Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-11594687-B2
Application number	US-201615763910-A
Country	US
Kind code	B2
Filing date	Sep 27, 2016
Priority date	Sep 28, 2015
Publication date	Feb 28, 2023
Grant date	Feb 28, 2023

Abstract

The present invention relates to an organic electroluminescent device comprising an anode, a cathode, an emission layer, an undoped electron transport layer comprising a first matrix compound, and an electron injection layer comprising a second matrix compound and an alkali organic complex and/or alkali halide, wherein the undoped electron transport layer and the electron injection layer are arranged between the emission layer and the cathode, wherein the reduction potential of the first matrix compound is less negative than, the reduction potential of 9,10-di(naphthalen-2-yl)anthracene and more negative than the reduction potential of 4,4′-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl, wherein the reduction potential in both cases is measured against Fc/Fc+ in tetrahydrofurane; and the dipole moment of the first matrix compound is selected ≥0 Debye and ≤2.5 Debye and the dipole moment of the second matrix compound is selected >2.5 and <10 Debye.

First claim

The invention claimed is:

1. Organic electroluminescent device comprising an anode, a cathode, an emission layer, an undoped electron transport layer comprising a first matrix compound, and an electron injection layer comprising a second matrix compound and an alkali organic complex and/or alkali halide,
wherein the undoped electron transport layer and the electron injection layer are arranged between the emission layer and the cathode,
wherein the reduction potential of the first matrix compound is less negative than the reduction potential of 9,10-di(naphthalen-2-yl)anthracene and more negative than the reduction potential of 4,4′-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl, wherein the reduction potential in both cases is measured against Fc/Fc + in tetrahydrofurane;
wherein the dipole moment of the first matrix compound is selected 0 Debye and ≤2.5 Debye and the dipole moment of the second matrix compound is selected >2.5 and <10 Debye;
the emission layer is in direct contact with the undoped electron transport layer;
the emission layer comprises an emission layer host; and
the off-set between the reduction potential of the emission layer host and the reduction potential of the first matrix compound is ≥0.1 and ≤0.3 V;
wherein the first matrix compound is selected from the following compounds or derivatives thereof, the compounds being dibenzo[c,h]acridine, dibenzo[a,j]acridine, benzo[c]acridine, triaryl borane compounds, 2-(benzo[d]thiazol-2-yl)phenoxy metal complex, triazine, benzothienopyrimidine, or mixtures thereof;
wherein the second matrix compound is selected from the following compounds or derivatives thereof, the compounds being phosphine oxide, benzimidazole, phenanthroline, or mixtures thereof; and
wherein the alkali organic complex is a lithium organic complex and/or the alkali halide is lithium halide.

2. Organic electroluminescent device according to claim 1 , wherein the first matrix compound comprises a triaryl borane compound of formula (I)

wherein R 1 , R 3 and R 7 are independently selected from a group consisting of H, D, C 1 -C 16 alkyl and C 1 -C 16 alkoxy;
R 2 , R 4 , R 5 and R 6 are independently selected from a group consisting of H, D, C 1 -C 16 alkyl, C 1 -C 16 alkoxy and C 6 -C 20 aryl;
Ar 0 is selected from substituted or unsubstituted C 6 -C 20 aryl, wherein, in case that Ar 0 is substituted, the substituents are independently selected from a group consisting of D, C 1 -C 12 alkyl, C 1 -C 16 alkoxy and C 6 -C 20 aryl; and
Ar 1 is selected from substituted or unsubstituted C 6 -C 20 arylene, wherein, in case that Ar 1 is substituted, the substituents are independently selected from a group consisting of D, C 1 -C 12 alkyl, C 1 -C 16 alkoxy and C 6 -C 20 aryl; and
Ar 2 is selected from a group consisting of H, D, substituted or unsubstituted C 6 -C 40 aryl and C 5 -C 40 heteroaryl.

3. Organic electroluminescent device according to claim 1 , wherein the first matrix compound comprises a dibenzo[c,h]acridine compound of formula (II)

and/or a dibenzo[a,j]acridine compound of formula (III)

and/or a benzo[c]acridine compound of formula (IV)

wherein Ar 3 is independently selected from C 6 -C 20 arylene;
Ar 4 is independently selected from unsubstituted or substituted C 6 -C 40 aryl;
and in case that Ar 4 is substituted, the one or more substituents may be independently selected from the group consisting of C 1 -C 12 alkyl and C 1 -C 12 heteroalkyl.

4. Organic electroluminescent device according to claim 1 , wherein the first matrix compound comprises a triazine compound of formula (V)

wherein Ar 5 is independently selected from unsubstituted or substituted C 6 -C 20 aryl or Ar 5.1 -Ar 5.2 ,
wherein Ar 5.1 is selected from unsubstituted or substituted C 6 -C 20 arylene and Ar 5.2 is selected from unsubstituted or substituted C 6 -C 20 aryl or unsubstituted and substituted C 5 -C 20 heteroaryl;
Ar 6 is selected from unsubstituted or substituted C 6 -C 20 arylene;
Ar 7 is independently selected from a group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, the aryl and the heteroaryl having 6 to 40 ring-forming atoms;
x is selected from 1 or 2,
wherein in case that Ar 5 is substituted the one or more substituents may independently be selected from C 1 -C 12 alkyl and C 1 -C 12 heteroalkyl;
and in case that Ar 7 is substituted, the one or more substituents may be independently selected from C 1 -C 12 alkyl and C 1 -C 12 heteroalkyl, and from C 6 -C 20 aryl.

5. Organic electroluminescent device according to claim 1 , wherein the first matrix compound comprises benzothienopyrimidine compound substituted with C 6 -C 40 aryl, C 5 -C 40 heteroaryl and/or C 1 -C 12 alkyl groups.

6. Organic electroluminescent device according to claim 1 , wherein the alkali organic complex is a compound of formula (VII)

wherein M is an alkali metal ion, each of A 1 -A 4 is independently selected from substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl.

7. Organic electroluminescent device according to claim 1 , wherein the thickness of the undoped electron transport layer is at least two times the thickness of the electron injection layer.

8. Organic electroluminescent device according to claim 1 , wherein the emission layer comprises a fluorescent blue emitter.

9. Organic electroluminescent device according to claim 8 , wherein the organic electroluminescent device is a fluorescent blue device.

10. Organic electroluminescent device according to claim 9 , wherein the emission layer further comprises an anthracene matrix compound substituted with C 6 -C 40 aryl, C 5 -C 40 heteroaryl and/or C 1 -C 12 alkyl groups.

11. Organic electroluminescent device according to claim 3 , wherein Ar 3 is phenylene, biphenylene, or fluorenylene.

12. Organic electroluminescent device according to claim 3 , wherein Ar 4 is phenyl, naphthyl, anthranyl, pyrenyl, or phenanthryl.

13. Organic electroluminescent device according to claim 4 , wherein Ar 6 is phenylene, biphenylene, terphenylene, or fluorenylene.

14. Organic electroluminescent device according to claim 4 , wherein Ar 7 is phenyl, naphthyl, phenantryl, fluorenyl, terphenyl, pyridyl, quinolyl, pyrimidyl, triazinyl, benzo[h]quinolinyl, or benzo[4,5]thieno[3,2-d]pyrimidine.

15. Organic electroluminescent device according to claim 5 , wherein the first matrix compound comprises 2-phenyl-4-(4′,5′,6′-triphenyl-[1,1′:2′,1″:3″,1′″-quaterphenyl]-3′″-yl)benzo[4,5]thieno[3,2-d]pyrimidine.

Assignees

• Novaled Gmbh

Inventors

• Pavicic Domagoj
• Rothe Carsten
• Jankus Vygintas
• Luschtinetz Regina
• Ganier Jerome

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/322

  comprising boron · CPC title

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title