Organic light-emitting element

Patent metadata

Field	Value
Publication number	US-10038152-B2
Application number	US-201314648494-A
Country	US
Kind code	B2
Filing date	Dec 24, 2013
Priority date	Dec 27, 2012
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

Provided is an organic light-emitting element improved in luminous efficiency and lifetime. The organic light-emitting element 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 benzo[f]isoquinoline of a specific structure as a ligand and a heterocycle-containing compound of a specific structure.

First claim

The invention claimed is:

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

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, and a 9,9-spirobifluorene 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 n comprises any one of structures represented by the following general formulae [2] to [4]:

in the formulae [2] to [4]:
R 9 to R 23 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,

in the formula [5]:
Z represents an oxygen atom or a sulfur atom;
a ring including Z is a five- or six-membered ring;
a ring B 1 and a ring B 2 each represent a cyclic structure selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a triphenylene ring, and a chrysene ring, and may be identical to or different from each other;
Y 1 and Y 2 each represent an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group;
a represents an integer of 0 to 4, and when a represents 2 or more, multiple Y 1 's may be identical to or different from each other;
b represents an integer of 0 to 4, provided that when the ring B 2 represents a benzene ring, b represents an integer of 0 to 3, and when b represents 2 or more, multiple Y 2 's may be identical to or different from each other;
Ar 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group;
Ar 2 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group; and
p represents an integer of 0 to 4, and when p represents 2 or more, multiple Ar 1 's may be identical to or different from each other,
wherein when:
(a) both of B 1 and B 2 are benzene rings,
(b) Z is a sulfur atom, and
(c) the ring including Z is a five-membered ring, then
p is not 0, and
the Ar 1 is selected from the group consisting of a naphthalenediyl group, a phenanthrenediyl group, an anthracenediyl group, a benzo[a]anthracenediyl group, a fluorenediyl group, a benzo[a]fluorenediyl group, a benzo[b]fluorenediyl group, a benzo[c]fluorenediyl group, a dibenzo[a,c]fluorenediyl group, a dibenzo[b,h]fluorenediyl group, a dibenzo[c,g]fluorenediyl group, an acenaphthylenediyl group, a chrysenediyl group, a benzo[b]chrysenediyl group, a pyrenediyl group, a benzo[e]pyrenediyl group, a triphenylenediyl group, a benzo[a]triphenylenediyl group, a benzo[b]triphenylenediyl group, a picenediyl group, a fluoranthenediyl group, a benzo[a]fluoranthenediyl group, a benzo[b]fluoranthenediyl group, a benzo[j]fluoranthenediyl group, a benzo[k]fluoranthenediyl group, a perylenediyl group, and a naphthacenediyl group.

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

3. The organic light-emitting element according to claim 1 , wherein the iridium complex represented by the general formula [1] comprises a compound represented by the following general formula [6]:

in the formula [6]:
R 24 to R 34 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;
*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 4-position in the benzo[f]isoquinoline skeleton; and
the ring A comprises any one of structures represented by the following general formulae [7] to [11]:

in the formulae [7] to [11]:
R 35 to R 56 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 4-position in the benzo[f]isoquinoline skeleton.

4. The organic light-emitting element according to claim 3 , wherein the ring A comprises the structure represented by the general formula [7].

5. The organic light-emitting element according to claim 1 , wherein in the heterocycle-containing compound represented by the general formula [5], a heterocycle formed of Z, the ring B 1 , and the ring B 2 comprises any one of heterocycles represented by the following general formulae [12] to [19]:

in the formulae [12] to [19], Z represents an oxygen atom or a sulfur atom.

6. The organic light-emitting element according to claim 1 , wherein the iridium complex represented by the general formula [1] comprises an iridium complex represented by the following general formula [20]:

in the formula [20]:
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.

7. The organic light-emitting element according to claim 1 , wherein the heterocycle-containing compound represented by the general formula [5] comprises a dibenzothiophene compound represented by the following general formula [21]:

in the formula [21], E 1 to E 3 each represent a hydrogen atom, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

8. The organic light-emitting element according to claim 7 wherein in the heterocycle-containing compounds represented by the general formulae [21] to [25]:
the p represents 1;
the Ar 1 represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted

Assignees

• Canon Kk

Inventors

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

Classifications

• G06F3/0412

  Digitisers structurally integrated in a display · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• G06F2203/04101

  2.5D-digitiser, i.e. digitiser detecting the X/Y position of the input means, finger or stylus, also when it does not touch, but is proximate to the digitiser's interaction surface and also measures the distance of the input means within a short range in the Z direction, possibly with a separate measurement setup · CPC title