Aromatic amine derivative, and organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-10246441-B2
Application number	US-201213435965-A
Country	US
Kind code	B2
Filing date	Mar 30, 2012
Priority date	Oct 2, 2009
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

An aromatic amine derivative including a substituent A and a substituent B each represented by the formula (1) or (2) and having an arylene group bound to a carbazole structure, in which the substituent A and the substituent B include groups different from each other in the position at which the arylene group is bonded to the carbazole structure, and the substituent A and the substituent B are bonded to the same nitrogen atom or different nitrogen atoms in the molecule; an organic electroluminescent device including an organic thin-film layer formed of one or more layers including at least a light emitting layer, the organic thin-film layer being interposed between a cathode and a anode, in which at least one layer of the organic thin-film layer contains the aromatic amine derivative, and the molecules are rarely crystallized.

First claim

The invention claimed is:

1. An organic electroluminescence device, comprising:
a cathode:
an anode; and
an organic thin-film layer interposed between the cathode and the anode, wherein the organic thin-film layer comprises a light emitting layer and at least one selected from the group consisting of a hole transporting layer and a hole injecting layer, and
wherein at least one selected from the group consisting of the hole transporting layer and the hole injecting layer comprises an aromatic amine derivative represented by formula (9):

wherein:
at least one of Ar 3 to Ar 5 represents the substituent A and at least one of Ar 3 to Ar 5 represents the substituent B;
a group out of Ar 3 to Ar 5 except the substituent A and the substituent B represents a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 ring carbon atoms, wherein an optional substituent of the aryl group and the heteroaryl group is a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a trialkylsilyl group having linear or branched alkyl groups each having 1 to 15 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 25 ring carbon atoms, an alkylarylsilyl group having a linear or branched alkyl group having 1 to 15 carbon atoms and an aryl group having 6 to 25 ring carbon atoms, an aryl group having 6 to 25 ring carbon atoms, a halogen atom, or a cyano group:
the substituent A is represented by formula (1);
the substituent B is represented by formula (2);

wherein:
L 1 and L 2 each represent a substituted or unsubstituted arylene group having 6 to 25 ring carbon atoms, and a substituent which L 1 and L 2 may have is a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a trialkylsilyl group having linear or branched alkyl groups each having 1 to 15 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 25 ring carbon atoms, an alkylarylsilyl group having a linear or branched alkyl group having 1 to 15 carbon atoms and an aryl group having 6 to 25 ring carbon atoms, an aryl group having 6 to 25 ring carbon atoms, a halogen atom, or a cyano group;
Ar 1 represents a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, and a substituent which Ar 1 may have is selected from the group consisting of a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a trialkylsilyl group having linear or branched alkyl groups each having 1 to 15 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 25 ring carbon atoms, an alkylarylsilyl group having a linear or branched alkyl group having 1 to 15 carbon atoms and an aryl group having 6 to 25 ring carbon atoms, an aryl group having 6 to 25 ring carbon atoms, a halogen atom, and a cyano group;
a represents an integer of 0 to 3, and b, c, and d each independently represent an integer of 0 to 4; and
R 1 to R 4 each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a trialkylsilyl group having linear or branched alkyl groups each having 1 to 15 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 25 ring carbon atoms, an alkylarylsilyl group having a linear or branched alkyl group having 1 to 15 carbon atoms and an aryl group having 6 to 25 ring carbon atoms, an aryl group having 6 to 25 ring carbon atoms, a halogen atom, or a cyano group, and a plurality of R 1 's to R 4 's adjacent to each other may be bonded to each other to form a saturated or unsaturated, divalent group that forms a ring.

2. The organic electroluminescence device according to claim 1 , wherein the substituent A has formula (3) or formula (4):

wherein:
L 3 is defined the same as L 1 and L 2 ;
Ar 2 is defined the same as Ar 1 ;
R 5 and R 6 are defined the same as R 1 to R 4 ;
e represents an integer of 0 to 3; and
f represents an integer of 0 to 4.

3. The organic electroluminescence device according to claim 2 , wherein the substituent A has formula (3).

4. The organic electroluminescence device according to claim 1 , wherein L 1 and L 2 are each independently represented by formula (5):

wherein:
R 7 represents a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a trialkylsilyl group having linear or branched alkyl groups each having 1 to 15 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 25 ring carbon atoms, an alkylarylsilyl group having a linear or branched alkyl group having 1 to 15 carbon atoms and an aryl group having 6 to 25 ring carbon atoms, an aryl group having 6 to 25 ring carbon atoms, a halogen atom, or a cyano group, and a plurality of R 7 's adjacent to each other may be bonded to each other to form a ring;
n and s each independently represent an integer of 0 to 4; and
when n represents 2 to 4, R 7 's on different benzene rings may be identical to or different from each other, and respective R 7 's present on benzene rings adjacent to each other may be bonded to each other to form a ring.

5. The organic electroluminescence device according to claim 1 , wherein L 1 and L 2 are each independently represented by any one of formulae (6) to (8):

wherein:
R 8 to R 12 each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a trialkylsilyl group having linear or branched alkyl groups each having 1 to 15 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 25 ring carbon atoms, an alkylarylsilyl group having a linear or branched alkyl group having 1 to 15 carbon atoms and an aryl group having 6 to 25 ring carbon atoms, an aryl group having 6 to 25 ring carbon atoms, a halogen atom, or a cyano group, and a plurality of R 8 's to R 12 's adjacent to each other may be bonded to each other to form a saturated or unsaturated ring;
R 13 and R 14 each independently represent a linear or branched alkyl group formed of a hydrocarbon having 1 to 15 carbon atoms, or a cycloalkyl group having 3 to 15 ring carbon atoms; and
g, h, and i each independently represent an integer of 0 to 4, and j and k each independently represent an integer of 0 to 3.

6. The organic electroluminescence device according to claim 1 , wherein, in formula (9):
Ar 3 represents the substituent A;
Ar 4 represents the substituent B; and
Ar 5 represents a substituent C represented by formula (1) or formula (2).

7. The organic electroluminescence device according to claim 6 , wherein in the formula (9), the substituent A, the substituent B, and the substituent C are different from one another in the position at which the L 1 in the formula (1) or the L 2 in the formula (2) is bonded to the carbazole structure.

8. The organic electroluminescence d

Assignees

• Kato Tomoki
• Idemitsu Kosan Co

Inventors

• Kato Tomoki

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H01L51/0072

  Electricity · mapped topic

• C09K2211/1011

  Condensed systems · CPC title