Polycarbonate resin, and optical lens and optical film using same

Patent metadata

Field	Value
Publication number	US-2025092194-A1
Application number	US-202218707785-A
Country	US
Kind code	A1
Filing date	Nov 10, 2022
Priority date	Nov 12, 2021
Publication date	Mar 20, 2025
Grant date	—

Abstract

A polycarbonate resin includes a constituent unit (a) given by general formula (1-IA); a constituent unit (b) given by general formula (1-1A), but different from the constituent unit (a); a constituent unit (c-1) given by general formula (1-2A) or a constituent unit (c-2) given by general formula (3-1); and a constituent unit (d) given by general formula (2), wherein the content of the constituent unit (a) is 1-50 mol %, the content of the constituent unit (b) is 1-70 mol %, the content of the constituent unit (c-1) or (c-2) is 1-50 mol %, and the content of the constituent unit (d) is 1-30 mol %, in each case with reference to the total amount of the constituent units (a) to (d).

First claim

1 . A polycarbonate resin comprising: a structural unit (a) represented by general formula (1-1A); a structural unit (b) represented by general formula (1-1A), but different from the structural unit (a); a structural unit (c-1) represented by general formula (1-2A) or a structural unit (c-2) represented by general formula (3-1); and a structural unit (d) represented by general formula (2),
wherein the content of the structural unit (a) is 1 to 50 mol %, the content of the structural unit (b) is 1 to 70 mol %, the content of the structural unit (c-1) or (c-2) is 1 to 50 mol %, and the content of the structural unit (d) is 1 to 30 mol %, in each case with reference to the total amount of the structural units (a) to (d):

wherein in formula (1-1A):
R a and R b are each independently selected from a halogen atom; an alkyl group having 1 to 20 carbon atoms; an alkoxyl group having 1 to 20 carbon atoms; a cycloalkyl group having 5 to 20 carbon atoms; a cycloalkoxyl group having 5 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; a heteroaryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, which contains at least one heterocyclic atom selected from O, N and S; and —C≡C—R h ;
R h represents an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 6 to 20 carbon atoms which contains at least one heterocyclic atom selected from O, N and S;
A and B each independently represent an alkylene group having 1 to 4 carbon atoms;
m and n each independently represent an integer of 1 to 6; and
a and b each independently represent an integer of 0 to 10,

wherein in formula (1-2A):
R a and R b are each independently selected from a hydrogen atom; a halogen atom; an alkyl group having 1 to 20 carbon atoms; an alkoxyl group having 1 to 20 carbon atoms; a cycloalkyl group having 5 to 20 carbon atoms; a cycloalkoxyl group having 5 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; a heteroaryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, which contains at least one heterocyclic atom selected from O, N and S; and —C≡C—R;
R h represents an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 6 to 20 carbon atoms which contains at least one heterocyclic atom selected from O, N and S;
A and B each independently represent an alkylene group having 1 to 4 carbon atoms;
m and n each independently represent an integer of 1 to 6; and
a and b each independently represent an integer of 0 to 10,

wherein in formula (3-1):
R a and R b are each independently selected from hydrogen, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms;
Y represents a fluorene group;
A and B each independently represent an alkylene group having 1 to 4 carbon atoms;
m and n each independently represent an integer of 0 to 4; and
a and b each independently represent an integer of 1 to 10,

wherein in formula (2): R z and R x each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; i represents an integer of 2 to 16; and p represents an integer of 1 to 600.

2 . The polycarbonate resin according to claim 1 , wherein the structural unit (a) is a structural unit derived from 2DNBINOL-2EO (6,6′-di-(2-naphthyl)-2,2′-bis-(2-hydroxyethoxy)-1,1′-binaphthyl) represented by a structural formula below; the structural unit (b) is a structural unit derived from DPBHBNA (6,6′-diphenyl-2,2′-bis-(2-hydroxyethoxy)-1,1′-binaphthyl) represented by a structural formula below; the structural unit (c-1) is a structural unit derived from BNEF (9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene) represented by a structural formula below; the structural unit (c-2) is a structural unit derived from BPPEF (9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene) represented by a structural formula below; and the structural unit (d) is a structural unit derived from a compound selected from the group consisting of diethylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,10-decanediol, and 1,12-dodecanediol:

3 . The polycarbonate resin according to claim 1 , which comprises an antioxidant and a catalyst deactivator.

4 . The polycarbonate resin according to claim 3 , wherein the antioxidant is pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] and 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane; and the catalyst deactivator is dodecylbenzenesulfonic acid tetrabutylphosphonium salt.

5 . The polycarbonate resin according to claim 1 , which has a refractive index (nD) of 1.685 to 1.800.

6 . The polycarbonate resin according to claim 1 , which has an Abbe number (ν) of 14.0 to 18.0.

7 . The polycarbonate resin according to claim 1 , which has a glass transition temperature of 130 to 160° C.

8 . The polycarbonate resin according to claim 1 , which has a melt volume-flow rate (MVR) of 30 to 100 cm 3 /10 min.

9 . The polycarbonate resin according to claim 1 , which has a water absorption rate of less than 0.11%.

10 . An optical lens comprising the polycarbonate resin according to claim 1 .

11 . An optical film comprising the polycarbonate resin according to claim 1 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Kato Noriyuki
• NISHIMORI Katsushi
• Motegi Atsushi
• Ishihara Kentaro
• Harada Yutaro
• FUKUI Kiyoshiro

Classifications

• C08K2201/014

  Additives containing two or more different additives of the same subgroup in C08K · CPC title

• C08K5/527

  Cyclic esters · CPC title

• C08K5/134

  Phenols containing ester groups · CPC title

• C08J2369/00

  Characterised by the use of polycarbonates; Derivatives of polycarbonates · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title