JP2009283373A - Organic electroluminescent element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic EL element that includes a high light emission efficiency and a longer service lifetime. <P>SOLUTION: The organic electroluminescent element includes an anode and a cathode, two or more light-emitting layers between the anode and the cathode, and an electron barrier layer sandwiched between the two light-emitting layers. The electron barrier layer shows a reversible cathodic reduction process by cyclic voltammetric measurement. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an organic electroluminescence element.

  In recent years, organic electroluminescence elements (organic EL elements) have been actively developed because they can be used for monochromatic display devices, lighting applications such as backlights, full color display devices using color filters, and the like. . In particular, when an organic EL element is used for illumination, for example, an organic EL element having high luminous efficiency that is equal to or higher than the luminous efficiency of a fluorescent lamp is required.

  Many methods for obtaining white light emission with an organic EL element have been disclosed. In these methods, there are few that obtain a white color with only one kind of light emitting material, and usually two or three kinds of light emitting materials are caused to emit light simultaneously in one organic EL element. When two kinds of light emitting materials are used, a light emitting material of blue to yellow and a color complementary to yellow is selected.

  Patent Document 1 discloses an organic electroluminescence device in which an electron trap material showing a reversible cathodic reduction process in a cyclic voltammetry measurement is contained in a hole transport layer. Patent Document 2 discloses an organic electroluminescence element having a plurality of light emitting layers and having an electron barrier layer between two light emitting layers. Patent Document 3 discloses an organic electroluminescence device having a hole injection / transport layer containing an aromatic amine derivative having a nitrogen-containing heterocyclic group.

Patent Document 1 also discloses a white light-emitting organic EL element having a plurality of light-emitting layers, but does not disclose or suggest a configuration in which an electrification barrier layer is sandwiched between two light-emitting layers. Patent Document 3 discloses a blue light-emitting organic EL element, but does not disclose or suggest a configuration in which an electrification barrier layer is sandwiched between two light-emitting layers. On the other hand, as disclosed in Patent Document 2, in a white organic EL device having a plurality of light emitting layers, an electron barrier layer is provided between the light emitting layers to distribute the carrier recombination regions in the plurality of light emitting layers at a desired ratio. Can be made. However, in the case where carriers are concentrated on the electron barrier layer, the deterioration of the device proceeds, and the life of the organic EL device may not be sufficiently increased.
JP-A-2005-310741 International Publication No. 07/138906 Pamphlet International Publication No. 07/148660 Pamphlet

  An object of this invention is to provide the organic EL element with high luminous efficiency and a long lifetime.

（式中、Ｚは置換又は無置換の含窒素複素環基であり、
Ｌ_２０１は置換又は無置換の核炭素数６〜４０のアリーレン基であり、
Ａｒ_２０１及びＡｒ_２０２は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。）
４．前記式（Ｉ）で表される化合物が、下記式（ＩＩ）で表される化合物である３に記載の有機エレクトロルミネッセンス素子。

（式中、Ｃｚは置換又は無置換のカルバゾリル基であり、
Ｌ_２０３は置換又は無置換の核炭素数１０〜４０のアリーレン基であり、
Ａｒ_２１５及びＡｒ_２１６は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。）
５．前記式（Ｉ）で表される化合物が、下記式（ＩＩＩ）で表される化合物である３又は４に記載の有機エレクトロルミネッセンス素子。

（式中、Ｒ_２０６は置換基であり、
Ｌ_２０４は置換又は無置換の核炭素数１０〜４０のアリーレン基であり、
Ａｒ_２１７及びＡｒ_２１８は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。）
６．前記式（Ｉ）で表される化合物が、式（ＩＶ）で表される化合物である３〜５のいずれかに記載の有機エレクトロルミネッセンス素子。

（式中、Ｒ_２０７〜Ｒ_２０９は、それぞれ置換基であり、Ｒ_２０７とＲ_２０８は互いに連結して飽和又は不飽和の環を形成してもよく、
Ａｒ_２１９及びＡｒ_２２０は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。）
７．陽極、第１発光層、電子障壁層、第２発光層及び陰極をこの順に積層して含む１〜６のいずれかに記載の有機エレクトロルミネッセンス素子。
８．陽極、第１発光層、電子障壁層、第２発光層、第３発光層及び陰極をこの順に積層して含む１〜６のいずれかに記載の有機エレクトロルミネッセンス素子。
９．陽極、第１発光層、第１電子障壁層、第２発光層、第２電子障壁層、第３発光層及び陰極をこの順に積層して含み、
前記第１電子障壁層及び前記第２電子障壁層の少なくとも１つがサイクリックボルタンメトリー測定で可逆な陰極還元過程を示す１〜６のいずれかに記載の有機エレクトロルミネッセンス素子。 The present inventor increases the luminous efficiency of the EL element by sandwiching an electron barrier layer between two light emitting layers constituting the organic EL element and including the specific hole transport material. The inventors have found that the lifetime can be extended and have completed the present invention.
According to the present invention, the following organic EL elements can be provided.
1. An anode and a cathode;
Two or more light-emitting layers between the anode and cathode;
An electron barrier layer sandwiched between two light emitting layers,
An organic electroluminescence device wherein the electron barrier layer exhibits a reversible cathodic reduction process by cyclic voltammetry measurement.
2. An anode and a cathode;
Two or more light-emitting layers between the anode and cathode;
An electron barrier layer sandwiched between two light emitting layers,
In cyclic voltammetry measurement with the first reduction potential value or less and the folding voltage -2.43 V or less, when the reduction current is Ipc and the oxidation current is Ipa, Ipc / Ipa exceeds 0.9 and 1. The organic electroluminescent element whose material which is less than 1 is a main component of the said electron barrier layer.
3. 3. The organic electroluminescence device according to 1 or 2, wherein the electron barrier layer contains a compound represented by the following formula (I).

Wherein Z is a substituted or unsubstituted nitrogen-containing heterocyclic group,
L ₂₀₁ is a substituted or unsubstituted arylene group having 6 to 40 nuclear carbon atoms,
Ar ₂₀₁ and Ar ₂₀₂ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )
4). 4. The organic electroluminescence device according to 3, wherein the compound represented by the formula (I) is a compound represented by the following formula (II).

(Wherein Cz is a substituted or unsubstituted carbazolyl group,
L ₂₀₃ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms,
Ar ₂₁₅ and Ar ₂₁₆ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )
5. 5. The organic electroluminescence device according to 3 or 4, wherein the compound represented by the formula (I) is a compound represented by the following formula (III).

Wherein R ₂₀₆ is a substituent,
L ₂₀₄ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms,
Ar ₂₁₇ and Ar ₂₁₈ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )
6). The organic electroluminescence device according to any one of 3 to 5, wherein the compound represented by the formula (I) is a compound represented by the formula (IV).

(Wherein R _{207 to} R ₂₀₉ are each a substituent, and R ₂₀₇ and R ₂₀₈ may _combine with each other to form a saturated or unsaturated ring,
Ar ₂₁₉ and Ar ₂₂₀ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )
7). The organic electroluminescence device according to any one of 1 to 6, comprising an anode, a first light emitting layer, an electron barrier layer, a second light emitting layer, and a cathode laminated in this order.
8). The organic electroluminescent device according to any one of 1 to 6, comprising an anode, a first light emitting layer, an electron barrier layer, a second light emitting layer, a third light emitting layer, and a cathode laminated in this order.
9. Including an anode, a first light emitting layer, a first electron barrier layer, a second light emitting layer, a second electron barrier layer, a third light emitting layer, and a cathode stacked in this order,
7. The organic electroluminescence device according to any one of 1 to 6, wherein at least one of the first electron barrier layer and the second electron barrier layer exhibits a reversible cathodic reduction process by cyclic voltammetry measurement.

  ADVANTAGE OF THE INVENTION According to this invention, the organic EL element with high luminous efficiency and a long lifetime can be provided.

  The organic EL device of the present invention has two or more light emitting layers between an anode and a cathode, and has an electron barrier layer sandwiched between two light emitting layers. The electron barrier layer of the organic EL device of the present invention exhibits a reversible cathodic reduction process by cyclic voltammetry measurement.

  The element of the present invention includes two or more light emitting layers, and a wide range of light emission colors can be obtained by combining light emission of various colors emitted from these light emitting layers. White light can also be obtained by combining a plurality of light emitting layers. For example, when there are two light emitting layers, white light is obtained by combining a blue to green light emitting layer and a yellow to red light emitting layer. When the light emitting layer has three layers, white light is obtained by combining the light emitting layers of three colors of blue, green, and red. The present invention is not limited to a combination of a plurality of light emitting layers that emits white light. A plurality of different emission colors may be combined, or similar emission colors may be combined.

  The electron barrier layer is a layer that restricts the injection of electrons from the light emitting layer on the cathode side that is in contact with the electron barrier layer to the light emitting layer on the anode side that is in contact with the electron barrier layer. The above light emitting layer emits light efficiently. In particular, in a white organic EL element, by providing an electron barrier layer, two or more light-emitting layers can emit light in a balanced manner, and white with better color rendering can be obtained.

  The electron barrier layer having the above function limits the injection of electrons into the anode-side light-emitting layer and transports electrons to the anode-side light-emitting layer. Compared to the hole transport layer of a normal organic EL device laminated only by a certain degree, it is exposed to excess electrons. As a result, the electron barrier layer is in a large amount of anion state, and this anion state is generally rich in reactivity and is in a material unstable state, which is a main cause of reducing the light emission lifetime of the organic EL element. It is said that.

The electron barrier layer of the organic EL device of the present invention (hereinafter sometimes simply referred to as the electron barrier layer of the present invention) exhibits a reversible cathodic reduction process by cyclic voltammetry measurement.
When the electron barrier layer exhibits a reversible cathodic reduction process, the anion is in a chemically stable state, and a reduction in the light emission lifetime of the organic EL element can be suppressed.

It can be judged from the cyclic voltammogram obtained by cyclic voltammetry that the electron barrier layer exhibits a reversible cathodic reduction process. For example, when the cathodic reduction process is repeated five times and the curves of the obtained five cyclic voltammograms appear almost overlapping, the electron barrier layer is defined as exhibiting a reversible cathodic reduction process. On the other hand, when the obtained five cyclic voltammogram curves deviate greatly without overlapping, it is defined that the electron barrier layer shows an irreversible cathodic reduction process.
When the organic EL element includes two or more electron barrier layers, at least one of the two or more electron barrier layers may exhibit a reversible cathodic reduction process by cyclic voltammetry measurement.

The electron barrier layer of the present invention preferably has an Ipc of a reduction current of Ipc and an oxidation current of Ipa in cyclic voltammetry measurement with a value equal to or less than the first reduction potential and a folding voltage of −2.43 V or less. / Ipa is preferably greater than 0.9 and less than 1.1.
It can be seen that when the main component material of the electron barrier layer satisfies the above requirements, the electron barrier layer exhibits a reversible cathodic reduction process by cyclic voltammetry measurement.

  In the present invention, the “main component” means that the electron barrier layer of the present invention contains 50% by weight or more of a material that satisfies the above requirements, and preferably the material of the electron barrier layer of the present invention is substantially from the material that satisfies the above requirements. Become.

It shows that reversibility is high when the reduction current Ipc and the oxidation current Ipa of the material which is the main component of the electron barrier layer take close values. That is, Ipc / Ipa, which is the ratio between the reduction current Ipc and the oxidation current Ipa, is a value close to 1, indicating that reversibility is high. This can also be determined from the Nicholson equation described in Non-Patent Documents 1 and 2 below.
Non-patent document 1: RSNicholson and Irving Shain, Analytical Chemistry, Vol. 36, No.4: 1964 pp706-723
Non-Patent Document 2: RSNicholson, Analytical Chemistry, Vol.38, No.10: 1966 pp1406

The Nicholson equation is shown below.
Ipc / Ipa = Ipco + 0.485 × Ipso / Ipao + 0.086
Ipco, Ipao, and Ipso in the Nicholson equation will be described with reference to FIG.
FIG. 1 is a diagram showing a cyclic voltammogram of Compound HT4 obtained in Evaluation Example 1 described later. First, when the sweep voltage is increased, the first reduction potential (Ered) is reached, and reduction starts. When further increased, the reduction proceeds, and the absolute value of the potential (potential) increases along the lower line. Current value when in the lowest end before the curve is located at the left end is iPAO, the potential at this time is E ^1. Further, the absolute value of the potential becomes large, and the current value when it is located at the left end of the curve is Ipso. Then, a current value Ipco when the absolute value is small curve of potential positioned at the uppermost end rises, the potential at this time is E ^2. The first reduction potential (E ^red ) of the material is determined by the following equation.
Ered = (E ¹ + E ² ) / 2
Ipc / Ipa can be calculated by inserting the values of Ipco, Ipao, and Ipso obtained from the cyclic voltammogram as described above into the Nicholson equation. It can be determined that the closer this value is to 1, the higher the reversibility.

Here, the relationship between the affinity level of the light emitting layer and the barrier layer and the ionization potential will be described.
The electron barrier layer is provided to adjust the carrier recombination region, and is provided in order to efficiently obtain light emission from each of the plurality of light emitting layers. In particular, a white element is provided in order to obtain a balanced light emission from a plurality of elements and to obtain a white color with better performance.

  In the case where the organic EL device of the present invention includes two light emitting layers, a first light emitting layer and a second light emitting layer, the first light emitting layer includes a hole transporting material as a host material, and the second light emitting layer has an electron transporting property. The material is preferably included as a host material, and the energy gap of the host material of the first light emitting layer is preferably smaller than the energy gap of the host material of the second light emitting layer.

Further, the affinity level of the electron barrier layer is 0.2 eV or more lower than the affinity level of the host material of the second light emitting layer, and the ionization potential (Ie1) of the electron barrier layer and the ionization potential (Ih1) of the host material of the first light emitting layer. ) Preferably satisfies the following relationship (1).
Ie1 <Ih1 + 0.1 (eV) (1)

More preferably, the affinity level (Afe1) of the electron barrier layer is greater than 1 eV, and is 0.2 eV or less smaller than the affinity level (Afh2) of the host material of the second light emitting layer (satisfies the following formula).
1 <Afe1 ≦ Afh2-0.2 (eV)

More preferably, the ionization potential (Ie1) of the electron barrier layer and the ionization potential (Ih1) of the host material of the first light emitting layer satisfy the following formula.
2.5 <Ie1 <Ih1 + 0.1 (eV)

More preferably, the energy gap (Egh1) of the host material of the first light emitting layer is larger than 1.5 eV, and is smaller than the energy gap (Egh2) of the host material of the second light emitting layer by 0.4 eV or more (satisfies the following formula) .
1.5 <Egh1 ≦ Egh2-0.4 (eV)

  In the organic EL element 20 of FIG. 2, the host material of the first light emitting layer 3 close to the anode 1 side is preferably a hole transporting material, and the host material of the second light emitting layer 5 close to the cathode 7 side is an electron transporting property. Material. An electron barrier layer 4 is provided between the first light emitting layer 3 and the second light emitting layer 5. By doing so, the injection of electrons into the first light emitting layer 3 and the injection of holes into the second light emitting layer 5 are performed in a well-balanced manner, and the electron blocking by the electron barrier layer 4 causes the electron barrier layer 4 and the second light emitting layer to The recombination region concentrates around the interface. For example, in the white element, when the second light emitting layer 5 is doped with a blue dopant, blue light emission can be obtained efficiently. Blue light emission is generally weak, but strong blue light emission can be obtained. Further, in the first light-emitting layer 3, the energy of blue light emitted from the second light-emitting layer 5 is changed to red in the first light-emitting layer 3 along with recombination of electrons injected through the electron barrier layer and holes from the anode side. The energy can also be transferred to obtain red light emission. Therefore, white light emission with high efficiency and excellent color balance can be obtained. As an example, a white element has been described. However, as long as the above energy relational expression is satisfied, not only a white element but also blue, green, and red light emitting elements may be used.

Here, “hole transportability” in the present invention means that the hole mobility of the layer is larger than the electron mobility in the electric field range of 10 ² to 10 ⁸ V / cm. Preferably, the hole mobility of the first light emitting layer is 10 ⁻⁵ cm ² / V · sec or more.
Further, “electron transportability” means that the electron mobility of the layer is larger than the hole mobility in the electric field range of 10 ² to 10 ⁸ V / cm. Preferably, the electron mobility of the second light emitting layer is 10 ⁻⁶ cm ² / V · sec or more. Hole or electron mobility is measured by the Time of flight method.

In addition, when both the host material of a 1st light emitting layer and a 2nd light emitting layer is an electron transport material, a recombination area | region will be biased to a 1st light emitting layer, and there exists a possibility that favorable light emission may not be obtained.
In addition, when the host materials of the first light emitting layer and the second light emitting layer are both hole transport materials, the recombination region is biased to the second light emitting layer contrary to the above, and it is difficult to obtain good light emission. . In addition, the recombination region tends to be biased particularly toward the cathode side in the second light emitting layer. For this reason, the light emission efficiency is lowered by the quenching action of the metal cathode.

  When the host material of the first light emitting layer is an electron transporting material and the host material of the second light emitting layer is a hole transporting material, electron injection into the first light emitting layer and holes into the second light emitting layer are performed. Both injections are difficult to perform, and there is a risk of a significant increase in drive voltage.

Consider a case where the organic EL device of the present invention is laminated in the order of an anode, a hole transporting blue light emitting layer, an electron transporting carrier recombination region control layer, an electron transporting red light emitting layer, and a cathode.
In this case, since the blue energy gap is large, the affinity level of the hole transporting blue light emitting layer is lowered. The affinity level of the electron transporting carrier recombination region control layer is generally high. Therefore, an electron injection barrier from the electron transporting carrier recombination region control layer to the hole transporting light emitting layer is increased, and the driving voltage of the device as a whole may be increased.
In this regard, with the above configuration, since the light emitting layer is disposed on the cathode side of the electron barrier layer, the gap of the affinity level does not become too large, and high voltage can be prevented.

  The organic EL element 20 of FIG. 2 includes an anode, a first light emitting layer, an electron barrier layer, a second light emitting layer, and a cathode stacked in this order. The first light emitting layer and the second light emitting layer each contain a host material and a dopant. Particularly in the case of a white element, white light emission can be obtained by setting the first light emitting layer 3 to red light emission and the second light emitting layer 5 to blue light emission. The reason why the second light-emitting layer 5 is doped with a blue dopant is to make blue, which is generally weak in light emission, shine well and balance as white.

In the organic EL element 20, it is preferable that the affinity level of the electron barrier layer 4 is 0.2 eV or less smaller than the affinity level of the host material of the second light emitting layer 5. Moreover, it is preferable that the ionization potential (Ie1) of the electron barrier layer 4 and the ionization potential (Ih1) of the host material of the first light emitting layer 3 satisfy the following relationship (1).
Ie1 <Ih1 + 0.1 (eV) (1)
This relationship will be described with reference to FIG. 3 showing energy levels.

  FIG. 3 shows the energy levels of the host material of the first light emitting layer 3, the electron barrier layer 4, and the host material of the second light emitting layer 5 of the organic EL element 20. In this figure, the upper side level indicates the affinity level of each layer, and the lower side indicates the ionization potential. In the energy level diagram, the lower part shows a larger value. In each layer, the difference between the ionization potential and the affinity level corresponds to the energy gap.

  In the organic EL element 20, it is preferable that the affinity level of the electron barrier layer 4 is 0.2 eV or less smaller than the affinity level of the second light emitting layer 5. That is, the affinity level of the electron barrier layer 4 in FIG. 2 is preferably 0.2 eV or more higher than the affinity level of the second light emitting layer 5 (ΔAf1 is 0.2 eV or more in FIG. 3).

  The electron barrier layer 4 is a layer that restricts the injection of electrons from the second light emitting layer 5 closer to the cathode 7 to the first light emitting layer 3 closer to the anode 1. It is provided to control the recombination amount of the hole pair and adjust the light emission amount from each light emitting layer. Considering this function, it is necessary to have an affinity level that is 0.2 eV or less smaller than the affinity level of the host material of the second light emitting layer. Preferably it has an affinity level smaller than 0.5 eV

  The relationship between the affinity level of the host material of the first light emitting layer 3 and the affinity level of the electron barrier layer 4 is not particularly limited, but from the viewpoint of driving voltage, the affinity level of the electron barrier layer 4 is preferably 0 eV or less. .

  Further, in the organic EL element 20, it is preferable that the ionization potential (Ie1) of the electron barrier layer 4 and the ionization potential (Ih1) of the host material of the first light emitting layer 3 satisfy the above (1). This is to prevent an increase in driving voltage when the electron barrier layer 4 becomes a barrier for holes, and to prevent it.

The relationship between the ionization potential (Ie1) of the electron barrier layer 4 and the ionization potential (Ih1) of the host material of the first light emitting layer 3 more preferably satisfies the following formula (1 ′).
Ie1 <Ih1-0.2 (eV) (1 ')
In the organic EL element 20, the energy gap of the host material of the first light emitting layer 3 is preferably smaller than the energy gap of the host material of the second light emitting layer 5, more preferably 0.4 eV or more. When the energy gap of the host material of the first light emitting layer 3 is larger or smaller than 0.4 eV, the difference in affinity level between the second light emitting layer 5 and the electron barrier layer 4 becomes too large. There are cases where the supply of electrons to one light-emitting layer 3 becomes too small to obtain good light emission.

Specifically, the energy gap of the host material of the first light emitting layer 3 is preferably 1.8 to 2.8 eV, and the energy gap of the host material of the second light emitting layer 5 is preferably 2.2 to 3.3 eV.
When the dopant of the first light emitting layer 3 is a red dopant and the dopant of the second light emitting layer 5 is a blue dopant, the first light emitting layer 3 emits red light, and the second light emitting layer 5 emits blue light. In addition to emitting light, balanced white light emission can be obtained by satisfying the above requirements.

The reason why the energy of the host material of the first light-emitting layer is preferably smaller than the energy of the host material of the second light-emitting layer is not clear, but is considered as follows.
Since the color in which the emission intensity is difficult to obtain is blue, exciton generation is performed mainly using this blue to emit light. Therefore, it is preferable that blue is located on the cathode side of the electron barrier layer. Then, red is arranged on the anode side of the electron barrier layer. When such an arrangement is performed, excitons are generated in the second light emitting layer (blue) which is the cathode side of the electron barrier layer, and this blue is well lit. Since the second light emitting layer has a wider energy gap than the first light emitting layer, the energy is moved to the first light emitting layer side. As a result, the red color of the second light emitting layer also shines.

（式中、Ｚは置換又は無置換の含窒素複素環基であり、
Ｌ_２０１は置換又は無置換の核炭素数６〜４０のアリーレン基であり、
Ａｒ_２０１及びＡｒ_２０２は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。） The electron barrier layer of the present invention preferably contains a compound represented by the following formula (I).

Wherein Z is a substituted or unsubstituted nitrogen-containing heterocyclic group,
L ₂₀₁ is a substituted or unsubstituted arylene group having 6 to 40 nuclear carbon atoms,
Ar ₂₀₁ and Ar ₂₀₂ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )

  In the present invention, “nuclear carbon” means a carbon atom constituting a ring such as a saturated ring, an unsaturated ring, or an aromatic ring. The “nuclear atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

In the formula (I), Z is a substituted or unsubstituted nitrogen-containing heterocyclic group.
Preferably, a nitrogen-containing complex having a skeleton such as pyrrole, imidazole, pyrazole, triazole, oxadiazole, pyridine, pyrazine, triazine, pyrimidine, carbazole, azacarbazole, diazacarbazole, indole, benzimidazole, imidazopyridine, indolizine, etc. A cyclic group is mentioned.
More preferably, it is a nitrogen-containing heterocyclic group having an imidazole skeleton, a carbazole skeleton, an indole skeleton, an indolizine skeleton, an imidazopyridine skeleton, a pyridine skeleton, a pyrimidine skeleton, or a triazine skeleton.

In the formula (I), L ₂₀₁ is a substituted or unsubstituted arylene group having 6 to 40 nuclear carbon atoms.
Preferably, phenylene group, biphenylene group, terphenylene group, quarterphenylene group, naphthylene group, anthracenylene group, phenanthrylene group, chrysenylene group, pyrenylene group, fluorenylene group, 2, -6-diphenylnaphthalene-4 ', 4''- Ene group, 2-phenylnaphthalene-2,4′-ene group, 1-phenylnaphthalene-1,4′-ene group, 2,7-diphenylfluorenylene-4 ′, 4 ″ -ene group, fluorenylene group 9,10-diphenylanthracenylene-4 ′, 4 ″ -ene group, 6,12-diphenylchrysenylene-4 ′, 4 ″ -ene group, and the like.
More preferably, biphenylene group, terphenylene group, fluorenylene group, 2-phenylnaphthalene-2,4′-ene group, 1-phenylnaphthalene-1,4′-ene group, 6,12-diphenylchrysenylene-4 ', 4''-ene group.

In Formula (I), Ar ₂₀₁ and Ar ₂₀₂ are substituted or unsubstituted aryl groups having 6 to 60 nuclear carbon atoms.
Preferably, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4- Biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3 -Yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenyl group) Nylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-ter A phenyl-4-yl group, a fluorenyl group, etc. are mentioned.

In the formula (I), examples of the substituent for Z, L ₂₀₁ , Ar _{201 to} Ar ₂₀₂ include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 carbon atom). -8, for example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having a carbon number). 2 to 20, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably carbon number) 2 to 20, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as propargyl, 3-pentynyl An amino group (preferably having 0 to 20 carbon atoms, more preferably 0 to 12 carbon atoms, and particularly preferably 0 to 6 carbon atoms. For example, amino, methylamino, dimethylamino, diethylamino, diphenylamino , Dibenzylamino, etc.), alkoxy groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as methoxy, ethoxy, butoxy and the like. And an aryloxy group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy and 2-naphthyloxy. ), An acyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, Acetyl, benzoyl, formyl, pivaloyl, etc.), alkoxycarbonyl groups (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl , Ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably having 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, particularly preferably 7 to 10 carbon atoms, such as phenyloxycarbonyl). An acyloxy group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy). Preferably 2-20 carbons, more preferably 2-16 carbons, particularly preferably carbon 2 to 10, such as acetylamino, benzoylamino and the like. ), An alkoxycarbonylamino group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino A group (preferably having 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino), a sulfonylamino group (preferably having a carbon number) 1-20, more preferably 1-16 carbon atoms, particularly preferably 1-12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc.), sulfamoyl groups (preferably 0-20 carbon atoms, More preferably, it has 0 to 16 carbon atoms, particularly preferably 0 to 12 carbon atoms. Moyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc.), carbamoyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to carbon atoms). For example, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.), alkylthio group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, methylthio, ethylthio, etc.), arylthio groups (preferably having 6-20 carbon atoms, more preferably 6-16 carbon atoms, particularly preferably 6-12 carbon atoms, such as phenylthio). ), A sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably charcoal) 1 to 16, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), sulfinyl group (preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably C1-C12, for example, methanesulfinyl, benzenesulfinyl, etc.), ureido group (preferably C1-C20, more preferably C1-C16, particularly preferably C1-C12 Yes, for example, ureido, methylureido, phenylureido, etc.), phosphoric acid amide group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, For example, diethyl phosphoric acid amide, phenyl phosphoric acid amide, etc.), hydroxy group, mercapto group, halogen atom (for example, fluorine source) Child, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms) Preferably it has 1 to 12 carbon atoms, and the hetero atom includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom. Specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxa Examples include zolyl, benzimidazolyl, benzothiazolyl, carbazolyl and the like. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl).

  These substituents may be further substituted. When there are two or more substituents, they may be the same or different. If possible, they may be linked to each other to form a ring.

（式中、Ｃｚは置換又は無置換のカルバゾリル基であり、
Ｌ_２０３は置換又は無置換の核炭素数１０〜４０のアリーレン基であり、
Ａｒ_２１５及びＡｒ_２１６は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。） The compound represented by the formula (I) is preferably a compound represented by the following formula (II).

(Wherein Cz is a substituted or unsubstituted carbazolyl group,
L ₂₀₃ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms,
Ar ₂₁₅ and Ar ₂₁₆ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )

In the formula (II), Cz is a substituted or unsubstituted carbazolyl group.
Examples of the carbazolyl group represented by Cz include 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and N-carbazolyl group. A 2-carbazolyl group, a 3-carbazolyl group, and an N-carbazolyl group are preferable.
These carbazolyl groups may have a substituent, and examples of the substituent include those similar to the substituents such as Z in the formula (I).

In the formula (II), L ₂₀₃ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms. Preferred groups as L _{203 are the same} as L _{201 in} formula (I).

In the formula (II), Ar ₂₁₅ and Ar ₂₁₆ represent a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. Preferred groups for Ar ₂₁₅ and Ar _{216 are the same} as Ar ₂₀₁ and Ar ₂₀₂ in formula (I).

（式中、Ｒ_２０６は置換基であり、
Ｌ_２０４は置換又は無置換の核炭素数１０〜４０のアリーレン基であり、
Ａｒ_２１７及びＡｒ_２１８は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。） The compound represented by the formula (I) is preferably a compound represented by the following formula (III).

Wherein R ₂₀₆ is a substituent,
L ₂₀₄ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms,
Ar ₂₁₇ and Ar ₂₁₈ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )

In the formula (III), L ₂₀₄ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms, and a preferred group is the same as L _{201 in the} formula (I).

In the formula (III), Ar ₂₁₇ and Ar ₂₁₈ represent a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. Preferred groups for Ar ₂₁₇ and Ar ₂₁₈ are the same as Ar ₂₀₁ and Ar ₂₀₂ in formula (I).

R ₂₀₆ represents a substituent. Specific examples include the same substituents as Z in formula (I). R ₂₀₆ can have 0-8. When two or more R ₂₀₆ are present, the plurality of R ₂₀₆ may be the same or different.

（式中、Ｒ_２０７〜Ｒ_２０９は、それぞれ置換基であり、Ｒ_２０７とＲ_２０８は互いに連結して飽和又は不飽和の環を形成してもよく、
Ａｒ_２１９及びＡｒ_２２０は、それぞれ置換又は無置換の核炭素数６〜６０のアリール基である。） The compound represented by the formula (I) is preferably a compound represented by the following formula (IV).

(Wherein R _{207 to} R ₂₀₉ are each a substituent, and R ₂₀₇ and R ₂₀₈ may _combine with each other to form a saturated or unsaturated ring,
Ar ₂₁₉ and Ar ₂₂₀ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )

In the formula (IV), R _{207 to} R ₂₀₉ are each a substituent, and specific examples thereof include those similar to the substituents such as Z in the formula (I).
R ₂₀₇ to R ₂₀₉ may have 0 to 8, respectively. When R _{207 to} R ₂₀₉ are each two or more, the plurality of R _{207 to} R ₂₀₉ may be the same or different.
R ₂₀₇ and R ₂₀₈ may be connected to each other to form a saturated or unsaturated ring. _Examples of the ring structure formed by R ₂₀₇ and R ₂₀₈ include the following.

The following structure is preferable.

In the formula (IV), Ar ₂₁₉ and Ar ₂₂₀ are substituted or unsubstituted aryl groups having 6 to 60 nuclear carbon atoms. Preferred groups for Ar ₂₁₉ and Ar ₂₂₀ are the same as Ar ₂₀₁ and Ar ₂₀₂ in formula (I).

In the aromatic amine compound having a carbazole skeleton, a compound having one carbazole group is preferable. Specific examples of the aromatic amine compound that can be used in the present invention are shown below.

（式中、Ａ^１〜Ａ^１２は、それぞれ水素原子、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数５〜５０のアリール基、置換もしくは無置換の核炭素数６〜５０のアラルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシル基、置換もしくは無置換の核炭素数５〜５０のアリールオキシ基、置換もしくは無置換の核炭素数５〜５０のアリールアミノ基、置換もしくは無置換の炭素数１〜２０のアルキルアミノ基、置換もしくは無置換の核原子数５〜５０の複素環基、又はハロゲン原子を表す。
ｍは０〜５の整数を表す。ｍが２以上の場合、Ａ^１〜Ａ^１２は、それぞれ同一でも異なっていてもよく、互いに連結して飽和もしくは不飽和の環を形成していてもよい。また、Ａ^１とＡ^２、Ａ^３とＡ^４、Ａ^５とＡ^６、Ａ^７とＡ^８、Ａ^９とＡ^１０、Ａ^１１とＡ^１２は、それぞれ、連結して飽和もしくは不飽和の環を形成していてもよい。
但し、式（１−１）においてＡ^１〜Ａ^４の全てが水素原子である場合はなく、式（１−２）においてＡ^５〜Ａ^８の全てが水素原子である場合はなく、式（１−３）においてＡ^９及びＡ^１０が共に水素原子である場合はなく、式（１−４）においてＡ^１１及びＡ^１２が共に水素原子である場合はない。
Ｒ^１〜Ｒ^４２は、それぞれ、水素原子、置換もしくは無置換の炭素数１〜２０のアルキル基、置換もしくは無置換の核炭素数６〜２０のアリール基、置換もしくは無置換の炭素数１〜２０のアラルキル基、又は置換もしくは無置換の炭素数３〜２０のシクロアルキル基又はシアノ基を表す。
Ｘ^１〜Ｘ^３は、それぞれ、置換もしくは無置換の核炭素数６〜２０のアリーレン基を表す。） One light emitting layer of the organic EL device of the present invention preferably contains a chrysene dopant represented by any of the following formulas (1-1) to (1-4).

(Wherein A ^{1 to} A ¹² are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted nucleus; Aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, substituted or unsubstituted carbon atoms having 5 to 50 carbon atoms Aryloxy group, substituted or unsubstituted arylamino group having 5 to 50 nuclear carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms Represents a group or a halogen atom.
m represents an integer of 0 to 5. When m is 2 or more, A ^{1 to} A ¹² may be the same as or different from each other, and may be connected to each other to form a saturated or unsaturated ring. A ¹ and A ² , A ³ and A ⁴ , A ⁵ and A ⁶ , A ⁷ and A ⁸ , A ⁹ and A ¹⁰ , A ¹¹ and A ¹² are connected to each other to form a saturated or unsaturated ring. May be formed.
However, not all of A ^{1 to} A ⁴ are hydrogen atoms in formula (1-1), and all of A ^{5 to} A ⁸ are not hydrogen atoms in formula (1-2). In 1-3), A ⁹ and A ¹⁰ are not both hydrogen atoms, and in Formula (1-4), A ¹¹ and A ¹² are not both hydrogen atoms.
R ^{1 to} R ⁴² are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms, a substituted or unsubstituted carbon atom having 1 to 2 carbon atoms. 20 represents an aralkyl group, or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms or a cyano group.
X ^{1 to} X ³ each represents a substituted or unsubstituted arylene group having 6 to 20 nuclear carbon atoms. )

In formulas (1-1) to (1-4), A ^{1 to} A ¹² are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 20 carbon atoms), A substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms (preferably 5 to 20 nuclear carbon atoms), a substituted or unsubstituted aralkyl group having 6 to 50 nuclear carbon atoms (preferably 6 to 20 nuclear carbon atoms) ), A substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably, having 5 to 12 core carbon atoms) cycloalkyl group, a substituted or unsubstituted cycloalkyl group having 1 to 50 (preferably having 1 to 6 carbon atoms), An alkoxyl group, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear carbon atoms (preferably 5 to 18 nuclear carbon atoms), a substituted or unsubstituted carbon atom number 5 to 50 (preferably 5 to 5 carbon atoms) 18) arylamino group, substituted Or an unsubstituted alkylamino group having 1 to 20 carbon atoms (preferably 1 to 6 carbon atoms), a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms (preferably 5 to 20 nuclear atoms). ) Or a halogen atom.

Examples of the substituted or unsubstituted alkyl group represented by A ^{1 to} A ¹² include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, and a heptyl group. Group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α , Α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group and the like.

Examples of the substituted or unsubstituted aralkyl group of A ^{1 to} A ¹² include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromo Nyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group P-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o -Cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.

Examples of the substituted or unsubstituted aryl group of A ^{1 to} A ¹² include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a biphenyl group, 4- Examples include methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group and the like.

Examples of the substituted or unsubstituted cycloalkyl group of A ^{1 to} A ¹² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

Examples of the substituted or unsubstituted alkoxyl group of A ^{1 to} A ¹² include, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and various pentyloxy groups. Group, various hexyloxy groups and the like.

Examples of the substituted or unsubstituted aryloxy group for A ^{1 to} A ¹² include a phenoxy group, a tolyloxy group, and a naphthyloxy group.
Examples of the substituted or unsubstituted arylamino group of A ^{1 to} A ¹² include a diphenylamino group, a ditolylamino group, a dinaphthylamino group, and a naphthylphenylamino group.

Examples of the substituted or unsubstituted alkylamino group of A ^{1 to} A ¹² include a dimethylamino group, a diethylamino group, and a dihexylamino group.

The halogen atom of A ¹ to A ^12, for example, a fluorine atom, a chlorine atom, and bromine atom.

Examples of the substituted or unsubstituted heterocyclic group represented by A ^{1 to} A ¹² include imidazole, benzimidazole, pyrrole, furan, thiophene, benzothiophene, oxadiazoline, indoline, carbazole, pyridine, quinoline, isoquinoline, benzoquinone, and pyralazine. , Residues such as imidazolidine, piperidine and the like.

However, not all of A ^{1 to} A ⁴ are hydrogen atoms in formula (1-1), and all of A ^{5 to} A ⁸ are not hydrogen atoms in formula (1-2). In 1-3), A ⁹ and A ¹⁰ are not both hydrogen atoms, and in Formula (1-4), A ¹¹ and A ¹² are not both hydrogen atoms.

m represents an integer of 0 to 5, preferably 0 to 3, and more preferably 0 to 2. When m is 2 or more, A ^{1 to} A ¹² may be the same as or different from each other, and may be connected to each other to form a saturated or unsaturated ring. A ¹ and A ² , A ³ and A ⁴ , A ⁵ and A ⁶ , A ⁷ and A ⁸ , A ⁹ and A ¹⁰ , A ¹¹ and A ¹² are connected to each other to form a saturated or unsaturated ring. May be formed.

  Examples of this ring include cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane and norbornane, cycloalkanes having 4 to 12 carbon atoms such as cyclobutene, cyclopentene, cyclohexene, cycloheptene and cyclooctene, cyclo C6-C12 cycloalkadiene such as hexadiene, cycloheptadiene, cyclooctadiene, benzene, naphthalene, phenanthrene, anthracene, pyrene, chrysene, acenaphthylene, etc. aromatic ring, imidazole, pyrrole, Examples thereof include C5-C50 heterocycles such as furan, thiophene and pyridine.

R ^{1 to} R ⁴² each represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 nuclear carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms, or a cyano group.

Specific examples of the substituted or unsubstituted alkyl group, aryl group, aralkyl group, and cycloalkyl group of R ^{1 to} R ⁴² include the same groups as those described above for A ^{1 to} A ¹² .

X ^{1 to} X ³ each represents a substituted or unsubstituted arylene group having 6 to 20 nuclear carbon atoms.
Examples of the substituted or unsubstituted arylene group of X ^{1 to} X ³ include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group, and a phenylene group, a naphthylene group, and a biphenylene group are preferable. .

Examples of the substituent for A ^{1 to} A ¹² and R ^{1 to} R ¹⁰ include a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group. Substituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 nuclear carbon atoms, substituted or unsubstituted nuclear carbon number Examples thereof include an arylthio group having 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group.

  Among these, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms are preferable, an alkyl group having 1 to 6 carbon atoms, and a cyclohexane having 5 to 7 carbon atoms. Alkyl groups are more preferred, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group. Is particularly preferred.

（式中、Ａ^１〜Ａ^４及びｍは前記と同じである。
式（１−５）においては、４つのｍの少なくとも１つは１以上の整数であって、その場合のＡ^１〜Ａ^４の少なくとも１つは、置換もしくは無置換の炭素数１〜５０のアルキル基又は置換もしくは無置換の核炭素数３〜５０のシクロアルキル基であり、このアルキル基が、メチル基、エチル基、イソプロピル基、ターシャリーブチル基であると好ましい。
また、このシクロアルキル基が、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、ビシクロヘプチル基、ビシクロオクチル基、アダマンチル基であると好ましい。） The chrysene dopant used in the present invention is preferably a compound in which R ^{1 to} R ²⁰ are hydrogen in the formula (1-1) or (1-2) represented by the following formula (1-5) or (1-6) It is.

^(Wherein, A 1 to A ⁴ and m are as defined above.
In the formula (1-5), at least one of the four m is an integer of 1 or more, and at least one of A ^{1 to} A ^{4 in} that case is a substituted or unsubstituted C 1-50. It is preferably an alkyl group or a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, and this alkyl group is preferably a methyl group, an ethyl group, an isopropyl group, or a tertiary butyl group.
The cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a bicycloheptyl group, a bicyclooctyl group, or an adamantyl group. )

（式中、Ａ^５〜Ａ^８、Ｘ^１、Ｘ^２、ｍは前記と同じである。
式（１−６）においては、４つのｍの少なくとも１つは１以上の整数であって、その場合のＡ^５〜Ａ^８の少なくとも１つは、置換もしくは無置換の炭素数１〜５０のアルキル基、又は置換もしくは無置換の核炭素数３〜５０のシクロアルキル基であり、このアルキル基が、メチル基、エチル基、イソプロピル基、ターシャリーブチル基であると好ましい。また、このシクロアルキル基が、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、ビシクロヘプチル基、ビシクロオクチル基、アダマンチル基であると好ましい。）

^{(Wherein, A 5 ~A 8, X 1} , X 2, m are as defined above.
In the formula (1-6), at least one of four m is an integer of 1 or more, and at least one of A ^{5 to} A ^{8 in} that case is a substituted or unsubstituted C 1-50. It is an alkyl group or a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, and this alkyl group is preferably a methyl group, an ethyl group, an isopropyl group, or a tertiary butyl group. The cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a bicycloheptyl group, a bicyclooctyl group, or an adamantyl group. )

Specific examples of the chrysene dopant represented by any of the above formulas (1-1) to (1-6) are shown below, but are not limited to these exemplified compounds. Me represents a methyl group.

（式中、Ａ^１〜Ａ^４及びＲ^１〜Ｒ^１０は前記と同じである。ａ〜ｄは、それぞれ、０〜３の整数を表わし、０〜１であると好ましい。複数のＡ^１〜Ａ^４は同一でも異なってもよい。） The chrysene-based dopant used in the present invention is preferably a compound having m of 2 to 5 in formula (1-1) represented by the following formula (1-7).

^(Wherein, A 1 to A ⁴ and ^R 1 ^{to R 10} are as defined above .a~d are each an integer of 0 to 3, preferably a 0-1. Multiple ^A 1 ~ A ⁴ may be the same or different.)

（式中、Ａ^１〜Ａ^４及びａ〜ｄは前記と同じである。） The chrysene dopant represented by the above formula (1-7) is preferably a structure represented by the following formula (1-8) in which R ^{1 to} R ¹⁰ are hydrogen atoms.

(In the formula, A ^{1 to} A ⁴ and a to d are the same as described above.)

In formulas (1-7) and (1-8), A ^{1 to} A ⁴ are each preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and A ^{1 to} A ⁴ are More preferably, each is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

  Specific examples of the chrysene dopants represented by formulas (1-7) and (1-8) in the present invention are shown below, but are not limited to these exemplified compounds.

  Among these compounds, compounds (D-1), (D-2), (D-5), (D-6), (D-9), (D-17), (D-18), (D-20), (D-21), (D-22), (D-23), (D-25) and (D-26) are preferred.

As mentioned above, although the suitable chrysene-type dopant was demonstrated, the dopant contained in the light emitting layer of this invention is not limited to these, For example, you may use a well-known dopant.
In the organic EL device of the present invention, the light emitting layer preferably contains 0.1 to 20% by weight of dopant, and more preferably 1 to 10% by weight.

  The organic EL device of the present invention has an anode, a cathode, two or more light-emitting layers between the anode and the cathode, and an electron barrier layer sandwiched between the two light-emitting layers. Other configurations are not particularly limited as long as a reversible cathodic reduction process is shown by cyclic voltammetry measurement.

The organic EL device of the present invention has an electron barrier layer between two light emitting layers. For example, the following three configurations are preferable.
(1) An element including an anode, a first light emitting layer, an electron barrier layer, a second light emitting layer, and a cathode laminated in this order. (2) Anode, first light emitting layer, electron barrier layer, second light emitting layer, and third light emission. (3) Anode, first light-emitting layer, first electron barrier layer, second light-emitting layer, second electron barrier layer, third light-emitting layer, and cathode are stacked in this order. Including elements Hereinafter, these configurations will be described in detail.

Embodiment 1
FIG. 2 is a diagram showing the configuration of the organic EL element according to Embodiment 1 of the present invention.
The organic EL element 20 shown in FIG. 2 has a structure in which an anode 1, a hole transport layer 2, a first light emitting layer 3, an electron barrier layer 4, a second light emitting layer 5, an electron transport layer 6 and a cathode 7 are laminated. ing.
In the element 20, for example, white light emission can be obtained by making the first light emitting layer 3 emit red light and the second light emitting layer 5 emit blue light.

  In the organic EL element 20 of the present embodiment, by providing the electrification barrier layer 4, the injection of holes and electrons into the first light emitting layer 3 and the second light emitting layer 5 is performed in a balanced manner, and the color balance is achieved with high efficiency. Excellent white light emission can be obtained.

In addition, the element structure of this embodiment is not limited to FIG. 2, For example, the following structures may be sufficient.
1. 1. Anode / first light emitting layer / electron barrier layer / second light emitting layer / cathode 2. Anode / hole transport layer / first light emitting layer / electron barrier layer / second light emitting layer / cathode 3. Anode / first light emitting layer / electron barrier layer / second light emitting layer / electron transport layer / cathode 4. Anode / hole transport layer / first light emitting layer / electron barrier layer / second light emitting layer / electron transport layer / cathode 5. Anode / hole injection layer / hole transport layer / first light emitting layer / electron barrier layer / second light emitting layer / electron transport layer / cathode Anode / hole injection layer / hole transport layer / first light emitting layer / electron barrier layer / second light emitting layer / electron transport layer / electron injection layer / cathode

Among these configurations, it is preferable to have a hole transport layer.
In addition to the layers described above, other organic layers or inorganic layers can be interposed. The intervening layer is not limited as long as it can transport electrons and holes. When it is in the light extraction direction, it is preferably transparent.

Embodiment 2
FIG. 4 is a diagram showing a configuration of an organic EL element according to Embodiment 2 of the present invention.
4 includes an anode 1, a hole transport layer 2, a first light emitting layer 3, an electron barrier layer 4, a second light emitting layer 5, a third light emitting layer 8, an electron transport layer 6, and a cathode 7. It has a laminated structure. That is, it has the same configuration as that of the first embodiment except that the third light emitting layer 8 is formed.
In the element 30, for example, the first light emitting layer 3 is made red light emission, the second light emitting layer 5 is made blue light emission, and the third light emitting layer 8 is made green light emission, so that the color rendering property is further improved. White light emission can be obtained.

  As in the first embodiment, the element configuration of the present embodiment is not limited to FIG. 4. For example, a configuration in which the third light emitting layer is formed in the element configuration 1-6 illustrated in the first embodiment may be used. One electron barrier layer may be formed by stacking a plurality of electron barrier layers.

Embodiment 3
FIG. 5 is a diagram showing a configuration of an organic EL element according to Embodiment 3 of the present invention.
The organic EL element 40 shown in FIG. 5 includes an anode 1, a hole transport layer 2, a first light emitting layer 3, a first electron barrier layer 4 a, a second light emitting layer 5, a second electron barrier layer 4 b, and a third light emitting layer 8. The electron transport layer 6 and the cathode 7 are stacked. That is, the configuration is the same as that of the second embodiment except that the second electron barrier layer 4b is formed.
Thus, by forming the second electron barrier layer 4b between the second light emitting layer 5 and the third light emitting layer 8, the second light emitting layer 5 and the third light emitting layer 8 can emit light in a balanced manner. . Therefore, it becomes easy to control the light emission balance of the three light emitting layers in the device. In the element 40, for example, the first light emitting layer 3 is made red light emission, the second light emitting layer 5 is made blue light emission, and the third light emitting layer 8 is made green light emission, so that white light emission excellent in color rendering properties can be obtained. Can be obtained.

As in the first and second embodiments, the device configuration of the present embodiment is not limited to FIG. 5. For example, the third light emitting layer 8 and the second electron barrier layer 4 b are added to the device configuration 1-6 illustrated in the first embodiment. In addition, the first electron barrier layer 4a and the second electron barrier layer 4b may be formed by stacking a plurality of electron barrier layers.
Hereinafter, examples of each member that can be used in the present invention will be described.

1. Yellow to orange or red light emitting layer The yellow to orange or red light emitting layer is preferably a light emitting layer having a maximum emission wavelength of 550 to 650 nm. The light emitting layer is preferably composed of a host material and a yellow to orange or red dopant.
As the host material, a compound represented by the following formula can be used.
X- (Y) n
(Wherein X is a condensed aromatic ring group having 3 or more carbon rings,
Y is a group selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted alkyl group;
n is an integer of 1 to 6, and when n is 2 or more, Y may be the same or different. )

X is preferably naphthacene, pyrene, anthracene, perylene, chrysene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, benzofluorene, fluoranthene, benzofluoranthene, naphthylfluoranthene, dibenzofluorene, dibenzopyrene, dibenzofluorane It is a group containing one or more skeletons selected from ten and acenaphthylfluoranthene. More preferably, it contains a naphthacene skeleton or an anthracene skeleton.
Y is preferably an aryl group or diarylamino group having 12 to 60 carbon atoms, more preferably an aryl group having 12 to 20 carbon atoms or a diarylamino group having 12 to 40 carbon atoms.
n is preferably 2.

（式中、Ｑ^１０、Ｑ^２０、Ｑ^３０、Ｑ^４０、Ｑ^５０、Ｑ^６０、Ｑ^７０、Ｑ^８０、Ｑ^１１０、Ｑ^１２０、Ｑ^１３０及びＱ^１４０は、それぞれ独立に水素原子、置換もしくは無置換の炭素数１〜２０のアルキル基、置換もしくは無置換の炭素数６〜３０のアリール基、置換もしくは無置換のアミノ基、置換もしくは無置換の炭素数１〜２０のアルコキシ基、置換もしくは無置換の炭素数１〜２０のアルキルチオ基、置換もしくは無置換の炭素数６〜３０のアリーロキシ基、置換もしくは無置換の炭素数６〜３０のアリールチオ基、置換もしくは無置換の炭素数１〜２０のアルケニル基、置換もしくは無置換の炭素数７〜３０のアラルキル基、又は置換もしくは無置換の複素環基を表しす。） Preferably, the compound represented by the formula (1) is a naphthacene derivative represented by the following formula (4).

(In the formula, Q ¹⁰ , Q ²⁰ , Q ³⁰ , Q ⁴⁰ , Q ⁵⁰ , Q ⁶⁰ , Q ⁷⁰ , Q ⁸⁰ , Q ¹¹⁰ , Q ¹²⁰ , Q ^130, and Q ¹⁴⁰ are each independently a hydrogen atom, Substituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Substituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 20 carbon atoms An alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group is represented.)

In the present invention, it is preferable that at least one of Q ¹⁰ , Q ²⁰ , Q ³⁰ and Q ^{40 in} the naphthacene derivative represented by the formula (4) is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. .

（式中、Ｑ^１０、Ｑ^２１〜Ｑ^２５、Ｑ^３１〜Ｑ^３５、Ｑ^４０〜Ｑ^８０、Ｑ^１１０〜Ｑ^１４０は、それぞれ独立に水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基、置換もしくは無置換のアミノ基、置換もしくは無置換のアルコキシ基、置換もしくは無置換のアルキルチオ基、置換もしくは無置換のアリーロキシ基、置換もしくは無置換のアリールチオ基、置換もしくは無置換のアルケニル基、置換もしくは無置換のアラルキル基、又は置換もしくは無置換の複素環基を表す。） More preferably, the naphthacene derivative represented by the formula (4) is a compound represented by the following formula (5).

^{(Wherein, Q 10, Q 21 ~Q 25} , Q 31 ~Q 35, Q 40 ~Q 80, Q 110 ~Q 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Aryl group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkenyl Represents a group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.)

Two or more adjacent Q ^{21 to} Q ²⁵ and Q ^{31 to} Q ³⁵ may be bonded to each other to form a ring.
According to such a configuration, the naphthacene derivative represented by the formula (3) has a substituent in at least one of the ortho positions of the two benzene rings bonded to naphthacene.

  When a substituent is introduced at the ortho position of two benzene rings bonded to naphthacene, steric hindrance occurs between the introduced substituent and the naphthacene skeleton. Due to this steric hindrance, the introduced substituent is directed out of plane with respect to the plane of the naphthacene skeleton. And the association of the naphthacene derivatives is prevented by the substituent protruding in the out-of-plane direction.

In addition, when two or more of Q ²¹ , Q ²⁵ , Q ³¹ and Q ³⁵ are substituents, these may be the same or different. Two or more adjacent ones may be bonded to each other to form a ring.
Examples of the substituent include a substituted or unsubstituted phenyl group.
Moreover, it is preferable that two or more of ortho positions of two benzene rings bonded to naphthacene are substituted.

Specific examples of the aromatic compound represented by the general formula (4) are shown below, but the present invention is not limited to these exemplified compounds.

  As the yellow to orange or red dopant, a fluorescent compound having at least one fluoranthene skeleton or perylene skeleton can be used, and examples thereof include compounds represented by the following formulas [2] to [18].

（式〔２〕〜〔１６〕式中、Ｘ^１〜Ｘ^２０は、それぞれ独立に、水素原子、直鎖、分岐もしくは環状の炭素原子数１〜２０のアルキル基、直鎖、分岐もしくは環状の炭素原子数１〜２０のアルコキシ基、置換もしくは無置換の炭素原子数６〜３０のアリール基、置換もしくは無置換の炭素原子数６〜３０のアリールオキシ基、置換もしくは無置換の炭素原子数６〜３０のアリールアミノ基、置換もしくは無置換の炭素原子数１〜３０のアルキルアミノ基、置換もしくは無置換の炭素原子数７〜３０のアリールアルキルアミノ基又は置換もしくは無置換炭素原子数８〜３０のアルケニル基である。
隣接する置換基及びＸ^１〜Ｘ^２０は結合して環状構造を形成していてもよい。
隣接する置換基がアリール基の時は、置換基は同一であってもよい。）

(In the formulas [2] to [16], X ^{1 to} X ²⁰ are each independently a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic group. An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 6 carbon atoms -30 arylamino group, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylalkylamino group having 7 to 30 carbon atoms, or substituted or unsubstituted carbon atoms 8 to 30 Of the alkenyl group.
Adjacent substituents and X ^{1 to} X ²⁰ may be bonded to form a cyclic structure.
When adjacent substituents are aryl groups, the substituents may be the same. )

In formulas [17] and [18], X ^{21 to} X ²⁴ are each independently an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and X ²¹ X ²² and / or X ²³ and X ²⁴ may be bonded via a carbon-carbon bond or —O— or —S—.
X ^{25 to} X ³⁶ are a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon An aryl group having 6 to 30 atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon atom of 1 A substituted or unsubstituted arylalkylamino group having 7 to 30 carbon atoms or a substituted or unsubstituted alkenyl group having 8 to 30 carbon atoms, an adjacent substituent, and X ^{25 to} X ^36. May be bonded to form a cyclic structure.

It is preferable that at least one of the substituents X ^{25 to} X ³⁶ in each formula contains an amine or alkenyl group.
Preference is given to indenoperylene derivatives of the formulas [13] and [14].

（式中、Ｒ^１５〜Ｒ^２１のうち少なくとも一つは芳香環を含むかあるいは隣接置換基との間に縮合環を形成し、残りはそれぞれ独立に水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる（これらの基において、炭素数としては１〜２０とする）。
Ｘは炭素または窒素であるが、窒素の場合には上記Ｒ^２１は存在しない。
金属錯体の金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金から選ばれる少なくとも一種である。） Moreover, as a yellow-orange or red dopant, a compound having a pyromethene skeleton represented by the following formula (2) or a metal complex thereof may be used.

(In the formula, at least one of R ^{15 to} R ²¹ contains an aromatic ring or forms a condensed ring with an adjacent substituent, and the rest are independently hydrogen, an alkyl group, a cycloalkyl group, and an aralkyl group. , Alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group , A carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, a condensed ring formed between adjacent substituents and an aliphatic ring (these groups In this case, the carbon number is 1 to 20).
X is carbon or nitrogen, but in the case of nitrogen, R ²¹ does not exist.
The metal of the metal complex is at least one selected from boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum. )

  Furthermore, the compound having a pyromethene skeleton represented by the formula (2) or a metal complex thereof is preferably represented by the following formula (2-1).

（式中、Ｒ^２２〜Ｒ^２８のうち少なくとも１つは芳香環を含むかあるいは隣接置換基との間に縮合芳香環を形成し、残りはそれぞれ独立に水素原子、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン原子、ハロアルキル基、ハロアルケニル基、ハロアルキニル基、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環及び脂肪族環の中から選ばれる。
Ｒ^２９及びＲ^３０は同じでも異なってもよく、ハロゲン原子、水素原子、アルキル、アリール、複素環基から選ばれる。
Ｘは炭素又は窒素であるが、窒素の場合には上記Ｒ^２８は存在しない。）

(In the formula, at least one of R ^{22 to} R ²⁸ contains an aromatic ring or forms a condensed aromatic ring with an adjacent substituent, and the rest are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, Aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group, halogen atom, haloalkyl group, haloalkenyl group, halo Alkynyl group, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, condensed ring formed between adjacent substituents and aliphatic ring Chosen from the inside.
R ²⁹ and R ³⁰ may be the same or different and are selected from a halogen atom, a hydrogen atom, an alkyl, an aryl, and a heterocyclic group.
X is carbon or nitrogen, but in the case of nitrogen, the above R ²⁸ does not exist. )

（式中、Ｒ^１〜Ｒ^９はそれぞれ独立に、水素原子、アルキル基、アルコキシアルキル基、アルコキシ基、アルコキシアルコキシ基、アリールオキシ基、アシル基、アルコキシカルボニル基、ジアルキルアミノカルボニル基、アルキルカルボニルアミノ基、アリールカルボニルアミノ基、アリールアミノカルボニル基、アリールオキシカルボニル基、アラルキル基、炭素環式アリール基、アルケニルオキシカルボニル基、アラルキルオキシカルボニル基、アルコキシカルボニルアルコキシカルボニル基、アルキルカルボニルアルコキシカルボニル基、ジ（アルコキシアルキル）アミノカルボニル基、またはアルケニル基を表し、
Ｒ^４は水素原子、シアノ基、アルキル基、アラルキル基、炭素環式アリール基、複素環式アリール基、又はアルケニル基を表し、
Ｒ^１０及びＲ^１１はフッ素原子、アルキル基、アルコキシ基、アラルキル基、炭素環式アリール基、または複素環式アリール基を表し、
Ｒ^１０及びＲ^１１の少なくとも一方はフッ素原子あるいはアルコキシ基を表す。） The compound having a pyromethene skeleton represented by the formula (2) or a metal complex thereof is preferably represented by the following formula (2-2).

(Wherein R ^{1 to} R ⁹ are each independently a hydrogen atom, alkyl group, alkoxyalkyl group, alkoxy group, alkoxyalkoxy group, aryloxy group, acyl group, alkoxycarbonyl group, dialkylaminocarbonyl group, alkylcarbonylamino. Group, arylcarbonylamino group, arylaminocarbonyl group, aryloxycarbonyl group, aralkyl group, carbocyclic aryl group, alkenyloxycarbonyl group, aralkyloxycarbonyl group, alkoxycarbonylalkoxycarbonyl group, alkylcarbonylalkoxycarbonyl group, di ( Represents an alkoxyalkyl) aminocarbonyl group or an alkenyl group,
R ⁴ represents a hydrogen atom, a cyano group, an alkyl group, an aralkyl group, a carbocyclic aryl group, a heterocyclic aryl group, or an alkenyl group,
R ¹⁰ and R ¹¹ represent a fluorine atom, an alkyl group, an alkoxy group, an aralkyl group, a carbocyclic aryl group, or a heterocyclic aryl group,
At least one of R ¹⁰ and R ¹¹ represents a fluorine atom or an alkoxy group. )

Specific examples of the aromatic compound represented by the general formula (2) are shown below, but the present invention is not limited to these exemplified compounds.

2. Blue light emitting layer The second light emitting layer is preferably a blue light emitting layer in view of the energy gap. Preferably, the peak wavelength of blue light emission is 450 to 500 nm. The light emitting layer is preferably made of a host material and a blue dopant. Contains the above chrysene dopant as a blue dopant

（式中、Ａｒ^１１及びＡｒ^１２は、それぞれ独立に、置換もしくは無置換の核炭素数６〜２０のアリール基であり、
Ｒ^１〜Ｒ^８は、それぞれ独立に、水素原子、置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核原子数５〜５０の複素環基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核炭素数６〜５０のアリールオキシ基、置換もしくは無置換の核炭素数６〜５０のアリールチオ基、置換もしくは無置換の炭素数２〜５０のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシル基から選ばれる基である。） As the host material, a compound having a structure represented by the following formula (2) having an anthracene central skeleton is preferable.

(In the formula, Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms,
R ^{1 to} R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted group. An alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon group having 7 to 50 carbon atoms. Aralkyl group, substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted Or, it is a group selected from an unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group. )

  The anthracene derivative of the above formula (2) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected according to the configuration of the organic EL element to be applied and the required characteristics.

(Anthracene derivative (A))
In the anthracene derivative, Ar ¹¹ and Ar ¹² in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. The anthracene derivative can be classified into a case where Ar ¹¹ and Ar ¹² are the same group, and a case where they are different groups. Specific examples include anthracene derivatives represented by the following formulas (2-1) to (2-3) and anthracene derivatives in which Ar ¹¹ and Ar ¹² in the formula (2) are different groups.

In the anthracene derivative represented by the following formula (2-1), Ar ¹¹ and Ar ¹² are substituted or unsubstituted 9-phenanthrenyl groups.

（式（２−１）中、Ｒ^１１は水素原子、置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核原子数５〜５０の複素環基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核炭素数６〜５０のアリールオキシ基、置換もしくは無置換の核炭素数６〜５０のアリールチオ基、置換もしくは無置換の炭素数２〜５０のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシル基から選ばれる基であり、ａは０〜９の整数である。ａが２以上の整数の場合、複数あるＲ^１１は、２つの置換もしくは無置換のフェナントレニル基が同一であることを条件に、それぞれが同一でも異なっていてもよい。）

(In the formula (2-1), R ¹¹ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, substituted or unsubstituted. An alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon group having 7 to 50 carbon atoms. An aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, It is a group selected from a substituted or unsubstituted silyl group, carboxyl group, halogen atom, cyano group, nitro group and hydroxyl group, and a is an integer of 0 to 9. a is an integer of 2 or more. In this case, a plurality of R ¹¹ may be the same or different on condition that two substituted or unsubstituted phenanthrenyl groups are the same.

（式（２−２）中、Ｒ^１１は式（２−１）と同様であり、ｂは１〜７の整数である。ｂが２以上の整数の場合、複数あるＲ^１１は、２つの置換もしくは無置換のβ−ナフチル基が同一であることを条件に、それぞれが同一でも異なっていてもよい。） In the anthracene derivative represented by the following formula (2-2), Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted β-naphthyl groups.

(In Formula (2-2), R ¹¹ is the same as in Formula (2-1), and b is an integer of 1 to 7. When b is an integer of 2 or more, a plurality of R ¹¹ are two Each may be the same or different, provided that the substituted or unsubstituted β-naphthyl groups are the same.

（式（２−２）中、Ｒ^１１及びｂは、式（２−１）と同様である。また、ｂが２以上の整数の場合、複数あるＲ^１１は、２つの置換もしくは無置換のα−ナフチル基が同一であることを条件に、それぞれが同一でも異なっていてもよい。） In the anthracene derivative represented by the following formula (2-3), Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted α-naphthyl groups.

(In the formula (2-2), R ¹¹ and b are the same as in the formula (2-1). When b is an integer of 2 or more, a plurality of R ¹¹ are two substituted or unsubstituted. Each may be the same or different, provided that the α-naphthyl groups are the same.)

As the anthracene derivative in which Ar ¹¹ and Ar ¹² in formula (2) are different groups, Ar ¹¹ and Ar ¹² are the above-described substituted or unsubstituted 9-phenanthrenyl group, substituted or unsubstituted α-naphthyl group. And a substituted or unsubstituted β-naphthyl group.

(Anthracene derivative (B))
In the anthracene derivative, one of Ar ¹¹ and Ar ¹² in Formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. Specific examples of the anthracene derivative include anthracene derivatives represented by the following formulas (2-4) and (2-5).

（式（２−４）中、Ａｒ^６は置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数７〜５０のアラルキル基、又は置換もしくは無置換の核原子数５〜５０の複素環基である。また、Ａｒ^６は置換しているフェニレン基と共に、置換もしくは無置換のフルオレニル基又は置換もしくは無置換のジベンゾフルオレニル基を形成していてもよい。Ｒ^１１及びｂは、式（２−１）と同様である。また、ｂが２以上の整数の場合、複数あるＲ^１１は、それぞれが同一でも異なっていてもよい。） In the anthracene derivative represented by the following formula (2-4), Ar ¹¹ in the formula (2) is a substituted or unsubstituted α-naphthyl group, and Ar ¹² is a substituted or unsubstituted phenyl group. .

(In the formula (2-4), Ar ⁶ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, or a substituted or unsubstituted nuclear carbon number. A cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, and Ar ⁶ is substituted. A substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group may be formed together with the phenylene group, and R ¹¹ and b are the same as those in the formula (2-1). When is an integer of 2 or more, the plurality of R ¹¹ may be the same or different.)

（式（２−５）中、Ａｒ^６は式（２−４）と同様であり、Ｒ^１１は、式（２−２）と同様である。また、ｂは０〜７の整数であり、ｂが２以上の整数の場合、複数あるＲ^１１は、それぞれが同一でも異なっていてもよい。） In the anthracene derivative represented by the following formula (2-5), Ar ¹¹ in the formula (2) is a substituted or unsubstituted β-naphthyl group, and Ar ¹² is a substituted or unsubstituted phenyl group. .

(In Formula (2-5), Ar ⁶ is the same as Formula (2-4), R ¹¹ is the same as Formula (2-2), and b is an integer of 0 to 7, When b is an integer of 2 or more, a plurality of R ¹¹ may be the same or different.

(Anthracene derivative (C))
The anthracene derivative is represented by the following formula (2-6), specifically, any one of the following formulas (2-6-1), (2-6-2), and (2-6-3) It is preferable that it is a derivative represented.

（式（２−６）中、Ｒ^１〜Ｒ^８は式（２）と同様である。Ａｒ^５は、式（２−４）のＡｒ^６と同様で、Ａｒ^６と独立に選択される。）

(In formula (2-6), R ^{1 to} R ⁸ are the same as in formula (2). Ar ⁵ is the same as Ar ^{6 in} formula (2-4), and is independently selected from Ar ⁶ . )

（式（２−６−１）中、Ｒ^１〜Ｒ^８は式（２）と同様である。）

(In formula (2-6-1), R ^{1 to} R ⁸ are the same as in formula (2).)

（式（２−６−２）中、Ｒ^１〜Ｒ^８は式（２）と同様である。Ａｒ^５は置換もしくは無置換の核炭素数１０〜２０の縮合アリール基である。）

(In Formula (2-6-2), R ^{1 to} R ⁸ are the same as in Formula (2). Ar ⁵ is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.)

（式（２−６−３）中、Ｒ^１〜Ｒ^８は式（２）と同様である。Ａｒ^５ａ及びＡｒ^６ａはそれぞれ独立に、置換もしくは無置換の核炭素数１０〜２０の縮合アリール基である。）

(In formula (2-6-3), R ^{1 to} R ⁸ are the same as those in formula (2). Ar ^5a and Ar ^6a are each independently a substituted or unsubstituted condensed aryl having 10 to 20 nuclear carbon atoms. Group.)

Examples of the substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms of A ¹¹ , A ¹² , Ar ⁵ and Ar ⁶ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group and a 2-anthryl group. Group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl Group, 2-pyrenyl group, 4-pyrenyl group, 6-chrenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4-benzo [c] Phenanthryl group, 5-benzo [c] phenanthryl group, 6-benzo [c] phenanthryl group, 1-benzo [g] chrysenyl group, 2- Benzo [g] chrysenyl group, 3-benzo [g] chrysenyl group, 4-benzo [g] chrysenyl group, 5-benzo [g] chrysenyl group, 6-benzo [g] chrysenyl group, 7-benzo [g] chrysenyl group Group, 8-benzo [g] chrysenyl group, 9-benzo [g] chrysenyl group, 10-benzo [g] chrysenyl group, 11-benzo [g] chrysenyl group, 12-benzo [g] chrysenyl group, 13-benzo [G] chrysenyl group, 14-benzo [g] chrysenyl group, 1-triphenyl group, 2-triphenyl group, 2-fluorenyl group, 9,9-dimethylfluoren-2-yl group, benzofluorenyl group, Dibenzofluorenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, and the like. Preferred is a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms, In particular, a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.

The substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms of Ar ^5a and Ar ^6a includes a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, and a 9-anthryl group. 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group 4-pyrenyl group, 6-chrycenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4-benzo [c] phenanthryl group, 5-benzo [C] phenanthryl group, 6-benzo [c] phenanthryl group, 1-benzo [g] chrysenyl group, 2-benzo [g] Risenyl group, 3-benzo [g] chrysenyl group, 4-benzo [g] chrysenyl group, 5-benzo [g] chrysenyl group, 6-benzo [g] chrysenyl group, 7-benzo [g] chrysenyl group, 8- Benzo [g] chrysenyl group, 9-benzo [g] chrysenyl group, 10-benzo [g] chrysenyl group, 11-benzo [g] chrysenyl group, 12-benzo [g] chrysenyl group, 13-benzo [g] chrysenyl group Group, 14-benzo [g] chrysenyl group, 1-triphenyl group, 2-triphenyl group, benzofluorenyl group, dibenzofluorenyl group, and the like. In particular, a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.

Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms of R ^{1 to} R ⁸ include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2- Yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-toluene Group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4 Examples include a '-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, and the like.

Examples of the substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms of R ^{1 to} R ⁸ include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, and 3-pyridinyl group. 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuran group Nyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group, 4-quinolyl group, 5- Quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8- Isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group N-tridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group Group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline-4-yl group, 1,7-phenanthroline-5-yl group, 1,7- Phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group 1,8-phenanthroline-3-yl group, 1,8-phenanthroline-4-yl group, 1,8-phenanthroline-5-yl group, 1,8-phene group Nantrolin-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline -7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group, 2,9-phenanthroline-1-yl group, 2,9-phenanthro N-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline-6-yl group, 2,9-phenanthroline-7-yl group 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group, 2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group, 2,8-phenanthroline -4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline-6-yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-yl group, 2,7-phenanthroline-3-yl group, 2,7-phenanthroline-4-yl group 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-phenanthroline-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline- 10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl -1-Indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1- Indolyl group, 2-t-butyl 3-indolyl group, 4-t-butyl 3-indolyl group and the like can be mentioned.

Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R ^{1 to} R ⁸ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, and t-butyl. Group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl Group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl Group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloro Propyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1 , 2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo -T-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3 -Diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-silane Noethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-tri Examples thereof include a nitropropyl group.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms of the substituents R ^{1 to} R ⁸ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 1-adamantyl group. , 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R ^{1 to} R ⁸ is a group represented by —OZ, and Z is the substituted or unsubstituted carbon group having 1 to 50 carbon atoms of R ^{1 to} R ^8. Selected from the following alkyl groups:

R ¹ substituted or unsubstituted C 7 to 50 aralkyl group substituent to R ⁸ (the aryl moiety 6 to 49 carbon atoms, the alkyl moiety is 1 to 44 carbon atoms) as are benzyl group, 1-phenylethyl Group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1 -Α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthyl Isopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p Chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl Group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, Examples include o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.

Aryloxy group and arylthio group R ¹ nuclear carbon atoms, a substituted or unsubstituted to R ⁸ 6 to 50 are respectively represented by -OY and -SY, Y represents a substituted or unsubstituted wherein ^R 1 to R ⁸ Selected from aryl groups having 6 to 50 nuclear carbon atoms.

A substituted or unsubstituted number 2-50 alkoxycarbonyl group having a carbon of R ¹ to R ⁸ (the alkyl moiety is 1 to 49 carbon atoms) is represented as -COOZ, Z is substituted or unsubstituted wherein ^R 1 to R ⁸ Selected from alkyl groups having 1 to 49 carbon atoms.

Examples of the substituted silyl group of R ^{1 to} R ⁸ include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.

Examples of the halogen atom for R ^{1 to} R ⁸ include fluorine, chlorine, bromine and iodine.

Specific examples of the anthracene derivative represented by the formula (2) include derivatives represented by the following formula.

Other specific examples of the anthracene derivative represented by the formula (2) include derivatives represented by the following formula.

3. The green light emitting layer is preferably a green light emitting layer. Preferably, the peak wavelength of green light emission is 500 to 550 nm.
As the host material of the third light emitting layer, a host material of a blue light emitting layer can be used. The host material is preferably the same material as the second light emitting layer.
As the green dopant, an aromatic amine compound represented by the formula (1) can be used.

In Formula (1), A ^{1 to} A ² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms), a substituted or unsubstituted nucleus. An aryl group having 5 to 50 carbon atoms (preferably 5 to 10 nuclear carbon atoms), a substituted or unsubstituted cycloalkyl group having 3 to 20 nuclear carbon atoms (preferably 5 to 10 carbon atoms), substituted or unsubstituted A substituted alkoxy group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms), a substituted or unsubstituted aryloxy group having 5 to 50 nuclear carbon atoms (preferably 5 to 10 carbon atoms), substituted or unsubstituted An unsubstituted arylamino group having 5 to 50 nuclear carbon atoms (preferably 5 to 20 nuclear carbon atoms), a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms), Or represents a halogen atom.

Examples of the substituted or unsubstituted alkyl group represented by A ^{1 to} A ² include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, and a heptyl group. Group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α , Α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group and the like.

Examples of the substituted or unsubstituted aryl group of A ^{1 to} A ² include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a biphenyl group, 4- Examples include methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group and the like.

Examples of the substituted or unsubstituted cycloalkyl group represented by A ^{1 to} A ² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a norbornel group, and an adamantyl group.

Examples of the substituted or unsubstituted alkoxy group of A ^{1 to} A ² include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and various pentyloxys. Group, various hexyloxy groups and the like.

Examples of the substituted or unsubstituted aryloxy group for A ^{1 to} A ² include a phenoxy group, a tolyloxy group, and a naphthyloxy group.
Examples of the substituted or unsubstituted arylamino group of A ^{1 to} A ² include a diphenylamino group, a ditolylamino group, a dinaphthylamino group, and a naphthylphenylamino group.
Examples of the substituted or unsubstituted alkylamino group of A ^{1 to} A ² include a dimethylamino group, a diethylamino group, a dihexylamino group, and the like.
Examples of the halogen atom for A ^{1 to} A ² include a fluorine atom, a chlorine atom, and a bromine atom.
In Formula (1), both A ¹ and A ² are not hydrogen atoms.

In the formula (1), d and e are each an integer of 1 to 5, preferably 1 to 3. When d and e are each 2 or more, the plurality of A ¹ and A ² may be the same or different, and may be connected to each other to form a saturated or unsaturated ring. Moreover, h is an integer of 1-9, and it is preferable in it being 1-3.

R ¹¹ represents a substituted or unsubstituted secondary or tertiary alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted secondary or tertiary cycloalkyl group having 3 to 10 carbon atoms.
The secondary or tertiary alkyl groups, substituted or unsubstituted 3-10 carbon atoms R ^11, for example, isopropyl, tert- butyl group, sec- butyl group, tert- pentyl, 1-methylbutyl group, 1-methylpentyl group, 1,1′-dimethylpentyl group, 1,1′-diethylpropyl group, 1-benzyl-2-phenylethyl group, 1-methoxyethyl group, 1-phenyl-1-methylethyl group, etc. Is mentioned.
The secondary or tertiary substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms R ^11, for example, a cyclopentyl group, a cyclohexyl group, norbornel group, adamantyl group and the like.
In Formula (1), f is an integer of 1-9, and it is preferable in it being 1-3. When f is 2 or more, the plurality of R ¹¹ may be the same or different.

R ¹² represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms), a substituted or unsubstituted aryl group having 5 to 50 carbon atoms (preferably a nucleus). 5 to 10 carbon atoms), a substituted or unsubstituted cycloalkyl group having 3 to 20 nuclear carbon atoms (preferably 5 to 10 carbon atoms), a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms (preferably 1-6), a substituted or unsubstituted aryloxy group having 5-50 carbon atoms (preferably 5-10 carbon atoms), a substituted or unsubstituted arylamino group having 5-50 carbon atoms. (Preferably 5 to 20 carbon atoms), a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms), or a halogen atom.

Specific examples of the substituted or unsubstituted alkyl group, aryl group, cycloalkyl group, alkoxy group, aryloxy group, arylamino group, alkylamino group and halogen atom for R ¹² are the same as those described above for A ^{1 to} A ² . Things.

In Formula (1), g is an integer of 0-8, and it is preferable in it being 0-2.
When g is 2 or more, the plurality of R ¹² may be the same or different.
Moreover, in Formula (1), f + g + h is an integer of 2-10, and it is preferable in it being 2-6.

［式（１−１）〜（１−７）中、Ａ^１、Ａ^２、ｄ、ｅ、Ｒ^１１及びＲ^１２は、式（１）と同じである。］ As the aromatic amine compound, compounds represented by formulas (1-1) to (1-7) are more preferable.

[In the formulas (1-1) to (1-7), A ¹ , A ² , d, e, R ¹¹ and R ¹² are the same as those in the formula (1). ]

4). Other organic layers (hole injection, transport layer)
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 5.6 eV or less. As such a hole injection and transport layer, a material that transports holes to the light emitting layer with a lower electric field strength is preferable. Further, when an electric field is applied with a hole mobility of, for example, 10 ⁴ to 10 ⁶ V / cm, It is preferable if it is at least 10 ⁻⁴ cm ² / V · sec.
In the present invention, the hole injection layer and the hole transport layer may each be a plurality of layers. The compounds of the above formulas (1) and (2) used in the device configuration of the present invention may form a hole transport layer alone, or may be used by mixing with other materials.

（Ａｒ^５７〜Ａｒ^６２、Ａｒ^５１〜Ａｒ^５３、Ａｒ^５４〜Ａｒ^５６は、それぞれ置換もしくは無置換の核炭素数６〜５０の芳香族基、又は核原子数５〜５０の複素芳香族基を表し、ａ〜ｃ、ｐ〜ｒは、それぞれ０〜３の整数であり、Ａｒ^５７とＡｒ^５８、Ａｒ^５９とＡｒ^６０、Ａｒ^６１とＡｒ^６２はそれぞれ互いに連結して飽和もしくは不飽和の環を形成してもよい。） The material for forming the hole injecting and transporting layer is not particularly limited as long as it has the above-mentioned preferred properties, and conventionally used as a charge transporting material for holes in an optical transmission material, or an EL element. Any of known materials used for the hole injection layer can be selected and used. In addition to the aromatic amine derivative layer and the nitrogen-containing heterocyclic derivative layer, there may be a layer constituting the hole transport zone, and the material for forming them may be any of the known materials as described above. Can be selected and used. As the aromatic amine derivative, a compound represented by the following formula can be considered.

(Ar ^{57 to} Ar ⁶² , Ar ^{51 to} Ar ⁵³ , Ar ^{54 to} Ar ⁵⁶ are each a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms or a heteroaromatic group having 5 to 50 nuclear atoms. And a to c and p to r are each an integer of 0 to 3, Ar ⁵⁷ and Ar ⁵⁸ , Ar ⁵⁹ and Ar ⁶⁰ , Ar ⁶¹ and Ar ⁶² are connected to each other to form a saturated or unsaturated ring. It may be formed.)

（Ａｒ^７１〜Ａｒ^７４は置換もしくは無置換の核炭素数６〜５０の芳香族基、又は核原子数５〜５０の複素芳香族基を表し、Ｌ^１２は連結基であり、単結合、もしくは置換もしくは無置換の核炭素数６〜５０の芳香族基、又は核原子数５〜５０の複素芳香族基を表し、ｘは０〜５の整数であり、Ａｒ^７２とＡｒ^７３は互いに連結して飽和もしくは不飽和の環を形成してもよい。）

(Ar ^{71 to} Ar ⁷⁴ represent a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms or a heteroaromatic group having 5 to 50 nuclear atoms, L ¹² is a linking group, a single bond, or A substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms or a heteroaromatic group having 5 to 50 nuclear atoms, x is an integer of 0 to 5, and Ar ⁷² and Ar ⁷³ are linked to each other. And may form a saturated or unsaturated ring.)

  Specific examples include, for example, triazole derivatives (see US Pat. No. 3,112,197), oxadiazole derivatives (see US Pat. No. 3,189,447, etc.), imidazole derivatives (Japanese Patent Publication No. 37-16096). Polyarylalkane derivatives (US Pat. Nos. 3,615,402, 3,820,989, 3,542,544, JP-B-45-555). 51-10983, JP-A-51-93224, 55-17105, 56-4148, 55-108667, 55-156953, 56-36656 Patent Publication etc.), pyrazoline derivatives and pyrazolone derivatives (US Pat. Nos. 3,180,729 and 4,278,746) JP-A-55-88064, JP-A-55-88065, JP-A-49-105537, JP-A-55-51086, JP-A-56-80051, JP-A-56-88141, JP-A-57-45545. , 54-1112637, 55-74546, etc.), phenylenediamine derivatives (US Pat. No. 3,615,404, JP-B 51-10105, 46-3712, 47-25336, 54-119925, etc.), arylamine derivatives (US Pat. Nos. 3,567,450, 3,240,597, 3,658,520). No. 4,232,103, No. 4,175,961, No. 4,012,376, JP 49-3 702, 39-27777, JP 55-144250, 56-119132, 56-22437, West German Patent 1,110,518, etc.), amino Substituted chalcone derivatives (see US Pat. No. 3,526,501 etc.), oxazole derivatives (disclosed in US Pat. No. 3,257,203 etc.), styryl anthracene derivatives (Japanese Patent Laid-Open No. 56-46234) Fluorenone derivatives (see JP 54-110837 A), hydrazone derivatives (US Pat. No. 3,717,462, JP 54-59143 A, 55-52063). Gazette, 55-52064 gazette, 55-46760 gazette, 57-11350 gazette, 57-14749 gazette, JP No. 2-31591), stilbene derivatives (Japanese Patent Laid-Open Nos. 61-210363, 61-228451, 61-14642, 61-72255, 62-47646) 62-36674, 62-10652, 62-30255, 60-93455, 60-94462, 60-174749, 60-175052, etc. Reference), silazane derivatives (US Pat. No. 4,950,950), polysilanes (JP-A-2-204996), aniline copolymers (JP-A-2-282263), conductive polymers Examples include oligomers (particularly thiophene oligomers).

In addition to the above, the hole injection layer may contain an amine derivative represented by the following formula.

In the formula (2), L ₂ is a substituted or unsubstituted arylene group having 10 to 40 carbon atoms, preferably a biphenylene group, a terphenylene group, a quarterphenylene group, a naphthylene group, an anthracenylene group, a phenanthrylene group, or a chrysenylene. Group, pyrenylene group, fluorenylene group, 2, -6-diphenylnaphthalene-4 ′, 4 ″ -ene group, 2-phenylnaphthalene-2,4′-ene group, 1-phenylnaphthalene-1,4′-ene Group, 2,7-diphenylfluorenylene-4 ′, 4 ″ -ene group, fluorenylene group, 9,10-diphenylanthracenylene-4 ′, 4 ″ -ene group, 6,12-diphenylchryseni A lene-4 ′, 4 ″ -ene group and the like, more preferably a biphenylene group, a terphenylene group, a fluorenylene group, 2-phenylnaphthalene-2, '- ene group, 1-phenyl-naphthalene-1,4'-ene group, 6,12-diphenyl chestnut Seni lens 4', 4 '' - a ene group.

Ar _{3 to} Ar _{6 in the} formula (2) each represents a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 6 to 60 nucleus atoms. Show.
In Ar _{3 to} Ar ₆ in the formula (2), examples of the substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 60 nuclear carbon atoms include a benzene ring monocyclic group or a group consisting of 2 to 5 condensed rings. Specifically, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, and the like can be given. Examples of the aromatic heterocyclic group include a 5- or 6-membered monocyclic ring or a 2-5 condensed ring, and specific examples include a pyridyl group, a triazinyl group, a pyrazinyl group, a quinoxalinyl group, and a thienyl group.

  Examples of the substituted or unsubstituted aromatic heterocyclic group having 6 to 60 nuclear atoms include a 5- or 6-membered monocyclic ring or a 2 to 5 condensed ring, specifically, a pyridyl group and a triazinyl group. , Pyrazinyl group, quinoxalinyl group and thienyl group.

式（３）において、Ａｒ_３〜Ａｒ_６は、式（２）のＡｒ_３〜Ａｒ_６と同様である。
式（３）において、Ｒ_ａは置換基を表す。Ｒ_ａの具体例は、上述した式（１）のＺ等の置換基と同様である。
ｎは２〜４の整数を表す。好ましくは２及び３である。 The amine derivative of the formula (2) is preferably a compound represented by the following formula (3).

In the formula _(3), Ar 3 to Ar ₆ are the same as _Ar 3 to Ar ₆ in the formula (2).
In Formula (3), R _a represents _a substituent. Specific examples of R _a are the same as the above-described substituents such as Z in the formula (1).
n represents an integer of 2 to 4. Preferably 2 and 3.

The amine derivative represented by the formula (2) is more preferably a compound represented by the following formula (4) or (5).

In the formula, R _{1 to} R ₅ are substituents, and specific examples thereof are the same as R _{a in the} formula (3). R ₁ , R ₂ and R _{3 to} R ₅ may be connected to each other to form a saturated or unsaturated ring.

In the formula, Ar _{7 to} Ar ₁₄ each represent a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 6 to 60 nucleus atoms. . Specific examples of Ar _{7 to} Ar ₁₄ include the same as Ar ₁ and Ar ₂ in formula (1).

The substituents for Ar _{7 to} Ar ₁₄ and R _{1 to} R ₅ are preferably the same as the substituents for R _{1 to} R ₁₀ in formula (1) and formula (2). Moreover, the following structures are mentioned as what R < ₁ >, R < ₂ > couple | bonded together and formed the substituted or unsubstituted ring. The same applies to the case where R _{3 to} R ₅ are bonded to form a ring.

The following structure is preferable.

Furthermore, at least one of Ar _{7 to} Ar _{10 in} the formula (4) and at least one of Ar _{11 to} Ar _{14 in} the formula (5) are preferably a substituted or unsubstituted biphenyl group.

As substituted or unsubstituted biphenyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, p-terphenyl group, m-terphenyl group, o-terphenyl group, 4′-methyl-biphenyl-4 -Yl group, 4'-t-butyl-biphenyl-4-yl group, 4 '-(1-naphthyl) -biphenyl-4-yl group, 4'-(2-naphthyl) -biphenyl-4-yl group, A 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, etc. are mentioned.
Preferred are 3-biphenyl group, 4-biphenyl group, p-terphenyl group, m-terphenyl group, and 9,9-dimethyl-2-fluorenyl group.
An arylamino group may be substituted at the terminal of this substituted or unsubstituted biphenyl group.

正孔輸送層は下記式（９）で表されるフルオレン系化合物を含むことができる。

Specific examples of the amine derivatives are shown below.

The hole transport layer may contain a fluorene compound represented by the following formula (9).

In the formula, X ₁ is unsubstituted or substituted as a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. An optionally substituted N-carbazoyl group, unsubstituted or substituted, as a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms N-phenoxadiyl group which may be mono- or poly-substituted, or unsubstituted or substituted with a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or represents a mono- or multiply optionally substituted N- phenothiazyl group with an aryl group having 6 to 10 carbon atoms, X ₂ is unsubstituted, or, as a substituent, a halogen atom, charcoal As an N-carbazoyl group, unsubstituted or substituted, which may be mono- or polysubstituted by an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms , A halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an N-phenoxadiyl group optionally monosubstituted or polysubstituted by an aryl group having 6 to 10 carbon atoms, As a substituent or a substituent, N may be monosubstituted or polysubstituted with a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. -Phenothiadiyl group or -NAr ^{21 '} Ar ^22' (where Ar ^{21 '} and Ar ^22' are unsubstituted or substituted with a halogen atom, alkyl group, alkyl And represents a carbocyclic aromatic group having 6 to 20 carbon atoms or a heterocyclic aromatic group having 3 to 20 carbon atoms, which may be mono- or polysubstituted by a alkoxy group or an aryl group.

B ₁ and B ₂ may be a hydrogen atom, a linear, branched or cyclic alkyl group, unsubstituted, or monosubstituted or polysubstituted with a halogen atom, an alkyl group, an alkoxy group, or an aryl group as a substituent. Good C6-C20 carbocyclic aromatic group or C3-C20 heterocyclic aromatic group, or unsubstituted or substituted with a halogen atom, alkyl group, alkoxy group, or aryl Represents an aralkyl group which may be mono- or polysubstituted by a group, and Z ₁ and Z ₂ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or A carbocyclic ring having a total carbon number of 6 to 20, which may be unsubstituted or monosubstituted or polysubstituted by a halogen atom, an alkyl group, an alkoxy group, or an aryl group. It represents a heterocyclic aromatic group of the aromatic group or the total carbon number of 3 to 20.

In the compound represented by the formula (9), X ₁ represents a substituted or unsubstituted N-carbazoyl group, a substituted or unsubstituted N-phenoxadiyl group, or a substituted or unsubstituted N-phenothiadiyl group, Is unsubstituted or monosubstituted or polysubstituted by, for example, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. An N-carbazoyl group, an N-phenoxadiyl group or an N-phenothiadiyl group which may be substituted, more preferably unsubstituted, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms. Or an N-carbazoyl group, an N-phenoxadiyl group, which may be mono- or polysubstituted by an aryl group having 6 to 10 carbon atoms, or Is an N-phenothiadiyl group, more preferably an unsubstituted N-carbazoyl group, an unsubstituted N-phenoxadiyl group, or an unsubstituted N-phenothiadiyl group.

Specific examples of X ₁ substituted or unsubstituted N-carbazoyl group, substituted or unsubstituted N-phenoxadiyl group, or substituted or unsubstituted N-phenothiadiyl group include, for example, N-carbazoyl group, 2- Methyl-N-carbazoyl group, 3-methyl-N-carbazoyl group, 4-methyl-N-carbazoyl group, 3-n-butyl-N-carbazoyl group, 3-n-hexyl-N-carbazoyl group, 3-n -Octyl-N-carbazoyl group, 3-n-decyl-N-carbazoyl group, 3,6-dimethyl-N-carbazoyl group, 2-methoxy-N-carbazoyl group, 3-methoxy-N-carbazoyl group, 3- Ethoxy-N-carbazoyl group, 3-isopropoxy-N-carbazoyl group, 3-n-butoxy-N-carbazoyl group, 3-n-octyloxy-N-carboxy Rubazoyl group, 3-n-decyloxy-N-carbazoyl group, 3-phenyl-N-carbazoyl group, 3- (4′-methylphenyl) -N-carbazoyl group, 3-chloro-N-carbazoyl group, N-phenoxy Examples thereof include a saziyl group, an N-phenothiadiyl group, and a 2-methyl-N-phenothiadiyl group. In the compound represented by the general formula (1), X ₂ represents a substituted or unsubstituted N-carbazoyl group, a substituted or unsubstituted N-phenoxadiyl group, a substituted or unsubstituted N-phenothiadiyl group, or —NAr. ^{21 ′} Ar ^{22 ′} (wherein Ar ^{21 ′} and Ar ^{22 ′} represent a substituted or unsubstituted aryl group).

X ₂ substituted or unsubstituted N- carbazoyl group, a substituted or unsubstituted N- phenoxazyl group, specific examples of the substituted or unsubstituted N- phenothiazyl group, for example, mentioned as specific examples of X ₁ Examples thereof include a substituted or unsubstituted N-carbazoyl group, a substituted or unsubstituted N-phenoxadiyl group, and a substituted or unsubstituted N-phenothiadiyl group.

In —NAr ^{21 ′} Ar ^{22 ′} , Ar ^{21 ′} and Ar ^{22 ′} represent a substituted or unsubstituted aryl group. The aryl group represents a carbocyclic aromatic group such as a phenyl group, a naphthyl group, and an anthryl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group, and a pyridyl group. Ar ^{21 ′} and Ar ^{22 ′} are preferably unsubstituted or have a total carbon number of 6 which may be mono- or polysubstituted by, for example, a halogen atom, an alkyl group, an alkoxy group, or an aryl group as a substituent. A -20 cyclic aromatic group or a heterocyclic aromatic group having 3 to 20 carbon atoms, more preferably an unsubstituted or halogen atom, an alkyl group having 1 to 14 carbon atoms, or 1 carbon atom. A carbocyclic aromatic group having a total carbon number of 6 to 20, which may be mono- or polysubstituted by an alkoxy group of -14 or an aryl group of 6 to 10 carbon atoms, more preferably unsubstituted or , A halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, which may be monosubstituted or polysubstituted, and having 6 to 16 carbon atoms in total ring Is an aromatic group.

Specific examples of Ar ^{21 ′} and Ar ^{22 ′} include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthryl group, 9-anthryl group, 4-quinolyl group, 4-pyridyl group, 3- Pyridyl group, 2-pyridyl group, 3-furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group 2-benzoimidazolyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec -Butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 2-neopentylphenyl group 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4- (2′-ethylbutyl) phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2′- Ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4′-methylcyclohexyl) phenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl Group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl Group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4-diethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4, 5-trimethylphenyl group, 2,6-diethylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert- Butylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl-2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group,

  4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl Group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4- Isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2'-ethylbutyl) oxyphenyl group 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4- -Dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-1-naphthyl group, 4-methoxy-1-naphthyl group, 4- n-butoxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n -Hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy-2-naphthyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3 -Methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methyl Phenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl Group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-phenylphenyl group 3-phenylphenyl group, 2-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (3′-methylphenyl) phenyl group, 4- (4′-methoxyphenyl) phenyl group, 4 -(4'-n-butoxyphenyl) phenyl group, 2- (2'-methoxyphenyl) phenyl group, 4- (4'-chlorophenyl) phenyl group, 3-methyl Til-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group,

  4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-chloro-1 -Naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6- Difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 3,4-dichlorophenyl group, 3, 5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,4-dichloro- -Naphtyl group, 1,6-dichloro-2-naphthyl group, 2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 3-fluoro-2-methylphenyl group, 3-fluoro-4 -Methylphenyl group, 2-methyl-4-fluorophenyl group, 2-methyl-5-fluorophenyl group, 3-methyl-4-fluorophenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5 -Methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methyl-4-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4,6- Dimethylphenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro Oro-6-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-methoxy-5-chlorophenyl group, 3-methoxy-6-chlorophenyl group, 5-chloro- Examples include 2,4-dimethoxyphenyl group, but are not limited thereto.

In the compound represented by the formula (9), B ₁ and B _{2 each} represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, Is a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, a substituted or unsubstituted aryl group having 4 to 16 carbon atoms, or a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms. And more preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted group having 7 to 12 carbon atoms. Represents an aralkyl group. More preferably, B ₁ and B ₂ are a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a carbocyclic aromatic group having 6 to 10 carbon atoms, or a carbocyclic aralkyl having 7 to 10 carbon atoms. Represents a group.

As specific examples of the substituted or unsubstituted aryl group of B ₁ and B _2, for example, can be exemplified substituted or unsubstituted aryl groups exemplified as specific examples of Ar ₁ and Ar _2. Specific examples of the linear, branched or cyclic alkyl group for B ₁ and B ₂ include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group, n-hexyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, cyclohexyl group, n-heptyl group, Examples thereof include cyclohexylmethyl group, n-octyl group, tert-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-tetradecyl group, n-hexadecyl group and the like. However, it is not limited to these.

Specific examples of the substituted or unsubstituted aralkyl group for B ₁ and B ₂ include, for example, benzyl group, phenethyl group, α-methylbenzyl group, α, α-dimethylbenzyl group, 1-naphthylmethyl group, 2 -Naphthylmethyl group, furfuryl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 4-n- Hexylbenzyl group, 4-nonylbenzyl group, 3,4-dimethylbenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n-hexyloxy Benzyl, 4-nonyloxybenzyl, 4-fluorobenzyl, 3-fluorobenzyl, 2-chlorobenzyl, 4-c It can be exemplified aralkyl groups such as Robenjiru group, but not limited thereto.

Z ₁ and Z ₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group, preferably a hydrogen atom, halogen An atom, a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 16 carbon atoms, or a substituted or unsubstituted aryl group having 4 to 20 carbon atoms More preferably, a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, or a C 6 to 12 carbon atom. It represents a substituted or unsubstituted aryl group, and more preferably a hydrogen atom.

As specific examples of the linear, branched or cyclic alkyl groups of Z ₁ and Z ₂ , for example, the linear, branched or cyclic alkyl groups mentioned as specific examples of B ₁ and B ₂ may be exemplified. it can. Further, specific examples of the substituted or unsubstituted aryl group of Z ₁ and Z ₂ include, for example, the substituted or unsubstituted aryl groups mentioned as specific examples of Ar ^{21 ′} and Ar ^{22 ′} .

Specific examples of the halogen atom of Z ₁ and Z ₂ , linear, branched or cyclic alkoxy group include, for example, halogen atoms such as fluorine atom, chlorine atom and bromine atom, such as methoxy group, ethoxy group and n-propoxy Group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, isopentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 2-ethylbutoxy group 3,3-dimethylbutoxy group, cyclohexyloxy group, n-heptyloxy group, cyclohexylmethyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-dodecyloxy Group, alkoxy such as n-tetradecyloxy group, n-hexadecyloxy group It can be mentioned.

Specific examples of the compound represented by the above formula (9) include the following compounds (numbers 1 to 100), but the present invention is not limited thereto.
-Exemplary compounds 7- (N′-carbazoyl) -N, N-diphenyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9-methyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (3′-methylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N-phenyl-N- (4′-ethylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N'-carbazoyl) -N-phenyl-N- (4'-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N-phenyl-N- (3 ′, 4′-dimethylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (3 ′, 5′-dimethylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N, N-di (3′-methylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N'-carbazoyl) -N, N-di (4'-methylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4′-ethylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N-phenyl-N- (3′-methoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N-phenyl-N- (4′-methoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N-phenyl-N- (4′-ethoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7. 7- (N′-carbazoyl) -N-phenyl-N- (4′-n-butoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4′-methoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine

18. 7- (N′-carbazoyl) -N- (3′-methylphenyl) -N- (4 ″ -methoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine 19. 7- (N′- Carbazoyl) -N- (4′-methylphenyl) -N- (4 ″ -methoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (3′-fluorophenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-chlorophenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-phenylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (1′-naphthyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (2′-naphthyl) -9,9-dimethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N- (4′-methylphenyl) -N- (2 ″ -naphthyl) -9,9-dimethyl-9H-fluoren-2-amine 26. 7- (N′-carbazoyl) ) -N-phenyl-N- (2'-furyl) -9,9-dimethyl-9H-fluoren-2-amine 27.7- (N'-carbazoyl) -N-phenyl-N- (2'-thienyl) ) -9,9-dimethyl-9H-fluoren-2-amine 28. 7- (N′-carbazoyl) -N, N-diphenyl-4-fluoro-9,9-dimethyl-9H-fluoren-2-amine 29 7- (N′-carbazoyl) -N, N-diphenyl-3-methoxy-9,9-dimethyl-9H-fluoren-2-amine 30. 7- (N′-carbazoyl) -N, N-diphenyl- 4-Phenyl-9,9-dimethyl 9H-Fluoren-2-amine 31. 7- (3'-Methyl-N'-carbazoyl) -N, N-diphenyl-9,9-dimethyl-9H-fluoren-2-amine 32.7- (3'- Methoxy-N′-carbazoyl) -N, N-diphenyl-9,9-dimethyl-9H-fluoren-2-amine 33.7- (3′-chloro-N′-carbazoyl) -N, N-diphenyl-9 , 9-Dimethyl-9H-fluoren-2-amine 34. 2,7-di (N-carbazoyl) -9,9-dimethyl-9H-fluorene 35. 7- (N′-phenoxadiyl) -N, N -Diphenyl-9,9-dimethyl-9H-fluoren-2-amine 36. 7- (N'-phenoxadiyl) -N, N-di (4'-methylphenyl) -9,9-dimethyl-9H- Fluoren-2-amine37. 2,7-di (N-phenoxadiyl) -9,9-dimethyl-9H-fluorene 38.7- (N'-phenothiadiyl) -N, N-diphenyl-9,9-dimethyl-9H-fluorene-2 -Amine 39.7- (N'-phenothiadiyl) -N-phenyl-N- (3'-methylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 40.7- (N'-phenothiadiyl) -N-phenyl-N- (4'-methylphenyl) -9,9-dimethyl-9H-fluoren-2-amine 41.7- (N'-phenothiadiyl) -N, N-di (4'-methylphenyl) ) -9,9-dimethyl-9H-fluoren-2-amine 42. 7- (N'-phenothiadiyl) -N-phenyl-N- (4'-methoxyphenyl) -9,9-dimethyl-9H-fluorene- 2- Min 43. 7- (N′-phenothiadiyl) -N-phenyl-N- (2′-naphthyl) -9,9-dimethyl-9H-fluoren-2-amine 2,7-di (N-phenothiadiyl) -9,9-dimethyl-9H-fluorene

45. 7- (N′-carbazoyl) -N, N-diphenyl-9,9-diethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9,9-diethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4′-methylphenyl) -9,9-diethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (3′-methoxyphenyl) -9,9-diethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-4-methyl-9,9-diethyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9-isopropyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9,9-di-n-propyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9,9-di-n-propyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methoxyphenyl) -9,9-di-n-propyl-9H-fluoren-2-amine 2,7-di (N-carbazoyl) -9,9-di-n-propyl-9H-fluorene 2,7-di (N-phenoxadiyl) -9,9-di-n-propyl-9H-fluorene 7- (N′-carbazoyl) -N, N-diphenyl-9,9-di-n-butyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4′-methylphenyl) -9,9-di-n-butyl-9H-fluoren-2-amine 2,7-di (N′-carbazoyl) -9,9-di-n-butyl-9H-fluorene 7- (N′-carbazoyl) -N-phenyl-N- (4′-methoxyphenyl) -9,9-di-n-pentyl-9H-fluoren-2-amine 7- (N′-phenoxadiyl) -N-phenyl-N- (3′-methoxyphenyl) -9,9-di-n-pentyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4 ″ -methoxyphenyl) -9,9-di-n-pentyl-9H-fluoren-2-amine 62. 2,7-di (N′- Carbazoyl) -9,9-di-n-pentyl-9H-fluorene 63. 7- (N′-carbazoyl) -N, N-diphenyl-9,9-di-n-hexyl-9H-fluoren-2-amine 64. 7- (N′-carbazoyl) -N, N-di (4′-methylphenyl) -9,9-di-n-hexyl-9H-fluoren-2-amine 65.7- (N′-carbazoyl) ) -N, N-diphenyl-9-cyclohexyl-9H-fluoren-2-amine 66. 7- (N'-carbazoyl) -N, N-diphenyl-9,9-di-n-octyl-9H-fluorene- 2-Amine 67. 7- (N′-phenoxa Yl) -N, N-di (4′-methylphenyl) -9,9-di-n-octyl-9H-fluoren-2-amine 68. 7- (N′-carbazoyl) -N, N-diphenyl- 9-Methyl-9-ethyl-9H-fluoren-2-amine 69. 7- (N′-carbazoyl) -N, N-diphenyl-9-methyl-9-n-propyl-9H-fluoren-2-amine 70 7- (N′-phenothiadiyl) -N, N-diphenyl-9-methyl-9-n-propyl-9H-fluoren-2-amine 71. 7- (N′-carbazoyl) -N, N-diphenyl- 9-Ethyl-9-n-hexyl-9H-fluoren-2-amine 72.7- (N′-carbazoyl) -N, N-diphenyl-9-ethyl-9-cyclohexyl-9H-fluoren-2-amine

73. 7- (N′-carbazoyl) -N, N-diphenyl-9-benzyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9,9-di (4′-methylbenzyl) -9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9,9-di (4′-methoxybenzyl) -9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4′-methylphenyl) -9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methoxyphenyl) -9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-phenylphenyl) -9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (2′-naphthyl) -9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-phenoxadiyl) -N-phenyl-N- (4′-methylphenyl) -9,9-dibenzyl-9H-fluoren-2-amine 7- (N′-phenothiadiyl) -N, N-di (4′-methylphenyl) -9,9-dibenzyl-9H-fluoren-2-amine 2,7-di (N-carbazoyl) -9,9-dibenzyl-9H-fluorene 85. 2,7-di (N-carbazoyl) -9,9-di (4′-methylbenzyl) -9H-fluorene 86. 2- (N-carbazoyl) -7- (N′-phenothiadiyl) -9,9-dibenzyl-9H-fluorene87. 7- (N′-carbazoyl) -N, N-diphenyl-9-methyl-9-benzyl-9H-fluoren-2-amine 88. 7- (N′-phenoxadiyl) -N, N-diphenyl-9-ethyl-9-benzyl-9H-fluoren-2-amine

89. 7- (N′-carbazoyl) -N, N-diphenyl-9,9-diphenyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9,9-diphenyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-di (4′-methylphenyl) -9,9-diphenyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (3′-methylphenyl) -9,9-di (4 ″ -methylphenyl) -9H-fluoren-2-amine 7- (N′-carbazoyl) -N-phenyl-N- (3′-methylphenyl) -9,9-di (4 ″ -methoxyphenyl) -9H-fluoren-2-amine 94. 7- (N′-phenoxadiyl) -N, N-di (4′-methylphenyl) -9,9-diphenyl-9H-fluoren-2-amine 7- (N′-phenothiadiyl) -N, N-diphenyl-9,9-diphenyl-9H-fluoren-2-amine 2,7-di (N′-carbazoyl) -9,9-di (4′-methylphenyl) -9H-fluorene97. 2- (N-carbazoyl) -7- (N′-phenoxadiyl) -9,9-diphenyl-9H-fluorene 98. 2- (N-phenoxadiyl) -7- (N′-phenothiadiyl) -9,9-diphenyl-9H-fluorene99. 7- (N′-carbazoyl) -N-phenyl-N- (4′-methylphenyl) -9-methyl-9-phenyl-9H-fluoren-2-amine 7- (N′-carbazoyl) -N, N-diphenyl-9-ethyl-9-phenyl-9H-fluoren-2-amine

  As the material for the hole injection layer and the hole transport layer, the above-mentioned materials can be used, and porphyrin compounds (disclosed in JP-A-63-295695 etc.), aromatic tertiary amine compounds and Styrylamine compounds (US Pat. No. 4,127,412, JP-A-53-27033, 54-58445, 55-79450, 55-144250, 56-119132 No. 61-295558, No. 61-98353, No. 63-295695, etc.), in particular, an aromatic tertiary amine compound is preferably used.

Further, for example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl having two condensed aromatic rings described in US Pat. No. 5,061,569 in the molecule. (Hereinafter abbreviated as NPD), and 4,4 ′, 4 ″ -tris (N- (3−3) in which three triphenylamine units described in JP-A-4-308688 are linked in a starburst type. And methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA).
In addition to the above-described aromatic dimethylidin compounds shown as the material for the light emitting layer, inorganic compounds such as p-type Si and p-type SiC can also be used as the material for the hole injection layer.

  The hole injection and transport layer can be formed by thinning the above-described compound by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. The thickness of the hole injection or transport layer is not particularly limited, but is usually 5 nm to 5 μm. As long as this hole injection and transport layer contains the compound of the present invention in the hole transport zone, it may be composed of one or more of the above materials, or the hole injection, A layer in which a hole injection / transport layer made of a compound different from the transport layer is laminated may be used.

An organic semiconductor layer may be further formed. This layer is a layer that assists hole injection or electron injection into the light emitting layer, and preferably has a conductivity of 10 ⁻¹⁰ S / cm or more. As the material for the organic semiconductor layer, electroconductive dendrimers, fullerenes derivatives such as C _60, such as a conductive oligomer, arylamine-containing dendrimers such as arylamine-containing oligomers disclosed in JP-A-8-193191, Copper phthalocyanine (CuPc), CF _x , MoO ₃ or the like can be used.

(Electron injection, transport layer)
The electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and has a high electron mobility. The adhesion improving layer is a layer made of a material that has a particularly good adhesion to the cathode in the electron injection layer.
In the present invention, the electron injection layer and the electron transport layer may each be a plurality of layers.

As a material used for the electron injection and transport layer, 8-hydroxyquinoline or a metal complex of a derivative thereof is preferable. Specific examples of the metal complex of 8-hydroxyquinoline or a derivative thereof include metal chelate oxinoid compounds containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline).
For example, Alq described in the section of the light emitting material can be used as the electron injection layer.

（式中Ａｒ^８１，Ａｒ^８２，Ａｒ^８３，Ａｒ^８５，Ａｒ^８６，Ａｒ^８９はそれぞれ置換又は無置換のアリール基を示し、それぞれ互いに同一であっても異なっていてもよい。またＡｒ^８４，Ａｒ^８７，Ａｒ^８８は置換又は無置換のアリーレン基を示し、それぞれ同一であっても異なっていてもよい） On the other hand, examples of the oxadiazole derivative include electron transfer compounds represented by the following general formula.

(In the formula, Ar ⁸¹ , Ar ⁸² , Ar ⁸³ , Ar ⁸⁵ , Ar ⁸⁶ , Ar ⁸⁹ each represents a substituted or unsubstituted aryl group, which may be the same or different from each other. Ar ⁸⁴ , Ar ⁸⁷ and Ar ⁸⁸ represent a substituted or unsubstituted arylene group, which may be the same or different.

Here, examples of the aryl group include a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group. Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group. This electron transfer compound is preferably a thin film-forming compound.
Specific examples of the electron transfer compound include the following.

  Moreover, the compound represented by following formula (C)-(G) can be used as a material used for an electron injection layer and an electron carrying layer.

HAr-L ¹⁴ -Ar ²⁴ -Ar ²⁵ (C)
(In the formula, HAr is a nitrogen-containing heterocyclic ring having 3 to 40 carbon atoms that may have a substituent, and L ¹⁴ has 6 to 60 carbon atoms that may have a single bond or a substituent. An arylene group, a C3-C60 heteroarylene group which may have a substituent, or a fluorenylene group which may have a substituent, and Ar ²⁴ may have a substituent. a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, Ar ²⁵ are carbon atoms, which may have an aryl group or a substituent having 6 to 60 carbon atoms which may have a substituent A nitrogen-containing heterocyclic derivative represented by 3 to 60 heteroaryl groups).

(In the formula, X ¹¹ and Y ¹¹ are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted or unsubstituted aryl group. , A substituted or unsubstituted hetero ring or a structure in which X ¹¹ and Y ¹¹ are combined to form a saturated or unsaturated ring, and R ^{85 to} R ⁸⁸ are each independently hydrogen, halogen atom, substituted or unsubstituted Alkyl group having 1 to 6 carbon atoms, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group Alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group Xy group, aryloxycarbonyloxy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, A silacyclopentadiene derivative represented by an isocyano group, a cyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a cyano group, or a substituted or unsubstituted ring condensed when adjacent.

Wherein R ^{91 to} R ⁹⁸ and Z ² are each independently a hydrogen atom, saturated or unsaturated hydrocarbon group, aromatic group, heterocyclic group, substituted amino group, substituted boryl group, alkoxy group or aryl. X ¹² , Y ¹² and Z ¹ each independently represents a saturated or unsaturated hydrocarbon group, aromatic group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group; The substituents of ¹ and Z ² may be bonded to each other to form a condensed ring, n represents an integer of 1 to 3, and when n is 2 or more, Z ¹ may be different, provided that n 1, X ¹² , Y ¹² and R ⁹² are methyl groups, and R ⁹⁸ is a hydrogen atom or a substituted boryl group, and n is 3 and Z ₁ is not a methyl group. Borane derivative.

[Wherein, Q ¹ and Q ² each independently represent a ligand represented by the following formula (G), and L ¹⁵ represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cyclohexane. An alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, —OR ^′ (R ^′ is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or An unsubstituted aryl group, a substituted or unsubstituted heterocyclic group) or —O—Ga—Q ³ (Q ⁴ ) (Q ³ and Q ⁴ are the same as Q ¹ and Q ² ). Represents a quantifier. ]

[Wherein rings A ²⁴ and A ²⁵ are 6-membered aryl ring structures condensed with each other, which may have a substituent. ]

  This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.

Specific examples of the substituents of the rings A ²⁴ and A ²⁵ forming the ligand of the formula (G) include chlorine, bromine, iodine, halogen atoms of fluorine, methyl group, ethyl group, propyl group, butyl Group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group and other substituted or unsubstituted alkyl groups, phenyl group, naphthyl group, 3-methylphenyl Group, 3-methoxyphenyl group, 3-fluorophenyl group, 3-trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitrophenyl group and the like substituted or unsubstituted aryl group, methoxy group, n-butoxy Group, t-butoxy group, trichloromethoxy group, trifluoroethoxy group, pentafluoropropoxy group, 2,2,3,3-tetrafur Substituted or unsubstituted alkoxy groups such as lopropoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 6- (perfluoroethyl) hexyloxy group, phenoxy group, p-nitrophenoxy Group, p-t-butylphenoxy group, 3-fluorophenoxy group, pentafluorophenyl group, substituted or unsubstituted aryloxy group such as 3-trifluoromethylphenoxy group, methylthio group, ethylthio group, t-butylthio group, Substituted or unsubstituted alkylthio groups such as hexylthio group, octylthio group, trifluoromethylthio group, phenylthio group, p-nitrophenylthio group, pt-butylphenylthio group, 3-fluorophenylthio group, pentafluorophenylthio Substitution of 3-group, 3-trifluoromethylphenylthio group, etc. Alternatively, mono- or di-substituted amino such as unsubstituted arylthio group, cyano group, nitro group, amino group, methylamino group, diethylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, diphenylamino group, etc. Group, bis (acetoxymethyl) amino group, bis (acetoxyethyl) amino group, bisacetoxypropyl) amino group, bis (acetoxybutyl) amino group, and the like, hydroxyl group, siloxy group, acyl group, carbamoyl group, methylcarbamoyl Group, dimethylcarbamoyl group, ethylcarbamoyl group, diethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group, phenylcarbamoyl group, etc., substituted or unsubstituted carbamoyl group, carboxylic acid group, sulfonic acid group, imide group, cyclopenta Group, cycloalkyl group such as cyclohexyl group, phenyl group, naphthyl group, biphenylyl group, anthryl group, phenanthryl group, fluorenyl group, aryl group such as pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, Indolinyl group, quinolinyl group, acridinyl group, pyrrolidinyl group, dioxanyl group, piperidinyl group, morpholidinyl group, piperazinyl group, triatinyl group, carbazolyl group, furanyl group, thiophenyl group, oxazolyl group, oxadiazolyl group, benzoxazolyl group, Examples thereof include heterocyclic groups such as thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group, imidazolyl group, benzoimidazolyl group, and pranyl group. Moreover, the above substituents may combine to form a further 6-membered aryl ring or heterocyclic ring.

  Further, it may be a polymer compound containing the nitrogen-containing heterocyclic group or nitrogen-containing heterocyclic derivative.

  In addition to the above compounds, the electron injection layer and the electron transport layer are a phosphine oxide compound (Japanese Patent Laid-Open No. 2004-203828), a phenanthroline derivative (Japanese Patent Laid-Open No. 5-33159, Japanese Patent Laid-Open No. 7-82551, Japanese Patent Laid-Open No. 10-79297). And Japanese Patent Application Laid-Open No. 2001-267080 and Japanese Patent Application Laid-Open No. 20001-113174).

  In a preferred embodiment of the present invention, there is an element containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer. Here, the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals. At least selected from the group consisting of oxides, halides of alkaline earth metals, oxides of rare earth metals or halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, organic complexes of rare earth metals One substance can be preferably used.

  More specifically, preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV). Particularly preferred are those having a work function of 2.9 eV or less, including at least one alkaline earth metal selected from the group consisting of: Among these, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb and Cs, further preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element. Further, as a reducing dopant having a work function of 2.9 eV or less, a combination of these two or more alkali metals is also preferable. Particularly, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, A combination of Cs, Na and K is preferred. By including Cs in combination, the reducing ability can be efficiently exhibited, and by adding to the electron injection region, the emission luminance and the life of the organic EL element can be improved.

  In the present invention, an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. As a result, current leakage can be effectively prevented and the electron injection property can be improved. As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.

Specifically, preferable alkali metal chalcogenides include, for example, Li ₂ O, LiO, Na ₂ S, Na ₂ Se, and NaO, and preferable alkaline earth metal chalcogenides include, for example, CaO, BaO, SrO, and BeO. , BaS, and CaSe. Further, preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl. Examples of preferable alkaline earth metal halides include fluorides such as CaF ₂ , BaF ₂ , SrF ₂ , MgF ₂ and BeF ₂ , and halides other than fluorides.

  Further, as a semiconductor constituting the electron transport layer, an oxide containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. , Nitrides or oxynitrides, or a combination of two or more. Moreover, it is preferable that the inorganic compound which comprises an electron carrying layer is a microcrystal or an amorphous insulating thin film. If the electron transport layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.

(cathode)
As the cathode, a metal, an alloy, an electrically conductive compound having a low work function (4 eV or less), and a mixture thereof and an electrode material thereof are used. Specific examples of such an electrode material include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / silver alloy, aluminum / aluminum oxide, aluminum / lithium alloy, indium, rare earth metal, and the like.
The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
Here, when light emitted from the light emitting layer is taken out from the cathode, it is preferable that the transmittance with respect to the light emitted from the cathode is larger than 10%.
The sheet resistance as a cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 5 nm to 1 μm, preferably 5 to 200 nm.
In addition, what is necessary is just to adjust the film thickness of said material, when making a cathode into a light semi-transmissive semi-reflective electrode.

(Insulating layer)
Since the organic EL applies an electric field to the ultrathin film, pixel defects are likely to occur due to leakage or short circuit. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes.
Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, cesium fluoride, cesium carbonate, aluminum nitride, Examples include titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide.
A mixture or laminate of these may be used.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail based on an Example, this invention is not limited to a following example, unless the summary is exceeded.

The evaluation method of the organic EL element obtained by the Example and comparative example of this invention is shown below.
(1) Initial performance: The device was caused to emit light with a direct current of 10 mA / cm ² , and voltage (V) and luminous efficiency (L / J), which were applied voltages at that time, were measured.
(2) Lifetime: Initial luminance 5000 cd / ^{m 2} at a constant current drive, the time when the luminance reaches 4500 cd / ^{m 2} L90, the time when the luminance reaches 4000 cd / ^{m 2} L80, and brightness The time when reaching 2500 cd / m ² was defined as L50.

In the following evaluation examples, examples and comparative examples, the following compounds were used.

Evaluation Example 1
The cyclic voltammetry measurement specifically includes the following steps.
(I) Inserting the working electrode, the counter electrode and the reference electrode in an organic solvent in which the target compound is dissolved, applying a sweep voltage between the working electrode and the counter electrode, and increasing the voltage until the sweep voltage reaches a predetermined value, Then descend. The predetermined value at which the sweep voltage is minimized is called a folding voltage.
(Ii) The measurement result is shown as a cyclic volta mock dam by repeating the increase and decrease of the sweep voltage by a predetermined number of sweeps and measuring the change in potential and current amount.
(Iii) The folding voltage is set to a different value, the measurement is repeated, and the characteristics of the folding voltage and the potential / current are evaluated for each measurement.

In the present invention, an electrochemical analyzer (model number ALS model electrochemical analyzer Model 630B manufactured by BHS) was used as a measuring instrument.
The measurement sample uses DMF (N, N-dimethylformamide) as a solvent, dissolves the target compound at 10 ⁻³ mol / liter, and tertiary butylammonium perchlorate as a supporting electrolyte at 10 ⁻¹ mol / liter. Dissolved and prepared.

Other conditions are as follows.
Sweep speed: 100 mV / second Number of sweeps: 5 Working electrode: Glassy carbon electrode (manufactured by BHS)
Reference electrode: Ag / AgCl (3M NaCl aqueous solution)

For HT4, cyclic voltammetry measurement was performed under the above conditions.
The measurement result when the folding voltage is −2.5V is shown in FIG. 1, the measurement result when the folding voltage is −2.6V is shown in FIG. 6, and the measurement when the folding voltage is −2.7V. The results are shown in FIG. The obtained physical properties are shown in Table 1.

Evaluation example 2
Cyclic voltammetry measurement was performed in the same manner as in Evaluation Example 1 using HT1 instead of HT4.
FIG. 8 shows the measurement result when the folding voltage is −2.4V, FIG. 9 shows the measurement result when the folding voltage is −2.5V, and the measurement when the folding voltage is −2.6V. The results are shown in FIG. 10, and the measurement results when the folding voltage is −2.7 V are shown in FIG. The obtained physical properties are shown in Table 1.

Based on the results obtained in Evaluation Examples 1 and 2, FIG. 12 shows the relationship between the folding voltages of HT4 and HT1 and Ipc / Ipa.
From FIG. 12, it can be seen that HT1 of Evaluation Example 2 has Ipc / Ipa exceeding 1.1 or more when the folding voltage is −2.43V or more. This indicates that HT1 exhibits irreversibility in the cathodic reduction process, and HT1 has low reduction resistance. On the other hand, in HT4 of Evaluation Example 1, Ipc / Ipa is 1.1 or less at a folding voltage of −2.43V or more. This shows that HT4 shows reversibility in the cathodic reduction process, and HT4 has strong reduction resistance.

Example 1
A 25 mm × 75 mm × 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatic) (ITO film thickness 130 nm) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning. 30 minutes. A glass substrate with a transparent electrode line after cleaning is attached to a substrate holder of a vacuum deposition apparatus, and a B-39 film having a film thickness of 10 nm is first covered on the surface on which the transparent electrode line is formed so as to cover the transparent electrode. Was deposited. This B-39 film functions as a hole injection layer. Subsequent to the formation of the B-39 film, an HT1 film having a thickness of 25 nm was formed on the B-39 film. This HT1 film functions as a hole transport layer.

Further, following the formation of the HT1 film, RH and RD were vapor-deposited at a film thickness of 5 nm so that the RD was 0.5% by weight to form a first light emitting layer. The first light emitting layer emits red light. Next, an HT4 film having a thickness of 5 nm was formed as an electron barrier layer. BH and D-5 were vapor-deposited on the electron barrier layer so that D-5 was 7.5% by weight to form a blue light-emitting layer (second light-emitting layer) having a thickness of 10 nm. On this film, BH and GD were vapor-deposited so that GD would be 10% by weight to form a green light-emitting layer (third light-emitting layer) having a film thickness of 10 nm. An ET film having a thickness of 40 nm was formed as an electron transport layer. Thereafter, a 1.6 nm LiF film was formed as an electron injection layer. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode, thereby producing an organic EL device.
The initial performance and lifetime of the obtained organic EL element were evaluated. The results are shown in Table 2.

Comparative Example 1
An organic EL device was produced and evaluated in the same manner as in Example 1 except that HT1 was used instead of HT4 as the electron barrier layer. The results are shown in Table 2.

  As can be seen from Table 2, by using HT1 having an irreversible cathodic reduction process in Comparative Example 1, the organic EL elements of LT90 and LT80 are particularly short, and the initial luminance reduction rate is large. On the other hand, the organic EL element of Example 1 not only has a long LT50, but also has a long LT90 and LT80, so that it can be seen that the reduction rate of the initial luminance can be suppressed small.

  The organic EL device of the present invention can be used for various display devices, backlights, full-color display devices using color filters, light sources for general illumination and special illumination.

It is a figure which shows the result of the cyclic voltammetry measurement of HT4 when a folding voltage is -2.5V. It is a figure which shows the structure of the organic EL element which concerns on one Embodiment of this invention. It is a figure which shows the energy level of the host material of the 1st light emitting layer of an organic EL element, the electron barrier layer, and the host material of a 2nd light emitting layer. It is a figure which shows the structure of the organic EL element which concerns on other embodiment of this invention. It is a figure which shows the structure of the organic EL element which concerns on other embodiment of this invention. It is a figure which shows the result of the cyclic voltammetry measurement of HT4 when a folding voltage is -2.6V. It is a figure which shows the result of the cyclic voltammetry measurement of HT4 when a folding voltage is -2.7V. It is a figure which shows the result of the cyclic voltammetry measurement of HT1 when a folding voltage is -2.4V. It is a figure which shows the result of the cyclic voltammetry measurement of HT1 when a folding voltage is -2.5V. It is a figure which shows the result of the cyclic voltammetry measurement of HT1 when a folding voltage is -2.6V. It is a figure which shows the result of the cyclic voltammetry measurement of HT1 when a folding voltage is -2.7V. It is a figure which shows the relationship between the folding voltage of HT4 and HT1, and Ipc / Ipa.

Explanation of symbols

20, 30, 40 Organic EL element 1 Anode 2 Hole transport layer 3 First light emitting layer 4 Electron barrier layer 4a First electron barrier layer 4b Second electron barrier layer 5 Second light emitting layer 6 Electron transport layer 7 Cathode 8 Third Luminescent layer

Claims (9)

An anode and a cathode;
Two or more light-emitting layers between the anode and cathode;
An electron barrier layer sandwiched between two light emitting layers,
An organic electroluminescence device wherein the electron barrier layer exhibits a reversible cathodic reduction process by cyclic voltammetry measurement. An anode and a cathode;
Two or more light-emitting layers between the anode and cathode;
An electron barrier layer sandwiched between two light emitting layers,
In cyclic voltammetry measurement with the first reduction potential value or less and the folding voltage -2.43 V or less, when the reduction current is Ipc and the oxidation current is Ipa, Ipc / Ipa exceeds 0.9 and 1. The organic electroluminescent element whose material which is less than 1 is a main component of the said electron barrier layer. The organic electroluminescent device according to claim 1, wherein the electron barrier layer contains a compound represented by the following formula (I).

Wherein Z is a substituted or unsubstituted nitrogen-containing heterocyclic group,
L ₂₀₁ is a substituted or unsubstituted arylene group having 6 to 40 nuclear carbon atoms,
Ar ₂₀₁ and Ar ₂₀₂ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. ) The organic electroluminescence device according to claim 3, wherein the compound represented by the formula (I) is a compound represented by the following formula (II).

(Wherein Cz is a substituted or unsubstituted carbazolyl group,
L ₂₀₃ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms,
Ar ₂₁₅ and Ar ₂₁₆ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. ) The organic electroluminescence device according to claim 3 or 4, wherein the compound represented by the formula (I) is a compound represented by the following formula (III).

Wherein R ₂₀₆ is a substituent,
L ₂₀₄ is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms,
Ar ₂₁₇ and Ar ₂₁₈ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. ) The organic electroluminescence device according to any one of claims 3 to 5, wherein the compound represented by the formula (I) is a compound represented by the formula (IV).

(Wherein R _{207 to} R ₂₀₉ are each a substituent, and R ₂₀₇ and R ₂₀₈ may _combine with each other to form a saturated or unsaturated ring,
Ar ₂₁₉ and Ar ₂₂₀ are each a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms. )   The organic electroluminescent element according to claim 1, comprising an anode, a first light emitting layer, an electron barrier layer, a second light emitting layer, and a cathode laminated in this order.   The organic electroluminescence device according to claim 1, comprising an anode, a first light emitting layer, an electron barrier layer, a second light emitting layer, a third light emitting layer, and a cathode laminated in this order. Including an anode, a first light emitting layer, a first electron barrier layer, a second light emitting layer, a second electron barrier layer, a third light emitting layer, and a cathode stacked in this order,
The organic electroluminescent device according to claim 1, wherein at least one of the first electron barrier layer and the second electron barrier layer exhibits a reversible cathodic reduction process by cyclic voltammetry measurement.

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