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

Patent metadata

Field	Value
Publication number	US-11073728-B2
Application number	US-201816164043-A
Country	US
Kind code	B2
Filing date	Oct 18, 2018
Priority date	Nov 28, 2016
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

The present invention provides a liquid crystal alignment film not only having an excellent alignment property and stability, but also having high film strength, and thus exhibiting excellent durability and a high residual image property, a method for preparing the same, and a liquid crystal display device using the same.

First claim

The invention claimed is:

1. A liquid crystal alignment film comprising: a polymer containing a first repeating unit including at least one selected from the group consisting of Chemical Formula 1 to Chemical Formula 3 below; and
a second repeating unit including at least one selected from the group consisting of Chemical Formula 4 and Chemical Formula 5 below,
wherein the liquid crystal alignment film has a retardation value of 3 nm or higher:

wherein, in Chemical Formulae 1 to 5,
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 5 are each independently a tetravalent organic group represented by Chemical Formula 6 below:

wherein, in Chemical Formula 6,
R 3 to R 8 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and
L 1 is any one selected from the group consisting of a direct bond, —O—, —CO—, —COO—, —S—, —SO—, —SO 2 —, —CR 9 R 10 —, —(CH 2 ) Z —, —O(CH 2 ) Z O—, —COO(CH 2 ) Z OCO—, —CONH—, phenylene, or a combination thereof,
wherein R 9 and R 10 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a fluoroalkyl group, and
Z is an integer of 1 to 10,
Y 1 to Y 5 are each independently a divalent organic group represented by Chemical Formula 7 below:

wherein, in Chemical Formula 7,
A is a tetravalent organic group represented by Chemical Formula 6, and
D 1 and D 2 are each independently an arylene group having 6 to 20 carbon atoms; and
in Chemical Formulae 4 and 5,

at least one of R′ and R″ is a functional group containing a mesogenic group, and the other is hydrogen,
wherein the functional group containing the mesogenic group is represented by Chemical Formulae 8 below:

wherein, in Chemical Formula 8,
Ar 1 and Ar 2 are each independently phenylene or naphthylene,
Q 1 and Q 2 are a direct bond, an alkylene group having 1 to 10 carbon atoms, or an alkyleneoxy group having 1 to 10 carbon atoms,
each L is independently a direct bond, —COO—, —C(CH 3 )═CH—, or —C(CH 3 )═N—N═C(CH 3 )—,
n is an integer of 0, 1, or 2, and
m is an integer of 1 to 10, and the mesogenic group in the Chemical Formula 8 is represented by:

2. The liquid crystal alignment film of claim 1 , wherein,
in Chemical Formula 8, Ar 1 and Ar 2 are each independently phenylene,
Q 1 and Q 2 are each independently an alkyleneoxy group having 1 to 3 carbon atoms,
L is —COO—,
n is 1, and m is 1.

3. The liquid crystal alignment film of claim 1 , wherein,
in Chemical Formula 8, Ar 1 and Ar 2 are each independently phenylene,
Q 1 and Q 2 are each independently an alkyleneoxy group having 1 to 3 carbon atoms,
L is —COO—,
n is 2, and m is 1.

4. The liquid crystal alignment film of claim 1 , wherein the polymer further includes a functional group represented by Chemical Formula 9 below or a functional group represented by Chemical Formula 10 below at at least one terminal end:

wherein, in Chemical Formula 9,
X 1 , Y 1 , R′, and R″ are as defined in claim 1 ,

wherein, in Chemical Formula 10,
R 11 and R 12 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and
X 2 , Y 2 , R′, and R″ are as defined in claim 1 .

5. The liquid crystal alignment film of claim 1 , wherein the polymer further includes a polymer containing a third repeating unit including at least one selected from the group consisting of Chemical Formulae 11 to 13, and a fourth repeating unit including at least one selected from the group consisting of Chemical Formulae 14 and 15:

wherein, in Chemical Formulae 11 to 15,
at least one of R 13 and R 14 is an alkyl group having 1 to 10 carbon atoms, and the other is hydrogen,
X 6 to X 10 are each independently a tetravalent organic group represented by Chemical Formula 6 defined in claim 1 , and
Y 6 to Y 10 are each independently a divalent organic group represented by Chemical Formula 16 below:

wherein, in Chemical Formula 16,
R 15 and R 16 are each independently hydrogen, a halogen, a cyano, a nitrile, an alkyl having 1 to 10 carbon atoms, an alkenyl having 1 to 10 carbon atoms, an alkoxy having 1 to 10 carbon atoms, a fluoroalkyl having 1 to 10 carbon atoms, or a fluoroalkoxy having 1 to 10 carbon atoms,
p and q are each independently an integer of 0 to 4,
L 2 is a direct bond, —O—, —CO—, —S—, —SO 2 —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CONH—, —COO—, —(CH 2 ) y —, —O(CH 2 ) y O—, —O(CH 2 ) y —, —NH—, —NH(CH 2 ) y —NH—, —NH(CH 2 ) y O—, —OCH 2 —C(CH 3 ) 2 —CH 2 O—, —COO—(CH 2 ) y —OCO—, or —OCO—(CH 2 ) y —COO—,
y is an integer of 1 to 10,
k and m are each independently an integer of 0 to 3,
n is an integer of 0 to 3, and
R′ and R″ are as defined in claim 1 ,

wherein when n=0, k is 1 to 3, and wherein when k=0, m and n are each independently 1 to 3.

6. The liquid crystal alignment film of claim 5 , wherein, in the liquid crystal alignment film, a weight ratio between the polymer including the third repeating unit including at least one selected from the group consisting of Chemical Formulae 11 to 13, and the fourth repeating unit including at least one selected from the group consisting of Chemical Formulae 14 and 15; and the polymer containing the first repeating unit including at least one selected from the group consisting of Chemical Formulae 1 to 3 defined in claim 1 and the second repeating unit including at least one selected from the group consisting of Chemical Formulae 4 and 5 is 10:90 to 90:10.

7. The liquid crystal alignment film of claim 1 , wherein the polymer has a weight average molecular weight of 5000 to 100,000 measured by the GPC method.

8. A liquid crystal display device including the liquid crystal alignment film of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

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

Classifications

• C09K19/56 Primary

  Aligning agents · CPC title

• C09K2219/03

  in the form of films, e.g. films after polymerisation of LC precursor · CPC title

• C08G73/10

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

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title

• C09K2323/027

  Polyimide · CPC title