Source: http://www.google.com/patents/US8021764?dq=6519629
Timestamp: 2016-12-10 19:07:53
Document Index: 676099393

Matched Legal Cases: ['Application No. 10', 'Application No. 07109066', 'Application No. 07109066', 'Application No. 05', 'Application No. 2007', 'Application No. 10', 'Application No. 10', 'Application No. 2004', 'Application No. 10', 'Application No. 200510121732', 'Application No. 2005']

Patent US8021764 - Phenylcarbazole-based compound and organic electroluminescent device ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA phenylcarbazole-based compound is represented by Formula 1, and has superior electric properties and charge transport abilities, and thus is useful as a hole injection material, a hole transport material, and/or an emitting material which is suitable for fluorescent and phosphorescent devices of all...http://www.google.com/patents/US8021764?utm_source=gb-gplus-sharePatent US8021764 - Phenylcarbazole-based compound and organic electroluminescent device employing the sameAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS8021764 B2Publication typeGrantApplication numberUS 11/286,421Publication dateSep 20, 2011Filing dateNov 25, 2005Priority dateNov 29, 2004Fee statusPaidAlso published asCN1978441A, CN1978441B, DE602005010961D1, EP1661888A1, EP1661888B1, US20060115680Publication number11286421, 286421, US 8021764 B2, US 8021764B2, US-B2-8021764, US8021764 B2, US8021764B2InventorsSeok-Hwan Hwang, Young-Kook Kim, Chang-Ho Lee, Seok-Jong Lee, Seung-gak Yang, Hee-Yeon KimOriginal AssigneeSamsung Mobile Display Co., Ltd.Export CitationBiBTeX, EndNote, RefManPatent Citations (57), Non-Patent Citations (28), Referenced by (18), Classifications (29), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetPhenylcarbazole-based compound and organic electroluminescent device employing the same
US 8021764 B2Abstract
each of R1, R2, R3, R1′, R2′ and R3′ is independently a mono or multi substituent selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heterocycle, a substituted or unsubstituted C6-C30 condensed polycyclic group, a hydroxy group, a cyano group, and a substituted or unsubstituted amino group, and two or more adjacent groups among R1, R2, R3, R1′, R2′ and R3′ can be connected to each other to form a saturated or unsaturated carbocycle; and
each Ar is independently selected from the group consisting of a phenyl group, an ethylphenyl group, an ethylbiphenyl group, an o-, m-, or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, and p-cumenyl group, a mesityl group, a phenoxyphenyl group, a (α,α-dimethylbenzene) phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl) aminophenyl group, a pentarenyl group, an indenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azurenyl group, a heptarenyl group, an acenaphthylrenyl group, a phenanthrenyl group, a fluorenyl group, an anthraquinolyl group, a triphenylene group, a pyrenyl group, a pherylenyl group, a chloropherylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a coroneryl group, a trinaphthylenyl group, a heptaphenyl group, and a carbazolyl group.
2. A compound represented by one selected from the group consisting of formulae (3) through (26):
3. The compound of claim 2, wherein the compound is represented by formulae (3):
4. The compound of claim 2, wherein the compound is represented by formulae (4):
5. An organic electroluminescent display device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, the organic layer comprising the compound of claim 1.
6. A method of preparing a compound represented by Formula (1), comprising:
each of R1, R2, R3, R1′, R2′ and R3′ is independently a mono or multi substituent selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heterocycle, a substituted or unsubstituted C6-C30 condensed polycyclic group, a hydroxy group, a cyano group, and a substituted or unsubstituted amino group, and two or more adjacent groups among R1, R2, R3, R1′, R2′ and R3′can be connected to each other to form a saturated or unsaturated carbocycle;
7. The method of claim 6, wherein the reaction is carried out in the presence of Pd2(dba)3 where dba is dibenzylideneacetone, sodium tert-butoxide, and tri(tert-butyl) phosphine at a temperature of 50 to 150° C.
each Ar is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group, wherein the substituent of the substituted C6-C30 aryl group and the substituted C2-C30 heteroaryl group are each independently selected from the group consisting of a C1-C10 alkyl group, a C1-C10 alkoxy group, a nitro group, a halogen atom, an amino group, a C6-C10 aryl group, a C2-C10 heteroaryl group, a cyano group, and a hydroxy group.
9. The organic electroluminescent device of claim 8, wherein the organic layer is a hole injection layer or a hole transport layer.
10. The organic electroluminescent device of claim 8, wherein the organic layer is a single layer serving as both a hole injection layer and a hole transport layer.
11. The organic electroluminescent device of claim 8, wherein the organic layer is an emitting layer.
12. The organic electroluminescent device of claim 11, wherein the emitting layer is composed of a phosphorescent or fluorescent material.
13. The organic electroluminescent device of claim 11, wherein the compound represented by Formula (1) is used as a fluorescent or phosphorescent host in the emitting layer.
an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a compound represented by one selected from the group consisting of the following formulae:
15. The organic electroluminescent device of claim 14, wherein the compound is represented by Formula (3) or Formula (4):
This application claims the benefit of Korean Patent Application No. 10-2004-0098747, filed on Nov. 29, 2004, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference.
where X is a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 heterocycle; each of R1, R2, R3, R1′, R2′ and R3′ is independently mono-substituted or multi-substituted substituent and a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heterocycle, a substituted or unsubstituted C6-C30 condensed polycyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and two or more adjacent groups among R1, R2, R3, R1′, R2′ and R3′ can be connected to each other to form a saturated or unsaturated carbocycle; and each Ar is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group.
Each Ar may be a phenyl group, an ethylphenyl group, an ethylbiphenyl group, an o-, m-, or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, and p-cumenyl group, a mesityl group, a phenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a pentarenyl group, an indenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azurenyl group, a heptarenyl group, an acenaphthylrenyl group, a phenanthrenyl group, a fluorenyl group, an anthraquinolyl group, a triphenylene group, a pyrenyl group, a pherylenyl group, a chloropherylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a coroneryl group, a trinaphthylenyl group, a heptaphenyl group, or a carbazolyl group.
where each of R1 to R3 and R1′ to R3′ is independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocycle, or a substituted or unsubstituted amino group; and each of R and R′ is a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocycle, or a substituted or unsubstituted amino group.
As set forth in the reaction scheme 1, the phenylcarbazole-based compound represented by Formula (1) is obtained by reacting carbazole (B′) with a diamine compound (C′).
In above Reaction Scheme 1, X is a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 heterocycle; each of R1, R2, R3, R1′, R2′ and R3′ is independently mono-substituted or multi-substituted substituent and a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heterocycle, a substituted or unsubstituted C6-C30 condensed polycyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and two or more adjacent groups among R1, R2, R3, R1′, R2′ and R3′ can be connected to each other to form a saturated or unsaturated carbocycle; each Ar is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group; and Y is a halogen atom.
An EML material is not particularly restricted, but may be the phenylcarbazole-based compound represented by Formula (1) as a fluorescent or phosphorescent host. Alq3 (tris(8-quinolinolate) aluminum) may be used as a fluorescent host. IDE102 and IDE105 available from Idemitsu Kosan Co., Ltd., and C545T available from Hayashibara may be used as fluorescent dopants, and Ir(PPy)3 (PPy=phenylpyridine) (green), F2Irpic (bis[2-(4,6-difluorophenyl)pyridinato-N,C2′] iridium picolinate) (blue), and RD61 (red) may be vacuum evaporated (doped) in combination as phosphorescent dopants.
2.433 g (10 mmol) of the intermediate compound A was added to 100 mL of 80% acetic acid, and then 1.357 g (5.35 mmol) of iodine (12) and 0.333 g (1.46 mmol) of ortho-periodinic acid (H5IO6) were added thereto. The resultant was stirred under nitrogen atmosphere at 80° C. for 2 hrs.
Further, Compound represented by Formula 3 was subjected to thermal analysis using TGA (Thermo Gravimetric Analysis) and DSC (Differential Scanning Calorimetry) (N2 atmosphere, temperature range: room temperature-600° C. (10° C./min)—TGA, room temperature-400° C.—DSC, Pan type: Pt pan in disposable Al pan (TGA), disposable Al pan (DSC)) to obtain Td 494° C. and Tg 153° C. (FIGS. 3 and 4).
Further, Compound represented by Formula 4 was subjected to thermal analysis using TGA and DSC (N2 atmosphere, temperature range: room temperature-600° C. (10° C./min)—TGA, room temperature-400° C.—DSC, Pan type: Pt pan in disposable Al pan (TGA), disposable Al pan (DSC)) to obtain Td 490° C., Tg 178° C., and Tm of 263° C. (FIGS. 6 and 7).
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