Light-emitting device, method of preparing the light-emitting device, and method of operating the light-emitting device

Patent metadata

Field	Value
Publication number	US-12384963-B2
Application number	US-202217696372-A
Country	US
Kind code	B2
Filing date	Mar 16, 2022
Priority date	Mar 16, 2021
Publication date	Aug 12, 2025
Grant date	Aug 12, 2025

Abstract

A light-emitting device, including: a carbon-containing film, wherein the carbon-containing film includes at least one carbon atom; and a light-emitting group represented by Formula 1, wherein the light-emitting group is chemically bonded to the at least one carbon atom on a surface of the carbon-containing film:

*—(C≡C)-(A 1 ) m1 -(A 2 ) m2   Formula 1

wherein * indicates a chemical bonding site to the at least one carbon atom on the surface of the carbon-containing film, A 1 is a linking group, A 2 is a group comprising a light-emitting moiety, and m1 and m2 are each independently an integer from 1 to 10.

First claim

What is claimed is:

1. A light-emitting device, comprising:
a carbon-containing film, wherein the carbon-containing film comprises at least one carbon atom; and
a light-emitting group represented by Formula 1,
wherein the light-emitting group is chemically bonded to the at least one carbon atom on a surface of the carbon-containing film:
*—(C≡C)-(A 1 ) m1 -(A 2 ) m2   Formula 1

wherein, in Formula 1,
* indicates a chemical bonding site to the at least one carbon atom on the surface of the carbon-containing film,
A 1 is a linking group,
A 2 is a group comprising a light-emitting moiety, and
m1 and m2 are each independently an integer from 1 to 10,
wherein, when m1 is 2 or greater, two or more A 1 are identical to or different from each other, and when m2 is 2 or greater, two or more A 2 are identical to each other or different from each other.

2. The light-emitting device of claim 1 , wherein
the carbon-containing film is flexible.

3. The light-emitting device of claim 1 , wherein
the carbon-containing film further comprises a carbon-containing material, wherein the carbon-containing material comprises the at least one carbon atom, and
the carbon-containing material is a carbon nanotube, a carbon nanorod, a carbon fiber, a graphene sheet, a carbon nanowire, a carbon-containing particle, a graphite, a glassy carbon, a fullerene, a carbon paste, or a combination thereof.

4. The light-emitting device of claim 3 , wherein the carbon-containing particle is a graphene particle, an active carbon particle, a porous carbon particle, or a combination thereof.

5. The light-emitting device of claim 1 , wherein
the carbon-containing film further comprises nitrogen (N), oxygen (O), silicon (Si), boron (B), or a combination thereof, in addition to the at least one carbon atom.

6. The light-emitting device of claim 1 , wherein
the surface of the carbon-containing film comprises a monolayer comprising a plurality of the groups comprising the light-emitting moiety, and
the monolayer is in direct contact with the surface of the carbon-containing film.

7. The light-emitting device of claim 6 , wherein
a thickness of the monolayer is from about 0.1 nanometers to about 5.0 nanometers.

8. The light-emitting device of claim 7 , wherein
the monolayer is a self-assembled monolayer.

9. The light-emitting device of claim 1 , wherein
A 1 of Formula 1 is a single bond, a substituted or unsubstituted C 2 -C 60 alkylene group, a substituted or unsubstituted C 2 -C 60 alkenylene group, a substituted or unsubstituted C 2 -C 60 alkynylene group, a substituted or unsubstituted C 5 -C 30 carbocyclic group, or a substituted or unsubstituted C 2 -C 30 heterocyclic group.

10. The light-emitting device of claim 1 , wherein
A 2 in Formula 1 is a monovalent group derived from a phosphorescent luminescent compound, a fluorescent luminescent compound, or a quantum dot.

11. The light-emitting device of claim 1 , wherein
A 2 in Formula 1 is a monovalent group derived from a transition metal-containing organometallic compound.

12. The light-emitting device of claim 1 , wherein
A 2 of Formula 1 is a monovalent group derived from a fluorescent luminescent compound,
wherein the fluorescent luminescent compound is a prompt-fluorescence luminescent compound or a delayed-fluorescence luminescent compound.

13. The light-emitting device of claim 1 , further comprising
a conductive film facing the carbon-containing film,
wherein A 2 of Formula 1 is oriented toward the conductive film.

14. The light-emitting device of claim 12 , further comprising
an interlayer located between the carbon-containing film and the conductive film, wherein
the interlayer comprises:
a hole transport material, a light-emitting material, an electron transport material, or a combination thereof; or
an insulating material, an electrolyte, air, or inert gas.

15. The light-emitting device of claim 1 , wherein
electron density of the light-emitting moiety changes based on a voltage change that is applied to the carbon-containing film.

16. The light-emitting device of claim 1 , wherein
a wavelength of light emitted from the light-emitting moiety changes based on a voltage change that is applied to the carbon-containing film.

17. The light-emitting device of claim 1 , wherein
a wavelength of light emitted from the light-emitting moiety continuously changes based on a continuously changing voltage that is applied to the carbon-containing film.

18. A method of manufacturing a light-emitting device, the method comprising:
providing a carbon-containing film, wherein the carbon-containing film comprises at least one carbon atom; and
contacting the carbon-containing film with a compound represented by Formula 1A and chemically bonding a light-emitting group represented by Formula 1 to the at least one carbon atom on a surface of the carbon-containing film:
A 4 -(C≡C)-(A 1 ) m1 -(A 2 ) m2   Formula 1A

*—(C≡C)-(A 1 ) m1 -(A 2 ) m2   Formula 1

wherein, in Formulae 1A and 1,
A 4 is an organic moiety,
* indicates a chemical bonding site to the at least one carbon atom on the surface of the carbon-containing film,
A 1 is a linking group,
A 2 is a group comprising a light-emitting moiety, and
m1 and m2 are each independently an integer from 1 to 10,
wherein, when m1 is 2 or greater, two or more A 1 are identical to or different from each other, and when m2 is 2 or more, two or more A 2 are identical to each other or different from each other.

19. A method of operating a light-emitting device, the method comprising
controlling a voltage applied to the carbon-containing film of the light-emitting device of claim 1 .

20. The method of claim 19 , wherein
the controlling of the voltage applied to the carbon-containing film of the light-emitting device comprises continuously or discontinuously changing the voltage applied to the carbon-containing film of the light-emitting device.

Assignees

• Samsung Electronics Co Ltd
• Korea Advanced Inst Sci & Tech

Inventors

• Jung Yongsik
• Baik Muhyun
• Kim Seoungtae
• Baek Seungyeol
• Jeong Jinhoon
• Kwak Seungyeon
• Kim Joonghyuk
• Choi Hyeonho
• Hwang Kyuyoung

Classifications

• H10K2102/311

  Flexible OLED · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K77/111

  Flexible substrates · CPC title

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title