Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-2017271599-A1
Application number	US-201515504804-A
Country	US
Kind code	A1
Filing date	Aug 6, 2015
Priority date	Aug 20, 2014
Publication date	Sep 21, 2017
Grant date	—

Abstract

The organic EL device of the invention has, in order, an anode, a hole transport layer, a luminous layer, an electron transport layer and a cathode. The hole transport layer includes an indenoacridan derivative represented by the following general formula (1), and the luminous layer includes an N-aromatic substituted indenoindole compound and/or an N-aromatic substituted carbazole compound. In the formula, A 1 is a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group or a single bond, B is a monovalent aromatic hydrocarbon group; a monovalent aromatic heterocyclic group; or a disubstituted amino group having, as a substituent, a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group; and R 1 to R 14 each represent a hydrogen atom or an alkyl group.

First claim

1 . An organic electroluminescent device comprising, in order, an anode, a hole transport layer, a luminous layer, an electron transport layer and a cathode, wherein the hole transport layer includes an indenoacridan derivative represented by the following general formula (1), and the luminous layer includes an N-aromatic substituted indenoindole compound and/or an N-aromatic substituted carbazole compound;

where
A 1 is a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group or a single bond,
B is a monovalent aromatic hydrocarbon group; a monovalent aromatic heterocyclic group; or a disubstituted amino group having, as a substituent, a vinyl group which may have a substituent, a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group;
when B is a disubstituted amino group, A 1 is not a single bond, and when A 1 is not a single bond, A 1 and B may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring,
R 1 to R 10 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, 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 methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring, and
R 11 to R 14 each represent 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 R 11 and R 12 , or R 13 and R 14 , may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring.

2 . The organic electroluminescent device according to claim 1 , wherein the N-aromatic substituted indenoindole compound is represented by the following general formula (2);

where
A 2 is a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group or a single bond,
Ar 1 is a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group,
R 15 to R 22 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, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, an aralkyl group, an aryloxy group, or a disubstituted amino group having, as a substituent, a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group, may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring, and some of R 15 to R 18 or some of R 19 to R 22 may be detached and the remaining groups of R 15 to R 18 or the remaining groups of R 19 to R 22 may be bonded to vacancies generated by the detachment via a methylene group which may have a substituent, an oxygen atom, a sulfur atom or a monoarylamino group to form a ring, and
R 23 and R 24 each represent an alkyl group having 1 to 6 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group or an aralkyl group, and may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring.

3 . The organic electroluminescent device according to claim 1 , wherein the N-aromatic substituted carbazole compound is represented by the following general formula (3);

where
A 3 is a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group or a single bond,
Ar 2 is a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group, and
R 25 to R 32 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, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, an aralkyl group, an aryloxy group, or a disubstituted amino group having, as a substituent, a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group, may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring, and some of R 25 to R 28 or some of R 29 to R 32 may be detached and the remaining groups of R 25 to R 28 or the remaining groups of R 29 to R 32 may be bonded to vacancies generated by the detachment via a methylene group which may have a substituent, an oxygen atom, a sulfur atom or a monoarylamino group to form a ring.

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

where
A 4 is a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group or a single bond,
E is a monovalent aromatic heterocyclic group,
C is a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group,
D is a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 6 carbon atoms, and
p is an integer of 7 or 8 and q is an integer of 1 or 2, with the proviso that the sum of p and q is 9.

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

where
A 4 is as defined in the formula (4),
Ar 3 , Ar 4 and Ar 5 each represent a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group,
R 33 to R 39 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, 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, a methylene group which may have a substituent, an oxygen atom or a sulfur atom to form a ring, and
X 1 , X 2 , X 3 and X 4 each represent a carbon atom or a nitrogen atom, provided that only one of these is a nitrogen atom, with none of R 33 to R 36 ,

Assignees

• Hodogaya Chemical Co Ltd
• Sfc Co Ltd

Inventors

• Hayashi Shuichi
• Kanda Daizou
• Mochiduki Shunji
• Lee Se-Jin
• Lee Oun-Gyu
• Shin Bong-Ki

Classifications

• C07D209/94

  containing carbocyclic rings other than six-membered · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D221/18

  Ring systems of four or more rings · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title