# US 2017/0283702 A1 · Alignment film composition, liquid crystal display device, and method of manufacturing liquid crystal display device

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- Number: US 2017/0283702 A1
- Document ID: US20170283702A1
- Status: Published application
- Kind: A1
- Application number: 15/400,496
- Filed: 2017-01-06
- Published: 2017-10-05
- Earliest claimed: 2016-04-05
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Suk Hoon KANG; Jong Hwan JEON; Jin Soo JUNG; In Ok KIM; Baek Kyun JEON
- Web page: https://patentgrep.com/patent/US20170283702A1

## CPC

- C08G 73/16: Polyester-imides
- C09K 19/56: Aligning agents
- B05D 1/005: {Spin coating}
- B05D 1/265: {Extrusion coatings}
- B05D 3/0254: {After-treatment}
- B05D 3/065: {After-treatment}
- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- C08G 73/1082: {wholly aromatic in the tetracarboxylic moiety}
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- G02F 1/133723: {Polyimide, polyamide-imide}
- G02F 1/13378: {by treatment of the surface, e.g. embossing, rubbing or light irradiation (G02F1/133711, G02F1/133734, G02F1/133753 take precedence)}
- G02F 1/133788: {by light irradiation, e.g. linearly polarised light photo-polymerisation}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K 2323/02: Alignment layer characterised by chemical composition
- C09K 2323/027: Polyimide
- G02F 1/133397: {for suppressing after-image or image-sticking}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- 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

An alignment film composition includes a copolymer of a dianhydride-based compound and a diamine-based compound, and a cross-linker. The copolymer has a structure represented by Chemical Formula Ia or Chemical Formula Ib, and the cross-linker is represented by Chemical Formula IIa or Chemical Formula IIb:

## Claims

### Claim 1

An alignment film composition, comprising:
a copolymer of a dianhydride-based compound and a diamine-based compound, the copolymer having a structure represented by Chemical Formula Ia or Chemical Formula Ib in a repetitive unit; and
a cross-linker represented by Chemical Formula IIa or Chemical Formula IIb,
wherein:
and
wherein:
in Chemical Formula Ia and Chemical Formula Ib:
R1 is a tetravalent organic group derived from an alicyclic dianhydride or an aromatic dianhydride; and
R2 is a divalent organic group derived from an alicyclic diamine or an aromatic diamine;
in Chemical Formula Ib, R3 and R4 are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group;
in Chemical Formula IIa and Chemical Formula IIb:
X1 to X4 are each independently any one of a hydroxyl group (—OH), an amino group (—NH2), an epoxy group, an aziridine group, a carbodiimide group, an acrylate group, a methacrylate group, and a vinyl group;
Y1 and Y2 are each independently any one of a single bond, —CO—, —COO—, —OCO—, —S—, —O—, —OOC— —CH2CH2O—, —OCH2CH2—, an aromatic compound of 6 to 30 carbon atoms, and an alicyclic compound of 4 to 20 carbon atoms;
m1 to m4 are each independently an integer of 0 to 6; and
n is an integer of 2 to 18; and
in Chemical Formula IIa, Z1 and Z2 are each independently any one of
R being H or an alkyl group of 1 to 3 carbon atoms, an aromatic compound of 6 to 30 carbon atoms, and an alicylic compound of 4 to 20 carbon atoms.

### Claim 2 (depends on 1)

The alignment film composition of claim 1, wherein in Chemical Formula Ia and Chemical Formula Ib, R2 is any one of

### Claim 3 (depends on 1)

The alignment film composition of claim 1, wherein in Chemical Formula IIa:
X1 and X4 are identical functional groups; and
X2 and X3 are identical functional groups.

### Claim 4 (depends on 3)

The alignment film composition of claim 3, wherein in Chemical Formula IIa and Chemical Formula IIb, X1 and X2 are identical functional groups.

### Claim 5 (depends on 3)

The alignment film composition of claim 3, wherein in Chemical Formula IIa and Chemical Formula IIb, X1 and X2 are different functional groups.

### Claim 6 (depends on 5)

The alignment film composition of claim 5, wherein in Chemical Formula IIa and Chemical Formula IIb, X1 is an aziridine group.

### Claim 7 (depends on 1)

The alignment film composition of claim 1, wherein the cross-linker comprises 2 wt % to 10 wt % with respect to the total weight of the alignment film composition.

### Claim 8

A method of manufacturing a liquid crystal display device, the method comprising:
providing a substrate;
applying an alignment film composition onto the substrate;
heat-treating the alignment film composition to form an alignment film;
irradiating the heat-treated alignment film with linearly polarized light; and
heat-treating the light-irradiated alignment film,
wherein the alignment film composition comprises:
a copolymer having a structure represented by Chemical Formula Ia or Chemical Formula Ib in a repetitive unit; and
a cross-linker represented by Chemical Formula IIa or Chemical Formula IIb below,
wherein:
and
wherein:
in Chemical Formula Ia and Chemical Formula Ib:
R1 is a tetravalent organic group derived from an alicyclic dianhydride or an aromatic dianhydride;
R2 is a divalent organic group derived from an alicyclic diamine or an aromatic diamine; in Chemical Formula Ib; and
R3 and R4 are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group;
in Chemical Formula IIa and Chemical Formula IIb:
X1 to X4 are each independently any one of a hydroxyl group (—OH), an amino group (—NH2), an epoxy group, an aziridine group, a carbodiimide group, an acrylate group, a methacrylate group, and a vinyl group;
Y1 and Y2 are each independently any one of a single bond, —CO—, —COO—, —OCO—, —S—, —O—, —OOC— —CH2CH2O—, —OCH2CH2—, an aromatic compound of 6 to 30 carbon atoms, and an alicyclic compound of 4 to 20 carbon atoms;
m1 to m4 are each independently an integer of 0 to 6; and
n is an integer of 2 to 18; and
in Chemical Formula IIa:
Z1 and Z2 are each independently any one of
R being H or an alkyl group of 1 to 3 carbon atoms, an aromatic compound of 6 to 30 carbon atoms, and an alicylic compound of 4 to 20 carbon atoms.

### Claim 9 (depends on 8)

The method of claim 8, wherein heat-treating the alignment film composition is performed at a temperature of 100° C. or lower before the irradiating the alignment film with light.

### Claim 10 (depends on 8)

The method of claim 8, wherein the copolymer is cross-linked with at least a part of the cross-linker during heat-treating the alignment film composition.

### Claim 11 (depends on 8)

The method of claim 8, wherein the copolymer is cross-linked with at least a part of the cross-linker during heat-treating the light-irradiated alignment film composition.

### Claim 12 (depends on 8)

The method of claim 8, wherein the heat-treated alignment film composition is irradiated with linearly polarized ultraviolet light having a wavelength of 250 nm to 330 nm, during irradiating the heat-treated alignment film with linearly polarized light.

### Claim 13 (depends on 8)

The method of claim 8, wherein the heat-treated alignment film composition is irradiated with linearly polarized light having an exposure amount of 0.01 J/cm2 to 3.0 J/cm2, during irradiating the heat-treated alignment film with linearly polarized light.

### Claim 14

A liquid crystal display device, comprising:
a substrate; and
an alignment film disposed on the substrate,
wherein the alignment film comprises:
a copolymer having a structure represented by Chemical Formula Ia or Chemical Formula Ib in a repetitive unit; and
a cross-linking combination comprising the copolymer cross-linked with a cross-linker represented by Chemical Formula Ia or Chemical Formula IIb,
wherein:
and
wherein:
in Chemical Formula Ia and Chemical Formula Ib:
R1 is a tetravalent organic group derived from an alicyclic dianhydride or an aromatic dianhydride;
R2 is a divalent organic group derived from an alicyclic diamine or an aromatic diamine; in Chemical Formula Ib; and
R3 and R4 are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group;
in Chemical Formula IIa and Chemical Formula IIb:
X1 to X4 are each independently any one of a hydroxyl group (—OH), an amino group (—NH2), an epoxy group, an aziridine group, a carbodiimide group, an acrylate group, a methacrylate group, and a vinyl group;
Y1 and Y2 are each independently any one of a single bond, —CO—, —COO—, —OCO—, —S—, —O—, —OOC— —CH2CH2O—, —OCH2CH2—, an aromatic compound of 6 to 30 carbon atoms, and an alicyclic compound of 4 to 20 carbon atoms;
m1 to m4 are each independently an integer of 0 to 6; and
n is an integer of 2 to 18; and
in Chemical Formula IIa:
Z1 and Z2 are each independently any one of
R being H or an alkyl group of 1 to 3 carbon atoms, an aromatic compound of 6 to 30 carbon atoms, and an alicylic compound of 4 to 20 carbon atoms.

### Claim 15 (depends on 14)

The liquid crystal display device of claim 14, wherein in Chemical Formula Ia and Chemical Formula Ib, R2 is any one of

### Claim 16 (depends on 14)

The liquid crystal display device of claim 14, wherein the alignment film further comprises a polymer chain having a structure represented by Chemical Formula Id or Chemical Formula Ie in a repetitive unit,
wherein:
and
wherein:
in Chemical Formula Id and Chemical Formula Ie:
R1 is a tetravalent organic group derived from an alicyclic dianhydride or an aromatic dianhydride; and
R2 is a divalent organic group derived from an alicyclic diamine or an aromatic diamine; and
in Chemical Formula Ie:
R3 and R4 are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

### Claim 17 (depends on 14)

The liquid crystal display device of claim 14, wherein in Chemical Formula IIa:
X1 and X4 are identical functional groups; and
X2 and X3 are identical functional groups.

### Claim 18 (depends on 17)

The liquid crystal display device of claim 17, wherein in Chemical Formula IIa and Chemical Formula IIb, X1 and X2 are identical functional groups.

### Claim 19 (depends on 17)

The liquid crystal display device of claim 17, wherein in Chemical Formula IIa and Chemical Formula IIb, X1 and X2 are different functional groups.

### Claim 20 (depends on 19)

The liquid crystal display device of claim 19, wherein in Chemical Formula IIa and Chemical Formula IIb, X1 is an aziridine group.