Organic iridium complex for organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9793499-B2
Application number	US-201515314648-A
Country	US
Kind code	B2
Filing date	Jun 9, 2015
Priority date	Jun 13, 2014
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

The present invention provides an organic metal complex having high heat resistance while making it possible to realize electroluminescence with high quantum efficiency as a light-emitting material for organic electroluminescent (EL) element. The present invention relates to an organic iridium complex for an organic EL element, wherein a C—N ligand including a substituent of a tricyclic-based structure obtained by condensing a heterocyclic ring and two benzene rings, and a β-diketone ligand composed of a propane-1,3-dione having two tert-butyl-substituted phenyl groups are coordinated with an iridium atom. The complex of the present invention has high heat resistance and contributes to lifetime prolongation of the organic EL element.

First claim

The invention claimed is:

1. An organic iridium complex for an organic electroluminescent element represented by the following Formula

wherein R 1 , R 2 , and R 3 are each a tert-butyl group or a hydrogen atom, and the β-diketone ligand has at least one tert-butyl group; they may bond each other to thereby form a saturated hydrocarbon ring when the β-diketone ligand has two tert-butyl groups; A is a substituent having a heterocyclic ring which is either a 5-membered ring or a 6-membered ring and containing nitrogen; the heterocyclic ring of A is optionally fused to a benzene ring and may include sulfur atom (S) or oxygen atom (O) as a hetero atom other than nitrogen (N); X is a hetero atom.

2. The organic iridium complex according to claim 1 , wherein
the β-diketone ligand is represented by any of the following Formula

R 1 and R 3 are each a tert-butyl group, and R 2 is hydrogen,

R 2 and R 3 are each a tert-butyl group, and R 1 is hydrogen,

R 2 and R 3 are each a tert-butyl group, which bond each other to form a saturated hydrocarbon ring, and R 1 is hydrogen.

3. The organic iridium complex according to claim 1 , wherein the A is a substituent composed of a condensed structure of the heterocyclic ring including nitrogen and a benzene ring.

4. The organic iridium complex according to claim 3 , wherein the heterocyclic ring or the benzene ring of the A has a substituent containing fluorine or oxygen.

5. The organic iridium complex according to claims 1 , wherein the heterocyclic ring of the A further includes sulfur atom (S) or oxygen atom (O) as the hetero atom.

6. The organic iridium complex according to claim 1 , wherein the A is represented by any of the following Formula

7. The organic iridium complex according to claim 1 , wherein X is an oxygen atom (O) or a sulfur atom (S).

8. The organic iridium complex according to claim 1 , wherein a PL quantum yield ΦPL when 4 wt % doping is performed in a polymer thin film is 0.4 or more.

9. An organic electroluminescent element including an emission layer having the organic iridium complex according to claim 1 .

10. The organic iridium complex according to claim 1 , wherein the A is a substituent composed of a condensed structure of the heterocyclic ring including nitrogen and a benzene ring.

11. The organic iridium complex according to claim 2 , wherein the heterocyclic ring of the A further includes sulfur atom (S) or oxygen atom (O) as the hetero atom.

12. The organic iridium complex according to claim 2 , wherein the A is represented by any of the following Formula

13. The organic iridium complex according to claim 2 , wherein X is an oxygen atom (O) or a sulfur atom (S).

14. The organic iridium complex according to claim 2 , wherein a PL quantum yield ΦPL 4 wt % doping is performed in a polymer thin film is 0.4 or more.

15. The organic iridium complex according to claim 3 , wherein the heterocyclic ring of the A further includes sulfur atom (S) or oxygen atom (O) as the hetero atom.

16. The organic iridium complex according to claim 3 , wherein the A is represented by any of the following Formula

17. The organic iridium complex according to claim 3 , wherein X is an oxygen atom (O) or a sulfur atom (S).

18. The organic iridium complex according to claim 3 , wherein a PL quantum yield ΦPL when 4 wt % doping is performed in a polymer thin film is 0.4 or more.

19. The organic iridium complex according to claim 4 , wherein the heterocyclic ring of the A further includes sulfur atom (S) or oxygen atom (O) as the hetero atom.

20. The organic iridium complex according to claim 4 , wherein the A is represented by any of the following Formula

Assignees

• Tanaka Precious Metal Ind
• Univ Osaka Prefect Public Corp

Inventors

• Masahiro Yasushi
• Yagi Shigeyuki
• Taniuchi Junichi

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title