Polycarbonate resin and preparation method thereof

Patent metadata

Field	Value
Publication number	US-12441836-B2
Application number	US-202218035572-A
Country	US
Kind code	B2
Filing date	Aug 12, 2022
Priority date	Mar 23, 2022
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

A polycarbonate resin including a unit of Chemical Formula 1 and a unit of Chemical Formula 2, a method for preparing the same, a polycarbonate resin composition including the same, and a molded article are disclosed herein:Ar1 and Ar2 are independently an aryl group, or a heteroaryl group, R1 is hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a silyl group, an aryl group, or a heteroaryl group, R2 and R3 are different from each other, r1 is 1 or 2, r2 and r3 are each an integer from 1 to 4, L1 and L2 are independently an arylene group, X1 to X8 are independently O or S, Z1 to Z4 are independently an alkylene group, or a cycloalkylene group, and a, b, c and d are independently an integer from 1 to 10.

First claim

The invention claimed is:

1. A polycarbonate resin, comprising:
a unit of the following Chemical Formula 1; and
a unit of the following Chemical Formula 2:

wherein, in Chemical Formulae 1 and 2,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
R1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
R2 and R3 are different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, an aryl group which is unsubstituted or substituted with deuterium, a halogen group, a hydroxyl group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryloxy group, an arylthio group, an alkylthio group, an aryl group, or a heteroaryl group, or a substituted or unsubstituted heteroaryl group,
r1 is 1 or 2, and when r1 is 2, each R1 is the same as or different from each other,
r2 and r3 are each an integer from 1 to 4, and when r2 is 2 to 4, two or more R2 are the same as or different from each other, and when r3 is 2 to 4, two or more R3 are the same as or different from each other,
L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group,
X1 to X8 are the same as or different from each other, and are each independently O or S,
Z1 to Z4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group, or a substituted or unsubstituted cycloalkylene group, and
a, b, c and d are the same as or different from each other, and are each independently an integer from 1 to 10, and when a and b are each 2 to 10, each of Z1-X1 and X2-Z2 are the same as or different from each other.

2. The polycarbonate resin of claim 1 , further comprising:
a unit of the following Chemical Formula 3:

wherein, in Chemical Formula 3,
L11 is a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a condensed ring group of a divalent aromatic hydrocarbon ring and an aliphatic hydrocarbon ring which is substituted or unsubstituted, or a substituted or unsubstituted arylene group,
l11 is an integer from 1 to 5, and when l11 is 2 to 5, two or more L11 are the same as or different from each other,
X11 to X14 are the same as or different from each other, and are each independently O or S,
Z11 and Z12 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group, or a substituted or unsubstituted cycloalkylene group, and
a′ and b′ are the same as or different from each other, and are each independently an integer from 0 to 10, and when a′ and b′ are each 2 to 10, each of Z11-X11 and X12-Z12 are the same as or different from each other.

3. The polycarbonate resin of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
R1 is hydrogen,
X1 to X4 are O, and
Z1 and Z2 are the same as or different from each other, and are each independently a straight-chained or branched alkylene group having 1 to 30 carbon atoms.

4. The polycarbonate resin of claim 1 , wherein R2 and R3 are different from each other, and are each independently hydrogen, or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
L1 and L2 are the same as or different from each other, and are each independently a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms,
X5 to X8 are O, and
Z3 and Z4 are the same as or different from each other, and are each independently a straight-chained or branched alkylene group having 1 to 30 carbon atoms.

5. The polycarbonate resin of claim 1 , wherein the polycarbonate resin has a weight average molecular weight (Mw) of 5,000 g/mol to 500,000 g/mol.

6. The polycarbonate resin of claim 1 , wherein the polycarbonate resin has a refractive index of 1.50 to 1.75, wherein the refractive index is measured at a wavelength of 587 nm.

7. The polycarbonate resin of claim 1 , wherein the polycarbonate resin has a glass transition temperature (Tg) of 80° C. to 200° C.

8. The polycarbonate resin of claim 1 , wherein the polycarbonate resin has an Abbe's Number of 5 to 45, wherein the Abbe's Number is measured at a wavelength of 486, 587, and 656 nm.

9. A method for preparing the polycarbonate resin according to claim 1 , the method comprising:
polymerizing a composition comprising a compound of the following Chemical Formula 1a, a compound of the following Chemical Formula 2a, and
a polycarbonate precursor:

wherein, in Chemical Formulae 1a and 2a,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
R1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
R2 and R3 are different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, an aryl group which is unsubstituted or substituted with deuterium, a halogen group, a hydroxyl group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryloxy group, an arylthio group, an alkylthio group, an aryl group, or a heteroaryl group, or a substituted or unsubstituted heteroaryl group,
r1 is 1 or 2, and when r1 is 2, each R1 is the same as or different from each other,
r2 and r3 are each an integer from 1 to 4, and when r2 is 2 to 4, two or more R2 are the same as or different from each other, and when r3 is 2 to 4, two or more R3 are the same as or different from each other,
L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group,

Assignees

• Lg Chemical Ltd

Inventors

• Choi Il Hwan
• Kim Kyeongmun
• Yim Hye Jin
• Bae Jaesoon
• Baek Jonghwa
• Shin Hyeonah
• Jung Min Suk

Classifications

• C08G64/307

  and phenols · CPC title

• C08L2201/10

  Transparent films; Clear coatings; Transparent materials · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08G64/30

  using carbonates · CPC title