Organic light emitting device, crosslinking agent compound for organic light emitting device and manufacturing method of the organic light emitting device

Patent metadata

Field	Value
Publication number	US-11780790-B2
Application number	US-202117248436-A
Country	US
Kind code	B2
Filing date	Jan 25, 2021
Priority date	May 6, 2020
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

An organic light emitting device of an embodiment of the present disclosure includes a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode, stacked one by one, wherein the hole transport region includes a hole transport material derived from a crosslinking agent compound represented by Formula 1. The organic light emitting device may be manufactured through a wet process, and the emission efficiency and driving voltage properties of the organic light emitting device may be improved.

First claim

What is claimed is:

1. An organic light emitting device, comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the hole transport region is derived from a hole transport material comprising a crosslinking agent compound represented by Formula 1:

and
wherein in Formula 1, A is a hydrogen atom or a deuterium atom,
L 1 and L 2 are each independently a direct linkage or a substituted or unsubstituted methylene group,
“m” is an integer of 1 to 100, and
“n 1 ” and “n 2 ” are each independently 1 or 2.

2. The organic light emitting device of claim 1 , wherein the hole transport region comprises:
a hole injection layer on the first electrode; and
a hole transport layer on the hole injection layer, and
wherein the hole transport layer is derived from the hole transport material comprising the crosslinking agent compound represented by Formula 1.

3. The organic light emitting device of claim 1 , wherein the hole transport region comprises a plurality of organic layers, and
wherein an organic layer adjacent to the emission layer among the plurality of organic layers is derived from the hole transport material comprising the crosslinking agent compound represented by Formula 1.

4. The organic light emitting device of claim 1 , wherein the crosslinking agent compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2:

and
wherein in Formula 1-1 and Formula 1-2, A is the same as defined in Formula 1.

5. The organic light emitting device of claim 1 , wherein the hole transport material further comprises a polymer compound comprising a substituted or unsubstituted triarylamine group.

6. The organic light emitting device of claim 5 , wherein the polymer compound is represented by Formula 2-1 or Formula 2-2:

and
wherein in Formula 2-1 and Formula 2-2,
R 1 to R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
“a 1 ” is an integer of 0 to 5,
“a 2 ” and “a 3 ” are each independently an integer of 0 to 4,
“a 4 ” and “a 5 ” are each independently an integer of 0 to 3, and
“p 1 ” and “p 2 ” are each independently an integer of 1 to 100.

7. The organic light emitting device of claim 6 , wherein the polymer compound is represented by any one selected from Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1:

and
wherein in Formula 2-1-1, Formula 2-1-2 and Formula 2-2-1,
“p 1 ” and “p 2 ” are the same as defined in Formula 2-1 and Formula 2-2.

8. The organic light emitting device of claim 5 , wherein a weight ratio of the polymer compound and the crosslinking agent compound comprised in the hole transport material is about 4:1 to about 19:1.

9. The organic light emitting device of claim 5 , wherein, in the hole transport region, the polymer compound is thermally-crosslinked or photo-crosslinked with the crosslinking agent compound.

10. A crosslinking agent compound represented by Formula 1:

wherein in Formula 1,
A is a hydrogen atom or a deuterium atom,
“m” is an integer of 1 to 100,
L 1 and L 2 are each independently a direct linkage or a substituted or unsubstituted methylene group, and
“n 1 ” and “n 2 ” are each independently 1 or 2.

11. The crosslinking agent compound of claim 10 , wherein the crosslinking agent compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2:

and
wherein in Formula 1-1 and Formula 1-2, A is the same as defined in Formula 1.

12. A method of manufacturing an organic light emitting device, the method comprising:
preparing a first electrode;
supplying a hole transport material on the first electrode to form a hole transport region;
forming an emission layer on the hole transport region; and
forming a second electrode on the emission layer,
wherein the hole transport material comprises a crosslinking agent compound represented by Formula 1:

and
wherein in Formula 1,
A is a hydrogen atom or a deuterium atom,
“m” is an integer of 1 to 100,
L 1 and L 2 are each independently a direct linkage, or a substituted or unsubstituted methylene group, and
“n 1 ” and “n 2 ” are each independently 1 or 2.

13. The method of manufacturing an organic light emitting device of claim 12 , wherein the hole transport region comprises:
a hole injection layer formed on the first electrode; and
a hole transport layer formed on the hole injection layer, and
wherein the hole transport layer is formed utilizing the hole transport material.

14. The method of manufacturing an organic light emitting device of claim 12 , wherein the crosslinking agent compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2:

and
wherein in Formula 1-1 and Formula 1-2, A is the same as defined in Formula 1.

15. The method of manufacturing an organic light emitting device of claim 12 , wherein the hole transport material further comprises a polymer compound comprising a substituted or unsubstituted triarylamine group.

16. The method of manufacturing an organic light emitting device of claim 15 , wherein the polymer compound is represented by Formula 2-1 or Formula 2-2:

and
wherein in Formula 2-1 and Formula 2-2,
R 1 to R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
“a 1 ” is an integer of 0 to 5,
“a 2 ” and “a 3 ” are each independently an integer of 0 to 4,
“a 4 ” and “a 5 ” are each independently an integer of 0 to 3, and
“p 1 ” and “p 2 ” are each independently an integer of 1 to 100.

17. The method of manufacturing an organic light emitting device of claim 15 , wherein a weight ratio of the polymer compound and the crosslinking agent compound, comprised in the hole transport material is about 4:1 to about 19:1.

18. The method of manufacturing an organic light emitting device of claim 15 , further comprising preparing the hole transport material by mixing the polymer compound, the crosslinking agent compound

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junwoo

Classifications

• C07C11/21 Primary

  Alkatrienes; Alkatetraenes; Other alkapolyenes · CPC title

• C07C15/28 Primary

  Anthracenes · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/141

  comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE · CPC title

• H10K85/111

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title