Aromatic amine derivative and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-2016181527-A1
Application number	US-201615045496-A
Country	US
Kind code	A1
Filing date	Feb 17, 2016
Priority date	Dec 16, 2009
Publication date	Jun 23, 2016
Grant date	—

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

1 . 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) and an anthracene derivative represented by the following formula (10):

wherein R 1 to R 8 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms,
at least one of R 1 to R 5 is a group other than a hydrogen atom, and
Ar 1 to Ar 4 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, at least one of Ar 1 to Ar 4 is an aryl group substituted with one or more substituents selected from 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 an aryl group other than a p-fluorophenyl group which is substituted with one or more substituents selected from a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group,

wherein Ar 11 and Ar 12 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and
R 101 to R 108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

2 . The organic electroluminescence device according to claim 1 , wherein the emitting layer comprises the aromatic amine derivative represented by the formula (1) and the anthracene derivative represented by the formula (10).

3 . The organic electroluminescence device according to claim 1 , wherein the aromatic amine derivative represented by the formula (1) is represented by the following formula (2):

wherein R 1 to R 8 , Ar 2 and Ar 4 are the same as those in the formula (1),
R 11 to R 20 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group, and
at least one of R 11 to R 15 is a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group, and at least one of R 16 to R 20 is a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group

4 . The organic electroluminescence device according to claim 3 , wherein one of R 11 to R 15 is a cyano group, and the remaining R 11 to R 15 are hydrogen atoms, and
one of R 16 to R 20 is a cyano group, and the remaining R 16 to R 20 are hydrogen atoms.

5 . The organic electroluminescence device according to claim 4 , wherein R 1 , R 3 , R 4 , R 5 , R 7 and R 5 are hydrogen atoms

6 . The organic electroluminescence device according to claim 5 , wherein R 2 and R 6 are independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms or a substituted or unsubstituted silyl group having 3 to 30 carbon atoms.

7 . The organic electroluminescence device according to claim 1 , wherein Ar 1 to Ar 4 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar 1 to Ar 4 is an aryl group having one or more cyano groups.

8 . The organic electroluminescence device according to claim 1 , wherein in the formula (10), Ar 11 and Ar 12 are independently a substituted or unsubstituted fused aromatic ring group having 10 to 30 ring carbon atoms.

9 . The organic electroluminescence device according to claim 1 , wherein in the formula (10), Ar 11 is a substituted or unsubstituted phenyl group, and Ar 12 is a substituted or unsubstituted fused aromatic ring group having 10 to 30 ring carbon atoms.

10 . The organic electroluminescence device according to claim 9 , wherein the anthracene derivative is represented by the following formula (10-4);

wherein R 101 to R 108 are the same as those in formula (10),
R 111 is 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 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom,
b is an integer of 0 to 7, and plural R 111 s may be the same or different when b is an integer of 2 or more, and
Ar 6 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or Ar 6 may form a ring with the benzene ring to which Ar 6 bonds.

11 . The organic electroluminescence device according to claim 9 , wherein the anthracene derivative is represented by the following formula (10-5):

wherein R 101 to R 108 are the same as those in formula (10),
R 111 is 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 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted

Assignees

• 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