Iridium complex-containing composition, organic light emitting device having the same, display apparatus, imaging apparatus, electronic equipment, lighting apparatus, and moving body

Patent metadata

Field	Value
Publication number	US-12312367-B2
Application number	US-202117224568-A
Country	US
Kind code	B2
Filing date	Apr 7, 2021
Priority date	Apr 9, 2020
Publication date	May 27, 2025
Grant date	May 27, 2025

Abstract

A composition that contains an iridium complex and an isomer of the iridium complex, in which the amount of the isomer of the iridium complex is decreased. The iridium complex is a homo-N-trans (HNT) iridium complex having an iridium atom, and a first ligand, a second ligand, and a third ligand that are bonded to the iridium atom. The isomer has an iridium atom, a fourth ligand, a fifth ligand, and the third ligand. The composition ratio of the isomer relative to a total of the iridium complex and the isomer is 1.0% or less.

First claim

What is claimed is:

1. A composition comprising:
a homo-N-trans (HNT) iridium complex having an iridium atom, and a first ligand, a second ligand, and a third ligand that are bonded to the iridium atom,
the second ligand having the same structure as the first ligand,
the third ligand having a different structure from the first and second ligands; and

an isomer of the iridium complex, the isomer having an iridium atom, a fourth ligand, a fifth ligand, and the third ligand,
the fourth ligand being a ligand represented by the same rational formula as that of the first ligand, and
the fifth ligand being a ligand represented by the same rational formula as that of the second ligand,

wherein a composition ratio of the isomer relative to a total of the iridium complex and the isomer is 1.0% or less and more than 0%.

2. The composition according to claim 1 , wherein the composition ratio of the isomer is 0.6% or less.

3. The composition according to claim 1 , wherein the isomer is a structural isomer of the iridium complex and satisfies at least one of (1) and (2) below:
(1) the first ligand has a structure different from the fourth ligand, and
(2) the second ligand has a structure different from the fifth ligand.

4. The composition according to claim 3 , wherein each of the first and second ligands has a structure having a substituent, and the fourth or fifth ligand has a structure having a substituent at a different substitution position from that in the first or second ligand.

5. The composition according to claim 3 , wherein (1) and (2) are both satisfied.

6. The composition according to claim 1 , wherein the isomer is a stereoisomer of the iridium complex and satisfies at least one of (3) and (4) below:
(3) the first ligand and the fourth ligand have different steric configurations with respect to the iridium atom, and
(4) the second ligand and the fifth ligand have different steric configurations with respect to the iridium atom.

7. The composition according to claim 6 , wherein (3) and (4) are both satisfied.

8. The composition according to claim 1 , wherein the iridium complex is represented by formula [1] or [2] below:

where, in formula [1] and formula [2], L represents a bidentate ligand, R 1 to R 18 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heteroaromatic group;
ring A represents a ring structure that may have a substituent and that is selected from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a 9,9-spirobifluorene ring, a chrysene ring, and a substituted or unsubstituted heteroaromatic group; and
IrL is represented by one of formulae [3] to [5] below:

where, in formulae [3] to [5], R 19 to R 33 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heteroaromatic group.

9. The composition according to claim 1 , wherein the iridium complex is represented by formula [6] below:

where, in formula [6], R 34 to R 48 are each independently selected from a hydrogen atom and a substituted or unsubstituted alkyl group, and R 42 to R 45 may bond to one another to form a ring structure.

10. The composition according to claim 9 , wherein, in the iridium complex represented by formula [6], R 45 represents a hydrogen atom and R 43 represents an alkyl group, and
in the isomer of the iridium complex represented by formula [6], R 45 represents an alkyl group and R 43 represents a hydrogen atom.

11. The composition according to claim 9 , wherein, in the iridium complex represented by formula [6], R 37 represents a cyano group.

12. The composition according to claim 1 , wherein the composition ratio of the isomer is 0.2% or more.

13. The composition according to claim 12 , wherein the composition ratio of the isomer is 0.9% or less.

14. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic compound layer disposed between the first electrode and the second electrode,
wherein the organic compound layer includes the composition according to claim 1 .

15. The organic light emitting device according to claim 14 , wherein the organic compound layer is a light emitting layer, and the light emitting layer further includes a first organic compound, and
the first organic compound is a compound having a lowest excited triplet energy larger than that of the iridium complex contained in the composition.

16. The organic light emitting device according to claim 15 , wherein the light emitting layer further includes a second organic compound, and
the second organic compound has a lowest excited triplet energy larger than or equal to the lowest excited triplet energy of the iridium complex contained in the composition but smaller than or equal to the lowest excited triplet energy of the first organic compound.

17. The organic light emitting device according to claim 15 , wherein the organic compound layer includes a first charge transport layer disposed between the first electrode and the light emitting layer and a second charge transport layer disposed between the second electrode and the light emitting layer, and
the first electrode is in contact with the first charge transport layer, and the second electrode is in contact with the second charge transport layer.

18. A display apparatus comprising:
a plurality of pixels, at least one of which is the organic light emitting device according to claim 14 ; and
a transistor connected to the organic light emitting device.

19. The display apparatus according to claim 18 , further comprising:
a color filter on a light emitting side of the organic light emitting device.

20. An imaging apparatus comprising:
an optical section that includes a plurality of lenses;
an imaging device that receives light that has passed through the optical section; and
a display section that displays an image captured by the imaging device,
wherein the display section includes the organic light emitting device according to claim 14 .

21. Electronic equipment comprising:
a display section that includes the organic light emitting device according to claim 14 ;
a casing in which the display section is disposed; and
a communication section that is disposed in the casing and communicates with external.

22. A lighting apparatus comprising:
a light source that includes the organic light emitting device according to claim 14 ; and
a light diffusing section or optical film that transmits light emitted from the light source.

23. A moving body comprising:
a lamp fixture that includes the organic light emitting device according to claim 14 ; and
a body on which the lamp fixture is disposed.

Assignees

• Canon Kk

Inventors

• Sekiguchi Takeshi
• Ito Kentaro
• Hotta Katsuyuki

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K59/38

  comprising colour filters or colour changing media [CCM] · CPC title