Heterocyclic compound and organic light emitting diode containing same

Patent metadata

Field	Value
Publication number	US-10873035-B2
Application number	US-201715761657-A
Country	US
Kind code	B2
Filing date	Feb 23, 2017
Priority date	Feb 23, 2016
Publication date	Dec 22, 2020
Grant date	Dec 22, 2020

Abstract

The present specification relates to a hetero-cyclic compound and an organic light emitting device including the same.

First claim

The invention claimed is:

1. A hetero-cyclic compound represented by the following Chemical Formula 1:

in Chemical Formula 1,
R1 to R3 and R5 are the same as or different from each other, and are each independently hydrogen; deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
R4 is hydrogen; deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; an unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, wherein the arylene group in L1 is not an anthracenylene group,
Ar1 is a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, wherein the aryl group in Ar1 is not an anthracenyl group,
r1 and r2 are each an integer from 1 to 5,
r3 is an integer from 1 to 4,
r4 is 1 or 2,
r5 is an integer from 1 to 3, and
when r1 to r5 are each present in a plural number, a plurality of structures in the parenthesis is the same as or different from each other.

2. The hetero-cyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following Chemical Formulae 2 to 5:

in Chemical Formulae 2 to 5,
the definitions of R1 to R5, r1 to r5, L1, and Ar1 are the same as those in Chemical Formula 1.

3. The hetero-cyclic compound of claim 1 , wherein L1 is a direct bond; an unsubstituted arylene group; or an unsubstituted heteroarylene group.

4. The hetero-cyclic compound of claim 1 , wherein Ar1 is an arylamine group which is unsubstituted or substituted with an alkyl group or a heteroaryl group; an N-arylheteroarylamine group which is unsubstituted or substituted with an aryl group; a phosphine oxide group which is substituted with an aryl group; an aryl group which is unsubstituted or substituted with an alkyl group or an aryl group; or a heteroaryl group which is unsubstituted or substituted with an aryl group.

5. An organic light emitting device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein the one or more layers of the organic material layer comprise the hetero-cyclic compound of claim 1 .

6. The organic light emitting device of claim 5 , wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the hetero-cyclic compound.

7. The organic light emitting device of claim 5 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the hetero-cyclic compound.

8. The organic light emitting device of claim 5 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the hetero-cyclic compound as a host of the light emitting layer.

9. The organic light emitting device of claim 5 , wherein the organic material layer comprises an electron transporting layer, and the electron transporting layer comprises the hetero-cyclic compound.

10. An organic light emitting device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein the organic material layer comprises at least one of a hole transporting layer, an electron blocking layer, or an electron transporting layer, and the at least one of the hole transporting layer the electron blocking layer, or the electron transporting layer comprises a hetero-cyclic compound represented by the following Chemical Formula 1:

in Chemical Formula 1,
R1 to R5 are the same as or different from each other, and are each independently hydrogen;
deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar1 is a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
r1 and r2 are each an integer from 1 to 5,
r3 is an integer from 1 to 4,
r4 is 1 or 2,
r5 is an integer from 1 to 3, and
when r1 to r5 are each present in a plural number, a plurality of structures in the parenthesis is the same as or different from each other.

11. A hetero-cyclic compound selected from the following compounds:

Assignees

• Lg Chemical Ltd

Inventors

• Cha Yongbum
• Cho Seongmi
• Kim Jungbum
• Hong Sung Kil
• Kwak Jiwon

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K85/6574

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

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C07D407/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title