Organic electroluminescence device and organic light emitting medium

Patent metadata

Field	Value
Publication number	US-10243145-B2
Application number	US-201815925968-A
Country	US
Kind code	B2
Filing date	Mar 20, 2018
Priority date	Jul 19, 2002
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

An organic electroluminescence device having a layer of an organic light emitting medium which comprises (A) a specific arylamine compound and (B) at least one compound selected from specific anthracene derivatives, spirofluorene derivatives, compounds having condensed rings and metal complex compounds and is disposed between a pair of electrodes and an organic light emitting medium comprising the above components (A) and (B) are provided. The organic electroluminescence device exhibits a high purity of color, has excellent heat resistance and a long life and efficiently emits bluish to yellowish light. The organic light emitting medium can be advantageously used for the organic electroluminescence device.

First claim

The invention claimed is:

1. An electroluminescence device comprising a pair of electrodes and a layer of an organic light emitting medium disposed between the pair of electrodes, wherein the layer of an organic light emitting medium comprises:
(A) an arylamine compound according to formula (V):

wherein:
X 3 is a substituted or unsubstituted residue of naphthalene, phenanthrene, fluoranthene, anthracene, pyrene, perylene, coronene, chrysene, picene, diphenylanthracene, fluorene, triphenylene, rubicene, benzoanthracene, phenylanthracene, bisanthracene, dianthracenylbenzene, or dibenzoanthracene; each Ar 5 and Ar 6 is independently a substituted or unsubstituted monovalent aromatic group having 6 to 40 carbon atoms; and p is an integer of 1 to 4; and
(B) a compound having a condensed ring according to formula (IV):

wherein:
Ar 2 is a substituted or unsubstituted anthracene residue; each of A 9 to A 11 is independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; each of A 12 to A 14 is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an aryloxyl group having 5 to 18 carbon atoms, an aralkyloxyl group having 7 to 18 carbon atoms, a nitro group, a cyano group, an ester group having 1 to 6 carbon atoms or a halogen atom; at least one of A 9 to A 14 is a group having condensed aromatic rings; and each substituent of each substituted group in formula (IV) is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an aryloxyl group having 5 to 18 carbon atoms, an aralkyloxyl group having 7 to 18 carbon atoms, a nitro group, a cyano group, an ester group having 1 to 6 carbon atoms, and a halogen atom; and
wherein the organic light emitting medium is free of styrylaryl compounds.

2. The electroluminescence device according to claim 1 , wherein each of Ar 5 and Ar 6 is selected from the group consisting of a phenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a coronyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a furanyl group, a thienyl group, a benzothienyl group, an indolyl group, and a carbazolyl group.

3. The electroluminescence device according to claim 1 , wherein each substituent of each substituted group in formula (V) is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an aryloxyl group having 5 to 18 carbon atoms, an aralkyloxyl group having 7 to 18 carbon atoms, an acylamino group having 5 to 16 carbon atoms, a nitro group, a cyano group, an ester group having 1 to 6 carbon atoms, and a halogen atom.

4. The electroluminescence device according to claim 1 , wherein p is 2.

5. The electroluminescence device according to claim 1 , wherein A 9 to A 11 are each independently a substituted or unsubstituted divalent residue of benzene, biphenyl, terphenyl, phenanthrene, fluoranthene, anthracene, pyrene, perylene, coronene, chrysene, picene, fluorene, carbazole, rubicene, benzoanthracene, or dibenzoanthracene.

6. The electroluminescence device according to claim 1 , wherein:
when any of A 12 to A 14 is an alkyl group having 1 to 6 carbon atoms, the alkyl group is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, various types of pentyl group, and various types of hexyl group;
when any of A 12 to A 14 is a cycloalkyl group having 3 to 6 carbon atoms, the cycloalkyl group is selected from the group consisting of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
when any of A 12 to A 14 is an alkoxyl group having 1 to 6 carbon atoms, the alkoxyl group is selected from the group consisting of a methoxyl group, an ethoxyl group, a propoxyl group, an isopropoxyl group, a butoxyl group, an isobutoxyl group, a sec-butoxyl group, a tert-butoxyl group, various types of pentyloxyl groups, and various types of hexyloxyl groups;
when any of A 12 to A 14 is an aryloxyl group having 5 to 18 carbon atoms, the aryloxyl group is selected from the group consisting of a phenoxyl group, a tolyloxyl group, and a naphthyloxyl group;
when any of A 12 to A 14 is an aralkyloxyl group having 7 to 18 carbon atoms, the aralkyloxyl group is selected from the group consisting of a benzyloxyl group, a phenetyloxyl group, and a naphthylmethoxyl group;
when any of A 12 to A 14 is an ester group having 1 to 6 carbon atoms, the ester group is selected from the group consisting of a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and an isopropoxycarbonyl group; and
when any of A 12 to A 14 is a halogen atom, the halogen atom is selected from the group consisting of a fluorine atom, a chlorine atom, and a bromine atom.

7. The electroluminescence device according to claim 1 , wherein a weight ratio of component (A) to component (B) in the organic light emitting medium is 1:99 to 20:80.

8. The electroluminescence device according to claim 1 , wherein a layer of a chalcogenide, a layer of a metal halide, or a layer of a metal oxide is disposed on at least one surface of the pair of electrodes.

9. The electroluminescence device according to claim 1 , wherein a mixed region comprising a reducing dopant and organic substances or a mixed region comprising an oxidizing dopant and organic substances is disposed on at least one surface of the pair of electrodes.

10. The electroluminescence device according to claim 1 , wherein a thickness of the layer of an organic light emitting medium is from 10 to 40 nm.

11. An electroluminescence device comprising a pair of electrodes and a layer of an organic light emitting medium disposed between the pair of electrodes, wherein the layer of an organic light emitting medium comprises:
(A) an arylamine compound according to formula (V-a):

wherein:
X 3 is a substituted or unsubstituted residue of naphthalene, phenanthrene, fluoranthene, anthracene, pyrene, perylene, coronene, chrysene, picene, diphenylanthracene, fluorene, triphenylene, rubicene, benzoanthracene, phenylanthracene, bisanthracene, dianthracenylbenzene, or dibenzoanthracene;
each of A 15 to A 18 is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxyl group having 5 to 50 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 carbon atoms, or a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms;
each of g, h, i, and j is an integer of 0 to 5, provided that at least one of g, h, i and j is 1 or greater and at least one of A 15 to A 18 is a substituted or unsubstituted secondary or tertiary alkyl

Assignees

• Idemitsu Kosan Co

Inventors

• Matsuura Masahide
• Funahashi Masakazu
• Fukuoka Kenichi
• Hosokawa Chishio

Classifications

• H01L51/5206

  Electricity · mapped topic

• H01L51/56

  Electricity · mapped topic

• H01L51/5024

  Electricity · mapped topic

• H01L51/0096

  Electricity · mapped topic

• C09K2211/1007

  Non-condensed systems · CPC title