JP2002313575A - Hydrocarbon compound and organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element with excellent emission efficiency and emitting light at high brightness, and a novel hydrocarbon compound suited for the element. SOLUTION: The organic electroluminescent element with excellent emission efficiency, which emits light at high brightness, has at least one layer containing at least one kind of benzo[4,5]indeno[1,2,3-cd]benzo[5,6]indeno[1,2,3-lm]perylene derivative and sandwiched between a pair of electrodes. A novel benzo[4,5]indeno[1,2,3-cd]benzo[5,6]indeno[1,2,3-lm]perylene derivative is also disclosed.

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 luminescent material has been developed [Appl. Phys. Lett., 51, 913 (19).
87)]. 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 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, the present invention provides at least a benzo [4,5] indeno [1,2,3-cd] benzo [5,6] indeno [1,2,3-lm] perylene derivative between a pair of electrodes. Provided is an organic electroluminescent device in which at least one layer containing one kind is sandwiched.

Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device as described above, wherein the layer containing the [5,6] indeno [1,2,3-lm] perylene derivative further contains a luminescent organometallic complex, This is a preferred embodiment.

Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device according to the above or the above, wherein the layer containing the [5,6] indeno [1,2,3-lm] perylene derivative further contains a triarylamine derivative, This is a preferred embodiment.

Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device according to the above, wherein the layer containing the [5,6] indeno [1,2,3-lm] perylene derivative is a light emitting layer.
This is a preferred embodiment of the present invention.

The above-described organic electroluminescent device having a hole injection / transport layer between a pair of electrodes is also a preferred embodiment of the present invention.

The above-mentioned or any one of the above-mentioned organic electroluminescent devices further comprising an electron injection / transport layer between a pair of electrodes is also a preferred embodiment of the present invention.

Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device according to any one of the above, wherein the [5,6] indeno [1,2,3-lm] perylene derivative is a compound represented by the general formula (1-A), This is a preferred embodiment.

[0013]

Embedded image (In the formula, X ^{1 to} X ²⁰ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. Represents.)

Further, the present invention provides a compound represented by the general formula (1-A).

[0015]

Embedded image (In the formula, X ^{1 to} X ²⁰ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. Represents.)

[0016]

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 a benzo [4,5] indeno [1,2,3-cd] benzo [5,6] indeno [1,2,3-lm] perylene derivative between a pair of electrodes. It is formed by sandwiching at least one layer containing at least one kind.

The benzo [4,5] indeno [1,2,3-] according to the present invention
cd] benzo [5,6] indeno [1,2,3-lm] perylene derivative (hereinafter abbreviated as compound A according to the present invention) is a compound having a skeleton represented by the general formula (1). It represents.

[0018]

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The skeleton represented by the general formula (1) may be substituted with various substituents.
Is preferably a compound represented by the general formula (1-A).

[0020]

Embedded image (Wherein, X ^{1 to} X ²⁰ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, 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 ²⁰ 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 ²⁰ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, Represents a linear, branched or cyclic alkoxy group having 1 to 20 or a substituted or unsubstituted aryl group having 4 to 20 carbon atoms.

The halogen atom represented by X ^{1 to} X ^{20 in} the general formula (1-A) includes a fluorine atom, a chlorine atom and a bromine atom.

Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,
Isobutyl group, sec-butyl group, tert-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-methyl Heptyl group, 2-ethylhexyl group, 2-propylpentyl 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-
Examples thereof include a linear, branched or cyclic alkyl group such as a tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

Examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, n-pentyloxy, neopentyloxy, and cyclopentyloxy. A, 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,
Linear, branched or cyclic alkoxy such as n-tetradecyloxy group, n-pentadecyloxy group, n-hexadecyloxy group, n-heptadecyloxy group, n-octadecyloxy group and n-eicosyloxy group And the like.

Examples of the aryl group include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, -N-butylphenyl group, 4-isobutylphenyl group, 4-tert-
Butylphenyl group, 4-n-pentylphenyl 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-dimethylphenyl 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-tert-butoxyphenyl 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-undecyloxy Phenyl 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 A 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, 2,4-difluorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2-
Methyl-4-chlorophenyl group, 3-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-
Substituted or unsubstituted aryl groups such as naphthyl group, 7-ethoxy-2-naphthyl group, 2-furyl group, 2-thienyl group, 3-thienyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group Can be mentioned.

More preferably, a hydrogen atom, a fluorine atom,
Chlorine atom, alkyl group having 1 to 10 carbon atoms, 1 to 1 carbon atom
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, benzo [4,5] indeno [1,2,3-cd] benzo [5,6] indeno [1,
It is characterized in that at least one 2,3-lm] perylene derivative is used. For example, benzo [4,5] indeno [1,2,3-c
When d] benzo [5,6] indeno [1,2,3-lm] perylene derivative is used as a light-emitting component in a light-emitting layer, organic electroluminescence that emits red light with high luminance and excellent durability, which has never existed before An element can be provided.

When a light emitting layer is formed in combination with another light emitting component, an organic electroluminescent element which emits white light with high luminance and excellent durability can be provided.

Specific examples of the compound A according to the present invention include the following A-1 to A-35, B-1 to B-10 and C-1
To C-62, but the present invention is not limited thereto.

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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, 3- (benzo [j] fluoranthene- represented by the following general formula (2)
The 3′-yl) benzo [k] fluoranthene derivative is converted to an oxidizing agent (eg, aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, lead tetraacetate, or ferric chloride) ) (See, for example, the method described in J. Amer. Chem. Soc., 118, 2374 (1996)).

[0061]

Embedded image (In the formula, X ^{1 to} X ²⁰ represent the same meaning as in the case of the general formula (1-A).)

The compound represented by the general formula (2) is, for example, a boric acid compound represented by the following general formula (3) and a 3-halogenobenzo [k] fluoranthene derivative represented by the following general formula (4). For example, by reacting in the presence of a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, sodium hydrogencarbonate, triethylamine). (Eg, Chem.Re
v., 95, 2457 (1995)).

[0063]

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Embedded image (In the formula, X ^{1 to} X ²⁰ 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, preferably a chlorine atom, a bromine atom and an iodine atom.

Similarly, the compound represented by the general formula (2) is, for example, a boric acid compound represented by the following general formula (5) and a 3-halogenobenzo [j] fluoranthene represented by the following general formula (6). It can also be produced using a derivative.

[0066]

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Embedded image (In the formula, X ^{1 to} X ²⁰ 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 preferably represents a chlorine atom, a bromine atom or an iodine atom.

The compounds represented by the general formulas (3) and (5) are, for example, the compounds represented by the general formulas (6) and (4)
From the compound represented by, for example, n-butyl lithium,
Lithium compounds or Grignard reagents that can be adjusted by the action of metallic magnesium and, for example, trimethoxyboron or triisopropoxyboron can be adjusted (for example, the method described in Chem. Rev., 95, 2457 (1995)). See).

The compound represented by the general formula (1-A) is, for example, a 3- (benzo [j] fluoranthene-4'-yl) benzo [k] fluoranthene derivative represented by the following general formula (7). Oxidizing agent (for example, aluminum chloride /
Cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, lead tetraacetate,
Or in the presence of ferric chloride) (for example, J. Amer. Chem. Soc., 118, 2
374 (1996)).

[0070]

Embedded image (In the formula, X ^{1 to} X ²⁰ represent the same meaning as in the case of the general formula (1-A).)

The compound represented by the general formula (7) includes, for example, a boric acid compound represented by the following general formula (8) and a 3-halogenobenzo [k] fluoranthene derivative represented by the following general formula (9). For example, by reacting in the presence of a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, sodium hydrogencarbonate, triethylamine). (Eg, Chem.Re
v., 95, 2457 (1995)).

[0072]

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Embedded image (In the formula, X ^{1 to} X ²⁰ represent the same meaning as in the case of the general formula (1-A), and Z ³ represents a halogen atom.)

In the general formula (9), Z ³ represents a halogen atom, preferably a chlorine atom, a bromine atom and an iodine atom.

Similarly, the compound represented by the general formula (7) includes, for example, a boric acid compound represented by the following general formula (10) and a 4-halogenobenzo [j] fluoranthene represented by the following general formula (11). It can also be produced using a derivative.

[0075]

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Embedded image (In the formula, X ^{1 to} X ²⁰ represent the same meaning as in the case of the general formula (1-A), and Z ⁴ represents a halogen atom.)

In the general formula (11), Z ⁴ represents a halogen atom, and preferably represents a chlorine atom, a bromine atom or an iodine atom.

The compounds represented by the general formulas (8) and (10) are, for example, n-butyllithium and metal magnesium more than the compounds represented by the general formulas (11) and (9). And a Grignard reagent that can be adjusted by the action of, for example, trimethoxyboron, triisopropoxyboron, or the like (for example, see the method described in Chem. Rev., 95, 2457 (1995)). ).

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 of the present invention but also such a solvate can be used.

When the compound A according to the present invention is used for an organic electroluminescent device, a compound having a higher purity by a recrystallization method, a column chromatography method, a sublimation purification method, or a combination thereof. It is preferred to use

The organic electroluminescent device 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 injection / transport layer containing an injection / transport component can also be provided.

For example, when the compound used in the light emitting layer has a good hole injecting function, a hole transporting function and / or an electron injecting function, and an electron transporting function, the light emitting layer is formed of the hole injecting and transporting layer and / or the electron injecting function. A structure of a device also serving as an injection / transport layer can be provided. Of course, depending on the case, a structure of a device (single-layer device) in which both the hole injection transport layer and the electron injection transport layer are not provided may be employed.

Each of the hole injecting / transporting layer, the electron injecting / transporting layer, and the light emitting layer may have a single-layer structure or a multilayer structure. The layers can be formed by separately providing a layer having an injection function and a layer having a transport function in each layer.

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, it is a device of a type in which a light emitting layer is sandwiched between electron injection 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, (FIG. 6), and a pair of electrodes in the form of a single layer in which the hole injection / transport component and the light emitting 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. Further, in each type of device, between the hole injection transport layer and the light emitting layer,
A mixed layer of a light emitting component and an electron injection / transport component may be provided between the hole injection / transport component and the light emitting component and / or between the light emitting layer and the electron injection / transport layer.

A more preferable structure of the organic electroluminescent device is as follows:
(A) element, (B) element, (C) element, (E) element, (F) element, (G) element or (H) element, and more preferably (A) element. ) Type element, (B) type element, (C) type element, (F) type element or (H) type element.

FIG. 1 shows the organic electroluminescent device of the present invention.
(A) anode / hole injection / transport layer / emission layer / electron injection / transport layer / cathode type device shown in FIG.

In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer, 5 is an electron injection / transport layer, 6
Indicates a cathode, and 7 indicates a power supply.

The electroluminescent device of the present invention is preferably supported on a substrate 1, and the substrate is not particularly limited, but is preferably transparent or translucent. Plastic sheets (eg, sheets of polyester, polycarbonate, polysulfone, polymethyl methacrylate, polypropylene, polyethylene, etc.), translucent plastic sheets,
Examples thereof include quartz, transparent ceramics, and a composite sheet obtained by combining these. 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.

Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, tin oxide, zinc oxide,
TO (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 a vapor deposition method and 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 set to several hundred Ω / □ or less, more preferably, to about 5 to 50 Ω / □.

Although the thickness of the anode depends on the material of the electrode substance to be used, it is generally set to about 5 to 1000 nm, more preferably 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 made of the compound A according to the present invention.
And / or other compounds having a hole injection / transport function (for example, phthalocyanine derivative, triarylmethane derivative, triarylamine derivative, oxazole derivative, hydrazone derivative, stilbene derivative, pyrazoline derivative, polysilane derivative, polyphenylenevinylene and derivatives thereof, Polythiophene and a derivative thereof, a poly-N-vinylcarbazole derivative, or the like). The compounds having a hole injection / transport function may be used alone or in combination.

As other compounds having a hole injecting / transporting function used in the present invention, triarylamine derivatives, polythiophenes and derivatives thereof, and poly-N-vinylcarbazole derivatives are preferable.

Examples of triarylamine derivatives include:
4,4'-bis [N-phenyl-N- (4 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] biphenyl, 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- (diphenylamino) 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 And the like.

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
It is adjusted to about 0.1 to 40% by weight.

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 comprises the compound A according to the present invention and / or
Or a compound having another light-emitting function, for example, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound, a triarylamine derivative,
Organometallic complexes, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamate derivatives, poly-N-vinylcarbazole 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 its derivatives, polythienylene vinylene and its derivatives, etc. Can be formed by using at least one of them.

Examples of the polycyclic aromatic compound include 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 and the like.

Examples of the triarylamine derivative include:
Examples of the compound having a hole injecting / transporting function include the compounds described above.

Examples of the organometallic complex include tris (8-quinolylate) aluminum, bis (10-benzo [h] quinolinolate) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzoxazole, 2- (2′- (Hydroxyphenyl) zinc salt of benzothiazole, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, 5-
Examples thereof include aluminum salts of hydroxyflavone.

The stilbene derivatives include 1,1,4,
4-tetraphenyl-1,3-butadiene, 4,4′-
Bis (2,2-diphenylvinyl) biphenyl, 4,
4'-bis [(1,1,2-triphenyl) ethenyl]
Biphenyl and the like can be mentioned.

Coumarin derivatives include 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 and the like.

Preferred examples of the pyran derivative include DCM1,
DCM2 and the like, and a preferred example of the oxazone derivative is Nile Red.

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 is used in combination with a compound having another light-emitting function, the ratio of the compound A according to the present invention in the light-emitting layer is preferably from 0.001 to 9
9.999% by weight, more preferably 0.01 to 9% by weight.
About 9.99% by weight, more preferably 0.1 to 9%
It is adjusted to about 9.9% by weight.

As the other compound having a light-emitting function used in the present invention, a light-emitting organometallic complex is preferable. For example, J. Appl. Phys., 65, 3610 (1989), JP-A-5-214.
As described in JP-A-332-332, the light-emitting layer can 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 compound A according to the present invention is used as a guest compound to form a light-emitting layer, examples of the host compound include the aforementioned compounds having another light-emitting function. Metal complexes or the aforementioned triarylamine derivatives are more preferred.

In this case, the compound A according to the present invention is compared with the luminescent organometallic complex or the triarylamine derivative.
Is preferably used in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, and particularly preferably about 0.1 to 20% by weight.

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 preferred, 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) Represents a substituted 8-quinolinolate ligand;
-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) Q represents a substituted 8-quinolinolate ligand)

Specific examples of the luminescent organometallic complex include, 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-phenylphenolate) 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-tert-butylphenolate) 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-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate)
(3-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenylphenol Late) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-di-tert-butylphenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-
Bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8)
-Quinolinolate) 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)
-Quinolinolate) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolate) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum-μ-oxo-bis (2 -Methyl-5-trifluoromethyl-8-quinolinolato) aluminum and the like. 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 made of the compound A according to the present invention.
And / or other compounds having an electron injecting and transporting function,
For example, tris (8-quinolinolate) aluminum,
Bis (10-benzo [h] quinolinolate) beryllium,
Organometallic complexes such as beryllium salt of 5-hydroxyflavone and aluminum salt of 5-hydroxyflavone;
3-bis [5 '-(p-tert-butylphenyl) -1,
Oxadiazole derivatives such as 3,4-oxadiazol-2'-yl] benzene; [for example, 3- (4'-
tert-butylphenyl) -4-phenyl-5- (4 "-
Triazole derivatives such as biphenyl) -1,2,4-triazole; triazine derivatives, perylene derivatives,
It can be formed using at least one of a quinoline derivative, a quinoxaline derivative, a diphenylquinone derivative, a nitro-substituted fluorenone derivative, and a thiopyrandioxide derivative.

When the compound A according to the present invention is used in combination with another compound having an electron injecting and transporting function, the proportion of the compound A according to the present invention in the electron injecting and transporting layer is preferably
It is adjusted to about 0.1 to 40% by weight.

In the present invention, an electron injection / transport layer is formed by using the compound A according to the present invention and an organometallic complex (for example, the compounds represented by the general formulas (a) to (c)) in combination. Is preferred.

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, and the like. Examples include yttrium, aluminum, an aluminum-lithium alloy, an aluminum-calcium alloy, an aluminum-magnesium alloy, and a graphite thin film. These electrode substances may be used alone or in combination.

The cathode is formed on the electron injecting and transporting layer by using these electrode materials by, for example, a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method, or a cluster ion beam method. Can be.

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.

Although the thickness of the cathode depends on the material of the electrode substance to be used, it is generally set to about 5 to 1000 nm, more preferably 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.
The material of the anode so that the transmittance of the emitted light is 70% or more,
It is more preferable to set the thickness.

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 injection / transport layer, the singlet quencher may be contained uniformly in the hole injection / transport layer. (An electron injection transport layer having a function).

The content of the singlet oxygen quencher is from 0.01 to 50% by weight, preferably from 0.0 to 50% by weight of the total amount constituting the contained layer (for example, the hole injection transport layer).
5 to 30% by weight, more preferably 0.1 to 20% by weight
It is.

The method for 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 (eg, a spin coating method, a cast Method, dip coating method,
It can be formed 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 evaporation method,
The conditions for vacuum deposition are not particularly limited,
It is preferable to carry out under a vacuum of about -3 Pa, a boat temperature (evaporation source temperature) of about 50 to 600 ° C., a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. .

In this case, the layers such as the hole injecting / transporting layer, the light emitting layer, and the electron injecting / transporting layer are continuously formed under vacuum to produce an organic electroluminescent device having more excellent properties. Can be.

When the layers such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are formed using a plurality of compounds by the vacuum evaporation method, each boat containing the compounds is individually temperature-controlled. Co-evaporation is preferred.

When each layer is formed by a solution coating method,
The components forming each layer or the components and the binder resin are dissolved or dispersed in a solvent to form a coating solution.

Examples of the binder resin usable for each of the hole injection transport layer, the light emitting layer and the electron injection transport layer include, for example,
Poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, polymethyl methacrylate, polyether, polycarbonate, polyamide, polyimide, polyamide imide, polyparaxylene, polyethylene, polyphenylene oxide, polyether sulfone, High molecular compounds such as polyaniline and its derivatives, polythiophene and its derivatives, polyphenylenevinylene and its derivatives, polyfluorene and its derivatives, and polythienylenevinylene and its derivatives can be given.
The binder resin may be used alone, or
A plurality of them may be used in combination.

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 an appropriate organic solvent and / or water to form a coating solution, and a thin film can be formed by various coating methods.

Examples of the organic solvent include hexane, octane, decane, toluene, xylene, ethylbenzene,
Hydrocarbon solvents such as methylnaphthalene; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; halogens such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene and chlorotoluene. Esters such as ethyl acetate, butyl acetate, and amyl acetate; Alcohol solvents such as methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, and ethylene glycol; dibutyl ether , Tetrahydrofuran, dioxane, anisole and other ether solvents; N, N-dimethylformamide, N, N-dimethyl Acetamide, 1-methyl-2-pyrrolidone, 1-methyl-2-imidazolidinone, a polar solvent such as dimethyl sulfoxide)

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 forming a desired thickness depending on the coating method to be performed. %, Preferably about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin is not particularly limited, but is generally relative to the components forming each layer (when forming a single-layer device, the total amount of each component is ), About 5 to 99.9% by weight, preferably 10 to 9% by weight.
About 9.9% by weight, more preferably 15 to 90% by weight
Set to about.

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.

For the purpose of preventing contact of the fabricated device with oxygen or moisture, a protective layer (sealing layer) may be provided.
In addition, the element, for example, paraffin, liquid paraffin,
It can be protected by being enclosed in an inert substance such as silicone oil, fluorocarbon oil, or zeolite-containing fluorocarbon oil.

As the material used for the protective layer, for example,
An organic polymer material, an inorganic material, and a photocurable resin can be used. The material used for the protective layer may be used alone or in combination. The protective layer may have a single-layer structure or a multilayer structure.

Examples of the organic polymer material include fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamide imide, polyparaxylene, polyethylene, polyphenylene oxide and the like. be able to.

Examples of the inorganic material include a diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide, and metal sulfide.

For example, a metal oxide film (for example, an aluminum oxide film) or a metal fluoride film can be provided as a protective layer on the electrode.

For example, an interface layer (intermediate layer) made of, for example, an organic phosphorus compound, polysilane, an aromatic amine derivative, or a phthalocyanine derivative may be provided on the surface of the anode.

Further, an electrode such as an anode may be used by treating its surface with, for example, an 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 example, as a panel type light source, various light emitting devices, various display devices, various labels, various sensors, and the like.

[0151]

EXAMPLES The present invention will be described in more detail with reference to Production Examples and Examples, which should not be construed as limiting the present invention.

(Production Example 1) Production of Exemplified Compound A-1 3- (benzo [j] fluoranthene-3'-yl) benzo
[k] 5.03 g of fluoranthene and cobalt trifluoride 1
1.59 g was 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 2.64 g of the compound A-1 exemplified above as purple crystals. Mass spectrometry: m / z = 500 Melting point: 250 ° C. or higher This compound sublimated under the conditions of 500 ° C. and 10 −3 Pa. Absorption maximum (in toluene) 582 nm

(Production Examples 2 to 50)
-(Benzo [j] fluoranthene-3'-yl) benzo [k]
According to the method described in Production Example 1, except that various 3- (benzo [j] fluoranthene-3′-yl) benzo [k] fluoranthene derivatives were used instead of using fluoranthene, various benzo [4, 5] Indeno [1,2,3-cd] benzo [5,6] indeno [1,2,3-lm] perylene derivatives were produced.

Table 1 shows the 3- (benzo [j] fluoranthene-3'-yl) benzo [k] fluoranthene derivative used and the benzo [4,5] indeno [1,2,3-cd] produced.
Benzo [5,6] indeno [1,2,3-lm] perylene derivatives are indicated by exemplified compound numbers. In addition, the absorption maximum in toluene (n
m) is also shown.

The produced compounds were purple crystals, and the melting points of those compounds were 250 ° C. or higher.

[0157]

[Table 1]

[0158]

[Table 2]

[0159]

[Table 3]

[0160]

[Table 4]

[0161]

[Table 5]

[0162]

[Table 6]

[0163]

[Table 7]

Example 1 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 −3 Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, bis (2-methyl-8)
-Quinolinolate) (4-phenylphenolato) aluminum and bisbenzo [4,5] indenoperylene (compound of Exemplified Compound No. A-1) were prepared from different evaporation sources at a deposition rate of 0.2 nm / sec and a thickness of 50 nm. Was co-evaporated (weight ratio: 100: 0.5) 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2420 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, the compound of Exemplified Compound No. A-2 (Example 2), Exemplified Compound No. A- Compound No. 4 (Example 3), Compound No. A-8 (Example 4), Compound No. A-9
(Example 5), the compound of Exemplified Compound No. A-11 (Example 6), the compound of Exemplified Compound No. A-14 (Example 7), the compound of Exemplified Compound No. A-16 (Example 8), Compound of Exemplified Compound No. A-18 (Example 9),
Compound of Exemplified Compound No. A-19 (Example 10), Compound of Exemplified Compound No. A-21 (Example 11), Compound of Exemplified Compound No. A-23 (Example 12), Compound of Exemplified Compound No. A-25 (Example 13), Compound of Exemplified Compound No. A-26 (Example 14), Exemplified Compound No. A-
Compound No. 29 (Example 15), Exemplified Compound No. A-31
(Example 16), compound of Exemplified Compound No. A-34 (Example 17), compound of Exemplified Compound No. B-1 (Example 18), compound of Exemplified Compound No. B-4 (Example 19), Compound of Exemplified Compound No. B-6 (Example 2
0), compound of Exemplified Compound No. B-7 (Example 21),
Compound of Exemplified Compound No. C-1 (Example 22), Compound of Exemplified Compound No. C-2 (Example 23), Compound of Exemplified Compound No. C-4 (Example 24), Exemplified Compound No. C-
Compound No. 6 (Example 25), Compound No. C-7 (Example 26), Compound No. C-9 (Example 27), Compound No. C-10 (Example 28) Compound of Exemplified Compound No. C-13 (Example 29), Compound of Exemplified Compound No. C-16 (Example 3)
0), Compound of Exemplified Compound No. C-18 (Example 3)
1), Compound of Exemplified Compound No. C-20 (Example 3)
2), Compound of Exemplified Compound No. C-22 (Example 3)
3), Compound of Exemplified Compound No. C-24 (Example 3)
4), Compound of Exemplified Compound No. C-26 (Example 3)
5), Compound of Exemplified Compound No. C-28 (Example 3)
6), Compound of Exemplified Compound No. C-31 (Example 3)
7), Compound of Exemplified Compound No. C-36 (Example 3)
8), Compound of Exemplified Compound No. C-39 (Example 3)
9), Compound of Exemplified Compound No. C-40 (Example 4)
0), Compound of Exemplified Compound No. C-42 (Example 4)
1), Compound of Exemplified Compound No. C-43 (Example 4)
2), Compound of Exemplified Compound No. C-45 (Example 4)
3), Compound of Exemplified Compound No. C-46 (Example 4)
4), Compound of Exemplified Compound No. C-48 (Example 4)
5), Compound of Exemplified Compound No. C-50 (Example 4)
6), Compound of Exemplified Compound No. C-51 (Example 4)
7), Compound of Exemplified Compound No. C-53 (Example 4)
8), Compound of Exemplified Compound No. C-58 (Example 4)
9), Compound of Exemplified Compound No. C-60 (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
It is shown in the table.

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-8-quinolinolate) (4-
Phenylphenolate) using only aluminum, 5
Example 1 except that a light emitting layer was formed by vapor deposition to a thickness of 0 nm.
An organic electroluminescent device was produced by the method described in (1). When a DC voltage of 12 V was applied to this device under a dry atmosphere, blue light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2.

Comparative Example 2 The procedure of Example 1 was repeated, except that N-methyl-2-methoxyacridone was used instead of the compound of Exemplified Compound No. A-1 in forming the light emitting layer. An organic electroluminescent device was produced by the method described in 1. This device was exposed to a 12 V
As a result, blue light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2.

[0171]

[Table 8]

[0172]

[Table 9]

Example 51 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, bis (2-methyl-8)
-Quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-8 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: 1.0). ) 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 are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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 under a dry atmosphere, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2360 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, bis (2-methyl-8)
-Quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-14 from different evaporation sources
Co-evaporation (weight ratio: 100: 2.0) was performed at a deposition rate of 0.2 nm / sec to a thickness of 50 nm 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2350 cd / m ² was confirmed.

Example 53 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-
Bis (2,4-dimethyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-19 were co-evaporated from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio 100: 4). .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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2390 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-25 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 6.0)
Thus, a light emitting layer was obtained.

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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2340 cd / m ² was confirmed.

Example 55 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-31 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Is co-deposited to a thickness of 50 nm (weight ratio 100: 10),
It was 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the current was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2460 cd / m ² was confirmed.

Example 56 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, tris (8-quinolinolate) aluminum and the compound of Exemplified Compound No. B-4 were co-deposited thereon from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio). 100: 1.0)
The light emitting layer also served as the electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 55 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2440 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, bis (2-methyl-8)
-Quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. C-1 were co-evaporated from different evaporation sources to a thickness of 50 nm at a deposition rate of 0.2 nm / sec (weight ratio 100: 1.0). ) 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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 under a dry atmosphere, the voltage was 56 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2440 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, bis (2-methyl-8)
-Quinolinolate) aluminum-μ-oxo-bis (2-methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. C-6 from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm. Evaporation (weight ratio 100: 2.0) was performed 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 are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 52 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2340 cd / m ² was confirmed.

Example 59 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-
Bis (2,4-dimethyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-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: 4). .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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 55 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2420 cd / m ² was confirmed.

Example 60 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-18 were further placed thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 6.0)
Thus, a light emitting layer was obtained.

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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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 under a dry atmosphere, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2330 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-24 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Is co-deposited to a thickness of 50 nm (weight ratio 100: 10),
It was 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2380 cd / m ² was confirmed.

Example 62 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-31 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
The light emitting layer also served as an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec.
The resultant was co-deposited (weight ratio 10: 1) to a thickness of 200 nm by using c to form a cathode, thereby producing an organic electroluminescent device. In addition, evaporation is
The test was performed while maintaining the reduced pressure of the vapor deposition tank.

When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2370 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, bis (2-methyl-8)
-Quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. C-40 were co-evaporated from different evaporation sources to a thickness of 50 nm at a deposition rate of 0.2 nm / sec (weight ratio 100: 1.0). ) 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2240 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, bis (2-methyl-8)
-Quinolinolate) aluminum-μ-oxo-bis (2-methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. C-45 from different evaporation sources
Co-evaporation (weight ratio: 100: 2.0) was performed at a deposition rate of 0.2 nm / sec to a thickness of 50 nm 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2350 cd / m ² was confirmed.

Example 65 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-
Bis (2,4-dimethyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-50 were co-evaporated from different evaporation sources to a thickness of 50 nm at a deposition rate of 0.2 nm / sec (weight ratio 100: 4). .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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 56 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2370 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-51 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 6.0)
Thus, a light emitting layer was obtained.

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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2350 cd / m ² was confirmed.

Example 67 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-53 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Is co-deposited to a thickness of 50 nm (weight ratio 100: 10),
It was 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 injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm 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 under a dry atmosphere, the voltage was 54 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2350 cd / m ² was confirmed.

Example 68 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
m to form a hole injecting and transporting layer.

Then, Exemplified Compound No. A-4
Was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm to form a light-emitting layer.

Next, 1,3-bis [5'-
(P-tert-butylphenyl) -1,3,4-oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 n.
Vapor deposition was performed to a thickness of 50 nm at m / sec to form an electron injection transport layer. Further thereon, magnesium and silver were co-deposited (weight ratio 10: 1) at a deposition rate of 0.2 nm / sec to a thickness of 200 nm 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 in a dry atmosphere, the voltage was 42 mA / c.
current of m ² was flowing. Red light emission with a luminance of 1870 cd / m ² was confirmed.

Example 69 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻³ Pa.

First, the compound of Exemplified Compound No. C-6 was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec.
The layer was deposited to a thickness of nm to form a light emitting layer.

Then, 1,3-bis [5'-
(P-tert-butylphenyl) -1,3,4-oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 n.
It was deposited at a thickness of 75 nm at m / sec to form an electron injection transport layer. Further thereon, magnesium and silver were co-deposited (weight ratio 10: 1) at a deposition rate of 0.2 nm / sec to a thickness of 200 nm 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 manufactured organic electroluminescent device in a dry atmosphere, the voltage was 61 mA / c.
current of m ² was flowing. Red light emission with a luminance of 1610 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, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 −3 Pa.

First, 4,4 ′,
4 ″ -tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine was deposited at a deposition rate of 0.1 n.
At 50 m / sec, the film was deposited to a thickness of 50 nm to form a first hole injection / transport layer.

Next, 4,4 ′,-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl and the compound of Exemplified Compound No. A-1 were mixed from different evaporation sources at an evaporation rate of 0.2 nm / Co-evaporation (weight ratio: 100: 5) was performed to a thickness of 20 nm in seconds to obtain a light emitting layer also serving as a second hole injection / transport layer.

Next, tris (8-quinolinolate) aluminum was deposited thereon 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 were further deposited thereon at a deposition rate of 0.2 n.
Co-deposition to a thickness of 200 nm at m / sec (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 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, the voltage was 61 mA / c.
current of m ² was flowing. Red light emission with a luminance of 2570 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-2 (Example 71), the exemplified compound Compound of No. A-8 (Example 72), Compound of Exemplified Compound No. A-11 (Example 7)
3), Compound of Exemplified Compound No. A-16 (Example 7)
4), Compound of Exemplified Compound No. A-19 (Example 7)
5), Compound of Exemplified Compound No. A-23 (Example 7)
6), Compound of Exemplified Compound No. A-26 (Example 7)
7), Compound of Exemplified Compound No. A-31 (Example 7)
8), Compound of Exemplified Compound No. B-1 (Example 79),
Compound of Exemplified Compound No. B-6 (Example 80), Compound of Exemplified Compound No. C-1 (Example 81), Compound of Exemplified Compound No. C-4 (Example 82), Exemplified Compound No. C
Compound No. -7 (Example 83), Exemplified Compound No. C-10
(Example 84), the compound of Exemplified Compound No. C-16 (Example 85), the compound of Exemplified Compound No. C-20 (Example 86), the compound of Exemplified Compound No. C-24 (Example 87), Compound of Exemplified Compound No. C-28 (Example 88), Compound of Exemplified Compound No. C-36 (Example 8)
9), Compound of Exemplified Compound No. C-40 (Example 9)
0), Compound of Exemplified Compound No. C-43 (Example 9)
1) Compound of Exemplified Compound No. C-46 (Example 92)
An organic electroluminescent device was produced by the method described in Example 70 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 3.

[0271]

[Table 10]

Example 93 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 and further washed with UV / ozone.

Next, poly-N-vinylcarbazole (weight average molecular weight: 150,000),
1,1,4,4, -tetraphenyl 1,3-butadiene (blue light-emitting component), coumarin 6 ["3- (2'-benzothiazolyl) -7-diethylaminocoumarin" (green light-emitting component)], and A 400 nm light emitting layer was formed by dip coating using a 3 wt% dichloroethane solution containing the compound of Exemplified Compound No. A-18 at a weight ratio of 100: 5: 3: 2.

Next, the glass substrate having the light emitting layer was
After fixing to the substrate holder of the vapor deposition device, the vapor deposition tank is 4 × 1
The pressure was reduced to 0-3 Pa. Further, on the light emitting layer,
(4′-tert-butylphenyl) -4-phenyl-5-
After (4 ″ -biphenyl) 1,2,4-triazole was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm, tris (8-quinolinolate) aluminum was further deposited thereon at a deposition rate of 0.2 nm. 30 nm / sec
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. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device under a dry atmosphere, the voltage was 62 mA / c.
current of m ² was flowing. White light emission with a luminance of 1300 cd / m ² was confirmed.

(Examples 94 to 102) In Example 93, instead of using the compound of Exemplified Compound No. A-18, a compound of Exemplified Compound No. A-19 (Example 94)
Compound of Exemplified Compound No. A-26 (Example 95), Compound of Exemplified Compound No. C-13 (Example 96), Compound of Exemplified Compound No. C-16 (Example 97), Compound of Exemplified Compound No. C-18 (Example 98), Exemplified Compound No. C
Compound No. -20 (Example 99), Exemplified Compound No. C-2
Compound No. 6 (Example 100), Exemplified Compound No. C-28
Example 93 except that the compound of Example 101 and the compound of Example Compound No. C-31 (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.

[0277]

[Table 11]

(Example 103) ITO having a thickness of 200 nm
A glass substrate having a 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: 150,000),
1,3-bis [5 ′-(p-tert-butylphenyl)-
1,3,4-oxadiazol-2′-yl] benzene and the compound of Exemplified Compound No. C-18 in a 3 wt% dichloroethane solution containing 100: 30: 3 by weight, respectively. By dip coating method, 3
A 00 nm light emitting layer was formed.

Next, the glass substrate having the light emitting layer was
After fixing to the substrate holder of the vapor deposition device, the vapor deposition tank is 4 × 1
The pressure was reduced to 0 ⁻³ Pa.

Further, on the light emitting layer, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode to produce an organic electroluminescent device. .

When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, the voltage was 62 mA / c.
current of m ² was flowing. Red light emission with a luminance of 1470 cd / m ² was confirmed.

(Comparative Example 3) In Example 103, when forming the light emitting layer, instead of the compound of Exemplified Compound No. C-18, 1,1,4,4-tetraphenyl-1,3-
An organic electroluminescent device was prepared by the method described in Example 103 except that butadiene was used. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 86 mA / cm ² flowed. Brightness 7
Blue light emission of 60 cd / m ² was confirmed.

(Example 104) ITO having a thickness of 200 nm
A glass substrate having a 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, polycarbonate (weight average molecular weight: 50,000), 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, bis (2-methyl- 8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8
-Quinolinolate) aluminum and the compound of Exemplified Compound No. C-31 in a weight ratio of 100: 40: 6, respectively.
A 300 nm light emitting layer was formed by dip coating using a 3% by weight dichloroethane solution containing 0: 1.

Next, the glass substrate having the light emitting layer was
After fixing to the substrate holder of the vapor deposition device, the vapor deposition tank is 4 × 1
The pressure was reduced to 0 ⁻³ Pa. Further, magnesium and silver were deposited on the light emitting layer at a deposition rate of 0.2 nm / sec for 200 n.
An organic electroluminescent device was prepared by co-evaporating the resultant to a thickness of 10 m (weight ratio: 10: 1) to form a cathode.

When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device under a dry atmosphere, the voltage was 61 mA / c.
current of m ² was flowing. Red light emission with a luminance of 970 cd / m ² was confirmed.

[0288]

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 4: light emitting layer 4 ′: light emitting layer (a layer in which a light emitting component and a hole injection / transport component are mixed) 4 ″: light emitting layer (light emitting component and electron injection / transport component) 4 ''': Light-emitting layer (layer in which a light-emitting component, a hole injection / transport component, and an electron injection / transport component are mixed) 5: Electron injection / transport layer 6: Cathode 7: Power supply

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat ゛ (Reference) C09K 11/06 660 C09K 11/06 660 H05B 33/12 H05B 33/12 C 33/22 33/22 D ( 72) Inventor Yoshimitsu Tanabe 580-32 Nagaura, Sodegaura-shi, Chiba Prefecture Mitsui Chemicals Co., Ltd. (72) Inventor Yoshiyuki Toya 580-32 Nagaura, Sodegaura-shi, Chiba Prefecture Mitsui Chemicals Co., Ltd. 580-32, Nagaura, Sodegaura City, F Mitsui Chemicals Co., Ltd. F-term (reference) 3K007 AB02 AB03 AB04 CA01 CB01 DA01 DB03 EB00 4H006 AA01 AA03 AB92 EA43

Claims (8)

[Claims] A benzo [4,5] indeno is provided between a pair of electrodes.
An organic electroluminescent device comprising at least one layer containing at least one layer containing [1,2,3-cd] benzo [5,6] indeno [1,2,3-lm] perylene derivative. 2. Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device according to claim 1, wherein the layer containing the [5,6] indeno [1,2,3-lm] perylene derivative further contains a luminescent organometallic complex. 3. Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device according to claim 1, wherein the layer containing the [5,6] indeno [1,2,3-lm] perylene derivative further contains a triarylamine derivative. 4. Benzo [4,5] indeno [1,2,3-cd] benzo
3. The organic electroluminescent device according to claim 1, wherein the layer containing the [5,6] indeno [1,2,3-lm] perylene derivative is a light emitting layer. 5. The organic electroluminescent device according to claim 4, further comprising a hole injection / transport layer between the pair of electrodes. 6. The organic electroluminescent device according to claim 4, further comprising an electron injection / transport layer between the pair of electrodes. 7. Benzo [4,5] indeno [1,2,3-cd] benzo
The organic electroluminescent device according to any one of claims 1 to 6, wherein the [5,6] indeno [1,2,3-lm] perylene derivative is a compound represented by the general formula (1-A). Embedded image (Wherein, X ^{1 to} X ²⁰ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. .) 8. A compound represented by the general formula (1-A). Embedded image (Wherein, X ^{1 to} X ²⁰ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. .)