Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-12052913-B2
Application number	US-201917264462-A
Country	US
Kind code	B2
Filing date	Sep 29, 2019
Priority date	Sep 28, 2018
Publication date	Jul 30, 2024
Grant date	Jul 30, 2024

Abstract

Provided is an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and one or more organic material layers provided between the cathode and the anode, the one or more organic material layers comprising a light emitting layer, an electron transport region and a hole transport region, wherein all of the organic materials, other than a dopant, contained in the one or more organic material layers have a triplet state energy of 2.5 eV or higher, at least three types of the organic materials having a triplet state energy of 2.5 eV or higher have a triplet state energy of 2.7 eV or higher, and at least two types of the organic materials having a triplet state energy of 2.5 eV or higher include a spiro compound.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising:
a cathode;
an anode; and
one or more organic material layers provided between the cathode and the anode and including an organic material,
wherein the one or more organic material layers comprise a light emitting layer, an electron transport region provided between the cathode and the light emitting layer, and a hole transport region provided between the anode and the light emitting layer,
all of the organic materials, except for a dopant, among the organic materials included in the one or more organic material layers, have a triplet energy (T org ) of 2.5 eV or more,
three or more of the organic materials having a triplet energy (T org ) of 2.5 eV or more have a triplet energy (T org ) of 2.7 eV or more, and
two or more of the organic materials having a triplet energy (T org ) of 2.5 eV or more comprise a spiro compound, and
the light emitting layer comprises two or more hosts.

2. The organic electroluminescent device of claim 1 , wherein all of the organic materials, except for a dopant, among the organic materials included in the one or more organic material layers, have a triplet energy (T org ) of 2.6 eV or more.

3. The organic electroluminescent device of claim 1 , wherein three or more of the organic materials having a triplet energy (T org ) of 2.5 eV or more comprise a spiro compound.

4. The organic electroluminescent device of claim 1 , wherein the organic electroluminescent device has a light emitting spectrum (λ max ) of 500 nm to 550 nm.

5. The organic electroluminescent device of claim 1 , wherein the spiro compound is a compound of Formula 1:

wherein in Formula 1:
Ring A to Ring D are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted hetero ring having 5 to 40 carbon atoms;
X1 and X2 are each independently a direct bond, CRR′, NR″, O, or S;
at least one of R, R′, R″, and R1 to R4 is -(L) a -(A) b , and the remaining one(s) are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl 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 heterocyclic group, or adjacent groups are optionally bonded to each other to form a substituted or unsubstituted ring;
R1 to R4 are optionally each independently bonded to any one of adjacent Ring A to Ring D to form a substituted or unsubstituted ring;
R and R′ are optionally bonded to each other to form a substituted or unsubstituted spiro ring;
L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted monocyclic heteroarylene group comprising N;
A is a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
a and b are each an integer from 1 to 2;
m, n, o, and w are each independently an integer from 0 to 4;
when a and b are each 2, the substituents in the parenthesis are the same as or different from each other, and
when m, n, o, and w are each 2 or more, the substituents in the parenthesis are the same as or different from each other.

6. The organic electroluminescent device of claim 1 , wherein the spiro compound is any one of the following Formulae 2 to 9:

wherein in Formulae 2 to 9:
X1 is CRR′, NR″, O, or S;
at least one of R, R′, R″, and R1 to R6 is -(L) a -(A) b , and the remaining ones are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl 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 heterocyclic group;
L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted monocyclic heteroarylene group comprising N;
A is a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
a and b are each an integer from 1 to 2;
m, n, o, w, u, and i are each independently an integer from 0 to 4; and
p is an integer from 0 to 3,
when a and b are each 2, the substituents in the parenthesis are the same as or different from each other, and
when m, n, o, p, w, u, and i are each 2 or more, the substituents in the parenthesis are the same as or different from each other.

7. The organic electroluminescent device of claim 5 , wherein three or more of the spiro compounds are included in the light emitting layer, between the anode and the light emitting layer, or between the cathode and the light emitting layer.

8. The organic electroluminescent device of claim 1 , wherein at least one selected from the group consisting of a hole injection layer, a hole transport layer, and a hole adjusting layer is provided in the hole transport region.

9. The organic electroluminescent device of claim 8 , wherein the hole adjusting layer is formed of a single layer or multiple layers having two or more layers.

10. The organic electroluminescent device of claim 1 , wherein at least one selected from the group consisting of an electron injection layer, an electron transport layer, and an electron adjusting layer is provided in the electron transport region.

11. The organic electroluminescent device of claim 5 , wherein the compound of Formula 1 is present between the cathode and the light emitting layer.

12. The organic electroluminescent device of claim 5 , wherein the compound of Formula 1 is present between the anode and the light emitting layer.

13. An organic electroluminescent device comprising:
a cathode;
an anode; and
one or more organic material layers provided between the c

Assignees

• Lg Chemical Ltd

Inventors

• Ha Jae Seung
• Kim Seong So
• Chun Minseung
• Suh Sang Duk
• Jung Min Woo
• Jang Boon Jae
• Cha Yongbum
• Heo Dong Uk
• Lee Jungha

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K85/624 Primary

  containing six or more rings · CPC title

• H10K85/631 Primary

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title