JP2006140059A - Production method for organic electroluminescent element, and organic electroluminescent element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a production method for an organic electroluminescent element high in quality with reduced unevenness of performance. <P>SOLUTION: A production method for an organic layer of an organic electroluminescent element having at least one organic layer between a pair of electrodes comprises the steps of: degassing a deposition material including at least one metal complex having a tridentate or higher ligand; and depositing the deposition material by heating after the degassing. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a method for producing an organic electroluminescent element (hereinafter also referred to as “light emitting element” or “EL element”) capable of emitting light by converting electric energy into light, and the organic electroluminescent element obtained thereby. About.

Today, research and development on various display elements are active. Among them, organic electroluminescence (EL) elements are attracting attention as promising display elements because they can emit light with high luminance at a low voltage.
In general, an organic electroluminescent device is composed of a light emitting layer or a counter electrode sandwiching a plurality of organic layers including a light emitting layer, and electrons injected from a cathode and holes injected from an anode are recombined in the light emitting layer. , Utilizing light emission from the generated exciton, or utilizing light emission from the exciton of another molecule generated by energy transfer from the exciton.

Conventionally, a vacuum deposition method is known as a technique for forming an organic layer of an organic electroluminescent element. In the vacuum deposition method, a thin film is formed by depositing a deposition material by appropriately combining an evaporation source and a deposition substrate in a vacuum chamber. Here, the evaporation source is used in the sense that the vapor deposition material, the heating source, and the storage container are the constituent elements.
Various means for creating an evaporation source (heating source) have been considered, and a so-called resistance heating vapor deposition method is known in which a current is passed through a metal container (metal boat) having a relatively high electric resistance and the raw material is evaporated by the heat generation. Yes. Also known is a so-called electron beam / laser beam vapor deposition method in which a raw material is directly irradiated with an electron beam or a laser beam, and the raw material is evaporated with the energy. Among them, a film forming method using resistance heating (resistance heating vapor deposition method) is widely used because the structure of the film forming apparatus is simple and a high-quality thin film can be formed at a low price.

Adsorption substances such as hydrogen, water, carbon monoxide and carbon dioxide in the atmosphere adhere to the vapor deposition material, the crucible and the like after the vapor deposition material is synthesized or before it is used for vapor deposition. The adsorbed material also adheres when the vacuum state of the vacuum vapor deposition apparatus is broken due to the installation of the substrate or vapor deposition material in the vacuum apparatus, the cleaning in the vacuum apparatus, or the like.
When the adsorbing substance is mixed in the organic thin film light emitting device, the efficiency of injection of electrons and holes injected from the electrode of the organic thin film light emitting device into the light emitting layer is lowered, and the chemical change of the thin film is caused. As a result, mixing of the adsorbing substance into the organic thin film light emitting element causes a decrease in luminance of the organic thin film light emitting element.

In order to remove the adsorbed material, for example, in the production of an organic thin film light emitting element, before the organic thin film is formed by a vacuum vapor deposition apparatus, the vapor deposition source is degassed (also referred to as degassing or degassing). Heating, heat insulation, and cooling have been performed. It is disclosed that a material degassed in advance outside the vacuum apparatus is automatically supplied into the vacuum apparatus (for example, see Patent Document 1).
A technique is disclosed in which a supply vapor deposition material is heated and melted in a reducing atmosphere and degassed and supplied to a molten metal of the vapor deposition material in the crucible (see, for example, Patent Document 2).

In particular, in the production of an organic thin film of an organic electroluminescent device, due to the characteristics of the organic material, the vapor pressure is high and it is easily decomposed and modified, so that the deposited material is decomposed and modified by heating, resulting in a decrease in luminance and driving durability. Such a decrease in brightness, brightness unevenness, dot defects, leakage current, etc. are likely to occur, and there is a need for a technique for sufficiently degassing without modifying the vapor deposition material.
JP 2004-22326 A JP-A-5-255839

  As described above, there has been a strong demand for the development of a method for manufacturing an organic electroluminescent element that can stably manufacture a high-quality organic electroluminescent element.

  An object of the present invention is to provide a method for producing an organic electroluminescence device having high quality and little performance variation.

The present inventors have intensively studied in view of the above circumstances, and found that the above problems can be solved, thereby completing the present invention.
That is, the present invention is achieved by the following means.

<1> A method for producing an organic layer of an organic electroluminescent device having at least one organic layer between a pair of electrodes, wherein a vapor deposition material containing at least one metal complex having a tridentate or higher ligand is removed. The manufacturing method of the organic layer of the organic electroluminescent element which has the process of gas-processing, and the process of heating and vapor-depositing this vapor deposition material after this degassing process.

<2> The method for producing an organic layer of an organic electroluminescent element according to <1>, wherein the vapor deposition material is not exposed to the atmosphere between the degassing step and the vapor deposition step. .

<3> The organic electroluminescent element as described in <1> or <2> above, wherein the temperature of the vapor deposition material in the degassing step is the same as or lower than the temperature of the vapor deposition material in the vapor deposition step Method for producing organic layer.

<4> The production of an organic layer of an organic electroluminescence device according to any one of <1> to <3>, wherein the tridentate or higher ligand is a chain ligand. Method.

<5> The organic electroluminescence according to any one of <1> to <3>, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (I): The manufacturing method of the organic layer of an element.

(In the general formula (I), M ¹¹ represents a metal ion, and L ¹¹ , L ¹² , L ¹³ , L ¹⁴ , and L ¹⁵ each represent a ligand coordinated to M ^11. Between L ¹¹ and L ¹⁴ In addition, L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand by further adding an atomic group to Y ¹¹ , Y ¹² , Y ¹³ represents a linking group, a single bond, or a double bond, respectively, and 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 , and Y ¹³ and L ¹⁴ each independently represent a single bond or a double bond, and n ¹¹ represents 0 to 4.)

<6> The method for producing an organic layer of an organic electroluminescent element according to the above <5>, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (II).

(In the general formula (II), M ^X1 .L is .Q ^X11 to Q ^X16 representing a metal ion represents a atomic group containing an atom coordinating to an atom or M ^X1 coordinating to M ^{X1 X11} ~L ^X14 Represents a single bond, a double bond or a linking group, that is, an atomic group consisting of Q ^X11 -L ^X11 -Q ^X12 -L ^X12 -Q ^X13 and Q ^X14 -L ^X13 -Q ^X15 -L ^X14 -Q ^X16 Each atomic group is a tridentate ligand. The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond or a covalent bond.)

<7> The method for producing an organic layer of an organic electroluminescent element according to any one of <1> to <3>, wherein the tridentate or higher ligand is a cyclic ligand.

<8> The method for producing an organic layer of an organic electroluminescence device according to <7>, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (III).

(In the 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.)

<9> The metal ion in the metal complex having a tridentate or higher ligand is at least one selected from the group consisting of platinum ion, iridium ion, rhenium ion, palladium ion, rhodium ion, ruthenium ion, and copper ion. The method for producing an organic layer of an organic electroluminescence device according to any one of <1> to <8>, wherein the organic layer is an organic layer.

<10> A method for producing an organic electroluminescent device having at least one organic layer between a pair of electrodes, wherein the at least one organic layer is the method according to any one of the above items <1> to <9>. A method for producing an organic electroluminescent element, characterized by being formed using a method for producing an organic layer of an organic electroluminescent element.

<11> An organic electroluminescence device formed using the method for producing an organic electroluminescence device according to <10>.

ADVANTAGE OF THE INVENTION According to this invention, the manufacturing method of the organic layer of the organic electroluminescent element which can manufacture the organic electroluminescent element which shows high luminous efficiency and was excellent also in durability for a long time can be provided. .
Moreover, according to this invention, the manufacturing method of the organic electroluminescent element which shows the high luminous efficiency including the organic layer obtained by the said manufacturing method, and was excellent also in durability can be provided.
Furthermore, the organic electroluminescent element obtained by the manufacturing method of the said organic electroluminescent element can be provided.

Hereinafter, the present invention will be described in detail.
The method for producing an organic layer of an organic electroluminescent device of the present invention is a method of degassing a vapor deposition material containing at least one metal complex having a tridentate or higher ligand (hereinafter also referred to as “metal complex of the present invention”). And a step of heating and depositing the deposition material after the degassing step.
By including this step, it is possible to provide a method for producing an organic layer of an organic electroluminescence device having high quality and little performance variation.
The method for producing the organic layer can include other known processes in addition to the degassing process and the vapor deposition process.

  Through the method for producing an organic layer of the organic electroluminescent element of the present invention, the method for producing an organic electroluminescent element having the organic layer, and the organic electroluminescent element, through the production process of the organic layer and description of the elements of the light emitting element, This will be described in detail below.

  The manufacturing method of the organic layer of the organic electroluminescent element of this invention needs to have the process of degassing before the said vapor deposition process.

-Degassing process-
The degassing step of the present invention is to heat the vapor deposition material and the container (crucible) before the step of vapor depositing the vapor deposition material containing at least one metal complex having a tridentate or higher ligand. Is a step of vaporizing and removing adsorbing substances such as hydrogen, water, carbon monoxide and carbon dioxide adsorbed on the vapor deposition material and the crucible, and impurities in the vapor deposition material.
In the present invention, from the viewpoint of simplification of the process, the degassing process and the vapor deposition process can be performed in the same vacuum apparatus.
In addition, it is preferable that the vapor deposition material is not exposed to the atmosphere, but if it is not exposed to the air, the vacuum apparatus for performing the degassing process and the vacuum apparatus for performing the vapor deposition process may be different. The two vacuum devices may be connected by a vacuum transfer chamber or the like to transfer the vapor deposition material so that it is not exposed to the atmosphere.

  As a specific example of performing the degassing process and the vapor deposition process in the same vacuum apparatus, for example, a movable shutter is installed between the crucible filled with the vapor deposition material installed in the vacuum apparatus and the substrate to be vapor deposited. Then, in a state where the shutter is closed and the pressure is reduced by a vacuum pump, the vapor deposition material is heated for a desired temperature and time to perform degassing treatment. The gas generated at this time is discharged out of the system by a vacuum pump.

  As a specific example in which the degassing process and the vapor deposition process are performed in different vacuum apparatuses, for example, a vacuum apparatus used in the degassing process and a vacuum apparatus used in the vapor deposition process are connected in a vacuum transfer chamber. After performing a degassing process similar to the above in the degassing vapor deposition apparatus, the vacuum for the vapor deposition process is removed from the vacuum apparatus for degassing without exposing the vapor deposition material to the atmosphere. It is transported into the device.

The temperature of the vapor deposition material in the degassing treatment is not particularly limited as long as the degassing is sufficiently performed, but is preferably the same as or lower than the vapor deposition temperature of the vapor deposition material from the viewpoint of decomposition of the vapor deposition material. Although the time of the degassing process varies depending on the amount of the vapor deposition material and the amount of the adsorbed substance or impurities, the degassing process is performed for a time sufficient for degassing. For example, whether or not degassing has been sufficiently performed can be determined by a vacuum gauge installed in the vacuum apparatus. That is, since gas is generated during the degassing process, the pressure in the vacuum device increases. When the pressure increase is finished, it can be determined that the degassing has been sufficiently performed.
For the heating, the same method as the heating in the vapor deposition step described later can be adopted, and the preferred method is also the same.

The degree of vacuum in the degassing treatment step is not particularly limited as long as degassing is efficiently performed according to conditions such as a deposition material to be used and heating, but is preferably 10 ⁻² Pa to 10 ⁻⁷ Pa, Among these, 10 ⁻³ Pa to 10 ⁻⁷ Pa is particularly preferable.
The degree of vacuum required in the degassing process is not particularly limited even before or after the heating of the vapor deposition material in the vacuum apparatus. .

In the degassing process, other means can be taken to efficiently perform the degassing process.
Other means are not particularly limited, and examples thereof include stirring of the vapor deposition material.

-Vapor deposition process-
In the method for producing an organic layer of an organic electroluminescent element in the present invention, the organic layer is formed by vapor deposition.
In general, the vapor deposition method is a vacuum vapor deposition method in which a substance is heated and evaporated under high vacuum (10 ⁻² Pa or less), and a gaseous substance is deposited on a target (substrate). However, the vapor deposition method referred to in this specification includes all the vapor deposition techniques in a broader sense. For example, a CVD method for forming a film by a chemical reaction on the target surface also includes the vapor deposition method in the present invention. Within the range.
Details of the vapor deposition method are described in Chapter 8 of "New Format / Vacuum Handbook" (edited by ULVAC, Inc.) published by Ohm.

The vapor deposition step in the present invention refers to a step of evaporating the vapor deposition material in the storage container by heating or the like to form a film on the substrate.
The heating or the like is not particularly limited as long as it is a method for evaporating the vapor deposition material, and examples thereof include a heating method and a method other than heating.

  As the heating method for evaporating the vapor deposition material, there are a resistance heating method, a high frequency heating method, an electron beam heating method, a laser heating method, etc., but resistance heating is performed in terms of simplicity (low cost and simple apparatus). The method is preferred. These heating methods may be indirect heating in which the storage container is heated, or any method in which the vapor deposition material is directly heated, but indirect heating in which the storage container is heated is preferable.

Moreover, there are a sputtering method, an ion plating method, a molecular beam epitaxy method and the like as a method for evaporating the material by a method other than the heating, which can be used properly depending on the purpose.
The heating temperature is generally 100 ° C. to 1000 ° C., preferably 100 ° C. to 500 ° C., although depending on the vapor deposition material used.

  In the case of forming a film with a mixture of two or more substances, a mixture of a plurality of substances may be evaporated in one storage container. However, in this method, the composition of the substance in the evaporated gas is kept constant. It is difficult, and a method in which molecules are simultaneously blown from different evaporation sources is common, and the latter is also preferable in the present invention.

  The organic layer created by the vapor deposition method does not contain impurities, oxygen, and moisture derived from solvents, binders, etc., as compared with the case where it is created by a wet film formation method typified by a spin coating method or an inkjet method. A light emitting layer thin film having a desired film thickness can be easily obtained without being concerned about driving durability and without worrying about dissolving an existing lower layer with a solvent.

  Further, by performing masking at the time of vapor deposition, different light emitting materials and host materials can be used for each pixel to have different light emitting characteristics, which is suitable for manufacturing a fine color display with high definition and high image quality.

-Other processes-
In the method for producing an organic layer of the organic electroluminescent element, the other steps are not particularly limited, and a known vapor deposition material installation step, substrate transfer installation step, and the like can be employed as necessary. .

The said vapor deposition material installation process means the process of installing vapor deposition material in a desired position in a vacuum vapor deposition apparatus, and is a process performed before a degassing process process and a vapor deposition process.
The said vapor deposition material in this invention is a material which has at least 1 type of metal complex which has a tridentate or more ligand, The detail about this metal complex is mentioned later.
The vacuum vapor deposition apparatus is not particularly limited as long as it can be vacuum vapor deposition described later, and a known apparatus can be appropriately selected and used.
The vapor deposition material may be installed in any form, but is preferably installed in a storage container.
The storage container for the vapor deposition material is particularly suitable for the shape and material of the container as long as it can store the vapor deposition material and can use the heating method described later or a method other than heating used for vapor deposition. There is no limitation, and the storage container and the apparatus such as the method may be the same or different.
Examples of the storage container include a metal plate, a so-called metal boat, and a cell-type crucible, which are made by processing a metal material such as tungsten, tantalum, and molybdenum having a high melting point into a thin plate shape to increase electric resistance.
As an example of the cell type crucible, for example, there is a crucible called a K cell (Kununsen cell). In the K cell, a crucible made of, for example, boron nitride is disposed inside the heating coil, and an appropriate amount of vapor deposition material is accommodated inside the crucible. A heat shielding plate made of tantalum or the like is provided outside the crucible to accurately control its temperature, and a thermocouple is provided below the crucible. When a current is passed through the heating coil, the crucible is heated and the vapor deposition material evaporates.

The substrate transport installation step refers to a step of transporting and setting the substrate to be deposited to a predetermined position in a vacuum deposition apparatus, and is performed after the deposition material is installed and before the degassing process.
As the transfer, manual transfer under atmospheric pressure, transfer by remote operation, or automatic transfer may be used to transfer and set the substrate. Alternatively, transfer by remote control under vacuum or automatic transfer is used to set the substrate. However, from the viewpoint of mass production, it is preferable to transport and set the substrate at a predetermined position by remote operation and / or automatic transport under vacuum. The remote operation and automatic transfer methods are not particularly limited, and known methods can be used as appropriate.

Next, the metal complex having a tridentate or higher ligand in the present invention will be described in detail.
The atom that coordinates to the metal ion in the metal complex is not particularly limited, but is preferably an oxygen atom, a nitrogen atom, a carbon atom, or a sulfur atom, more preferably an oxygen atom, a nitrogen atom, or a carbon atom, and a nitrogen atom or a carbon atom. Is more preferable.

  The metal ion in the metal complex is not particularly limited, but iridium ion, platinum ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, rare earth ion (for example, europium ion, cadmium ion, terbium ion), Palladium ions, copper ions, cobalt ions, magnesium ions, zinc ions, nickel ions, lead ions, and aluminum ions are preferred.

  As the metal complex having a tridentate or higher ligand in the present invention, a metal complex having a tridentate or higher and a hexadentate or lower ligand is more preferable, and a metal complex having a tridentate or tetradentate ligand is more preferable. A metal complex having a tetradentate ligand is preferable.

The ligand of the metal complex in the present invention is preferably linear or cyclic, and is a central metal (for example, M ¹¹ is represented in the case of a compound represented by the general formula (II) described later). It is preferable to have at least one nitrogen-containing heterocycle coordinated with nitrogen (for example, a pyridine ring, a quinoline ring, a pyrrole ring, etc.). The nitrogen-containing heterocycle is more preferably a nitrogen-containing 6-membered heterocycle.

  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.).

  When the ligand of the metal complex in the present invention is a chain ligand, the metal complex may be a compound represented by general formula (I) or general formula (II) described in detail below. preferable.

  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. There is no further atomic group between L ¹¹ and L ¹⁴ to form a cyclic ligand. L ¹⁵ does not 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 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 ions, platinum ions, iridium ions, rhenium ions, palladium ions, rhodium ions, ruthenium ions, copper ions, europium ions, gadolinium ions, and terbium ions are preferable, and platinum ions, iridium ions, and europium ions. Ions are more preferable, platinum ions and iridium ions are more preferable, and platinum ions are particularly preferable.

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, or a carbon atom is preferable, and a nitrogen atom, an oxygen atom, or A carbon atom is more preferred.

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, condensed rings containing them (eg, quinoline ligands, benzothiazole ligands, etc.) and their tautomerism Body).

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 Azole ligands, thiadiazole ligands, and condensed rings containing them (for example, quinoline ligands, benzoxazole ligands, benzimidazole ligands, etc.) 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, a 5-membered heterocyclic ligand of the compound (24) described later and a 5-membered terminal heterocycle of the compound (64). Ring ligand, The 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 carbon numbers) 2 to 20, particularly preferably 2 to 10 carbon atoms, such as methylamino), arylamino ligands (such as phenylamino), acylamino ligands (preferably having carbon atoms) 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino), alkoxycarbonylamino ligands (preferably 2 to 2 carbon atoms). 30 and more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino and the like. A xyloxycarbonyl 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 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.). Examples include carbonyl ligands (eg, ketone ligands, ester ligands, amide ligands, etc.), ether ligands (eg, dialkyl ether ligands, diaryl ether ligands, furyl ligands, etc.) It is done.

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 ligands (examples) In thioketone ligand, a thioester ligand, etc.), 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 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, etc.) or a tautomer thereof, etc.) are preferred, an aromatic carbocyclic ligand, an ant Ruoxy ligands, arylthio ligands, arylamino ligands, as well as pyridine ligands, pyrazine ligands, imidazole ligands, or condensed ligand bodies containing them (for example, quinoline ligands, A quinoxaline 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 Are more preferable, and an aromatic carbocyclic ligand or an aryloxy ligand is particularly preferable.

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, indolenine ring) and their tautomers Pyridine ring, pyrazine ring, pyrimidine ring, pyrrole ring, condensed ring containing them (for example, quinoline ring, benzpyrrole, etc.) and tautomers thereof are more preferable, pyridine ring, pyrazine Ring, pyrimidine ring, and condensed ring containing them (for example, quinoline ring, etc.) are more preferable, including pyridine ring and pyridine ring. Condensed body (e.g., a quinoline ring) is 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 ligand (eg, picolinic acid ligand, 2- (2-hydroxyphenyl) -pyridine ligand, etc.), L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , L ¹⁴ And a monoanionic bidentate ligand containing a 1,3-diketone ligand (for example, an acetylacetone ligand) or a pyridine ligand (for example, a picolinic acid ligand). A tetradentate ligand formed by L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , L ¹⁴ , and the like. Preferably, a 1,3-diketone ligand (eg, acetylacetone ligand) And a monoanionic bidentate ligand containing a pyridine ligand (for example, a picolinic acid ligand, 2- (2-hydroxyphenyl) -pyridine ligand, etc.), Particularly preferred are diketone ligands (eg, acetylacetone ligands). 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 general formula (I), Y ¹¹ , Y ¹² , and Y ¹³ each independently represent a linking group, a single bond, or a double bond. The linking group is not particularly limited, and for example, 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, a silicon atom linking group, or And a linking group composed of a combination of these. 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.

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

In general formula (II), M ^X1 represents a metal ion. Q ^X11 to Q ^X16 represents an atomic group containing an atom coordinating to an atom or M ^X1 coordinating to M ^X1. L ^{X11 to} L ^{X14 each} represent a single bond, a double bond or a linking group.
That is, in the general formula (II), an atomic group consisting of Q ^X11 -L ^X11 -Q ^X12 -L ^X12 -Q ^X13 and an atomic group consisting of Q ^X14 -L ^X13 -Q ^X15 -L ^X14 -Q ^X16 are Each forms a tridentate ligand.
The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond or a covalent bond.

The compound represented by formula (II) will be described in detail.
In general formula (II), M ^X1 represents a metal ion. Although it does not specifically limit as a metal ion, A monovalent to trivalent metal ion is preferable, a bivalent or trivalent metal ion is more preferable, and a trivalent metal ion is further more preferable. Specifically, platinum ion, iridium ion, rhenium ion, palladium ion, rhodium ion, ruthenium ion, copper ion, europium ion, gadolinium ion and terbium ion are preferable, iridium ion and europium ion are more preferable, and iridium ion is further preferable.

Q ^X11 to Q ^X16 represents an atomic group containing a coordinating atom to the coordinating atom or M ^X1 to M ^X1.
When Q ^{X11 to} Q ^X16 represent an atom coordinated to M ^X1 , specific atoms include a carbon atom, a nitrogen atom, an oxygen atom, a silicon atom, a phosphorus atom, a sulfur atom, and preferably nitrogen. An atom, an oxygen atom, a sulfur atom, and a phosphorus atom, more preferably a nitrogen atom and an oxygen atom.
If Q ^X11 to Q ^X16 represents an atomic group containing an atom coordinating to M ^X1, as containing a coordinating carbon atom to M ^X1 is, for example, an imino group, an aromatic hydrocarbon Hajime Tamaki (benzene, naphthalene Etc.), heterocyclic groups (thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, triazole, etc.) and fused rings containing them, and tautomers thereof.

Examples of those coordinated to M ^X1 with a nitrogen atom include nitrogen-containing heterocyclic groups (pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, triazole, etc.), amino groups (alkylamino) A group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as methylamino), an arylamino group (such as phenylamino), and the like. An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably Or an aryloxycarbonylamino group (preferably having a carbon number of 7-30, more preferably having a carbon number of 7-20, and particularly preferably having a carbon number of 7). -12, for example, phenyloxycarbonylamino, etc.), sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, And methanesulfonylamino, benzenesulfonylamino, etc.) and imino groups. These groups may be further substituted.

Coordinated to M ^X1 with an oxygen atom is 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, such as 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, and particularly preferably 1 to 12 carbon atoms, for example, pyridyl. Oxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyloxy groups (preferably having 2 to 30 carbon atoms, more preferably Alternatively, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.), Silyloxy group (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms). Particularly preferably, it has 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy, triphenylsilyloxy, etc.), carbonyl group (for example, ketone group, ester group, amide group, etc.), ether group (for example, dialkyl ether group, Diaryl ether group, furyl group, etc.).

Coordinating M ^X1 with a silicon atom includes an alkylsilyl group (preferably having 3 to 30 carbon atoms, such as a trimethylsilyl group), an arylsilyl group (preferably having 18 to 30 carbon atoms). For example, a triphenylsilyl group etc. are mentioned. These groups may be further substituted.

As the one coordinated to M ^X1 with a sulfur atom, 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, ethylthio, etc.) An arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenylthio), a heterocyclic thio group ( Preferably it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolyl Thiocarbonyl group (eg thioketone group, thioester group etc.), thioether group (eg dialkylthio). Ether groups, diaryl thioether, etc. thiofuryl group).

Examples of the group coordinated to M ^X1 with a phosphorus atom include a dialkylphosphino group, a diarylphosphino group, a trialkylphosphine, a triarylphosphine, and a phosphinin group. These groups may be further substituted.

As an atomic group represented by Q ^{X11 to} Q ^X16 , preferably, M ^X1 is coordinated by an aromatic hydrocarbon ring group coordinated by a carbon atom, an aromatic heterocyclic group coordinated by a carbon atom, or a nitrogen atom. Nitrogen-containing aromatic heterocyclic group, alkyloxy group, aryloxy group, alkylthio group, arylthio group, dialkylphosphino group, more preferably aromatic hydrocarbon ring group coordinated by carbon atom, coordinated by carbon atom And a nitrogen-containing aromatic heterocyclic group coordinated by a nitrogen atom.
The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond or a covalent bond.

In general formula (II), L ^{X11 to} L ^X14 represent a single bond, a double bond, or a linking group. Although it does not specifically limit as a coupling group, The coupling group comprised including the atom selected from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom is preferable. Although the specific example of this connection is shown below, it is not limited to these.

These linking groups may be further substituted, and as the substituent, those exemplified as the substituents represented by R ^{21 to} R ²⁴ in the following general formula (2) can be applied, and the preferred range is also the same. L ^{X11 to} L ^X14 are preferably a single bond, a dimethylmethylene group, or a dimethylsilylene group.

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.

一般式（１）

General formula (1)

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 examples thereof include 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 Examples of the condensed ring include quinoline ring, benzoxazole ring, benzimidazole ring, indolenine ring, and the like 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 a condensed ring containing them (for example, quinoline ring, benzoxazole ring, benzimidazole ring, etc.) and tautomers thereof, more preferably pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, pyrrole. A ring and a condensed ring containing them (for example, quinoline ring) and tautomers thereof, and more preferably a pyridine ring and a condensed ring thereof (for example, quinoline ring). Particularly preferred 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 includes, for example, 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. Examples thereof include a linking group.

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, it is an alkyl group (preferably C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, 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 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 20 carbon atoms, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl. Preferably it has 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, and an amino group (preferably). Has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms. Examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino. ),

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, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, Famoyl 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, such as ureido, methylureido, phenylureido, etc.). ),

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, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic ring A 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, for example, imidazolyl, pyridyl, quinolyl, furyl and thienyl. , Piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl , An 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). ), 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). Is mentioned. 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 forming a ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) and a halogen atom are more preferable, an aryl group and a halogen atom are further preferable, and an aryl group is particularly preferable.

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.

  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 , 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. A ring.

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, and more preferably a benzene ring, a pyridine ring, and a condensed ring thereof. Preferably, 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 includes, for example, 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 combinations thereof. Examples thereof include a linking group.

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, For example, a group that forms a benzo-fused ring, a pyridine-fused ring, etc.

  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 each independently have the same meaning as 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 and n ^C6 represent an integer of 0 to 3, n ^C4 and n ^C5 represent an integer of 0 to 4, and when each of R ^C3 , R ^C4 , R ^C5 and R ^C6 includes a 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 and 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 , X ^B2 are M ²¹ in the general formula (1). , Y ²² , Y ²³ , R ²¹ , R ²² , R ²³ , R ²⁴ , L ²⁵ , n ²¹ , X ²¹ , X ²² , respectively, and the 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.

A preferred form of the metal complex having a tridentate ligand in the present invention is a compound represented by the following general formula (5).
The compound represented by the general formula (5) will be described.

In General Formula (5), M ⁸¹ has the same meaning as M ¹¹ in General Formula (I), and the preferred range is also the same.

L ⁸¹ , L ⁸² , and L ⁸³ are each independently synonymous with L ¹¹ , L ¹² , L ¹⁴ in the general formula (I), and the preferred range is also the same.

Y ⁸¹ and Y ⁸² are each independently synonymous with Y ¹¹ and Y ¹² in the general formula (I), and their preferred ranges are also the same.

L ⁸⁵ represents a ligand coordinated to M ⁸¹ . L ⁸⁵ is preferably a 1 to 3 ligand, more preferably a 1 to 3 anionic ligand. No particular limitation is imposed on the anionic ligand 1-3 seat, tridentate ligand formed by halogen ^{ligand, L 81, Y 81, L} 82, Y 82, L 83 is preferably, L ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² and L ⁸³ are more preferable. Never L ⁸⁵ is connected to the L ^81, L ⁸³ without passing through the metal. The number of coordination sites and the number of ligands do not exceed the coordination number of the metal.

n ⁸¹ represents 0 to 5. When M ⁸¹ is a metal having a coordination number of 4, n ⁸¹ is 1 and L ⁸⁵ represents a monodentate ligand. When M ⁸¹ is a metal having a coordination number of 6, n ⁸¹ is preferably 1 to 3, more preferably 1, 3 and even more preferably 1. When M ⁸¹ is coordination number 6 and n ⁸¹ is 1, L ⁸⁵ represents a tridentate ligand, and when M ⁸¹ is coordination number 6 and n ⁸¹ is 2, L ⁸⁵ is one monodentate ligand and bidentate. ligand one of the stands, when L ⁸⁵ of n ⁸¹ in M ⁸¹ is coordination number of 6 3 represents a monodentate ligand. When M ⁸¹ is a metal having a coordination number of 8, n ⁸¹ is preferably 1 to 5, more preferably 1 or 2, and more preferably 1. When M ⁸¹ is coordination number 8 and n ⁸¹ is 1, L ⁸⁵ represents a pentadentate ligand, and when n ⁸¹ is 2, L ⁸⁵ represents one tridentate ligand and one bidentate ligand. , N ⁸¹ is 3, L ⁸⁵ represents one tridentate ligand and two monodentate ligands, or two bidentate ligands and one monodentate ligand, and when n ⁸¹ is 4, L ⁸⁵ Represents one bidentate ligand and three monodentate ligands, and when n ⁸¹ is 5, L ⁸⁵ represents five monodentate ligands. When ⁿ⁸¹ is plural, the plural ^L85s may be the same or different.

A preferred form of the general formula (5) is an aromatic carbocyclic or heterocyclic ring in which L ⁸¹ , L ⁸² and L ^{83 in the} general formula (5) are carbon atoms and coordinate to M ⁸¹ , or a nitrogen atom and M ⁸¹ represents coordinating nitrogen-containing heterocyclic ring, at least one of L ^81, L ^82, L ⁸³ is a nitrogen-containing heterocycle. Coordinating aromatic carbocyclic these carbon atoms, heterocycles and nitrogen coordinating nitrogen-containing hetero ring atoms coordinating ligands and a nitrogen atom in a carbon atom to M ¹¹ described by the general formula (I) Examples of coordination are given, and the preferred range is also the same. Y ⁸¹ and Y ⁸² preferably represent a single bond or a methylene group.
Other preferable forms of the compound represented by the general formula (5) are a compound represented by the following general formula (5-A) and a compound represented by the following general formula (5-B).
First, the compound represented by formula (5-A) will be described.

In the general formula (5-A), M ⁹¹ has the same meaning as M ⁸¹ in Formula (5), and their preferable ranges are also the same.

Q ⁹¹ and Q ⁹² represent a group that forms a nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ⁹¹ ). The nitrogen-containing heterocycle formed by Q ⁹¹ and Q ⁹² is not particularly limited, and examples thereof include pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, thiazole ring, oxazole ring, pyrrole ring, pyrazole ring, imidazole. Examples thereof include a ring, a triazole ring, and a condensed ring containing them (for example, a quinoline ring, a benzoxazole ring, a benzimidazole ring, an indolenine ring, and the like) and tautomers thereof.

The nitrogen-containing heterocycle formed by Q ⁹¹ and Q ⁹² is preferably a pyridine ring, a pyrazole ring, a thiazole ring, an imidazole ring, a pyrrole ring, and a condensed ring containing them (for example, a quinoline ring, a benzthiazole ring) Benzimidazole ring, indolenine ring, etc.) and tautomers thereof, more preferably pyridine ring, pyrrole ring, and condensed ring containing them (for example, quinoline ring, etc.), and these Tautomers thereof, more preferably a pyridine ring, and a condensed ring containing them (for example, a quinoline ring), and particularly preferably a pyridine ring.

Q ⁹³ represents a group forming a (ring containing coordinating nitrogen M ⁹¹⁾ nitrogen-containing heterocyclic ring. No particular limitation is imposed on the nitrogen-containing heterocyclic ring formed by Q ^93, a pyrrole ring, an imidazole ring, tautomers of the triazole ring, and a condensed ring body thereof (for example, benzopyrrole, etc.) are preferred, a pyrrole ring And tautomers of condensed rings containing a pyrrole ring (for example, benzpyrrole) are more preferable.

W ⁹¹ and W ⁹² are each independently synonymous with W ⁵¹ and W ⁵² in the general formula (2), and preferred ranges are also the same.

L ⁹⁵ has the same meaning as L ⁸⁵ in Formula (5), and their preferable ranges are also the same.

n ⁹¹ has the same meaning as n ⁸¹ in Formula (5), and their preferable ranges are also the same.

  The compound represented by formula (5-B) will be described.

Formula (5-B) in, M ¹⁰¹ has the same meaning as M ⁸¹ in Formula (5), and their preferable ranges are also the same.

Q ¹⁰² is synonymous with Q ²¹ in the general formula (1), and the preferred range is also the same.

Q ¹⁰¹ has the same meaning as Q ⁹¹ in formula (5-A), and the preferred range is also the same.

Q ¹⁰³ represents a group that forms an aromatic ring. No particular limitation is imposed on the aromatic ring formed by Q ^103, a benzene ring, furan ring, thiophene ring, pyrrole ring, and condensed rings containing these (e.g., naphthalene ring), more preferably a benzene ring and a benzene ring Are more preferable, and a benzene ring is particularly preferable.

Y ¹⁰¹ and Y ¹⁰² are independently the same as Y ²² in the general formula (1), and the preferred range is also the same.

L ¹⁰⁵ has the same meaning as L ⁸⁵ in Formula (5), and their preferable ranges are also the same.

n ¹⁰¹ has the same meaning as n ⁸¹ in Formula (5), and their preferable ranges are also the same.

X ¹⁰¹ has the same meaning as X ²¹ in formula (1), and the preferred range is also the same.

Another preferred embodiment of the metal complex having a tridentate ligand in the present invention is a compound represented by the general formula (II), more preferably among the compounds represented by the general formula (II). Is a compound represented by the following general formula (X2), more preferably a compound represented by the following general formula (X3).
First, the compound represented by general formula (X2) is demonstrated.

In general formula (X2), M ^X2 represents a metal ion. Y ^X21 to Y ^X26 represents a coordinating atom M ^X2, Q ^X21 ~Q ^X26 represents an atomic group forming an aromatic ring or aromatic heterocyclic ring with the respective Y ^X21 to Y ^X26. L ^{X21 to} L ^X24 represent a single bond, a double bond or a linking group. Binding of M ^X2 and Y ^X21 to Y ^X26 may be a covalent bond, and each of coordination bond.

The compound represented by formula (X2) will be described in detail.
In general formula (X2), M ^X2 has the same meaning as M ^X1 in general formula (II), and the preferred range is also the same. Y ^X21 to Y ^X26 represent an atom coordinating to M ^X2. The bond between Y ^{X21 to} Y ^X26 and M ^X2 may be a coordinate bond or a covalent bond. Y ^{X21 to} Y ^X26 include a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom, preferably a carbon atom and a nitrogen atom. Q ^X21 to Q ^X26 represents an atomic group forming an aromatic hydrocarbon ring or aromatic heterocyclic ring each include Y ^X21 to Y ^X26. The aromatic hydrocarbon ring and aromatic heterocycle formed in this case are benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrole ring, pyrazole ring, imidazole ring, triazole ring, oxazole ring. , Thiazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan ring, preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyrazole ring, imidazole ring, triazole ring, more preferably benzene. A ring, a pyridine ring, a pyrazine ring, a pyrazole ring and a triazole ring, and particularly preferably a benzene ring and a pyridine ring. These may further have a condensed ring or a substituent.

L ^{X21 to} L ^X24 are synonymous with L ^{X11 to} L ^X14 in the general formula (II), and preferred ranges thereof are also the same.

The compound represented by the general formula (II) is more preferably a compound represented by the following general formula (X3).
General formula (X3) is demonstrated.

In general formula (X3), M ^X3 represents a metal ion. Y ^{X31 to} Y ^{X36 each} represent a carbon atom, a nitrogen atom, or a phosphorus atom. L ^{X31 to} L ^{X34 each} represent a single bond, a double bond or a linking group. The bond between M ^X3 and Y ^X31 to Y ^X36 may be a coordinate bond or a covalent bond.

M ^X3 has the same meaning as M ^X1 in formula (II), and the preferred range is also the same. Y ^{X31 to} Y ^X36 each represent an atom coordinated to M ^X3 . The bond between Y ^{X31 to} Y ^X36 and M ^X3 may be a coordinate bond or a covalent bond. Y ^{X31 to} Y ^X36 include a carbon atom, a nitrogen atom and a phosphorus atom, and preferably a carbon atom and a nitrogen atom. L ^{X31 to} L ^X34 are synonymous with L ^{X11 to} L ^X14 in the general formula (II), and preferred ranges thereof are also the same.

  Specific examples of the compounds represented by the general formula (I), the general formula (II), and the general formula (5) include compounds (1) to (242) described in Japanese Patent Application No. 2004-162849. (The structure is shown below), but is not limited thereto.

(Method for synthesizing metal complex in the present invention)
Metal complexes in the present invention [general formulas (I), (1), (1-A), (2), (3), (3-A), (3-B), (3-C), ( 4), (4-A), (5), (5-A), and (5-B), and the compounds represented by the general formulas (II), (X2), and (X3)] It 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, potassium carbonate, etc.) 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.

The metal complex of the present invention is appropriately selected from the ligands that form the partial structure of the target complex, whereby the general formulas (I), (1), (1-A), (2), (3), (3-A), (3-B), (3-C), (4), (4-A), (5), (5-A), and (5-B), and The compounds represented by the compounds represented by the general formulas (II), (X2), 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 (such as 1,10-phenanthroline) and an anisole derivative (such as 4-fluoroanisole) 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 After the Suzuki coupling reaction using a modified anisole derivative (such as 2-bromoanisole) as a starting material, the methyl group is deprotected (the method described in Journal of Organic Chemistry, 741, 11, (1946), Alternatively, it can also be synthesized by using a method such as heating in pyridine hydrochloride.

  When the ligand of the metal complex in the present invention is a cyclic ligand as described above, the metal complex is preferably a compound represented by the following general formula (III).

  Hereinafter, the compound represented by the following general formula (III) will be described.

In the 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, and M ^Y1 represents Furthermore, the metal ion which may have a ligand is represented.

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, and 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 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, 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, 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, nitrogen atom, oxygen atom, sulfur atom, specifically 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, and examples thereof include trimethylsilyl and triphenylsilyl), silyloxy group (Preferably 3 to 40 carbon atoms, more preferably 3 to 3 carbon atoms. , Particularly preferably 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, still more preferably a phenyl group or a fluorine atom. It is.

  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, and 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 even more preferably an oxygen atom or a nitrogen atom.

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, a general formula ( The compound represented by j) or a tautomer thereof is preferable, 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 respectively Z ¹¹ , Z ¹² , Z ¹³ , Z ¹¹ , in the corresponding general formula (III). Z ^12, Z ^13, M ¹¹ in the above formula, the preferred range is also the same.

Q ²¹ and Q ²² each represent a group that forms a nitrogen-containing heterocycle. Q ^21, it is not particularly restricted but includes nitrogen-containing heterocyclic ring formed by Q ^22, a pyrrole ring, an imidazole ring, a triazole ring, a condensed ring body thereof (for example, benzopyrrole), and these tautomeric (For example, a nitrogen-containing 5-membered ring substituted with R ⁴³ , R ⁴⁴ , R ⁴⁵ , and R ^{46 in} the general formula (b) described below is defined as a pyrrole tautomer). And 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 , M ⁴¹ are the same as 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 are synonymous and the preferred range is 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) A group in which R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) is preferable. An alkyl group, an aryl group, R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded. To form a ring structure (for example, 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 (for example, benzo-fused ring, pyridine-fused ring). Etc.) are more preferred.

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, more preferably a single bond, an alkylene linking group, an alkenylene linking group or an imino linking group. A single bond and an alkylene linking group are 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 group to be positioned.

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.

As the group that coordinates to M ¹⁰¹ with a sulfur atom, a sulfide group, a thiophene group, and a thiazole group are preferable, and a thiophene group is more preferable.

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 group coordinated to M ¹⁰¹ by a nitrogen atom, a group coordinated by a phosphorus atom, a group coordinated by an oxygen atom, or a group coordinated by a sulfur atom, and a group coordinated by a nitrogen atom is More preferred.

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 are respectively in the corresponding general formula (c). Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , and M ¹⁰¹ are synonymous and the preferred range is also the same. ^Z204 , ^Z205 , ^Z206 , ^Z210 , ^Z211 and ^Z212 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 general formula (e), ^Z301 , ^Z302 , ^Z303 , ^Z304 , ^Z305 , ^Z306 , ^Z307 , ^Z308 , ^Z309 , ^Z310 , ^L301 , ^L302 , ^L303 , ^L304 , 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} , has the same meaning as M ^101, and 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 are synonymous and the preferred range is 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 , 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 are synonymous and the preferred range is also the same.

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

In the 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 , M ⁷⁰¹ denotes Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁸ , Z ²⁰⁹ , Z ²⁰⁴ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹² , L ¹⁰¹ , L in the corresponding general formulas (d) and (c), respectively. ^102, L ^103, L ^104, has the same meaning as M ^101, and the preferred range is also the same.

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

In 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 are Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ^{209 in the} corresponding general formulas (d), (c), and (f), respectively ^. , Z ²⁰⁴ , Z ²⁰⁵ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , M ¹⁰¹ , X ⁴⁰¹ , X ⁴⁰² , and the preferred range is also the same. .

  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.

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. Although it does not specifically limit as a metal ion, A bivalent metal ion is preferable, Pt ^<2+> , Pd ^<2+> , Cu ^<2+> , Ni ^<2+> , Co ^<2+> , Zn ^<2+> , Mg ^<2+> , 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, or a linkage composed of carbon, nitrogen, silicon, sulfur, oxygen, germanium, phosphorus, etc. 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 divalent aromatic group An 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 hetero group Examples of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 , which is a cyclic group, particularly preferably a single bond, a substituted or unsubstituted methylene group, include the following: Can be mentioned.

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 alkyl groups (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 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, 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 6-20, especially preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy.),

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, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, 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 a sulfonyl group (preferably It 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, etc. Is lower.), A sulfinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methane sulfinyl, and the like benzenesulfinyl.),

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, 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, it has 3 to 24 carbon atoms, and examples thereof include trimethylsilyl, triphenylsilyl, etc.), silyloxy group (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 carbon atoms). For example, trimethylsilyloxy, triphenylsilyloxy, etc. It is.), 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 or 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 with a nitrogen atom is preferably a substituted amino group or a nitrogen-containing hetero five-membered heteroaryl group bonded with a nitrogen atom, and particularly preferably a nitrogen-containing hetero five-membered heteroaryl group bonded with 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). M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , L ^A14, and preferable ranges are also the same. It is.
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). M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , L ^A14, and preferable ranges are also the same. It is.
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). M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , L ^A14, and preferable ranges are also the same. It is.
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 each independently represent a carbon atom or a nitrogen atom. 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 , 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 , 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 the general 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 correspond to each other. 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 in the general formula (B-1) It is synonymous and the preferable 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 correspond to each other. 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 in the general formula (B-1) It is synonymous and the preferable 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 correspond to each other. 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 in the general formula (B-1) It is synonymous and the preferable 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 in the corresponding general formula (A-1), respectively. ^It is synonymous with ^A12 , and its preferable 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). , 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, 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 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 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, 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 6-20, especially preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy.),

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, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, halogen atoms (for example, fluorine) Atom, chlorine atom, bromine atom, 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, it has 3 to 24 carbon atoms, and examples thereof include trimethylsilyl, triphenylsilyl, etc.), silyloxy group (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 carbon atoms). For example, trimethylsilyloxy, triphenylsilyloxy, etc. It is.), 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 and 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 , and L ^C12 in the general formula (C-1), respectively. , Q ^C11 , Q ^C12 , G ^C11 and G ^C12 , and the preferred range is 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 and 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 and 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 correspond to M ^C1 , L ^C11 , L ^C12 , G ^C11 , G in the general formula (C-1), respectively. ^It is synonymous with ^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 in the corresponding general formula (C-1), respectively. ^It is synonymous with ^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 are synonymous with M ^C1 , L ^C11 , L ^C12 , G ^C11 , and G ^{C12 in the} corresponding general formula (C-1), respectively, and a preferable range. Is 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 thereof are also the same. is there.
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 have the same ^{meanings as} M ^D1 , L ^D11 , L ^D12 , G ^D11 and G ^D12 in the general formula (D-1), and preferred ranges are also the same. .
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 It has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 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, such as phenyl, p-methylphenyl, naphthyl, etc.), a substituted carbonyl group; (Preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, etc. A substituted sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl).

Heterocyclic group (there is an aliphatic heterocyclic group or an aromatic heterocyclic group. Preferably, it contains any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to carbon atoms. 30 and particularly preferably 2 to 12 carbon atoms, and examples thereof include imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl group, and the like. 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 ^{D12 in the} corresponding general formula (D-1), respectively. The preferred 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 respectively correspond to M ^D1 , L ^D11 , L ^D12 , G ^D11 and G in the general formula (D-1). ^It is synonymous with ^D12 , and a preferable range is 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 (E-1), 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 and J ^E32 each independently represent an atomic group necessary for forming a five-membered ring. 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 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 , Y ^E14, and 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 are the corresponding M in general formula (E-1). ^{E 1} , G ^E11 , G ^E12 , G ^E13 , G ^E14 , Y ^E11 , Y ^E12 , Y ^E13 , 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 , and L ^{A13 in} general formula (A-1), respectively. , Q ^A11 and Q ^A12 , and the preferred range is 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 , in the general formula (F-1), 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, 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.

Next, the configuration of the organic electroluminescent element of the present invention will be described.
The organic electroluminescent element of the present invention is configured to have at least one organic layer between a pair of anode and cathode electrodes provided on a substrate. The organic layer includes at least one light emitting layer, and other organic layers other than the light emitting layer include a hole transport layer, a hole injection layer, an electron injection layer, an electron transport layer, and the like. The layer structure of a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is particularly preferable.
In addition, each of these layers may have other functions, and the same layer may be laminated. Various materials can be used for forming each layer. Moreover, you may provide a protective layer etc. as another layer.

<Anode>
The anode supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like, and a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. 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 these metals and conductive metal oxides. Mixtures or laminates thereof, inorganic conductive substances such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene and polypyrrole, and laminates of these with ITO, preferably conductive It is a metal oxide, and ITO is particularly preferable in terms of productivity, high conductivity, transparency, and the like.
The thickness of the anode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 500 nm.

Usually, the anode is formed by layering on the above-mentioned soda-lime glass, non-alkali glass, transparent resin substrate or the like. When glass is used, it is preferable to use non-alkali glass as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. Transparent resin substrates include polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyethylene, polycarbonate, polyethersulfone, polyarylate, allyl diglycol carbonate, polyimide, polycycloolefin, norbornene resin, poly (chlorotrine). Fluoroethylene), Teflon (registered trademark), and polytetrafluoroethylene-polyethylene copolymer.
The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but when glass is used, a thickness of 0.2 mm or more, preferably 0.7 mm or more is usually used.
Various methods are used for producing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating vapor deposition method, a chemical reaction method (such as a sol-gel method), a dispersion of indium tin oxide is used. A film is formed by a method such as coating.
The anode can be driven to lower the drive voltage of the element or increase the light emission efficiency by washing or other processing. For example, in the case of ITO, UV-ozone treatment, plasma treatment, etc. are effective.

<Cathode>
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.
As a material for 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 The fluoride or oxide, alkaline earth metal (eg, Mg, Ca, etc.) and the fluoride or oxide thereof, gold, silver, lead, aluminum, sodium-potassium alloy or mixed metal thereof, lithium-aluminum alloy or 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 the like. A mixed metal, a magnesium-silver alloy, or a mixed metal thereof.
The cathode can take not only a single layer structure of the above-mentioned compounds and a mixture thereof but also a laminated structure containing the above-mentioned compounds and a mixture thereof. For example, a laminated structure of aluminum / lithium fluoride and aluminum / lithium oxide is preferable.
The thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 1 μm.
For production of the cathode, methods such as an electron beam method, a sputtering method, a resistance heating vapor deposition method, a coating method, and a transfer method are used, and a metal can be vapor-deposited alone or two or more components can be vapor-deposited simultaneously. Furthermore, a plurality of metals can be vapor-deposited simultaneously to form an alloy electrode, or a previously prepared alloy may be vapor-deposited.
The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

<Organic layer>
The organic layer in the present invention will be described.
The organic electroluminescent element of the present invention is an element manufactured using the above-described manufacturing method, and has an organic layer including at least one light emitting layer. As described above, other organic layers may be included in addition to the light-emitting layer, and other organic layers that are preferably used include the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer. In addition, each layer such as a charge blocking layer and an exciton blocking layer can be used.
The organic layer containing a metal complex having a tridentate or higher ligand needs to be produced by a vapor deposition method after degassing treatment. Among them, the organic layer is preferably a light emitting layer.
Each layer constituting the organic layer other than the organic layer containing the metal complex of the present invention includes a dry film forming method such as a vapor deposition method and a sputtering method, a dipping method, a spin coating method, a dip coating method, a casting method, a die coating method, and a roll. A film can be suitably formed by any of a wet film forming method such as a coating method, a bar coating method, and a gravure coating method, a transfer method, a printing method, and the like.
The content of the metal complex in the organic layer containing the metal complex having a tridentate or higher ligand in the present invention can be used without any particular limitation, but from the viewpoint of durability and luminous efficiency, it is an all solid substance. 0.1 mass%-20 mass% are preferable with respect to quantity, 1 mass%-15 mass% are more preferable, 2 mass%-12 mass% are especially preferable. When the organic layer containing the compound of the present invention is a plurality of layers, it is preferable from the viewpoint of durability and luminous efficiency that each layer is in the above range.

(Light emitting layer)
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.
The light emitting layer in the present invention has a charge transport function and light emission in order to obtain better performance, or to prevent a phenomenon in which agglomeration occurs in a high concentration light emitting material and the excited state is non-radiatively deactivated (concentration quenching). It is preferable that the function is separated and the light-emitting material is doped into the charge transport material (host material) as a dopant.

-Charge transport material (host material)-
As the host material applied to the light-emitting layer, a compound can be used alone, or a plurality of compounds may be mixed and used.
Examples of the host material include carbazole and derivatives thereof (for example, those described in “Applied Physics Letters”, 1999, Vol. 74, No. 3, p. 442), tribenzoazepine and derivatives thereof ( JP-A-10-59943, JP-A-10-219241, JP-A-10-316875, JP-A-10-324680, JP-A-10-330365, JP-A-2001-97953), triazole and derivatives thereof (US Pat. No. 3,121,197) Oxazole and derivatives thereof (US Pat. No. 3,257,203), imidazole and derivatives thereof (Japanese Patent Publication No. 37-16096), polyarylalkanes and derivatives thereof (US Pat. Nos. 3,615,402, 3,820,989, and 35425). 44, JP-B-45-555, JP-A-51-10983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148, JP-A-55-108667, JP-A-55-156953, JP-A-56. -36656), polyarylbenzenoids and derivatives thereof (JP-A-10-255985, JP-A-2002-260861), arylamines and derivatives thereof (US Pat. Nos. 3,567,450, 3,180,703, 3,240,597, 3,658,520). No. 4,232,103, No. 4,175,961, No. 401,376, Japanese Examined Patent Publication No. 49-35702, No. 39-27577, JP-A Nos. 55-144250, No. 56-119132, No. 56-22437, West German Patent No. 110518), styrylanthracene and its derivatives (special 56-46234), stilbene and derivatives thereof (Japanese Patent Laid-Open Nos. 61-210363, 61-228451, 61-14642, 61-72255, 62-47646, 62-36684, 62-10552, 62-30255, 60-93445, 60-94462, 60-174749, 60-175052), aromatic tertiary amine compounds and styrylamine compounds Sho 63-295695, 53-27033, 54-58445, 54-149634, 54-64299, 55-79450, 55-144250, 56-119132, 61 -295558, 61-98353, JP-A-8-239655, US Pat. No. 4,127,412 Aromatic dimethylidene compounds (JP-A-6-330034), pyrazoline derivatives and pyrazolone derivatives (US Pat. Nos. 3,180,729 and 4,278,746, JP-A-55-88064, JP-A-55-88065, JP-A-49-105537) 55-51086, 56-80051, 56-88141, 57-45545, 54-112737, 55-74546), phenylenediamine and its derivatives (US Pat. No. 3,615,404, JP-B-51-10105, JP-B-46-3712, JP-B-47-25336, JP-A-54-53435, JP-B-54-10536, JP-B-54-11925), amino-substituted chalcones and derivatives thereof (US Patent No. 3526501), fluorenone and its derivatives (Japanese Patent Laid-Open No. Sho 54). -11037), hydrazone and derivatives thereof (US Pat. No. 3,717,462, JP-A-54-59143, 55-52063, 55-52064, 55-46760, 55-85495, 57) -11350, 57-148749), silazane and derivatives thereof (US Pat. No. 4,950,950), porphyrin compounds (JP-A 63-295695), anthraquinodimethane and derivatives thereof, and anthrone and derivatives thereof (specialty) Nos. 57-149259, 58-55450, 63-104061, JP-A-61-225151, 61-233750), diphenoquinone and its derivatives, thiopyran dioxide and its derivatives, and carbodiimide and its Derivatives ("polymer prepurines Tsutsu, Japan (Polymer Preprints, Japan) ", 1988, Vol. 37, No. 3, p. 681), fluorenylidenemethane and derivatives thereof (JP-A-60-69657, 61-143765, 61-148159)), distyrylpyrazine and derivatives thereof ("Chemistry Letters", 1990). P.189, JP-A-2-252793, JP-A-5-178842), heterocyclic tetracarboxylic anhydrides and derivatives thereof ("Japanese Journal of Applied Physics", 1988, Vol. 27). L269), porphyrin, phthalocyanine and derivatives thereof (Japanese Patent Laid-Open No. 63-295965), metal complexes of 8-quinolinol and derivatives thereof (Journal of the Institute of Electronics, Information and Communication Engineers, 1990, C) -, P.661), metal complexes having benzoxazole and its derivatives as ligands, metal complexes having benzothiazole and its derivatives as ligands, and the like.

In order to efficiently transfer energy from the triplet excited state of the host material to the light emitting material, the energy level (T ₁ level) of the lowest triplet excited state of the host material is higher than the T ₁ level of the light emitting material. Is preferably high. Since the T ₁ level of the luminescent material becomes higher as the emission wavelength is shorter, a high T ₁ host material is required in the light emitting layer for a short wave light emitting element, while T ₁ is the highest occupied orbit of the host material ( HOMO) and the lowest unoccupied orbit (LUMO), which are related to the ability to inject and transport charges (generally, the larger the energy difference between HOMO and LUMO, the less the charge is injected and the higher the electrical insulation) Therefore, it is important to select an optimal T ₁ level host material.
In particular, the T ₁ level of the light emitting layer host material for a blue light emitting element having an emission maximum wavelength of 500 nm or less is 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol or less). Preferably, they are 65 kcal / mol or more (272 kJ / mol or more) and 80 kcal / mol or less (334 kJ / mol or less).

The material constituting the light emitting layer of the present invention preferably contains only a material having a molecular weight of 3000 or less from the viewpoint of forming by a vapor deposition method. In particular, polymer materials such as polymers and oligomers are not preferable because they are low in volatility and difficult to deposit, and the materials themselves have a molecular weight distribution, making it difficult to obtain light emission with good reproducibility.
High molecular weight compounds having a molecular weight of 3000 or more are difficult to evaporate by heating even under high vacuum conditions, and thin film formation by vacuum deposition tends to be difficult.
In particular, when a substance outside the range of 200 or more and 2000 or less is selected, a low molecular weight compound having a molecular weight of 200 or less is too volatile and difficult to form a thin layer upon vacuum deposition. This is because it tends to be difficult to evaporate by heating underneath.
Moreover, from the easiness of vapor deposition, it is preferable that the material which comprises a light emitting layer is not an ionic compound but a neutral molecular compound.
The light-emitting layer thin film formed by vapor deposition is preferably a uniform non-crystalline thin film (amorphous film) free from defects such as peeling and pinholes, and changes in performance of the light-emitting element when recrystallization occurs over time or heat Therefore, the melting point and the glass transition temperature (Tg) are preferably high. The melting point of the material constituting the light emitting layer is preferably 150 ° C. or higher, more preferably 200 ° C. or higher, further preferably 250 ° C. or higher, and Tg is preferably 70 ° C. or higher, more preferably 100 ° C. or higher, and still more preferably 120 ° C. It is above ℃.
As a host material satisfying the above required performance, a carbazole derivative that has a high T ₁ level, is unlikely to cause crystallization, has a long excited state lifetime, and can be expected to have high emission efficiency is most preferable.

-Luminescent material-
In the present invention, the metal complex of the present invention is used as described above, but a single compound may be used or a plurality thereof may be used. It can also be used in combination with other light emitting materials. The light-emitting material that may be used in combination may be either a fluorescent compound that emits light from singlet excitons or a phosphorescent compound that emits light from triplet excitons.
Examples of light emitting materials that can be used in combination in the present invention include benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives. , Condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styryl Of amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidene compounds, metal complexes of 8-quinolinol derivatives and pyromethene derivatives Various metal complexes represented by transition metal complexes such as genus complex, rare earth complex, iridium trisphenylpyridine complex and platinum porphyrin complex, polymer compounds such as polythiophene, polyphenylene and polyphenylene vinylene, and compounds such as organic silane derivatives .

Although the film thickness of a light emitting layer is not specifically limited, Usually, the thing of the range of 1 nm-5 micrometers is preferable, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm.
The light emitting layer may be a single layer or a plurality of layers, and each light emitting layer emits light with a different emission color, for example, may emit white light as a whole, or white light may be emitted from a single light emitting layer. It may emit light. When there are a plurality of light emitting layers, each light emitting layer may be formed of a single material or may be formed of a plurality of compounds. For example, in the case of a mixed system including a host material and a light emitting material, the host material may be a single material or a mixture of a plurality of types. The light emitting material may be a single material or a mixture of a plurality of materials.
The content of the metal complex having a tridentate or higher ligand in the light emitting layer in the present invention can be used without any particular limitation. However, from the viewpoint of durability and light emission efficiency, the content of the metal complex is about 0. 1 mass%-20 mass% are preferable, 1 mass%-15 mass% are more preferable, and 2 mass%-12 mass% are especially preferable.
The content of the host material can be used without any particular limitation, but is preferably 80% by mass to 99.9% by mass, more preferably 85% by mass to 99% by mass with respect to the total amount of solid substances. -98 mass% is particularly preferred.

Next, another organic layer preferably used in the present invention will be described.
(Hole injection layer, hole transport layer)
The material contained in the hole injection layer and the hole transport layer has one of the function of injecting holes from the anode, the function of transporting holes, or the function of blocking electrons injected from the cathode. If it is.
Materials constituting the hole injection layer and the hole transport layer include tribenzazepine and derivatives thereof, triazole and derivatives thereof, oxazole and derivatives thereof, oxadiazole and derivatives thereof, imidazole and derivatives thereof, polyarylalkane and derivatives thereof. Derivatives, polyarylbenzenes and derivatives thereof, arylamines and derivatives thereof, styrylanthracene and derivatives thereof, stilbenes and derivatives thereof, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, 8-quinolinol and derivatives thereof Metal complexes, pyrazolines and derivatives thereof, pyrazolones and derivatives thereof, phenylenediamines and derivatives thereof, amino-substituted chalcones and derivatives thereof, fluorenones and derivatives thereof, hydrazones And its derivatives, silazane and its derivatives, is preferably at least one selected from the group of metal complexes and porphyrin compounds of the present invention. Preferable examples of these compounds include the same examples as the corresponding compounds described in the section of the host material that can be used in combination.

Further, when the hole transport layer is a layer adjacent to the light emitting layer containing the phosphorescent compound, the triplet excitons generated in the light emitting layer are prevented from moving to the hole transport layer. The energy level (T ₁ level) in the lowest triplet excited state is preferably higher than the T ₁ level of the light emitting material or the host material contained in the light emitting layer. In particular, the T ₁ level of a hole transport material for a blue light emitting device having an emission maximum wavelength of 500 nm or less is preferably 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol or less), and 65 kcal. / Mol or more (272 kJ / mol or more) and 80 kcal / mol or less (334 kJ / mol or less).
As a hole transport material satisfying the above physical property values, a hole transport material described in JP-A No. 2002-1000047 is preferable, and a preferable range is as described in the same publication.
Among the above compound groups, tribenzazepine derivatives can be expected to have high luminous efficiency at high T ₁ , and arylamine derivatives can be expected to improve durability due to high stability. More preferred.
In addition, carbazole, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films, and derivatives thereof as necessary Can be added.

The thickness of the hole injection layer is not particularly limited, but is usually preferably in the range of 0.2 nm to 1 μm, more preferably 1 nm to 0.2 μm, and further preferably 2 nm to 100 nm. .
The thickness of the hole transport layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and even more preferably 10 nm to 500 nm.
The hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the materials described above, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

The method for forming the hole injection layer and hole transport layer when containing the metal complex of the present invention is formed by the degassing step and vapor deposition method, but is not particularly limited when not containing it. In addition to the vacuum deposition method, an LB method, a method in which the hole injecting and transporting material is dissolved or dispersed in a solvent, a coating method, an ink jet method, a printing method, and a transfer method can be used.
In the case of the coating method, the hole injecting and transporting material can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, and polyphenylene. Oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin Etc.

Among the above-described layer forming methods, the hole transport layer is preferably installed by vapor deposition. By installing by the vapor deposition method, a thin film having a uniform and constant film thickness can be formed, and the durability tends to be improved.
When the hole transport layer is installed by vapor deposition, the material of the hole transport layer may be composed of a low molecular organic compound having a molecular weight of 3000 or less and / or a low molecular organic metal compound having a molecular weight of 3000 or less, like the light emitting layer material. preferable.

(Electron injection layer, electron transport layer)
As a material included in the electron injection layer and the electron transport layer, any material having one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode Good.

  Specific examples of materials that can be used for the electron injection layer and the electron transport layer include triazole, oxazole, oxadiazole, imidazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, and fluorenylidenemethane. , Distyrylpyrazine, naphthalene, perylene, and other aromatic ring tetracarboxylic anhydrides, metal complexes of phthalocyanine, 8-quinolinol, metal phthalocyanines, metal complexes having benzoxazole and benzothiazole as ligands , Organosilanes, derivatives thereof, and metal complexes of the present invention. Preferable examples of these compounds are the same as the corresponding compounds described in the description of the host material.

  In the organic electroluminescent device of the present invention, it is preferable to use a layer containing a compound having an ionization potential of 5.9 eV or more (more preferably 6.0 eV or more) between the cathode and the light emitting layer. It is more preferable to use an electron transport layer having an ionization potential of 5.9 eV or more. Luminous efficiency due to holes passing through the light emitting layer and flowing into the electron transport layer by providing a layer containing a compound having an ionization potential of 5.9 eV or more (more preferably 6.0 eV or more) between the cathode and the light emitting layer. Reduction and deterioration of durability can be prevented.

Further, when the electron transport layer is a layer adjacent to the light emitting layer containing the phosphorescent compound, the lowest triplet of the electron transport material is prevented so that triplet excitons generated in the light emitting layer do not move to the electron transport layer. The energy level (T ₁ level) in the excited state is preferably higher than the T ₁ level of the light emitting material or the light emitting layer host material. In particular, the T ₁ level of a hole transport material for a blue light emitting device having an emission maximum wavelength of 500 nm or less is preferably 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol or less), and 65 kcal. / Mol or more (272 kJ / mol or more) and 80 kcal / mol or less (334 kJ / mol or less).
Examples of other electron transporting materials that satisfy the above physical property values include the electron transporting materials described in JP-A No. 2002-1000047, and their preferred ranges are also described in the same publication.

  In addition, carbazole, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films, and derivatives thereof as necessary Can be added.

The thickness of the electron injection layer is not particularly limited, but is usually preferably in the range of 0.2 nm to 1 μm, more preferably 1 nm to 0.2 μm, and further preferably 2 nm to 100 nm.
Although the film thickness of an electron carrying layer is not specifically limited, Usually, the thing of the range of 1 nm-5 micrometers is preferable, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
As a method for forming the electron injection layer and the electron transport layer when containing the metal complex of the present invention, it is formed by the degassing treatment step and the vapor deposition method. In addition to the vapor deposition method, an LB method, a method in which the electron injecting and transporting material is dissolved or dispersed in a solvent, a coating method, an ink jet method, a printing method, a transfer method, or the like can be used.
In the case of the coating method, the electron injecting and transporting material can be dissolved or dispersed together with the resin component. Examples of the resin component include those exemplified for the hole injecting and transporting layer.
Among the layer forming methods described above, the electron transport layer is preferably installed by vapor deposition. By installing by the vapor deposition method, a thin film having a uniform and constant film thickness can be formed, and the durability tends to be improved.
Moreover, when installing an electron carrying layer by a vapor deposition method, it is preferable that the material of an electron carrying layer also consists of a low molecular organic compound with a molecular weight of 3000 or less and / or a low molecular organometallic compound with a molecular weight of 3000 or less like the light emitting layer material. .

(Protective layer)
The organic electroluminescent element of the present invention may have a protective layer in order to prevent moisture and oxygen from entering. As a material contained in the protective layer, any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni, MgO, SiO, SiO ₂ , Al ₂ O ₃ , GeO, NiO, CaO, BaO, and Fe ₂ O. ₃ , metal oxides such as Y ₂ O ₃ and TiO ₂ , metal fluorides such as MgF ₂ , LiF, AlF ₃ , and CaF ₂ , SiN _x , SiO _x N _y Such as nitride, polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene And a copolymer obtained by copolymerizing a monomer mixture containing at least one comonomer, a fluorine-containing copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more, a water absorption of 0 .1% or less of moisture-proof substances and the like.
There is also no particular limitation on the method for forming the protective layer. For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency excitation) (Ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, transfer method can be applied.

<Sealing>
Furthermore, the organic electroluminescent element of this invention may seal the whole element using a sealing container.
Further, a moisture absorbent or an inert liquid may be sealed in a space between the sealing container and the light emitting element. Although it does not specifically limit as a moisture absorber, For example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride Cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, magnesium oxide and the like. The inert liquid is not particularly limited, and examples thereof include fluorinated solvents such as paraffins, liquid paraffins, perfluoroalkanes, perfluoroamines, perfluoroethers, chlorinated solvents, and silicone oils. It is done.

The light-emitting element of the present invention can improve the light extraction efficiency by various known devices. For example, by processing the substrate surface shape (for example, forming a fine concavo-convex pattern), controlling the refractive index of the substrate / ITO layer / organic layer, controlling the film thickness of the substrate / ITO layer / organic layer, etc. It is possible to improve light extraction efficiency and external quantum efficiency.

  The light-emitting element of the present invention may be a so-called top emission type in which light emission is extracted from the anode side.

  The organic electroluminescence device of the present invention can be suitably used for display devices, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like.

  The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable. 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, JP-A-8-234585, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6023308, and the like can be applied.

The driving durability of the organic electroluminescent element in the present invention can be measured by the luminance half time at a specific luminance. For example, using a source measure unit 2400 made by KEITHLEY, a direct voltage is applied to the organic electroluminescence device to emit light, and a continuous driving test is performed under the condition of an initial luminance of 2000 cd / m ² , and the luminance is 1000 cd / m ^2. The brightness half-life time can be obtained by comparing the brightness half-life time with a conventional light emitting device. This numerical value was used in the present invention.
An important characteristic value of this organic electroluminescence device is external quantum efficiency. The external quantum efficiency is calculated by “external quantum efficiency φ = number of photons emitted from the device / number of electrons injected into the device”, and it can be said that the larger this value, the more advantageous the device in terms of power consumption.

  The external quantum efficiency of the organic electroluminescent element is determined by “external quantum efficiency φ = internal quantum efficiency × light extraction efficiency”. In an organic electroluminescent device using fluorescence emission from an organic compound, the limit value of the internal quantum efficiency is 25% and the light extraction efficiency is approximately 20%. Therefore, the limit value of the external quantum efficiency is approximately 5%. It is said that.

The external quantum efficiency of the device is preferably 6% or more, and particularly preferably 12% or more, from the viewpoint of reducing power consumption and driving durability.
Figures external quantum efficiency, the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or around 100~300cd / m ² when the device is driven at 20 ° C. (preferably 200 cd / m ²⁾ The value of external quantum efficiency at can be used.
In the present invention, a KEITHLEY source measure unit 2400 type is used to apply a DC constant voltage to an EL element to emit light, and its luminance is measured using a Topcon luminance meter BM-8, and is 200 cd / m ^2. A value obtained by calculating the external quantum efficiency at is used.

  Further, the external quantum efficiency of the light emitting element can be calculated from the result and the relative luminous efficiency curve obtained by measuring the light emission luminance, the light emission spectrum, and the current density. That is, the number of input electrons can be calculated using the current density value. The emission luminance can be converted into the number of photons emitted by integral calculation using the emission spectrum and the relative visibility curve (spectrum). From these, the external quantum efficiency (%) can be calculated by “(number of photons emitted / number of electrons input to the device) × 100”.

  The light emitting device manufactured according to the present invention can be suitably used in the fields of display devices, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like.

The present invention will be described using examples, but is not limited thereto.
(Comparative Example 1)
<Creation of Sample 1-1>
Using an ITO target having an In ₂ O ₃ content of 95% by mass on a glass substrate having a thickness of 0.7 mm and a 2.5 cm square, DC magnetron sputtering (conditions: substrate temperature 100 ° C., oxygen pressure 1 × 10 ⁻³ Pa), an ITO thin film (thickness 0.2 μm) was formed as a transparent anode. The surface resistance of the ITO thin film was 10Ω / □.
Next, the substrate on which the transparent anode was formed was placed in a cleaning container and subjected to IPA cleaning, and then UV-ozone treatment was performed for 30 minutes.
Subsequently, the substrate on which the transparent anode was formed was placed in a vacuum deposition apparatus, and a hole injection layer having a thickness of 10 nm was formed on the transparent anode by copper phthalocyanine at a rate of 0.5 nm / second by a vacuum deposition method. It was.
Further, 4,4 ′, 4 ″ -tris (2-methylphenylphenylamino) triphenylamine (m-MTDATA) is transported by a vacuum deposition method at a rate of 0.5 nm / sec. A layer was provided.
On top of this, as the light emitting layer, the metal complex EM-1 of the present invention (corresponding to the compound (83) of the specific example of the compound represented by the general formula (I)), the compound H-1 and the compound E- 1 was co-evaporated at a ratio of 8/50/42 by a vacuum evaporation method to provide a light emitting layer having a thickness of 30 nm. A tungsten metal boat was used as the metal complex storage container, heated by resistance heating, and evaporated. The temperature was controlled so that the deposition rate was 0.1 nm / second. The temperature at that time was in the range of about 220 ° C to 270 ° C. The degree of vacuum at the start of vapor deposition of the light emitting layer was 1 × 10 ⁻⁴ Pa.

On the light-emitting layer, Balq ₂ is deposited as an electron transport material in the electron transport layer by a vacuum deposition method at a thickness of 10 nm at a rate of 0.5 nm / second, and then Alq ₃ is deposited as an electron transport material in a vacuum. The electron transport layer having a film thickness of 35 nm was provided by vapor deposition at a rate of 0.2 nm / second by the method.
Further, a patterned mask (a mask having a light emission area of 2 mm × 2 mm) was placed on the electron transport layer, and lithium fluoride was deposited by a vacuum deposition method to provide a 1 nm electron injection layer.
Aluminum was vapor-deposited thereon by a vacuum vapor deposition method to provide a 0.15 μm cathode.
Aluminum lead wires were respectively connected from the anode and the cathode to form a light emitting laminate.

The obtained light-emitting laminate is put in a glove box substituted with argon gas, and sealed with a stainless steel sealing can provided with a desiccant and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba). Sample 1-1 was obtained.
The operations from the deposition of copper phthalocyanine to the sealing were performed in a vacuum or nitrogen atmosphere, and the device was fabricated without exposure to the atmosphere.

Example 1
<Creation of sample 1-2>
In the production method of Sample 1-1, degassing treatment was performed before vapor deposition of the metal complex EM-1 of the present invention. During the degassing process, the film was shielded by using a shutter so as not to be deposited on the substrate, and the deposited material was gradually heated while being monitored by a vacuum gauge, and kept at a temperature at which the pressure in the vacuum apparatus began to rise. The temperature at that time was approximately 200 ° C. After the pressure increase was finished, heating was stopped, and degassing was performed again until the degree of vacuum reached 1 × 10 ⁻⁴ Pa, and the degassing step was completed. Thereafter, an element was produced in exactly the same manner as Sample 1-1, and Sample 1-2 was obtained.

(Comparative Example 2)
<Creation of Samples 2-1 and 2-2>
Samples 1-1 and 1-2 were prepared in the same manner as Samples 1-1 and 1-2 except that FIrpic (bidentate ligand complex) was used instead of the metal complex EM-1. 2-1, 2-2 was obtained.

[Evaluation]
Evaluation was performed by the following method using the light-emitting element obtained as described above.
-External quantum efficiency-
The waveform of the emission spectrum of the manufactured light-emitting element was measured using a multi-channel analyzer PMA-11 manufactured by Hamamatsu Photonics. The wavelength value of the emission peak was determined from this measurement data. Further, the external quantum efficiency was calculated from the waveform of the emission spectrum and the current / brightness (200 cd / m ² ) at the time of measurement, and evaluated according to the following criteria. The results are shown in Table 1 below.

[Evaluation criteria]
◎: 10% or more ○: 5% or more and less than 10% △: 3% or more and less than 5% ×: less than 3%

-Driving durability test-
Using a source measure unit 2400 made by KEITHLEY, DC voltage was applied to the organic electroluminescence device so as to have an initial luminance of 300 cd / m ² , a continuous driving test was performed, and the luminance became 150 cd / m ² The luminance half-life time T (1/2). The luminance half time was evaluated according to the following evaluation criteria.

[Evaluation criteria]
◎: 300 hr or more ○: 150 hr or more and less than 300 hr Δ: 100 hr or more and less than 150 ×: Less than 100 hr

-Light emitting surface-
The light emitting surface state of the obtained device was visually confirmed, and the presence or absence of dark spots or bright spots was evaluated.

  As is apparent from Table 1, the device obtained by the production method of the present invention has improved light emitting efficiency of the device, excellent driving durability, and good light emitting surface shape. On the other hand, in the comparative sample 1-4, by performing the degassing process, the light emission efficiency and the durability are deteriorated, and the light emitting surface state is also deteriorated. Although it is not certain, it seems that the degassing treatment modified the luminescent material and deposited it, affecting the device.

(Example 2)
Sample 1 was prepared in the same manner as Sample 1-2 except that the metal complex EM-2 of the present invention described below was used instead of the metal complex EM-1 in the preparation of Sample 1-2 of Example 1. As a result of evaluation in the same manner as in Example 1, good results were obtained as in Example 1.

From the above, it can be seen that according to the present invention, a high-quality organic electroluminescence device is obtained by performing degassing treatment using the metal complex of the present invention.
It is.

  The organic electroluminescent device obtained by the production method of the present invention is used in the fields of display device, display, backlight, electrophotography, illumination light source, recording light source, exposure light source, reading light source, sign, signboard, interior, optical communication, etc. It can be suitably used.

Claims (11)

A method for producing an organic layer of an organic electroluminescent device having at least one organic layer between a pair of electrodes, wherein a vapor deposition material containing at least one metal complex having a tridentate or higher ligand is degassed. The manufacturing method of the organic layer of the organic electroluminescent element which has a process and the process of heating and vapor-depositing this vapor deposition material after this degassing process. The method for producing an organic layer of an organic electroluminescent element according to claim 1, wherein the vapor deposition material is not exposed to the atmosphere between the degassing step and the vapor deposition step. The method for producing an organic layer of an organic electroluminescent element according to claim 1 or 2, wherein the temperature of the vapor deposition material in the degassing step is the same as or lower than the temperature of the vapor deposition material in the vapor deposition step. . The method for producing an organic layer of an organic electroluminescent element according to any one of claims 1 to 3, wherein the tridentate or higher ligand is a chain ligand. The said metal complex which has a tridentate or more ligand is represented by the following general formula (I), The manufacture of the organic layer of the organic electroluminescent element of any one of Claims 1-3 characterized by the above-mentioned. Method.

(In the general formula (I), M ¹¹ represents a metal ion, and L ¹¹ , L ¹² , L ¹³ , L ¹⁴ and L ¹⁵ each represent a ligand coordinated to M ^11. Between L ^{11 and} L ¹⁴ In addition, L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand by further adding an atomic group to Y ¹¹ , Y ¹² , Y ¹³ represents a linking group, a single bond, or a double bond, respectively, and 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 , and Y ¹³ and L ¹⁴ each independently represent a single bond or a double bond, and n ¹¹ represents 0 to 4.) The method for producing an organic layer of an organic electroluminescent element according to claim 5, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (II).

(In the general formula (II), M ^X1 .L is .Q ^X11 to Q ^X16 representing a metal ion represents a atomic group containing an atom coordinating to an atom or M ^X1 coordinating to M ^{X1 X11} ~L ^X14 Represents a single bond, a double bond or a linking group, that is, an atomic group consisting of Q ^X11 -L ^X11 -Q ^X12 -L ^X12 -Q ^X13 and Q ^X14 -L ^X13 -Q ^X15 -L ^X14 -Q ^X16 Each atomic group is a tridentate ligand. The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond or a covalent bond.) The method for producing an organic layer of an organic electroluminescent element according to any one of claims 1 to 3, wherein the tridentate or higher ligand is a cyclic ligand. The method for producing an organic layer of an organic electroluminescent element according to claim 7, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (III).

(In the general formula (III), Q ¹¹ represents an atomic group forming a nitrogen-containing heterocyclic ^{ring, Z 11, Z 12, Z} 13 represents a substituted or unsubstituted, respectively, represent a carbon atom or a nitrogen atom, M ^Y1 Represents a metal ion which may further have a ligand.) The metal ion in the metal complex having a tridentate or higher ligand is at least one selected from the group consisting of platinum ion, iridium ion, rhenium ion, palladium ion, rhodium ion, ruthenium ion, and copper ion. The manufacturing method of the organic layer of the organic electroluminescent element of any one of Claims 1-8 characterized by the above-mentioned. A method for producing an organic electroluminescent device having at least one organic layer between a pair of electrodes, wherein the at least one organic layer is an organic material of the organic electroluminescent device according to any one of claims 1 to 9. A method for producing an organic electroluminescent element, characterized by being formed using a method for producing a layer. An organic electroluminescent element formed by using the manufacturing method according to claim 10.