Material for organic electroluminescent elements, and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-9923151-B2
Application number	US-201113976246-A
Country	US
Kind code	B2
Filing date	Dec 26, 2011
Priority date	Dec 28, 2010
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

A material for organic electroluminescence device having a specific structure, in which an aromatic ring of a dibenzofuran skeleton, a carbazole skeleton, or a dibenzothiophene skeleton has a nitrogen atom as a heteroatom, and an organic electroluminescence device including an organic thin film layer which includes one or more layers between a cathode and an anode. The organic thin film layer includes a light emitting layer which includes a phosphorescent emitting material. At least one layer of the organic thin film layer includes the material for organic electroluminescence device. The organic EL device employing the material for organic EL device has a high external quantum efficiency even when driving the device at low voltage and also has a long lifetime.

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein:
at least one of G 11 to G 18 represents a nitrogen atom, another of G 11 to G 18 represents a carbon atom bonded to L 1 , and the other or others of G 11 to G 18 represent C(R 1 );
one of G 21 to G 28 represents a carbon atom bonded to L 2 and the others represent C(R 2 ) or a nitrogen atom;
one of G 31 to G 38 represents a carbon atom bonded to L 2 and the others represent C(R 3 ) or a nitrogen atom;
each R 1 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group comprising 5 to 18 ring atoms, a substituted or unsubstituted aryloxy group comprising 6 to 18 ring carbon atoms, a substituted or unsubstituted amino group comprising 0 to 20 carbon atoms, a substituted or unsubstituted silyl group comprising 0 to 30 carbon atoms, a fluorine atom, or a cyano group;
each R 2 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group, wherein the heteroaryl group is selected from the group consisting of a carbolinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrrolyl group, a furyl group, a thienyl group, a silolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a benzofuryl group, a benzothiophenyl group, an imidazolyl group, a benzimidazolyl group, a pyrimidyl group, a selenophenyl group, an oxadiazolyl group, a triazolyl group, an azaphenanthryl group, and a phenanthrolinyl group, a substituted or unsubstituted aryloxy group comprising 6 to 18 ring carbon atoms, a substituted or unsubstituted amino group comprising 0 to 20 carbon atoms, a substituted or unsubstituted silyl group comprising 0 to 30 carbon atoms, a fluorine atom, or a cyano group;
R 1 groups and R 2 groups may be the same or different;
each R 3 represents a hydrogen atom;
each optional substituent of R 1 and R 2 is independently an alkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 3 to 20 ring carbon atoms, an alkoxy group comprising 1 to 20 carbon atoms, a cycloalkoxy group comprising 3 to 20 ring carbon atoms, an aryl group comprising 6 to 18 ring carbon atoms, a heteroaryl group comprising 5 to 18 ring atoms, an aryloxy group comprising 6 to 18 ring carbon atoms, an amino group comprising 0 to 20 carbon atoms, a silyl group comprising 0 to 30 carbon atoms, a fluorine atom, or a cyano group;
X 1 represents an oxygen atom, a sulfur atom, or —N(R 4 )—;
R 4 represents a hydrogen atom, an alkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 3 to 20 ring carbon atoms, an aryl group comprising 6 to 18 ring carbon atoms, or a heteroaryl group comprising 5 to 18 ring atoms;
L 1 represents a single bond, an alkylene group comprising 1 to 20 carbon atoms, a cycloalkylene group comprising 3 to 20 ring carbon atoms, an arylene group comprising 6 to 18 ring carbon atoms, or a heteroarylene group comprising 5 to 18 ring atoms, provided that divalent residues of dibenzofuran and dibenzothiophene are excluded;
L 2 represents a single bond, an alkylene group comprising 1 to 20 carbon atoms, a cycloalkylene group comprising 3 to 20 ring carbon atoms, an arylene group comprising 6 to 18 ring carbon atoms, a heteroarylene group selected from the group consisting of residues obtained by removing one hydrogen atom from a carbolinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrrolyl group, a furyl group, a thienyl group, a silolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a benzofuryl group, a benzothiophenyl group, an imidazolyl group, a benzimidazolyl group, a pyrimidyl group, a selenophenyl group, an oxadiazolyl group, a triazolyl group, an azaphenanthryl group, and a phenanthrolinyl group, an oxygen-comprising divalent linking group, a silicon-comprising divalent linking group, a phosphorous-comprising divalent linking group, or a sulfur-comprising divalent linking group;
Y represents an oxygen atom, a sulfur atom, or —N(-L 3 -R 5 )—, wherein Y represents an oxygen atom or a sulfur atom when L 2 represents a single bond;
L 3 represents a single bond, an alkylene group comprising 1 to 20 carbon atoms, a cycloalkylene group comprising 3 to 20 ring carbon atoms, an arylene group comprising 6 to 18 ring carbon atoms, or a heteroarylene group comprising 5 to 18 ring atoms; and
R 5 represents a hydrogen atom, an alkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 3 to 20 ring carbon atoms, an aryl group comprising 6 to 18 ring carbon atoms, or a heteroaryl group comprising 5 to 18 ring atoms;
provided that when X 1 represents an oxygen atom or a sulfur atom, only one of G 11 to G 18 represents a nitrogen atom, and when X 1 represents —N(R 4 )—, Y represents —N(-L 3 -R 5 )—and simultaneously each of R 2 and R 3 represents a hydrogen atom.

2. The compound of claim 1 , wherein G 14 of formula (1) represents a nitrogen atom.

3. The compound of claim 1 , wherein X 1 of formula (1) represents an oxygen atom or a sulfur atom.

4. The compound of claim 1 , wherein:
Y of formula (1) represents —N(-L 3 -R 5 )—; and
R 5 represents a heteroaryl group represented by formula (A):

wherein:
one of G 41 to G 48 represents a carbon adorn bonded to L 3 and the others represent a nitrogen atom or C(R 6 );
R 6 represents a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group comprising 5 to 18 ring atoms, a substituted or unsubstituted aryloxy group comprising 6 to 18 ring carbon atoms, a substituted or unsubstituted amino group comprising 0 to 20 carbon atoms, a substituted or unsubstituted silyl group comprising 0 to 30 carbon atoms, a fluorine atom, or a cyano group, provided that R 6 groups may be the same or different;
each optional substituent of R 6 is independently an alkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 3 to 20 ring carbon atoms, an alkoxy group comprising 1 to 20 carbon atoms, a cycloalkoxy group comprising 3 to 20 ring carbon atoms, an aryl group comprising 6 to 18 ring carbon atoms, a heteroaryl group comprising 5 to 18 ring atoms, an aryloxy group comprising 6 to 18 ring carbon atoms, an amino group comprising 0 to 20 carbon atoms, a silyl group comprising 0 to 30 carbon atoms, a fluorine atom, or a cyano group;
X 2 represents an oxygen atom, a sulfur atom, or —N(R 7 )—; and
R 7 repres

Assignees

• Numata Masaki
• Idemitsu Kosan Co

Inventors

• Numata Masaki

Classifications

• H01L51/0072 Primary

  Electricity · mapped topic

• C09K2211/1011

  Condensed systems · CPC title

• H01L51/5056

  Electricity · mapped topic

• H01L51/0073

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic