Organometallic complexes, and organic electroluminescence device and display using the same

Patent metadata

Field	Value
Publication number	US-9425414-B2
Application number	US-201314062506-A
Country	US
Kind code	B2
Filing date	Oct 24, 2013
Priority date	Nov 2, 2012
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

Disclosed are an organometallic complex, and an organic electroluminescence device and a display device including the same. The organometallic complex is represented by the following Chemical Formula 1.

The definition of the above Chemical Formula 1 is the same as described in the detailed description.

First claim

What is claimed is:

1. An organometallic complex represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
CyN-M-CyC forms a heterocyclic ring and CyN—CyC is a cyclometalating ligand bonded with M through a nitrogen atom and a carbon atom; or CyN is a substituted or unsubstituted C2 to C60 heterocyclic group comprising a nitrogen atom bonded with M or a substituted or unsubstituted C3 to C60 heteroaryl group including a nitrogen atom bonded with M, CyC is a substituted or unsubstituted C4 to C60 carbon cyclic group including a carbon atom bonded with M, a substituted or unsubstituted C3 to C60 heterocyclic group including a carbon atom bonded with M, a substituted or unsubstituted C6 to C60 aryl group including a carbon atom bonded with M, a substituted or unsubstituted C7 to C60 arylalkyl group including a carbon atom bonded with M, or a substituted or unsubstituted C3 to C60 heteroaryl group including a carbon atom bonded with M, and CyN—CyC is a cyclometalating ligand bonded with M through a nitrogen atom and a carbon atom,
X 1 to X 3 are independently N or CR′, provided at least one of X 1 to X 3 is a nitrogen atom,
R 1 to R 3 and R′ are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, SF 5 , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted diaryl boronyl, or at least two of R 1 to R 3 are fused to form a fused ring, and
n is an integer ranging from 0 to 2.

2. The organometallic complex of claim 1 , wherein the organometallic complex is represented by Chemical Formula 2:

wherein, in Chemical Formula 2,
M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
CyN-M-CyC forms a heterocyclic ring and CyN—CyC is a cyclometalating ligand bonded with M through a nitrogen atom and a carbon atom; or CyN is a substituted or unsubstituted C2 to C60 heterocyclic group comprising a nitrogen atom bonded with M or a substituted or unsubstituted C3 to C60 heteroaryl group comprising a nitrogen atom bonded with M, CyC is a substituted or unsubstituted C4 to C60 carbon cyclic group including a carbon atom bonded with M, a substituted or unsubstituted C3 to C60 heterocyclic group including a carbon atom bonded with M, a substituted or unsubstituted C6 to C60 aryl group including a carbon atom bonded with M, a substituted or unsubstituted C7 to C60 arylalkyl group including a carbon atom bonded with M, or a substituted or unsubstituted C3 to C60 heteroaryl group including a carbon atom bonded with M, and CyN—CyC is a cyclometalating ligand bonded with M through a nitrogen atom and a carbon atom,
X 1 to X 6 are independently N or CR′, provided at least one of X 1 to X 3 is a nitrogen atom and at least one of X 4 to X 6 is a nitrogen atom,
R 1 to R 6 and R′ are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, SF 5 , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted diaryl boronyl, or at least two of R 1 to R 6 are fused to form a fused ring,
n and m are independently integers ranging from 0 to 2, and m+n≦3.

3. The organometallic complex of claim 1 , wherein the organometallic complex is represented by Chemical Formula 3:

wherein, in Chemical Formula 3,
M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
X 1 to X 9 are independently N or CR′, provided at least one of X 1 to X 3 is atom N, at least one of X 4 to X 6 is atom N, and at least one of X 7 to X 9 is atom N,
R 1 to R 9 and R′ are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, SF 5 , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted diaryl boronyl, or R 1 to R 9 are fused to form a fused ring,
n and m are independently integers ranging from 0 to 2, and m+n≦3.

4. The organometallic complex of claim 1 , wherein the cyclometalating ligand (CyN—CyC) is one of chemical formulae:

wherein, in the above chemical formulae,
R 11 , R 12 , R 13 , R 14 , and R 15 are independently a monosubstituted or multisubstituted group, hydrogen, a halogen, —OR, —N(R) 2 , —P(R) 2 , —POR, —PO 2 R, —PO 3 R, —SR, —Si(R) 3 , —B(R) 2 , —B(OR) 2 , —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, a C1 to C20 alkyl group, or a C6 to C20 aryl group,
wherein R is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C7 to C40 arylalkyl group, a substituted or unsubstituted C7 to C40 alkylaryl group, a substituted or unsubstituted C2 to C40 heteroaryl group, or a substituted or unsubstituted C3 to C40 heteroarylalkyl group, and
Z is S, O, or NW 0 wherein R 0 is hydrogen or a C1 to C20 alkyl group.

5. The organometallic complex of claim 1 , wherein the M is Ir or Pt.

6. The organometallic complex of claim 1 , wherein at least two of X 1 to X 3 are nitrogen atoms.

7. The organometallic complex of claim 1 , wherein all of X 1 to X 3 are nitrogen atoms.

8. The organometallic complex of claim 2 , whe

Assignees

• Samsung Electronics Co Ltd
• Cheil Ind Inc

Inventors

• Das Rupasree Ragini
• Noh Chang Ho
• Kravchuk Dmitry
• Kwon O Hyun
• Choi Hyeon Ho

Classifications

• C09K2211/185

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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07F17/02

  of metals of Groups 8, 9 or 10 of the Periodic Table · CPC title