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Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device

a technology of pyridoindole and pyridoidole, which is applied in the direction of luminescent compositions, organic chemistry, thermoelectric devices, etc., can solve the problems of low electron transport properties, reduce efficiency, and cannot consider the hole-blocking capability of materials, etc., and achieve excellent hole-blocking ability, excellent thermal resistance, and high luminous efficiency

Inactive Publication Date: 2013-12-26
YOKOYAMA NORIMASA +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention is a compound with a unique structure that can be used in organic EL devices. It has excellent hole-blocking ability and is stable in a thin-film state, as well as excellent thermal resistance. The organic EL device made with this compound has high luminous efficiency and low practical driving voltage, which improves durability. Additionally, it can lower the light emission initiation voltage.

Problems solved by technology

However, since the mobility of holes is higher than the mobility of electrons, a problem of reduction in efficiency caused by a part of the holes passing through the light-emitting layer arises.
However, since it has a work function of 5.8 eV, it cannot be considered that the material has hole-blocking capability.
However, TAZ has a great problem of having low electron transport property, and it is necessary to prepare an organic electroluminescence device in combination with an electron-transport material having a higher electron transport property (see e.g., Non-Patent Document 4).Non-Patent Document 4: Japan Society of Applied Physics, Journal of Organic Molecules / Bioelectronics Section, Vol. 11, No. 1, pp.
Further, BCP has a work function as large as 6.7 eV and a high hole-blocking ability, but has a low glass transition point (Tg) which is 83° C., so that it is poor in thin-film stability and thus it cannot be considered that it sufficiently functions as a hole-blocking layer.
All the materials are insufficient in thin-film stability or are insufficient in the function of blocking holes.

Method used

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  • Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
  • Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
  • Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 9,10-Diphenyl-2-(5H-pyrido[4,3-b]indol-5-yl)anthracene (Compound 3)

[0070]In a nitrogen atmosphere, 4.7 g of 2-bromo-9,10-diphenylanthracene, 2.6 g of 5H-pyrido[4,3-b]indole, 0.4 g of copper powder, 4.3 g of potassium carbonate, 0.3 ml of dimethyl sulfoxide and 30 ml of n-dodecane were added to a reaction vessel, then heated and stirred at 210° C. for 18 hours. After cooling to room temperature, 300 ml of chloroform and 30 ml of methanol were added thereto and insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to obtain a crude product, and the crude product was purified by column chromatography (carrier: NH silica gel, eluent: toluene / chloroform) to obtain 1.7 g (yield: 30%) of 9,10-diphenyl-2-(5H-pyrido[4,3-b]indol-5-yl)anthracene (Compound 3) as a yellow powder.

[0071]The structure of the obtained yellow powder was identified using NMR. FIG. 1 shows the results of 1H-NMR measurement.

[0072]The following 24 hydrogen signa...

example 2

Synthesis of 9,10-Diphenyl-2-[4-(5H-pyrido[4,3-b]indol-5-yl)phenyl]anthracene (Compound 9)

[0073]In a nitrogen atmosphere, 4.7 g of 9,10-diphenylanthracene-2-boronic acid, 2.8 g of 5-(4-bromophenyl)-5H-pyrido[4,3-b]indole, 0.50 g of tetrakistriphenylphosphine palladium, 15 ml of an aqueous 2 M potassium carbonate solution, 20 ml of toluene and 1.5 ml of ethanol were added to a reaction vessel, then heated under reflux with stirring for 18 hours. After cooling to room temperature, a crude product was collected by filtration, and the crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / ethyl acetate) to obtain 1.6 g (yield: 32%) of 9,10-diphenyl-2-[4-(5H-pyrido[4,3-b]indol-5-yl)phenyl]anthracene (Compound 9) as a yellow powder.

[0074]The structure of the obtained yellow powder was identified using NMR. FIG. 2 shows the results of 1H-NMR measurement.

[0075]The following 28 hydrogen signals were detected on 1H-NMR (CDCl3). δ (ppm)=9.39 (1H), 8.52 (1H), ...

example 3

Synthesis of 9,10-Diphenyl-2-[6-(5H-pyrido[4,3-b]indol-5-yl)pyridin-3-yl]anthracene (Compound 15)

[0076]In a nitrogen atmosphere, 4.5 g of 9,10-diphenylanthracene-2-boronic acid, 3.0 g of 5-(5-bromopyridin-2-yl)-5H-pyrido[4,3-b]indole, 0.55 g of tetrakistriphenylphosphine palladium, 19 ml of an aqueous 2 M potassium carbonate solution, 72 ml of toluene and 18 ml of ethanol were added to a reaction vessel, then heated under reflux with stirring for 18 hours. After cooling to room temperature, 100 ml of toluene and 100 ml of water were added thereto, followed by stirring, and the organic layer was separated by liquid separation. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: NH silica gel, eluent: toluene) to obtain 3.0 g (yield: 57%) of 9,10-diphenyl-2-[6-(5H-pyrido[4,3-b]indol-5-yl)pyridin-3-yl]anthracene (Compound 15) as a yellow powder.

[0077...

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Abstract

The present invention provides an organic compound having excellent properties, which is excellent in electron-injection / transport performance, has hole-blocking ability and is high stability in a thin-film state, as a material for an organic electroluminescence device having a high efficiency and a high durability, and provides is an organic electroluminescence device having a high efficiency and a high durability using the compound. The present invention relates to a compound having a substituted anthracene ring structure and a pyridoindole ring structure represented by general formula (1); and an organic electroluminescence device having a pair of electrodes and at least one organic layer interposed between the electrodes in which the at least one organic layer contains the compound.

Description

REFERENCE TO PRIOR APPLICATIONS[0001]This application is a continuation of U.S. application Ser. No. 13 / 120,665, filed Mar. 24, 2011, now allowed; which is a 371 of International application PCT / JP2009 / 066450, filed Sep. 18, 2009; and to Japanese patent application 2008-243937, filed Sep. 24, 2008, all incorporated herein by reference.TECHNICAL FIELD[0002]The present invention relates to a compound suitable for an organic electroluminescence device which is a self-luminescent device suitable for various displaying devices and a device. More specifically, it relates to a compound having a substituted anthracene ring structure and a pyridoindole ring structure and to an organic electroluminescence device using the compound.BACKGROUND ART[0003]Since organic electroluminescence devices are self-luminescent devices, they are bright and excellent in visibility as compared with liquid-crystalline devices and capable of giving clear display, so that the organic electroluminescence devices h...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L51/00
CPCH01L51/0072H01L51/0067C07D471/04C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029H05B33/14H10K85/626H10K85/631H10K85/6572H10K50/14H10K50/171H10K85/615H10K85/654
Inventor YOKOYAMA, NORIMASAHAYASHI, SHUICHIIZUMI, SAWAKABASAWA, NAOAKIKUSANO, SHIGERU
Owner YOKOYAMA NORIMASA
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