Thermoplastic resin, optical film made therefrom, diol compound, diester compound

Patent metadata

Field	Value
Publication number	US-12065541-B2
Application number	US-202117456259-A
Country	US
Kind code	B2
Filing date	Nov 23, 2021
Priority date	Jun 24, 2019
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

A thermoplastic resin including a structural unit of formula (1):

wherein A 1 to A 8 are each independently ═CH— or ═N—, and at least one of A 1 to A 8 is ═N—. R 1 to R 8 are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or the like. At least two adjacent groups out of R 1 to R 8 are optionally bonded to each other to form a ring. R 9 and R 10 are each independently a direct bond or an optionally substituted alkylene group having 1 to 20 carbon atoms. X is an oxygen atom, a carbonyl group, or an optionally substituted amino group, and n is an integer of 1 to 5. A retardation film, a circularly polarizing plate containing the thermoplastic resin are disclosed.

First claim

The invention claimed is:

1. A thermoplastic resin comprising a structural unit of formula (1):

wherein A 1 to A 8 are each independently ═CH— or ═N—, and at least one of A 1 to A 8 is ═N—,
R 1 to R 8 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted aryl group having 6 to 11 carbon atoms, an optionally substituted heteroaryl group having 3 to 10 carbon atoms, an optionally substituted acyl group having 1 to 10 carbon atoms, an optionally substituted alkoxy group having 1 to 10 carbon atoms, an optionally substituted aryloxy group having 6 to 11 carbon atoms, an optionally substituted amino group, an optionally substituted vinyl group having 2 to 10 carbon atoms, an optionally substituted ethynyl group having 2 to 10 carbon atoms, a silicon atom having a substituent, a sulfur atom having a substituent, a halogen atom, a nitro group or a cyano group,
wherein at least two adjacent groups out of R 1 to R 8 are optionally bonded to each other to form a ring, R 9 and R 10 are each independently a direct bond or an optionally substituted alkylene group having 1 to 20 carbon atoms, X is an oxygen atom, a carbonyl group, or an optionally substituted amino group, and n is an integer of 1 to 5.

2. The thermoplastic resin of claim 1 , comprising the structural unit of formula (1) in an amount in a range of from 1 to 70 wt %.

3. The thermoplastic resin of claim 1 , having an absolute value of a photoelastic coefficient of 20× 10 −12 Pa −1 or less.

4. The thermoplastic resin of claim 1 , having a glass transition temperature in a range of from 110 to 160° C.

5. The thermoplastic resin of claim 1 , comprising at least one selected from the group consisting of a polycarbonate, a polyester, and a polyester carbonate.

6. The thermoplastic resin of claim 1 , further comprising at least one of a structural unit of formula (10) and a structural unit of formula (11):

7. The thermoplastic resin of claim 1 , wherein the structural unit of formula (1) comprises at least one selected from the group consisting of formula (V-1), formula (V-2), and formula (V-3):

8. A transparent film, comprising the resin of claim 1 .

9. A retardation film, comprising the transparent film of claim 8 , stretched in at least one direction.

10. The retardation film of claim 9 , wherein an R450/R550 ratio of a retardation at a wavelength of 450 nm (R450) and a retardation at a wavelength of 550 nm (R550) satisfies formula (I):
0.50≤ R 450/ R 550≤1.02  (I).

11. A circularly polarizing plate, comprising the retardation film of claim 9 .

12. A diol compound of formula (7):

wherein A 1 to A 8 are each independently ═CH— or ═N—, and at least one of A 1 to A 8 is ═N—,
R 1 to R 8 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted aryl group having 6 to 11 carbon atoms, an optionally substituted heteroaryl group having 3 to 10 carbon atoms, an optionally substituted acyl group having 1 to 10 carbon atoms, an optionally substituted alkoxy group having 1 to 10 carbon atoms, an optionally substituted aryloxy group having 6 to 11 carbon atoms, an optionally substituted amino group, an optionally substituted vinyl group having 2 to 10 carbon atoms, an optionally substituted ethynyl group having 2 to 10 carbon atoms, a silicon atom having a substituent, a sulfur atom having a substituent, a halogen atom, a nitro group or a cyano group, wherein at least two adjacent groups out of R 1 to R 8 are optionally bonded to each other to form a ring, R 9 and R 10 are each independently a direct bond or an optionally substituted alkylene group having 1 to 20 carbon atoms, and n is an integer of 1 to 5.

13. The diol compound of claim 12 , wherein the formula (7) comprises at least one of formula (W-1) and formula (W-2):

14. A diester compound of formula (8):

wherein A 1 to A 8 are each independently ═CH— or ═N—, and at least one of A 1 to A 8 is ═N—,
R 1 to R 8 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted aryl group having 6 to 11 carbon atoms, an optionally substituted heteroaryl group having 3 to 10 carbon atoms, an optionally substituted acyl group having 1 to 10 carbon atoms, an optionally substituted alkoxy group having 1 to 10 carbon atoms, an optionally substituted aryloxy group having 6 to 11 carbon atoms, an optionally substituted amino group, an optionally substituted vinyl group having 2 to 10 carbon atoms, an optionally substituted ethynyl group having 2 to 10 carbon atoms, a silicon atom having a substituent, a sulfur atom having a substituent, a halogen atom, a nitro group or a cyano group,
wherein at least two adjacent groups out of R 1 to R 8 are optionally bonded to each other to form a ring, R 9 and R 10 are each independently a direct bond or an optionally substituted alkylene group having 1 to 20 carbon atoms,
R 11 and R 12 are each a hydrogen atom, an optionally substituted aryl group having 6 to 11 carbon atoms, an optionally substituted heteroaryl group having 3 to 10 carbon atoms, or an optionally substituted alkyl group having 1 to 10 carbon atoms, wherein R 11 and R 12 are same or different from each other, and
and n is an integer of 1 to 5.

15. The diester compound of claim 14 , wherein the formula (8) comprises at least one of formula (X-1) and formula (X-2):

Assignees

• Mitsubishi Chem Corp

Inventors

• Namiki Shingo
• Hirami Yuuichi
• Nakamura Koji
• Hayashi Hiroyuki
• Maeda Tomoko
• Satake Kenichi

Classifications

• G02B5/3025

  Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state (G02B5/3008, G02B5/3016 take precedence) · CPC title

• C08J2367/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence) · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G63/83

  Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• C08G63/81

  using solvents (C08G63/79 takes precedence) · CPC title