WO2009107596A1 - Organic luminescent medium and organic el element - Google Patents

Organic luminescent medium and organic el element Download PDF

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WO2009107596A1
WO2009107596A1 PCT/JP2009/053247 JP2009053247W WO2009107596A1 WO 2009107596 A1 WO2009107596 A1 WO 2009107596A1 JP 2009053247 W JP2009053247 W JP 2009053247W WO 2009107596 A1 WO2009107596 A1 WO 2009107596A1
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舟橋 正和
河村 昌宏
光則 伊藤
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出光興産株式会社
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0059Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H01L51/006Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1011Condensed systems
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0052Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H01L51/0054Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5012Electroluminescent [EL] layer

Abstract

Disclosed is an organic luminescent medium comprising a diaminopyrene derivative represented by formula (1) and an anthracene derivative represented by formula (2).

Description

The organic light emitting medium and an organic EL device

The present invention relates to an organic light emitting medium and an organic EL device using the same.

Conventionally, organic EL devices (organic electroluminescent device) has been known which utilizes the emission of organic compounds. The organic EL element has a plurality of organic thin films are stacked between an anode and a cathode. In this configuration, when a voltage is applied between the anode and the cathode, the organic thin film, from the anode and the cathode, holes and electrons are injected, respectively. It molecules in the excited state in the emission layer in the organic thin film produced by the injected holes and electrons. Then, the energy in returning from the excited state to the ground state is emitted as light.

Examples of materials used for the light emitting layer, Patent Document 1, the combination of the anthracene host and arylamine is disclosed. Patent Document 2 to 4, a combination of an anthracene host diaminodiphenyl pyrene dopant having a specific structure are disclosed. Furthermore, Patent Documents 5 and 6, the host material of anthracene is disclosed.
However, in the blue light-emitting element is also using a combination of host and dopant disclosed in these documents, maintaining a long service life, and to obtain a short-wavelength blue light emission is difficult. Further, the green light-emitting device maintains high efficiency, and it is difficult to obtain a long-life organic EL device.
WO2004 / 018588 JP WO2004 / 018587 JP JP 2004-204238 JP WO2005 / 108348 JP WO2005 / 054162 JP WO2005 / 061656 JP

An object of the present invention, and long life blue luminescence emission with a short wavelength, also the organic EL device comprising a combination of a specific host material and a dopant material that can achieve and long life green light with high efficiency, and the organic it is to provide an organic light emitting medium which can be used in the organic thin film layer of the EL element.
Another object of the present invention is able to obtain high luminous efficiency, long life, organic EL element comprising a combination of a specific host material and a dopant material, and be used in the organic thin film layer of the organic EL device it is possible to provide an organic light emitting medium.

Result of intensive studies to solve the above problems, the present inventors have found that can solve the problem by the following present invention.
According to the present invention, such as the following organic light-emitting medium.

A diaminopyrene derivative represented by the following formula (1), an organic light emitting medium comprising the anthracene derivative represented by the following formula (2).

Figure JPOXMLDOC01-appb-C000007

(In the formula (1), R 21 ~ R 24 each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted a cycloalkyl group having 3 to 50 ring carbon atoms substituted, or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, when there is one or two pairs of adjacent alkyl groups on the same benzene ring, said adjacent alkyl groups may form a divalent linking group bonded to a substituted or unsubstituted with one another, provided that if said adjacent alkyl groups to form a naphthyl group together with the benzene ring to which they are attached except.
n1 ~ n4 are each independently an integer of 0-5.
R a and R b are each independently a hydrogen atom, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted a cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted 6 to 50 carbon atoms aryloxy group, a substituted or unsubstituted silyl group, a halogen atom or a cyano group.
However, if R a and R b are hydrogen atoms at the same time is excluded. )
Figure JPOXMLDOC01-appb-C000008

(In the formula (2), Ar 11 and Ar 12 each independently represent a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms,
R 1 ~ R 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted having 7 to 50 carbon atoms aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a group selected from cyano group.
However, when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group and the other is not 4- (1-naphthyl) phenyl-1-yl group.
Further, at least not one but a substituted or unsubstituted anthryl group Ar 11 and Ar 12. )

The organic light emitting medium comprising 'a diaminopyrene derivative represented by the following formula (2)' the following formula (1) and anthracene derivative represented by.

Figure JPOXMLDOC01-appb-C000009

( 'In, R 21' Equation (1) ~ R 24 'each independently represent a hydrogen atom, having 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted 1 to 50 carbon atoms alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 20 carbon atoms, If there are identical alkyl groups adjacent one or two pairs on the benzene ring, the alkyl group may form a divalent bonding group or a substituted or unsubstituted bonded to each other in contact 該隣.
n1 '~ n4' are each independently an integer of 1-5.
R a 'and R b' are independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. )
Figure JPOXMLDOC01-appb-C000010

( 'In, Ar 11' Equation (2) and Ar 12 'each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a heterocyclic group having 5 to 50 ring atoms,
R 1 '~ R 8' are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic ring group having 6 to 50 arylthio group, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a group selected from nitro and hydroxyl groups.
However, a R 1 '~ R 8' is hydrogen atom, when one of Ar 11 'and Ar 12' is an unsubstituted 2-naphthyl group, the other 4- (1-naphthyl) phenyl-1- not-yl group. )

An anode, a cathode, and a least one organic thin layer between the anode and the cathode, the organic electroluminescent device at least one layer containing the organic luminescent medium of the organic thin film layer.

According to the present invention, and long life blue luminescence emission with a short wavelength, also the organic EL device comprising a combination of a specific host material and a dopant material that can achieve and long life green light with high efficiency, and the organic it is possible to provide an organic light emitting medium which can be used in the organic thin film layer of the EL element.
According to the present invention, it is possible to obtain high luminous efficiency, it is possible to provide an organic light emitting medium which can be used in the organic thin film layer of a long lifetime organic EL device, and the organic EL element.

Organic luminescent medium]
The organic luminescent medium of the present invention is an organic light emitting medium I, there are aspects of the organic luminescent medium II, respectively, include a specific diaminopyrene derivative, and a specific anthracene derivative. The organic luminescent medium contributes to light emission as a constituent of the organic thin film layer of the organic EL element, for example, present in the layer as a deposit. When used in the organic EL device, the organic light emitting medium I, to allow the beginning and the short wavelength emitting blue emission of high color purity, can contribute to the long life, or obtain a high luminous efficiency it can. Also in the organic luminescent medium II, it can be realized and long lifetime green organic EL element with high luminous efficiency. Hereinafter, an organic light emitting medium I, II will be described.

In the present invention, the "ring carbon" means a carbon atom constituting a saturated ring, unsaturated ring, or an aromatic ring. The "ring atoms" refers to a heterocyclic (saturated ring, unsaturated ring, and an aromatic ring) carbon atoms and hetero atoms constituting the.
In each formula of definition of the invention, examples of the substituent in the "substituted or unsubstituted ...", alkyl groups as described below, an aryl group, a cycloalkyl group, an alkoxy group, a heterocyclic group, an aralkyl group , an aryloxy group, an arylthio group, an alkoxycarbonyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxyl group and the like, preferably an alkyl group, an aryl group, a cycloalkyl group, a heterocyclic group.

Organic luminescent medium I]
The organic luminescent medium I includes a diaminopyrene derivative according to the present invention represented by the following formula (1), the anthracene derivative represented by the following formula (2).

(Diaminopyrene derivative)
Diaminopyrene derivative according to the organic light emitting medium I is represented by the following formula (1).

Figure JPOXMLDOC01-appb-C000011

Wherein (1), R 21 ~ R 24 each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nuclear cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, when there is one or two pairs of adjacent alkyl groups on the same benzene ring, the adjacent alkyl groups may form a divalent linking group bonded to a substituted or unsubstituted with one another, provided that if said adjacent alkyl groups to form a naphthyl group together with the benzene ring to which they are attached except.
n1 ~ n4 are each independently an integer of 0-5.
R a and R b are each independently a hydrogen atom, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted a cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted 6 to 50 carbon atoms aryloxy group, a substituted or unsubstituted silyl group, a halogen atom or a cyano group. However, if R a and R b are hydrogen atoms at the same time is excluded.

R a and R b is preferably an alkyl group, a cycloalkyl group.
The alkyl group, more preferably an alkyl group having 1 to 6 carbon atoms, such as methyl group, ethyl group, n- propyl group, an isopropyl group, n- butyl group, a t- butyl group.
The cycloalkyl group is more preferably a C 3-6 cycloalkyl group having a carbon, such as cyclopropanyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group.

The substituted or unsubstituted aryl group R 21 ~ R 24, for example, a phenyl group, methylphenyl group, ethylphenyl group, a biphenyl group, cyclopentyl phenyl group, phenyl group, methyl biphenyl group, an ethyl biphenyl group, cyclopentyl phenyl group, cyclohexyl biphenyl group, terphenyl group, a naphthyl group, a methylnaphthyl group, an anthryl group, a pyrenyl group, a fluoranthenyl group, a perylenyl group, a fluorenyl group and the like, preferably a phenyl group, a naphthyl group, a fluorenyl a group.

The substituted or unsubstituted alkyl group of R 21 ~ R 24, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, sec- butyl group, tert- butyl group, a pentyl group, a hexyl group, a heptyl group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group and the like, preferably methyl group, an ethyl group, a propyl group, tert- butyl group.

If there is the same benzene ring one or two pairs of adjacent alkyl groups on (a benzene ring bonded directly to the nitrogen atom), an alkyl group is a divalent saturated or unsaturated bonds and substituted or unsubstituted with one another each adjacent it may form a bond group of saturated.

The substituents the benzene ring and bonding group directly bonded to the nitrogen atom to form, it is preferable to form the mother nucleus represented by the following general formula (3-1) to (3-6), these nucleus further alkyl groups, the alkenyl group, an alkynyl group, which may have a substituent such as an aryl group. However, when forming a 1-naphthyl group are excluded.

Figure JPOXMLDOC01-appb-C000012

(Wherein, A, D, E, G, J, respectively -CH 2 -, - representing the (each R 50 and R 51 substituents), - - CR 50 R 51 O -, - S -, - N-, or a -CO-,
a ~ h represents an integer of 1 to 10.
a, b, c, g, if h is 2 or more, A presence of a plurality, D, E, G, J may have respectively the same or different. )

Preferably a ~ c is 5 or 6 respectively, it is preferred that the d ~ f are each 2, g, h are preferably are each 1.
Substituents R 50, R 51 is preferably a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, the ring carbon atoms of 6 to 14 aryl group, a heterocyclic group having ring carbon atoms of 5 to 14, more preferably an alkyl group, an aryl group having ring carbon atoms of 6 to 14 from 1 to 6 carbon atoms.

Substituents the benzene ring and bonding group directly bonded to the nitrogen atom is formed, more preferably a ring of the following structure.

Figure JPOXMLDOC01-appb-C000013

The cycloalkyl group of R 21 ~ R 24, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, heptyl group cyclopropyl, cyclooctyl group, cyclononyl group, bicycloheptyl group, bicyclooctyl group, tri cycloheptyl group, adamantyl group and the like, cyclopentyl group, cyclohexyl group, heptyl group cycloalkyl, bicycloheptyl group, bicyclooctyl group, an adamantyl group are preferred.

The substituted or unsubstituted aralkyl group R 21 ~ R 24, for example, benzyl, 1-phenylethyl, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenyl-isopropyl group, a phenyl -t- butyl groups, alpha-naphthylmethyl group, 1-alpha-naphthylethyl group, 2-alpha-naphthylethyl group, 1-alpha-naphthyl isopropyl group, 2-alpha-naphthyl isopropyl, beta-naphthylmethyl group, 1-beta- naphthylethyl group, 2-beta-naphthylethyl group, 1-beta-naphthyl isopropyl group, 2-beta-naphthyl isopropyl, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p- methylbenzyl group, m - methylbenzyl group, o- methylbenzyl group, p- chlorobenzyl group, m- chlorobenzyl group, o- chlorobenzyl group, p- Bro Benzyl, m- bromobenzyl group, o- bromobenzyl group, p- iodobenzyl group, m- iodobenzyl group, o- iodobenzyl group, p- hydroxybenzyl, m- hydroxybenzyl, o- hydroxybenzyl , p- aminobenzyl group, m- aminobenzyl group, o- aminobenzyl group, p- nitrobenzyl group, m- nitrobenzyl group, o- nitrobenzyl group, p- cyanobenzyl group, m- cyanobenzyl group, o - cyanobenzyl group, 1-hydroxy-2-phenyl-isopropyl, 1-chloro-2-phenyl isopropyl group, alpha-phenoxybenzyl group, alpha, alpha-dimethylbenzyl group, alpha, alpha-methyl phenyl benzyl group, alpha, alpha-ditrifluoromethylbenzyl group, triphenylmethyl group, alpha-benzyloxybenzyl group, and the like, et al. That.

Examples of R a and R b are the same as those for R 1 ~ R 8 of formula (2) described later.

In a preferred embodiment of the present invention, diaminopyrene derivative of formula (1) is represented by the following formula.

Figure JPOXMLDOC01-appb-C000014

In the above formula, R 21 ~ R 24, R a and R b are as defined above. R 21 ~ R 24 may be the same as or different from each other but, R 21 and R 23 and is preferably R 22 and R 24 are the same respectively. Furthermore, R a and R b may be the same or different, but are preferably the same.

Specific examples of the diaminopyrene derivative represented by the formula (1) include compounds represented by the following formula.

Figure JPOXMLDOC01-appb-C000015

Figure JPOXMLDOC01-appb-C000016

Figure JPOXMLDOC01-appb-C000017

Figure JPOXMLDOC01-appb-C000018

Figure JPOXMLDOC01-appb-C000019

Figure JPOXMLDOC01-appb-C000020

Figure JPOXMLDOC01-appb-C000021

Figure JPOXMLDOC01-appb-C000022

Figure JPOXMLDOC01-appb-C000023

Figure JPOXMLDOC01-appb-C000024

Figure JPOXMLDOC01-appb-C000025

Figure JPOXMLDOC01-appb-C000026

Figure JPOXMLDOC01-appb-C000027

Figure JPOXMLDOC01-appb-C000028

Figure JPOXMLDOC01-appb-C000029

(Anthracene derivative)
Anthracene derivative according to the organic light emitting medium I is represented by the following formula (2).

Figure JPOXMLDOC01-appb-C000030

(In the formula (2), Ar 11 and Ar 12 each independently represent a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms,
R 1 ~ R 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted having 7 to 50 carbon atoms aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a group selected from cyano group.
However, when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group and the other is not 4- (1-naphthyl) phenyl-1-yl group.
Further, at least not one but a substituted or unsubstituted anthryl group Ar 11 and Ar 12. )

Anthracene derivative represented by the formula (2) preferably when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group and the other is not a phenyl group aryl-substituted.

Anthracene derivative according to the present invention, the following anthracene derivatives (A), (B), and be either (C) are preferably selected, the configuration and determining characteristics of the organic EL elements to be applied.

(Anthracene derivative (A))
The anthracene derivatives, Ar 11 and Ar 12 in the formula (2) are each independently has a substituted or unsubstituted fused aryl group having 10 to 20 carbon atoms. As the anthracene derivative, it may be divided into a case when Ar 11 and Ar 12 are the same substituted or unsubstituted condensed aryl group, and a different substituted or unsubstituted condensed aryl group.
Specifically, the following formulas (2-1) to the anthracene derivative represented by (2-3), and anthracene derivatives Ar 11 and Ar 12 in the formula (2) are different substituted or unsubstituted condensed aryl group and the like.

Anthracene derivative represented by the following formula (2-1) may, Ar 11 and Ar 12 has a substituted or unsubstituted 9-phenanthrenyl group.

Figure JPOXMLDOC01-appb-C000031

(In the formula (2-1), R 1 ~ R 8 are as defined above,
R 11 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted an aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, carboxyl group, a halogen atom, a cyano group, a group selected from nitro and hydroxyl groups,
a is an integer from 0 to 9. when a is an integer of 2 or more, plural R 11 are the two substituted or condition that unsubstituted phenanthrenyl group are identical, each may be the same or different. )

Anthracene derivative represented by the following formula (2-2), Ar 11 and Ar 12 in the formula (2) has a substituted or unsubstituted 2-naphthyl group.

Figure JPOXMLDOC01-appb-C000032

(In the formula (2-2), R 1 ~ R 8 and R 11 are as defined above,
b is an integer of 1 to 7. If b is an integer of 2 or more, plural R 11 are the two substituted or condition that unsubstituted 2-naphthyl group are the same, each may be the same or different. )

Anthracene derivative represented by the following formula (2-3), Ar 11 and Ar 12 in the formula (2) has a substituted or unsubstituted 1-naphthyl group.

Figure JPOXMLDOC01-appb-C000033

(In the formula (2-2), R 1 ~ R 8, R 11 and b are as defined above. Also, if b is an integer of 2 or more, plural R 11 are the two substituted or unsubstituted on condition that 1-naphthyl group are the same, each may be the same or different.)

The anthracene derivative Ar 11 and Ar 12 are different substituted or unsubstituted condensed aryl group in formula (2), a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, and substituted or it is preferably either unsubstituted 2-naphthyl group.
Specifically, Ar 11 is a 1-naphthyl group, and when Ar 12 is a 2-naphthyl group, when Ar 11 is a 1-naphthyl group, and Ar 12 is a 9-phenanthryl group, and Ar 11 is 2- naphthyl group and Ar 12 is the case of 9-phenanthryl group.

(Anthracene derivative (B))
The anthracene derivative is one substituted or unsubstituted phenyl group of Ar 11 and Ar 12 in the formula (2) and the other is a fused aryl group or a substituted or unsubstituted 10 to 20 carbon atoms. As the anthracene derivative, and specific examples thereof include anthracene derivatives represented by the following formula (2-4) and (2-5).

Anthracene derivative represented by the following formula (2-4) is the Ar 11 is a substituted or unsubstituted 1-naphthyl group in the formula (2), Ar 12 has a substituted or unsubstituted phenyl group .

Figure JPOXMLDOC01-appb-C000034

(In the formula (2-4), R 1 ~ R 8, R 11 and b are as defined above,
Ar 6 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, 9,9-dimethyl-fluoren-1-yl group, 9,9-dimethyl-fluorene-2 yl group, 9,9-dimethyl-fluoren-3-yl group, 9,9-dimethyl-fluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or a dibenzofuran -4-yl group. Moreover, Ar 6, together with the benzene ring to which it is attached, may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzo fluorenyl group. If b is an integer of 2 or more, plural R 11 are each may be the same or different. )

Anthracene derivative represented by the following formula (2-5) is the Ar 11 is a substituted or unsubstituted 2-naphthyl group in the formula (2), Ar 12 has a substituted or unsubstituted phenyl group .

Figure JPOXMLDOC01-appb-C000035

(In the formula (2-5), R 1 ~ R 8, R 11 and b are as defined above,
Ar 7 represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or a cycloalkyl group having 3 to 50 ring carbon atoms unsubstituted, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or a dibenzofuran-4-yl group. Further, Ar 7 together with the benzene ring to which it is attached, may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzo fluorenyl group. If b is an integer of 2 or more, plural R 11 are each may be the same or different.
However, Ar 7 except the case of forming together with the adjacent phenylene group 4- (1-naphthyl) phenyl-1-yl group. )

(Anthracene derivative (C))
The anthracene derivative is represented by the following formula (2-6), specifically, the following formulas (2-6-1), with either (2-6-2) and (2-6-3) it is preferably a derivative represented.

Figure JPOXMLDOC01-appb-C000036

(In the formula (2-6), R 1 ~ R 8 and Ar 6 are as defined above,
Ar 5 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a heterocyclic group of the substituted or unsubstituted atoms 5 to 50, Ar 5 and Ar 6 are each independently selected. )
Figure JPOXMLDOC01-appb-C000037

(In the formula (2-6-1), R 1 ~ R 8 are as defined above.)
Figure JPOXMLDOC01-appb-C000038

(In the formula (2-6-2), R 1 ~ R 8 is a fused aryl group of the same in which .Ar 8 is a substituted or unsubstituted aromatic ring group having 10-20.)
Figure JPOXMLDOC01-appb-C000039

(In the formula (2-6-3), R 1 ~ R 8 is the same as equation (2).
Ar 5a and Ar 6a are each independently a fused substituted or unsubstituted aryl group having 10 to 20 ring carbon atoms. )

The aryl group of Ar 11, Ar 12 substituted or unsubstituted aromatic ring group having 6 to 20, a phenyl group, 1-naphthyl, 2-naphthyl, 1-anthryl group, 2-anthryl group, 9-anthryl group , 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group , 4-pyrenyl group, 6-chrysenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4-benzo [c] phenanthryl group, 5- benzo [c] phenanthryl group, 6-benzo [c] phenanthryl group, 1-benzo [g] chrysenyl, 2-benzo [g] click Seniru group, 3-benzo [g] chrysenyl group, 4-Benzo [g] chrysenyl group, 5-benzo [g] chrysenyl group, 6-benzo [g] chrysenyl, 7-benzo [g] chrysenyl group, 8- benzo [g] chrysenyl group, 9-benzo [g] chrysenyl group, 10-benzo [g] chrysenyl group, 11-benzo [g] chrysenyl group, 12-benzo [g] chrysenyl group, 13-benzo [g] chrysenyl group, 14-benzo [g] chrysenyl group, 1-triphenylmethyl group, 2-triphenyl group, 2-fluorenyl group, 9,9-dimethyl-fluoren-2-yl group, benzofluorenyl group, dibenzo fluorenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p- terphenyl-4-yl group, p- terphenyl-3-yl group, p- Taaffe 2-yl group, m- terphenyl-4-yl group, m- terphenyl-3-yl group, m- terphenyl-2-yl group, o- tolyl group, m- tolyl group, p- tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4 ' -. methylbiphenyl-yl group, 4 "-t-butyl -p- terphenyl-4-yl group is preferably a substituted phenyl group and a substituted or unsubstituted aryl group having 10 to 14 carbon atoms (e.g. , 1-naphthyl, 2-naphthyl, 9-phenanthryl group).

Further, Ar 5a, the substituted or unsubstituted fused aryl group having 10 to 20 ring carbon atoms of Ar 6a and Ar 8, 1-naphthyl, 2-naphthyl, 1-anthryl group, 2-anthryl group, 9 - anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2 - pyrenyl group, 4-pyrenyl group, 2-fluorenyl group and the like. In particular, 1-naphthyl, 2-naphthyl, 9-phenanthryl group are preferable.

The aryl group of R 1 ~ R 8, R 11 , Ar 5 and substituted or unsubstituted C 6 to C 50 Ar 6, phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl group, 2 - anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1 - pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p- terphenyl-4-yl group, p- terphenyl-3-yl group, p- terphenyl-2-yl group, m- terphenyl-4-yl group, m- terphenyl-3-yl group, m- terphenyl-2-yl group, o- Lil group, m- tolyl group, p- tolyl group, p-t-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl-yl group, 4 "-t-butyl -p- terphenyl-4-yl group and the like.

The heterocyclic group of R 1 ~ R 8, R 11 and Ar 5 ~ substituted or unsubstituted 5 to 50 ring atoms of Ar 7, 1-pyrrolyl, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group , 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group , 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl, 3-furyl group, 2-benzofuranyl group , 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-Isobe Zofuraniru group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4 - phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthroline-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline - 4-yl group, 1,7-phenanthroline-5-yl group, 1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group, 1 7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8-phenanthroline-4 yl group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8 - phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthryl Phosphorus-10-yl group, 1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group , 2,9-phenanthroline-1-yl group, 2,9-phenanthroline-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline 6-yl group, 2,9-phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group, 2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group, 2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline -6 - yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-yl group, 2, 7-phenanthroline-3-yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-phenanthroline-8 yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenol thiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, - phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl, 3-thienyl group, 2 - methyl pyrrol-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group, 3-methyl-pyrrol-1-yl group, 3 - methyl pyrrol-2-yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group, 2-t-butyl-pyrrol-4-yl group, 3- (2-phenylpropyl) pyrrole 1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl , 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group, and 4-t-butyl-3-indolyl group and the like.

The alkyl group of R 1 ~ R 8, R 11 and Ar 5 ~ substituted or unsubstituted C 1 -C 50 Ar 7, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl group, s- butyl group, an isobutyl group, t- butyl group, n- pentyl group, n- hexyl, n- heptyl, n- octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxy isobutyl, 1,2-dihydroxyethyl group, 1,3-dihydroxy isopropyl, 2,3-dihydroxy -t- butyl group, 1,2,3-hydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloro isobutyl group, 1,2-dichloroethyl group, 1,3-dichloro isopropyl group, 2,3-dichloro -t- Bed Group, 1,2,3-trichloro propyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromo isobutyl group, 1,2-dibromo ethyl group, 1,3-dibromo isopropyl group, 2, 3-dibromo -t- butyl group, 1,2,3-bromopropyl group, an iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodo isobutyl group, 1,2 Jiyodoechiru group, 1,3 diiodo isopropyl group, 2,3-diiodo -t- butyl group, 1,2,3-triiodo-propyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-amino isobutyl group, 1 , 2-diaminoethyl group, 1,3-diamino isopropyl, 2,3-diamino -t- butyl group, 1,2,3-aminopropyl group, a cyanomethyl group , 1-cyanoethyl, 2-cyanoethyl, 2-cyano isobutyl group, 1,2-dicyano ethyl, 1,3-dicyano isopropyl group, 2,3-dicyano -t- butyl group, 1,2,3 tricyanobenzene propyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitro isobutyl group, 1,2 Jinitoroechiru group, 1,3-dinitro-isopropyl, 2,3-dinitro -t- butyl , 1,2,3-trinitro-propyl group and the like.

The cycloalkyl group of R 1 ~ R 8, R 11 and Ar 5 ~ substituents a substituted or unsubstituted aromatic ring group having 3 to 50 of the Ar 7, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4 - methylcyclohexyl group, 1-adamantyl, 2-adamantyl, 1-norbornyl group, 2-norbornyl group and the like.

Alkoxy group R 1 ~ R 8, and substituted or unsubstituted C 1 -C 50 R 11 is a group represented by -OZ, Z, the R 1 ~ carbon atoms substituted or unsubstituted R 8 It is selected from alkyl groups of 1 to 50.

R 1 ~ R 8, R 11 and Ar 5 ~ Ar number 7 carbon atoms of the substituted or unsubstituted substituent 7-50 aralkyl group (the aryl moiety having 6 to 49 alkyl moiety is a number 1-44 carbon atoms) as is benzyl, 1-phenylethyl, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenyl-isopropyl group, a phenyl -t- butyl group, alpha-naphthylmethyl group, 1-alpha-naphthylethyl group, 2-alpha-naphthylethyl group, 1-alpha-naphthyl isopropyl group, 2-alpha-naphthyl isopropyl, beta-naphthylmethyl group, 1-beta-naphthylethyl group, 2-beta-naphthylethyl group, 1-beta- naphthylisopropyl group, 2-beta-naphthyl isopropyl, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p- methylbenzyl group, m- methylbenzyl Group, o- methylbenzyl group, p- chlorobenzyl group, m- chlorobenzyl group, o- chlorobenzyl group, p- bromobenzyl group, m- bromobenzyl group, o- bromobenzyl group, p- iodobenzyl group, m- iodobenzyl group, o- iodobenzyl group, p- hydroxybenzyl, m- hydroxybenzyl, o- hydroxybenzyl group, p- aminobenzyl group, m- aminobenzyl group, o- aminobenzyl group, p- nitrobenzyl group, m- nitrobenzyl group, o- nitrobenzyl group, p- cyanobenzyl group, m- cyanobenzyl group, o- cyanobenzyl group, 1-hydroxy-2-phenyl-isopropyl, 1-chloro-2- phenyl isopropyl group and the like.

Aryloxy group R 1 ~ R 8, and substituted or unsubstituted aromatic ring group having 6 to 50 R 11 is represented as -OY, Y, the R 1 ~ ring carbon atoms of the substituted or unsubstituted R 8 selected from aryl groups 6-50.

Arylthio group, a substituted or unsubstituted aromatic ring group having 6 to 50 R 11 is represented as -SY, Y is aryl group of the R 1 ~ substituted or unsubstituted aromatic ring group having 6 to 50 R 8 To be elected.

Substituted or unsubstituted C 2-50 alkoxycarbonyl group R 11 (alkyl moiety 1-49 carbon atoms) is represented as -COOZ, Z is the number of carbon atoms of the substituted or unsubstituted wherein R 1 ~ R 8 selected from alkyl groups of 1-49.

The substituted silyl group of R 1 ~ R 8 and R 11, a trimethylsilyl group, triethylsilyl group, t- butyl dimethyl silyl group, a vinyl dimethyl silyl group, propyldimethylsilyl group, a triphenylsilyl group and the like.

Examples of the halogen atom of R 1 ~ R 8 and R 11, fluorine, chlorine, bromine, and iodine.

The above equation (2), the formula (2-1) to (2-6), formula (2-6-1), anthracene derivatives represented by (2-6-2) and (2-6-3) in, preferably all of R 1 ~ R 8 is a hydrogen atom.

Specific examples of the anthracene derivative represented by the formula (2), include derivatives of the following formula.

Figure JPOXMLDOC01-appb-C000040

Figure JPOXMLDOC01-appb-C000041

Figure JPOXMLDOC01-appb-C000042

Figure JPOXMLDOC01-appb-C000043

Figure JPOXMLDOC01-appb-C000044

Figure JPOXMLDOC01-appb-C000045

Figure JPOXMLDOC01-appb-C000046

Figure JPOXMLDOC01-appb-C000047

Figure JPOXMLDOC01-appb-C000048

Figure JPOXMLDOC01-appb-C000049

Figure JPOXMLDOC01-appb-C000050

Figure JPOXMLDOC01-appb-C000051

Figure JPOXMLDOC01-appb-C000052

Figure JPOXMLDOC01-appb-C000053

Figure JPOXMLDOC01-appb-C000054

Figure JPOXMLDOC01-appb-C000055

Figure JPOXMLDOC01-appb-C000056

Figure JPOXMLDOC01-appb-C000057

Figure JPOXMLDOC01-appb-C000058

Figure JPOXMLDOC01-appb-C000059

Diaminopyrene derivative represented by the formula (1) may, for example, after introducing a substituent in a manner known to dibromopyrene obtained by bromination of commercially available pyrene, brominated again, under the metal catalyst, the corresponding it can be synthesized by reacting a secondary amine compound. Further, the anthracene derivative represented by the formula (2), for example, can be synthesized by the method of No. WO2004 / 018 587 publication.

The organic luminescent medium of the present invention is in a state in which the anthracene derivative represented by the diaminopyrene derivative type represented by the formula (1) as previously described (2) coexist.
The mass ratio of the anthracene derivative represented by the diaminopyrene derivative and represented by the formula (1) (2) is 50:50 to 0.1: is preferably 99.9, 20:80 to 1 : and more preferably 99.

Organic luminescent medium II]
The organic luminescent medium II includes 'a diaminopyrene derivative according to the present invention represented by the following formula (2)' the following formula (1) an anthracene derivative represented by the.

(Diaminopyrene derivative)
Diaminopyrene derivative according to the organic light emitting medium II is represented by the following formula (1) '.

Figure JPOXMLDOC01-appb-C000060

'During, R 21' Equation (1) ~ R 24 'each independently represent a hydrogen atom, an alkyl substituted or unsubstituted aryl group, a substituted or unsubstituted C 1 -C 50 having 6 to 50 ring carbon atoms group, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 20 carbon atoms, the same If there are alkyl groups adjacent one or two pairs on the benzene ring of the alkyl groups may form a divalent bonding group or a substituted or unsubstituted bonded to each other in contact 該隣.
n1 '~ n4' are each independently an integer of 1-5.
R a 'and R b' are independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

Examples of substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group of R 21 '~ R 24' having 6 to 50 ring carbon atoms are the same as those of R 21 ~ R 24 in the formula (1) is there.

If there is the same benzene ring one or two pairs of adjacent alkyl groups on (a benzene ring bonded directly to the nitrogen atom), an alkyl group is a divalent saturated or unsaturated bonds and substituted or unsubstituted with one another each adjacent it may form a bond group of saturated.

The substituents the benzene ring and bonding group directly bonded to the nitrogen atom to form, it is preferable to form the mother nucleus represented by the general formula (3-1) to (3-6), these nucleus further alkyl groups, the alkenyl group, an alkynyl group, which may have a substituent such as an aryl group.

Figure JPOXMLDOC01-appb-C000061

(Wherein, A, D, E, G, J, respectively -CH 2 -, - representing the (each R 50 and R 51 substituents), - - CR 50 R 51 O -, - S -, - N-, or a -CO-,
a ~ h represents an integer of 1 to 10.
a, b, c, g, if h is 2 or more, A presence of a plurality, D, E, G, J may have respectively the same or different. )

Preferably a ~ c is 5 or 6 respectively, it is preferred that the d ~ f are each 2, g, h are preferably are each 1.
Substituents R 50, R 51 is preferably a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, the ring carbon atoms of 6 to 14 aryl group, a heterocyclic group having ring carbon atoms of 5 to 14, more preferably an alkyl group, an aryl group having ring carbon atoms of 6 to 14 from 1 to 6 carbon atoms.

Substituents the benzene ring and bonding group directly bonded to the nitrogen atom is formed, more preferably a ring of the following structure.

Figure JPOXMLDOC01-appb-C000062

Examples of cycloalkyl groups, substituted or unsubstituted aralkyl group R 21 '~ R 24' in R 21 '~ R 24' are the same as those of R 21 ~ R 24 in the formula (1).

R 21 '~ R 24' is preferably a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t- butyl group, a substituted or unsubstituted cyclohexyl group, or a substituted or unsubstituted trimethylsilyl group.

Aryl groups R a 'and R b' substituted or unsubstituted aromatic ring group having 6 to 50 are, ~ R 11 ring carbon atoms, "substituted or unsubstituted as defined in 6 below Formula (2) '50 it is similar to the aryl group ", preferably a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

In a preferred embodiment of the present invention, diaminopyrene derivative of formula (1) 'is expressed by the following equation.

Figure JPOXMLDOC01-appb-C000063

In the above formula, R 21 '~ R 24' , R a ' and R b' are as defined above. R 21 may be the same or different '~ R 24' each is, R 21 'and R 23', and is preferably R 22 'and R 24' are the same, respectively. Furthermore, R a 'and R b' are it may be the same or different, but are preferably the same.

Specific examples of the diaminopyrene derivative represented by the formula (1) ', include compounds represented by the following formula.

Figure JPOXMLDOC01-appb-C000064

Figure JPOXMLDOC01-appb-C000065

Figure JPOXMLDOC01-appb-C000066

Figure JPOXMLDOC01-appb-C000067

Figure JPOXMLDOC01-appb-C000068

Figure JPOXMLDOC01-appb-C000069

Figure JPOXMLDOC01-appb-C000070

Figure JPOXMLDOC01-appb-C000071

Figure JPOXMLDOC01-appb-C000072

Figure JPOXMLDOC01-appb-C000073

Figure JPOXMLDOC01-appb-C000074

Figure JPOXMLDOC01-appb-C000075

Figure JPOXMLDOC01-appb-C000076

Figure JPOXMLDOC01-appb-C000077

Figure JPOXMLDOC01-appb-C000078

Figure JPOXMLDOC01-appb-C000079

(Anthracene derivative)
Anthracene derivative according to the organic light emitting medium II is represented by the following formula (2) '.

Figure JPOXMLDOC01-appb-C000080

( 'In, Ar 11' Equation (2) and Ar 12 'each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a heterocyclic group having 5 to 50 ring atoms,
R 1 '~ R 8' are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic ring group having 6 to 50 arylthio group, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a group selected from nitro and hydroxyl groups.
However, when one of Ar 11 'and Ar 12' is an unsubstituted 2-naphthyl group and the other is not 4- (1-naphthyl) phenyl-1-yl group. )

Anthracene derivative of the present invention, preferably when one of Ar 11 'and Ar 12' is an unsubstituted 2-naphthyl group and the other is not a phenyl group aryl-substituted.

Anthracene derivative according to the present invention, the following anthracene derivatives (A) ', (B)', and be either (C) 'are preferably selected, the configuration and determining characteristics of the organic EL elements to be applied.

(Anthracene derivative (A) ')
The anthracene derivative is and Ar 12 '' Ar 11 'in formula (2), each independently, are a substituted or unsubstituted fused aryl group having 10 to 50 carbon atoms. As the anthracene derivative, when Ar 11 'and Ar 12' are the same substituted or unsubstituted condensed aryl group, and can be divided in the case of different substituted or unsubstituted condensed aryl group.
Specifically, the following formula (2-1) 'to (2-3)' anthracene derivative represented by a, and a substituted or unsubstituted fused aryl formula (2), and Ar 12 '' Ar 11 'in different include anthracene derivative is a group.

Formula (2-1) 'anthracene derivative represented by, Ar 11' and Ar 12 'has become a substituted or unsubstituted 9-phenanthrenyl group.

Figure JPOXMLDOC01-appb-C000081

( 'In, R 1' formula (2-1) ~ R 8 'are as defined above,
R 11 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted an aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, carboxyl group, a halogen atom, a cyano group, a group selected from nitro and hydroxyl groups,
a is an integer from 0 to 9. when a is an integer of 2 or more, plural R 11 are the two substituted or condition that unsubstituted phenanthrenyl group are identical, each may be the same or different. )

Formula (2-2) 'anthracene derivative represented by the formula (2)' is Ar 11 'and Ar 12' in, and has a substituted or unsubstituted 2-naphthyl group.

Figure JPOXMLDOC01-appb-C000082

( 'In, R 1' formula (2-2) ~ R 8 'and R 11 are as defined above,
b is an integer of 1 to 7. If b is an integer of 2 or more, plural R 11 are the two substituted or condition that unsubstituted 2-naphthyl group are the same, each may be the same or different. )

Formula (2-3) 'anthracene derivative represented by the formula (2)' is Ar 11 'and Ar 12' in, and has a substituted or unsubstituted 1-naphthyl group.

Figure JPOXMLDOC01-appb-C000083

( 'In, R 1' formula (2-2) ~ R 8 ', R 11 and b are as defined above. Also, if b is an integer of 2 or more, plural R 11 are the two substituted or on condition that unsubstituted 1-naphthyl group are the same, each may be the same or different.)

In addition to the anthracene derivative represented by the above formula (2-1) 'to (2-3)', equation (2) and Ar 12 'are identical' Ar 11 'in a substituted or unsubstituted fluoranthenyl group anthracene derivative is, and also anthracene derivatives and Ar 12 'are the same substituted or unsubstituted pyrenyl group' Ar 11 'in formula (2) preferably.

'As the anthracene derivative is a different substituted or unsubstituted condensed aryl group, Ar 11' and Ar 12 'Ar 11' in formula (2) and Ar 12 'is of the formula (2-1)' - (2- 3) ', substituted or unsubstituted 9-phenanthrenyl group that, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, and is either substituted or unsubstituted fluoranthenyl group It is preferred.
Specifically, when the case Ar 11 'is a 1-naphthyl group, and Ar 12' are 2-naphthyl group, Ar 11 'is 1-naphthyl and Ar 12' are 9-phenanthryl group, and Ar 11 '2-naphthyl and Ar 12' is when it is a 9-phenanthryl group.

(Anthracene derivative (B) ')
The anthracene derivative is one substituted or unsubstituted phenyl group and Ar 12 '' Ar 11 'in formula (2), the other is a fused aryl group having 10 to 50 ring carbon atoms substituted or unsubstituted ing. As the anthracene derivative, and specific examples thereof include anthracene derivatives represented by the following formula (2-4) 'and (2-5)'.

Formula (2-4) 'anthracene derivative represented by the formula (2)' 'is a substituted or unsubstituted 1-naphthyl group, Ar 12' Ar 11 in is substituted or unsubstituted phenyl group It has become.

Figure JPOXMLDOC01-appb-C000084

( 'In, R 1' formula (2-4) ~ R 8 ', R 11 and b are as defined above,
Ar 6 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, 9,9-dimethyl-fluoren-1-yl group, 9,9-dimethyl-fluorene-2 yl group, 9,9-dimethyl-fluoren-3-yl group, 9,9-dimethyl-fluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or a dibenzofuran -4-yl group. Moreover, Ar 6, together with the benzene ring to which it is attached, may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzo fluorenyl group. If b is an integer of 2 or more, plural R 11 are each may be the same or different. )

Formula (2-5) 'anthracene derivative represented by the formula (2)' 'is a substituted or unsubstituted 2-naphthyl group, Ar 12' Ar 11 in is substituted or unsubstituted phenyl group It has become.

Figure JPOXMLDOC01-appb-C000085

( 'In, R 1' formula (2-5) ~ R 8 ', R 11 and b are as defined above,
Ar 7 represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or a cycloalkyl group having 3 to 50 ring carbon atoms unsubstituted, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or a dibenzofuran-4-yl group. Further, Ar 7 together with the benzene ring to which it is attached, may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzo fluorenyl group. If b is an integer of 2 or more, plural R 11 are each may be the same or different.
However, Ar 7 except the case of forming together with the adjacent phenylene group 4- (1-naphthyl) phenyl-1-yl group. )

In addition to the anthracene derivative represented by the above formula (2-4) 'and the formula (2-5)', equation (2) 'Ar 11' in is a substituted or unsubstituted fluoranthenyl group, Ar 12 'are preferred anthracene derivative is a substituted or unsubstituted phenyl group.

(Anthracene derivative (C) ')
The anthracene derivative is 'expressed in, specifically, the following formula (2-6-1)' formula (2-6), (2-6-2) 'and (2-6-3)' it is preferably a derivative represented by any one of the.

Figure JPOXMLDOC01-appb-C000086

( 'In, R 1' formula (2-6) ~ R 8 'and Ar 6 are as defined above,
Ar 5 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a heterocyclic group of the substituted or unsubstituted atoms 5 to 50, Ar 5 and Ar 6 are each independently selected. )
Figure JPOXMLDOC01-appb-C000087

( 'In, R 1' formula (2-6-1) ~ R 8 'are as defined above.)
Figure JPOXMLDOC01-appb-C000088

( 'In, R 1' formula (2-6-2) ~ R 8 'is a fused aryl group of the same in which .Ar 8 is a substituted or unsubstituted aromatic ring group having 10-20.)
Figure JPOXMLDOC01-appb-C000089

( 'In, R 1' formula (2-6-3) ~ R 8 'has the formula (2)' is the same as.
Ar 5a and Ar 6a are each independently a fused substituted or unsubstituted aryl group having 10 to 20 ring carbon atoms. )

Examples of the aryl group R 11, Ar 5 and Ar 6, Ar 11 'and Ar 12' substituted or unsubstituted aromatic ring group having 6 to 50 are the same as those of Ar 11 and Ar 12 in the formula (2) it is. Preferably, an unsubstituted phenyl group, a substituted phenyl group and a substituted or unsubstituted carbon atoms 10-14 of the aryl groups (e.g., 1-naphthyl, 2-naphthyl, 9-phenanthryl group), a substituted or unsubstituted fluorenyl group (2-fluorenyl group), and substituted or unsubstituted pyrenyl group (1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group).

Further, examples of fused aryl groups Ar 5a, Ar 6a and substituted or unsubstituted C 10 -C 20 Ar 8 is the same as this of Ar 5a, Ar 6a and Ar 8 in the formula (2) . In particular, 1-naphthyl, 2-naphthyl, 9-phenanthryl group, pyrenyl group (1-pyrenyl group, 2-pyrenyl group, and a 4-pyrenyl group), and a fluorenyl group (2-fluorenyl group).

Examples of the heterocyclic group of R 11 and Ar 5 ~ substituted or unsubstituted 5 to 50 ring atoms of Ar 7, this of R 1 ~ R 8, R 11 and Ar 5 ~ Ar 7 in the above formula (2) is the same as that. Preferably, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, a 9-carbazolyl group.

Examples of the alkyl group R 1 '~ R 8', R 11 and Ar 5 ~ substituted or unsubstituted C 1-50 of Ar 7 is, R 1 ~ R 8 in the above formula (2), R 11 and Ar is the same as this of 5 ~ Ar 7. Preferably, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl group, s- butyl group, an isobutyl group, a t- butyl group.

The R 1 '~ R 8', the cycloalkyl group of R 11 and Ar 5 ~ substituents a substituted or unsubstituted aromatic ring group having 3 to 50 of the Ar 7, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group , 4-methylcyclohexyl group, 1-adamantyl, 2-adamantyl, 1-norbornyl group, 2-norbornyl group and the like. Preferably, a cyclopentyl group, a cyclohexyl group.

Alkoxy group R 1 '~ R 8' and substituted or unsubstituted C 1-50 of R 11 is a group represented by -OZ, Z is substituted or unsubstituted of said R 1 '~ R 8' It is selected from alkyl groups having 1 to 50 carbon atoms substituted.

R 1 '~ R 8', R 11 and Ar 5 ~ Ar number 7 carbon atoms of the substituted or unsubstituted substituent 7-50 aralkyl group (the aryl moiety having a carbon number of 6 to 49 alkyl moiety having a carbon number of 1 to 44 examples of) is the same as this of R 1 ~ R 8, R 11 and Ar 5 ~ Ar 7 in the above formula (2).

R 1 substituted or unsubstituted aryloxy group and arylthio group having 6 to 50 carbon atoms' ~ R 8 'and R 11 are each represented as -OY and -SY, Y, the R 1' ~ R 8 selected from substituted or unsubstituted aryl group having 6 to 50 carbon atoms'.

R 1 substituted or unsubstituted C 2-50 alkoxycarbonyl group '~ R 8' and R 11 (1 ~ 49 alkyl moiety having a carbon number) is expressed as -COOZ, Z, the R 1 '~ R 8 selected from substituted or unsubstituted alkyl group having a carbon number of 1 to 49 '.

The substituted silyl group of R 1 '~ R 8' and R 11, a trimethylsilyl group, triethylsilyl group, t- butyl dimethyl silyl group, a vinyl dimethyl silyl group, propyldimethylsilyl group, a triphenylsilyl group and the like.

Examples of the halogen atom of R 1 '~ R 8' and R 11, fluorine, chlorine, bromine, and iodine.

Specific examples of the anthracene derivative represented by the formula (2) 'of the present invention include the following.

Figure JPOXMLDOC01-appb-C000090

Figure JPOXMLDOC01-appb-C000091

Figure JPOXMLDOC01-appb-C000092

Figure JPOXMLDOC01-appb-C000093

Figure JPOXMLDOC01-appb-C000094

Figure JPOXMLDOC01-appb-C000095

Figure JPOXMLDOC01-appb-C000096

Figure JPOXMLDOC01-appb-C000097

Figure JPOXMLDOC01-appb-C000098

Figure JPOXMLDOC01-appb-C000099

Figure JPOXMLDOC01-appb-C000100

Figure JPOXMLDOC01-appb-C000101

Figure JPOXMLDOC01-appb-C000102

Figure JPOXMLDOC01-appb-C000103

Figure JPOXMLDOC01-appb-C000104

Figure JPOXMLDOC01-appb-C000105

Figure JPOXMLDOC01-appb-C000106

Figure JPOXMLDOC01-appb-C000107

Figure JPOXMLDOC01-appb-C000108

Figure JPOXMLDOC01-appb-C000109

Diaminopyrene derivative represented by the formula (1) ', for example, after introducing a substituent in a manner known to dibromopyrene obtained by bromination of commercially available pyrene, brominated again, under the metal catalyst, the corresponding it can be synthesized by reacting a secondary amine compound to be. Further, the anthracene derivative represented by the formula (2) ', for example, can be synthesized by the method of No. WO2004 / 018 587 publication.

The organic luminescent medium of the present invention is in a state in which the anthracene derivative represented by the 'diaminopyrene derivative type represented by (2)' above expression like (1) coexist.
The mass ratio of the anthracene derivative represented by the formula (1) 'diaminopyrene derivative of the formula represented by (2)' is 50:50 to 0.1: is preferably 99.9 20:80 ~ 1: and more preferably 99.

[Organic EL Device]
The organic EL device of the present invention is a single or device in which an organic thin film layer is formed of a plurality of layers between an anode and a cathode. If the organic thin film layer has a plurality of layers, and further has a light-emitting layer. When the organic thin film layer is further provided between the anode and the cathode, the light emitting layer as the organic thin film layer is formed. At least one layer of the organic thin film layer (preferably light-emitting layer) contained the organic luminescent medium of the present invention, further, holes injected from the anode or electrons injected from the cathode in order to transport to the light-emitting material it may contain a hole injecting material or electron injecting material. Further, at least one layer (preferably light-emitting layer) of the organic thin film layer may be formed from an organic luminescent medium of the present invention. The organic luminescent medium of the present invention has high emission characteristics.

Further, the organic EL device of the present invention, organic invention between an organic EL device in which an organic thin film layer composed of two or more layers including at least a light emitting layer between a cathode and an anode, an anode and a light emitting layer preferred may have an organic layer mainly composed of light-emitting medium. As the organic layer, a hole injection layer, a hole transport layer, and the like.

In the present invention, the organic thin film layer organic EL device of the plurality of layers form, (anode / hole injecting layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole a laminate of an injection layer / light emitting layer / electron injection layer / cathode), such as a configuration and the like.
The multiple layers, if necessary, additional known light emitting material in addition to the organic luminescent medium of the present invention, doping material, also use a hole injecting material or electron injecting material. The organic EL element, by the organic thin film layer multilayer structure, it is possible to prevent a decrease in luminance or lifetime due to quenching. If necessary, can be used in combination luminescent material, doping material, hole injecting materials and electron injecting materials. Further, it doping materials, improvements in emission luminance and luminous efficiency, also give a red or blue light emission. The hole injection layer, light emitting layer, an electron injection layer may be formed of a layer structure of two or more layers. At that time, in the case of a hole injection layer, a hole injection layer a layer for injecting a hole from the electrode, and a hole injection layer hole transport layer a layer which transports holes to the hole to receive the light emitting layer from call. Similarly, when the electron injection layer, an electron injection layer a layer which injects electrons from the electrode, called the layer that transports electrons from the electron injecting layer an electron to receive the light emitting layer and the electron transport layer. These layers, the energy level of a material, heat resistance, is selected for use by each factors such as adhesion to the organic layers or the metal electrodes.

As the host material or the doping material can be used in the light emitting layer together with the organic luminescent medium of the present invention, for example, naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenyl cyclo pentadiene, fluorene, spirofluorene, 9,10-diphenyl anthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynyl-anthracenyl) fused multimeric aromatic compounds such as benzene and their derivatives, tris (8-quinolinolato) aluminum, bis - (2-methyl-8-quinolinolato) -4-organometallic complex, triarylamine derivatives such as (phenyl Fe laver diisocyanate) aluminum, styrylamine derivative Conductor, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole derivatives, acridone derivatives, quinacridone derivatives, and but it is not limited thereto.

As the hole injecting material, having an ability of transporting a hole, the hole injection effect from an anode and has an excellent hole injection effect to a light emitting layer or an organic light emitting medium, generated in the light emitting layer excitons electron injection layer or preventing the movement thereof to its electron-injecting material, and excellent ability of forming a thin film is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazole thione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl alkanes, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, derivatives thereof, and polyvinyl carbazole, polysilane, and polymer materials such as conductive polymers , but it is not limited thereto.

Of the hole injecting materials that can be used in the organic EL device of the present invention, more effective hole injecting materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
Examples of the aromatic tertiary amine derivative, e.g., triphenylamine, tritolylamine, tolyldiphenylamine, N, N'-diphenyl -N, N '- (3- methylphenyl) -1,1'-biphenyl-4,4 '- diamine, N, N, N', N '- (4- methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N', N '- (4- methylphenyl ) -1,1'-biphenyl-4,4'-diamine, N, N'-diphenyl -N, N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N, N '- ( methylphenyl) -N, N '- (4-n- butylphenyl) - phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl - cyclohexane, or oligomer having these aromatic tertiary amine skeletons Or is a polymer, but is not limited thereto.

The phthalocyanine (Pc) derivative, for example, H 2 Pc, CuPc, CoPc , NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, VOPc, TiOPc, MoOPc, there are phthalocyanine and naphthalocyanine derivatives such as GaPc-O-GaPc, but is not limited thereto.

Further, the organic EL device of the present invention, between the light emitting layer and the anode, a layer containing these aromatic tertiary amine derivatives and / or phthalocyanine derivatives, for example, the hole transport layer or a hole injection layer preferably formed composed.

As the electron injecting material, having an ability of transporting electrons, electron injection effect from a cathode, the light emitting layer or has an excellent electron injection effect to the light emitting material, the hole injection layer of an exciton generated in the light emitting layer to prevent movement of the, and excellent ability of forming a thin film is preferable.
Specific examples of the electron injecting material, a metal complex of 8-hydroxyquinoline or derivatives thereof and oxadiazole derivatives are preferable. Specific examples of metal complexes of 8-hydroxyquinoline or derivatives thereof, oxine (generally 8-quinolinol or 8-hydroxyquinoline) metal chelate oxinoid compounds including a chelate of electron injection, for example, tris (8-quinolinolato) aluminum it can be used as a material.

On the other hand, the oxadiazole derivative include electron transfer compounds represented by the following general formula.

Figure JPOXMLDOC01-appb-C000110

(In the formula, Ar 1, Ar 2, Ar 3, Ar 5, Ar 6, and Ar 9 each represent a substituted or unsubstituted aryl group, each may have be the same or different from each other.
Ar 4, Ar 7, Ar 8 represents a substituted or unsubstituted arylene group, may each be the same or different)

Examples of the aryl group include phenyl group, biphenyl group, anthranyl group, perylenyl group, and a pyrenyl group. As the arylene group, a phenylene group, a naphthylene group, biphenylene group, anthranylene group, perylenylene group, pyrenylene group, and the like. Further, examples of the substituent include an alkoxy group or a cyano group an alkyl group having 1 to 10 carbon atoms having 1 to 10 carbon atoms. The electron-transporting compound is preferably one from which a thin film-forming.

Specific examples of the electron transfer compounds are given below.

Figure JPOXMLDOC01-appb-C000111

Me is methyl, tBu represents a t-butyl.

Further, as the electron injecting material, it may be used those represented by the following general formula (A) ~ (F).

Figure JPOXMLDOC01-appb-C000112

(In the general formula (A) and (B), A 1 ~ A 3 are each independently a nitrogen atom or a carbon atom.
Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted 5 to 60 ring atoms of the heterocyclic group,
Ar 2 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted 5 to 60 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms group, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or a these divalent groups.
However, either one of Ar 1 and Ar 2, a substituted or unsubstituted fused ring group having a carbon number of 10 to 60, or a substituted or unsubstituted monohetero fused ring group having 5 to 60 ring atoms.
L 1, L 2 and L each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted 5 to 60 ring atoms heteroarylene group, or a substituted or an unsubstituted fluorenylene group.
R is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted 5 to 60 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having a carbon number of 1 ~ 20, n is an integer from 0 to 5, when n is 2 or more, plural R may be the same or different, also, adjacent attached at a plurality of R groups to each other to, they may form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.
R 1 is hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, heteroaryl group or a substituted or unsubstituted 3 to 60 carbon atoms, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms group, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or -L 1 -Ar 1 -Ar 2. Nitrogen-containing heterocyclic derivative represented by).

HAr-L-Ar 1 -Ar 2 (C)
(Wherein, HAr is a nitrogen-containing heterocyclic ring of 3 to 40 carbon atoms which may have a substituent,
L represents a single bond, an arylene group of ~ 60 good nuclear carbon atoms 6 may have a substituent, a heteroarylene group, or a substituent ~ 60 5 good number ring atoms which may have a substituent even though a good fluorenylene group,
Ar 1 is a divalent aromatic hydrocarbon group having 6 to good nucleation 60 carbon atoms have a substituent,
Ar 2 is a heterocyclic group of the aryl group or may have a substituent group having 5 to 60 ring atoms of not having 6 to good nucleation 60 carbon atoms have a substituent. Nitrogen-containing heterocyclic derivative represented by).

Figure JPOXMLDOC01-appb-C000113

(Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, alkynyloxy group, hydroxy group, a substituted or unsubstituted aryl group, a substituted or an unsubstituted hetero ring, or X and Y are to form a ring bonded to a saturated or unsaturated structure,
R 1 ~ R 4 are each independently hydrogen, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, a sulfinyl group, a sulfonyl group, a sulfanyl group, silyl group, a carbamoyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, a nitro group, a formyl group, nitroso group, formyloxy group, isocyano group, a cyanate group, isocyanate group, thiocyanate group, Isochi If the cyanate were group or cyano group, or adjacent a structure substituted or the unsubstituted rings are fused. Borane derivatives represented by).

Figure JPOXMLDOC01-appb-C000114

(Wherein, R 1 ~ R 8 and Z 2 are independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, an alkoxy group or an aryl group,
X, Y and Z 1 each independently represents a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, an alkoxy group or an aryloxy group,
Substituents of Z 1 and Z 2 may form a condensed ring bonded to each other, n represents an integer of 1 to 3, when n is 2 or more, Z 1 may be different.
However, an n is 1, X, Y and R 2 are a methyl group, R 8 is a hydrogen atom or a substituted boryl group, and n is Z 1 in 3 does not include the case of methyl group. Borane derivatives represented by).

Figure JPOXMLDOC01-appb-C000115

Wherein, Q 1 and Q 2 each independently represent a ligand represented by the following general formula (G),
L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, -OR 1 (R 1 is a hydrogen atom , substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group.) or -O-Ga-Q 3 (Q 4) (Q 3 and Q 4 have the same as Q 1 and Q 2) represents a ligand represented by. ]

Figure JPOXMLDOC01-appb-C000116

Wherein rings A 1 and A 2 are six-membered aryl ring structure fused together may have a substituent. ]

The metal complexes have the strong nature of an n-type semiconductor and large ability of injecting electrons. Furthermore, the energy generated at the time complexation, bonding between the metal and the ligand of the formed metal complex becomes strong, and the fluorescent quantum efficiency becomes large as the emitting material.

Formula and specific examples of the substituents of ring A 1 and A 2 forming the ligand (G), chlorine, bromine, iodine, halogen atom such as fluorine, methyl group, ethyl group, propyl group, butyl, s- butyl, t- butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, a substituted or unsubstituted alkyl group such as a trichloromethyl group, a phenyl group, a naphthyl group, 3-methyl phenyl, 3-methoxyphenyl group, 3-fluorophenyl group, 3-trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitro-substituted or unsubstituted aryl group such as a phenyl group, a methoxy group, n- butoxy, t-butoxy group, trichloromethoxy group, trifluoroethoxy group, pentafluoropropoxy propoxy group, 2,2,3,3 Tetorafuru Ropuropokishi group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 6- (perfluoroethyl) substituted or unsubstituted alkoxy groups such as a hexyl group, a phenoxy group, p- nitrophenoxy group, p-t-butyl phenoxy group, 3-fluorophenoxy group, pentafluorophenoxy group, 3-trifluoromethylphenoxy substituted or unsubstituted aryloxy group such as a group, methylthio group, ethylthio group, t-butylthio group, hexylthio group, octylthio group, a substituted or unsubstituted alkylthio group such as a trifluoromethylthio group, a phenylthio group, p- nitrophenyl-thio group, p-t-butylphenyl thio group, 3-fluorophenylthio group, pentafluorophenylthio groups, substituted and 3-trifluoromethylphenylthio group Or unsubstituted arylthio group, a cyano group, a nitro group, an amino group, methylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, mono- or di-substituted amino groups such as diphenylamino group, bis ( acetoxymethyl) amino group, bis (acetoxyethyl) amino group, bis acetoxy propyl) amino group, bis (acetoxybutyl) acylamino group such as an amino group, a hydroxyl group, siloxy group, acyl group, methylcarbamoyl group, dimethylcarbamoyl group, ethyl carbamoyl group, diethylcarbamoyl group, Ploy pin carbamoyl group, butylcarbamoyl group, a carbamoyl group such as phenylcarbamoyl group, a carboxylic acid group, sulfonic acid group, an imide group, a cyclopentane group, cycloalkyl groups such as cyclohexyl group, phenyl , Naphthyl group, biphenyl group, anthranyl group, phenanthryl group, fluorenyl group, an aryl group such as a pyrenyl group, a pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, indolinyl group, quinolinyl group, acridinyl group, pyrrolidinyl group, dioxanyl group, piperidinyl group, morpholinyl group, piperazinyl group, carbazolyl group, furanyl group, thiophenyl group, oxazolyl group, oxadiazolyl group, benzoxazolyl group, a thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group, an imidazolyl group, benzimidazolyl group it is a heterocyclic group and the like. It is also possible to form a six-membered aryl ring or heterocyclic ring bonded to each other more substituents.

The preferred mode of the organic EL device of the present invention, region or in an interfacial region between the cathode and the organic layer transporting electrons, there is a device containing a reducing dopant. The reducing dopant is defined electron transporting compound as a substance which can reduce. Therefore, as long as it has a certain reducing, various ones can be used, for example, alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, alkaline earth metals oxides, alkaline earth metal halides, halides of oxide or a rare earth metal of the rare earth metals, alkali metal carbonates, alkaline earth metal carbonates, organic complexes of alkali metals, organic complexes of alkaline earth metals , it can be suitably used at least one material selected from the group consisting of organic complexes of rare earth metals.

More specific examples of the preferable reductive dopant, Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 at least one alkaline earth metal selected from the group consisting of .95eV), Ca (work function: 2.9eV), Sr (work function: 2.0 ~ 2.5eV), and Ba (work function: 2.52 eV at least one alkaline earth work function metals) selected from the group consisting of or less are particularly preferred 2.9 eV. Among these, more preferable reductive dopant, K, at least one alkali metal selected from the group consisting of Rb and Cs, more preferably, Rb or Cs, the most preferably is given to Cs . These alkali metals have particularly high reducibility, addition of a relatively small amount thereof to an electron injecting zone can enhance luminance intensity and lifetime of the organic EL device. As the reducing dopant having a work function of 2.9 eV, these combination of two or more alkali metals is also preferable, in particular, the combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and is preferably a combination of Na and K. By including a combination of cs, it can be efficiently exhibit the reducing ability by the addition thereof to the electron injecting zone can enhance luminance intensity and lifetime of the organic EL device.

It may further include an electron injecting layer made of an insulator or a semiconductor and disposed between the cathode and the organic layer in the present invention. In this case, it is possible to effectively prevent a current leak, thereby enhancing electron injectability. Such insulators, alkali metal chalcogenides, alkaline earth metal chalcogenides, to use at least one metal compound selected from the group consisting of halides and alkaline earth metal halides of alkali metals preferred. When the electron injecting layer is constituted with the above alkali metal chalcogenide or the like, preferable in that it can further improve the electron injection property.
Preferable examples of the alkali metal chalcogenide, for example, Li 2 O, K 2 O , Na 2 S, Na 2 Se and Na 2 O, as the preferred alkali earth metal chalcogenides, for example, CaO, BaO , SrO, BeO, BaS, and CaSe. Preferable halides of alkali metals, for example, LiF, NaF, KF, CsF, LiCl, KCl and NaCl. Preferable halides of alkaline earth metals, for example, fluorides such as CaF 2, BaF 2, SrF 2 , MgF 2 and BeF 2, and halides other than fluorides.

The oxide as the semiconductor constituting the electron injection layer, containing Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, at least one element of Sb and Zn , and alone or in combinations of two or more such nitride or oxynitride is. The inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. When the electron injecting layer is constituted with the insulating thin films, more uniformed thin film is formed, thereby reducing pixel defects such as dark spots. Examples of such an inorganic compound include alkali metal chalcogenides as described above, the alkaline earth metal chalcogenides, halides and halides of alkaline earth metals of the alkali metals.

Then, as a cathode, a small work function (4 eV or less) metal, an alloy, an electroconductive compound, or a mixture thereof as an electrode substance are employed. Specific examples of the electrode substance include sodium, sodium - potassium alloy, magnesium, lithium, cesium, magnesium-silver alloy, aluminum / aluminum oxide, Al / Li 2 O, Al / LiO, Al / LiF, aluminum lithium alloys, indium, rare earth metals.
By this cathode to form a thin film by a method such as vapor deposition or sputtering of the electrode material, it can be manufactured.

When the light emitted from the light emitting layer from the cathode, the transmittance of the cathode to the luminescence is preferably larger than 10%. The sheet resistance is preferably several hundreds Omega / □ or less of the cathode, further, the film thickness is usually 10 nm ~ 1 [mu] m, preferably 50 ~ 200 nm.

In general, the organic EL device, so that an electric field is applied to ultra-thin films, tends to form defects in pixels due to leak and short circuit. To prevent this, it may insert an insulative thin layer between the pair of electrodes.

The material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide , germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide and vanadium oxide. These may also be used in mixture or laminate.

The organic EL device of the present invention, the temperature, humidity, in order to improve humidity and ambient atmosphere, or a protective layer on the surface of the device, silicone oils, also possible to protect the entire device by a resin or the like it is.

As the conductive material used for the anode of the organic EL device of the present invention, is suitably those having a work function of greater than 4 eV, carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum , palladium, and alloys thereof, ITO (indium tin oxide) substrate, tin oxide used in the NESA substrate, metal oxides such as indium oxide, and organic conductive resins such as polythiophene and polypyrrole. As the conductive material used for the cathode, is suitably those having a work function of smaller than 4 eV, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride and the like, and their alloy is used, but not limited thereto. As an alloy, a magnesium / silver, magnesium / indium and lithium / aluminum, etc. Representative examples are not intended to be limited thereto. The ratio of the alloy, the temperature of the deposition source, atmosphere, is controlled by the degree of vacuum, and is selected to be an appropriate ratio. The anode and the cathode, may be formed of a layer constitution having two or more layers if necessary.

In the organic EL device of the present invention, in order to efficiently emit light, at least one surface is desirably sufficiently transparent in the emission wavelength region of the device. Further, the substrate is desirably transparent. The transparent electrode is produced from the above electrically conductive material, a predetermined light-transmitting a deposition or sputtering method is set so as to ensure. Electrode of the light emitting surface, it is preferable that the light transmittance of 10% or more. Substrate, mechanical, have a thermal strength, but is not limited as long as it has transparency, there is a glass substrate and a transparent resin film.
Examples of the transparent resin film include polyethylene, ethylene - vinyl acetate copolymer, ethylene - vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone , polysulfone, polyether sulfone, tetrafluoroethylene - perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene - ethylene copolymer, tetrafluoroethylene - hexafluoropropylene copolymer, polychlorotrifluoroethylene, include polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene etc. It is.

Formation of each layer of the organic EL device of the present invention, vacuum deposition, sputtering, applying plasma, dry deposition method or a spin coating such as ion plating, dipping, any method of wet film-forming method such as flow coating be able to. The film thickness is not particularly limited, it is necessary to have a proper thickness. If the thickness is too thick, efficiency requires an increased applied voltage for obtaining a constant light output is deteriorated. Thickness pinholes occurs too thin, so sufficient emission luminance can not be obtained even when an electric field is applied. Normally the thickness is suitable range of 5 nm ~ 10 [mu] m, more preferably in the range of 10 nm ~ 0.2 [mu] m.

For wet film-forming method, a material forming each layer, ethanol, chloroform, tetrahydrofuran, forms a suitable solvent for dissolving or dispersing in a thin film such as dioxane, the solvent may be any one. In any organic thin layer, improving film formability may be using the appropriate resins and additives for preventing a pin hole in the layer. Possible resins for use, polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, an insulating resin and copolymers thereof such as cellulose, poly -N- vinyl carbazole, photoconductive resins polysilane, polythiophene, and conductive resin polypyrrole. As the additive, an antioxidant, an ultraviolet absorber, and a plasticizer.

The organic EL device of the present invention can be used flat light emitting body such as a wall-mounted TV flat panel displays, copiers, printers, back light or instruments and the like of the light source of the liquid crystal display, display panel, marker lights, and the like. Further, the material of the present invention, not only an organic EL device, an electrophotographic photoreceptor, a photoelectric conversion element, a solar cell, can be used in the fields such as an image sensor.

Next, synthesis examples, examples and comparative examples, but the present invention will be described in more detail, the present invention is not limited thereto.

Example 1
After performing 25 mm × 75 mm × 1.1 mm thick (manufactured by GEOMATEC CO) ITO transparent electrode (anode) coated glass substrate 5 minutes ultrasonic cleaning in isopropyl alcohol, and then subjected to UV ozone cleaning for 30 minutes. The substrate with transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus, first, the compound of the so as to cover the transparent electrode film thickness 60nm on the surface of the side where the transparent electrode lines were formed A-1 the film was formed. After the formation of the A-1 film was formed A-2 having a thickness of 20nm on the A-1 film. Further, the host material EM1 and the dopant material DM7-4 of the present invention with a thickness of 40nm on the A-2 film 40: formed by two film thickness ratio was blue emitting layer.

Figure JPOXMLDOC01-appb-C000117

The Alq having the following structure was formed by vapor deposition in a film thickness 20nm as an electron-transporting layer in this film. After this, by forming a LiF in a thickness of 1nm. The metallic Al to form a metal cathode was 150nm deposited on the LiF film to form an organic EL device.

Figure JPOXMLDOC01-appb-C000118

Alq

Example 2-174
In Example 1, the host material EM1, An organic EL device was fabricated in the same manner by using a host material and a dopant materials shown in Table 1-5 in place of the dopant material DM7-4.

Comparative Example 1
In Example 1, the following compound A instead of the host material EM1, An organic EL device was fabricated in the same manner in place of the dopant material DM7-4 using the following compound B.

Figure JPOXMLDOC01-appb-C000119

Comparative Example 2
In Example 1, the following compound C instead of the host material EM1, An organic EL device was fabricated in the same manner using the following compound D instead of the dopant material DM7-4.

Figure JPOXMLDOC01-appb-C000120

Comparative Example 3
In Example 1, the following compounds E, instead of the host material EM1, An organic EL device was fabricated in the same manner by using the following compound F instead of the dopant material DM7-4.

Figure JPOXMLDOC01-appb-C000121

Table 1-5 shows the half-life at the emission wavelength and the initial luminance 1000 cd / m 2 of the organic EL element.

Figure JPOXMLDOC01-appb-T000122

Figure JPOXMLDOC01-appb-T000123

Figure JPOXMLDOC01-appb-T000124

Figure JPOXMLDOC01-appb-T000125

Figure JPOXMLDOC01-appb-T000126

Examples 175-430
In Example 1, the host material EM1, to produce an organic EL device in the same manner by using a host material and a dopant materials shown in Table 6-12 in place of the dopant material DM7-4.

Comparative Example 4
In Example 1, 'the dopant material DM2-4 instead of the dopant material DM7-4' following compound H-1 in place of the host material EM1 An organic EL device was fabricated similarly used.

Figure JPOXMLDOC01-appb-C000127

Comparative Example 5
In Example 1, 'the dopant material DM10-4 instead of the dopant material DM7-4' the Compound H-1 in place of the host material EM1 An organic EL device was fabricated similarly used.

Comparative Example 6
In Example 1, 'the following compound D-1 in place of the dopant material DM7-4' following compound H-2 instead of the host material EM1 An organic EL device was fabricated similarly used.

Figure JPOXMLDOC01-appb-C000128

Comparative Example 7
In Example 1, 'the following compound D-2 in place of the dopant material DM7-4' following compound H-3 instead of the host material EM1 An organic EL device was fabricated similarly used.

Figure JPOXMLDOC01-appb-C000129

Table 6-12 shows the half-life of light emission efficiency and an initial luminance 1000 cd / m 2 of the organic EL elements obtained in Examples 175 to 430 and Comparative Examples 4-7.

Figure JPOXMLDOC01-appb-T000130
Figure JPOXMLDOC01-appb-T000131
Figure JPOXMLDOC01-appb-T000132
Figure JPOXMLDOC01-appb-T000133
Figure JPOXMLDOC01-appb-T000134
Figure JPOXMLDOC01-appb-T000135
Figure JPOXMLDOC01-appb-T000136

The organic EL device using an organic luminescent medium of the present invention are useful, for example, as a light source such as a wall-mounted television planar light emitter or a display backlight.
All the documents described in the specification are incorporated herein.

Claims (38)

  1. A diaminopyrene derivative represented by the following formula (1), an organic light emitting medium comprising the anthracene derivative represented by the following formula (2).
    Figure JPOXMLDOC01-appb-C000001

    (In the formula (1), R 21 ~ R 24 each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted a cycloalkyl group having 3 to 50 ring carbon atoms substituted, or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, when there is one or two pairs of adjacent alkyl groups on the same benzene ring, said adjacent alkyl groups may form a divalent linking group bonded to a substituted or unsubstituted with one another, provided that if said adjacent alkyl groups to form a naphthyl group together with the benzene ring to which they are attached except.
    n1 ~ n4 are each independently an integer of 0-5.
    R a and R b are each independently a hydrogen atom, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted a cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted 6 to 50 carbon atoms aryloxy group, a substituted or unsubstituted silyl group, a halogen atom or a cyano group.
    However, if R a and R b are hydrogen atoms at the same time is excluded. )
    Figure JPOXMLDOC01-appb-C000002

    (In the formula (2), Ar 11 and Ar 12 each independently represent a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms,
    R 1 ~ R 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted 5 to 50 ring atoms of the heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted having 7 to 50 carbon atoms aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a group selected from cyano group.
    However, when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group and the other is not 4- (1-naphthyl) phenyl-1-yl group.
    Further, at least not one but a substituted or unsubstituted anthryl group Ar 11 and Ar 12. )
  2. In the anthracene derivative represented by the formula (2), when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group, an organic light emitting medium according to claim 1 other is not a phenyl group aryl-substituted .
  3. Formula Ar 11 and Ar 12 are in (2), each independently, an organic light emitting medium according to claim 1 or 2 which is fused an aryl group substituted or unsubstituted 10 to 20 carbon atoms.
  4. The organic luminescent medium according to claim 3 Ar 11 and Ar 12 are of the same group in the formula (2).
  5. Formula Ar 11 and Ar 12 in (2) is an organic light emitting medium according to claim 4 is a substituted or unsubstituted 9-phenanthrenyl group.
  6. Formula Ar 11 and Ar 12 in (2) is an organic light emitting medium according to claim 4 is a substituted or unsubstituted 2-naphthyl group.
  7. Formula Ar 11 and Ar 12 in (2) is an organic light emitting medium according to claim 4 is a substituted or unsubstituted 1-naphthyl group.
  8. The organic luminescent medium according to claim 3 Ar 11 and Ar 12 in the formula (2) are different groups.
  9. Formula Ar 11 and Ar 12 are in (2), a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, and in the claims is either substituted or unsubstituted 2-naphthyl group the organic luminescent medium according to 8.
  10. Is one substituted or unsubstituted phenyl group of Ar 11 and Ar 12 in the formula (2), according to claim 1 or 2 other is a fused substituted or unsubstituted aryl group having 10 to 20 ring carbon atoms organic light-emitting medium.
  11. The substituted or unsubstituted condensed aryl group having 10 to 20 ring carbon atoms is, organic light emitting medium according to claim 10 which is a substituted or unsubstituted 1-naphthyl group.
  12. The substituted or unsubstituted condensed aryl group having 10 to 20 ring carbon atoms is, organic light emitting medium according to claim 10 which is a substituted or unsubstituted 2-naphthyl group.
  13. The anthracene derivative represented by formula (2) is an organic light emitting medium according to claim 1 represented by the following formula (2-6).
    Figure JPOXMLDOC01-appb-C000003

    (In the formula (2-6), R 1 ~ R 8 is the same as equation (2).
    Ar 5 and Ar 6 each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or 5 to 50 ring atoms unsubstituted heterocyclic group. )
  14. Formula (2-6) an organic light emitting medium according to claim 13 Ar 5 and Ar 6 are substituted or unsubstituted phenyl group independently in.
  15. Is one substituted or unsubstituted phenyl group of Ar 5 and Ar 6 in the formula (2-6) in, to claim 13 the other is a fused substituted or unsubstituted aryl group having 10 to 20 ring carbon atoms the organic luminescent medium according.
  16. Formula (2-6) an organic light emitting medium according to claim 13 Ar 5 and Ar 6 are substituted or unsubstituted fused aryl group having 10 to 20 carbon atoms each independently being.
  17. Formula (2) or the formula (2-6) an organic light emitting medium according to any one of claims 1 to 16 all R 1 ~ R 8 is a hydrogen atom in the.
  18. The organic light emitting medium comprising 'a diaminopyrene derivative represented by the following formula (2)' the following formula (1) and anthracene derivative represented by.
    Figure JPOXMLDOC01-appb-C000004

    ( 'In, R 21' Equation (1) ~ R 24 'each independently represent a hydrogen atom, having 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted 1 to 50 carbon atoms alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 20 carbon atoms, If there are identical alkyl groups adjacent one or two pairs on the benzene ring, the alkyl group may form a divalent bonding group or a substituted or unsubstituted bonded to each other in contact 該隣.
    n1 '~ n4' are each independently an integer of 1-5.
    R a 'and R b' are independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. )
    Figure JPOXMLDOC01-appb-C000005

    ( 'In, Ar 11' Equation (2) and Ar 12 'each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a heterocyclic group having 5 to 50 ring atoms,
    R 1 '~ R 8' are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic ring group having 6 to 50 arylthio group, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a group selected from nitro and hydroxyl groups.
    However, a R 1 '~ R 8' is hydrogen atom, when one of Ar 11 'and Ar 12' is an unsubstituted 2-naphthyl group, the other 4- (1-naphthyl) phenyl-1- not-yl group. )
  19. 'In the anthracene derivative represented by, Ar 11' the formula (2) when one of and Ar 12 'is an unsubstituted 2-naphthyl group, the other of claim 18 is not a phenyl group aryl-substituted organic light emitting medium.
  20. The equation (2) 'Ar 11' in and Ar 12 ', each independently, an organic light emitting medium according to claim 18 or 19 which is a fused aryl group or a substituted or unsubstituted 10 to 50 carbon atoms.
  21. The organic luminescent medium according to claim 20 wherein the formula (2) 'Ar 11' in and Ar 12 'are of the same group.
  22. Formula (2), and Ar 12 '' Ar 11 'in an organic light emitting medium according to claim 21 which is a substituted or unsubstituted 9-phenanthrenyl group.
  23. Formula (2), and Ar 12 '' Ar 11 'in an organic light emitting medium according to claim 21 which is a substituted or unsubstituted 2-naphthyl group.
  24. Formula (2), and Ar 12 '' Ar 11 'in an organic light emitting medium according to claim 21 which is a substituted or unsubstituted 1-naphthyl group.
  25. The organic luminescent medium according to claim 20 wherein the formula (2) 'Ar 11' in and Ar 12 'are different groups.
  26. The equation (2) 'Ar 11' in and Ar 12 ', a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, a substituted or unsubstituted fluoranthenyl group, and an organic light emitting medium according to claim 25 which is either a substituted or unsubstituted pyrenyl group.
  27. Is one substituted or unsubstituted phenyl group of the formula (2) 'Ar 11' in and Ar 12 ', according to claim 18 or the other is a fused aryl group having 10 to 50 ring carbon atoms substituted or unsubstituted the organic light emitting medium according to 19.
  28. The substituted or unsubstituted condensed aryl group having 10 to 50 ring carbon atoms is, organic light emitting medium according to claim 27 which is a substituted or unsubstituted 1-naphthyl group.
  29. The substituted or unsubstituted condensed aryl group having 10 to 50 ring carbon atoms is, organic light emitting medium according to claim 27 which is a substituted or unsubstituted 2-naphthyl group.
  30. The substituted or unsubstituted condensed aryl group having 10 to 50 ring carbon atoms is, organic light emitting medium according to claim 27 which is a substituted or unsubstituted fluoranthenyl group.
  31. The substituted or unsubstituted condensed aryl group having 10 to 50 ring carbon atoms is, organic light emitting medium according to claim 27 which is a substituted or unsubstituted pyrenyl group.
  32. Formula (2) 'anthracene derivative represented by the following formula (2-6)' organic luminescent medium according to claim 18 or 19 represented by.
    Figure JPOXMLDOC01-appb-C000006

    ( 'In, R 1' formula (2-6) ~ R 8 'has the formula (2)' is the same as.
    Ar 5 and Ar 6 each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aromatic ring group having 3 to 50 cycloalkyl group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or 5 to 50 ring atoms unsubstituted heterocyclic group. )
  33. Formula (2-6) one of Ar 5 and Ar 6 in 'is a substituted or unsubstituted phenyl group, Claim 32 other is a fused substituted or unsubstituted aryl group having 10 to 20 ring carbon atoms the organic light emitting medium according to.
  34. The organic luminescent medium according to claim 32 which is a fused aryl group of the formula (2-6) 'in the Ar 5 and Ar 6 are substituted or unsubstituted C10-20 independently.
  35. Formula (1) and R b 'are each independently' R a 'in organic according to any one of claims 18 to 34, which is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group light-emitting media.
  36. Formula (1) ~ R 24 'are each independently' R 21 'in a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted substituents t- butyl group, a substituted or unsubstituted cyclohexyl group, or a substituted or unsubstituted organic light emitting medium according to any one of claims 18 to 35 as a trimethylsilyl group.
  37. The anode and the cathode,
    And a least one organic thin layer between the anode and the cathode,
    At least one layer organic electroluminescent device containing the organic light emitting medium according to any one of claims 1 to 36 of the organic thin film layer.
  38. The organic electroluminescence device according to claim 37 organic thin film layer containing the organic luminescent medium is a light-emitting layer.
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