AROMATIC AMINE DERIVATIVE AND ELECTROLUMINESCENCE DEVICE USING THE SAME

• US 20070278938A1
• Filed: 04/04/2007
• Published: 12/06/2007
• Est. Priority Date: 04/26/2006
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Yabunouchi, Nobuhiro, Inoue, Tetsuya
• Granted Patent: US 8,129,038 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: H05B 33/14 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 Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Provided are a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin layer comprising a single layer or plural layers including a light emitting layer is interposed between a cathode and an anode, wherein at leas one layer of the above organic thin layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Thus, the organic electroluminescence device is less liable to be crystallized in molecules, improved in a yield in producing the organic electroluminescence device and extended in a lifetime.

Claims

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

wherein R₁ is a hydrogen atom, a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or non-substituted arylthio group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 50 carbon atoms, an amino group substituted with a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group;

a is an integer of 0 to 4, and b is an integer of 1 to 3;

plural R₁ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

at least one of Ar₁ to Ar₄ is represented by the following Formula (2);

(wherein R₂ and R₃ each are selected independently from the same groups as those of R₁ in Formula (1) described above;

X is oxygen, sulfur, selenium or tellurium;

c is an integer of 0 to 6;

d is an integer of 0 to 3;

and e is an integer of 1 to 3;

plural R₂ or R₃ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when e is 2 or more and d is not 0, plural R₃ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted);

in Formula (1), among Ar₁ to Ar₄, the groups which are not represented by Formula (2) each are independently a substituted or non-substituted aryl group having 6 to 50 ring carbon atoms or a substituted or non-substituted aromatic heterocyclic group having 5 to 50 ring carbon atoms.

2. The aromatic amine compound as described in claim 1, wherein in Formula (1) described above, at least one of Ar₁ to Ar₄ is represented by the following Formula (3):

(wherein R₄ to R₆ each are selected independently from the same groups as those of R₁ in Formula (1) described above;

X is an oxygen or sulfur atom;

f and h each are an integer of 0 to 4;

g is an integer of 0 to 3; and

i is an integer of 1 to 3;

plural R₄ or R₅ or R₆ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when i is 2 or more and h is not 0, plural R₆ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted).

3. The aromatic amine compound as described in claim 1 or 2, wherein in Formula (1) described above, Ar₁ and Ar₂ are represented by Formula (2) or (3) described above.

4. The aromatic amine compound as described in claim 1 or 2, wherein in Formula (1) described above, Ar₁ and Ar₃ are represented by Formula (2) or (3) described above.

5. The aromatic amine compound as described in claim 1 or 2, wherein in Formula (1) described above, only Ar₁ is represented by Formula (2) or (3) described above.

6. The aromatic amine compound as described in any of claims 1 to 5, wherein in Formula (1), b is 2.

7. The aromatic amine compound as described in any of claims 1 to 6, wherein in Formula (2), e is 1.

8. The aromatic amine compound as described in any of claims 1 to 6, wherein in Formula (3), i is 1.

9. The aromatic amine compound as described in any of claims 1 to 8, wherein in Formula (2), X is an oxygen atom.

10. The aromatic amine compound as described in claim 1 or 2, wherein in Formula (1) described above, Ar₂ is represented by the following Formula (4):

wherein R₇ is selected from the same groups as those of R₁ in Formula (1) described above;

j is an integer of 0 to 4, and k is an integer of 1 to 3;

plural R₇ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when k is 2 or more and j is not 0, plural R₇ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

Ar₆ and Ar₆ each are independently a substituted or non-substituted aryl group having 6 to 50 ring carbon atoms or a substituted or non-substituted aromatic heterocyclic group having 5 to 50 ring carbon atoms.

11. The aromatic amine compound as described in claim 1 or 2, wherein in Formula (1) described above, Ar₂ and Ar₄ each are represented independently by Formula (4) described above.

13. The aromatic amine compound as described in any of claims 1 to 12, wherein it is a material for an organic electroluminescence device.

14. The aromatic amine compound as described in any of claims 1 to 12, wherein it is a hole injecting material or a hole transporting material for an organic electroluminescence device.

15. An organic electroluminescence device in which an organic thin layer comprising a single layer or plural layers including at least a light emitting layer is interposed between a cathode and an anode, wherein at least one layer of the above organic thin layer contains the aromatic amine derivative as described in any of claims 1 to 12 in the form of a single component or a mixed component.

16. The organic electroluminescence device as described in claim 15, wherein the organic thin layer described above comprises a hole injecting layer or a hole transporting layer, and the aromatic amine derivative as described in any of claims 1 to 12 is contained in the above hole injecting layer or hole transporting layer.

17. The organic electroluminescence device as described in claim 15, wherein styrylamine and/or arylamine is contained in the light emitting layer described above.

18. The organic electroluminescence device as described in any of claims 15 to 17 emitting blue light.

12. An aromatic amine derivative represented by the following Formula (5):

wherein at least one of Ar₇ to Ar₉ is represented by the following Formula (3);

(wherein R₄ to R₆ each are independently a hydrogen atom, a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or non-substituted arylthio group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 50 carbon atoms, an amino group substituted with a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group;

X is an oxygen or sulfur atom;

f and h each are an integer of 0 to 4;

g is an integer of 0 to 3; and

i is an integer of 1 to 3;

plural R₄ or R₅ or R₆ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when i is 2 or more and h is not 0, plural R₆ may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted);

in Formula (5), among Ar₁ to Ar₃, the groups which are not represented by Formula (3) each are independently a hydrogen atom, a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or non-substituted arylthio group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 50 carbon atoms, an amino group substituted with a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group.