# US 11,078,180 B2 · Cured product, optical member, lens, compound, and curable composition

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- Number: US 11,078,180 B2
- Document ID: US11078180B2
- Status: Granted
- Kind: B2
- Application number: 16/803,896
- Filed: 2020-02-27
- Published: 2020-06-25
- Granted: 2021-08-03
- Earliest claimed: 2017-08-30
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Naoyuki Morooka; Naozumi Shiraiwa
- Web page: https://patentgrep.com/patent/US11078180B2

## CPC

- C07D 339/06: having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
- G02B 1/041: {Lenses}
- C07D 277/82: Nitrogen atoms
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C08F 220/28: containing no aromatic rings in the alcohol moiety
- C08F 222/10: Esters
- C08F 222/1025: {of aromatic dialcohols}
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## 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. Pol1-Sp1-L1-Ar-L2-Sp2-Pol2 (General Formula 1) In formula, Ar is an aromatic ring group represented by General Formula 2-2 and the like. In formula, Z1 and Z2 each represent a hydrogen atom, a methyl group, and the like; A1 and A2 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); L1 and L2 each represent a single bond, —O—, —OC(═O)—, —OC(═O)O—, —OC(═O)NH—, and the like; Sp1 and Sp2 each represent a single bond or a divalent linking group; Pol1 and Pol2 each represent a hydrogen atom or a polymerizable group; and a compound represented by General Formula 1 has at least one polymerizable group.

## Claims

### Claim 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,
Pol1-Sp1-L1-Ar-L2-Sp2-Pol2 (General Formula 1)
in formula, Ar is an aromatic ring group represented by General Formula 2-2, and
in formula
Z1 and Z2 each independently represent a hydrogen atom, a methyl group, or an ethyl group
A1 and A2 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,
L1 and L2 each independently represent —O—, —OC(═O)—, —C(═O)—, —OC(═O)O—, —OC(═O)NH—, or —NHC(═O)O—,
Sp1 and Sp2 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 —CH2— or two or more non-adjacent —CH2—'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
Pol1 and Pol2 each independently represent a (meth)acryloyloxy group.

### Claim 2 (depends on 1)

The cured product according to claim 1,
wherein L1 and L2 are all —O—, —OC(═O)—, —OC(═O)O—, or O—C(═O)NH—.

### Claim 3 (depends on 2)

The cured product according to claim 2,
wherein L1 and L2 are all —O—.

### Claim 4 (depends on 1)

A lens comprising the cured product according to claim 1.

### Claim 5

A compound represented by General Formula 1,
Pol1-Sp1-L1-Ar-L2-Sp2-Pol2 (General Formula 1)
in formula, Ar is an aromatic ring group represented by General Formula 2-2, and
in formula,
Z1 and Z2 each independently represent a hydrogen atom, a methyl group, or an ethyl group
A1 and A2 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,
L1 and L2 each independently represent —O—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —OC(═O)NH—, or —NHC(═O)O—,
Sp1 and Sp2 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 —CH2— or two or more non-adjacent —CH2—'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
Pol1 and Pol2 each independently represent a (meth)acryloyloxy group.

### Claim 6 (depends on 5)

The compound according to claim 5,
wherein L1 and L2 are all —O—, —OC(═O)—, —OC(═O)O—, or O—C(═O)NH—.

### Claim 7 (depends on 6)

The compound according to claim 6,
wherein L1 and L2 are all —O—.

### Claim 8 (depends on 5)

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

### Claim 9 (depends on 5)

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.

### Claim 10 (depends on 6)

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.

### Claim 11 (depends on 8)

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.

### Claim 12 (depends on 1)

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
Sp1 and Sp2 each represent a linking group selected from the following formulae;
wherein ##represents a position bonding to L1 or L2 and #represents a position bonding to Pol1 or Pol2.

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 5)

The compound according to claim 5,
wherein X represents any one of the following formulae;
in the formulae * represents a bonding position, and
Sp1 and Sp2 each represent a linking group selected from the following formulae;
wherein ##represents a position bonding to L1 or L2 and #represents a position bonding to Pol1 or Pol2.

### Claim 16 (depends on 5)

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