Optical composition, cured product, and optical element

Patent metadata

Field	Value
Publication number	US-10370474-B2
Application number	US-201715494956-A
Country	US
Kind code	B2
Filing date	Apr 24, 2017
Priority date	May 6, 2016
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

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).

First claim

What is claimed is:

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):
X 1 , X 2 , Y 1 , and Y 2 each represents O or S, and may be identical to or different from one another;
R 1 to R 4 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;
Z 1 , Z 4 , and Z 6 each represents a structure represented by general formula (3);
Z 2 , Z 3 , Z 5 , and Z 7 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
Z 8 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—C n H 2n —O—**;
*—S—C n H 2n —O—**;
*—O—C n H 2n —S—**; and
*—S—C n H 2n —S—**,
where, in each of the Z 1 to the Z 7 , * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and
where, in the Z 8 , 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 C n H 2n 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.

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):
X 1 , X 2 , Y 1 , and Y 2 each represents O or S, and may be identical to or different from one another;
R 1 to R 4 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;
Z 1 , Z 4 , and Z 6 each represents a structure represented by general formula (3);
Z 2 , Z 3 , Z 5 , and Z 7 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
Z 8 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—C n H 2n —O—**;
*—S—C n H 2n —O—**;
*—O—C n H 2n —S—**; and
*—S—C n H 2n —S—**,
where, in each of the Z 1 to the Z 7 , * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and
where, in the Z 8 , 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 C n H 2n 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.

3. 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.

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

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

6. The material according to claim 1 , wherein the X 1 , the X 2 , the Y 1 , and the Y 2 each represents O.

7. The material according to claim 1 , wherein:
the R 1 to the R 4 each represents one selected from the group consisting of a methyl group, an ethyl group, a propyl group, and an isopropyl group; and
the Z 2 , the Z 3 , the Z 5 , and the Z 7 each represents one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, and an isopropyl group.

8. The material according to claim 1 , wherein:
the R 1 to the R 4 each represents a methyl group or an isopropyl group; and
the Z 2 , the Z 3 , the Z 5 , and the Z 7 each represents a hydrogen atom.

9. 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—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 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—**; and
*—S—CH 2 C(CH 3 ) 2 CH 2 —S—**,
provided that in each of the Z 1 to the Z 7 , * represents a bonding site with an alkylene moiety and ** represents a bonding site with a (meth)acryloyl group, and in the Z 8 , the V does not represent *—O—** and *—S—**, and both of * and ** each represents a bonding site with an alkylene moiety.

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):
X 1 , X 2 , Y 1 , and Y 2 each represents O or S, and may be identical to or different from one another;
R 1 to R 4 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,

Assignees

• Canon Kk

Inventors

• Saitoh Terunobu

Classifications

• G02B1/041 Primary

  Lenses · CPC title

• B32B2551/00

  Optical elements · CPC title

• C08F228/04

  Thioethers · CPC title

• B32B2307/412

  Transparent · CPC title

• C08F222/24 Primary

  Esters containing sulfur · CPC title