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

Patent metadata

Field	Value
Publication number	US-11512255-B2
Application number	US-201917043310-A
Country	US
Kind code	B2
Filing date	Nov 12, 2019
Priority date	Nov 20, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The present invention relates to a liquid crystal alignment composition comprising first liquid crystal alignment polymer; second liquid crystal alignment polymer; and a cross-linking agent compound, a method for preparing a liquid crystal alignment film using the same, a liquid crystal alignment film and a liquid crystal display using the same.

First claim

The invention claimed is:

1. A liquid crystal alignment composition comprising
a first liquid crystal alignment polymer comprising at least one repeat units selected from a group of repeat units represented by Chemical Formula 1, repeat units represented by Chemical Formula 2, or repeat units represented by Chemical Formula 3;
a second liquid crystal alignment polymer comprising at least one repeat units selected from a group of repeat units represented by Chemical Formula 4, repeat units represented by Chemical Formula 5, or repeat units represented by Chemical Formula 6: and
a cross-linking agent compound represented by Chemical Formula 9:

in the Chemical Formulae 1 to 6,
at least one of R 1 and R 2 is a C1-10 alkyl group, and the other is hydrogen,
at least one of R 3 and R 4 is a C1-10 alkyl group, and the other is hydrogen,
X 1 to X 6 are each independently, a tetravalent organic group,
Y 1 to Y 3 are each independently, a divalent organic group represented by Chemical Formula 7,

in the Chemical Formula 7,
T is a tetravalent organic group, and
D 1 and D 2 are each independently, a C1-20 alkylene group, a C1-10 heteroalkylene group, a C3-20 cycloalkylene group, a C6-20 arylene group, or a C2-20 heteroarylene group, and
Z 1 to Z 3 are each independently, a divalent organic group represented by Chemical Formula 8,

in the Chemical Formula 8,
A 1 is a Group 15 element selected from a group of nitrogen (N), phosphorus (P), arsenic (As), antimony (Sb) or bismuth (Bi),
R 5 is hydrogen, or a C1-10 alkyl group,
a is an integer of 1 to 3, and
A 2 , A 3 , A 4 , and A 5 are each independently nitrogen or carbon, provided that at least one of A 2 to A 5 is nitrogen and the others are carbon,

in the Chemical Formula 9,
A 6 is at least one of mono- to tetravalent functional groups,
j is an integer of 1 to 4,
L 2 and L 3 are identical to or different from each other, and each independently, a C1-10 alkylene group or a C6-20 arylene group, and
R 6 and R 7 are each independently, a silicon-containing monovalent functional group.

2. The liquid crystal alignment composition according to claim 1 , wherein X 1 to X 6 are each independently, a tetravalent group represented by Chemical Formula 10:

in the Chemical Formula 10,
R 8 to R 13 are each independently, hydrogen, or a C1-10 alkyl group,
L 4 is a direct bond, —O—, —CO—, —S—, —SO—, —SO 2 —, —CR 14 R 15 —, —CONH—, —COO—, —(CH 2 ) b —, —O(CH 2 ) b O—, —COO—(CH 2 ) b —OCO—, —R 16 N—(CH 2 ) b —NR 17 —, phenylene, or a combination thereof,
R 14 to R 17 are each independently, hydrogen, a C1-10 alkyl group, or a C1-10 haloalkyl group, and
b is an integer of 1 to 10.

3. The liquid crystal alignment composition according to claim 1 , wherein in the Chemical Formula 8, one of A 2 to A 5 is nitrogen, and the others are carbon.

4. The liquid crystal alignment composition according to claim 1 , wherein in the Chemical Formula 8, one of A 2 and A 5 is nitrogen and the other is carbon, and A 3 and A 4 are carbon.

5. The liquid crystal alignment composition according to claim 1 , wherein in the Chemical Formula 8, A 1 is nitrogen, R 5 is hydrogen, and a is 1.

6. The liquid crystal alignment composition according to claim 1 , wherein the Chemical Formula 8 includes a divalent functional group selected from a group of a divalent functional group represented by Chemical Formula 8-1, a divalent functional group represented by Chemical Formula 8-2 or a divalent functional group represented by Chemical Formula 8-3:

in the Chemical Formulae 8-1 to 8-3,
A 1 to A 5 , R 5 , and a are as defined in claim 1 .

7. The liquid crystal alignment composition according to claim 1 , wherein the first liquid crystal alignment polymer and the second liquid crystal alignment polymer are included at a weight ratio of 5:95 to 95:5.

8. The liquid crystal alignment composition according to claim 1 , wherein the second liquid crystal alignment polymer further comprises at least one repeat units selected from a group of repeat units represented by Chemical Formula 11, repeat units represented by Chemical Formula 12, or repeat units represented by Chemical Formula 13:

in the Chemical Formulae 11 to 13,
at least one of R 18 and R 19 is a C1-10 alkyl group, and the other is hydrogen,
X 7 to X 9 are each independently, a tetravalent functional group,
Z 4 to Z 6 are each independently, a divalent functional group represented by Chemical Formula 14,

in the Chemical Formula 14,
R 20 and R 21 are each independently, halogen, cyano, C1-10 alkyl, C2-10 alkenyl, C1-10 alkoxy, C1-10 fluoroalkyl, or C1-10 fluoroalkoxy,
p′ and q′ are each independently, an integer of 0 to 4,
L 6 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—, —OCH(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 of 1 to 10,
k′ and m′ are each independently, an integer of 0 to 3, and
n′ is an integer of 0 to 3.

9. The liquid crystal alignment composition according to claim 1 , wherein in the Chemical Formula 9,
A 6 is a C1-10 alkylene group,
J is 2,
L 2 and L 3 are each independently, a C1-5 alkylene group, and
R 6 and R 7 are each independently, the silicon-containing monovalent functional group.

10. The liquid crystal alignment composition according to claim 1 , wherein the silicon-containing monovalent functional group is represented by Chemical Formula 15:

in the Chemical Formula 15, R 22 , R 23 and R 24 are each independently, hydrogen, or C1-10 alkyl.

11. A method for preparing a liquid crystal alignment film, comprising steps of:
applying the liquid crystal alignment composition of claim 1 on a substrate to form a coating;
drying the coating;
irradiating light to the coating or rubbing the coating to progress alignment treatment; and
heat treating the alignment-treated coating to cure.

12. The method according to claim 11 , wherein in the step of heat treating the alignment-treated coating to cure, the alignment-treated coating contains a cross-linking agent compound represented by the following Chemical Formula 16:

in the Chemical Formula 16,
A 6 , j, L 2 , and L 3 are as defined in claim 1 .

13. A liquid crystal alignment

Assignees

• Lg Chemical Ltd

Inventors

• Yoon Jun Young
• Koo Kichul
• Jo Jung Ho
• Kwon Soonho
• Yun Hyeongseuk
• Park Hoonseo

Classifications

• C09K19/56 Primary

  Aligning agents · CPC title

• C09D179/08

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

• C08G73/1071

  Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain · CPC title

• C08G73/1067

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

• C08L79/08

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