Liquid crystal alignment agent composition, method for preparing liquid crystal alignment film using same, and liquid crystal alignment film and liquid crystal display using same

Patent metadata

Field	Value
Publication number	US-11149204-B2
Application number	US-201916628906-A
Country	US
Kind code	B2
Filing date	Apr 17, 2019
Priority date	May 17, 2018
Publication date	Oct 19, 2021
Grant date	Oct 19, 2021

Abstract

Provided is a liquid crystal alignment agent composition comprising a terminal modifier compound containing an amino group together with a polyimide containing an acid anhydride group at its terminus or a precursor polymer thereof, a method for preparing a liquid crystal alignment film using the same, and a liquid crystal alignment film and a liquid crystal display using the same.

First claim

The invention claimed is:

1. A liquid crystal alignment agent composition comprising:
a terminal modifier compound containing an amino group; and
a polymer containing at least one repeating unit selected from the group consisting of a repeating unit of the following Chemical Formula 1, a repeating unit of the following Chemical Formula 2, and a repeating unit of the following Chemical Formula 3, in which an acid anhydride group is bonded to at least one terminus thereof:

wherein in the Chemical Formulas 1 to 3:
one of R 1 and R 2 is an alkyl group having 1 to 10 carbon atoms and the other is hydrogen or an alkyl group having 1 to 10 carbon atoms;
X 1 to X 3 are each independently a tetravalent organic group;
Y 1 to Y 3 are each independently a divalent organic group of the following Chemical Formula 4:

wherein in the Chemical Formula 4:
A is a Group 15 element;
R 3 is one of hydrogen and an alkyl group having 1 to 10 carbon atoms;
a is an integer from 1 to 3; and
one of Z 1 and Z 3 is nitrogen and the other is carbon, and Z 2 and Z 4 are carbon.

2. The liquid crystal alignment agent composition according to claim 1 , wherein in the Chemical Formula 4, A is nitrogen, R 3 is hydrogen, and a is 1.

3. The liquid crystal alignment agent composition according to claim 1 , wherein the divalent organic group of the Chemical Formula 4 is selected from the group consisting of divalent organic groups of the following Chemical Formulas 4-1, 4-2, and 4-3:

4. The liquid crystal alignment agent composition according to claim 1 , wherein X 1 to X 3 are each independently a tetravalent organic group having one of the following formulas:

wherein:
R 4 to R 9 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms;
L 1 is any one selected from the group consisting of a direct bond, —O—, —CO—, —S—, —SO—, —SO 2 —, —CR 10 R 11 —, —CONH—, —COO—, —(CH 2 ) b —, —O(CH 2 ) b —O—, —COO—(CH 2 ) b —OCO—, phenylene, and a combination thereof;
R 10 and R 11 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a haloalkyl group having 1 to 10 carbon atoms; and
b is an integer from 1 to 10.

5. The liquid crystal alignment agent composition according to claim 1 , wherein the terminal modifier compound containing an amino group is a compound of the following Chemical Formula 6:

wherein in the Chemical Formula 6:
L 2 and L 3 are each independently any one selected from among a direct bond, —O—, —CO—, —S—, —CONH—, —COO—, —O(CH 2 ) t O—, —COO—(CH 2 ) t —OCO—, an alkylene group having 1 to 10 carbon atoms, a haloalkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, a heterocycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 30 carbon atoms, and a heteroarylene group having 3 to 20 carbon atoms;
t is an integer from 1 to 10; and
X is any one of hydrogen, a hydroxy group, a nitro group, and an alkyl group having 1 to 10 carbon atoms.

6. The liquid crystal alignment agent composition according to claim 1 , wherein the content of the terminal modifier compound containing an amino group is 0.1% to 20% by weight based on the total weight of the liquid crystal alignment agent composition.

7. The liquid crystal alignment agent composition according to claim 1 , wherein the polymer includes:
a first polymer containing at least one repeating unit selected from the group consisting of the repeating unit of the Chemical Formula 1, the repeating unit of the Chemical Formula 2, and the repeating unit of the Chemical Formula 3 in which an acid anhydride group is bonded to at least one terminus thereof; and
a second polymer containing at least one repeating unit selected from the group consisting of the repeating unit of the Chemical Formula 1, the repeating unit of the Chemical Formula 2, and the repeating unit of the Chemical Formula 3 and having at least one terminal functional group selected from the group consisting of the following Chemical Formulas 7, 8, and 9 at one or more termini thereof:

wherein in the Chemical Formulas 7 to 9:
one of R 1 ′ and R 2 ′ is an alkyl group having 1 to 10 carbon atoms and the other is hydrogen or an alkyl group having 1 to 10 carbon atoms;
X 1 ′ to X 3 ′ are each independently a tetravalent organic group;
Y 1 ′ to Y 3 ′ are each independently a divalent organic group of the following Chemical Formula 4;
L 2 ′ and L 3 ′ are each independently any one selected from among a direct bond, —O—, —CO—, —S—, —CONH—, —COO—, —O(CH 2 ) t O—, —COO—(CH 2 ) t —OCO—, an alkylene group having 1 to 10 carbon atoms, a haloalkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, a heterocycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 30 carbon atoms, and a heteroarylene group having 3 to 20 carbon atoms;
t is an integer from 1 to 10; and
X′ is hydrogen, a hydroxy group, a nitro group, or an alkyl group having 1 to 10 carbon atoms;

wherein in the Chemical Formula 4:
A is a Group 15 element;
R 3 is one of hydrogen and an alkyl group having 1 to 10 carbon atoms;
a is an integer from 1 to 3; and
at least one of Z 1 to Z 4 is nitrogen and the rest are carbon.

8. The liquid crystal alignment agent composition according to claim 7 , wherein the second polymer is contained in an amount from 0.5% to 40% by weight based on the total weight of the liquid crystal alignment agent composition.

9. A method for preparing a liquid crystal alignment film, comprising the steps of:
coating the liquid crystal alignment agent composition of claim 1 onto a substrate to form a coating film;
drying the coating film;
irradiating the dried coating film with light or rubbing the dried coating film to perform alignment treatment; and
heat-treating and curing the alignment-treated coating film.

10. The method for preparing a liquid crystal alignment film according to claim 9 , wherein the step of drying the coating film is performed at a temperature of 50° C. to 150° C.

11. The method for preparing a liquid crystal alignment film according to claim 9 , wherein the step of heat-treating and curing the alignment-treated coating film is performed at a temperature of 180° C. to 300° C.

12. A liquid crystal alignment film, prepared by the method of claim claim 9 .

13. A liquid crystal alignment film, comprising an aligned cured product of the liquid crystal alignment agent composition of claim 1 .

14. A liquid crystal display, comprising the liquid crystal alignment film of claim 13 .

Assignees

• Lg Chemical Ltd

Inventors

• Kim Seongku
• Jo Jung Ho
• Park Hoonseo
• Han Hee
• Yoon Jun Young

Classifications

• C09K19/56 Primary

  Aligning agents · CPC title

• C08G73/1017

  in the form of (mono)amine · CPC title

• G02F1/133711

  by organic films, e.g. polymeric films · CPC title

• C08G73/1085

  Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties · CPC title

• C08G73/1067

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title