(Meth)acrylate compound, additive for optical resin, optical element, and optical device

Patent metadata

Field	Value
Publication number	US-11142636-B2
Application number	US-201916459923-A
Country	US
Kind code	B2
Filing date	Jul 2, 2019
Priority date	Jan 17, 2017
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

Provided is an additive for an optical resin including a (meth)acrylate compound represented by general formula (1) below:[in general formula (1), each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom; m represents an integer of 0 to 5; R1 represents an alkylene group or an oxyalkylene group having a carbon number of 1 to 8; and R2 represents a hydrogen atom or a methyl group].

First claim

What is claimed is:

1. A (meth)acrylate compound represented by general formula (1):

wherein, in the general formula (1),
each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom;
m represents 0;
R 1 represents an alkylene group having a carbon number of 2 or of 4 to 8 or an oxyalkylene group having a carbon number of 1 to 8; and
R 2 represents a hydrogen atom or a methyl group.

2. An additive for an optical resin comprising a (meth)acrylate compound represented by general formula (1):

wherein, in the general formula (1),
each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom;
m represents 0;
R 1 represents an alkylene group having a carbon number of 2 or of 4 to 8 or an oxyalkylene group having a carbon number of 1 to 8; and
R 2 represents a hydrogen atom or a methyl group.

3. A resin precursor composition comprising: bifunctional (meth)acrylate (A Component); monofunctional (meth)acrylate (B Component); and a photopolymerization initiator (C Component), wherein the B Component is a compound represented by general formula (1) below:

wherein, in the general formula (1),
each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom;
m represents 0;
R 1 represents an alkylene group having a carbon number of 2 or of 4 to 8 or an oxyalkylene group having a carbon number of 1 to 8; and
R 2 represents a hydrogen atom or a methyl group.

4. The resin precursor composition according to claim 3 , wherein the A Component is a compound represented by general formula (6) below:

wherein, in the general formula (6) and the general formula (7), each R independently represents a hydrogen atom or a methyl group; p and q each independently represent an integer of 1 to 3; in the general formula (7), R 4 and R 5 each independently represent a hydrogen atom or an alkyl group having a carbon number of 1 to 2; and R 6 , R 7 , R 8 , and R 9 each independently represent any one of a hydrogen atom, a fluorine atom, an alkyl group having a carbon number of 1 to 6, and a phenyl group in which one or some of hydrogen atoms are optionally substituted with an alkyl group having a carbon number of 1 to 6.

5. An optical resin composition comprising:
a constitutional unit represented by general formula (8):

wherein, in the general formula (8),
each R independently represents a hydrogen atom or a methyl group;
each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom;
m represents 0; and
R 1 represents an alkylene group having a carbon number of 2 or of 4 to 8 or an oxyalkylene group having a carbon number of 1 to 8-8.

6. The optical resin composition according to claim 5 , wherein the optical resin composition has a refractive index nd at d-line (587.56 nm) of 1.53 or smaller and an Abbe number νd of 39 or smaller.

7. The optical resin composition according to claim 5 , wherein the optical resin composition has a storage elastic modulus at 100° C. of 50 MPa or higher.

8. The optical resin composition according to claim 5 , wherein the optical resin composition has a linear expansion coefficient from 25° C. to 70° C. of 2.0×10 −4 (1/K) or lower.

9. An optical resin precursor composition comprising:
(a) the additive for an optical resin according to claim 2 ;
(b) an optical resin compound; and
(c) a photopolymerization initiator.

10. An optical element comprising:
a resin composition obtained by curing the optical resin composition according to claim 5 .

11. An optical element comprising:
an optical resin composition obtained by curing the optical resin composition according to claim 5 ; and
an optical resin composition having a high refractive index and low dispersion compared with the obtained optical resin composition.

12. An optical device comprising
the optical element according to claim 10 .

Assignees

• Nikon Corp

Inventors

• Kasuya Masakatsu
• Inokuchi Yosuke
• Nishimura Shiho
• Nakamura Toru

Classifications

• C08L33/14 Primary

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• C07C69/653

  Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters · CPC title

• G02B5/1876

  Diffractive Fresnel lenses; Zone plates; Kinoforms (G02B5/1842, G02B5/1847 take precedence; optical systems having diffractive correction means G02B27/0037; Fresnel lenses operating by refraction G02B3/08) · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title