IP Library Granted Patent US 9,601,704
Granted Patent B2
US 9,601,704 · App. 14/764,204 · Granted Mar 21, 2017

Organic light-emitting device and display apparatus

Inventors: Hirokazu Miyashita (Tokyo, JP); Kengo Kishino (Tokyo, JP); Jun Kamatani (Tokyo, JP); Shigemoto Abe (Yokohama, JP); Naoki Yamada (Inagi, JP); Tetsuya Kosuge (Yokohama, JP); Takayuki Horiuchi (Tokyo, JP); Yosuke Nishide (Kawasaki, JP); Akihito Saitoh (Gotemba, JP)
Assignee: Canon Kabushiki Kaisha
H01L51/0085C07D215/24C07D221/10C07D221/18C07D233/64C07D235/18C07D263/56C07D277/66C09B57/00C09B57/10C09K11/06G09G3/3216H01L27/3234H01L27/3248H01L51/0077H01L51/0092C09K2211/1007C09K2211/1029C09K2211/185G09G2320/043G09G2320/045H01L51/5016H01L51/5028
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Quick Facts
Patent No.
US 9,601,704
App. No.
14/764,204
Granted
Mar 21, 2017
Kind
B2
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.

Claims (42)

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.

Assignments (2)
CHANGE OF NAME Recorded Jun 18, 2019
From: CANON KABUSHIKI KAISHA
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 049501/0097 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 28, 2015
From: MIYASHITA, HIROKAZU; KISHINO, KENGO; KAMATANI, JUN; ABE, SHIGEMOTO; YAMADA, NAOKI; KOSUGE, TETSUYA; HORIUCHI, TAKAYUKI; NISHIDE, YOSUKE; SAITOH, AKIHITO
To: CANON KABUSHIKI KAISHA
Reel/Frame 036444/0205 →
Priority Claims (1)
JP 2013-021048 · Feb 6, 2013 · national
Continuity (1)
Related Publication 20150364703A1 · Dec 17, 2015