JP2007073845A - Organic laser oscillator - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic laser oscillator with excellent driving durability. <P>SOLUTION: The organic laser oscillator includes an organic light emitting area having a light emitting material, and a resonator structure for resonating light emission from the light emitting area between first and second surfaces so as to perform amplifying. The oscillator includes a light emitting material having metallic complex with a ligand to be coordinated over tridentate. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an organic laser oscillation element excellent in driving durability.

  Semiconductor lasers have the merit that laser oscillators can be dramatically reduced in size and weight compared to other gas or solid-state lasers, and recording media such as optical integrated circuits, optical fibers, optical disks, and optical memories. As a light source, it has been put to practical use in various fields. In particular, in recent years, attention has been focused on organic laser oscillation elements that can oscillate lasers of various wavelengths by using organic semiconductors. The organic laser oscillation element is expected to be further developed in the future due to the advantage that it can be mass-produced at low cost, in addition to the diversity in which laser light in any desired wavelength range can be obtained by selecting an organic material. The organic laser oscillating element extracts light with amplified directivity by resonating light emitted by optical excitation by an external excitation light source. Basically, all of the light obtained by light excitation by light excitation by an external excitation light source is diffuse light, and only light in one direction is repeatedly reflected between the two reflecting surfaces to resonate. In order to increase the energy density and obtain strong laser light, it is necessary to fill the light emitting material with a high density and increase the amount of excitation light. As a result, there is a problem that the organic light emitting material is deteriorated by light or heat generation. It was.

An attempt to improve durability by suppressing molecular motion using an asymmetric rare earth complex as a light emitting material has been disclosed (see Patent Document 1). There has been proposed an attempt to obtain laser light by amplifying light emitted from an excimer state using a phosphorescent material as a light emitting material (see Patent Document 2). Phosphorescence is triplet emission and has a long excitation lifetime, and therefore has the advantage of being able to emit light with low excitation energy. As a phosphorescent material, a bidentate platinum complex is disclosed.
However, these disclosed means are not sufficient for the demand for improvement in driving durability, and further improvement has been demanded.
JP 2004-179296 A JP 2004-327634 A

  An object of the present invention is to provide an organic laser oscillation element excellent in driving durability.

The above-described problems of the present invention have been solved by the following means.
<1> An organic laser oscillation element including an organic light emitting region containing a light emitting material and a resonator structure that resonates and amplifies light emitted from the light emitting region between a first surface and a second surface. An organic laser oscillation element, wherein the light emitting material includes a metal complex having a ligand capable of coordinating at three or more positions.
<2> The organic laser oscillation element according to <1>, wherein the light emitting region further contains a host material.
<3> The organic laser oscillation according to <1> or <2>, wherein the light emitting material emits light from an excimer state, and the resonator structure amplifies light in one direction of the light emission element.
<4> The organic laser oscillation element according to any one of <1> to <3>, wherein the light emitting material is excited by excitation light from an external excitation light source.
<5> The organic compound according to any one of <1> to <4>, wherein the metal complex having a tridentate or higher ligand is a compound represented by the following general formula (I): Laser oscillator:

(In the general formula (I), M ¹¹ represents a metal ion, and L ^{11 to} L ¹⁵ each represents a ligand coordinated to M ^{11. An} atomic group further exists between L ¹¹ and L ^14. L ¹⁵ may be bonded to both L ¹¹ and L ¹⁴ to form a cyclic ligand, 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 These bonds may be any of coordination bond, ionic bond, and covalent bond.)
<6> The organic laser oscillation device according to <5>, wherein the tridentate or higher ligand is a chain ligand.
<7> The metal complex having a tridentate or higher ligand is a compound represented by the following general formula (II), according to any one of <1> to <4>, Organic laser oscillator:

(In the general formula (II), M ^X1 .L is .Q ^X11 to Q ^X16 representing a metal ion represents a atomic group containing an atom coordinating to an atom or M ^X1 coordinating to M ^{X1 X11} ~L ^X14 Represents a single bond, a double bond or a linking group, that is, an atomic group consisting of Q ^X11 -L ^X11 -Q ^X12 -L ^X12 -Q ^X13 and Q ^X14 -L ^X13 -Q ^X15 -L ^X14 -Q ^X16 Each atomic group is a tridentate ligand, and the bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond, an ionic bond, or a covalent bond.
<8> The metal complex having a tridentate or higher ligand is a compound represented by the following general formula (III), according to any one of <1> to <4>, Organic laser oscillator:

(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).
<9> The organic laser oscillation element according to any one of <1> to <8>, wherein the metal ion in the metal complex having a tridentate or higher ligand is a transition metal ion. .
<10> 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 <9>, which is one or more selected from the group consisting of copper ion, cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, and gallium ion Organic laser oscillation element.
<11> The organic laser oscillation element according to any one of <1> to <8>, wherein the metal ion in the metal complex having a tridentate or higher ligand is a rare earth metal ion. .

  According to the present invention, an organic laser oscillation element excellent in driving durability is provided.

Hereinafter, the organic laser oscillation element of the present invention will be described in detail.
1. SUMMARY OF THE INVENTION An organic laser oscillation device of the present invention includes an organic light emitting region containing a light emitting material, and a resonator structure that resonates and amplifies light emitted from the light emitting region between a first surface and a second surface. The light emitting material includes a metal complex having a ligand capable of coordinating in three or more positions. The light emitting region preferably further contains a host material.

The light emitted from the light emitting material in the present invention has light emitted from an excimer state, and is amplified in one direction amplified by repeating resonance between two reflecting surfaces sandwiching a layer region including the light emitting material. Light is extracted as laser light.
Preferably, the light emitting material is caused to emit light by excitation light from an external excitation light source. The external excitation light source only needs to be able to excite the light emitting material. For example, a semiconductor laser, a solid-state laser, a gas laser, an LED, an organic EL, a halogen lamp, a flash lamp, a mercury lamp, or the like can be used. Contains the luminescent component of the region.

2. Configuration of Organic Laser Oscillating Element The light emitting region in the present invention is a region having a function of emitting light by recombination of electrons and holes generated by light from an external excitation source.
The resonator structure according to the present invention has a function of amplifying light obtained by light emission in the light emitting region by resonance and generating directional laser light, and has at least two light reflecting surfaces of a first surface and a second surface. Have

  The organic laser oscillation element of the present invention has a light emitting region between two reflecting plates. The light emitting region contains a light emitting material. In the case where a host material is included in the light emitting region, the host material may be a charge transporting material or a non-charge transporting material.

  In addition, the organic laser oscillation device of the present invention uses an organic material that can achieve a current density capable of forming an inversion distribution state of a light emitting material as a host material or a charge transport material, so that a light emitting region is held between electrodes. An organic laser oscillation element having the above-described configuration can be taken.

2-1. Resonator structure The optical resonator structure in the organic laser oscillation device of the present invention can be used in combination with a multilayer mirror or a metal mirror in which two types of layers having different refractive indexes are alternately stacked. The optical length of the optical resonator is set so that light emission becomes a single mode in which low-order modes are not mixed in the spectrum and light having strong directivity in front of the element. Specifically, the resonator structure described in Laser Handbook 2nd edition (Ohm company publication), Applied Physics Handbook 2nd edition (Maruzensha publication), etc. can be used.
The multilayer mirror is a multilayer film in which two types of oxide, nitride, or semiconductor layers having different refractive indexes are alternately stacked. Typical examples of the combination include dielectrics such as TiO ₂ and SiO ₂ , SiNx and SiO ₂ , Ta ₂ O ₅ and SiO _2, and semiconductor multilayer films such as GaAs and GaInAs.
The multilayer mirror reflects light at the interface of each layer. However, the light reflected from each interface is intensified by λ / 4 with respect to the wavelength of light used (target emission wavelength) λ. Set to thickness.

2-2. Host Material The host material in the present invention constitutes a matrix that holds a dispersion of a light emitting material as a light emitting region.

  Examples of the host material in the present invention include a carbazole derivative, a triazole derivative, an oxazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, and an arylamine having hole transport properties. Derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidine compounds, porphyrin compounds, polysilane compounds, poly ( N-vinylcarbazole) derivatives, aniline copolymers, thiophene oligomers and conductive polymer oligomers such as polythiophene, organosilane compounds, carbon Film, and a metal complex of the present invention.

  Further, metal chelated oxinoid compounds, polyarylene compounds, condensed aromatic carbocyclic compounds, non-heteroaromatic heterocyclic compounds, etc. having electron transporting properties. In particular, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine Derivatives, tetracarboxylic anhydrides of aromatic rings such as naphthalene and perylene, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives, metal complexes represented by metalated phthalocyanine, benzoxazole or benzothiazole ligands Complexes, organosilane compounds and the like are also preferable.

  As the non-charge transporting host material, polyimide, polyamide, polymethyl methacrylate, polyacrylate, polyester, polyurethane, polycarbonate, epoxy resin, polystyrene, siloxane polymer, or the like can also be used.

  In the organic laser oscillation device of the present invention, the content of the light emitting material in the light emitting region is preferably 1% by mass or more and 100% by mass or less, and more preferably 10% by mass or more.

2-3. Multidentate metal complex having 3 or more sites The metal complex having a tridentate or higher ligand in the present invention will be described.
1) Metal ion The atom coordinated to the metal ion in the metal complex is not particularly limited, but is preferably an oxygen atom, a nitrogen atom, a carbon atom, a sulfur atom or a phosphorus atom, more preferably an oxygen atom, a nitrogen atom or a carbon atom, More preferred are nitrogen or carbon atoms.

  The metal ion in the metal complex is not particularly limited, but is preferably a transition metal ion or a rare earth metal ion, more preferably an iridium ion or a platinum ion, from the viewpoints of improving luminous efficiency, improving durability, and reducing driving voltage. , Gold ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, palladium ion, silver ion, copper ion, cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, gallium ion, or rare earth metal ion (E.g., europium ion, cadolinium ion, or terbium ion) is preferable, and iridium ion, platinum ion, gold ion, rhenium ion, tungsten ion, palladium ion, zinc ion, aluminum is more preferable. Ion, a gallium ion, europium ion, gadolinium ion or terbium ion, an iridium ion, a platinum ion, a rhenium ion, a tungsten ion, europium ion, gadolinium ion or terbium ion are particularly preferred.

2) Coordination number 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 or lower ligand from the viewpoint of improving luminous efficiency and durability. In the case of a metal ion that easily forms a hexacoordinate complex represented by iridium ion, a metal complex having a tridentate, tetradentate, or hexadentate ligand is more preferable, and platinum ion is representative. In the case of a metal ion that easily forms a tetracoordinate complex, a metal complex having a tridentate or tetradentate ligand is more preferable, and a metal complex having a tetradentate ligand is more preferable.

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

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

4) Preferred Metal Complex Structure The metal complex in the present invention is preferably a compound represented by the following general formula (I), general formula (II) or general formula (III).
Preferably, the ligand of the metal complex has at least one substituent, and the steric parameter of the substituent is −2.6 or more. Preferably, the steric parameter of at least one linking group of the metal complex is −2.6 or more. (However, the steric parameter of the linking group refers to the sum of the steric parameters of the portion excluding the atom linking the ligand. For example, in the case of dimethylmethylene linking, the two methyl moieties are the target of steric parameter calculation. When expressed using the following Es value, −1.24 × 2 = −2.48)) The one having a larger steric parameter (that is, a smaller steric hindrance) forms an excimer dimer or exciplex. It is because it is easy to do.
Here, the steric parameter (usually expressed as “Es value”) is a substituent constant defined by Taft. In particular, the Es value used in the present invention is a value represented by a relative value based on a hydrogen atom, and typical substituent values are exemplified below. As the Es value for the linking group, the same value as the Es value of the substituent in which a hydrogen atom is introduced at one end of the linking group is adopted.
H (0), CH ₃ (−1.24), C ₂ H ₅ (−1.31), i-C ₃ H ₇ (−1.71), t-C ₄ H ₉ (−2.78) , F (−0.46), Cl (−0.97), Br (−1.16), CF ₃ (−2.40), C ₆ H ₅ (−1.01), CH ₂ C ₆ H ₅ (−1.61).

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

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

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

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

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

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

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a nitrogen atom are not particularly limited, but each independently includes a nitrogen-containing heterocyclic ligand (eg, pyridine ligand, pyrazine coordination) Ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxadi 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, the 5-membered heterocyclic ligand of the compound (24) and the terminal 5-membered heterocyclic ring of the compound (64) described later. Ligand The 5-membered heterocyclic ligand of the product (145) is also defined as a pyrrole tautomer.) Amino ligands (alkylamino ligands (preferably having 2 to 30 carbon atoms, more preferably 2 carbon atoms) To 20, particularly preferably 2 to 10 carbon atoms, such as methylamino), arylamino ligands (such as phenylamino), acylamino ligands (preferably having 2 carbon atoms). To 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino ligand (preferably 2 to 30 carbon atoms). More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino and the like. Sicarbonylamino 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), sulfonylamino coordination 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, and 2-ethylhexyloxy), aryloxy ligands (preferably 6 to 30 carbon atoms, and more). Preferably it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), heterocyclic oxy ligands (preferably carbon 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, And quinolyloxy), acyloxy ligands (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). ), 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 and triphenylsilyloxy. ), Carbonyl ligands (eg, ketone ligands, ester ligands, amide ligands, etc.), ether ligands (eg, dialkyl ether ligands, diaryl ether ligands, furyl ligands, etc.) Etc.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, and 2-ethylhexyloxy). 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, and 2-naphthyloxy). And 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, and quinolyloxy. An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms) Preferably it has 1 to 12 carbon atoms, for example, acetyl, benzoyl, formyl, pivaloyl, etc.), alkoxycarbonyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably C2-C12, for example, methoxycarbonyl, ethoxycarbonyl, etc.), aryloxycarbonyl groups (preferably C7-30, more preferably C7-20, particularly preferably C7-C7) 12 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 ), Sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc. ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenyl Sulfamoyl etc.),

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl). An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 carbon atoms). To 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimid And sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to carbon atoms). 12 such as mesyl, tosyl, etc.), 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 methanesulfinyl, Benzenesulfinyl, etc.), ureido groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido and phenylureido) ),

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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. The 1-3-dentate anionic ligand is not particularly limited, but a tridentate ligand formed by a halogen ligand, L ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² , and L ⁸³ is preferable. ^A tridentate ligand formed by ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² , and L ⁸³ is more preferred. 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 that is M It represents coordinating a nitrogen-containing hetero ring ^81, L ^81, L ^82, and at least one of 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. For example, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, thiazole ring, oxazole ring, pyrrole ring, pyrazole ring, imidazole 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 tautomers thereof. And 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.

<Metal complex represented by general formula (II)>
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 or terbium ion are preferable, iridium ion and europium ion are more preferable, and iridium ion is preferable. Further preferred.

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 examples of the atom include a carbon atom, a nitrogen atom, an oxygen atom, a silicon atom, a phosphorus atom, and a sulfur atom. A nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom, more preferably a nitrogen atom or 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 (such as thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, or triazole) 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, or triazole), amino groups (alkyl An amino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, methylamino), an arylamino group (for example, 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, and examples thereof include acetylamino and benzoylamino), alkoxycarbonylamino group ( Preferably 2-30 carbons, more preferably 2-20 carbons, Preferably have 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), an aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably carbon atoms). 7-12, for example, phenyloxycarbonylamino, etc.), sulfonylamino groups (preferably 1-30 carbon atoms, more preferably 1-20 carbon atoms, particularly preferably 1-12 carbon atoms, Examples thereof include methanesulfonylamino, benzenesulfonylamino, etc.), imino group and the like. 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. , And 2-ethylhexyloxy), aryloxy groups (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, etc.), 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, Pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyloxy group (preferably having 2 to 2 carbon atoms). 0, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), silyloxy group (preferably 3 to 40 carbon atoms, more preferably carbon atoms) 3 to 30, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy and triphenylsilyloxy), carbonyl groups (such as ketone groups, ester groups and amide groups), ether groups (such as dialkyls) Ether group, diaryl ether group or furyl group).

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

As the one coordinated to M ^X1 with a sulfur atom, an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.) An arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenylthio), a heterocyclic thio group ( Preferably it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, and 2-benzthia. Zolylthio etc.), thiocarbonyl group (eg thioketone group, thioester group etc.), thioether group (eg dial) Thioether group, diaryl thioether or thiofuryl group, etc.,) and the like.

Examples of those 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. A nitrogen-containing aromatic heterocyclic group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, or a dialkylphosphino group, more preferably an aromatic hydrocarbon ring group coordinated at a carbon atom, or a 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, or 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 (2) can be applied, and the preferred ranges are 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, or triazole ring, more preferably A benzene ring, a pyridine ring, a pyrazine ring, a pyrazole ring, or a triazole ring, particularly preferably a benzene ring or a pyridine ring. These may further have a condensed ring or a substituent.

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

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

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

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

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

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 and water) or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, and carbonic acid) Potassium or the like), or in the absence of a base, at room temperature or lower, or by heating (in addition to normal heating, a method of heating with microwaves 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 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 (for example, 1,10-phenanthroline and the like) and an anisole derivative (for example, 4-fluoroanisole and the like) are reacted by the method described in Journal of OrganIc ChemIstry, 741,11, (1946). Can be synthesized. In addition, halogenated 2,2′-bipyridyl derivatives (eg, 2,9-dibromo-1,10-phenanthroline) and 2-methoxyphenylboronic acid derivatives (eg, 2-methoxy-5-fluorophenylboron) After the Suzuki coupling reaction using an acid or the like as a starting material, the methyl group is deprotected (the method described in Journal of OrganIc ChemIstry, 741, 11, (1946), the method of heating in pyridine hydrochloride, etc. Can be synthesized. In addition, 2,2′-bipyridylboronic acid derivatives (eg, 6,6′-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolyl) -2,2′-bipyridyl) and halogens A methyl group is deprotected after a Suzuki coupling reaction using a modified anisole derivative (eg, 2-bromoanisole) as a starting material (Journal of OrganIc ChemIstry, 741, 11, (1946), Alternatively, it can also be synthesized by using a method such as heating in pyridine hydrochloride.

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

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

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

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

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

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

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 phenyl sulfamoyl and the like.),

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like), alkylthio. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 to 6 carbon atoms). 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like, and a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 carbon atom). -20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolyl Oh, 2-benzoxazolyl thio, and 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, ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide groups (preferably C1-C30, more preferably carbon 1 to 20, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide. Is lower.), Hydroxy group, a mercapto group, a halogen atom (e.g. fluorine atom, chlorine atom, bromine atom or iodine atom),

Cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, As, for example, a nitrogen atom, an oxygen atom, a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl and triphenylsilyl), silyloxy Group (preferably 3 to 40 carbon atoms, more preferably carbon number 30, particularly preferably from 3 to 24 carbon atoms, for example trimethylsilyloxy, etc. triphenylsilyl oxy and the like.) And the like. These substituents may be further substituted.
Among these substituents, the substituent on the carbon atom is preferably an alkyl group, an aryl group, a heterocyclic group, or a halogen atom, more preferably an aryl group or a halogen atom, and further preferably a phenyl group or a fluorine atom. Is an atom.

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

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

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

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

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

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

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

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

Q ²¹ and Q ²² each represent a group that forms a nitrogen-containing heterocycle. The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is not particularly limited, but includes a pyrrole ring, an imidazole ring, a triazole ring, and a condensed ring containing them (eg, benzpyrrole), and tautomers thereof. (For example, in the general formula (b) described later, a nitrogen-containing 5-membered ring substituted by R ⁴³ , R ⁴⁴ , R ⁴⁵ , and R ⁴⁶ is 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 , and M ⁴¹ are Z ²¹ in the general formula (a). , Z ²² , Z ²³ , Z ²⁴ , Z ²⁵ , Z ²⁶ , X ²¹ , X ²² , X ²³ , X ²⁴ , and M ²¹ , and preferred ranges are also the same.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 may further have a substituent. Examples of the substituent that can be introduced include an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms. For example, methyl, ethyl, Iso-propyl, tert- Butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably Has 2 to 10 carbon atoms, such as 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 , Having 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. Groups (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino And alkoxy groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, and 2-ethylhexyl). Siloxy and the like), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably Properly 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy and the like.),

Heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and 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, and pivaloyl), an alkoxycarbonyl group (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), aryloxycarbonyl group (preferably carbon 7 to 30, more preferably 7 to 20 carbon atoms, particularly preferably A prime number 7-12, and for example, phenyloxycarbonyl.),

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

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

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

Ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include ureido, methylureido, phenylureido), phosphoric acid amide group (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), hydroxy group, mercapto Group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group,

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and the hetero atom is, for example, a nitrogen atom, an oxygen atom, or 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 3 carbon atoms). 30, particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyl, triphenylsilyl, etc.), silyloxy group (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably carbon atoms) For example, trimethylsilyloxy, triphenylsilylo Shi and the like.), And the like.

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

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

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

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

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

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

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

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

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

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

The compound represented by formula (C-5) will be described in detail.
M ^C5 , L ^C51 , L ^C52 , G ^C51 , and G ^C52 have the same ^meanings as M ^C1 , L ^C11 , L ^C12 , G ^C11 , and G ^{C12 in the} corresponding general formula (C-1), and are preferable. The 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 are also included. It is the same.
G ^D11 and G ^D12 have the same ^meanings as G ^C11 and G ^C12 in the corresponding general formula (C-1), and preferred ranges are also the same.
J ^D11 , J ^D12 , J ^D13 and J ^D14 represent an atomic group necessary for forming a nitrogen-containing hetero five-membered ring together with the atomic group to which they are bonded.

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

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

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

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

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

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

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

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, 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, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), hetero A cyclic group (an aliphatic heterocyclic group or an aromatic heterocyclic group; preferably an oxygen atom, a sulfur atom, or Includes any nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 12 carbon atoms. For example, imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxa And azolyl and triazolyl groups). R ^D21 , R ^D22 and R ^D23 are preferably an alkyl group, an aryl group or an aromatic heterocyclic group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.

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

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

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

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

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

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

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

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

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

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

The general formula (E-3) will be described in detail.
In general formula (E-3), M ^E3 , G ^E31 , G ^E32 , G ^E33 , G ^E34 , Y ^E31 , Y ^E32 , Y ^E33 , and Y ^E34 are respectively in the corresponding general formula (E-1). It is synonymous with M ^E1 , G ^E11 , G ^E12 , G ^E13 , G ^E14 , Y ^E11 , Y ^E12 , Y ^E13 , and Y ^E14 , and the preferred range is also the same. X ^E31 and X ^E32 have the same meaning as X ^E21 and X ^E22 in the corresponding general formula (E-2), and preferred ranges are also the same.

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

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

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

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

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

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

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

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

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

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

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

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

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

3. Specific Examples of Configuration of Organic Laser Oscillation Element Specific examples of the configuration of the organic laser oscillation element in the present invention will be described with reference to the drawings, but the present invention is not limited to these configurations.
FIG. 1 is a conceptual diagram showing an example of a stacked organic laser oscillation element. The light emitting material of the light emitting layer 12 is excited by the light from the external excitation light source 14 to emit light. The light emitting layer contains the tridentate or higher metal complex of the present invention as a light emitting material, and light emission including light emission from an excimer state and phosphorescence can be obtained. In order to generate stronger light, the light emitting material is preferably dispersed and contained in the medium at a high concentration, and the content of the light emitting material is preferably 10% by mass or more. The emitted light is repeatedly reflected between the first surface of the reflective layer 11 and the second surface of the translucent reflective layer 13, resonated and amplified, and directed from the translucent reflective layer 13 to the direction intersecting the light emitting layer. Oscillates a laser beam having the property

  FIG. 2 is a conceptual diagram showing an example of the configuration of a fiber type laser oscillation element. Light from the external excitation light source 24 is irradiated through the lens 25 over the width of the cylindrical light emitting region 21 to excite the light emitting material to emit light. The emitted light is confined in the light emitting region 21 by the clad material 22 having a refractive index smaller than that of the light emitting region, is repeatedly reflected between the first surface of the reflective layer and the second surface of the translucent reflective layer, and resonates and amplifies. The laser beam is extracted through the second surface.

  FIG. 3 is a conceptual diagram showing an example of a waveguide type organic laser oscillation element. Light from the external excitation light source 34 is irradiated through the lens 35 over the width of the stripe-shaped light emitting region 32 functioning as an optical waveguide, thereby exciting the light emitting material to emit light. The emitted light is confined in the light emitting region 32 by the clad material 36 having a refractive index smaller than that of the light emitting region 32, and is repeatedly reflected between the first surface of the reflective layer and the second surface of the translucent reflective layer, and resonates. The amplified laser light is extracted through the second surface.

  FIG. 4 is a conceptual diagram showing an example of a microsphere type organic laser oscillation element. Light from the external excitation light source 44 is applied to the microsphere 41 that functions as an optical resonator, and the light emitting material 42 dispersed in the microsphere is excited to emit light. The emitted light is confined in the microsphere, is repeatedly reflected on the inner surface of the microsphere, and resonated and amplified laser light is extracted from the surface of the microsphere. As a feature of this structure, the resonance wavelength can be controlled by the size of the microsphere.

  FIG. 5 is a conceptual diagram showing an example of a light source stacked organic laser oscillation element. For example, a light source stacked organic laser oscillation element in which an organic EL excitation light source is disposed adjacent to a light emitting layer containing a laser light emitting material sandwiched between reflective layers on a first surface and a second surface is shown. An organic EL light source having an organic light emitting layer 54b is built in between the electrode 54a and the electrode 54c, and excitation light is emitted by energization between both electrodes. Then, this light emission is guided to a laser oscillation unit having a resonator structure, and the light emitted from the second light emitting layer 52 containing the laser light emitting material is resonated and amplified between the semitransparent first surface and the second surface. Laser oscillation.

4). Applications The application of the organic laser oscillation device of the present invention is not particularly limited, but can be applied to a wide range of fields such as optical communication, optical integrated circuits, and light sources for recording media such as optical disks and optical memories.

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

Example 1
A dielectric thin film of TiO ₂ and SiO ₂ is laminated in this order so that each film thickness has an optical length corresponding to ¼ of the resonance wavelength on a glass substrate, and a dielectric multilayer having a reflectivity of 99%. A film was formed. A light absorbing layer made of carbon was formed on the surface of the glass substrate opposite to the surface on which the dielectric multilayer film was formed, and a pinhole of 0.5 mm was formed at the center. On the dielectric multilayer film, a SiO ₂ spacer layer, a light emitting layer of the multidentate metal complex compound of the present invention (243) (20% by mass) (100 nm), a SiO ₂ spacer layer, and an Ag layer (500 nm) are vacuum heated by resistance heating. Deposited sequentially by the method. The optical distance between the dielectric multilayer film and the Ag layer is 1.5 times the peak wavelength of 570 nm of the excimer emission spectrum of the compound (243), and the light-emitting layer is at the center of the dielectric multilayer film and the Ag layer. The SiO ₂ spacer layer was adjusted so as to be arranged. An organic laser oscillation element arranged so as to irradiate the third harmonic (355 nm) of the Nd: YAG laser from the end face of the light emitting layer was produced.

(Example 2)
The tip of the quartz fiber having a cavity in the center was immersed in a heated and melted multidentate metal complex compound (243) (20% by mass) of the present invention and introduced into the cavity by capillary action to form a light emitting region. The optical distance of the quartz fiber was cut so as to be an integral multiple of 570 nm, which is the peak wavelength of the excimer emission spectrum of the compound (243), and both ends were optically polished. An Ag mirror layer (first surface) having a transmittance of 0% was formed on one of the optically polished end surfaces, and an Ag mirror layer (second surface) having a transmittance of 1% was formed on the other end surface. An organic laser oscillation element arranged so as to linearly irradiate the third harmonic (355 nm) of the Nd: YAG laser from the side surface of the quartz fiber was produced.

(Example 3)
A device was produced in the same manner as in Example 1 except that the light emitting layer was the multidentate metal complex compound (135) (20% by mass) (100 nm) of the present invention.

(Comparative example)
A device was produced in the same manner as in Example 1 except that the light emitting layer was changed to FPt (acac) (20 mass%) (100 nm) as a comparative compound.

<Evaluation of device>
The elements manufactured in Examples 1 to 3 and the comparative example were excited with a Nd: YAG laser with an excitation intensity of 10 mJ and oscillated, and the laser output was detected with a photomultiplier. The initial output from each element and the output after 60 min excitation were measured, and the output retention rate after 60 min excitation relative to the initial output was calculated.

<Evaluation results>
Table 1 shows output retention ratios after excitation for 60 minutes with respect to the initial outputs of the devices of Examples 1 to 3 and the comparative example.

  Compared with the element of a comparative example, the output maintenance factor of the element of Examples 1-3 became high. This indicates that the Pt complex having the tridentate and tetradentate ligands in Examples is more excited than the Pt complex having bidentate ligands when used in a laser element. It shows that the durability against is high.

It is a conceptual diagram which shows a lamination type organic laser oscillation element. It is a conceptual diagram which shows a fiber type organic laser oscillation element. It is a conceptual diagram which shows a waveguide type organic laser oscillation apparatus. It is a conceptual diagram which shows a microsphere type organic laser oscillation apparatus. It is a conceptual diagram which shows a light source lamination type organic laser oscillation apparatus.

Explanation of symbols

11: Reflective layer 12: Light emitting layer 13: Translucent reflective layer 14, 44: Excitation light source 22, 36: Clad material 21, 32: Light emitting region 24, 34: Excitation light source 25, 35: Lens 41: Microsphere 42: Light emission Region 54: Organic EL light source 54a: Electrode 54b: Organic layer (including light emitting layer)
54c: Transparent electrode 52: Laser emission layer 51, 53: Translucent reflection layer

Claims (11)

  An organic laser oscillation element comprising: an organic light emitting region containing a light emitting material; and a resonator structure that resonates and amplifies light emitted from the light emitting region between a first surface and a second surface, An organic laser oscillation element, wherein the light emitting material includes a metal complex having a ligand capable of coordinating at three or more positions.   The organic light emitting element according to claim 1, wherein the light emitting region further contains a host material.   3. The organic laser oscillation element according to claim 1, wherein the light emitting material emits light from an excimer state, and the resonator structure amplifies light in one direction of the light emission.   The organic laser oscillation element according to claim 1, wherein the luminescent material is excited by excitation light from an external excitation light source. The organic laser oscillation element according to any one of claims 1 to 4, wherein the metal complex having a tridentate or higher ligand is a compound represented by the following general formula (I): :

(In the general formula (I), M ¹¹ represents a metal ion, and L ^{11 to} L ¹⁵ each represents a ligand coordinated to M ^{11. An} atomic group further exists between L ¹¹ and L ^14. L ¹⁵ may be bonded to both L ¹¹ and L ¹⁴ to form a cyclic ligand, 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 These bonds may be any of coordination bond, ionic bond, and covalent bond.)   The organic laser oscillation element according to claim 5, wherein the tridentate or higher ligand is a chain ligand. The organic laser oscillation according to any one of claims 1 to 4, wherein the metal complex having a tridentate or higher ligand is a compound represented by the following general formula (II): 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 Each atomic group is a tridentate ligand, and the bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond, an ionic bond, or a covalent bond. The organic laser oscillation according to any one of claims 1 to 4, wherein the metal complex having a tridentate or higher ligand is a compound represented by the following general formula (III): element:

(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 organic laser oscillation element according to any one of claims 1 to 8, wherein a metal ion in the metal complex having a tridentate or higher ligand is a transition metal ion.   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, copper ions. The organic laser according to any one of claims 1 to 9, wherein the organic laser is at least one selected from the group consisting of cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, and gallium ion. Oscillating element.   The organic laser oscillation element according to any one of claims 1 to 8, wherein a metal ion in the metal complex having a tridentate or higher ligand is a rare earth metal ion.

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