WO2009102026A1 - Organic luminescent medium and organic el device - Google Patents

Abstract

Disclosed is an organic luminescent medium containing a specific diaminopyrene derivative and a specific anthracene derivative. Also disclosed is an organic electroluminescent device wherein one or more organic thin film layers including a light-emitting layer are arranged between a cathode and an anode, and at least one of the organic thin film layers contains the organic luminescent medium.

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, a voltage is applied between the anode and the cathode. Then, 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, any of the materials has a problem that it is difficult to obtain short-wavelength light emission (for example, blue light emission) with high light emission efficiency and a short lifetime.

WO 2004/018588 WO2004 / 018587 JP 2004-204238 A WO2005 / 108348 publication WO2005 / 054162 publication WO2005 / 061656

The present invention provides an organic EL element that can obtain short-wavelength light emission (for example, blue light emission) with high light emission 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. The purpose is to provide.

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.
That is, this invention is an organic luminescent medium containing the diaminopyrene derivative represented by following formula (1), and the anthracene derivative represented by following formula (2).

(In the formula (1), Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. R ²¹ and R ²² are each independently a group selected from a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms. (However, one or more of Ar ¹ to Ar ⁴ are α-naphthyl groups, and R ²¹ and R ²² are not simultaneously hydrogen atoms.)

(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, and R ¹ to R ⁸ are each independently a hydrogen atom or a substituted group. Or an unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear 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 arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, Gen atom, a cyano group, a group selected from nitro group and a hydroxyl group.)

In addition, the present invention has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers contains the organic light emitting medium of the present invention. It is an element.

ADVANTAGE OF THE INVENTION According to this invention, the light emission of short wavelength (for example, blue light emission) can be obtained by high luminous efficiency, and the organic light emission which can be used for the organic thin film layer of the organic EL element with the long lifetime, and the said organic EL element A medium can be provided.

[Organic light-emitting medium]
The organic light-emitting medium of the present invention contains 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. And when it uses for an organic EL element, light emission of a short wavelength including blue light emission with high luminous efficiency is enabled, and it can contribute to lifetime improvement. Hereinafter, the diaminopyrene derivative and the anthracene derivative according to the present invention will be described.

(Diaminopyrene derivative)
The diaminopyrene derivative according to the present invention is represented by the following formula (1).

(In the formula (1), Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. R ²¹ and R ²² are each independently a group selected from a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms. (However, one or more of Ar ¹ to Ar ⁴ are α-naphthyl groups, and R ²¹ and R ²² are not simultaneously hydrogen atoms.)

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 addition, examples of the substituent in “substituted or unsubstituted...” Include alkyl groups, aryl groups, cycloalkyl groups, alkoxy groups, heterocyclic groups, aralkyl groups, aryloxy groups, arylthio groups, alkoxy groups as described later. Examples thereof include a carbonyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, a dibenzofuranyl group, and a fluorenyl group.

Examples of the aryl group of Ar ¹ to Ar ⁴ having 6 to 50 nuclear carbon atoms include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group, chrysenyl group, fluoranthenyl Group, perylenyl group and the like.
The number of nuclear carbons is preferably 6 to 20 and more preferably 6 to 12 from the viewpoint of vapor deposition temperature.

Examples of the heterocyclic group of Ar ¹ to Ar ⁴ having 5 to 50 nuclear atoms include imidazole, benzimidazole, pyrrole, furan, thiophene, oxadiazoline, indoline, carbazole, pyridine, quinoline, isoquinoline, benzoquinone, pyralazine, Residues such as imidazolidine, piperidine and the like can be mentioned.
The number of nucleus atoms is preferably 5 to 20 and more preferably 5 to 12 from the viewpoint of vapor deposition temperature.

Two of Ar ¹ to Ar ^{4 in} Formula (1) are preferably α-naphthyl groups, and Ar ¹ and Ar ³ are more preferably α-naphthyl groups. In the formula (1), R ²¹ and R ²² are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 nuclear carbon atoms. It is preferable. Furthermore, R ²¹ and R ²² in formula (1) are preferably the same group (for example, the above substituent).

The substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R ²¹ and R ²² includes a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, t -Butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl 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, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-tri Lolopropyl 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, -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- A trinitropropyl group etc. are mentioned.
The carbon number is preferably from 1 to 10, more preferably from 1 to 6, from the viewpoint of vapor deposition temperature. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl are preferred.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms of the substituent of R ²¹ and R ²² include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1- Examples thereof include an adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.
The number of nuclear carbons is preferably from 3 to 10, more preferably from 5 to 8, from the viewpoint of vapor deposition temperature. Of these, a cyclopentyl group and a cyclohexyl group are preferable.

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

(Anthracene derivative)
The anthracene derivative according to the present invention 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 20 nuclear carbon atoms, and R ¹ to R ⁸ are each independently a hydrogen atom or a substituted group. Or an unsubstituted aryl group having 6 to 50 nuclear carbon atoms (including a condensed aryl group), a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and 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 An aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group; Group, a carboxyl group, a halogen atom, a cyano group, a group selected from nitro group and a hydroxyl 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 group, and a case where they are different groups. Specific examples include anthracene derivatives represented by the following formulas (2-1) to (2-3) and anthracene derivatives in which Ar ¹¹ and Ar ¹² in the formula (2) are different 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 ¹¹ is 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, substituted or unsubstituted. 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. An aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, A group selected from a substituted or unsubstituted silyl group, carboxyl group, halogen atom, cyano group, nitro group and hydroxyl group, a is an integer of 0 to 9. a is an integer of 2 or more If, a plurality of R ¹¹ are the two substituted or condition that unsubstituted phenanthrenyl group are identical, each may be the same or different.)

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

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

(In the formula (2-2), R ¹¹ and b are the same as those in the formula (2-1). 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 α-naphthyl groups are the same.)

As the anthracene derivative in which Ar ¹¹ and Ar ¹² in the formula (2) are different groups, Ar ¹¹ and Ar ¹² are the aforementioned substituted or unsubstituted 9-phenanthrenyl group, substituted or unsubstituted α-naphthyl group. And a substituted or unsubstituted β-naphthyl 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 α-naphthyl group, and Ar ¹² is a substituted or unsubstituted phenyl group. .

(In the formula (2-4), 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, or a substituted or unsubstituted nuclear carbon number. A cycloalkyl group having 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 nucleus atoms, and Ar ⁶ is substituted. A substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group may be formed together with the phenylene group, and R ¹¹ and b are the same as in the formula (2-1). If is an integer of 2 or more, plural R ¹¹ are each 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 β-naphthyl group, and Ar ¹² is a substituted or unsubstituted phenyl group. .

(In formula (2-5), Ar ⁶ is the same as in formula (2-4), and R ¹¹ and b are the same as in formula (2-1). Also, when b is an integer of 2 or more And the plurality of R ¹¹ may be the same or different.)

(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 Formula (2-6), R ¹ to R ⁸ are the same as in Formula (2). Ar ⁵ is the same as Ar ^{6 in} Formula (2-4), and is independently selected from Ar ⁶ . )

(In formula (2-6-1), R ¹ to R ⁸ are the same as in formula (2).)

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

The aryl group of ^{Ar 11, Ar 12, Ar 5} , Ar 6 substituted or unsubstituted aromatic ring group having 6 to 20, a phenyl group, 1-naphthyl, 2-naphthyl, 1-anthryl group, 2-anthryl Group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl Group, 2-pyrenyl group, 4-pyrenyl group, 6-chrysenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4-benzo [c] Phenanthryl group, 5-benzo [c] phenanthryl group, 6-benzo [c] phenanthryl group, 1-benzo [g] chrysenyl group, 2-ben Zo [g] chrysenyl 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 Group, 8-benzo [g] chrysenyl group, 9-benzo [g] chrysenyl group, 10-benzo [g] chrysenyl group, 11-benzo [g] chrysenyl group, 12-benzo [g] chrysenyl group, 13-benzo [G] chrysenyl group, 14-benzo [g] chrysenyl group, 1-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 Terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p- Tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4 Examples include a '-methylbiphenylyl group, a 4 "-t-butyl-p-terphenyl-4-yl group, and the like. Preferred is a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms, particularly 1 A -naphthyl group, 2-naphthyl group, or 9-phenanthryl group is preferred.

The substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms of Ar ^5a and Ar ^6a includes 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] chrysene 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, benzofluorenyl group, dibenzofluorenyl group, and the like. 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 nuclear carbon atoms of R ¹ to R ⁸ 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, 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-tolyl group, m-tolyl group, p-tol 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 Examples include a '-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, and the like.
The number of nuclear carbons is preferably 6 to 30, and more preferably 6 to 20, from the viewpoint of vapor deposition temperature.

Examples of the substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms of R ¹ to R ⁸ include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, and 3-pyridinyl group. 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 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 Group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuran group Nyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group, 4-quinolyl group, 5- Quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8- Isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phena N-tridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group 1,7-phenanthroline-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline-4-yl group, 1,7-phenanthroline-5-yl group, 1,7- Phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group 1,8-phenanthroline-3-yl group, 1,8-phenanthroline-4-yl group, 1,8-phenanthroline-5-yl group, 1,8-phene group Nthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline -7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-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-phenanthro 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-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-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, -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) pyrrol-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 Group, 2-t-butyl 3-indolyl group, 4-t-butyl 3-indolyl group and the like.
The number of nucleus atoms is preferably from 5 to 30, more preferably from 5 to 20, from the viewpoint of the deposition temperature.

Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R ¹ to R ⁸ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, and t-butyl. Group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl 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-trichloro group Pill 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-cyano Ethyl 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-tri Examples thereof include a nitropropyl group.
The carbon number is preferably from 1 to 10, more preferably from 1 to 6, from the viewpoint of vapor deposition temperature.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms represented by R ¹ to R ⁸ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 1-adamantyl group. , 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
The number of nuclear carbons is preferably from 3 to 10, more preferably from 5 to 8, from the viewpoint of vapor deposition temperature.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R ¹ to R ⁸ is a group represented by —OZ, and Z is the substituted or unsubstituted carbon number of 1 to 50 of R ¹ to R ^8. Selected from the following alkyl groups:
From the viewpoint of vapor deposition temperature, 1 to 10 is preferable, and 1 to 6 is more preferable.

The substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms (the aryl moiety has 6 to 49 carbon atoms and the alkyl moiety has 1 to 44 carbon atoms) as the substituent of R ¹ to R ⁸ includes a 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, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthyl Isopropyl, 1-pyrrolylmethyl, 2- (1-pyrrolyl) ethyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-methyl Lorobenzyl 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-phenylisopropyl group and the like.
The carbon number is preferably from 7 to 20, and more preferably from 7 to 10, from the viewpoint of vapor deposition temperature.

Aryloxy and arylthio groups of R ¹ ~ substituted or unsubstituted aromatic ring group having 6 to 50 R ⁸ each is represented by -OY and -SY, Y represents a substituted or unsubstituted wherein R ¹ ~ R ⁸ Selected from aryl groups having 6 to 50 nuclear carbon atoms.
The number of nuclear carbons is preferably 6 to 20, more preferably 6 to 10, from the viewpoint of the deposition temperature.

A substituted or unsubstituted alkoxy group having 2 to 50 carbon atoms of R ¹ to R ⁸ (the alkyl moiety has 1 to 49 carbon atoms) is represented as —COOZ, and Z is a substituted or unsubstituted group of R ¹ to R ^8. Or an alkyl group having 1 to 49 carbon atoms.
The carbon number is preferably from 2 to 20, more preferably from 2 to 6, from the viewpoint of vapor deposition temperature.

Examples of the substituted silyl group of R ¹ to R ⁸ 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 include fluorine, chlorine, bromine and iodine.

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

In addition, other specific examples of the anthracene derivative represented by the formula (2) include derivatives represented by the following formula.

By using an organic light emitting medium containing the diaminopyrene derivative represented by the above formula (1) and the anthracene derivative represented by the above formula (2) for the organic thin film layer of the organic EL element, light emission at a short wavelength can be achieved. It can be obtained with high luminous efficiency, and the lifetime of the element can be extended.
This is because the α-naphthyl group is bonded to diaminopyrene, so that it becomes difficult to conjugate, and in addition to shortening the wavelength, an alkyl group or a cycloalkyl group is substituted on the pyrene mother nucleus, thereby It is presumed that it has a short wavelength and long life effect. This effect can be realized specifically only in combination with a host material having a specific structure taken up in the present application. If this specific combination is used, it is assumed that an organic thin film can be formed in which the host, the dopant, and the dopant maintain an appropriate distance.
Among them, the diaminopyrene derivative represented by the formula (1) is preferably combined with the anthracene derivative represented by the formula (2-4), the formula (2-5) and the formula (2-6-3).

The diaminopyrene derivative represented by the formula (1) can be synthesized, for example, by reacting dialkyldibromopyrene with a corresponding secondary amine compound in the presence of a metal catalyst. 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 diaminopyrene derivative formulas (1) and (2) represented by the formula (1) as described above coexist. 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 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. The organic light-emitting medium of the present invention has high light-emitting properties and has excellent hole-injecting properties, hole-transporting properties, electron-injecting properties, and electron-transporting properties. Can be used.

The organic light emitting medium contained in at least one layer (preferably the light emitting layer) of the organic thin film layer is preferably 0.1 to 20% by mass, and more preferably 1 to 10% by mass. In addition, the organic light-emitting medium of the present invention has extremely high fluorescence quantum efficiency, high hole transport ability and electron transport ability, and can form a uniform thin film. is there.
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, an excellent electron injection effect for the light emitting layer or light emitting material, and a hole injection layer of excitons generated in the light emitting layer 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 an electron transfer compound 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, which 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.

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 each independently represents 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 is a hydrogen atom, substituted or unsubstituted An 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 carbon group having 1 to 20 alkoxy groups, or these divalent groups. However, either one of Ar ¹ and Ar ^2, a substituted or unsubstituted fused ring group having a carbon number of 10 to 60, or a substituted or unsubstituted monohetero fused ring group having 5 to 60 ring atoms.
L ¹ , L ² and L 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. The nitrogen-containing heterocyclic derivative represented by this.

HAr-L-Ar ¹ -Ar ² (C)
(In the formula, HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent, and L is a single bond or a nuclear carbon atom having 6 to 60 which may have a substituent. arylene group, have a heteroarylene group, or a substituent ~ 60 5 good number ring atoms which may have a substituent is also optionally fluorenylene group, Ar ¹ is, have a substituent A divalent aromatic hydrocarbon group having 6 to 60 nuclear carbon atoms, and Ar ² may have an aryl group or substituent having 6 to 60 nuclear carbon atoms which may have a substituent. A nitrogen-containing heterocyclic derivative represented by the formula:

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, and R ₁ to R ₄ are each independently hydrogen, halogen atom, substituted or unsubstituted carbon number 1 To 6 alkyl groups, alkoxy groups, aryloxy groups, perfluoroalkyl groups, perfluoroalkoxy groups, amino groups, alkylcarbonyl groups, arylcarbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, azo groups, alkylcarbonyloxy Group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxy group Bonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heterocyclic, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, A silacyclopentadiene derivative represented by an isocyanate group, a thiocyanate group, an isothiocyanate group, a cyano group, or a substituted or unsubstituted ring condensed when adjacent.

(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, and X, Y and Z ₁ each independently represent a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, an alkoxy group or an aryloxy group. , 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. , N is 1, X, Y and R ₂ is a methyl group, and R ₈ is a hydrogen atom or a substituted boryl group, and n is 3 and Z ₁ is not a methyl group. Borane derivative.

[Wherein, Q ¹ and Q ² each independently represent a ligand represented by the following general formula (G), and L represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cyclohexane. An alkyl 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, substituted or unsubstituted An 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 ). Represents a quantifier. ]

[Wherein the 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 that form 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-tetrafluoro Substituted or unsubstituted alkoxy groups such as propoxy 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, pentafluorophenyl 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 Substitution of 3-group, 3-trifluoromethylphenylthio group, etc. Is an unsubstituted arylthio group, cyano group, nitro group, amino group, methylamino group, diethylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, diphenylamino group, or other mono- or disubstituted amino group , Acylamino groups such as bis (acetoxymethyl) amino group, bis (acetoxyethyl) amino group, bisacetoxypropyl) amino group, bis (acetoxybutyl) amino group, hydroxyl group, siloxy group, acyl group, methylcarbamoyl group, dimethylcarbamoyl group Group, ethylcarbamoyl group, diethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group, phenylcarbamoyl group, etc., carbamoyl group, carboxylic acid group, sulfonic acid group, imide group, cyclopentane group, cyclohexyl group, etc. Group, phenyl group, naphthyl group, biphenyl group, anthranyl group, phenanthryl group, fluorenyl group, pyrenyl group, aryl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, indolinyl group, quinolinyl group, acridinyl group , Pyrrolidinyl group, dioxanyl group, piperidinyl group, morpholidinyl group, piperazinyl group, triatinyl group, carbazolyl group, furanyl group, thiophenyl group, oxazolyl group, oxadiazolyl group, benzoxazolyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group And heterocyclic groups such as a triazolyl group, an imidazolyl group, a benzimidazolyl group, and a pranyl group. 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 the organic EL device of the present invention, in the light emitting layer, in addition to at least one aromatic amine derivative selected from the general formula (1), at least one of a light emitting material, a doping material, a hole injecting material, and an electron injecting material. The seed may be contained in the same layer. In order to improve the stability of the organic EL device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.

As the conductive material used for the anode of the organic EL device 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 Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins 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 be 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.

Synthesis Example 1 (Synthesis of Compound (DM-5-2))
In a 300 ml three-necked flask equipped with a condenser tube under an argon stream, 4.4 g (10 mmol) of 1,6-diisopropyl-3,8-dibromopyrene, 5.8 g (25 mmol) of Nm-tolyl-1-naphthylamine, acetic acid After adding 0.03 g (1.5 mol%) of palladium, 0.06 g (3 mol%) of tri-t-butylphosphine, 2.4 g (25 mmol) of sodium t-butoxide, and 100 ml of dry toluene, the mixture was added at 100 ° C. The mixture was stirred overnight. After completion of the reaction, the precipitated crystals were collected by filtration and washed with 50 ml of toluene and 100 ml of methanol to obtain 6.0 g of a pale yellow powder. This was confirmed to be m / e = 748 by FD-MS (field desorption mass spectrum) measurement and identified as compound (DM-5-2).

Synthesis Example 2 (Synthesis of Compound (DM-5-3))
Synthesis was performed in the same manner as in Synthesis Example 1 except that N-3,5-dimethylphenyl-1-naphthylamine was used instead of Nm-tolyl-1-naphthylamine. This was confirmed to be m / e = 776 by FD-MS measurement and identified as Compound (DM-5-3).

Synthesis Example 3 (Synthesis of Compound (DM-5-4))
Synthesis was performed in the same manner as in Synthesis Example 1 except that N-4-isopropylphenyl-1-naphthylamine was used instead of Nm-tolyl-1-naphthylamine. This was confirmed to be m / e = 804 by FD-MS measurement and identified as Compound (DM-5-4).

Synthesis Example 4 (Synthesis of Compound (DM-9-5))
Under a stream of argon, 5.2 g (10 mmol) of 1,6-dicyclohexyl-3,8-dibromopyrene and 6.8 g (25 mmol) of N-4-tert-butylphenyl-1-naphthylamine were placed in a 300 ml three-necked flask equipped with a cooling tube. ), 0.03 g (1.5 mol%) of palladium acetate, 0.06 g (3 mol%) of tri-t-butylphosphine, 2.4 g (25 mmol) of sodium t-butoxide, and 100 ml of dry toluene, and then 100 ° C. And stirred overnight. After completion of the reaction, the precipitated crystals were collected by filtration and washed with 50 ml of toluene and 100 ml of methanol to obtain 6.7 g of a pale yellow powder. This was confirmed to be m / e = 912 by FD-MS measurement and identified as Compound (DM-9-5).

Synthesis Example 5 (Synthesis of Compound (DM-9-6))
In Synthesis Example 4, synthesis was performed in the same manner using Np-tolyl-1-naphthylamine instead of N-4-t-butylphenyl-1-naphthylamine. This was confirmed to be m / e = 828 by FD-MS measurement and identified as Compound (DM-9-6).

Synthesis Example 6 (Synthesis of Compound (DM-10-8))
Synthesis was performed in the same manner as in Synthesis Example 4 except that N-4-cyclopentylphenyl-1-naphthylamine was used instead of N-4-t-butylphenyl-1-naphthylamine. This was confirmed to be m / e = 936 by FD-MS measurement and identified as Compound (DM-10-8).

Example 1
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the following compound A-1 is first formed to a thickness of 60 nm so as to cover the transparent electrode on the surface where the transparent electrode line is formed. It formed into a film so that it might become. Thereafter, the following compound A-2 was formed to a thickness of 20 nm on the film made of the compound A-1.

Further, the host material (anthracene derivative) EM1 and the dopant material (diaminopyrene derivative) DM5-2 of the present invention are formed on the film made of the compound A-2 by co-evaporation at a weight ratio of 40: 2. A light emitting medium was formed to form a blue light emitting layer having a thickness of 40 nm.

On the blue light emitting layer, an 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 film made of LiF, metal Al was deposited so as to have a thickness of 150 nm to form a metal cathode, and an organic EL light emitting device was produced.

(Examples 2 to 204)
In Example 1, organic EL devices were similarly fabricated using the materials shown in Tables 1 to 5 below instead of the host material EM1 and the dopant material DM5-2.

(Comparative Example 1)
In Example 1, an organic EL device was prepared in the same manner using EM74 instead of the host material EM1 and compound A having the following structure instead of the dopant material DM5-2.

(Comparative Example 2)
In Example 1, an organic EL device was produced in the same manner using Compound B having the following structure instead of the host material EM1 and Compound C having the following structure instead of the dopant material DM5-2.

Tables 1 to 5 below show the light emission wavelengths and the half lives at an initial luminance of 1000 cd / m ² of the organic EL elements of Examples and Comparative Examples.

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.

Claims (21)

1. 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), Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. R ²¹ and R ²² are each independently a group selected from a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms. Provided that at ^{least one} of Ar ¹ to Ar ⁴ is an α-naphthyl group, and R ²¹ and R ²² do not simultaneously become hydrogen atoms.)
   
   

   

   (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, and R ¹ to R ⁸ are each independently a hydrogen atom or a substituted group. Or an unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear 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 arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, Gen atom, a cyano group, a group selected from nitro group and a hydroxyl group.)
2. The organic light-emitting medium according to claim 1, wherein two of Ar ¹ to Ar ^{4 in} the formula (1) are α-naphthyl groups.
3. The organic light-emitting medium according to claim 3, wherein Ar ¹ and Ar ³ in the formula (1) are α-naphthyl groups.
4. R ²¹ and R ²² in the formula (1) are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 nuclear carbon atoms. Item 2. The organic light emitting medium according to Item 1.
5. The organic light-emitting medium according to claim 1 or 4, wherein R ²¹ and R ²² in the formula (1) are the same group.
6. The organic light-emitting medium according to claim 1, 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.
7. The organic light-emitting medium according to claim 6, wherein Ar ¹¹ and Ar ¹² in the formula (2) are the same group.
8. The organic light-emitting medium according to claim 7, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 9-phenanthrenyl groups.
9. The organic light-emitting medium according to claim 7, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted β-naphthyl groups.
10. The organic light-emitting medium according to claim 7, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted α-naphthyl groups.
11. The organic light-emitting medium according to claim 6, wherein Ar ¹¹ and Ar ¹² in the formula (2) are different groups.
12. Ar ¹¹ and Ar ¹² in the formula (2) are any one of a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted α-naphthyl group, and a substituted or unsubstituted β-naphthyl group. 11. The organic luminescent medium according to 11.
13. 2. The organic according to claim 1, wherein 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 20 nuclear carbon atoms. Luminescent medium.
14. 14. The organic light-emitting medium according to claim 13, wherein the substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms is a substituted or unsubstituted α-naphthyl group.
15. 14. The organic light-emitting medium according to claim 13, wherein the substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms is a substituted or unsubstituted β-naphthyl group.
16. 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 formula (2-6), R ¹ to R ⁸ are the same as those in formula (2). Ar ⁵ and Ar ⁶ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, substituted Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted nucleus. (It is a heterocyclic group having 5 to 50 atoms.)
17. The organic light-emitting medium according to claim 16, wherein Ar ⁵ and Ar ⁶ in the formula (2-6) are substituted or unsubstituted phenyl groups.
18. 17. 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 as described.
19. The organic light-emitting medium according to claim 16, wherein Ar ⁵ and Ar ⁶ in the formula (2-6) are substituted or unsubstituted condensed aryl groups having 10 to 20 nuclear carbon atoms.
20. One or more organic thin film layers including a light emitting layer are provided between the cathode and the anode, and at least one of the organic thin film layers contains the organic light emitting medium according to any one of claims 1 to 19. Organic electroluminescence device.
21. The organic electroluminescent device according to claim 20, wherein the light emitting layer contains the organic light emitting medium.