Source: https://patents.google.com/patent/US8021765?oq=5%2C960%2C411
Timestamp: 2018-04-26 23:34:14
Document Index: 447101017

Matched Legal Cases: ['Application No. 10', '§120', 'Application No. 11', 'Application No. 07109066', 'Application No. 07109066', 'Application No. 05111348', 'Application No. 2007', 'Application No. 10', 'Application No. 10', 'Application No. 2004', 'Application No. 10', 'Application No. 200510121732', 'Application No. 2005']

US8021765B2 - Phenylcarbazole-based compound and organic electroluminescent device employing the same - Google Patents
Phenylcarbazole-based compound and organic electroluminescent device employing the same Download PDF
US8021765B2
US8021765B2 US11979267 US97926707A US8021765B2 US 8021765 B2 US8021765 B2 US 8021765B2 US 11979267 US11979267 US 11979267 US 97926707 A US97926707 A US 97926707A US 8021765 B2 US8021765 B2 US 8021765B2
US11979267
US20080107919A1 (en )
Seung-gak Yang
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. This application is a Continuation-in-Part of application Ser. No. 11/286,421 filed on the 25 Nov. 2005, and assigned to the assignee of the present invention. All benefits accruing under 35 U.S.C. §120 from the present application are also hereby claimed.
A HTL material is not particularly restricted, but may be the phenylcarbazole-based compound represented by Formula (1), or any compound known to be used in the HTL. For example, carbazole derivatives, such as N-phenylcarbazole and polyvinylcarbazole, general amine derivatives having an aromatic condensed ring, such as N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), N,N′-di(naphthalen-1-yl)-N,N′-diphenyl benzidine (α-NPD), etc. are used.
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).
Further, Compound 5 was subjected to thermal analysis using Thermo Gravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC) (N2 atmosphere, temperature range: room temperature—600° C. (10° C./min)—TGA, room temperature—400° C.—DSC, Pan Type Pt Pan in disposal Al Pan (TGA), disposable Al pan (DSC)) to obtain Td 480° C. and Tg 155° C.
Further, Compound 7 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 disposal Al Pan (TGA), disposal Al pan (DSC)) to obtain Td 533° C. and Tg 174° C.
Further, Compound 27 was subjected to 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 disposal Al Pan (TGA), disposal Al pan (DSC)) to obtain Td 464° C., Tg 151° C., and Tm 299° C.
A corning 15 Ω/cm2 (1200 Å) ITO glass substrate as an anode was cut to a size of 50 mm×50 mm×0.7 mm and ultrasonically washed with isopropyl alcohol and pure water, for 5 min each wash. Then, the washed glass substrate was irradiated with a UV radiation for 30 min and washed by exposing to ozone, and then, installed in a vacuum evaporator.
An organic EL device was manufactured in the same manner as in Example 3, except that Compound 29 of Synthesis Reference Example 2, which is a derivative of TLB1, instead of Compound 3 was used to form a HIL.
Driving Color Luminous
Hole injection voltage (V) Luminance coordination efficiency
material (@100 A/cm2) (cd/m2) (x, y) (cd/A)
Example 3 Compound 3 7.18 7,253 (0.144, 0.244) 7.25
Example 4 Compound 5 7.07 7,715 (0.144, 0.235) 7.72
Example 5 Compound 7 6.72 7,104 (0.143, 0.232) 7.10
Example 6 Compound 27 6.87 7,931 (0.145, 0.246) 7.93
Comparative IDE 406 8.38 6,528 (0.143, 0.243) 6.53
Comparative TLB1 7.25 7,104 (0.143, 0.235) 7.10
Comparative Compound 28 7.25 7,342 (0.145, 0.239) 7.34
Comparative Compound 29 7.18 7,681 (0.144, 0.245) 7.68
1. A compound represented by one of formulae (5), (7) and (27):
2. A method of preparing a compound represented by Formula (1), comprising:
where X is a biphenyl group;
3. The method of claim 2, 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.
4. An organic electroluminescent display device, comprising:
an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a compound represented by Formulae 5, 7 and 27:
5. The organic electroluminescent device of claim 4, wherein the organic layer is a hole injection layer or a hole transport layer.
6. The organic electroluminescent device of claim 4, wherein the organic layer is a single layer serving as both a hole injection layer and a hole transport layer.
7. The organic electroluminescent device of claim 4, wherein the organic layer is an emitting layer.
8. The organic electroluminescent device of claim 7, wherein the emitting layer is composed of a phosphorescent or fluorescent material.
9. The organic electroluminescent device of claim 7, wherein the compound is used as a fluorescent or phosphorescent host in the emitting layer.
10. The organic electroluminescent device of claim 4, wherein the compound is a compound represented by Formula (5):
11. The organic electroluminescent device of claim 4, wherein the compound is a compound represented by Formula (7):
12. The organic electroluminescent device of claim 4, wherein the compound is a compound represented by Formula (27):
13. The compound of claim 1, wherein the compound is represented by formulae (5).
14. The compound of claim 1, wherein the compound is represented by formulae (7).
15. The compound of claim 1, wherein the compound is represented by formulae (27).
US11979267 2004-11-29 2007-10-31 Phenylcarbazole-based compound and organic electroluminescent device employing the same Active 2027-12-23 US8021765B2 (en)
KR20040098747A KR100787425B1 (en) 2004-11-29 2004-11-29 Phenylcarbazole-based compound and Organic electroluminescence display employing the same
KR10-2004-0098747 2004-11-29
US11286421 US8021764B2 (en) 2004-11-29 2005-11-25 Phenylcarbazole-based compound and organic electroluminescent device employing the same
US11979267 US8021765B2 (en) 2004-11-29 2007-10-31 Phenylcarbazole-based compound and organic electroluminescent device employing the same
US11286421 Continuation-In-Part US8021764B2 (en) 2004-11-29 2005-11-25 Phenylcarbazole-based compound and organic electroluminescent device employing the same
US20080107919A1 true US20080107919A1 (en) 2008-05-08
US8021765B2 true US8021765B2 (en) 2011-09-20
ID=39360065
US11979267 Active 2027-12-23 US8021765B2 (en) 2004-11-29 2007-10-31 Phenylcarbazole-based compound and organic electroluminescent device employing the same
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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HWANG, SEOK-HWAN;KIM, YOUNG-KOOK;LEE, CHANG-HO;AND OTHERS;REEL/FRAME:020769/0159