Coating composition, method for producing organic electroluminescent device using same, and organic electroluminescent device produced thereby

Patent metadata

Field	Value
Publication number	US-11081646-B2
Application number	US-201716328466-A
Country	US
Kind code	B2
Filing date	Nov 7, 2017
Priority date	Nov 7, 2016
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

The present specification relates to a hole injection or transfer layer coating composition of an organic light emitting diode comprising an organic metal complex of a transition metal; a fluorine-based polymer comprising sulfonic acid or sulfonate; and an organic solvent, a method for manufacturing an organic light emitting diode and an organic light emitting diode using the same.

First claim

The invention claimed is:

1. A hole injection or transfer layer coating composition of an organic light emitting diode, the composition comprising:
an organic metal complex of a transition metal;
a polymer comprising a unit of the following Chemical Formula 1; and
an organic solvent:

in Chemical Formula 1,
A is at least one selected from an aromatic hydrocarbon ring, a heteroring or a substituted or unsubstituted alkylene group wherein optionally at least one carbon atom of the alkylene group is replaced by O, S, C(═O), S(═O) or S(═O) 2 ;
X 1 is O or S, X 2 is CR 5 R 6 , O or S, n is an integer of 1 to 10, p is an integer of 1 to 10 and m is an integer of 0 to 10;
Y is SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 Rb or SO 3 Cs; and
R 1 to R 6 are each independently hydrogen, fluorine, an alkyl group or a fluoroalkyl group, and at least one of R 1 and R 2 is fluorine.

2. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein, in the organic metal complex of a transition metal, the transition metal is a transition metal of group 3 to group 11.

3. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein, in the organic metal complex of a transition metal, the transition metal is Mo, W, V, Re, Mn or Rh.

4. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein a content of the organic metal complex of a transition metal in the coating composition is from 0.01% by weight to 50% by weight.

5. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein the polymer comprising the unit of Chemical Formula 1 has a weight average molecular weight of 2,000 or greater.

6. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein, in A of Chemical Formula 1, the alkylene group is further substituted with fluorine.

7. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2:

in Chemical Formulae 1-1 and 1-2, q, r, s and t are each independently an integer of 1 to 500, and the remaining substituents are the same as defined in Chemical Formula 1.

8. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein a content of the polymer is from 0.01% by weight to 50% by weight with respect to the whole coating composition.

9. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein the organic solvent comprises at least one of ether-based, alcohol-based, ketone-based or ester-based solvents.

10. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein the organic solvent comprises a solvent represented by the following Chemical Formula 5:

in Chemical Formula 5,
n is an integer of 1 to 20;
l and m are each or simultaneously an integer of 0 to 5; and
R 1 , R 2 , R 3 and R 4 are each or simultaneously a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 40 atoms, a heteroaryl group having 2 to 40 carbon atoms, or an ester group having 1 to 20 carbon atoms.

11. The hole injection or transfer layer coating composition of an organic light emitting diode of claim 1 , wherein the organic solvent comprises at least one of ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monopentyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol dibutyl ether, ethylene glycol dipentyl ether, ethylene glycol dihexyl ether, 1,2 propanediol, 1,3-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, ethylene glycol diacetate, PEG 600 or triethylene glycol.

12. A method for manufacturing an organic light emitting diode comprising:
preparing a substrate;
forming a first electrode on the substrate;
forming at least one organic material layer on the first electrode;
and forming a second electrode on the organic material layer,
and further comprising forming a hole injection or transfer layer between the first electrode and the organic material layer or between the second electrode and the organic material layer through a coating method using the coating composition of claim 1 .

13. The method for manufacturing an organic light emitting diode of claim 12 , wherein the hole injection or transfer layer formed using the coating composition has a thickness of 1 nm to 1,000 nm.

14. The method for manufacturing an organic light emitting diode of claim 12 , further comprising annealing after the forming of a hole injection or transfer layer using the coating composition.

15. An organic light emitting diode comprising:
a first electrode;
a second electrode; and
at least one organic material layer provided between the first electrode and the second electrode,
and further comprising a hole injection or transfer layer provided between the first electrode and the organic material layer or between the second electrode and the organic material layer, and formed using the coating composition of claim 1 .

16. An organic light emitting diode comprising:
a first electrode;
a second electrode; and
at least one organic material layer provided between the first electrode and the second electrode,
and further comprising a hole injection or transfer layer provided between the first electrode and the organic material layer or between the second electrode and the organic material layer, and comprising a transition metal oxide and a polymer comprising a unit of the following Chemical Formula 1:

in Chemical Formula 1,
A is at least one selected from an aromatic hydrocarbon ring, a heteroring or a substituted or unsubstituted alkylene group wherein optionally at least one carbon atom of the alkylene group is replaced by O, S, C(═O), S(═O) or S(═O) 2 ;
X 1 is O or S, X 2 is CR 5 R 6 , O or S, n is an integer of 1 to 10, p is an integer of 1 to 10 and m is an integer of 0 to 10;
Y is SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 Rb or SO 3 Cs; and
R 1 to R 6 are each independently hydrogen, fluorine, an alkyl group or a fluoroalkyl group, and at least one of R 1 and R 2 is fluorine.

17. The hole injection or transfer layer coating composition of an organic li

Assignees

• Lg Chemical Ltd

Inventors

• Yoon Seokhee
• Lee Jaechol
• Kim Jinseck
• Lee Donggu
• Kim Hwakyung
• Jeong Jae Hak
• Shin Jiyeon
• Kim Daeho

Classifications

• H10P95/90

  Thermal treatments, e.g. annealing or sintering · CPC title

• C08F28/02

  by a bond to sulfur · CPC title

• C08F16/30

  Monomers containing sulfur · CPC title

• C09D141/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur; Coating compositions based on derivatives of such polymers · CPC title

• C09D129/10

  Homopolymers or copolymers of unsaturated ethers (C09D135/08 takes precedence) · CPC title