Cured product, optical member, lens, compound, and curable composition

Patent metadata

Field	Value
Publication number	US-11078180-B2
Application number	US-202016803896-A
Country	US
Kind code	B2
Filing date	Feb 27, 2020
Priority date	Aug 30, 2017
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

According to the present invention, a cured product obtained by curing a curable composition including a compound represented by General Formula 1, in which a birefringence Δn (587 nm) is 0.00≤Δn (587 nm)≤0.01, is provided, and this cured product is suitable for manufacturing an optical member.

Pol 1 - Sp 1 - L 1 -Ar- L 2 - Sp 2 - Pol 2   (General Formula 1)

In formula, Ar is an aromatic ring group represented by General Formula 2-2 and the like.

In formula, Z 1 and Z 2 each represent a hydrogen atom, a methyl group, and the like; A 1 and A 2 each represent —S— and the like; X represents C(Rz) 2 and the like (where Rz is a substituent, and two Rz's may form a ring); L 1 and L 2 each represent a single bond, —O—, —OC(═O)—, —OC(═O)O—, —OC(═O)NH—, and the like; Sp 1 and Sp 2 each represent a single bond or a divalent linking group; Pol 1 and Pol 2 each represent a hydrogen atom or a polymerizable group; and a compound represented by General Formula 1 has at least one polymerizable group.

First claim

What is claimed is:

1. A cured product obtained by curing a curable composition including a compound represented by General Formula 1,
wherein a birefringence Δn at a wavelength of 587 nm is 0.00≤Δn≤0.01,
Pol 1 - Sp 1 - L 1 -Ar- L 2 - Sp 2 - Pol 2   (General Formula 1)

in formula, Ar is an aromatic ring group represented by General Formula 2-2, and

in formula
Z 1 and Z 2 each independently represent a hydrogen atom, a methyl group, or an ethyl group
A 1 and A 2 each independently represent —S—,
X represents C to which two cyano groups are bonded, C to which a cyano group and an alkoxy carbonyl group are bonded, or a ring represented by the following formula;

wherein the ring represented by the above formula may be substituted by one or two alkyl groups having 1 to 6 carbon atoms and * represents a bonding position,
L 1 and L 2 each independently represent —O—, —OC(═O)—, —C(═O)—, —OC(═O)O—, —OC(═O)NH—, or —NHC(═O)O—,
Sp 1 and Sp 2 each independently represent a linking group selected from the group consisting of a linear alkylene group which has 2 to 30 carbon atoms and may be substituted with a methyl group or a linear alkylene group which has 1 to 30 carbon atoms and may be substituted with a methyl group and in which one —CH 2 — or two or more non-adjacent —CH 2 —'s are substituted by —O—, —S—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —NHC(═O)—, —C(═O)NH—, —OC(═O)NH—, or —NHC(═O)O, and
Pol 1 and Pol 2 each independently represent a (meth)acryloyloxy group.

2. The cured product according to claim 1 ,
wherein L 1 and L 2 are all —O—, —OC(═O)—, —OC(═O)O—, or O—C(═O)NH—.

3. The cured product according to claim 2 ,
wherein L 1 and L 2 are all —O—.

4. A lens comprising the cured product according to claim 1 .

5. A compound represented by General Formula 1,
Pol 1 - Sp 1 - L 1 -Ar- L 2 - Sp 2 - Pol 2   (General Formula 1)

in formula, Ar is an aromatic ring group represented by General Formula 2-2, and

in formula,
Z 1 and Z 2 each independently represent a hydrogen atom, a methyl group, or an ethyl group
A 1 and A 2 each independently represent —S—,
X represents C to which two cyano groups are bonded, C to which a cyano group and an alkoxy carbonyl group are bonded, or a ring represented by the following formula;

wherein the ring represented by the above formula may be substituted by one or two alkyl groups having 1 to 6 carbon atoms and * represents a bonding position,
L 1 and L 2 each independently represent —O—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —OC(═O)NH—, or —NHC(═O)O—,
Sp 1 and Sp 2 each represent a linking group selected from the group consisting of a linear alkylene group which has 2 to 30 carbon atoms and may be substituted with a methyl group or a linear alkylene group which has 1 to 30 carbon atoms and may be substituted with a methyl group and in which one —CH 2 — or two or more non-adjacent —CH 2 —'s are substituted by —O—, —S—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —NHC(═O)—, —C(═O)NH—, —OC(═O)NH—, or —NHC(═O)O, and
Pol 1 and Pol 2 each independently represent a (meth)acryloyloxy group.

6. The compound according to claim 5 ,
wherein L 1 and L 2 are all —O—, —OC(═O)—, —OC(═O)O—, or O—C(═O)NH—.

7. The compound according to claim 6 ,
wherein L 1 and L 2 are all —O—.

8. The compound according to claim 5 ,
which is represented by any one of the following formulae:

9. A curable composition comprising:
the compound according to claim 5 ; and
a polyfunctional (meth)acrylate monomer having three or more (meth)acryloyl groups in a molecule.

10. A curable composition comprising:
the compound according to claim 6 ; and
a polyfunctional (meth)acrylate monomer having three or more (meth)acryloyl groups in a molecule.

11. A curable composition comprising:
the compound according to claim 8 ; and
a polyfunctional (meth)acrylate monomer having three or more (meth)acryloyl groups in a molecule.

12. The cured product according to claim 1 ,
wherein X represents any one of the following formulae;

wherein * represents a bonding position of the C, and
Sp 1 and Sp 2 each represent a linking group selected from the following formulae;

wherein ##represents a position bonding to L 1 or L 2 and #represents a position bonding to Pol 1 or Pol 2 .

13. The cured product according to claim 1 ,
wherein the compound represented by General Formula 1 is represented by any one of the following formulae

14. The cured product according to claim 1 ,
wherein the compound represented by General Formula 1 is represented by any one of the following formulae

15. The compound according to claim 5 ,
wherein X represents any one of the following formulae;

in the formulae * represents a bonding position, and
Sp 1 and Sp 2 each represent a linking group selected from the following formulae;

wherein ##represents a position bonding to L 1 or L 2 and #represents a position bonding to Pol 1 or Pol 2 .

16. The compound according to claim 5 ,
which is represented by any one of the following formulae

Assignees

• Fujifilm Corp

Inventors

• Morooka Naoyuki
• Shiraiwa Naozumi

Classifications

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• C08F220/28

  containing no aromatic rings in the alcohol moiety · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D339/06 Primary

  having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates · CPC title