JP2002110355A - Hydrocarbon compound and organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element that has an excellent luminous efficiency and a high luminance. SOLUTION: This is a compound as expressed in Formula (1-A) and the electroluminescent element uses the compound. In Formula, each of X1-X24 expresses independently hydrogen atom, halogen atom, a straight chain, branched or cyclic alkyl group, a straight chain, branched or cyclic alkoxy group, or a substituted or a non-substituted aryl group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device and a novel hydrocarbon compound which can be suitably used for the device.

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent element has been used as a panel-type light source such as a backlight. However, driving the light emitting element requires a high AC voltage. Recently, an organic electroluminescent device (organic electroluminescent device: organic EL device) using an organic material as a light emitting material has been developed [Appl. Phys. Lett., 51, 913].
(1987)]. An organic electroluminescent element has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, and electrons and holes are injected into the thin film and recombined to form excitons. (Exciton), and emits light using light emitted when the exciton is deactivated. The organic electroluminescent element can emit light at a low DC voltage of about several volts to several tens of volts, and can have various colors (for example, red, blue, and green) by selecting the type of the fluorescent organic compound. Light emission is possible. Organic electroluminescent devices having such characteristics are expected to be applied to various light emitting devices, display devices, and the like. However, in general, the emission luminance is low and is not practically sufficient.

As a method for improving the light emission luminance, an organic electroluminescent device using, for example, tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative or a pyran derivative as a guest compound (dopant) has been proposed as a light emitting layer. [J. Appl. Phys., 65, 3610 (198
9)]. Further, as the light emitting layer, for example, bis (2-methyl-8-quinolinolate) (4-phenylphenolate)
An organic electroluminescent device using aluminum as a host compound and an acridone derivative (for example, N-methyl-2-methoxyacridone) as a guest compound has been proposed (JP-A-8-67873). However, it is difficult to say that these light emitting elements also have sufficient light emission luminance. At present, an organic electroluminescent device that emits light with higher luminance is desired.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device which is excellent in luminous efficiency and emits light with high luminance. Another object is to provide a novel hydrocarbon compound that can be suitably used for the light-emitting element.

[0005]

Means for Solving the Problems The present inventors have made intensive studies on the organic electroluminescent device, and as a result, have completed the present invention. That is, according to the present invention, indeno [1,2,3-cd] benzo [8 ', 9'] is provided between a pair of electrodes.
Fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,2,3
organic electroluminescent device comprising at least one layer containing at least one [-lm] perylene derivative, indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno
The organic electroluminescent device according to the above, wherein the layer containing the [3 ′, 4 ′: 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative is a light-emitting layer; 2,3-cd] benzo [8 ', 9'] fluorantheno
The layer containing [3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative, further comprising a luminescent organometallic complex. Or the organic electroluminescent device described, indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno
The layer containing [3 ′, 4 ′: 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative, further comprising a triarylamine derivative, The organic electroluminescent device according to any one of the above-described items, wherein the organic electroluminescent device further includes a hole injecting and transporting layer between the pair of electrodes, and further includes the electron injecting and transporting layer between the pair of electrodes. An organic electroluminescent device according to any of the above, wherein indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno
The [3 ′, 4 ′: 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative is a compound represented by the general formula (1-A) (Formula 3). The organic electroluminescent device according to any one of the above,
It is about.

[0006]

Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. Furthermore, the present invention relates to a hydrocarbon compound represented by the general formula (1-A) (Formula 4).

[0007]

Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. )

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The organic electroluminescent device of the present invention includes an indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno between a pair of electrodes.
[3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative sandwiched at least one layer containing at least one layer. Indeno [1,2,3-c according to the present invention
d] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-
The indaceno [1,2,3-lm] perylene derivative (hereinafter abbreviated as compound A according to the present invention) is represented by the general formula (1)
And a compound having a skeleton represented by The skeleton represented by the general formula (1) may be substituted with various substituents, and the compound A according to the present invention is preferably represented by the general formula (1-A) Compound.

[0009]

Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. )

In the compound represented by the general formula (1-A), X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkyl group. Represents an alkoxy group or a substituted or unsubstituted aryl group. In the present invention, the aryl group means a carbocyclic aromatic group such as a phenyl group and a naphthyl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group and a pyridyl group. In the compound represented by the general formula (1-A), preferably, X _{1 to} X ₂₄ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms. Represents a linear, branched or cyclic alkoxy group or a substituted or unsubstituted aryl group having 4 to 20 carbon atoms.

Specific examples of X _{1 to} X ₂₄ in the general formula (1-A) include, for example, a hydrogen atom; for example, a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom;
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, te
rt-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-
Methylpentyl group, 4-methyl-2-pentyl group, 3,
3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propyl Pentyl group, n-nonyl group, 2,2-dimethylheptyl group,
2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, n-undecyl group,
1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n
-Pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl Linear, branched or cyclic alkyl groups such as groups;

For example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, n-pentyloxy, neopentyloxy, cyclopentyloxy,
n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2
-Ethylhexyloxy group, n-nonyloxy group, n-
Decyloxy group, n-undecyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy group, n-hexadecyloxy group, n-heptadecyloxy group , N-octadecyloxy group, n-eicosyloxy group and other straight-chain,
A branched or cyclic alkoxy group;

For example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4
-Ethylphenyl group, 4-n-propylphenyl group, 4
-Isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-undecylphenyl group, 4-n -Dodecylphenyl group, 4-n-
Tetradecylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethyl Phenyl group, 3,
4,5-trimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-indanyl group, 1,2,3
4-tetrahydro-5-naphthyl group, 1,2,3,4-
Tetrahydro-6-naphthyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 4-n-propoxyphenyl group, 4-isopropoxyphenyl Group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 4-n-pentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n-heptyloxyphenyl group , 4-n-octyloxyphenyl group, 4-n-
Nonyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-undecyloxyphenyl group, 4-n-
Dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group,

2,3-dimethoxyphenyl group, 2,4-
Dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy -5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 2-fluorophenyl group,
3-fluorophenyl group, 4-fluorophenyl group, 2
-Chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-trifluoromethylphenyl group, 2,4-difluorophenyl group,
2,4-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-methyl-4-
Chlorophenyl group, 2-chloro-4-methylphenyl group, 3-chloro-4-methylphenyl group, 2-chloro-
4-methoxyphenyl group, 3-methoxy-4-fluorophenyl group, 3-methoxy-4-chlorophenyl group, 3
-Fluoro-4-methoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (4'-methoxyphenyl) phenyl group, 1-naphthyl group, 2-naphthyl group, 4
-Methyl-1-naphthyl group, 4-ethoxy-1-naphthyl group, 6-n-butyl-2-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group, 2
And substituted or unsubstituted aryl groups such as -furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl and 4-pyridyl.

More preferably, a hydrogen atom, a fluorine atom,
Chlorine atom, C1-C10 alkyl group, C1-C1
An alkoxy group having 0 or an aryl group having 6 to 12 carbon atoms, more preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 6 carbon atoms,
It is an alkoxy group having 6 or an aryl group having 6 to 10 carbon atoms.

In the organic electroluminescent device of the present invention, indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ',
4 ': 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative is characterized by using at least one derivative.
Indeno [1,2,3-cd] benzo [8 ', 9'] fluoranteno [3 ',
When a 4 ': 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative is used as a light-emitting component in a light-emitting layer, it emits red light with high luminance and excellent durability, which has not existed conventionally. It is possible to provide an organic electroluminescent device having the following characteristics. Further, when a light-emitting layer is formed in combination with another light-emitting component, an organic electroluminescent element that emits white light with high luminance and excellent durability can be provided. Specific examples of the compound A according to the present invention include, for example, the following compounds (Chemical Formulas 6 to 48), but the present invention is not limited thereto.

[0017]

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[0030]

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[0035]

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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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[0052]

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[0053]

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[0054]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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The compound A according to the present invention, for example, the compound represented by the general formula (1-A) can be produced, for example, by the following method. That is, for example, 3- (3′-fluoranthenyl) benzo [k] naphtho [1 ′, 8 ′: 5,6,7] -s-indaceno represented by the general formula (2) The 1,2,3-cd] fluoranthene derivative is treated with an oxidizing agent such as aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, lead tetraacetate, or ferric chloride. ) To close the ring [for example, J. Amer. Chem. Soc., 102,
6504 (1980), Chem. Rev., 87, 357 (1987) can be referred to].

[0061]

Embedded image [In the above formula, X _{1 to} X ₂₄ represent the same meaning as in the case of the general formula (1-A)]

Incidentally, the compound represented by the general formula (2) is, for example, a boric acid compound represented by the general formula (3) (formula 50) and a general formula (4) (formula 50). 3-halogenobenzo [k] naphtho [1 ', 8': 5,6,7] -s-indaceno [1,2,3
-cd] fluoranthene derivative and, for example, a palladium compound [for example, tetrakis (triphenylphosphine)
Reaction in the presence of palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate, triethylamine) [eg, the method described in Chem. Rev., 95, 2457 (1995)]. Can be referred to].

[0063]

Embedded image [In the above formula, X _{1 to} X ₂₄ represent the same meaning as in the case of the general formula (1-A), and Z ₁ represents a halogen atom.] In the general formula (4), Z ₁ represents a halogen atom, and is preferably Represents a chlorine atom, a bromine atom and an iodine atom.

The compound represented by the general formula (2)
For example, a boric acid compound represented by the general formula (5) (Chemical Formula 51) is combined with a 3-halogenofluoranthene derivative represented by the general formula (6) (Chemical Formula 51) and, for example, a palladium compound [eg, tetrakis] (Triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate,
(For example, the method described in Chem. Rev., 95, 2457 (1995) can be referred to).

[0065]

Embedded image [In the above formula, X _{1 to} X ₂₄ represent the same meaning as in the case of the general formula (1-A), and Z ₂ represents a halogen atom.] In the general formula (6), Z ₂ represents a halogen atom, and is preferably Represents a chlorine atom, a bromine atom and an iodine atom.

The compounds represented by the general formulas (3) and (5) are, for example, more n-butyllithium than the compounds represented by the general formulas (6) and (4), respectively. Can be prepared by using a lithiated compound or a Grignard reagent that can be prepared by allowing metallic magnesium to act, for example, trimethoxyboron, triisopropoxyboron, or the like (for example, Chem. Rev., 95, 2457).
(1995).] The compound represented by the general formula (4) can be produced, for example, by the following method. That is, for example,
It can be produced by reacting the compound represented by the general formula (7) (Formula 52) with a 5-halogenoacenaphthylene derivative represented by the general formula (8) (Formula 52).

[0067]

Embedded image [In the above formula, X _{9 to} X ₂₄ represent the same meaning as in the case of the general formula (1-A), and Z ₁ represents a halogen atom.] In the general formula (8), Z ₁ represents a halogen atom, and is preferably Represents a chlorine atom, a bromine atom and an iodine atom.
The compound represented by the general formula (7) is, for example, a compound represented by the general formula (9)
It can be produced by reacting with a compound represented by the following formula (53).

[0068]

Embedded image [In the above formula, X _{11 to} X ₂₂ have the same meaning as in the case of the general formula (1-A)] The compound represented by the general formula (9) is, for example, a compound represented by the general formula (11) ) Is reacted with a pyracilloquinone derivative represented by the general formula (12) (Formula 54).
3) It can be produced by dehydrating the compound represented by (Chemical Formula 54) [for example, J. Am. Chem. Soc., 91,
918 (1969)].

[0069]

Embedded image [In the above formula, X _{12 to} X ₂₁ represent the same meaning as in the case of the general formula (1-A)]

The compound A according to the present invention may be produced in the form of a solvation with a solvent (for example, an aromatic hydrocarbon solvent such as toluene) used in some cases. The compound A according to the present invention includes such a solvate. Needless to say, a non-solvate containing no solvent is also included. In the organic electroluminescent device of the present invention, not only a non-solvate of the compound A according to the present invention but also such a solvate can be used. When the compound A according to the present invention is used in an organic electroluminescent device, a recrystallization method, a column chromatography method,
It is preferable to use a purification method such as a sublimation purification method, or a compound having an increased purity by using these methods in combination.

The organic electroluminescent element usually has at least one light-emitting layer containing at least one light-emitting component sandwiched between a pair of electrodes. In consideration of the functional levels of hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer, a hole injection transport layer containing a hole injection transport component and / or an electron may be provided as desired. An electron injection / transport layer containing an injection / transport component can also be provided. For example, when the hole injection function, hole transport function and / or electron injection function, and electron transport function of the compound used for the light emitting layer are good, the light emitting layer is formed of the hole injection transport layer and / or the electron injection transport layer. The element can also be configured to serve as Of course, depending on the case, a structure of a device (single-layer device) without both the hole injection transport layer and the electron injection transport layer may be employed. Also,
Each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single-layer structure or a multilayer structure. In the layer, a layer having an injection function and a layer having a transport function may be separately provided.

In the organic electroluminescent device of the present invention, the compound A according to the present invention is preferably used for a hole injection / transport component, a light emitting component or an electron injection / transport component, and is preferably used for a hole injection / transport component or a light emitting component. Is more preferable,
It is particularly preferable to use it for a light emitting component. In the organic electroluminescent device of the present invention, the compound A according to the present invention may be used alone or in combination.

The structure of the organic electroluminescent device of the present invention is not particularly limited.
Hole injection / transport layer / emission layer / electron injection / transport layer / cathode device (FIG. 1), (B) anode / hole injection / transport layer / emission layer / cathode device (FIG. 2), (C) anode / emission Layer / electron injection / transport layer / cathode type device (FIG. 3), (D) anode / light emitting layer / cathode type device (FIG. 4) and the like. Further, the device is of a type in which a light emitting layer is sandwiched between electron injection and transport layers (E).
Anode / hole injection / transport layer / electron injection / transport layer / emission layer / electron injection / transport layer / cathode type device (FIG. 5).
The element configuration of the (D) type includes an element of a type in which a light-emitting component is sandwiched between a pair of electrodes in a single layer form. Further, for example, (F) a hole injection / transport component, Component (FIG. 6) sandwiched between a pair of electrodes in the form of a single layer in which the component and the electron injecting and transporting component are mixed. There is an element of the type sandwiched between (FIG. 7) and (H) an element of the type sandwiched between a pair of electrodes (FIG. 8) in the form of a single layer in which a light emitting component and an electron injection transport component are mixed.

The organic electroluminescent device of the present invention is not limited to these device configurations, and each device may be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers. Can be. In each type of device, a mixed layer of a hole injection transport component and a light emitting component is provided between the hole injection transport layer and the light emitting layer, and / or
A mixed layer of a light emitting component and an electron injection / transport component can be provided between the light emitting layer and the electron injection / transport layer. More preferred configurations of the organic electroluminescent element include (A) type element, (B) type element, (C) type element, (E) type element, (F) type element,
(G) type element or (H) type element, more preferably (A) type element, (B) type element, (C) type element,
(F) type element or (H) type element. As the organic electroluminescent device of the present invention, for example, (A) anode / hole injection / transport layer / emission layer / electron injection / transport layer / cathode device shown in FIG. 1 will be described. In FIG. 1, 1
Is a substrate, 2 is an anode, 3 is a hole injection transport layer, 4 is a light emitting layer,
Reference numeral 5 denotes an electron injection / transport layer, 6 denotes a cathode, and 7 denotes a power supply.

The electroluminescent device of the present invention is preferably supported on a substrate 1. The substrate is not particularly limited, but it is preferably transparent or translucent. Plastic sheets (eg, sheets of polyester, polycarbonate, polysulfone, polymethyl methacrylate, polypropylene, polyethylene, etc.), translucent plastic sheets,
Quartz, transparent ceramics, or a composite sheet obtained by combining them can be used. Further, on the substrate, for example, a color filter film, a color conversion film,
Emission color can also be controlled by combining dielectric reflection films.

As the anode 2, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively large work function as an electrode material. As the electrode material used for the anode, for example, gold, platinum, silver, copper, cobalt, nickel,
Palladium, vanadium, tungsten, tin oxide, zinc oxide, ITO (indium tin oxide), polythiophene, polypyrrole, and the like can be given. These electrode substances may be used alone or in combination of two or more. The anode can be formed on a substrate by using such an electrode material, for example, by a method such as an evaporation method or a sputtering method. Further, the anode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the anode is preferably several hundred Ω.
/ □ or less, more preferably about 5 to 50Ω / □. The thickness of the anode depends on the material of the electrode substance to be used, but is generally about 5 to 1000 nm, more preferably,
It is set to about 10 to 500 nm.

The hole injection / transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes (holes) from the anode and a function of transporting the injected holes. The hole injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having a hole injecting and transporting function (for example, phthalocyanine derivative, triarylmethane derivative, triarylamine derivative, oxazole derivative, hydrazone derivative, stilbene derivative) , Pyrazoline derivatives, polysilane derivatives, polyphenylenevinylene and its derivatives,
Polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, and the like). The compounds having a hole injection / transport function may be used alone or in combination of two or more.

Other compounds having a hole injection / transport function used in the present invention include triarylamine derivatives (for example, 4,4′-bis [N-phenyl-N- (4 ″)).
-Methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N-
(3 "-methoxyphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (1 "-naphthyl) amino] biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] Biphenyl, 1,1-bis [4 ′-[N, N-di (4 ″ -methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 "-N-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-
N, N-bis [4 ″, 4 ″ ′-bis [N ′, N′-di (4-methylphenyl) amino] biphenyl-4-yl] aniline, N, N′-bis [4- (diphenyl Amino) phenyl] -N, N′-diphenyl-1,3-diaminobenzene, N, N′-bis [4- (diphenylamino) phenyl] -N, N′-diphenyl-1,4-diaminobenzene, 5 , 5 "-bis [4- (bis [4-methylphenyl] amino) phenyl] -2,2 ': 5',
2 "-terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4 ', 4" -tris (N-carbazolyyl) triphenylamine, 4,4', 4 "-
Tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine, 4,4 ′, 4 ″ -tris [N, N-bis (4 ′ ″-tert-butylbiphenyl-
4 ""-yl) amino] triphenylamine, 1,3
5-tris [N- (4'-diphenylaminophenyl)
-N-phenylamino] benzene), polythiophene and derivatives thereof, and poly-N-vinylcarbazole derivatives are preferred. When the compound A according to the present invention is used in combination with another compound having a hole injecting and transporting function, the proportion of the compound A according to the present invention in the hole injecting and transporting layer is preferably 0.1 to 40% by weight. Prepare to about.

The light emitting layer 4 has a hole and electron injection function,
This is a layer containing a compound having a transport function thereof and a function of generating excitons by recombination of holes and electrons. The light-emitting layer is formed of the compound A according to the present invention and / or a compound having a light-emitting function (eg, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [eg, rubrene, anthracene, tetracene, pyrene). , Perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclohexadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) ) Benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl], a triarylamine derivative (for example, the compounds described above as compounds having a hole injecting and transporting function), and organometallic complexes [For example, Tris (8- Rirato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2-
Zinc salt of (2′-hydroxyphenyl) benzoxazole, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine, 3
-Hydroxyflavone zinc salt, 5-hydroxyflavone beryllium salt, 5-hydroxyflavone aluminum salt], stilbene derivatives [for example, 1,1,4,4
-Tetraphenyl-1,3-butadiene, 4,4'-bis (2,2-diphenylvinyl) biphenyl, 4,4 '
-Bis [(1,1,2-triphenyl) ethenyl] biphenyl],

Coumarin derivatives [for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 10
6, Coumarin 138, Coumarin 151, Coumarin 15
2, Coumarin 153, Coumarin 307, Coumarin 31
1. Coumarin 314, Coumarin 334, Coumarin 33
8, coumarin 343, coumarin 500], pyran derivatives [eg, DCM1, DCM2], oxazone derivatives [eg, Nile Red], benzothiazole derivatives,
Benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamate derivatives, poly-
N-vinyl carbazole and its derivatives, polythiophene and its derivatives, polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and Derivatives, polythienylenevinylene and its derivatives)
Can be formed using at least one of them.

In the organic electroluminescent device of the present invention, the light emitting layer preferably contains the compound A of the present invention. When the compound A according to the present invention and a compound having another light-emitting function are used in combination, the ratio of the compound A according to the present invention in the light-emitting layer is preferably 0.001 to 99.99.
About 9% by weight, more preferably 0.01 to 99.99
% By weight, more preferably about 0.1 to 99.9% by weight.

As the other compound having a light-emitting function used in the present invention, a light-emitting organic metal complex is preferable. For example, J. Appl. Phys., 65, 3610 (1989);
As described in JP-A-143332, the light-emitting layer may be composed of a host compound and a guest compound (dopant).

A light emitting layer can be formed by using the compound A according to the present invention as a host compound, and further, a light emitting layer can be formed by using a compound A as a guest compound.
When the light emitting layer is formed using the compound A according to the present invention as a guest compound, examples of the host compound include the compounds having the other light emitting functions described above.
For example, a luminescent organometallic complex or the above triarylamine derivative is more preferred. In this case, the compound A according to the present invention is preferably used in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, based on the luminescent organometallic complex or the triarylamine derivative. Particularly preferably, about 0.1 to 20% by weight is used.

The luminescent organometallic complex used in combination with the compound A according to the present invention is not particularly limited, but a luminescent organoaluminum complex is preferable, and a luminescent organometallic complex having a substituted or unsubstituted 8-quinolinolate ligand is preferred. Organic aluminum complexes are more preferred. Preferred luminescent organic metal complexes include, for example, luminescent organic aluminum complexes represented by general formulas (a) to (c). (Q) _3- Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) _2- Al-OL (b) (wherein Q represents substituted 8 -Represents a quinolinolate ligand, O
-L is a phenolate ligand, and L represents a hydrocarbon group having 6 to 24 carbon atoms including a phenyl moiety.) (Q) _2- Al-O-Al- (Q) ₂ (c) Represents a substituted 8-quinolinolate ligand)

As specific examples of the luminescent organometallic complex, for example, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, tris ( 3,4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum,

Bis (2-methyl-8-quinolinolate)
(Phenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3
-Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (4-methylphenolate)
Aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (4-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolate) (2
3-dimethylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,6-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(3,5-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,5-di-te
rt-butylphenolato) aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-triphenylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1
-Naphtholate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2-naphtholate) aluminum, bis (2,4-dimethyl-8-quinolinolate)
(2-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum , Bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenylphenolate) )aluminum,

Bis (2-methyl-8-quinolinolate)
Aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, Bis (2-methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-
4-ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolate) aluminum, bis (2-
Methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-
Quinolinolate) aluminum, bis (2-methyl-5)
-Trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum. Of course, the luminescent organometallic complex may be used alone or in combination.

The electron injecting / transporting layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and a function of transporting the injected electrons. The electron injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having an electron injecting and transporting function (eg, an organometallic complex [eg, tris (8-quinolinolate) aluminum, bis (10-benzo [h] quinolinolate) ) Beryllium, 5
Beryllium salt of -hydroxyflavone, aluminum salt of 5-hydroxyflavone], oxadiazole derivative [for example, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazole] -2'-yl] benzene], a triazole derivative [eg, 3-
(4′-tert-butylphenyl) -4-phenyl-5-
(4 "-biphenyl) -1,2,4-triazole],
Triazine derivatives, perylene derivatives, quinoline derivatives,
Quinoxaline derivative, diphenylquinone derivative, nitro-substituted fluorenone derivative, thiopyrandioxide derivative, etc.). When the compound A according to the present invention and another compound having an electron injecting and transporting function are used in combination, the proportion of the compound A according to the present invention in the electron injecting and transporting layer is preferably from 0.1 to 0.1.
It is adjusted to about 40% by weight. In the present invention, the compound A according to the present invention and an organometallic complex [for example, the compounds represented by the general formulas (a) to (c)] are used in combination.
It is preferable to form an electron injection transport layer.

As the cathode 6, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively small work function as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium,
Manganese, yttrium, aluminum, an aluminum-lithium alloy, an aluminum-calcium alloy, an aluminum-magnesium alloy, a graphite thin film, and the like can be given. These electrode substances may be used alone or in combination. The cathode is
Using these electrode materials, for example, a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method,
It can be formed on the electron injection transport layer by a method such as a cluster ion beam method. Further, the cathode may have a single-layer structure or a multilayer structure. Note that the sheet electric resistance of the cathode is preferably set to several hundred Ω / □ or less. The thickness of the cathode depends on the material of the electrode substance used, but is generally about 5 to 1000 nm,
More preferably, it is set to about 10 to 500 nm.
In order to efficiently extract light emitted from the organic electroluminescent device, it is preferable that at least one of the anode and the cathode is transparent or translucent, and the transmittance of emitted light is generally 70% or more. It is more preferable to set the material and thickness of the anode.

Further, in the organic electroluminescent device of the present invention, at least one layer may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited and includes, for example, rubrene,
Nickel complexes, diphenylisobenzofuran and the like can be mentioned, and rubrene is particularly preferred. The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer.
For example, when a singlet quencher is contained in the hole injecting and transporting layer, it may be contained uniformly in the hole injecting and transporting layer.
(Electron injection / transport layer having a light emitting function). The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.05 to 3% by weight of the total amount of a contained layer (for example, a hole injection transport layer).
0% by weight, more preferably 0.1 to 20% by weight.

The method of forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited. For example, a vacuum evaporation method, an ionization evaporation method, a solution coating method (for example, spin coating, casting, Method, dip coating method,
It can be manufactured by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, an inkjet method, or the like. When each layer is formed by a vacuum deposition method, the conditions for the vacuum deposition are not particularly limited, but the vacuum deposition is performed under a vacuum of about 10 ^-5 Torr and 50 to 6 Torr.
Boat temperature of about 00 ° C (evaporation source temperature), -50 to 30
It is preferable to carry out at a substrate temperature of about 0 ° C. and at a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as a hole injection transport layer, a light emitting layer, an electron injection transport layer,
By continuously forming the organic electroluminescent element under vacuum, an organic electroluminescent device having more excellent various characteristics can be manufactured. When each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer is formed using a plurality of compounds by a vacuum evaporation method,
It is preferable that the temperature of each boat containing the compound be individually controlled and co-evaporated.

When each layer is formed by a solution coating method, the components forming each layer or the components and a binder resin are dissolved or dispersed in a solvent to form a coating solution. Examples of the binder resin that can be used for each of the hole injection transport layer, the light emitting layer, and the electron injection transport layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, and polymethyl methacrylate. , Polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylenevinylene and its derivatives, polyfluorene and its derivatives, polythienyl And high molecular compounds such as lenvinylene and derivatives thereof. The binder resin may be used alone or in combination of two or more.

When each layer is formed by a solution coating method, the components forming each layer or the components and a binder resin are combined with a suitable organic solvent (for example, hexane, octane, decane, toluene, xylene, ethylbenzene, 1-methylnaphthalene, etc.). Hydrocarbon solvents, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone, for example, dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, halogens such as chlorobenzene, dichlorobenzene, chlorotoluene Hydrocarbon solvents, for example, ethyl acetate, butyl acetate, ester solvents such as amyl acetate, for example, methanol, propanol, butanol, pentanol,
Alcohol solvents such as hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, and ethylene glycol, for example, ether solvents such as dibutyl ether, tetrahydrofuran, dioxane, and anisole, for example, N, N-dimethylformamide, N, N-
Dimethylacetamide, 1-methyl-2-pyrrolidone,
A polar solvent such as 1-methyl-2-imidazolidinone and dimethyl sulfoxide) and / or dissolved or dispersed in water to form a coating solution, and a thin film can be formed by various coating methods.

The method of dispersion is not particularly limited. For example, the particles can be dispersed into fine particles using a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like. The concentration of the coating solution is not particularly limited, and can be set to a concentration range suitable for producing a desired thickness depending on a coating method to be performed, and is generally about 0.1 to 50% by weight. Preferably, the solution concentration is about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin is not particularly limited. 5) to 99.9% by weight
Level, preferably about 10 to 99.9% by weight, more preferably about 15 to 90% by weight.

The thicknesses of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer are not particularly limited, but are generally preferably set to about 5 nm to 5 μm.
A protective layer (sealing layer) may be provided on the manufactured device for the purpose of preventing contact with oxygen or moisture, or the device may be formed of, for example, paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite, or the like. It can be protected by being enclosed in an inert substance such as a contained fluorocarbon oil. Examples of the material used for the protective layer include organic polymer materials (for example, fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene) , Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide,
Metal sulfide), furthermore, a photocurable resin, and the like. The material used for the protective layer may be used alone or in combination of two or more. The protective layer may have a single-layer structure or a multilayer structure.

Further, a metal oxide film (for example, an aluminum oxide film) or a metal fluoride film may be provided as a protective layer on the electrode. Also, for example, on the surface of the anode,
For example, an interface layer (intermediate layer) composed of an organic phosphorus compound, polysilane, an aromatic amine derivative, and a phthalocyanine derivative
Can also be provided. Further, electrodes, eg, anodes, can be used by treating the surface with, eg, acid, ammonia / hydrogen peroxide, or plasma.

The organic electroluminescent device of the present invention is generally used as a DC-driven device, but can also be used as a pulse-driven or AC-driven device.
The applied voltage is generally about 2 to 30V. The organic electroluminescent device of the present invention can be used for, for example, a panel light source, various light emitting devices, various display devices, various labels, various sensors, and the like.

[0098]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Production Examples and Examples, but of course, the present invention is not limited thereto. Production Example 1 Production of Compound of Exemplified Compound A-1 3- (3′-Fluoranthenyl) benzo [k] naphtho [1 ′,
8 ': 5,6,7] -s-indaceno [1,2,3-cd] fluoranthene 6.51 g and cobalt trifluoride 11.59 g were stirred in 100 ml of trifluoroacetic acid at room temperature for 5 hours. After adding 500 ml of water, the precipitated crystals were collected by filtration and washed with water. The crystals were subjected to silica gel column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to obtain 3.14 g of a compound of Exemplified Compound A-1 as purple crystals. Mass spectrometry: m / z = 648 Elemental analysis: (C ₅₂ as H ₂₄₎ C H Calculated (%) 96.27 3.73 Found (%) 96.32 3.68 mp 250 ° C. or higher In addition, Compound Sublimed under the conditions of 500 ° C. and 10 ⁻⁵ Torr. Absorption maximum (in toluene) 604 nm

Production Examples 2 to 50 In Production Example 1, 3- (3'-fluoranthenyl) benzo [k] naphtho [1 ', 8': 5,6,7] -s-indaceno [1,2, Three
-cd] Instead of using fluoranthene, various 3-
(3′-Fluoranthenyl) benzo [k] naphtho [1 ′, 8 ′:
According to the method described in Production Example 1, except that a 5,6,7] -s-indaceno [1,2,3-cd] fluoranthene derivative was used, various indeno [1,2,3-cd] benzo [ 8 ′, 9 ′] Fluorantheno [3 ′, 4 ′: 5,6,7] -s-indaceno [1,2,3-lm] perylene derivative was prepared. In Table 1 (Tables 1 to 10), the used 3- (3'-fluoranthenyl) benzo [k] naphtho [1 ', 8': 5,6,7] -s-indaceno [1,2 , 3-cd] fluoranthene derivative and the produced indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1, [2,3-lm] perylene derivatives are indicated by exemplified compound numbers. The maximum absorption (nm) in toluene is also shown. The produced compounds were purple crystals, and the melting points of those compounds were 250 ° C. or higher.

[0100]

[Table 1]

[0101]

[Table 2]

[0102]

[Table 3]

[0103]

[Table 4]

[0104]

[Table 5]

[0105]

[Table 6]

[0106]

[Table 7]

[0107]

[Table 8]

[0108]

[Table 9]

[0109]

[Table 10]

Example 1 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolato) aluminum and indeno [1,2,3-cd] benzo were formed thereon.
[8 ', 9'] Fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm] perylene (compound of Exemplified Compound No. A-1) was used in different evaporation sources From, deposition rate 0.2nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 0.5)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
Red light emission of 480 cd / m ² was confirmed.

Examples 2 to 50 In Example 1, instead of using the compound of Exemplified Compound A-1 in forming the light emitting layer, Exemplified Compound No. A
-8 (Example 2), Exemplified Compound No. A-10 (Example 3), Exemplified Compound No. A-12 (Example 4), Exemplified Compound No. A-18 (Example 5) ), Compound of Exemplified Compound No. A-19 (Example 6), compound of Exemplified Compound No. A-25 (Example 7),
Compound of Exemplified Compound No. A-29 (Example 8), Compound of Exemplified Compound No. A-34 (Example 9), Compound of Exemplified Compound No. B-1 (Example 10), Exemplified Compound No. B-
Compound No. 3 (Example 11), Compound No. B-8 (Example 12), Compound No. C-1 (Example 13), Compound No. C-4 (Example 14) Compound of Exemplified Compound No. C-6 (Example 1)
5), Compound of Exemplified Compound No. C-7 (Example 16),
Compound of Exemplified Compound No. C-10 (Example 17), Compound of Exemplified Compound No. C-12 (Example 18), Compound of Exemplified Compound No. C-16 (Example 19), Compound of Exemplified Compound No. C-18 (Example 20), Exemplified Compound No. C
Compound No. -24 (Example 21), Exemplified Compound No. C-3
Compound No. 0 (Example 22), Compound Compound No. C-38 (Example 23), Compound Compound No. C-40 (Example 24), Compound Compound No. C-42 (Example 25) Compound of Exemplified Compound No. C-47 (Example 26), Compound of Exemplified Compound No. C-49 (Example 27), Compound of Exemplified Compound No. C-50 (Example 2)
8), Compound of Exemplified Compound No. C-51 (Example 2)
9), Compound of Exemplified Compound No. C-52 (Example 3)
0), Compound of Exemplified Compound No. C-58 (Example 3)
1), Compound of Exemplified Compound No. C-60 (Example 3)
2), compound of Exemplified Compound No. D-1 (Example 33),
Compound of Exemplified Compound No. D-2 (Example 34), Compound of Exemplified Compound No. D-5 (Example 35), Compound of Exemplified Compound No. D-8 (Example 36), Exemplified Compound No. D-
15 compounds (Example 37), Exemplified Compound No. D-17
(Example 38), compound of Exemplified Compound No. E-1 (Example 39), compound of Exemplified Compound No. E-3 (Example 40), compound of Exemplified Compound No. E-4 (Example 4)
1) a compound of Exemplified Compound No. E-5 (Example 42);
Compound of Exemplified Compound No. E-7 (Example 43), Compound of Exemplified Compound No. E-9 (Example 44), Compound of Exemplified Compound No. E-10 (Example 45), Exemplified Compound No. E
Compound No. -13 (Example 46), Exemplified Compound No. E-1
Compound No. 7 (Example 47), Compound Compound No. E-18 (Example 48), Compound Compound No. E-23 (Example 49), Compound Compound No. E-24 (Example 50) An organic electroluminescent device was produced by the method described in Example 1 except that was used. When a DC voltage of 12 V was applied to each element under a dry atmosphere, orange-red to red light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2 (Tables 11 and 12).

Comparative Example 1 In Example 1, when forming the light-emitting layer, the compound of Exemplified Compound No. A-1 was not used, and bis (2-methyl-
An organic electroluminescent device was prepared by the method described in Example 1, except that only 8-quinolinolate) (4-phenylphenolate) aluminum was used to form a light emitting layer by vapor deposition to a thickness of 50 nm. 1
When a DC voltage of 2 V was applied, blue light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2.

Comparative Example 2 In Example 1, instead of using the compound of Exemplified Compound No. A-1 in forming the light emitting layer, N-methyl-
An organic electroluminescent device was produced by the method described in Example 1 except that 2-methoxyacridone was used. When a DC voltage of 12 V was applied to this device under a dry atmosphere, blue light emission was confirmed. Further investigate its properties,
The results are shown in Table 2.

[0114]

[Table 11]

[0115]

[Table 12]

Example 51 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-8 were further deposited thereon from a different evaporation source at a deposition rate of 0. 2nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
Red light emission of 350 cd / m ² was confirmed.

Example 52 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-12 were co-deposited from different deposition sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere,
A current of mA / cm ² flowed. Brightness 2410 cd / m ²
Red light emission was confirmed.

Example 53 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. A-19 were formed thereon. From different evaporation sources, a deposition rate of 0.2 nm / sec.
Co-deposition to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2
Red light emission of 360 cd / m ² was confirmed.

Example 54 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-29 were deposited thereon from different evaporation sources at a deposition rate of 0,0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 6.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm /
The film was deposited to a thickness of 50 nm in sec to form an electron injecting and transporting layer. Further, magnesium and silver were further deposited thereon at a vapor deposition rate of 0.1 mm.
Co-deposition to a thickness of 200 nm at 2 nm / sec (weight ratio 1
0: 1) to form a cathode to produce an organic electroluminescent device.
In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank.
When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Red light emission with a luminance of 2370 cd / m ² was confirmed.

Example 55 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-6 were deposited thereon from different evaporation sources at a deposition rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
10) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm /
A co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm in sec to form an organic electroluminescent device as a cathode. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed.
Red light emission with a luminance of 2320 cd / m ² was confirmed.

Example 56 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-10 were deposited thereon from different evaporation sources at a deposition rate of 0.1 mm.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 1.0) to obtain a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver were further deposited thereon at a vapor deposition rate of 0.1 mm.
Co-deposition to a thickness of 200 nm at 2 nm / sec (weight ratio 1
0: 1) to form a cathode to produce an organic electroluminescent device.
In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank.
When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Red light emission with a luminance of 2390 cd / m ² was confirmed.

Example 57 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. C-12 were further deposited thereon from different evaporation sources at a deposition rate of 0. 2nm / se
Co-deposition to a thickness of 50 nm with c (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2
Red light emission of 330 cd / m ² was confirmed.

Example 58 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-24 were co-deposited from different deposition sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio: 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere,
A current of mA / cm ² flowed. Brightness 2340 cd / m ²
Red light emission was confirmed.

Example 59 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. C-30 were formed thereon. From different evaporation sources, a deposition rate of 0.2 nm / sec.
Co-deposition to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
Red light emission of 350 cd / m ² was confirmed.

Example 60 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. D-1 were deposited thereon from different evaporation sources at a deposition rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
6.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm.
/ Sec to co-evaporate to a thickness of 200nm (weight ratio 10: 1)
This was used as a cathode to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed.
Red light emission with a luminance of 2360 cd / m ² was confirmed.

Example 61 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. D-8 were deposited thereon from different evaporation sources at an evaporation rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
10) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm /
A co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm in sec to form an organic electroluminescent device as a cathode. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed.
Red light emission with a luminance of 2360 cd / m ² was confirmed.

Example 62 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-4 were deposited thereon from different evaporation sources at an evaporation rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
1.0) to form a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm.
/ Sec to co-evaporate to a thickness of 200nm (weight ratio 10: 1)
This was used as a cathode to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed.
Red light emission with a luminance of 2290 cd / m ² was confirmed.

Example 63 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. E-7 were further deposited thereon from different evaporation sources at a deposition rate of 0. 2nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
Red light emission of 360 cd / m ² was confirmed.

Example 64 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-10 were co-deposited from different deposition sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio: 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere,
A current of mA / cm ² flowed. Brightness 2410 cd / m ²
Red light emission was confirmed.

Example 65 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. E-17 were formed thereon. From different evaporation sources, a deposition rate of 0.2 nm / sec.
Co-deposition to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 53 mA / cm ² flowed. Brightness 2
Red light emission of 340 cd / m ² was confirmed.

Example 66 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-18 were deposited thereon from different evaporation sources at a deposition rate of 0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 6.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm /
The film was deposited to a thickness of 50 nm in sec to form an electron injecting and transporting layer. Further, magnesium and silver were further deposited thereon at a vapor deposition rate of 0.1 mm.
Co-deposition to a thickness of 200 nm at 2 nm / sec (weight ratio 1
0: 1) to form a cathode to produce an organic electroluminescent device.
In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank.
When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Red light emission with a luminance of 2320 cd / m ² was confirmed.

Example 67 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-23 were further deposited thereon from different evaporation sources at a deposition rate of 0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0:10) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / se.
The film was vapor-deposited to a thickness of 50 nm at c to form an electron injection transport layer.
Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 n.
Co-deposition at 200 m / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Red light emission with a luminance of 2310 cd / m ² was confirmed.

Example 68 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, a compound of Exemplified Compound No. D-1 was further deposited thereon with a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form a light emitting layer. Then, thereover, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazol-2′-yl]
Benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further on that,
Magnesium and silver are deposited at a deposition rate of 0.2 nm / sec.
Co-deposit (weight ratio 10: 1) to a thickness of nm to form a cathode,
An organic electroluminescent device was manufactured. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 42 mA / cm ² flowed. Brightness 1860c
Red light emission of d / m ² was confirmed.

Example 69 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, the compound of Exemplified Compound No. E-4 was deposited on the ITO transparent electrode to a thickness of 55 nm at a deposition rate of 0.2 nm / sec to form a light emitting layer. Then, on top of that, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-
[Oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the produced organic electroluminescent device under a dry atmosphere, 65 mA / c was obtained.
m ² of current flowed. Red light emission with a luminance of 1550 cd / m ² was confirmed.

Example 70 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4 ′, 4 ″ -tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec.
Then, it was deposited to a thickness of 50 nm to form a first hole injection transport layer. Then, 4,4'-bis [N-phenyl-N-
(1 "-naphthyl) amino] biphenyl and the compound of Exemplified Compound No. A-1 were obtained from different evaporation sources at an evaporation rate of 0.1.
Co-deposition to a thickness of 20 nm at 2 nm / sec (weight ratio 10
0: 5) to form a light-emitting layer also serving as a second hole injection / transport layer. Then, on top of this, tris (8-quinolinolate)
Aluminum is deposited at 50 nm at a deposition rate of 0.2 nm / sec.
To form an electron injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 00 nm to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 63 mA / cm ² flowed. Brightness 255
Red light emission of 0 cd / m ² was confirmed.

Examples 71 to 92 In Example 70, instead of using the compound of Exemplified Compound A-1 in forming the light emitting layer, the compound of Exemplified Compound No. A-10 (Example 71) and the Exemplified Compound No. A −
Compound No. 18 (Example 72), Exemplified Compound No. A-25
(Example 73), compound of Exemplified Compound No. B-1 (Example 74), compound of Exemplified Compound No. B-8 (Example 75), compound of Exemplified Compound No. C-1 (Example 7)
6), compound of Exemplified Compound No. C-4 (Example 77),
Compound of Exemplified Compound No. C-10 (Example 78), Compound of Exemplified Compound No. C-16 (Example 79), Compound of Exemplified Compound No. C-47 (Example 80), Compound of Exemplified Compound No. D-1 (Example 81), Exemplified Compound No. D-
Compound No. 5 (Example 82), Compound Compound No. D-8 (Example 83), Compound Compound No. D-15 (Example 84), Compound Compound No. D-17 (Example 85) Compound of Exemplified Compound No. E-1 (Example 8
6), a compound of Exemplified Compound No. E-3 (Example 87),
Compound of Exemplified Compound No. E-4 (Example 88), Compound of Exemplified Compound No. E-9 (Example 89), Compound of Exemplified Compound No. E-10 (Example 90), Exemplified Compound No. E
Compound No. -13 (Example 91), Exemplified Compound No. E-1
Example 7 except that the compound of Example 8 (Example 92) was used.
An organic electroluminescent device was produced by the method described in No. 0. When a DC voltage of 12 V was applied to each element under a dry atmosphere, orange-red to red light emission was confirmed. The characteristics were further examined, and the results are shown in Table 3 (Table 13).

[0137]

[Table 13]

Example 93 A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50,000), 1,1,4,4-tetraphenyl-1,
3-butadiene (blue light-emitting component), coumarin 6 ["3
-(2′-benzothiazolyl) -7-diethylaminocoumarin ”(green light-emitting component)] and the compound of Exemplified Compound No. A-18 at a weight ratio of 100: 5: 3:
Using a 3% by weight dichloroethane solution containing 2 parts by weight, a 400 nm light emitting layer was formed by dip coating. Next, after fixing the glass substrate having the light emitting layer to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was set to 3 × 10
^The pressure was reduced to ^-6 Torr. Further, on the light emitting layer,
(4′-tert-butylphenyl) -4-phenyl-5-
After depositing (4 "-biphenyl) -1,2,4-triazole at a deposition rate of 0.2 nm / sec to a thickness of 20 nm, tris (8-quinolinolato) aluminum is further deposited thereon at a deposition rate of 0.2 nm. An electron injecting and transporting layer was deposited at a thickness of 2 nm / sec at a thickness of 30 nm, and magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 00 nm to produce an organic electroluminescent device. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 63 mA / cm ² flowed. Brightness 124
White light emission of 0 cd / m ² was confirmed.

Examples 94 to 102 In Example 93, instead of using the compound of Exemplified Compound No. A-18, the compound of Exemplified Compound No. A-19 (Example 94) and the compound of Exemplified Compound No. A-29 (Ex. Example 95), compound of Exemplified Compound No. C-18 (Example 96), compound of Exemplified Compound No. C-30 (Example 9)
7), Compound of Exemplified Compound No. C-49 (Example 9)
8), Compound of Exemplified Compound No. D-5 (Example 99),
Example 93 except that the compound of Exemplified Compound No. D-8 (Example 100), the compound of Exemplified Compound No. E-7 (Example 101), and the compound of Exemplified Compound No. E-9 (Example 102) were used. An organic electroluminescent device was produced by the method described in (1). When a DC voltage of 12 V was applied to each device under a dry atmosphere, white light emission was observed.
The characteristics were further examined, and the results are shown in Table 4 (Table 14).

[0140]

[Table 14]

Example 103 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,3-bis [5 '-(p-tert-butylphenyl) -1,3,4-oxadiazole-2'-
[Il] benzene and a compound of Exemplified Compound No. C-12 were formed by dip coating using a 3% by weight dichloroethane solution containing 100: 30: 3 by weight to form a 300 nm light emitting layer. Next, after fixing the glass substrate having the light emitting layer to the substrate holder of the vapor deposition apparatus, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were co-deposited (weight ratio: 10: 1) to a thickness of 200 nm at a deposition rate of 0.2 nm / sec to form an organic electroluminescent device. In a dry atmosphere, add 1
When a DC voltage of 5 V was applied, a current of 67 mA / cm ² flowed. Red light emission with a luminance of 1450 cd / m ² was confirmed.

Comparative Example 3 In Example 103, 1,1,4,4 was used instead of the compound of Exemplified Compound No. C-12 in forming the light emitting layer.
An organic electroluminescent device was produced by the method described in Example 103 except that -tetraphenyl-1,3-butadiene was used. When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, the voltage was 86 mA / c.
m ² of current flowed. Blue light emission with a luminance of 760 cd / m ² was confirmed.

Example 104 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight: 50,000),
4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, bis (2-methyl-8-
Quinolinolate) aluminum-μ-oxo-bis (2
-Methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. D-8 were each added at a weight ratio of 10
Using a 3% by weight dichloroethane solution containing 0: 40: 60: 1 at a ratio of 30% by a dip coating method.
A 0 nm light emitting layer was formed. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device,
The pressure in the evaporation tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-evaporation (weight ratio 10: 1) was carried out to a thickness of 200 nm at c to obtain a cathode, thereby producing an organic electroluminescent device. When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 62 mA / cm ² flowed. Red light emission with a luminance of 980 cd / m ² was confirmed.

[0144]

According to the present invention, it has become possible to provide an organic electroluminescent device having excellent light emission luminance. Further, it has become possible to provide a hydrocarbon compound suitable for the light-emitting element.

[Brief description of the drawings]

FIG. 1 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 2 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 3 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 4 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 5 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 6 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 7 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 8 is a schematic structural diagram of an example of an organic electroluminescent device.

[Explanation of symbols]

 1: substrate 2: anode 3: hole injection / transport layer 3a: hole injection / transport component 4: light emitting layer 4a: light emitting component 5: electron injection / transport layer 5 ': electron injection / transport layer 5a: electron injection / transport component 6: cathode 7: Power supply

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification FI FI Theme Court ゛ (Reference) C09K 11/06 610 C09K 11/06 610 (72) Inventor Yoshiyuki Toya Takuji Nagaura Joji, Sodegaura City, Chiba Prefecture 580 Address 32 Mitsui Chemicals Co., Ltd. (72) Inventor Masakatsu Nakatsuka 580-2 32 Mitsui Chemicals Co., Ltd. EA43 GP03

Claims (8)

[Claims] An indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,1] is provided between a pair of electrodes. An organic electroluminescent device comprising at least one layer containing at least one 2,3-lm] perylene derivative. 2. Indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm]
2. The layer containing a perylene derivative is a light emitting layer.
The organic electroluminescent device according to claim 1. 3. Indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm]
3. The organic electroluminescent device according to claim 1, wherein the layer containing a perylene derivative further contains a luminescent organometallic complex. 4. Indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm]
3. The organic electroluminescent device according to claim 1, wherein the layer containing a perylene derivative further contains a triarylamine derivative. 5. The organic electroluminescent device according to claim 1, further comprising a hole injection / transport layer between the pair of electrodes. 6. The organic electroluminescent device according to claim 1, further comprising an electron injection / transport layer between the pair of electrodes. 7. Indeno [1,2,3-cd] benzo [8 ', 9'] fluorantheno [3 ', 4': 5,6,7] -s-indaceno [1,2,3-lm]
The organic electroluminescent device according to any one of claims 1 to 6, wherein the perylene derivative is a compound represented by the general formula (1-A) (Formula 1). Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. ) 8. A hydrocarbon compound represented by the general formula (1-A) (formula 2). Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. )