# US 11,441,075 B2 · Liquid crystal alignment agent composition, method of producing liquid crystal alignment film using the same, and liquid crystal alignment film using the same

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- Number: US 11,441,075 B2
- Document ID: US11441075B2
- Status: Granted
- Kind: B2
- Application number: 16/619,688
- Filed: 2018-10-10
- Published: 2020-05-28
- Granted: 2022-09-13
- Earliest claimed: 2017-10-20
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Soon Ho Kwon; Seongku Kim; Sung Joon Min; Hoonseo Park; Hyeong Seuk Yun; Sang Mi Lee; Jung Ho Jo
- Web page: https://patentgrep.com/patent/US11441075B2

## CPC

- C09K 19/56: Aligning agents
- C08G 73/1042: {Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds}
- C08G 73/1078: {wholly aromatic in the diamino moiety}
- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- G02F 1/133723: {Polyimide, polyamide-imide}
- G02F 1/133788: {by light irradiation, e.g. linearly polarised light photo-polymerisation}
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- C09K 2323/027: Polyimide
- 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)
- 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

A liquid crystal alignment agent composition for producing a liquid crystal alignment film having enhanced alignment property and stability and a high voltage holding ratio, a method of producing a liquid crystal alignment film using the same, and a liquid crystal alignment film and a liquid crystal display device using the same, are provided.

## Claims

### Claim 1

A liquid crystal alignment film comprising a liquid crystal alignment agent composition comprising a first polymer for a first liquid crystal alignment agent including a repeating unit represented by Chemical Formula 1 and one or more repeating units selected from the group of a repeating unit represented by Chemical Formula 2 and a repeating unit represented by Chemical Formula 3, wherein the repeating unit represented by Chemical Formula 1 is included in an amount of 5 mol % to 74 mol % with respect to a total of the repeating units represented by the following Chemical Formulae 1 to 3; and
a second polymer for a second liquid crystal alignment agent including one or more repeating units selected from the group of a repeating unit represented by Chemical Formula 4, a repeating unit represented by Chemical Formula 5, and a repeating unit represented by Chemical Formula 6:
wherein, in the Chemical Formulae 1 to 6,
R1, R2, R3, and R4 are each independently hydrogen or a C1-10 alkyl, provided that R1 and R2 are not both hydrogen, and that R3 and R4 are not both hydrogen,
X1 is a tetravalent organic group represented by Chemical Formula 7:
wherein, in the Chemical Formula 7,
R5, R6, R7, and R8 are each independently hydrogen or a C1-6 alkyl,
X2, X3, X4, X5, and X6 are each independently a tetravalent organic group derived from a hydrocarbon having 4 to 20 carbon atoms, or a tetravalent organic group derived from a hydrocarbon having 4 to 20 carbon atoms wherein one or more of H is substituted with a halogen, or one or more of —CH2— is substituted with —O—, —CO—, —S—, —SO—, —SO2—, or —CONH— to prevent direct binding with oxygen or sulfur atoms in the tetravalent organic group,
in the Chemical Formulae 1 to 3,
Y1 to Y3 are each independently a divalent organic group represented by Chemical Formula 8:
wherein, in the Chemical Formula 8,
R9 and R10 are each independently a halogen, a cyano, a C1-10 alkyl, a C2-10 alkenyl, a C1-10 alkoxy, a C1-10 fluoroalkyl, or a C1-10 fluoroalkoxy,
p and q are each independently an integer of 0 to 4,
L1 is a single bond, —O—, —CO—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —CONH—, —COO—, —(CH2)z—, —O(CH2)zO—, —O (CH2)z—, —OCH2—C(CH3)2—CH2O—, —COO—(CH2)z—OCO—, or —OCO—(CH2)z—COO—, wherein z is an integer of 1 to 10,
k and m are each independently an integer of 1 to 3,
n is an integer of 0 to 3,
in Chemical the Formulae 4 to 6,
Z1, Z2, and Z3 are each independently a divalent organic group represented by Chemical Formula 9:
wherein, in the Chemical Formula 9,
A1 is an element of nitrogen, phosphorus, arsenic, tin or bismuth,
R11 is hydrogen or a C1-10 alkyl,
a is an integer of 1 to 3, and
A2, A3, A4, and A5 are nitrogen or carbon, provided that at least one of A2 or A5 is nitrogen and the other is carbon and A3 and A4 are carbon,
wherein X2, X3, X4, X5, and X6 are each independently a tetravalent
organic group represented by Chemical Formula 10:
[Chemical Formula 10]
wherein, in Chemical Formula 10,
R5, R6, R7, and R8 are each independently hydrogen or a C1-6 alkyl,
R12 and R13 are each independently hydrogen or a C1-10 alkyl, and
L2 is any one selected from the group consisting of a single bond, —O—, —CO—, —S—, —SO—, —SO2—, —CR14R15—, —CONH—, —COO—, —(CH2)b—, —O—(CH2)bO—, —COO—(CH2)b—OCO—, —HN—(CH2)b—NH—, —R14N—(CH2)b—NR15—, phenylene, and combinations thereof, wherein R14 and R15 are each independently hydrogen, a C1-10 alkyl, or a C1-10 fluoroalkyl, and each b is independently an integer of 1 to 10,
wherein, Y1 of the repeating unit represented by Chemical Formula 1 is connected to an adjacent repeating unit represented by Chemical Formula 1 as N—Y1—N—, or to an adjacent repeating unit represented by Chemical Formula 2 or 3 as —HN—Y1—N—; Y2 of the repeating unit represented by Chemical Formula 2 is connected to an adjacent repeating unit represented by Chemical Formula 2 or 3 as —HN—Y2—NH—, or to an adjacent repeating unit represented by Chemical Formula 1 as —N—Y2—NH—; and Y3 of the repeating unit represented by Chemical Formula 3 is connected to an adjacent repeating unit represented by Chemical Formula 2 or 3 as —NH—Y3—NH— or to an adjacent repeating unit represented by Chemical Formula 1 as —N—Y3—NH—,
wherein, Z1 of the repeating unit represented by Chemical Formula 4 is connected to an adjacent repeating unit represented by Chemical Formula 4 as —N—Z1—N—, or to an adjacent repeating unit represented by Chemical Formula 5 or 6 as —HN—Z1—N—; Z2 of the repeating unit represented by Chemical Formula 5 is connected to an adjacent repeating unit represented by Chemical Formula 5 or 6 as —HN—Z2—NH—, or to an adjacent repeating unit represented by Chemical Formula 4 as —N—Z2—NH—; and Z3 of the repeating unit represented by Chemical Formula 6 is connected to an adjacent repeating unit represented by Chemical Formula 5 or 6 as —NH—Z3—NH— or to an adjacent repeating unit represented by Chemical Formula 4 as —N—Z3—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.

### Claim 2 (depends on 1)

The liquid crystal alignment agent film of claim 1, wherein the Chemical Formula 8 is a divalent organic group represented by Chemical Formula 11 or Chemical Formula 12:
wherein, in Chemical Formula 12,
L3 is a single bond, —O—, —SO2—, or —CR16R17—, wherein R16 and R17 are each independently hydrogen or a C1-10 alkyl.

### Claim 3 (depends on 1)

The liquid crystal alignment agent film of claim 1, wherein in the Chemical Formula 9, A1 is nitrogen, R11 is hydrogen, and a is 1.

### Claim 4 (depends on 1)

The liquid crystal alignment agent film of claim 1, wherein the Chemical Formula 9 includes one or more repeating units selected from the group of Chemical Formula 9-1, Chemical Formula 9-2, and Chemical Formula 9-3:
wherein, in the Chemical Formulae 9-1 to 9-3,
A1 to A5, R11, and a are as defined in claim 1.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

The liquid crystal alignment agent film of claim 1, wherein the second polymer for the second liquid crystal alignment agent further includes one or more repeating units selected from the group of a repeating unit represented by Chemical Formula 13, a repeating unit represented by Chemical Formula 14, and a repeating unit represented by Chemical Formula 15:
wherein, in the Chemical Formulae 13 to 15,
at least one of R18 and R19 is an alkyl group having 1 to 10 carbon atoms and the other is hydrogen,
X7 to X9 are each independently a tetravalent organic group, and
Z4 to Z6 are each independently a divalent organic group represented by Chemical Formula 16:
wherein, in the Chemical Formula 16,
R20 and R21 are each independently a halogen, a cyano, a C1-10 alkyl, a C2-10 alkenyl, a C1-10 alkoxy, a C1-10 fluoroalkyl, or a C1-10 fluoroalkoxy,
p′ and q′ are each independently an integer of 0 to 4,
L4 is a single bond, —O—, —CO—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —CONH—, —COO—, —(CH2)z—, —O (CH2)zO—, —O (CH2)z—, —OCH2—C(CH3)2—CH2O—, —COO—(CH2)z—OCO—, or —OCO—(CH2)z—COO—, wherein each z is independently 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
when n′=0, k′ is 1 to 3, and when k′=0, m and n are each independently 1 to 3.

### Claim 7 (depends on 6)

The liquid crystal alignment agent film of claim 6, wherein the Chemical Formula 16 is Chemical Formula 17 or Chemical Formula 18:
wherein, in the Chemical Formula 18,
L5 is a single bond, —O—, —SO2—, or —CR22R23—, wherein R22 and R23 are each independently hydrogen or a C1-10 alkyl.

### Claim 8 (depends on 1)

A method of producing the liquid crystal alignment film of claim 1, the method comprising the steps of:
coating a solution or a dispersion, of the liquid crystal alignment agent composition comprising the first polymer for a first liquid crystal alignment agent and the second polymer for a second liquid crystal alignment agent onto a substrate to form a coating film;
drying the coating film;
irradiating the coating film with light immediately after the step of drying the coating film to perform an alignment treatment; and
heat-treating and curing the alignment-treated coating film.

### Claim 9 (depends on 8)

The method of producing the liquid crystal alignment film of claim 8, wherein the liquid crystal alignment agent composition is dissolved or dispersed in an organic solvent.

### Claim 10 (depends on 8)

The method of producing the liquid crystal alignment film of claim 8, wherein the step of drying the coating film is performed at 50° C. to 150° C.

### Claim 11 (depends on 8)

The method of producing the liquid crystal alignment film of claim 8, wherein in the alignment treatment step, the light irradiation is performed by irradiating polarized ultraviolet rays having a wavelength of 150 nm to 450 nm.

### Claim 12 (depends on 8)

The method of producing the liquid crystal alignment film of claim 8, wherein in the step of heat-treating and curing the coating film, the heat treatment temperature is 150° C. to 300° C.

### Claim 13 (depends on 1)

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