Organic light-emitting device and display apparatus

Patent metadata

Field	Value
Publication number	US-9601704-B2
Application number	US-201414764204-A
Country	US
Kind code	B2
Filing date	Feb 4, 2014
Priority date	Feb 6, 2013
Publication date	Mar 21, 2017
Grant date	Mar 21, 2017

Abstract

Provided is a long-lifetime organic light-emitting element having a good device lifetime characteristic. The organic light-emitting device includes: a pair of electrodes; and an organic compound layer placed between the pair of electrodes, in which the organic compound layer includes an iridium complex having a specific structure and a different kind of metal complex.

First claim

The invention claimed is:

1. An organic light-emitting device, comprising:
a pair of electrodes; and
an organic compound layer placed between the pair of electrodes,
wherein the organic compound layer comprises an iridium complex represented by the following general formula [1] and a metal complex represented by the following general formula [5]:

in the formula [1]:
m represents an integer of 1 to 3, and n represents an integer of 0 to 2, provided that a relationship of m+n=3 is satisfied;
R 1 to R 14 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and may be identical to or different from one another, provided that when m represents 3 or when X is free of an alkyl group, at least one of substituents represented by R 1 to R 14 comprises an alkyl group;
X represents a bidentate ligand; and
a partial structure IrX n represents any one of partial structures represented by the following general formulae [2] to [4]:

in the formulae [2] to [4], R 15 to R 29 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and may be identical to or different from one another, provided that when none of R 1 to R 14 represents an alkyl group, at least one of substituents represented by R 15 to R 29 comprises an alkyl group, and when n represents 2, multiple substituents represented by any one of R 15 to R 29 may be identical to or different from each other;
ML 2   [5]

in the formula [5]:
M represents a divalent metal atom selected from beryllium, magnesium, and zinc;
L represents a bidentate ligand;
when M represents beryllium or magnesium, a partial structure ML comprises any one of structures represented by the following general formulae [6] to [11]; and
when M represents zinc, the partial structure ML comprises any one of structures represented by the following general formulae [7] to [11]:

in the formulae [6] to [11], R 30 to R 57 each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group, and in the formulae [8] to [11], a ring B comprises any one of cyclic structures represented by the following general formulae [12] to [14], *1 represents a bonding position with an oxygen atom, and *2 represents a bonding position with a carbon atom in a five-membered heterocyclic skeleton:

in the formulae [12] to [14], R 58 to R 71 each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group.

2. The organic light-emitting device according to claim 1 , wherein the m represents 2 and the n represents 1.

3. The organic light-emitting device according to claim 1 , wherein the iridium complex represented by the general formula [1] comprises a compound represented by the following general formula [15]:

in the formula [15]:
R 72 to R 88 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, provided that at least one of R 72 to R 88 represents an alkyl group; and
m represents an integer of 1 to 3, and n represents an integer of 0 to 2, provided that a relationship of m+n=3 is satisfied.

4. The organic light-emitting device according to claim 1 , wherein the iridium complex represented by the general formula [1] comprises a compound represented by the following general formula [16]:

in the formula [16], Q 1 to Q 10 each represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, or a substituted or unsubstituted phenyl group, provided that at least one of Q 1 to Q 10 represents an alkyl group.

5. The organic light-emitting device according to claim 1 , wherein the organic compound layer comprises an emission layer including a host and a guest;
the guest comprises the iridium complex represented by the general formula [1]; and
the host comprises the metal complex compound represented by the general formula [5].

6. The organic light-emitting device according to claim 5 , wherein the organic compound layer further includes an assist material different from the host and the guest.

7. The organic light-emitting device according to claim 6 , wherein the assist material comprises an iridium complex.

8. The organic light-emitting device according to claim 1 , wherein the device emits red light.

9. A display apparatus, comprising multiple pixels, wherein the pixels each include the organic light-emitting device according to claim 1 and an active device connected to the organic light-emitting device.

10. A lighting apparatus comprising:
the organic light-emitting device according to claim 1 ; and
an AC/DC converter circuit connected to the organic light-emitting device.

11. An image-forming apparatus comprising:
a photosensitive member;
charging unit for charging a surface of the photosensitive member;
exposing unit for exposing the photosensitive member to form an electrostatic latent image; and
developing unit for developing the electrostatic latent image formed on the surface of the photosensitive member,
wherein the exposing unit includes the organic light-emitting device according to claim 1 .

12. An exposing apparatus for exposing a photosensitive member, comprising a plurality of the organic light-emitting devices according to claim 1 , wherein the organic light-emitting devices are arranged to form a line along a predetermined direction.

Assignees

• Canon Kk

Inventors

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

Classifications

• H10K85/342

  comprising iridium · CPC title

• C07D263/56 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2 · CPC title

• H01L27/3248

  Electricity · mapped topic

• C09K2211/185

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

• G09G2320/045

  Compensation of drifts in the characteristics of light emitting or modulating elements · CPC title