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

Patent metadata

Field	Value
Publication number	US-11630350-B2
Application number	US-201715777846-A
Country	US
Kind code	B2
Filing date	Jun 20, 2017
Priority date	Jun 21, 2016
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

The present invention relates to a liquid crystal alignment composition for the preparation of a liquid crystal alignment film having enhanced alignment property and stability and exhibiting a high voltage holding ratio, a method for preparing a liquid crystal alignment film using the same, and a liquid crystal alignment film and a liquid crystal display device using the same.

First claim

The invention claimed is:

1. A liquid crystal alignment composition comprising:
(i) a copolymer for liquid crystal alignment agent including a repeating unit represented by Chemical Formula 1 below, a repeating unit represented by Chemical Formula 2 below and a repeating unit represented by Chemical Formula 3 below, wherein the repeating unit represented by Chemical Formula 1 below is contained in an amount of 5 to 74 mol % relative to the total repeating units represented by Chemical Formulae 1 to 3 below, and the repeating unit represented by Chemical Formula 3 below is contained in an amount of 10 to 90 mol % relative to the total repeating units represented by Chemical Formulae 1 to 3 below, and
(ii) a compound having two or more epoxy groups,
wherein the molecular weight of the compound having two or more epoxy groups is not more than 10,000, and the compound is contained in an amount of 0.1 to 30% by weight based on the weight of the copolymer for liquid crystal alignment agent,
wherein the repeating unit represented by the Chemical Formula 1 is formed from a diamine that is a reaction product of a compound comprising X 1 represented by Chemical Formula 4 and a compound comprising Y 1 represented by Chemical Formula 5,

in the Chemical Formulae 1 to 3,
R 1 and R 2 are each independently hydrogen, or C 1-10 alkyl, with the proviso that both R 1 and R 2 are not hydrogen,
X 1 is a tetravalent organic group represented by the Chemical Formula 4 below,

in the Chemical Formula 4,
R 3 to R 6 are each independently hydrogen, or C 1-6 alkyl,
X 2 and X 3 are each independently a tetravalent organic group derived from a hydrocarbon having 4 to 20 carbon atoms, a tetravalent organic group in which at least one hydrogen in the tetravalent organic group is substituted with a halogen, or a tetravalent organic group in which at least one —CH 2 — is replaced by —O—, —CO—, —S—, —SO—, —SO 2 —, or —CONH— such that oxygen or sulfur atoms are not directly linked, and
Y 1 , Y 2 and Y 3 are each independently a divalent organic group represented by the Chemical Formula 5 below,

in the Chemical Formula 5,
R 7 and R 8 are each independently halogen, cyano, C 1-10 alkyl, C 2-10 alkenyl, C 1-10 alkoxy, C 1-10 fluoroalkyl, or C 1-10 fluoroalkoxy,
p and q are each independently an integer of 0 to 4,
L 1 is a single bond, —O—, —CO—, —S—, —SO 2 —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CONH—, —COO—, —(CH 2 ) z —, —O(CH 2 ) z O—, —O(CH 2 ) z —, —NH—, —NH(CH 2 ) z —NH—, —NH(CH 2 ) z O—, —OCH 2 —C(CH 3 ) 2 —CH 2 O—, —COO—(CH 2 ) z —OCO—, or —OCO—(CH 2 ) z —COO—,
z is an integer of 1 to 10,
k and m are each independently an integer of 1 to 3, and
n is an integer of 0 to 3, and
wherein the compound having two or more epoxy groups is any one or more of the compounds represented by Chemical Formulae 11, 12 and 14 below:

in the Chemical Formulae 11 and 12,
R 20 and R 21 are each independently hydrogen, or halogen,
R 22 and R 23 are each independently hydrogen, or methyl,
h and i are each independently an integer of 0 to 3, and
j is an integer of 1 to 20,

in the Chemical Formula 14,
w is each independently an integer of 1 to 10.

2. The liquid crystal alignment composition according to claim 1 , wherein
X 2 and X 3 are each independently a tetravalent organic group represented by Chemical Formula 6 below:

in the Chemical Formula 6,
R 3 to R 6 are each independently hydrogen, or C 1-6 alkyl, and
L 2 is any one selected from the group consisting of a single bond, —O—, —CO—, —S—, —SO—, —SO 2 —, —CR 9 R 10 —, —CONH—, phenylene, or a combination thereof,
wherein R 9 and R 10 are each independently hydrogen, an alkyl group or a fluoroalkyl group having 1 to 10 carbon atoms.

3. A method for preparing a liquid crystal alignment film comprising the steps of:
coating the liquid crystal alignment composition according to claim 1 onto a substrate to form a coating film, wherein the liquid crystal alignment composition is dissolved or dispersed in a solvent prior to the coating step;
drying the coating film;
irradiating the coating film with light immediately after the drying step to perform alignment treatment; and
curing the alignment-treated coating film by heat treatment.

4. The method for preparing a liquid crystal alignment film according to claim 3 , wherein
the liquid crystal alignment composition is dissolved or dispersed in an organic solvent.

5. The method for preparing a liquid crystal alignment film according to claim 3 , wherein
the step of drying the coating film is carried out at 50 to 50° C.

6. The method for preparing a liquid crystal alignment film according to claim 3 , wherein,
in the alignment treatment step, the light irradiation is performed by irradiating polarized ultraviolet rays having a wavelength of 150 to 450 nm.

7. The method for preparing a liquid crystal alignment film according to claim 3 , wherein,
the heat treatment is carried out at a temperature of 150 to 300° C.

8. A liquid crystal alignment film prepared by the method preparing the liquid crystal alignment film according to claim 3 .

9. A liquid crystal display device including the liquid crystal alignment film according to claim 8 .

Assignees

• Lg Chemical Ltd

Inventors

• Jo Jung Ho
• Han Hee
• Park Hang Ah
• Kwon Soon Ho
• Yoon Jun Young
• Yun Hyeong Seuk

Classifications

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• G02F1/133711

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

• G02F1/133723 Primary

  Polyimide, polyamide-imide · CPC title

• C09K2323/025

  Polyamide · CPC title

• C09K19/56 Primary

  Aligning agents · CPC title