Liquid crystal aligning agent composition, method for producing liquid crystal alignment film using same, and liquid crystal alignment film using same

Patent metadata

Field	Value
Publication number	US-11230670-B2
Application number	US-201816484766-A
Country	US
Kind code	B2
Filing date	Jun 26, 2018
Priority date	Jun 30, 2017
Publication date	Jan 25, 2022
Grant date	Jan 25, 2022

Abstract

The present invention relates to a liquid crystal aligning agent composition for producing a liquid crystal alignment film having improved film strength together with liquid crystal alignment properties, a method for producing 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 aligning agent composition comprising:
i) a first polymer for a liquid crystal aligning agent including two or more repeating units selected from the group consisting of a repeating unit represented by Chemical Formula 1, a repeating unit represented by Chemical Formula 2, and a repeating unit represented by Chemical Formula 3, wherein the first polymer includes the repeating unit represented by Chemical Formula 1 in an amount of 36.4 mol % to 74 mol % with respect to a total of the repeating units represented by the following Chemical Formulae 1 to 3,
ii) a second polymer for a liquid crystal aligning agent including a repeating unit represented by Chemical Formula 4,
iii) a compound having two or more epoxy groups in a molecule, and
iv) a phosphine-based compound represented by Chemical Formula 5,
wherein a weight ratio between the first polymer for a liquid crystal aligning agent and the second polymer for a liquid crystal aligning agent is 2:8 to 8:2:

wherein, in Chemical Formulae 1 to 5,
at least one of R 1 and R 2 is a C 1-10 alkyl, and the rest is hydrogen,
R 3 and R 4 are each independently hydrogen or a C 1-10 alkyl,
A 1 , A 2 , and A 3 are each independently hydrogen, a C 1-20 alkyl, a C 3-20 cycloalkyl, a C 6-20 aryl, or a C 6-20 aryl substituted with at least one C 1-20 alkyl group,
X 1 is a tetravalent organic group represented by Chemical Formula 6,
X 2 , X 3 , and X 4 are each independently a tetravalent organic group derived from a hydrocarbon having 4 to 20 carbon atoms, or a tetravalent organic group in which at least one H in the tetravalent organic group is substituted with a halogen, or 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

wherein, in Chemical Formula 6,
R 5 to R 8 are each independently hydrogen or a C 1-6 alkyl,
Y 1 , Y 2 , Y 3 , and Y 4 are each independently a divalent organic group represented by Chemical Formula 7,

wherein, in Chemical Formula 7,
R 9 and R 10 are each independently a halogen, a cyano, a C 1-10 alkyl, a C 2-10 alkenyl, a C 1-10 alkoxy, a C 1-10 fluoroalkyl, or a C 1-10 fluoroalkoxy,
p and q are each independently an integer between 0 and 4, and
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—,
wherein z is an integer between 1 and 10,
m is an integer between 0 and 3.

2. The liquid crystal aligning agent composition of claim 1 , wherein in the Chemical Formula 5, A 1 , A 2 , and A 3 are each independently hydrogen or a C 1-3 alkyl.

3. The liquid crystal aligning agent composition of claim 1 , wherein the phosphine-based compound is included in an amount of 0.03 parts by weight to 30 parts by weight based on a total of 100 parts by weight of the first polymer for the liquid crystal aligning agent and the second polymer for the liquid crystal aligning agent.

4. The liquid crystal aligning agent composition of claim 1 , wherein the X 2 , X 3 , and X 4 are each independently a tetravalent organic group represented by Chemical Formula 8:

wherein, in Chemical Formula 8,
R 11 to R 14 are each independently hydrogen or a C 1-6 alkyl, and
L 2 is a single bond, —O—, —CO—, —S—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CONH—, —COO—, —(CH 2 ) z —, —O(CH 2 ) z O—, or —COO—(CH 2 ) z —OCO—, wherein z is an integer between 1 and 10.

5. The liquid crystal aligning agent composition of claim 1 , wherein the molecular weight of the compound having two or more epoxy groups in a molecule is 100 g/mol to 10,000 g/mol.

6. The liquid crystal aligning agent composition of claim 1 , wherein the compound having two or more epoxy groups in a molecule is a cycloaliphatic-based epoxy, a bisphenol-based epoxy, or a novolac-based epoxy.

7. The liquid crystal aligning agent composition of claim 1 , wherein the compound having two or more epoxy groups in a molecule is included in an amount of 0.1 parts by weight to 30 parts by weight based on a total of 100 parts by weight of the first polymer for a liquid crystal aligning agent and the second polymer for a liquid crystal aligning agent.

8. A method for producing a liquid crystal alignment film comprising the steps of:
1) coating the liquid crystal aligning agent composition of claim 1 onto a substrate to form a coating film;
2) drying the coating film;
3) subjecting the coating film to alignment treatment immediately after the drying step; and
4) heat-treating and curing the alignment-treated coating film.

9. The method for producing a liquid crystal alignment film of claim 8 , wherein the liquid crystal aligning agent composition is dissolved or dispersed in an organic solvent.

10. The method for producing a liquid crystal alignment film of claim 8 , wherein the drying of Step 2 is performed at a temperature of 50° C. to 130° C.

11. The method for producing a liquid crystal alignment film of claim 8 , wherein the alignment treatment of Step 3 is performed by irradiating polarized ultraviolet rays having a wavelength of 150 nm to 450 nm.

12. The method for producing a liquid crystal alignment film of claim 8 , wherein Step 4 comprises the steps of:
4-1) subjecting the alignment-treated coating film to a low-temperature heat treatment at 200° C. or less; and
4-2) heat-treating and curing the heat-treated coating film at a temperature of higher than that of the low-temperature heat treatment.

13. The method for producing a liquid crystal alignment film of claim 12 , wherein the low-temperature heat treatment of Step 4-1 is performed at a temperature of 110° C. to 200° C.

14. The method for producing a liquid crystal alignment film of claim 12 , wherein the heat treatment of Step 4-2 is performed at a temperature of 200° C. to 250° C.

15. A liquid crystal alignment film comprising an aligned and cured product of the liquid crystal aligning agent composition of claim 1 .

16. A liquid crystal display device comprising the liquid crystal alignment film of claim 15 .

Assignees

• Lg Chemical Ltd

Inventors

• Lee Sang Mi
• Han Hee
• Jo Jung Ho
• Min Sung Joon
• Park Hang Ah
• Kwon Soon Ho
• Yoon Jun Young
• Yun Hyeong Seuk
• Kim Seongku
• Park Hoonseo

Classifications

• C09K2323/00

  Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition · CPC title

• C08G59/245

  aromatic · CPC title

• C08G73/10

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

• C09K2323/027

  Polyimide · CPC title

• G02F1/133723

  Polyimide, polyamide-imide · CPC title