Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-10505119-B2
Application number	US-201615541849-A
Country	US
Kind code	B2
Filing date	Jan 5, 2016
Priority date	Jan 8, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

The organic EL device of the present invention has an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in the order of description. The hole transport layer includes an arylamine compound represented by the following general formula (1):

in the formula,
Ar 1 to Ar 4 each represent a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group, and the luminous layer includes an N-aromatic substituted nitrogen-containing heterocyclic compound.

First claim

The invention claimed is:

1. An organic electroluminescence device having an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in the order of description, wherein the hole transport layer includes an arylamine compound represented by the following formula (1):

wherein
Ar 1 represents an unsubstituted phenyl group, a phenyl group substituted with a naphthyl group or a fluorenyl group, an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, an unsubstituted naphthyl group, or an unsubstituted spirofluorenyl group;
Ar 2 represents an unsubstituted phenyl group or an unsubstituted biphenylyl group;
Ar 3 and Ar 4 each represents an unsubstituted phenyl group, a phenyl group substituted with a naphthyl group or a fluorenyl group, an unsubstituted biphenylyl group, an unsubstituted fluorenyl group, a fluorenyl group substituted with an alkyl group or a phenyl group, an unsubstituted phenanthrenyl group, or an unsubstituted spirofluorenyl group;
the luminous layer includes an N-aromatic substituted nitrogen-containing heterocyclic compound selected from A) an indenoindole compound represented by one of the following formulae (2a) to 2(c):

in which
Ar 1 represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a single bond;
Ar 5 represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group;
R 1 to R 8 each represents 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, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, an aralkyl group, an aryloxy group, or a di-aromatic substituted amino group;
R 1 to R 8 may be bonded to each other via a single bond, an optionally substituted methylene group, an oxygen atom, or a sulfur atom to form a ring; further, some of R 1 to R 4 or some of R 5 to R 8 may be detached from the benzene ring, and the remaining groups of R 1 to R 4 or the remaining groups of R 5 to R 8 may be bonded to vacancies in the benzene ring generated by the detachment via an optionally substituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring;
R 9 and R 10 are each an alkyl group having 1 to 6 carbon atoms, a monovalent aromatic hydrocarbon group, or a monovalent aromatic heterocyclic group and may be bonded to each other via a single bond, an optionally substituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and
X is a divalent linking group and represents an optionally substituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group;
and B) a carbazole compound represented by one of the following formulas (3a-1) to (3a-4), (3b-1), and (3-16):

in which
A 2 represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a single bond;
Ar 6 represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group;
R 11 to R 18 each represents 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, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, an aralkyl group, an aryloxy group, or a di-aromatic substituted amino group; and
these R 11 to R 18 may be bonded to each other via a single bond, an optionally substituted methylene group, an oxygen atom, or a sulfur atom to form a ring; further, some of R 11 to R 14 or some of R 15 to R 18 may be detached from the benzene ring, and the remaining groups of R 11 to R 14 or the remaining groups of R 15 to R 18 may be bonded to vacancies in the benzene ring generated by the detachment via an optionally substituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring;
wherein the hole transport layer has a two-layer structure including a first hole transport layer and a second hole transport layer, and the second hole transport layer is positioned on a side of the luminous layer and includes the arylamine compound represented by formula (1).

2. The organic electroluminescence device according to claim 1 , wherein the arylamine compound is represented by the following formula (1a):

wherein
A 1 to A 3 are as defined in the formula (1); and
Ar 7 and A 8 each represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group.

3. The organic electroluminescence device according to claim 2 , wherein the arylamine compound is represented by the following formula (1b):

wherein
Ar 1 , Ar 2 , Ar 7 , and Ar 8 are as defined in the formula (1) or the formula (1a); and
Ar 9 and Ar 10 each represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group.

4. The organic electroluminescence device according to claim 1 , wherein the electron transport layer includes an anthracene derivative represented by the following formula (4):

wherein
A 3 represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a single bond;
B represents a monovalent aromatic heterocyclic group;
C represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group;
D represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, a monovalent aromatic hydrocarbon group, or a monovalent aromatic heterocyclic group; and
in p and q, p is an integer of 7 or 8 and q is an integer of 1 or 2 provided that a sum of p and q is 9.

5. The organic electroluminescence device according to claim 4 , wherein the anthracene derivative is represented by the following formula (4a):

wherein
A 3 is as defined in the general formula (4);
Ar 11 , Ar 12 , and Ar 13 each represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group;
R 19 to R 25 is each 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, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, an aralkyl group, or an aryloxy group and may be bonded to each other via a single bond, an optionally substituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and
X 1 , X 2 , X 3 , and X 4 each represent

Assignees

• Hodogaya Chemical Co Ltd
• Sfc Co Ltd

Inventors

• Yokoyama Norimasa
• Hayashi Shuichi
• Yamamoto Takeshi
• Kabasawa Naoaki
• Kanda Daizo
• Mochiduki Shunji
• Lee Se-Jin
• Lee Oun-Gyu
• Shin Bong-Ki

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07C211/54 Primary

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title