JP2007080677A - Organic electroluminescent element and its manufacturing method - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a manufacturing method of an organic electroluminescent element using a liquid phase method capable of manufacturing stably the organic electroluminescent element having a high luminous efficiency and superior in durability, and the organic electroluminescent element manufactured using the same. <P>SOLUTION: This is the manufacturing method of an organic electroluminescent element having at least a luminous layer between a pair of electrodes and the luminous layer is formed by a liquid phase method using a liquid containing at least one kind of a metal complex having a ligand of three seats or more. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an organic electroluminescence device that emits light by converting electric energy into light.

Research and development related to various display elements are being actively performed today, and organic electroluminescence (EL) elements are attracting attention because they can emit light with high luminance at a low voltage. For example, a light-emitting element having an organic thin film formed by vapor deposition of an organic compound is known (see, for example, Non-Patent Document 1).
This light-emitting element uses tris (8-hydroxyquinolinato) aluminum complex (Alq) as an electron transport material, and is laminated with a hole transport material made of an amine compound, so that it can be compared with a conventional single-layer element. It shows significantly improved emission characteristics.
However, since the film thickness of the organic thin film (organic layer) of this light-emitting element is as thin as about 100 nm, there is a problem that it is easily short-circuited when manufactured in an environment with a low cleanness. In addition, a smooth thin film of about 100 nm can be produced relatively easily by vapor deposition, but there is a problem that it is very difficult to produce such a thin film by a coating method, a printing method, a transfer method, an ink jet method, or the like. .

On the other hand, all the elements having the above structure form each layer by a dry process such as a vacuum deposition method, whereas there is a method of forming an element by a so-called wet film forming method such as a spin coat method or a cast method (for example, patents). References 1, 2 etc.).
That is, at least one or more materials forming the hole transport layer, electron transport layer, and light emitting layer are dissolved in a suitable solvent together with a polymer binder, and this is applied to the electrode surface to form the light emitting layer. An electrode is formed on the light emitting layer by vapor deposition or the like (hereinafter referred to as a polymer dispersion type light emitting element).

As compared with the organic light-emitting device produced by the dry process, the following points are mentioned as advantages of the polymer-dispersed light-emitting device.
(1) Materials that are difficult to form in a dry process such as vapor deposition can also be used.
(2) A small amount of doping, which is difficult to control in a dry process, can be easily realized.
(3) The area can be easily increased.
(4) It can be manufactured at low cost.
(5) By introducing a plurality of light emitting materials, light emission from each light emitting material can be easily obtained simultaneously (white light emission is possible).
(6) While each layer is in an amorphous state in a conventional stacked light emitting device, a polymer dispersed light emitting device is thermally stable because each material is dispersed in a polymer binder.

  The structure of the light-emitting layer of the conventional polymer-dispersed light-emitting device includes polyvinylcarbazole in which a perinone derivative or tris (8-quinolinolato) aluminum is dispersed as a light-emitting material, and tris (8-quinolinolato) aluminum and tetra as a light-emitting material in polycarbonate. There are those in which phenylbenzidine is dispersed (see, for example, Patent Documents 1 and 2).

However, in any of these, the problem that the liquid phase deteriorates with the lapse of time when the liquid phase is applied on the electrode, and the light emission efficiency and durability of the light emitting element still deteriorates remains.
Japanese Patent Laid-Open No. 3-790 Japanese Patent Laid-Open No. 3-171590 “Applied Physics Letters”, 1987, Vol. 51, p. 913

An object of the present invention is to provide a method for producing an organic electroluminescent device using a liquid phase method, which can stably produce an organic electroluminescent device having high luminous efficiency and excellent durability.
Another object of the present invention is to provide an organic electroluminescence device having high luminous efficiency and excellent durability.

In view of the above circumstances, the present inventors have conducted extensive research 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 liquid phase method using an organic electroluminescence device having at least a light emitting layer between a pair of electrodes, wherein the light emitting layer contains at least one metal complex having a tridentate or higher ligand. A method for producing an organic electroluminescent element, characterized by comprising:
<2> The method for producing an organic electroluminescent element according to <1>, wherein the tridentate or higher ligand is a chain ligand.

<3> The method for producing an organic electroluminescent element according to the above <1> or <2>, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (I).

(In the general formula (I), M ¹¹ represents a metal ion, and L ^{11 to} L ¹⁵ each represents a ligand coordinated to M ^{11. An} atomic group further exists between L ¹¹ and L ^14. L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand, Y ¹¹ , Y ¹² and Y ¹³ are each a linking group, Represents a single bond or a double bond, 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 the bond between Y ¹³ and L ¹⁴ each independently represents a single bond or a double bond, n ¹¹ represents 0 to 4. M ¹¹ and L ^{11 to} L ¹⁵ The bonds may be any of coordination bonds, ionic bonds, and covalent bonds.)

<4> The organic electric field 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 (II): Manufacturing method of light emitting element.

(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 (Atom groups are tridentate ligands. The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond, an ionic bond, or a covalent bond, respectively.)

<5> The method for producing an organic electroluminescent element according to <1>, 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.)

<6> The organic electroluminescence according to any one of <1> to <5>, wherein the metal ion in the metal complex having a tridentate or higher ligand is a transition metal ion. Device manufacturing method.
<7> The metal ions in the metal complex having a tridentate or higher ligand are iridium ions, platinum ions, gold ions, rhenium ions, tungsten ions, rhodium ions, ruthenium ions, osmium ions, palladium ions, silver ions. <1> to <6>, which is at least one selected from the group consisting of copper ion, cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion and gallium ion The manufacturing method of the organic electroluminescent element.

<8> The organic electroluminescence according to any one of <1> to <7>, wherein the metal ion in the metal complex having a tridentate or higher ligand is a rare earth metal ion. Device manufacturing method.
<9> The above <1> to <8, wherein the liquid containing a metal complex having a tridentate or higher ligand is a polymer dispersion containing a polymer for dispersing the metal complex. The manufacturing method of the organic electroluminescent element of any one of>.
<10> The method for producing an organic electroluminescent element according to any one of <1> to <6>, wherein the liquid phase method is a coating method or a printing method.
<11> The above <1> to <1>, wherein the coating method or the printing method includes one selected from a spin coating method, a bar coating method, a dip coating method, a flow coating method, and a screen printing method. 10> The manufacturing method of the organic electroluminescent element of any one of 10>.
<12> An organic electroluminescent device manufactured using the method for manufacturing an organic electroluminescent device according to any one of <1> to <11>.

ADVANTAGE OF THE INVENTION According to this invention, the manufacturing method of the organic electroluminescent element using the liquid phase method which can manufacture stably the organic electroluminescent element with high luminous efficiency and excellent driving durability can be provided.
In addition, according to the present invention, an organic electroluminescent element having high luminous efficiency and excellent durability can be provided.

The method for producing an organic electroluminescent element of the present invention includes a metal complex having at least a light emitting layer between a pair of electrodes, and the light emitting layer having a tridentate or higher ligand (hereinafter referred to as “metal complex of the present invention”). It is formed by a liquid phase method using a liquid containing at least one kind.
By forming the light-emitting layer by a liquid phase method using a metal complex having a tridentate or higher ligand having excellent stability in a liquid, an organic compound having good performance with little deterioration over time in the manufacturing process. An electroluminescent element can be manufactured.

Hereinafter, the manufacturing method of the organic electroluminescent element of the present invention will be described in detail.
The light emitting layer in the organic electroluminescent element of the present invention is formed by a liquid phase method using a liquid containing a metal complex having a tridentate or higher ligand between a pair of electrodes. If it is a method, it will not specifically limit, Methods, such as a coating method and a printing method, can be used.
Here, the liquid phase method refers to a method of forming a liquid film between the pair of electrodes.

  As the coating method, a bar coating method, a dip coating method, a flow coating method, a spin coating method, a cast coating method, a roll coating method, a doctor blade method, or the like can be used.

Examples of the printing method include those described in JP-A No. 2001-52872, JP-A No. 2001-76874, JP-A No. 2001-93668, JP-A No. 2001-155858, JP-A No. 2001-155661, and the like. Screen printing, offset printing, letterpress printing, gravure printing, and the like can be used.
Among the liquid phase methods, a coating method or a printing method is preferable, and further, one type selected from a spin coating method, a bar coating method, a dip coating method, a flow coating method, and a screen printing method is preferable.

  When the light emitting layer is applied and formed by a liquid phase method, the solvent used for preparing the coating liquid by dissolving or dispersing the material of the light emitting layer is not particularly limited, and is appropriately selected according to the type of components constituting the light emitting layer. can do. For example, alcohols such as water, methanol, ethanol, 1-methoxy-2-propanol, methoxyethanol, phenoxyethanol, etc., ketones such as acetone, methyl ethyl ketone, diethyl ketone, n-propyl methyl ketone, cyclohexanone, dibutyl ether, tetrahydrofuran, Ethers such as dioxane, ethyl acetate, butyl acetate, ethyl 2-ethylhexanoate, methyl propionate, ethyl propionate, γ-butyrolactone, esters such as diethyl carbonate, formamide, N, N-dimethylformamide (DMF), Amides such as N, N-dimethylacetamide, aliphatic hydrocarbons such as hexane, heptane, octane and cyclohexane, aromatic hydrocarbons such as benzene, toluene and xylene, chloroform, Examples include halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, 1,2-dichloroethane, organic solvents or inorganic solvents such as N-methylpyrrolidone (NMP), dimethylimidazoline (DMI), dimethyl sulfoxide (DMSO), and the like. Two or more solvents may be appropriately mixed. and so on. It is also possible to use a mixture of these solvents. There is no restriction | limiting in particular in the solid content in the coating liquid for light emitting layers, The viscosity can be arbitrarily selected according to the wet film forming method.

Furthermore, the light emitting layer formed by the liquid phase method preferably contains a polymer binder.
As polymer binder, polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, Polyurethane, melamine resin, unsaturated polyester, alkyd resin, epoxy resin, silicone resin, polyvinyl butyral, polyvinyl acetal, and the like can be used. These may be used alone or in combination of two or more. The light-emitting layer containing the polymer binder can be easily applied and formed on a large area by a wet film forming method.

  Although the specific example in the case of forming the light emitting layer containing the metal complex in this invention by the apply | coating method is demonstrated by the example using the bar-coat method, it is not limited to this.

(1) First, the metal complex in the present invention is dissolved or dispersed in a solvent to prepare a metal complex-containing liquid. The metal complex-containing liquid can contain a constituent component of the light emitting layer containing the metal complex.
The metal complex-containing liquid is not particularly limited, whether it is a solution or a dispersion, but is preferably a polymer dispersion containing a polymer for dispersing the metal complex in the present invention. When the metal complex-containing liquid is a polymer dispersion liquid, the constituent component of the light emitting layer containing the metal complex in the present invention is preferably dispersed in the polymer. By dispersing the constituent components of the light-emitting layer containing the metal complex in the polymer, the stability of the constituent components in the dispersion is improved, and an organic electroluminescent device that is further excellent in luminous efficiency and durability can be obtained. . As the polymer used for dispersion, for example, polymers described in JP-A Nos. 2001-11568, 2002-25779, and 2004-152746 are preferably used.

The solvent for dissolving or dispersing the metal complex in the present invention is not particularly limited, and examples of the solvent used for preparing the coating solution by dissolving or dispersing the material of the light emitting layer include the solvents described above. It is also possible to use a mixture of these solvents.
The best solvent is selected depending on the molecular weight of the metal complex and the like used in the present invention, the type of substituent, the structure, and the like.

(2) The metal complex-containing liquid obtained above is bar-coated on a pre-cleaned temporary support using a bar coater (for example, # 10 manufactured by Matsubo Co., Ltd.) to produce a thin film of a light emitting layer, A thin film having an arbitrary film thickness can be produced by drying under normal pressure or reduced pressure at room temperature or under heating.
The drying conditions for the thin film can be appropriately selected according to various conditions such as the compound to be used, the solvent and the like, but in general, the drying pressure can be performed under normal pressure or reduced pressure.

When a polymer dispersion is used as the metal complex-containing liquid, liquids having various viscosities can be used, and the solution viscosity varies depending on the coating method. Therefore, it is preferable to prepare a solution having a viscosity suitable for the coating method.
The polymer dispersion is prepared by dissolving a polymer (for example, PVK) and a metal complex according to the present invention in a solvent (for example, toluene and chloroform 1: 1) for a time necessary for dissolving or dispersing using a dispersion apparatus, and dissolving or dispersing the polymer. Can be prepared. A dispersion apparatus is not specifically limited, A well-known apparatus can be used.
(3) Next, an organic electroluminescent element can be manufactured by vapor-depositing a cathode material (for example, aluminum) etc. in a vapor deposition apparatus on the light emitting layer obtained above.

Next, each element etc. which comprise the organic electroluminescent element of this invention are demonstrated.
[Metal complex having a tridentate or higher ligand]
The metal complex having the tridentate or higher ligand in the present invention will be described.
The atom coordinated to the metal ion in the metal complex is not particularly limited, but is preferably an oxygen atom, a nitrogen atom, a carbon atom, a sulfur atom or a phosphorus atom, more preferably an oxygen atom, a nitrogen atom or a carbon atom, a nitrogen atom or a carbon atom. Atoms are more preferred.

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

  The metal complex having a tridentate or higher ligand in the present invention is preferably a metal complex having a tridentate or higher and a hexadentate ligand from the viewpoint of improving luminous efficiency and durability, and is typified by iridium ions. In the case of a metal ion that easily forms a hexacoordinated complex, a metal complex having a tridentate, tetradentate, or hexadentate ligand is more preferable, and a tetracoordinate complex represented by a platinum ion In the case of a metal ion that easily forms a metal complex, a metal complex having a tridentate or tetradentate ligand is more preferable, and a metal complex having a tetradentate ligand is more preferable.

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

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

  The metal complex in the present invention is preferably a compound represented by general formula (I), general formula (II) or general formula (III) described in detail below.

  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 bond between M ¹¹ and L ^{11 to} L ¹⁵ may be any of a coordination bond, an ionic bond, and a covalent bond.

The compound represented by formula (I) will be described in detail.
In the general formula (I), M ¹¹ represents a metal ion. Although it does not specifically limit as a metal ion, A bivalent or trivalent metal ion is preferable. As the divalent or trivalent metal 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, a carbon atom, or a phosphorus atom is preferable, and a nitrogen atom, oxygen An atom, a sulfur atom, or a carbon atom is more preferable, and a nitrogen atom, an oxygen atom, or a carbon atom is still more preferable.

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

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a carbon atom are not particularly limited, but are each independently an imino ligand, an aromatic carbocyclic ligand (for example, a benzene ligand) , Naphthalene ligand, anthracene ligand, phenanthracene ligand, etc.), heterocyclic ligand (eg thiophene ligand, pyridine ligand, pyrazine ligand, pyrimidine ligand, thiazole coordination) Children, oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, 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). And examples thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, and the like, and thiocarbonyl ligands ( Example, if thioketone ligand, etc. thioester ligands), or thioether ligands (e.g. dialkyl thioether ligands, diaryl thioether ligands, etc. thiofuryl ligand), and the like. These substituted ligands may be further substituted.

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

L ¹¹ and L ¹⁴ are each independently an aromatic carbocyclic ligand, alkyloxy ligand, aryloxy ligand, ether ligand, alkylthio ligand, arylthio ligand, alkylamino coordination Ligand, arylamino ligand, acylamino ligand, nitrogen-containing heterocyclic ligand (eg pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand) Ligands, oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands, oxadiazole ligands, thiadiazole ligands, or condensed ligand bodies containing them (For example, a quinoline ligand, a benzoxazole ligand, a benzimidazole ligand, 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 represents a ligand forming a coordination bond with M ¹¹ Preferably, M ¹¹
Examples of ligands that form a coordination bond with pyridine ring, pyrazine ring, 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, etc.) and tautomers thereof, and pyridine ring, pyrazine ring, pyrimidine ring, pyrrole ring, and condensed ring containing them (for example, quinoline ring) , Benzpyrrole and the like, and tautomers thereof are more preferable, pyridine ring, pyrazine ring, pyrimidine ring, and condensed ring containing them (for example, quinoline ring) are more preferable, pyridine ring, and A condensed ring containing a pyridine ring (for example, a quinoline ring) is particularly preferable.

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

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

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

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

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

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

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

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

Q ²¹ and Q ²² each independently represents an atomic group forming a nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ²¹ ). The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is not particularly limited, and 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 ), A sulfonylamino 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 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, phenylsulfuryl). 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). To 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazoli Thio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like), a sulfonyl 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, mesyl, tosyl, etc.), sulfinyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzene And ureido groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include ureido, methylureido, and phenylureido. ),

A phosphoric acid amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide); Hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, 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 that forms a ring (for example, a benzo-fused ring, a pyridine-fused ring, etc.) and a halogen atom are more preferred, an aryl group and a halogen atom are more preferred, and an aryl group is particularly preferred.

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

  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 general formula (3-A) is demonstrated.

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, A group that forms a benzo-fused ring, a pyridine-fused ring, etc.) is particularly preferred.

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

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

Y ⁷¹ , Y ⁷² and Y ⁷³ 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). R ⁷¹ and R ⁷² , R ⁷³ and R 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. R ^C3 , R ^C4 , R ^C5 , and R ^C6 each independently represent a hydrogen atom or a substituent, and the substituent is synonymous with the substituent 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 substituted at the 1,2-position, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or an alkylene group having 1 to 8 carbon atoms.

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 a nitrogen-containing heterocycle that is coordinated to each other, and at least one of L ⁸¹ , L ⁸² , and 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 following general formula (II).

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, the atomic group consisting of Q ^X11 -L ^X11 -Q ^X12 -L ^X12 -Q ^X13 and the atomic group consisting of Q ^X14 -L ^X13 -Q ^X15 -L ^X14 -Q ^X16 are each a tridentate ligand. The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond, an ionic bond, or a covalent bond, respectively.

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 with M ^X1 by 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 is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio. ), Thiocarbonyl groups (for example, thioketone groups, thioester groups, etc.), thioether groups (for example, dialkyls) Thioether group, 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. Specific examples of the linking group are shown below, but are not limited thereto.

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 general formula (1) 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.

Of the compounds represented by the general formula (II), more preferred are compounds represented by the following general formula (X2), and still more preferred are compounds 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. , And compounds (243) and (244) (the structures are shown below), but are not limited thereto.

  Among the compounds represented by the above compound examples, a tetradentate ligand containing bipyridyl or phenanthroline in a partial structure, a Schiff base type tetradentate ligand, a phenylbipyridyl tridentate ligand, a diphenylpyridine tridentate ligand, A compound excluding a compound having a ligand selected from terpyridine tridentate ligands is more preferable.

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

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

In general formula (III), Q ¹¹ represents a group of atoms that form 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). To 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazoli Thio, 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, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, 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.
As the compound represented by the general formula (III), a compound represented by the general formula (a) and the general formula (b) or a tautomer thereof is more preferable, and a compound represented by the general formula (b) or Its tautomer is more preferred.
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 and M ^Y1 have the same meaning, and 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 exemplarily 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 position group.

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

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

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

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

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 ^. , ^Z204 , ^Z205 , ^Z206 , ^Z210 , ^Z211 , ^Z212 , ^L101 , ^L102 , ^L103 , ^L104
, M ¹⁰¹ , X ⁴⁰¹ , and 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), and compound (27) described in Japanese Patent Application No. 2004-88575. -Compound (32), Compound (36)-Compound (38), Compound (42)-Compound (44), Compound (50)-Compound (52), and Compound (57)-Compound (154) (below The structure is shown), 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, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl 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, etc.), sulfonyl group (preferably carbon Number 1-30, more preferably number 1-20, particularly preferably number 1-12, such as mesyl, tosyl, etc. And the like.), 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 by a nitrogen atom is preferably a substituted amino group or a nitrogen-containing hetero five-membered heteroaryl group bonded by a nitrogen atom, and particularly preferably a nitrogen-containing hetero five-membered heteroaryl group bonded by a nitrogen atom.

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

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

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

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

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

The compound represented by formula (A-2) will be described in detail.
M ^A2 , Y ^A21 , Y ^A24 , Y ^A25 , Y ^A28 , Y ^A22 , Y ^A23 , Y ^A26 , Y ^A27 , L ^A21 , L ^A22 , L ^A23 , and L ^A24 correspond to the general formula (A-1). 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 represents a carbon atom or a nitrogen atom independently. Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^B11 , L ^B12 , L ^B13 and L ^B14 each represent a linking group. Q ^B11 and Q ^B12 each represents a partial structure containing an atom bonded to M ^B1 through a covalent bond.

General formula (B-1) is demonstrated in detail.
In the general formula (B-1), M ^B1 , Y ^B11 , Y ^B14 , Y ^B15 , Y ^B18 , Y ^B12 , Y ^B13 , Y ^B16 , Y ^B17 , L ^B11 , L ^B12 , L ^B13 , L ^B14 , Q ^B11 , 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 atoms) , 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, 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, G ^C32 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C31 and L ^C32 each represent a linking group. Z ^C31 , Z ^C32 , Z ^C33 , Z ^C34 , Z ^C35 and Z ^C36 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

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

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

The compound represented by formula (C-3) will be described in detail.
In the general formula (C-3), M ^C3 , L ^C31 , L ^C32 , G ^C31 , and G ^C32 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 ^(E1), M E1 represents a metal ion. J ^E11 and J ^E12 represent an atomic group necessary for forming a five-membered ring. G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

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

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

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

In formula (E-3), M ^E3 represents a metal ion. 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 , It is synonymous with L ^F13 , R ^F11 , R ^F12 , R ^F13 and R ^F14 , and the preferred range is also the same.
Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 and Z ^F46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 and Z ^F46 are preferably substituted or unsubstituted carbon atoms, and more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.
X ^F41 and X ^F42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^F41 and X ^F42 are preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

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

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

[Organic electroluminescence device]
Hereinafter, the organic electroluminescent element of the present invention (hereinafter sometimes referred to as “organic EL element” as appropriate) will be described.
The light-emitting element of the present invention has a cathode and an anode on a substrate, and an organic compound layer including an organic light-emitting layer (hereinafter sometimes simply referred to as “light-emitting layer”) between both electrodes. In view of the properties of the light emitting element, at least one of the anode and the cathode is preferably transparent.

  As an aspect of lamination of the organic compound layer in the present invention, an aspect in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated in this order from the anode side is preferable. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. A hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Further, the light emitting layer may be only one layer, or the light emitting layer may be divided into a first light emitting layer, a second light emitting layer, a third light emitting layer, and the like. Furthermore, each layer may be divided into a plurality of secondary layers.

-Light emitting layer-
When an electric field is applied to the light emitting element, holes injected from the anode, hole injection layer or hole transport layer in the light emitting layer recombine with electrons injected from the cathode, electron injection layer or electron transport layer, Emits light. The material forming the light-emitting layer has the function of receiving holes from the anode, etc. when an electric field is applied, the function of receiving electrons from the cathode, etc., the function of moving charges, and the function of emitting light by providing a field for recombination of holes and electrons. There is no particular limitation as long as it can form a layer having s.

  The light-emitting layer contains a metal complex having a tridentate or higher ligand, and the metal complex (A) functions as a light-emitting material, and (B) a host material (hereinafter also referred to as “charge transport material”). Therefore, an embodiment using each function is preferable.

  When the metal complex is used as a material having the function of the light-emitting material (A), the light-emitting material other than the metal complex further uses one that emits light from either singlet excitons or triplet excitons. May be. For example, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, perylene, perinone, oxadiazole, aldazine, pyralidine, cyclopentadiene, bisstyrylanthracene, quinacridone, Pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, aromatic dimethylidin compounds, metal complexes other than the metal complexes of the present invention (metal complexes of 8-quinolinol derivatives, rare earth complexes, etc.), polymer light emitting materials (polythiophene, polyphenylene) , Polyphenylene vinylene, etc.), organosilanes, transition metal complexes other than the metal complex of the present invention (iridium trisphenylpyridine complex, etc.), and derivatives thereof can be used. . In addition, cyanine dyes, merocyanine dyes, styryl dyes, anthracene derivatives, porphyrin derivatives, phthalocyanine derivatives, dyes such as coumarin, DCM, and Nile red, laser dyes, and the like can be used.

  Although content in particular of the luminescent compound in a light emitting layer is not restrict | limited, For example, it is preferable that it is 0.1-70 mass%, and it is more preferable that it is 1-20 mass%. If the content of the luminescent compound is less than 0.1% by mass or exceeds 70% by mass, the effect may not be sufficiently exhibited.

  The thickness of the light emitting layer is preferably 10 to 200 nm, and more preferably 20 to 80 nm. When the thickness exceeds 200 nm, the driving voltage may increase. On the other hand, if it is less than 10 nm, the organic EL device may be short-circuited.

  As described above, the light emitting layer may be formed of a single material or a plurality of materials. In addition, the light emitting layer may be one or plural, and each layer may emit light with a different emission color to emit white light or the like. White light may be emitted from a single light emitting layer. When there are a plurality of light emitting layers, each light emitting layer may be formed of a single material or a plurality of materials. The method for forming the light emitting layer is as described above.

  Regarding other components such as a substrate, an electrode, each organic layer, and other layers in the organic electroluminescence device of the present invention, for example, [0441] to [0442] of JP-A-2004-221068, [0443] to [0444] of Japanese Patent Application Laid-Open No. 2004-214178, [0445] to [0446] of Japanese Patent Application Laid-Open No. 2004-146067, [0447] to [0448] of Japanese Patent Application Laid-Open No. 2004-103577, and Japanese Patent Application Laid-Open No. 2003-2003. [0449] to [0450] of Japanese Patent No. 323987, [0451] to [0452] of Japanese Patent Laid-Open No. 2002-305083, [0453] to [0454] of Japanese Patent Laid-Open No. 2001-172284, and Japanese Patent Laid-Open No. 2000-186094. From [0455] to [0456] of the gazette and from [0457] of the Japanese translations of PCT publication No. 2003-515897 0458] as described in the like can be similarly applied to the present invention. However, the present invention is not limited to these.

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.
With respect to the driving method of the organic electroluminescent device of the present invention, for example, JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-241047. No. 2,784,615, U.S. Pat. Nos. 5,828,429, 6023308, and the like, and the like can be applied.

  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.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to them.

[Comparative Example 1A]
A transparent support substrate is obtained by forming a ITO film with a thickness of 150 nm on a glass substrate of 25 mm × 25 mm × 0.7 mm (manufactured by Tokyo Sanyo Vacuum Co., Ltd.). This transparent support substrate is etched and cleaned.
The ITO glass substrate was spin-coated with Baytron P (PEDOT-PSS solution (polyethylenedioxythiophene-polystyrene sulfonic acid dope) / Bayer) as a hole injection / transport layer, and then vacuum-dried at 100 ° C. for 1 hour. And a hole injection / transport layer (film thickness of about 100 nm).
On top of this, polyvinylcarbazole (Mw = 63000, manufactured by Aldrich): 40 parts by mass, tris (2-phenylpyridine) iridium complex (orthometalated complex): 3 parts by mass, 1,2-dichloroethane: 3200 parts by mass The light emitting layer composition liquid is spin-coated to form a light emitting layer (film thickness of about 50 nm).
Next, electron transport materials BAlq ₂ and Alq ₃ are sequentially deposited so as to have film thicknesses of 20 nm and 30 nm, respectively, to form an electron transport layer.
Furthermore, LiF is deposited in a vacuum of 10 ⁻³ to 10 ⁻⁴ Pa in order with a film thickness of about 3 nm under conditions at a substrate temperature of room temperature.
A patterned mask (a mask having a light emission area of 2 mm × 2 mm) is placed thereon, and aluminum is deposited to a thickness of about 400 nm to produce a device.
The produced element is sealed in a dry glove box.

[Example 1A]
In the device of Comparative Example 1A, a device is produced in the same manner as in Comparative Example 1A, except that compound Pt-1 is used instead of the tris (2-phenylpyridine) iridium complex.

[Comparative Example 2A]
In the device of Comparative Example 1A, a device is produced in exactly the same manner as Comparative Example 1A, except that Compound Ir-1 is used instead of the tris (2-phenylpyridine) iridium complex.

[Example 2A]
In the device of Example 1A, a device is fabricated in exactly the same manner as in Example 1A, except that compound Pt-2 is used instead of compound Pt-1.

(Element evaluation)
(1) Luminous efficiency: External quantum efficiency Using a source measure unit 2400 made by KEITHLEY, a direct current voltage is applied to each element to emit light. The luminance is measured using a luminance meter BM-8 manufactured by Topcon Corporation, and the emission spectrum and emission wavelength are measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these numerical values, the external quantum efficiency with a luminance of around 1000 cd / m ² was calculated by the luminance conversion method and evaluated according to the following criteria.

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

(2) driving durability: Like the luminance half-life above (1), a DC voltage was applied to each element so that the luminance 1000 cd / m ^2, to measure the time until the brightness becomes 500 cd / m ² . The luminance half time was evaluated according to the following evaluation criteria.

[Evaluation criteria]
○: 2000 hr or more Δ: 1000 hr or more and less than 2000 ×: less than 1000 hr

[Examples 1B and 2B and Comparative Examples 1B and 2B]
In the preparation of each element of Examples 1A, 2A, and Comparative Examples 1A, 2A, the composition solution for the light emitting layer was spin-coated after 5 hours. Otherwise, Examples 1A, 2A, and Comparative Examples 1A, Each element is fabricated in exactly the same manner as 2A.

(Element evaluation)
(3) External quantum efficiency and luminance half-life of the solution-aged product The external quantum efficiency and luminance half-time of the device produced as described above are measured by the same methods as in (1) and (2), respectively.
The above results are summarized in the table below.

[Examples 3A and 3B and Comparative Examples 3A and 3B]
In the devices of Examples 1A and 1B, the devices of Examples 3A and 3B are formed in exactly the same manner as in Examples 1A and 1B except that Pt-3 is used instead of the compound Pt-1. Moreover, the element of Comparative Example 3A, 3B is created using Ir-3 (comparative compound) instead of the tris (2-phenylpyridine) iridium complex of the element of Comparative Example 1A, 1B.
The emission color of the elements of Examples 3A and 3B and Comparative Examples 3A and 3B is blue. Examples 3A and 3B are superior to Comparative Examples 3A and 3B in the external quantum efficiency and driving durability before and after solution aging.

[Examples 4A, 4B to 6A, 6B]
In the devices of Examples 1A, 1B to 3A, and 3B, the light-emitting layers were formed in the same manner as in Examples 1A, 1B to 3A, and 3B, except that the light-emitting layer was formed by the bar coating method instead of the spin coating method, and corresponded to each. An element is formed. Similar to Examples 1A, 1B-3A, 3B, good results are obtained.

  As is clear from the above results, the device using the metal complex of the present invention is superior in luminous efficiency and driving durability as compared with a comparative device using a conventional metal complex having a bidentate ligand. Moreover, in the comparative element using the metal complex having a bidentate ligand in the related art, the performance deterioration is caused by the aging of the solution, whereas in the element of the present invention, the performance deterioration after the aging of the solution is small, and the manufacturing factor fluctuates. It is understood that the performance change due to can be suppressed.

Claims (12)

A method for producing an organic electroluminescent device having at least a light emitting layer between a pair of electrodes, wherein the light emitting layer uses a liquid containing at least one metal complex having a tridentate or higher ligand. A method for producing an organic electroluminescent element, characterized by comprising: The method for producing an organic electroluminescent element according to claim 1, wherein the tridentate or higher ligand is a chain ligand. The method for producing an organic electroluminescent element according to claim 1 or 2, wherein the metal complex having a tridentate or higher ligand is represented by the following general formula (I).

(In the general formula (I), M ¹¹ represents a metal ion, and L ^{11 to} L ¹⁵ each represents a ligand coordinated to M ^{11. An} atomic group further exists between L ¹¹ and L ^14. L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand, Y ¹¹ , Y ¹² and Y ¹³ are each a linking group, Represents a single bond or a double bond, 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 the bond between Y ¹³ and L ¹⁴ each independently represents a single bond or a double bond, n ¹¹ represents 0 to 4. M ¹¹ and L ^{11 to} L ¹⁵ The bonds may be any of coordination bonds, ionic bonds, and covalent bonds.) The method for producing an organic electroluminescent element according to claim 1, 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 (Atom groups are tridentate ligands. The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond, an ionic bond, or a covalent bond, respectively.) The method for producing an organic electroluminescent element according to claim 1, 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 method for producing an organic electroluminescent element according to claim 1, wherein the metal ion in the metal complex having a tridentate or higher ligand is a transition metal ion. The metal ion in the metal complex having a tridentate or higher ligand is iridium ion, platinum ion, gold ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, palladium ion, silver ion, copper ion. The organic electroluminescent element according to claim 1, wherein the organic electroluminescent element is one or more selected from the group consisting of cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, and gallium ion. Production method. The method for producing an organic electroluminescent element according to any one of claims 1 to 7, wherein a metal ion in the metal complex having a tridentate or higher ligand is a rare earth metal ion. The liquid containing a metal complex having a tridentate or higher ligand is a polymer dispersion containing a polymer for dispersing the metal complex. The manufacturing method of the organic electroluminescent element of description. The method for producing an organic electroluminescent element according to claim 1, wherein the liquid phase method is a coating method or a printing method. The coating method or the printing method includes one selected from a spin coating method, a bar coating method, a dip coating method, a flow coating method, and a screen printing method. The manufacturing method of the organic electroluminescent element as described in a term. It manufactures using the manufacturing method of the organic electroluminescent element of any one of Claims 1-11, The organic electroluminescent element characterized by the above-mentioned.