Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-10454042-B2
Application number	US-201514953934-A
Country	US
Kind code	B2
Filing date	Nov 30, 2015
Priority date	Aug 31, 2009
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

An object of the present invention is to provide an organic electroluminescence device having excellent light emission efficiency and durability, in particular, durability when driving at a high temperature. Provided is an organic electroluminescence device including on a substrate a pair of electrodes, and at least one layer of an organic layer including a light emitting layer containing a light emitting material disposed between the electrodes, wherein the light emitting layer includes at least each one of specific indolocarbazole derivatives and specific condensed ring metal complexes.

First claim

The invention claimed is:

1. An organic electroluminescence device, comprising on a substrate:
a pair of electrodes; and
at least one organic light emitting layer between the electrodes,
wherein the light emitting layer contains at least each one of a compound represented by the following Formula (3) and a compound selected from the group consisting of A-6, B-7, and B-9:
Z 3 Y 3 ) n 3   (3)

wherein Z 3 represents benzene, pyridine, triazine, pyrimidine, biphenyl, phenylpyridine, bipyridine, a silicon atom or a carbon atom, and may be further substituted by at least one group selected from the group consisting of an alkyl group, an aryl group, a silyl group, a cyano group, a fluorine atom and a combination thereof;
Y 3 represents a group represented by the following Formula (3a-1) or (3a-2); and
n 3 represents an integer of 1 to 4:

in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring or a heterocyclic ring, represented by Formula (3b), which is condensed with an adjacent ring;
the ring B represents a heterocyclic ring represented by Formula (3c), which is condensed with an adjacent ring;
X 3 represents C—R″ in which R″ represents a hydrogen atom or a substituent, or a nitrogen atom;
each of R 34 and R 311 independently represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom;
R 33 represents a hydrogen atom;
each of R 31 and R 32 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6 carbon atoms and a phenyl group; and
* represents a bond for linking to Z 3 :

2. The organic electroluminescence device according to claim 1 ,
wherein the compound represented by Formula (3) is represented by the following Formula (1):

wherein the ring A represents an aromatic ring or a heterocyclic ring, represented by Formula (1a), which is condensed with an adjacent ring;
the ring B represents a heterocyclic ring represented by Formula (1b), which is condensed with an adjacent ring;
X 1 represents C—R″ in which R″ represents a hydrogen atom or a substituent, or a nitrogen atom;
each of R 11 and R 15 independently represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom;
R 14 represents a hydrogen atom; and
each of R 12 and R 13 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6 carbon atoms and a phenyl group.

3. The organic electroluminescence device according to claim 2 ,
wherein the compound represented by Formula (1) is represented by the following Formula (15):

wherein X 151 to X 153 represent a nitrogen atom or C—R 153 ;
R 153 represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group or a fluorine atom;
each of R 151 and R 152 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group or a fluorine atom; and
Y 15 represents a group represented by any one of the following Formulas (15a) to (15c):

wherein R 155 represents a hydrogen atom;
each of R 154 and R 156 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6 carbon atoms and a phenyl group; and
R 157 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom.

4. The organic electroluminescence device according to claim 3 ,
wherein the compound represented by Formula (15) is represented by the following Formula (16):

wherein X 161 to X 163 represent a nitrogen atom or C—H, and each of R 161 and R 162 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group or a fluorine atom; and
Y 16 represents a group represented by any one of the Formulas (15a) to (15c).

5. The organic electroluminescence device according to claim 4 , wherein the compound represented by Formula (16) is represented by the following Formula (17):

wherein each of R 171 and R 172 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group or a fluorine atom; and
Y 17 represents a group represented by any one of the Formulas (15a) to (15c).

6. The organic electroluminescence device according to claim 4 ,
wherein the compound represented by Formula (16) is represented by the following Formula (18):

wherein each of R 181 and R 182 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group or a fluorine atom; and
Y 18 represents a group represented by any one of the Formulas (15a) to (15c).

7. The organic electroluminescence device according to claim 1 ,
wherein the compound represented by Formula (3) is represented by the following Formula (9):

wherein each of R 91 to R 910 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group, a fluorine atom or a group represented by any one of the following Formula (10), (10-2) and (10-3), provided that each of at least two of R 91 to R 910 is independently a group represented by any one of the following Formula (10), (10-2) and (10-3); and
L 1 repres

Assignees

• UDC Ireland
• Udc Ireland Ltd

Inventors

• Fukuzaki Eiji

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09B57/10

  Metal complexes of organic compounds not being dyes in uncomplexed form · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title