etc. of mixing as it is. In preparing the optical composition for obtaining the cured product of the embodiments (A), (B) and (C), the method of mixing in a solvent is preferable because the method is uniform. On the other hand, when preparing the composition for optics for obtaining the hardened | cured material of the aspect of said (D), the method of heating a material and mixing as it is preferable in consideration of the low solubility to the solvent of a matrix monomer.

  The method for removing the solvent is not particularly limited as long as the amount of residual solvent in the composition for optical use is reduced, and examples thereof include a reduced pressure distillation method and a distillation method. In the reduced pressure distillation method, since the polymerization reaction may be promoted under reduced pressure, it is preferable to carry out the reduced pressure distillation while flowing a gas containing oxygen. Further, in the distillation method, since the polymerization reaction may be promoted by heating, it is preferable to appropriately adjust the addition of the polymerization inhibitor and the heating temperature.

  When the composition for optics of this embodiment is polymerized and the hardened | cured material of the aspect of said (A)-(D) is manufactured, a polymerization reaction is started by the polymerization initiator in the composition for optics. When the polymerization initiator is a photopolymerization initiator that generates active species by light irradiation, the cured product of the present embodiment is produced by irradiating light of a suitable wavelength at which the photopolymerization initiator generates active species. Do. The light of suitable wavelength includes, for example, ultraviolet light or visible light. When the polymerization initiator is a thermal polymerization initiator that generates active species by heating, the cured product of the present embodiment can be produced by heating the thermal polymerization initiator to a suitable temperature that generates the active species. Do. A suitable temperature is, for example, 80 ° C. or more and 180 ° or less.

(Optical Element and Method of Manufacturing Optical Element)
Next, the optical element of the present embodiment and the method of manufacturing the same will be described with reference to the drawings.

  The optical element of the present embodiment is characterized in that the cured product of the aspects (A) to (D) is molded. FIG. 2 is a schematic view showing an optical lens as an example of the optical element of the present embodiment. In the optical element of FIG. 2A, a thin film (optical member 10) formed by molding the cured product of the present embodiment is provided on one surface of a lens substrate 20 as a base material.

  As a method of manufacturing the optical element of FIG. 2 (a), the method of forming the hardened | cured material of this embodiment of thin layer structure of thin film thickness is mentioned, for example on the base material which consists of light transmissive materials. Specifically, a mold made of a metal material or the like is provided at a certain distance from the glass substrate, and the gap between the mold and the glass substrate is filled with the optical composition of the present embodiment of fluidity. After that, molding is performed by holding the mold lightly. Then, while the mold is held down, the optical composition is polymerized. The polymerization reaction is carried out by light irradiation or heating.

  In the case of polymerizing an optical composition by photopolymerization, for example, with respect to a light transmitting material used as a substrate, specifically, a raw material such as a monomer of an optical composition being molded through a glass substrate Apply light uniformly. The amount of light to be irradiated is appropriately selected according to the reaction mechanism using the photopolymerization initiator and according to the content ratio of the photopolymerization initiator to be contained.

  As described above, in the production of the cured product of the optical composition by the photopolymerization reaction, it is more preferable that the irradiated light be uniformly irradiated on the whole of the raw material such as the monomer being molded. Therefore, it is more preferable to select the light of the wavelength which can be uniformly performed via the light transmissive material used for a board | substrate, for example, a glass substrate, for the light irradiation utilized. Under the present circumstances, it is more suitable for this embodiment to thin the thickness of the composition for optics formed on the board | substrate of a transparent material.

  When the optical composition is polymerized by thermal polymerization, the optical composition may be polymerized by heating the mold, and the molded optical composition is heated in a heating apparatus such as an oven. The optical composition may be polymerized by heating. The heating temperature is appropriately selected according to the reaction mechanism using the thermal polymerization initiator and according to the content ratio of the photopolymerization initiator to be contained.

  Similar to the production of a cured product of the optical composition by the photopolymerization reaction, it is more preferable that heat be uniformly applied to the entire raw material of the optical composition being molded. Therefore, as a heating method to be used, it is more preferable that the molded optical composition be uniformly heated in a heating apparatus. Further, by thinning the thickness of the cured product formed on the mold, the optical composition can be uniformly heated even by a manufacturing method in which the optical composition is polymerized by heating the mold.

  On the other hand, in the optical element of FIG. 2B, the thin film (optical member 10) formed by molding the cured product of the present embodiment is between two substrates, ie, between the lens substrate 30 and the lens substrate 40. It is provided. As a method of manufacturing the optical element of FIG. 2B, for example, an uncured optical composition or the like is poured between the lens substrate 30 and the lens substrate 40, and molding is performed by lightly suppressing the composition. And it is set as hardened | cured material by photopolymerizing an unhardened resin composition, keeping it in this state. As a result, it is possible to obtain an optical element in which the cured product of the present embodiment is sandwiched between the lens substrate 30 and the lens substrate 40.

  It is also possible to form a cured product by a thermal polymerization method. In this case, it is desirable to make the overall temperature more uniform, and to reduce the film thickness of the cured product of the polymerizable composition formed on the substrate of the light transmitting material is more preferable to the optical element of this embodiment. It becomes suitable.

  When the thickness of the cured product to be formed is increased, the film thickness, the irradiation amount of light in consideration of the light absorption of the resin component, the irradiation intensity of light, the light source, etc., and the heating temperature, heating time, etc. are appropriately selected. It is possible to thicken the cured product.

  On the other hand, when using the hardened | cured material of this embodiment in the aspect of said (C), a melt molding method can be used as a shaping | molding method of hardened | cured material. By using the melt molding method, it is possible to obtain a molded product excellent in properties such as low birefringence, mechanical strength and dimensional accuracy. Examples of the melt molding method include press molding, extrusion molding, injection molding and the like, but injection molding is preferable from the viewpoint of moldability and productivity.

  The molding conditions in the molding step are appropriately selected depending on the purpose of use or the molding method. The temperature of the cured product in injection molding is preferably in the range of 150 ° C. to 400 ° C., more preferably in the range of 200 ° C. to 350 ° C., and still more preferably in the range of 200 ° C. to 330 ° C. By molding the cured product in this temperature range, it is possible to impart appropriate fluidity to the resin at the time of molding, and to prevent the occurrence of sink marks and distortion of the optical element of the present embodiment which is a molded product. Further, by molding the cured product in this temperature range, it is possible to prevent the generation of silver streaks due to the thermal decomposition of the cured product, and to effectively prevent the yellowing of the optical element.

  The optical element of the present embodiment can be used, for example, as an optical lens such as a camera lens. In addition, the optical element of the present embodiment can be used for an optical apparatus having an optical element, such as a telescope, binoculars, a microscope, a camera, an endoscope and the like.

  Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to the examples described below as long as the gist of the present invention is not exceeded.

(Synthesis of compounds)
The following compound A to compound O were synthesized based on JP-A-2014-43565 and JP-A-2012-167019. In addition, the optical composition having the general formula (1) and / or (3) and the general formula (2) is mixed in a solvent in which all the necessary materials are all dissolved, and the solvent is distilled off under reduced pressure Manufactured. At that time, in order to suppress the polymerization of the optical composition, it was carried out while passing a gas containing 5% oxygen into the liquid.

(Preparation procedure of evaluation sample)
(1) Preparation of Optical Composition The content of the compound represented by the general formula (1) or the general formula (3) and the compound represented by the general formula (2) is shown in each example or each comparative example. The respective materials were weighed and mixed so as to achieve the desired content. 0.2% by mass of 4-methoxyphenol as a polymerization inhibitor, 0.2% by mass of 1-hydroxy-cyclohexylphenyl ketone as a polymerization initiator (IRGACURE 184 / BASF (formerly Ciba)) relative to the mixture Product was weighed. The above mixture and the weighed compounds were dissolved in acetone and mixed, and then the acetone was distilled off to prepare an optical composition. Further, the additives mentioned in the explanation of the composition for optics may be added as additional additives. For example, 10% by mass of acrylic monomer or the like.

(2) Preparation of Sample for Evaluation (2a) Sample for Refractive Index Measurement Two disc-shaped glass substrates each having a diameter of 30 mm are prepared, and the above optical composition containing a polymerization inhibitor to be measured, a polymerization initiator, etc. The object was sandwiched by a glass substrate provided with a spacer so as to be uniform at a thickness of 500 μm. The sample was irradiated with ultraviolet light to cure the optical composition sandwiched between the two glass substrates, thereby manufacturing an optical element for a sample for refractive index measurement.

(2b) Sample for Confirming Crystallization The optical composition of each of Examples and Comparative Examples to be measured was filled with 5 ± 1 g in a brown bottle (10 ml) and allowed to stand in a thermostat at 80 ° C. for 1 hour. Then, it was left to stand in a 23 ° C. thermostat.

(Evaluation method of preparation sample)
(2) Measurement and evaluation (2a) Refractive index, dispersion characteristic (Abbe number), second-order dispersion characteristic (θg, F)
The refractive index at a wavelength of 587.6 nm and the dispersion characteristics and secondary dispersion characteristics calculated from the following equation are shown in the table.
Abbe number (dispersion characteristic): [ν _d ] = (n _d −1) / (n _F −n _C )
Secondary dispersion _{characteristic: [θg, F] = (} n g -n F) / (n F -n C)

(2b) Confirmation of Crystallization The sample for confirmation of crystallization was taken out of the thermostat after being allowed to stand in a thermostat at 23 ° C. for 24 hours. Then, light is irradiated to the sample for crystallization confirmation from the outside of the brown bottle with LED light of SPA-10SD manufactured by Hayashi Watch Industrial Co., Ltd., and crystals of the size which can be visually confirmed in the sample for crystallization confirmation (the longest side is The presence or absence of generation | occurrence | production of the crystal | crystallization of 2 mm or more was confirmed. The following criteria were evaluated.
A: Crystal did not occur.
B: A crystal with a longest side less than 1 mm was generated.
C: Crystals having a longest side of 1 mm or more and less than 2 mm were generated.
D: A crystal having a longest side of 2 mm or more was generated.

(Examples 1 to 20)
In Examples 1 to 20, each material was weighed at the addition ratio described in Table 1, and the polymerization initiator and the polymerization inhibitor were further weighed, and dissolved and mixed in about 10 times the total volume of acetone. The respective optical compositions were prepared by evaporating the solvent.

  The optical element of the sample for evaluation was produced and evaluated by said method using the obtained composition for optics. The evaluation results are as shown in Table 1.

(Comparative Examples 1 to 6)
In Comparative Examples 1 to 6, an optical element for a sample for evaluation was produced in the same manner as in Example 1 except that the materials listed in Table 2 were used. The evaluation results are as shown in Table 2.

(Evaluation)
While the optical elements of Examples 1 to 20 have θg and F as high as 0.70 or more and 0.76 or less, optical elements which are difficult to be crystallized are obtained.

  On the other hand, in the optical elements of Comparative Examples 1 to 6, only .theta.g and F were less than 0.70 or optical elements that were easily crystallized.

The cured product of the present invention and the optical element of the present invention formed by molding the cured product have high dispersion characteristics (Abbe number (数_d )) and secondary dispersion characteristics (θg, F) of refractive index (high θg, F characteristic) has a high characteristic of the chromatic aberration correction function. Furthermore, since the amount of generation of unevenness in the step of producing a cured product is also reduced, the generation of refractive index distribution in the optical element can be suppressed. Therefore, it can be used for an apparatus having a plurality of lenses such as a camera lens.

10 optical members 20, 30, 40 substrates

Claims (16)

A cured product obtained by polymerizing at least a compound represented by the following general formula (1) and / or a compound represented by the general formula (3), and a compound represented by the following general formula (2),
A cured product characterized in that the compound represented by the general formula (2) contains 0.1 to 50.0% by mass of the total amount of the compounds represented by the general formula (1) and the general formula (3).

(In the general formula (1), X and Y are O or S, and may be the same or different. R ₁ and R ₂ each represent a carbon atom bonded to X and Y, respectively. The substituent may have the same or different molecular weight of 15 or more and less than 170. Z ₁ and Z ₂ may be any one of hydrogen, carbon, oxygen, sulfur, nitrogen or halogen, which is bonded to a benzene ring The substituents having a molecular weight of 1 or more and less than 200 as atoms may be the same or different.
At least one of R ₁ , R ₂ , Z ₁ and Z ₂ has a polymerizable functional group, a and b are 1 or 2, and when a and / or b are 2, Z ₁ and Z ₂ May be the same or different. )

(In the general formula (2), R ₅ and R ₆ are heterocyclic compounds and may be the same or different. The substituent on the heterocycle is a substituent having a molecular weight of 1 or more and less than 200. In the case where there are a plurality of substituents on the hetero ring, the substituents may be the same or different, and the total molecular weight of the substituents is 2 or more and 200 or more. Less than a substituent))

(In the general formula (3), Q is O or S and may be the same or different. R ₃ and R ₄ each have a molecular weight such that the bonding atom to S and Q is a carbon atom 15 or more and less than 170 substituents, which may be the same or different, and Z ₃ is a substituent having a molecular weight of 1 or more and less than 200, which has hydrogen, carbon, oxygen, sulfur or nitrogen as a bonding atom And at least one of R ₃ , R ₄ and Z ₃ has a polymerizable functional group, and c is 1 or 2.) A cured product obtained by polymerizing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (2), wherein the compound represented by the general formula (2) is a compound represented by the general formula (1) The hardened | cured material of Claim 1 characterized by containing 0.1-50.0 mass% of the compound represented by these.

(In the general formula (1), X and Y are O or S, and may be the same or different. R ₁ and R ₂ each represent a carbon atom bonded to X and Y, respectively. The substituent may have the same or different molecular weight of 15 or more and less than 170. Z ₁ and Z ₂ may be any one of hydrogen, carbon, oxygen, sulfur, nitrogen or halogen, which is bonded to a benzene ring The substituents having a molecular weight of 1 or more and less than 200 as atoms may be the same or different.
At least one of R ₁ , R ₂ , Z ₁ and Z ₂ has a polymerizable functional group, a and b are 1 or 2, and when a and / or b are 2, Z ₁ and Z ₂ May be the same or different. )

(In the general formula (2), R ₅ and R ₆ are heterocyclic compounds and may be the same or different. The substituent on the heterocycle is a substituent having a molecular weight of 1 or more and less than 200. In the case where there are a plurality of substituents on the hetero ring, the substituents may be the same or different, and the total molecular weight of the substituents is 2 or more and 200 or more. Less than a substituent)) R ₁ and R _{2 each} represent a methyl group, an ethyl group, a 2-hydroxyethyl group, a 2-mercaptoethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 3-mercaptopropyl group, a 2-mercaptopropyl group, (Meth) acryloyl group, 2- (meth) acryloyloxyethyl group, 2-methyl-2- (meth) acryloyloxyethyl group, 1-methyl-2- (meth) acryloyloxyethyl group, 3- (meth) acryloyl group Oxypropyl group, 2-methyl-3- (meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxypropyl group, 2- (meth) acryloyloxypropyl group, 4- (meth) acryloyl group Oxybutyl group, 3- (meth) acryloyloxybutyl group, 2- (meth) acryloylo Is any one of Shibuchiru group,
Z ₁ and Z _{2 each} represents a hydrogen atom, chloro, methyl, methoxy, ethoxy, methylthio, ethylthio, dimethylamino, diethylamino, 2- (meth) acryloyloxyethoxy, 3- (meth) The cured product according to claim 2, wherein the cured product is any one of an acryloyloxypropoxy group, a 4- (meth) acryloyloxybutoxy group, and a substituent represented by the following general formula (4).

(In the general formula (4), m is a range in which the substituent of the general formula (4) does not have a molecular weight exceeding 200. W is a hydrogen or a methyl group. V is a substituent of the general formula (4) The molecular weight does not exceed 200.) R ₁ and R _{2 each} represents a methyl group, 2-hydroxyethyl group, 2-mercaptoethyl group, 3-hydroxypropyl group, 3-mercaptopropyl group, 2-mercaptopropyl group, (meth) acryloyl group, 2- (meth) group ) Acryloyloxyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl-3- (meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxypropyl group, 4- (meth) ) An acryloyloxybutyl group,
Z ₁ and Z _{2 each} represents a hydrogen atom, a methyl group, a methoxy group, a methylthio group, a dimethylamino group, a 2- (meth) acryloyloxyethoxy group, a 3- (meth) acryloyloxypropoxy group, or the following general formula (4) The cured product according to claim 2 or 3, which is a substituent represented by

(M is 0, V is selected from the groups shown below,
* -O-**,
* -S-**,
* -O-C _n H _2n -O-**,
_{* -S-C n H 2n -O} - **,
* -O-C _n H _2n -S-**,
_{* -S-C n H 2n -S} - **,
* Represents a bond to an alkylene moiety, ** represents a bond to a (meth) acryloyl group, and n is an integer of 2 to 5. ) R ₁ and R _{2 each} represent a methyl group, a (meth) acryloyl group, a 2- (meth) acryloyloxyethyl group, a 3- (meth) acryloyloxypropyl group, a 2-methyl-3- (meth) acryloyloxypropyl group , 2,2-dimethyl-3- (meth) acryloyloxypropyl group, 4- (meth) acryloyloxybutyl group,
Z ₁ and Z _{2 each} represents a hydrogen atom, a methyl group, a methoxy group, a methylthio group, a 2- (meth) acryloyloxyethoxy group, a 3- (meth) acryloyloxypropoxy group, or a substituent represented by the following general formula (4) The cured product according to any one of claims 2 to 4, which is a group, and may be the same or different.

(M is 0, V is selected from the groups shown below,
* -O-**,
* -S-**,
_{* -O-CH 2 CH 2 -O} - **,
_{* -O-CH 2 CH 2 CH} 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -S-CH 2 CH 2 -S} - **,
_{* -S-CH 2 CH 2 CH} 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **,
_{* -S-CH 2 C (CH} 3) 2 CH 2 -S - **
* Represents a bond to an alkylene moiety, and ** represents a bond to a (meth) acryloyl group. ) A cured product obtained by polymerizing at least a compound represented by the following general formula (3) and a compound represented by the following general formula (2),
2. The cured product according to claim 1, wherein the compound represented by the general formula (2) contains 0.1 to 50.0% by mass of the compound represented by the general formula (1).

(In the general formula (3), Q is O or S and may be the same or different. R ₃ and R ₄ each have a molecular weight such that the bonding atom to S and Q is a carbon atom 15 or more and less than 170 substituents, which may be the same or different, and each of Z ₃ is a molecular weight of 1 or more in which hydrogen, carbon, oxygen, sulfur, nitrogen or halogen is a bonding atom to a benzene ring It is a substituent less than 200. At least one of R ₃ , R ₄ and Z ₃ has a polymerizable functional group, and c is 1 or 2.)

(In the general formula (2), R ₅ and R ₆ are heterocyclic compounds and may be the same or different. The substituent on the heterocycle is a substituent having a molecular weight of 1 or more and less than 200. In the case where there are a plurality of substituents on the hetero ring, the substituents may be the same or different, and the total molecular weight of the substituents is 2 or more and 200 or more. Less than a substituent)) The Q is O,
R ₃ and R _{4 each} represent a methyl group, a (meth) acryloyl group, a 2- (meth) acryloyloxyethyl group, a 2-methyl-2- (meth) acryloyloxyethyl group, a 1-methyl-2- (meth) Acryloyloxyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl-3- (meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) acryloyloxypropyl group, 2- (meth) Any of acryloyloxypropyl groups, which may be the same or different,
Z ₃ represents a hydrogen atom, chloro group, methyl group, methoxy group, methylthio group, dimethylamino group, 2- (meth) acryloyloxyethoxy group, 3- (meth) acryloyloxypropoxy group, 4- (meth) acryloyl group 7. The cured product according to claim 6, which is an oxybutoxy group or any of the substituents represented by the following general formula (4).

(M is 0, V is selected from the groups shown below,
* -O-**,
* -S-**,
_{* -O-CH 2 CH 2 -O} - **,
_{* -O-CH 2 CH 2 CH} 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 -O - **,
_{* -O-CH 2 CH 2 CH} 2 CH 2 CH 2 -O - **,
_{* -O-CH 2 C (CH} 3) 2 CH 2 -O - **,
_{* -S-CH 2 CH 2 -S} - **,
_{* -S-CH 2 CH 2 CH} 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 -S - **,
_{* -S-CH 2 CH 2 CH} 2 CH 2 CH 2 -S - **, * - S-CH 2 C (CH 3) 2 CH 2 -S - **
* Represents a bond to an alkylene moiety, and ** represents a bond to a (meth) acryloyl group. ) The R ₃ and the R ₄ may be the same as or different from each other, and a (meth) acryloyl group, a 2- (meth) acryloyloxyethyl group, a 2-methyl-2- (meth) acryloyloxyethyl group 1-Methyl-2- (meth) acryloyloxyethyl group, 3- (meth) acryloyloxypropyl group, 2-methyl-3- (meth) acryloyloxypropyl group, 2,2-dimethyl-3- (meth) Either an acryloyloxypropyl group or a 2- (meth) acryloyloxypropyl group,
Z ₃ represents a hydrogen atom, chloro group, methyl group, methoxy group, methylthio group, dimethylamino group, 2- (meth) acryloyloxyethoxy group, 3- (meth) acryloyloxypropoxy group, 4- (meth) acryloyl group The cured product according to claim 7, which is an oxybutoxy group. In the general formula (2), R ₅ and R ₆ are any one selected from the following general formulas (5) to (20), and R ₅ and R ₆ may be the same or different. ,
The substituent on the heterocycle is a substituent having a molecular weight of 1 or more and less than 200, and may be the same or different. When Z ₄ on the heterocycle is plural, Z ₄ is the same. The cured product according to any one of claims 1 to 8, wherein the total molecular weight of the substituents is 2 or more and less than 200.

(In the general formulas (5) to (20), Z ₄ is a substituent having a molecular weight of 1 to less than 200, d is an integer of 1 to 5, and d is an integer of 2 to 5) The substituents may be the same or different, and the total molecular weight of Z4 is 2 or more and less than 200.) Z ₄ is a hydrogen atom, methyl group, methoxy group, ethoxy group, methylthio group, ethylthio group, dimethylamino group, diethylamino group, 2- (meth) acryloyloxyethoxy group, (meth) acryloyloxymethyl group, 2- (2) (Meth) acryloyloxyethoxymethyl group, 3- (meth) acryloyloxypropoxymethyl group, 4- (meth) acryloyloxybutoxymethyl group, 3- (meth) acryloyloxy-2-methylpropoxymethyl group, (meth) acryloyloxy group -1-ethyl group, 2- (meth) acryloyloxyethoxy-1-ethyl group, 3- (meth) acryloyloxypropoxy-1-ethyl group, 4- (meth) acryloyloxybutoxy-1-ethyl group, 3- (Meth) acryloyloxy-2-methylpropoxy-1 The cured product according to claim 9, which is any one of -ethyl group. Wherein Z ₄ is a hydrogen atom, a methyl group, a methoxy group, methylthio group, dimethylamino group, 2- (meth) acryloyloxy ethoxy, (meth) acryloyloxy methyl group is the (meth) acryloyloxy-1-ethyl group The hardened | cured material of Claim 10 characterized by the above-mentioned. A base material, and an optical element in which a resin is provided on the base material,
An optical element characterized in that the resin is a cured product according to any one of claims 1 to 11. An optical element in which a resin is provided between two substrates,
An optical element characterized in that the resin is a cured product according to any one of claims 1 to 11.   The optical element according to claim 12 or 13, wherein the optical element is a lens.   An optical apparatus comprising the optical element according to any one of claims 12 to 14. Providing the cured product according to any one of claims 1 to 11 on or between the substrates;
And b. Molding the cured product.

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