MONOAMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT USING SAME

• US 20120199820A1
• Filed: 08/05/2011
• Published: 08/09/2012
• Est. Priority Date: 08/05/2010
• Status: Abandoned Application

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Ito, Mitsunori, Ogiwara, Toshinari, Nishimura, Kazuki, Inoue, Tetsuya, Hibino, Kumiko
• Application Number:
  US13/500,109
• Publication Number:
  US 20120199820A1
• Time in Patent Office: Days
• US Class Current: 257/40
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/58 Naphthylamines; N-substituted derivatives thereof
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 2603/24 Anthracenes; Hydrogenated anthracenes
• CPC Class Codes: C07C 2603/26 Phenanthrenes; Hydrogenated phenanthrenes
• CPC Class Codes: C07C 2603/40 containing four condensed rings
• CPC Class Codes: C07C 2603/52 containing five condensed rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• 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 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/90 Multiple hosts in the emissive layer
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Abstract

An organic electroluminescence device includes: an anode; a cathode being opposed to the anode; and an emitting layer being provided between the anode and the cathode. The emitting layer includes a host material and a phosphorescent dopant material. The host material includes a monoamine derivative represented by a formula-(1A) below.

In the formula (1A), each of Ar¹, Ar² and Ar⁴ is a substituted or unsubstituted aryl group or heteroaryl group, Ar³ is a substituted or unsubstituted arylene group or heteroarylene group, n is an integer of 0 to 5, Ar³ may be mutually the same or different when n is 2 or more, and at least one of Ar¹, Ar², Ar³, and Ar⁴ is a group derived from a fused aromatic hydrocarbon skeleton having 3 or more rings.

Claims

1. An organic electroluminescence device, comprising:

an anode;

a cathode opposed to the anode; and

an emitting layer between the anode and the cathode,

wherein the emitting layer comprises a host material and a phosphorescent dopant material,

the host material comprises a monoamine derivative of formula (1A);

2. The organic electroluminescence device of claim 1, wherein the fused aromatic hydrocarbon skeleton having 3 or more rings is of any of formulae (2A) to (5A):

3. The organic electroluminescence device of claim 1,

wherein the emitting layer comprises a first host material, a second host material, and a phosphorescent dopant material, and

the second host material is the monoamine derivative.

4. The organic electroluminescence device of claim 3, wherein Ar⁴ comprises a fused aromatic hydrocarbon skeleton having 3 or more rings.

5. The organic electroluminescence device of claim 3, wherein Ar⁴ is a monovalent group comprising a phenanthrene skeleton;

a benzophenanthrene skeleton;

a dibenzophenanthrene skeleton;

a chrysene skeleton;

a benzochrysene skeleton;

a dibenzochrysene skeleton;

a fluoranthene skeleton;

a benzofluoranthene skeleton;

a triphenylene skeleton;

a benzotriphenylene skeleton;

a dibenzotriphenylene skeleton;

a picene skeleton;

a benzopicene skeleton;

or a dibenzopicene skeleton.

6. The organic electroluminescence device of claim 1, wherein the phosphorescent dopant material is an ortho-metalated complex of iridium (Ir), osmium (Os), or platinum (Pt).

7. A monoamine derivative of formula (1):

8. The monoamine derivative of claim 7, wherein when n is 2 or more, at least one of Ar¹, Ar², and Ar⁴ comprises a fused aromatic hydrocarbon skeleton having 3 or more rings.

9. The monoamine derivative of claim 7, wherein the fused aromatic hydrocarbon skeleton having 3 or more rings is of any of formulae (2) to (5):

10. The monoamine derivative of claim 9, wherein Ar⁴ is a monovalent group comprising a skeleton of any of formulae (2) to (5).

11. The monoamine derivative of claim 10, wherein Ar⁴ is a monovalent group comprising a phenanthrene skeleton;

a benzophenanthrene skeleton;

a dibenzophenanthrene skeleton;

a chrysene skeleton;

a benzochrysene skeleton;

a dibenzochrysene skeleton;

a fluoranthene skeleton;

a benzofluoranthene skeleton;

a triphenylene skeleton;

a benzotriphenylene skeleton;

a dibenzotriphenylene skeleton;

a picene skeleton;

a benzopicene skeleton;

or a dibenzopicene skeleton.

12. The monoamine derivative of claim 7,

wherein when n is 0, the monoamine derivative is of formula (6):

13. The monoamine derivative of claim 7,

wherein when n is 1, the monoamine derivative of formula (7):

14. The monoamine derivative of claim 7,

wherein when n is 2 or more, Ar⁴ is an aromatic hydrocarbon group or a fused aromatic hydrocarbon group selected from the group consisting of a phenyl group;

a naphthyl group;

a phenanthrenyl group;

a benzophenanthrenyl group;

a dibenzophenanthrenyl group;

a benzochrysenyl group;

a dibenzochrysenyl group;

a fluoranthenyl group;

a benzofluoranthenyl group;

a triphenylenyl group;

a benzotriphenylenyl group;

a dibenzotriphenylenyl group;

a picenyl group;

a benzopicenyl group;

a dibenzopicenyl group;

a phenalenyl group; and

a diazaphenanthrenyl group, and

when each of Ar¹ and Ar² is a phenyl group, (Ar³)_n—

Ar⁴ is not of formula (8);

15. The monoamine derivative of claim 12,

wherein each of Ar¹ and Ar² is a phenyl group or a naphthyl group, and

Ar⁴ is a benzochrysenyl group, a triphenylenyl group, or a phenanthrenyl group.

16. The monoamine derivative of claim 13, wherein

each of Ar¹ and Ar² is a phenyl group or a naphthyl group,

Ar³ is a phenylene group or a naphthylene group, and

Ar⁴ a benzochrysenyl group, a triphenylenyl group, or a phenanthrenyl group.

17. The monoamine derivative of claim 14, wherein

each of Ar¹ and Ar² is a phenyl group or a naphthyl group,

Ar³ is a phenylene group or a naphthylene group, and

Ar⁴ is a benzochrysenyl group, a triphenylenyl group, or a phenanthrenyl group.

18. The monoamine derivative of claim 7, wherein the monoamine derivative is configured to be a phosphorescent host material in an organic electroluminescence device.

19. An organic electroluminescence device, comprising:

a cathode;

an anode; and

a single-layered or multilayered organic thin-film layer provided between the cathode and the anode,

wherein at least one layer of the organic thin-film layer comprises the monoamine derivative of claim 7.

20. The organic electroluminescence device of claim 19, wherein the organic thin-film layer further comprises a phosphorescent material.

21. The organic electroluminescence device of claim 19, wherein the at least one layer of the organic thin-film layer is an emitting layer, and

at least one layer of the emitting layer comprises the monoamine derivative and the phosphorescent material.

22. The organic electroluminescence device of claim 21,

wherein the emitting layer comprises a first host material;

a second host material; and

a phosphorescent dopant material,

the second host material comprises the monoamine derivative, and

the phosphorescent dopant material is the phosphorescent material.

23. The organic electroluminescence device of claim 22,

wherein the first host material is a fused aromatic compound of any of formulae (11) and (12):

Ar^a—

Ar^b—

Ar^c 

 

(11)

Ar^d—

Ar^e—

Ar^f—

Ar^g 

 

(12),

Ar^a, Ar^b, Ar^c, Ar^d, Ar^e, Ar^f, and Ar^g each independently comprise a substituted or unsubstituted benzene skeleton;

a substituted or unsubstituted naphthalene skeleton;

or a substituted or unsubstituted fused aromatic hydrocarbon skeleton having 3 or more rings.

24. The organic electroluminescence device of claim 23, wherein the fused aromatic hydrocarbon skeleton having 3 or more rings is of any of formulae (13) to (16):

25. The organic electroluminescence device of claim 24, wherein the first host material comprises at least one fused aromatic hydrocarbon skeleton having 3 or more rings selected from the group consisting of a phenanthrene skeleton;

a benzophenanthrene skeleton;

a dibenzophenanthrene skeleton;

a chrysene skeleton;

a benzochrysene skeleton;

a dibenzochrysene skeleton;

a fluoranthene skeleton;

a benzofluoranthene skeleton;

a triphenylene skeleton;

a benzotriphenylene skeleton;

a dibenzotriphenylene skeleton;

a picene skeleton;

a benzopicene skeleton; and

a dibenzopicene skeleton.

26. The organic electroluminescence device of claim 20,

wherein the phosphorescent material comprises a metal complex,

the metal complex comprises a metal atom selected from the group consisting of Ir, Pt, Os, Au, Re, and Ru, and

the metal complex further comprises a ligand.

27. The organic electroluminescence device of claim 26, wherein the ligand has an ortho-metal bond with the metal atom of the metal complex.

28. The organic electroluminescence device of claim 21, wherein a maximum emission wavelength of the phosphorescent material is from 520 nm to 720 nm.

29. A monoamine derivative of formula (1B):