Compound and organic light emitting device comprising same

Patent metadata

Field	Value
Publication number	US-12137609-B2
Application number	US-202017292621-A
Country	US
Kind code	B2
Filing date	Jul 17, 2020
Priority date	Aug 2, 2019
Publication date	Nov 5, 2024
Grant date	Nov 5, 2024

Abstract

A compound represented by Chemical Formula 1 and an organic light emitting device comprising the same, the compound used as a material of an organic material layer of the organic light emitting device and providing improved efficiency, low driving voltage and improved lifetime characteristics.

First claim

The invention claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
A is a benzene ring fused with two adjacent pentagonal rings,
at least one of Ar 1 , Ar 2 and Ar 3 is a biphenylyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a 9,9-dimethylfluorenyl group; a 9,9-diphenylfluorenyl group; a carbazol-9-yl group; a 9-methyl-carbazolyl group; or a 9-phenyl-carbazolyl group, and the rest are a phenyl group, and Ar 2 and Ar 3 are not a biphenylyl group at the same time,
at least one of Ar 1 , Ar 2 and Ar 3 is substituted with one or more deuterium, and the rest are unsubstituted,
R is hydrogen; deuterium; halogen; cyano; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 1-60 alkoxy group; a substituted or unsubstituted C 2-60 alkenyl group; a substituted or unsubstituted C 2-60 alkynyl group; a substituted or unsubstituted C 3-60 cycloalkyl group; a substituted or unsubstituted C 6-60 aryl group; a substituted or unsubstituted C 2-60 heteroaryl group containing any one or more heteroatoms selected from the group consisting of N, O, and S; a substituted or unsubstituted tri (C 1-60 alkyl) silyl group; or a substituted or unsubstituted tri (C 6-60 aryl) silyl group, and
n is an integer of 0 to 10.

2. The compound of claim 1 , wherein the compound is represented by any one of the following Chemical Formulas 1-1 to 1-6:

wherein, in Chemical Formulas 1-1 to 1-6, Ar 1 , Ar 2 , Ar 3 , R and n are the same as defined in claim 1 .

3. The compound of claim 1 , wherein Ar 1 , Ar 2 or Ar 3 is any one selected from the group consisting of the following Chemical Formulas 2-1 to 2-4:

wherein, in Chemical Formulas 2-1 to 2-4,
X is O; S; —NR 1 ; or —CR 2 R 3 ,
R 1 , R 2 and R 3 are each independently a methyl group; or a phenyl group,
one of Y 1 , Y 2 , Y 3 and Y 4 is a single bond linked to a carbon atom in the triazinyl group or a nitrogen atom in the indolocarbazole group, and the rest are deuterium,
all Z 1 are hydrogen or all Z 1 are deuterium, all Z 2 are hydrogen or all Z 2 are deuterium, and all Z 1 and all Z 2 are not simultaneously hydrogen.

4. The compound of claim 1 , wherein Ar 1 , Ar 2 or Ar 3 is any one selected from the group consisting of the following formulas:

5. The compound of claim 1 , wherein one of Ar 1 , Ar 2 and Ar 3 is a biphenylyl group, and the rest are a phenyl group, and
at least one of Ar 1 , Ar 2 and Ar 3 is substituted with one or more deuterium, and the rest are unsubstituted.

6. The compound of claim 1 , wherein one of Ar 1 , Ar 2 and Ar 3 is represented by Chemical Formula 2-3, and the rest are an unsubstituted phenyl group:

wherein, in Chemical Formula 2-3,
all Z 1 are deuterium and all Z 2 are hydrogen.

7. The compound of claim 1 , wherein one of Ar 1 , Ar 2 and Ar 3 is an unsubstituted biphenylyl group, the rest are a phenyl group, and at least one of the rest is represented by Chemical Formula 2-4.

8. The compound of claim 1 , wherein Ar 1 has a biphenylyl group,
one of Ar 2 and Ar 3 is a biphenylyl group, and the other is a phenyl group, and
at least one of Ar 1 , Ar 2 and Ar 3 is substituted with one or more deuterium, and the rest are unsubstituted.

9. The compound of claim 1 , wherein Ar 1 , Ar 2 and Ar 3 is an unsubstituted dibenzofuranyl group; an unsubstituted dibenzothiophenyl group; an unsubstituted 9,9-dimethylfluorenyl group; an unsubstituted carbazol-9-yl group; or an unsubstituted 9-phenyl-carbazolyl group, and the rest are a phenyl group, and at least one of the rest is substituted with deuterium.

10. The compound of claim 1 , wherein one of Ar 1 , Ar 2 and Ar 3 is a dibenzofuranyl group substituted with deuterium; a dibenzothiophenyl group substituted with deuterium; or a 9,9-dimethylfluorenyl group substituted with deuterium, and the rest are an unsubstituted phenyl group.

11. The compound of claim 1 , wherein all R are hydrogen, or all R are deuterium.

12. The compound of claim 1 , wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of the following compounds:

Assignees

• Lg Chemical Ltd

Inventors

• Suh Sang Duk
• Lee Dong Hoon
• Jang Boon Jae
• Jung Min Woo
• Lee Jungha
• Han Su Jin
• Park Seulchan
• Hwang Sunghyun

Classifications

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title