Aromatic amine derivative and organic electroluminescence element using same

Patent metadata

Field	Value
Publication number	US-9640773-B2
Application number	US-201214344941-A
Country	US
Kind code	B2
Filing date	Sep 14, 2012
Priority date	Sep 16, 2011
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

An aromatic amine derivative is represented by the following formula (1). In the formula (1), R 1 to R 10 each independently represent a hydrogen atom and a substituent. In the formula (1); R 1 is represented by the following formula (2); any one of R 2 to R 5 and R 7 to R 10 is represented by the following formula (2); and L 1 to L 3 each independently represent a single bond, a divalent residue of an aryl group, or the like. In the formula (2); Ar 1 is a monovalent substituent having a partial structure represented by the following formula (3); X represents an oxygen atom or a sulfur atom; and A and B represent a six-membered ring. In the formula (2), Ar 2 is an aryl group, a monovalent substituent having a partial structure represented by the formula (3), and the like.

First claim

The invention claimed is:

1. An aromatic amine derivative represented by a formula (1):

wherein:
R 1 is represented by a formula (2);
any one of R 2 to R 5 and R 7 to R 10 is represented by the formula (2), and the remaining ones of R 2 to R 5 and R 7 to R 10 each independently represent: a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; and
R 6 represents: a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

wherein:
L 1 , L 2 and L 3 each independently represent a single bond, a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Ar 1 is a monovalent substituent having a partial structure represented by a formula (3):

wherein:
X represents an oxygen atom or a sulfur atom; and
A and B represent a six-membered ring; the six-membered ring represented by A and B is optionally fused with another ring; and

Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent substituent having a partial structure represented by the formula (3).

2. The aromatic amine derivative according to claim 1 , wherein R 1 and R 3 are represented by the formula (2).

3. The aromatic amine derivative according to claim 1 , wherein R 1 and R 8 are represented by the formula (2).

4. The aromatic amine derivative according to claim 1 , wherein the monovalent substituent having the partial structure represented by the formula (3) is a monovalent residue represented by a formula (4):

wherein:
X represents an oxygen atom or a sulfur atom;
R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, with the proviso that, in the formula (2); when Ar 1 is a monovalent residue of the formula (4), one of R 11 to R 18 is a single bond to be bonded to L 1 ; and when Ar e is a monovalent residue of the formula (4), one of R 11 to R 18 is a single bond to be bonded to L 2 ; and
at least one combination of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 optionally forms a saturated or unsaturated ring.

5. An organic electroluminescence device comprising:
a cathode;
an anode; and
an organic compound layer interposed between the cathode and the anode,
wherein the organic compound layer comprises the aromatic amine derivative according to claim 1 .

6. The organic electroluminescence device according to claim 5 , wherein the organic compound layer comprises a plurality of organic thin-film layers comprising an emitting layer, and
wherein at least one of the plurality of organic thin-film layers comprises the aromatic amine derivative.

7. The organic electroluminescence device according to claim 6 , wherein at least one of the plurality of organic thin-film layers comprises the aromatic amine derivative and an anthracene derivative represented by a formula (20):

wherein:
Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted fused ring group having 10 to 30 ring atoms, or a group provided by combining the monocyclic group and the fused ring group; and
R 101 to R 108 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted fused ring group having 10 to 30 ring atoms, a group provided by combining the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted silyl group.

8. The organic electroluminescence device according to claim 7 , wherein, in the formula (20), Ar 11 and Ar 12 are each independently a substituted or unsubstituted fused ring group having 10 to 30 ring atoms.

9. The organic electroluminescence device according to claim 7 , wherein, in the formula (20), one of Ar 11 and Ar 12 is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other of Ar 11 and Ar 12 is a substituted or unsubstituted fused ring group having 10 to 30 ring atoms.

10. The organic electroluminescence device according to claim 9 , wherein, in the formula (20), Ar 12 is selected from a naphthyl group, phenanthryl group, benzoanthryl group and dibenzofuranyl group, and Ar 11 is an unsubstituted phenyl group or a phenyl group substituted by at leas

Assignees

• Mizuki Yumiko
• Ito Hirokatsu
• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Hirokatsu

Classifications

• H01L51/0073

  Electricity · mapped topic

• H01L51/0094

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic

• H01L51/0074

  Electricity · mapped topic

• C07D333/76 Primary

  Dibenzothiophenes · CPC title