Nitrogenated aromatic heterocyclic derivative, and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-10043977-B2
Application number	US-201214233066-A
Country	US
Kind code	B2
Filing date	Jul 11, 2012
Priority date	Jul 15, 2011
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

A nitrogen-containing aromatic heterocyclic derivative in which a nitrogen atom of an indenocarbazole skeleton optionally having a hetero atom or an indenoindole skeleton optionally having a hetero atom is bonded to a dibenzofuran or a dibenzothiophene directly or indirectly. The derivative realizes an organic EL device with a high emission efficiency and a long lifetime.

First claim

What is claimed is:

1. An aromatic heterocyclic derivative selected from the group consisting of formulae (2-1), (3-1), (3-2) and (4-1):

wherein:
X is NR 5 ;
each of R 1 and R 3 to R 5 independently represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or unsubstituted silyl group, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group comprising from 5 to 30 ring atoms, a halogen atom, or a cyano group, or adjacent two groups of R 1 and R 3 to R 5 are bonded to each other to from a saturated or unsaturated divalent group which completes a ring;
each of a and d independently represents an integer of 0 to 4;
e represents an integer of 0 to 2; and
Q represents a structure represented by formula (1c):

wherein:
Y represents an oxygen atom or a sulfur atom;
L 2 represents a structure represented by any one of formulae (7a) to (7c):

wherein
each of R 11 to R 13 independently represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or an unsubstituted silyl group, an aryl group comprising from 6 to 20 ring carbon atoms, a heteroaryl group comprising from 5 to 20 ring atoms, a halogen atom, or a cyano group, or adjacent two groups of R 11 to R 13 are bonded to each other to from a saturated or an unsaturated divalent group which completes a ring;
each of R 14 and R 15 independently represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, an aryl group comprising from 6 to 20 ring carbon atoms, or a heteroaryl group comprising from 5 to 20 ring atoms; and
each of k1 to k3 independently represents an integer of 0 to 4;
L 2 is bonded to a carbon atom at a 4-position of the structure represented by formula (1c);
each of R 8 and R 9 independently represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or an unsubstituted silyl group, an aryl group comprising from 6 to 30 ring carbon atoms, a heteroaryl group comprising from 5 to 30 ring atoms, a halogen atom, or a cyano group, or adjacent too groups of R 8 and R 9 are bonded to each other to from a saturated or an unsaturated divalent group which completes a ring;
f represents an integer of 0 to 3; and
g represents an integer of 0 to 4.

2. The aromatic heterocyclic derivative according to claim 1 , wherein Y represents an oxygen atom.

3. The aromatic heterocyclic derivative according to claim 1 , wherein Y represents a sulfur atom.

4. A material for organic electroluminescence device, comprising the aromatic heterocyclic derivative according to claim 1 .

5. A hole transporting material for organic electroluminescence device, comprising the aromatic heterocyclic derivative according to claim 1 .

6. An organic electroluminescence device, comprising:
a light emitting layer, and
organic thin film layers between an anode and a cathode,
wherein at least one of the organic thin film layers comprises the aromatic heterocyclic derivative according to claim 1 .

7. The organic electroluminescence device according to claim 6 , wherein
the organic thin film layers comprise a hole transporting layer, and
the hole transporting layer comprises the aromatic heterocyclic derivative.

8. The organic electroluminescence device according to claim 7 , wherein
the hole transporting layer contacts a layer comprising a compound represented by formula (A):

R 21 to R 26 each independently represent a cyano group, —CONH 2 , a carboxyl group, or —COOR 27 ,

R 27 represents an alkyl group comprising from 1 to 20 carbon atoms or a cycloalkyl group comprising from 3 to 20 carbon atoms; and
one or more of a pair of R 21 and R 22 , a pair of R 23 and R 24 , and a pair of R 25 and R 26 optionally bond to each other to form a group represented by —CO—O—CO—.

9. The organic electroluminescence device according to claim 6 , wherein the light emitting layer comprises a phosphorescent material.

10. The organic electroluminescence device according to claim 9 , wherein the phosphorescent material is an ortho metallated complex of a metal selected from the group consisting of iridium (Ir), osmium (Os) and platinum (Pt).

11. The aromatic heterocyclic derivative according to claim 1 , wherein R 5 is a heteroaryl group and is selected from the group consisting of a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, and a xanthenyl group.

12. The aromatic heterocyclic derivative according to claim 1 , wherein R 5 is a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or unsubstituted silyl group, an aryl group having 6 to 30 ring carbon atoms, a halogen atom, or a cyano group.

13. The aromatic heterocyclic derivative according to claim 1 , wherein
R 5 represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or unsubstituted silyl group, an aryl group having 6 to 30 ring carbon atoms, a halogen atom, or a cyano group,
Y represents an oxygen atom, and
L 2 is bonded to a carbon atom at 4-position of the structure represented by formula (1c).

14. The aromatic heterocyclic derivative according to claim 1 , wherein
R 5 represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or unsubstituted silyl group, an acyl group having 6 to 30 ring carbon atoms, a halogen atom, or a cyano group,
Y represents an oxygen atom,
L 2 represents a structure represented by any one of formulae (7a) to (7c):

each of R 11 to R 13 independently represents a linear or branched alkyl group comprising from 1 to 15 carbon atoms, a cycloalkyl group comprising from 3 to 15 ring carbon atoms, a substituted or

Assignees

• Kato Tomoki
• Yabunouchi Nobuhiro
• Fujiyama Takahiro
• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Yabunouchi Nobuhiro
• Fujiyama Takahiro

Classifications

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title