Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-10056558-B2
Application number	US-201214360497-A
Country	US
Kind code	B2
Filing date	Nov 22, 2012
Priority date	Nov 25, 2011
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

An aromatic amine derivative is represented by a formula (1) below. In the formula (1), R 2 to R 5 , R 7 to R 9 and R 10 are each independently a hydrogen atom or a substituent. In the formula (1), R 1 and R 6 are represented by a formula (2) below, and L 1 to L 3 are each independently a single bond and the like. In the formula (2), Ar 1 is a monovalent residue derived from the ring structure represented by a formula (4) below, X is an oxygen atom or a sulfur atom, and at least one of R 11 to R 18 is an alkyl group. In the formula (1), Ar 2 is an aryl group or a monovalent residue derived from the ring structure represented by the formula (4).

First claim

The invention claimed is:

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

where: R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and 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 trifluoroalkyl group having 1 to 20 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 a proviso that, in the formula (1), R 1 and R 6 are represented by a formula (2) below,

where: 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 residue derived from a ring structure represented by a formula (4) below,

where: X represents an oxygen atom or a sulfur atom,
R 11 to R 17 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 trifluoroalkyl group having 1 to 20 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;
R 18 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; with a proviso that, when at least one of R 11 to R 18 is an unsubstituted methyl group, R 11 , R 12 , R 14 , R 15 , R 17 or R 18 is the unsubstituted methyl group;
one of R 11 to R 17 is a single bond to be bonded with L 1 ;
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 , and R 16 and R 17 optionally forms a saturated or unsaturated ring;
in the formula (2), 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 residue derived from the ring structure represented by the formula (4H)

wherein X represents an oxygen atom or a sulfur atom,
R 21 to R 28 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 trifluoroalkyl group having 1 to 20 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;
at least one of R 21 to R 28 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; with a proviso that, when at least one of R 21 to R 28 is an unsubstituted methyl group, R 21 , R 22 , R 24 , R 25 , R 27 or R 28 is the unsubstituted methyl group;
one of R 21 to R 28 is a single bond to be bonded with L 2 ;
at least one combination of R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 optionally forms a saturated or unsaturated ring.

2. The aromatic amine derivative according to claim 1 , wherein R 11 in Ar 1 is bonded to L 1 by a single bond.

3. The aromatic amine derivative according to claim 1 , wherein Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

4. The aromatic amine derivative according to claim 1 , wherein each of L 1 , L 2 and L 3 in the formula (2) is a single bond.

5. An organic-EL-device material comprising: the aromatic amine derivative according to claim 1 .

6. An organic electroluminescence device comprising a cathode, an organic compound layer and an anode in this order, wherein the organic compound layer comprises the aromatic amine derivative according to claim 1 .

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

8. The organic electroluminescence device according to claim 7 , 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) below,

where: 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:
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.

9. The organic electroluminescence device according to claim 8 , wherein Ar 11 and Ar 12

Assignees

• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Hirokatsu

Classifications

• C07F13/00

  Compounds containing elements of Groups 7 or 17 of the Periodic Table · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D407/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D307/78

  Benzo [b] furans; Hydrogenated benzo [b] furans · CPC title

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title