WO2009107596A1

WO2009107596A1 - Organic luminescent medium and organic el element

Info

Publication number: WO2009107596A1
Application number: PCT/JP2009/053247
Authority: WO
Inventors: 正和舟橋; 昌宏河村; 光則伊藤
Original assignee: 出光興産株式会社
Priority date: 2008-02-25
Filing date: 2009-02-24
Publication date: 2009-09-03

Abstract

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

Description

Organic light-emitting medium and organic EL device

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

Conventionally, an organic EL element (organic electroluminescence element) using light emission of an organic compound is known. The organic EL element has a plurality of organic thin films stacked between an anode and a cathode. In this configuration, when a voltage is applied between the anode and the cathode, holes and electrons are injected into the organic thin film from the anode and the cathode, respectively. Excited molecules are generated in the light emitting layer in the organic thin film by the injected holes and electrons. Then, energy when returning from the excited state to the ground state is emitted as light.

As an example of the material used for the light emitting layer, Patent Document 1 discloses a combination of an anthracene host and an arylamine. Patent Documents 2 to 4 disclose a combination of an anthracene host having a specific structure and a diaminopyrene dopant. Furthermore, Patent Documents 5 and 6 disclose anthracene-based host materials.
However, even if the combination of the host and the dopant disclosed in these documents is used, it is difficult for the blue light emitting device to maintain a long lifetime and to obtain short wavelength blue light emission. In addition, in the green light emitting element, it is difficult to obtain an organic EL element that maintains high efficiency and has a long lifetime.
WO 2004/018588 WO2004 / 018587 JP 2004-204238 A WO2005 / 108348 publication WO2005 / 054162 publication WO2005 / 061656

An object of the present invention is to provide an organic EL element including a combination of a specific host material and a dopant material capable of realizing short-wavelength light emission and long-lifetime blue light emission and high-efficiency and long-lifetime green light emission. An organic light-emitting medium that can be used for an organic thin film layer of an EL element is provided.
Another object of the present invention is to use an organic EL element including a combination of a specific host material and a dopant material, which can obtain high luminous efficiency and has a long lifetime, and an organic thin film layer of the organic EL element. It is to provide an organic light-emitting medium that can be used.

As a result of intensive studies to solve the above problems, the present inventors have found that the following problems can be solved by the present invention.
According to the present invention, the following organic light emitting media and the like are provided.

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

(In the formula (1), R ²¹ to R ²⁴ each independently represents a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted When a substituted cycloalkyl group having 3 to 50 carbon atoms or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms and one or two pairs of adjacent alkyl groups on the same benzene ring, The adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group, provided that the adjacent alkyl group forms a 1-naphthyl group together with the benzene ring to which they are bonded. Is excluded.
n1 to n4 are each independently an integer of 0 to 5.
R ^a and R ^b are each independently a hydrogen atom, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nucleus, 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 nucleus having 6 to 50 carbon atoms An aryloxy group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
However, it excludes when R ^a and R ^b are hydrogen atoms at the same time. )

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

An organic light-emitting medium comprising a diaminopyrene derivative represented by the following formula (1) ′ and an anthracene derivative represented by the following formula (2) ′.

(In the formula (1) ′, R ^{21 ′} to R ^{24 ′} each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted 1 to 50 carbon atoms, An alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear 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, When there are one or two sets of adjacent alkyl groups on the same benzene ring, the adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group.
n1 ′ to n4 ′ are each independently an integer of 1 to 5.
R ^{a ′} and R ^{b ′} are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. )

(In the formula (2) ′, Ar ^{11 ′} and Ar ^{12 ′} are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms,
R ^{1 ′} to R ^{8 ′} each independently represents 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 nuclear carbon atoms, substituted or unsubstituted An 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 nuclear carbon atoms, a substituted or unsubstituted nuclear carbon number 6 to It is a group selected from 50 arylthio groups, substituted or unsubstituted alkoxycarbonyl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, carboxyl groups, halogen atoms, cyano groups, nitro groups and hydroxyl groups.
Provided that when R ^{1 ′} to R ^{8 ′} are hydrogen atoms and one of Ar ^{11 ′} and Ar ^{12 ′} is an unsubstituted 2-naphthyl group, the other is 4- (1-naphthyl) phenyl-1- It is not an ill group. )

An organic electroluminescence device comprising an anode, a cathode, and one or more organic thin film layers between the anode and the cathode, wherein at least one of the organic thin film layers contains the organic light emitting medium.

According to the present invention, an organic EL element including a combination of a specific host material and a dopant material capable of realizing short-wavelength light emission and long-lifetime blue light emission, and high-efficiency and long-lifetime green light emission, and the organic An organic light-emitting medium that can be used for an organic thin film layer of an EL element can be provided.
According to the present invention, it is possible to provide an organic EL element that can obtain high luminous efficiency and has a long lifetime, and an organic light emitting medium that can be used for an organic thin film layer of the organic EL element.

[Organic light-emitting medium]
The organic light-emitting medium of the present invention includes the organic light-emitting medium I and the organic light-emitting medium II, each including a specific diaminopyrene derivative and a specific anthracene derivative. The organic light-emitting medium contributes to light emission as a constituent component of the organic thin film layer of the organic EL element, and is present in the layer as, for example, a deposit. When used in an organic EL device, the organic light emitting medium I can emit light of a short wavelength including blue light emission with high color purity, contributes to a long life, or obtains high light emission efficiency. it can. In addition, the organic light emitting medium II can realize a green organic EL element having a high light emission rate and a long lifetime. Hereinafter, the organic light emitting media I and II will be described.

In the present invention, “nuclear carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. The “nuclear atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
In the definition of each formula of the present invention, the substituent in “substituted or unsubstituted...” Is an alkyl group, aryl group, cycloalkyl group, alkoxy group, heterocyclic group, aralkyl group as described later. , 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, and a heterocyclic group.

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

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

In formula (1), R ²¹ to R ²⁴ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group. When the cycloalkyl group is a cycloalkyl group having 3 to 50 nuclear carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and one or two adjacent alkyl groups are present on the same benzene ring, Adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group, provided that the adjacent alkyl group forms a 1-naphthyl group together with the benzene ring to which they are bonded. except.
n1 to n4 are each independently an integer of 0 to 5.
R ^a and R ^b are each independently a hydrogen atom, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nucleus, 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 nucleus having 6 to 50 carbon atoms An aryloxy group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group. However, it excludes when R ^a and R ^b are hydrogen atoms at the same time.

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

Examples of the substituted or unsubstituted aryl group represented by R ²¹ to R ²⁴ include a phenyl group, a methylphenyl group, an ethylphenyl group, a biphenyl group, a cyclopentylphenyl group, a cyclohexylphenyl group, a methylbiphenyl group, an ethylbiphenyl group, and a cyclopentylphenyl. Group, cyclohexylbiphenyl group, terphenyl group, naphthyl group, methylnaphthyl group, anthryl group, pyrenyl group, chrysenyl group, fluoranthenyl group, perylenyl group, fluorenyl group, etc., preferably phenyl group, naphthyl group, fluorenyl group It is a group.

Examples of the substituted or unsubstituted alkyl group of R ²¹ to R ²⁴ include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl Group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, and the like. Preferred are methyl group, ethyl group, propyl group, and tert-butyl group.

When there are one or two pairs of adjacent alkyl groups on the same benzene ring (a benzene ring directly bonded to a nitrogen atom), the adjacent alkyl groups are bonded to each other to form a substituted or unsubstituted divalent saturated or unsubstituted group. A saturated linking group may be formed.

As the substituent formed by the bonding group and the benzene ring directly bonded to the nitrogen atom, it is preferable to form a mother nucleus represented by the following general formulas (3-1) to (3-6). May further have a substituent such as an alkyl group, an alkenyl group, an alkynyl group, and an aryl group. However, this does not apply when a 1-naphthyl group is formed.

Wherein A, D, E, G and J are —CH ₂ —, —CR ⁵⁰ R ⁵¹ — (R ⁵⁰ and R ⁵¹ each represent a substituent), —O—, —S—, — N- or -CO-
a to h each represents an integer of 1 to 10;
When a, b, c, g, and h are 2 or more, a plurality of A, D, E, G, and J may be the same or different. )

a to c are each preferably 5 or 6, d to f are each preferably 2, and g and h are each preferably 1.
The substituent for R ⁵⁰ and 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, or a nucleus having 6 to 14 carbon atoms. An aryl group, a heterocyclic group having 5 to 14 nuclear atoms, and more preferably an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 14 nuclear carbon atoms.

The substituent formed by the bonding group and the benzene ring directly bonded to the nitrogen atom is more preferably a ring having the following structure.

Examples of the cycloalkyl group represented by R ²¹ to R ²⁴ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a bicycloheptyl group, a bicyclooctyl group, and a tricycloheptyl group. A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a bicycloheptyl group, a bicyclooctyl group, and an adamantyl group.

Examples of the substituted or unsubstituted aralkyl group of R ²¹ to R ²⁴ include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 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-bromine Benzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, 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-phenylisopropyl group, 1-chloro-2-phenylisopropyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group, etc. That.

Examples of R ^a and R ^b include the same as R ¹ to R ⁸ in the formula (2) described later.

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

In the above formula, R ²¹ to R ²⁴ , R ^a and R ^b are the same as described above. R ²¹ to R ²⁴ may be the same or different from each other, but it is preferable that R ²¹ and R ²³ , and R ²² and R ²⁴ are the same. 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.

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

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

The anthracene derivative according to the present invention is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected depending on the configuration of the organic EL element to be applied and the required characteristics.

(Anthracene derivative (A))
In the anthracene derivative, Ar ¹¹ and Ar ¹² in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. The anthracene derivative can be classified into a case where Ar ¹¹ and Ar ¹² are the same substituted or unsubstituted condensed aryl group and a case where they are different substituted or unsubstituted condensed aryl groups.
Specifically, anthracene derivatives represented by the following formulas (2-1) to (2-3) and anthracene derivatives in which Ar ¹¹ and Ar ¹² in formula (2) are different substituted or unsubstituted condensed aryl groups Is mentioned.

In the anthracene derivative represented by the following formula (2-1), Ar ¹¹ and Ar ¹² are substituted or unsubstituted 9-phenanthrenyl groups.

(In the formula (2-1), R ¹ to R ⁸ are the same as above,
R ¹¹ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxyl A group selected from a group, a halogen atom, a cyano group, a nitro group and a hydroxyl group,
a is an integer of 0 to 9. When a is an integer of 2 or more, a plurality of R ^{11 s} may be the same or different on condition that two substituted or unsubstituted phenanthrenyl groups are the same. )

In the anthracene derivative represented by the following formula (2-2), Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 2-naphthyl groups.

(In the formula (2-2), R ¹ to R ⁸ and R ¹¹ are the same as above,
b is an integer of 1 to 7. When b is an integer of 2 or more, a plurality of R ¹¹ may be the same or different on condition that two substituted or unsubstituted 2-naphthyl groups are the same. )

In the anthracene derivative represented by the following formula (2-3), Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 1-naphthyl groups.

(In the formula (2-2), R ¹ to R ⁸ , R ¹¹ and b are the same as described above. When b is an integer of 2 or more, a plurality of R ¹¹ are two substituted or unsubstituted. Each may be the same or different, provided that the 1-naphthyl groups are the same.)

Examples of the anthracene derivative in which Ar ¹¹ and Ar ¹² in Formula (2) are different substituted or unsubstituted condensed aryl groups include a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, and substituted or unsubstituted It is preferably any one of unsubstituted 2-naphthyl groups.
Specifically, when Ar ¹¹ is a 1-naphthyl group and Ar ¹² is a 2-naphthyl group, Ar ¹¹ is a 1-naphthyl group and Ar ¹² is a 9-phenanthryl group, and Ar ¹¹ is 2- This is the case where the naphthyl group and Ar ¹² are a 9-phenanthryl group.

(Anthracene derivative (B))
In the anthracene derivative, one of Ar ¹¹ and Ar ¹² in Formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. Specific examples of the anthracene derivative include anthracene derivatives represented by the following formulas (2-4) and (2-5).

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

(In the formula (2-4), R ¹ to R ⁸ , R ¹¹ and b are the same as above,
Ar ⁶ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Or an unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a 9,9-dimethylfluoren-1-yl group, or a 9,9-dimethylfluorene-2- Yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or dibenzofuran It is a -4-yl group. Ar ⁶ may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar ⁶ is bonded. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different. )

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

(In the formula (2-5), R ¹ to R ⁸ , R ¹¹ and b are the same as above,
Ar ⁷ is a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted group Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a dibenzofuran-1-yl group, a dibenzofuran-2-yl group, a dibenzofuran-3-yl group, or a dibenzofuran-4-yl group. Ar ⁷ may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar ⁷ is bonded. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different.
However, Ar ⁷ excludes the case where 4- (1-naphthyl) phenyl-1-yl group is formed with the adjacent phenylene group. )

(Anthracene derivative (C))
The anthracene derivative is represented by the following formula (2-6), specifically, any one of the following formulas (2-6-1), (2-6-2), and (2-6-3) It is preferable that it is a derivative represented.

(In the formula (2-6), R ¹ to R ⁸ and Ar ⁶ are the same as above,
Ar ⁵ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Alternatively, it is an unsubstituted aralkyl group having 7 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and Ar ⁵ and Ar ⁶ are each independently selected. )

(In formula (2-6-1), R ¹ to R ⁸ are as defined above.)

(In formula (2-6-2), R ¹ to R ⁸ are the same as described above. Ar ⁸ is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.)

(In the formula (2-6-3), R ¹ to R ⁸ are the same as in the formula (2).
Ar ^5a and Ar ^6a are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. )

Examples of the substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms of Ar ¹¹ and Ar ¹² include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, and a 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-chrycenyl 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 group, 2-benzo [g] group Senyl group, 3-benzo [g] chrysenyl group, 4-benzo [g] chrysenyl group, 5-benzo [g] chrysenyl group, 6-benzo [g] chrysenyl group, 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 Group, 14-benzo [g] chrysenyl group, 1-triphenyl group, 2-triphenyl group, 2-fluorenyl group, 9,9-dimethylfluoren-2-yl group, benzofluorenyl group, dibenzofluorenyl Group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphe Ru-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl Group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4 ′ -Methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group and the like. Preferably, a substituted phenyl group and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms (for example, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group).

In addition, Ar ^5a , Ar ^6a and Ar ⁸ substituted or unsubstituted condensed aryl groups having 10 to 20 nuclear carbon atoms include 1-naphthyl group, 2-naphthyl group, 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 can be mentioned. In particular, a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.

Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms of R ¹ to R ⁸ , R ¹¹ , Ar ⁵ and Ar ⁶ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 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- A tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group and the like.

Examples of the substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms of R ¹ to R ⁸ , R ¹¹ and Ar ⁵ to Ar ⁷ include 1-pyrrolyl group, 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 group, 3-furyl group, 2-benzofuranyl group 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isofuranyl group Zofuranyl 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 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 Group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-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 Group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenant Rin-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-pheno 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-flazanyl group, 2-thienyl group, 3-thienyl group, 2 -Methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3 -Methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-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 group , 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.

Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R ¹ to R ⁸ , R ¹¹ and Ar ⁵ to Ar ⁷ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s- Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxy Isobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl Group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2, 3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3- Diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1 , 2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3- Tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group 1,2,3-trinitropropyl group and the like.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms of the substituents R ¹ to R ⁸ , R ¹¹ and Ar ⁵ to Ar ⁷ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, 4 -Methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R ¹ to R ⁸ and R ¹¹ is a group represented by —OZ, and Z is the substituted or unsubstituted carbon number of R ¹ to R ^8. Selected from 1 to 50 alkyl groups.

^{^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 Are benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β- Naphthylisopropyl group, 2-β-naphthylisopropyl group, 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 group, m-hydroxybenzyl group, 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-phenylisopropyl group, 1-chloro-2- A phenyl isopropyl group etc. are mentioned.

The substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms of R ¹ to R ⁸ and R ¹¹ is represented as —OY, and Y represents the substituted or unsubstituted nuclear carbon number of the above R ¹ to R ^8. Selected from 6 to 50 aryl groups.

The substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms represented by R ¹¹ is represented by —SY, and Y represents the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms represented by R ¹ to R ^8. To be elected.

The substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms of R ¹¹ (the alkyl part has 1 to 49 carbon atoms) is represented as —COOZ, and Z is the substituted or unsubstituted carbon number of R ¹ to R ^8. It is selected from 1 to 49 alkyl groups.

Examples of the substituted silyl group of R ¹ to R ⁸ and R ¹¹ include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.

Examples of the halogen atom for R ¹ to R ⁸ and R ¹¹ include fluorine, chlorine, bromine, iodine and the like.

Anthracene derivatives represented by the above formula (2), formula (2-1) to (2-6), formula (2-6-1), (2-6-2) and (2-6-3) Preferably, all of R ¹ to R ⁸ are hydrogen atoms.

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

The diaminopyrene derivative represented by the formula (1) is, for example, introduced into a dibromopyrene obtained by bromination of commercially available pyrene by a known method, then brominated again, and correspondingly reacted under a metal catalyst. It can be synthesized by reacting with a secondary amine compound. Moreover, the anthracene derivative represented by Formula (2) is compoundable by the method of WO2004 / 018587, for example.

The organic light-emitting medium of the present invention is in a state in which the anthracene derivative represented by the diaminopyrene derivative represented by the formula (1) as described above coexists.
The mass ratio of the diaminopyrene derivative represented by the formula (1) and the anthracene derivative represented by the formula (2) is preferably 50:50 to 0.1: 99.9, and 20:80 to 1 : 99 is more preferable.

[Organic light emitting medium II]
The organic light emitting medium II includes a diaminopyrene derivative according to the present invention represented by the following formula (1) ′ and an anthracene derivative represented by the following formula (2) ′.

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

In formula (1) ′, R ^{21 ′} to R ^{24 ′} each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. A substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear 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, and the same When there are one or two sets of adjacent alkyl groups on the benzene ring, the adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group.
n1 ′ to n4 ′ are each independently an integer of 1 to 5.
R ^{a ′} and R ^{b ′} are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.

Examples of the substituted or unsubstituted aryl group and substituted or unsubstituted alkyl group having 6 to 50 nuclear carbon atoms of R ^{21 ′} to R ^{24 ′} are the same as those of R ²¹ to R ^{24 in} the above formula (1). is there.

As the substituent formed by the benzene ring directly bonded to the nitrogen atom and the bonding group, it is preferable to form a mother nucleus represented by the above general formulas (3-1) to (3-6). May further have a substituent such as an alkyl group, an alkenyl group, an alkynyl group, and an aryl group.

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 ′} to R ^{24 ′} are 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, substituted or unsubstituted An unsubstituted cyclohexyl group, or a substituted or unsubstituted trimethylsilyl group.

The substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms of R ^{a ′} and R ^{b ′} is defined as “substituted or unsubstituted nuclear carbon atoms of 6 to 50 defined by R ¹¹ in formula (2) ′ described later. And is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

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

In the above formula, R ^{21 ′} to R ^{24 ′} , R ^{a ′} and R ^{b ′} are the same as described above. R ^{21 ′} to R ^{24 ′} may be the same or different, but it is preferable that R ^{21 ′} and R ^{23 ′} and R ^{22 ′} and R ^{24 ′} are the same. 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.

(Anthracene derivative)
An anthracene derivative according to the organic light-emitting medium II is represented by the following formula (2) ′.

(In the formula (2) ′, Ar ^{11 ′} and Ar ^{12 ′} are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms,
R ^{1 ′} to R ^{8 ′} each independently represents 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 nuclear carbon atoms, substituted or unsubstituted An 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 nuclear carbon atoms, a substituted or unsubstituted nuclear carbon number 6 to It is a group selected from 50 arylthio groups, substituted or unsubstituted alkoxycarbonyl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, carboxyl groups, halogen atoms, cyano groups, nitro groups and hydroxyl groups.
However, when one of Ar ^{11 ′} and Ar ^{12 ′} is an unsubstituted 2-naphthyl group, the other is not a 4- (1-naphthyl) phenyl-1-yl group. )

In the anthracene derivative of the present invention, preferably, when one of Ar ^{11 ′} and Ar ^{12 ′} is an unsubstituted 2-naphthyl group, the other is not an aryl-substituted phenyl group.

The anthracene derivative according to the present invention is preferably any of the following anthracene derivatives (A) ′, (B) ′, and (C) ′, and is selected depending on the configuration of the organic EL element to be applied and the required characteristics.

(Anthracene derivative (A) ')
In the anthracene derivative, Ar ^{11 ′} and Ar ¹² ′ in the formula (2) ′ are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. The anthracene derivative can be classified into a case where Ar ^{11 ′} and Ar ^{12 ′} are the same substituted or unsubstituted condensed aryl group and a case where they are different substituted or unsubstituted condensed aryl groups.
Specifically, anthracene derivatives represented by the following formulas (2-1) ′ to (2-3) ′, and substituted or unsubstituted condensed aryl in which Ar ^{11 ′} and Ar ^{12 ′} in formula (2) ^′ are different And anthracene derivatives as groups.

In the anthracene derivative represented by the following formula (2-1) ′, Ar ^{11 ′} and Ar ^{12 ′} are substituted or unsubstituted 9-phenanthrenyl groups.

(In the formula (2-1) ′, R ^{1 ′} to R ^{8 ′} are the same as above,
R ¹¹ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxyl A group selected from a group, a halogen atom, a cyano group, a nitro group and a hydroxyl group,
a is an integer of 0 to 9. When a is an integer of 2 or more, a plurality of R ^{11 s} may be the same or different on condition that two substituted or unsubstituted phenanthrenyl groups are the same. )

In the anthracene derivative represented by the following formula (2-2) ′, Ar ^{11 ′} and Ar ^{12 ′} in the formula (2) ^′ are substituted or unsubstituted 2-naphthyl groups.

(In the formula (2-2) ′, R ^{1 ′} to R ^{8 ′} and R ¹¹ are the same as above,
b is an integer of 1 to 7. When b is an integer of 2 or more, a plurality of R ¹¹ may be the same or different on condition that two substituted or unsubstituted 2-naphthyl groups are the same. )

In the anthracene derivative represented by the following formula (2-3) ′, Ar ^{11 ′} and Ar ^{12 ′} in the formula (2) ^′ are substituted or unsubstituted 1-naphthyl groups.

(In the formula (2-2) ′, R ^{1 ′} to R ^{8 ′} , R ¹¹ and b are the same as those described above. When b is an integer of 2 or more, a plurality of R ¹¹ are substituted with two substituents or Each may be the same or different, provided that the unsubstituted 1-naphthyl groups are the same.

In addition to the anthracene derivatives represented by the above formulas (2-1) ′ to (2-3) ′, Ar ^{11 ′} and Ar ^{12 ′} in the formula (2) ^′ are the same substituted or unsubstituted fluoranthenyl group. And an anthracene derivative in which Ar ^{11 ′} and Ar ^{12 ′} in the formula (2) ^′ are the same substituted or unsubstituted pyrenyl group are also preferable.

As an anthracene derivative in which Ar ^{11 ′} and Ar ¹² ′ in formula (2) ′ are different substituted or unsubstituted condensed aryl groups, Ar ^{11 ′} and Ar ^{12 ′} are represented by formulas (2-1) ′ to (2- 3) ′, a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, and a substituted or unsubstituted fluoranthenyl group Is preferred.
Specifically, when Ar ^{11 ′} is a 1-naphthyl group and Ar ^{12 ′} is a 2-naphthyl group, Ar ^{11 ′} is a 1-naphthyl group and Ar ^{12 ′} is a 9-phenanthryl group, and Ar ^This is the case where ^{11 ′} is a 2-naphthyl group and Ar ^{12 ′} is a 9-phenanthryl group.

(Anthracene derivative (B) ')
In the anthracene derivative, one of Ar ^{11 ′} and Ar ¹² ′ in the formula (2) ′ is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. ing. Specific examples of the anthracene derivative include anthracene derivatives represented by the following formulas (2-4) ′ and (2-5) ′.

In the anthracene derivative represented by the following formula (2-4) ′, Ar ^{11 ′} in the formula (2) ^′ is a substituted or unsubstituted 1-naphthyl group, and Ar ^{12 ′} is a substituted or unsubstituted phenyl group. It has become.

(In the formula (2-4) ′, R ^{1 ′} to R ^{8 ′} , R ¹¹ and b are the same as above,
Ar ⁶ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Or an unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a 9,9-dimethylfluoren-1-yl group, or a 9,9-dimethylfluorene-2- Yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or dibenzofuran It is a -4-yl group. Ar ⁶ may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar ⁶ is bonded. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different. )

In the anthracene derivative represented by the following formula (2-5) ′, Ar ^{11 ′} in the formula (2) ^′ is a substituted or unsubstituted 2-naphthyl group, and Ar ^{12 ′} is a substituted or unsubstituted phenyl group. It has become.

(In the formula (2-5) ′, R ^{1 ′} to R ^{8 ′} , R ¹¹ and b are the same as above,
Ar ⁷ is a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted group Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a dibenzofuran-1-yl group, a dibenzofuran-2-yl group, a dibenzofuran-3-yl group, or a dibenzofuran-4-yl group. Ar ⁷ may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar ⁷ is bonded. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different.
However, Ar ⁷ excludes the case where 4- (1-naphthyl) phenyl-1-yl group is formed with the adjacent phenylene group. )

In addition to the anthracene derivatives represented by the above formulas (2-4) ′ and (2-5) ′, Ar ^{11 ′} in the formula (2) ^′ is a substituted or unsubstituted fluoranthenyl group, and Ar Anthracene derivatives in which ^{12 ′} is a substituted or unsubstituted phenyl group are also preferable.

(Anthracene derivative (C) ')
The anthracene derivative is represented by the following formula (2-6) ′, specifically, the following formulas (2-6-1) ′, (2-6-2) ′ and (2-6-3) ′. It is preferable that it is a derivative represented by either.

(In the formula (2-6) ′, R ^{1 ′} to R ^{8 ′} and Ar ⁶ are the same as defined above;
Ar ⁵ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Alternatively, it is an unsubstituted aralkyl group having 7 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and Ar ⁵ and Ar ⁶ are each independently selected. )

(In formula (2-6-1) ′, R ^{1 ′} to R ^{8 ′} are the same as described above.)

(In the formula (2-6-2) ′, R ^{1 ′} to R ^{8 ′} are the same as described above. Ar ⁸ is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.)

( '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 substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. )

Examples of substituted or unsubstituted aryl groups having 6 to 50 nuclear carbon atoms of R ¹¹ , Ar ⁵ and Ar ⁶ , Ar ^{11 ′} and Ar ^{12 ′} are the same as those of Ar ¹¹ and Ar ^{12 in} the above formula (2). It is. Preferably, an unsubstituted phenyl group, a substituted phenyl group, and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms (eg, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group), substituted or unsubstituted A fluorenyl group (2-fluorenyl group) and a 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 group, 2-naphthyl group, 9-phenanthryl group, pyrenyl group (1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group), and fluorenyl group (2-fluorenyl group) are preferable.

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. Preferably, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group Group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group.

Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R ^{1 ′} to R ^{8 ′} , R ¹¹ and Ar ⁵ to Ar ⁷ include R ¹ to R ⁸ , R ¹¹ and Ar in the above formula (2). This is the same as ⁵ to Ar ⁷ . Preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group and t-butyl group.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms of the substituents R ^{1 ′} to R ^{8 ′} , R ¹¹ and Ar ⁵ to Ar ⁷ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like. Preferably, they are a cyclopentyl group and a cyclohexyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R ^{1 ′} to R ^{8 ′} and R ¹¹ is a group represented by —OZ, and Z is the substituted or unsubstituted group of R ^{1 ′} to R ^{8 ′.} It is selected from substituted alkyl groups having 1 to 50 carbon atoms.

R ^{1 ′} to R ^{8 ′} , R ¹¹ and Ar ⁵ to Ar ⁷ substituted or unsubstituted C 7-50 aralkyl groups (the aryl moiety has 6 to 49 carbon atoms, the alkyl moiety has 1 to 44 carbon atoms) ) Are the same as those of R ¹ to R ⁸ , R ¹¹ and Ar ⁵ to Ar ^{7 in} the above formula (2).

The substituted or unsubstituted aryloxy group and arylthio group having 6 to 50 nuclear carbon atoms of R ^{1 ′} to R ^{8 ′} and R ¹¹ are represented by —OY and —SY, respectively, and Y represents the above R ^{1 ′} to R ^{It is selected from 8 '} substituted or unsubstituted aryl groups having 6 to 50 nuclear carbon atoms.

A substituted or unsubstituted alkoxy group having 2 to 50 carbon atoms (the alkyl moiety has 1 to 49 carbon atoms) of R ^{1 ′} to R ^{8 ′} and R ¹¹ is represented as —COOZ, and Z represents the above R ^{1 ′} to R ^{It is selected from 8 '} substituted or unsubstituted alkyl groups having 1 to 49 carbon atoms.

Examples of the substituted silyl group of R ^{1 ′} to R ^{8 ′} and R ¹¹ include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.

Examples of the halogen atom for R ^{1 ′} to R ^{8 ′} and R ¹¹ include fluorine, chlorine, bromine and iodine.

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

The diaminopyrene derivative represented by the formula (1) ′ is prepared by, for example, introducing a substituent into dibromopyrene obtained by bromination of commercially available pyrene by a known method, and then brominating it again under a metal catalyst. Can be synthesized by reacting with a secondary amine compound. In addition, the anthracene derivative represented by the formula (2) ′ can be synthesized, for example, by the method described in WO 2004/018585.

The organic light-emitting medium of the present invention is in a state where an anthracene derivative represented by the diaminopyrene derivative formula (2) ′ represented by the formula (1) ′ as described above coexists.
The mass ratio of the diaminopyrene derivative represented by the formula (1) ′ and the anthracene derivative represented by the formula (2) ′ is preferably 50:50 to 0.1: 99.9, and 20:80 More preferably, it is ˜1: 99.

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

Further, the organic EL device of the present invention is an organic EL device in which an organic thin film layer comprising at least two layers including at least a light emitting layer is sandwiched between a cathode and an anode, and the organic EL device of the present invention is interposed between the anode and the light emitting layer. It is also preferable to have an organic layer whose main component is a luminescent medium. Examples of the organic layer include a hole injection layer and a hole transport layer.

In the present invention, organic EL elements having a plurality of organic thin film layers are (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole). (Injection layer / light emitting layer / electron injection layer / cathode) and the like.
In addition to the organic light-emitting medium of the present invention, further known light-emitting materials, doping materials, hole-injecting materials, and electron-injecting materials can be used for the multiple layers as needed. The organic EL element can prevent the brightness | luminance and lifetime fall by quenching by making the said organic thin film layer into a multilayer structure. If necessary, a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection layer, a layer that injects electrons from an electrode is referred to as an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.

Examples of host materials or doping materials that can be used in the light emitting layer together with the organic light emitting medium of the present invention include, for example, naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentaene. Condensed polyaromatic compounds such as pentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and the like Derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinato) aluminum, triarylamine derivatives, styrylamido Derivatives, 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, etc. However, it is not limited to these.

As a hole injection material, it has the ability to transport holes, has a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or organic light emitting medium, and excitons generated in the light emitting layer The compound which prevents the movement to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl Examples include alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers. However, it is not limited to these.

Among the hole injection materials that can be used in the organic EL device of the present invention, more effective hole injection materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
Examples of the aromatic tertiary amine derivative include triphenylamine, tolylamine, 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, etc. Or oligomers having these aromatic tertiary amine skeletons Or is a polymer, but is not limited thereto.

Examples of the phthalocyanine (Pc) derivative include H ₂ Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl ₂ SiPc, (HO) AlPc, (HO) GaPc, Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc—O—GaPc.

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

As an electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, and an excellent electron injection effect for the light emitting layer or light emitting material. The compound which prevents the movement to and is excellent in thin film forming ability is preferable.
As specific examples of the electron injecting material, 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable. As a specific example of the metal complex of 8-hydroxyquinoline or its derivative, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), such as tris (8-quinolinolato) aluminum, is injected. It can be used as a material.

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

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

Here, examples of the aryl group include a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group. Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group. This electron transfer compound is preferably a thin film-forming compound.

Specific examples of the electron transfer compound include the following.

Me represents methyl and tBu represents tbutyl.

Further, materials represented by the following general formulas (A) to (F) can also be used as the electron injection material.

(In the general formulas (A) and (B), A ¹ to 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 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms,
Ar ² represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or a divalent group thereof.
However, any ^one of Ar ¹ and Ar ² is a substituted or unsubstituted condensed ring group having 10 to 60 nuclear carbon atoms, or a substituted or unsubstituted monoheterocondensed ring group having 5 to 60 nucleus atoms.
L ¹ , L ² and L are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, or a substituted or unsubstituted An unsubstituted fluorenylene group.
R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is 2 or more, a plurality of R may be the same or different and adjacent to each other A plurality of R groups may be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.
R ¹ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or —L ¹ —Ar ¹ —Ar ² . The nitrogen-containing heterocyclic derivative represented by this.

HAr-L-Ar ¹ -Ar ² (C)
(Wherein HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent,
L has a single bond, an arylene group having 6 to 60 nuclear carbon atoms which may have a substituent, a heteroarylene group having 5 to 60 nuclear atoms which may have a substituent, or a substituent. A fluorenylene group which may be
Ar ¹ is an optionally substituted divalent aromatic hydrocarbon group having 6 to 60 nuclear carbon atoms,
Ar ² is an aryl group having 6 to 60 nuclear carbon atoms which may have a substituent or a heterocyclic group having 5 to 60 nuclear atoms which may have a substituent. The nitrogen-containing heterocyclic derivative represented by this.

Wherein X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, alkoxy group, alkenyloxy group, alkynyloxy group, hydroxy group, substituted or unsubstituted aryl group, substituted Or an unsubstituted heterocyclic ring or a structure in which X and Y are combined to form a saturated or unsaturated ring,
R ₁ to R ₄ each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, Alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl group, sulfonyl group, sulfanyl group, Silyl, carbamoyl, aryl, heterocyclic, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isothi If the cyanate were group or cyano group, or adjacent a structure substituted or the unsubstituted rings are fused. A silacyclopentadiene derivative represented by:

(Wherein R ₁ to R ₈ and Z ₂ are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, or an alkoxy group. Or an aryloxy group,
X, Y and Z ₁ each independently represent a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group;
The substituents of Z ₁ and Z ₂ may be bonded to each other to form a condensed ring. N represents an integer of 1 to 3, and when n is 2 or more, Z ₁ may be different.
However, the case where n is 1, X, Y and R ₂ are methyl groups and R ₈ is a hydrogen atom or a substituted boryl group and the case where n is 3 and Z ₁ is a methyl group are not included. A borane derivative represented by:

[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, 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 —O—Ga—Q ³ (Q ⁴ ) (Q ³ and Q ⁴ are the same as Q ¹ and Q ² ). ]

[Wherein, rings A ¹ and A ² are 6-membered aryl ring structures condensed with each other which may have a substituent. ]

This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.

Specific examples of the substituents of the rings A ¹ and A ² forming the ligand of the general formula (G) include chlorine, bromine, iodine, halogen atoms of fluorine, methyl group, ethyl group, propyl group, Substituted or unsubstituted alkyl groups such as butyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group, phenyl group, naphthyl group, 3-methyl A substituted or unsubstituted aryl group such as phenyl group, 3-methoxyphenyl group, 3-fluorophenyl group, 3-trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitrophenyl group, methoxy group, n- Butoxy group, t-butoxy group, trichloromethoxy group, trifluoroethoxy group, pentafluoropropoxy group, 2,2,3,3-tetrafur Substituted or unsubstituted alkoxy group such as lopropoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 6- (perfluoroethyl) hexyloxy group, phenoxy group, p-nitrophenoxy Group, pt-butylphenoxy group, 3-fluorophenoxy group, pentafluorophenoxy group, substituted or unsubstituted aryloxy group such as 3-trifluoromethylphenoxy group, methylthio group, ethylthio group, t-butylthio group, Substituted or unsubstituted alkylthio groups such as hexylthio group, octylthio group, trifluoromethylthio group, phenylthio group, p-nitrophenylthio group, pt-butylphenylthio group, 3-fluorophenylthio group, pentafluorophenylthio Group, 3-trifluoromethylphenylthio group, etc. Or an unsubstituted arylthio group, a cyano group, a nitro group, an amino group, a methylamino group, an ethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, a diphenylamino group or the like mono or disubstituted amino group, bis ( Acetoxymethyl) amino group, bis (acetoxyethyl) amino group, bisacetoxypropyl) amino group, bis (acetoxybutyl) amino group and other acylamino groups, hydroxyl group, siloxy group, acyl group, methylcarbamoyl group, dimethylcarbamoyl group, ethyl Carbamoyl group, diethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group, carbamoyl group such as phenylcarbamoyl group, carboxylic acid group, sulfonic acid group, imide group, cyclopentane group, cycloalkyl group such as cyclohexyl group, phenyl Aryl groups such as naphthyl group, biphenyl group, anthranyl group, phenanthryl group, fluorenyl group, pyrenyl group, 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, thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group, imidazolyl group, benzimidazolyl group And the like. Moreover, the above substituents may combine to form a further 6-membered aryl ring or heterocyclic ring.

Favorable forms of the organic EL device of the present invention include a device containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer. Here, the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals. Oxides, alkaline earth metal halides, rare earth metal oxides or rare earth metal halides, alkali metal carbonates, alkaline earth metal carbonates, alkali metal organic complexes, alkaline earth metal organic complexes In addition, at least one substance selected from the group consisting of organic complexes of rare earth metals can be preferably used.

More specifically, preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV). Particularly preferred are those having a work function of 2.9 eV or less, including at least one alkaline earth metal selected from the group consisting of: Among these, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. . These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element. Further, as a reducing dopant having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable. Particularly, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs. And a combination of Na and K. By including Cs in combination, the reducing ability can be efficiently exhibited, and by adding to the electron injection region, the emission luminance and the life of the organic EL element can be improved.

In the present invention, an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented and the electron injection property can be improved. As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
Specifically, preferable alkali metal chalcogenides include, for example, Li ₂ O, K ₂ O, Na ₂ S, Na ₂ Se, and Na ₂ O, and preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe. Further, preferable alkali metal halides include, for example, LiF, NaF, KF, CsF, LiCl, KCl, and NaCl. Examples of preferable alkaline earth metal halides include fluorides such as CaF ₂ , BaF ₂ , SrF ₂ , MgF ₂ and BeF ₂ , and halides other than fluorides.

In addition, as a semiconductor constituting the electron injection layer, an oxide containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. , Nitrides or oxynitrides, or a combination of two or more. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.

Next, as a cathode, what uses a metal, an alloy, an electroconductive compound, and a mixture thereof with a small work function (4 eV or less) as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, cesium, magnesium / silver alloy, aluminum / aluminum oxide, Al / Li ₂ O, Al / LiO, Al / LiF, aluminum Examples include lithium alloys, indium, and rare earth metals.
The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.

Here, when light emitted from the light emitting layer is taken out from the cathode, it is preferable that the transmittance of the light emitted from the cathode is larger than 10%. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 200 nm.

In general, since an organic EL element applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leakage or short circuit. In order to prevent this, an insulating thin film layer may be inserted between the pair of electrodes.

Examples of 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, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.

In order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., it is possible to provide a protective layer on the surface of the device, or to protect the entire device with silicon oil, resin, etc. It is.

As the conductive material used for the anode of the organic EL element of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Further, palladium, etc. and alloys thereof, ITO (indium tin oxide) substrate, tin oxide used for NESA substrate, metal oxide such as indium oxide, and organic conductive resin such as polythiophene and polypyrrole are used. Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.

In the organic EL device of the present invention, in order to emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the light emission wavelength region of the device. The substrate is also preferably transparent. The transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
Transparent resin films 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, polyethersulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, Polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene, etc. It is.

For the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to. The film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.

In the case of the wet film-forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used. In any organic thin film layer, an appropriate resin or additive may be used for improving film formability and preventing pinholes in the film. Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

The organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like. The material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.

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

Example 1
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The glass substrate with the transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and first, a compound A-1 having a film thickness of 60 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. Was deposited. Subsequent to the formation of the A-1 film, A-2 having a thickness of 20 nm was formed on the A-1 film. Further, the host material EM1 and the dopant material DM7-4 of the present invention were formed on the A-2 film at a film thickness ratio of 40: 2 to form a blue light emitting layer.

On this film, Alq having a thickness of 20 nm was deposited as an electron transport layer by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode to form an organic EL light emitting device.

Alq

Examples 2 to 174
In Example 1, organic EL devices were similarly produced using the host materials and dopant materials shown in Tables 1 to 5 instead of the host material EM1 and the dopant material DM7-4.

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

Comparative Example 2
In Example 1, an organic EL device was similarly prepared using the following compound C instead of the host material EM1 and the following compound D instead of the dopant material DM7-4.

Comparative Example 3
In Example 1, an organic EL device was similarly prepared using the following compound E instead of the host material EM1 and the following compound F instead of the dopant material DM7-4.

Tables 1 to 5 show the light emission wavelength and the half-life at an initial luminance of 1000 cd / m ² of the organic EL element.

Examples 175-430
In Example 1, organic EL devices were similarly produced using the host materials and dopant materials shown in Tables 6 to 12 instead of the host material EM1 and the dopant material DM7-4.

Comparative Example 4
In Example 1, the following compound H-1 ′ was used instead of the host material EM1, and the dopant material DM2-4 ′ was used instead of the dopant material DM7-4, and an organic EL device was similarly produced.

Comparative Example 5
In Example 1, an organic EL device was produced in the same manner using the compound H-1 ′ in place of the host material EM1 and the dopant material DM10-4 ′ in place of the dopant material DM7-4.

Comparative Example 6
In Example 1, the following compound H-2 ′ was used in place of the host material EM1, and the following compound D-1 ′ was used in place of the dopant material DM7-4 to similarly produce an organic EL device.

Comparative Example 7
In Example 1, the following compound H-3 ′ was used in place of the host material EM1, and the following compound D-2 ′ was used in place of the dopant material DM7-4 to similarly produce an organic EL device.

Tables 6 to 12 show the luminous efficiencies of the organic EL devices obtained in Examples 175 to 430 and Comparative Examples 4 to 7 and the half lives at an initial luminance of 1000 cd / m ² .

The organic EL element using the organic light emitting medium of the present invention is useful as a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.
The entire contents of the documents described in this specification are incorporated herein by reference.

Claims

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

(In the formula (1), R 21 to R 24 each independently represents a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted When a substituted cycloalkyl group having 3 to 50 carbon atoms or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms and one or two pairs of adjacent alkyl groups on the same benzene ring, The adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group, provided that the adjacent alkyl group forms a 1-naphthyl group together with the benzene ring to which they are bonded. Is excluded.
n1 to n4 are each independently an integer of 0 to 5.
R a and R b are each independently a hydrogen atom, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nucleus, 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 nucleus having 6 to 50 carbon atoms An aryloxy group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
However, it excludes when R a and R b are hydrogen atoms at the same time. )

(In the formula (2), Ar 11 and Ar 12 are each independently a substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms,
R 1 to R 8 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted group; An 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 carbon group having 7 to 50 carbon atoms. A group selected from an aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.
However, when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group, the other is not a 4- (1-naphthyl) phenyl-1-yl group.
Further, at least one of Ar 11 and Ar 12 is not a substituted or unsubstituted anthryl group. )
The organic light-emitting medium according to claim 1, wherein in the anthracene derivative represented by the formula (2), when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group, the other is not an aryl-substituted phenyl group. .
The organic light-emitting medium according to claim 1 or 2, wherein Ar 11 and Ar 12 in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.
The organic light-emitting medium according to claim 3, wherein Ar 11 and Ar 12 in the formula (2) are the same group.
The organic light-emitting medium according to claim 4, wherein Ar 11 and Ar 12 in the formula (2) are substituted or unsubstituted 9-phenanthrenyl groups.
The organic light-emitting medium according to claim 4, wherein Ar 11 and Ar 12 in the formula (2) are substituted or unsubstituted 2-naphthyl groups.
The organic light-emitting medium according to claim 4, wherein Ar 11 and Ar 12 in the formula (2) are substituted or unsubstituted 1-naphthyl groups.
The organic light-emitting medium according to claim 3, wherein Ar 11 and Ar 12 in the formula (2) are different groups.
Ar 11 and Ar 12 in the formula (2) are any one of a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, and a substituted or unsubstituted 2-naphthyl group. 9. The organic light emitting medium according to 8.
3. The formula (2), wherein one of Ar 11 and Ar 12 is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. Organic light-emitting medium.
The organic light-emitting medium according to claim 10, wherein the substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms is a substituted or unsubstituted 1-naphthyl group.
The organic light-emitting medium according to claim 10, wherein the substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms is a substituted or unsubstituted 2-naphthyl group.
The organic light-emitting medium according to claim 1, wherein the anthracene derivative represented by the formula (2) is represented by the following formula (2-6).

(In the formula (2-6), R 1 to R 8 are the same as in the formula (2).
Ar 5 and Ar 6 are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nuclear carbon number of 3 to 50 A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. )
The organic light-emitting medium according to claim 13, wherein Ar 5 and Ar 6 in the formula (2-6) are each independently a substituted or unsubstituted phenyl group.
14. In the formula (2-6), one of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. An organic light-emitting medium as described.
The organic light-emitting medium according to claim 13, wherein Ar 5 and Ar 6 in the formula (2-6) are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.
The organic light-emitting medium according to any one of claims 1 to 16, wherein all of R 1 to R 8 in the formula (2) or the formula (2-6) are hydrogen atoms.
An organic light-emitting medium comprising a diaminopyrene derivative represented by the following formula (1) ′ and an anthracene derivative represented by the following formula (2) ′.

(In the formula (1) ′, R 21 ′ to R 24 ′ each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted 1 to 50 carbon atoms, An alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear 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, When there are one or two sets of adjacent alkyl groups on the same benzene ring, the adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group.
n1 ′ to n4 ′ are each independently an integer of 1 to 5.
R a ′ and R b ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. )

(In the formula (2) ′, Ar 11 ′ and Ar 12 ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms,
R 1 ′ to R 8 ′ each independently represents 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 nuclear carbon atoms, substituted or unsubstituted An 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 nuclear carbon atoms, a substituted or unsubstituted nuclear carbon number 6 to It is a group selected from 50 arylthio groups, substituted or unsubstituted alkoxycarbonyl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, carboxyl groups, halogen atoms, cyano groups, nitro groups and hydroxyl groups.
Provided that when R 1 ′ to R 8 ′ are hydrogen atoms and one of Ar 11 ′ and Ar 12 ′ is an unsubstituted 2-naphthyl group, the other is 4- (1-naphthyl) phenyl-1- It is not an ill group. )
19. The anthracene derivative represented by the formula (2) ′, wherein when one of Ar 11 ′ and Ar 12 ′ is an unsubstituted 2-naphthyl group, the other is not an aryl-substituted phenyl group. Organic luminescent medium.
The organic light-emitting medium according to claim 18 or 19, wherein Ar 11 ' and Ar 12 ' in the formula (2) 'are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms.
The organic light-emitting medium according to claim 20, wherein Ar 11 ' and Ar 12 ' in the formula (2) 'are the same group.
The organic light-emitting medium according to claim 21, wherein Ar 11 ' and Ar 12 ' in the formula (2) 'are substituted or unsubstituted 9-phenanthrenyl groups.
The organic light-emitting medium according to claim 21, wherein Ar 11 ' and Ar 12 ' in the formula (2) 'are substituted or unsubstituted 2-naphthyl groups.
The organic light-emitting medium according to claim 21, wherein Ar 11 ' and Ar 12 ' in the formula (2) 'are substituted or unsubstituted 1-naphthyl groups.
The organic luminescent medium according to claim 20, wherein Ar 11 ' and Ar 12 ' in the formula (2) 'are different groups.
Ar 11 ′ and Ar 12 ′ in the formula (2) ′ are substituted or unsubstituted 9-phenanthrenyl group, substituted or unsubstituted 1-naphthyl group, substituted or unsubstituted 2-naphthyl group, substituted or unsubstituted The organic luminescent medium according to claim 25, which is any one of a fluoranthenyl group and a substituted or unsubstituted pyrenyl group.
19. In the formula (2) ′, one of Ar 11 ′ and Ar 12 ′ is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. 19. The organic light emitting medium according to 19.
The organic light-emitting medium according to claim 27, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 1-naphthyl group.
The organic light-emitting medium according to claim 27, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 2-naphthyl group.
The organic light-emitting medium according to claim 27, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted fluoranthenyl group.
The organic light-emitting medium according to claim 27, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted pyrenyl group.
The organic light-emitting medium according to claim 18 or 19, wherein the anthracene derivative represented by the formula (2) 'is represented by the following formula (2-6)'.

(In the formula (2-6) ′, R 1 ′ to R 8 ′ are the same as in the formula (2) ′.
Ar 5 and Ar 6 are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nuclear carbon number of 3 to 50 A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. )
In the formula (2-6) ′, one of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. The organic luminescent medium described in 1.
The organic light-emitting medium according to claim 32, wherein Ar 5 and Ar 6 in the formula (2-6) ′ are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.
The organic compound according to claim 18, wherein R a ′ and R b ′ in the formula (1) ′ are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. Luminescent medium.
In formula (1) ′, R 21 ′ to R 24 ′ each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, substituted or unsubstituted The organic light-emitting medium according to any one of claims 18 to 35, which is a substituted t-butyl group, a substituted or unsubstituted cyclohexyl group, or a substituted or unsubstituted trimethylsilyl group.
An anode and a cathode;
Having one or more organic thin film layers between the anode and the cathode;
An organic electroluminescence device, wherein at least one of the organic thin film layers contains the organic light-emitting medium according to any one of claims 1 to 36.
38. The organic electroluminescence device according to claim 37, wherein the organic thin film layer containing the organic light emitting medium is a light emitting layer.