JP2000133457A - Hydrocarbon compound and organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To emit the light of high luminescence with high durability and high luminous efficiency by holding a layer including bisphenanthreno[9',10':6,7]indeno[1,2,3-cd:1',2',3'-1m]perylene derivative, between a pair of electrodes. SOLUTION: An organic electroluminescent element is manufactured by forming a luminescent layer, and further a hole injection transporting layer and an electron injection and transfer layer when necessary, between a pair of electrodes. This luminescent layer includes a bisphenanthreno[9',10':6,7]indeno[1,2,3-cd:1',2',3'-1m]perylene derivative represented by a formula (X1-X28 are independently a hydrogen atom, a halogen atom, a straight chained, branched or cyclic alkyl group, a straight chained, branched or cyclic alkoxy group, or an optionally substituted aryl group, or the groups adjacent to one another optionally form an optionally substituted carbon ring-type alicyclic ring with a substituted carbon atom by bonded with one another), and includes a luminescent organic metallic complex and a triarylamine derivative when necessary.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

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

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent 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 electroluminescent device (organic electroluminescent device: organic EL device) using an organic material as a light emitting material has been developed [Appl. Phys. Lett., 51 ,
913 (1987)]. The organic electroluminescent element has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode,
An exciton is generated by injecting electrons and holes into the thin film and recombining them, and emits light using light emitted when the exciton is deactivated. is there. The organic electroluminescent element can emit light at a low DC voltage of about several volts to several tens of volts, and various colors (for example, red, blue, and green) can be obtained by selecting the type of the fluorescent organic compound. ) Is possible. Organic electroluminescent devices having such features include various light emitting devices,
Application to display elements and the like is expected. However,
Generally, the light emission luminance is low and is not practically sufficient.

As a method for improving the light emission luminance, for example, an organic electroluminescent device using tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative, and a pyran derivative as a guest compound (dopant) as a light emitting layer has been proposed. J. Appl. Phys., 65 , 361
0 (1989)]. Further, as a light emitting layer, for example, a screw (2
An organic electroluminescent device using -methyl-8-quinolinolate) (4-phenylphenolate) 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 device.

[0005]

Means for Solving the Problems The present inventors have made intensive studies on the organic electroluminescent device and the compounds used in the device, and as a result, completed the present invention. That is,
The present invention provides at least a bisphenanthreno [9 ′, 10 ′: 6,7] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative between a pair of electrodes. Bisphenanthreno [9 ', 10': 6,7] indeno [1,2,3-cd: an organic electroluminescent device comprising at least one layer containing at least one type thereof.
The organic electroluminescent device according to the above, wherein the layer containing at least one 1 ', 2', 3'-lm] perylene derivative is a light-emitting layer, and bisphenanthreno [9 ', 10': 6,7] indeno [ 1,2,3-cd:
The organic electroluminescent device according to the above, wherein the layer containing at least one 1 ', 2', 3'-lm] perylene derivative contains a luminescent organometallic complex. , 7] indeno [1,2,3-cd:
The organic electroluminescent device according to or described above, wherein the layer containing at least one [1 ', 2', 3'-lm] perylene derivative contains a triarylamine derivative, further comprising a hole injection transport layer between a pair of electrodes. The organic electroluminescent device according to any one of the above-mentioned, wherein, between a pair of electrodes, further, the organic electroluminescent device according to any one of the above-described having an electron injection transport layer, bisphenanthreno [9 ′, 10 ': 6,7] indeno [1,2,3-cd:
The present invention relates to the organic electroluminescent device according to any one of the above, wherein the [1 ′, 2 ′, 3′-lm] perylene derivative is a compound represented by the general formula (1-A) (Formula 3). Furthermore, the present invention relates to a compound represented by the general formula (1-A).

[0006]

Embedded image (Wherein, X _{1 to} X ₂₈ 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, a substituted or unsubstituted aryl group, and adjacent groups selected from X _{1 to} X ₂₈ are bonded to each other to form a substituted or unsubstituted group together with a substituted carbon atom. It may form a carbocyclic aliphatic ring. )

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The organic electroluminescent device of the present invention, between a pair of electrodes,
Bisphenanthreno [9 ', 10': 6,7] indeno [1,2,3-cd:
[1 ', 2', 3'-lm] Perylene derivative is sandwiched between at least one layer containing at least one kind thereof. Bisphenanthreno [9 ', 10': 6,7] indeno [1,2,3-c according to the present invention
[d: 1 ′, 2 ′, 3′-lm] perylene derivative (hereinafter abbreviated as compound A according to the present invention) represents a compound having a skeleton represented by general formula (1) (formula 4) And the general formula (1)
The skeleton represented by may have various substituents, and is preferably a compound represented by the general formula (1-A) (Formula 4).

[0008]

Embedded image (Wherein, X _{1 to} X ₂₈ 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, a substituted or unsubstituted aryl group, and adjacent groups selected from X _{1 to} X ₂₈ are bonded to each other to form a substituted or unsubstituted group together with a substituted carbon atom. It may form a carbocyclic aliphatic ring. )

In the compound represented by the general formula (1-A), X _{1 to} X ₂₈ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkyl group. Represents an alkoxy group or a substituted or unsubstituted aryl group. In the present invention, the aryl group means a carbocyclic aromatic group such as a phenyl group and a naphthyl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group and a pyridyl group. In the compound represented by the general formula (1-A), more preferably, X _{1 to} X ₂₈
Is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, or 4 to 20 carbon atoms.
Represents a substituted or unsubstituted aryl group.

Specific examples of X _{1 to} X ₂₈ 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, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 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-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5
-Trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl , N-heptadecyl group, n-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group. Linear chains such as cyclooctyl groups,
A branched or cyclic alkyl group;

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
A linear, branched or cyclic alkoxy group such as -octadecyloxy group, n-eicosyloxy group;

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

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

More preferably, a hydrogen atom, a fluorine atom,
A chlorine atom, a straight-chain, branched or cyclic alkyl group having 1 to 16 carbon atoms, a straight-chain, branched or cyclic alkoxy group having 1 to 16 carbon atoms, or an aryl group having 6 to 20 carbon atoms, more preferably A hydrogen atom, a fluorine atom, a chlorine atom, a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, a straight-chain, branched or cyclic alkoxy group having 1 to 10 carbon atoms, or substitution having 6 to 16 carbon atoms Or an unsubstituted aryl group. Further, groups adjacent to each other in X _{1 to} X ₂₈ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with the substituted carbon atom, It may form a substituted or unsubstituted carbocyclic aliphatic ring having 4 to 7 carbon atoms.

In the general formula (1-A), X ₉ , X ₁₄ ,
X ₂₃ and X ₂₈ are a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, and other compounds wherein X is a hydrogen atom. More preferred are compounds in which X ₉ , X ₁₄ , X ₂₃ and X ₂₈ are a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, and other X is a hydrogen atom.

In the organic electroluminescent device of the present invention, bisphenanthreno [9 ', 10': 6,7] indeno [1,2,3-cd: 1 ',
It is characterized by using at least one kind of 2 ′, 3′-lm] perylene derivative. For example, bisphenanthreno [9 ′, 10 ′]:
The use of 6,7] indeno [1,2,3-cd: 1 ', 2', 3'-lm] perylene derivative in the light-emitting layer as a light-emitting component provides unprecedented high brightness and excellent durability An organic electroluminescent device that emits red light can be provided. Further, when a light-emitting layer is formed in combination with another light-emitting component, an organic electroluminescent element that emits white light with high luminance and excellent durability can be provided. Specific examples of the compound A according to the present invention include, for example, the following compounds (Chemical Formulas 5 to 29), but the present invention is not limited thereto.

[0017]

Embedded image

[0018]

Embedded image

[0019]

Embedded image

[0020]

Embedded image

[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

The compound A according to the present invention, for example, the compound represented by the general formula (1-A) is, for example, a compound represented by the general formula (2)
A compound represented by the formula (3) and a compound of the formula (3)
Can be produced, for example, by reacting with a compound represented by the formula (I) in the presence of aluminum chloride / sodium chloride, cobalt trifluoride, or thallium trifluoroacetate (for example, J. Amer. Chem. Soc. , 118 , 23
74 (1996)].

[0043]

Embedded image [In the above formula, X _{1 to} X ₂₈ represent the same meaning as in the general formula (1-A). ]

Acenaphtho [1,2-b] triphenylene derivatives represented by the general formulas (2) and (3) are described in, for example, Indian J. Chem. Sect. B, 22B , 225 (1983). It can be manufactured according to the method described. That is, acenaphth represented by the general formulas (2) and (3)
[1,2-b] triphenylene derivatives include, for example, 2H-cyclopenta [l] phenanthrene-2-one derivatives [for example, Chem. Rev., 65, 261 (1965), J. Amer. Chem. So
c., 109, 4660 (1987).)
After reacting with the acenaphthylene derivative, removing carbon monoxide, and then reacting with, for example, chloranil, the compound can be produced by dehydrogenation. Acenaphtho [1,2-b] triphenylene derivatives represented by the general formulas (2) and (3) include, for example, 2H-cyclopenta [l] phenanthrene-2-one derivative and 1-halogenoacenaphthylene The derivative can be produced by reacting and then removing carbon monoxide.

Further, the compound A according to the present invention, for example,
The compound represented by the general formula (1-A) is, for example, a compound represented by the general formula (4) (Formula 31) represented by an oxidizing agent (e.g., Reaction and ring closure in the presence of aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, ferric chloride, thallium trifluoroacetate, or lead tetraacetate) [see, for example, J. Amer. Chem. Soc., 102 , 65
04 (1980), Chem. Rev., 87 , 357 (1987) can be referred to].

[0046]

Embedded image [In the above formula, X _{1 to} X ₂₈ represent the same meaning as in the case of the general formula (1-A). ]

The compound represented by the general formula (4) is, for example, a benzo [k] fluoranthene derivative represented by the general formula (5) and a compound represented by the general formula (6): The resulting acenaphtho [1,2-b] triphenylene derivative is reacted, for example, in the presence of nickel chloride, triphenylphosphine and zinc, and optionally sodium bromide [see, for example, J. Org. Chem. , 51 , 2627 (1986)
Can be referred to).

[0048]

Embedded image [In the above formula, X _{1 to} X ₂₈ represent the same meaning as in the case of the general formula (1-A), and Z ₁ and Z ₂ represent a halogen atom. In the general formulas (5) and (6), Z ₁ and Z ₂ represent a halogen atom, and preferably represent a chlorine atom, a bromine atom and an iodine atom.

The compound represented by the general formula (4)
For example, a compound represented by the general formula (5) and a compound represented by the general formula (6)
Is reacted with, for example, palladium acetate in the presence of tetra-n-butylammonium bromide (for example, Tetrahedron Lett., 39 , 2559 (199
The method described in 8) can be referred to]. Further, the compound represented by the general formula (4) is, for example, a compound represented by the general formula (5) in the presence of a nickel complex [for example, bis (1,5-cyclooctadiene) nickel]. It can be produced by reacting a compound represented by the general formula (6) [for example, J. Amer. Chem. Soc., 103 , 6460].
(1981), Macromolecules, 25 , 1214 (1992).

Acenaphtho [1,2-b] triphenylene derivatives represented by the general formulas (5) and (6) are described in, for example, Indian J. Chem. Sect. B, 22B , 225 (1983). It can be produced with reference to the method described. That is, acenaphtho [1,2-b] triphenylene derivatives represented by the general formulas (5) and (6) are, for example, 2H-
Cyclopenta [l] phenanthren-2-one derivative and 5
After the reaction of the halogenoacenaphthylene derivative, the carbon monoxide is removed therefrom, and then, for example, the compound can be produced by dehydrogenation with chloranil or the like. Acenaphtho [1,2-b] triphenylene derivatives represented by the general formulas (5) and (6) include, for example, 2H-cyclopenta [l] phenanthrene-2-one derivative and 1,5-dihalogeno derivative. It can be produced by reacting the acenaphthylene derivative and then removing carbon monoxide.

The compound represented by the general formula (4) is
For example, a compound represented by the general formula (6) and a compound represented by the general formula (7)
For example, a boric acid compound represented by (Chemical Formula 33) is converted into a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, hydrogen carbonate) Sodium, triethylamine)
(Eg, Chem. Rev., 95 , 2457).
(1995) can be referred to]. Similarly, the compound represented by the general formula (4) is obtained by, for example, using a compound represented by the general formula (5) and a boric acid compound represented by the general formula (8) (Formula 33). Can also be manufactured.

[0052]

Embedded image [In the above formula, X _{1 to} X ₂₈ represent the same meaning as in the case of the general formula (1-A). ]

The compound represented by the general formula (7) is, for example, more n-type than the compound represented by the general formula (5).
Butyllithium, a lithiated compound or a Grignard reagent that can be prepared by the action of metallic magnesium, and, for example, trimethoxyboron, triisopropoxyboron or the like (for example, Chem. Rev., 9
5 , 2457 (1995)]. Similarly, the compound represented by the general formula (8) can be prepared, for example, from the compound represented by the general formula (6).

The compound A according to the present invention, for example, the compound represented by the general formula (1-A) may be a solvent (for example, an aromatic hydrocarbon solvent such as toluene) used in some cases.
May be produced in a form that forms a solvate with
In the present invention, such a solvate is included. Needless to say, a non-solvate containing no solvent is also included. In the organic electroluminescent device of the present invention, not only a non-solvate of the compound A of the present invention but also such a solvate can be used. Compound A according to the present invention,
For example, when the compound represented by the general formula (1-A) is used for an organic electroluminescent device, a purification method such as a recrystallization method, a column chromatography method, a sublimation purification method, or a combination of these methods is used. It is preferable to use a compound with increased purity.

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 Needless to say, depending on the case, a structure of a device (single-layer device) in which both the hole injection transport layer and the electron injection transport layer are not provided may be employed. 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 include, A layer having an injection function and a layer having a transport function may be separately provided.

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

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

The organic electroluminescent device of the present invention is not limited to these device configurations, but may be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers 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 injecting and transporting component may be provided between the light emitting layer and the electron injecting and transporting 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,
It is a (G) type element or an (H) type element, and more preferably an (A) type element, a (B) type element, a (C) type element or a (F) type element. As the organic electroluminescent device of the present invention, for example, (A) anode / hole injection / transport layer / emission layer / electron injection / transport layer / cathode device shown in FIG. 1 will be described. In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer, 5 is an electron injection / transport layer, 6
Indicates a cathode, and 7 indicates a power supply.

The organic electroluminescent device of the present invention is preferably supported on a substrate 1. The substrate is not particularly limited, but is preferably transparent or translucent. Transparent plastic sheet (for example, polyester, polycarbonate, polysulfone, polymethyl methacrylate, polypropylene,
A sheet made of polyethylene or the like), a translucent plastic sheet, quartz, a transparent ceramic, or a composite sheet combining these. Further, the luminescent color can be controlled by combining, for example, a color filter film, a color conversion film, and a dielectric reflection film on the substrate.

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 the substrate by using such an electrode material by, for example, a vapor deposition method, a sputtering method, or the like. 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 / □.
Hereinafter, more preferably, it is set to about 5 to 50 Ω / □. The thickness of the anode 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.

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-vinyl carbazole derivative, and the like). The compounds having a hole injection / transport function may be used alone or in combination of two or more.

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

The light emitting layer 4 has a hole and electron injection function,
This is a layer containing a compound having a transport function thereof and a function of generating excitons by recombination of holes and electrons. The light-emitting layer is formed of the compound A according to the present invention and / or a compound having a light-emitting function (eg, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [eg, rubrene, anthracene, tetracene, pyrene). , Perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 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- Rinorato) 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 salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [for example, 1,1,4,
4-tetraphenyl-1,3-butadiene, 4,4′-
Bis (2,2-diphenylvinyl) biphenyl, 4,
4'-bis [(1,1,2-triphenyl) ethenyl]
Biphenyl], coumarin derivatives [for example, coumarin 1,
Coumarin 6, Coumarin 7, Coumarin 30, Coumarin 10
6, Coumarin 138, Coumarin 151, Coumarin 15
2, Coumarin 153, Coumarin 307, Coumarin 31
1. Coumarin 314, Coumarin 334, Coumarin 33
8, coumarin 343, coumarin 500], pyran derivatives [eg, DCM1, DCM2], oxazone derivatives [eg, Nile Red], benzothiazole derivatives,
Benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamate derivatives, poly-
N-vinyl carbazole and its derivatives, polythiophene and its derivatives, polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and Derivatives, polythienylenevinylene and derivatives thereof) can be used.

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

As the other compound having a light emitting function used in the present invention, a light emitting organic metal complex is more preferable. For example, as described in J. Appl. Phys., 65 , 3610 (1989) and JP-A-5-214332, 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 light emitting layer is formed using the compound A according to the present invention as a guest compound, the host compound includes
For example, the above-mentioned compounds having another light-emitting function can be mentioned. For example, a light-emitting organic metal complex or a triarylamine derivative is more preferable. In this case, for the luminescent organometallic complex or the triarylamine derivative,
Compound A, preferably about 0.001 to 40% by weight,
More preferably, it is used in an amount of about 0.01 to 30% by weight, particularly preferably about 0.1 to 20% by weight.

The luminous organometallic complex used in combination with the compound A according to the present invention is not particularly limited, but a luminous organoaluminum complex is preferable, and a luminescence 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) (wherein Q represents substituted 8 Represents a quinolinolate ligand, OL represents 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) (wherein Q represents a substituted 8-quinolinolate ligand)

Specific examples of the luminescent organometallic complex include, for example, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, tris ( 3,4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) (Phenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum,
Bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinolate) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolate) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8- Quinolinolate) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8
-Quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate) ) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate)
(3-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) ) Aluminum, bis (2,4-dimethyl-8-)
Quinolinolate) (3,5-di-tert-butylphenolate) aluminum,

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

The electron injection / transport 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 (for example, an organometallic complex [for example, tris (8-quinolinolate) aluminum, bis (10-benzo [h] quinolinolate) ) Beryllium, 5
-Beryllium salt of hydroxyflavone, aluminum salt of 5-hydroxyflavone], oxadiazole derivative, triazole derivative, triazine derivative, perylene derivative, quinoline derivative, quinoxaline derivative, diphenylquinone derivative, nitro-substituted fluorenone derivative, thiopyrandioxide derivative And the like can be formed using at least one of them. When the compound A according to the present invention and a compound having another 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 about 0.1 to 40% by weight. Prepare.
In the present invention, it is preferable to form the electron injecting and transporting layer by using the compound A according to the present invention and an organometallic complex [for example, the compounds represented by the general formulas (a) to (c)] in combination.

As the cathode 6, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively low 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 of two or more. The cathode, these electrode substances, for example, a vapor deposition method, a sputtering method,
It can be formed on the electron injection transport layer by a method such as an ionization vapor deposition method, an ion plating method, and a cluster ion beam method. Further, the cathode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the cathode is preferably set to several hundreds 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 preferable. 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 oxygen quencher is contained in the hole injecting and transporting layer, the singlet oxygen quencher may be contained uniformly in the hole injecting and transporting layer. (Electron injection / transport layer having a light emitting function). The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.0
5 to 30% by weight, more preferably 0.1 to 20% by weight
It is.

The method for forming the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer is not particularly limited, and may be, for example, a vacuum evaporation method, an ionization evaporation method, a solution coating method (for example, a spin coating method, a casting method, or the like). Method, dip coating method,
It can be manufactured by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, an inkjet method, or the like. By vacuum evaporation method,
In the case of forming each layer, the conditions of vacuum deposition are not particularly limited, but the vacuum deposition is performed under a vacuum of about 10 ⁻⁵ Torr or less.
Boat temperature of about 0 to 600 ° C (evaporation source temperature), -50
At a substrate temperature of about 300 ° C. to about 0.005 to 50 nm /
It is preferable to carry out at a deposition rate of about sec. In this case, by forming each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer continuously under a vacuum, an organic electroluminescent element having more excellent 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 deposition method, each boat containing the compounds is individually temperature-controlled,
Co-evaporation is preferred.

When each layer is formed by a solution coating method,
The components forming each layer or the components and a binder resin or the like are dissolved or dispersed in a solvent to form a coating liquid. 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 the like.
Polymethyl methacrylate, polyether, polycarbonate, polyamide, polyimide, polyamide imide,
Polyparaxylene, polyethylene, polyethylene ether, polypropylene ether, polyphenylene oxide, polyether sulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylene vinylene and its derivatives, polyfluorene and its derivatives, polythienylene vinylene and its derivatives, etc. High molecular compounds are exemplified. The binder resin may be used alone or in combination.

When each layer is formed by a solution coating method,
The components forming each layer or the components and a binder resin are combined 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, trichloroethane, Halogenated hydrocarbon solvents such as tetrachloroethane, chlorobenzene, dichlorobenzene and chlorotoluene, for example, ethyl acetate, butyl acetate, ester solvents such as amyl acetate, for example, methanol, ethanol, propanol, butanol, pentanol, hexanol, Alcohol-based solvents such as cyclohexanol, methyl cellosolve, ethyl cellosolve, and ethylene glycol, for example, dibutyl ether, tetrahydrofuran, dioxane Down, ether solvents anisole, for example, N, N-dimethylformamide, N, N-
Dimethylacetamide, 1-methyl-2-pyrrolidone,
A polar solvent such as 1,3-dimethyl-2-imidazolidinone and dimethyl sulfoxide) and / or dissolved or dispersed in water to form a coating solution, and a thin film can be formed by various coating methods. .

The method of dispersion is not particularly limited. For example, the particles can be dispersed into fine particles using a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like. The concentration of the coating solution is not particularly limited, and can be set to a concentration range suitable for producing a desired thickness depending on a coating method to be performed, and is generally about 0.1 to 50% by weight. Preferably, the solution concentration is about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin is not particularly limited. However, in general, the amount of the binder resin is limited to the components forming each layer (when forming a single-layer element, the total 5) to 99.9% by weight
Level, preferably about 10 to 99% 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.
A protective layer (sealing layer) may be provided on the fabricated device for the purpose of preventing contact with oxygen, moisture, or the like, 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, an aluminum oxide film) or a metal fluoride film may be provided as a protective film on the electrode. Also, for example, on the surface of the anode,
For example, an interface layer (intermediate layer) made of an organic phosphorus compound, polysilane, an aromatic amine derivative, a phthalocyanine derivative (for example, copper phthalocyanine), or carbon can be provided. In addition, electrodes, for example, anodes,
For example, it can be used after being treated with an acid, ammonia / hydrogen peroxide, or plasma.

The organic electroluminescent device of the present invention is generally used as a DC-driven device, but can also be used as a pulse-driven or AC-driven device.
Incidentally, the applied voltage is generally about 2 to 30 V. 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.

[0079]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Production Examples and Examples, but of course, the present invention is not limited thereto. Production Example 1: Production of Compound of Exemplified Compound No. D-1 5 g of 9,16-diphenylacenaphtho [1,2-b] triphenylene and 5 g of cobalt trifluoride were heated in trifluoroacetic acid (150 ml) for 20 hours. And refluxed. After trifluoroacetic acid was distilled off under reduced pressure, water (100 m
After l) was added, the solid was filtered. This solid was washed with acetone and then treated by alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to obtain 2.4 g of a compound of Exemplified Compound No. D-1 as purple crystals. Melting point is 250 ° C or higher. This compound was able to sublime at 480 ° C. and 10 ⁻⁵ torr. The absorption maximum (in toluene) was 595 nm.

Production Examples 2 to 24 In Production Example 1, 9,16-diphenylacenaphtho
According to the method described in Production Example 1, except that various acenaphtho [1,2-b] triphenylene derivatives were used instead of using [1,2-b] triphenylene, various bisphenanthreno [9 ' , 10 ': 6,7] indeno [1,2,3-cd: 1', 2 ', 3'-lm]
A perylene derivative was produced. In Table 1 (Tables 1 to 5),
Acenaphtho [1,2-b] triphenylene used and bisphenanthreno [9 ', 10': 6,7] indeno [1,2,3 prepared
[cd: 1 ', 2', 3'-lm] perylene derivatives are shown by the example compound numbers. The maximum absorption (nm) in toluene is also shown. In addition, the produced compound was a red purple to blue purple crystal, and its melting point was 250 ° C. or higher. Depending on the type of acenaphtho [1,2-b] triphenylene derivative used, bisphenanthreno [9 ′, 10 ′: 6,
7] Indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivatives may be produced as a mixture, but the proportion of the mixture is almost the same.

[0081]

[Table 1]

[0082]

[Table 2]

[0083]

[Table 3]

[0084]

[Table 4]

[0085]

[Table 5]

Preparation Example 25: Preparation of Compound of Exemplified Compound No. D-53 ]
5 g of triphenylene and 7 g of cobalt trifluoride were heated and refluxed in trifluoroacetic acid (150 ml) for 36 hours. After trifluoroacetic acid was distilled off under reduced pressure, water (100 ml) was added to the residue, and the solid was filtered. This solid was washed with acetone and then separated and purified by alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to obtain 3.5 g of a compound of Exemplified Compound No. D-53 as purple crystals. The melting point was 250 ° C. or higher, and the absorption maximum (in toluene) was 595 nm.

The used 9,16-diphenyl-
9 ', 16'-bis (4 "-methylphenyl) -12,
12′-Biasenaphtho [1,2-b] triphenylene was produced by the following method. That is, 12- (9,16-
3 g of diphenylacenaphtho [1,2-b] triphenylenyl) borate, 3.3 g of 12-bromo-9,16-bis (4′-methylphenyl) acenaphtho [1,2-b] triphenylene 3.3
g, 2 g of sodium carbonate, and 200 mg of tetrakis (triphenylphosphine) palladium were refluxed in toluene (100 ml) and water (20 ml) for 5 hours. After the toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was separated and purified by alumina 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 give 9,16 as yellow crystals.
4.7 g of -diphenyl-9 ', 16'-bis (4 "-methylphenyl) -12,12'-biasenaphtho [1,2-b] triphenylene was obtained.

Production Examples 26 to 31 In Production Example 25, 9,16-diphenyl-9 ', 1
6'-bis (4 "-methylphenyl) -12,12'-
In accordance with the method described in Production Example 25, various bis-naphtho [1,2-b] triphenylenes were used in place of using various 12,12′-biasenaphtho [1,2-b] triphenylene derivatives. Phenanthreno [9 ', 10': 6,7]
Indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivatives were prepared. In Table 2 (Tables 6 and 7), the used 12, 12 '
-Biasenaphtho [1,2-b] triphenylene derivative and bisphenanthreno [9 ′, 10 ′: 6,7] indeno [1,
[2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative is shown by an example compound number. The maximum absorption (nm) in toluene is also shown. In addition, the produced compound was a red purple to blue purple crystal, and its melting point was 250 ° C. or higher.

[0089]

[Table 6]

[0090]

[Table 7]

Example 1 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr.
First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was 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 9,14,23,28-
Tetraphenylbisphenanthreno [9 ', 10': 6,7] indeno [1,2,3-cd: 1 ', 2', 3'-lm] perylene (Exemplary Compound No. D
-1) from different deposition sources at a deposition rate of 0.2
Co-deposition to a thickness of 50 nm at 10 nm / sec (weight ratio 10
0: 0.5) 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 seconds to obtain an electron injection transport layer. Further thereon, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, 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 55 mA / cm ² flowed. Red light emission with a luminance of 2420 cd / m ² was confirmed.

Examples 2 to 28 In Example 1, instead of using the compound of Exemplified Compound No. D-1 in forming the light emitting layer, the compound of Exemplified Compound No. D-2 (Example 2) D-3
(Example 3), compound of Exemplified Compound No. D-4 (Example 4), compound of Exemplified Compound No. D-6 (Example 5), compound of Exemplified Compound No. D-7 (Example 6), Compound of Exemplified Compound No. D-8 (Example 7), Compound of Exemplified Compound No. D-17 (Example 8), Exemplified Compound No. D
-18 (Example 9), Exemplified Compound No. D-20
And the same amount mixture of Exemplified Compound No. D-21 (Example 1
0), Compound of Exemplified Compound No. D-24 (Example 1)
1), Compound of Exemplified Compound No. D-26 (Example 1)
2), Compound of Exemplified Compound No. D-27 (Example 1)
3), Compound of Exemplified Compound No. D-29 (Example 1)
4), Compound of Exemplified Compound No. D-35 (Example 1)
5), Compound of Exemplified Compound No. D-36 (Example 1)
6), Compound of Exemplified Compound No. D-40 (Example 1)
7), Compound of Exemplified Compound No. D-41 (Example 1)
8), Compound of Exemplified Compound No. D-45 (Example 1)
9), Compound of Exemplified Compound No. D-48 (Example 2)
0), Compound of Exemplified Compound No. D-51 (Example 2)
1), Compound of Exemplified Compound No. D-53 (Example 2)
2), Compound of Exemplified Compound No. D-54 (Example 2)
3), Compound of Exemplified Compound No. D-56 (Example 2)
4), Compound of Exemplified Compound No. D-57 (Example 2)
5), Compound of Exemplified Compound No. D-60 (Example 2)
6), Compound of Exemplified Compound No. D-61 (Example 2)
7), Compound of Exemplified Compound No. D-63 (Example 28)
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
The results are shown in Tables (Tables 8 and 9).

Comparative Example 1 In Example 1, when forming the light emitting layer, the compound of Exemplified Compound No. D-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 3.

Comparative Example 2 In Example 1, when forming the light emitting layer, instead of using the compound of Exemplified Compound No. D-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 3.

[0095]

[Table 8]

[0096]

[Table 9]

Example 29 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-methyl-8-quinolinolate) (2-phenylphenolate) aluminum and the compound of Exemplified Compound No. D-1 were deposited thereon from different evaporation sources at a deposition rate of 0. .2 nm / s
ec to a thickness of 50 nm (weight ratio: 100: 1.
0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Furthermore, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm.
/ Sec to co-deposition 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 58 mA / cm ² flowed. Red light emission with a luminance of 2380 cd / m ² was confirmed.

Example 30 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. A hole injecting and transporting layer was formed thereon, and then bis (2-methyl-8-quinolinolate) aluminum-
μ-oxo-bis (2-methyl-8-quinolinolate)
Aluminum and the compound of Exemplified Compound No. D-3 were deposited at a deposition rate of 0.2 nm / sec and 50 nm from different deposition sources.
(Thickness: 100: 2.0) to obtain a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec.
Co-deposit (weight ratio 10: 1) to a thickness of nm to form a cathode,
An organic electroluminescent device was manufactured. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Brightness 2340c
Red light emission of d / m ² was confirmed.

Example 31 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. A hole injecting and transporting layer was formed thereon, and then bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. D- 26 compounds were obtained from different evaporation sources at a deposition rate of 0.2 nm / s
ec to 50 nm thickness (weight ratio 100: 4.
0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Furthermore, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm.
/ Sec to co-deposition 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 60 mA / cm ² flowed. Red light emission with a luminance of 2270 cd / m ² was confirmed.

Example 32 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-4 were deposited thereon from different evaporation sources to a thickness of 50 nm at an evaporation rate of 0.2 nm / sec. The light emitting layer was formed by vapor deposition (weight ratio: 100: 6.0).
-Quinolinolate) aluminum at a deposition rate of 0.2 n
It was deposited at a thickness of 50 nm at m / sec to form an electron injecting and transporting layer. Further thereon, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In a dry atmosphere, add 1
When a DC voltage of 2 V was applied, a current of 60 mA / cm ² flowed. Red light emission with a luminance of 2260 cd / m ² was confirmed.

Example 33 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. D-17 were deposited thereon from different evaporation sources to a thickness of 50 nm at an evaporation rate of 0.2 nm / sec. The light emitting layer was formed by vapor deposition (weight ratio: 100: 10).
Quinolinolate) aluminum at a deposition rate of 0.2 nm
The film was deposited at a thickness of 50 nm / sec to form an electron injecting and transporting layer. Further thereon, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, 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 60 mA / cm ² flowed. Red light emission with a luminance of 2320 cd / m ² was confirmed.

Example 34 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 to a thickness of 50 nm at an evaporation rate of 0.2 nm / sec. Evaporation (weight ratio: 100: 1.0) was performed to form a light emitting layer also serving as an electron injecting and transporting layer, and magnesium and silver were further co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm ( A weight ratio of 10: 1) was used as a cathode to produce an organic electroluminescent device, and vapor deposition was performed while maintaining the reduced pressure of the vapor deposition tank.
When a DC voltage of V was applied, a current of 58 mA / cm ² flowed. Red light emission with a luminance of 1980 cd / m ² was confirmed.

Example 35 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, a compound of Exemplified Compound No. D-2 was further deposited thereon with a vapor deposition rate of 0.2 nm /.
Vapor deposition was performed to a thickness of 50 nm in seconds to form a light emitting layer. Next, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazole-2′-
Yl] benzene at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / s.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 200 nm using ec 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 produced organic electroluminescent device in a dry atmosphere, a current of 48 mA / cm ² flowed.
Red light emission with a luminance of 1820 cd / m ² was confirmed.

Example 36 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. D-1 was vapor-deposited on the ITO transparent electrode to a thickness of 55 nm at a vapor deposition rate of 0.2 nm / sec to form a light-emitting layer. Then, on top of that,
Bis [5 '-(p-tert-butylphenyl) -1,3,3
[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 injection transport layer. Further thereon, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, 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 15 V was applied to the produced organic electroluminescent device under a dry atmosphere, the voltage was 68 m.
A / cm ² current flowed. Red light emission with a luminance of 1280 cd / m ² was confirmed.

Example 37 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 was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec.
Then, it was deposited to a thickness of 50 nm to form a first hole injection transport layer. Then, 4,4'-bis [N-phenyl-N-
(1 "-Naphthyl) amino] biphenyl and Exemplified Compound D
-1 compound from different deposition sources, deposition rate 0.2 nm
/ Sec, co-evaporation to a thickness of 20 nm (weight ratio 100:
5) Then, a light emitting layer also serving as the second hole injection / transport layer was formed. Next, tris (8-quinolinolato) 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 are further deposited thereon at a deposition rate of 0.2 nm / sec.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 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 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 68 mA / cm ² flowed. Brightness 295
Red light emission of 0 cd / m ² was confirmed.

Examples 38 to 45 In Example 37, the compound of Exemplified Compound No. D-3 (Example 38) and the compound of Exemplified Compound No. D-6 (Example 38) were used instead of using the compound of Exemplified Compound No. D-1. Example 3
9), Compound of Exemplified Compound No. D-18 (Example 4)
0), Compound of Exemplified Compound No. D-26 (Example 4)
1), Compound of Exemplified Compound No. D-36 (Example 4)
2), Compound of Exemplified Compound No. D-48 (Example 4)
3), Compound of Exemplified Compound No. D-53 (Example 4)
4), Compound of Exemplified Compound No. D-56 (Example 45)
An organic electroluminescent device was prepared by the method described in Example 37 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 4 (Table 10).

[0107]

[Table 10]

Example 46 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
50,000), 1,1,4,4-tetraphenyl-1,
3-butadiene (blue light-emitting component), coumarin 6 ["3
-(2′-benzothiazolyl) -7-diethylaminocoumarin ”(green light-emitting component)] and the compound of Exemplified Compound No. D-10 at a weight ratio of 100: 5: 3:
A 400 nm light emitting layer was formed by dip coating using a 3% by weight dichloroethane solution containing 2 parts by weight. Next, after fixing the glass substrate having the light emitting layer to the substrate holder of the vapor deposition device, the vapor deposition tank was set to 3 × 10 ^−6.
The pressure was reduced to Torr. Furthermore, 3- (4 ′)
-Tert-butylphenyl) -4-phenyl-5-
(4 "-biphenyl) -1,2,4-triazole
After vapor deposition to a thickness of 20 nm at a vapor deposition rate of 0.2 nm / sec, tris (8-quinolinolate) aluminum was further deposited thereon at a vapor deposition rate of 0.2 nm / sec.
It was deposited to a thickness of 0 nm to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / s.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 200 nm using ec to produce an organic electroluminescent device. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 74 mA / cm ² flowed. White light emission with a luminance of 1210 cd / m ² was confirmed.

Examples 47 to 51 In Example 46, instead of using the compound of Exemplified Compound No. D-10, the compound of Exemplified Compound No. D-8 (Example 47) and the compound of Exemplified Compound No. D-13 (Example 47) Example 48), compound of Exemplified Compound No. D-29 (Example 49), compound of Exemplified Compound No. D-30 (Example 5)
0), Compound of Exemplified Compound No. D-57 (Example 51)
An organic electroluminescent device was manufactured by the method described in Example 46 except that was used. When a DC voltage of 12 V was applied to each element under a dry atmosphere, white light emission was confirmed. The characteristics were further examined, and the results are shown in Table 5 (Table 11).

[0110]

[Table 11]

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 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. D-8 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) to a thickness of 200 nm at a deposition rate of 0.2 nm / sec 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 76 mA / cm ² flowed. Red light emission with a luminance of 1450 cd / m ² was confirmed.

Comparative Example 3 In Example 52, 1,1,4,4-tetraphenyl-1,3-butadiene was used in place of the compound of Exemplified Compound No. D-8 in forming the light emitting layer. ,
An organic electroluminescent device was produced by the method described in Example 52. 15 V under dry atmosphere
Was applied, a current of 86 mA / cm ² flowed. Blue light emission with a luminance of 750 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 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-30 in a weight ratio of 10
Using a 3% by weight dichloroethane solution containing 0: 40: 60: 1 at a ratio of 300 by dip coating.
A light emitting layer of nm 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 vapor deposition 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.
By co-evaporation (weight ratio 10: 1) to a thickness of 200 nm by using c, a cathode was obtained, 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 66 mA / cm ² flowed. Red light emission with a luminance of 870 cd / m ² was confirmed.

[0114]

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 symbol FI Theme coat ゛ (Reference) C09K 11/06 602 C09K 11/06 602 610 610 660 660 660

Claims (8)

[Claims] A bisphenanthreno is provided between a pair of electrodes.
[9 ', 10': 6,7] Indeno [1,2,3-cd: 1 ', 2', 3'-lm] Organic comprising at least one layer containing at least one perylene derivative Electroluminescent device. 2. A layer containing at least one bisphenanthreno [9 ′, 10 ′: 6,7] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative. The organic electroluminescent device according to claim 1, wherein is a light emitting layer. 3. A layer containing at least one bisphenanthreno [9 ′, 10 ′: 6,7] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative. 3. The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device contains a luminescent organometallic complex. 4. A layer containing at least one bisphenanthreno [9 ′, 10 ′: 6,7] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative. The organic electroluminescent device according to claim 1, wherein the compound contains a triarylamine derivative. 5. The organic electroluminescent device according to claim 1, further comprising a hole injection transport layer between the pair of electrodes. 6. The organic electroluminescent device according to claim 1, further comprising an electron injection / transport layer between the pair of electrodes. 7. A bisphenanthreno [9 ′, 10 ′: 6,7] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative represented by the general formula (1)
The organic electroluminescent device according to any one of claims 1 to 6, wherein the compound is represented by -A) (formula 1). Embedded image (Wherein, X _{1 to} X ₂₈ 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, a substituted or unsubstituted aryl group, and adjacent groups selected from X _{1 to} X ₂₈ are bonded to each other to form a substituted or unsubstituted group together with a substituted carbon atom. It may form a carbocyclic aliphatic ring. ) 8. A compound represented by the general formula (1-A): Embedded image (Wherein, X _{1 to} X ₂₈ 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, a substituted or unsubstituted aryl group, and adjacent groups selected from X _{1 to} X ₂₈ are bonded to each other to form a substituted or unsubstituted group together with a substituted carbon atom. It may form a carbocyclic aliphatic ring. )