Organic light-emitting device and display apparatus

Patent metadata

Field	Value
Publication number	US-9960370-B2
Application number	US-201314648095-A
Country	US
Kind code	B2
Filing date	Dec 25, 2013
Priority date	Dec 27, 2012
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Provided is an organic light-emitting device improved in emission efficiency and lifetime. The organic light-emitting device includes a pair of electrodes and an organic compound layer disposed between the pair of electrodes, in which: the organic compound layer includes a benzo[f]isoquinoline iridium complex of a specific structure and a hydrocarbon compound of a specific structure; and the hydrocarbon compound is a compound formed only of an SP 2 carbon atom and a hydrogen atom.

First claim

The invention claimed is:

1. An organic light-emitting device comprising:
a pair of electrodes; and
an organic compound layer disposed between the pair of electrodes,
wherein the organic compound layer includes an iridium complex represented by the following general formula [1] and a hydrocarbon compound represented by the following general formula [5]; and
the hydrocarbon compound comprises a compound formed only of an SP 2 carbon atom and a hydrogen atom:

in the formula [1]:
R 1 to R 8 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;
m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n equals 3;
a ring A represents a cyclic structure selected from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a 9,9-spirobifluorene ring, and a chrysene ring, and is covalently bonded to a benzo[f]isoquinoline skeleton and an Ir metal, and the ring A may further have a substituent;
X represents a bidentate ligand; and
a partial structure IrX x comprises any one of structures represented by the following general formulae [2] to [4]:

in the formulae [2] to [4]:
R 10 to R 24 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;
Ar 1 -(Ar 2 ) p —(Ar 3 ) q —Ar 1   [5]

in the formula [5]:
p and q each represent 0 or 1, and p+q is equal to or more than 1;
Ar 1 represents any one of substituents represented in the following substituent group α; and
Ar 2 and Ar 3 each represent any one of substituents represented in the following substituent group β, and Ar 2 and Ar 3 may be identical to or different from each other

[Substituent group α]

[Substituent group β]

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

3. The organic light-emitting device according to claim 1 , wherein the iridium complex is represented by the following formula [11]:

in the formula [11]:
R 61 to R 71 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;
t represents an integer of 1 to 3 and u represents an integer of 0 to 2, provided that t+u equals 3;
*1 represents a bond between the ring A and the Ir metal, and *2 represents a bond between the ring A and a carbon atom at a 1-position in the benzo[f]isoquinoline skeleton; and
the ring A comprises any one of structures represented by the following general formulae [12] to [16]:

in the formulae [12] to [16]:
R 72 to R 93 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group; and
1 represents a bonding position with the Ir metal and *2 represents a bonding position with the carbon atom at the 1-position in the benzo[f]isoquinoline skeleton.

4. The organic light-emitting device according to claim 3 , wherein the ring A comprises the structure represented by the general formula [12].

5. The organic light-emitting device according to claim 1 , wherein the iridium complex comprises an iridium complex represented by the following general formula [17]:

in the formula [17]:
Q 1 to Q 9 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, or a cyano group; and
G represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, or a substituted or unsubstituted phenyl group.

6. The organic light-emitting device according to claim 1 , wherein the organic compound layer is formed of the iridium complex, the hydrocarbon compound, and a third component.

7. The organic light-emitting device according to claim 6 , wherein a highest occupied molecular orbital (HOMO) level of the third component is larger in energy than a HOMO of the hydrocarbon compound.

8. The organic light-emitting device according to claim 6 , wherein a lowest unoccupied molecular orbital (LUMO) level of the third component is smaller in energy than a LUMO of the hydrocarbon compound.

9. A display apparatus comprising multiple pixels, wherein each pixel has the organic light-emitting device according to claim 1 and a transistor connected to the organic light-emitting device.

10. The display apparatus according to claim 9 , wherein the transistor includes an electrode formed of a transparent oxide semiconductor.

11. The display apparatus according to claim 9 , further comprising a color filter.

12. An imaging apparatus comprising:
a display portion, the display portion comprising the display apparatus according to claim 9 .

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

14. An organic light-emitting device comprising:
a pair of electrodes; and
an organic compound layer disposed between the pair of electrodes,
wherein the organic compound layer includes an iridium complex represented by the following general formula [6] and a hydrocarbon compound represented by the following general formula [10]:

in the formula [6]:
R 31 to R 38 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;
k represents an integer of 1 to 3 and 1 represents an integer of 0 to 2, provided that k+1 equals 3;
a ring A represents a cyclic structure selected from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a 9,9-spirobifluorene ring, and a chrysene ring, and is covalently bonded to a benzo[f]isoquinoline skeleton and an Ir metal, and the ring A may further have a substituent;
X represents a bidentate ligand; and
a partial structure IrX 1 comprises any one of structures represented by the following general formulae [7] to [9]:

in the formulae [7] to [9]:
R 39 to R 53 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydr

Assignees

• Canon Kk

Inventors

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

Classifications

• C09K2211/185

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

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0058

  Electricity · mapped topic