# US 2013/0158208 A1 · Liquid Crystal Alignment Agent, Liquid Crystal Alignment Film Using the Same, and Liquid Crystal Display Device Including the Liquid Crystal Alignment Film

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- Number: US 2013/0158208 A1
- Document ID: US20130158208A1
- Status: Published application
- Kind: A1
- Application number: 13/591,614
- Filed: 2012-08-22
- Published: 2013-06-20
- Earliest claimed: 2011-12-19
- Assignees: Cheil Industries Inc.
- Inventors: Jae-Deuk YANG; Yong-Sik YOO; Guk-Pyo JO
- Web page: https://patentgrep.com/patent/US20130158208A1

## CPC

- C08G 73/16: Polyester-imides
- C09K 2323/027: Polyimide
- G02F 1/133788: {by light irradiation, e.g. linearly polarised light photo-polymerisation}
- Y10T 428/31721: Of polyimide
- Y10T 428/31725: Of polyamide
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Disclosed are a liquid crystal alignment agent, a liquid crystal alignment film manufactured using the same, and a liquid crystal display including the liquid crystal alignment film. The liquid crystal alignment agent includes a polymer comprising a polyamic acid including a repeating unit represented by Chemical Formula 1, polyimide including a repeating unit represented by Chemical Formula 2, or a combination thereof: wherein Y1 and Y2 are each independently a divalent organic group derived from diamine, wherein the diamine includes photodiamine represented by Chemical Formula 3 and functional diamine represented by Chemical Formula 5: and wherein the other substituents are the same as defined in the detailed description.

## Claims

### Claim 1

A liquid crystal alignment agent, comprising
a polymer including polyamic acid including a repeating unit represented by the following Chemical Formula 1, polyimide including a repeating unit represented by the following Chemical Formula 2, or a combination thereof:
wherein, in Chemical Formulae 1 and 2,
X1 and X2 are the same or different and are each independently a tetravalent organic group derived from alicyclic acid dianhydride or aromatic acid dianhydride, and
Y1 and Y2 are the same or different and are each independently a divalent organic group derived from diamine, wherein the diamine includes a photodiamine represented by the following Chemical Formula 3 and a functional diamine represented by the following Chemical Formula 5,
wherein, in Chemical Formula 3,
R1, R3, and R6 are the same or different and are each independently hydrogen or substituted or unsubstituted C1 to C10 alkyl,
R2 and R4 are the same or different and are each independently a single bond, substituted or unsubstituted C1 to C10 alkylene, —O—, —CO—O—, —CO—NH—, —NH—CO—, or —O—CO—,
R5 is substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, or a substituted or unsubstituted C2 to C30 ether group,
n1 is an integer ranging from 0 to 3, n3 and n6 are the same or different and are each independently integers ranging from 0 to 4, and
m is an integer ranging from 1 to 5,
wherein, in Chemical Formula 5,
each R7 is independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heteroaryl,
R8 is a single bond, —O—, —S—, —NH—, —CO—, —CO—O—, —O—CO—, —CO—NH—, or —NH—CO—,
R9 is hydrogen, a substituted or unsubstituted C1 to C40 aliphatic organic group, a substituted or unsubstituted C2 to C40 aromatic organic group, or a substituted or unsubstituted C3 to C40 alicyclic organic group, and
n7 is an integer ranging from 0 to 3.

### Claim 2 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein the photodiamine comprises a compound represented by the following Chemical Formula 4:

### Claim 3 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein the functional diamine comprises a compound represented by the following Chemical Formula 6.

### Claim 4 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein the diamine comprises about 50 to about 95 mol % of the photodiamine and about 5 to about 50 mol % of the functional diamine.

### Claim 5 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein the diamine further comprises at least one aromatic diamine comprising a compound represented by the following Chemical Formulae 7-1 to 7-4, or a combination thereof:
wherein, in Chemical Formulae 7-1 to 7-4,
R50 to R59 are the same or different and are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heteroaryl, wherein each of the alkyl, aryl, and heteroaryl further includes —O—, —CO—O—, —CO—NH—, —NH—CO—, —O—CO—, or a combination thereof,
A1 to A6 are the same or different and are each independently a single bond, —O—, —SO2— or —C(R203)(R204)—, wherein, R203 and R204 are the same or different and are each independently hydrogen or substituted or unsubstituted C1 to C6 alkyl, and
n1 to n10 are the same or different and are each independently integers ranging from 0 to 4.

### Claim 6 (depends on 5)

The liquid crystal alignment agent of claim 5, wherein the diamine comprises about 50 to about 70 mol % of the photodiamine, about 5 to about 30 mol % of the functional diamine, and about 5 to about 30 mol % of the aromatic diamine.

### Claim 7 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein each of the polyamic acid and the polyimide has a weight average molecular weight of about 10,000 to about 300,000 g/mol.

### Claim 8 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein the polyamic acid and the polyimide are included in a weight ratio of about 1:99 to about 50:50 when the polymer comprises the polyamic acid and the polyimide.

### Claim 9 (depends on 1)

The liquid crystal alignment agent of claim 1, wherein the liquid crystal alignment agent has a solid content of about 0.1 to about 30 wt %.

### Claim 10 (depends on 1)

A liquid crystal alignment film manufactured by applying the liquid crystal alignment agent of claim 1 to a substrate.

### Claim 11 (depends on 10)

A liquid crystal display comprising the liquid crystal alignment film of claim 10.