JP4959270B2 - Organic electroluminescence device - Google Patents

Description

  The present invention relates to a light emitting device, particularly an organic electroluminescent device (EL device).

  Today, research and development on various display elements are active. Among them, organic electroluminescence (EL) elements are attracting attention as promising display elements because they can emit light with high luminance at a low voltage.

In recent organic EL device development, various studies on improving external quantum efficiency have been conducted. Among them, a trisphenylpyridine iridium complex (see, for example, Patent Document 1) and a platinum complex such as an octaethylporphyrin platinum complex. An element containing a phosphorescent material such as Patent Documents 2 and 3 shows high efficiency and has attracted attention.
However, devices containing these phosphorescent materials are not satisfactory in terms of durability, and further improvements have been demanded.

On the other hand, there are vacuum deposition methods using low-molecular materials, ink-jet methods using high-molecular materials, printing methods, etc., as methods for mass production of panels. Is being considered.
As described above, in order to obtain an organic light emitting device with high luminous efficiency and a large area, a phosphorescent polymer material is required. As such a phosphorescent polymer material, a polymer incorporating an iridium complex (for example, see Patent Documents 4 and 5) has been disclosed, but in terms of luminous efficiency and driving durability, it is practically used. Further improvements are desired. In addition, polymers used in organic electroluminescent devices are usually used after being dissolved in a solvent at the time of production. However, known phosphorescent polymers are improved in that performance fluctuations are likely to occur due to fluctuations in the solution storage state during production. There are issues to be solved, and these improvements are desired.
International Publication No. 00/070655 US Pat. No. 6,303,238 B1 US Pat. No. 6,653,564B1 JP 2003-77675 A JP 2003-342325 A

  An object of the present invention is to provide an organic electroluminescent device exhibiting high luminous efficiency and excellent durability. It is another object of the present invention to provide an organic electroluminescence device that is less susceptible to performance fluctuations due to fluctuation factors of manufacturing conditions when manufacturing in a large area.

The present invention has been made in view of the above problems, and is achieved by the following means.
<1> An organic electroluminescent device having an organic electroluminescent device having at least one organic layer between a pair of electrodes, the polymer having a structure represented by the following formula P1 .

(In formula P1, n represents a positive integer.)

< 2 > The organic electroluminescent element according to <1> , wherein the polymer contains a hole transporting functional site.
< 3 > The organic electroluminescent element as described in <1> , wherein the polymer contains an electron transporting functional site.

  The light-emitting element of the present invention exhibits high luminous efficiency, is excellent in durability, and hardly undergoes performance fluctuations due to fluctuation factors during production.

Hereinafter, the organic electroluminescent element of the present invention (hereinafter sometimes referred to as “organic EL element” as appropriate) will be described in detail.
The light-emitting element of the present invention has a cathode and an anode on a substrate, and an organic compound layer including an organic light-emitting layer (hereinafter sometimes simply referred to as “light-emitting layer”) between both electrodes. In view of the properties of the light emitting element, at least one of the anode and the cathode is preferably transparent.
The organic compound layer in the present invention may be either a single layer or a laminate. As an aspect in the case of lamination, an aspect in which a hole transport layer, a light emitting layer, and an electron transport layer are sequentially laminated from the anode side is preferable. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. A hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Each layer may be divided into a plurality of secondary layers.

Next, the polymer material used for the organic electroluminescent element of the present invention will be described in detail.
The polymer used in the present invention has a metal complex having a tridentate or higher ligand in the molecule.
Below, the metal complex which has a tridentate or more ligand is demonstrated, and the polymer which has these is demonstrated.

1. Metal complex having a tridentate or higher ligand First, a metal complex having a tridentate or higher ligand will be described.
The atom coordinated to the metal ion in the metal complex is not particularly limited, but is preferably an oxygen atom, a nitrogen atom, a carbon atom, a sulfur atom or a phosphorus atom, more preferably an oxygen atom, a nitrogen atom or a carbon atom, a nitrogen atom or a carbon atom. Atoms are more preferred.

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

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

The ligand of the metal complex in the present invention is preferably a chain or a ring from the viewpoint of improving luminous efficiency and durability, and a central metal (for example, a compound represented by the general formula (I) described later) in the case of representing the M ^11.) coordinating hetero ring (e.g., a nitrogen-containing nitrogen in a pyridine ring, a quinoline ring, a pyrimidine ring, a pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, oxazole ring, thiazole A ring, an oxadiazole ring, a thiadiazole ring, or a 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. In the case of the chain ligand, the carbon number is preferably 12 to 50, and more preferably 12 to 40 (for example, terpyridyl ligand). Further, that the ligand of the metal complex is cyclic means that a plurality of ligands in the metal complex are bonded to each other to form a closed structure (for example, phthalocyanine ligand, crown ether coordination). Etc.).

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

  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 , or Y ¹³ represents a linking group, a single bond, or a double bond, respectively. 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, Alternatively, europium ions are more preferable, platinum ions and iridium ions are more preferable, and platinum ions are particularly preferable.

In general formula (I), L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ each independently represent a ligand that coordinates to M ¹¹ . The atoms contained in L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ and coordinated to M ¹¹ are preferably a nitrogen atom, an oxygen atom, a sulfur atom, a carbon atom, or a phosphorus atom. 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 consisting of L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and L ¹⁴ is an anionic ligand (a ligand in which at least one anion binds to a metal). Is preferred. 1-3 are preferable, as for the number of anions in an anionic ligand, 1 and 2 are more preferable, and 2 is further more preferable.

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

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a nitrogen atom are not particularly limited, but each independently includes a nitrogen-containing heterocyclic ligand (eg, pyridine ligand, pyrazine coordination). Ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxadi Azole ligands, thiadiazole ligands, and condensed rings containing them (for example, quinoline ligands, benzoxazole ligands, benzimidazole ligands, etc.) and tautomers thereof (note that In the present invention, in addition to the usual isomers, the following examples are also defined as tautomers, for example, the 5-membered heterocyclic ligand of the compound (24) described later and the 5-membered terminal of the compound (64). Arocyclic ligands, 5-membered heterocyclic ligands of the compound (145) are also defined as pyrrole tautomers, etc.) amino ligands (alkylamino ligands (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 methylamino.), An arylamino ligand (preferably 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 20, particularly preferably having 6 to 12 carbon atoms, such as phenylamino, etc.), an acylamino ligand (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably carbon atoms). 2-10, for example, acetylamino, benzoylamino, etc.), an alkoxycarbonylamino ligand (preferably 2-30 carbons, more preferably 2-2 carbons). 20, particularly preferably having 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), an aryloxycarbonylamino ligand (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, especially Preferably, it is C7-12, for example, phenyloxycarbonylamino etc. are mentioned), a sulfonylamino ligand (preferably C1-30, more preferably C1-20, and particularly preferably carbon number). 1 to 12, for example, methanesulfonylamino, benzenesulfonylamino, etc.), imino ligands, etc.) These ligands may be further substituted.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ with an oxygen atom are not particularly limited, but are independently an alkoxy ligand (preferably having 1 to 30 carbon atoms, more preferably having carbon atoms). 1 to 20, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy), aryloxy ligands (preferably 6 to 30 carbon atoms, more preferably Has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like, and a heterocyclic oxy ligand (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, Noryloxy, etc.), 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, benzoyloxy and the like. ), 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.) Can be mentioned.

Although it does not specifically limit as L < ¹¹ >, L < ¹² >, L <^13> , and L < ¹⁴ > coordinated to M < ¹¹ > by a sulfur atom, Each is independently alkylthio ligand (preferably C1-C30, More preferably, carbon number. 1 to 20, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio, etc.), an arylthio ligand (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably Has 6 to 12 carbon atoms, for example, phenylthio and the like, and a heterocyclic thio ligand (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). And examples thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio), and thiocarbo. Le ligands (e.g. thioketone ligand, etc. thioester ligands), or thioether ligands (e.g. dialkyl thioether ligands, diaryl thioether ligands, etc. thiofuryl ligand), and the like. These substituted ligands may be further substituted.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a phosphorus atom are not particularly limited, but are each independently a dialkylphosphino group (preferably having 2 to 30 carbon atoms, more preferably carbon atoms). 2 to 20, particularly preferably 2 to 12 carbon atoms, such as dicyclohexylphosphino), diarylphosphino group (preferably 12 to 40 carbon atoms, more preferably 12 to 30 carbon atoms). Particularly preferably, it has 12 to 20 carbon atoms, such as diphenylphosphino, etc.), trialkylphosphine (preferably 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 12 carbon atoms, such as tributylphosphine, tri-tert-butylphosphine, and tricyclohexyl Phosphine, etc.), triarylphosphine (preferably having 18 to 40 carbon atoms, more preferably 18 to 30 carbon atoms, and particularly preferably 18 to 20 carbon atoms. For example, triphenylphosphine, diphenyl ( p-tolyl) phosphine, tri-p-tolylphosphine, (R)-(+)-2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, and (S)-(−) — 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, etc.), alkylarylphosphine (preferably having 8 to 40 carbon atoms, more preferably 8 to 30 carbon atoms, particularly preferably , Having 13 to 30 carbon atoms, such as dicyclophenylphosphine, bis (diphenylphosphino) methane, 1,2-bis (diphenylphosphino) Ethane, and 1,3-bis and the like (diphenylphosphino) propane.), Phosphinine group and the like. 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 rings containing them (for example, Quinoline ligands, benzoxazole ligands, benzimidazole ligands, etc.) or tautomers thereof) are preferred, aromatic carbocyclic ligands, Oxyoxy ligands, arylthio ligands, arylamino ligands, and pyridine ligands, pyrazine ligands, imidazole ligands or condensed rings containing them (for example, quinoline ligands, quinoxaline ligands) A ligand, a benzimidazole ligand, or the like, or a tautomer thereof, more preferably an aromatic carbocyclic ligand, an aryloxy ligand, an arylthio ligand, or an arylamino ligand. Further preferred are aromatic carbocyclic ligands or aryloxy ligands.

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

In the general formula (I), L ¹⁵ represents a ligand coordinated to M ¹¹ . L ¹⁵ is preferably a monodentate to tetradentate ligand, and more preferably a monodentate to tetradentate anionic ligand. Although it does not specifically limit as a monodentate-tetradentate anionic ligand, The monoanion containing a halogen ligand, a 1, 3- diketone ligand (for example, acetylacetone ligand etc.), and a pyridine ligand Sex bidentate ligands (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 is preferred, and a monoanionic bidentate ligand (eg, picoline) containing a 1,3-diketone ligand (eg, acetylacetone ligand) or a pyridine ligand. Acid ligands, 2- (2-hydroxyphenyl) -pyridine ligands, etc.), L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and L ¹⁴ Child is preferred, 1,3 Monoanionic bidentate ligands (eg, picolinic acid ligands, 2- (2-hydroxyphenyl) -pyridine coordination, including diketone ligands (eg, acetylacetone ligands) Are more preferable, and 1,3-diketone ligands (such as acetylacetone ligands) are particularly preferable. The number of coordination sites and the number of ligands do not exceed the coordination number of the metal.

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

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

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

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

In the general formula ^{(I), n 11} represents 0 to 4. If M ¹¹ is a metal coordination number ^{4, n 11} is ^0, when ^{M 11} is a metal coordination number ^{6, n 11} is 1, 2 is preferable, 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, 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, a plurality of L ¹⁵ may be different even in the same.

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 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 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.
Formula ^{(1), M 21} has the same meaning as ^{M 11} in the above formula (I), and their preferable ranges are also the same.

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

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

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

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

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

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

R ²¹ , R ²² , R ²³ , and R ²⁴ each independently represent 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, and cyclohexyl), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 2 carbon atoms). 20, particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl). 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, such as pyridyloxy, pyrazyloxy, pyrimidyloxy and quinolyloxy). An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferred). Or having 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably having 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, 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-benzimizo Luthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 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 (for example, fluorine atom, chlorine atom, bromine atom or iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, or 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, or a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazoly , A carbazolyl group, an azepinyl group, etc.), a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl, triphenyl, etc. And silyloxy groups (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, such as 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, benzo condensed ring, pyridine condensed ring). A group which forms a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) by bonding R ²¹ and R ²² or R ²³ and R ²⁴ is more preferred.

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, X ²¹ and X ²² are a sulfur atom, a metal complex representing 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 the 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 , Z ³⁴ and Z ^35. , Z ³⁵ and Z ³⁶ may be bonded via a linking group to form a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.), and Z ³¹ and T ³¹ , Z ³⁶ and T ³⁸ may be a linking group. 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, 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 their preferred ranges are also the same.

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

In the general formula ^{(2), M 51} has the same meaning as ^{M 11} in the above formula (I), and their preferable ranges are also the same.

Q ⁵¹ and Q ⁵² are each independently synonymous with Q ²¹ and Q ²² in the general formula (1), and a preferred range is 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 the ^{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 a nitrogen atom, preferably an unsubstituted carbon atom or a 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 range is also the same.

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

Formula (3-A) ^{in, M 61} has the same meaning as ^{M 11} in the above formula (I), and their preferable ranges are also the same.

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

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

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

Y ⁶² and Y ⁶³ each independently represent a linking group or a single bond. The linking group is not particularly limited, and includes, for example, a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, and combinations thereof. Examples thereof include a linking group.

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

L ⁶⁵ has the same meaning as that of ^{L 15} in Formula (I), and their preferable ranges are also the same.

n ⁶¹ has the same meaning as ^{n 11} in the general formula (I), and their preferable ranges are 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 carbon include the groups described for R ²¹ in the general formula (1), and Z ⁶¹ and Z ⁶² , Z ⁶² and Z ⁶³ , Z ⁶³ and Z ⁶⁴ , Z ⁶⁵ and Z ^66. , Z ⁶⁶ and Z ⁶⁷ , Z ⁶⁷ and Z ⁶⁸ may be bonded via a linking group to form a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.). The ring formed by Q ⁶¹ and Q ⁶² may be bonded to Z ⁶¹ and Z ⁶⁸ via a linking group to form a ring.

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

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

In the general formula ^{(3-B), M 71} has the same meaning as ^{M 11} in the above formula (I), and their preferable ranges are also the same.
Y ⁷¹ , Y ⁷² and Y ⁷³ are each independently synonymous with Y ⁶² in the general formula (3-A), and the preferred range is also the same.

L ⁷⁵ has the same meaning as that of ^{L 15} in Formula (I), and their preferable ranges are also the same.
n ⁷¹ has the same meaning as ^{n 11} in the general formula (I), and their preferable ranges are also the same.

Z ⁷¹ , Z ⁷² , Z ⁷³ , Z ⁷⁴ , Z ⁷⁵ , and Z ⁷⁶ each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom, preferably a substituted or unsubstituted carbon atom. Examples of the substituent on carbon include the group 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 ranges are 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 the general formula (3-C), R ^C1 and R ^C2 each independently represent a hydrogen atom or a substituent, and the substituent is described as a substituent of R ²¹ to R ²⁴ in the general formula (1). Represents an alkyl group or an aryl group. The substituents represented by R ^C3 , R ^C4 , R ^C5 and R ^C6 are also synonymous with the substituents of R ²¹ to R ²⁴ in the general formula (1). n ^C3 and n ^{C6 each} represent an integer of 0 to 3, n ^C4 and n ^{C5 each} represent an integer of 0 to 4, and when each of R ^C3 , R ^C4 , R ^C5 , and R ^C6 includes a plurality of R ^C3 , R ^C4 , R ^C5 and R ^C6 may be the same or different and may be linked to form a ring. R ^C3 , R ^C4 , R ^C5 and R ^C6 are preferably an alkyl group, an aryl group, a heteroaryl group, 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 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 the substituent is the alkyl group, aryl group, or 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 and 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 1,2-position.

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 the general formula ^{(5), M 81} has the same meaning as ^{M 11} in the above formula (I), and their preferable ranges are also the same.

L ⁸¹ , L ⁸² , and L ⁸³ are each independently synonymous with L ¹¹ , L ¹² , and L ¹⁴ in the general formula (I), and the preferred ranges are 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 ligand is preferably of 1 seat to 3 seats, and more preferably anionic ligands 1 seat to 3 seats. No particular limitation is imposed on the anionic ligand of 1 seat to 3 seats, halogen ^{ligand, L 81, Y 81, L} 82, Y 82, and tridentate ligands which are formed by ^{L 83} is preferably, The tridentate ligand formed by L 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. If metal M ⁸¹ is coordination number ^{6, n 81} preferably 1 to 3, more preferably 1 and 3, 1 is more preferred. 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. If M ⁸¹ is a metal coordination number ^{8, n 81} is 1 to 5, more preferably 1, 2, 1 being more preferred. 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 the bidentate ligand and one monodentate three ^represents, when ^{n 81} is 5 ^{L 85} represents a 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 coordinated to M ⁸¹ as a carbon atom, or M as a nitrogen atom. 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. Aromatic carbocycles, heterocycles and nitrogen-containing heterocycles coordinated with nitrogen atoms are coordinated with M ¹¹ described in the above general formula (I) and ligands and nitrogen atoms coordinated with carbon atoms 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 forming 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, or an indolenine ring) 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 or a benzthiazole ring). Benzimidazole ring or indolenine ring), and tautomers thereof, more preferably pyridine ring, pyrrole ring, and condensed ring containing them (for example, quinoline ring), and These tautomers, 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 nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ⁹¹ ). No particular limitation is imposed on the nitrogen-containing heterocyclic ring formed by Q ^93, a pyrrole ring, an imidazole ring, or a tautomer of a triazole ring, a condensed ring body thereof (for example, benzopyrrole, etc.) are preferred, pyrrole A tautomer of a ring and a condensed ring containing a pyrrole ring (for example, benzpyrrole, etc.) are more preferable.

W ⁹¹ and W ⁹² are each independently synonymous with W ⁵¹ and W ⁵² in the general formula (2), and their 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 ¹⁰¹ has the same meaning as Q ⁹¹ in formula (5-A), and the preferred range is also the same.

Q ¹⁰² and Q ¹⁰³ represent a group that forms an aromatic ring. The aromatic ring formed by Q ¹⁰² and Q ¹⁰³ is not particularly limited, but includes a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a furan ring, a thiophene ring, an isothiazole ring, a pyrrole ring, an isoxazole ring, and A condensed ring containing (eg, naphthalene ring) is preferred, a condensed ring containing a benzene ring and a benzene ring (eg naphthalene ring) is more preferred, and a benzene ring is particularly preferred.

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

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

n ¹⁰¹ has the same meaning as ^{n 81} in Formula (5), and their preferable ranges are also the same.
X ¹⁰¹ has the same meaning as X ²¹ in formula (1), and the preferred range is also the same.

  Another preferred embodiment of the metal complex having a tridentate ligand in the present invention is a compound represented by the following general formula (II).

In general formula (II), M ^X1 represents a metal ion. Q ^X11 to Q ^X16 represents an atomic group containing an atom coordinating to an atom or ^{M X1} coordinating to ^{M X1.} L ^{X11 to} L ^{X14 each} represent a single bond, a double bond or a linking group. ^{That, Q X11 -L X11 -Q X12 -L} X12 -Q consisting ^X13 atomic group and ^Q X14 ^-L X13 ^-Q X15 ^-L X14 consisting ^{-Q X16} atomic group is a ligand of each tridentate. 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 (thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, triazole, etc.) and fused rings containing them, and tautomers thereof.

Examples of the group coordinated to M ^X1 with a nitrogen atom include a nitrogen-containing heterocyclic group (pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, or triazole, etc.), amino group (alkyl An amino group (preferably having 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as methylamino, dimethylamino, and diethylamino), an arylamino group (Preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 20 carbon atoms, and examples thereof include phenylamino, diphenylamino, and phenyl-1-naphthylamino). An acylamino group (preferably having 2 to 30 carbon atoms, more preferably carbon A prime number of 2 to 20, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). , Particularly preferably having 2 to 12 carbon atoms, such as methoxycarbonylamino, and the like, and an aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, particularly preferably carbon). 7 to 12, for example, phenyloxycarbonylamino, etc.), a sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, methanesulfonylamino, benzenesulfonylamino, etc.), imino group And the like. These groups may be further substituted.

As the one coordinated with M ^X1 by an oxygen atom, an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, for example, methoxy, ethoxy, butoxy , 2-ethylhexyloxy, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1 -Naphthyloxy, 2-naphthyloxy and the like), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, for example, pyridyl. Oxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyloxy groups (preferably having 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy, benzoyloxy and the like, and a silyloxy group (preferably 3 to 40 carbon atoms, more preferably 3 to 3 carbon atoms). 30, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), carbonyl groups (such as ketone groups, ester groups, or amide groups), ether groups (preferably carbon The number is 2 to 30, more preferably 2 to 20, and particularly preferably 2 to 12, and examples thereof include a dialkyl ether group, a diaryl ether group, and a 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 (preferably carbon A prime number of 2 to 30, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include a dialkylthioether group, a diarylthioether group, and a thiofuryl group.

As the one coordinated with M ^X1 by a phosphorus atom, a dialkylphosphino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, dicyclohexylphosphine And diarylphosphino groups (preferably having 12 to 40 carbon atoms, more preferably 12 to 30 carbon atoms, particularly preferably 12 to 20 carbon atoms, and examples thereof include diphenylphosphino). ), Trialkylphosphine (preferably having 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 12 carbon atoms, such as tributylphosphine, tri-tert-butylphosphine, and tricyclohexylphosphine. A triarylphosphine group (preferably having 18 to 40 carbon atoms, More preferably, it has 18 to 30 carbon atoms, particularly preferably 18 to 20 carbon atoms. For example, triphenylphosphine, diphenyl (p-tolyl) phosphine, tri-p-tolylphosphine, (R)-(+)-2. , 2'-bis (diphenylphosphino) -1,1'-binaphthyl, (S)-(-)-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl, and the like. ), And phosphinine groups. These groups may be further substituted.

Preferably, the atomic group represented by Q ^{X11 to} Q ^X16 is coordinated to M ^X1 with an aromatic hydrocarbon ring group coordinated with a carbon atom, an aromatic heterocyclic group coordinated with 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 with 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 any of a coordination bond, an ionic bond, and a covalent bond.

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

These linking groups may be further substituted, and as the substituent, those exemplified as the substituents represented by R ^{21 to} R ²⁴ in the general formula (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} is coordination bond, an ionic bond, and or a covalent 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 any of a coordination bond, an ionic bond, and a covalent bond. ^Examples of 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, and 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, and furan ring, preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyrazole ring, imidazole ring, 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 represent a single bond, a double bond or a linking group. The bond between M ^X3 and Y ^X31 to Y ^X36 may be any of a coordination bond, an ionic bond, and 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 represents an atom coordinated to M ^X3 . The bond between Y ^{X31 to} Y ^X36 and M ^X3 may be a coordination bond, an ionic bond, or a covalent bond. ^Examples of Y ^{X31 to} Y ^X36 include a carbon atom, a nitrogen atom, and a phosphorus atom, and preferably a carbon atom and a nitrogen atom. L ^{X31 to} L ^X34 are synonymous with L ^{X11 to} L ^X14 in the general formula (II), and preferred ranges thereof are also the same.

  Specific examples of the compounds represented by the general formula (I), the general formula (II), and the general formula (5) include compounds (1) to (242) described in Japanese Patent Application No. 2004-162849. , And compound (243) to compound (245) (the structures are shown below), but are not limited thereto.

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

(Method for synthesizing metal complex in the present invention)
Metal complexes in the present invention [general formulas (I), (1), (1-A), (2), (3), (3-A), (3-B), (3-C), ( 4), (4-A), (5), (5-A), and (5-B), and the compounds represented by the general formulas (II), (X2), and (X3)] It can be synthesized by various methods.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic various bases such as sodium methoxide, t-butoxypotassium, triethylamine, and potassium carbonate) Etc.), 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 a microwave is also effective).

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

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

The metal complex of the present invention is appropriately selected from the ligands that form the partial structure of the target complex, whereby the general formulas (I), (1), (1-A), (2), (3), (3-A), (3-B), (3-C), (4), (4-A), (5), (5-A), and (5-B), and 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 equivalents to the metal compound. It can be synthesized by adding 6 equivalents, more preferably 0.5 to 4 equivalents. 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.

  When the said ligand of the metal complex in this invention is a cyclic ligand, it is preferable that this metal complex is a compound represented by the following general formula (III).

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

In general formula (III), Q ¹¹ represents an atomic group that includes two carbon atoms to which Q ¹¹ is bonded and a nitrogen atom that is 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, and cyclohexyl), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). , Particularly preferably having 2 to 10 carbon atoms, such as propargyl and 3-pentynyl).

  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, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably Preferably, 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). To 30, 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, particularly preferably 1 to 12 carbon atoms, and examples thereof include 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 7 to 12 carbon atoms, such as phenyloxycarbonyl, etc.), an acyloxy group (preferably 2 to 30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, for example acetoxy, benzoyl And an acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino. ),

An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino group ( Preferably it has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino, etc., and a sulfonylamino group (preferably 1 to 1 carbon atoms). 30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, methanesulfonylamino, benzenesulfonylamino, etc.), a sulfamoyl group (preferably C0-30, more preferably) Has 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms. Amoiru, methylsulfamoyl, dimethylsulfamoyl, and the like phenylsulfamoyl, 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, 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-benzimizo Lucio, 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, a ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide groups (preferably C1-C30, more preferably carbon number) 1 to 20, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide That.), Hydroxy group, a mercapto group, a halogen atom (e.g. fluorine atom, chlorine atom, bromine atom, or iodine atom),

A cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, or a heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, Examples of the atom include a nitrogen atom, an oxygen atom, or a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, and azepinyl group. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). A silyloxy group (preferably having 3 to 40 carbon atoms, more preferably Prime 3-30, 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), ^MY1 represents a metal ion which may further have a ligand, and a metal ion having no other ligand is more preferable.

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

The ligand that ^MY1 may further have is not particularly limited, but a monodentate or bidentate ligand is preferable, and a bidentate ligand is more preferable. 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, a general formula ( The compound represented by j) or a tautomer thereof is preferable, the compound represented by the general formula (h) or the tautomer thereof, the compound represented by the general formula (i) or the tautomer thereof More preferred is a compound represented by formula (h) or a tautomer thereof.

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

The compound represented by the general formula (a) will be described.
In the general formula (a), Z ²¹ , Z ²² , Z ²³ , Z ²⁴ , Z ²⁵ , Z ²⁶ , and M ²¹ are Z ¹¹ , Z ¹² , Z ¹³ , Z ^{11 in the} corresponding general formula (III), respectively. , Z ¹² , Z ¹³ and M ^Y1 , and the preferred range is also the same.

Q ^a21 and Q ^a22 each represent a group that forms a nitrogen-containing heterocycle. Although it does not specifically limit as a nitrogen-containing heterocycle formed by ^Qa21 and ^Qa22 , A pyrrole ring, an imidazole ring, a triazole ring, and a condensed ring (for example, benzpyrrole) containing them, and these tautomers Preferred (for example, a nitrogen-containing 5-membered ring substituted with R ⁴³ , R ⁴⁴ , R ⁴⁵ , and R ^{46 in} the general formula (b) described below is defined as a tautomer of pyrrole). A condensed ring containing a ring and 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 each independently represent 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). As the substituent, an alkyl group, an aryl group, a group in which R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are combined to form a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) is preferable. An aryl group, a group in which R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are combined to form a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) is more preferred. R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ^{A group in which 46} is bonded to form a ring structure (for example, benzo-fused ring, pyridine-fused ring, etc.) is more preferred.

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

In General Formula (c), Z ¹⁰¹ , Z ¹⁰² , and Z ¹⁰³ each independently represent a substituted or unsubstituted carbon atom or nitrogen atom. It is preferable that at least one of Z ¹⁰¹ , Z ¹⁰² , and Z ¹⁰³ is 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.

As the group coordinated to M ¹⁰¹ by a phosphorus atom, an alkylphosphine group coordinated by a phosphorus atom,
Arylphosphine group coordinated by phosphorus atom, alkoxyphosphine group coordinated by phosphorus atom, aryloxyphosphine group coordinated by phosphorus atom, heteroaryloxyphosphine group coordinated by phosphorus atom, phosphinine coordinated by phosphorus atom And a phosphole group coordinated with a phosphorus atom, an alkylphosphine group coordinated with a phosphorus atom, and an arylphosphine group coordinated with a phosphorus atom are more preferable.

The group that coordinates to M ¹⁰¹ with an oxygen atom is preferably an oxy group or a carbonyl group that coordinates with an oxygen atom, and more preferably an oxy group.

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

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

Q ¹⁰² represents a 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 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 , and the preferred range is also the same.

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

In 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 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), respectively ^. , Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , and M ¹⁰¹ , and the preferred range is also the same. X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom, a substituted or unsubstituted nitrogen atom or a sulfur atom, preferably an oxygen atom or a substituted nitrogen atom, and more preferably an oxygen atom.

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

In the general formula (g), Z ⁵⁰¹ , Z ⁵⁰² , Z ⁵⁰³ , L ⁵⁰¹ , L ⁵⁰² , L ⁵⁰³ , L ⁵⁰⁴ , Q ⁵⁰¹ , Q ⁵⁰² , Q ⁵⁰³ , and M ⁵⁰¹ are respectively represented by 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 in FIG.

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

In general formula (h), Z ⁶⁰¹ , Z ⁶⁰² , Z ⁶⁰³ , Z ⁶⁰⁴ , Z ⁶⁰⁵ , Z ⁶⁰⁶ , Z ⁶⁰⁷ , Z ⁶⁰⁸ , Z ⁶⁰⁹ , Z ⁶¹⁰ , Z ⁶¹¹ , Z ⁶¹² , L ⁶⁰¹ , L ⁶⁰² , 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 , and the preferred range is also the same.

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

In the general formula (i), Z ⁷⁰¹ , Z ⁷⁰² , Z ⁷⁰³ , Z ⁷⁰⁴ , Z ⁷⁰⁵ , Z ⁷⁰⁶ , Z ⁷⁰⁷ , Z ⁷⁰⁸ , Z ⁷⁰⁹ , Z ⁷¹⁰ , L ⁷⁰¹ , L ⁷⁰² , L ⁷⁰³ , L ⁷⁰⁴ , 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 , respectively in the corresponding general formulas (d) and (c). ^{L 102, L 103, L 104} , and has the same meaning as ^{M 101,} and the preferred range is also the same.

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

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

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

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 bonded to M ^A1 through a coordinate bond, an ionic bond, or a covalent bond.

The compound represented by formula (A-1) will be described in detail.
M ^A1 represents a metal ion. Although it does not specifically limit as a metal ion, A bivalent metal ion is preferable, Pt ^<2+> , Pd ^<2+> , Cu ^<2+> , NI ^<2+> , Co ^<2+> , Zn ^<2+> , Mg ^<2+> or Pb <^2+> is preferable, Pt ^<2+>. Cu ²⁺ is 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, phosphorus, or the like. 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, substituted or unsubstituted carbon atom, substituted or unsubstituted nitrogen atom, substituted silicon atom, divalent aromatic hydrocarbon ring group, or divalent 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, For example And the like of it.

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 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, and anthranyl). An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino; , And methylphenylamino), 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 group (preferably It has 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, 4-phenylphenyloxy, and 4-cyano. Phenyl 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, 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, and examples thereof include 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 carbon 7 to 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 thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably). Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl. And the like.), A sulfinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methane sulfinyl, and the like benzenesulfinyl.),

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

Heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically imidazolyl, pyridyl, quinolyl, Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms). , Particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyl, triphenylsilyl, etc.), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably carbon numbers). 3 to 24, such as trimethylsilyloxy, triphenylsilyloxy, etc. 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 bonded to M ^A1 through a coordinate bond, an ionic bond, or a covalent bond. Q ^A11 and Q ^A12 are each 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, or 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 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 the 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 corresponding 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, and 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, 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, more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 and L ^A14 in formula (A-1) can be applied.
X ^A41 and X ^A42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^A41 and X ^A42 are preferably each independently an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

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

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

In formula (B-1), M ^B1 represents a metal ion. Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom. Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^B11 , L ^B12 , L ^B13 , and L ^B14 each represent a linking group. Q ^B11 and Q ^B12 each represents a partial structure containing an atom bonded to M ^B1 through a coordinate bond, an ionic bond, or 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 , in the general formula (A-1). It is synonymous with L ^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, an oxygen atom or a sulfur atom. L ^B21 , L ^B22 , L ^B23 , and L ^B24 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 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, an oxygen atom or a sulfur atom. L ^B41 , L ^B42 , L ^B43 , and L ^B44 each represent a linking group. Z ^B41 , Z ^B42 , Z ^B43 , Z ^B44 , Z ^B45 and Z ^B46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^B41 and X ^B42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

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

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

The compound represented by formula (B-4) will be described in detail.
In the general formula (B-4), M ^B4 , Y ^B41 , Y ^B44 , Y ^B45 , Y ^B48 , Y ^B42 , Y ^B43 , Y ^B46 , Y ^B47 , L ^B41 , L ^B42 , L ^B43 , and L ^B44 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 its preferable range is also the same.
Z ^B41 , Z ^B42 , Z ^B43 , Z ^B44 , Z ^B45 and Z ^B46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^B41 , Z ^B42 , Z ^B43 , Z ^B44 , Z ^B45 and Z ^B46 are preferably substituted or unsubstituted carbon atoms, 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 ^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 general 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 bonded to M ^C1 by a coordinate bond, an ionic bond or a covalent bond.

The general formula (C-1) will be described in detail.
In 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 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). , For example, methyl, ethyl, Iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms). More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl, 3-pen Such as alkylsulfonyl and the like.),

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, etc.), 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, 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 carbon atoms 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, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, halogen atoms (for example, fluorine) Atom, chlorine atom, bromine atom or iodine atom), cyano group,

Heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically imidazolyl, pyridyl, quinolyl, Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms). , Particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyl, triphenylsilyl, etc.), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably carbon numbers). 3 to 24, such as trimethylsilyloxy, triphenylsilyloxy, etc. 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 R ^C11 and R ^C12 , and R ^C13 and R ^C14 are particularly preferably a group that forms a five-membered ring by bonding to each other.

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

In general formula (C-2), M ^C2 represents a metal ion.
Y ^C21 , Y ^C22 , Y ^C23 and Y ^C24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. G ^C21 and G ^C22 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C21 and L ^C22 each represent a linking group. Q ^C21 and Q ^C22 each represent a partial structure containing an atom bonded to M ^C2 by a coordinate bond, an ionic bond, or 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 and G ^C32 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C31 and L ^C32 each represent a linking group. Z ^C31 , Z ^C32 , Z ^C33 , Z ^C34 , Z ^C35 and Z ^C36 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

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

In general formula (C-5), ^MC5 represents a metal ion.
Y ^C51 , Y ^C52 , Y ^C53 and Y ^C54 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. G ^C51 and G ^C52 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. L ^C51 and L ^C52 represent a linking group. Z ^C51 , Z ^C52 , Z ^C53 , Z ^C54 , Z ^C55 and Z ^C56 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^C51 and X ^C52 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

The compound represented by formula (C-3) will be described in detail.
In the general formula (C-3), M ^C3 , L ^C31 , L ^C32 , G ^C31 , and G ^C32 correspond respectively to M ^C1 , L ^C11 , L ^C12 , G ^C11 , And GC ¹² 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, 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 GC ¹² and the preferred range is also the same.
Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 are preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom.

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

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

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

In 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 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), respectively, and preferred ranges thereof 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 these 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 general 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 general 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. As the substituent represented by R ^D21 , R ^D22 and R ^D23 , an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, 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, propargyl, 3-pentynyl, etc. are mentioned. ),

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, and naphthyl), substituted carbonyl Groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, and phenylaminocarbonyl ), A substituted sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). ,

Heterocyclic group (there is an aliphatic heterocyclic group or an aromatic heterocyclic group. Preferably, it contains any of an oxygen atom, a sulfur atom, or a nitrogen atom, and preferably has 1 to 50 carbon atoms, more preferably 1 carbon atom. To 30 and particularly preferably 2 to 12 carbon atoms, and examples thereof include imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl, quinolyl, carbazoyl, and thienyl. 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 ^D32 in the corresponding general formula (D-1), respectively. have the same meaning as G ^D12, the preferred ranges are 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 general formula (D-2), respectively, and preferred ranges are also the same.
Y ^D31 , Y ^D32 , Y ^D33 and Y ^D34 have the same ^{meanings as} Y ^D21 , Y ^D22 , Y ^D23 and Y ^D24 in General Formula (D-2), respectively, and preferred ranges thereof are also the same.

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

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

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

In general formula (E-1), M ^E1 represents a metal ion. J ^E11 and J ^E12 represent an atomic group necessary for forming a five-membered ring. G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

The general formula (E-1) will be described in detail.
In formula (E-1), M ^E1 has the same meaning as M ^A1 in formula (A-1), and the preferred range is also the same. G ^E11 , G ^E12 , G ^E13 and G ^E14 have the same ^{meanings as} G ^C11 and G ^C12 in formula (C-1), and preferred ranges are also the same.
J ^E11 and J ^E12 have the same ^{meanings as} J ^{D12 to} J ^D14 in formula (D-1), and preferred ranges thereof are also the same. Y ^E11 , Y ^E12 , Y ^E13, and Y ^E14 have the same meanings as Y ^{C21 to} Y ^C24 in General Formula (C-2), respectively, and 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 —, or —C (R ^E22 ) R ^E23 —. R ^E21 , R ^E22 and R ^E23 each independently represent a hydrogen atom or a substituent.

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

General formula (E-2) is demonstrated in detail.
In general formula (E-2), M ^E2 , G ^E21 , G ^E22 , G ^E23 , G ^E24 , Y ^E21 , Y ^E22 , Y ^E23 , and Y ^E24 are respectively the M in the corresponding general formula (E-1). ^{E 1} , G ^E11 , G ^E12 , G ^E13 , G ^E14 , Y ^E11 , Y ^E12 , Y ^E13 , and Y ^E14 have the same ^meanings , and preferred ranges are also the same. Y ^E25 and Y ^E26 are each independently synonymous with Y ^E11 and Y ^E12 in General Formula (E-1), and preferred ranges thereof 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 the 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 a preferable range is also the same. Y ^E35 and Y ^E36 are each independently synonymous with Y ^E11 and Y ^E12 in General Formula (E-1), and preferred ranges are also the same. X ^E31 and X ^E32 have the same meaning as X ^E21 and X ^E22 in the corresponding general formula (E-2), and preferred ranges are also the same.

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

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

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

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 has the same meaning as ^{Q A12,} 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 , R ^F13 and R ^F14 are connected 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 groups 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), ^MF2 represents a metal ion. L ^F21 , L ^F22 and L ^F23 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 , 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), ^MF3 represents a metal ion. L ^F31 , L ^F32 and L ^F33 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 ^combine with each other to form a ring if possible. However, the ring formed by R ^F31 and R ^F32 , 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), ^MF4 represents a metal ion. L ^F41 , L ^F42 and L ^F43 represent a linking group. R ^F41 , R ^F42 , R ^F43 and R ^F44 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 ^F24 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 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 , and R in Formula (F-1). It is synonymous with L ^F13 , R ^F11 , R ^F12 , R ^F13 and R ^F14 , and the preferred range is also the same.
Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 and Z ^F46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 and Z ^F46 are preferably substituted or unsubstituted carbon atoms, 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 metal complex is preferably a metal complex represented by the general formula (1), more preferably a compound represented by the general formula (2), (3), or (4), and still more preferably. Is a compound represented by the general formula (3), particularly preferably a compound represented by the general formula (3-B), and most preferably a compound represented by the general formula (3-C).
The compounds represented by the general formulas (A-1) to (F-1) can be synthesized by a known method.

2. Next, the polymer containing a metal complex in the present invention will be described.
As the polymer used in the present invention, a metal complex portion may be contained in the polymer main chain, or may be contained in the polymer side chain. Further, it may be a homopolymer compound or a copolymer. In the case of a copolymer, any of a random copolymer, an alternating copolymer, and a block copolymer may be used.
In the case of a copolymer, the monomer unit to be combined with the metal complex preferably has a site having an electron transporting function and / or a hole transporting function.
As the skeleton having an electron transporting functional site, for example, those exemplified as the material of the electron transport layer described later can be applied. Moreover, as a skeleton having a hole transporting functional part, for example, those exemplified as the material of the hole transporting layer described later can be applied.

  The polymer used in the present invention is preferably a compound represented by the following general formula (P-1).

  In General Formula (P-1), Uem represents a unit containing a metal complex having a tridentate or higher ligand. Up represents a unit containing a hole transporting functional site. Ue represents a unit containing an electron transporting functional site. m represents a positive number, and n and p each represents a number of 0 or more, and represents the mol% constituting the polymer so that m + n + p = 100 mol%.

The general formula (P-1) will be described in detail below.
As the metal complex constituting the unit containing a metal complex having a tridentate or higher ligand represented by Uem, those described as the above metal complex can be applied, and the preferred range is also the same. The metal complex is preferably phosphorescent from the viewpoint of luminous efficiency.
Uem may contain a metal complex part having a tridentate or higher ligand on the polymer main chain or in the side chain.
As the hole transporting material constituting the unit containing the hole transporting functional site represented by Up, a material constituting the hole injection layer and the hole transporting layer, which will be described later, can be used. Preferably, carbazole is used. A derivative, an azacarbazole derivative, an arylamine derivative, or a thiophene derivative, and more preferably a carbazole derivative, an azacarbazole derivative, or an arylamine derivative.
Specific examples of the hole transport function site include the following. (* Represents a site bonded to the polymer chain.)

The hole transporting functional site may have a substituent, and as the substituent, those exemplified as the substituents of R ^{21 to} R ²⁴ in the general formula (1) can be applied.
As the electron transport material constituting the unit containing the electron transport function site represented by Ue, the electron injection layer, the material constituting the electron transport layer, and the like described later can be used, but preferably a pyridine derivative or a quinoline derivative. Phenanthroline derivatives, silole derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, or azabenzimidazole derivatives, more preferably phenanthroline derivatives, silole derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, It is a benzimidazole derivative or an azabenzimidazole derivative.
Specific examples of the electron transport function site include the following. (* Represents a site bonded to the polymer chain.)

Said electron transport function site | part may have a substituent and what was mentioned as a substituent of R < ²¹ > -R < ²⁴ > in General formula (1) is applicable as a substituent.
In addition, the hole transport functional site and the electron transport functional site may be conjugated polymers represented by the following. (* Represents a site bonded to the polymer chain.)

Said conjugated polymer may have a substituent and what was quoted as the substituent of R < ²¹ > -R < ²⁴ > in General formula (1) is applicable as a substituent. The substituent in this case is preferably an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, 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 aryl group (preferably 6-30 carbon atoms, more preferably 6-20 carbon atoms, especially Preferably it has 6 to 12 carbon atoms, for example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), an alkoxy group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, especially Preferably it has 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, and 2-ethylhexyloxy. An aryloxy 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 phenyloxy, 1-naphthyloxy, and 2 -Naphthyloxy, etc.), heterocyclic oxy groups (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 , And quinolyloxy), acyl groups (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. Etc.), an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 carbon atom) 20, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio, etc.), an arylthio group (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 carbon atoms). To 12 and includes, for example, phenylthio), a heterocyclic thio 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 pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), 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, Examples include thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, and azepinyl group. ), 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, triphenylsilyl, etc.), a silyloxy group (preferably Is a carbon number of 3-40, more preferably a carbon number of 3-30, particularly preferably a carbon number of 3-24, such as trimethylsilyloxy, triphenylsilyloxy, etc.), more preferably an alkyl group, An aryl group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a cyano group, a heterocyclic group, a silyl group, or a silyloxy group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or a cyano group It is.

m represents a positive number, and n and p are each a number of 0 or more, and represents the mol% constituting the polymer so that m + n + p = 100 mol%, but high efficiency light emission, low voltage driving, high durability From the viewpoint of conversion, it is preferable to satisfy the relationship of 0.0001 ≦ m / (m + n + p) ≦ 0.5, more preferably satisfy 0.001 ≦ m / (m + n + p) ≦ 0.4, and 0.01 ≦ It is more preferable to satisfy m / (m + n + p) ≦ 0.3, and it is particularly preferable to satisfy 0.05 ≦ m / (m + n + p) ≦ 0.2.
When two or more of the above polymers are used, a polymer with n = 0 and a polymer with p = 0 may be mixed or laminated. In the case where a light emitting polymer is used in combination with at least one of a hole transporting polymer and an electron transporting polymer, the light emitting polymer may be used in an amount of 0.01% by mass to 50% by mass in the total polymer. Preferably, it is used in an amount of 0.1% to 40% by mass, more preferably 1% to 30% by mass, and particularly preferably 5% to 20% by mass.

  The weight average molecular weight (polystyrene conversion) of a polymer becomes like this. Preferably it is 1000-5 million, More preferably, it is 2000-1 million, More preferably, it is 3000-100000. In the preferable molecular weight range, the film-forming property, the luminous efficiency and the durability are excellent.

  Examples of the polymer compound used in the present invention are shown below, but the present invention is not limited thereto.

Mole% ratio m: n = 90: 10


Mole% ratio m: n = 85: 15

3. Components of Organic Electroluminescent Device Next, the components that constitute the luminescent material of the present invention will be described in detail.

<Board>
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic compound layer. Specific examples include zirconia-stabilized yttrium (YSZ), inorganic materials such as glass, polyesters such as polyethylene terephthalate, polybutylene phthalate, and polyethylene naphthalate, polystyrene, polycarbonate, polyethersulfone, polyarylate, polyimide, and polycycloolefin. , Norbornene resins, and organic materials such as poly (chlorotrifluoroethylene).
For example, when glass is used as the substrate, alkali-free glass is preferably used as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

  There is no restriction | limiting in particular about the shape of a board | substrate, a structure, a magnitude | size, It can select suitably according to the use, purpose, etc. of a light emitting element. In general, the shape of the substrate is preferably a plate shape. The structure of the substrate may be a single layer structure, a laminated structure, may be formed of a single member, or may be formed of two or more members.

  The substrate may be colorless and transparent or colored and transparent, but is preferably colorless and transparent in that it does not scatter or attenuate light emitted from the organic light emitting layer.

The substrate can be provided with a moisture permeation preventing layer (gas barrier layer) on the front surface or the back surface.
As a material for the moisture permeation preventive layer (gas barrier layer), inorganic materials such as silicon nitride and silicon oxide are preferably used. The moisture permeation preventing layer (gas barrier layer) can be formed by, for example, a high frequency sputtering method.
When a thermoplastic substrate is used, a hard coat layer, an undercoat layer, or the like may be further provided as necessary.

<Anode>
The anode usually has a function as an electrode for supplying holes to the organic compound layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element. , Can be appropriately selected from known electrode materials. As described above, the anode is usually provided as a transparent anode.

  Suitable examples of the material for the anode include metals, alloys, metal oxides, conductive compounds, and mixtures thereof. Specific examples of the anode material include conductive metals such as tin oxide doped with antimony and fluorine (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metals such as oxides, gold, silver, chromium, or nickel, and mixtures or laminates of these metals and conductive metal oxides, inorganic conductive materials such as copper iodide and copper sulfide, polyaniline, polythiophene, and polypyrrole Organic conductive materials such as, and a laminate of these and ITO. Among these, conductive metal oxides are preferable, and ITO is particularly preferable from the viewpoints of productivity, high conductivity, transparency, and the like.

  The anode is composed of, for example, a wet method such as a printing method and a coating method, a physical method such as a vacuum deposition method, a sputtering method, and an ion plating method, and a chemical method such as a CVD and a plasma CVD method. It can be formed on the substrate according to a method appropriately selected in consideration of suitability with the material to be processed. For example, when ITO is selected as the anode material, the anode can be formed according to a direct current or high frequency sputtering method, a vacuum deposition method, an ion plating method, or the like.

  In the organic electroluminescent element of the present invention, the formation position of the anode is not particularly limited and can be appropriately selected according to the use and purpose of the light emitting element. Is preferably formed on the substrate. In this case, the anode may be formed on the entire one surface of the substrate, or may be formed on a part thereof.

  The patterning for forming the anode may be performed by chemical etching such as photolithography, or may be performed by physical etching such as laser, or vacuum deposition or sputtering with a mask overlapped. It may be performed by a lift-off method or a printing method.

  The thickness of the anode can be appropriately selected depending on the material constituting the anode and cannot be generally defined, but is usually about 10 nm to 50 μm, and preferably 50 nm to 20 μm.

The resistance value of the anode is preferably 10 ³ Ω / □ or less, and more preferably 10 ² Ω / □ or less. When the anode is transparent, it may be colorless and transparent or colored and transparent. In order to take out light emission from the transparent anode side, the transmittance is preferably 60% or more, and more preferably 70% or more.

  The transparent anode is described in detail in the book “New Development of Transparent Electrode Films” published by CMC (1999), supervised by Yutaka Sawada, and the matters described here can be applied to the present invention. In the case of using a plastic substrate having low heat resistance, a transparent anode formed using ITO or IZO at a low temperature of 150 ° C. or lower is preferable.

<Cathode>
The cathode usually has a function as an electrode for injecting electrons into the organic compound layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.

  Examples of the material constituting the cathode include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Specific examples include alkali metals (eg, LI, Na, K, or Cs), alkaline earth metals (eg, Mg, Ca, etc.), gold, silver, lead, aluminum, sodium-potassium alloys, lithium-aluminum alloys, Examples thereof include magnesium-silver alloys, rare earth metals such as indium and ytterbium. These may be used alone, but two or more can be suitably used in combination from the viewpoint of achieving both stability and electron injection.

Among these, as a material constituting the cathode, an alkali metal or an alkaline earth metal is preferable from the viewpoint of electron injecting property, and a material mainly composed of aluminum is preferable from the viewpoint of excellent storage stability.
The material mainly composed of aluminum is aluminum alone, an alloy of aluminum and 0.01% by mass to 10% by mass of alkali metal or alkaline earth metal, or a mixture thereof (for example, lithium-aluminum alloy, magnesium-aluminum alloy). Etc.).

  The materials for the cathode are described in detail in JP-A-2-15595 and JP-A-5-121172, and the materials described in these public relations can also be applied in the present invention.

  There is no restriction | limiting in particular about the formation method of a cathode, According to a well-known method, it can carry out. For example, the cathode described above is configured from a wet method such as a printing method or a coating method, a physical method such as a vacuum deposition method, a sputtering method, or an ion plating method, or a chemical method such as CVD or plasma CVD method. It can be formed according to a method appropriately selected in consideration of suitability with the material. For example, when a metal or the like is selected as the cathode material, one or more of them can be simultaneously or sequentially performed according to a sputtering method or the like.

  Patterning when forming the cathode may be performed by chemical etching such as photolithography, physical etching by laser, or the like, or by vacuum deposition or sputtering with the mask overlaid. It may be performed by a lift-off method or a printing method.

In the present invention, the cathode formation position is not particularly limited, and may be formed on the entire organic compound layer or a part thereof.
Further, a dielectric layer made of an alkali metal or alkaline earth metal fluoride or oxide may be inserted between the cathode and the organic compound layer with a thickness of 0.1 nm to 5 nm. This dielectric layer can also be regarded as a kind of electron injection layer. The dielectric layer can be formed by, for example, a vacuum deposition method, a sputtering method, an ion plating method, or the like.

The thickness of the cathode can be appropriately selected depending on the material constituting the cathode and cannot be generally defined, but is usually about 10 nm to 5 μm, and preferably 50 nm to 1 μm.
Further, the cathode may be transparent or opaque. The transparent cathode can be formed by depositing a thin cathode material to a thickness of 1 nm to 10 nm and further laminating a transparent conductive material such as ITO or IZO.

<Organic compound layer>
The organic compound layer in the present invention will be described.
The organic electroluminescent element of the present invention has at least one organic compound layer including a light emitting layer, and the organic compound layer other than the organic light emitting layer includes a hole transport layer, an electron transport layer as described above. , Charge blocking layer, hole injection layer, electron injection layer and the like.

-Formation of organic compound layer-
In the organic electroluminescent element of the present invention, each layer constituting the organic compound layer can be suitably formed by any of a dry film forming method such as a vapor deposition method and a sputtering method, a transfer method, a printing method, and an ink jet method.

-Organic light emitting layer-
The organic light emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer having a function of providing a field to emit light.
The light emitting layer in the present invention may be composed of only a light emitting material, or may be a mixed layer of a host material and a light emitting material. The light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the dopant may be one type or two or more types. The host material is preferably a charge transport material. The host material may be one type or two or more types, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Further, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or two or more layers, and each layer may emit light in different emission colors.
As the light emitting material that can be used in the present invention, other fluorescent light emitting materials and phosphorescent light emitting materials can be used in addition to the polymer compound of the present invention. These light emitting materials used in combination may be a low molecular compound or a high molecular compound.

  Examples of fluorescent light-emitting materials that can be used in the present invention include, for example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives. , Condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styryl Of amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidin compounds, metal complexes of 8-quinolinol derivatives and pyromethene derivatives Various metal complexes typified by metal complex, polythiophene, polyphenylene, polyphenylene vinylene polymer compounds such as, and compounds such as organic silane derivatives.

Examples of the phosphorescent material that can be used in the present invention include complexes containing transition metal atoms or lanthanoid atoms.
Although it does not specifically limit as a transition metal atom, Preferably, ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, and platinum are mentioned, More preferably, they are rhenium, iridium, and platinum.
Examples of lanthanoid atoms include lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. Among these lanthanoid atoms, neodymium, europium, and gadolinium are preferable.

Examples of the ligand of the complex include G.I. WIlkInson et al., ComprehensIve CoordInatIon ChemIstry, published by Pergamon Press, 1987, H.C. YersIn, “Photochemistry and Photophysics of CoordInatIon Compounds”, published by SprInger-Verlag, Inc., 1987, Akio Yamamoto, “Organic Metal Chemistry-Fundamentals and Applications,” published by Soukabo, Inc., published in 1982, etc. .
The specific ligand is preferably a halogen ligand (preferably a chlorine ligand), a nitrogen-containing heterocyclic ligand (for example, phenylpyridine, benzoquinoline, quinolinol, bipyridyl, or phenanthroline), A diketone ligand (for example, acetylacetone), a carboxylic acid ligand (for example, acetic acid ligand), a carbon monoxide ligand, an isonitrile ligand, and a cyano ligand, more preferably Nitrogen heterocyclic ligand. The complex may have one transition metal atom in the compound, or may be a so-called binuclear complex having two or more. Different metal atoms may be contained at the same time.

  The phosphorescent material is preferably contained in the light emitting layer in an amount of 0.1% by mass to 40% by mass, and more preferably 0.5% by mass to 20% by mass.

  Examples of the host material contained in the light emitting layer in the present invention include those having a carbazole skeleton, those having a diarylamine skeleton, those having a pyridine skeleton, those having a pyrazine skeleton, those having a triazine skeleton, and aryl. Examples thereof include materials having a silane skeleton and materials exemplified in the section of a hole injection layer, a hole transport layer, an electron injection layer, or an electron transport layer described later.

  Although the thickness of a light emitting layer is not specifically limited, Usually, it is preferable that they are 1 nm-500 nm, it is more preferable that they are 5 nm-200 nm, and it is still more preferable that they are 10 nm-100 nm.

-Hole injection layer, hole transport layer-
The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
The hole injection layer and the hole transport layer preferably contain an electron-accepting dopant from the viewpoint of lowering voltage and driving durability.

  As the electron-accepting dopant introduced into the hole-injecting layer or the hole-transporting layer, an inorganic compound or an organic compound can be used as long as it has an electron-accepting property and oxidizes an organic compound. As the compound, metal halides such as ferric chloride, aluminum chloride, gallium chloride, indium chloride, and antimony pentachloride, and metal oxides such as vanadium pentoxide and molybdenum trioxide can be suitably used.

In the case of an organic compound, a compound having a nitro group, halogen, cyano group, trifluoromethyl group or the like as a substituent, a quinone compound, an acid anhydride compound, fullerene, or the like can be preferably used.
Specifically, hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane, tetrafluorotetracyanoquinodimethane, p-fluoranyl, p-chloranil, p-bromanyl, p-benzoquinone, 2,6-dichlorobenzoquinone 2,5-dichlorobenzoquinone, tetramethylbenzoquinone, 1,2,4,5-tetracyanobenzene, o-dicyanobenzene, p-dicyanobenzene, 1,4-dicyanotetrafluorobenzene, 2,3-dichloro-5 , 6-dicyanobenzoquinone, p-dinitrobenzene, m-dinitrobenzene, o-dinitrobenzene, p-cyanonitrobenzene, m-cyanonitrobenzene, o-cyanonitrobenzene, 1,4-naphthoquinone, 2,3-dichloronaphthoquinone, 1 Nitronaphthalene, 2-nitronaphthalene, 1,3-dinitronaphthalene, 1,5-dinitronaphthalene, 9-cyanoanthracene, 9-nitroanthracene, 9,10-anthraquinone, 1,3,6,8-tetranitrocarbazole, 2,4,7-trinitro-9-fluorenone, 2,3,5,6-tetracyanopyridine, maleic anhydride, phthalic anhydride, fullerene C60, fullerene C70 and the like. 11-111463, 11-251067, JP 2000-196140, 2000-286054, 2000-315580, 2001-102175, 2001-160493, 2002-252085, 2002-56985, 2003. 157981, 20 3-271862, the 2003-229278, said 2004-342614, said 2005-72012, the 2005-166637, compounds can be suitably used according to the 2005-209643 or the like.

  Among these, hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane, tetrafluorotetracyanoquinodimethane, p-fluoranyl, p-chloranil, p-bromanyl, p-benzoquinone, 2,6-dichlorobenzoquinone, 2 , 5-dichlorobenzoquinone, 1,2,4,5-tetracyanobenzene, 1,4-dicyanotetrafluorobenzene, 2,3-dichloro-5,6-dicyanobenzoquinone, p-dinitrobenzene, m-dinitrobenzene, o-dinitrobenzene, 1,4-naphthoquinone, 2,3-dichloronaphthoquinone, 1,3-dinitronaphthalene, 1,5-dinitronaphthalene, 9,10-anthraquinone, 1,3,6,8-tetranitrocarbazole, 2,4,7-trinitro-9- Luenone, 2,3,5,6-tetracyanopyridine, or fullerene C60 is preferred, and hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane, tetrafluorotetracyanoquinodimethane, p-fluoranyl, p- Chloranil, p-bromanyl, 2,6-dichlorobenzoquinone, 2,5-dichlorobenzoquinone, 2,3-dichloronaphthoquinone, 1,2,4,5-tetracyanobenzene, 2,3-dichloro-5,6-dicyano Benzoquinone or 2,3,5,6-tetracyanopyridine is more preferred, and tetrafluorotetracyanoquinodimethane is particularly preferred.

These electron-accepting dopants may be used alone or in combination of two or more.
Although the usage-amount of an electron-accepting dopant changes with kinds of material, it is preferable that it is 0.01 mass%-50 mass% with respect to hole transport layer material, and it is 0.05 mass%-20 mass%. It is further more preferable and it is especially preferable that it is 0.1 mass%-10 mass%. When the amount used is less than 0.01% by mass with respect to the hole transporting material, the effect of the present invention is insufficient because it is insufficient, and when it exceeds 50% by mass, the hole transporting ability is impaired. .

Specifically, the hole injection layer and the hole transport layer are carbazole derivatives, azacarbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, thiophene derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives. , Phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrins A layer containing a compound, an organic silane derivative, carbon, or the like is preferable.
The thicknesses of the hole injection layer and the hole transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the hole transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the hole injection layer is preferably 0.1 nm to 200 nm, more preferably 0.5 nm to 100 nm, and still more preferably 1 nm to 100 nm.
The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the materials described above, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. .

-Electron injection layer, electron transport layer-
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
The electron injection layer and the electron transport layer preferably contain an electron donating dopant from the viewpoint of lowering voltage and driving durability.

The electron donating dopant introduced into the electron injecting layer or the electron transporting layer only needs to have an electron donating property and a property of reducing an organic compound, such as an alkali metal such as Li or an alkaline earth metal such as Mg. Transition metals including rare earth metals and reducing organic compounds are preferably used.
As the metal, a metal having a work function of 4.2 eV or less can be preferably used. Specifically, Li, Na, K, Be, Mg, Ca, Sr, Ba, Y, Cs, La, Sm, Gd , And Yb. Examples of the reducing organic compound include a nitrogen-containing compound, a chalcogen element compound (such as a sulfur-containing compound, a selenium compound, or a tellurium-containing compound), a phosphorus-containing compound, and the like. In addition, materials described in JP-A-6-212153, JP-A-2000-196140, 2003-68468, 2003-229278, 2004-342614, and the like can be used.

  These electron donating dopants may be used alone or in combination of two or more. The amount of the electron donating dopant varies depending on the type of material, but is preferably 0.1% by mass to 99% by mass, and 1.0% by mass to 80% by mass with respect to the electron transport layer material. Is more preferable, and 2.0 mass% to 70 mass% is particularly preferable. When the amount used is less than 0.1% by mass with respect to the electron transport layer material, the effect of the present invention is insufficient because it is insufficient, and when it exceeds 99% by mass, the electron transport ability is impaired.

  Specifically, the electron injection layer and the electron transport layer are pyridine derivatives, quinoline derivatives, phenanthroline derivatives, silole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, azabenzimidazole derivatives, fluorenone. Derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives Metal complexes represented by metal complexes of 8-quinolinol derivatives, metal phthalocyanines, benzoxazole and benzothiazole ligands, organic It is preferable that a layer containing a run-derivatives, and the like.

The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and still more preferably 0.5 nm to 50 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

-Hole blocking layer-
The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic compound layer adjacent to the light emitting layer on the cathode side.
Examples of the organic compound constituting the hole blocking layer include aluminum complexes such as BAlq, triazole derivatives, phenanthroline derivatives such as BCP, and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm.
The hole blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

<Protective layer>
In the present invention, the entire organic EL element may be protected by a protective layer.
As a material contained in the protective layer, any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, TI, and NI, MgO, SIO, SIO ₂ , Al ₂ O ₃ , GeO, NIO, CaO, BaO, and Fe _2. Metal oxides such as O ₃ , Y ₂ O ₃ , or TIO ₂ , metal nitrides such as SIN _x , SIN _x O _y , metal fluorides such as MgF ₂ , LIF, AlF ₃ , or CaF ₂ , polyethylene, polypropylene , Polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, or a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and at least one comonomer A copolymer obtained by copolymerizing a monomer mixture containing Examples thereof include a fluorine-containing copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more, and a moisture-proof substance having a water absorption of 0.1% or less.

  The method for forming the protective layer is not particularly limited, and for example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency) Excited ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, or transfer method can be applied.

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

<Drive>
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving method described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429, 6023308, and the like can be applied.

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

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

(Use of the present invention)
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.

  The present invention will be specifically described using examples, but the present invention is not limited to these examples.

Comparative Example 1
A transparent support substrate was prepared by depositing ITO to a thickness of 150 nm on a 25 mm × 25 mm × 0.7 mm glass substrate to form a film (Tokyo Sanyo Vacuum Co., Ltd.). This transparent support substrate was etched and washed. On this ITO glass substrate, Baytron P (PEDOT-PSS solution (polyethylenedioxythiophene-polystyrene sulfonic acid dope) / manufactured by Bayer) of the hole injection and transport layer was spin-coated and then vacuumed at 100 ° C. for 1 hour. It dried and was set as the positive hole injection and transport layer (film thickness of about 100 nm). A solution obtained by dissolving 40 mg of compound PA (compound described in JP-A No. 2003-77675) in 3 mL of 1,2-dichloroethane was spin-coated thereon to form a light emitting layer (film thickness: about 50 nm). Next, electron transport materials BAlq and Alq were sequentially deposited to a thickness of 20 nm and 30 nm, respectively, to form an electron transport layer. Further, LiF was deposited to a film thickness of about 3 nm. Deposition was performed in a vacuum of 10 ⁻³ Pa to 10 ⁻⁴ Pa and a substrate temperature at room temperature. A patterned mask (a mask having a light emission area of 2 mm × 2 mm) was placed thereon, and aluminum was deposited to a thickness of about 400 nm to produce a device. The produced element was sealed in a dry glove box.

Comparative Example 2
In the device of Comparative Example 1, a device was produced in exactly the same manner as Comparative Example 1, except that Compound P-B (compound described in JP-A-2003-77675) was used instead of Compound PA.

Example 1
In the device of Comparative Example 1, a device was fabricated in exactly the same manner as in Comparative Example 1, except that Compound P1 was used instead of Compound PA.

Example 2
In the device of Comparative Example 1, a device was fabricated in exactly the same manner as in Comparative Example 1 except that Compound P3 was used instead of Compound PA.

(Element evaluation)
(1) External quantum efficiency Using a source measure unit 2400 manufactured by Toyo Technica Co., Ltd., a direct current voltage is applied to each element to emit light. The brightness was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these numerical values, the external quantum efficiency when the luminance was around 1000 cd / m ² was calculated by the luminance conversion method.

(2) driving durability: a luminance half-life each element by applying a DC voltage so that the luminance 1000 cd / ^{m 2,} the time was measured until the brightness is 500 cd / ^{m 2.} This luminance half time was used as an index of driving durability.
(3) External quantum efficiency and luminance half-life when a metal complex solution is aged In the preparation of each device, a solution obtained by dissolving the metal complex polymer according to the present invention and a comparative metal complex in 1,2-dichloroethane is aged for 5 hours. After that, spin coating was performed, and the device was fabricated in exactly the same manner as in Examples and Comparative Examples. The external quantum efficiency and luminance half time of the device thus fabricated were measured by the same methods as in (1) and (2), respectively.
The results obtained are summarized in Table 1 and Table 2 below.

  As is clear from the above results, the device of the present invention was superior in luminous efficiency and driving durability compared to the comparative device. Moreover, the performance degradation after aging of the solution was small, and the performance change due to the fluctuation of the manufacturing factor could be suppressed.

Claims (3)

An organic electroluminescent device comprising an organic electroluminescent device having at least one organic layer between a pair of electrodes, the polymer having a structure represented by the following formula P1 .

(In formula P1, n represents a positive integer.) The organic electroluminescent element according to claim 1, wherein the polymer contains a hole transporting functional site. The organic electroluminescence device according to claim 1, wherein the polymer contains an electron transporting functional site.