IP Library Granted Patent US 10,243,145
Granted Patent B2
US 10,243,145 · App. 15/925,968 · Granted Mar 26, 2019

Organic electroluminescence device and organic light emitting medium

Inventors: Masahide Matsuura (Chiba, JP); Masakazu Funahashi (Chiba, JP); Kenichi Fukuoka (Chiba, JP); Chishio Hosokawa (Chiba, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0058C07C13/567C07C13/72C07C15/28C07C15/30C07C15/38C07C15/52C09K11/06H01L51/006H01L51/0052H01L51/0054H01L51/0056H01L51/0072H05B33/14B82Y30/00C07C2603/46C07C2603/50C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1018H01L51/0055H01L51/0059H01L51/0062H01L51/0096H01L51/5012H01L51/5024H01L51/5052H01L51/5206H01L51/5221H01L51/56Y10S428/917Y10S977/755
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,243,145
App. No.
15/925,968
Granted
Mar 26, 2019
Kind
B2
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.

Claims (52)

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 group having 3 to 10 carbon atoms;

when any of g, h, i, and j is an integer of 2 or greater, two or more of A 15 to A 18 may be the same or different and may be bonded to each other to form a saturated or unsaturated ring; and

n is an integer of 0 to 3;

or

an arylamine compound according to formula (V-b):

wherein:

X 3 , A 15 to A 18 , g, h, i, and j are as defined in formula (V-a);

each of R 24 and R 25 is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryloxyl group having 5 to 50 carbon atoms; and

each of k and m is an integer of 0 to 2, provided that at least one of k and m is 1 or greater and at least one of R 24 and R 25 is a substituted or unsubstituted secondary or tertiary alkyl group having 3 to 10 carbon atoms; and

(B) a compound having a condensed ring according to formula (IV):

wherein:

Ar 2 is a substituted or unsubstituted anthracene residue;

A 9 to A 11 are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms;

A 12 to A 14 are each 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;

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

the organic light emitting medium does not include a styrylaryl compound.

Priority Claims (1)
JP 2002-211308 · Jul 19, 2002 · national
Continuity (7)
Continuation 15638805 · Jun 30, 2017
Continuation 13964203 · Aug 12, 2013
Continuation 13675037 · Nov 13, 2012
Division 12773307 · May 4, 2010
Continuation 11207933 · Aug 22, 2005
Division 10617397 · Jul 11, 2003
Related Publication 20180212152A1 · Jul 26, 2018
Cited By (1)
US 12,606,741