Polymer for liquid crystal alignment agent, liquid crystal alignment agent comprising the same, and liquid crystal alignment film and liquid crystal display device using the same

Patent metadata

Field	Value
Publication number	US-11286348-B2
Application number	US-201816484390-A
Country	US
Kind code	B2
Filing date	May 14, 2018
Priority date	May 22, 2017
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

The present invention relates to a polymer having excellent liquid crystal alignment and electrical properties and thus is suitable for use as a liquid crystal alignment agent, a liquid crystal alignment agent containing the same, a liquid crystal aligning film formed from the liquid crystal alignment agent, and a liquid crystal display device containing the liquid crystal aligning film.

First claim

The invention claimed is:

1. A liquid crystal alignment film comprising a liquid crystal alignment agent comprising a copolymer comprising 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, in Chemical Formulae 1 to 3,
at least one of R 1 and R 2 is an alkyl group having 1 to 10 carbon atoms, and the other is hydrogen,
X 1 to X 3 are each independently a tetravalent organic group represented by Chemical Formula 5,

wherein, in Chemical Formula 5,
R 9 to R 14 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,
L 2 is any one selected from the group consisting of a direct bond, —O—, —CO—, —S—, —SO—, —SO 2 —, —CR 15 R 16 —, —CONH—, —COO—, —(CH 2 ) b —, —O(CH 2 ) b O—, —COO—(CH 2 ) b —OCO—, phenylene, or a combination thereof,
R 15 and R 16 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a fluoroalkyl group having 1 to 10 carbon atoms, and b is an integer of 1 to 10, and
Y 1 to Y 3 are each independently a divalent organic group represented by the following Chemical Formula 4:

wherein, in Chemical Formula 4,
A is a Group 16 element selected from oxygen (O), sulfur (S), selenium (Se), tellurium (Te), or polonium (Po),
and
at least one of Z 1 to Z 4 is nitrogen and the rest are carbon,
wherein, Y 1 of the repeating unit represented by Chemical Formula 1 is connected to an adjacent repeating unit as —N—Y 1 —N or —HN—Y 1 —N—, Y 2 of the repeating unit represented by Chemical Formula 2 is connected to an adjacent repeating unit as —HN—Y 2 —NH— or —N—Y 2 —NH—, and Y 3 of the repeating unit represented by Chemical Formula 3 is connected to an adjacent repeating unit as —NH—Y 3 —NH— or —N—Y 3 —NH—, and
wherein the liquid crystal alignment film is prepared by an alignment treatment including irradiating with polarized light or rubbing in one direction, without preceding or concurrent curing, prior to a curing heat treatment.

2. The liquid crystal alignment film according to claim 1 , wherein in the Chemical Formula 4, one of Z 1 to Z 4 is nitrogen and the rest are carbon.

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

4. The liquid crystal alignment film according to claim 1 , wherein the Chemical Formula 4 includes one or more divalent organic groups selected from the group consisting of Chemical Formulae 4-1, 4-2, and 4-3:

wherein, in Chemical Formulae 4-1, 4-2, and 4-3, A, Z 1 , Z 2 , Z 3 , and Z 4 are as defined in the Chemical Formula 4.

5. The liquid crystal alignment film according to claim 1 , further comprising one or more repeating units selected from the group consisting of a repeating unit represented by Chemical Formula 11, a repeating unit represented by Chemical Formula 12, and a repeating unit represented by Chemical Formula 13:

wherein, in Chemical Formulae 11 to 13,
at least one of R 3 and R 4 is an alkyl group having 1 to 10 carbon atoms and the other is hydrogen,
X 4 to X 6 are each independently a tetravalent organic group, and
Y 4 to Y 6 are each independently a divalent organic group represented by Chemical Formula 14:

wherein, in Chemical Formula 14,
R 5 and R 6 are each independently hydrogen, 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 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 0 to 3, and
n is an integer of 0 to 3,
when n=0, k is 1 to 3, and when k=0, m and n are each independently 1 to 3.

6. The liquid crystal alignment film according to claim 5 , wherein the Chemical Formula 14 is represented by Chemical Formula 15 or Chemical Formula 16:

wherein, in Chemical Formula 16,
D is a direct bond, O, SO 2 , or C(R 7 )(R 8 ), wherein R 7 and R 8 are each independently hydrogen, or an alkyl group having 1 to 10 carbon atoms.

7. A liquid crystal display device comprising the liquid crystal alignment film of claim 5 .

8. The liquid crystal alignment film according to claim 1 , wherein the copolymer has a weight average molecular weight of 1000 g/mol to 200,000 g/mol.

9. A liquid crystal display device comprising the liquid crystal alignment film of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

• Kwon Soon Ho
• Koo Kichul
• Jo Jung Ho
• Min Sung Joon
• Lee Sang Mi
• Yoon Jun Young
• Yun Hyeong Seuk
• Lim Yoon Bin

Classifications

• C08G73/1035

  from tetracarboxylic acids or derivatives and diisocyanates · CPC title

• C09K2323/027

  Polyimide · CPC title

• C09K2323/025

  Polyamide · CPC title

• C08G73/1071

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

• C09K19/56 Primary

  Aligning agents · CPC title