JP4886975B2 - Electroluminescent device - Google Patents

Description

  The present invention relates to a novel organic electroluminescent device. More specifically, the present invention relates to a novel organic electroluminescent device comprising a 3,6-diarylcarbazole derivative having high efficiency and excellent durability.

  In recent years, organic electroluminescence devices are self-luminous, so they have a wide viewing angle dependency, high visibility, and because they are thin-film type solid-state devices, they have been attracting attention from the viewpoint of space saving, etc. Deployment to has started. However, there are many problems to be solved such as further improvement of energy conversion efficiency and light emission quantum efficiency, and addition of stability of the organic thin film over time.

  So far, organic electroluminescent elements have been reported to use low molecules and polymers. For low molecular weight materials, it has been reported that high efficiency is achieved by adopting various laminated structures, and that durability is improved by well controlling the doping method. However, in the case of a low molecular aggregate, it has been reported that the film state changes with time for a long time, and has an essential problem regarding the stability of the film.

On the other hand, with regard to polymer materials, until now, vigorous studies have been made mainly on poly-p-phenylene vinylene (PPV) series, poly-thiophene, and the like. However, it is difficult to increase the purity of these material systems, and the fluorescence quantum yield is essentially low, so that a high-performance organic electroluminescence device has not been obtained at present. In the case of a polymer material, considering that the glass state is essentially stable, an excellent organic electroluminescence device can be constructed if high fluorescence quantum efficiency can be imparted.
As described above, it is known that there are advantages and disadvantages in the one using the low molecular weight material and the one using the high molecular weight material.

  Recently, high efficiency using triplet excitons has also been intensively studied (C. Adachi, MA Baldo, SR Forrest and ME Thompson, Appl. Phys. Lett. , 77, 904 (2000), etc.), it was revealed that the luminous efficiency is greatly improved. Along with this, reports of host materials used for the light emitting layer are increasing.

  Among these, a representative host material is 4,4′-bis (carbazolyl-9) biphenyl (CBP) represented by the following formula, and CBP crystallization progresses in the light emitting layer by subsequent studies. It has been found that this shortens the lifetime of the device (WO01 / 72927 A1... Patent Document 1).

  In order to avoid this problem, WO01 / 72927 A1, Japanese Patent Application Laid-Open No. 9-310066 (Patent Document 2) and the like have studied a carbazole compound replacing CBP.

WO01 / 72927 A1 JP-A-9-310066

  The present invention has been made in view of the current state of the prior art described above, and is a novel organic electroluminescence that is highly efficient and excellent in durability, particularly containing a 3,6-diarylcarbazole derivative as a component constituting the organic layer. An object is to provide an element.

As a result of intensive studies, the present inventors have found that an organic electroluminescence device having an organic layer containing a 3,6-diarylcarbazole derivative represented by the following general formula (1) has excellent light emission characteristics. It came to complete.
That is, according to the present invention, the following (1) to ( 5 ) are provided.
(1) In an organic electroluminescent device composed of a single layer or a plurality of organic layers between an anode and a cathode facing each other, at least a 3,6-diarylcarbazole derivative represented by the following general formula (2): An organic electroluminescence device comprising one layer.

（式中、Ｒ１及びＲ２は、無置換のアルキル基、無置換のアルコキシ基またはハロゲン原子を表し、Ｒ３及びＲ４は、水素原子を表し、Ｒ５は、無置換のアルキル基、無置換のフェニル基、無置換のアルキルフェニル基、無置換のアルコキシフェニル基、または、無置換のビフェニリル基を表す。）
（２）互いに対向する陽極と陰極間に、単層もしくは複数層の有機層から構成される有機電界発光素子において、下記一般式（２）で表される３，６−ジアリールカルバゾール誘導体を、少なくとも一層に含有することを特徴とする有機電界発光素子。

Wherein R1 and R2 represent an unsubstituted alkyl group, an unsubstituted alkoxy group or a halogen atom, R3 and R4 represent a hydrogen atom, R5 represents an unsubstituted alkyl group, an unsubstituted phenyl group. , unsubstituted alkyl phenyl group, an unsubstituted alkoxyphenyl group, or an unsubstituted biphenyl group.)
(2) In an organic electroluminescent device composed of a single layer or a plurality of organic layers between an anode and a cathode facing each other, at least a 3,6-diarylcarbazole derivative represented by the following general formula (2): An organic electroluminescence device comprising one layer.

（式中、Ｒ１及びＲ２は、水素原子を表し、Ｒ３及びＲ４は、水素原子を表し、Ｒ５は、無置換のアルキル基を表す。）

（３）互いに対向する陽極と陰極間に、単層もしくは複数層の有機層から構成される有機電界発光素子において、該有機層の内の単層または複数層からなるホール輸送層に前記（１）項または（２）項に記載の一般式（２）で表される３，６−ジアリールカルバゾール誘導体を、少なくとも一層に含有することを特徴とする有機電界発光素子。
（４）互いに対向する陽極と陰極間に、単層もしくは複数層の有機層から構成される有機電界発光素子において、該有機層の内の単層または複数層からなる発光層に前記（１）項または（２）項に記載の上記一般式（２）で表される３，６−ジアリールカルバゾール誘導体を、少なくとも一層に含有することを特徴とする有機電界発光素子。
（５）互いに対向する陽極と陰極間に、単層もしくは複数層の有機層から構成される有機電界発光素子において、該有機層の内の単層または複数層からなる電子輸送層に前記（１）項または（２）項に記載の上記一般式（２）で表される３，６−ジアリールカルバゾール誘導体を、少なくとも一層に含有することを特徴とする有機電界発光素子。

(In the formula, R1 and R2 represent a hydrogen atom, R3 and R4 represent a hydrogen atom, and R5 represents an unsubstituted alkyl group. )

( 3 ) In an organic electroluminescent device composed of a single layer or a plurality of organic layers between an anode and a cathode facing each other, the hole transporting layer composed of a single layer or a plurality of layers (1) ) Or 3,6-diarylcarbazole derivative represented by the general formula ( 2 ) described in the item ( 2 ), at least in one layer.
( 4 ) In an organic electroluminescent device composed of a single layer or a plurality of organic layers between an anode and a cathode facing each other, the light emitting layer composed of a single layer or a plurality of layers among the organic layers is provided with (1) An organic electroluminescent device comprising the 3,6-diarylcarbazole derivative represented by the general formula ( 2 ) described in the item or (2) in at least one layer.
( 5 ) In an organic electroluminescent device composed of a single layer or a plurality of organic layers between an anode and a cathode facing each other, the above-mentioned (1 ) Or 3,6-diarylcarbazole derivative represented by the general formula ( 2 ) described in the item ( 2 ), at least in one layer.

An organic electroluminescent device containing the 3,6-diarylcarbazole derivative of the present invention in at least one layer of a single layer or a plurality of organic layers (hole transport layer, light emitting layer, electron transport layer, etc.) is novel and has a high It is extremely efficient and durable.

Hereinafter, the present invention will be described in more detail.
First, the 3,6-diarylcarbazole derivative used in the present invention will be described in more detail.
3,6-diarylcarbazole derivatives represented by the following general formula (1) used in the present invention,

（式中、Ｒ′およびＲ′′は水素原子、置換または無置換のアルキル基あるいは置換基を有してもよいアリール基を表し、Ｒ′′′は置換または無置換のアルキル基あるいは置換基を有してもよいアリール基を表し、Ａｒ_１およびＡｒ_２は置換基を有してもよいアリール基を表す。）
例えば一般式（２）で表される３，６−ジフェニルカルバゾール誘導体は下記経路（反応工程）で製造できる。

Wherein R ′ and R ″ represent a hydrogen atom, a substituted or unsubstituted alkyl group or an aryl group which may have a substituent, and R ″ ′ represents a substituted or unsubstituted alkyl group or substituent. And Ar ₁ and Ar ₂ represent an aryl group which may have a substituent.
For example, the 3,6-diphenylcarbazole derivative represented by the general formula (2) can be produced by the following route (reaction process).

第１段階の３，６−ジアリール−９Ｈ−カルバゾール誘導体は、パラジウム触媒を用いるアリールホウ素化合物と有機ハロゲン化物のクロスカップリング反応として知られているＳｕｚｕｋｉ−Ｍｉｙａｕｒａ反応により得られる。

The first stage 3,6-diaryl-9H-carbazole derivative is obtained by a Suzuki-Miyaura reaction known as a cross-coupling reaction between an aryl boron compound and an organic halide using a palladium catalyst.

  Instead of the aryl boronic acid described above, an aryl boronic acid ester synthesized from an aryl halide using bis (pinacolato) diboron which is thermally stable and can be easily handled in air may be used.

  The halogen atom in the 3,6-dihalogeno-9H-carbazole derivative is preferably an iodide or bromide from the viewpoint of reactivity.

Various catalysts such as Pd (PPh ₃ ) 4, PdCl ₂ (PPh ₃ ) ₂ , Pd (OAc) _2, and PdCl ₂ can be used as the palladium catalyst, but most commonly used is Pd (PPh ₃ ) _4. Can be used.

This reaction always requires a base, but relatively weak bases such as Na ₂ CO ₃ , NaHCO ₃ give good results. When affected by steric hindrance or the like, strong bases such as Ba (OH) ₂ and K ₃ PO ₄ are effective. Other caustic soda, caustic potash, metal alkoxide, etc., for example, potassium t-butoxide, sodium t-butoxide, lithium t-butoxide, potassium 2-methyl-2-butoxide, sodium 2-methyl-2-butoxide, sodium methoxide, sodium ethoxide , Potassium ethoxide, potassium methoxide and the like can also be used. An organic base such as triethylamine can also be used.

  Examples of the reaction solvent include alcohols such as methanol, ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane, and bis (2-methoxyethyl) ether, and ether ethers, and cyclic ethers such as dioxane and tetrahydrofuran. Benzene, toluene, xylene, dimethyl sulfoxide, N, N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and the like.

  The 3,6-diaryl-9H-carbazole derivative obtained in the first stage is derived into the 3,6-diphenylcarbazole derivative used in the present invention by the Ullmann reaction in the second stage.

  The present inventors separately proposed a 3,6-diphenylcarbazole derivative.

  Specific examples of the 3,6-diarylcarbazole derivative represented by the general formula (I) and the 3,6-diphenylcarbazole derivative represented by the general formula (2) used in the present invention thus obtained are as follows. Shown in

In the general formulas (I) and (2), when R′R ″ R ″ ′ and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ are substituted or unsubstituted alkyl groups, Things can be mentioned.
A linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, and these alkyl groups are further substituted with a fluorine atom, a cyano group, a phenyl group, a halogen atom or a linear or branched alkyl group It may contain a phenyl group. Specifically, methyl group, ethyl group, n-propyl group, i-propyl group, t-butyl group, s-butyl group, n-butyl group, i-butyl group, pentyl group, hexyl group, heptyl group, Octyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, 2-ethylhexyl group, trifluoromethyl group, 2-cyanoethyl group, benzyl group, 4-chlorobenzyl group, 4-methylbenzyl group, cyclopentyl group, A cyclohexyl group etc. are mentioned.

When R ₁ and R ₂ are substituted or unsubstituted alkoxy groups, specific examples include those in which an oxygen atom is inserted into the bonding position of the substituted or unsubstituted alkyl group to form an alkoxy group.

When R ₁ and R ₂ are halogen atoms, examples thereof include fluorine, chlorine and bromine atoms.

In the general formulas ( 1 ) and (2), R′R ″ R ″ ′ and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and Ar ₁ and Ar ₂ may have a substituent. When a good aryl group is represented, the following can be mentioned.
Phenyl group, a bicycloalkyl Feniriru group, and a non-condensed hydrocarbon aromatic polycyclic group such as data Feniriru groups which substituted or unsubstituted alkyl group described above, an alkoxy group, and a fluorine atom, a chlorine atom, a bromine atom And may have a halogen atom such as an iodine atom as a substituent.

Here, the 3,6-diarylcarbazole derivative used in the present invention is a carbocyclic aromatic group in which at least one of Ar ₁ and Ar ₂ may have a linking group in the general formula (1). More preferably, both of Ar ₁ and Ar ₂ are those of a carbocyclic aromatic group that may have a linking group. Further, the carbocyclic aromatic group is preferably one having no linking group.

  A 3,6-diarylcarbazole derivative such as the 3,6-diphenylcarbazole derivative described above can be used for any of a hole transport layer, a light emitting layer, and an electron transport layer. It is well known that the carbazole compound has a bipolar property. However, depending on its molecular design, the hole transport layer, the light emitting layer, and the electron transport as described above depending on the functions required as an organic electroluminescent device. Can be applied as a layer.

  Among the organic layers in the organic electroluminescent device of the present invention, a layer containing a 3,6-diarylcarbazole derivative such as the 3,6-diphenylcarbazole derivative is known together with a known thermoplastic polymer such as a spin coating method and a casting method. The film can be made thin by this method. In addition to the wet film forming method, a dry film forming method such as a vacuum deposition method or a sputtering method can be used.

  The organic layer constituting the organic electroluminescent element may be composed of a single organic layer or a plurality of layers. In the case where the organic layer is composed of a single layer, the layer may be composed of a single 3,6-diarylcarbazole derivative such as 3,6-diphenylcarbazole derivative, or in some cases, a low electron transporting property. Dispersion of molecular compounds, blends with polymer compounds, blends with other charge transporting polymers, and doping of fluorescent molecules with extremely high fluorescence quantum efficiency are also effective for achieving high efficiency.

  As the electron transporting substance, an existing material having the ability to transport electrons can be used. For example, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (Hereinafter abbreviated as BCP), 2,9-diethyl-4,7-diphenyl-1,10-phenanthroline and its derivatives, and oxadiazole derivatives that have been reported to have excellent electron transport properties, Triazole derivatives can be used.

As fluorescent molecules with extremely high fluorescence quantum efficiency, it is possible to use laser dyes that exhibit strong fluorescence in the solution state, and existing low-molecular fluorescent materials that have been used as light emitting materials in organic electroluminescent devices. is there. For example, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, Bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazolequinolated oxinoid compound, quinacridone, rubrene Etc. and their derivatives. Among the above metal complexes, 8-hydroxyquinolinol aluminum complexes (hereinafter abbreviated as Alq ₃ ) excellent in film formability or chelate metal complex compounds containing derivatives thereof are preferably used.

  Furthermore, if necessary, the organic layer can be composed of a plurality of layers. In the present invention, when a 3,6-diarylcarbazole derivative-containing layer such as the 3,6-diphenylcarbazole derivative represented by the general formulas (1) and (2) is used as a hole injecting and transporting layer, a spin is further formed on the upper portion. An electron injecting and transporting layer, a light emitting layer, and the like can be laminated by a coating method or a vacuum deposition method. In the present invention, a hole injecting and transporting layer is formed before forming a 3,6-diarylcarbazole derivative-containing layer such as the 3,6-diphenylcarbazole derivative represented by the general formulas (1) and (2). Doing so may also be effective in improving performance.

  As materials constituting the hole injecting and transporting layer, existing phthalocyanine compounds, porphyrin compounds, oxadiazoles, triazoles, triphenylamine compounds, polysilanes, etc., which have been reported to function in organic electroluminescence devices so far. It is possible to use materials. Among these, tertiary amine compounds represented by triphenylamine include N, N'-di-m-tolyl-N, N'-diphenyl-4,4'-diphenyldiamine (hereinafter abbreviated as TPD) and N, N'-di-1-naphthyl-N, N'-diphenyl-4,4'-diphenyldiamine (hereinafter abbreviated as NPD) is preferred.

  In the present invention, when a 3,6-diarylcarbazole derivative-containing layer such as the 3,6-diphenylcarbazole derivative represented by the general formulas (1) and (2) is used as an electron injecting and transporting layer, spin is further formed on the upper part. It is possible to laminate a hole injection transport layer, a light emitting layer, and the like by a coating method or a vacuum deposition method.

  In the present invention, it is also very useful to use a 3,6-diarylcarbazole derivative such as the 3,6-diphenylcarbazole derivative represented by the general formulas (1) and (2) as a host material in the light emitting layer. By combining with a phosphorescent dopant, the triplet exciton state of a 3,6-diarylcarbazole derivative such as the 3,6-diphenylcarbazole derivative can be effectively used.

The phosphorescent dopant is preferably a metal complex containing at least one metal selected from the group consisting of Ir, Ru, Pd, Pt, Os and Re having a phenylpyridine skeleton as a ligand. Specifically, tris (2-phenylpyridine) iridium (hereinafter abbreviated as Ir (ppy) ₃ ), tris (2-phenylpyridine) ruthenium, and the like are preferable.
When a 3,6-diarylcarbazole derivative such as the 3,6-diphenylcarbazole derivative of the present invention is used as a host material, a phosphorescent dopant is added to a 3,6-diarylcarbazole derivative such as a 3,6-diphenylcarbazole derivative. It is preferably 0.1 to 25% by weight.

  The film thickness of the organic layer thus formed is not particularly limited, and is usually selected in the range of 5 nm to 20 μm. More preferably, it is in the range of 5 nm to 0.2 μm. The film thickness is adjusted in consideration of the occurrence of film defects such as pinholes, optical interference within the device at the emission wavelength, and the increase in applied voltage due to the increase in film thickness.

As the anode of the organic electroluminescent device in the present invention, a metal, alloy, metal oxide or the like having a work function larger than 4 eV, preferably larger than 4.8 eV is used. Specific examples of such electrode materials include use of transparent electrodes such as gold, platinum, palladium, silver, tungsten, nickel, cobalt, ITO, CuI, SnO ₂ , and ZnO. An ITO substrate is particularly preferable. In the case of an ITO substrate, a substrate having a smooth surface is preferable, and the surface is cleaned well before use. As a cleaning method, a known method may be used, but a method in which ultraviolet irradiation in an ozone atmosphere or plasma treatment in an oxygen atmosphere is performed is preferable.

  On the other hand, a metal, an alloy or the like having a work function smaller than 4 eV is used as the cathode. Specific examples of such substances include cesium, sodium, calcium, magnesium, lithium, aluminum, samarium, and alloys thereof.

  When an organic electroluminescent device is used as a surface light emitting device, it is desirable that at least one of these electrodes is sufficiently transparent in the light emitting wavelength region of the device, and the opposite side has a sufficiently high reflectance in the light emitting wavelength region. In the case of edge emission, it is not necessary to be transparent. As the transparent electrode, ITO described above is preferable, and a transparent glass plate or plastic plate is used as the substrate.

It is effective to provide a protective layer on the surface of the device or to seal the device with a nitride film or the like in order to improve the environmental temperature and humidity and the stability of the organic electroluminescent device obtained.
When the positive electrode is connected to the anode and the negative electrode is connected to the cathode and the voltage is applied to the organic electroluminescence device of the present invention thus obtained, EL emission can be observed.

  In the organic electroluminescent device, Joule heat is generated by energization, and the heat causes recrystallization of the organic layer, progress of aggregation, and diffusion of low molecular weight materials, all of which lower the durability of the device. In the organic electroluminescence device of the present invention, by using a 3,6-diarylcarbazole derivative such as a 3,6-diphenylcarbazole derivative in the organic layer, it is possible to suppress device deterioration due to crystallization or aggregation or device deterioration due to diffusion, An element having high efficiency and good durability can be obtained.

  The present invention will be described more specifically with reference to the following examples. However, the present invention is not limited to these examples.

Production Example 1
Take 20.0 g of 3,6-dibromocarbazole, 20.6 g of 4-methoxyphenylboronic acid and 2.23 g of tetrakis (triphenylphosphine) palladium in 60 ml of ethanol and 250 ml of toluene, and add 120 ml of 22% aqueous solution of sodium carbonate to this. The mixture was heated to reflux under a nitrogen atmosphere for 5.5 hours. After removing insoluble matter using a filter aid during heating, the organic layer was separated and the solvent was distilled off under reduced pressure. After washing with water and drying, 20.2 g of a light brown powder was obtained. This was recrystallized from a mixed solvent of toluene / ethanol to obtain 13.5 g of colorless needle-like 3,6-bis (4-methoxyphenyl) carbazole.
Melting point 213.0-214.0 ° C
Elemental analysis value (%) Measured value / calculated value C: 82.69 / 82.30 H: 5.61 / 5.58 N: 3.70 / 3.69
Infrared absorption spectrum (KBr tablet method)
NH stretching vibration 3426 cm ⁻¹ COC stretching vibration 1235, 1035 cm ⁻¹

Production Example 2
13.4 g of 3,6-bis (4-methoxyphenyl) carbazole, 40 ml of iodobenzene, 19.3 g of potassium carbonate and 1.0 g of copper powder were heated to reflux for 3 hours under a nitrogen atmosphere. After cooling to 100 ° C., toluene was added, and insoluble matters were removed using a filter aid. The solvent was distilled off under reduced pressure, followed by washing with methanol to obtain 14.8 g of colorless needle-like 3,6-bis (4-methoxyphenyl) -9-phenylcarbazole (referred to as CBZ1). Melting point: 169.5-170.5 ° C. This was recrystallized from a mixed solvent of toluene / ethanol to obtain colorless needle crystals.
Melting point 170.0-171.0 ° C
Elemental analysis value (%) Measured value / calculated value C: 84.31 / 84.37 H: 5.44 / 5.53 N: 3.06 / 3.07

Production Examples 3-22
3,6-diphenylcarbazole used in the present invention by using the Suzuki coupling method shown in Production Example 1 and the Ullmann reaction shown in Production Example 2 (when R ₅ is an alkyl group, by a conventional alkylation method) A derivative was obtained. The results are shown in Table 1.

Example 1
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ1 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 1 and showed a maximum quantum efficiency of 6.6%.
In addition, as shown in FIG. 2, a good current-voltage characteristic was exhibited, and a maximum current density of 4.065 A / cm ² and a maximum light emission luminance of 122264 cd / m ² (FIG. 3) were observed at an applied voltage of 14.4 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 510 nm was observed.

Example 2
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ2 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 4 and a maximum quantum efficiency of 6.0%.
Further, as shown in FIG. 5, the current-voltage characteristics were good, and a maximum current density of 2.575 A / cm ² and a maximum light emission luminance of 131078 cd / m ² (FIG. 6) were observed at an applied voltage of 14.9 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 3
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ3 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 7 and showed a maximum quantum efficiency of 5.1%.
Further, as shown in FIG. 8, the current-voltage characteristics were good, and a maximum current density of 2.670 A / cm ² and a maximum light emission luminance of 117793 cd / m ² (FIG. 9) were observed at an applied voltage of 16.9 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 4
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ4 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 10, and showed a maximum quantum efficiency of 4.5%.
In addition, as shown in FIG. 11, a good current-voltage characteristic was exhibited, and a maximum current density of 3.715 A / cm ² and a maximum light emission luminance of 114104 cd / m ² (FIG. 12) were observed at an applied voltage of 15.2 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 510 nm was observed.

Example 5
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ5 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 13 and showed a maximum quantum efficiency of 3.1%.
Moreover, as shown in FIG. 14, it showed a favorable current-voltage characteristic, and a maximum current density of 1.408 A / cm ² and a maximum light emission luminance of 48747 cd / m ² (FIG. 15) were observed at an applied voltage of 14.3 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 509 nm was observed.

Example 6
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ6 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 16 and showed a maximum quantum efficiency of 4.8%.
Moreover, as shown in FIG. 17, it showed a favorable current-voltage characteristic, and a maximum current density of 2.115 A / cm ² and a maximum light emission luminance of 101601 cd / m ² (FIG. 18) were observed at an applied voltage of 15.2 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 508 nm was observed.

Example 7
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ7 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 19, and showed a maximum quantum efficiency of 11.2%.
Moreover, as shown in FIG. 20, it showed a favorable current-voltage characteristic, and a maximum current density of 2.640 A / cm ² and a maximum emission luminance of 132424 cd / m ² (FIG. 21) were observed at an applied voltage of 15.8 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 511 nm was observed.

Example 8
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ8 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 22 and showed a maximum quantum efficiency of 5.0%.
Moreover, as shown in FIG. 23, the current-voltage characteristic was excellent, and a maximum current density of 1.012 A / cm ² and a maximum light emission luminance of 22035 cd / m ² (FIG. 24) were observed at an applied voltage of 16.1 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 508 nm was observed.

Example 9
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ11 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 25, and showed a maximum quantum efficiency of 6.7%.
In addition, as shown in FIG. 26, good current-voltage characteristics were exhibited, and a maximum current density of 2.386 A / cm ² and a maximum light emission luminance of 127522 cd / m ² (FIG. 27) were observed at an applied voltage of 14.5 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 10
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ12 and Ir (ppy) ₃ were formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 28, and showed a maximum quantum efficiency of 9.2%.
Further, as shown in FIG. 29, a good current-voltage characteristic was exhibited, and a maximum current density of 2.605 A / cm ² and a maximum light emission luminance of 154756 cd / m ² (FIG. 30) were observed at an applied voltage of 15.5 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 509 nm was observed.

Example 11
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ13 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 31 and showed a maximum quantum efficiency of 5.5%.
Further, as shown in FIG. 32, good current-voltage characteristics were exhibited, and a maximum current density of 4.269 A / cm ² and a maximum light emission luminance of 91595 cd / m ² (FIG. 33) were observed at an applied voltage of 14.2 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 508 nm was observed.

Example 12
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ14 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 34, and showed a maximum quantum efficiency of 7.0%.
Further, as shown in FIG. 35, good current-voltage characteristics were exhibited, and a maximum current density of 4.317 A / cm ² and a maximum light emission luminance of 128782 cd / m ² (FIG. 36) were observed at an applied voltage of 14.7 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 13
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ16 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 37, and showed a maximum quantum efficiency of 7.9%.
Further, as shown in FIG. 38, good current-voltage characteristics were exhibited, and a maximum current density of 3.737 A / cm ² and a maximum light emission luminance of 142984 cd / m ² (FIG. 39) were observed at an applied voltage of 15.1 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 14
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ19 and Ir (ppy) ₃ were formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The element showed a current-quantum efficiency relationship as shown in FIG. 40, showing a maximum quantum efficiency of 0.8%.
As shown in FIG. 41, good current-voltage characteristics were exhibited, and a maximum current density of 2.594 A / cm ² and a maximum light emission luminance of 18231 cd / m ² (FIG. 42) were observed at an applied voltage of 17.3 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 510 nm was observed.

Example 15
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ20 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 43, showing a maximum quantum efficiency of 7.2%.
Further, as shown in FIG. 44, good current-voltage characteristics were exhibited, and a maximum current density of 3.384 A / cm ² and a maximum light emission luminance of 130163 cd / m ² (FIG. 45) were observed at an applied voltage of 15.4 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 16
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ21 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 46, and showed a maximum quantum efficiency of 8.0%.
Further, as shown in FIG. 47, good current-voltage characteristics were exhibited, and a maximum current density of 2.195 A / cm ² and a maximum light emission luminance of 119564 cd / m ² (FIG. 48) were observed at an applied voltage of 18.0 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 508 nm was observed.

Example 17
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ22 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 49, and showed a maximum quantum efficiency of 4.2%.
Further, as shown in FIG. 50, good current-voltage characteristics were exhibited, and a maximum current density of 2.698 A / cm ² and a maximum light emission luminance of 96058 cd / m ² (FIG. 51) were observed at an applied voltage of 17.6 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 508 nm was observed.

Example 18
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 50 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, CBZ24 and Ir (ppy) ₃ were formed as a light emitting layer to a thickness of 20 nm by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq ₃ were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 52, and showed a maximum quantum efficiency of 5.5%.
Further, as shown in FIG. 53, good current-voltage characteristics were exhibited, and a maximum current density of 3.565 A / cm ² and a maximum emission luminance of 111574 cd / m ² (FIG. 54) were observed at an applied voltage of 15.1 V. . In the emission spectrum, emission from Ir (ppy) ₃ centered at 512 nm was observed.

Example 19
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 30 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ25 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq3 were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 55, and showed a maximum quantum efficiency of 6.9%.
Moreover, as shown in FIG. 56, the favorable current-voltage characteristic was shown. In the emission spectrum, emission from Ir (ppy) ₃ centered at 515 nm was observed (FIG. 57).

Example 20
The ITO substrate having a film thickness of 110 nm was sufficiently washed with a neutral detergent, acetone and isopropanol, boiled and washed with isopropanol, then treated in a UV-ozone chamber for 12 minutes, and placed in a vacuum deposition apparatus. A TPD of 30 nm was formed as a hole transport layer under a vacuum of 1 × 10 ⁻⁴ Pa. Next, 20 nm of CBZ26 and Ir (ppy) ₃ was formed as a light emitting layer by a co-evaporation method. At this time, the concentration of Ir (ppy) ₃ was maintained at 6 wt%. Further, 10 nm of BCP and 30 nm of Alq3 were deposited as an electron transport layer. Finally, MgAg / Ag was deposited as a cathode with a film thickness of 100/10 nm through a shadow mask to complete the device.
The device showed a current-quantum efficiency relationship as shown in FIG. 55, and showed a maximum quantum efficiency of 7.3%.
Moreover, as shown in FIG. 56, the favorable current-voltage characteristic was shown. In the emission spectrum, emission from Ir (ppy) ₃ centered at 515 nm was observed (FIG. 57).

4 is a graph showing a relationship with current-quantum efficiency of the organic electroluminescent element of Example 1. 4 is a graph showing a relationship between current and voltage of the organic electroluminescent element of Example 1. 3 is a graph showing a relationship between light emission luminance and current of the organic electroluminescent element of Example 1. 6 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 2. 4 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 2. 4 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 2. 6 is a graph showing a relationship with current-quantum efficiency of the organic electroluminescent element of Example 3. 6 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 3. 6 is a graph showing the relationship between light emission luminance and current of the organic electroluminescent element of Example 3. 6 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 4. 6 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 4. 6 is a graph showing the relationship between light emission luminance and current of the organic electroluminescent element of Example 4. 6 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 5. 6 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 5. 6 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 5. 6 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 6. 6 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 6. 6 is a graph showing the relationship between light emission luminance and current of the organic electroluminescent element of Example 6. 6 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 7. 6 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 7. 10 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 7. 10 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 8. 10 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 8. 10 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 8. 10 is a graph showing a relationship with current-quantum efficiency of the organic electroluminescent element of Example 9. 10 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 9. 10 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 9. It is a graph which shows the relationship between the electric current of the organic electroluminescent element of Example 10, and quantum efficiency. It is a graph which shows the relationship with the current 1 voltage of the organic electroluminescent element of Example 10. FIG. 10 is a graph showing a relationship between light emission luminance and current of the organic electroluminescent element of Example 10. 10 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 11. 6 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 11. 10 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 11. It is a graph which shows the relationship with the current 1 quantum efficiency of the organic electroluminescent element of Example 12. It is a graph which shows the relationship with the electric current 1 voltage of the organic electroluminescent element of Example 12. FIG. It is a graph which shows the relationship between the light-emitting luminance of the organic electroluminescent element of Example 12, and an electric current. 14 is a graph showing the relationship between the current single quantum efficiency of the organic electroluminescent element of Example 13. 14 is a graph showing a relationship between current and voltage of an organic electroluminescent element of Example 13. 14 is a graph showing a relationship between light emission luminance and current of the organic electroluminescent element of Example 13. It is a graph which shows the relationship with the current 1 quantum efficiency of the organic electroluminescent element of Example 14. FIG. It is a graph which shows the relationship with the electric current 1 voltage of the organic electroluminescent element of Example 14. FIG. It is a graph which shows the relationship between the light-emitting luminance of the organic electroluminescent element of Example 14, and an electric current. It is a graph which shows the relationship with the current 1 quantum efficiency of the organic electroluminescent element of Example 15. It is a graph which shows the relationship with the current 1 voltage of the organic electroluminescent element of Example 15. It is a graph which shows the relationship between the light-emitting luminance of the organic electroluminescent element of Example 15, and an electric current. 14 is a graph showing a relationship with current-quantum efficiency of an organic electroluminescent element of Example 16. It is a graph which shows the relationship with the electric current 1 voltage of the organic electroluminescent element of Example 16. FIG. 14 is a graph showing the relationship between light emission luminance and current of the organic electroluminescent element of Example 16. 14 is a graph showing a relationship with current-quantum efficiency of an organic electroluminescent element of Example 17. It is a graph which shows the relationship with the electric current 1 voltage of the organic electroluminescent element of Example 17. FIG. 14 is a graph showing the relationship between the light emission luminance and current of the organic electroluminescent element of Example 17. 14 is a graph showing a relationship with current-quantum efficiency of an organic electroluminescent element of Example 18. It is a graph which shows the relationship with the electric current 1 voltage of the organic electroluminescent element of Example 18. FIG. 14 is a graph showing the relationship between light emission luminance and current of the organic electroluminescent element of Example 18. It is a graph which shows the relationship with the current 1 quantum efficiency of the organic electroluminescent element of Example 19 and 20. It is a graph which shows the relationship with the current 1 voltage of the organic electroluminescent element of Examples 19 and 20. FIG. It is a graph which shows the emission spectrum of the organic electroluminescent element of Examples 19 and 20.

Claims (5)

In an organic electroluminescent device composed of a single layer or a plurality of organic layers between an anode and a cathode facing each other, at least one layer contains a 3,6-diarylcarbazole derivative represented by the following general formula (2) An organic electroluminescent element characterized by comprising:

Wherein R1 and R2 represent an unsubstituted alkyl group, an unsubstituted alkoxy group or a halogen atom, R3 and R4 represent a hydrogen atom, R5 represents an unsubstituted alkyl group, an unsubstituted phenyl group. , unsubstituted alkyl phenyl group, an unsubstituted alkoxyphenyl group, or an unsubstituted biphenyl group.) Between opposing anode and a cathode with each other, in the organic electroluminescent device comprised of an organic layer of a single layer or multiple layers, a 3,6-diaryl carbazole derivative represented by the following general formula (2), containing in at least one layer An organic electroluminescent element characterized by comprising:

(In the formula, R1 and R2 represent a hydrogen atom, R3 and R4 represent a hydrogen atom, and R5 represents an unsubstituted alkyl group. ) In the organic electroluminescent element comprised of a single layer or a plurality of organic layers between an anode and a cathode facing each other, the hole transport layer composed of a single layer or a plurality of layers of the organic layer is defined in claim 1 or 2 . An organic electroluminescent device comprising a 3,6-diarylcarbazole derivative represented by the general formula (2) described in at least one layer. Between opposing anode and a cathode with each other, in the organic electroluminescent device comprised of an organic layer of a single layer or multiple layers, according to claim 1 or 2 in the light-emitting layer composed of a single layer or multiple layers of the organic layer An organic electroluminescence device comprising at least one 3,6-diarylcarbazole derivative represented by the general formula (2): 3. An organic electroluminescent device comprising a single layer or a plurality of organic layers between an anode and a cathode facing each other, wherein the electron transport layer comprising a single layer or a plurality of layers of the organic layers is defined in claim 1 or 2. An organic electroluminescent device comprising a 3,6-diarylcarbazole derivative represented by the general formula (2) described in at least one layer .

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