AROMATIC AMINE COMPOUND, ORGANIC ELECTROLUMINESCENT ELEMENT INCLUDING THE SAME, AND DISPLAY DEVICE INCLUDING ORGANIC ELECTROLUMINESCENT ELEMENT

• US 20100109555A1
• Filed: 11/05/2009
• Published: 05/06/2010
• Est. Priority Date: 11/06/2008
• Status: Active Grant

• Current Assignee: JDI Design and Development GK
• Original Assignee: Sony Corporation (Sony Group Corp.)
• Inventors: Miyabayashi, Yoshihisa, Ichimura, Mari
• Granted Patent: US 8,357,821 B2
• Time in Patent Office: Days
• US Class Current: 315/291
• CPC Class Codes: C07C 255/58 containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Abstract

An aromatic amine compound is represented by general formula [I]:

wherein X¹ and X² each represent a group selected from an alkyl group, an aryl group, an allyl group, an alkoxy group, and an aryloxy group, X¹ and X² may be the same or different, Ar¹ and Ar² each represent an arylene group, n≧1, at least one of substituents Y is a substituent selected from a trifluoromethyl group, a cyano group, and a halogen group, and other substituents Y are groups each selected from a hydro group, an alkyl group, an aryl group, an allyl group, an alkoxy group, and an aryloxy group.

Claims

1. An aromatic amine compound represented by general formula [I]:

2. The aromatic amine compound according to claim 1,

wherein, in X¹ and X², the alkyl group has 1 to 12 carbon atoms when the alkyl group does not have a substituent, and the alkyl group may have a substituent;

the aryl group has 6 to 25 carbon atoms when the aryl group does not have a substituent, and the aryl group may have a substituent;

the allyl group may have a substituent;

the alkoxy group has 1 to 12 carbon atoms when the alkoxy group does not have a substituent, and the alkoxy group may have a substituent;

the aryloxy group has 6 to 25 carbon atoms when the aryloxy group does not have a substituent, and the aryloxy group may have a substituent;

Ar1 has 6 to 25 carbon atoms when Ar1 does not have a substituent, and Ar1 may have a substituent;

Ar2 has 6 to 25 carbon atoms when Ar2 does not have a substituent; and

in Y, the alkyl group has 1 to 12 carbon atoms when the alkyl group does not have a substituent, and the alkyl group may have a substituent;

the aryl group has 6 to 25 carbon atoms when the aryl group does not have a substituent, and the aryl group may have a substituent;

the allyl group may have a substituent;

the alkoxy group has 1 to 12 carbon atoms when the alkoxy group does not have a substituent, and the alkoxy group may have a substituent;

the aryloxy group has 6 to 25 carbon atoms when the aryloxy group does not have a substituent, and the aryloxy group may have a substituent.

3. The aromatic amine compound according to claim 2,

wherein, in general formula [I], X¹ and X² are the same aryl group or different aryl groups and each of X¹ and X² may have a substituent selected from a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a tert-butyl group, a cyclohexyl group, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, an anthranyl group which may have a substituent, and an allyl group which may have a substituent;

Ar¹ is a group selected from general formulae (1) to (44); and

a group represented by general formula [a] is a group selected from general formulae (45) to (69), and at least one selected from R^ms (where m is an integer in the range of 456 to

     732) of the selected group is a substituent selected from a trifluoromethyl group, a cyano group, and a halogen group, each of other R^ms (where m is an integer in the range of 456 to

     732) and R^ks (where k is an integer in the range of 1 to

     453) of the selected Ar¹ is a group selected from a hydro group, a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a tert-butyl group, a cyclohexyl group, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, an anthranyl group which may have a substituent, an allyl group which may have a substituent, a methoxy group, an ethoxy group, a n-propoxy group, an iso-propoxy group, a n-butoxy group, an iso-butoxy group, a tert-butoxy group, a cyclohexyloxy group, a phenoxy group which may have a substituent, a naphthoxy group which may have a substituent, and an anthranyloxy group which may have a substituent.

4. The aromatic amine compound according to claim 3,

wherein each of R^ks (where k is an integer in the range of 1 to 453) of Ar¹ is a hydro group, and

two of R^ms (where m is an integer in the range of 456 to 732) of the group represented by general formula [a] are each a group selected from a trifluoromethyl group, a cyano group, and a halogen group.

5. The aromatic amine compound according to claim 1,

wherein X¹ is a phenyl group, X² is a 2-naphthyl group, Ar¹ is a 2,6-naphthylene group, and a group represented by general formula [a] is a 3-phenanthryl group having cyano groups at the 9-position and the 10-position and a methyl group at the 6-position, and

the aromatic amine compound is a tertiary amine compound represented by formula [Ia].

6. The aromatic amine compound according to claim 1,

wherein X¹ is a phenyl group, X² is a 1-naphthyl group, Ar¹ is a 2,6-naphthylene group, and a group represented by general formula [a] is a 2-anthryl group having cyano groups at the 9-position and the 10-position, and

the aromatic amine compound is a tertiary amine compound represented by formula [Ib].

7. An organic electroluminescent element comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein at least one layer constituting the organic layer is an amine-compound-containing layer including, as a dopant material, at least one aromatic amine compound represented by general formula [I];

8. The organic electroluminescent element according to claim 7, wherein the organic layer has a structure in which a hole-transporting layer and an electron-transporting layer are stacked.

9. The organic electroluminescent element according to claim 8, wherein at least the hole-transporting layer is the amine-compound-containing layer.

10. The organic electroluminescent element according to claim 8, wherein at least the electron-transporting layer is the amine-compound-containing layer.

11. The organic electroluminescent element according to claim 7, wherein the organic layer has a structure in which a hole-transporting layer, a light-emitting layer, and an electron-transporting layer are stacked.

12. The organic electroluminescent element according to claim 11, wherein at least the light-emitting layer is the amine-compound-containing layer.

13. The organic electroluminescent element according to claim 11,

wherein the light-emitting layer is the amine-compound-containing layer containing the dopant material and a host material, and

the host material is a compound having an anthracene skeleton.

14. The organic electroluminescent element according to claim 13, wherein the content of the dopant material contained in the amine-compound-containing layer is 50% or less.

15. A display device comprising:

a pixel portion in which a plurality of pixels each including an organic electroluminescent element are arranged, the organic electroluminescent element including; and

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein at least one layer constituting the organic layer is an amine-compound-containing layer including, as a dopant material, at least one aromatic amine compound represented by general formula [I];

16. The display device according to claim 15, wherein the control unit includes a switching element.