IP Library Granted Patent US 9,257,663
Granted Patent B2
US 9,257,663 · App. 14/407,825 · Granted Feb 9, 2016

Organic electroluminescent element and display device

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Quick Facts
Patent No.
US 9,257,663
App. No.
14/407,825
Granted
Feb 9, 2016
Kind
B2
Abstract

An organic electroluminescence device that includes, between an anode 41 and a cathode 42 , an organic layer stacked structure 43 that comprises stacked plural emitting layers that emit light of different colors, wherein the organic electroluminescent device comprises, between the emitting layers, at least one intermediate layer that comprises a compound represented by the following formula (1) in which at least one of Ar 1 , Ar 2 and Ar 3 is a group represented by the following formula (2):

Claims (31)

1. An organic electroluminescence device that comprises, between an anode and a cathode, an organic layer stacked structure that comprises stacked plural emitting layers that emit light of different colors,

wherein the organic electroluminescent device comprises, between the emitting layers, at least one intermediate layer that comprises a compound represented by the following formula (1):

wherein in the formula (1), Ar 1 to Ar 3 are independently a substituted or unsubstituted aromatic hydrocarbon group including 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms, and any one pair of Ar 1 and Ar 2 , Ar 1 and Ar 3 and Ar 2 and Ar 3 may be bonded to each other to form a substituted or unsubstituted nitrogen-containing heterocyclic ring including a nitrogen atom in the formula (1),

provided that at least one of Ar 1 to Ar 3 is a heterocyclic group represented by the following formula (2):

wherein in the formula (2), X is an oxygen atom or a sulfur atom and Y 1 to Y 8 are a carbon atom;

one of Y 1 to Y 8 is a carbon atom that is bonded to the following L 1 and the other seven of Y 1 to Y 8 are independently a carbon atom that is bonded to the following R or form a substituted or unsubstituted ring that includes an adjacent carbon atom;

L 1 is a linkage group that is bonded to a nitrogen atom in the formula (1), and is a single bond or a substituted or unsubstituted aromatic hydrocarbon group including 6 to 50 ring carbon atoms;

R is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 10 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group including 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group including 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group including 8 to 15 carbon atoms (an aryl part includes 6 to 14 ring carbon atoms), a substituted or unsubstituted aromatic hydrocarbon group including 6 to 16 ring carbon atoms, a substituted amino group, a group including a substituted amino group, a halogen atom or a cyano group.

2. The organic electroluminescence device according to claim 1 , wherein at least one emitting layer of the plural emitting layers comprises an anthracene derivative as a host material.

3. The organic electroluminescence device according to claim 2 , wherein the anthracene derivative is a compound represented by the following formula (3):

wherein in the formula (3), B 1 and B 2 are independently a substituted or unsubstituted aromatic hydrocarbon group including 6 to 20 ring carbon atoms; and

R 11 to R 18 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group including 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group including 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms.

4. The organic electroluminescence device according to claim 2 , wherein at least one emitting layer of the remaining emitting layers other than the emitting layer that comprises an anthracene derivative as a host material comprises at least compound A having an ionization potential of less than 5.6 eV as a host material.

5. The organic electroluminescence device according to claim 4 , wherein the compound A is a polycyclic aromatic hydrocarbon compound including a 4 to 7-membered mother skeleton.

6. The organic electroluminescence device according to claim 5 , wherein the mother skeleton of the polycyclic aromatic hydrocarbon compound is pyrene, benzopyrene, chrysene, naphthacene, benzonaphthacene, dibenzonaphthacene, perylene or coronene.

7. The organic electroluminescence device according to claim 4 , wherein the compound A is a compound represented by the following formula (4):

wherein in the formula (4), R 21 to R 28 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group including 3 to 30 carbon atoms, a substituted or unsubstituted arylsily group including 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms.

8. The organic electroluminescence device according to claim 4 , wherein the emitting layer including the compound A comprises, as a dopant material, a perylene derivative, a diketo-pyrrolo-pyrrole derivative, a pyrromethene complex, a pyrane derivative or a styryl derivative.

9. The organic electroluminescence device according to claim 4 that comprises, between an anode and a cathode, a first emitting layer, an intermediate layer, a second emitting layer and a third emitting layer being stacked in this sequence from the anode side,

wherein

the first emitting layer comprises at least the compound A as a host material; and

the second emitting layer and the third emitting layer comprise an anthracene derivative as a host material.

10. The organic electroluminescence device according to claim 2 , wherein at least one emitting layer of the remaining emitting layers other than the emitting layer that comprises an anthracene derivative as a host material comprises at least a phosphorescent emitting material as a host material.

11. The organic electroluminescence device according to claim 10 , wherein the phosphorescent emitting material is a carbazole derivative or a quinoline complex derivative.

12. The organic electroluminescence device according to claim 10 that comprises, between an anode and a cathode, a first emitting layer, an intermediate layer and a second emitting layer being stacked from the anode side,

wherein

the first emitting layer comprises at least a phosphorescent emitting material as a host material, and

the second emitting layer comprises an anthracene derivative as a host material.

13. The organic electroluminescence device according to claim 1 , wherein a part of the organic layer stacked structure, said part being in contact with the anode, comprises a hole-supplying layer, and a part of the organic layer stacked structure, said part being in contact with the cathode, comprises an electron-supplying layer.

14. The organic electroluminescence device according to claim 1 , that emits white light by overlapping of light emitted from the plural emitting layers.

15. A display that comprises the organic electroluminescence devices according to claim 1 that are arranged in a two-dimensional matrix form.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2025
From: JDI DESIGN AND DEVELOPMENT G.K.
To: MAGNOLIA BLUE CORPORATION
Reel/Frame 072039/0656 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2024
From: JOLED, INC.
To: JDI DESIGN AND DEVELOPMENT G.K.
Reel/Frame 066382/0619 →
CORRECTION BY AFFIDAVIT FILED AGAINST REEL/FRAME 063396/0671 Recorded Jun 12, 2023
From: JOLED, INC.
To: JOLED, INC.
Reel/Frame 064067/0723 →
SECURITY INTEREST Recorded Apr 20, 2023
From: JOLED, INC.
To: INCJ, LTD.
Reel/Frame 063396/0671 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2017
From: SONY CORPORATION
To: JOLED INC.
Reel/Frame 043071/0901 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2015
From: NAKAMURA, MASATO; KAMBE, EMIKO; FUNAHASHI, MASAKAZU
To: SONY CORPORATION
Reel/Frame 035571/0526 →