# US 12,225,809 B2 · Coating composition including functionalized graphene oxide, method for forming stacked structure using the same and method for manufacturing display device using the same

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- Number: US 12,225,809 B2
- Document ID: US12225809B2
- Status: Granted
- Kind: B2
- Application number: 17/029,855
- Filed: 2020-09-23
- Published: 2021-04-08
- Granted: 2025-02-11
- Earliest claimed: 2019-10-07
- Assignees: Samsung Display Co., Ltd.; Dongjin Semichem Co., Ltd.
- Applicants: Samsung Display Co., LTD.; Dongjin Semichem Co., Ltd.
- Inventors: Hee Kyun Shin; Dong Kyun Seo; Jun Ho Sim; Woo Jin Cho; Byung Hoon Kang; Seung Jun Moon; Sun Chan Park; Hee Won Seo; Ji Eun Cho; Kyu Soon Shin
- Web page: https://patentgrep.com/patent/US12225809B2

## CPC

- H10K 85/20: Carbon compounds, e.g. carbon nanotubes or fullerenes
- C09D 1/00: Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
- C09D 7/63: organic
- H10K 59/8731: {multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers}
- H10K 71/00: Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K 71/80: using temporary substrates
- H10K 77/111: {Flexible substrates}
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- B82Y 40/00: Manufacture or treatment of nanostructures
- H10K 59/12: Active-matrix OLED [AMOLED] displays
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present disclosure is directed to a coating composition including a graphene oxide and a solvent. At least one of a carboxyl group and an epoxide group of the graphene oxide is functionalized by an amine. The amine has an activation energy to an epoxide group of the graphene oxide of about −3 kcal/mol to about 8 kcal/mol. A method of forming a stacked structure using the coating composition is provided. A method of manufacturing a display device using the coating composition is provided.

## Claims

### Claim 1

A coating composition comprising:
a graphene oxide;
a water-soluble polymer; and
a solvent, wherein
the water-soluble polymer includes at least one selected from the group consisting of PSS (poly(styrene sulfonate)), PEI (polyetherimide), PDDA (poly(diallyldimethylammonium chloride)), PMA (poly(methacrylic acid)), PVS (poly(vinyl sulfate)), poly(amic acid), and PAH (poly(allylamine hydrochloride)),
a weight ratio of the water-soluble polymer to the graphene oxide is 0.01 to 1,
at least one of a carboxyl group and an epoxide group of the graphene oxide is functionalized by an amine,
the amine has an activation energy to an epoxide group of the graphene oxide of −3 kcal/mol to 8 kcal/mol,
a zeta potential of the coating composition is +30 mV to +60 mV, and
a solution conductivity of the coating composition is 0.001 mS/cm to 0.05 mS/cm.

### Claim 2 (depends on 1)

The coating composition of claim 1, wherein the coating composition has a graphene oxide content of 0.00001 wt % to 4 wt %.

### Claim 3 (depends on 1)

The coating composition of claim 1, wherein the amine is represented by Formula 1:
wherein in Formula 1,
R1 is a straight or branched alkylene group of 3 to 10 carbon atoms, an aromatic ring group, an aliphatic ring group, or a combination thereof, and
R2 and R3 are independently hydrogen or a methyl group.

### Claim 4 (depends on 3)

The coating composition of claim 3, wherein the amine includes at least one selected from the group consisting of N,N-dimethyl-p-phenylene diamine, p-phenylene diamine, 3-dimethylamino-1-propyl amine, and 2,2-(1,2-phenylene)bis(1H-benzo[d]imidazol-5-amine).

### Claim 5 (depends on 1)

The coating composition of claim 1, wherein the graphene oxide has a thickness of 0.5 nm to 2 nm.

### Claim 6 (depends on 1)

The coating composition of claim 1, wherein the solvent includes at least one selected from the group consisting of heptane, hexane, ethanol, methanol, butanol, propanol, methylene chloride, trichloroethylene, ethyl acetate, acetone, methylethylketone, diethylamine, di-isopropylamine, isopropylamine, and water.

### Claim 7 (depends on 1)

A method for forming a stacked structure, the method comprising:
A forming a first coating layer by providing the coating composition of claim 1, wherein the graphene oxide is positively electric-charged, on a substrate; and
forming a second coating layer by providing a second coating composition including a negatively electric-charged graphene oxide on the substrate, the second coating layer being interlayer-bonded to the first coating layer by electrostatic force.

### Claim 8 (depends on 7)

The method of claim 7, wherein the amine includes at least one selected from the group consisting of N,N-dimethyl-p-phenylene diamine, p-phenylene diamine, 3-dimethylamino-1-propyl amine, and 2,2-(1,2-phenylene)bis(1H-benzo[d]imidazol-5-amine).

### Claim 9 (depends on 7)

The method of claim 7, wherein the positively electric-charged graphene oxide has a thickness of about 0.5 nm to about 2 nm.

### Claim 10 (depends on 7)

The method of claim 7, wherein:
a zeta potential of the second coating composition is about −30 mV to about −60 mV, and
a solution conductivity of the second coating composition is about 0.001 mS/cm to about 0.05 mS/cm.

### Claim 11 (depends on 10)

The method of claim 10, wherein the negatively electric-charged graphene oxide has a thickness of about 0.5 nm to about 1 nm.

### Claim 12 (depends on 7)

The method of claim 7, wherein the negatively electric-charged graphene oxide has an oxygen content of about 35 wt % to about 48 wt %.

### Claim 13 (depends on 1)

A method for manufacturing a display device, the method comprising:
forming a first graphene oxide layer by providing the coating composition of claim 1, wherein the graphene oxide is positively electric-charged, on a carrier substrate;
forming a second graphene oxide layer by providing a second coating composition including a negatively electric-charged graphene oxide on the carrier substrate, the graphene oxide layer being interlayer-bonded to the first graphene oxide layer by electrostatic force;
forming a flexible substrate on a barrier adhesion layer including the first graphene oxide layer and the second graphene oxide layer;
forming a display element part on the flexible substrate;
forming a protective film on the display element part; and
separating the flexible substrate from the carrier substrate.

### Claim 14 (depends on 13)

The method of claim 13, wherein the flexible substrate includes at least one selected from the group consisting of polyester, polyvinyl, polycarbonate, polyethylene, polypropylene, polyacetate, polyimide, polyethersulphone, polyacrylate, polyethylenenaphthelate, and polyethyleneterephehalate.

### Claim 15 (depends on 13)

The method of claim 13, wherein the amine includes at least one selected from the group consisting of N,N-dimethyl-p-phenylene diamine, p-phenylene diamine, 3-dimethylamino-1-propyl amine, and 2,2-(1,2-phenylene)bis(1H-benzo[d]imidazol-5-amine).

### Claim 16 (depends on 13)

The method of claim 13, wherein the positively electric-charged graphene oxide has a thickness of about 0.5 nm to about 2 nm.

### Claim 17 (depends on 13)

The method of claim 13, wherein the negatively electric-charged graphene oxide has an oxygen content of about 35 wt % to about 48 wt %.