Curable composition and optical material comprising cured product thereof

Patent metadata

Field	Value
Publication number	US-12410284-B2
Application number	US-202017604253-A
Country	US
Kind code	B2
Filing date	May 21, 2020
Priority date	May 24, 2019
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

A curable composition comprising an episulfide compound represented by Chemical Formula 1 and an aromatic ring compound containing two or more hydroxyl groups represented by Chemical Formula 2 or 3, and an optical material including a cured product of the curable composition.

First claim

What is claimed is:

1. A curable composition for forming a high refractive index optical material, the curable composition comprising:
an episulfide compound represented by the following Chemical Formula 1; and
an aromatic ring compound containing two or more hydroxyl groups represented by the following Chemical Formula 2 or 3,
wherein a weight ratio of the episulfide compound and the aromatic ring compound containing two or more hydroxyl groups is 7:3 to 9:1,
wherein the curable composition does not contain a thiol compound,

in Chemical Formula 1,
R 1 and R 2 are each independently hydrogen or an alkyl having 1 to 10 carbon atoms,
R 3 and R 4 are each independently a single bond or an alkylene having 1 to 10 carbon atoms,
a is an integer of 0 to 4, and
b is an integer of 0 to 6,

in Chemical Formula 2,
R 5 and R 6 are each independently deuterium, halogen, cyano, nitrile, nitro, amino, an alkyl having 1 to 40 carbon atoms, an alkoxy having 1 to 40 carbon atoms, a cycloalkyl having 3 to 40 carbon atoms, an alkenyl having 1 to 40 carbon atoms, an aryl having 6 to 60 carbon atoms, or a heteroaryl having 1 to 40 carbon atoms containing at least one of O, N, Si and S,
c and d are each independently an integer of 1 to 7,
e and f are each independently an integer of 0 to 6,
c+e is 7 or less, d+f is 7 or less, and c+d is 2 or more,

in Chemical Formula 3,
Ar 1 and Ar 2 are each independently an aryl having 6 to 60 carbon atoms including one or more hydroxyl groups,
R 7 and R 8 are each independently deuterium, halogen, cyano, nitrile, nitro, amino, an alkyl having 1 to 40 carbon atoms, an alkoxy having 1 to 40 carbon atoms, a cycloalkyl having 3 to 40 carbon atoms, an alkenyl having 1 to 40 carbon atoms, an aryl having 6 to 60 carbon atoms, or a heteroaryl having 1 to 40 carbon atoms containing at least one of O, N, Si and S, and
m and n are each independently an integer of 0 to 4.

2. The curable composition according to claim 1 , wherein the weight ratio of the episulfide compound and the aromatic ring compound containing two or more hydroxyl groups is 8:2 to 9:1.

3. The curable composition according to claim 1 , wherein the episulfide compound comprises at least one selected from the group consisting of bis(β-epithiopropyl)sulfide, bis(β-epithiopropyl)disulfide, bis(β-epithiopropylthio)methane, 1,2-bis(β-epithiopropylthio)ethane, 1,3-bis(β-epithiopropylthio) propane, and 1,4-bis(β-epithiopropylthio)butane.

4. The curable composition according to claim 1 , wherein the aromatic ring compound containing two or more hydroxyl groups comprises at least one selected from the following compounds:

5. The curable composition according to claim 1 , wherein the curable composition further comprises a catalyst.

6. An optical material comprising a cured product of a curable composition, the curable composition comprises:
an episulfide compound represented by the following Chemical Formula 1; and
an aromatic ring compound containing two or more hydroxyl groups represented by the following Chemical Formula 2 or 3,
wherein the episulfide compound and the aromatic ring compound containing two or more hydroxyl groups is contained in a weight ratio of 7:3 to 9:1,
wherein the curable composition does not contain a thiol compound,

in Chemical Formula 1,
R 1 and R 2 are each independently hydrogen or an alkyl having 1 to 10 carbon atoms,
R 3 and R 4 are each independently a single bond or an alkylene having 1 to 10 carbon atoms,
a is an integer of 0 to 4, and
b is an integer of 0 to 6,

in Chemical Formula 2,
R 5 and R 6 are each independently deuterium, halogen, cyano, nitrile, nitro, amino, an alkyl having 1 to 40 carbon atoms, an alkoxy having 1 to 40 carbon atoms, a cycloalkyl having 3 to 40 carbon atoms, an alkenyl having 1 to 40 carbon atoms, an aryl having 6 to 60 carbon atoms, or a heteroaryl having 1 to 40 carbon atoms containing at least one of O, N, Si and S,
c and d are each independently an integer of 1 to 7,
e and f are each independently an integer of 0 to 6,
c+e is 7 or less, d+f is 7 or less, and c+d is 2 or more,

in Chemical Formula 3,
Ar 1 and Ar 2 are each independently an aryl having 6 to 60 carbon atoms including one or more hydroxyl groups,
R 7 and R 8 are each independently deuterium, halogen, cyano, nitrile, nitro, amino, an alkyl having 1 to 40 carbon atoms, an alkoxy having 1 to 40 carbon atoms, a cycloalkyl having 3 to 40 carbon atoms, an alkenyl having 1 to 40 carbon atoms, an aryl having 6 to 60 carbon atoms, or a heteroaryl having 1 to 40 carbon atoms containing at least one of O, N, Si and S, and
m and n are each independently an integer of 0 to 4.

7. The optical material according to claim 6 , wherein the optical material has a refractive index of 1.65 or more.

8. The optical material according to claim 6 , wherein the optical material has a glass transition temperature (Tg) of 80° C. or more.

9. The optical material according to claim 6 , wherein the optical material has a transmittance of 80% or more.

10. The optical material according to claim 6 , wherein the optical material has a haze of 1% or less.

11. The optical material according to claim 6 , wherein the optical material has a yellowness index (YI) of 0.1-10.

12. The optical material according to claim 6 , wherein the optical material is for a lens of a wearable device.

Assignees

• Lg Chemical Ltd

Inventors

• Choi Hee Jung
• Kim Heon
• Kim Jaeyoung

Classifications

• G02B1/041

  Lenses · CPC title

• C08G61/02

  Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes · CPC title

• C08L81/02

  Polythioethers; Polythioether-ethers · CPC title

• C08G75/14 Primary

  Polysulfides · CPC title

• C08G75/18 Primary

  Polysulfoxides · CPC title