Aromatic amine derivative and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-9331285-B2
Application number	US-201013138443-A
Country	US
Kind code	B2
Filing date	Dec 15, 2010
Priority date	Dec 16, 2009
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

An aromatic amine derivative represented by the following formula (1):

wherein at least one of R 1 to R 8 is a group other than a hydrogen atom, Ar 1 to Ar 4 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

First claim

The invention claimed is:

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

wherein R 1 , R 3 to R 5 , R 7 and R 8 are a hydrogen atom, R 2 and R 6 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group or a n-hexyl group,
at least one of R 2 and R 6 is a group other than a hydrogen atom, and
Ar 1 to Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group, a halogen atom, a halogenated alkyl group, a nitro group and a carbonyl group, at least one of A 1 to Ar 4 is a phenyl group substituted with one or more substituents selected from the group consisting of a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group,
provided that, when at least one of Ar 1 to Ar 4 is a p-fluorophenyl group, at least one of Ar 1 to Ar 4 which are not a p-fluorophenyl group is a phenyl group other than a p-fluorophenyl group which is substituted with one or more substituents selected from the group consisting of a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group.

2. The aromatic amine derivative according to claim 1 , which is represented by the following formula (2):

wherein R 1 to R 8 , are the same as those in the formula (1),
Ar 2 and Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group, a halogen atom, a halogenated alkyl group and a nitro group,
R 11 to R 20 are independently a hydrogen atom, an alkyl group, an alkylsilyl group, a cyano group, a halogen atom, a halogenated alkyl group a nitro group or a carbonyl group, and
at least one of R 11 to R 20 is a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group.

3. The aromatic amine derivative according to claim 2 , wherein
Ar 2 and Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group and a fluorine atom.

4. An organic electroluminescence device comprising a cathode, an anode, and one or more organic thin film layers comprising an emitting layer therebetween,
wherein at least one layer of the organic thin film layers comprises an aromatic amine derivative represented by the following formula (1) singly or as a component of a mixture:

wherein R 1 , R 3 to R 5 , R 7 and R 8 are a hydrogen atom R 2 and R 6 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group or a n-hexyl group,
at least one of R 2 and R 6 is a group other than a hydrogen atom, and
Ar 1 to Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group, a halogen atom, a halogenated alkyl group, a nitro group and a carbonyl group, at least one of Ar 1 to Ar 4 is a phenyl group substituted with one or more substituents selected from the group consisting of a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group,
provided that, when at least one of Ar 1 to Ar 4 is a p-fluorophenyl group, at least one of Ar 1 to Ar 4 which are not a p-fluorophenyl group is a phenyl group other than a p-fluorophenyl group which is substituted with one or more substituents selected from the group consisting of a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group.

5. The organic electroluminescence device according to claim 4 , wherein the emitting layer comprises the aromatic amine derivative represented by the formula (1).

6. The aromatic amine derivative according to claim 2 , wherein A 2 and A 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, alkylsilyl group, a cyano group and a flourine atom,
R 11 to R 20 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl nitro group or a carbonyl group, and
at least one of R 11 to R 20 is a cyano group, a fluorine atom, a nitro group or a carbonyl group.

7. The aromatic amine derivative according to claim 2 , wherein A 2 and Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group, a halogen atom, a halogenated alkyl group and a nitro group,
R 11 to R 20 are independently a hydrogen atom or a cyano group, and
at least one of R 11 to R 15 is a cyano group, and at least one of R 16 to R 20 is a cyano group.

8. The aromatic amine derivative according to claim 2 , wherein Ar 2 and Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group and a fluorine atom,
R 11 to R 20 are independently a hydrogen atom or a cyano group, and
at least one of R 11 to R 15 is cyano group, and at least one of R 16 to R 20 is a cyano group.

9. The aromatic amine derivative according to claim 2 , wherein A 2 and Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group a cyano group, a halogen atom a halogenated alkyl group and a nitro group,
R 11 , R 15 , R 16 and R 20 are independently a hydrogen atom or a fluorine atom,
R 12 to R 14 and R 17 to R 19 are a hydrogen atom, and
at least one of R 11 and R 15 is a fluorine atom, and at least one of R 16 and R 20 is a fluorine atom.

10. The aromatic amine derivative according to claim 2 , wherein A 2 and Ar 4 are independently an unsubstituted phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkylsilyl group, a cyano group and a fluorine atom,
R 11 , R 15 , R 16 and R 20 are independently a hydrogen atom or a fluorine atom,
R 12 to R 14 and R 17 to R 19 are a hydrogen atom, and
at least one of R 11 and R 15 is a fluorine atom, and at least one of R 16 and R 20 is a fluorine atom.

11. The aromatic amine derivative according to claim 1 , wherein the alkyl group is a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group or a n-he

Assignees

• Mizuki Yumiko
• Kawamura Masahiro
• Mizutani Sayaka
• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Kawamura Masahiro
• Mizutani Sayaka

Classifications

• C07D235/08

  Radicals containing only hydrogen and carbon atoms · CPC title

• C07C255/58

  containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton · CPC title

• C07C211/54 Primary

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C07C211/61

  with at least one of the condensed ring systems formed by three or more rings · CPC title