Xanthene derivative compound having high refractive index and (co)polymer comprising same

Patent metadata

Field	Value
Publication number	US-2024190836-A1
Application number	US-202318372913-A
Country	US
Kind code	A1
Filing date	Sep 26, 2023
Priority date	Sep 26, 2022
Publication date	Jun 13, 2024
Grant date	—

Abstract

The present disclosure relates to a xanthene derivative compound with a high refractive index and a manufacturing method therefor. More specifically, provided herein is a compound that has a xanthene-based complex cardo structure and a high refractive index and can be used as a monomer in optical resins requiring a refractive index of 1.7 or higher, and a (co)polymer and an optical lens manufactured therefrom. Given, the xanthene-based complex cardo structure of the compound maximally suppresses the fluidity of the molecular chains and can find applications in the production of resins with high glass transition temperature and excellent thermal stability.

First claim

1 . A compound having a chemical structure of the following Chemical Formula 1:

wherein X, R 1a , and R 1b represent substituents;
X is O, S, or SO 2 ;
m1 and m2 are each independently an integer of 0 to 4 (with a proviso that m1+m2 is an integer of 1 to 8),
R 1a and R 1b are each selected from the substituents having the chemical structures of Chemical Formulas 1-1 to 1-3, below:

wherein, n1 and n2 are each independently an integer of 1 to 5, with a proviso that n1+n2 is 2 to 10;

wherein, n1 and n2 are each independently an integer of 1 to 5, with a proviso that n1+n2 is 2 to 10; and

2 . The compound of claim 1 , wherein the compound has any one of the chemical structures of the following Chemical Formulas 2-1 to 2-3:

wherein,
X is O, S, or SO 2 , and
n is an integer of 1 to 5.

3 . The compound of claim 1 , wherein X is SO 2 .

4 . The compound of claim 3 , wherein the compound has the chemical structure of the following Chemical Formula 3-1 or 3-2:

5 . The compound of claim 1 , wherein X is O.

6 . The compound of claim 5 , wherein the compound has the chemical structure of the following Chemical Formula 4-1 or 4-2

7 . The compound of claim 1 , wherein X is S.

8 . The compound of claim 7 , wherein the compound has the chemical structure of the following Chemical Formula 5-1 or 5-2:

9 . A (co)polymer, prepared from the polymerization components comprising:
(a) the compound of claim 1 ; and (b) a diisocyanate compound or a polycarbonate precursor.

10 . The (co)polymer of claim 9 , wherein the diisocyanate compound is at least one selected from the group consisting of methylene diphenyl diisocyanate (MDI), p-phenylene diisocyanate (PPDI), tolylene-2,4-diisocyanate (2,4-TDI), tolylene-2,6-diisocyanate (2,6-TDI), xylylene diisocyanate (XDI), 1,5-naphthalene diisocyanate (NDI), hexamethylene diisocyanate (HDI), 4,4′-methylene dicyclohexyldiisocyanate (H12MDI), 1,4-cyclohexane diisocyanate (CHDI), isophoroene diisocyanate (IPDI), and 1,3-bis(isocyanatomethyl) cyclohexane (H6XDI).

11 . The (co)polymer, wherein the polycarbonate precursor is represented by the following Chemical Formula:

wherein, Rb1 and Rb2 are same or different and are each independently a halogen, a substituted or unsubstituted alkyl, or a substituted or unsubstituted aryl, and
b1 and b2 are each independently 0 or 1.

12 . An optical lens, comprising the (co)polymer of claim 9 .

Assignees

• Research & Business Found Sungkyunkwan Univ

Inventors

• Kim Younchul
• Hegazy Hend A
• Choi Ju Young
• Song Changsik

Classifications

• C09D175/04

  Polyurethanes · CPC title

• C08G18/246

  containing also tin-carbon bonds · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title