JPH06330031A - Organic electroluminescent element - Google Patents

Abstract

PURPOSE:To obtain an organic electroluminescent element having excellent aging stability of luminescent characteristics and suppressed dark spot generation and useful for a light source of a plane light, a display board, etc., by placing a boundary layer containing a specific quinacridone compound between an organic luminescent layer and a cathode. CONSTITUTION:The organic electroluminescent element is composed of an anode, an organic luminescent layer and a cathode laminated one upon another. In the above element, a boundary layer containing a quinacridone compound of formula [R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7> and R<8> are H, halogen, alkyl, aralkyl, alkenyl, allyl, (substituted) aromatic hydrocarbon ring, (substituted) aromatic heterocyclic group, amide group, alkoxy, alkoxycarbonyl or (substituted) amino; R<1> and R<2>, R<3> and R<4>, R<5> and R<6>, and R<7> and R<8> may be bonded together to form (substituted) aromatic hydrocarbon ring or (substituted) aromatic heterocyclic group] is placed between the organic luminescent layer and the cathode.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device, and more particularly, to a thin film type device which emits light by applying an electric field to a light emitting layer made of an organic compound.

[0002]

2. Description of the Related Art Conventionally, as a thin film type electroluminescent device,
ZnS and Ca which are II-VI group compound semiconductors of inorganic materials
In S, SrS, etc., Mn, which is the emission center, and rare earth elements (E
(U, Ce, Tb, Sm, etc.) is generally doped, but the electroluminescent device made from the above inorganic material is 1) AC drive is required (50 to 1000 Hz), 2) High drive voltage. (Up to 200V), 3) full colorization is difficult (especially blue color is a problem), and 4) peripheral drive circuit cost is high.

However, in recent years, in order to improve the above problems,
Electroluminescent devices using organic thin films have been developed. In particular, the electrode type was optimized for the purpose of improving the efficiency of carrier injection from the electrode in order to increase the light emission efficiency, and an organic hole transport layer composed of an aromatic diamine and a light emitting layer composed of an aluminum complex of 8-hydroxyquinoline. Of an organic electroluminescent device provided with (Appl. Phys.
Lett. , 51, 913, 1987),
Compared with the conventional electroluminescent device using a single crystal such as anthracene, the luminous efficiency has been significantly improved.

As the organic light emitting layer, poly (p-phenylene vinylene) (Nature, Volume 347, 539) is used.
P., 1990; Appl. Phys. Lett. , 6
1, 2793, 1992), poly [2-methoxy, 5- (2'-ethylhexoxy) -1,4-phenylenevinylene] (Appl. Phys. Lett., 5).
Volume 8, 1982, 1991; Thin Solid.
Films, 216, 96, 1992; Nat
ure, 357, p. 477, 1992), poly (3
-Alkylthiophene) (Jpn.J.Appl.Ph)
ys, vol. 30, L1938, 1991; App
l. Phys. , 72, 564, 1992), etc., and development of polymer materials such as polyvinylcarbazole and luminescent materials and electron transfer materials (applied physics, 61, 1044, 1992). Being developed.

In the organic electroluminescent device as described above, indium tin oxide (IT) is usually used as the anode.
Although a transparent electrode such as O) is used, a metal electrode having a low work function is used for the cathode in order to efficiently inject electrons, and magnesium alloy, calcium or the like is used. The biggest problem of the organic electroluminescence device is the life of the device, and one of the factors that limits the life is the occurrence of dark spots (indicating the part of the device that does not emit light) due to the cathode material. For this reason, the number and size of dark spots in the organic electroluminescent device increase when the device is stored for a long period of time, resulting in a shorter device life.

[0006]

In the organic electroluminescent devices disclosed so far, electroluminescence is brought about by the recombination of holes injected from the anode and electrons injected from the cathode. In general, the injection of carriers is
It must be done by overcoming the injection barrier at the interface between the cathode and the organic light emitting layer. In order to lower the electron injection barrier and improve the injection efficiency, a low work function metal electrode such as magnesium alloy or calcium is used as the cathode. However, since these metal materials have poor adhesion to the organic light emitting layer, they may peel off from the organic light emitting layer,
When the cathode is vapor-deposited on the organic light-emitting layer, or after vapor deposition, a reaction occurs between the cathode material and the organic light-emitting layer material, resulting in deterioration of the light-emitting characteristics of the device or the generation of dark spots during long-term storage. That was a problem.

[0007]

In view of the above situation, the present inventors provide an organic electroluminescent device capable of maintaining stable light emitting characteristics for a long period of time and suppressing the generation of dark spots. As a result of intensive studies for the purpose, it was found that it is preferable to provide an interface layer containing a quinacridone compound between the organic light emitting layer and the cathode, and the present invention has been completed.

That is, the gist of the present invention is an organic electroluminescent device in which an anode, an organic light emitting layer and a cathode are sequentially laminated, and the following general formula (I) is provided between the organic light emitting layer and the cathode.

[0009]

[Chemical 2]

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an allyl group, an aromatic hydrocarbon ring which may have a substituent, or a substituent. R ¹ and R ² , R ³ represents an aromatic heterocycle which may have, an amide group, an alkoxy group, an alkoxycarbonyl group or an amino group which may have a substituent.
And R ⁴ , R ⁵ and R ⁶ , R ⁷ and R ⁸ are bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent. The organic electroluminescent device is characterized in that an interface layer containing a quinacridone compound represented by (may form a ring) is provided.

The organic electroluminescent device of the present invention will be described below with reference to the drawings. FIG. 1 is a cross-sectional view schematically showing a structural example of the organic electroluminescent element of the present invention, in which 1 is a substrate and 2 is
a and 2b are conductive layers, 3 is an organic light emitting layer, and 4 is an interface layer. The substrate 1 serves as a support for the organic electroluminescent element of the present invention, and a plate of quartz or glass, a metal plate or a metal foil, a plastic film or a sheet, and the like are used, and a glass plate, polyester, polymeta A transparent synthetic resin substrate such as acrylate, polycarbonate or polysulfone is preferable.

A conductive layer 2a is provided on the substrate 1,
The conductive layer 2a is usually aluminum, gold, silver,
Metals such as nickel, palladium and tellurium, metal oxides such as indium and / or tin oxides, copper iodide, carbon black or poly (3-methylthiophene)
It is composed of a conductive polymer such as. The conductive layer is usually formed by a sputtering method, a vacuum deposition method or the like, but metal fine particles such as silver or copper iodide, carbon black, conductive metal oxide fine particles, conductive polymer fine powder, etc. In this case, it can also be formed by dispersing it in an appropriate binder resin solution and applying it on a substrate. Further, in the case of a conductive polymer, a thin film can be directly formed on the substrate by electrolytic polymerization or can be formed by coating on the substrate (Appl. Phys. Let.
t. , 60, 2711, 1992). Conductive layer 2a
Thickness depends on the transparency required, but when transparency is required, it is desirable that the visible light transmittance is 60% or more, preferably 80% or more. In this case,
The thickness is usually 5 to 1000 nm, preferably 10 to 5
It is about 00 nm.

The conductive layer 2a may be the same as the substrate 1 if it is opaque. Further, the above conductive layer can be formed by stacking different materials. In the example of FIG. 1, the conductive layer 2a plays a role of hole injection as an anode. On the other hand, the conductive layer 2b serves as a cathode to inject electrons into the organic light emitting layer 3 through the interface layer 4. The material used for the conductive layer 2b can be the material for the conductive layer 2a, but a metal having a low work function is preferable for efficient electron injection, and tin, magnesium, indium, aluminum, A suitable metal such as silver or an alloy thereof is used.
The thickness of the conductive layer 2b is usually the same as that of the conductive layer 2a. Although not shown in FIG. 1, a substrate similar to the substrate 1 may be further provided on the conductive layer 2b. However, it is necessary for at least one of the conductive layers 2a and 2b that the electroluminescent element has good transparency. From this, one of the conductive layers 2a and 2b has a thickness of 10 to 500 nm.
It is preferable that the film thickness is, and good transparency is desired.

The organic light emitting layer 3 is provided on the conductive layer 2a. The organic light emitting layer 3 has holes injected from the anode and electrons injected from the cathode between the electrodes to which an electric field is applied. It is formed from a material that efficiently transports and recombines, and that recombination efficiently emits light. Usually, in order to improve the luminous efficiency, the organic light emitting layer 3 is divided into a hole transporting layer 3a and an electron transporting layer 3b so as to have a function separation type (Appl. Phys). . Le
tt. , 51, 913, 1987).

In the above-mentioned function-separated device, the hole transport material has a high hole injection efficiency from the conductive layer 2a,
At the same time, it is necessary that the material is capable of efficiently transporting the injected holes. For that purpose, it is required that the ionization potential is small, the hole mobility is large, the stability is excellent, and the impurities serving as traps are not easily generated during manufacturing or use.

Examples of such hole transport compounds are described in, for example, JP-A-59-194393 and US Pat. No. 4,175,960, columns 13 to 14.
N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine:
1,1'-bis (4-di-p-tolylaminophenyl)
Cyclohexane: 4,4'-bis (diphenylamino)
Aromatic amine compounds such as quadrophenyl, hydrazone compounds disclosed in JP-A-2-311591,
Examples thereof include silazane compounds shown in US Pat. No. 4,950,950. These compounds may be used alone or, if necessary, may be mixed and used.
In addition to the above compounds, polyvinylcarbazole and polysilane (Appl. Phys. Lett., Vol. 59, 27
60, 1991) and the like.

The above organic hole transport material is laminated on the conductive layer 2a by a coating method or a vacuum deposition method to form the hole transport layer 3a. In the case of coating, a coating solution prepared by adding one or more organic hole-transporting compounds and a binder resin that does not become a hole trap if necessary, and an additive such as a leveling agent or other coating improver is dissolved. The organic hole-transporting layer 3 is prepared by adjusting, coating on the conductive layer 2a by a method such as spin coating, and drying. Examples of the binder resin include polycarbonate, polyarylate, polyester and the like. The addition amount of the binder resin decreases the hole mobility when it is added in a large amount. Therefore, it is preferable that the addition amount is 50% by weight or less.

In the case of the vacuum deposition method, the organic hole transporting material is placed in a crucible installed in a vacuum container, the interior of the vacuum container is evacuated to 10 ^-6 Torr by an appropriate vacuum pump,
The crucible is heated to evaporate the hole transport material and form a layer on the substrate placed facing the crucible. The thickness of the hole transport layer 3a is usually 10 to 300 nm, preferably 3
It is 0 to 100 nm. In order to uniformly form such a thin film, the vacuum evaporation method is often used.

As the material of the hole transport layer 3a, it is possible to use an inorganic material instead of an organic compound. The conditions required for the inorganic material are the same as those for the organic hole transport compound. The inorganic material used for the hole transport layer 3 is p
Examples thereof include p-type hydrogenated amorphous silicon, p-type hydrogenated amorphous silicon carbide, p-type hydrogenated microcrystalline silicon carbide, p-type zinc sulfide, and p-type zinc selenide. These inorganic hole transport layers are formed by a CVD method, a plasma CVD method, a vacuum deposition method, a sputtering method, or the like.

The thickness of the inorganic hole transporting layer is usually 10 to 300 nm, preferably 30 to 1 like the organic hole transporting layer.
00 nm. The electron transport layer 3 is formed on the hole transport layer 3a.
b is provided, the electron transport layer 3b is formed of a compound capable of efficiently transporting electrons from the cathode toward the hole transport layer between the electrodes to which an electric field is applied.

As the organic electron transport compound, the conductive layer 2b is used.
It is necessary that the compound has a high efficiency of injecting electrons from the compound and can efficiently transport the injected electrons. For that purpose, it is required that the compound has a high electron affinity, a high electron mobility, excellent stability, and an impurity that becomes a trap and is less likely to be generated at the time of production or use.

As a material satisfying such a condition, an aromatic compound such as tetraphenyl butadiene (Japanese Patent Application Laid-Open No. Sho 5 (1999) -58138)
7-51781), a metal complex such as an aluminum complex of 8-hydroxyquinoline (JP-A-59-1943).
93), a cyclopentadiene derivative (JP-A-2-
289675), perinone derivatives (JP-A-2-2)
No. 89676), an oxadiazole derivative (JP-A-2-216791), and a bisstyrylbenzene derivative (JP-A 1-245087, 2-222248).
4), perylene derivative (JP-A-2-189890).
JP-A No. 3-791), coumarin compounds (JP-A-2-191694, JP-A-3-792), rare earth complexes (JP-A-1-256584), and distyrylpyrazine derivatives (JP-A-2-252793). Gazette), p-phenylene compound (JP-A-3-33183), thiadiazolopyridine derivative (JP-A-3-37292), pyrrolopyridine derivative (JP-A-3-37293), naphthyridine derivative (special Kaihei 3-203982
Issue).

The organic electron transporting layer using these compounds plays a role of transporting electrons and a role of producing light emission upon recombination of holes and electrons, and also serves as a light emitting layer. When the organic hole transport compound has a light emitting function, the organic electron transport layer serves only to transport electrons.

For the purpose of improving the light emission efficiency of the device and changing the light emission color, for example, a fluorescent dye for laser such as coumarin is doped with aluminum complex of 8-hydroxyquinoline as a host material (J. Appl. Ph.
ys. , 65, 3610, 1989). Also in the present invention, the emission characteristics of the device can be further improved by doping the above-mentioned organic electron transport material as a host material with various fluorescent dyes at 10 ⁻³ to 10 mol%. The thickness of the electron transport layer 3b is usually 10 to 10.
It is 200 nm, preferably 30 to 100 nm.

The organic electron transporting layer can be formed by the same method as the organic hole transporting layer, but the vacuum vapor deposition method is usually used. As a method for further improving the luminous efficiency of the organic electroluminescent device, it is conceivable to stack another electron transport layer 3c on the electron transport layer 3b (see FIG. 3).
The compound used for the electron transport layer 3c is required to be capable of easily injecting electrons from the cathode and have a higher electron transport capability. As such an electron transport material,

[0026]

[Chemical 3]

[0027]

[Chemical 4]

Oxadiazole derivatives such as (App
l. Phys. Lett. , 55, 1489, 19
1989; Jpn. J. Appl. Phys. , 31 volumes,
1812, 1992) or a system in which they are dispersed in a resin such as polymethylmethacrylate (Appl. Phys.
Lett. , 61, 2793, 1992), or n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, n-type zinc selenide, and the like. The thickness of the electron transport layer 3c is
Usually, it is 5 to 200 nm, preferably 10 to 100 nm.

As the single-layer type organic light emitting layer 3 which does not perform the function separation, the above-mentioned poly (p-phenylene vinylene) (Nature, 347, 539, 1990) is used.
Year; Appl. Phys. Lett. , Volume 61, 279
P. 3, 1992), poly [2-methoxy, 5- (2 '
-Ethylhexoxy) -1,4-phenylene vinylene]
(Appl. Phys. Lett., 58, 1982.
P., 1991; Thin Solid Films,
216, 96, 1992; Nature, 357.
Vol., 477, 1992), poly (3-alkylthiophene) (Jpn. J. Appl. Phys, vol. 30,
L 1938, 1991; Appl. Phy
s. , Vol. 72, p. 564, 1992), or a system in which a light emitting material and an electron transfer material are mixed with a polymer such as polyvinylcarbazole (Applied Physics, 61, 1044).
Page, 1992).

An interface layer 4 is provided on the organic light emitting layer.
The role of the interface layer is that it has an affinity with the organic light-emitting layer and at the same time has good adhesion to the cathode, and is chemically stable to allow the reaction between the organic light-emitting layer and the cathode during and / or after formation of the cathode. It has a suppressing effect. It is also important to provide a uniform thin film shape from the viewpoint of adhesion with the cathode. The present inventors, as a material that plays such a role,
It has been found that quinacridone compounds are suitable.

The interface layer made of a quinacridone compound is formed by a coating method or a vacuum vapor deposition method as in the case of the organic hole transport material described above. In the present invention, excellent stability of the device can be achieved by using the quinacridone compound represented by the general formula (I) as an interface layer material between the organic light emitting layer and the cathode in the organic electroluminescent device. It

In the general formula (I), R ¹ , R ² ,
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each a hydrogen atom; a halogen atom such as a chlorine atom or a bromine atom; a C 1-6 alkyl group such as a methyl group or an ethyl group; Alkoxyalkyl groups such as ethyl group, ethoxyethyl group; aryloxyalkyl groups such as phenyloxyethyl group, naphthyloxyethyl group, p-chlorophenyloxyethyl group; benzyl group, phenethyl group, p-chlorobenzyl group, p-nitro Arylalkyl groups such as benzyl group; cycloalkylalkyl groups such as cyclohexylmethyl group, cyclohexylethyl group, cyclopentylethyl group; alkenyloxyalkyl groups such as allyloxyethyl group, 3-bromoallyloxyethyl group; cyanoethyl group, cyanomethyl group Cyanoalkyl groups such as; hydroxyethyl groups, hydroxy Hydroxyalkyl group such as methyl group; substituted or unsubstituted alkyl group such as tetrahydrofuryl group, tetrahydrofurylalkyl group such as tetrahydrofurylethyl group, allyl group; substituted or unsubstituted alkenyl group such as 2-chloroallyl group; phenyl group A substituted or unsubstituted aryl group such as a p-methylphenyl group, a naphthyl group, and a m-methoxyphenyl group; a cycloalkyl group such as a cyclohexyl group and a cyclopentyl group; an amide group; An alkoxy group of 6;
An alkoxycarbonyl group having 1 to 6 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group; an amino group which may have a substituent can be mentioned, but preferably a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. To be elected.

R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , R
⁷ and R ⁸ may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocycle which may have a substituent, preferably ,
A condensed aromatic ring such as a benzene ring or a naphthalene ring may be formed. These quinacridone compounds and their synthesis methods are described, for example, in Dyes and Chemicals, Vol. 13, p. 81, 196.
It is shown in 8 years etc.

Specific examples of the quinacridone compound represented by the general formula (I) are shown in Table 1 below, but the invention is not limited thereto.

[0035]

[Table 1]

In addition to those shown in Table 1, 3, 4, 1
0,11-dibenzo body, 1,2,8,9-dibenzo body,
2,3,9,10-dibenzo form, 3,4,10,11-
A derivative such as a dinaphtho compound may also be mentioned. When the quinacridone compound shown above is used for the interface layer, these compounds may be further mixed and used.

Examples of the organic electroluminescent device of the present invention having an interface layer made of a quinacridone compound include those having the following layer structures.

[0038]

[Table 2] Anode / organic light emitting layer / interface layer / cathode, anode / polymer organic light emitting layer / interface layer / cathode, anode / polymer dispersed organic light emitting layer / interface layer / cathode, anode / positive Pore transport layer / organic electron transport light emitting layer / interface layer / cathode, anode / organic hole transport light emitting layer / organic electron transport layer / interface layer / cathode, anode / hole transport layer / organic electron transport light emitting layer / The thickness of the electron transport layer / interface layer / cathode, interface layer is usually 2 to 100 nm, preferably 5
~ 30 nm.

In each of the above layer constitutions, as the interface layer,
A quinacridone compound is added in the vicinity of the cathode interface of the organic light emitting layer, the organic electron transporting light emitting layer, the organic electron transporting layer or the electron transporting layer.
A region (layer) containing 0 mol% or more may be provided. That is, in the present invention, a quinacridone compound is used as an interface layer between the organic light emitting layer and the cathode in the organic electroluminescent device.
By providing the layer containing 0 mol% or more, excellent stability of the device is achieved.

It is also possible to have a structure opposite to that shown in FIG. 1, that is, the conductive layer 2b, the interface layer 4, the organic light emitting layer 3 and the conductive layer 2a may be laminated in this order on the substrate, and at least as described above. It is also possible to provide the organic electroluminescent element of the present invention between two substrates, one of which is highly transparent. Similarly, it is also possible to stack in a structure opposite to that of FIGS.

[0041]

EXAMPLES Next, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 An organic electroluminescent device having the structure shown in FIG. 2 was produced by the following method.

A glass substrate on which a transparent conductive film of indium tin oxide (ITO) is deposited to a thickness of 120 nm is ultrasonically cleaned with acetone, washed with pure water, ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen, and UV / ozone. After the cleaning, it was installed in a vacuum vapor deposition apparatus and evacuated using an oil diffusion pump until the degree of vacuum in the apparatus became 2 × 10 ⁻⁶ Torr or less.

As the organic hole transport layer material, N, N'-diphenyl-N, N '-(3 represented by the following structural formula (H1) is used.
-Methylphenyl) -1,1'-biphenyl-4,4 '
-Diamine

[0044]

[Chemical 5]

[0045] was placed in a ceramic crucible and heated by a tantalum wire heater around the crucible for vapor deposition. The temperature of the crucible at this time was controlled in the range of 160 to 170 ° C. The degree of vacuum during vapor deposition was 2 × 10 ⁻⁶ Torr, and an organic hole transport layer 3a having a film thickness of 60 nm was obtained with a vapor deposition time of 3 minutes and 20 seconds. Then, as the material of the organic electron-transporting layer 3b, the aluminum shown in the following structural formulas (E1) 8- hydroxyquinoline complex _{Al (C 9 H 6 NO)} 3

[0046]

[Chemical 6]

The above was vapor-deposited on the organic hole transport layer 3a in the same manner. The temperature of the crucible at this time is 230-2
The temperature was controlled in the range of 70 ° C. The degree of vacuum during vapor deposition is 2 × 10 ^-6
Torr, vapor deposition time was 3 minutes and 30 seconds, and film thickness was 75 nm. This layer serves as a light emitting layer. Next, as the interface layer 4, the quinacridone compound (1) shown in Table 1 is used.

[0048]

[Chemical 7]

On the organic electron transporting light emitting layer 3b,
Vapor deposition was performed in the same manner as the hole transport layer 3a. True when vapor deposition
The vacancy is 2 × 10^-6Torr, vapor deposition time 1 minute, film thickness 1
It was 0 nm. Finally, as the cathode, magnesium and silver
Alloy electrode of 150 nm thickness by two-source simultaneous vapor deposition method
It was vapor-deposited. Deposition is performed using a molybdenum boat, and the degree of vacuum is
3 x 10 ^-6Torr, vapor deposition time is 4 minutes and 30 seconds
A film was obtained. The atomic ratio of magnesium to silver is 10:
It was 1.5.

Table 2 shows the results of the emission characteristics measured by applying a positive DC voltage to the ITO electrode (anode) and a negative DC voltage to the magnesium-silver alloy electrode (cathode) of the organic electroluminescent device thus produced. Show. This device showed uniform yellow-green light emission, and the emission peak wavelength was 560 nm. Table 2 shows the results of measuring the emission characteristics of the device after storing it in a vacuum. The area of the dark spot shows a value quantified by image analysis after photographing the light emission from the device using a CCD camera.

Comparative Example 1 An organic electroluminescent device having the structure shown in FIG. 2 was prepared in the same manner as in Example 1 except that the interface layer 4 was not provided. Table 2 shows the measurement results of the emission characteristics of the device after it was manufactured and after it was stored in vacuum. The occurrence of dark spots was clear.

[0052]

[Table 3]

Example 2 After depositing the quinacridone compound (1) shown in Table 1 in a film thickness of 100 nm on a glass substrate, in the same manner as in Example 1, an alloy electrode of magnesium and silver was simultaneously vapor-deposited. The film was vapor-deposited using a contact mask in a strip shape of 2 mm × 20 mm with a film thickness of 150 nm by the method. When a peeling test of the above electrode was conducted using a Scotch tape, the thin film of the quinacdrine compound was peeled off from the glass substrate together with the electrode, and the adhesive force with the above metal electrode was good.

Comparative Example 2 A sample for an electrode peeling test was prepared in the same manner as in Example 2 except that the aluminum 8-hydroxyquinoline complex (E1) was used instead of the quinacridone compound (1). When a peeling test of the above electrode was conducted using Scotch tape, the electrode peeled from the organic layer and the adhesion was poor.

[0055]

In the organic electroluminescent device of the present invention, an anode, an organic light emitting layer and a cathode are sequentially provided on a substrate, and an interface layer containing a specific compound is provided between the organic light emitting layer and the cathode. Therefore, when voltage is applied with both conductive layers as electrodes,
Stable light emission characteristics can be obtained over a long period of time.

Therefore, the organic electroluminescent device of the present invention is a light source (for example, a light source for a copying machine, a liquid crystal display) which makes the most of the field of flat panel displays (for OA computers and wall-mounted televisions) and the characteristics as a surface light emitter. Light sources for backlights of instruments and instruments), display boards, and sign lamps are considered to have great technical value.

[Brief description of drawings]

FIG. 1 is a schematic cross-sectional view showing an example of an organic electroluminescence device of the present invention.

FIG. 2 is a schematic cross-sectional view showing another embodiment of the organic electroluminescent element of the present invention.

FIG. 3 is a schematic cross-sectional view showing another embodiment of the organic electroluminescent element of the present invention.

[Explanation of symbols]

DESCRIPTION OF SYMBOLS 1 Substrate 2a, 2b Conductive layer 3 Organic light emitting layer 3a Hole transport layer 3b Organic electron transport layer 3c Organic electron transport layer composed of a compound different from 3b 4 Interface layer

Claims (1)

[Claims] 1. An organic electroluminescent device in which an anode, an organic light emitting layer, and a cathode are sequentially laminated, wherein the following general formula (I) is provided between the organic light emitting layer and the cathode. (In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently a hydrogen atom, a halogen atom,
Alkyl group, aralkyl group, alkenyl group, allyl group,
Aromatic hydrocarbon ring optionally having substituent (s), aromatic heterocycle optionally having substituent (s), amide group, alkoxy group, alkoxycarbonyl group or amino group optionally having substituent (s) R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ are each bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or a substituent. An organic electroluminescent device comprising an interface layer containing a quinacridone compound represented by the formula (which may form a heteroaromatic ring which may have a group).