IP Library Granted Patent US 12,225,809
Granted Patent B2
US 12,225,809 · App. 17/029,855 · Granted Feb 11, 2025

Coating composition including functionalized graphene oxide, method for forming stacked structure using the same and method for manufacturing display device using the same

Inventors: Hee Kyun Shin (Incheon, KR); Dong Kyun Seo (Seoul, KR); Jun Ho Sim (Hwaseong-si, KR); Woo Jin Cho (Yongin-si, KR); Byung Hoon Kang (Hwaseong-si, KR); Seung Jun Moon (Cheonan-si, KR); Sun Chan Park (Hwaseong-si, KR); Hee Won Seo (Hwaseong-si, KR); Ji Eun Cho (Hwaseong-si, KR); Kyu Soon Shin (Hwaseong-si, KR)
Assignees: SAMSUNG DISPLAY CO., LTD.; DONGJIN SEMICHEM CO., LTD.
H10K71/80C09D1/00C09D7/63H10K50/8445H10K71/00H10K77/111B82Y30/00B82Y40/00H10K50/844
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,225,809
App. No.
17/029,855
Granted
Feb 11, 2025
Kind
B2
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 (39)

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.

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

3. 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.

4. 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).

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

6. 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.

7. 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.

8. 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).

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

10. 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.

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

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

13. 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.

14. 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.

15. 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).

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

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2020
From: SHIN, HEE KYUN; SEO, DONG KYUN; SIM, JUN HO; CHO, WOO JIN; KANG, BYUNG HOON; MOON, SEUNG JUN; PARK, SUN CHAN; SEO, HEE WON; CHO, JI EUN; SHIN, KYU SOON
To: SAMSUNG DISPLAY CO., LTD.; DONGJIN SEMICHEM CO., LTD.
Reel/Frame 053862/0668 →
Priority Claims (1)
KR 10-2019-0123941 · Oct 7, 2019 · national
Continuity (1)
Related Publication 20210104672A1 · Apr 8, 2021
References Cited (24)
US 10029215B2 · Park et al. · 2018 [cited by applicant]
US 20110315204A1 · Gleason et al. · 2011 [cited by applicant]
US 20150021631A1 · Huh et al. · 2015 [cited by applicant]
US 20170015483A1 · Park et al. · 2017 [cited by applicant]
CN 106061593 · 2016 [cited by applicant]
CN 106102883 · 2016 [cited by applicant]
KR 1020110115539 · 2011 [cited by applicant]
KR 1020120105380 · 2012 [cited by applicant]
KR 1020130125668 · 2013 [cited by applicant]
KR 1020130134446 · 2013 [cited by applicant]
KR 1020140023730 · 2014 [cited by applicant]
KR 1020150009289 · 2015 [cited by applicant]
KR 1020150029045 · 2015 [cited by applicant]
KR 1020150105236 · 2015 [cited by applicant]
KR 1020180000781 · 2018 [cited by applicant]
WO 2014027833 · 2014 [cited by applicant]
WO WO2018187588A1 · 2018 [cited by examiner]
Ma et al. “Functionalization and Reduction of Graphene Oxide with p-Phenylene Diamine for Electrically Conductive and Thermally Stable Polystyrene Composites”, 2012. ACS Applied Materials & Interfaces, p. 1948-1953. (Ye… [cited by examiner]
Yong et al. English translation of KR 2013/0125668 A. (Year: 2013). [cited by examiner]
Saini et al. “Spectroscopic and electronic properties of polyallylamine functionalized graphene oxide films”, 2018. Vacuum, p. 110-114. (Year: 2018). [cited by examiner]
Liu et al. “Reduced Graphene Oxide-Based Double Network Polymeric Hydrogels for Pressure and Temperature Sensing”. Sensors 2018, 18, 3162. (Year: 2018). [cited by examiner]
Satti et al. “Improvement of mechanical properties of graphene oxide/poly(allylamine) composites by chemical crosslinking”. Carbon 48 (2010) p. 3376-3381. (Year: 2010). [cited by examiner]
Stankovich et al. “Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide”. Carbon 45 (2007) p. 1558-1565. (Year: 2007). [cited by examiner]
Korean Office Action with English translation for Korean Patent Application No. 10-2019-0123941, dated Apr. 29, 2024. [cited by applicant]