JP2007073900A - Organic electroluminescent element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element contrived to attain a high luminance with a low drive voltage. <P>SOLUTION: In an organic electroluminescent element having at least one light emitting layer between a pair of opposing anode and cathode, the light emitting layer contains a metal complex having a ligand of four or more seats as a luminescent material by 30-100 mass% of the entire mass of the light emitting layer, and main emission in emission spectrum is emission by a monomer of the metal complex. A high luminance can be attained with a low drive voltage by the organic electroluminescent element. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an improved organic electroluminescence device capable of obtaining high luminance with a low driving voltage.

  An organic electroluminescent element using a thin film material that emits light when excited by passing an electric current is known. Since organic electroluminescent devices can emit light with high brightness at low voltage, they are widely used in a wide range of fields including mobile phone displays, personal digital assistants (PDAs), computer displays, automobile information displays, TV monitors, or general lighting. It has potential applications and has advantages such as thinning, lightening, miniaturization, and power saving of devices in these fields. For this reason, the expectation as a leading role of the future electronic display market is great. However, in order to be practically used in these fields in place of conventional displays, many technical improvements such as light emission luminance and color tone, durability under a wide range of usage conditions, low cost and large productivity are problems. ing.

One particular problem is improvement in luminance and driving power. Many of the above-described devices have a problem of achieving high brightness first in reducing the thickness, weight, and size. In reducing the thickness and weight, not only the device but also the drive power source must be made compact and lightweight. In particular, when power is supplied from a primary battery or a secondary battery, power saving is a major issue, and there is a strong demand for high brightness with a low driving voltage. Conventionally, in order to achieve high brightness, a high voltage is required, resulting in an accelerated power consumption. Also, high brightness and high voltage have resulted in a loss of device durability.
There has been known an attempt to achieve high luminance by using a phosphorescent material for a light emitting layer (see, for example, Patent Documents 1 to 3). However, as described in these documents, it has been difficult to obtain sufficient luminance with a light emitting material.
Moreover, the organic electroluminescent element which used the multidentate ligand metal complex for the luminescent material is disclosed (refer patent documents 4-6). However, in these light emitting materials, when the packing density of the light emitting material is increased, an interaction between the light emitting materials is generated and light emission is inhibited, so that it is difficult to increase the luminance.
JP 2002-158091 A US Pat. No. 6,303,238 US Pat. No. 6,822,257 WO Patent 2004/108857 JP 2003-73355 A JP 2003-147345 A

  An object of the present invention is to provide an improved organic electroluminescent device capable of obtaining high luminance with a low driving voltage. In particular, this object is achieved by filling the light emitting layer with a new light emitting material at a high density.

The above-described problems of the present invention have been solved by the following means.
<1> An organic electroluminescence device having at least one light emitting layer between a pair of opposing anodes and cathodes, wherein the light emitting layer emits light from a metal complex having a tetradentate or more ligand as a light emitting material. An organic electroluminescence device comprising 30% by mass or more and 100% by mass or less of the total mass of the layer, wherein main emission in an emission spectrum is emission by a monomer body of the metal complex.
<2> The organic electroluminescent element according to <1>, wherein the metal complex is contained in an amount of 50% by mass to 100% by mass with respect to the total mass of the light emitting layer.
<3> The organic electroluminescent device according to <1> or <2>, wherein the metal complex having a tetradentate or higher ligand is a compound represented by the following general formula (I):

(In the general formula (I), M ¹¹ represents a metal ion, and L ^{11 to} L ¹⁵ each represents a ligand coordinated to M ^{11. An} atomic group further exists between L ¹¹ and L ^14. L ¹⁵ may be bonded to both L ¹¹ and L ¹⁴ to form a cyclic ligand, and Y ¹¹ , Y ¹² , and Y ¹³ are each a linking group. In addition, when Y ¹¹ , Y ¹² or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and The bonds between L ¹³ , L ¹³ and Y ¹³ , and Y ¹³ and L ¹⁴ each independently represent a single bond or a double bond, n ¹¹ represents 0 to 4. M ¹¹ and L ^{11 to} L ¹⁵ The bond to each may be any of a coordination bond, an ionic bond, and a covalent bond.)
<4> The organic electroluminescent element according to <1> or <2>, wherein the metal complex having a tetradentate or higher ligand is a compound represented by the following general formula (III):

(In General Formula (III), Q ¹¹ represents an atomic group forming a nitrogen-containing heterocycle, Z ¹¹ , Z ¹² and Z ¹³ each represents a substituted or unsubstituted carbon atom or nitrogen atom; ^Y1 represents a metal ion which may further have a ligand.)
<5> The organic electroluminescent element according to any one of <1> to <4>, wherein the metal ion in the metal complex having a tetradentate or higher ligand is a transition metal ion. .
<6> The metal ions in the metal complex having a tetradentate or higher ligand are iridium ions, platinum ions, gold ions, rhenium ions, tungsten ions, rhodium ions, ruthenium ions, osmium ions, palladium ions, silver ions. <1> to <5>, which is at least one selected from the group consisting of copper ion, cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, and gallium ion Organic electroluminescent element.
<7> The organic electroluminescent element according to any one of <1> to <4>, wherein the metal ion in the metal complex having a tetradentate or higher ligand is a rare earth metal ion. .

  The inventors of the present invention have searched for a method for filling a light emitting material at a high density to obtain a high luminance by obtaining a high light emission intensity. Conventionally, the mechanism of light emission inhibition (also called concentration quenching) due to the interaction between luminescent materials has been elucidated, and the planarity of the molecular structure of the luminescent material and the planar alignment by intermolecular attractive force called stacking. I found out that it was caused. Even if it contains a metal complex having a tetradentate or higher ligand at a high filling rate, it is possible to eliminate these interactions and achieve high luminance by using a light emitting layer mainly showing light emission by a monomer body, In addition, the inventors have found that high luminance can be realized with a low driving voltage, and have led to the inventions <1> and <2>. Moreover, the luminescent material of the preferable structure which this invention achieves was discovered, and it came to invention of <3>-<7>.

  ADVANTAGE OF THE INVENTION According to this invention, a low drive voltage and a high-intensity organic electroluminescent element are provided. According to the present invention, it is possible to lower the driving voltage while maintaining high luminance by filling the light emitting layer with a new light emitting material at high density.

Hereinafter, the organic electroluminescence device of the present invention will be described in detail.
1. SUMMARY OF THE INVENTION An organic electroluminescent device of the present invention is an organic electroluminescent device having at least one luminescent layer between a pair of opposing anodes and cathodes, and the luminescent layer is arranged in four or more positions as a luminescent material. A metal complex having a ligand is contained in an amount of 30% by mass to 100% by mass with respect to the total mass of the light emitting layer, and main light emission in an emission spectrum is light emission by a monomer body of the metal complex. Preferably, the metal complex is contained in an amount of 50% by mass to 100% by mass with respect to the total mass of the light emitting layer.
The main light emission in the present invention means light emission exhibiting peak intensity in the visible wavelength range of the emission spectrum, and in the present invention, light emission with peak intensity is caused by the monomer body of the light emitting material. Preferably, the light emission amount (photon number) from other than the monomer body is less than 10% with respect to the total light emission amount (photon number) from the light emitting layer.
Preferably, the metal complex having a tetradentate or higher ligand is a compound represented by the following general formula (I).

In the general formula (I), M ¹¹ represents a metal ion, L ¹¹ ~L ¹⁵ represents a ligand coordinated to M ^11, respectively. An atomic group may further exist between L ¹¹ and L ¹⁴ to form a cyclic ligand. L ¹⁵ may combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand. Y ¹¹ , Y ¹² , and Y ¹³ each represent a linking group, a single bond, or a double bond. When Y ¹¹ , Y ¹² , or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and L ¹³ , L ¹³ and Y ¹³ , Y ¹³ And the bond between L ¹⁴ each independently represents a single bond or a double bond. n ¹¹ represents the 0-4. The bond between M ¹¹ and L ^{11 to} L ¹⁵ may be any of a coordination bond, an ionic bond, and a covalent bond.
Another preferable metal complex having a tetradentate or higher ligand is a compound represented by the following general formula (III).

In the general formula (III), Q ¹¹ represents a group of atoms forming a nitrogen-containing heterocycle, Z ¹¹ , Z ¹² , and Z ¹³ each represents a substituted or unsubstituted carbon atom or nitrogen atom, and M ^Y1 Represents a metal ion which may further have a ligand.
It is preferable to increase the steric hindrance by imparting a substituent or a linking group to the ligand of the metal complex because the interaction between the metal complexes can be reduced.

  Preferably, the metal ion in the metal complex having a tetradentate or higher ligand is a transition metal ion. Preferably, the metal ion in the metal complex having a tetradentate or higher ligand is iridium ion, platinum ion, gold ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, palladium ion, silver ion. , Copper ions, cobalt ions, zinc ions, nickel ions, lead ions, aluminum ions, and gallium ions. Preferably, the metal ion in the metal complex having a tetradentate or higher ligand is a rare earth metal ion.

2. Each component which comprises an organic electroluminescent element Hereinafter, each component which comprises the organic electroluminescent element of invention is demonstrated in detail.
The organic electroluminescent element in the present invention is preferably composed of a plurality of thin organic compound layers between the cathode and the anode. As a lamination mode of the organic compound layer, a mode in which a hole transport layer, a light emitting layer, and an electron transport layer are stacked in this order from the anode side is preferable. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer.
A hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Further, the light emitting layer may be only one layer, or the light emitting layer may be divided into a first light emitting layer, a second light emitting layer, a third light emitting layer, and the like. Furthermore, each layer may be divided into a plurality of secondary layers.

2-1. Anode <function>
The anode is a layer having a function of supplying holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like.
The anode in the present invention may be patterned according to the pixel.

<Material>
As the material of the anode, a metal, an alloy, a metal oxide, a conductive compound, or a mixture thereof can be used. Among them, a material having a work function of 4 eV or more is preferable. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO), metals such as gold, silver, chromium, and nickel, and mixtures or laminates of these metal oxides and metals. Inorganic conductors such as copper iodide and copper sulfide, organic conductors such as polyaniline, polythiophene, and polypyrrole, and laminates of ITO and these materials are preferable, and conductive metal oxides are preferable. Among these materials, ITO is particularly preferable from the viewpoints of productivity, high conductivity, and transparency.

<Film thickness>
The thickness of the anode is usually from 10 nm to 5 μm, preferably from 50 nm to 1 μm, particularly preferably from 100 nm to 500 nm. If the film thickness is too small, the conductivity necessary for the electrode cannot be obtained, and luminance unevenness due to a voltage drop occurs. If it is too large, the transparency is lowered.

<Formation method>
As a method for forming the anode, a known method can be used. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating vacuum deposition method, a chemical reaction method (sol-gel method, etc.), or a coating method is used. Available. In addition, the anode cleaning method can reduce the driving voltage and improve the light emission efficiency. For example, in the case of ITO, UV ozone cleaning or plasma cleaning is effective.

2-2. Cathode <function>
The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, etc., and the adhesion, ionization potential, and stability between the negative electrode and the adjacent layer such as the electron injection layer, the electron transport layer, and the light emitting layer. It is selected in consideration of etc. The cathode in the present invention may be patterned according to the pixel.

<Material>
As a material of the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples include alkali metals (for example, LI, Na, K, etc.) and their Fluorides or oxides, alkaline earth metals (eg Mg, Ca, etc.) and their fluorides or oxides, gold, silver, lead, aluminum, sodium-potassium alloys or their mixed metals, lithium-aluminum alloys or their Examples thereof include mixed metals, magnesium-silver alloys or mixed metals thereof, rare earth metals such as indium and ytterbium, preferably materials having a work function of 4 eV or less, more preferably aluminum, lithium-aluminum alloys or mixtures thereof. Metal, magnesium-silver alloy or mixed metal thereof.
Among these materials, aluminum is particularly preferable from the viewpoints of low work function, chemical stability, cost, and production suitability.

<Layer structure>
The cathode in the present invention can be formed not only as a single layer structure but also as a laminated structure.
From the viewpoint of preventing a voltage drop, it is preferable to use materials having a lower volume resistivity than, for example, silver and copper as the cathode material. However, these materials emit light due to a decrease in electron injection efficiency due to the work function. In some cases, the luminance and the light emission efficiency are reduced. From this point of view, in the present invention, the laminated structure has a volume resistivity higher than that of a layer having a work function of 4 eV or less and a layer having a work function of 4 eV or less in this order from the organic compound layer side. It is preferred to include a layer that is a low material. Specifically, the cathode has a laminated structure, and among the layers constituting the laminated structure, as a layer positioned on the organic compound layer side, for example, a layer using a lower work function material such as aluminum is formed, By forming a layer using a material having a lower volume resistivity such as silver or copper adjacent to the layer, it is preferable to achieve both the voltage drop prevention, the light emission luminance, and the light emission efficiency. By making the cathode have a laminated structure as described above, the same voltage drop prevention, high luminance and high efficiency can be achieved with a thinner film than when the cathode is formed of a single material.

<Film thickness>
The thickness of the cathode is preferably 0.4 μm or more and 2 μm or less, more preferably 0.6 μm or more and 1.5 μm or less, from the viewpoint of suppressing voltage drop and preventing occurrence of luminance unevenness. When the thickness of the cathode is 2 μm or more, the internal stress after the cathode is made too large may cause a failure such as peeling.

<Formation method>
As a method for forming the cathode, known methods can be used, and an electron beam method, a sputtering method, a resistance heating vacuum deposition method, a coating method, a transfer method, and the like can be used.

  The sheet resistance of the anode and the cathode is preferably lower for the reasons described above, and is preferably several hundred Ω / □ or less.

2-3. Light emitting layer <function>
The light-emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer which has the function to provide and to emit light.
<Material>
The light emitting layer in the present invention contains a metal complex having a tetradentate or higher ligand described later as a light emitting material. The metal complex having a tetradentate or higher ligand in the present invention preferably emits light at a high density of 30% by mass to 100% by mass, more preferably 50% by mass to 100% by mass of the total mass of the light emitting layer. Contained in the layer.

  The light emitting layer in the present invention may be composed of only a light emitting material, or may be a mixed layer of a host material and a light emitting material. The light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the light emitting material may be one type or two or more types. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, for example, a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.

<Film thickness>
The thickness of the light emitting layer is preferably 0.03 μm or more and 0.5 μm or less, and more preferably 0.06 μm or more and 0.4 μm or less from the viewpoint of luminance unevenness, driving voltage, and luminance. If the light-emitting layer is thin, it can be driven with high brightness and low voltage, but the device resistance becomes small, so it is more susceptible to changes in brightness due to voltage drop, resulting in increased brightness unevenness. It becomes. If the thickness of the light emitting layer is large, the drive voltage increases, leading to a decrease in light emission efficiency and limiting the application.

<Layer structure>
The light emitting layer may be one layer or two or more layers, and each layer may emit light in different emission colors. In the case where the light emitting layer has a laminated structure, the film thickness of each layer constituting the laminated structure is not particularly limited, but it is preferable that the total film thickness of each light emitting layer is in the above-described range.

2-4. Multidentate metal complex The metal complex which has a tetradentate or more ligand in this invention is demonstrated.
1) Metal ion The atom coordinated to the metal ion in the metal complex is not particularly limited, but is preferably an oxygen atom, a nitrogen atom, a carbon atom, a sulfur atom or a phosphorus atom, more preferably an oxygen atom, a nitrogen atom or a carbon atom, More preferred are nitrogen or carbon atoms.

  The metal ion in the metal complex is not particularly limited, but is preferably a transition metal ion or a rare earth metal ion, more preferably an iridium ion or a platinum ion, from the viewpoints of improving luminous efficiency, improving durability, and reducing driving voltage. , Gold ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, palladium ion, silver ion, copper ion, cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, gallium ion, or rare earth metal ion (E.g., europium ion, cadolinium ion, or terbium ion) is preferable, and iridium ion, platinum ion, gold ion, rhenium ion, tungsten ion, palladium ion, zinc ion, aluminum is more preferable. Ions, gallium ions, europium ions, cadmium ions, or terbium ions, and when the metal complex is used as a light emitting material, iridium ions, platinum ions, rhenium ions, tungsten ions, europium ions, cadmium ions, or Terbium ions are particularly preferred, and iridium ions, platinum ions, palladium ions, zinc ions, aluminum ions, or gallium ions are particularly preferred when the metal complex is used as a charge transport material or a host material in the light emitting layer.

2) Coordination number The metal complex having a tetradentate or higher ligand in the present invention is preferably a metal complex having a tetradentate or higher and a hexadentate ligand from the viewpoint of improving luminous efficiency and durability. In the case of a metal ion that easily forms a hexacoordinate complex represented by iridium ion, a metal complex having a tetradentate or hexadentate ligand is more preferable, and a tetracoordinate represented by platinum ion. In the case of a metal ion that easily forms a type complex, a metal complex having a tetradentate ligand is more preferable, and a metal complex having a tetradentate ligand is more preferable.

3) Ligand From the viewpoint of improving luminous efficiency and durability, the ligand of the metal complex in the present invention is preferably a chain or a ring, and a central metal (for example, the general formula (I) described later) In the case of a compound represented by the formula, N ¹¹ represents a nitrogen-containing heterocycle coordinated with nitrogen (for example, pyridine ring, quinoline ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring). Oxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, or triazole ring). The nitrogen-containing heterocycle is more preferably a nitrogen-containing 6-membered heterocycle or a nitrogen-containing 5-membered heterocycle. These heterocycles may form condensed rings with other rings.

  That the ligand of the metal complex is a chain means that the ligand of the metal complex does not have a cyclic structure (for example, a terpyridyl ligand). Further, that the ligand of the metal complex is cyclic means that a plurality of ligands in the metal complex are bonded to each other to form a closed structure (for example, phthalocyanine ligand, crown ether coordination). Etc.).

4) Preferred Metal Complex Structure The metal complex in the present invention is preferably a compound represented by the following general formula (I), general formula (II) or general formula (III).

<Metal Complex Represented by General Formula (I)>
First, the compound represented by formula (I) will be described.

In the general formula (I), M ¹¹ represents a metal ion, L ¹¹ ~L ¹⁵ represents a ligand coordinated to M ^11, respectively. An atomic group may further exist between L ¹¹ and L ¹⁴ to form a cyclic ligand. L ¹⁵ may combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand.
Y ¹¹ , Y ¹² , and Y ¹³ each represent a linking group, a single bond, or a double bond. When Y ¹¹ , Y ¹² , or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and L ¹³ , L ¹³ and Y ¹³ , Y ¹³ And the bond between L ¹⁴ each independently represents a single bond or a double bond. n ¹¹ represents the 0-4. The bond between M ¹¹ and L ^{11 to} L ¹⁵ may be any of a coordination bond, an ionic bond, and a covalent bond.

The compound represented by formula (I) will be described in detail.
In the general formula (I), M ¹¹ represents a metal ion. Although it does not specifically limit as a metal ion, A bivalent or trivalent metal ion is preferable. As the divalent or trivalent metal ion, platinum ion, iridium ion, rhenium ion, palladium ion, rhodium ion, ruthenium ion, copper ion, europium ion, gadolinium ion, terbium ion are preferable, platinum ion, iridium ion, or Europium ions are more preferred, platinum ions and iridium ions are more preferred, and platinum ions are particularly preferred.

In general formula (I), L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ each independently represent a ligand that coordinates to M ¹¹ . As an atom contained in L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ and coordinated to M ¹¹ , a nitrogen atom, an oxygen atom, a sulfur atom, a carbon atom, or a phosphorus atom is preferable, and a nitrogen atom, oxygen An atom, a sulfur atom, or a carbon atom is more preferable, and a nitrogen atom, an oxygen atom, or a carbon atom is still more preferable.

The bonds formed by M ¹¹ and L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ may each independently be a covalent bond, an ionic bond, or a coordinate bond. For convenience of explanation, the ligand in the present invention shall be used not only in the case of a coordination bond but also in the case of being formed by other ionic bonds or covalent bonds.
The ligand composed of L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and L ¹⁴ is an anionic ligand (a ligand in which at least one anion binds to a metal). Is preferred. 1-3 are preferable, as for the number of anions in an anionic ligand, 1 and 2 are more preferable, and 2 is further more preferable.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a carbon atom are not particularly limited, but are each independently an imino ligand, an aromatic carbocyclic ligand (for example, a benzene ligand) , Naphthalene ligand, anthracene ligand, phenanthracene ligand, etc.), heterocyclic ligand (eg thiophene ligand, pyridine ligand, pyrazine ligand, pyrimidine ligand, thiazole coordination) Children, oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, and condensed rings (for example, quinoline ligands, benzothiazole ligands, and the like) and tautomers thereof ).

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a nitrogen atom are not particularly limited, but each independently includes a nitrogen-containing heterocyclic ligand (eg, pyridine ligand, pyrazine coordination) Ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxadi An azole ligand, a thiadiazole ligand, and a condensed ring containing them (for example, a quinoline ligand, a benzoxazole ligand, or a benzimidazole ligand), and tautomers thereof (note that In the present invention, in addition to the usual isomers, the following examples are also defined as tautomers, for example, the 5-membered heterocyclic ligand of the compound (24) and the terminal 5-membered heterocyclic ring of the compound (64) described later. Ligand A 5-membered heterocyclic ligand of the compound (145) is also defined as a pyrrole tautomer.) Amino ligands (alkylamino ligands (preferably having 2 to 30 carbon atoms, more preferably 2 carbon atoms) To 20, particularly preferably 2 to 10 carbon atoms, such as methylamino), arylamino ligands (such as phenylamino), acylamino ligands (preferably having 2 carbon atoms). To 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino ligand (preferably 2 to 30 carbon atoms). More preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, methoxycarbonylamino and the like. An oxycarbonylamino ligand (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino), a sulfonylamino group; A ligand (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), imino ligand These ligands may be further substituted.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by an oxygen atom are not particularly limited, but are independently an alkoxy ligand (preferably having 1 to 30 carbon atoms, more preferably carbon numbers). 1 to 20, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy), aryloxy ligands (preferably 6 to 30 carbon atoms, more preferably Has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like, and a heterocyclic oxy ligand (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy And an acyloxy ligand (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy. ), A silyloxy ligand (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy, triphenylsilyloxy, etc.). Carbonyl ligands (such as ketone ligands, ester ligands, or amide ligands), ether ligands (such as dialkyl ether ligands, diaryl ether ligands, or furyl ligands), etc. Is mentioned.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a sulfur atom are not particularly limited, but each independently represents an alkylthio ligand (preferably having 1 to 30 carbon atoms, more preferably carbon numbers). 1 to 20, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio, etc.), an arylthio ligand (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably Has 6 to 12 carbon atoms, for example, phenylthio and the like, and a heterocyclic thio ligand (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), thiocarbonyl coordination (E.g. thioketone ligand, etc. thioester ligands), or thioether ligands (e.g. dialkyl thioether ligands, diaryl thioether ligands, etc. thiofuryl ligand), and the like. These substituted ligands may be further substituted.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a phosphorus atom are not particularly limited, but each independently represents a dialkylphosphino group, a diarylphosphino group, a trialkylphosphine, a triarylphosphine, And a phosphinin group. These groups may be further substituted.

L ¹¹ and L ¹⁴ are each independently an aromatic carbocyclic ligand, alkyloxy ligand, aryloxy ligand, ether ligand, alkylthio ligand, arylthio ligand, alkylamino coordination Ligand, arylamino ligand, acylamino ligand, nitrogen-containing heterocyclic ligand (eg pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand) Ligands, oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands, oxadiazole ligands, thiadiazole ligands, or condensed ligand bodies containing them ( For example, a quinoline ligand, a benzoxazole ligand, a benzimidazole ligand, or the like, or a tautomer thereof is preferable, and an aromatic carbocyclic ligand, aryl Xy ligands, arylthio ligands, arylamino ligands, and pyridine ligands, pyrazine ligands, imidazole ligands, or condensed ligand bodies containing them (eg, quinoline ligands, quinoxalines) A ligand, a benzimidazole ligand, or the like, or a tautomer thereof, more preferably an aromatic carbocyclic ligand, an aryloxy ligand, an arylthio ligand, or an arylamino ligand. Aromatic carbocyclic ligands or aryloxy ligands are preferred.

L ¹² and L ¹³ each independently ligands preferably form a coordinate bond with M ^11, as ligands forming a coordination bond with M ^11, a pyridine ring, a pyrazine ring, a pyrimidine ring, Triazine ring, thiazole ring, oxazole ring, pyrrole ring, triazole ring, and condensed ring containing them (for example, quinoline ring, benzoxazole ring, benzimidazole ring, or indolenine ring) and their tautomers And a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrrole ring, and a condensed ring containing them (for example, a quinoline ring, a benzpyrrole, etc.) and a tautomer thereof are more preferable, and a pyridine ring, a pyrazine ring, Pyrimidine rings and condensed rings containing them (for example, quinoline rings and the like) are more preferable, and pyridine rings and condensed rings containing pyridine rings are more preferable. Body (e.g., a quinoline ring) are particularly preferred.

In the general formula (I), L ¹⁵ represents a ligand coordinated to M ¹¹ . L ¹⁵ is preferably a 1-4-dentate ligand, and more preferably a 1-4-dentate anionic ligand. Although it does not specifically limit as an anionic ligand of 1-4 tetradentate, The monoanionic property containing a halogen ligand, a 1, 3- diketone ligand (for example, acetylacetone ligand etc.), and a pyridine ligand Bidentate ligands (eg, picolinic acid ligands, 2- (2-hydroxyphenyl) -pyridine ligands), L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and L ^The tetradentate ligand formed by ¹⁴ is preferred, and a monoanionic bidentate ligand containing a 1,3-diketone ligand (eg, acetylacetone ligand) or a pyridine ligand (eg, picolinic acid) Ligands, 2- (2-hydroxyphenyl) -pyridine ligands, etc.), L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and a tetradentate ligand formed by L ¹⁴ Are more preferred, and 1,3-diketone ligands (e.g. And a monoanionic bidentate ligand containing a pyridine ligand (for example, a picolinic acid ligand, 2- (2-hydroxyphenyl) -pyridine ligand, etc.), 1,3-diketone ligands (such as acetylacetone ligands) are particularly preferred.
The number of coordination sites and the number of ligands do not exceed the coordination number of the metal. However, L ¹⁵ does not bind to both L ¹¹ and L ¹⁴ to form a cyclic ligand.

In the general formula (I), Y ¹¹ , Y ¹² and Y ¹³ each independently represent a linking group, a single bond or a double bond. Although it does not specifically limit as a coupling group, For example, the coupling group comprised including the atom selected from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, or a phosphorus atom is preferable. Specific examples of such a linking group include the following.

When Y ¹¹ , Y ¹² , or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and L ¹³ , L ¹³ and Y ¹³ , Y ¹³ And the bond between L ¹⁴ each independently represents a single bond or a double bond.

Y ¹¹ , Y ¹² , and Y ¹³ are each independently preferably a single bond, a double bond, a carbonyl linking group, an alkylene linking group, or an alkenylene group. Y ¹¹ is more preferably a single bond or an alkylene group, and still more preferably an alkylene group. Y ¹² and Y ¹³ are more preferably a single bond or an alkenylene group, and even more preferably a single bond.

Ring formed by Y ¹² , L ¹¹ , L ¹² and M ¹¹ , Ring formed by Y ¹¹ , L ¹² , L ¹³ and M ¹¹ , Formed by Y ¹³ , L ¹³ , L ¹⁴ and M ¹¹ The ring to be formed preferably has 4 to 10 ring members, more preferably 5 to 7 ring members, and further preferably 5 or 6 ring members.

In the general formula (I), n ¹¹ represents 0 to 4. When M ¹¹ is a metal having a coordination number of 4, n ¹¹ is 0. When M ¹¹ is a metal having a coordination number of 6, n ¹¹ is preferably 1, 2, and more preferably 1. When M ¹¹ is coordination number 6 and n ¹¹ is 1, L ¹⁵ represents a bidentate ligand, and when M ¹¹ is coordination number 6 and n ¹¹ is 2, L ¹⁵ represents a monodentate ligand. When M ¹¹ is a metal having a coordination number of 8, n ¹¹ is preferably 1 to 4, more preferably 1 or 2, and more preferably 1. When M ¹¹ is coordination number 8 and n ¹¹ is 1, L ¹⁵ represents a tetradentate ligand, and when M ¹¹ is coordination number 8 and n ¹¹ is 2, L ¹⁵ represents a bidentate ligand. When n ¹¹ is plural, the plural L ¹⁵ may be the same or different.

  Preferred forms of the compound represented by the general formula (I) include the following compounds represented by the general formula (1), the general formula (2), the general formula (3), and the general formula (4). It is.

  The compound represented by the general formula (1) will be described.

In the general formula (1), M ²¹ represents a metal ion, and Y ²¹ represents a linking group, a single bond, or a double bond. Y ²² and Y ²³ each represent a single bond or a linking group. Q ²¹ and Q ²² each represent an atomic group forming a nitrogen-containing heterocycle, and the bond between the ring formed by Q ²¹ and Y ²¹ and the bond between the ring formed by Q ²² and Y ²¹ are as follows: Represents a single bond or a double bond. X ²¹ and X ²² each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. R ²¹ , R ²² , R ²³ , and R ²⁴ each independently represent a hydrogen atom or a substituent, and R ²¹ and R ²² , and R ²³ and R ²⁴ may be bonded to each other to form a ring. L ²⁵ represents a ligand coordinated to M ²¹ . n ²¹ represents an integer of 0 to 4.

The general formula (1) will be described in detail.
In the general formula (1), M ²¹ has the same meaning as M ¹¹ in the general formula (I), and the preferred range is also the same.

Q ²¹ and Q ²² each independently represents an atomic group forming a nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ²¹ ). The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is not particularly limited, and includes, for example, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, and the like. Examples thereof include a condensed ring (for example, a quinoline ring, a benzoxazole ring, a benzimidazole ring, or an indolenine ring) and tautomers thereof.

The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is preferably a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrazole ring, imidazole ring, oxazole ring, pyrrole ring, benzazole ring, And condensed rings containing them (for example, quinoline ring, benzoxazole ring or benzimidazole ring) and tautomers thereof, more preferably pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, pyrrole ring , And condensed rings containing them (for example, quinoline ring and the like) and tautomers thereof, more preferably pyridine rings and condensed rings (for example, quinoline ring and the like), particularly preferably It is a pyridine ring.

X ²¹ and X ²² are each independently an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom, more preferably an oxygen atom, a sulfur atom, or a substituted nitrogen atom, and even more preferably an oxygen atom or a sulfur atom. An oxygen atom is particularly preferable.

Y ²¹ has the same meaning as Y ¹¹ in formula (I), and the preferred range is also the same.

Y ²² and Y ²³ each independently represent a single bond or a linking group, and preferably a single bond. The linking group is not particularly limited, and examples thereof include a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, and a combination thereof. Groups and the like.

The linking group represented by Y ²² or Y ²³ is preferably a carbonyl linking group, an alkylene linking group or an alkenylene linking group, more preferably a carbonyl linking group or an alkenylene linking group, and even more preferably a carbonyl linking group.

R ²¹ , R ²² , R ²³ , and R ²⁴ each independently represents a hydrogen atom or a substituent. Although it does not specifically limit as a substituent, For example, alkyl group (preferably C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, methyl, ethyl, Iso-propyl, for example. , Tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). , Particularly preferably having 2 to 10 carbon atoms, such as propargyl and 3-pentynyl). Ru group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, and anthranyl). An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and Ditolylamino, etc.),

An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like. ), A heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like.) An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably carbon number) -12, for example, acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms). For example, methoxycarbonyl, ethoxycarbonyl, etc.), aryloxycarbonyl group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, particularly preferably having 7 to 12 carbon atoms, such as phenyl And oxycarbonyl).

An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), an acylamino group (preferably having a carbon number) 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino and the like, and aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably carbon atoms). 7 to 20, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonylamino ), Sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc. ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenyl Sulfamoyl etc.),

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like), alkylthio. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 to 6 carbon atoms). 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like, and a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 carbon atom). -20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolyl E, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, mesyl, tosyl, etc.), sulfinyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzene And ureido groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include ureido, methylureido, and phenylureido. ),

A phosphoric acid amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide); Hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom or iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, hetero A cyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, Thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carba And 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. For example, trimethylsilyl, triphenylsilyl, etc.) ), A silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy and triphenylsilyloxy. Etc.). These substituents may be further substituted.

R ²¹ , R ²² , R ²³ , and R ²⁴ are each independently an alkyl group, an aryl group, R ²¹ and R ^22, or R ²³ and R ²⁴ bonded to form a ring structure (for example, a benzo condensed ring or a pyridine condensed ring). A group that forms a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) by combining R ²¹ and R ²² or R ²³ and R ²⁴ .

L ²⁵ has the same meaning as L ¹⁵ in formula (I), and the preferred range is also the same.

n ²¹ has the same meaning as n ¹¹ in the general formula (I), and their preferable ranges are also the same.

In the general formula (1), when the ring formed by Q ²¹ and Q ²² is a pyridine ring, Y ²¹ is a metal complex representing a linking group, the ring formed by Q ²¹ and Q ²² is a pyridine ring, ²¹ is a single bond or a double bond, and X ²¹ and X ²² are a sulfur atom and a substituted or unsubstituted nitrogen atom, or the ring formed by Q ²¹ and Q ²² is a nitrogen-containing hetero-5 A metal complex representing a membered ring or a nitrogen-containing six-membered ring containing two or more nitrogen atoms is preferable.

  A preferred form of the compound represented by the general formula (1) is a compound represented by the following general formula (1-A).

General formula (1-A) is demonstrated.
Formula (1-A) in, M ³¹ has the same meaning as M ¹¹ in the above formula (I), and their preferable ranges are also the same.

Z ³¹ , Z ³² , Z ³³ , Z ³⁴ , Z ³⁵ , and Z ³⁶ each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom is more preferable. Examples of the substituent on carbon include the groups described for R ²¹ in the general formula (1), and Z ³¹ and Z ³² , Z ³² and Z ³³ , Z ³³ and Z ³⁴ , and Z ³⁴ and Z ^35. , Z ³⁵ and Z ³⁶ may be bonded via a linking group to form a condensed ring (for example, benzo condensed ring, pyridine condensed ring, etc.), and Z ³¹ and T ³¹ , Z ³⁶ and T ³⁸ are connected to each other. To form a condensed ring (for example, benzo condensed ring, pyridine condensed ring, etc.).

  As the substituent on the carbon, an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.), a halogen atom is preferable, an alkylamino group, A group that forms an aryl group or a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) is more preferable, and a group that forms an aryl group or a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) is more preferable. A group that forms a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) is particularly preferable.

T ³¹ , T ³² , T ³³ , T ³⁴ , T ³⁵ , T ³⁶ , T ³⁷ , and T ³⁸ each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom Is more preferable. Examples of the substituent on carbon include the groups described for R ²¹ in the general formula (1), and T ³¹ and T ³² , T ³² and T ³³ , T ³³ and T ³⁴ , T ³⁵ and T ^36. , T ³⁶ and T ³⁷ , and T ³⁷ and T ³⁸ may be bonded via a linking group to form a condensed ring (for example, a benzo condensed ring).

  As the substituent on the carbon, an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group that forms a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.), and a halogen atom are preferable. A group that forms a ring (for example, a benzo-fused ring, a pyridine-fused ring, etc.) and a halogen atom are more preferred, an aryl group and a halogen atom are more preferred, and an aryl group is particularly preferred.

X ³¹ and X ³² are each independently synonymous with X ²¹ and X ²² in the general formula (1), and the preferred range is also the same.

  Next, the compound represented by the general formula (2) will be described.

In the general formula (2), M ⁵¹ has the same meaning as M ¹¹ in the general formula (I), and the preferred range is also the same.

Q ⁵¹ and Q ⁵² are each independently synonymous with Q ²¹ and Q ²² in the general formula (1), and their preferred ranges are also the same.

Q ⁵³ and Q ⁵⁴ each independently represent a group that forms a nitrogen-containing heterocycle (a ring containing a nitrogen coordinated to M ⁵¹ ). The nitrogen-containing heterocycle formed by Q ⁵³ and Q ⁵⁴ is not particularly limited, but a tautomer of a pyrrole derivative or a tautomer of an imidazole derivative (for example, a hetero 5-membered ring of the following exemplified compound (29) Ligands, etc.), tautomers of thiazole derivatives (eg, hetero 5-membered ring ligands of the following exemplified compound (30)), tautomers of oxazole derivatives (eg, heterocycles of the exemplified compound (31) below) 5-membered ring ligands etc.) are preferred, tautomers of pyrrole derivatives, tautomers of imidazole derivatives, and tautomers of thiazole derivatives are more preferred, tautomers of pyrrole derivatives, and tautomers of imidazole derivatives. Mutants are more preferred, and tautomers of pyrrole derivatives are particularly preferred.

Y ⁵¹ has the same meaning as Y ¹¹ in formula (I), and the preferred range is also the same.

L ⁵⁵ has the same meaning as that of L ¹⁵ in Formula (I), and their preferable ranges are also the same.

n ⁵¹ has the same meaning as n ¹¹ , and the preferred range is also the same.

W ⁵¹ and W ⁵² each independently represent a substituted or unsubstituted carbon atom or nitrogen atom, preferably an unsubstituted carbon atom or nitrogen atom, and more preferably an unsubstituted carbon atom.

  The compound represented by the general formula (3) will be described.

In the general formula (3), M ^A1 , Q ^A1 , Q ^A2 , Y ^A1 , Y ^A2 , Y ^A3 , R ^A1 , R ^A2 , R ^A3 , R ^A4 , L ^A5 , and n ^A1 are the same as those in the general formula (1). Are the same as M ²¹ , Q ²¹ , Q ²² , Y ²¹ , Y ²² , Y ²³ , R ²¹ , R ²² , R ²³ , R ²⁴ , L ²⁵ , and n ²¹ , and the preferred range is also the same.

A preferable form of the compound represented by the general formula (3) is a compound represented by the following general formula (3-A) and a compound represented by the following general formula (3-B).
First, the compound represented by the general formula (3-A) will be described.

In General Formula (3-A), M ⁶¹ has the same meaning as M ¹¹ in General Formula (I), and the preferred range is also the same.

Q ⁶¹ and Q ⁶² each independently represent a group forming a ring. The ring formed by Q ⁶¹ and Q ⁶² is not particularly limited, and examples thereof include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a thiophene ring, an isothiazole ring, a furan ring, an isoxazole ring, and a condensed ring thereof. The body is mentioned.

The ring formed by Q ⁶¹ and Q ⁶² is preferably a benzene ring, a pyridine ring, a thiophene ring, a thiazole ring, and a condensed ring thereof, more preferably a benzene ring, a pyridine ring, and a condensed ring thereof, A benzene ring and its condensed ring are more preferable.

Y ⁶¹ has the same meaning as Y ¹¹ in formula (I), and the preferred range is also the same.

Y ⁶² and Y ⁶³ each independently represent a linking group or a single bond. The linking group is not particularly limited, and examples thereof include a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, and a combination thereof. Groups and the like.

Y ⁶² and Y ⁶³ are each independently preferably a single bond, a carbonyl linking group, an alkylene linking group or an alkenylene group, more preferably a single bond or an alkenylene group, and even more preferably a single bond.

L ⁶⁵ has the same meaning as L ¹⁵ in formula (I), and the preferred range is also the same.

n ⁶¹ has the same meaning as n ¹¹ in formula (I), and the preferred range is also the same.

Z ⁶¹ , Z ⁶² , Z ⁶³ , Z ⁶⁴ , Z ⁶⁵ , Z ⁶⁶ , Z ⁶⁷ , and Z ⁶⁸ each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom Is preferred. Examples of the substituent on the carbon include the groups described for R ²¹ in the general formula (1), and also include Z ⁶¹ and Z ⁶² , Z ⁶² and Z ⁶³ , Z ⁶³ and Z ⁶⁴ , Z ⁶⁵ and Z ^66. , Z ⁶⁶ and Z ⁶⁷ , Z ⁶⁷ and Z ⁶⁸ may be bonded via a linking group to form a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.). The ring formed by Q ⁶¹ and Q ⁶² may be bonded to Z ⁶¹ and Z ⁶⁸ via a linking group to form a ring.

  As the substituent on the carbon, an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) or a halogen atom is preferable. A group that forms a group or a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.) is more preferable, a group that forms an aryl group or a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.) is more preferable, A group that forms a benzo-fused ring, a pyridine-fused ring, etc.) is particularly preferred.

  The compound represented by formula (3-B) will be described.

In the general formula (3-B), M ⁷¹ has the same meaning as M ¹¹ in the above formula (I), and their preferable ranges are also the same.

Y ⁷¹ , Y ⁷² , and Y ⁷³ are each independently synonymous with Y ⁶² in the general formula (3-A), and the preferred range is also the same.

L ⁷⁵ has the same meaning as that of L ¹⁵ in Formula (I), and their preferable ranges are also the same.

n ⁷¹ has the same meaning as n ¹¹ in the general formula (I), and their preferable ranges are also the same.

Z ⁷¹ , Z ⁷² , Z ⁷³ , Z ⁷⁴ , Z ⁷⁵ , and Z ⁷⁶ each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom, preferably a substituted or unsubstituted carbon atom. Examples of the substituent on carbon include the groups described for R ²¹ in the general formula (1). Z ⁷¹ and Z ⁷² , Z ⁷³ and Z ⁷⁴ may be bonded via a linking group to form a ring (for example, a benzene ring or a pyridine ring). R ^{71 to} R ⁷⁴ are synonymous with the substituents of R ^{21 to} R ²⁴ in the general formula (1), and the preferred range is also the same.

A preferred form of the compound represented by the general formula (3-B) is a compound represented by the following general formula (3-C).
The compound represented by formula (3-C) will be described.

In general formula (3-C), R ^C1 and R ^C2 each independently represent a hydrogen atom or a substituent, and the substituent is described as the substituent of R ²¹ to R ²⁴ in general formula (1). Represents an alkyl group or an aryl group. The substituents represented by R ^C3 , R ^C4 , R ^C5 and R ^C6 are also synonymous with the substituents of R ²¹ to R ²⁴ in the general formula (1). n ^C3, n ^C6 is an integer of 0 to 3, n ^C4, n ^C5 represents an integer of 0 to 4, R ^C3, R ^C4, when R ^C5, and having a plurality of R ^C6 each plurality of R ^C3 , R ^C4 , R ^C5 , and R ^C6 may be the same or different and may be linked to form a ring. R ^C3 , R ^C4 , R ^C5 and R ^C6 are preferably an alkyl group, an aryl group, a heteroaryl group, or a halogen atom.

  The compound represented by the general formula (4) will be described.

In the general formula (4), M ^B1 , Y ^B2 , Y ^B3 , R ^B1 , R ^B2 , R ^B3 , R ^B4 , L ^B5 , n ^B3 , X ^B1 , and X ^B2 are M in the general formula (1). ²¹ , Y ²² , Y ²³ , R ²¹ , R ²² , R ²³ , R ²⁴ , L ²⁵ , n ²¹ , X ²¹ , and X ²² are synonymous with each other and preferred ranges are also the same.

Y ^B1 represents a linking group and is the same as Y ²¹ in the general formula (1), preferably a vinyl group substituted at the 1,2-position, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or a carbon number of 2 8 represents a methylene group.
R ^B5 and R ^B6 each independently represent a hydrogen atom or a substituent, and examples of the substituent include the alkyl group, aryl group, and heterocyclic group described as the substituent of R ²¹ to R ²⁴ in the general formula (1). Represents. However, Y ^B1 is not linked to R ^B5 or R ^B6 . n ^B1 and n ^B2 each independently represents an integer of 0 to 1.

A preferred form of the compound represented by the general formula (4) is a compound represented by the following general formula (4-A).
The compound represented by formula (4-A) will be described.

In General Formula (4-A), R ^D3 and R ^D4 each independently represent a hydrogen atom or a substituent, and R ^D1 and R ^D2 each represent a substituent. The substituent represented by R ^D1 , R ^D2 , R ^D3 , and R ^D4 has the same meaning as the substituent represented by R ^B5 , R ^B6 in the general formula (4), and the preferred range is also the same. n ^D1, n ^D2 represents an integer of 0 to 4, when having a plurality of R ^D1, R ^D2, respectively, a plurality of R ^D1, R ^D2 may be the same or different, a linked ring It may be formed. Y ^D1 represents a vinyl group, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, or a methylene group having 1 to 8 carbon atoms substituted at the 1 and 2 positions.

  Specific examples of the compound represented by the general formula (I) include the following compounds, but are not limited thereto.

  Among the compounds represented by the above compound examples, a tetradentate ligand containing bipyridyl or phenanthroline in a partial structure, a Schiff base type tetradentate ligand, a phenylbipyridyl tridentate ligand, a diphenylpyridine tridentate ligand, Or the compound except the compound which has a ligand chosen from a terpyridine tridentate ligand is more preferable.

Metal complexes in the present invention [general formulas (I), (1), (1-A), (2), (3), (3-A), (3-B), (3-C), ( 4) and (4-A) can be synthesized by various methods.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic or organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, and potassium carbonate) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

  The reaction time for synthesizing the metal complex of the present invention varies depending on the activity of the reaction raw material and is not particularly limited, but is preferably 1 minute to 5 days, more preferably 5 minutes to 3 days, and more preferably 10 minutes to 1 day. Is more preferable.

  The reaction temperature for synthesizing the metal complex of the present invention varies depending on the activity of the reaction and is not particularly limited, but is preferably 0 ° C. or higher and 300 ° C. or lower, more preferably 5 ° C. or higher and 250 ° C. or lower, and further preferably 10 ° C. or higher and 200 ° C. or lower.

In the metal complex of the present invention, by appropriately selecting a ligand that forms a partial structure of the target complex, the general formulas (I), (1), (1-A), (2), Compounds represented by the compounds represented by (3), (3-A), (3-B), (3-C), (4), (4-A), and (X3) can be synthesized.
For example, when synthesizing the compound represented by the general formula (1-A), 6,6′-bis (2-hydroxyphenyl) -2,2′-bipyridyl ligand or a derivative thereof (for example, 2, 9-bis (2-hydroxyphenyl) -1,10-phenanthroline ligand, 2,9-bis (2-hydroxyphenyl) -4,7-diphenyl-1,10-phenanthroline ligand, 6,6 ′ -Bis (2-hydroxy-5-tert-butylphenyl) -2,2'-bipyridyl ligand, etc.) is preferably 0.1 equivalent to 10 equivalents, more preferably 0.3 equivalent to the metal compound. Equivalent to 6 equivalents, more preferably 0.5 to 4 equivalents can be added for synthesis.
In the method for synthesizing the compound represented by the general formula (1-A), each of the reaction solvent, the reaction time, and the reaction temperature is the same as that described in the method for synthesizing the metal complex of the present invention.

Derivatives of 6,6′-bis (2-hydroxyphenyl) -2,2′-bipyridyl ligand can be synthesized using various known methods.
For example, a 2,2′-bipyridyl derivative (for example, 1,10-phenanthroline and the like) and an anisole derivative (for example, 4-fluoroanisole and the like) are reacted by the method described in Journal of OrganIc ChemIstry, 741,11, (1946). Can be synthesized. In addition, halogenated 2,2′-bipyridyl derivatives (eg, 2,9-dibromo-1,10-phenanthroline) and 2-methoxyphenylboronic acid derivatives (eg, 2-methoxy-5-fluorophenylboron) After the Suzuki coupling reaction using an acid or the like as a starting material, the methyl group is deprotected (the method described in Journal of OrganIc ChemIstry, 741, 11, (1946), the method of heating in pyridine hydrochloride, etc. Can be synthesized. In addition, 2,2′-bipyridylboronic acid derivatives (eg, 6,6′-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolyl) -2,2′-bipyridyl) and halogens A methyl group is deprotected after a Suzuki coupling reaction using a modified anisole derivative (eg, 2-bromoanisole) as a starting material (Journal of OrganIc ChemIstry, 741, 11, (1946), Alternatively, it can also be synthesized by using a method such as heating in pyridine hydrochloride.

<Metal complex represented by general formula (III)>
Next, the compound represented by the following general formula (III) will be described.

In the general formula (III), Q ¹¹ represents a group of atoms forming a nitrogen-containing heterocycle, Z ¹¹ , Z ¹² , and Z ¹³ each represents a substituted or unsubstituted carbon atom or nitrogen atom, and M ^Y1 Represents a metal ion which may further have a ligand.

In the general formula (III), Q ¹¹ represents an atomic group that includes two carbon atoms to which Q ¹¹ is bonded and a nitrogen atom directly bonded to these carbon atoms to form a nitrogen-containing heterocycle. The number of ring members of the nitrogen-containing heterocycle formed by Q ¹¹ is not particularly limited, but is preferably 12 to 20 ring members, more preferably 14 to 16 ring members, and still more preferably 16 ring members.

Z ¹¹ , Z ¹² , and Z ¹³ each independently represent a substituted or unsubstituted carbon atom or nitrogen atom. The combination of Z ^11, Z ^12, and Z ^13, Z ^11, it is preferred Z ^12, and that at least one nitrogen atom of Z ^13.

  Examples of the substituent on the carbon atom include an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms such as methyl, ethyl, Iso-propyl. , Tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 2 carbon atoms). 20, particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl).

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl and the like), amino. Group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc. An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc. An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy, and the like, and heterocyclic oxy groups (preferably having 1 to 30 carbon atoms, more preferably ) Has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, and the like.

An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group ( Preferably it has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably having a carbon number). 7 to 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl, and acyloxy groups (preferably 2 to 30 carbon atoms, more preferably carbon atoms). 2 to 20, particularly preferably 2 to 10 carbon atoms, for example, acetoxy, benzoyloxy An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino). ,

An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino group ( Preferably it has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino, etc., and a sulfonylamino group (preferably 1 to 1 carbon atoms). 30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, methanesulfonylamino, benzenesulfonylamino, etc.), a sulfamoyl group (preferably C0-30, more preferably) Has 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms. Amoiru, methylsulfamoyl, dimethylsulfamoyl, and the like phenylsulfamoyl.),

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like), alkylthio. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 to 6 carbon atoms). 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like, and a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 carbon atom). -20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolyl Oh, 2-benzoxazolyl thio, and 2-benzthiazolylthio the like.),

A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), a sulfinyl group (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), ureido groups (preferably 1 to 30 carbon atoms, more preferably C1-C20, Most preferably, it is C1-C12, for example, a ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide groups (preferably C1-C30, more preferably carbon number) 1 to 20, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide That.), Hydroxy group, a mercapto group, a halogen atom (e.g. fluorine atom, chlorine atom, bromine atom or 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, more preferably 1 to 12 carbon atoms, As, for example, a nitrogen atom, an oxygen atom, a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl and triphenylsilyl), silyloxy Group (preferably 3 to 40 carbon atoms, more preferably carbon number 30, particularly preferably from 3 to 24 carbon atoms, for example trimethylsilyloxy, etc. triphenylsilyl oxy and the like.) And the like. These substituents may be further substituted.
Among these substituents, the substituent on the carbon atom is preferably an alkyl group, an aryl group, a heterocyclic group, or a halogen atom, more preferably an aryl group or a halogen atom, and further preferably a phenyl group or a fluorine atom. Is an atom.

  As a substituent on a nitrogen atom, the substituent illustrated as a substituent on the said carbon atom is mentioned, A preferable range is also the same.

In general formula (III), M ^Y1 represents a metal ion which may further have a ligand, and a metal ion having no other ligand is more preferable.

The metal ion represented by ^MY1 is not particularly limited, but a divalent or trivalent metal ion is preferable. As the divalent or trivalent metal ion, cobalt ion, magnesium ion, zinc ion, palladium ion, nickel ion, copper ion, platinum ion, lead ion, aluminum ion, iridium ion, and europium ion are preferable, cobalt ion, magnesium ion Ions, zinc ions, palladium ions, nickel ions, copper ions, platinum ions, or lead ions are more preferable, copper ions and platinum ions are more preferable, and platinum ions are particularly preferable. M ^Y1 may or may not be bonded to an atom contained in Q ¹¹ , and is preferably bonded.

The ligand that M ^Y1 may further have is not particularly limited, but is preferably a monodentate or bidentate ligand, and more preferably a bidentate ligand. The coordination atom is not particularly limited, but is preferably an oxygen atom, a sulfur atom, a nitrogen atom, a carbon atom, or a phosphorus atom, more preferably an oxygen atom, a nitrogen atom, or a carbon atom, and further an oxygen atom or a nitrogen atom. preferable.

Preferable examples of the compound represented by the general formula (III) are compounds represented by the following general formulas (a) to (j), or tautomers thereof.
The compound represented by the general formula (III) is more preferably a compound represented by the general formula (a) or the general formula (b) or a tautomer thereof, and a compound represented by the general formula (b). Or its tautomer is more preferable.
Moreover, as a compound represented by general formula (III), the compound represented by general formula (c) or general formula (g) is also preferable.
The compound represented by the general formula (c) includes a compound represented by the general formula (d) or a tautomer thereof, a compound represented by the general formula (e) or a tautomer thereof, a general formula ( The compound represented by f) or a tautomer thereof is preferable, the compound represented by the general formula (d) or the tautomer thereof, the compound represented by the general formula (e) or the tautomer thereof More preferred is a compound represented by formula (d) or a tautomer thereof.

  As the compound represented by the general formula (g), a compound represented by the general formula (h) or a tautomer thereof, a compound represented by the general formula (I) or a tautomer thereof, The compound represented by j) or a tautomer thereof is preferred, the compound represented by the general formula (h) or the tautomer thereof, the compound represented by the general formula (I) or the tautomer thereof More preferred is a compound represented by formula (h) or a tautomer thereof.

  Hereinafter, the compounds represented by the general formulas (a) to (j) will be described in detail.

The compound represented by the general formula (a) will be described.
In the general formula (a), Z ²¹ , Z ²² , Z ²³ , Z ²⁴ , Z ²⁵ , Z ²⁶ , and M ²¹ are Z ¹¹ , Z ¹² , Z ¹³ , Z ^{11 in the} corresponding general formula (III). , Z ¹² , Z ¹³ , and M ¹¹ , and the preferred range is also the same.

Q ²¹ and Q ²² each represent a group that forms a nitrogen-containing heterocycle. The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is not particularly limited, but a pyrrole ring, an imidazole ring, a triazole ring, and a condensed ring containing them (for example, benzpyrrole), and tautomers thereof ( For example, in the general formula (b) described later, a nitrogen-containing 5-membered ring substituted by R ⁴³ , R ⁴⁴ , R ⁴⁵ , and R ⁴⁶ is preferably defined as a pyrrole tautomer, A condensed ring containing a pyrrole ring (for example, benzpyrrole) is more preferable.

X ²¹ , X ²² , X ²³ and X ²⁴ each independently represent a substituted or unsubstituted carbon atom or nitrogen atom, preferably an unsubstituted carbon atom or nitrogen atom, more preferably a nitrogen atom.

  The compound represented by formula (b) will be described.

In the general formula (b), Z ⁴¹ , Z ⁴² , Z ⁴³ , Z ⁴⁴ , Z ⁴⁵ , Z ⁴⁶ , X ⁴¹ , X ⁴² , X ⁴³ , X ⁴⁴ , and M ⁴¹ are Z ²¹ in the general formula (a). , Z ²² , Z ²³ , Z ²⁴ , Z ²⁵ , Z ²⁶ , X ²¹ , X ²² , X ²³ , X ²⁴ , and M ²¹ , and preferred ranges are also the same.

R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ are each independently a hydrogen atom, or an alkyl group, aryl group, R ⁴³ and R ⁴⁴ exemplified as a substituent on Z ¹¹ or Z ¹² in the general formula (III). Or a group in which R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (for example, benzo-fused ring, pyridine-fused ring, etc.), and an alkyl group, aryl group, R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded. To form a ring structure (eg, benzo-fused ring, pyridine-fused ring, etc.), and R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (eg, benzo-fused ring, pyridine-fused ring). And more preferably a group that forms a ring).

R ⁴³ , R ⁴⁴ , R ⁴⁵ , and R ⁴⁶ each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups described for the substituent on the carbon atom for Z ¹¹ or Z ¹² in the general formula (III).

  The compound represented by formula (c) will be described.

In the general formula (c), Z ¹⁰¹ , Z ¹⁰² , and Z ¹⁰³ each independently represent a substituted or unsubstituted carbon atom or nitrogen atom. At least one of Z ¹⁰¹ , Z ¹⁰² , and Z ¹⁰³ is preferably a nitrogen atom.

L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , and L ¹⁰⁴ each independently represent a single bond or a linking group. The connection is not particularly limited. For example, carbonyl linking group, alkylene group, alkenylene group, arylene group, heteroarylene group, nitrogen-containing heterocyclic linking group, oxygen atom linking group, amino linking group, imino linking group, carbonyl linking group. And a linking group composed of a combination thereof.

L ¹⁰¹ , L ¹⁰² , L ¹⁰³ and L ¹⁰⁴ are each independently preferably a single bond, an alkylene group, an alkenylene group, an amino linking group or an imino linking group, and a single bond, an alkylene linking group, an alkenylene linking group or an imino linking group. A group is more preferable, and a single bond or an alkylene linking group is more preferable.

Q ¹⁰¹ and Q ¹⁰³ are each independently a group coordinated to M ¹⁰¹ by a carbon atom, a group coordinated by a nitrogen atom, a group coordinated by a phosphorus atom, a group coordinated by an oxygen atom, or a sulfur atom. Represents a position group.

The group coordinated to M ¹⁰¹ by a carbon atom is preferably an aryl group coordinated by a carbon atom, a 5-membered heteroaryl group coordinated by a carbon atom, or a 6-membered heteroaryl group coordinated by a carbon atom, An aryl group coordinated with a carbon atom, a nitrogen-containing 5-membered heteroaryl group coordinated with a carbon atom, and a nitrogen-containing 6-membered heteroaryl group coordinated with a carbon atom are more preferred, and an aryl group coordinated with a carbon atom Is more preferable.

The group coordinated to M ¹⁰¹ by a nitrogen atom is preferably a nitrogen-containing 5-membered heteroaryl group coordinated by a nitrogen atom or a nitrogen-containing 6-membered heteroaryl group coordinated by a nitrogen atom, and coordinated by a nitrogen atom The nitrogen-containing 6-membered heteroaryl group is more preferable.

Examples of the group coordinated to M ¹⁰¹ by a phosphorus atom include an alkylphosphine group coordinated by a phosphorus atom, an arylphosphine group coordinated by a phosphorus atom, an alkoxyphosphine group coordinated by a phosphorus atom, and an aryl coordinated by a phosphorus atom. Preferred are an oxyphosphine group, a heteroaryloxyphosphine group coordinated by a phosphorus atom, a phosphinine group coordinated by a phosphorus atom, and a phosphole group coordinated by a phosphorus atom, and an alkylphosphine group coordinated by a phosphorus atom, coordinated by a phosphorus atom. More preferred are arylphosphine groups that are located.

As the group coordinated to M ¹⁰¹ by an oxygen atom, an oxy group and a carbonyl group coordinated by an oxygen atom are preferable, and an oxy group is more preferable.

The group that coordinates to M ¹⁰¹ with a sulfur atom is preferably a sulfide group, a thiophene group, or a thiazole group, and more preferably a thiophene group.

Q ¹⁰¹ and Q ¹⁰³ are preferably a group coordinated to M ¹⁰¹ by a carbon atom, a group coordinated by a nitrogen atom, or a group coordinated by an oxygen atom, a group coordinated by a carbon atom, or a group coordinated by a nitrogen atom Are more preferable, and a group coordinated by a carbon atom is more preferable.

Q ¹⁰² represents a coordinating group, coordinating group phosphorus atom, coordinating group with an oxygen atom or a coordinating group with a sulfur atom, a nitrogen atom in M ^101, more is coordinated group nitrogen atom preferable.

M ¹⁰¹ has the same meaning as M ¹¹ in formula (I), and the preferred range is also the same.

  The compound represented by formula (d) will be described.

In the general formula (d), Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , L ²⁰¹ , L ²⁰² , L ²⁰³ , L ²⁰⁴ , and M ²⁰¹ each correspond to the corresponding general formula (c). Are the same as Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , and M ¹⁰¹ , and the preferred range is also the same. Z ²⁰⁴ , Z ²⁰⁵ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹¹ , and Z ²¹² each represent a substituted or unsubstituted carbon atom or a nitrogen atom, preferably a substituted or unsubstituted carbon atom.

  The compound represented by the general formula (e) will be described.

In the general formula (e), Z ³⁰¹ , Z ³⁰² , Z ³⁰³ , Z ³⁰⁴ , Z ³⁰⁵ , Z ³⁰⁶ , Z ³⁰⁷ , Z ³⁰⁸ , Z ³⁰⁹ , Z ³¹⁰ , L ³⁰¹ , L ³⁰² , L ³⁰³ , L ³⁰⁴ , and M ³⁰¹ represents Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁴ , Z ²⁰⁶ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , Z ²¹⁰ , Z ²¹² , L ¹⁰¹ , in the corresponding general formulas (d) and (c), respectively. ^{L 102, L 103, L 104} , and M ¹⁰¹ in the above formula, the preferred range is also the same.

  The compound represented by formula (f) will be described.

In the general formula (f), Z ⁴⁰¹ , Z ⁴⁰² , Z ⁴⁰³ , Z ⁴⁰⁴ , Z ⁴⁰⁵ , Z ⁴⁰⁶ , Z ⁴⁰⁷ , Z ⁴⁰⁸ , Z ⁴⁰⁹ , Z ⁴¹⁰ , Z ⁴¹¹ , Z ⁴¹² , L ⁴⁰¹ , L ⁴⁰² , L ⁴⁰³ , L ⁴⁰⁴ , and M ⁴⁰¹ are respectively Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁴ , Z ²⁰⁵ , Z ²⁰⁶ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , in the corresponding general formulas (d) and (c), Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , and M ¹⁰¹ have the same meanings, and preferred ranges are also the same. X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom, a substituted or unsubstituted nitrogen atom, or a sulfur atom, preferably an oxygen atom or a substituted nitrogen atom, and more preferably an oxygen atom.

  The compound represented by the general formula (g) will be described.

In the general formula (g), Z ⁵⁰¹ , Z ⁵⁰² , Z ⁵⁰³ , L ⁵⁰¹ , L ⁵⁰² , L ⁵⁰³ , L ⁵⁰⁴ , Q ⁵⁰¹ , Q ⁵⁰² , Q ⁵⁰³ , and M ⁵⁰¹ are the corresponding general formula (c). Are the same as Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , Q ¹⁰¹ , Q ¹⁰³ , Q ¹⁰² , and M ¹⁰¹ , and the preferred range is also the same.

  The compound represented by the general formula (h) will be described.

In the general formula (h), ^Z601 , ^Z602 , ^Z603 , ^Z604 , ^Z605 , ^Z606 , ^Z607 , ^Z608 , ^Z609 , ^Z610 , ^Z611 , ^Z612 , ^L601 , ^L602 , L ⁶⁰³ , L ⁶⁰⁴ , and M ⁶⁰¹ are Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , Z ²⁰⁴ , Z ²⁰⁵ , Z ²⁰⁶ , in the corresponding general formulas (d) and (c), respectively. Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , and M ¹⁰¹ have the same meanings, and preferred ranges are also the same.

  The compound represented by formula (i) will be described.

In general formula (i), Z ⁷⁰¹ , Z ⁷⁰² , Z ⁷⁰³ , Z ⁷⁰⁴ , Z ⁷⁰⁵ , Z ⁷⁰⁶ , Z ⁷⁰⁷ , Z ⁷⁰⁸ , Z ⁷⁰⁹ , Z ⁷¹⁰ , L ⁷⁰¹ , L ⁷⁰² , L ⁷⁰³ , L ⁷⁰⁴ , and M ⁷⁰¹ represents Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , Z ²⁰⁴ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹² , L ¹⁰¹ , in the corresponding general formulas (d) and (c), respectively. ^{L 102, L 103, L 104} , and M ¹⁰¹ in the above formula, the preferred range is also the same.

  The compound represented by formula (j) will be described.

In the general formula ^{(j), Z 801, Z} 802, Z 803, Z 804, Z 805, Z 806, Z 807, Z 808, Z 809, Z 810, Z 811, Z 812, L 801, L 802, L ⁸⁰³ , L ⁸⁰⁴ , M ⁸⁰¹ , X ⁸⁰¹ , and X ⁸⁰² represent Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z in the corresponding general formulas (d), (c), and (f), respectively. ²⁰⁹ , Z ²⁰⁴ , Z ²⁰⁵ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , M ¹⁰¹ , X ⁴⁰¹ , and X ⁴⁰² are the same, and the preferred range is also the same It is.

  Specific examples of the compound represented by the general formula (III) include compound (2) to compound (8), compound (15) to compound (20), compound (27) to compound (described in Japanese Patent Application No. 2004-88575). 32), compound (36) -compound (38), compound (42) -compound (44), compound (50) -compound (52), and compound (57) -compound (154) (the structure is shown below) )), But is not limited thereto.

<Other preferred metal complexes>
Furthermore, as a preferable example of the metal complex in this invention, the following general formula (A-1), the following general formula (B-1), the following general formula (C-1), the following general formula (D-1), the following Each compound represented by general formula (E-1) and the following general formula (F-1) is mentioned.
General formula (A-1) is demonstrated.

In general formula (A-1), M ^A1 represents a metal ion. Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 each independently represent a carbon atom or a nitrogen atom. Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group, and these linking groups may have the same structure or different structures. Q ^A11 and Q ^A12 each represent a partial structure containing an atom that is covalently bonded to M ^A1 .

The compound represented by formula (A-1) will be described in detail.
M ^A1 represents a metal ion. The metal ion is not particularly limited, but a divalent metal ion is preferable, and Pt ²⁺ , Pd ²⁺ , Cu ²⁺ , NI ²⁺ , Co ²⁺ , Zn ²⁺ , Mg ²⁺ , or Pb ²⁺ is preferable, Pt ²⁺ and Cu ²⁺ are more preferable, and Pt ²⁺ is particularly preferable.
Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 each independently represent a carbon atom or a nitrogen atom. Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 are preferably carbon atoms.
Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 are preferably a substituted or unsubstituted carbon atom or a substituted or unsubstituted nitrogen atom.
L ^A11 , L ^A12 , L ^A13 and L ^A14 represent a divalent linking group. The divalent linking groups represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 are each independently composed of a single bond, carbon, nitrogen, silicon, sulfur, oxygen, germanium, or phosphorus. And more preferably a single bond, a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, a substituted silicon atom, an oxygen atom, a sulfur atom, a divalent aromatic hydrocarbon ring group, A monovalent aromatic heterocyclic group, more preferably a single bond, a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, a substituted silicon atom, a divalent aromatic hydrocarbon ring group, a divalent aromatic The divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 , which is a group heterocyclic group, particularly preferably a single bond, a substituted or unsubstituted methylene group, includes, for example: Things.

The divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 may further have a substituent. Examples of the substituent that can be introduced include an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms. For example, methyl, ethyl, Iso-propyl, tert- Butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably Has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl.), An alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly Preferably, it has 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl.

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, and anthranyl). An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino; And alkoxy groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, and 2-ethylhexyl). Siloxy and the like), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably Properly 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy and the like.),

Heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyl A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably 7 carbon atoms). To 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 1 carbon atoms. , And the like such as phenyloxycarbonyl.),

An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), an acylamino group (preferably having a carbon number) 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino and the like, and aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably carbon atoms). 7 to 20, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonylamino And the like.),

A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), a sulfamoyl group ( Preferably it is C0-30, More preferably, it is C0-20, Most preferably, it is C0-12, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc. are mentioned. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl. ),

An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 carbon atoms). To 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, and examples include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, and the like, and sulfonyl groups (preferably. Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, mesyl, tosyl ), Sulfinyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.) ,

Ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include ureido, methylureido, phenylureido), phosphoric acid amide group (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), hydroxy group, mercapto Group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom or 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, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically imidazolyl, pyridyl, quinolyl, Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms). , Particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyl, triphenylsilyl, etc.), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably carbon numbers). 3 to 24, such as trimethylsilyloxy, triphenylsilyloxy And the like.), And the like.

  These substituents may be further substituted. The substituent is preferably an alkyl group, an aryl group, a heterocyclic group, a halogen atom, or a silyl group, more preferably an alkyl group, an aryl group, a heterocyclic group, or a halogen atom, still more preferably an alkyl group, An aryl group, an aromatic heterocyclic group, or a fluorine atom.

Q ^A11 and Q ^A12 each represent a partial structure containing an atom that is covalently bonded to M ^A1 . Q ^A11 and Q ^A12 are independently a group bonded to M ^A1 by a carbon atom, a group bonded by a nitrogen atom, a group bonded by a silicon atom, a group bonded by a phosphorus atom, a group bonded by an oxygen atom, and a sulfur atom. A group to be bonded is preferable, a group bonded to a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom is more preferable, a group bonded to a carbon atom or a nitrogen atom is further preferable, and a group bonded to a carbon atom is particularly preferable.

  The group bonded by carbon atom is preferably an aryl group bonded by carbon atom, a five-membered heteroaryl group bonded by carbon atom, or a six-membered heteroaryl group bonded by carbon atom, and an aryl group bonded by carbon atom A nitrogen-containing five-membered heteroaryl group bonded with a carbon atom and a nitrogen-containing six-membered heteroaryl group bonded with a carbon atom are more preferable, and an aryl group bonded with a carbon atom is particularly preferable.

  The group bonded by a nitrogen atom is preferably a substituted amino group or a nitrogen-containing hetero five-membered heteroaryl group bonded by a nitrogen atom, and particularly preferably a nitrogen-containing hetero five-membered heteroaryl group bonded by a nitrogen atom.

  The group bonded by a phosphorus atom is preferably a substituted phosphino group. As the group bonded by a silicon atom, a substituted silyl group is preferable. The group bonded by an oxygen atom is preferably an oxy group, and the group bonded by a sulfur atom is preferably a sulfide group.

  The compound represented by the general formula (A-1) is more preferably a compound represented by the general formula (A-2), the general formula (A-3), or the general formula (A-4).

In general formula (A-2), M ^A2 represents a metal ion. Y ^A21 , Y ^A24 , Y ^A25 and Y ^A28 each independently represent a carbon atom or a nitrogen atom. Y ^A22 , Y ^A23 , Y ^A26 and Y ^A27 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^A21 , L ^A22 , L ^A23 and L ^A24 represent a linking group. Z ^A21 , Z ^A22 , Z ^A23 , Z ^A24 , Z ^A25 and Z ^A26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In general formula (A-3), M ^A3 represents a metal ion. Y ^A31 , Y ^A34 , Y ^A35 and Y ^A38 each independently represent a carbon atom or a nitrogen atom. Y ^A32 , Y ^A33 , Y ^A36 and Y ^A37 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^A31 , L ^A32 , L ^A33 and L ^A34 each represent a linking group. Z ^A31 , Z ^A32 , Z ^A33 and Z ^A34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In general formula (A-4), M ^A4 represents a metal ion. Y ^A41 , Y ^A44 , Y ^A45 and Y ^A48 each independently represent a carbon atom or a nitrogen atom. Y ^A42 , Y ^A43 , Y ^A46 and Y ^A47 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^A41 , L ^A42 , L ^A43 , and L ^A44 each represent a linking group. Z ^A41 , Z ^A42 , Z ^A43 , Z ^A44 , Z ^A45 and Z ^A46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^A41 and X ^A42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

The compound represented by formula (A-2) will be described in detail.
M ^A2 , Y ^A21 , Y ^A24 , Y ^A25 , Y ^A28 , Y ^A22 , Y ^A23 , Y ^A26 , Y ^A27 , L ^A21 , L ^A22 , L ^A23 , and L ^A24 correspond to the general formula (A-1 ) ^Are the same as M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , and L ^A14. Is the same.
Z ^A21 , Z ^A22 , Z ^A23 , Z ^A24 , Z ^A25 and Z ^A26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^A21 , Z ^A22 , Z ^A23 , Z ^A24 , Z ^A25 and Z ^A26 are preferably each independently a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.

The compound represented by formula (A-3) will be described in detail.
M ^A3 , Y ^A31 , Y ^A34 , Y ^A35 , Y ^A38 , Y ^A32 , Y ^A33 , Y ^A36 , Y ^A37 , L ^A31 , L ^A32 , L ^A33 , and L ^A34 correspond to the general formula (A-1 ) ^Are the same as M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , and L ^A14. Is the same.
Z ^A31 , Z ^A32 , Z ^A33 and Z ^A34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^A31 , Z ^A32 , Z ^A33 and Z ^A34 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.

The compound represented by formula (A-4) will be described in detail.
M ^A4 , Y ^A41 , Y ^A44 , Y ^A45 , Y ^A48 , Y ^A42 , Y ^A43 , Y ^A46 , Y ^A47 , L ^A41 , L ^A42 , L ^A43 , and L ^A44 correspond to the general formula (A-1 ) ^Are the same as M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , and L ^A14. Is the same.
Z ^A41 , Z ^A42 , Z ^A43 , Z ^A44 , Z ^A45 and Z ^A46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^A41 , Z ^A42 , Z ^A43 , Z ^A44 , Z ^A45 and Z ^A46 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.
X ^A41 and X ^A42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^A41 and X ^A42 are preferably each independently an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

  Specific examples of the compound represented by formula (A-1) are listed below, but the present invention is not limited to these compounds.

  Of the metal complexes in the present invention, one of the preferred compounds is a compound represented by the following general formula (B-1).

In formula (B-1), M ^B1 represents a metal ion. Y ^B11, Y ^B14, Y ^B15 and Y ^B18 represents a carbon atom or a nitrogen atom independently. Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^B11 , L ^B12 , L ^B13 , and L ^B14 each represent a linking group. Q ^B11 and Q ^B12 each represents a partial structure containing an atom bonded to M ^B1 through a covalent bond.

General formula (B-1) is demonstrated in detail.
In the general formula (B-1), M ^B1 , Y ^B11 , Y ^B14 , Y ^B15 , Y ^B18 , Y ^B12 , Y ^B13 , Y ^B16 , Y ^B17 , L ^B11 , L ^B12 , L ^B13 , L ^B14 , Q ^B11 , And Q ^B12 respectively correspond to M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L in the general formula (A-1). It is synonymous with ^A12 , L ^A13 , L ^A14 , Q ^A11 , and Q ^A12 , and the preferred range is also the same.

  The compound represented by the general formula (B-1) is more preferably a compound represented by the following general formula (B-2), general formula (B-3), or general formula (B-4). .

In formula (B-2), M ^B2 represents a metal ion. Y ^B21 , Y ^B24 , Y ^B25 and Y ^B28 each independently represent a carbon atom or a nitrogen atom. Y ^B22 , Y ^B23 , Y ^B26 and Y ^B27 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, oxygen atom or sulfur atom. L ^B21 , L ^B22 , L ^B23 , and L ^B24 each represent a linking group. Z ^B21 , Z ^B22 , Z ^B23 , Z ^B24 , Z ^B25 and Z ^B26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In formula (B-3), M ^B3 represents a metal ion. Y ^B31 , Y ^B34 , Y ^B35 and Y ^B38 each independently represent a carbon atom or a nitrogen atom. Y ^B32 , Y ^B33 , Y ^B36 and Y ^B37 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^B31 , L ^B32 , L ^B33 , and L ^B34 each represent a linking group. Z ^B31 , Z ^B32 , Z ^B33 and Z ^B34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In formula (B-4), M ^B4 represents a metal ion. Y ^B41 , Y ^B44 , Y ^B45 and Y ^B48 each independently represent a carbon atom or a nitrogen atom. Y ^B42 , Y ^B43 , Y ^B46 and Y ^B47 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, oxygen atom or sulfur atom. L ^B41 , L ^B42 , L ^B43 , and L ^B44 each represent a linking group. Z ^B41 , Z ^B42 , Z ^B43 , Z ^B44 , Z ^B45 and Z ^B46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^B41 and X ^B42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

The compound represented by formula (B-2) will be described in detail.
In formula (B-2), M ^B2 , Y ^B21 , Y ^B24 , Y ^B25 , Y ^B28 , Y ^B22 , Y ^B23 , Y ^B26 , Y ^B27 , L ^B21 , L ^B22 , L ^B23 , and L ^B24 are each M ^B1 , Y ^B11 , Y ^B14 , Y ^B15 , Y ^B18 , Y ^B12 , Y ^B13 , Y ^B16 , Y ^B17 , L ^B11 , L ^B12 , L ^B13 , and L in the general formula (B-1) ^It is synonymous with ^B14 , and the preferred range is also the same.
Z ^B21 , Z ^B22 , Z ^B23 , Z ^B24 , Z ^B25 and Z ^B26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^B21 , Z ^B22 , Z ^B23 , Z ^B24 , Z ^B25 and Z ^B26 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.

The compound represented by formula (B-3) will be described in detail.
In the general formula (B-3), M ^B3 , Y ^B31 , Y ^B34 , Y ^B35 , Y ^B38 , Y ^B32 , Y ^B33 , Y ^B36 , Y ^B37 , L ^B31 , L ^B32 , L ^B33 , and L ^B34 are each M ^B1 , Y ^B11 , Y ^B14 , Y ^B15 , Y ^B18 , Y ^B12 , Y ^B13 , Y ^B16 , Y ^B17 , L ^B11 , L ^B12 , L ^B13 , and L in the general formula (B-1) ^It is synonymous with ^B14 , and the preferred range is also the same.
Z ^B31 , Z ^B32 , Z ^B33 , and Z ^B34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^B31 , Z ^B32 , Z ^B33 , and Z ^B34 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.

The compound represented by formula (B-4) will be described in detail.
In the general formula (B-4), M ^B4 , Y ^B41 , Y ^B44 , Y ^B45 , Y ^B48 , Y ^B42 , Y ^B43 , Y ^B46 , Y ^B47 , L ^B41 , L ^B42 , L ^B43 , and L ^B44 are each M ^B1 , Y ^B11 , Y ^B14 , Y ^B15 , Y ^B18 , Y ^B12 , Y ^B13 , Y ^B16 , Y ^B17 , L ^B11 , L ^B12 , L ^B13 , and L in the general formula (B-1) ^It is synonymous with ^B14 , and the preferred range is also the same.
Z ^B41 , Z ^B42 , Z ^B43 , Z ^B44 , Z ^B45 and Z ^B46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^B41 , Z ^B42 , Z ^B43 , Z ^B44 , Z ^B45 and Z ^B46 are preferably substituted or unsubstituted carbon atoms, more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.
X ^B41 and X ^B42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^B41 and X ^B42 are preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

  Specific examples of the compound represented by formula (B-1) are listed below, but the present invention is not limited to these compounds.

  Among the metal complexes in the present invention, one of the preferable compounds is a compound represented by the general formula (C-1).

In formula (C-1), M ^C1 represents a metal ion. R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent that is connected to each other to form a five-membered ring, or a substituent that is not connected to each other. R ^C13 and R ^C14 each independently represent a hydrogen atom, a substituent that is connected to each other to form a five-membered ring, or a substituent that is not connected to each other. G ^C11 and G ^C12 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C11 and L ^C12 each represent a linking group. Q ^C11 and Q ^C12 each represents a partial structure containing an atom that is covalently bonded to M ^C1 .

The general formula (C-1) will be described in detail.
In the general formula (C-1), M ^C1 , L ^C11 , L ^C12 , Q ^C11 , and Q ^C12 are M ^A1 , L ^A11 , L ^A12 , Q ^A11 , and Q ^A11 in the corresponding general formula (A-1), respectively. And Q ^A12 has the same meaning, and the preferred range is also the same.
G ^C11 and G ^C12 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, preferably a nitrogen atom or an unsubstituted carbon atom, and more preferably a nitrogen atom.
R ^C11 and R ^C12 each independently represent a hydrogen atom or a substituent. R ^C11 and R ^C12 may ^combine with each other to form a five-membered ring. R ^C13 and R ^C14 each independently represent a hydrogen atom or a substituent. R ^C13 and R ^C14 may ^combine with each other to form a five-membered ring.

The substituent represented by R ^C11 , R ^C12 , R ^C13 and R ^C14 is an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms). And methyl, ethyl, Iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms). More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc. It is below.),

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, and anthranyl). An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and And dtolylamino), an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, and 2-ethyl Hexyloxy and the like), an aryloxy group (preferably having 6 to 30 carbon atoms, Ri preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy and the like.),

Heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyl A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably 7 carbon atoms). To 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 1 carbon atoms. , And the like such as phenyloxycarbonyl.),

An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), an acylamino group (preferably having a carbon number) 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino and the like, and aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably carbon atoms). 7 to 20, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonylamino And the like.),

An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 carbon atoms). To 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, and examples include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, and the like, halogen atoms (for example, Fluorine atom, chlorine atom, bromine atom or iodine atom), cyano group,

Heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically imidazolyl, pyridyl, quinolyl, Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms). , Particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyl, triphenylsilyl, etc.), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably carbon numbers). 3 to 24, such as trimethylsilyloxy, triphenylsilyloxy And the like.), And the like.

As the substituent represented by R ^C11 , R ^C12 , R ^C13 and R ^C14 , an alkyl group, an aryl group, a group in which R ^C11 and R ^C12 , R ^C13 and R ^C14 are bonded to each other to form a five-membered ring Particularly preferably, R ^C11 and R ^C12 , and R ^C13 and R ^C14 are bonded to each other to form a five-membered ring.

  The compound represented by the general formula (C-1) is more preferably a compound represented by the general formula (C-2).

In formula (C-2), M ^C2 represents a metal ion.
Y ^C21 , Y ^C22 , Y ^C23 and Y ^C24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. G ^C21, G ^C22 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C21 and L ^C22 each represent a linking group. Q ^C21 and Q ^C22 each represents a partial structure containing an atom bonded to M ^C2 through a covalent bond.

General formula (C-2) is demonstrated in detail.
In the general formula (C-2), M ^C2 , L ^C21 , L ^C22 , Q ^C21 , Q ^C22 , G ^C21 , and G ^C22 correspond to M ^C1 , L ^C11 , L in the general formula (C-1), respectively. ^{C12, Q C11, Q C12,} G C11, and have the same meaning as G ^C12, preferred ranges are also the same.
Y ^C21 , Y ^C22 , Y ^C23 and Y ^C24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom. It is.

  The compound represented by the general formula (C-2) is more preferably a compound represented by the following general formula (C-3), general formula (C-4), or general formula (C-5).

In general formula (C-3), M ^C3 represents a metal ion.
Y ^C31 , Y ^C32 , Y ^C33 and Y ^C34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. G ^C31, G ^C32 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C31 and L ^C32 each represent a linking group. Z ^C31 , Z ^C32 , Z ^C33 , Z ^C34 , Z ^C35 and Z ^C36 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In formula (C-4), M ^C4 represents a metal ion. Y ^C41 , Y ^C42 , Y ^C43 and Y ^C44 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. G ^C41, G ^C42 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C41 and L ^C42 each represent a linking group. Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In formula (C-5), M ^C5 represents a metal ion.
Y ^C51 , Y ^C52 , Y ^C53 and Y ^C54 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. G ^C51 and G ^C52 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C51 and L ^C52 represent a linking group. Z ^C51 , Z ^C52 , Z ^C53 , Z ^C54 , Z ^C55 and Z ^C56 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^C51 and X ^C52 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

The compound represented by formula (C-3) will be described in detail.
In the general formula (C-3), M ^C3 , L ^C31 , L ^C32 , G ^C31 , and G ^C32 respectively correspond to M ^C1 , L ^C11 , L ^C12 , G ^C11 , in the general formula (C-1). And G ^C12 , and the preferred range is also the same.
Z ^C31 , Z ^C32 , Z ^C33 , Z ^C34 , Z ^C35 and Z ^C36 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^C31 , Z ^C32 , Z ^C33 , Z ^C34 , Z ^C35 and Z ^C36 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms.

The compound represented by formula (C-4) will be described in detail.
In the general formula (C-4), M ^C4 , L ^C41 , L ^C42 , G ^C41 , and G ^C42 are M ^C1 , L ^C11 , L ^C12 , G ^C11 , and G ^C42 in the corresponding general formula (C-1), respectively. And G ^C12 , and the preferred range is also the same.
Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 are preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom.

The compound represented by formula (C-5) will be described in detail.
M ^C5 , L ^C51 , L ^C52 , G ^C51 , and G ^C52 have the same ^meanings as M ^C1 , L ^C11 , L ^C12 , G ^C11 , and G ^{C12 in the} corresponding general formula (C-1). The preferable range is also the same.
Z ^C51 , Z ^C52 , Z ^C53 , Z ^C54 , Z ^C55 and Z ^C56 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^C51 , Z ^C52 , Z ^C53 , Z ^C54 , Z ^C55 and Z ^C56 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms.
X ^C51 and X ^C52 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^C51 and X ^C52 are preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

  Specific examples of the compound represented by formula (C-1) are listed below, but the present invention is not limited to these compounds.

  Among the metal complexes in the present invention, one of the preferable compounds is a compound represented by the following general formula (D-1).

In general formula (D-1), M ^D1 represents a metal ion.
G ^D11 and G ^D12 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. J ^D11 , J ^D12 , J ^D13 and J ^D14 represent an atomic group necessary for forming a five-membered ring. L ^D11 and L ^D12 each represent a linking group.

The general formula (D-1) will be described in detail.
In the general formula (D-1), M ^D1 , L ^D11 , and L ^D12 have the same ^meanings as M ^A1 , L ^A11 , and L ^{A12 in the} corresponding general formula (A-1), respectively, and preferred ranges are also included. It is the same.
G ^D11 and G ^D12 have the same ^meanings as G ^C11 and G ^C12 in the corresponding general formula (C-1), and preferred ranges are also the same.
J ^D11 , J ^D12 , J ^D13 and J ^D14 represent an atomic group necessary for forming a nitrogen-containing hetero five-membered ring together with the atomic group to which they are bonded.

  The compound represented by the general formula (D-1) is more preferably a compound represented by the following general formula (D-2), general formula (D-3), or general formula (D-4).

In general formula (D-2), M ^D2 represents a metal ion.
G ^D21 and G ^D22 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
Y ^D21 , Y ^D22 , Y ^D23 and Y ^D24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
X ^D21 , X ^D22 , X ^D23 and X ^D24 each independently represent an oxygen atom, a sulfur atom, —NR ^D21 —, —C (R ^D22 ) R ^D23 —.
R ^D21 , R ^D22 and R ^D23 each independently represent a hydrogen atom or a substituent. L ^D21 and L ^D22 each represent a linking group.

In formula (D-3), M ^D3 represents a metal ion.
G ^D31 and G ^D32 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
Y ^D31 , Y ^D32 , Y ^D33 and Y ^D34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
X ^D31 , X ^D32 , X ^D33 and X ^D34 each independently represent an oxygen atom, a sulfur atom, —NR ^D31 —, —C (R ^D32 ) R ^D33 —.
R ^D31 , R ^D32 and R ^D33 each independently represent a hydrogen atom or a substituent. L ^D31 and L ^D32 each represent a linking group.

In formula (D-4), M ^D4 represents a metal ion.
G ^D41 and G ^D42 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
Y ^D41 , Y ^D42 , Y ^D43 and Y ^D44 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
X ^D41 , X ^D42 , X ^D43 and X ^D44 each independently represent an oxygen atom, a sulfur atom, —NR ^D41 —, —C (R ^D42 ) R ^D43 —. R ^D41 , R ^D42 and R ^D43 each independently represent a hydrogen atom or a substituent. L ^D41 and L ^D42 each represent a linking group.

General formula (D-2) is demonstrated in detail.
M ^D2 , L ^D21 , L ^D22 , G ^D21 , and G ^D22 are synonymous with M ^D1 , L ^D11 , L ^D12 , G ^D11 , and G ^D12 in the general formula (D-1), and preferred ranges are also the same. It is.
Y ^D21 , Y ^D22 , Y ^D23 and Y ^D24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom. is there.

X ^D21 , X ^D22 , X ^D23 and X ^D24 each independently represent an oxygen atom, a sulfur atom, —NR ^D21 —, —C (R ^D22 ) R ^D23 —, preferably a sulfur atom, —NR ^D21 —, — C (R ^D22 ) R ^D23 —, more preferably —NR ^D21 —, —C (R ^D22 ) R ^D23 —, and still more preferably —NR ^D21 —.

R ^D21 , R ^D22 and R ^D23 each independently represent a hydrogen atom or a substituent. Examples of the substituent represented by R ^D21 , R ^D22 and R ^D23 include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms. , Ethyl, Iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably Has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl.), An alkynyl group (preferably having 2 to 20 carbon atoms, and more). Preferably it is C2-C12, Most preferably, it is C2-C8, for example, a propargyl, 3-pentynyl etc. are mentioned).

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, and naphthyl), substituted carbonyl Groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms such as acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, and phenylaminocarbonyl A substituted sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Heterocyclic groups (including aliphatic heterocyclic groups and aromatic heterocyclic groups, preferably oxygen atoms, sulfur atoms Any one of nitrogen atoms, preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxa And azolyl and triazolyl groups). R ^D21 , R ^D22 and R ^D23 are preferably an alkyl group, an aryl group or an aromatic heterocyclic group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.

General formula (D-3) is demonstrated in detail.
In the general formula (D-3), M ^D3 , L ^D31 , L ^D32 , G ^D31 , and G ^D32 are M ^D1 , L ^D11 , L ^D12 , G ^D11 , and G in the corresponding general formula (D-1), respectively. ^It is synonymous with ^D12 , and a preferable range is also the same.
X ^D31 , X ^D32 , X ^D33 and X ^D34 have the same ^{meanings as} X ^D21 , X ^D22 , X ^D23 and X ^{D24 in the} corresponding general formula (D-2), and preferred ranges are also the same.
Y ^D31 , Y ^D32 , Y ^D33 and Y ^D34 have the same meaning as Y ^D21 , Y ^D22 , Y ^D23 and Y ^{D24 in the} corresponding general formula (D-2), and preferred ranges are also the same.

General formula (D-4) will be described in detail.
In the general formula (D-4), M ^D4 , L ^D41 , L ^D42 , G ^D41 , and G ^D42 correspond to M ^D1 , L ^D11 , L ^D12 , G ^D11 , and in the general formula (D-1), respectively. have the same meaning as G ^D12, the preferred ranges are also the same.
X ^D41 , X ^D42 , X ^D43 and X ^D44 are synonymous with X ^D21 , X ^D22 , X ^D23 and X ^{D24 in the} corresponding general formula (D-2), respectively, and preferred ranges are also the same. Y ^D41 , Y ^D42 , Y ^D43 and Y ^D44 have the same ^{meanings as} Y ^D21 , Y ^D22 , Y ^D23 and Y ^{D24 in the} corresponding general formula (D-2), and preferred ranges are also the same.

  Specific examples of the compound represented by the general formula (D-1) are listed below, but the present invention is not limited to these compounds.

  Of the metal complexes in the present invention, one of the preferable compounds is a compound represented by the following general formula (E-1).

In Formula ^(E1), M E1 represents a metal ion. J ^E11 and J ^E12 represent an atomic group necessary for forming a five-membered ring. G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

The general formula (E-1) will be described in detail.
In formula (E-1), M ^E1 has the same meaning as M ^A1 in formula (A-1), and the preferred range is also the same. G ^E11 , G ^E12 , G ^E13 and G ^E14 have the same ^{meanings as} G ^C11 and G ^C12 in formula (C-1), and preferred ranges are also the same.
J ^E11 and J ^E12 have the same ^{meanings as} J ^{D12 to} J ^D14 in formula (D-1), and preferred ranges are also the same. Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 have the same meanings as Y ^{C21 to} Y ^C24 in the general formula (C-2), and the preferred ranges are also the same.

  The compound represented by the general formula (E-1) is more preferably a compound represented by the following general formula (E-2) or general formula (E-3).

In formula (E-2), M ^E2 represents a metal ion. G ^E21 , G ^E22 , G ^E23 and G ^E24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Y ^E21 , Y ^E22 , Y ^E23 , Y ^E24 , Y ^E25 and Y ^E26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.
X ^E21 and X ^E22 each independently represent an oxygen atom, a sulfur atom, —NR ^E21 —, —C (R ^E22 ) R ^E23 —. R ^E21, R ^E22 and R ^E23 each independently represent a hydrogen atom or a substituent.

In formula (E-3), M ^E3 represents a metal ion. J ^E31, J ^E32 represents an atomic group necessary for forming a five-membered ring each independently. G ^E31 , G ^E32 , G ^E33 and G ^E34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Y ^E31 , Y ^E32 , Y ^E33 , Y ^E34 , Y ^E35 and Y ^E36 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^E31 and X ^E32 each independently represent an oxygen atom, a sulfur atom, —NR ^E31 —, or —C (R ^E32 ) R ^E33 —. R ^E31 , R ^E32 and R ^E33 each independently represent a hydrogen atom or a substituent.

General formula (E-2) is demonstrated in detail.
In the general formula (E-2), M ^E2 , G ^E21 , G ^E22 , G ^E23 , G ^E24 , Y ^E21 , Y ^E22 , Y ^E23 , and Y ^E24 are M ^E1 in the corresponding general formula (E-1). , G ^E11 , G ^E12 , G ^E13 , G ^E14 , Y ^E11 , Y ^E12 , Y ^E13 , and Y ^E14 , and the preferred ranges are also the same. X ^E21 and X ^E22 have the same ^meanings as X ^D21 and X ^D22 in formula (D-2), and preferred ranges are also the same.

The general formula (E-3) will be described in detail.
In general formula (E-3), M ^E3 , G ^E31 , G ^E32 , G ^E33 , G ^E34 , Y ^E31 , Y ^E32 , Y ^E33 , and Y ^E34 correspond to M in general formula (E-1), respectively. ^{E 1} , G ^E11 , G ^E12 , G ^E13 , G ^E14 , Y ^E11 , Y ^E12 , Y ^E13 , and Y ^E14 have the same ^meanings , and preferred ranges are also the same. X ^E31 and X ^E32 have the same meaning as X ^E21 and X ^E22 in the corresponding general formula (E-2), and preferred ranges are also the same.

  Specific examples of the compound represented by the general formula (E-1) are listed below, but the present invention is not limited to these compounds.

  One of the preferable compounds among the metal complexes in the present invention is a compound represented by the following general formula (F-1).

In general formula (F-1), M ^F1 represents a metal ion. L ^F11 , L ^F12 and L ^F13 each represent a linking group. R ^F11 , R ^F12 , R ^F13 and R ^F14 each independently represent a hydrogen atom or a substituent, and R ^F11 and R ^F12 , R ^F12 and R ^F13 , and R ^F13 and R ^F14 are linked to each other if possible. The ring formed by R ^F11 and R ^F12 , R ^F13 and R ^F14 is a five-membered ring. Q ^F11 and Q ^F12 each represents a partial structure containing an atom that is covalently bonded to M ^F1 .

The compound represented by formula (F-1) will be described in detail.
In general formula (F-1), M ^F1 , L ^F11 , L ^F12 , L ^F13 , Q ^F11 , and Q ^F12 correspond to M ^A1 , L ^A11 , L ^A12 , L in general formula (A-1), respectively. ^A13, Q ^A11, and Q ^A12 in the above formula, preferred ranges are also the same. R ^F11 , R ^F12 , R ^F13 and R ^F14 each independently represent a hydrogen atom or a substituent, and R ^F11 and R ^F12 , R ^F12 and R ^F13 , and R ^F13 and R ^F14 are linked to each other if possible. A ring may be formed, but the ring formed by R ^F11 and R ^F12 , R ^F13 and R ^F14 is a five-membered ring. As the substituents represented by R ^F11 , R ^F12 , R ^F13 and R ^F14 , those ^exemplified as the substituents represented by R ^{C11 to} R ^C14 in the corresponding general formula (C-1) can be applied. R ^F11 , R ^F12 , R ^F13 and R ^F14 are preferably a group in which R ^F11 and R ^F12 , R ^F13 and R ^F14 are bonded to each other to form a five-membered ring, or R ^F12 and R ^F13 are bonded to each other It is a group that forms an aromatic ring.

  The compound represented by the general formula (F-1) is more preferably a compound represented by the following general formula (F-2), general formula (F-3), or general formula (F-4).

In general formula (F-2), M ^F2 represents a metal ion. L ^F21 , L ^F22 and L ^F23 each represent a linking group. R ^F21 , R ^F22 , R ^F23 and R ^F24 represent substituents, and R ^F21 and R ^F22 , R ^F22 and R ^F23 , and R ^F23 and R ^F24 may be linked to each other to form a ring, if possible. However, the ring formed by R ^F21 and R ^F22 and R ^F23 and R ^F24 is a five-membered ring. Z ^F21 , Z ^F22 , Z ^F23 , Z ^F24 , Z ^F25 and Z ^F26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In general formula (F-3), M ^F3 represents a metal ion. L ^F31 , L ^F32 and L ^F33 each represent a linking group. R ^F31 , R ^F32 , R ^F33 and R ^F34 represent a substituent, and R ^F31 and R ^F32 , R ^F32 and R ^F33 , and R ^F33 and R ^F34 may be connected to each other to form a ring, if possible. However, the ring formed by R ^F31 and R ^F32 and R ^F33 and R ^F34 is a five-membered ring. Z ^F31 , Z ^F32 , Z ^F33 and Z ^F34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In general formula (F-4), M ^F4 represents a metal ion. L ^F41 , L ^F42 and L ^F43 each represent a linking group. R ^F41 , R ^F42 , R ^F43 and R ^F44 each represent a substituent, and R ^F41 and R ^F42 , R ^F42 and R ^F43 , and R ^F43 and R ^F44 may be linked to each other to form a ring, if possible. However, the ring formed by R ^F41 and R ^F42 and R ^F43 and R ^F44 is a five-membered ring. Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 , and Z ^F46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^F41 and X ^F42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

The compound represented by formula (F-2) will be described in detail.
M ^F2 , L ^F21 , L ^F22 , L ^F23 , R ^F21 , R ^F22 , R ^F23 and R ^F24 are M ^F1 , L ^F11 , L ^F12 , L ^F13 , R ^F11 , R ^F11 in the corresponding general formula (F-1), respectively. It is synonymous with R ^F12 , R ^F13 and R ^F14 , and the preferred range is also the same.
Z ^F21 , Z ^F22 , Z ^F23 , Z ^F24 , Z ^F25 and Z ^F26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^F21 , Z ^F22 , Z ^F23 , Z ^F24 , Z ^F25 and Z ^F26 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.

The compound represented by formula (F-3) will be described in detail.
In general formula (F-3), M ^F3 , L ^F31 , L ^F32 , L ^F33 , R ^F31 , R ^F32 , R ^F33 and R ^F34 correspond to M ^F1 and L ^F11 in general formula (F-1), respectively. , L ^F12 , L ^F13 , R ^F11 , R ^F12 , R ^F13 and R ^F14, and preferred ranges are also the same. Z ^F31 , Z ^F32 , Z ^F33 and Z ^F34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^F31 , Z ^F32 , Z ^F33 and Z ^F34 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.

The compound represented by formula (F-4) will be described in detail.
In the general formula (F-4), M ^F4 , L ^F41 , L ^F42 , L ^F43 , R ^F41 , R ^F42 , R ^F43 and R ^F44 are M ^F1 , L ^F11 , L ^F12 , It is synonymous with L ^F13 , R ^F11 , R ^F12 , R ^F13 and R ^F14 , and the preferred range is also the same.
Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 and Z ^F46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 and Z ^F46 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.
X ^F41 and X ^F42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^F41 and X ^F42 are preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

  Specific examples of the compound represented by formula (F-1) are listed below, but the present invention is not limited to these compounds.

  The compounds represented by the general formulas (A-1) to (F-1) can be synthesized by a known method.

4) Other components The organic electroluminescent element of the present invention may have the following components.
<Host material>
The host material is a component constituting the light-emitting layer, and the holes received from the anode, the hole injection layer, the hole transport layer, etc., and the electrons received from the cathode, the electron injection layer, the electron transport layer, etc. Or excitons generated by recombination of holes and electrons are transmitted to the light emitting material. The host material is selected in consideration of each energy level such as the ionization potential and electron affinity of the material of the adjacent layer and the light emitting material, preferably an amine compound (triarylamine compound, etc.), aluminum, zinc, or other transition metal Metal chelated oxinoid compounds (having a metal-oxygen bond), polyarylene compounds (hexaphenylbenzene derivatives, etc.) composed of a metal such as 8-hydroxyquinoline derivatives and 2- (2-pyridino) phenol derivatives ), Condensed aromatic carbocyclic compounds, non-heteroaromatic nitrogen-containing heterocyclic compounds (such as carbazole compounds), and the like.

<Board>
As the substrate, soda lime glass, non-alkali glass, transparent resin substrate and the like can be used. In the case of a glass substrate, non-alkali glass is preferred because it reduces the elution of ions from the glass. When soda lime glass is used, it is preferable to provide a barrier layer such as silica. When a glass substrate is used, the thickness of the substrate is preferably 0.2 mm or more, and more preferably 0.7 mm or more.

<Hole injection / transport layer>
The hole injection / transport layer has a function of injecting and transporting holes from the anode and blocking electrons injected from the cathode. The hole injection / transport layer is selected in consideration of each energy level such as the ionization potential and electron affinity of the material of the adjacent layer, preferably a carbazole derivative, a triazole derivative, an oxazole derivative, an oxadiazole derivative, an imidazole derivative. , Polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine Compounds, aromatic dimethylidyne compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, aniline copolymers, thiophene oligomers and polymers Conductive polymer oligomers thiophene, etc., organic silane compound, a metal complex or the like of the carbon film, and the present invention. In particular, the material for the hole injection layer is copper phthalocyanine or a starburst amine compound.

Although there is no restriction | limiting in particular as a film thickness of a positive hole injection layer, 1 nm or more and 5 micrometers or less are preferable, 5 nm or more and 1 micrometer or less are more preferable, and 10 nm or more and 500 nm or less are especially preferable. Although there is no restriction | limiting in particular as a film thickness of a positive hole transport layer, 1 nm or more and 5 micrometers or less are preferable, 5 nm or more and 1 micrometer or less are more preferable, and 10 nm or more and 500 nm or less are especially preferable. The hole injection layer or the hole transport layer may be a single layer or a laminated structure of two or more layers.
A positive hole injection layer and a positive hole transport layer can be formed by well-known methods, such as a vacuum evaporation method, LB method, the apply | coating method, the inkjet method, the printing method, the transfer method.

<Electron injection / transport layer>
The electron injection / transport layer has a function of injecting and transporting electrons from the cathode and blocking holes injected from the anode. The electron injection / transport layer is selected in consideration of each energy level such as the ionization potential and electron affinity of the material of the adjacent layer, preferably a metal chelated oxinoid compound, a polyarylene compound, a condensed aromatic carbocyclic compound, Non-heteroaromatic heterocyclic compounds and the like. In particular, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine Derivatives, tetracarboxylic anhydrides of aromatic rings such as naphthalene and perylene, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives, metal complexes such as metalated phthalocyanines, benzoxazole or metal complexes having a benzothiazole ligand Complexes, organosilane compounds and the like.

The thickness of the electron injection layer is not particularly limited, but is preferably 1 nm to 5 μm, more preferably 5 nm to 1 μm, and particularly preferably 10 nm to 500 nm. The thickness of the electron transport layer is not particularly limited, but is preferably 1 nm to 5 μm, more preferably 5 nm to 1 μm, and particularly preferably 10 nm to 500 nm. The electron injection layer or the electron transport layer may be a single layer or a laminated structure of two or more layers.
A positive hole injection layer and a positive hole transport layer can be formed by well-known methods, such as a vacuum evaporation method, LB method, the apply | coating method, the inkjet method, the printing method, the transfer method.

<Charge blocking layer>
The charge blocking layer has a function of blocking holes injected from the anode or electrons injected from the cathode and limiting a light emitting region. The charge blocking layer is an electron blocking layer disposed between the light emitting layer and the anode, or a hole blocking layer disposed between the light emitting layer and the cathode, and each of the ionization potential, electron affinity, etc. of the material contained in the light emitting layer Select with energy level in mind. In general, the electron blocking layer can be selected from an electron transporting material, and the hole blocking layer can be selected from an electron transporting material. In particular, the hole blocking layer is preferably disposed between the light emitting layer and the electron transporting layer, and the ionization potential of the material contained in the hole blocking layer is preferably 5.9 eV or more.

<Others>
Other components such as other substrates, electrodes, organic layers, and other layers in the organic electroluminescent device of the present invention are described in, for example, paragraph numbers (0013) to (0082) of JP-A-2004-221068. No. 2004-214178, paragraph numbers (0017) to (0091), JP-A No. 2004-146067, paragraph numbers (0024) to (0035), JP-A No. 2004-103577, paragraph numbers (0017) to (0068), Paragraph numbers (0014) to (0062) of JP-A No. 2003-323987, paragraph numbers (0015) to (0077) of JP-A No. 2002-305083, paragraph numbers (0008) to (0028) of JP-A No. 2001-172284 JP-A-2000-186094, paragraph numbers (0013) to (0075), Special Table 2003 Those from 15897 Paragraph Nos (0016) according to (0118) and the like can be similarly applied to the present invention. However, the present invention is not limited to these.

3. Driving method of organic electroluminescence device The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, and JP-A-8-234585. The driving methods described in the publications of U.S. Pat. No. 8-2441047, Japanese Patent No. 2784615, U.S. Pat. Nos. 5,828,429, 6023308, and the like can be applied.

In the present invention, light emission can be obtained by applying a direct current (which may include an alternating current component if necessary) voltage (usually 2 to 30 volts, or a direct current) between the anode and the cathode.
In the present invention, a constant current source (400 μA) was applied to an EL element to emit light using a source measure unit type 2400 manufactured by Toyo Technica, and the driving voltage and power efficiency at that time were calculated. The luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation. On the other hand, the emission peak wavelength and the waveform of the emission spectrum were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics, and the x and y coordinates of the CIE color coordinates were obtained.

  In the present invention, the light extraction efficiency is 20% or more by devising the substrate shape, electrode shape, organic layer thickness, inorganic layer thickness, organic layer refractive index, inorganic layer refractive index, and the like. It is possible to

4). Applications Applications of the organic electroluminescent device of the present invention are not particularly limited, but can be applied to a wide range of fields such as mobile phone displays, personal digital assistants (PDAs), computer displays, automobile information displays, TV monitors, or general lighting.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

(Example)
An ITO anode having a width of 2 mm and a film thickness of 200 nm was formed on a 20 mm × 20 mm × 0.7 mm soda glass substrate. On the ITO anode, larger than the pixel region, CuPC (10 nm), NPD (30 nm), multidentate metal complex compound (215) (100 nm), Balq (10 nm), Alq (40 nm), LiF (0.5 nm) are resisted. Vapor deposition was performed sequentially by the heating vapor deposition method.
An Al cathode having a width of 2 mm and a film thickness of 200 nm was formed by resistance heating vapor deposition so as to be orthogonal to the ITO anode. After connecting the lead lines to the anode and the cathode, the pixel region was sealed with a sealing member provided with a desiccant.
At this time, an element in which the content of the compound (215) in the light emitting layer was 35% by mass, 55% by mass, and 75% by mass was produced.

(Comparative example)
A device was fabricated in the same manner as in Example except that the content of the compound (215) in the light emitting layer was 25% by mass.

<Evaluation results>
The power efficiency and emission color of the devices of the examples and comparative examples are shown in the table below.

  The device of the example showed higher power efficiency than the device of the comparative example, and almost no change in chromaticity was observed. It has been found that the device of the present invention can emit light with high efficiency without causing so-called concentration quenching even when the content of the light emitting material exceeds 30% by mass, and does not generate long wavelength light emission due to aggregates or the like. Furthermore, the drive voltage decreased at a content of 50% by mass or more. This is considered to be due to the fact that the charge injection and movement of the light emitting layer is easier than the low content.

Claims (7)

  An organic electroluminescence device having at least one light emitting layer between a pair of opposing anodes and cathodes, wherein the light emitting layer has a metal complex having a tetradentate or more ligand as a light emitting material. An organic electroluminescence device comprising 30% by mass to 100% by mass of the mass, wherein main light emission in an emission spectrum is light emission by a monomer body of the metal complex.   2. The organic electroluminescent element according to claim 1, wherein the metal complex is contained in an amount of 50% by mass to 100% by mass with respect to the total mass of the light emitting layer. The organic electroluminescent device according to claim 1 or 2, wherein the metal complex having a tetradentate or higher ligand is a compound represented by the following general formula (I):

(In the general formula (I), M ¹¹ represents a metal ion, and L ^{11 to} L ¹⁵ each represents a ligand coordinated to M ^{11. An} atomic group further exists between L ¹¹ and L ^14. L ¹⁵ may be bonded to both L ¹¹ and L ¹⁴ to form a cyclic ligand, and Y ¹¹ , Y ¹² , and Y ¹³ are each a linking group. In addition, when Y ¹¹ , Y ¹² or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and The bonds between L ¹³ , L ¹³ and Y ¹³ , and Y ¹³ and L ¹⁴ each independently represent a single bond or a double bond, n ¹¹ represents 0 to 4. M ¹¹ and L ^{11 to} L ¹⁵ The bond to each may be any of a coordination bond, an ionic bond, and a covalent bond.) The organic electroluminescent device according to claim 1 or 2, wherein the metal complex having a tetradentate or higher ligand is a compound represented by the following general formula (III):

(In General Formula (III), Q ¹¹ represents an atomic group forming a nitrogen-containing heterocycle, Z ¹¹ , Z ¹² and Z ¹³ each represents a substituted or unsubstituted carbon atom or nitrogen atom; ^Y1 represents a metal ion which may further have a ligand.)   The organic electroluminescent element according to any one of claims 1 to 4, wherein a metal ion in the metal complex having a tetradentate or higher ligand is a transition metal ion.   The metal ions in the metal complex having a tetradentate or higher ligand are iridium ions, platinum ions, gold ions, rhenium ions, tungsten ions, rhodium ions, ruthenium ions, osmium ions, palladium ions, silver ions, copper ions. The organic electric field according to any one of claims 1 to 5, wherein the organic electric field is at least one selected from the group consisting of cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, and gallium ion. Light emitting element.   The organic electroluminescent element according to any one of claims 1 to 4, wherein a metal ion in the metal complex having a tetradentate or higher ligand is a rare earth metal ion.