JP2003272866A - Organic electroluminescence element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescence element that has high luminous intensity and luminous efficiency and high color purity, and emits red color. <P>SOLUTION: This is an organic electroluminescence element in which an organic film layer made of one layer or plural layers is interposed between a positive electrode and a negative electrode. At least one layer of the organic film layers contains a compound that is expressed by the formula (1) having a naphthofluoranthene structure. In the formula, R<SB>2</SB>-R<SB>20</SB>express each independently a hydrogen atom, a halogen atom, a straight chain, branched or cyclic alkyl group having carbon 1-18, a straight chain, branched or cyclic alkenyl group having carbon 2-20, a straight chain, branched or cyclic alkoxy group having carbon 1-18, a dialkylamino group and diphenylamino group having carbon 2-18, or an aryl group having carbon 6-20. The adjoining groups of R<SB>15</SB>-R<SB>18</SB>may form a monocyclic or polynuclear aromatic ring. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence element (organic EL element), and more particularly to an organic EL element which has high emission brightness and emission efficiency, high color purity, and emits reddish light.

[0002]

2. Description of the Related Art An organic EL element using an organic substance is expected to be used as a solid-state light emitting inexpensive large area full color display element, and many developments have been made. In general,
The organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. In the light emission of the organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode side,
This is a phenomenon in which holes are injected from the anode side, electrons are recombined with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state. Recently, an organic EL element display has been put into practical use, but a full-color display element is under development.
In particular, there is a demand for an organic EL element which has high color purity and high emission efficiency and emits reddish light. As an attempt to solve these problems, for example, Japanese Unexamined Patent Publication (Kokai) No. 8-31142 discloses a red light emitting device in which a naphthacene or pentacene derivative is added to a light emitting layer. The light emitting device has excellent red purity. However, the applied voltage was as high as 11 V and the half-life time of luminance was about 150 hours, which was insufficient.
Japanese Unexamined Patent Publication (Kokai) No. 3-162481 discloses a device in which a dicyanomethylene compound is added to a light emitting layer, but the purity of red color is insufficient. JP 2001-81451 A
Japanese Patent Publication discloses a red light emitting device in which an amine-based aromatic compound is added to a light emitting layer. This light emitting device has a color purity of CIE chromaticity (0.64, 0.33), but a driving voltage. Was as high as 10V or higher. Japanese Patent Laid-Open No. 2001-160
Japanese Patent No. 489 discloses an element in which an azafluoranthene compound is added to a light emitting layer, but it emits yellow to green light and does not yet emit sufficient red light. Further, for example, J. Amer. Chem. Soc., 118, 2374 (1996) describes 5,10,15,20-tetraphenylbisbenzo.
[5,6] Indeno [1,2,3-cd: 1 ', 2', 3'-lm] perylene is described, and a device using this compound is disclosed in JP-A-2000-865.
49 and Japanese Patent Application Laid-Open No. 10-330295. However, the compounds and their derivatives described in these publications have an absorption maximum wavelength of 590n.
m to 600 nm, and the emission wavelength has a maximum value of 610 n
m, and further long wavelength light emission, high light emission efficiency, high brightness light emission at low voltage, and the like have been desired for red organic EL light emission for display specifications.

[0003]

SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and provides an organic EL element which has high emission brightness and emission efficiency, high color purity, and emits reddish light. The purpose is to

[0004]

Means for Solving the Problems As a result of intensive studies for solving the above problems, the present inventors have found that by using a compound having a naphthofluoranthene structure as a material for an organic thin film layer of an organic EL device, The present invention has been found to solve the above problems, and the present invention has been solved.

That is, according to the present invention, an organic E layer in which one or a plurality of organic thin film layers are sandwiched between a cathode and an anode.
In the L element, at least one of the organic thin film layers provides an organic EL element containing a compound represented by the following formula (1) or (2) having a naphthofluoranthene structure.

[0006]

[Chemical 3] (In the formula, R _{1 to} R ₂₀ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic carbon atom having 2 to 20 carbon atoms. Alkenyl group, linear, branched or cyclic C1-C18 alkoxy group, C2-C18 dialkylamino group, substituted or unsubstituted diphenylamino group, or substituted or unsubstituted C6-C20 Represents an aryl group.
Adjacent groups of R _{15 to} R ₁₈ may form a monocyclic or polycyclic aromatic ring, and the formed aromatic rings are each independently a hydrogen atom, a halogen atom, a straight chain, a branched chain or a Cyclic C1-C18 alkyl group, linear, branched or cyclic C2-C20 alkenyl group, linear, branched or cyclic C1-C18 alkoxy group, C2-C18 dialkyl An amino group, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms may be bonded. )

[0007]

[Chemical 4] (In the formula, R _{21 to} R ₃₈ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic C 1-18 alkyl group, a linear, branched or cyclic C 2-20 Alkenyl group, linear, branched or cyclic C1-C18 alkoxy group, C2-C18 dialkylamino group, substituted or unsubstituted diphenylamino group, or substituted or unsubstituted C6-C20 Represents an aryl group.
Adjacent groups of R _{33 to} R ₃₈ may form a monocyclic or polycyclic aromatic ring, and the formed aromatic rings each independently represent a hydrogen atom, a halogen atom, a straight chain, or a branched chain. Or a cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, and 2 to 18 carbon atoms
Dialkylamino group, substituted or unsubstituted diphenylamino group, or substituted or unsubstituted carbon number 6 to 20
The aryl group of may be bonded. )

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The organic EL device of the present invention is an organic EL device in which one or more organic thin film layers are sandwiched between a cathode and an anode, and at least one of the organic thin film layers is a naphtho group. It contains a compound represented by the above formula (1) or (2) having a fluoranthene structure. In the general formula (1), R _{1 to} R ₂₀ are each independently
Hydrogen atom, halogen atom, linear, branched or cyclic C1-C18 alkyl group, linear, branched or cyclic C2
To 20 alkenyl groups, linear, branched or cyclic carbon number 1
It represents an alkoxy group having 18 to 18, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine, with fluorine and chlorine being preferred. Examples of the linear, branched or cyclic C1-C20 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- group.
Butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, dodecyl group, hexadecyl group, octadecyl 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- group 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-tri Nitropropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, phenethyl group, α-methylbenzyl group, phenylpropyl group, benzyl group, diphenylmethyl group, 4
-A biphenylmethyl group, a cyclohexylmethyl group, etc. are mentioned. Among these, a methyl group, a t-butyl group,
The isopropyl group is preferred.

The linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms includes ethenyl group, 1-propenyl group,
Examples thereof include a 2-propenyl group, a 1-methylpropenyl group, a 2-methylpropenyl group, a 1-butenyl group, a 2-methylallyl group, a styryl group, and a 2-phenylstyryl group. Among these, a styryl group and a 2-phenylstyryl group are preferable.

The linear, branched or cyclic C1-C18 alkoxy group is a group represented by --OY, and examples of Y include a methyl group, an ethyl group, a propyl group, an isopropyl group and 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-tri Iodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3
-Diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2
-Cyanoisobutyl group, 1,2-dicyanoethyl group,
1,3-dicyanoisopropyl group, 2,3-dicyano-
t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group , 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, phenyl group, biphenyl group, benzyl group, phenylethyl group, Examples thereof include a phenylpropyl group. Among these, Y is a methyl group, t
-A butyl group and a phenyl group are preferred.

Examples of the dialkylamino group having 2 to 18 carbon atoms include dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, methylethylamino group, dibenzylamino group, dicyclohexylamino group,
Etc. Among these, dimethylamino group,
The diethylamino group is preferred. The substituted or unsubstituted aryl group having 6 to 20 carbon atoms includes phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, fluorenyl group, fluoranthenyl group, biphenyl group, terphenyl group, stilbene group. Groups and the like. Among these, a phenyl group, a biphenyl group, a naphthyl group and a stilbene group are preferable.

In the general formula (1), adjacent groups of R _{15 to} R ₁₈ may form a monocyclic or polycyclic aromatic ring, for example, benzene ring, naphthalene ring, anthracene ring, acenaphthyl ring. , A phenalene ring, a phenanthrene ring, a fluoranthene ring and the like, and a benzene ring, a naphthalene ring and an anthracene ring are preferable. The formed aromatic rings are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic C1-C18 alkyl group, a linear, branched or cyclic C2-C20 alkenyl group. , A linear, branched or cyclic C1-C18 alkoxy group, a C2-C18 dialkylamino group, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted C6-20 aryl group. May be bonded. Specific examples of these bonding groups include the same as those mentioned above. In the general formula (1),
As each substituent, 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, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted Examples thereof include a substituted alkoxycarbonyl group and a carboxyl group.

In the above general formula (2), R _{21 to} R _21
38 is each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic C1-C18 alkyl group, a linear, branched or cyclic C2-C20 alkenyl group, a linear, branched or It represents a cyclic alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In the general formula (2), adjacent groups of R _{33 to} R ₃₈ may respectively form a monocyclic or polycyclic aromatic ring, and specific examples thereof are the same as those in the general formula (1). There are things. The formed aromatic rings are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic C1-C18 alkyl group, a linear, branched or cyclic C2-C20 alkenyl group. , A linear, branched or cyclic C1-C18 alkoxy group, a C2-C18 dialkylamino group, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted C6-20 aryl group. May be bonded. Specific examples thereof include the same as those in the above general formula (1).

In the general formula (2), each substituent is 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. Base,
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 Examples thereof include a substituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group and a carboxyl group.

Specific examples of the compounds having the naphthofluoranthene structure represented by the general formulas (1) and (2) in the present invention are shown below, but the compounds are not limited to these exemplified compounds.

[Chemical 5]

[0017]

[Chemical 6]

The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between the anode and the cathode as described above. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material for transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. Further, it is preferable that the light emitting material has extremely high fluorescence quantum efficiency, high hole transporting ability and electron transporting ability, and forms a uniform thin film. The multilayer organic EL device includes (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 the organic EL device of the present invention, it is preferable that the layer containing the compound having a naphthofluoranthene structure is a light emitting layer. Further, if necessary, in addition to the compound of the general formula (1) or (2), further known host materials, light emitting materials, doping materials, hole injection materials and electron injection materials are used and used in combination. You can also When the organic EL element has a multi-layered structure, it is possible to prevent a decrease in brightness and life due to quenching, and by using another doping material, improvement in emission brightness and emission efficiency,
It is also possible to obtain red or white light emission, and by using it in combination with another doping material that contributes to phosphorescence emission, it is possible to improve conventional light emission brightness and light emission efficiency. In addition, the hole injection layer in the organic EL device of the present invention,
The light emitting layer and the electron injecting layer may each be formed by a layer structure of two or more layers. In that case, in the case of a hole injection layer, a layer that injects holes from the electrode is called a hole injection layer, and a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer is called a hole transport layer. Similarly, in the case of the electron injection layer, the layer that injects electrons from the electrode is called an electron injection layer, and the layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on various factors such as the energy level of the material, heat resistance, and adhesion to the organic thin film layer or the metal electrode.

As the light emitting material or host material which can be used in the organic thin film layer together with the compound having the naphthofluoranthene structure, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone. , Phthaloperinone, naphthaloperinone,
Diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, imine, diphenylethylene, vinylanthracene, diaminoanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole Chelated oxinoid compounds, quinacridone,
Examples include rubrene, stilbene derivatives, fluorescent dyes, quinoline metal complexes, aminoquinoline metal complexes, benzoquinoline metal complexes, and the like. Particularly, quinoline metal complexes, aminoquinoline metal complexes, benzoquinoline metal complexes, and aromatic compounds having anthracene skeleton. It is preferable to use a compound or an acenaphthofluoranthene derivative because energy transfer is smoothly performed.

The hole-injecting material has the ability to transport holes, has the effect of injecting holes from the anode, and has an excellent effect of injecting holes into the light-emitting layer or the light-emitting material. A compound that prevents excitons from moving to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivative, naphthalocyanine derivative, porphyrin derivative, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole,
Hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and their derivatives, and polyvinylcarbazole, polysilane, conductive polymers, etc. Examples thereof include polymeric materials, but the present invention is not limited thereto.

Among these hole injecting materials, the more effective hole injecting materials are aromatic tertiary amine derivatives or phthalocyanine derivatives. Specific examples of the aromatic tertiary amine derivative include triphenylamine, tritolylamine, tolyldiphenylamine, N, N′-diphenyl-
N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N, N', N '-(4
-Methylphenyl) -1,1'-phenyl-4,4'-
Diamine, N, N, N ', N'-(4-methylphenyl) -1,1'-biphenyl-4,4'-diamine,
N, N'-diphenyl-N, N'-dinaphthyl-1,
1'-biphenyl-4,4'-diamine, N, N'-
(Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N
-Bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane and the like, or oligomers or polymers having these aromatic tertiary amine skeletons, but not limited thereto. Specific examples of the phthalocyanine (Pc) derivative include H ₂ Pc, CuPc and Co.
Pc, NiPc, ZnPc, PdPc, FePc, Mn
Pc, ClAlPc, ClGaPc, ClInPc, C
lSnPc, Cl ₂ SiPc, (HO) AlPc, (H
O) GaPc, VOPc, TiOPc, MoOPc, G
It is a phthalocyanine derivative such as aPc-O-GaPc and a naphthalocyanine derivative, but is not limited thereto.

The electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode, and an excellent electron injecting effect to the light emitting layer or the light emitting material. A compound that prevents migration to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, quinoxaline, fluorenylidene methane, anthraquinodimethane, anthrone and the like. However, the present invention is not limited to these.

Among these electron injecting materials, a more effective electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specific examples of the metal complex compound include lithium 8-hydroxyquinolinate, bis (8-hydroxyquinolinate) zinc, and bis (8-hydroxyquinolinate).
Copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, Bis (10-hydroxybenzo [h] quinolinate) beryllium, bis (10-hydroxybenzo [h]
Quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinate) (2-
Examples thereof include, but are not limited to, naphtholate) gallium and the like.

The nitrogen-containing five-membered derivative is preferably an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative. In particular,
2,5-bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) ) -1,3,4-Oxadiazole, 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-oxadiazole, 1,4
-Bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-thiadiazole, 1,4-
Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-butylphenyl) -5- (
4 "-biphenyl) -1,3,4-triazole, 2,
5-bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)
Examples thereof include, but are not limited to, benzene and the like.

The charge injection property can be improved by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material. As the conductive material used for the anode of the organic EL device of the present invention, those having a work function larger than 4 eV are suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum. , Palladium and alloys thereof, tin oxide used for ITO substrates, NESA substrates,
A metal oxide such as indium oxide, or an organic conductive resin such as polythiophene or polypyrrole is used. As the conductive material used for the cathode, one having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium,
Ruthenium, manganese, aluminum, etc., and alloys thereof are used, but not limited to these.
Typical examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, etc., but are not limited to these. The alloy ratio is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected as an appropriate ratio. The anode and the cathode may be formed in a layered structure of two or more layers if necessary.

At least one of the organic EL devices of the present invention is
Having an inorganic compound layer between the electrode and the organic thin film layer
You may stay. Preferred mineralization used for inorganic compound layers
Compounds include alkali metal oxides and alkaline earth oxides
Compounds, rare earth oxides, alkali metal halides, alkali
Re-earth halide, rare earth halide, SiO_X,
AlO_X, SiN_X, SiON, AlON, GeO_X,
LiO_X, LiON, TiO_X, TiON, TaO_X,
TaON, TaN_X, C, various oxides, nitrides, oxidation
It is a nitride. In particular, the component of the layer in contact with the anode is S
iO_X, AlO _X, SiN_X, SiON, AlON, G
eO_X, C form a stable injection interface layer, which is preferable. Well
In particular, as the component of the layer in contact with the cathode, LiF, Mg
F₂, CaF₂, MgF₂, NaF are preferred.

In order to make the organic EL device of the present invention emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the emission wavelength region of the device. It is also desirable that the substrate is transparent. The transparent electrode is made of the above-mentioned conductive material and is set by a method such as vapor deposition or sputtering so as to ensure a predetermined translucency. The electrodes on the light emitting surface are
It is desirable that the light transmittance is 10% or more. The board is
Although it is not limited as long as it has mechanical and thermal strength and transparency, examples thereof include a glass substrate and a transparent resin film. As a transparent resin film,
Polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethylmethacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone, polysulfone,
Polyether sulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidenefluor Ride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene and the like can be mentioned.

In the organic EL device of the present invention, a protective layer may be provided on the surface of the device or the entire device may be protected by silicone oil, resin or the like in order to improve stability against temperature, humidity, atmosphere and the like. Is. For formation of each layer of the organic EL device of the present invention, any one of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating and wet film forming methods such as spin coating, dipping and flow coating can be applied. You can Although the film thickness of each layer is not particularly limited, it is necessary to set an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, and the light emission efficiency deteriorates. If the film thickness is too thin, pinholes and the like will occur, and even if an electric field is applied, sufficient emission brightness cannot be obtained. The normal film thickness is preferably in the range of 5 nm to 10 μm, but 10 nm to
The range of 0.2 μm is more preferable.

In the case of the wet film forming method, the materials for forming the respective layers are ethanol, chloroform, tetrahydrofuran,
The thin film is formed by dissolving or dispersing in a suitable solvent such as dioxane, and any solvent may be used. Also,
Appropriate resins and additives may be used in any of the layers in order to improve film-forming properties and prevent pinholes in the film. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethylmethacrylate, polymethylacrylate and cellulose, and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Further, examples of the additive include an antioxidant, an ultraviolet absorber, a plasticizer and the like. As described above, by using the compound having the naphthofluoranthene structure represented by the general formula (1) or (2) for the organic thin film layer of the organic EL element, the emission brightness and the emission efficiency are high, and the red light is emitted. An organic EL element can be obtained, and the organic EL element is, for example, an electrophotographic photoreceptor,
It is preferably used for flat light emitters such as flat panel displays for wall-mounted televisions, light sources for copiers, printers, backlights of liquid crystal displays or measuring instruments, display plates, indicator lights, accessories and the like.

[0031]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Synthesis Example 1 (Synthesis of Compound (P-1)) The above compound (P-
The synthetic route of 1) is shown below.

[Chemical 7]

(1) 7,14-diphenyl-7 ', 1
Synthesis of 4'-diphenyl-3,3'-binaphtho [k] fluoranthene 0.15 g of nickel chloride (anhydride), 2.2 g of triphenylamine, 3.1 g of zinc powder and 3.6 g of sodium bromide were added to N. , N-dimethylacetamide (50 ml) was added, and the mixture was heated with stirring at 80 ° C. for 2 hours. next,
4.8 g (9 mmol) of 3-bromo-7,12-dimethylnaphtho [k] fluoranthene was mixed with N, N-dimethylformamide and N, N-dimethylacetamide (1:
1) To 320 ml of the mixed solution, a solution dissolved at 80 ° C. was added all at once, and the mixture was heated and stirred at the same temperature for 24 hours. After allowing to cool, 2N hydrochloric acid was added to the reaction product, and the mixture was stirred and extracted with 600 ml of dichloromethane. The extract was washed with distilled water and saturated brine, dried with Glauber's salt, and the solvent was distilled off to obtain an orange powder. Further, it was treated with silica gel column chromatography (eluent: hexane: dichloromethane = 1: 1) to obtain 4.28 g (4.
72 mmol) was obtained (yield 52%). This one is N
According to the measurement of MR, IR and FD-MS (field diffusion mass analysis), 7,14-diphenyl-
7 ', 14'-diphenyl-3,3'-binaphtho [k]
It was identified as fluoranthene (raw material 1 and raw material 2 in Table 1).

(2) Synthesis of compound (P-1) 2.4 g of sodium chloride, 12 g of anhydrous aluminum chloride
Is heated and stirred at an oil bath temperature of 150 ° C. to be melted, and then 7,14-diphenyl-7 ′, 14′-diphenyl-is added therein.
1 g of 3,3'-binaphtho [k] fluoranthene (1.1
(Mmol) and stirred for 5 minutes. After the reaction, the mixture was allowed to cool and the black solid substance precipitated was added with 2N hydrochloric acid (20 ml) and dissolved, and the mixture was refluxed for 1 hour. After standing to room temperature, the solid was filtered and washed with water. After washing this solid with methanol, alumina column chromatography (eluent: toluene / n-hexane = 1 /
Processed in 4). The solvent was distilled off under reduced pressure to obtain 0.4 g of black-purple crystals. This product has NMR, IR and FD-
It was identified as the compound (P-1) by MS measurement (yield 40%). Melting point: 300 ° C. or higher, absorption maximum wavelength (in toluene): 623 nm.

Synthesis Example 2 (Synthesis of Compound (P-2)) The synthetic route of the compound (P-2) is shown below.

[Chemical 8]

(1) Synthesis of 3- (7,14-diphenylnaphtho [k] fluoranthenyl) boric acid Under a stream of argon, 8 g (15 mmol) of 3-bromo-7,14-diphenylnaphtho [k] fluoranthene was added. It was dissolved in 15 ml of ether and 150 ml of toluene, cooled to -30 ° C to -40 ° C, and an n-butyllithium hexane solution (BuLi: 15 mmol) was added dropwise with stirring. Remove the refrigerant and raise the temperature to 20 ° C,
Stir for 1 hour. Then, the reaction solution was cooled to −70 ° C., and 4.5 ml (45 mmol) of trimethoxyboron was added.
10 ml of the ether solution of was slowly added dropwise.
Stirring was continued for 1 hour, cooling was stopped, and the temperature was returned to room temperature. After adding 2N hydrochloric acid to the reaction solution and stirring, the organic layer was separated, washed with distilled water and a saturated saline solution, and dried by adding Glauber's salt, and the solvent was distilled off. Further wash with toluene to give a pale yellow powder 5
g (10 mmol) was obtained. This one is NMR, IR
It was identified as 3- (7,14-diphenylnaphtho [k] fluoranthenyl) boric acid (raw material (1-2) in Table 1) by FD-MS measurement (yield 67%).

(2) Synthesis of Intermediate (A-2) Under a stream of argon, 3-bromo-7,12-diphenylbenzo [k] fluoranthene (the starting material (2-
2)) 2.4 g (5 mmol) was dissolved in 100 ml of ethylene glycol dimethyl ether, 0.25 g of tetrakis (triphenylphosphine) palladium was added, and the mixture was stirred for 15 minutes. Next, 3.5 g (7) of 3- (7,14-diphenylnaphtho [k] fluoranthenyl) boric acid of (1) suspended in 20 ml of ethanol.
(Mmol) and stirred for 15 minutes. Next, 25 ml of a 2M sodium carbonate aqueous solution was added, and the stirring under reflux was continued for 24 hours. After the reaction, dichloromethane was added to the solution to separate the organic layer, which was washed with distilled water and saturated saline, and dried by adding Glauber's salt, and the solvent was distilled off. Treated with silica gel column chromatography (eluent; hexane: dichloromethane = 6: 4) to give 2.75 g of yellowish orange target powder.
(3.2 mmol) was obtained (yield 64%). This was identified as the intermediate (A-2) in Table 1 by measurement of NMR, IR and FD-MS.

(3) Synthesis of compound (P-2) 2.2 g (3.84 mmol) of tin tetrachloride and 2.4 g (9 mmol) of anhydrous aluminum chloride were added to dehydrated benzene 60.
The mixture was added to milliliter, suspended, and refluxed. (2)
A solution prepared by dissolving 1.2 g (1.4 mmol) of the intermediate (A-2) in Example 1 in 60 ml of benzene was added at once and refluxed for 5 minutes. After allowing the reaction solution to cool, 1N
200 ml of a hydrochloric acid solution was added and stirred, the organic layer was separated, washed with distilled water and saturated saline, added with magnesium sulfate and dried, and the solvent was distilled off. Treated with silica gel column chromatography (eluent; hexane: dichloromethane = 8: 2) to obtain 0.4 g of the target compound of black-red color.
(0.47 mmol) was obtained (yield 34%). This compound was identified as the compound (P-2) by measurement of NMR, IR and FD-MS. Melting point 250 ° C. or higher, absorption maximum wavelength (in toluene) 616 nm.

Synthesis Example 3 (Synthesis of Compound (P-3)) As a raw material (2-3) in place of 3-bromo-7,12-diphenylbenzo [k] fluoranthene in Synthesis Example 2 (2). Compound (P-3) was synthesized in the same manner except that 3-bromo-7,8,9,10-tetraphenylfluoranthene was used. The obtained compound was black-purple crystals and had a melting point of 250 ° C. or higher. Table 1 shows the raw materials 1 and 2, the intermediate A and the target compound, and their absorption maximum wavelengths (in toluene). Synthesis Example 4 (Synthesis of Compound (P-4)) In Synthesis Example 2 (2), 3-bromo-7,12-diphenylbenzo [k] fluoranthene was used in place of 3-bromo as a raw material (2-4). Compound (P-4) was synthesized in the same manner except that -8,13-diphenylnaphtho [k] fluoranthene was used. The obtained compound was black-purple crystals and had a melting point of 250 ° C. or higher. Table 1 shows the raw materials 1 and 2, the intermediate A and the target compound, and their absorption maximum wavelengths (in toluene).

Synthesis Example 5 (Synthesis of Compound (P-5)) In Synthesis Example 2 (1), 3-bromo-7,14-diphenylnaphtho [k] fluoranthene was used in place of 3-bromo-7,14-diphenylnaphtho [k] fluoranthene.
The raw material (1-5) was synthesized using bromo-8,13-diphenylnaphtho [k] fluoranthene, and in (2), 3-bromo-7,12-diphenylbenzo [k] was used as the raw material (2-5). Compound (P-5) was synthesized in the same manner except that 3-bromo-8,13-diphenylnaphtho [k] fluoranthene was used instead of fluoranthene. The obtained compound was black-purple crystals and had a melting point of 250 ° C. or higher. Table 1 shows the raw materials 1 and 2, the intermediate A and the target compound, and their absorption maximum wavelengths (in toluene). Synthesis Example 6 (Synthesis of Compound (P-6)) In Synthesis Example 2 (1), 3-bromo-7,14-diphenylnaphtho [k] fluoranthene was used in place of 3-bromo-7,14-diphenylnaphtho [k] fluoranthene.
Compound (P-6) was synthesized in the same manner except that raw material (1-6) was synthesized using bromo-8,13-diphenylnaphtho [k] fluoranthene. The obtained compound was black-purple crystals and had a melting point of 250 ° C. or higher.
Table 1 shows the raw materials 1 and 2, the intermediate A and the target compound, and their absorption maximum wavelengths (in toluene).

[0040]

[Table 1]

Synthesis Example 7 (Synthesis of Compound (P-7)) The synthetic route of the compound (P-7) is shown below.

[Chemical 9]

(1) Synthesis of ring-closed compound (B-7) In the same manner as in (1) of Synthesis Example 2, 3- (7,14-diphenylnaphtho [k] fluoranthenyl) was used as the starting material (1-7). Boric acid was synthesized to give 3 in (2) of Synthesis Example 2.
Instead of -bromo-7,12-diphenylbenzo [k] fluoranthene, 5-bromofluoranthene was used as the starting material (2-7) to synthesize the intermediate (A-7), and ), The cyclization is carried out in the same manner as
-7) was synthesized. (2) Synthesis of bromo compound (C-7) 9.8 g (15 mmol) of ring-closed compound (B-7) was dissolved in 100 ml of dimethylformamide, and 2.85 g of N-bromosuccinimide was added to 10 ml of dimethylformamide. (16 mmol) dissolved in 0
The mixture was added dropwise at ° C and stirred for 6 hours. The reaction solution is distilled water 300
The solid produced in addition to milliliter was filtered off and washed with methanol and distilled water to obtain 9.2 g of a light brown powder. This product was identified as the target monobromo compound (C-7) (a small amount of dibromo compound was confirmed by MS) by NMR and FD-MS measurements (84% yield).

(3) Synthesis of compound (P-7) Under a stream of argon gas, bromo compound (C-7) 1.
0.36 g of diphenylamine to 5 g (2 mmol)
(2.1 mmol), palladium acetate 120 mg, tris (t-butyl) phosphine 120 mg, sodium t
-Butoxide (404 mg) was dissolved in toluene (50 ml) and refluxed for 6 hours. Toluene 50 after reaction
After adding milliliter, 200 ml of distilled water was added and stirred, the organic layer was separated, washed with distilled water and saturated saline solution, added with magnesium sulfate and dried, and the solvent was distilled off. It was treated with silica gel column chromatography (eluent; hexane: dichloromethane = 8: 2) to obtain 0.6 g (0.73 mmol) of a black-red compound (P-7) (yield 36.5%). . The melting point was 250 ° C. or higher. This compound was identified as a compound (P-7) by measurement of NMR and FD-MS. Table 2 shows the absorption maximum wavelength (in toluene) of the target compound.

Synthesis Example 8 (1) Synthesis of ring-closed compound (B-8) In (1) of Synthesis Example 2, instead of 3-bromo-7,14-diphenylnaphtho [k] fluoranthene, 3-
Raw material (1-8) was synthesized using bromo-8,13-diphenylnaphtho [k] fluoranthene, and the raw material ((8) was used instead of 3-bromo-7,12-diphenylbenzo [k] fluoranthene in (2). The intermediate (A-8) was synthesized by using 5-bromofluoranthene as 2-8), and cyclized in the same manner as in (3) of Synthesis Example 2 to give the ring-closed compound (B-8). Synthesized. Then, a bromo compound (C-8) was synthesized in the same manner as in (2) of Synthesis Example 7, and diphenylamination was performed in the same manner as in (3) to obtain a black red compound (P-
8) was synthesized. The melting point was 250 ° C. or higher. Table 2 shows the absorption maximum wavelength (in toluene) of the target compound.

Synthesis Example 9 A raw material (1-9) was synthesized in the same manner as in (1) of Synthesis Example 2, and in (2), instead of 3-bromo-7,12-diphenylbenzo [k] fluoranthene. , Raw material (2-
Using 9-bromoanthracene as 9), the intermediate (A
-9) was synthesized and cyclized in the same manner as in Synthesis Example 2 (3) to synthesize a ring-closed body (B-9). Next, Synthesis Example 7
A bromo compound (C-9) was synthesized in the same manner as in (2) of
Diphenylamination was performed in the same manner as in (3) to synthesize a black-red compound (P-9). The melting point was 250 ° C. or higher. Table 2 shows the maximum absorption wavelength (in toluene) of the target compound.
Shown in.

Synthesis Example 10 The starting material (1-10) was synthesized in the same manner as in (1) of Synthesis Example 2, and in (2), instead of 3-bromo-7,12-diphenylbenzo [k] fluoranthene. , Raw material (2
Intermediate (A-10) was synthesized using 1-bromonaphthalene as -10), and cyclized in the same manner as in Synthesis Example 2 (3) to synthesize a ring-closed body (B-10). next,
A bromo compound (C-10) was synthesized in the same manner as in (2) of Synthesis Example 7, and diphenylamination was performed in the same manner as in (3) to synthesize a black-red compound (P-10). Melting point is 250
It was above ℃. Table 2 shows the absorption maximum wavelength (in toluene) of the target compound.

Synthetic Example 11 The raw material (1-11) was synthesized in the same manner as in (1) of Synthetic Example 2, and in (2), 3-bromo-7,12-diphenylbenzo [k] fluoranthene was used instead. , Raw material (2
Using 3-bromopyrene as -11), the intermediate (A-
11) was synthesized and cyclized in the same manner as in Synthesis Example 2 (3) to synthesize a ring-closed body (B-11). Then, a bromo compound (C-11) was synthesized in the same manner as in (2) of Synthesis Example 7, and diphenylamination was performed in the same manner as in (3) to synthesize a black-red compound (P-11). The melting point was 250 ° C. or higher. Absorption maximum wavelength of target compound (in toluene)
Is shown in Table 2.

Synthetic Example 12 The starting material (1-12) was synthesized in the same manner as in (1) of Synthetic Example 2, and in (2), instead of 3-bromo-7,12-diphenylbenzo [k] fluoranthene. , Raw material (2
Intermediate (A-12) was synthesized by using 5-bromophenanthrene as -12), and cyclized in the same manner as in Synthesis Example 2 (3) to synthesize a ring-closed body (B-12). . Then, in the same manner as in (2) of Synthesis Example 7, a bromo compound (C-1
1) was synthesized, and diphenylamination was performed in the same manner as in (3) to synthesize a black-red compound (P-11). The melting point was 250 ° C. or higher. Table 2 shows the absorption maximum wavelength (in toluene) of the target compound.

[0049]

[Table 2]

Example 1 A transparent electrode made of indium tin oxide having a film thickness of 120 nm was provided on a glass substrate having a size of 25 × 75 × 1.1 mm. The glass substrate was irradiated with ultraviolet rays and ozone to be washed, and then the glass substrate was placed in a vacuum vapor deposition apparatus. First, the following TPD74 was deposited to a thickness of 60 nm, and then the following NPD was deposited to a thickness of 20 nm thereon. Then, the above compound (P-1) as a light emitting material and the following DPVDPAN were co-deposited at a weight ratio of 2:40 to obtain a thickness of 5
A 0 nm luminescent medium layer was formed. Furthermore, Alq (8-
Aluminum complex of hydroxyquinoline) was evaporated to a thickness of 10 nm. TPD74, NPD, compound (P-
1): The layers formed by depositing DPVDPAN and Alq are a hole injection layer, a hole transport layer, a light emitting medium layer, and an electron injection layer, respectively. Next, an alkali metal halide, LiF, was evaporated to a thickness of 0.2 nm, and then aluminum was evaporated to a thickness of 150 nm. This Al / LiF
Acts as a cathode. In this way, an organic EL device was produced. When conducting an energization test on this element,
1 at a voltage of 5.5 V and a current density of 2.78 mA / cm ² .
A red emission of 12 cd / m ² was obtained, and the chromaticity coordinate (0.6
4, 0.33), and the luminous efficiency was 2.30 lumen / W.

[0051]

[Chemical 10]

Examples 2 to 6 Organic EL devices were prepared in the same manner as in Example 1 except that the compounds (P-2) to (P-6) were used instead of the compound (P-1). DC voltage of the obtained device 5.5
The current density at V, emission luminance, emission color, and chromaticity coordinates were measured, and the results are shown in Table 1.

Example 7 In Example 1, the compound (P-1) as a light emitting material:
Compound (P-7) instead of DPVDPAN: D below
An organic EL device was produced in the same manner except that PVTP was used. Current density of the obtained device at a DC voltage of 6.0 V,
The emission brightness, emission color, and chromaticity coordinates were measured, and the results are shown in Table 1.
It was shown to.

[0054]

[Chemical 11]

Examples 8 to 12 Organic EL devices were produced in the same manner as in Example 7, except that the compounds (P-8) to (P-12) were used instead of the compound (P-7). DC voltage of this element 6.0V
Current density, emission brightness, emission color, and chromaticity coordinates at
The results are shown in Table 1.

Example 13 In Example 1, the compound (P-1) as a light emitting material:
Compound (P-2) instead of DPVDPAN: D below
DAF (3,10-bis (di-p-tolylamino)-
An organic EL device was produced in the same manner except that 7,14-diphenyl-acenaphtho [1,2-K] fluoranthene) was used. The current density, emission luminance, emission color, and chromaticity coordinate of the obtained device at a DC voltage of 6.0 V were measured, and the results are shown in Table 1.

[0057]

[Chemical 12]

Example 14 In Example 13, the compound (P-
2): instead of DDAF, compound (P-9): DDA
Organic EL was used in the same manner except that F was used in a weight ratio of 1:40.
A device was produced. The current density, emission luminance, emission color, and chromaticity coordinate of the obtained device at a DC voltage of 6.0 V were measured, and the results are shown in Table 1.

Comparative Example 1 In Example 1, instead of the compound (P-1), the following compound (P-0) (5,10,15,20-tetraphenylbisbenzo [5,6] indeno [1,6] 2,3-cd: 1 ', 2', 3'-lm]
An organic EL device was produced in the same manner except that perylene) was used. The current density, emission luminance, emission color, and chromaticity coordinates of the obtained device at a DC voltage of 8.0 V were measured, and the results are shown in Table 1.

[Chemical 13] Comparative Example 2 An organic EL device was produced in the same manner as in Example 13 except that the compound (P-0) was used instead of the compound (P-1). The current density, emission luminance, emission color, and chromaticity coordinate of the obtained device at a DC voltage of 6.0 V were measured, and the results are shown in Table 1.

[0060]

[Table 3]

As shown in Table 1, compounds (P-1) to
The organic EL devices of Examples 1 to 14 using (P-14) functioned as a red dopant material having high emission brightness and emission efficiency and high chromaticity. On the other hand, the compound (P
The organic EL device of Comparative Example 1 using −0) has 100 cd
The applied voltage for obtaining a luminance of / m ² was high and the luminous efficiency was insufficient. The organic EL device of Comparative Example 2 had insufficient luminous efficiency and the emission color was reddish orange.

[0062]

As described in detail above, the organic electroluminescence device of the present invention using the compound represented by the general formula (1) or (2) as the material of the organic thin film layer has a luminous brightness and a luminous efficiency. , High color purity, and emits reddish light. Therefore, the organic electroluminescent element of the present invention is extremely useful as a light source for various electronic devices.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Toshihiro Iwakuma             1280 Kamizumi, Sodegaura, Chiba Prefecture (72) Inventor Tadashi Kusumoto             1280 Kamizumi, Sodegaura, Chiba Prefecture F-term (reference) 3K007 AB02 AB03 AB04 DB03                 4H006 AA03 AB91

Claims (6)

[Claims] 1. In an organic electroluminescence device in which an organic thin film layer consisting of one or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers comprises
An organic electroluminescence device containing a compound represented by the following formula (1) having a naphthofluoranthene structure. [Chemical 1] (In the formula, R _{1 to} R ₂₀ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic carbon atom having 2 to 20 carbon atoms. Alkenyl group, linear, branched or cyclic C1-C18 alkoxy group, C2-C18 dialkylamino group, substituted or unsubstituted diphenylamino group, or substituted or unsubstituted C6-C20 Represents an aryl group.
Adjacent groups of R _{15 to} R ₁₈ may form a monocyclic or polycyclic aromatic ring, and the formed aromatic rings are each independently a hydrogen atom, a halogen atom, a straight chain, a branched chain or a Cyclic C1-C18 alkyl group, linear, branched or cyclic C2-C20 alkenyl group, linear, branched or cyclic C1-C18 alkoxy group, C2-C18 dialkyl An amino group, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms may be bonded. ) 2. In an organic electroluminescence device in which an organic thin film layer consisting of one or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers comprises:
An organic electroluminescence device containing a compound represented by the following formula (2) having a naphthofluoranthene structure. [Chemical 2] (In the formula, R _{21 to} R ₃₈ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic C 1-18 alkyl group, a linear, branched or cyclic C 2-20 Alkenyl group, linear, branched or cyclic C1-C18 alkoxy group, C2-C18 dialkylamino group, substituted or unsubstituted diphenylamino group, or substituted or unsubstituted C6-C20 Represents an aryl group.
Adjacent groups of R _{33 to} R ₃₈ may form a monocyclic or polycyclic aromatic ring, and the formed aromatic rings each independently represent a hydrogen atom, a halogen atom, a straight chain, or a branched chain. Or a cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, and 2 to 18 carbon atoms
Dialkylamino group, substituted or unsubstituted diphenylamino group, or substituted or unsubstituted carbon number 6 to 20
The aryl group of may be bonded. ) 3. The organic electroluminescence device according to claim 1, wherein the layer containing the compound having a naphthofluoranthene structure is a light emitting layer. 4. The organic electroluminescence device according to claim 1, wherein the layer containing the compound having a naphthofluoranthene structure contains a light emitting organometallic complex. 5. The organic electroluminescent device according to claim 1, further comprising a hole injecting and transporting layer between the cathode and the anode. 6. The organic electroluminescent device according to claim 1, further comprising an electron injecting and transporting layer between the cathode and the anode.