JP2000208262A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element with high brightness. SOLUTION: As a component material for an organic electroluminescent element, a specific pyrromethene metallic complex compound represented in a formula is used. In the formula, M represents an n valence metal ion; n is any one of 1, 2 and 3. R1 to R7 respectively independently express a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or non-substituted amino group, a nitro group, a cyano group, a substituted or non-substituted alkyl group, a substituted or non-substituted alkenyl group, a substituted or non- substituted cycloalkyl group, a substituted or non-substituted alkoxy group, a substituted or non-substituted aromatic hydrocarbon group, a substituted or non-substituted aromatic heterocyclic group, a substituted or non-substituted aralkyl group, a substituted or non-substituted aryloxy group, a substituted or non-substituted alkoxycarbonyl group, and a carboxyl group. R1 to R7 may form a ring with two thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device having excellent light emission characteristics.

[0002]

2. Description of the Related Art Organic electroluminescence (EL)
The element is a self-luminous element utilizing the principle that a fluorescent substance emits light by the recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied.

[0003] Eastman Kodak C.I. W. Ta
ng et al. report on a low-voltage driven organic EL device using a stacked device (CW Tang, SA VanSlyk).
e, Applied Physics Letters (Applied
Physics Letters), 51, 913
P. 1987), research on organic EL elements using organic materials as constituent materials has been actively conducted.

Tang et al. Use tris (8-hydroxyquinolinol aluminum) for a light emitting layer and a triphenyldiamine derivative for a hole transport layer. The advantages of the stacked structure include that the efficiency of injecting holes into the light emitting layer is increased,
Examples include increasing the efficiency of generating excitons generated by recombination by blocking electrons injected from the cathode, and confining excitons generated in the light emitting layer.

[0005] As in this example, the element structure of the organic EL element has a two-layer structure of a hole transporting (injecting) layer and an electron transporting light emitting layer, or a hole transporting (injecting) layer, a light emitting layer, and an electron transporting (electron transporting) layer. Injection) layers are well known.

[0006] In order to increase the recombination efficiency of injected holes and electrons in such a stacked structure element, the element structure and the forming method are devised.

As the hole transporting material, 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine or N, N'-diphenyl-N, N'-bis ( 3-methylphenyl)-
Triphenylamine derivatives such as [1,1'-biphenyl] -4,4'-diamine and aromatic diamine derivatives are well known (for example, JP-A-8-20771,
JP-A-8-40995, JP-A-8-40997, JP-A-8-54397, JP-A-8-
87122).

[0008] Oxadiazole derivatives, triazole derivatives and the like are well known as electron transporting materials.

Further, as light emitting materials, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. Is also reported to emit light in the visible region from blue to red, and the realization of a color display element is expected (for example,
JP-A-8-239655, JP-A-7-13856
No. 1, JP-A-3-200289, etc.).

Further, Japanese Patent Application Laid-Open No. 9-289081 discloses that
Pyrromethene -BF ₂ complexes are disclosed as a luminescent material.

[0011]

Recently, an organic EL device having a high luminance and a long life has been disclosed or reported, but it is not necessarily sufficient. Therefore, there is a strong demand for the development of materials exhibiting high performance. The purpose of the present invention is
An object of the present invention is to provide a high-luminance organic EL element.

[0012]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that an organic E prepared by using a specific pyromethene metal complex compound as a light emitting material.
It has been found that the L element emits light with higher luminance than before.

Further, it is found that the material has a high carrier transporting property, and an organic EL device manufactured by using the material as a hole transporting material or an electron transporting material; and the above material and another hole transporting material or an electron transporting material. It has been found that an organic EL device produced by using a mixed thin film of the present invention emits light with higher luminance than the conventional one, and has led to the present invention.

That is, the present invention relates to an organic electroluminescent device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula [Chemical Formula 2] ]:

Embedded image (Wherein, M represents an n-valent metal ion; n is 1, 2, 3)
One of R ^{1 to} R ⁷ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group, Unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted Represents an aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. Further, R ^{1 to} R ⁷ may form a ring with two of them. An organic electroluminescent device comprising the pyromethene metal complex compound represented by the formula (1) alone or in a mixture.

Further, the present invention provides an organic electroluminescence device having at least a light emitting layer as the organic thin film layer, wherein the light emitting layer contains the compound represented by the general formula [2] alone or as a mixture. It is.

Further, the present invention has at least a hole transport layer as the organic thin film layer, and the light emitting layer has a general formula [Chemical Formula 2]
An organic electroluminescent device comprising the compound represented by the formula (1) alone or as a mixture.

Further, the present invention has at least an electron transport layer as the organic thin film layer, and the light emitting layer has a general formula [Chemical Formula 2]
An organic electroluminescent device comprising the compound represented by the formula (1) alone or as a mixture.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The compound according to the present invention is a compound having a structure represented by the general formula [Formula 2]. (Wherein, M is .n representing an n-valent metal ions consisting of either 1, 2, 3 ^.R 1 ~
R ⁷ is each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group,
Cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted It represents a substituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, and a carboxyl group. Further, R ^{1 to} R ⁷ may form a ring with two of them. )

Examples of the metal which can be used for M representing an n-valent metal ion include aluminum, beryllium, bismuth, cadmium, cerium, cobalt, copper, iron, gallium, germanium, mercury, indium, lanthanum, magnesium, molybdenum, Niobium, antimony, scandium, tin, tantalum, thorium, titanium, uranium, tungsten, zirconium, vanadium, zinc,
Examples include, but are not limited to, silver, gold, platinum, chromium, manganese, yttrium, nickel, palladium, lead, selenium, tellurium, thallium, calcium, strontium, barium, neodymium, europium, and erbium.

R ^{1 to} R ⁷ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group. A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, Represents an unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. Further, R ^{1 to} R ⁷ may form a ring with two of them.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

The substituted or unsubstituted amino group is --NX ¹
X ² , X ¹ and X ² are each independently
Hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, 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 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-bromo Isobutyl 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-trinitro Propyl group, phenyl group,
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, 4-styrylphenyl 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, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, 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′-methylbiphenylyl group,
A 4 ''-t-butyl-p-terphenyl-4-yl group,
2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-
Pyridinyl group, 3-pyridinyl group, 4-pyridinyl group,
2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-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 -Isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-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-quinoxa Group, 1-carbazolyl group,
2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phen Nanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-
Acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,
7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthroline-4
-Yl group, 1,7-phenanthrolin-5-yl group,
1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group Group, 1,8-phenanthrolin-2-yl group, 1,8-
Phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1, 8
Phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10
-Yl group, 1,9-phenanthrolin-2-yl group,
1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group Group, 1,9-phenanthrolin-7-yl group, 1,9-
Phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2
-Yl group, 1,10-phenanthrolin-3-yl group,
1,10-phenanthrolin-4-yl group, 1,10-
Phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2, 9
-Phenanthroline-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthroline-7-
Yl group, 2,9-phenanthroline-8-yl group, 2,
9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthroline-
3-yl group, 2,8-phenanthrolin-4-yl group,
2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group Group, 2,8-phenanthrolin-10-yl group, 2,7
-Phenanthroline-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthroline-4-
Yl group, 2,7-phenanthrolin-5-yl group, 2,
7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthroline-9
An -yl group, a 2,7-phenanthroline-10-yl group,
1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4 -Phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole-1 -Yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrole-2 -Yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-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, 2-t-butyl 3-indolyl group, 4-t- And a butyl 3-indolyl group.

Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group and a t-butyl group.
Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxy Ethyl 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-trinitro And a propyl group.

Examples of the substituted or unsubstituted alkenyl group include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, and
-Methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2- Phenylallyl group, 3
-Phenylallyl group, 3,3-diphenylallyl group,
Examples thereof include a 1,2-dimethylallyl group, a 1-phenyl-1-butenyl group, and a 3-phenyl-1-butenyl group.

Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a 4-methylcyclohexyl group. The substituted or unsubstituted alkoxy group is a group represented by -OY, wherein Y is a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a 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, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 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, 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
T-butyl iodide, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 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 aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl and 1-phenanthryl. , 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-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.

The substituted or unsubstituted aromatic heterocyclic group includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 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-isobenzofuranyl group, 3-
Isobenzofuranyl group, 4-isobenzofuranyl group, 5
-Isobenzofuranyl group, 6-isobenzofuranyl group,
7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3- Isoquinolyl group, 4-isoquinolyl group, 5
-Isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group,
5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group , 3-
Phenanthridinyl group, 4-phenanthridinyl group, 6
-Phenanthridinyl group, 7-phenanthridinyl group,
8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1 , 7-phenanthroline-2-yl group, 1,7-phenanthroline-3
-Yl group, 1,7-phenanthrolin-4-yl group,
1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group Group, 1,7-phenanthrolin-10-yl group, 1,8
-Phenanthroline-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthroline-4-
Yl group, 1,8-phenanthrolin-5-yl group, 1,
8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthroline-9
-Yl group, 1,8-phenanthrolin-10-yl group,
1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl Group, 1,9-phenanthrolin-6-yl group, 1,9-
Phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10-
An yl group, a 1,10-phenanthrolin-2-yl group,
1,10-phenanthrolin-3-yl group, 1,10-
Phenanthroline-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthroline-1-
Yl group, 2,9-phenanthrolin-3-yl group, 2,
9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthroline-6
-Yl group, 2,9-phenanthrolin-7-yl group,
2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl Group, 2,8-phenanthrolin-4-yl group, 2,8-
Phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2, 8
-Phenanthroline-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthroline-3
-Yl group, 2,7-phenanthrolin-4-yl group,
2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group Group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, -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-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole- 3-yl group, 2-methylpyrrole-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-butylpyrrole-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, 2-t-butyl 3-indolyl group,
4-t-butyl 3-indolyl group, and the like.

The substituted or unsubstituted aralkyl group includes benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthyl Methyl 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-bromo Benzyl 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,
Examples thereof include an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group, and the like.

A substituted or unsubstituted aryloxy group is represented by —OZ, where Z is a phenyl group, 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-
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′-methylbiphenylyl group, 4 ″ -t- Butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4
-Pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-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-isobenzofuranyl group, 3-
Isobenzofuranyl group, 4-isobenzofuranyl group, 5
-Isobenzofuranyl group, 6-isobenzofuranyl group,
7-isobenzofuranyl group, 2-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, 1-phenanthridinyl group,
2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9- Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthroline-2-yl Group, 1,7-phenanthrolin-3-yl group, 1,7-
Phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthroline-8-yl group, 1, 7
-Phenanthroline-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthroline-2
-Yl group, 1,8-phenanthrolin-3-yl group,
1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group Group, 1,8-phenanthrolin-9-yl group, 1,8-
Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-
Yl group, 1,9-phenanthrolin-4-yl group, 1,
9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthroline-7
-Yl group, 1,9-phenanthroline-8-yl group,
1,9-phenanthrolin-10-yl group, 1,10-
Phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthroline-4
-Yl group, 1,10-phenanthrolin-5-yl group,
2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group Group, 2,9-phenanthrolin-6-yl group, 2,9-
Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-
Yl group, 2,8-phenanthrolin-1-yl group, 2,
8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthroline-5
-Yl group, 2,8-phenanthrolin-6-yl group,
2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl Group, 2,7-phenanthrolin-3-yl group, 2,7-
Phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-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, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-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-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl
Yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl 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, 2-t-butyl 3-indolyl group , 4-t-butyl 3-indolyl group and the like.

A substituted or unsubstituted alkoxycarbonyl group is represented by —COOY, wherein Y represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group,
s-butyl group, 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 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-dinitro Isopropyl group, 2,
Examples include a 3-dinitro t-butyl group and a 1,2,3-trinitropropyl group.

Examples of the divalent group forming a ring include:
Tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethane-2,2'-diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-
4,4'-diyl group, 1,3-butadiene-1,4-diyl group and the like.

Examples of the compounds according to the present invention are shown by the following chemical formulas from [formula 3] to [formula 10].
The present invention is not limited to these.

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The element structure of the organic EL element in the present invention is a structure in which one or more organic layers are laminated between electrodes, and examples thereof are shown in FIGS.

The device structure shown in FIG. 1 comprises an anode 2, a light emitting layer 4 and a cathode 6 provided on a substrate 1.

The device structure shown in FIG. 2 comprises an anode 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode 6 provided on a substrate 1.

The element structure shown in FIG. 3 comprises an anode 2, a hole transport layer 3, a light emitting layer 4 and a cathode 6 provided on a substrate 1.

The device structure shown in FIG. 4 comprises an anode 2, a light emitting layer 4, an electron transport layer 5, and a cathode 6 provided on a substrate 1. Here, the hole transport layer 3, the light emitting layer 4, and the electron transport layer 5
Corresponds to the organic layer.

The compound in the present invention may be used in any of the above organic layers, and can be doped into other hole transporting materials, luminescent materials and electron transporting materials.

The hole transporting material used in the present invention is not particularly limited, and any compound which is usually used as a hole transporting agent may be used. For example, the following bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane [formula 11], N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′- Biphenyl-
Tris such as 4,4'-diamine [formula 12] and N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4'-diamine [formula 13] Phenyldiamines and starburst-type molecules ([Chemical Formula 14] ~
[Formula 16]) and the like.

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The electron transporting material used in the present invention is not particularly limited, and any compound which is usually used as an electron transporting material may be used. For example, as shown below,
-(4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole [formula 17], bis {2- (4-t-butylphenyl) -1,3,4 Oxadiazole derivatives such as -oxadiazole} -m-phenylene [Chemical Formula 18];
9] and [Formula 20], and quinolinol-based metal complexes (such as [Formula 21] to [Formula 24]).

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The anode 2 of the organic thin film EL element has a role of injecting holes into the hole transport layer 3 or the light emitting layer 4, and it is effective that the anode 2 has a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention,
Indium tin oxide alloy (ITO), tin oxide (NES)
A), gold, silver, platinum, copper and the like can be applied.

The cathode 6 is preferably made of a material having a small work function in order to inject electrons into the electron transport layer 5 or the light emitting layer 4. The cathode material is not particularly limited, but specifically, indium, aluminum, magnesium, a magnesium-indium alloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, an aluminum-scandium-lithium alloy, a magnesium-silver alloy, or the like can be used.

The method for forming each layer of the organic EL device of the present invention is not particularly limited. A conventionally known formation method such as a vacuum evaporation method and a spin coating method can be used. The organic thin film layer containing the compound represented by the general formula [Chemical Formula 2] used in the organic EL device of the present invention may be formed by vacuum evaporation, molecular beam evaporation (MBE), dipping of a solution dissolved in a solvent, spinning, or the like. It can be formed by a known method such as a coating method, a casting method, a bar coating method, and a roll coating method.

The thickness of each organic layer of the organic EL device of the present invention is not particularly limited. In general, if the thickness is too small, defects such as pinholes are likely to occur. In general, the thickness is preferably in the range of several nm to 1 μm.

Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist of the present invention.

(Synthesis Example 1) Synthesis of 5-phenyl-4,6-dipyrine. Trifluoroacetic acid was added to a toluene solution of benzoaldehyde and pyrrole, and the mixture was refluxed for 3 hours. The obtained reaction solution was washed with an aqueous sodium carbonate solution and then dried. This was purified according to a conventional method to obtain 5-phenyldipyrromethane. The thus obtained dipyrromethane was made into a chloroform solution, 2,3-dichloro-5,6-dicyano-1,4-quinone was added, and the mixture was stirred at room temperature. After concentrating the reaction solution, it was purified by column chromatography to obtain the desired 5-phenyl-4,6-dipyrine.

(Synthesis Example 2) 5-p-cyanophenyl-
Synthesis of 4,6-dipyrine. Except for using 4-cyanobenzaldehyde instead of benzaldehyde, the same procedure as in Synthesis Example 1 was performed to obtain the desired 5-p-cyanophenyl-4,6-dipyrine.

Synthesis Example 3 Synthesis of 2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrine Except that 3,4-dimethylpyrrole is used in place of pyrrole, the objective 2, 3, 7,
8-Tetramethyl-5-phenyl-4,6-dipyrine was obtained.

Synthesis Example 4 Synthesis of 2,3,7,8-tetramethyl-5-p-cyanophenyl-4,6-dipyrine Except that 3,4-dimethylpyrrole was used instead of pyrrole, the objective 2, 3, 7,
8-tetramethyl-5-p-cyanophenyl-4,6-
Dipyrine was obtained.

(Synthesis Example 5) Synthesis of compound (tri (5-phenyl-4,6-dipyrine) aluminum complex) represented by chemical formula [Formula 3]. Aluminum chloride was added to a toluene solution of 5-phenyl-4,6-dipyrine, and the mixture was refluxed for 8 hours. After concentrating the reaction solution, the reaction solution was purified by column chromatography using silica gel to obtain the desired compound represented by the chemical formula [Chemical Formula 3].

(Synthesis Example 6) Synthesis of a compound (tri (5-p-cyanophenyl-4,6-dipyrine) aluminum complex) represented by the chemical formula [Formula 4]. Instead of 5-phenyl-4,6-dipyrine, 5-p-
Except that cyanophenyl-4,6-dipyrine was used, the same method as in Synthesis Example 5 was carried out to obtain the desired compound represented by the chemical formula [Formula 4].

(Synthesis Example 7) Synthesis of a compound (tri (2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrine) aluminum complex) represented by the chemical formula [Formula 5]. Instead of 5-phenyl-4,6-dipyrine, 2,3,
Except for using 7,8-tetramethyl-5-phenyl-4,6-dipyrine, the same procedure as in Synthesis Example 5 was carried out to obtain the desired compound represented by the chemical formula [Formula 5].

(Synthesis Example 8) A compound represented by the chemical formula [Formula 6] (tri (2,3,7,8-tetramethyl-5-p-
Synthesis of cyanophenyl-4,6-dipyrine) aluminum complex). Instead of 5-phenyl-4,6-dipyrine, 2,3,
7,8-tetramethyl-5-p-cyanophenyl-4,
Except for using 6-dipyrine, the same procedure as in Synthesis Example 5 was performed to obtain the desired compound represented by the chemical formula [Chemical Formula 6].

(Synthesis Example 9) Synthesis of a compound (di (5-phenyl-4,6-dipyrine) zinc complex) represented by the chemical formula [Formula 7]. Zinc acetate was added to a methanol solution of 5-phenyl-4,6-dipyrine and refluxed for 4 hours. After concentrating the reaction solution, the reaction solution was purified by column chromatography using silica gel to obtain the desired compound represented by the chemical formula [Chemical Formula 7].

(Synthesis Example 10) Synthesis of a compound (di (5-p-cyanophenyl-4,6-dipyrine) zinc complex) represented by the chemical formula [Formula 8]. Instead of 5-phenyl-4,6-dipyrine, 5-p-
Except for using cyanophenyl-4,6-dipyrine, the same procedure as in Synthesis example 9 was performed to obtain the desired compound represented by the chemical formula [Formula 8].

(Synthesis Example 11) Synthesis of a compound (di (2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrine) zinc complex) represented by the chemical formula [Formula 9]. Instead of 5-phenyl-4,6-dipyrine, 2,3,
Except for using 7,8-tetramethyl-5-phenyl-4,6-dipyrine, a compound represented by the target chemical formula [Formula 9] was obtained in the same manner as in Synthesis Example 9.

(Synthesis Example 12) A compound represented by the chemical formula [Formula 10] (di (2,3,7,8-tetramethyl-5-p
-Cyanophenyl-4,6-dipyrine) zinc complex). Instead of 5-phenyl-4,6-dipyrine, 2,3,
7,8-tetramethyl-5-p-cyanophenyl-4,
Except for using 6-dipyrine, a compound represented by the target chemical formula [Formula 10] was obtained in the same manner as in Synthesis Example 5.

Hereinafter, Examples using the compound of the present invention as a light-emitting layer are shown in Examples 1 to 25 and Examples 31 to 34. In Example 26, a mixed thin film of the compound of the present invention and a hole transport material was used as a light emitting layer.
To Example 30. Examples using the mixed thin film of the compound of the present invention and the electron transporting material as the light-emitting layer are described in Examples 35 to 39 below, and Examples using the compound of the present invention as the hole transporting layer are described below. Example 4 described below
Examples 0 to 41 show examples using the electron transport layer in Examples 42 to 43 described below.

Example 1 FIG. 1 shows a cross-sectional structure of an element used in Example 1. Hereinafter, a procedure for manufacturing the organic thin film EL device used in Example 1 of the present invention will be described. The device is composed of an anode 2 / a light emitting layer 4 / a cathode 6 formed on a substrate 1. An ITO was formed on a glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / □. A compound represented by the chemical formula [Formula 3] is formed on the anode 2 as a light emitting layer 4 by 40 n by a vacuum evaporation method.
m. Next, a 200 nm-thick magnesium-silver alloy was formed as a cathode 6 on the light-emitting layer 4 by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to this device, light emission of 400 cd / m ² was obtained.

Example 2 An organic EL device was manufactured in the same manner as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 4] was used as a light emitting material. When a DC voltage of 5 V was applied to this device, light emission of 370 cd / m ² was obtained.

Example 3 An organic EL device was manufactured in the same manner as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 5] was used as a light emitting material. When a DC voltage of 5 V was applied to this device, light emission of 650 cd / m ² was obtained.

Example 4 An organic EL device was manufactured in the same manner as in Example 1 except that the compound represented by the chemical formula [Chemical Formula 6] was used as a light emitting material. When a DC voltage of 5 V was applied to this device, light emission of 540 cd / m ² was obtained.

Example 5 An organic EL device was manufactured in the same manner as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 7] was used as a light emitting material. When a DC voltage of 5 V was applied to this element, light emission of 350 cd / m ² was obtained.

Example 6 An organic EL device was manufactured in the same manner as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 8] was used as a light emitting material. When a DC voltage of 5 V was applied to this device, light emission of 300 cd / m ² was obtained.

Example 7 An organic EL device was manufactured in the same manner as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 9] was used as a light emitting material. When a DC voltage of 5 V was applied to this device, light emission of 380 cd / m ² was obtained.

Example 8 An organic EL device was manufactured in the same manner as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 10] was used as a light emitting material. When a DC voltage of 5 V was applied to this device, light emission of 310 cd / m ² was obtained.

(Example 9) The cross-sectional structure of the device used in Example 9 is composed of an anode 2 / a light emitting layer 4 / a cathode 6 formed on a substrate 1, as shown in FIG. Hereinafter, the procedure for manufacturing the organic thin film EL device used in Example 9 of the present invention will be described. An ITO was formed on a glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / □. The light emitting layer 4 having a layer thickness of 40 nm was formed thereon by a spin coating method using a chloroform solution of the compound represented by the chemical formula [7]. Next, a magnesium-silver alloy was formed as the cathode 6 to a thickness of 200 nm on the light-emitting layer 4 by a vacuum evaporation method to produce an organic EL device. A DC voltage of 5 V is applied to this element.
Upon application, light emission of 120 cd / m ² was obtained.

Example 10 An organic EL device was manufactured in the same manner as in Example 9 except that the compound represented by the chemical formula [Chemical Formula 9] was used instead of the compound represented by the chemical formula [Chemical Formula 7]. When a DC voltage of 5 V was applied to this element, 130
Light emission of cd / m ² was obtained.

(Embodiment 11) FIG. 2 shows a sectional structure of an element used in Embodiment 11. The device is composed of an anode 2 / a hole transport layer 3 / a light emitting layer 4 / an electron transport layer 5 / a cathode 6 formed on a substrate 1.
It consists of. Example 1 of the present invention is described below.
The procedure for manufacturing the organic thin-film EL element used in No. 1 will be described. An ITO was formed on a glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / □. As a hole transport layer 3 on the anode 2, N, N′-diphenyl-N, N′-bis (3-methylphenyl)-[1,1′-biphenyl] represented by the chemical formula [Formula 3]
-4,4'-Diamine was formed to a thickness of 50 nm by a vacuum evaporation method. Next, as a light emitting layer 4 on the hole transport layer 3,
The compound represented by the chemical formula [Chemical Formula 3] is subjected to vacuum evaporation by 40
It was formed to a thickness of nm. Next, on the light emitting layer 4, as the electron transport layer 5, 2- (4-
Biphenylyl) -5- (4-t-butylphenyl)-
1,3,4-oxadiazole by vacuum evaporation 20n
m. Next, the cathode 6 is placed on the electron transport layer 5.
A magnesium-silver alloy is formed by vacuum evaporation.
An organic EL device was manufactured by forming the layer to a thickness of 00 nm. When a DC voltage of 10 V was applied to this element, 2370 c
Light emission of d / m ² was obtained.

Example 12 An organic EL device was manufactured in the same manner as in Example 11, except that a compound represented by the chemical formula [4] was used as a light emitting material. When a DC voltage of 10 V was applied to this element, 1860 cd / m ²
Was obtained.

Example 13 An organic EL device was manufactured in the same manner as in Example 11, except that a compound represented by the chemical formula [Chemical Formula 5] was used as a light emitting material. When a DC voltage of 10 V was applied to this element, 2510 cd / m ²
Was obtained.

Example 14 An organic EL device was manufactured in the same manner as in Example 11, except that a compound represented by the chemical formula [Chemical Formula 6] was used as a light emitting material. When a DC voltage of 10 V was applied to this element, 1970 cd / m ²
Was obtained.

Example 15 An organic EL device was manufactured in the same manner as in Example 11, except that the compound represented by the chemical formula [Chemical Formula 7] was used as the light emitting material. When a DC voltage of 10 V was applied to this element, 1260 cd / m ²
Was obtained.

(Example 16) An organic EL device was manufactured in the same manner as in Example 11, except that a compound represented by the chemical formula [Chemical Formula 8] was used as a light emitting material. When a DC voltage of 10 V was applied to this element, 1070 cd / m ²
Was obtained.

Example 17 An organic EL device was manufactured in the same manner as in Example 11, except that a compound represented by the chemical formula [Chemical Formula 9] was used as a light emitting material. When a DC voltage of 10 V was applied to this element, 1380 cd / m ²
Was obtained.

Example 18 Example 11 was repeated except that the compound represented by the chemical formula [Chemical Formula 10] was used as the light emitting material.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 1110 cd / m
² luminescence was obtained.

(Example 19) As the hole transport layer 3, N, N'-diphenyl-N- represented by the chemical formula [Formula 13] was used.
N-bis (1-naphthyl) -1,1'-biphenyl)-
4,4′-Diamine is used as the electron transporting layer 5 to form the compound bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-
An organic EL device was manufactured in the same manner as in Example 11 except that phenylene was used. Apply a DC voltage of 10 to this element.
When V was applied, light emission of 2240 cd / m ² was obtained.

Example 20 The compound represented by the chemical formula [Formula 14] was used as the hole transport layer 3, the compound represented by the chemical formula [Formula 4] was used as the light emitting layer 4, and the electron transport layer 5 was used as the electron transport layer 5. An organic EL device was manufactured in the same manner as in Example 11, except that the compound represented by the chemical formula [Chemical Formula 21] was used. When a DC voltage of 10 V was applied to this element, 16
Emission of 80 cd / m ² was obtained.

Example 21 The compound represented by the chemical formula [Formula 15] was used as the hole transport layer 3, the compound represented by the chemical formula [Formula 5] was used as the light emitting layer 4, and the electron transport layer 5 was used as the electron transport layer 5.
An organic EL device was manufactured in the same manner as in Example 11, except that the compound represented by the chemical formula [Chemical Formula 22] was used. When a DC voltage of 10 V was applied to this element, 25
Light emission of ²⁰ cd / m ² was obtained.

Example 22 FIG. 4 shows a cross-sectional structure of the device used in Example 22. The device is composed of an anode 2 / a light emitting layer 4 / an electron transport layer 5 / a cathode 6 formed on a substrate 1. Hereinafter, the organic thin film E used in Example 22 of the present invention will be described.
The procedure for manufacturing the L element will be described. Sheet resistance is 20Ω / by sputtering ITO on the glass substrate 1.
A film was formed so as to be □, and the anode 2 was obtained. On the anode 2, a compound represented by the chemical formula [Formula 3] was formed as a light emitting layer 4 to a thickness of 40 nm by a vacuum evaporation method. Next, on the light emitting layer 4, as an electron transporting layer 5, a chemical formula [Chemical Formula 19]
Was formed to a thickness of 50 nm by a vacuum evaporation method. Next, a magnesium-silver alloy was formed on the electron transport layer 5 as the cathode 6 to a thickness of 200 nm to produce an EL element. When a DC voltage of 10 V was applied to this device, light emission of 1090 cd / m ² was obtained.

Example 23 The light emitting layer 4 had the chemical formula [Chemical Formula 3]
An organic EL device was produced in the same manner as in Example 22, except that the compound represented by Chemical Formula 4 was used instead of the compound represented by Chemical Formula 4. DC voltage is applied to this element by 1
When 0 V was applied, light emission of 960 cd / m ² was obtained.

(Example 24) The light emitting layer 4 had the chemical formula [Formula 3]
In the same manner as in Example 22, except that a compound represented by the chemical formula [Chemical Formula 5] was used instead of the compound represented by the formula, an organic EL device was produced. When a DC voltage of 10 V was applied to this element, the voltage was 1220 cd / m ^2.
Was obtained.

(Example 25) The light emitting layer 4 had the chemical formula [Chemical Formula 3]
An organic EL device was manufactured in the same manner as in Example 22, except that the compound represented by Chemical Formula 6 was used instead of the compound represented by Chemical Formula 6. DC voltage is applied to this element by 1
When 0 V was applied, light emission of 1020 cd / m ² was obtained.

(Example 26) As the light emitting layer 4, N, N'-diphenyl-NN represented by the chemical formula [Formula 13] was used.
-Bis (1-naphthyl) -1,1'-biphenyl)-
A thin film produced by co-evaporation of 4,4′-diamine and a compound represented by the chemical formula [Chemical Formula 3] at a weight ratio of 1:10 was prepared.
An organic EL device was manufactured in the same manner as in Example 22, except that the organic EL device was formed to a thickness of nm. When a DC voltage of 10 V was applied to this device, light emission of 1290 cd / m ² was obtained.

(Example 27) The light emitting layer 4 had the chemical formula [Chemical Formula 3]
An organic EL device was produced in the same manner as in Example 26, except that the compound represented by Chemical Formula 4 was used instead of the compound represented by Chemical Formula 4. Apply a DC voltage of 10 to this element.
When V was applied, light emission of 1060 cd / m ² was obtained.

(Example 28) The light emitting layer 4 had the chemical formula [Chemical Formula 3]
An organic EL device was produced in the same manner as in Example 26, except that the compound represented by Chemical Formula 5 was used instead of the compound represented by Chemical Formula 5. Apply a DC voltage of 10 to this element.
When V was applied, light emission of 1450 cd / m ² was obtained.

(Example 29) The light emitting layer 4 had the chemical formula [Formula 3]
An organic EL device was produced in the same manner as in Example 26, except that the compound represented by Chemical Formula 6 was used instead of the compound represented by Chemical Formula 6. Apply a DC voltage of 10 to this element.
When V was applied, light emission of 1170 cd / m ² was obtained.

(Embodiment 30) FIG. 4 shows a sectional structure of an element used in Embodiment 30. The device is composed of an anode 2 / a light emitting layer 4 / an electron transport layer 5 / a cathode 6 formed on a substrate 1. Hereinafter, the organic thin film E used in Example 30 of the present invention will be described.
The procedure for manufacturing the L element will be described. Sheet resistance is 20Ω / by sputtering ITO on the glass substrate 1.
A film was formed so as to be □, and the anode 2 was obtained. On the anode 2, a compound represented by the chemical formula [Chemical Formula 6] and a chemical formula [Chemical Formula 13]
N, N'-diphenyl-NN-bis (1
-Naphthyl) -1,1'-biphenyl) -4,4'-diamine was formed into a 40-nm-thick light-emitting layer 4 by a spin coating method using a chloroform solution containing a molar ratio of 1:10. . Next, an electron transport layer 5 having a thickness of 50 nm is formed on the light emitting layer 4 by a vacuum deposition method using a compound represented by the chemical formula [Formula 11], and magnesium-silver as a cathode 6 is formed on the electron transport layer 5. The alloy is vacuum-deposited 2
An organic EL device was manufactured by forming the layer to a thickness of 00 nm. When a DC voltage of 10 V was applied to this element, 730 cd
/ M ² was obtained.

(Example 31) The device used in Example 31
FIG. 3 shows the cross-sectional structure. The device is formed on the substrate 1
It is composed of electrode 2 / hole transport layer 3 / light emitting layer 4 / cathode 6.
ing. The organic thin film E used in Example 31 of the present invention will be described below.
The procedure for manufacturing the L element will be described. On the glass substrate 1
Sheet resistance is 20Ω / by sputtering ITO.
A film was formed so as to be □, and the anode 2 was obtained. On the anode 2
As the hole transport layer 3, represented by the chemical formula [Formula 13]
N, N} -diphenyl-NN-bis (1-naphthyl)
-1,1'-biphenyl) -4,4'-diamine.
A film having a thickness of 50 nm was formed by a vacuum evaporation method. Next
Next, on the hole transport layer 3, as the light emitting layer 4,
3] is a film obtained by vacuum-depositing the compound represented by formula
Formed. Next, on the light emitting layer 4,
Forming a layer of a shim-silver alloy to a thickness of 200 nm and EL
An element was manufactured. A DC voltage of 10 V was applied to this element.
However, 1820 cd / m ²Was obtained.

(Example 32) As the light emitting layer 4, instead of the compound represented by the chemical formula [Chemical Formula 3], a chemical formula [Chemical Formula 4] was used.
An organic EL device was produced in the same manner as in Example 31, except that the compound represented by the following formula was used. When a DC voltage of 10 V was applied to this device, light emission of 1560 cd / m ² was obtained.

(Example 33) As the light-emitting layer 4, instead of the compound represented by the chemical formula [Chemical Formula 3], a chemical formula [Chemical Formula 5] was used.
An organic EL device was produced in the same manner as in Example 31, except that the compound represented by the following formula was used. When a DC voltage of 10 V was applied to this device, light emission of 2020 cd / m ² was obtained.

(Example 34) As the light emitting layer 4, instead of the compound represented by the chemical formula [Chemical Formula 3], a chemical formula [Chemical Formula 6] was used.
An organic EL device was produced in the same manner as in Example 31, except that the compound represented by the following formula was used. When a DC voltage of 10 V was applied to this device, light emission of 1760 cd / m ² was obtained.

(Example 35) As the light emitting layer 4, a film obtained by vacuum co-evaporation of a compound represented by the chemical formula [Chemical Formula 21] and a compound represented by the chemical formula [Chemical Formula 3] at a weight ratio of 20: 1 was used. An organic EL device was manufactured in the same manner as in Example 31 except that the organic EL device was formed to have a thickness of 50 nm. When a DC voltage of 10 V was applied to this device, light emission of 2190 cd / m ² was obtained.

(Example 36) As the light emitting layer 4, a film obtained by vacuum co-evaporation of a compound represented by the chemical formula [Formula 21] and a compound represented by the chemical formula [Formula 4] at a weight ratio of 20: 1 was used. An organic EL device was manufactured in the same manner as in Example 31 except that the organic EL device was formed to have a thickness of 50 nm. When a DC voltage of 10 V was applied to this device, light emission of 1960 cd / m ² was obtained.

Example 37 As the light emitting layer 4, a film obtained by vacuum co-evaporation of a compound represented by the chemical formula [Formula 21] and a compound represented by the chemical formula [Formula 5] at a weight ratio of 20: 1 was used. An organic EL device was manufactured in the same manner as in Example 31 except that the organic EL device was formed to have a thickness of 50 nm. When a DC voltage of 10 V was applied to this device, light emission of 2320 cd / m ² was obtained.

(Example 38) As the light emitting layer 4, a film obtained by vacuum co-evaporation of a compound represented by the chemical formula [Formula 21] and a compound represented by the chemical formula [Formula 6] at a weight ratio of 20: 1 was used. An organic EL device was manufactured in the same manner as in Example 31 except that the organic EL device was formed to have a thickness of 50 nm. When a DC voltage of 10 V was applied to this device, light emission of 2030 cd / m ² was obtained.

(Example 39) As the hole transport layer 3, N, N'-diphenyl-N, represented by the chemical formula [Chemical Formula 12], was used.
N′-bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine was used as the light emitting layer 4 with a compound represented by the chemical formula [Formula 23] and a chemical formula [Formula 6] An organic EL device was produced in the same manner as in Example 31, except that a film produced by vacuum co-evaporation of the compound represented by the formula (1) at a weight ratio of 20: 1 was used. DC voltage is applied to this element by 1
When 0 V was applied, light emission of 2080 cd / m ² was obtained.

Example 40 A compound represented by the chemical formula [Chemical Formula 3] was used as the hole transport material contained in the hole transport layer 3, and a compound represented by the chemical formula [Chemical Formula 23] was used as the light emitting layer 4. An organic EL device was manufactured in the same manner as in Example 11 except that the organic EL device was used. When a DC voltage of 10 V was applied to this device, light emission of 240 cd / m ² was obtained.

Example 41 An organic EL device was prepared in the same manner as in Example 40 except that the compound represented by the chemical formula [Chemical Formula 5] was used as the hole transport material contained in the hole transport layer 3.
An element was manufactured. When a DC voltage of 10 V was applied to this device, light emission of 270 cd / m ² was obtained.

Example 42 Example 11 was repeated except that the compound represented by the chemical formula [Chemical Formula 3] was used as the electron transporting layer 5 and the compound represented by the chemical formula [Chemical Formula 21] was used as the light emitting layer 4. The same operation was performed to produce an organic EL device.
When a DC voltage of 10 V was applied to this element, 760 c
Light emission of d / m ² was obtained.

(Example 43) Example 4 was repeated except that the compound represented by the chemical formula [4] was used as the electron transport layer 5.
The same operation as in Example 2 was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 890 cd /
emission of m ² was obtained.

[0102]

As described above, when the compound of the present invention is used as a constituent material of an organic EL device, light emission with higher luminance than before can be obtained, and the effect of the present invention is great.

[Brief description of the drawings]

FIG. 1 is a sectional view of an element of the present invention.

FIG. 2 is a cross-sectional view of the device of the present invention.

FIG. 3 is a sectional view of the device of the present invention.

FIG. 4 is a cross-sectional view of the device of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Hole transport layer 4 Light emitting layer 5 Electron transport layer 6 Cathode

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yukiko Morioka 5-7-1 Shiba, Minato-ku, Tokyo Inside NEC Corporation (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo Japan F term in the electric company (reference) 3K007 AB02 CB01 CB03 DA00 DA01 DB03 EB00 FA01

Claims (4)

[Claims] 1. An organic electroluminescence device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula [Chemical Formula 1]: ] (In the chemical formula, M represents an n-valent metal ion. R ^{1 to} R ⁷
Are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl Group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted Alternatively, it represents an unsubstituted alkoxycarbonyl group or a carboxyl group. Further, R ^{1 to} R ⁷ may form a ring with two of them. n is one of 1, 2, and 3. An organic electroluminescent device comprising the pyromethene metal complex compound represented by the formula (1) alone or in a mixture. 2. The organic thin-film layer has the light-emitting layer, and the light-emitting layer contains the compound represented by the general formula [Chem. 1] alone or as a mixture. Organic electroluminescence element. 3. The organic thin film layer has a hole transport layer containing a hole transport material, and the hole transport layer contains the compound represented by the general formula [Chem. 1] alone or as a mixture. The organic electroluminescence device according to claim 1, wherein: 4. The organic thin-film layer has an electron transporting layer containing an electron transporting material, wherein the electron transporting layer contains the compound represented by the general formula [1] alone or as a mixture. The organic electroluminescence device according to claim 1, wherein