# US 10,370,474 B2 · Optical composition, cured product, and optical element

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- Number: US 10,370,474 B2
- Document ID: US10370474B2
- Status: Granted
- Kind: B2
- Application number: 15/494,956
- Filed: 2017-04-24
- Published: 2017-11-09
- Granted: 2019-08-06
- Earliest claimed: 2016-05-06
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Terunobu Saitoh
- Web page: https://patentgrep.com/patent/US10370474B2

## CPC

- G02B 1/041: {Lenses}
- B32B 27/286: {comprising polysulphones; polysulfides}
- C08F 228/04: Thioethers
- B32B 2307/412: Transparent
- B32B 2551/00: Optical elements
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

Provided is a cured product having the following characteristics: the dispersion characteristic and secondary dispersion characteristic of refractive indices are high, the cured product hardy crystallizes, and a chromatic aberration-correcting function is high. The cured product contains at least a structure represented by the general formula (4) and a structure represented by the general formula (5), in which a content of the structure represented by the general formula (5) in the cured product is 0.01 or more and 0.10 or less in terms of a substance amount ratio with respect to the structure represented by the general formula (4).

## Claims

### Claim 1

A material comprising:
first compound represented by general formula (1) and
a second compound represented by general formula (2),
wherein the first compound and the second compound are polymerized with each other, and
wherein a content of the second compound in the material is 1.0 mass % to 10.0 mass % with respect to the first compound:
wherein, in the general formula (1) and the general formula (2):
X1, X2, Y1, and Y2 each represents O or S, and may be identical to or different from one another;
R1 to R4 each represents one selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, an allyl group, a 2-(meth)acryloyloxyethyl group, a 3-(meth)acryloyloxypropyl group, and a 4-(meth)acryloyloxybutyl group, and may be identical to or different from one another;
Z1, Z4, and Z6 each represents a structure represented by general formula (3);
Z2, Z3, Z5, and Z7 each represents one selected from the group consisting of 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 2-(meth)acryloyloxyethoxy group, a 3-(meth)acryloyloxypropoxy group, a 4-(meth)acryloyloxybutoxy group, and a structure represented by the general formula (3), and may be identical to or different from one another; and
Z8 represents V in a structure represented by the general formula (3):
wherein, in the general formula (3), m represents 0 or 1, W represents a hydrogen atom or a methyl group, and V is selected from the group consisting of:
*—O—**;
*—S—**;
*—O—CnH2n—O—**;
*—S—CnH2n—O—**;
*—O—CnH2n—S—**; and
*—S—CnH2n—S—**,
where, in each of the Z1 to the Z7, * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and
where, in the Z8, the V does not represent *—O—** and *—S—**, and each of * and ** represents a bonding site with an alkylene moiety, and a structure represented by CnH2n in the V may have a substituent on a carbon atom, and n represents an integer selected from the group consisting of 2 to 5.

### Claim 2

An optical element comprising an optical member,
wherein the optical member comprises:
a first compound represented by general formula (1): and
a second compound represented by general formula (2),
wherein the first compound and the second compound are polymerized with each other, and
wherein a content of the second compound in the optical member is 1.0 mass% to 10.0 mass% with respect to the first compound:
wherein, in the general formula (1) and the general formula (2):
X1, X2, Y1, and Y2 each represents O or S, and may be identical to or different from one another;
R1 to R4 each represents one selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, an allyl group, a 2-(meth)acryloyloxyethyl group, a 3-(meth)acryloyloxypropyl group, and a 4-(meth)acryloyloxybutyl group, and may be identical to or different from one another;
Z1, Z4, and Z6 each represents a structure represented by general formula (3);
Z2, Z3, Z5, and Z7 each represents one selected from the group consisting of 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 2-(meth)acryloyloxyethoxy group, a 3-(meth)acryloyloxypropoxy group, a 4-(meth)acryloyloxybutoxy group, and a structure represented by the general formula
Z8 represents V in a structure represented by the general formula (3):
wherein, in the general formula (3), m represents 0 or 1, W represents a hydrogen atom or a methyl group, and V is selected from the group consisting of:
*—O—**;
*—S—**;
*—O—CnH2n—O—**;
*—S—CnH2n—O—**;
*—O—CnH2n—S—**; and
*—S—CnH2n—S—**,
where, in each of the Z1 to the Z7, * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and
where, in the Z8, the V does not represent *—O—** and *—S—**, and each of * and ** represents a bonding site with an alkylene moiety, and a structure represented by CnH2n in the V may have a substituent on a carbon atom, and n represents an integer selected from the group consisting of 2 to 5.

### Claim 3 (depends on 2)

An optical element according to claim 2, wherein the optical element is a lens comprising a base material, and
wherein the optical member is arranged to the base material.

### Claim 4 (depends on 2)

An optical element according to claim 2, wherein the optical element is a arranged between two base materials.

### Claim 5 (depends on 2)

An optical apparatus, comprising the optical element of claim 2.

### Claim 6 (depends on 1)

The material according to claim 1, wherein the X1, the X2, the Y1, and the Y2 each represents O.

### Claim 7 (depends on 1)

The material according to claim 1, wherein:
the R1 to the R4 each represents one selected from the group consisting of a methyl group, an ethyl group, a propyl group, and an isopropyl group; and
the Z2, the Z3, the Z5, and the Z7 each represents one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, and an isopropyl group.

### Claim 8 (depends on 1)

The material according to claim 1, wherein:
the R1 to the R4 each represents a methyl group or an isopropyl group; and
the Z2, the Z3, the Z5, and the Z7 each represents a hydrogen atom.

### Claim 9 (depends on 1)

The material according to claim 1, wherein, in the general formula (3), the m represents 0 and the V represents any one of:
*—O—**;
*—S—**;
*—O—CH2CH2—O—**;
*—O—CH2CH2CH2—O—**;
*—O—CH2CH2CH2CH2—O—**;
*—O—CH2C(CH3)2CH2—O—**;
*—S—CH2CH2—S—**;
*—S—CH2CH2CH2—S—**;
*—S—CH2CH2CH2CH2—S—**; and
*—S—CH2C(CH3)2CH2—S—**,
provided that in each of the Z1 to the Z7, * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and in the Z8, the V does not represent *—O—** and *—S—**, and both of * and ** each represents a bonding site with an alkylene moiety.

### Claim 10

A method of producing a material, comprising:
preparing an optical composition containing at least a first compound represented by general formula (1) and a second compound represented by general formula (2), a content of the second compound in the optical composition being 1.0 mass % to 10.0 mass % with respect to the first compound; and
polymerizing the optical composition to cure the composition:
wherein, in the general formula (1) and the general formula (2):
X1, X2, Y1, and Y2 each represents O or S, and may be identical to or different from one another;
R1 to R4 each represents one selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, an allyl group, a 2-(meth)acryloyloxyethyl group, a 3-(meth)acryloyloxypropyl group, and a 4-(meth)acryloyloxybutyl group, and may be identical to or different from one another;
Z1, Z4, and Z6 each represents a structure represented by general formula (3);
Z2, Z3, Z5, and Z7 each represents one selected from the group consisting of 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 2-(meth)acryloyloxyethoxy group, a 3-(meth)acryloyloxypropoxy group, a 4-(meth)acryloyloxybutoxy group, and a structure represented by the general formula (3), and may be identical to or different from one another; and
Z8 represents V in a structure represented by the general formula (3):
wherein, in the general formula (3), m represents 0 or 1, W represents a hydrogen atom or a methyl group, and V is selected from the group consisting of:
*—O—**;
*—S—**;
*—O—CnH2n—O—**;
*—S—CnH2n—O—**;
*—O—CnH2n—S—**; and
*—S—CnH2n—S—**,
where, in each of the Z1 to the Z7, * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and
where, in the Z8, the V does not represent *—O—** and *—S—**, and each of * and ** represents a bonding site with an alkylene moiety, and a structure represented by CnH2n in the V may have a substituent on a carbon atom, and n represents an integer selected from the group consisting of 2 to 5.

### Claim 11 (depends on 10)

The method according to claim 10, wherein the optical composition further contains a polymerizable material capable of copolymerizing with the first compound and the second compound.

### Claim 12 (depends on 11)

The method according to claim 11, wherein the first compound and the second compound are dispersed into the polymerizable material.

### Claim 13 (depends on 10)

The method according to claim 10, wherein the optical composition further contains a matrix polymer compound.

### Claim 14 (depends on 5)

The optical apparatus according to claim 5, wherein the optical apparatus is a camera.