Organic electroluminescence device and organic light emitting medium

Patent metadata

Field	Value
Publication number	US-9728727-B2
Application number	US-201313964203-A
Country	US
Kind code	B2
Filing date	Aug 12, 2013
Priority date	Jul 19, 2002
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

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) at least one arylamine compound of formula (V):

wherein:
X 3 is an unsubstituted pyrene residue;
each of Ar 5 and Ar 6 is independently a substituted or unsubstituted aromatic group 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;
p is 2; and
(B) at least one anthracene derivative of formula (I):
A 1 -L-A 2   (I)

wherein:
A 1 and A 2 may be the same or different and each of A 1 and A 2 is independently a substituted or unsubstituted monophenylanthryl group or a substituted or unsubstituted diphenylanthryl group; and
L is a single bond or a divalent bonding group; and
a weight ratio of component (A) to component (B) is from 1:99 to 20:80.

2. The electroluminescence device according to claim 1 , wherein the anthracene derivative is of formula (I-a):

wherein:
each of R 1 to R 10 is independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, an alkoxyl group, an aryloxyl group, an alkylamino group, an alkenyl group, an arylamino group, or a heterocyclic group which may be substituted:
each of a and b is an integer of 1 to 5
when each of a and b represents an integer of 2 or greater, atoms or groups represented by a plurality of R 1 and R 2 may be the same or different and may be bonded to each other to form a ring;
groups represented by combinations of R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , and R 9 and R 10 may be bonded to each other to form a ring; and
L 1 is a single bond, —O—, —S—, —N(R)— wherein R is an alkyl group or an aryl group which may be substituted, an alkylene group, or an arylene group.

3. The electroluminescence device according to claim 1 , wherein the anthracene derivative is of formula (I-b):

wherein:
each of R 11 to R 20 is independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, an alkoxyl group, an aryloxyl group, an alkylamino group, an arylamino group, or a heterocyclic group which may be substituted:
each of c, d, e, and f is an integer of 1 to 5;
when each of c, d, e, and f represents an integer of 2 or greater, atoms or groups represented by a plurality of R 11 , R 12 , R 16 , and R 17 may be the same or different and may be bonded to each other to form a ring;
groups represented by combinations of R 13 and R 14 , and R 18 and R 19 may be bonded to each other to form a and
L 2 is a single bond, —O—, —S—, —N(R)— wherein R is an alkyl group or an aryl group which may be substituted, an alkylene group, or an arylene group.

4. 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.

5. 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.

6. 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.

7. The electroluminescence device of claim 1 , wherein at least one of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group.

8. The electroluminescence device of claim 1 , wherein each of Ar 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group.

9. The electroluminescence device of claim 1 , wherein each of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group.

10. The electroluminescence device of claim 1 , wherein each optional substituent of Ar 5 and Ar 6 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 arylamino 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.

11. The electroluminescence device of claim 1 , wherein each optional substituent of Ar 5 and Ar 6 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, a cyano group, and a halogen atom.

12. The electroluminescence device of claim 1 , wherein each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

13. The electroluminescence device of claim 1 , wherein:
each of Ar 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group; and
each optional substituent of Ar 5 and Ar 6 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, a cyano group, and a halogen atom.

14. The electroluminescence device of claim 1 , wherein:
at least one of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group; and
each optional substituent of Ar 5 and Ar 6 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, a cyano group, and a halogen atom.

15. The electroluminescence device of claim 1 , wherein:
each of A 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group; and
each optional substituent of A 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

16. The electroluminescence device of claim 1 , wherein:
at least one of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group; and
each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

17. The electroluminescence device of claim 1 , wherein:
each of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group; and
each optional substituent of Ar 5 and Ar 6 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, a cyano group, and a halogen atom.

18. The electroluminescence device of clai

Assignees

• Idemitsu Kosan Co

Inventors

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

Classifications

• H01L51/006

  Electricity · mapped topic

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C07C15/28

  Anthracenes · CPC title

• C07C2103/46

  Chemistry & Metallurgy · mapped topic

• H01L51/0052

  Electricity · mapped topic