Organometallic complex and organic light-emitting element using the complex

Patent metadata

Field	Value
Publication number	US-9917264-B2
Application number	US-201414761049-A
Country	US
Kind code	B2
Filing date	Jan 20, 2014
Priority date	Jan 21, 2013
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

Provided is an organic light-emitting element having high light-emitting efficiency and a long element lifetime, the organic light-emitting element including an anode, a cathode, and an organic compound layer placed between the anode and the cathode, in which: the organic compound layer includes an emission layer; the emission layer includes a host and a guest; the host is an aromatic hydrocarbon compound; the guest is an iridium complex of a specific structure; and a content of the host is 50 wt % or more with reference to the total amount of the constituent materials for the emission layer.

First claim

The invention claimed is:

1. An iridium complex comprising a compound represented by the following general formula [1]:
Ir(L 1 )(L 2 )(L 3 )  [1]

in the general formula [1]:
L 1 , L 2 , and L 3 represent bidentate ligands different from one another; and
the partial structure IrL 1 comprises a partial structure represented by the following general formula [2]:

in the general formula [2]:
the ring A 1 represents an aromatic ring or an aromatic heterocycle, and the ring A 1 can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group; and
R 1 to R 8 each represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group, and can be identical to or different from one another, and when any one of substituents represented by R 1 to R 8 is an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, or an aryloxy group, the substituent can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group;

in the general formula [1]:
the partial structure IrL 2 comprises a partial structure represented by the following general formula [3]:

in the general formula [3]:
the ring A 2 represents an aromatic ring or an aromatic heterocycle, and the ring A 2 can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group; and
the ring B represents a nitrogen-containing aromatic heterocycle, and the ring B can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group; and
L 3 represents a monovalent bidentate ligand having a first atom that forms a bond with iridium and is selected from N, O, S, and P, and a second atom that forms a bond with iridium and is selected from N, O, S, and P, and the first atom and the second atom can be identical to or different from each other.

2. The iridium complex according to claim 1 , wherein the ring A 1 is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring; and
the ring A 1 can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group.

3. The iridium complex according to claim 1 , wherein the partial structure represented by the general formula [2] comprises a partial structure represented by the following general formula [4]:

in the general formula [4]:
the ring A 3 is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring and the ring A 3 can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group; and
R 9 to R 12 each represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, or a phenyl group, and when any one of substituents represented by R 9 to R 12 is an alkyl group having 1 or more and 4 or less carbon atoms or a phenyl group, the substituent can further have a substituent selected from the group consisiting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group, and R 9 to R 12 can be identical to or different from one another.

4. The iridium complex according to claim 1 , wherein the ring A 2 represents a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring;
the ring A 2 can further have a substituent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group;
the ring B represents a pyridine ring, a quinoline ring, an isoquinoline ring, a benzo[f]quinoline ring, a benzo[h]quinoline ring, a benzo[f]isoquinoline ring, a benzo[h]isoquinoline ring, an oxazole ring, a benzo[d]oxazole ring, a benzo[d]thiazole ring, or an imidazole ring; and
the ring B can futher have a substutent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group.

5. The iridium complex according to claim 1 , wherein the partial structure represented by IrL 1 comprises a partial structure represented by the following general formula [8]:

in the formula [8]:
a ring A 4 represents any one of partial structures represented by the following general formula [9] to [13];
*1 represents a bond between the ring A 4 and an isoquinoline skeleton and *2 represents a bond between the ring A 4 and an Ir metal; and
R 24 to R 27 each represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, or a phenyl group, and may be identical to or different from one another, and when any one of substituents represented by R 24 to R 27 is an alkyl group having 1 or more and 4 or less carbon atoms or a phenyl group, the substituent can futher have a substutent selected from the group consisting of an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, and a cyano group:

in the general formulae [9] to [13], R 28 to R 50 each represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, a substituted amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group, and when any one of substituents represented by R 28 to R 50 is an alkyl group having 1 or more and 4 or less carbon atoms, an aralkyl group, an aryl group, a heterocyclic

Assignees

• Canon Kk

Inventors

• Horiuchi Takayuki
• Kishino Kengo
• Miyashita Hirokazu
• Nishide Yosuke
• Kosuge Tetsuya
• Yamada Naoki
• Kamatani Jun
• Saitoh Akihito
• Abe Shigemoto

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H05B45/60

  Circuit arrangements for operating LEDs comprising organic material, e.g. for operating organic light-emitting diodes [OLED] or polymer light-emitting diodes [PLED] · CPC title