Aromatic amine derivative, and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-11444246-B2
Application number	US-202016903952-A
Country	US
Kind code	B2
Filing date	Jun 17, 2020
Priority date	Aug 31, 2012
Publication date	Sep 13, 2022
Grant date	Sep 13, 2022

Abstract

An aromatic amine derivative represented by formula (1):wherein R1, R2, R3, L, Ar1, Ar2, k, m, and n are the same as defined in the specification, is useful as a material for an organic EL device and realizes an organic EL device with a high efficiency and a long lifetime even when driving it at a low voltage.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising, in the order listed:
an anode;
a first hole transporting layer;
a second hole transporting layer;
a light emitting layer; and
a cathode;
wherein at least one of the first hole transporting layer and second hole transporting layer comprises an aromatic amine derivative represented by formula (1):

wherein in formula (1):
R 1 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a phenyl group;
R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,
k represents an integer of 1 to 5;
m represents an integer of 1 to 4;
n represents an integer of 1 to 3;
when groups R 1 exist, the groups R 1 may be the same or different, when groups R 2 exist, the groups R 2 may be the same or different; and when groups R 3 exist; the groups R 3 may be the same or different;
L represents a single bond or a divalent group represented by formula (16):

wherein in formula (16):
R 1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group;
m represents an integer of 1 to 4; and
when groups R 1 exist, the groups R 1 may be the same or different;
Ar 1 represents a group represented by formula (30):

wherein in formula (30):
R 1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group;
m represents an integer of 1 to 4;
when groups R 1 exist, the groups R 1 may be the same or different; and
two R 4 may be the same or different and each independently represents a methyl group or a phenyl group;
Ar 2 represents a group represented by formula (7):

wherein in formula (7):
R 1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group;
k represents an integer of 1 to 5;
m represents an integer of 1 to 4; and
when groups R 1 exist, the groups R 1 may be the same or different.

2. The organic electroluminescence device according to claim 1 , wherein two R 4 represent methyl groups.

3. The organic electroluminescence device according to claim 1 , wherein one of two R 4 represents a methyl group and the other represents a phenyl group.

4. The organic electroluminescence device according to claim 1 , wherein two R 4 represent phenyl groups.

5. The organic electroluminescence device according to claim 1 , wherein Ar 2 represents a group represented by formula (7-1) or (7-2):

wherein R 1 , k and m are as defined in formulae (7).

6. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (1) each independently represents a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group or a phenyl group.

7. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (30) represents a hydrogen atom or a phenyl group.

8. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (7) represents a hydrogen atom, a methyl group, a t-butyl group, or a phenyl group.

9. The organic electroluminescence device according to claim 1 , wherein R 1 , R 2 and R 3 in formula (1) represent hydrogen atoms.

10. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (16) represents a hydrogen atoms.

11. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (30) represents a hydrogen atom.

12. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (7) represents a hydrogen atom.

13. The organic electroluminescence device according to claim 1 , wherein R 1 , R 2 and R 3 in formula (1), R 1 in formula (16), R 1 in formula (30), and R 1 in formula (7) represent hydrogen atoms.

14. The organic electroluminescence device according to claim 1 , wherein the aromatic amine derivative is any one of the following compounds:

15. The organic electroluminescence device according to claim 1 , wherein the first hole transporting layer comprises the aromatic amine derivative.

16. The organic electroluminescence device according to claim 1 , wherein R 2 and R 3 in formula (1) each independently represents a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, or a t-butyl group.

17. The organic electroluminescence device according to claim 1 , wherein R 1 in formula (1) each independently represents a hydrogen atom or a phenyl group.

18. The organic electroluminescence device according to claim 1 , wherein in (R 1 )m of formula (1):
R 1 represents a phenyl group and m represents 1; and
wherein in (R 1 )n of formula (1):
R 1 represents a hydrogen atom and n represents 3.

Assignees

• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Sado Takayasu
• Fujiyama Takahiro

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · 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

• C07C217/92

  the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C211/61 Primary

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