Method of manufacturing liquid crystal alignment layer, liquid crystal alignment layer manufactured by using the same, and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10696901-B2
Application number	US-201615751737-A
Country	US
Kind code	B2
Filing date	Nov 2, 2016
Priority date	Nov 11, 2015
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

Provided are a method of manufacturing a liquid crystal alignment layer, a liquid crystal alignment layer manufactured by using the same, and a liquid crystal display device including the liquid crystal alignment layer. More specifically, provided are the method of manufacturing the liquid crystal alignment layer with enhanced alignment property and stability, in which a liquid crystal aligning agent is applied onto a substrate, and after drying, alignment treatment is immediately performed by light irradiation while omitting a high-temperature heat treatment process, and then the alignment-treated coating film is cured by heat treatment, thereby reducing light irradiation energy required in the process and simplifying the process by omitting the high-temperature heat treatment process before light irradiation, the liquid crystal alignment layer, and the liquid crystal display device including the same.

First claim

What is claimed is:

1. A method of manufacturing a liquid crystal alignment layer, the method comprising the steps of:
forming a coating film by applying a liquid crystal aligning agent onto a substrate, the liquid crystal aligning agent including a polymer for liquid crystal alignment including two or more repeating units selected from the group consisting of a repeating unit represented by the following Chemical Formula 1, a repeating unit represented by the following Chemical Formula 2, and a repeating unit represented by the following Chemical Formula 3, wherein the repeating unit represented by the following Chemical Formula 1 is included in an amount of 5 mol % to 74 mol % with respect to a total of the repeating units represented by the following Chemical Formulae 1 to 3;
drying the coating film;
performing alignment treatment of the coating film by light irradiation immediately after the drying step; and
curing the alignment-treated coating film by heat treatment:

wherein R 1 and R 2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, provided that R 1 and R 2 are not all hydrogen,
X 1 is a tetravalent organic group represented by the following Chemical Formula 4,

R 3 to R 6 are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms,
X 2 and X 3 are each independently a tetravalent organic group derived from hydrocarbon having 4 to 20 carbon atoms, or a tetravalent organic group, in which one or more hydrogens are substituted with halogen, or one or more —CH 2 — groups are substituted with —O—, —CO—, —S—, —SO—, —SO 2 — or —CONH— to prevent direct linkage of oxygen or sulfur atoms,
Y 1 to Y 3 are each independently a divalent organic group represented by the following Chemical Formula 5,

wherein R 7 and R 8 are each independently halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluoroalkyl group having 1 to 10 carbon atoms, or a fluoroalkoxy group having 1 to 10 carbon atoms,
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 —, —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, and
m is an integer of 0 to 3.

2. The method of manufacturing the liquid crystal alignment layer of claim 1 , wherein X 2 and X 3 are each independently a tetravalent organic group represented by the following Chemical Formula 6:

wherein R 3 to R 6 are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms,
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 combinations thereof, and
R 9 and R 10 are each independently hydrogen, or an alkyl or fluoroalkyl group having 1 to 10 carbon atoms.

3. The method of manufacturing the liquid crystal alignment layer of claim 1 , wherein the liquid crystal aligning agent is prepared by dissolving or dispersing the polymer for liquid crystal alignment in an organic solvent.

4. The method of manufacturing the liquid crystal alignment layer of claim 1 , wherein the step of drying the coating film is performed at 50° C. to 150° C.

5. The method of manufacturing the liquid crystal alignment layer of claim 1 , wherein the light irradiation in the alignment treatment step is performed by irradiating polarized ultraviolet rays having a wavelength of 150 nm to 450 nm.

6. The method of manufacturing the liquid crystal alignment layer of claim 1 , wherein a heat treatment temperature in the step of curing the coating film is 150° C. to 300° C.

7. A method of manufacturing a liquid crystal alignment layer, the method comprising the steps of:
forming a coating film by applying a liquid crystal aligning agent onto a substrate, the liquid crystal aligning agent including a polymer for liquid crystal alignment including two or more repeating units selected from the group consisting of a repeating unit represented by the following Chemical Formula 1, a repeating unit represented by the following Chemical Formula 2, and a repeating unit represented by the following Chemical Formula 3, wherein the repeating unit represented by the following Chemical Formula 1 is included in an amount of 5 mol % to 74 mol % with respect to a total of the repeating units represented by the following Chemical Formulae 1 to 3;
drying the coating film;
performing alignment treatment of the coating film by light irradiation immediately after the drying step; and
curing the alignment-treated coating film by heat treatment:

wherein R 1 and R 2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, provided that R 1 and R 2 are not all hydrogen,
X 1 is a tetravalent organic group,
X 2 and X 3 are each independently a tetravalent organic group derived from hydrocarbon having 4 to 20 carbon atoms, or a tetravalent organic group, in which one or more hydrogens are substituted with halogen, or one or more —CH 2 — groups are substituted with —O—, —CO—, —S—, —SO—, —SO 2 — or —CONH— to prevent direct linkage of oxygen or sulfur atoms,
Y 1 to Y 3 are each independently a divalent organic group represented by the following Chemical Formula 5,

wherein R 7 and R 8 are each independently halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluoroalkyl group having 1 to 10 carbon atoms, or a fluoroalkoxy group having 1 to 10 carbon atoms,
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 —, —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, and
m is an integer of 0 to 3.

Assignees

• Lg Chemical Ltd

Inventors

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

Classifications

• C08G73/1042 Primary

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• G02F1/133723

  Polyimide, polyamide-imide · CPC title

• C08L79/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/1007

  from tetracarboxylic acids or derivatives and diamines · CPC title