Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-2017358753-A1
Application number	US-201615541429-A
Country	US
Kind code	A1
Filing date	Jan 5, 2016
Priority date	Jan 7, 2015
Publication date	Dec 14, 2017
Grant date	—

Abstract

The present invention provides an organic electroluminescent device having at least an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein the hole transport layer contains an arylamine compound having a specific structure, and the luminous layer contains an indenoindole derivative or a carbazole derivative having a specific structure. The organic EL device of the present invention is an organic EL device improved in luminous efficiency, driving voltage and durability.

First claim

1 . An organic electroluminescent device having at least an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein
the hole transport layer contains an arylamine compound represented by the following general formula (1), and the luminous layer contains an indenoindole derivative represented by the following general formula (2) or a carbazole derivative represented by the following general formula (3):

where
Ar 1 to Ar 4 each represent an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group,

where
A 1 represents a divalent group of an aromatic hydrocarbon, a divalent group of an aromatic heterocycle, a divalent group of a condensed polycyclic aromatic ring, or a single bond,
Ar 5 represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group,
R 1 to R 8 each represent a hydrogen atom; a deuterium atom; a fluorine atom; a chlorine atom; a cyano group; a nitro group; an alkyl group having 1 to 6 carbon atoms; a cycloalkyl group having 5 to 10 carbon atoms; an alkenyl group having 2 to 6 carbon atoms; an alkyloxy group having 1 to 6 carbon atoms; a cycloalkyloxy group having 5 to 10 carbon atoms; an aromatic hydrocarbon group; an aromatic heterocyclic group; a condensed polycyclic aromatic group; an aryloxyl group; or a di-substituted amino group having an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group as a substituent,
R 1 to R 4 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring,
R 5 to R 8 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring,
part of R 1 to R 4 may be detached, and remaining group of R 1 to R 4 may be bonded to a vacancy, which has been produced by detachment, via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring,
part of R 5 to R 8 may be detached, and remaining group of R 5 to R 8 may be bonded to a vacancy, which has been produced by detachment, via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring, and
R 9 and R 10 each represent an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group, and R 9 and R 10 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring,

where
A 2 represents a divalent group of an aromatic hydrocarbon, a divalent group of an aromatic heterocycle, a divalent group of a condensed polycyclic aromatic ring, or a single bond,
Ar 6 represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group,
R 11 to R 18 each represent a hydrogen atom; a deuterium atom; a fluorine atom; a chlorine atom; a cyano group; a nitro group; an alkyl group having 1 to 6 carbon atoms; a cycloalkyl group having 5 to 10 carbon atoms; an alkenyl group having 2 to 6 carbon atoms; an alkyloxy group having 1 to 6 carbon atoms; a cycloalkyloxy group having 5 to 10 carbon atoms; an aromatic hydrocarbon group; an aromatic heterocyclic group; a condensed polycyclic aromatic group; an aryloxyl group; or a di-substituted amino group having an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group as a substituent,
R 11 to R 14 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring,
R 15 to R 18 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring,
part of R 11 to R 14 may be detached, and remaining group of R 11 to R 14 may be bonded to a vacancy, which has been produced by detachment, via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring, and
part of R 15 to R 18 may be detached, and remaining group of R 15 to R 18 may be bonded to a vacancy, which has been produced by detachment, via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring.

2 . The organic electroluminescent device according to claim 1 , wherein
the electron transport layer contains a pyrimidine derivative represented by the following general formula (4):

where
Ar 7 represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group,
Ar 8 and Ar 9 each represent a hydrogen atom, an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group, and Ar 8 and Ar 9 are each not a hydrogen atom simultaneously, and
B represents a monovalent group represented by the following structural formula (5):

where
Ar 10 represents an aromatic heterocyclic group,
R 19 to R 22 each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group, and
R 19 to R 22 and Ar 10 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.

3 . The organic electroluminescent device according to claim 2 , wherein
the pyrimidine derivative is represented by the following general formula (4a):

where
Ar 7 to Ar 9 and B are as defined in the general formula (4).

4 . The organic electroluminescent device according to claim 2 , wherein
the pyrimidine derivative is represented by the following general formula (4b):

where
Ar 7 to Ar 9 and B are as defined in the general formula (4).

5 . The organic electroluminescent device according to claim 2 , wherein
in the general formula (4), B is a monovalent group represented by the following structural formula (5a):

where
Ar 10 and R 19 to R 22 are as defined in the structural formula (5).

6 . The organic electroluminescent device according to claim 1 , wherein
the hole transport layer has a two-layer structure composed of a first hole transport layer and a second hole transport layer, and the second hole transport layer is located on a side of the luminous lay

Assignees

• Hodogaya Chemical Co Ltd
• Sfc Co Ltd

Inventors

• Hayashi Shuichi
• Kabasawa Naoaki
• Mochiduki Shunji
• Lee Se-Jin
• Lee Oun-Gyu
• Shin Bong-Ki

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H01L51/0072

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0059 Primary

  Electricity · mapped topic

• C09K2211/185

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