# US 11,078,424 B2 · Liquid crystal aligning agent composition, method for preparing liquid crystal alignment film using same, and liquid crystal alignment film and liquid crystal display device using same

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- Number: US 11,078,424 B2
- Document ID: US11078424B2
- Status: Granted
- Kind: B2
- Application number: 16/497,330
- Filed: 2019-01-23
- Published: 2021-01-14
- Granted: 2021-08-03
- Earliest claimed: 2018-02-21
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Hyeongseuk Yun; Jung Ho Jo; Jun Young Yoon; Hoonseo Park
- Web page: https://patentgrep.com/patent/US11078424B2

## CPC

- C09K 19/56: Aligning agents
- C08G 73/16: Polyester-imides
- C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers
- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- G02F 1/1337: Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- C09K 2219/03: in the form of films, e.g. films after polymerisation of LC precursor
- C09K 2323/027: Polyimide
- C09K 2323/035: Ester polymer, e.g. polycarbonate, polyacrylate or polyester
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- 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

## Abstract

Provided is a liquid crystal aligning agent composition including a liquid crystal polymer together with a polyimide-based (co)polymer, a method for preparing a liquid crystal alignment film using the same, and a liquid crystal alignment film and a liquid crystal display device using the same.

## Claims

### Claim 1

A liquid crystal aligning agent composition, comprising:
a polyimide-based (co)polymer containing at least one repeating unit selected from the group consisting of a polyamic acid repeating unit, a polyamic acid ester repeating unit, and a polyimide repeating unit; and
an aromatic polyester-based polymer that includes a repeating unit of the following Chemical Formula 1-1:
wherein in Chemical Formula 1-1:
Ar is an arylene group having 10 to 15 carbon atoms; and
R3 is an alkylene group having 8 to 14 carbon atoms.

### Claim 2 (depends on 1)

The liquid crystal aligning agent composition of claim 1, wherein the polyimide-based (co)polymer and the aromatic polyester-based polymer are mixed in a weight ratio of 1:99 to 1:0.5.

### Claim 3 (depends on 1)

The liquid crystal aligning agent composition of claim 1, wherein the aromatic polyester-based polymer has a weight average molecular weight of 10,000 g/mol to 100,000 g/mol.

### Claim 4 (depends on 1)

The liquid crystal aligning agent composition of claim 1, wherein the aromatic polyester-based polymer has liquid crystallinity at 200° C. to 240° C.

### Claim 5 (depends on 1)

The liquid crystal aligning agent composition of claim 1, wherein the polyimide repeating unit has the following Chemical Formula 2, the polyamic acid ester repeating unit has the following Chemical Formula 3, and the polyamic acid repeating unit has the following Chemical Formula 4:
wherein in Chemical Formulae 2 to 4:
one of R4 and R5 is an alkyl group having 1 to 10 carbon atoms and the other is selected from the group consisting of hydrogen and an alkyl group having 1 to 10 carbon atoms;
X1 to X3 are the same as or different from each other, and are each independently a tetravalent organic group; and
Y1 to Y3 are the same as or different from each other and are each independently a divalent organic group of the following Chemical Formula 5:
wherein in Chemical Formula 5:
T is a tetravalent organic group; and
D1 and D2 are each independently an alkylene group having 1 to 20 carbon atoms, a heteroalkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 2 to 20 carbon atoms.

### Claim 6 (depends on 5)

The liquid crystal aligning agent composition of claim 5, wherein X1 to X3 and T are each independently a tetravalent organic group having one of the following formulae:
wherein:
R6 to R11 are each independently any substituent selected from the group consisting of hydrogen and an alkyl group having 1 to 6 carbon atoms;
L1 is a single bond, —O—, —CO—, —COO—, —S—, —SO—, —SO2—, —CR12R13—, —(CH2)t—, —O(CH2)tO—, —COO(CH2)tOCO—, —CONH—, phenylene, or a combination thereof;
R12 and R13 are each independently hydrogen, or an alkyl group having 1 to 10 carbon atoms or a haloalkyl group having 1 to 10 carbon atoms; and
t is an integer from 1 to 10.

### Claim 7 (depends on 1)

A method for preparing a liquid crystal alignment film, comprising:
coating the liquid crystal aligning agent composition of claim 1 onto a substrate to form a coating film;
drying the coating film;
irradiating the dried coating film with light or rubbing the coating film to provide an alignment-treated coating film; and
heat-treating and curing the alignment-treated coating film.

### Claim 8 (depends on 7)

The method of claim 7, wherein the step of drying the coating film is performed at a temperature of 50° C. to 150° C.

### Claim 9 (depends on 7)

The method of claim 7, wherein the step of heat-treating and curing the alignment-treated coating film is performed at a temperature of 180° C. to 300° C.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 10)

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

### Claim 12 (depends on 7)

The method of claim 7, wherein the step of heat-treating and curing the alignment-treated coating film is performed at a temperature of 200° C. to 300° C.

### Claim 13 (depends on 7)

The method of claim 7, wherein the step of heat-treating and curing the alignment-treated coating film is performed at a temperature of 200° C. to 240° C.

### Claim 14 (depends on 1)

The liquid crystal aligning agent composition of claim 1, wherein the polyimide-based (co)polymer and the aromatic polyester-based polymer are mixed in a weight ratio of 1:20 to 1:0.5.

### Claim 15 (depends on 1)

The liquid crystal aligning agent composition of claim 1, wherein the polyimide-based (co)polymer and the aromatic polyester-based polymer are mixed in a weight ratio of 1:9 to 1:0.45.

### Claim 16 (depends on 7)

A liquid crystal alignment film, prepared by the method of claim 7.