Organic electroluminescence composition, material for organic electroluminescence element, solution of material for organic electroluminescence element, and organic electroluminescence element

Patent metadata

Field	Value
Publication number	US-10833281-B2
Application number	US-201414911235-A
Country	US
Kind code	B2
Filing date	Aug 8, 2014
Priority date	Aug 9, 2013
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

An organic electroluminescence composition including two or more compounds each having a specific structure combining a hole transporting ability and an electron transporting ability; an organic electroluminescence composition including one or more compounds each having a specific structure combining a hole transporting ability and an electron transporting ability and a different compound having an electron transporting skeleton; and a material for organic electroluminescence devices, a solution of a material for organic electroluminescence devices and an organic electroluminescence device, each including the aromatic heterocyclic derivative.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising a cathode, an anode, and at least one organic thin film layer disposed between the cathode and the anode,
wherein:
the at least one organic thin film layer includes a light emitting layer comprising two host materials in total;
the two host materials consist of two compounds represented by formula (1), or the two host materials consist of one compound represented by formula (1) and one compound represented by formula (3) which is different from the compound represented by formula (1):

A represents a substituted or unsubstituted aromatic heterocyclic group having at least one nitrogen atom;
L 1 represents a single bond, a substituted or unsubstituted aromatic hydrocarbon ring group, or a substituted or unsubstituted aromatic heterocyclic group;
m represents an integer of 2 or more;
groups L 1 may be the same or different, and residues B may be the same or different;
each X 5 and each Y 5 represent a single bond, —CR 2 —, —NR—, —O—, —S—, or —SiR 2 —, provided that X 5 and Y 5 cannot all be a single bond;
R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aromatic hydrocarbon ring group, or a substituted or unsubstituted aromatic heterocyclic group;
Z 7 and Z 8 each independently represent a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted aliphatic heterocyclic group, a substituted or unsubstituted aromatic hydrocarbon ring group, or a substituted or unsubstituted aromatic heterocyclic group, provided that each of Z 7 and Z 8 does not represent an alicyclic hydrocarbon group having three or more fused rings, an aliphatic heterocyclic group having three or more fused rings, an aromatic hydrocarbon ring group having three or more fused rings, or an aromatic heterocyclic group having three or more fused rings;
t represents an integer of 1 or more;
L 3 represents a single bond, a substituted or unsubstituted aromatic hydrocarbon ring group, a substituted or unsubstituted aromatic heterocyclic group, or a combination thereof, provided that when t is 1, L 3 is not a single bond;
B of formula (1) is a group represented by formula (2-A) or (2-B):

in formula (2-A),
Xb 12 represents —NR—, —O—, —S—, or —SiR 2 —,
Rb 11 , Rb 12 , and Rb 13 , and Rb 14 each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon, atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 24 ring carbon atoms,
s 1 is an integer of 0 to 4, and when s 1 is 2 or more, groups Rb 11 may be the same or different,
t 1 is an integer of 0 to 3, and when t 1 is 2 or more, groups Rb 12 may be the same or different,
u 1 is an integer of 0 to 3, and when u 1 is 2 or more, groups Rb 13 may tae the same or different, and
v 1 is an integer of 0 to 4, and when v 1 is 2 or more, groups Rb 14 may be the same or different, and
* is a bonding site to L 1 of formula (1);

in formula (2-B),
s 1 represents an integer of 0 to 3;

the aromatic heterocyclic group of A in formula (1) is at least one selected from the group consisting of pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, aziridine, azaindolizine, indolizine, imidazole, indole, isoindole, indazole, purine, pteridine, β-carboline, naphthyridine, benzo[f]quinazoline, benzo[h]quinazoline, azafluoranthene, diazafluoranthene, pyrazole, tetrazole, quinolizine, cinnoline, phthalazine, biscarbazole, phenazine, azatriphenylene, diazatriphenylene, hexaazatriphenylene, azacarbazole, azadibenzofuran, azadibenzothiophene, and dinaphtho[2′3′:2,3:2′,3′:6,]carbazole; and
an optional substituent of the substituted or unsubstituted aromatic heterocyclic group of A in formula (1) is at least one selected from the group consisting of a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 ring carbon atoms, an aralkyl group having 7 to 51 carbon atoms which includes an aryl group having 6 to 50 ring carbon atoms, an amino group, a mono- or di-substituted amino group, wherein the substituent is selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, an alkoxy group having an alkyl group having 1 to 50 carbon atoms, an aryloxy group having an aryl group having 6 to 50 ring carbon atoms, a mono-, di- or tri-substituted silyl group, wherein the substituent is selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, a nitro group, a substituted sulfonyl group, wherein the substituent is selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, a di-substituted phosphoryl group, wherein the substituent is selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, an alkylsulfonyloxy group, an arylsulfonyloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, a boron-containing group, a zinc-containing group, a tin-containing group, a silicon-containing group, a magnesium-containing group, a lithium-containing group, a hydroxyl group, an alkyl-substituted or aryl-substituted carbonyl group, a carboxyl group, a vinyl group, a (meth)acryloyl group, an epoxy group, and oxetanyl group.

2. An organic electroluminescence composition comprising a compound represented by formula (1) and at least one compound which is different from the compound represented by formula (1) and selected from compounds represented by formula (7):
A L 1 -B) m   (1)

wherein:
A represents a substituted or unsubstituted aromatic heterocyclic group having at least one nitrogen atom;
L 1 represents a single bond, a substituted or unsubstituted aromatic hydrocarbon ring, group, or a substituted or unsubstituted aromatic heterocyclic group;
B represents a residue of a structure represented by any one of formulae (2-a-1) to (2-a-6);
m represents an integer of 2 or more, and
groups L 1 may be the same or different, and residues B may be the same or different;

in formula (2-a-1), Xa 11 and Xa 12 each independently represent, —CR 2 —, —NR—, —O—, —S—, or —SiR 2 —; R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aromatic hydrocarbon ring group, or a substituted or unsubstituted aromatic heterocyclic group; each Ra 1 independently represent a substituted or unsubstituted alkyl group having 1 to 20

Assignees

• Idemitsu Kosan Co
• Joled Inc

Inventors

• Kawakami Hironori
• Funahashi Masakazu
• Yoshinaga Tadahiko
• Toyoshima Hiroaki

Classifications

• C07D209/14

  Radicals substituted by nitrogen atoms, not forming part of a nitro radical · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title

• C07D471/14

  Ortho-condensed systems · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D409/10

  linked by a carbon chain containing aromatic rings · CPC title