ORGANIC LIGHT EMITTING COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME, AND METHOD OF MANUFACTURING THE ORGANIC LIGHT EMITTING DEVICE

• US 20080122344A1
• Filed: 05/31/2007
• Published: 05/29/2008
• Est. Priority Date: 11/24/2006
• Status: Abandoned Application

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: Samsung Electronics Co. Ltd.
• Inventors: SON, Jhun-mo, KIM, Myeong-suk, KWON, O-hyun, CHOI, Byoung-ki, SHIN, Dong-woo, HAN, Eun-sil, SON, Young-mok, LYU, Yi-yeol, PAEK, Woon-jung
• Application Number:
  US11/756,105
• Publication Number:
  US 20080122344A1
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• 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 2211/1029 containing one nitrogen atom as the 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 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 85/623 containing five rings, e.g. pentacene
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

Provided are an organic light emitting compound represented by Formula 1 below, an organic light emitting device comprising the same, and a method of manufacturing the light emitting device:

wherein CY1, CY2, Ar₁, R₁ and R₂ are described in the detailed description of the invention. An organic light emitting device comprising the organic light emitting compound has low turn-on voltage, high efficiency, high color purity and high luminance.

Claims

1. An organic light emitting compound represented by Formula 1:

wherein CY1 and CY2 are each independently a benzene ring or a naphthalene ring;

Ar₁ is a substituted or unsubstituted C₃₁-C₁₀₀ aryl group;

R₁ and R₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C₁-C₅₀ alkyl group, a substituted or unsubstituted C₁-C₅₀ alkoxy group, a substituted or unsubstituted C₅-C₅₀ cycloalkyl group, a substituted or unsubstituted C₅-C₅₀ heterocycloalkyl group, a substituted or unsubstituted C₆-C₅₀ aryl group, a substituted or unsubstituted C₂-C₅₀ heteroaryl group, or —

N(Z₁)(Z₂) or —

Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄ and Z₅ are each independently a hydrogen atom, a substituted or unsubstituted C₁-C₅₀ alkyl group, a substituted or unsubstituted C₆-C₅₀ aryl group, a substituted or unsubstituted C₂-C₅₀ heteroaryl group, a substituted or unsubstituted C₅-C₅₀ cycloalkyl group or a substituted or unsubstituted C₅-C₅₀ heterocycloalkyl group;

with the proviso that CY1 and CY2 are not both benzene rings.

2. The organic light emitting compound of claim 1, wherein the compound is represented by Formula 2:

wherein Ar₁ is a substituted or unsubstituted C₃₁-C₁₀₀aryl group; and

R₁ and R₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C₁-C₅₀ alkyl group, a substituted or unsubstituted C₁-C₅₀ alkoxy group, a substituted or unsubstituted C₅-C₅₀ cycloalkyl group, a substituted or unsubstituted C₅-C₅₀ heterocycloalkyl group, a substituted or unsubstituted C₆-C₅₀ aryl group, a substituted or unsubstituted C₂-C₅₀ heteroaryl group, or —

N(Z₁)(Z₂) or —

Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄ and Z₅ are each independently a hydrogen atom, a substituted or unsubstituted C₁-C₅₀ alkyl group, a substituted or unsubstituted C₆-C₅₀ aryl group, a substituted or unsubstituted C₂-C₅₀ heteroaryl group, a substituted or unsubstituted C₅-C₅₀ cycloalkyl group or a substituted or unsubstituted C₅-C₅₀ heterocycloalkyl group.

3. The organic light emitting compound of claim 1, wherein the compound is represented by Formula 3:

wherein Ar₁ is a substituted or unsubstituted C₃₁-C₁₀₀aryl group; and

R₁ and R₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C₁-C₅₀ alkyl group, a substituted or unsubstituted C₁-C₅₀ alkoxy group, a substituted or unsubstituted C₅-C₅₀ cycloalkyl group, a substituted or unsubstituted C₅-C₅₀ heterocycloalkyl group, a substituted or unsubstituted C₆-C₅₀ aryl group, a substituted or unsubstituted C₂-C₅₀ heteroaryl group, or —

N(Z₁)(Z₂) or —

Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄ and Z₅ are each independently a hydrogen atom, a substituted or unsubstituted C₁-C₅₀ alkyl group, a substituted or unsubstituted C₆-C₅₀ aryl group, a substituted or unsubstituted C₂-C₅₀ heteroaryl group, a substituted or unsubstituted C₅-C₅₀ cycloalkyl group or a substituted or unsubstituted C₅-C₅₀ heterocycloalkyl group.

4. The organic light emitting compound of claim 1, wherein substituents of the alkyl group, the alkoxy group, the aryl group, the heteroaryl group, the cycloalkyl group and the heterocycloalkyl group are selected from the group consisting of —

F;

—

Cl;

—

Br;

—

CN;

—

NO₂;

—

OH;

an unsubstituted C₁-C₅₀ alkyl group or a C₁-C₅₀ alkyl group substituted with —

F, —

Cl, —

Br, —

CN, —

NO₂ or —

OH;

an unsubstituted C₁-C₅₀ alkoxy group or a C₁-C₅₀ alkoxy group substituted with —

F, —

Cl, —

Br, —

CN, —

NO₂ or —

OH;

an unsubstituted C₆-C₅₀ aryl group or a C₆-C₅₀ aryl group substituted with a C₁-C₅₀ alkyl group, a C₁-C₅₀ alkoxy group, —

F, —

Cl, —

Br, —

CN, —

NO₂ or —

OH;

an unsubstituted C₂-C₅₀ heteroaryl group or a C₂-C₅₀ heteroaryl group substituted with a C₁-C₅₀ alkyl group, a C₁-C₅₀ alkoxy group, —

F, —

Cl, —

Br, —

CN, —

NO₂ or —

OH;

an unsubstituted C₅-C₅₀ cycloalkyl group or a C₅-C₅₀ cycloalkyl group substituted with a C₁-C₅₀ alkyl group, a C₁-C₅₀ alkoxy group, —

F, —

Cl, —

Br, —

CN, —

NO₂ or —

OH;

an unsubstituted C₅-C₅₀ heterocycloalkyl group or a C₅-C₅₀ heterocycloalkyl group substituted with a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, —

F, —

Cl, —

Br, —

CN, —

NO₂ or —

OH; and

—

N(Z₉)(Z₁₀) where Z₉ and Z₁₀ may be each independently a hydrogen atom, a C₁-C₅₀ alkyl group, or a C₆-C₅₀ aryl group substituted with a C₁-C₅₀ alkyl group.

5. The organic light emitting compound of claim 1, wherein Ar₁ is selected from the group consisting of a di(C₆-C₅₀aryl)benzo[k]fluoranthenyl group, a (C₁₁-C₅₀ aryl)benzo[k]fluoranthenyl group, a (pentaC₆-C₅₀ aryl)phenyl group, a (C₁₃-C₅₀ aryl)terphenyl group, a 9,9-di(C₁₂-C₅₀ aryl)fluorenyl group, a (C₁₅-C₅₀ aryl)fluoranthenyl group, a 9-(C₆-C₅₀aryl)-10-(C₁₁-C₅₀aryl)anthryl group, a (C₁₃-C₅₀ aryl)naphthacenyl group, a (C₁₇-C₅₀ aryl)anthryl group, a ((C₁₁-C₅₀ aryl)naphthyl)naphthyl group, a (C₆-C₅₀ aryl)sexyphenyl group, a ter(di(C₆-C₅₀ aryl)fluorenyl group, a bis(biphenylene)-9,9-di(C₆-C₅₀aryl)fluorenyl group, a (C₁₁-C₅₀ aryl)benzo[j]fluoranthenyl group, a (C₂₃-C₅₀aryl)pentarenyl group, a (C₂₂-C₅₀aryl)indenyl group, a (C₂₁-C₅₀aryl)naphthyl group, a (C₁₉-C₅₀aryl)biphenylenyl group, a (C₇-C₅₀aryl)anthryl group, a (C₂₁-C₅₀aryl)azulenyl group, a (C₁₉-C₅₀aryl) heptalenyl group, a (C₁₉-C₅₀ aryl)acenaphthylenyl group, a (C₁₈-C₅₀ aryl)phenarenyl group, a (C₁₈-C₅₀ aryl)fluorenyl group), a (C₁₆-C₅₀ aryl)methylanthryl group, a (C₁₇-C₅₀ aryl)phenanthrenyl group, a (C₁₇-C₅₀ aryl)pyrenyl group, a (C₁₃-C₅₀ aryl)chrysenyl group, a (C₉-C₅₀ aryl)pycenyl group, a (C₁₃-C₅₀ aryl)perylenyl group, a (C₉-C₅₀ aryl)pentaphenyl group, a (C₉-C₅₀ aryl)pentacenyl group, a (C₇-C₅₀ aryl)tetraphenylenyl group, a (C₅-C₅₀aryl)hexaphenyl group, a (C₅-C₅₀aryl)hexacenyl group, a (C₅-C₅₀ aryl)rubicenyl group, a (C₇-C₅₀ aryl)coronenyl group, a (C₅-C₅₀ aryl)trinaphthylenyl group, a (C₅-C₅₀ aryl)heptaphenyl group, a (C₅-C₅₀ aryl)heptacenyl group, a (C₁₈-C₅₀ aryl)fluorenyl group, a (C₅-C₅₀ aryl)pyranthrenyl group, a (C₅-C₅₀ aryl)ovarenyl group and derivatives thereof.

6. The organic light emitting compound of claim 1, wherein Ar₁ is a 7,12-diphenylbenzo[k]fluoranthenyl group, a (pentaphenyl)phenyl group, a 9,9-di(1-biphenyl)fluorenyl group, a 7,8,9,10-tetraphenylfluoranthenyl group, a 9-(4′

-biphenyl-4-yl)-10-phenylanthryl group, a 5,6,11,12-tetraphenylnaphthacenyl group, a 9,10-di(2-naphthyl)anthracenyl group, a 4-(1-biphenyl)-1,1-binaphthyl group, a 6-(terphenyl)chrysenyl group, a 4-sexyphenyl group, a ter(9,9-di(C₆-C₅₀aryl)fluorenyl group, a 2,7-bis(biphenylene)-9,9-di(C₆-C₅₀aryl)fluorenyl group, or a 12-(biphenyl-2-yl)benzo[j]fluoranthenyl group and derivatives thereof.

7. The organic light emitting compound of claim 1, wherein R₁ and R₂ are each independently selected from the group consisting of a hydrogen atom, a C₁-C₅₀ alkyl group, a C₁-C₅₀ alkoxy group, a phenyl group, a tolyl group, a biphenyl group, a pentarenyl group, an indenyl group, a naphthyl group, a biphenylenyl group, an anthryl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a phenarenyl group, a fluorenyl group, a methylanthryl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a pycenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a fluorenyl group, a pyranthrenyl group, an ovarenyl group, a carbazolyl group, a thiophenyl group, an indolyl group, a purinyl group, a benzimidazolyl group, a quinolinyl group, a benzothiophenyl group, a parathiazinyl group, a pyrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolynyl group, a oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thianthrenyl group, a cyclopentyl group, a cyclohexyl group, an oxyranyl group, a pyrrolidinyl group, a pyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, a piperazinyl group, a morpolinyl group, a di(C₆-C₅₀ aryl)amino group, a di(C₆-C₅₀ aryl)aminophenyl group, a tri(C₆-C₅₀ aryl)silyl group and derivatives thereof.

8. The organic light emitting compound of claim 1, wherein R₁ and R₂ are each independently a methyl group, a methoxy group, a phenyl group, a tolyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, an imidazolynyl group, an indolyl group, a quinolinyl group, a diphenylamino group, a 2,3-di-p-tolylaminophenyl group, a naphthylphenylamino group, a dinaphthylamino group, or a triphenylsilyl group and derivatives thereof.

9. The organic light emitting compound of claim 1, wherein the compound is represented by any one of Formulae 4 through 19:

10. An organic light emitting device comprising:

a first electrode;

a second electrode; and

an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises an organic light emitting compound according to claim 1.

11. The organic light emitting device of claim 10, wherein the organic layer is an emission layer, a hole injection layer or a hole transport layer.

12. The organic light emitting device of claim 10, further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer, between the first electrode and the second electrode.

13. The organic light emitting device of claim 11, wherein the emission layer further comprises a red, green, blue or white phosphorescent or fluorescent dopant.

14. The organic light emitting device of claim 13, wherein the phosphorescent dopant is an organometallic compound comprising at least one atom selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm.

15. The organic light emitting device of claim 10, comprising a first electrode/hole injection layer/emission layer/electron transport layer/electron injection layer/second electrode structure, a first electrode/hole injection layer/hole transport layer/emission layer/electron transport layer/electron injection layer/second electrode structure or a first electrode/hole injection layer/hole transport layer/emission layer/hole blocking layer/electron transport layer/electron injection layer/second electrode structure.

16. A method of manufacturing an organic light emitting device comprising:

forming a first electrode;

forming an organic thin film comprising the organic light emitting compound according to claim 1 on the first electrode; and

forming a second electrode on the organic thin film.

17. The method of claim 16, wherein the organic thin film is formed using a wet spinning method or a heat transfer method.

18. The method of claim 17, wherein the wet spinning method is one selected from the group consisting of deposition, spin coating, inkjet printing and spray printing.