Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11217754-B2
Application number	US-201515329083-A
Country	US
Kind code	B2
Filing date	Jul 27, 2015
Priority date	Jul 29, 2014
Publication date	Jan 4, 2022
Grant date	Jan 4, 2022

Abstract

According to the present invention, there is provided an organic electroluminescent device which has an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode arranged in order of description. The device is characterized in that: the hole transport layer includes a specific arylamine compound, and that the luminous layer includes a specific indenoindole derivative or a specific carbazole derivative. The organic EL device of the present invention has improved efficiency of hole transport from the hole transport layer to the luminous layer and also improved efficiency of electron transport from the electron transport layer to the luminous layer, in comparison to conventional organic EL devices.

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 order of description, wherein
the hole transport layer includes Compound (1-5), Compound (1-6), Compound (1-32), Compound (1-37), Compound (1-39), Compound (1-41), Compound (1-42), or Compound (1-45):

and
the luminous layer includes an indenoindole derivative represented by the following formula (2):

wherein
A 1 represents a divalent group of an aromatic hydrocarbon, a divalent group of an aromatic heterocyclic ring, or a single bond;
Ar 5 represents an aromatic hydrocarbon group or an 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, an aromatic hydrocarbon group, an aromatic heterocyclic group, an aryloxy group, or a disubstituted amino group having an aromatic hydrocarbon group or an aromatic heterocyclic group as a substituent;
respective groups among 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;
respective groups among 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;
some of R 1 to R 4 may be detached and the remaining groups of R 1 to R 4 may be bonded to vacancies generated by the detachment via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring;
some of R 5 to R 8 may be detached and the remaining groups of R 5 to R 8 may be bonded to vacancies generated by the 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 are each an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group, or an aromatic heterocyclic group and 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;
or a carbazole derivative represented by the following formula (3):

wherein,
A 2 represents a divalent group of an aromatic hydrocarbon, a divalent group of an aromatic heterocyclic ring, or a single bond;
Ar 6 represents an aromatic hydrocarbon group or an 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, an aromatic hydrocarbon group, an aromatic heterocyclic group, an aryloxy group, or a disubstituted amino group having an aromatic hydrocarbon group or an aromatic heterocyclic group as a substituent;
respective groups among 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;
respective groups among 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;
some of R 11 to R 14 may be detached and the remaining groups of R 11 to R 14 may be bonded to vacancies generated by the detachment via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring; and
some of R 15 to R 18 may be detached and the remaining groups of R 15 to R 18 may be bonded to vacancies generated by the detachment via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monoarylamino group to form a ring;
provided that when any of Ar 1 to Ar 4 has a substituent, the substituent is a deuterium, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aromatic hydrocarbon group.

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

wherein,
Ar 7 represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
Ar 8 represents a hydrogen atom, a deuterium atom, an aromatic hydrocarbon group or an aromatic heterocyclic group;
R 19 to R 26 each 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, an aromatic hydrocarbon group, or an aromatic heterocyclic group;
m represents an integer of 0 to 2;
when m is 2, a plurality of existing R 19 , R 20 , R 21 , and R 22 may be the same or different.

3. The organic electroluminescence device according to claim 1 , wherein the electron transport layer includes an anthracene derivative represented by the following formula (5):

wherein,
in p and q, p is an integer of 7 or 8 and q is an integer of 1 or 2 such that a sum of p and q being 9 is maintained;
A 3 represents a divalent group of an aromatic hydrocarbon, a divalent group of an aromatic heterocyclic ring, or a single bond;
B represents an aromatic heterocyclic group;
C represents an aromatic hydrocarbon group or an aromatic heterocyclic group; when q is 2, a plurality of existing C may be the same or different; and
D represents 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 a plurality of existing D may be the same or different.

4. The organic electroluminescence device according to claim 3 , wherein the anthracene derivative is represented by the following formula (5a′):

wherein,
Ar 9 to Ar 11 each represents an aromatic hydrocarbon group or an aromatic heterocyclic group; and
R 27 , R 28 , and R 30 to R 33 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, an aromatic hydrocarbon group, an aromatic heterocyclic group, or an aryloxy group and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an

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

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D493/04

  Ortho-condensed systems · CPC title

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title