Organoiridium complex for organic electroluminescent elements

Patent metadata

Field	Value
Publication number	US-9859511-B2
Application number	US-201515502695-A
Country	US
Kind code	B2
Filing date	Aug 26, 2015
Priority date	Aug 28, 2014
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The present invention provides an organometallic complex having a high quantum efficiency even in a polymer thin film as a emitting material for organic electroluminescent (EL) element. The present invention relates to an organoiridium complex for an organic electroluminescent element represented by the following Formula; wherein a C—N ligand including two atomic groups (A 1 , A 2 ), and a β-diketone ligand in line symmetry having two tert-butyl-substituted phenyl groups are coordinated with an iridium atom. The organoiridium complex of the present invention has a high quantum efficiency even in a polymer thin film with respect to green to yellow electroluminescence.

(In the aforementioned Formula, R 1 , R 2 , and R 3 are each a tert-butyl group or a hydrogen atom, and have at least one tert-butyl group; they may bond each other to thereby form a saturated hydrocarbon ring, when having two tert-butyl groups; A 1 , A 2 are each an unsaturated hydrocarbon ring, at least one is a single ring, and at least one is a heterocyclic ring).

First claim

The invention claimed is:

1. An organoiridium complex for an organic electroluminescent element represented by Chemical Formula 1, wherein a C—N ligand comprising two atomic groups (A 1 , A 2 ), and a β-diketone ligand in line symmetry having two tert-butyl-substituted phenyl groups are coordinated with an iridium atom,

wherein R 1 , R 2 , and R 3 are each a tert-butyl group or a hydrogen atom, and two of R 1 , R 2 , and R 3 are a tert-butyl group, and each phenyl ring of the β-diketone is substituted with the two tert-butyl groups, wherein the two tert-butyl groups may bond each other to thereby form a saturated hydrocarbon ring, and wherein the β-diketone ligand is represented by any of the formula in Chemical Formula 2;

wherein A 1 is an unsubstituted or substituted benzene ring or an unsubstituted or substituted 6-membered heteroaryl ring, wherein the 6-membered heteroaryl ring contains one N as a heteroatom, and A 2 is an unsubstituted or substituted 6-membered heteroaryl ring which contains one N as a heteroatom.

2. The organoiridium complex according to claim 1 , wherein the A 1 is substituted with a fluorine atom (F), a trifluoro (—CF 3 ) group, or a cyano (—CN) group.

3. The organoiridium complex according to claim 1 , wherein the A 2 is substituted with a fluorine atom (F), a trifluoro (—CF 3 ) group, an alkyl group (—R), or an alkoxy group (—OR).

4. The organoiridium complex according to claim 1 , wherein a PL quantum yield Φ PL when 0.05 mmol/g doping is performed in a polymer thin film is 0.45 or more.

5. The organoiridium complex according to claim 1 , wherein the light emission wavelength (λ PL ) in the polymer thin film is 510 nm or more and 580 nm or less.

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

7. The organoiridium complex according to claim 2 , wherein the A 2 is substituted with a fluorine atom (F), a trifluoro (—CF 3 ) group, an alkyl group (—R), or an alkoxy group (—OR).

Assignees

• Tanaka Precious Metal Ind
• Univ Osaka Prefect Public Corp

Inventors

• Masahiro Yasushi
• Yagi Shigeyuki
• Taniuchi Junichi

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/185

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

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title