JP2002043062A - Hydrocarbon compound and organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide the organic electroluminescent element having the superior luminous efficiency and the high luminance. SOLUTION: This electroluminescent element uses a compound expressed by general formula 1-A. (In the formula, X1-X24 are independently a hydrogen atom, a halogen atom, a straight-chain, branch or cyclic alkyl group, a straight- chain, branch or cyclic alkoxy group, or a substituent or non-substituent aryl group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an organic electroluminescent device and a novel hydrocarbon compound which can be suitably used for the light emitting device.

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent device has been used as a panel-type light source such as a backlight. However, driving the light emitting device requires a high AC voltage. Recently, an organic electroluminescence device using an organic material as an emission material (organic electroluminescence device: organic EL device) 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. The organic electroluminescent device having such characteristics is expected to be applied to various light emitting devices, display devices, and the like. However, the light emission luminance is generally 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 relates to a method for producing benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′: 5,6] indeno [1,2,3-lm] perylene between a pair of electrodes. An organic electroluminescent device in which at least one layer containing at least one derivative is sandwiched, benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ', 1
0 ': 5,6] Indeno [1,2,3-lm] perylene derivative is a light-emitting layer, wherein the organic electroluminescent device is as described above, wherein benzo [5,6] indeno [1,2,3 -cd] phenanthro [9 ', 1
The organic electroluminescent device according to the above or the above, wherein the layer containing the 0 ': 5,6] indeno [1,2,3-lm] perylene derivative further contains a luminescent organometallic complex. [5,6] indeno [1,2,3-cd] phenanthro [9 ', 1
0 ': 5,6] Indeno [1,2,3-lm] perylene derivative-containing layer further contains a triarylamine derivative; The organic electroluminescent device according to any one of the above-mentioned items, further comprising a hole injection transport layer between the electrodes, and the organic electric field device according to any one of the above items further comprising an electron injection transport layer between a pair of electrodes. Light-emitting element, benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ', 1
0 ′: 5,6] indeno [1,2,3-lm] perylene derivative is a compound represented by the following general formula (1-A):
The organic electroluminescent device according to any one of the above,

[0006]

Embedded image

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

[0008]

Embedded image

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

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The organic electroluminescent device of the present invention has a structure in which benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ', 1
At least one layer containing at least one 0 ': 5,6] indeno [1,2,3-lm] perylene derivative is sandwiched therebetween. Benzo [5,6] indeno [1,2,3-c according to the present invention
d] phenanthro [9 ′, 10 ′: 5,6] indeno [1,2,3-lm] perylene derivative (hereinafter abbreviated as compound A according to the present invention) is represented by the general formula (1) ) Represents a compound having a skeleton represented by The skeleton represented by the general formula (1) is
The compound A according to the present invention, which may be substituted with various substituents, is preferably a compound represented by the general formula (1-A).

[0011]

Embedded image

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

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

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

For example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4
-Ethylphenyl group, 4-n-propylphenyl group, 4
-Isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-undecylphenyl group, 4-n -Dodecylphenyl group, 4-n-
Tetradecylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethyl Phenyl group, 3,
4,5-trimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-indanyl group, 1,2,3
4-tetrahydro-5-naphthyl group, 1,2,3,4-
A 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-methoxyphenyl group n-
Butoxyphenyl group, 4-isobutoxyphenyl group, 4
-N-pentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n-heptyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-nonyloxyphenyl group A 4-n-decyloxyphenyl group, a 4-n-undecyloxyphenyl group, a 4-n-dodecyloxyphenyl group, a 4-n-tetradecyloxyphenyl group,

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

More preferably, a hydrogen atom, a fluorine atom,
Chlorine atom, 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 [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′: 5,
It is characterized by using at least one 6] indeno [1,2,3-lm] perylene derivative. For example, benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′] : 5,6] indeno [1,
When a [2,3-lm] perylene derivative is used as a light-emitting component in a light-emitting layer, it is possible to provide an organic electroluminescent device that emits orange-red to red light with high luminance and excellent durability, which has not existed conventionally. . In addition, when a light-emitting layer is formed in combination with another light-emitting component, an organic electroluminescent element that emits white light with high luminance and excellent durability can be provided.

Specific examples of the compound A according to the present invention include:
For example, the following compounds (Chemical Formulas 6 to 48) can be exemplified, but the present invention is not limited thereto.

[0021]

Embedded image

[0022]

Embedded image

[0023]

Embedded image

[0024]

Embedded image

[0025]

Embedded image

[0026]

Embedded image

[0027]

Embedded image

[0028]

Embedded image

[0029]

Embedded image

[0030]

Embedded image

[0031]

Embedded image

[0032]

Embedded image

[0033]

Embedded image

[0034]

Embedded image

[0035]

Embedded image

[0036]

Embedded image

[0037]

Embedded image

[0038]

Embedded image

[0039]

Embedded image

[0040]

Embedded image

[0041]

Embedded image

[0042]

Embedded image

[0043]

Embedded image

[0044]

Embedded image

[0045]

Embedded image

[0046]

Embedded image

[0047]

Embedded image

[0048]

Embedded image

[0049]

Embedded image

[0050]

Embedded image

[0051]

Embedded image

[0052]

Embedded image

[0053]

Embedded image

[0054]

Embedded image

[0055]

Embedded image

[0056]

Embedded image

[0057]

Embedded image

[0058]

Embedded image

[0059]

Embedded image

[0060]

Embedded image

[0061]

Embedded image

[0062]

Embedded image

[0063]

Embedded image

The compound A according to the present invention, for example, the compound represented by the general formula (1-A) can be produced, for example, by the following method. That is, for example, a compound represented by the general formula (2) (Formula 49) is converted to an oxidizing agent (for example, aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, The reaction is performed in the presence of lead acetate or ferric chloride to close the ring [for example, J. Amer. Chem. Soc., 102 , 6
504 (1980), Chem. Rev., 87 , 357 (1987) can be referred to].

[0065]

Embedded image

[In the above formula, X _{1 to} X ₂₄ represent the general formula (1-
A represents the same meaning as in the case of A). The compound represented by the general formula (2) is, for example, a benzo [k] fluoranthene derivative represented by the general formula (3) Acenaphtho represented by (Formula 50)
A [1,2-b] triphenylene derivative is reacted with, for example, nickel chloride, triphenylphosphine and zinc, and optionally, in the presence of sodium bromide [for example, J. Org. Chem., 51 , 2627 (1986) can be referred to]. Further, for example, a compound represented by the general formula (3) is reacted with a compound represented by the general formula (4) in the presence of, for example, palladium acetate and tetra-n-butylammonium bromide [for example, Tetrahedron Lett., 39, 2
559 (1998) can be referred to].

Further, for example, a compound represented by the general formula (3) and a compound represented by the general formula (4) in the presence of a nickel complex [eg, bis (1,5-cyclooctadiene) nickel]. The compound can be produced by reacting (for example, J. Amer. Chem. Soc., 103 , 6
460 (1981), Macromolecules, 25 , 1214 (1992).)

[0068]

Embedded image

[In the above formula, X _{1 to} X ₂₄ represent the general formula (1-
A represents the same meaning as in the case of A), and Z ₁ and Z ₂ represent a halogen atom.] In the general formulas (3) and (4), Z ₁ and Z ₂ represent a halogen atom, preferably a chlorine atom , A bromine atom and an iodine atom.

The benzo [k] fluoranthene derivative represented by the general formula (3) is described in, for example, J. Org. Chem., 62 , 530 (1).
997). That is, it can be produced, for example, by reacting a 5-halogenoasenaphthylene derivative with an isobenzofuran derivative, followed by dehydration. In addition, the compound represented by the general formula (3) can be produced by reacting a 3-halogenocyclopenta [a] acenaphthylene-8-one derivative with a benzyne derivative [for example, Ind. J. Chem. Sec
tB, 15B , 32 (1977) can be referred to].

Further, acenaphth represented by the general formula (4)
[1,2-b] triphenylene derivatives are described, for example, in Indian J. Ch.
em. Sect. B , 22B , 225 (1983). That is, the acenaphtho [1,2-k] triphenylene derivative represented by the general formula (4) can be obtained, for example, by reacting a 2H-cyclopenta [l] phenanthrene-2-one derivative with a 5-halogenoacenaphthylene derivative,
After decarbonization, it can be produced by dehydrogenation (for example, using chloranyl, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a dehydrogenating agent). it can. Also, the general formula (4)
The acenaphtho [1,2-k] triphenylene derivative represented by the formula is, for example, 2H-cyclopenta [l] phenanthrene-
It can be produced by reacting a 2-one derivative with a 1,5-dihalogenoacenenaphthylene derivative and then removing carbon monoxide.

The compound represented by the general formula (2) is
For example, a compound represented by the general formula (4) and a compound represented by the general formula (5)
A boric acid compound represented by the following formula (51) may be used, for example, with a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, hydrogen carbonate) Sodium, triethylamine)
(For example, Chem. Rev., 95 , 2457 (19).
The method described in 95) can be referred to]. Similarly, the general formula (2)
Can also be produced using, for example, a compound represented by the general formula (3) and a boric acid compound represented by the general formula (6) (Formula 51).

[0073]

Embedded image

In the above formula, X _{1 to} X ₂₄ are represented by the general formula (1-
It has the same meaning as in case A). The compound represented by the general formula (5) is, for example, a compound represented by the general formula (3) and a litho compound or a Grignard reagent which can be prepared by reacting with n-butyllithium or magnesium metal. For example, it can be prepared using trimethoxyboron, triisopropoxyboron, etc. [For example, the method described in Chem. Rev., 95 , 2457 (1995) can be referred to]. Similarly, the compound represented by the general formula (6) can be prepared, for example, from the compound represented by the general formula (4).

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

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

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

The structure of the organic electroluminescent device of the present invention is not particularly limited.
Hole injection / transport layer / emission layer / electron injection / transport layer / cathode device (FIG. 1), (B) anode / hole injection / transport layer / emission layer / cathode device (FIG. 2), (C) anode / emission Layer / electron injection / transport layer / cathode type device (FIG. 3), (D) anode / light emitting layer / cathode type device (FIG. 4) and the like. Further, the device is of a type in which a light emitting layer is sandwiched between electron injection and transport layers (E).
Anode / hole injection / transport layer / electron injection / transport layer / emission layer / electron injection / transport layer / cathode type device (FIG. 5).
The element configuration of the (D) type includes an element of a type in which a light-emitting component is sandwiched between a pair of electrodes in a single layer form. Further, for example, (F) a hole injection / transport component, (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, but may include a plurality of hole injection / transport layers, a light emitting layer, and an electron injection / transport layer in each type of device. 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. More preferred configurations of the organic electroluminescent element include (A) type element, (B) type element, (C) type element, (E) type element, (F) type element,
(G) type element or (H) type element, more preferably (A) type element, (B) type element, (C) type element,
(F) type element or (H) type element. As the organic electroluminescent device of the present invention, for example, (A) anode / hole injection / transport layer / emission layer / electron injection / transport layer / cathode device shown in FIG. 1 will be described. (FIG. 1)
Is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer,
Reference numeral 5 denotes an electron injection / transport layer, 6 denotes a cathode, and 7 denotes a power supply.

The electroluminescent device of the present invention is preferably supported on a substrate 1, 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. As the electrode material used for the anode, for example, gold, platinum, silver, copper, cobalt, nickel,
Palladium, vanadium, tungsten, tin oxide, zinc oxide, ITO (indium tin oxide), polythiophene, polypyrrole, and the like can be given. These electrode substances may be used alone or in combination of two or more. The anode can be formed on a substrate by using such an electrode material by a method such as an evaporation method or a sputtering method. Further, the anode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the anode is preferably several hundred Ω.
/ □ or less, more preferably about 5 to 50Ω / □. The thickness of the anode depends on the material of the electrode substance to be used, but is generally about 5 to 1000 nm, more preferably,
It is set to about 10 to 500 nm.

The hole injection / transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes (holes) from the anode and a function of transporting the injected holes. The hole injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having a hole injecting and transporting function (for example, a phthalocyanine derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, a hydrazone derivative, a stilbene derivative). , Pyrazoline derivatives, polysilane derivatives, polyphenylenevinylene and its derivatives,
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.

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

The light emitting layer 4 has a hole and electron injection function,
This is a layer containing a compound having a transport function thereof and a function of generating excitons by recombination of holes and electrons. The light-emitting layer is formed of the compound A according to the present invention and / or another compound having a light-emitting function (eg, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [eg, rubrene, anthracene, tetracene, pyrene). , Perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclohexadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) ) Benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl], a triarylamine derivative [for example, the compounds described above as compounds having a hole injecting and transporting function], and organometallic complexes [For example, Tris (8- Rirato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2-
Zinc salt of (2′-hydroxyphenyl) benzoxazole, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine,
Zinc salts of -hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivatives [for example, 1,1,4,4
-Tetraphenyl-1,3-butadiene, 4,4'-bis (2,2-diphenylvinyl) biphenyl, 4,4 '
-Bis [(1,1,2-triphenyl) ethenyl] biphenyl, coumarin derivatives [for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin 153, coumarin 307, coumarin 311, coumarin 314, coumarin 334, coumarin 338, coumarin 343, coumarin 500], pyran derivative [for example, D
CM1, DCM2], oxazone derivative [for example, Nile Red], benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamate derivative, 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) It can be formed using at least one kind. In the organic electroluminescent device of the present invention, the light emitting layer preferably contains the compound A according to the present invention. When the compound A according to the present invention and a compound having another light emitting function are used in combination, the ratio of the compound A according to the present invention in the light emitting layer is preferably 0.00
About 1 to 99.999% by weight, more preferably about 0.0
About 1 to 99.99% by weight, more preferably 0.1 to 99.99% by weight.
It is adjusted to about 99.9% by weight.

As the other compound having a light-emitting function used in the present invention, a light-emitting organic metal complex is preferable. For example, J. Appl. Phys., 65 , 3610 (1989), 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). The compound A according to the present invention can be used as a host compound to form a light-emitting layer, and further can be used as a guest compound to form a light-emitting layer. 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 compounds having the other light-emitting functions, such as a light-emitting organometallic complex or The above triarylamine derivatives are more preferred. In this case, the compound A according to the present invention is preferably used in an amount of 0.001 to 40% by weight based on the luminescent organometallic complex or the triarylamine derivative.
Level, more preferably about 0.01 to 30% by weight, particularly preferably about 0.1 to 20% by weight.

The light-emitting organometallic complex used in combination with the compound A according to the present invention is not particularly limited, but a light-emitting organic aluminum complex is preferable, and a light-emitting organic compound having a substituted or unsubstituted 8-quinolinolate ligand. 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) Late) 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-butylphenolato) aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6- Triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,5,6-tetra Methyl phenolate)
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-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenylphenolate) aluminum , Bis (2-methyl-8-quinolinolate) aluminum Mu-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2
4-dimethyl-8-quinolinolato) aluminum-μ
-Oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8)
-Quinolinolate) aluminum- [mu] -oxo-bis (2-methyl-4-ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) aluminum- [mu] -oxo-bis (2-methyl -4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5)
-Cyano-8-quinolinolate) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum and the like Can be mentioned. Of course, the luminescent organometallic complex may be used alone or in combination.

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

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

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

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. 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. By vacuum evaporation method,
In the case of forming each layer, the conditions of vacuum deposition are not particularly limited, but under a vacuum of about 10 ^-5 Torr, 50 to 6
Boat temperature of about 00 ° C (deposition source temperature), -50 to 30
It is preferable to perform the deposition at a substrate temperature of about 0 ° C. and at a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer,
By continuously forming the organic electroluminescent element under vacuum, an organic electroluminescent device having more excellent various characteristics can be manufactured. When each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer is formed using a plurality of compounds by a vacuum evaporation method,
It is preferred that the temperature of each boat containing the compound be individually controlled and co-evaporated.

When each layer is formed by a solution coating method,
The components forming each layer or the components and the binder resin are dissolved or dispersed in a solvent to form a coating solution. Examples of the binder resin that can be used for each of the hole injection transport layer, the light emitting layer, and the electron injection transport layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, and polymethyl methacrylate. , Polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylenevinylene and its derivatives, polyfluorene and its derivatives, polythienyl And high molecular compounds such as lenvinylene and derivatives thereof. The binder resin may be used alone or in combination of two or more. When each layer is formed by a solution coating method, a component forming each layer or the component and a binder resin are mixed with a suitable organic solvent (for example, hexane, octane, decane,
Toluene, xylene, ethylbenzene, hydrocarbon solvents such as 1-methylnaphthalene, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone, for example, dichloromethane,
Chloroform, tetrachloromethane, dichloroethane,
Halogenated hydrocarbon solvents such as trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, for example, ethyl acetate, butyl acetate,
Ester solvents such as amyl acetate, for example, methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, alcohol solvents such as ethylene glycol, for example, dibutyl ether, tetrahydrofuran, dioxane, anisole and the like Ether solvents such as polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1-methyl-2-imidazolidinone, dimethylsulfoxide) and / or Alternatively, a thin film can be formed by various coating methods by dissolving or dispersing in water to form a coating solution.

The method of dispersion is not particularly limited. For example, the particles can be dispersed in 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 a coating method to be performed, and is generally about 0.1 to 50% by weight. Preferably, the solution concentration is about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin is not particularly limited, but is generally relative to the components forming each layer (when forming a single-layer device, the total amount of each component is 5) to 99.9% by weight
Degree, preferably about 10 to 99.9% by weight, more preferably about 15 to 90% by weight.

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

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

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

[0097]

EXAMPLES The present invention will be described below in more detail with reference to Production Examples and Examples, but it should be understood that the present invention is not limited by these.

Preparation Example 1 Preparation of Compound of Exemplified Compound A-1 6.02 g of 12- (benzo [k] fluoranthene-3′-yl) acenaphtho [1,2-b] triphenylene and 11.59 g of cobalt trifluoride were prepared. In 100 ml of trifluoroacetic acid,
The mixture was stirred 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 4.98 g of a compound of Exemplified Compound A-1 as purple crystals. Mass spectrometry: m / z = 600 Melting point: 250 ° C. or more This compound sublimated under the conditions of 500 ° C. and 10 ⁻⁵ torr. Absorption maximum (in toluene) 562 nm 12- (benzo [k] fluoranthene-
3′-yl) acenaphtho [1,2-b] triphenylene was produced by the following method.

8.62 g of 12-bromoacenaphtho [1,2-b] triphenylene, benzo [k] fluoranthene-3'-
5.92 g of ilboric acid, 4.24 g of sodium carbonate and 0.69 g of tetrakis (triphenylphosphine) palladium were dissolved in toluene (100 ml) and water (50 ml).
ml) for 5 hours. After the toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was subjected to silica gel column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized with a mixed solvent of toluene and acetone to give 12-
(Benzo [k] fluoranthene-3'-yl) acenaphtho
9.63 g of [1,2-b] triphenylene as yellow crystals
Obtained.

Production Examples 2 to 50 In Production Example 1, instead of using 12- (benzo [k] fluoranthene-3′-yl) acenaphtho [1,2-b] triphenylene, various 12- (benzo [k] ] Fluoranthene-3'-yl) acenaphtho [1,2-b] triphenylene derivative, except that various benzo [5,6] indeno [1,2,3-cd ] Phenanthro [9 ', 10': 5,6] indeno [1,2,3-lm] perylene derivatives were prepared. In Table 1 (Tables 1 to 8), the used 12- (benzo [k] fluoranthen-3′-yl) acenaphtho [1,2-
b] triphenylene derivative and benzo [5,6] produced
Indeno [1,2,3-cd] phenanthro [9 ', 10': 5,6] indeno
[1,2,3-lm] perylene derivatives are indicated by exemplified compound numbers.
The maximum absorption (nm) in toluene is also shown.
The produced compounds were purple crystals, and the melting points of those compounds were 250 ° C. or higher.

[0101]

[Table 1]

[0102]

[Table 2]

[0103]

[Table 3]

[0104]

[Table 4]

[0105]

[Table 5]

[0106]

[Table 6]

[0107]

[Table 7]

[0108]

[Table 8]

Example 1 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was washed with a neutral detergent, acetone,
Ultrasonic cleaning was performed using 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 ^-6 Torr. First, on the ITO transparent electrode,
4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form a hole injecting and transporting layer. In addition, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ', 10': 5,6]
Indeno [1,2,3-lm] perylene (compound of Exemplified Compound No. A-1) was obtained from different evaporation sources at an evaporation rate of 0.2 nm /
Co-deposition to a thickness of 50 nm in sec (weight ratio 100: 0.
5) Then, a light emitting layer was obtained. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec for 5 minutes.
Evaporation was performed to a thickness of 0 nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm /
A co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm in sec to obtain a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Orange-red light emission with a luminance of 2460 cd / m ² was confirmed.

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

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

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

[0113]

[Table 9]

[0114]

[Table 10]

[0115]

[Table 11]

Example 51 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-8 were further deposited thereon from a different evaporation source at a deposition rate of 0. 2nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain 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 manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
An orange-red emission of 410 cd / m ² was confirmed.

Example 52 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-12 were co-deposited from different deposition sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio: 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere,
A current of 5 mA / cm ² flowed. Orange-red light emission with a luminance of 2360 cd / m ² was confirmed.

Example 53 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. A-19 were formed thereon. From different evaporation sources, a deposition rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain 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 manufactured organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Brightness 2
Orange-red light emission of 380 cd / m ² was confirmed.

Example 54 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-29 were deposited thereon from different evaporation sources at a deposition rate of 0,0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 6.0) to obtain a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm /
Vapor deposition was performed to a thickness of 50 nm in sec to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. The prepared organic electroluminescent device was dried under an atmosphere of 12
When a DC voltage of V was applied, a current of 56 mA / cm ² flowed. Orange-red light emission with a luminance of 2,320 cd / m ² was confirmed.

Example 55 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-6 were deposited thereon from different evaporation sources at a deposition rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
10) to form a light emitting layer. Next, tris (8-quinolinolate) 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. Furthermore, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm.
/ Sec co-deposition to a thickness of 200 nm (weight ratio 10: 1)
This was used as a cathode to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 53 mA / cm ² flowed. Emission of orange-red light having a luminance of 2220 cd / m ² was confirmed.

Example 56 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-10 were deposited thereon from different evaporation sources at a deposition rate of 0.1 mm.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 1.0) to obtain a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. The prepared organic electroluminescent device was dried under an atmosphere of 12
When a DC voltage of V was applied, a current of 54 mA / cm ² flowed. Orange-red light emission with a luminance of 2340 cd / m ² was confirmed.

Example 57 A glass substrate having a 200 nm thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. C-12 were further deposited thereon from different evaporation sources at a deposition rate of 0. 2nm / se
Co-deposition to a thickness of 50 nm with c (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain 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 manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
An orange-red emission of 320 cd / m ² was confirmed.

Example 58 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. C-24 were co-deposited from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio: 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere,
A current of 6 mA / cm ² flowed. Orange-red light emission with a luminance of 2330 cd / m ² was confirmed.

Example 59 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. C-30 were formed thereon. From different evaporation sources, a deposition rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain 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 manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Brightness 2
An orange-red emission of 320 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, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. D-1 were deposited thereon from different evaporation sources at an evaporation rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
6.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver 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 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Orange-red light emission with a luminance of 2360 cd / m ² was confirmed.

Example 61 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. D-8 were deposited thereon from different evaporation sources at an evaporation rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
10) to form a light emitting layer. Next, tris (8-quinolinolate) 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. Furthermore, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm.
/ Sec co-deposition to a thickness of 200 nm (weight ratio 10: 1)
This was used as a cathode to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Orange-red light emission with a luminance of 2310 cd / m ² was confirmed.

Example 62 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-4 were deposited thereon from different evaporation sources at an evaporation rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
1.0) to form a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver 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 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 53 mA / cm ² flowed. Emission of orange-red light having a luminance of 2250 cd / m ² was confirmed.

Example 63 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. E-7 were further deposited thereon from different evaporation sources at a deposition rate of 0. 2nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain 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 manufactured organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2
An orange-red emission of 350 cd / m ² was confirmed.

Example 64 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. E-10 were co-evaporated from different evaporation sources to a thickness of 50 nm at an evaporation rate of 0.2 nm / sec (weight ratio: 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere,
A current of 7 mA / cm ² flowed. Orange-red light emission with a luminance of 2370 cd / m ² was confirmed.

Example 65 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. E-17 were formed thereon. From a different evaporation source at a deposition rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain 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 manufactured organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2
An orange-red emission of 340 cd / m ² was confirmed.

Example 66 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-18 were deposited thereon from different evaporation sources at a deposition rate of 0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 6.0) to obtain a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm /
Vapor deposition was performed to a thickness of 50 nm in sec to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. The prepared organic electroluminescent device was dried under an atmosphere of 12
When a DC voltage of V was applied, a current of 56 mA / cm ² flowed. Orange-red light emission with a luminance of 2,320 cd / m ² was confirmed.

Example 67 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-23 were further deposited thereon from different evaporation sources at a deposition rate of 0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0:10) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / se.
The film was deposited by c 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.
at 200 nm / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 53 mA / cm ² flowed. Emission of orange-red light with a luminance of 2410 cd / m ² was confirmed.

Example 68 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, a compound of Exemplified Compound No. D-1 was further deposited thereon with a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form a light emitting layer. Then, thereover, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazol-2′-yl]
Benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Further on that,
Magnesium and silver are deposited at a deposition rate of 0.2 nm / sec.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 0 nm to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 43 mA / cm ² flowed. Brightness 1890
An orange-red emission of 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, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, the compound of Exemplified Compound No. E-4 was deposited on the ITO transparent electrode to a thickness of 55 nm at a deposition rate of 0.2 nm / sec to form a light emitting layer. Then, on top of that, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-
[Oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form an electron injecting and transporting layer. On top of that, magnesium and silver,
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 200 nm at an evaporation rate of 0.2 nm / sec to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the manufactured organic electroluminescent device under a dry atmosphere, the voltage was 62 mA / cm.
^Two currents flowed. Orange-red light emission with a luminance of 1480 cd / m ² was confirmed.

Example 70 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4 ′, 4 ″ -tris [N
-(3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine at a deposition rate of 0.1 nm / sec.
The first hole injection transport layer was deposited to a thickness of nm. Next, 4,4 ′,-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl and the compound of Exemplified Compound No. A-1 were deposited from different evaporation sources at an evaporation rate of 0.2 nm / se.
Co-deposited with c to a thickness of 20 nm (weight ratio 100: 5),
The light emitting layer also served as the second hole injection / transport layer. Next, tris (8-quinolinolate) aluminum was deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 15 V was applied in a dry atmosphere,
A current of 3 mA / cm ² flowed. Emission of orange-red light with a luminance of 2,720 cd / m ² was confirmed.

Examples 71 to 92 In Example 70, instead of using the compound of Exemplified Compound A-1 in forming the light emitting layer, the compound of Exemplified Compound No. A-10 (Example 71), Exemplified Compound No. A −
Compound No. 18 (Example 72), Exemplified Compound No. A-25
(Example 73), compound of Exemplified Compound No. B-1 (Example 74), compound of Exemplified Compound No. B-8 (Example 75), compound of Exemplified Compound No. C-1 (Example 7)
6), a compound of Exemplified Compound No. C-4 (Example 77),
Compound of Exemplified Compound No. C-10 (Example 78), Compound of Exemplified Compound No. C-16 (Example 79), Compound of Exemplified Compound No. C-47 (Example 80), Compound of Exemplified Compound No. D-1 (Example 81), Exemplified Compound No. D
-5 (Example 82), compound of Exemplified Compound No. D-8 (Example 83), compound of Exemplified Compound No. D-15 (Example 84), compound of Exemplified Compound No. D-17 (Example 85) ), Compound of Exemplified Compound No. E-1 (Example 86), compound of Exemplified Compound No. E-3 (Example 8)
7), Compound of Exemplified Compound No. E-4 (Example 88),
Compound of Exemplified Compound No. E-9 (Example 89), Compound of Exemplified Compound No. E-10 (Example 90), Compound of Exemplified Compound No. E-13 (Example 91), Compound of Exemplified Compound No. E-18 An organic electroluminescent device was manufactured by the method described in Example 70 except that (Example 92) 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 (Table 12).

[0137]

[Table 12]

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, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,1,4,4, -tetraphenyl 1,
3-butadiene (blue light-emitting component), coumarin 6 ["3
-(2′-benzothiazolyl) -7-diethylaminocoumarin ”(green light-emitting component)] and the compound of Exemplified Compound No. A-18 at a weight ratio of 100: 5: 3:
Using a 3% by weight dichloroethane solution containing 2 parts by weight, a 400 nm light emitting layer was formed by dip coating. Next, after fixing the glass substrate having the light emitting layer to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was set to 3 × 10
^The pressure was reduced to ^-6 Torr. Further, on the light emitting layer, 3- (4 ′
-Tert-butylphenyl) -4-phenyl-5- (4 "
-Biphenyl) 1,2,4-triazole was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm, and tris (8-quinolinolate) aluminum was further deposited thereon at a deposition rate of 0.2 nm / sec. Evaporation was performed to a thickness of 30 nm to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec for 200 nm.
And a cathode was formed by co-evaporation (weight ratio: 10: 1) to obtain an organic electroluminescent device. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 64 mA / cm ² flowed. Brightness 1220cd
/ M ² was confirmed.

Examples 94-102 Instead of using the compound of Exemplified Compound No. A-18 in Example 93, the compound of Exemplified Compound No. A-19 (Example 94) and the compound of Exemplified Compound No. A-29 (Example Example 95), compound of Exemplified Compound No. C-18 (Example 96), compound of Exemplified Compound No. C-30 (Example 9)
7), Compound of Exemplified Compound No. C-49 (Example 9)
8), Compound of Exemplified Compound No. D-5 (Example 99),
Example 93 except that the compound of Exemplified Compound No. D-8 (Example 100), the compound of Exemplified Compound No. E-7 (Example 101), and the compound of Exemplified Compound No. E-9 (Example 102) were used. An organic electroluminescent device was produced by the method described in (1). When a DC voltage of 12 V was applied to each device under a dry atmosphere, white light emission was observed.
The characteristics were further examined, and the results are shown in Table 4 (Table 13).

[0140]

[Table 13]

Example 103 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,3-bis [5 '-(p-tert-butylphenyl) -1,3,4-oxadiazole-2'-
[Il] benzene and a compound of Exemplified Compound No. C-12 were formed by dip coating using a 3% by weight dichloroethane solution containing 100: 30: 3 by weight to form a 300 nm light emitting layer. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
Further, on the light emitting layer, magnesium and silver were co-deposited (weight ratio: 10: 1) at a deposition rate of 0.2 nm / sec to a thickness of 200 nm to form an organic electroluminescent device. The prepared organic electroluminescent device was dried under a dry atmosphere for 15 minutes.
When a DC voltage of V was applied, a current of 68 mA / cm ² flowed. Orange-red light emission with a luminance of 1480 cd / m ² was confirmed.

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

Example 104 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight: 50,000),
4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, bis (2-methyl-8-
Quinolinolate) aluminum-μ-oxo-bis (2
-Methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. D-15 were each added at a weight ratio of 10
Using a 3% by weight dichloroethane solution containing 0: 40: 60: 1 at a ratio of 30% by a dip coating method.
A 0 nm light emitting layer was formed. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device,
The pressure in the evaporation tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were deposited at a deposition rate of 0.2 nm / 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. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 61 mA / cm ² flowed. Brightness 96
An orange-red emission of 0 cd / m ² was confirmed.

[0144]

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

[Brief description of the drawings]

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

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

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

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

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

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

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

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

[Explanation of symbols]

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

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat ゛ (Reference) C09K 11/06 620 C09K 11/06 620 660 660 F Term (Reference) 3K007 AB02 AB04 CA01 CB01 DA01 DB03 DC00 EB00 4H006 AA01 AA03 AB92 GP03

Claims (8)

[Claims] A benzo [5,6] indeno is provided between a pair of electrodes.
[1,2,3-cd] phenanthro [9 ', 10': 5,6] indeno [1,2,3-l
[m] An organic electroluminescence device comprising at least one layer containing at least one perylene derivative. 2. A layer containing a benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′: 5,6] indeno [1,2,3-lm] perylene derivative. The organic electroluminescent device according to claim 1, which is a light emitting layer. 3. A layer containing a benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′: 5,6] indeno [1,2,3-lm] perylene derivative. The organic electroluminescent device according to claim 1, further comprising a luminescent organic metal complex. 4. A layer containing a benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′: 5,6] indeno [1,2,3-lm] perylene derivative. The organic electroluminescent device according to claim 1, further comprising a triarylamine derivative. 5. The organic electroluminescent device according to claim 1, further comprising a hole injection transport layer between the pair of electrodes. 6. The organic electroluminescent device according to claim 1, further comprising an electron injection / transport layer between the pair of electrodes. 7. A benzo [5,6] indeno [1,2,3-cd] phenanthro [9 ′, 10 ′: 5,6] indeno [1,2,3-lm] perylene derivative represented by the general formula: The organic electroluminescent device according to any one of claims 1 to 6, which is a compound represented by 1-A) (formula 1). Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. ) 8. A hydrocarbon compound represented by the general formula (1-A) (formula 2). Embedded image (Wherein X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. )