Organic light emitting diode

Patent metadata

Field	Value
Publication number	US-9502669-B2
Application number	US-201514912537-A
Country	US
Kind code	B2
Filing date	Jul 16, 2015
Priority date	Aug 12, 2014
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

The present specification relates to an organic light emitting diode.

First claim

The invention claimed is:

1. An organic light emitting diode comprising:
a cathode;
an anode provided to face the cathode;
a light emitting layer provided between the cathode and the anode;
an electron transporting layer provided between the cathode and the light emitting layer; and
an electron adjusting layer provided between the light emitting layer and the electron transporting layer,
wherein the electron transporting layer comprises an organic compound containing an aromatic hetero ring,
the electron adjusting layer comprises a heterocyclic compound represented by the following Formula 1, and
an ionization potential (Ip m ) of the electron transporting layer is larger than an ionization potential (IP a ) of the electron adjusting layer:

in Formula 1,
X1 is CR1 or N and X2 is CR2 or N,
Y1 is CR5 or N, Y2 is CR6 or N, Y3 is CR7 or N, and Y4 is CR8 or N,
Z1 is CR9 or N, Z2 is CR10 or N, Z3 is CR11 or N, and Z4 is CR12 or N,
X1, X2, Y1 to Y4, and Z1 to Z4 are not simultaneously N, and
R1, R2, and R5 to R12 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or adjacent substituents of R1, R2, and R5 to R12 combine with each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted hetero ring.

2. The organic light emitting diode of claim 1 , wherein the electron adjusting layer is provided to be in contact with the light emitting layer.

3. The organic light emitting diode of claim 1 , wherein a thickness of the electron transporting layer is larger than a thickness of the electron adjusting layer.

4. The organic light emitting diode of claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by the following Formula 1A or 1B:

in Formulae 1A and 1B,
Y1 to Y4, Z1 to Z4, and R2 are the same as those defined in Formula 1,
X3 to X6 are the same as or different from each other, and are each independently CR3 or N, and
R3's are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted hetero ring.

5. The organic light emitting diode of claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulae 1-1 to 1-4:

in Formulae 1-1 to 1-4,
a, b, and c are each an integer of 1 to 4,
d and e are each an integer of 1 to 6, and
when a, b, c, d, and e are each an integer of 2 or more, the two or more structures in the parenthesis are the same as or different from each other, and
A1 to A5 and R2 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted phosphine oxide group.

6. The organic light emitting diode of claim 1 , wherein at least one of R1, R2, and R5 to R12 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; or a phosphine oxide group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents combine with each other to form a hydrocarbon ring which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.

7. The organic light emitting diode of claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulae 1-1-1 to 1-1-7, 1-2-1 to 1-2-10, 1-3-1 to 1-3-5, and 1-4-1 to 1-4-7:

8. The organic light emitting diode of claim 1 , wherein the electron transporting layer comprises an organic compound containing an aromatic hetero ring represented by the following Formula 2:

in Formula 2,
X5 and X6 are the same as or different from each other, and are each independently N or CH, and
Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

9. The organic light emitting diode of claim 8 , wherein Ar1 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted fluorenyl group.

10. The organic light emitting diode of claim 8 , wherein at least one of Ar1 to Ar3 is represented by the following Formula 3:

in Formula 3,
o, p, and q are 0 or 1,
1≦o+p+q≦3,
r is 1 or 2, and
when r is 2, two Ar's are the same as or different from each other,
L1 to L3 are the same as or different from each other, and are each independently a phenylene group; or a naphthalene group; or a fluorenylene group, and
Ar is an aryl group which is unsubstituted or substituted with one or two or substituents selected from the group consisting of an aryl group and a heterocyclic group; or a heterocyclic group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

11. The organic light emitting diode of claim 8 , wherein the organic compound containing the aromatic hetero ring represented by Formula 2 is represented by any one of the following Formulae 2-1 to 2-13:

Assignees

• Lg Chemical Ltd

Inventors

• Huh Jungoh
• Lee Dong Hoon
• Chun Minseung
• Jang Boonjae
• JUNG Wonik

Classifications

• H01L2251/558

  Electricity · mapped topic

• C09K2211/1011

  Condensed systems · CPC title

• H01L51/0054

  Electricity · mapped topic

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title