JP2000228286A - Organic electric field light emitting element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an element excellent in light emission efficiency, emitting light with high luminance by clamping at least one layer containing at least a compound containing an isoindole ring between a pair of electrodes. SOLUTION: This organic electric field light emitting element contains at least one layer of a compound expressed by formula I. Actually, a compound expressed by formula II is used. In formula I, Ar1 and Ar2 are aryl group; R1-R6 are H, halogen atom, cyano group, alkyl group, alkoxy group, aralkyl group, or aryl group; X1 is H, alkyl group, aralkyl group, or aryl group; and X2 is H, cyano group, alkyl group, aralkyl group, or aryl group. Preferably, the compound expressed by formula I is used for an electron hole injection transport component and a light emission component. Preferably, in the light emission layer, the compound expressed by formula I and a light emitting organometal compound having a light emission function or a triaryl amine derivative are used jointly, and the proportion of the compound expressed by formula I is preferably about 0.001 to 99.999 wt.%.

Description

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device.
About. 2. Description of the Related Art Conventionally, inorganic electroluminescent elements have been
It has been used as a panel-type light source such as a backlight.
However, a high AC voltage is required to drive the light-emitting element.
It is. Recently, organic materials using organic materials as light emitting materials
Electroluminescent device (organic electroluminescent device: yes
EL device) was developed [Appl. Phys. Lett., 51 ,
913 (1987)]. Organic electroluminescent devices are fluorescent organic compounds
Having a structure sandwiched between an anode and a cathode,
Inject electrons and holes into the thin film and recombine
Excitons are generated by this
Emits light using the light emitted when the exciton is deactivated.
Device. The organic electroluminescent element is about several V to several tens V
Can emit light at a low DC voltage, and
By selecting the type of compound, various colors (eg,
(Red, blue, green). like this
Organic electroluminescent devices having various characteristics, 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, a light emitting layer
For example, tris (8-quinolinolate) aluminum
Ni as host compound, coumarin derivative, pyran derivative
Electric field generation using as a guest compound (dopant)
Optical devices have been proposed [J. Appl. Phys., 65 , 3610 (1
989)]. Further, as a light emitting layer, tris (8-quinolino)
Lat) aluminum as host compound, pyromethene derivative
Body (eg, 1,3,5,7,8-pentamethyl-4,
4-difluoro-4-bora-3a, 4a-diaza-s-
Organic electroluminescence using Indacene) as guest compound
An element has been proposed (Japanese Unexamined Patent Publication No. Hei 9-118880).
Information). However, the use of the pyromethene derivative
It is said that the electroluminescent device also has sufficient light emission brightness.
It turned out to be difficult. Further, the pyrromethene derivative is
Poor adhesion between the containing layer and the electrode (eg, cathode)
It is necessary to improve it for long-term use.
It turned out. At present, organic electric field generators that emit light with high brightness
Optical devices are desired. [0004] The object of the present invention is to provide a luminous effect.
To provide an organic electroluminescent device that emits light with high efficiency and high brightness
Is Rukoto. [0005] The present inventors have proposed an organic electric field.
As a result of intensive studies on light emitting elements, the present invention is completed
Reached. That is, the present invention relates to a method represented by general formulas (1) and (2) between a pair of electrodes.
Sandwich at least one layer containing at least one compound
An organic electroluminescent device comprising: (Wherein, Ar ₁ And Ar _Two Is replaced or unplaced
Represents a substituted aryl group, ₁ ~ R ₆ Are independent of each other,
Hydrogen atom, halogen atom, cyano group, straight chain, branched or
Cyclic alkyl group, linear, branched or cyclic alkoxy
Group, substituted or unsubstituted aralkyl group, or
Or an unsubstituted aryl group, X ₁ Is a hydrogen atom,
Chain, branched or cyclic alkyl group, substituted or unsubstituted
Aralkyl groups or substituted or unsubstituted aryl groups
And X _Two Is a hydrogen atom, a cyano group, a straight-chain, branched or
A cyclic alkyl group, a substituted or unsubstituted aralkyl group,
Alternatively, it represents a substituted or unsubstituted aryl group. The layer containing the compound represented by the general formula (1) emits light.
The organic electroluminescent device as described above, wherein the layer containing the compound represented by the general formula (1) is
The organic electroluminescent device according to the above description, which is an injection / transport layer, wherein the layer containing the compound represented by the general formula (1) further comprises:
A luminescent organometallic complex or a triarylamine derivative
The body according to any of the above-mentioned, wherein at least one body is contained.
Before the organic electroluminescent element further has a hole injection / transport layer between the pair of electrodes
The organic electroluminescent device according to any one of to above, further comprising an electron injection transport layer between the pair of electrodes.
The organic electroluminescent device according to any one of to
Things. Hereinafter, the present invention will be described in detail.
I do. The organic electroluminescent device of the present invention, between a pair of electrodes,
At least one compound represented by the general formula (1)
It comprises at least one layer containing seeds.
You. [0009] (Wherein, Ar ₁ And Ar _Two Is replaced or unplaced
Represents a substituted aryl group, ₁ ~ R ₆ Are independent of each other,
Hydrogen atom, halogen atom, cyano group, straight chain, branched or
Cyclic alkyl group, linear, branched or cyclic alkoxy
Group, substituted or unsubstituted aralkyl group, or
Or an unsubstituted aryl group, X ₁ Is a hydrogen atom,
Chain, branched or cyclic alkyl group, substituted or unsubstituted
Aralkyl groups or substituted or unsubstituted aryl groups
And X _Two Is a hydrogen atom, a cyano group, a straight-chain, branched or
A cyclic alkyl group, a substituted or unsubstituted aralkyl group,
Alternatively, it represents a substituted or unsubstituted aryl group. In the compound represented by the general formula (1),
Ar ₁ And Ar _Two Represents a substituted or unsubstituted aryl group.
Then R ₁ ~ R ₆ Are each independently a hydrogen atom, a halogen
Atom, cyano group, linear, branched or cyclic alkyl group,
Straight, branched or cyclic alkoxy group, substituted or unsubstituted
A substituted aralkyl group or a substituted or unsubstituted aryl
X represents ₁ Is a hydrogen atom, linear, branched or cyclic
An alkyl group, a substituted or unsubstituted aralkyl group, or
Represents a substituted or unsubstituted aryl group; _Two Is hydrogen field
, Cyano group, linear, branched or cyclic alkyl group,
Substituted or unsubstituted aralkyl groups, or substituted or unsubstituted
Represents a substituted aryl group. In addition, the aryl group is, for example,
For example, a phenyl group, a carbocyclic aromatic group such as a naphthyl group,
For example, complex groups such as furyl, thienyl and pyridyl groups
Represents a cyclic aromatic group. In the compound represented by the general formula (1),
Ar ₁ And Ar _Two Represents a substituted or unsubstituted aryl group.
You. Ar ₁ And Ar _Two May have a substituent, for example,
For example, halogen atom, alkyl group, alkoxy group, aral
Kill group, aryl group, aryloxy group, amino group,
Mono- or poly-substituted by substituted amino group, cyano group, etc.
May be. Preferably, Ar ₁ And Ar _Two Is 3 carbon atoms
~ 24 substituted or unsubstituted aryl groups (e.g.
Nyl group, 2-methylphenyl group, 3-methylphenyl
Group, 4-methylphenyl group, 4-ethylphenyl group, 4
-N-propylphenyl group, 2-isopropylphenyl
Group, 4-isopropylphenyl group, 4-n-butylphen
Nyl group, 4-tert-butylphenyl group, 4-isopentene
Ruphenyl group, 4-tert-pentylphenyl group, 4-n
-Hexylphenyl group, 4-cyclohexylphenyl
Group, 4-n-octylphenyl group, 4-n-decylfe
Nyl group, 2,3-dimethylphenyl group, 2,4-dimethyl
Phenyl group, 2,5-dimethylphenyl group, 3,4-
Dimethylphenyl group, 2,4-diisopropylphenyl
Group, 5-indanyl group, 1,2,3,4-tetrahydro
-5-naphthyl group, 1,2,3,4-tetrahydro-
6-naphthyl group, 2-methoxyphenyl group, 3-methoxy
Cyphenyl group, 4-methoxyphenyl group, 3-ethoxy
Phenyl group, 4-n-propoxyphenyl group, 4-iso
Propoxyphenyl group, 4-n-butoxyphenyl group,
4-tert-butoxyphenyl group, 4-isopentyloxy
Cyphenyl group, 4-n-hexyloxyphenyl group, 4
-Cyclohexyloxyphenyl group, 4-n-decylo
A xyphenyl group, a 4-n-dodecyloxyphenyl group,
4-n-tetradecyloxyphenyl group, 4-n-hex
Sadesyloxyphenyl group, 4-n-octadecyloxy
Cyphenyl group, 2,3-dimethoxyphenyl group, 2,4
-Dimethoxyphenyl group, 2,5-dimethoxyphenyl
Group, 3,4-dimethoxyphenyl group, 2,4-diethoxy
A cyphenyl group, a 2-methoxy-5-methylphenyl group,
3-methyl-4-methoxyphenyl group, 2-fluorophenyl
Phenyl, 3-fluorophenyl, 4-fluorophenyl
Nyl group, 2-chlorophenyl group, 3-chlorophenyl
Group, 4-chlorophenyl group, 4-bromophenyl group, 4
-Trifluoromethylphenyl group, 3,4-dichloroph
Phenyl, 2-methyl-4-chlorophenyl, 2-
Loro-4-methylphenyl group, 3-chloro-4-methyl
Phenyl group, 2-chloro-4-methoxyphenyl group, 2
-Benzylphenyl group, 4-benzylphenyl group, 4-
(4'-methylbenzyl) phenyl group, 4- (4'-
Lorobenzyl) phenyl group, 4-cumylphenyl group, 2
-Phenylphenyl group, 3-phenylphenyl group, 4-
Phenylphenyl group, 4- (4′-methylphenyl) phenyl
Phenyl group, 4- (4′-methoxyphenyl) phenyl
Group, 2-phenyloxyphenyl group, 4-phenyloxy
Cyphenyl group, 4- (4′-methylphenyloxy) phenyl
Phenyl, 4- (4′-methoxyphenyloxy) phenyl
Nyl group, 4- (4′-chlorophenyloxy) phenyl
Group, 2-aminophenyl group, 3-aminophenyl group, 4
-Aminophenyl group, 2-N-methylaminophenyl
Group, 3-N-methylaminophenyl group, 4-N-methyl
Aminophenyl group, 2-N-ethylaminophenyl group,
4-N-ethylaminophenyl group, 4-Nn-propyl
Aminophenyl group, 4-N-isopropylaminophen
Nyl group, 4-N-n-butylaminophenyl group, 4-N
-Sec-butylaminophenyl group, 4-N-n-pliers
Aminophenyl group, 4-N-cyclohexylaminop
Phenyl, 4-Nn-octylaminophenyl, 4
-Nn-decylaminophenyl group, 4-Nn-dode
A silaminophenyl group, 2- (N, N-dimethylamino) phenyl
Group, 3- (N, N-dimethylamino) phenyl group, 4-
(N, N-dimethylamino) phenyl group, 4- (N-meth
Tyl-N-ethylamino) phenyl group, 4- (N, N-
Diethylamino) phenyl group, 4- (N, N-di-n-
Propylamino) phenyl group, 4- (N-methyl-N-
Isopropylamino) phenyl group, 4- (N, N-di-
n-butylamino) phenyl group, 4- (N-methyl-N
-N-butylamino) phenyl group, 4- (N-methyl-
N-cyclohexylamino) phenyl group, 4-N-fe
Nylaminophenyl group, 4-N- (4′-methylphenyl
L) aminophenyl group, 2- (N, N-diphenylamido)
(No) phenyl group, 3- (N, N-diphenylamino) phenyl
Phenyl group, 4- (N, N-diphenylamino) phenyl
Group, 4- [N, N-di (3'-methylphenyl) amido
No] phenyl group, 4- [N, N-di (4'-methyl
Nyl) amino] phenyl group, 4- [N, N-di (4′-
Methoxyphenyl) amino] phenyl group, 4- [N-f
Enyl-N- (3'-methylphenyl) amino] phenyl
Group, 4- [N-phenyl-N- (4′-methylphenyl)
L) amino] phenyl group, 4- [N-phenyl-N-
(4′-methoxyphenyl) amino] phenyl group, 4-
[N-phenyl-N- (1′-naphthyl) amino] fe
Nyl group, 4- (N-methyl-N-phenylamino) phenyl
Nyl group, 4- (N-ethyl-N-phenylamino) phenyl
Nyl group, 2-methyl-4- (N, N-dimethylamino)
Phenyl group, 2- (N, N-dimethylamino) -4-me
Tylphenyl group, 2-chloro-4- (N, N-diethyl
Amino) phenyl group, 3-methoxy-4- (N, N-di
Ethylamino) phenyl group, 4- (N-piperidino) phenyl
Phenyl, 4- (N-pyrrolidino) phenyl, 4-
(N-morpholino) phenyl group, juroidyl group,
Tramethyljuroidyl group, 2-cyanophenyl group, 4
-Cyanophenyl group, 1-naphthyl group, 2-naphthyl
Group, 6-ethyl-2-naphthyl group, 6-methoxy-2-
Naphthyl group, 4-n-butyl-1-naphthyl group, 4-E
Toxic-1-naphthyl group, 5-methyl-1-naphthyl
Aromatic groups such as a group, 7-ethoxy-2-naphthyl group
Group, for example, 2-furyl, 3-furyl, 2-thier
Nyl group, 3-thienyl group, 2-pyridyl group, 3-pyridyl
Group, 4-pyridyl group, 2-oxazolyl group, 2-thia
Zolyl group, 2-quinolinyl group, 2-benzoxazolyl
Group, heterocyclic aromatic group such as 2-benzothiazolyl group)
And more preferably a carbocyclic ring having 6 to 20 carbon atoms.
It is an aromatic group. In the compound represented by the general formula (1),
R ₁ ~ R ₆ Are each independently a hydrogen atom or a halogen atom
, Cyano group, linear, branched or cyclic alkyl group,
Chain, branched or cyclic alkoxy group, substituted or unsubstituted
Aralkyl group or substituted or unsubstituted aryl
Represents a group. Preferably, R ₁ ~ R ₆ Is a hydrogen atom, halo
Gen atoms (for example, fluorine, chlorine, bromine, etc.)
), A cyano group, a linear, branched or cyclic C 1-20 group
Alkyl group (for example, methyl group, ethyl group, n-
Propyl group, isopropyl group, n-butyl group, isobutyl
Group, sec-butyl group, tert-butyl group, n-pentyl
Group, isopentyl group, neopentyl group, tert-pentyl
Group, cyclopentyl group, n-hexyl group, 3,3-dimethyl
Butyl groups, cyclohexyl groups, n-heptyl groups,
Chlohexylmethyl group, n-octyl group, tert-octyl
Group, 2-ethylhexyl group, n-nonyl group, n-decyl
Group, n-dodecyl group, n-tetradecyl group, n-hexyl
Sadesyl group, n-octadecyl group, n-eicosyl group
), Linear, branched or cyclic alcohols having 1 to 20 carbon atoms
Xy group (for example, methoxy group, ethoxy group, n-propo group)
Xy, isopropoxy, n-butoxy, isobut
Xy, sec-butoxy, tert-butoxy, n-pe
Pentyloxy group, isopentyloxy group, neopentyl
Oxy group, tert-pentyloxy group, cyclopentylthio
Xy group, n-hexyloxy group, 3,3-dimethylbutyi
Loxy, cyclohexyloxy, n-heptyl
Xy group, cyclohexylmethoxy group, n-octyloxy
Si group, tert-octyloxy group, 2-ethylhexylo group
Xy group, n-nonyloxy group, n-decyloxy group, n
-Dodecyloxy group, n-tetradecyloxy group, n-
Hexadecyloxy group, n-eicosyloxy group
), Substituted or unsubstituted aralkyl having 5 to 24 carbon atoms
Group (for example, benzyl group, phenethyl group, α-methyl
Benzyl group, α, α-dimethylbenzyl group, 1-naphthyl
Methyl group, 2-naphthylmethyl group, furfuryl group, 2-
Methylbenzyl group, 3-methylbenzyl group, 4-methyl
Benzyl group, 3-ethylbenzyl group, 4-ethylbenzyl
Group, 4-isopropylbenzyl group, 4-tert-butyl
Benzyl group, 4-n-hexylbenzyl group, 4-n-no
N-benzyl group, 4-n-dodecylbenzyl group, 4-n
-Tetradecylbenzyl group, 4-n-heptadecylben
Zyl group, 2,4-dimethylbenzyl group, 3,4-dimethyl
Benzyl group, 3-methoxybenzyl group, 4-methoxy
Benzyl group, 4-ethoxybenzyl group, 4-n-butoxy
Cibenzyl group, 4-n-hexyloxybenzyl group, 4
-N-octyloxybenzyl group, 3,4-dimethoxy
Benzyl group, 3-fluorobenzyl group, 4-fluorobe
Benzyl group, 2-chlorobenzyl group, 3-chlorobenzyl
Group, 4-chlorobenzyl group, 3,4-dichlorobenzyl
Group or the like, or a substituted or unsubstituted group having 3 to 24 carbon atoms.
Aryl groups (eg, Ar ₁ And Ar _Two As a concrete example of
And more preferred substituents).
Are hydrogen, fluorine, chlorine, bromine,
Ano group, alkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms
An alkoxy group, an aralkyl group having 7 to 14 carbon atoms, carbon
It is a carbocyclic aromatic group of the number 6 to 14. In the compound represented by the general formula (1),
X ₁ Is a hydrogen atom, a linear, branched or cyclic alkyl group,
A substituted or unsubstituted aralkyl group, or a substituted or
Represents an unsubstituted aryl group. Preferably, X ₁ Is hydrogen
Atom, linear, branched or cyclic alkyl having 1 to 20 carbon atoms
(For example, R ₁ ~ R ₆ Substituents listed as specific examples of
Can be mentioned), substituted with 5 to 24 carbon atoms, or
Unsubstituted aralkyl groups (eg, R ₁ ~ R ₆ Examples of
The substituents mentioned above), and having 5 to 5 carbon atoms
24 substituted or unsubstituted aryl groups (eg, Ar ₁ You
And Ar _Two Substituents mentioned as specific examples of
), More preferably a hydrogen atom, having 1 to 10 carbon atoms.
Alkyl group, aralkyl group having 7 to 14 carbon atoms, 6 carbon atoms
To 14 carbocyclic aromatic groups. In the compound represented by the general formula (1),
X _Two Represents a hydrogen atom, a cyano group, a linear, branched or cyclic
Alkyl, substituted or unsubstituted aralkyl, or
Represents a substituted or unsubstituted aryl group. Preferably, X
_Two Is a hydrogen atom, a cyano group, a linear chain having 1 to 20 carbon atoms,
A branched or cyclic alkyl group (eg, R ₁ ~ R ₆ Concrete
Substituents mentioned as examples), and the number of carbon atoms
7-20 substituted or unsubstituted aralkyl groups (for example,
R ₁ ~ R ₆ Examples of the substituents mentioned as specific examples of
Can be substituted) or substituted or unsubstituted having 4 to 16 carbon atoms
Aryl groups (eg, Ar ₁ And Ar _Two As a specific example of
The above-mentioned substituents can be mentioned).
Or a hydrogen atom, a cyano group, an alkyl having 1 to 10 carbon atoms.
Aralkyl group having 7 to 14 carbon atoms, 6 to 14 carbon atoms
Is a carbocyclic aromatic group. The compound represented by the general formula (1) according to the present invention
Specific examples of the product include, for example, the following compounds (Chem.
42), but the present invention exemplifies these.
It is not limited to compounds. Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image The compound represented by the general formula (1) according to the present invention
The product can be manufactured according to a method known per se.
You. For example, J. Chem. Commun., 1129 (1994)
It can be manufactured according to the method. That is, for example
For example, a compound represented by the general formula (2) and a compound represented by the general formula (3)
Compound in the presence of an acid (eg, hydrogen bromide).
It can be manufactured by combining them. Also, for example
For example, a compound represented by the general formula (4) and a compound represented by the general formula (5)
Compound in the presence of an acid (eg, hydrogen bromide).
It can also be manufactured by combining them. Embedded image [Wherein Ar ₁ , Ar _Two , R ₁ ~ R ₆ , X ₁ You
And X _Two Represents the same meaning as in the case of the general formula (1). The organic electroluminescent element is usually provided at least between a pair of electrodes.
Also sandwich at least one light emitting layer containing one light emitting component.
It is something you can carry. Holes of compounds used in the light emitting layer
Injection and hole transport, electron injection and electron transport functions
Considering the level, if necessary, include the hole injection transport component.
Hole injection transport layer and / or electron injection transport component
May be provided. example
For example, the hole injection function and hole transport of the compound used in the light emitting layer
Good function and / or electron injection function and electron transport function
In some cases, the light emitting layer is a hole injection transport layer and / or
The device can also be configured as a device that also serves as a
You. Of course, in some cases, the hole injection transport layer and the electron
A device in which both layers of the injection transport layer are not provided (a single-layer device)
Child). Also, hole injection transport
Each of the layer, the electron injection transport layer and the light emitting layer
It may have a layered structure or a multi-layered structure.
The transport layer and the electron injection transport layer, in each layer,
Separate layer with injection function and layer with transport function
It can also be configured. In the organic electroluminescent device of the present invention,
The compound represented by the formula (1) has a hole injection / transport component,
Component, electron injection transport component
Component, more preferably used for the electron injection transport component,
It is particularly preferable to use it for a light emitting component. The organic electrode of the present invention
In a field emission device, a compound represented by the general formula (1)
May be used alone or in combination.
No. As the constitution of the organic electroluminescent device of the present invention,
Is not particularly limited. For example, (A) anode /
Hole injection / transport layer / light-emitting layer / electron injection / transport layer / cathode device
(FIG. 1), (B) anode / hole injection / transport layer / light emitting layer / cathode
Type element (FIG. 2), (C) anode / light-emitting layer / electron injection / transport layer
/ Cathode element (Fig. 3), (D) Anode / Light emitting layer / Cathode element
(FIG. 4). Furthermore, luminescence
(E) A device in which a layer is sandwiched between electron injection and transport layers.
Anode / hole injection / transport layer / electron injection / transport layer / emission layer / electron
An injection / transport layer / cathode type device (FIG. 5) can also be used.
As the element configuration of the (D) type, a light emitting component is formed in one layer.
Of course, the device of the type sandwiched between a pair of electrodes is
Include, for example, (F) a hole injecting and transporting component, a light emitting component,
And a pair of electrodes in the form of a single layer mixed with
Device of the type sandwiched between (FIG. 6), (G) hole injection transport
Pair of electrodes in the form of a single layer in which the components and the luminescent components are mixed
An element of the type sandwiched between (FIG. 7), (H) a light emitting component and
And a pair of electrodes in the form of a single layer mixed with
There is an element of the type sandwiched between (FIG. 8). In the organic electroluminescent device of the present invention,
It is not limited to these element configurations, but each type of element.
A hole injection transport layer, a light emitting layer, an electron injection transport layer
May be provided in plural layers. Also, each
In the device of the type, between the hole injection transport layer and the light emitting layer,
A mixed layer of a hole injection transport component and a light emitting component and / or
Between the light layer and the electron injection transport layer, the light emitting component and the electron injection transport
A mixed layer of the feed components can be provided. More preferred
The configuration of the electroluminescent device is as follows: (A) device, (B) device
Element, (C) type element, (E) type element, (F) type element,
(G) type element or (H) type element, more preferably
Or (A) type element, (B) type element, (C) type element,
(F) type element or (H) type element. As the electroluminescent device of the present invention, for example,
For example, (A) anode / hole injection / transport layer / light emission shown in FIG.
The layer / electron injection / transport layer / cathode will be described. (Fig. 1)
Wherein 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 is a cathode, 7 is a power supply
Is shown. The organic electroluminescent device according to the present invention
It is preferable that the substrate is particularly limited
It is not intended to be transparent, but transparent or translucent
More preferably, for example, a glass plate, a transparent plastic sheet
(Eg polyester, polycarbonate, polysul
Phone, polymethyl methacrylate, polypropylene,
Sheet such as polyethylene), translucent plastic sheet
Glass, quartz, transparent ceramics or a combination of these
And a composite sheet that has been coated. Sa
Furthermore, the substrate, for example, a color filter film, color conversion
Combining film and dielectric reflective film to control emission color
You can also The anode 2 has a relatively large work function.
Metals, alloys, or electrically conductive compounds as electrode materials
Is preferred. Examples of electrode materials used for the anode include:
For example, gold, platinum, silver, copper, cobalt, nickel, palladium
, Vanadium, tungsten, tin oxide, zinc oxide,
ITO (Indium Tin Oxide), Polythio
Fen, polypyrrole, and the like can be given. this
These electrode materials may be used alone or in combination.
You may use together. The anode compares these electrode materials,
For example, by a method such as a vapor deposition method and a sputtering method,
Can be formed on. The anode has a single-layer structure.
Or a multilayer structure. anode
Sheet resistance is preferably several hundred Ω / □ or less,
More preferably, it is set to about 5 to 50 Ω / □. Anode
The thickness depends on the material of the electrode substance used, but in general,
About 5 to 1000 nm, more preferably 10 to 500 nm
Set to about nm. The hole injecting / transporting layer 3 is formed from the anode to the hole (hole).
Function) to facilitate the injection of holes, and the injected holes
This is a layer containing a compound having a transport function. Hole
The injection / transport layer is a compound represented by the general formula (1) according to the present invention.
And / or other compounds having a hole injection / transport function
(Eg, phthalocyanine derivatives, triarylmeta
Derivatives, triarylamine derivatives, oxazole derivatives
Conductor, hydrazone derivative, stilbene derivative, pyrazoly
Derivatives, polysilane derivatives, polyphenylene vinylene
And its derivatives, polythiophene and its derivatives,
Poly-N-vinylcarbazole derivatives)
Can also be formed using one kind. In addition, hole injection transport
Compounds having a function may be used alone or
May be used in combination. Other Hole Injection and Transport Machine Used in the Present Invention
Compounds having a function include triarylamine derivatives
(For example, 4,4'-bis [N-phenyl-N- (4 "
-Methylphenyl) amino] biphenyl, 4,4'-bi
[N-phenyl-N- (3 "-methylphenyl) amido
No] biphenyl, 4,4'-bis [N-phenyl-N-
(3 "-methoxyphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (1 "-naphthyl) a
Mino] biphenyl, 3,3'-dimethyl-4,4'-bi
[N-phenyl-N- (3 "-methylphenyl) amido
No] biphenyl, 1,1-bis [4 ′-[N, N-di
(4 "-methylphenyl) amino] phenyl] cyclo
Xan, 9,10-bis [N- (4′-methylphenyi)
) -N- (4 "-n-butylphenyl) amino]
Nantrene, 3,8-bis (N, N-diphenylamido
G) -6-phenylphenanthridine, 4-methyl-
N, N-bis [4 ", 4"'-bis[N',N'-di (4
-Methylphenyl) amino] biphenyl-4-yl] a
Nirin, N, N'-bis [4- (diphenylamino) phenyl
Enyl] -N, N'-diphenyl-1,3-diaminobe
Nsen, N, N'-bis [4- (diphenylamino) phenyl
Enyl] -N, N'-diphenyl-1,4-diaminobe
Benzene, 5,5 "-bis [4- [bis (4-methyl
Nyl) amino] phenyl] -2,2 ': 5', 2 "-ta
-Thiophene, 1,3,5-tris (diphenylamido
G) benzene, 4,4 ', 4 "-tris (N-carbazo
Yl) triphenylamine, 4,4 ', 4 "-tris
[N- (3 "'-methylphenyl) -N-phenylamido
No] triphenylamine, 4,4 ', 4 "-tris
[N, N-bis- (4 "'-tert-butylbiphenyl-
4 ""-yl) amino] triphenylamine, 1,3
5-tris [N- (4'-diphenylaminophenyl)
-N-phenylamino] benzene), polythiophene
And its derivatives, poly-N-vinylcarbazole
Conductors are more preferred. A compound represented by the general formula (1)
When used in combination with other compounds having a hole injection transport function,
Compound represented by the general formula (1) occupying in the hole injection transport layer
The product ratio is preferably adjusted to about 0.1 to 40% by weight.
To make. The light emitting layer 4 has a hole and electron injection function,
Excitons by their transport function, recombination of holes and electrons
This is a layer containing a compound having a function of generating. Departure
The optical layer comprises a compound represented by the general formula (1) and / or
Compounds having other luminescent functions (for example, acridone induction
Body, quinacridone derivative, diketopyrrolopyrrole induction
, Polycyclic aromatic compounds (for example, rubrene, anthracene
, Tetracene, pyrene, perylene, chrysene, dekashi
Clen, coronene, tetraphenylcyclopentadie
Pentaphenylcyclopentadiene, 9,10-di
Phenylanthracene, 9,10-bis (phenylethyl
Nyl) anthracene, 1,4-bis (9′-ethynyl
(Nthracenyl) benzene, 4,4'-bis (9 "-ethyl)
Nilanthracenyl) biphenyl], triarylamido
Derivatives (for example, a compound having a hole injection / transport function)
And the compounds described above)
Complexes [for example, tris (8-quinolinolate) aluminum
Um, bis (10-benzo [h] quinolinolato) berili
, 2- (2'-hydroxyphenyl) benzoxa
Zol salt of sol, 2- (2'-hydroxyphenyl) be
Benzothiazole zinc salt, 4-hydroxyacridine
Zinc salt, zinc salt of 3-hydroxyflavone, 5-hydro
Beryllium salt of xyflavone, 5-hydroxyflavone
Aluminum salts], stilbene derivatives [eg, 1,
1,4,4-tetraphenyl-1,3-butadiene,
4,4'-bis (2,2-diphenylvinyl) biphenyl
4,4'-bis [(1,1,2-triphenyl)
Tenyl] biphenyl], coumarin derivatives [for example, bear
Phosphorus 1, Coumarin 6, Coumarin 7, Coumarin 30, Bear
Phosphorus 106, Coumarin 138, Coumarin 151, Kumari
152, coumarin 153, coumarin 307, coumarin
311, coumarin 314, coumarin 334, coumarin 3
38, Coumarin 343, Coumarin 500], Pyran induction
[Eg, DCM1, DCM2], oxazone derivatives
[E.g., Nile Red], benzothiazole derivative,
Benzoxazole derivatives, benzimidazole derivatives
Body, pyrazine derivative, cinnamate derivative, poly-
N-vinyl carbazole and its derivatives, polythiophene
And its derivatives, polyphenylene and its derivatives
Body, polybiphenylene vinylene and its derivatives, poly
Terphenylene vinylene and its derivatives, polynaphthi
Lenvinylene and its derivatives, polythienylene vinylene
And at least one derivative thereof)
can do. In the organic electroluminescent device of the present invention,
The optical layer contains a compound represented by the general formula (1).
Is preferred. Compounds represented by the general formula (1) and other compounds
When a compound having a light function is used in combination, it occupies in the light emitting layer.
The ratio of the compound represented by the general formula (1) is preferably
Is preferably about 0.001 to 99.999% by weight, more preferably
About 0.01 to 99.99% by weight, more preferably
It is adjusted to about 0.1 to 99.9% by weight. It has another light emitting function used in the present invention.
Compounds such as luminescent organometallic compounds or tria
Reelamine derivatives are more preferred. For example, J. Appl.
Phy., 65 , 3610 (1989), JP-A-5-214332.
As described in the official gazette, the light-emitting layer
It can also be composed of a compound (dopant). General
Using a compound represented by the formula (1) as a host compound
The light emitting layer can be formed by
The light-emitting layer can also be formed by using the material. General formula
Using the compound represented by (1) as a guest compound
When forming a light-emitting layer, the host compound may have a light-emitting property.
An organometallic complex or the triarylamine derivative
More preferred. In this case, the luminescent organometallic complex or
For the arylarylamine derivative, represented by the general formula (1)
The compound to be prepared is preferably added in an amount of about 0.001 to 40% by weight.
Degree, more preferably 0.01 to 30% by weight, particularly preferably
Or about 0.1 to 20% by weight. The compound represented by the general formula (1) is used in combination.
The luminescent organometallic complex is not particularly limited.
However, a luminescent organic aluminum complex is preferred,
With unsubstituted or unsubstituted 8-quinolinolate ligands
Organic aluminum complexes are more preferred. Preferred luminescence
As the organic aluminum complex, for example, the general formula (a)
-Luminescent organoaluminum complex represented by general formula (c)
Can be mentioned. (Q) _Three -Al (a) (wherein Q is a substituted or unsubstituted 8-quinolinolate group)
(Q) _Two -Al-OL (b) (wherein Q represents a substituted 8-quinolinolate ligand;
-L is a phenolate ligand, L is a phenyl moiety
(Q represents a hydrocarbon group having 6 to 24 carbon atoms) _Two -Al-O-Al- (Q) _Two (C) (wherein Q represents a substituted 8-quinolinolate ligand) As specific examples of the luminescent organometallic complex,
For example, tris (8-quinolinolate) aluminum,
Lis (4-methyl-8-quinolinolate) aluminium
, Tris (5-methyl-8-quinolinolate) aluminum
, Tris (3,4-dimethyl-8-quinolinollar
G) aluminum, tris (4,5-dimethyl-8-ki)
Norinolate) aluminum, tris (4,5-dimethyl)
8-quinolinolate) aluminum, bis (2-meth
Chill-8-quinolinolate) (phenolate) alumini
, Bis (2-methyl-8-quinolinolate) (2-
Methyl phenolate) aluminum, bis (2-methyl)
-8-quinolinolate) (3-methylphenolate)
Luminium, bis (2-methyl-8-quinolinolate)
(4-methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2-phenylphenol)
) Aluminum, bis (2-methyl-8-quinolino)
Latet) (3-phenylphenolato) aluminum,
Bis (2-methyl-8-quinolinolate) (4-phenyl
Rufenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinoler)
G) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolate) (3,4-di
Methyl phenolate) aluminum, bis (2-methyl)
-8-quinolinolate) (3,5-dimethylphenolate)
G) aluminum, bis (2-methyl-8-quinolinola)
(3,5-di-tert-butylphenolate) al
Minium, bis (2-methyl-8-quinolinolate)
(2,6-diphenylphenolate) aluminum,
(2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethyl
Rufenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,4,5,6-tetramethylfuran)
Enolate) aluminum, bis (2-methyl-8-ki)
Norinolate) (1-naphtholate) aluminum,
(2-methyl-8-quinolinolate) (2-naphthra
) Aluminum, bis (2,4-dimethyl-8-ki)
Norinolate) (2-phenylphenolate) alumini
Um, bis (2,4-dimethyl-8-quinolinolate)
(3-phenylphenolate) aluminum, bis
(2,4-dimethyl-8-quinolinolate) (4-fe
Nylphenolate) aluminum, bis (2,4-dimension)
Tyl-8-quinolinolate) (3,5-dimethylpheno
Lat) aluminum, bis (2,4-dimethyl-8-
Quinolinolate) (3,5-di-tert-butylphenol)
) Aluminum, bis (2-methyl-8-quinolino)
Lat) aluminum-μ-oxo-bis (2-methyl)
-8-quinolinolato) aluminum, bis (2,4-
Dimethyl-8-quinolinolato) aluminum-μ-o
Oxo-bis (2,4-dimethyl-8-quinolinolate)
Aluminum, bis (2-methyl-4-ethyl-8-ki
Norinolate) aluminum-μ-oxo-bis (2-
Methyl-4-ethyl-8-quinolinolate) aluminum
, Bis (2-methyl-4-methoxy-8-quinolinola)
) Aluminum-μ-oxo-bis (2-methyl-
4-methoxy-8-quinolinolate) aluminum, bi
(2-methyl-5-cyano-8-quinolinolate)
Luminium-μ-oxo-bis (2-methyl-5-cia
(No-8-quinolinolato) aluminum, bis (2-meth
Tyl-5-trifluoromethyl-8-quinolinolate)
Aluminum-μ-oxo-bis (2-methyl-5-to
Trifluoromethyl-8-quinolinolate) aluminum
And the like. Of course, luminescent organometallic complexes
May be used alone or in combination.
No. Further, the compound represented by the general formula (1)
The triarylamine derivative used is not particularly limited.
Although not a thing, for example, has a hole injection transport function
Examples of the compound include the compounds described above.
Of course, the triarylamine derivative may be used alone.
Or a plurality of them may be used in combination. The electron injecting / transporting layer 5 is formed by injecting electrons from the cathode.
Function to facilitate entry, and transport injected electrons
This is a layer containing a compound having a function. Electron injection transport
The layer is made of a compound represented by the general formula (1) and / or
Compounds having an electron injecting and transporting function (eg, organic metal
Complexes [for example, tris (8-quinolinolate) aluminum
Um, bis (10-benzo [h] quinolinolato) berili
Beryllium salt of 5-hydroxyflavone, 5-hydr
Roxiflavone aluminum salt], oxadiazole
Derivatives [eg, 1,3-bis [5 ′-(p-tert-butyl)
Tylphenyl) -1,3,4-oxadiazole-2 ′
-Yl] benzene], a triazole derivative [eg, 3
-(4'-tert-butylphenyl) -4-phenyl-5
-(4 "-biphenyl) -1,2,4-triazoe
), Triazine derivatives, perylene derivatives, quinoline derivatives
Conductor, quinoxaline derivative, diphenylquinone derivative,
Nitro-substituted fluorenone derivatives, thiopyrandioxai
Derivatives).
it can. In the organic electroluminescent device of the present invention, the electron injection
The compound represented by the general formula (1)
Is preferred. A compound represented by the general formula (1)
When used in combination with other compounds having an electron injection transport function,
In the general formula (1) according to the present invention, which occupies the electron injection transport layer.
The proportion of the compound represented is preferably 0.1% by weight or less.
Above, more preferably about 0.1 to 40% by weight, furthermore
Preferably, it is about 0.2 to 30% by weight, particularly preferably.
Is adjusted to about 0.5 to 20% by weight. In the present invention
And a compound represented by the general formula (1) and an organometallic complex [Example
For example, compounds represented by the general formulas (a) to (c)
To form an electron injecting and transporting layer.
New The cathode 6 has a relatively small work function.
Use metals, alloys or electrically conductive compounds as electrode materials.
It is preferred to use As an electrode material used for the cathode
Is, for example, lithium, lithium-indium alloy,
Thorium, sodium-potassium alloy, calcium,
Gnesium, magnesium-silver alloy, magnesium-a
Indium alloy, indium, ruthenium, titanium,
Manganese, yttrium, aluminum, aluminum
-Lithium alloy, aluminum-calcium alloy, aluminum
Minium-magnesium alloy, graphite thin film etc.
Can be mentioned. These electrode materials are used alone
Or a plurality of them may be used in combination. The cathode converts these electrode materials into, for example, steam.
Deposition method, sputtering method, ionization vapor deposition method, ion press
Method, cluster ion beam method, etc.
Alternatively, it can be formed on the electron injection transport layer. Ma
The cathode may have a single-layer structure or a multilayer structure.
It may be. The sheet electric resistance of the cathode is several hundred Ω.
/ □ or less is preferably set. The thickness of the cathode
Although it depends on the material of the electrode material to be used, it is generally 5 to 100.
About 0 nm, more preferably about 10 to 500 nm
Set. It should be noted that the light emission of the organic electroluminescent element is efficiently taken.
At least one of the anode and cathode electrodes
Is preferably transparent or translucent, and in general,
Material of the anode so that the transmittance of the emitted light is 70% or more.
It is more preferable to set the material and thickness. In the organic electroluminescent device of the present invention,
Is a singlet oxygen quencher in at least one of its layers
May be contained. As a singlet oxygen quencher
Is not particularly limited, for example, rubrene,
Nickel complexes, diphenylisobenzofuran, etc.
And particularly preferably rubrene. Singlet oxygen
The layer containing the enzyme is not particularly limited.
Preferably, but not necessarily, the emissive layer or hole injection transport
It is a transport layer, more preferably a hole injection transport layer.
In addition, for example, a singlet oxygen quencher is
Is contained uniformly in the hole injection transport layer.
And a layer adjacent to the hole injection transport layer (e.g., light emitting
Layer, an electron injecting and transporting layer having a light emitting function)
You may let it. As the content of singlet oxygen quencher
Constitutes a contained layer (for example, a hole injection transport layer).
0.01 to 50% by weight, preferably 0.0
5 to 30% by weight, more preferably 0.1 to 20% by weight
It is. Hole injection transport layer, light emitting layer, electron injection transport layer
The method of forming is not particularly limited.
For example, vacuum evaporation method, ionization evaporation method, solvent coating method (for example,
For example, spin coating, casting, dip coating,
Bar coating method, roll coating method, Langmuir Blouse
To form a thin film by a printing method, an inkjet method, etc.)
It can be manufactured by the following. By vacuum evaporation method,
When forming each layer, the conditions of vacuum deposition are particularly limited.
Not something, but 10 ^-Five Under vacuum of about Torr or less, 50
~ 600 ° C boat temperature (deposition source temperature), -50 ~
At a substrate temperature of about 300 ° C., 0.005 to 50 nm / se
It is preferable to carry out at a deposition rate of about c. This place
Each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer.
Has various properties by forming continuously under vacuum.
A more excellent organic electroluminescent device can be manufactured.
Hole injection transport layer, light emitting layer, electron injection by vacuum evaporation method
When each layer such as a transport layer is formed using multiple compounds
Temperature control for each boat containing the compound
Preferably, it is deposited. When each layer is formed by a solution coating method,
Components forming each layer or their components and binder resin
And the like are dissolved or dispersed in a solvent to form a coating liquid. Correct
Used for hole injection transport layer, light emitting layer, electron injection transport layer
Examples of the binder resin that can be used include poly-N-vinyl
Rucarbazole, polyarylate, polystyrene, poly
Esters, polysiloxane, polymethyl acrylate,
Polymethyl methacrylate, polyether, polycarbonate
, Polyamide, polyimide, polyamideimide,
Polyparaxylene, polyethylene, polyethylene ether
, Polypropylene ether, polyphenylene oxide
, Polyether sulfone, polyaniline and the like
Derivatives, polythiophenes and their derivatives, polyphenylene
Lenvinylene and its derivatives, polyfluorene and
Derivatives thereof, polythienylenevinylene and its derivatives
And the like. The binder resin is
They may be used alone or in combination. When each layer is formed by a solution coating method,
Components forming each layer or their components and binder resin
Etc. with a suitable organic solvent (for example, hexane, octane,
Decane, toluene, xylene, ethylbenzene, 1-methyl
Hydrocarbon solvents such as tilnaphthalene, for example, aceto
, Methyl ethyl ketone, methyl isobutyl ketone,
Ketone solvents such as clohexanone, for example, dichloromethan
Tan, chloroform, tetrachloromethane, dichloroe
Tan, trichloroethane, tetrachloroethane, chloro
Halo such as benzene, dichlorobenzene, chlorotoluene
Genated hydrocarbon solvents such as ethyl acetate, butyric acetate
, An ester solvent such as amyl acetate, for example, methanol
, Ethanol, propanol, butanol, pentano
, Hexanol, cyclohexanol, methylcello
Solvent, ethyl cellosolve, ethylene glycol, etc.
Alcohol-based solvents such as dibutyl ether,
Ether solvents such as drofuran, dioxane and anisole
Medium, for example, N, N-dimethylformamide, N, N-
Dimethylacetamide, 1-methyl-2-pyrrolidone,
1,3-dimethyl-2-imidazolidinone, dimethyls
Soluble in polar solvents such as rufoxide) and / or water
Dissolve or disperse to form a coating solution, and use various coating methods
Thus, a thin film can be formed. The method of dispersing is not particularly limited.
Although not intended, for example, ball mills, sand mills,
Int shaker, attritor, homogenizer, etc.
To disperse them in the form of fine particles. Concentration of coating liquid
Is not particularly limited.
The concentration range suitable for producing the desired thickness.
And generally, about 0.1 to 50% by weight.
Degree, preferably at a solution concentration of about 1 to 30% by weight.
You. When using a binder resin, the amount
Although not particularly limited, generally, each
For the components forming the layer (for forming a single-layer device)
5 to 99.9% by weight based on the total amount of each component)
Degree, preferably about 10 to 99% by weight, more preferably
Alternatively, it is set to about 15 to 90% by weight. Hole injection / transport layer, light emitting layer, electron injection / transport layer
Although there is no particular limitation on the film thickness of
It is preferable to set the thickness to about 5 nm to 5 μm.
Prevents the fabricated device from coming into contact with oxygen, moisture, etc.
To provide a protective layer (sealing layer)
For example, paraffin, liquid paraffin, silicon oxide
Il, fluorocarbon oil, zeolite-containing fluoroca
It can be protected by enclosing it in an inert substance such as
it can. As a material used for the protective layer, for example, an organic
Polymer materials (for example, fluorinated resin, epoxy resin,
Silicone resin, epoxy silicone resin, polystyrene
Polyester, polycarbonate, polyamide, polyester
Liimide, polyamideimide, polyparaxylene, poly
Ethylene, polyphenylene oxide), inorganic materials (examples)
For example, diamond thin film, amorphous silica,
Marginal glass, metal oxide, metal nitride, metal carbide,
Metal sulfide), and photo-curable resin
The material used for the protective layer may be used alone.
Or a plurality of them may be used in combination. The protective layer has a single-layer structure
Or a multilayer structure. As a protective film on the electrode, for example, a metal
Oxide film (for example, aluminum oxide film), metal fluoride film
Can also be provided. Also, for example, on the surface of the anode,
For example, organic phosphorus compounds, polysilanes, aromatic amines
Conductor, phthalocyanine derivative (for example, copper phthalocyanine
To provide an interface layer (intermediate layer) made of carbon
You can also. In addition, electrodes, for example, anodes,
For example, acid, ammonia / hydrogen peroxide, or plasma
It can also be used after processing with a machine. The organic electroluminescent device of the present invention generally has a direct
It is used as a current-driven element,
Can also be used as an AC-driven element.
Incidentally, the applied voltage is generally about 2 to 30 V. Departure
Ming organic electroluminescent devices are, for example, panel-type light sources, various
Light-emitting elements, various display elements, various signs, various sensors
It can be used for sir and so on. The present invention will be described in more detail with reference to the following examples.
As will be described, of course, the present invention is not limited to these.
Absent. Example 1 Glass having 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
-N- (1 "-naphthyl) amino] biphenyl is
Deposit to a thickness of 75 nm at a deposition rate of 0.2 nm / sec.
The hole injection transport layer was used. Then, Tris (8-
Quinolinolate) aluminum and exemplary compound number A-1
From different evaporation sources, a deposition rate of 0.2 nm / 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-quinolinola)
G) 50 aluminum at a deposition rate of 0.2 nm / sec.
This was vapor-deposited to a thickness of nm to form an electron injection transport layer. further,
On top of that, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
c to 200nm thickness by co-evaporation (weight ratio 10: 1)
An organic electroluminescent device was prepared as a cathode. In addition, evaporation is
The test was performed while maintaining the reduced pressure state of the vapor deposition tank. Organic prepared
A DC voltage of 12 V was applied to the electroluminescent element in a dry atmosphere.
When added, 55 mA / cm ^Two Current flowed. Luminance
2840 cd / m ^Two Orange light emission was confirmed. Examples 2 to 46 In Example 1, when forming the light emitting layer,
Instead of using the compound of the number A-1, the exemplified compound number
No. A-4 (Example 2), Exemplified Compound No. A-7
(Example 3), Compound of Exemplified Compound No. A-9
(Example 4), Compound of Exemplified Compound No. A-15 (Example
Example 5), Compound of Exemplified Compound No. A-18 (Example
6), Compound of Exemplified Compound No. A-22 (Example 7),
Compound of Exemplified Compound No. A-24 (Example 8), Exemplified
Compound No. A-28 (Example 9), Exemplified Compound No.
No. A-30 (Example 10), Exemplified Compound No. A
-32 (Example 11), Exemplified Compound No. A-3
Compound No. 6 (Example 12), Exemplified Compound No. A-37
Compound (Example 13), Compound of Exemplified Compound No. A-41
(Example 14), Compound of Exemplified Compound No. A-42
(Example 15), Compound of Exemplified Compound No. B-2 (Example
Example 16), Compound of Exemplified Compound No. B-4 (Example 1)
7), Compound of Exemplified Compound No. B-5 (Example 18),
Compound of Exemplified Compound No. B-9 (Example 19), Exemplified
Compound No. B-11 (Example 20), Exemplified compound
Compound No. C-1 (Example 21), Exemplified Compound No. C
-6 (Example 22), Exemplified Compound No. D-5
Compound (Example 23), Compound of Exemplified Compound No. D-10
(Example 24), Compound of Exemplified Compound No. D-13
(Example 25), Compound (exemplary compound No. D-16)
Example 26), compound of Exemplified Compound No. E-4 (Example 2)
7), Compound of Exemplified Compound No. E-5 (Example 28),
Compound of Exemplified Compound No. E-10 (Example 29), Exemplified
Compound No. E-12 (Example 30), exemplifying compound
Compound of Compound No. E-13 (Example 31), Exemplified Compound No.
No. E-17 (Example 32), Exemplified Compound No. E
Compound No. -21 (Example 33), Exemplified Compound No. F-2
(Example 34), Compound of Exemplified Compound No. F-3
(Example 35), Compound (exemplary compound No. F-6)
Example 36), Compound of Exemplified Compound No. F-10 (Example
37), Compound of Exemplified Compound No. G-1 (Example 3)
8), Compound of Exemplified Compound No. G-8 (Example 39),
Compound of Exemplified Compound No. G-10 (Example 40), Exemplified
Compound No. H-5 (Example 41), Exemplified compound
Compound No. H-7 (Example 42), Exemplified Compound No. H
Compound No. -10 (Example 43), Exemplified Compound No. H-1
Compound No. 3 (Example 44), Compound No. H-17
Compound (Example 45), Compound of Exemplified Compound No. H-24
Example 1 except that the product (Example 46) was used.
An organic electroluminescent device was produced by the method. Each element
A DC voltage of 12 V was applied to the
After that, orange or red light emission was confirmed. Further features
The properties were examined, and the results are shown in Table 1 (Tables 1 to 3). Comparative Example 1 In Example 1, when forming the light emitting layer,
Without using the compound of No. A-1, Tris (8-quinoli
Nolate) 50 nm thick, using only aluminum
The method described in Example 1 except that the light-emitting layer was
To produce an organic electroluminescent device. Dry this element
Under the atmosphere, when a DC voltage of 12 V was applied, a green
Light emission was confirmed. The characteristics were further examined and the results
The results are shown in Table (Table 3). Comparative Example 2 In Example 1, when forming the light emitting layer,
Instead of using the compound of number A-1, 1,3,5
7,8-pentamethyl-4,4-difluoro-4-bora
Except using -3a, 4a-diaza-s-indacene
Manufactured an organic electroluminescent device by the method described in Example 1.
Made. A DC voltage of 12 V is applied to the device under a dry atmosphere.
, Green light emission was confirmed. More
Were examined, and the results are shown in Table 1 (Table 3). [Table 1] [Table 2] [Table 3] Example 47 Glass having a 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
Ru-N- (3 "-methylphenyl) amino] biphenyl
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm.
Thus, a hole injection transport layer was obtained. Then, on top of it, Tris
(8-quinolinolate) aluminum and exemplified compound numbers
The compound of D-14 was obtained 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:
2.0) to form a light emitting layer. Next, Tris (8-kinori)
Nolate) 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. Sa
In addition, magnesium and silver are further deposited thereon at a deposition rate of 0.2 n.
Co-deposition at 200 m / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. A dry atmosphere was applied to the produced organic electroluminescent device.
Below, when a DC voltage of 12 V was applied, 58 mA / c
m ^Two Current flowed. Brightness 2970 cd / m ^Two Red orange
Was confirmed. Example 48 Glass having a 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
Ru-N- (3 "-methylphenyl) amino] biphenyl
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm.
Thus, a hole injection transport layer was obtained. Then, on top of that,
(2-methyl-8-quinolinolato) aluminum-μ
-Oxo-bis (2-methyl-8-quinolinolato) a
Luminium and the compound of Exemplified Compound No. H-17 are different
50 nm thick at a deposition rate of 0.2 nm / sec from the deposition source
Then, co-evaporation (weight ratio: 100: 4.0) was performed to form a light emitting layer.
Was. Next, tris (8-quinolinolate) aluminum
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm.
Thus, an electron injection transport layer was obtained. In addition, magne
200 nm at a deposition rate of 0.2 nm / sec.
Co-deposit (weight ratio 10: 1) to the thickness to form a cathode,
A field emission device was manufactured. The evaporation was performed under reduced pressure in the evaporation tank.
Was carried out while maintaining. In the manufactured organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere,
0mA / cm ^Two Current flowed. Brightness 2830 cd / m
^Two Red light emission was confirmed. Example 49 A glass having a 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
Ru-N- (3 "-methylphenyl) amino] biphenyl
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm.
Thus, a hole injection transport layer was obtained. Then, on top of that,
(2,4-dimethyl-8-quinolinolate) aluminum
Mu-μ-oxo-bis (2,4-dimethyl-8-quinolyl
Nolate) Conversion of aluminum to Exemplified Compound No. E-18
Compound from different evaporation sources at a deposition rate of 0.2 nm / sec
Co-deposition (weight ratio 100: 8.0) to a thickness of 50 nm,
It was a light emitting layer. Next, tris (8-quinolinolate)
Luminium was deposited at 50 nm at a deposition rate of 0.2 nm / sec.
This was vapor-deposited to a thickness to form an electron injection transport layer. Moreover
And magnesium and silver at a deposition rate of 0.2 nm / sec.
Co-deposit to a thickness of 00 nm (weight ratio 10: 1)
Then, an organic electroluminescent device was produced. In addition, vapor deposition is performed in a vapor deposition tank.
This was carried out while maintaining the reduced pressure state. Organic electric field generated
A DC voltage of 12 V was applied to the optical element under a dry atmosphere.
However, 61 mA / cm ^Two Current flowed. Brightness 268
0 cd / m ^Two Orange light emission was confirmed. Example 50 Glass having 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4 ', 4 "-tris [N
-(3 "'-methylphenyl) -N-phenylamino]
Triphenylamine was deposited at a deposition rate of 0.1 nm / sec.
Evaporation was performed to a thickness of 0 nm to form a first hole injection transport layer. Next
4,4'-bis [N-phenyl-N- (1 "-na
Phthyl) amino] biphenyl and Exemplified Compound No. A-1
Compounds are deposited from different evaporation sources at a deposition rate of 0.2 nm / sec.
Co-deposition to a thickness of 20 nm with a weight ratio of 100: 2.0
Thus, the light emitting layer also served as the second hole injection / transport layer. Next
In addition, tris (8-quinolinolate) aluminum
At a deposition rate of 0.2 nm / sec to a thickness of 50 nm.
Vapor deposition was performed to form an electron injection transport layer. Furthermore, on top of that,
Gnesium and silver are deposited at a deposition rate of 0.2 nm / sec for 200 n.
m with a thickness of 10: 1 to form a cathode.
An electroluminescent device was fabricated. In addition, the evaporation was performed under reduced pressure in the evaporation tank.
The test was performed while maintaining the condition. Organic electroluminescent device fabricated
And a DC voltage of 12 V was applied in a dry atmosphere.
Filter, 55mA / cm ^Two Current flowed. Brightness 3350c
d / m ^Two Orange light emission was confirmed. Examples 51 to 65 In Example 50, when forming the light emitting layer,
Instead of using the compound of article number A-1,
Compound No. A-12 (Example 51), Exemplified Compound No.
Compound of A-16 (Example 52), Exemplified Compound No. A-
Compound No. 31 (Example 53), Exemplified Compound No. A-42
(Example 54), Compound of Exemplified Compound No. B-10
Compound (Example 55), Compound of Exemplified Compound No. D-12
(Example 56), Compound (exemplary compound No. D-15)
Example 57), Compound of Exemplified Compound No. E-5 (Example 5)
8), Compound of Exemplified Compound No. E-11 (Example 5)
9), Compound of Exemplified Compound No. E-14 (Example 6)
0), compound of Exemplified Compound No. F-4 (Example 61),
Compound of Exemplified Compound No. G-1 (Example 62), Exemplification
Compound No. H-5 (Example 63), Exemplified Compound No.
No. H-17 (Example 64), Exemplified Compound No. H
-22 except that the compound of Example -22 was used (Example 65).
An organic electroluminescent device was prepared by the method described in Example 50.
Was. A 12V DC voltage was applied to each element in a dry atmosphere.
When pressure was applied, orange or red light emission was confirmed.
Was. The characteristics were further examined, and the results are shown in Table 2 (Table 4).
did. [Table 4] Example 66 Glass having 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
Ru-N- (3 "-methylphenyl) amino] biphenyl
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm.
Thus, a hole injection transport layer was obtained. Then, on top of it, Tris
(8-quinolinolate) aluminum and exemplified compound numbers
The compound of E-8 was deposited at a deposition rate of 0.2 n from different deposition sources.
m / sec at a thickness of 50 nm (weight ratio 100:
5.0) to form a light-emitting layer also serving as an electron injection / transport layer. Sa
In addition, magnesium and silver are further deposited thereon at a deposition rate of 0.2 n.
Co-deposition at 200 m / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. Production
12V DC under dry atmosphere
When voltage was applied, 58 mA / cm ^Two Current flows
Was. Brightness 2540 cd / m ^Two Orange emission of
Was. Example 67 Glass having 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
Ru-N- (3 "-methylphenyl) amino] biphenyl
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm.
Thus, a hole injection transport layer was obtained. Then, 1,1,
4,4-tetraphenyl-1,3-butadiene is deposited
Evaporate at a rate of 0.2 nm / sec to a thickness of 50 nm and emit light
Layers. Then, on top of this, Tris (8-quinolinola)
The compound of Exemplified Compound No. A-1 with aluminum
50n at a deposition rate of 0.2nm / sec from different deposition sources
m (thickness ratio 100: 8.0)
The layer was used as the transport layer. And on top of that, magnesium and silver
To a thickness of 200 nm at a deposition rate of 0.2 nm / sec.
An organic electroluminescent device which is attached (weight ratio 10: 1) to form a cathode.
Was prepared. In addition, the evaporation was performed while maintaining the reduced pressure in the evaporation tank.
I did it. Dry atmosphere on the manufactured organic electroluminescent device
Below, when a DC voltage of 14 V was applied, 52 mA / c
m ^Two Current flowed. Brightness 2370cd / m ^Two The blue
Light emission was confirmed. Example 68 Glass having a 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
4,4'-bis [N-phenyl]
Ru-N- (3 "-methylphenyl) amino] biphenyl
Is deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm.
Thus, a hole injection transport layer was obtained. Then, on top of that,
Compound No. H-8 was deposited at a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form a light emitting layer. Then, 1,
3-bis [5 '-(p-tert-butylphenyl) -1,
3,4-oxadiazol-2'-yl] benzene,
Deposit to a thickness of 50 nm at a deposition rate of 0.2 nm / sec.
An electron injection transport layer was used. Furthermore, on top of it, magnesium
Silver with a thickness of 200 nm at a deposition rate of 0.2 nm / sec
Into a cathode by co-evaporation (weight ratio 10: 1)
An optical element was manufactured. In the deposition, the depressurized state of the deposition tank was maintained.
It was carried out as it was. Dry the organic electroluminescent device
When a DC voltage of 12 V was applied in an atmosphere, 49 m
A / cm ^Two Current flowed. Brightness 2080 cd / m ^Two of
Red light emission was confirmed. Example 69 A glass having a 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
After UV / ozone cleaning, the substrate holder of the evaporation system
After fixing to 3 × 10 ^-6 The pressure was reduced to Torr. Ma
First, the compound of Exemplified Compound No. H-23 was formed on the ITO transparent electrode.
The compound was formed to a thickness of 55 nm at a deposition rate of 0.2 nm / sec.
Evaporation was performed to form a light emitting layer. Next, 1,3-bis [5′-
(P-tert-butylphenyl) -1,3,4-oxadi
Azol-2'-yl] benzene at a deposition rate of 0.2 n
m / sec to a thickness of 75 nm, and
did. In addition, magnesium and silver are deposited on top
Co-deposition to a thickness of 200 nm at 0.2 nm / sec (weight ratio
10: 1) to form an organic electroluminescent device as a cathode.
Was. The deposition was performed while maintaining the reduced pressure of the deposition tank.
Was. The organic electroluminescent device thus prepared was dried under a dry atmosphere at 15
V DC voltage of 67 mA / cm ^Two No electricity
The current flowed. Brightness 1630 cd / m ^Two Red-orange emission of
confirmed. Example 70 Glass having a 200-nm-thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas.
UV / ozone cleaning. First, on the ITO transparent electrode
Poly-N-vinylcarbazole (weight average molecular weight 1)
50,000), 1,1,4,4-tetraphenyl-1,
3-butanediene (blue light-emitting component), coumarin 6 ["
3- (2'-benzothiazolyl) -7-diethylamino
Coumarin ”(green light-emitting component)]
No. D-11 was added in a weight ratio of 100: 5:
A 3% by weight dichloroethane solution containing 3: 2 was prepared.
Using a dip coating method, a 400 nm thick
An optical layer was formed. Next, a glass substrate having this light emitting layer
Is fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank is 3 × 1
0 ^-6 The pressure was reduced to Torr. Further, on the light emitting layer,
(4′-tert-butylphenyl) -4-phenyl-5-
(4 "-biphenyl) -1,2,4-triazole
Deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec.
After that, tris (8-quinolinolate)
Luminium is deposited at 30 nm at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness to form an electron injection transport layer. Further on that,
Magnesium and silver are deposited at a deposition rate of 0.2 nm / sec.
Co-deposit (weight ratio 10: 1) to a thickness of nm to form a cathode,
An organic electroluminescent device was manufactured. In addition, for evaporation, the number of evaporation tanks was reduced.
The test was performed while maintaining the pressure state. Organic electroluminescent element fabricated
A DC voltage of 12 V was applied to the
Filter, 74mA / cm ^Two Current flowed. Brightness 1450c
d / m ^Two White light emission was confirmed. Examples 71 to 78 In Example 70, when forming the light emitting layer,
Instead of using the compound of article number D-11,
Compound of Compound No. D-16 (Example 71), Exemplified Compound No.
No. E-19 (Example 72), Exemplified Compound No. F
Compound No.-12 (Example 73), Exemplified Compound No. H-1
Compound No. 1 (Example 74), Exemplified Compound No. H-19
Compound (Example 75), Compound of Exemplified Compound No. H-21
(Example 76), Compound of Exemplified Compound No. H-26
(Example 77), Compound of Exemplified Compound No.
Example 78) except that Example 78) was used.
To produce an organic electroluminescent device. Each element
And a DC voltage of 12 V was applied in a dry atmosphere.
After that, white light emission was confirmed. Further investigate its properties,
The results are shown in Table 3 (Table 5). [Table 5] Example 79 Glass having a 200 nm thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
UV / ozone cleaning. First, on the ITO transparent electrode
Poly-N-vinylcarbazole (weight average molecular weight 1)
50,000), 1,3-bis [5 ′-(p-tert-butyl
Ruphenyl) -1,3,4-oxadiazole-2′-
Yl] benzene and compound of Exemplified Compound No. A-19
In a weight ratio of 100: 30: 3, respectively.
Dip coating method using 3% by weight dichloroethane solution
As a result, a light emitting layer having a thickness of 300 nm was formed. Next,
The substrate having the luminescent layer is fixed to the substrate holder of the vapor deposition device.
And set the evaporation tank to 3 × 10 ^-6 The pressure was reduced to Torr. In addition,
On the light layer, magnesium and silver were deposited at a deposition rate of 0.2 nm /
co-evaporate (weight ratio 10: 1) to 200nm thickness in sec
The cathode was used as a cathode to produce an organic electroluminescent device. Made
DC voltage of 15V under dry atmosphere
When applied, 74 mA / cm ^Two Current flowed. Shine
Degree 1570 cd / m ^Two Red-orange emission was confirmed. Comparative Example 3 In Example 79, when forming the light emitting layer,
Instead of the compound of the article number A-19, 1,1,4,4-
Other than using tetraphenyl-1,3-butadiene
Is an organic electroluminescent device according to the method described in Example 79.
Produced. Dry atmosphere on the manufactured organic electroluminescent device
Below, when a DC voltage of 15 V was applied, 86 mA / c
m ^Two Current flowed. Brightness 680 cd / m ^Two The blue departure
Light was confirmed. Example 80 Glass having a 200-nm-thick ITO transparent electrode (anode)
Substrate with neutral detergent, acetone and ethanol
Sonic cleaning was performed. The substrate is dried using nitrogen gas,
UV / ozone cleaning. First, on the ITO transparent electrode
, Polycarbonate (weight average molecular weight 50,000),
4,4-bis [N-phenyl-N- (3 "-methylphen
Nyl) amino] biphenyl, bis (2-methyl-8-ki
Norinolate) aluminum-μ-oxo-bis (2-
Methyl-8-quinolinolate) aluminum and examples
Compound No. A-44 was added at a weight ratio of 10
3% by weight dichloro containing 0: 40: 60: 1
By dip coating using ethane solution, a thickness of 30
A 0 nm light emitting layer was formed. Next, having this light emitting layer
The substrate is fixed to the substrate holder of the vapor deposition device, and the vapor deposition tank is
× 10 ^-6 The pressure was reduced to Torr. In addition, on the light emitting layer,
Nesium and silver are deposited at 200 nm at a deposition rate of 0.2 nm / sec.
Co-deposited (weight ratio 10: 1) to the thickness of
An electroluminescent device was manufactured. Organic electroluminescent device fabricated
Was applied a DC voltage of 15 V in a dry atmosphere.
Filter, 67mA / cm ^Two Current flowed. Brightness 1050c
d / m ^Two Orange light emission was confirmed. Example 81 A glass substrate was washed with a neutral detergent, acetone and ethanol.
Ultrasonic cleaning. Dry the substrate using nitrogen gas
Then, after UV / ozone cleaning, the substrate
After fixing it to the rudder, set the evaporation tank to 3 × 10 ^-6 Decompress to Torr
Was. Next, the compound of Exemplified Compound No. A-1 was formed on a glass substrate.
The compound is deposited to a thickness of 100 nm at a deposition rate of 0.2 nm / sec.
Was deposited. On top of that, magnesium and silver are deposited at the evaporation rate
Co-deposition to a thickness of 200 nm at 0.2 nm / sec (weight
A ratio of 10: 1) was used as a cathode. In addition, evaporation was performed under reduced pressure in the evaporation tank.
The test was performed while maintaining the condition. Then scotch on the cathode
I stuck the tape. Scotch tape peeled off
And a thin film of the compound of Exemplified Compound No. A-1 together with the cathode
Also peels off from the glass substrate and has good adhesion to the cathode
It has been found. Comparative Example 4 In Example 81, the compound of Exemplified Compound No. A-1
Instead, 1,3,5,7,8-pentamethyl-4,4
-Difluoro-4-bora-3a, 4a-diaza-s-i
The procedure described in Example 81 was followed except that dascene was used.
A thin film on which a cathode was deposited was prepared. Then, on the cathode
Scotch tape was applied. Peel off scotch tape
As a result, the cathode and 1,3,5,7,8-pentamethyl-
4,4-difluoro-4-bora-3a, 4a-diaza-
Peeled between the thin films of s-indacene, the adhesion to the cathode was
It turned out to be bad. According to the present invention, an organic light emitting device having excellent light emission luminance is provided.
It has become possible to provide a field emission element.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic structural diagram of an example (A) of an organic electroluminescent device. FIG. 2 is a schematic structural diagram of an example (B) of an organic electroluminescent element. FIG. 3 is a schematic structural view of an example (C) of an organic electroluminescent element. FIG. 4 is a schematic structural diagram of an example (D) of an organic electroluminescent element. FIG. 5 is a schematic structural diagram of an example (E) of an organic electroluminescent element. FIG. 6 is a schematic structural diagram of an example (F) of an organic electroluminescent element. FIG. 7 is a schematic structural diagram of an example (G) of an organic electroluminescent element. FIG. 8 is a schematic structural view of an example (H) of an organic electroluminescent element. [Description of Signs] 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

Continuation of front page    (72) Inventor Taizo Nishimoto             1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Mitsui             Chemical Co., Ltd. F term (reference) 3K007 AB02 AB03 BB06 CA01 CA02                       CA05 CA06 CB01 DA00 DA01                       DB03 EB00 FA01 FA03

Claims (1)

Claims 1. A general formula (1) between a pair of electrodes.
An organic electroluminescent element comprising at least one layer containing at least one compound represented by the following formula: Embedded image (Wherein, Ar ₁ and Ar ₂ represent a substituted or unsubstituted aryl group, and R _{1 to} R ₆ each independently represent a hydrogen atom, a halogen atom, a cyano group, a linear, branched or cyclic alkyl group, Represents a chain, branched or cyclic alkoxy group, substituted or unsubstituted aralkyl group, or substituted or unsubstituted aryl group, and X ₁ represents a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aralkyl group. Group,
Alternatively, X ₂ represents a substituted or unsubstituted aryl group, and X ₂ represents a hydrogen atom, a cyano group, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. 2. The organic electroluminescent device according to claim 1, wherein the layer containing the compound represented by the general formula (1) is a light emitting layer. 3. The organic electroluminescent device according to claim 1, wherein the layer containing the compound represented by the general formula (1) is an electron injection / transport layer. 4. The layer containing the compound represented by the general formula (1) further contains at least one kind of a luminescent organometallic complex or a triarylamine derivative.
The organic electroluminescent device according to any one of the above. 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.