Organic metal complex, and organic light emitting device and display apparatus using the same

Patent metadata

Field	Value
Publication number	US-11793064-B2
Application number	US-202016859356-A
Country	US
Kind code	B2
Filing date	Apr 27, 2020
Priority date	Nov 8, 2007
Publication date	Oct 17, 2023
Grant date	Oct 17, 2023

Abstract

Provided is an organic metal complex having a structure represented by the following general formula (1):MLmL′n  (1)where: M represents a metal atom selected from Ir, Pt, Rh, Os, and Zn; L and L′, which are different from each other, each represent a bidentate ligand; m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n is 3; a partial structure MLm represents a structure represented by the following general formula (2):and a partial structure ML′n represents a structure including a monovalent bidentate ligand.

First claim

What is claimed is:

1. An organic metal complex having a structure represented by the following general formula (1):
ML m L′ n   (1)

where:
M represents a metal atom selected from Ir, Pt, Rh, Os, and Zn;
L and L′, which are different from each other, each represent a bidentate ligand;
m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n is 3;
a partial structure ML m represents a structure represented by the following general formula (2):

where:
A represents a structure represented by the following general formula (3), which has, as a basic skeleton, a benzo[f]isoquinoline ring:

where:
R 1 to R 8 , which may be identical to or different from each other, each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aralkyl group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and adjacent substituents among R 1 to R 8 may be bonded to form a ring; and
B represents a fused ring which may have a substituent and the fused ring is a naphthalene ring; and
a partial structure ML′ n represents a structure including a monovalent bidentate ligand; provided that:
i) at least one of R 1 to R 8 is not a hydrogen atom,
ii) B represents a fused ring which has a substituent not being a hydrogen atom, or
iii) at least one of R 1 to R 8 is not a hydrogen atom and B represents a fused ring, which has a substituent not being a hydrogen atom.

2. The organic metal complex according to claim 1 , wherein:
the partial structure ML m has a structure represented by the following general formula (8):

wherein, of those substituents represented by R 41 to R 44 , adjacent substituents are bonded to form a naphthalene ring; wherein R 41 to R 52 each represents a hydrogen atom, halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aralkyl group, an amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
provided that
i) at least one of R 45 to R 52 is not a hydrogen atom,
ii) the naphthalene ring has a substituent not being a hydrogen atom, or
iii) at least one of R 45 to R 52 is not a hydrogen atom and the naphthalene ring has a substituent not being a hydrogen atom.

3. The organic metal complex according to claim 1 , wherein:
M represents Ir; and
the partial structure ML′ n has a structure represented by any one of the following general formulae (10) to (12):

where R 65 to R 79 , which may be identical to or different from each other, each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aralkyl group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and adjacent substituents among R 65 to R 72 , among R 73 to R 76 , or among R 77 to R 79 may be bonded to form a ring.

4. The organic metal complex according to claim 1 , wherein R 3 and R 4 may be bonded to form a benzene ring that is fused with the benzo[f]isoquinoline ring represented in the formula (3).

5. The organic metal complex according to claim 2 , wherein R 47 and R 48 may be bonded to form a benzene ring that is fused with the benzo[f]isoquinoline ring represented in the formula (8).

6. The organic metal complex according to claim 3 , wherein adjacent substituents among R 65 to R 68 , may be bonded to form a ring that is fused with the benzene ring represented in the formula (10).

7. The organic metal complex according to claim 3 , wherein adjacent substituents among R 77 to R 79 may be bonded to form a ring that is fused with a backbone represented in the formula (12).

8. An organic light emitting device, comprising:
an anode;
a cathode; and
a layer formed of an organic compound, which is sandwiched between the anode and the cathode,
wherein the layer formed of an organic compound comprises the organic metal complex according to claim 1 .

9. The organic light emitting device according to claim 8 , wherein the organic metal complex is incorporated in an emission layer.

10. The organic light emitting device according to claim 9 , wherein the emission layer comprises a host material and another material which is different from the host material, and the another material is the organic metal complex.

11. The organic light emitting device according to claim 10 , wherein the weight ratio of the organic metal complex is 0.01 to 20 wt % with respect to the host material.

12. The organic light emitting device according to claim 8 , wherein the organic light emitting device emits a red light.

13. An apparatus comprising the organic light emitting device according to claim 8 ; and a substrate.

14. The apparatus according to claim 13 , wherein the organic light emitting device being provided on the substrate,
wherein the apparatus has a bottom emission structure in which the light which the organic light emitting device emits is extracted from the substrate side.

15. The apparatus according to claim 14 , wherein the organic light emitting device being provided on the substrate,
wherein the apparatus has a top emission structure in which the light which the organic light emitting device emits is extracted from a side opposite to the substrate.

16. A luminescent ink comprising a solvent and the organic metal complex according to claim 1 .

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kamatani Jun
• Hashimoto Masashi
• Igawa Satoshi
• Okada Shinjiro

Classifications

• H10K71/40

  Thermal treatment, e.g. annealing in the presence of a solvent vapour · CPC title

• H10K85/342 Primary

  comprising iridium · CPC title

• C07C17/14 Primary

  in the side-chain of aromatic compounds · CPC title

• C07C45/00

  Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds · CPC title

• C07F15/0033

  Iridium compounds · CPC title