JP2000058267A - Organic electroluminescence element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic EL element having large luminescence intensity and capable of exerting stable performance in repeated use by containing indanthrene pigment in a positive hole injected layer on the organic EL element provided with at least an anode, the positive hole injected layer, a positive hole transportation layer, a luminescence layer and a cathode. SOLUTION: The indanthrene pigment contained in a positive hole injected layer is expressed by the formula I and/or the formula II, and practically it is a compound expressed by the formulas III, IV. The compound of the formula III is formed into a thin film at the thickness of 10 nm as a positive hole injected layer on an indium-tin oxide-coated glass substrate, and N,N'-diphenyl-N,N'- bis(3-methyl phenyl)-1,1'-diphenyl-4,4'-diamine is formed into a thin film at the thickness of 50 nm as a positive hole transportation layer on the positive hole injected on layer. Aluminum trisoxine is formed into a thin film at the thickness of 60 nm as an organic luminescence layer on it. Magnesium is formed into a thin film at the thickness of 200 nm as a 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.

[0002]

2. Description of the Related Art An organic electroluminescence element is an element which emits light in response to an electric signal and is constituted by using an organic compound as a light emitting substance. The organic electroluminescence element basically includes an organic light emitting layer and a pair of counter electrodes sandwiching the organic light emitting layer. In the light emission, electrons are injected from one of the electrodes and holes are injected from the other electrode, so that the luminescent material in the luminescent layer is excited to a higher energy level, and the excited luminescent material is returned to its original base. When returning to the state, the extra energy is emitted as light.

In order to increase the luminous efficiency, in addition to the above-mentioned basic structure, a structure in which a hole injection layer is further provided for an electrode for injecting holes, and an electron transport layer is provided for an electrode for injecting electrons. Has been taken.

[0004] As an example of an organic electroluminescent device, a device using a single crystal anthracene or the like as a light emitting body is described in US Pat. No. 3,530,325.

Japanese Patent Application Laid-Open No. Sho 59-194393 proposes a combination of a hole injection layer and an organic light emitting layer.

Japanese Unexamined Patent Publication (Kokai) No. 63-265695 proposes a combination of an organic hole injection / transport layer and an organic electron injection / transport layer.

[0007] These organic EL devices having a laminated structure have a structure in which an organic phosphor, a charge-transporting organic substance (charge-transporting material) and an electrode are laminated, and holes and electrons injected from each electrode are laminated. Move through the charge transporting material and emit light when they recombine. As the organic phosphor, an organic dye which emits fluorescence such as an 8-quinolinol aluminum complex or a coumarin compound is used. As the charge transport material, for example, N, N '
-Di (m-tolyl) N, N'-diphenylbenzine,
Diamino compounds such as 1,1-bis [N, N-di (p-tolyl) aminophenyl] cyclohexane,
(N, N-diphenyl) aminobenzaldehyde-N,
And N-diphenylhydrazone compounds. Further, porphyrin compounds such as copper phthalocyanine have been proposed.

[0008] Although organic electroluminescent devices have high light-emitting characteristics, they are not sufficient in terms of stability during light emission and storage stability, and have not been put to practical use. It has been pointed out that the stability of the charge transporting material is one of the problems in the light emission stability and storage stability of the device.
A layer formed of an organic material of an organic electroluminescence element is very thin, several tens to several hundreds of nanometers, and a voltage applied per unit thickness is very high. In addition, heat is generated by light emission and energization. Therefore, the charge transporting material is required to have electrical, thermal or chemical stability.

[0009]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an organic electroluminescent device having a high emission intensity and exhibiting stable performance even when used repeatedly. An object of the present invention is to provide a luminescence element.

[0010]

According to the present invention, there is provided an organic electroluminescence device provided with at least an anode, a hole injection layer, a hole transport layer, a light emitting layer and a cathode, wherein the hole injection layer comprises an indanthrene pigment. The present invention relates to an organic electroluminescent device characterized by containing.

More preferably, in an organic electroluminescent device provided with at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode, the hole injection layer is
An organic electroluminescent device comprising an indanthrene pigment represented by the following general formulas [I] and / or [II]:

Embedded image (Wherein, R _{1 to} R ₃ each independently represent hydrogen, a halogen atom, a hydroxyl group, or an arylamide group;
Is a residue which forms a condensed polycyclic group by bonding to a nitrogen atom and an anthraquinone ring, and may have a substituent).

The organic electroluminescent device of the present invention comprises at least a hole injecting layer, a hole transporting layer and a photosensitive layer between electrodes, and basically contains an indanthrene pigment in the hole injecting layer. Features. Preferably, the indanthrene pigment contains an indanthrene pigment represented by the following general formula [I] or [II].

Embedded image

In the above formula, R _{1 to} R ₃ are each independently
It represents a halogen atom such as a hydrogen atom, a chlorine atom or a bromine atom, a hydroxyl group, or an arylamide group such as a benzamide group. Z is a residue bonded to a nitrogen atom and an anthraquinone ring to form a condensed heterocyclic group required for forming an indanthrene pigment, and may have a substituent. Examples of the substituent of the condensed heterocyclic group include an alkyl group, a halogen atom, a hydroxyl group and an arylamide group.

Specific examples of the indanthrene pigments represented by the general formulas [I] and [II] include, but are not limited to, the following.

[0015]

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[0016]

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[0017]

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[0018]

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[0019]

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[0020]

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Various indanthrene pigments represented by the general formulas [I] and [II] are commercially available.
Further, it can be manufactured by a known method. For example, the indanthrene pigment of the compound example (1) can be easily produced by subjecting a 1-amino-2-bromoanthraquinone compound to two-molecule condensation in a high boiling point solvent using copper (I) chloride. .

FIG. 1 schematically shows an organic electroluminescence device according to the present invention. In the figure, (1) is an anode, on which a hole injection layer (2), a hole transport layer (3), an organic light emitting layer (4), and a cathode (5) are sequentially laminated. And the hole injection layer contains an indanthrene pigment represented by the general formula [I].

In FIG. 2, (1) is an anode, on which a hole injection layer (2) and a hole transport layer (3), an organic light emitting layer (4) and an electron transport layer (6) are provided. The cathode (5) has a configuration in which the cathode (5) is sequentially laminated, and the hole injection layer has a general formula [I]
It contains an indanthrene pigment represented by

In FIG. 3, (1) is an anode, on which a hole injection layer (2) and a hole transport layer (3), an organic light emitting layer (4), an electron transport layer (6), an electron The injection layer (7) and the cathode (5) are sequentially laminated, and the hole injection layer contains the indanthrene pigment represented by the general formula [I].

In FIG. 4, (1) is an anode, on which a hole injection layer (2), a hole transport layer (3), an organic light emitting layer (4), a cathode (5), and a sealing film. (8) is sequentially laminated, and the hole injection layer contains an indanthrene pigment represented by the general formula [I].

In the organic electroluminescent device having the above structure, the anode (1) and the cathode (5) are connected by a lead wire (9), and a voltage is applied between the anode (1) and the cathode (5). The organic light emitting layer (4) emits light.

Since the indanthrene pigment represented by the general formula [I] used in the present invention generally has a low ionization potential and a large hole transporting ability, it is necessary for the organic electroluminescent device of the present invention to emit light. It is considered that the light emission starting voltage may be low, the heat resistance is good, and the light emission can be stably performed for a long time in order to prevent crystallization of the hole transport material.

As the conductive substance used as the anode (1) of the organic electroluminescence element, those having a work function larger than 4 eV are preferable, and carbon, aluminum, vanadium, iron, cobalt, nickel, copper, zinc,
Tungsten, silver, tin, gold, and alloys thereof, and conductive metal compounds such as tin oxide, indium oxide, antimony oxide, zinc oxide, and zirconium oxide are used.

The metal forming the cathode (5) is 4 eV
Those having a lower work function are preferred, and magnesium, calcium, titanium, yttrium, lithium, gadolinium, ytterbium, ruthenium, manganese, and alloys thereof are used.

In the organic electroluminescence element, at least the anode (1) or the cathode (5) needs to be a transparent electrode so that light emission can be seen. On this occasion,
If a transparent electrode is used for the cathode, the transparency is likely to be impaired. Therefore, it is preferable that the anode be a transparent electrode.

When forming a transparent electrode, on a transparent substrate,
Using a conductive material as described above, a device such as vapor deposition, sputtering, or a method such as a sol-gel method or a method of dispersing and applying in a resin or the like is used to secure desired translucency and conductivity. I just need.

The transparent substrate is not particularly limited as long as it has an appropriate strength, is not adversely affected by heat due to vapor deposition or the like when producing an organic electroluminescent device, and is transparent. It is also possible to use a glass substrate, a transparent resin such as polyethylene, polypropylene, polyethersulfone, polyetheretherketone, and the like. As a transparent electrode formed on a glass substrate, commercially available products such as ITO and NESA are known, but these may be used.

The production of an organic electroluminescence device having the structure shown in FIG. 1 using the above-described electrodes will be described as an example. First, a hole injection layer (2) is formed on the above-mentioned anode (1). The hole injection layer (2) may be formed by vapor deposition of an indanthrene pigment represented by the general formula [I], or may be a solution in which the compound is dispersed or a solution in which a suitable resin is dispersed. It may be formed by coating or spin coating.

When the hole injection layer is formed by a vapor deposition method, its thickness is usually 1 to 30 nm, and when it is formed by a coating method, the thickness may be about 1 to 50 nm.

It is necessary to increase the applied voltage for emitting light as the thickness of the formed film is larger, so that the luminous efficiency is poor and the organic electroluminescent element is liable to be deteriorated. When the film thickness is small, the luminous efficiency is improved, but the breakdown is easy and the life of the organic electroluminescent element is shortened.

A hole transport layer (3) is formed on the hole injection layer (2). As the hole transporting material used for the hole transporting layer, known materials can be used. For example, N, N '
-Diphenyl-N, N'-bis (3-methylphenyl)
-1,1′-diphenyl-4,4′-diamine, N,
N′-diphenyl-N, N′-bis (4-methylphenyl) -1,1′-diphenyl-4,4′-diamine;
N, N′-diphenyl-N, N′-bis (1-naphthyl) -1,1′-diphenyl-4,4′-diamine;
N, N′-diphenyl-N, N′-bis (2-naphthyl) -1,1′-diphenyl-4,4′-diamine;
N, N'-tetra (4-methylphenyl) -1,1'-
Diphenyl-4,4'-diamine, N, N'-tetra (4-methylphenyl) -1,1'-bis (3-methylphenyl) -4,4'-diamine, N, N'-diphenyl-N , N'-bis (3-methylphenyl) -1,1 '
-Bis (3-methylphenyl) -4,4'-diamine,
N, N′-bis (N-carbazolyl) -1,1′-diphenyl-4,4′-diamine, 4,4 ′, 4 ″ -tris (N-carbazolyl) triphenylamine, N, N ′,
N "-triphenyl-N, N ', N" -tris (3-methylphenyl) -1,3,5-tri (4-aminophenyl) benzene, 4,4', 4 "-tris [N, N ',
N "-triphenyl-N, N ', N" -tris (3-methylphenyl)] triphenylamine, N, N'-diphenyl-N, N'-bis (4-methylphenyl) -1,
1'-bis (3-methylphenyl) -4,4'-diamine and the like can be mentioned. These may be used as a mixture of two or more.

When the hole transport layer is formed by a vapor deposition method, its thickness is usually 30 to 100 nm, and when it is formed by a coating method, the thickness may be about 50 to 200 nm.

It is necessary to increase the applied voltage for emitting light as the thickness of the formed film is larger, so that the luminous efficiency is poor and the organic electroluminescent element is liable to be deteriorated. When the film thickness is small, the luminous efficiency is improved, but the breakdown is easy and the life of the organic electroluminescent element is shortened.

As the organic luminescent material used in the organic luminescent layer, known luminescent materials can be used.
2,5-bis [5,7-di-t-pentyl-2-benzooxazolyl] thiophene, 2,2 ′-(1,4-phenylenedivinylene) bisbenzothiazole, 2,2′-
(4,4′-biphenylene) bisbenzothiazole, 5
-Methyl-2- {2- [4- (5-methyl-2-benzoxazolyl) phenyl] vinyl} benzoxazole, 2,5-bis (5-methyl-2-benzooxazolyl) thiophene, anthracene , Naphthalene, phenanthrene, pyrene, chrysene, perylene, perinone, 1,
4-diphenylbutadiene, tetraphenylbutadiene, coumarin, acridine, stilbene, 2- (4-biphenyl) -6-phenylbenzoxazole, aluminum trisoxin, magnesium bisoxin, bis (benzo-8-quinolinol) zinc, bis (2 -Methyl-8-quinolinolato) aluminum oxide, indium trisoxine, aluminum tris (5-methyloxin), lithium oxine, gallium trisoxin, calcium bis (5-chlorooxin), polyzinc-bis (8-hydroxy -5-quinolinolyl) methane, dilithium epindridione, zinc bisoxin, 1,2-phthaloperinone, 1,2-naphthaloperinone, and the like.

Further, general fluorescent dyes such as fluorescent coumarin dyes, fluorescent perylene dyes, fluorescent pyran dyes, fluorescent thiopyran dyes, fluorescent polymethine dyes, fluorescent methyanine dyes, fluorescent imidazole dyes and the like can also be used. this house,
Particularly preferred are chelated oxinoid compounds.

The organic light-emitting layer may have a single-layer structure of the above-described light-emitting substance, or may have a multi-layer structure in order to adjust characteristics such as light emission color and light emission intensity. Further, two or more kinds of light-emitting substances may be mixed or the light-emitting layer may be doped.

When formed by the vapor deposition method, the thickness is usually 1 to 200 nm, and when formed by the coating method, the thickness is 5 to 200 nm.
The thickness may be about 500 nm. As the film thickness is larger, the applied voltage for emitting light needs to be higher, so that the luminous efficiency is poor and the organic electroluminescent element is likely to be deteriorated. When the film thickness is small, the luminous efficiency is improved, but the breakdown is easy and the life of the organic electroluminescent element is shortened.

Next, the above-mentioned cathode is formed on the organic light emitting layer.

A pair of transparent electrodes of a cathode and an anode are connected to appropriate leads (9) such as a nichrome wire, a gold wire, a copper wire, a platinum wire and the like, and the organic electroluminescent element is connected to both electrodes. Light is emitted by applying an appropriate voltage (Vs).

In the organic electroluminescence device of the present invention, an electron transport layer may be formed between the light emitting layer (4) and the cathode (5) as shown in FIG.

As the electron transporting material used for the electron transporting layer, known materials can be used. For example, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,3 4-oxadiazole, 2- (1-naphthyl) -5- (4-tert-butylphenyl) -1,
3,4-oxadiazole, 1,4-bis {2- [5-
(4-tert-butylphenyl {-1,3,4-oxadiazolyl]} benzene, 1,3-bis} 2- [5-
(4-tert-butylphenyl) -1,3,4-oxadiazolyl] {benzene, 4,4′-bis} 2- [5
-(4-tert-butylphenyl) -1,3,4-oxadiazolyl] biphenyl, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,
3,4-thiodiazole, 2- (1-naphthyl) -5
(4-tert-butylphenyl) -1,3,4-thiodiazole, 1,4-bis {2- [5- (4-tert
-Butylphenyl) -1,3,4-thiodiazolyl]}
Benzene, 1,3-bis {2- [5- (4-tert-
Butylphenyl) -1,3,4-thiodiazolyl] {benzene, 4,4′-bis} 2- [5- (4-tert-
Butylphenyl) -1,3,4-thiodiazolyl] biphenyl, 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4
-Triazole, 3- (1-naphthyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,2
4-triazole, 1,4-bis {3- [4-phenyl-5- (4-tert-butylphenyl) -1,2,4
-Triazolyl] {benzene, 1,3-bis} 3- [4
-Phenyl-5- (4-tert-butylphenyl)-
1,3,4-oxadiazolyl]｝ benzene, 4,4 ′
-Bis {2- [4-phenyl-5- (4-tert-butylphenyl) -1,3,4-oxadiazolyl]} biphenyl, 1,3,5-tris} 2- [5- (4-te
rt-butylphenyl) -1,3,4-oxadiazolyl] @benzene. These may be used as a mixture of two or more.

When the electron transporting layer is formed by a vapor deposition method, its thickness is usually 5 to 200 nm, and when it is formed by a coating method, the thickness may be about 10 to 1000 nm.

When an electron injection layer (7) is provided in addition to the electron transport layer as shown in FIG.
It is formed to have a thickness of about 0 nm. As the material used for the electron injecting layer, the same material as the above-described electron transporting material can be used. However, since the electron injecting layer is generally provided for the purpose of improving the electron injecting property, work with a cathode having little electron transporting ability is performed. The one with a small function difference is used.

As shown in FIG. 4, when a protective film is formed, a thin film is formed by a vacuum deposition method using a compound such as silicon oxide, zinc oxide, magnesium fluoride, and magnesium oxide. It is formed to have a thickness of about 5 to 1000 nm.

The organic electroluminescent device of the present invention is applicable to various display devices, display devices, and the like.

Hereinafter, the present invention will be described by way of examples.

Example 1 A thin film having a thickness of 10 nm was formed on a substrate of indium tin oxide-coated glass by vapor deposition of compound (1) as a hole injection layer. Next, on the hole injection layer, N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-diphenyl-4,4, ′-diamine was formed as a hole transport layer. Was formed into a thin film having a thickness of 50 nm by vapor deposition. A thin film was formed thereon as an organic light emitting layer by vapor deposition of aluminum trisoxine to a thickness of 60 nm. Next, magnesium was vapor-deposited for 200 as a cathode.
A thin layer was formed to a thickness of nm. Thus, an organic electroluminescence device was manufactured.

Examples 2-3 In Example 1, instead of using compound (1),
An organic electroluminescent device was produced in exactly the same manner as in Example 1 except that the compounds (3) and (7) were used.

Example 4 A thin film having a thickness of 5 nm was formed by vapor deposition of compound (1) as a hole injection layer on a substrate of indium tin oxide coated glass. Next, on the hole injection layer, N, N′-diphenyl-N, N′-bis (1-naphthyl) -1,1′-diphenyl-4,4′-diamine was used as a hole transport layer. A thin film having a thickness of 55 nm was formed by vapor deposition. Next, a thin film having a thickness of 20 nm was formed as an organic light emitting layer by vapor deposition of aluminum trisoxine.

Next, a thin film having a thickness of 40 nm was formed by vapor deposition of the following oxadiazole compound (A) as an electron transporting layer.

Embedded image Next, magnesium was evaporated to 200 nm as a cathode.
A thin film was formed to have a thickness of. In this way,
An organic electroluminescence device was manufactured.

Examples 5-6 In Example 4, instead of using compound (1),
An organic electroluminescent device was produced in exactly the same manner as in Example 4 except that the compounds (8) and (10) were used instead.

Example 7 A thin film having a thickness of 15 nm was formed on a substrate of indium tin oxide-coated glass by vapor deposition of compound (1) as a hole injection layer. Next, on the hole injection layer, N, N'-diphenyl-N, N'-bis (4-methylphenyl) -1,1'-bis (3-methylphenyl)-was formed as a hole transport layer.
A thin film having a thickness of 45 nm was formed by vapor deposition of 4,4′-diamine. An organic light emitting layer was formed thereon by co-evaporation of aluminum trisoxin doped with 5% by weight of rubrene to form a thin film having a thickness of 30 nm. Next, a thin film having a thickness of 30 nm was formed by vapor deposition of the oxadiazole compound (A) as an electron transport layer. Next, as a cathode, a thin film was formed by vapor deposition of Mg and Ag at an atomic ratio of 10: 1 to a thickness of 200 nm. Thus, an organic electroluminescence device was manufactured.

Examples 8-9 In Example 7, instead of using compound (1),
Example 7 except that compounds (11) and (14) were used instead.
An organic electroluminescent device was produced in exactly the same manner as in 1.

Example 10 Compound (1) was coated on a substrate of indium tin oxide coated glass.
9) was vacuum-deposited to obtain a 10-nm-thick hole injection layer. Further, N, N'-diphenyl-N, N '-(3-
Methylphenyl) -1,1′-biphenyl-4,4′-
Diamine was vacuum deposited to obtain a hole transport layer having a thickness of 50 nm. Next, a thin film was formed by vapor deposition of a tris (8-hydroxyquinoline) aluminum complex so as to have a thickness of 50 nm. Next, as a cathode, a 10: 1 atomic ratio of M
g and Ag were deposited to form a thin film having a thickness of 200 nm. Finally, a 300 nm protective film was formed by vacuum evaporation using a resistance heating method with silicon oxide as an evaporation source. Thus, an organic electroluminescence device was manufactured.

COMPARATIVE EXAMPLE 1 N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-diphenyl-4, N, N'-diphenyl-N, N'-bis (3-methylphenyl) was used as a hole transport layer on a glass substrate coated with indium tin oxide. A thin film having a thickness of 60 nm was formed by vapor deposition of 4′-diamine. A thin film was formed thereon as an organic light emitting layer by vapor deposition of aluminum trisoxine to a thickness of 60 nm. Next, magnesium was vapor-deposited for 200 as a cathode.
A thin film was formed to have a thickness of nm. Thus, an organic electroluminescence device was manufactured.

Comparative Example 2 N, N′-diphenyl-N, N′-bis (1-naphthyl) -1,1′-diphenyl-4,4 was formed as a hole transport layer on a substrate of indium tin oxide coated glass. A thin film having a thickness of 60 nm was formed by vapor deposition of '-diamine. next,
A thin film was formed as an organic light emitting layer by vapor deposition of aluminum trisoxine to a thickness of 20 nm. Next, a thin film having a thickness of 40 nm was formed by vapor deposition of the following oxadiazole compound (A) as an electron transport layer. Next, a thin film was formed as a cathode by evaporation of magnesium to have a thickness of 200 nm. Thus, an organic electroluminescence device was manufactured.

Evaluation The organic electroluminescent devices obtained in Examples 1 to 10 and Comparative Examples 1 and 2 were applied with a voltage (V) at which light emission started when a DC voltage was gradually applied to the glass electrode as an anode. ) And emission luminance (cd / m ² ) when a DC voltage of 5 V was applied. Further, the maintenance rate (%) of the initial output when operated at a current density of 5 mA / cm ² for 5 hours (output (mW / cm ² ) after 5 hours / initial output (mW / cm ² ) × 10
0) was determined. Table 1 summarizes the measurement results.

[0063]

[Table 1]

As can be seen from Table 1, the organic electroluminescence device of the present invention started to emit light at a low potential and exhibited good emission luminance. In addition, the organic electroluminescent device of the present invention was able to observe stable light emission having a small output and a long lifetime.

The organic electroluminescent device of the present invention achieves an improvement in luminous efficiency, luminous brightness and a long life, and is used together with a luminescent substance, a luminescent auxiliary material, a charge transport material, a sensitizer, The invention is not limited to resin, electrode material, and the like, and the element manufacturing method.

[0066]

According to the present invention, an organic electroluminescence device having a high light emission intensity, a low light emission starting voltage and excellent durability can be obtained by incorporating an indanthrene pigment in the hole injection layer of the organic electroluminescence device. be able to.

[Brief description of the drawings]

FIG. 1 is a schematic cross-sectional view of one configuration example of an organic electroluminescence element of the present invention.

FIG. 2 is a schematic cross-sectional view of one configuration example of the organic electroluminescence element of the present invention.

FIG. 3 is a schematic cross-sectional view of one configuration example of the organic electroluminescence element of the present invention.

FIG. 4 is a schematic cross-sectional view of one configuration example of the organic electroluminescence element of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 anode 2 hole injection layer 3 hole transport layer 4 organic light emitting layer 5 cathode 6 electron transport layer 7 electron injection layer 8 protective film 9 lead wire

Claims (2)

[Claims] 1. An organic electroluminescence device provided with at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode, wherein the hole injection layer contains an indanthrene pigment. Organic electroluminescent element. 2. An organic electroluminescence device provided with at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode, wherein the hole injection layer has the following general formula [I]
And / or an organic electroluminescent device containing an indanthrene pigment represented by [II]: (Wherein, R _{1 to} R ₃ each independently represent hydrogen, a halogen atom, a hydroxyl group, or an arylamide group;
Is a residue which forms a condensed polycyclic group by bonding to a nitrogen atom and an anthraquinone ring, and may have a substituent).