Heterocyclic compound and organic light emitting device comprising same

Patent metadata

Field	Value
Publication number	US-12133459-B2
Application number	US-202017282678-A
Country	US
Kind code	B2
Filing date	Jan 13, 2020
Priority date	Jan 15, 2019
Publication date	Oct 29, 2024
Grant date	Oct 29, 2024

Abstract

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

First claim

The invention claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
two adjacent carbons of C 1 to C 4 are respectively connected to 1 and 2 of Chemical Formula 2, where C 1 and C 2 are not connected to 2 and 1 of Chemical Formula 2 respectively, and C 4 and C 3 are not connected to 1 and 2 of Chemical Formula 2 respectively,
L 1 is a direct bond; or a substituted or unsubstituted C 6-60 arylene,
R 1 is hydrogen; deuterium; a substituted or unsubstituted C 1-60 alkyl; or a substituted or unsubstituted C 6-60 aryl, or is fused with an adjacent ring to form a benzene ring,
R 2 to R 4 are each independently hydrogen; deuterium; a substituted or unsubstituted C 1-60 alkyl; a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
n is an integer of 0 to 8,
m and 0 are each independently an integer of 0 to 3,
1 is an integer of 0 to 4,
X 1 is NR′ and X 2 is O or S; or X 1 is O or S and X 2 is NR′,
R′ is

L 2 is a direct bond; or a substituted or unsubstituted C 6-60 arylene,
Y 1 , Y 2 and Y 3 are each independently CH or N, and at least two of Y 1 , Y 2 and Y 3 are N, and
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S.

2. The compound of claim 1 ,
wherein the compound is any one selected from the group consisting of compounds represented by Chemical Formulas 3 to 6:

wherein, in Chemical Formulas 3 to 6,
X 1 , X 2 , L 1 , R 1 , R 2 , R 3 , R 4 , n, m, o and 1 are the same as defined in claim 1 .

3. The compound of claim 1
wherein L 1 and L 2 are each independently a direct bond; phenylene unsubstituted or substituted with deuterium; or naphthylene unsubstituted or substituted with deuterium.

4. The compound of claim 1 ,
wherein R 1 is hydrogen; deuterium; methyl; ethyl; propyl; phenyl unsubstituted or substituted with deuterium; biphenylyl unsubstituted or substituted with deuterium; or is fused with an adjacent ring to form a benzene ring.

5. The compound of claim 1 ,
wherein R 2 to R 4 are each independently hydrogen; deuterium; methyl; ethyl; propyl; phenyl unsubstituted or substituted with deuterium; or biphenylyl unsubstituted or substituted with deuterium.

6. The compound of claim 1 ,
wherein Ar 1 and Ar 2 are each independently phenyl substituted or unsubstituted with deuterium; biphenylyl unsubstituted or substituted with deuterium; dibenzofuranyl unsubstituted or substituted with deuterium; or dibenzothiophenyl unsubstituted or substituted with deuterium.

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

8. An organic light emitting device comprising: a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers that are provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers include the compound according to claim 1 .

9. The organic light emitting device of claim 8 ,
wherein the organic material layer including the compound is a light emitting layer.

10. The organic light emitting device of claim 9 ,
wherein the light emitting layer further includes a compound represented by Chemical Formula 7:

wherein, in Chemical Formula 7,
Ar 3 and Ar 4 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl comprising any one or more heteroatoms selected from the group consisting of N, O and S,
R 4 and R 5 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted C 1-60 alkyl; a substituted or unsubstituted C 3-60 cycloalkyl; or a substituted or unsubstituted C 2-60 alkenyl; a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S, and
a and b are each independently an integer of 0 to 7.

11. The organic light emitting device of claim 10 ,
wherein Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphth

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

• H10K85/6574

  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

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title