JP2009076509A - Organic electroluminescent element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic EL element showing high luminous efficiency and durability. <P>SOLUTION: The organic electroluminescent element has at least one organic layer including a luminescent layer between a pair of electrodes, wherein: a layer containing a carbene compound is formed between the luminescent layer and an anode; the luminescent layer contains at least one of electron transporting material and at least one of hole transporting material; at least one of the electron transporting material and hole transporting material is a luminescent material; and the concentration of the electron transporting material of the luminescent layer decreases from a cathode side to the anode side. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent device (hereinafter abbreviated as an organic EL device). In particular, the present invention relates to an organic electroluminescent device having high luminous efficiency and excellent durability.

  The organic EL element is composed of a light emitting layer or a plurality of organic layers including a light emitting layer and a counter electrode sandwiching the organic layer. In the organic EL element, electrons injected from the cathode and holes injected from the anode are recombined in the organic layer, emitted light from the generated excitons, and other molecules generated by energy transfer from the excitons. It is an element for obtaining light emission using at least one of light emission from the excitons.

  Until now, organic EL elements have been developed with greatly improved brightness and element efficiency by using a laminated structure with separated functions. For example, as described in Science, Vol. 267, No. 3, 1995, p. 1332 (Non-patent Document 1), a two-layer stacked element in which a hole transport layer and a light emitting / electron transport layer are stacked, Commonly used are three-layer stacked devices with a hole transport layer, light-emitting layer, and electron transport layer stacked, and four-layer stacked devices with a hole transport layer, light-emitting layer, hole blocking layer, and electron transport layer stacked. It is done.

  However, many problems still remain in practical use of organic EL elements, such as improving luminous efficiency and driving durability. In particular, increasing the light emission efficiency can reduce power consumption and is also advantageous in terms of driving durability, and thus many improvement means have been disclosed so far. However, in general, an element whose luminous efficiency is improved by providing a charge blocking layer has a short driving durability, and an element having excellent driving durability often has a low luminous efficiency. It has not been easy to achieve both improvement in driving performance and driving durability.

  Various methods are known as methods for increasing the light emission efficiency of the element, but reducing the drive voltage is also highly effective in reducing power consumption. As a method for reducing the driving voltage, for example, a method using a transport material having high charge mobility is known, and a carbene compound is known as a material excellent in hole transportability (Patent Document 1). The carbene compound is generally rich in hole transport properties, and by using it in the hole transport layer, the effect of improving the light emission efficiency and lowering the driving voltage can be obtained. However, carbene compounds are generally poor in stability to electrons, and it has been found that when used close to the light emitting layer, the light emitting efficiency is improved and the driving voltage is lowered and the driving durability is deteriorated at the same time. . When a carbene compound is used for the hole transport layer, it is necessary to use it for a layer from which electrons do not flow, and there are currently limited methods for using the carbene compound.

As a means for improving the light emission efficiency, a method of providing a gradient in the concentration in the film thickness direction of the material constituting the light emitting layer has been proposed (for example, see Patent Document 2). In the device in which the electron transporting compound and the hole transporting compound constitute the light emitting layer, the structure in which the electron transporting compound decreases from the cathode to the anode and the hole transporting compound increases from the cathode to the anode is described. Has been. The charge injected from the cathode proceeds by hopping on the electron transporting compound. However, since the concentration of the electron transporting compound is reduced, the movement of electrons is limited as it approaches the anode. Similarly, holes injected from the anode proceed on the hole transporting compound by hopping, but the concentration of the hole transporting compound decreases toward the cathode. Movement is restricted.
Science, 267, 3, 1995, p. 1332 JP2007-96259 JP 2001-155862 A

  An object of the present invention is to provide an organic EL device having high luminous efficiency and excellent durability.

It has been found that the above-mentioned problems of the present invention can be solved by the following means.
<1> An organic electroluminescence device having at least one organic layer including a light-emitting layer between a pair of electrodes, wherein the light-emitting layer includes a layer containing a carbene compound between the light-emitting layer and the anode. At least one electron transporting material and at least one hole transporting material, wherein at least one of the electron transporting material and the hole transporting material is a light emitting material, and the electron transporting material in the light emitting layer The organic electroluminescent element is characterized in that the concentration of is reduced from the cathode side toward the anode side.
<2> The organic electroluminescent element according to <1>, wherein the electron transporting material is a light emitting material.
<3> The organic electroluminescent element according to <1>, wherein the hole transporting material is a light emitting material.
<4> The organic electroluminescent element according to any one of <1> to <3>, wherein the layer containing the carbene compound is in contact with the light emitting layer.
<5> The concentration of the electron transporting material in a region near the anode side interface of the light emitting layer is 0% or more to 50% of the concentration of the electron transporting material in a region near the cathode side interface of the light emitting layer. % Or less, The organic electroluminescent element according to any one of <1> to <4>.
<6> Any one of <1> to <5>, wherein the concentration of the electron transporting material in the light emitting layer is 0% by mass or more and 30% by mass or less in a region near the anode side interface. 2. The organic electroluminescent element according to item 1.
<7> The organic luminescence device according to any one of <1> to <6>, wherein the carbene compound is a compound represented by the following general formula (C1):

(In the formula, M represents a transition metal atom or a transition metal ion. R ¹¹ and R ¹² represent a hydrogen atom or a substituent, and R ¹¹ and R ¹² may be independently bonded to M. R ¹¹ , R ¹² may be bonded to each other to form a ring structure, L ¹¹ represents a ligand and may be bonded to at least one of R ¹¹ and R ^12. X ¹¹ represents a counter ion. n ¹¹ represents an integer of 0 to 5, n ¹² represents an integer of 1 to 6, and n ¹³ represents an integer of 0 to 3. C represents a carbene carbon, and the carbene carbon is represented by R ¹¹ and R ¹² . Bind and coordinate to M.).
<8> The organic electroluminescent element according to <7>, wherein the carbene compound represented by the general formula (C1) is a compound represented by the following general formula (C2):

(In the formula, M represents a transition metal atom or a transition metal ion. R ²¹ , R ²² , R ²³ , and R ²⁴ represent a hydrogen atom or a substituent, and R ²¹ , R ²² , R ²³ , and R ²⁴⁾ May be independently bonded to M. R ²¹ , R ²² , R ²³ , and R ²⁴ may be bonded to each other to form a ring structure, L ²¹ represents a ligand, R ²¹ , It may be bonded to at least one of R ²² , R ²³ , and R ^24. X ²¹ represents a counter ion, n ²¹ represents an integer of 0 to 5, n ²² represents an integer of 1 to 6, and n ²³ represents an integer of 0 to 3. C represents a carbene carbon, which binds to two nitrogen atoms and coordinates to M).
<9> The organic electroluminescent element as described in any one of <1> to <8>, wherein the light emitting layer contains a phosphorescent material.

  The authors found that carbene compounds with high hole transportability are often insufficiently stable to electrons, and as a result of intensive investigations into solutions, the constituent materials of the light-emitting layer have a concentration gradient. The present inventors have found that the leakage of electrons to the carbene compound layer is suppressed, and that the excellent transportability of the carbene compound can be exhibited without deteriorating the durability of the device. .

According to the present invention, an organic EL device having high luminous efficiency and excellent durability is provided.
In particular, an organic EL element having excellent driving durability with high luminous efficiency using a phosphorescent material is provided.

  The organic EL device of the present invention is an organic electroluminescent device having at least one organic layer including a light emitting layer between a pair of electrodes, and has a layer containing a carbene compound between the light emitting layer and the anode. The light emitting layer includes at least one electron transporting material and at least one hole transporting material, and at least one of the electron transporting material and the hole transporting material is a light emitting material, The concentration of the electron transporting material is decreased from the cathode side toward the anode side. In the present invention, the meaning of “the concentration decreases from the cathode side toward the anode side” as a whole means that the concentration decreases from the cathode side toward the anode side. The main point is that it may change continuously or stepwise. Alternatively, even if there is a region that is partially increased or decreased, it is within the intended scope of the present application if it is generally decreased. In the present application, a pattern in which the density continuously changes is preferable.

  Preferably, the concentration of the electron transporting material in the light emitting layer gradually decreases from the cathode side toward the anode side, and the concentration of the electron transporting material in a region near the anode side interface of the light emitting layer is It is 0% or more and 50% or less with respect to the concentration of the electron transporting material in the region near the cathode side interface of the layer. More preferably, it is 0% or more and 20% or less.

Preferably, the layer containing the carbene compound is in contact with the light emitting layer.
Preferably, the light emitting layer contains a phosphorescent material.

  The carbene compound-containing layer in the present invention is disposed on the anode side of the light emitting layer, and the driving voltage is reduced due to its excellent hole transportability. The light emitting layer in the present invention has a structure in which the concentration of the electron transporting material in the light emitting layer is inclined as described above and gradually decreases from the cathode side toward the anode side. In the light emitting layer having a tilted structure in the present invention, the movement balance of electrons and holes in the light emitting layer is preferably adjusted, and the electron and hole efficiency can be recombined across the entire light emitting layer. Improves and the drive voltage decreases. Furthermore, since electrons injected from the cathode are efficiently recombined in the light emitting layer, electrons do not leak from the light emitting layer to the anode side. Therefore, damage to the layer containing the carbene compound due to electrons is eliminated, and driving durability is dramatically improved. In particular, when the carbene compound is adjacent to the light emitting layer, the effects of the present invention are remarkably exhibited.

1. Organic EL element structure As a form of lamination | stacking of the organic compound layer in this invention, the aspect laminated | stacked in order of the positive hole transport layer, the light emitting layer, and the electron carrying layer from the anode side is preferable. Further, a hole injection layer may be provided between the hole transport layer and the anode, and an electron injection layer may be provided between the electron transport layer and the cathode. An electron transporting intermediate layer that blocks holes leaking from the light emitting layer may be provided between the light emitting layer and the electron transporting layer.
In the present invention, the carbene compound-containing layer is disposed between the anode and the light emitting layer, preferably between the hole injection layer or the hole transport layer and the light emitting layer.

  For example, the organic EL element according to the present invention may employ the following layer structure, but is not limited thereto, and may be appropriately determined according to the purpose and the like.

Anode / light-emitting layer / cathode Anode / hole transport layer / light-emitting layer / electron transport layer / cathode Anode / hole transport layer / light-emitting layer / block layer / electron transport layer / cathode Anode / hole transport layer / Light emitting layer / block layer / electron transport layer / electron injection layer / cathode ・ Anode / hole injection layer / hole transport layer / light emission layer / block layer / electron transport layer / cathode ・ Anode / hole injection layer / hole transport Layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode A preferred embodiment of the organic compound layer in the organic electroluminescence device of the present invention is, in order from the anode side, at least (1) a hole injection layer, a positive layer. Hole transport layer (hole injection layer and hole transport layer may be combined), carbene compound-containing layer, light emitting layer, electron transport layer, and electron injection layer (electron transport layer and electron injection layer may be combined) (2) hole injection layer, hole transport layer (the hole injection layer and the hole transport layer serve as both And may be), carbene compound-containing layer, light emitting layer, an electron transporting intermediate layer is an aspect which has electron transporting layer, and an electron injection layer (electron transport layer and the electron injection layer may also have the role).

The electron transporting intermediate layer preferably has at least one of a function of promoting electron injection into the light emitting layer and a function of blocking holes.
In order to effectively develop the functions of hole injection promotion, electron injection promotion, hole block, electron block, and exciton block, the carbene compound-containing layer and the electron transporting intermediate layer are adjacent to the light emitting layer. Preferably it is.
Each layer may be divided into a plurality of secondary layers.

The organic EL element in the present invention may have a resonator structure. For example, a multilayer mirror made of a plurality of laminated films having different refractive indexes, a transparent or translucent electrode, a light emitting layer, and a metal electrode are superimposed on a transparent substrate. The light generated in the light emitting layer resonates repeatedly with the multilayer mirror and the metal electrode as a reflection plate.
In another preferred embodiment, a transparent or translucent electrode and a metal electrode each function as a reflector on a transparent substrate, and light generated in the light emitting layer repeats reflection and resonates between them.
In order to form a resonant structure, the optical path length determined from the effective refractive index of the two reflectors and the refractive index and thickness of each layer between the reflectors is adjusted to the optimum value to obtain the desired resonant wavelength. Is done. The calculation formula in the case of the first embodiment is described in JP-A-9-180883. The calculation formula in the case of the second aspect is described in Japanese Patent Application Laid-Open No. 2004-127795.

  Each layer constituting the organic compound layer can be suitably formed by any of dry film forming methods such as vapor deposition and sputtering, transfer methods, printing methods, coating methods, ink jet methods, and spray methods.

  Next, the element which comprises the organic EL element of this invention is demonstrated in detail.

2. Light-emitting layer The light-emitting layer receives holes from the anode, hole-injection layer, and hole-transport layer when an electric field is applied, and receives electrons from the cathode, electron-injection layer, and electron-transport layer. It is a layer which has the function to provide and to emit light.
The light emitting layer in the present invention contains at least one kind of electron transporting material and at least one kind of hole transporting material, and at least one of the electron transporting material and the hole transporting material is a light emitting material, The concentration of the electron transporting material in the light emitting layer decreases from the cathode side toward the anode side.
As the electron transporting material, an electron transporting light emitting material and / or an electron transporting host material are used. As the hole transporting material, a hole transporting light emitting material and / or a hole transporting host material are used. In the present invention, the electron transporting light-emitting material is preferably the electron transporting material having the concentration gradient.

The concentration of the electron transporting material in the light emitting layer is preferably 0% by mass or more and 30% by mass or less, more preferably 0% by mass or more and 10% by mass or less in the region near the anode side interface.
In the specification of the present application, the “region near the cathode side interface of the light emitting layer” is defined as a region having a thickness of 10% of the thickness of the entire light emitting layer from the cathode side interface of the light emitting layer. The “region near the anode side interface” is defined as a region having a thickness of 10% of the thickness of the entire light emitting layer from the anode side interface of the light emitting layer. Further, the density in the region is defined as indicating the average density in the region. Furthermore, the concentration of each material in the “region near the cathode side (anode side) interface of the light-emitting layer” is the time of flight secondary ion mass spectrometry (TOF-SIMS), etching X-ray photoelectron spectroscopy (XPS / ESCA), etc. It can be measured by the method.
When the concentration of the electron transporting material in the region near the anode side interface is 50% or more with respect to the concentration of the electron transporting material in the region near the cathode side interface, the concentration gradient is insufficient and recombination does not occur. The amount of electrons passing through the light emitting layer is increased, and the carbene compound layer is adversely affected. Further, if the concentration of the electron transporting material in the region near the anode side interface is 30% or more of the composition of the previous light emitting layer, the electron transporting property is not sufficiently limited even on the anode side, and a concentration gradient is given to the electron transporting material. This is not preferable because it is difficult to obtain the desired effect.

  The light emitting material in the present invention is an electron transporting light emitting material or a hole transporting light emitting material.

(Electron transporting luminescent material)
The electron transporting light emitting material used in the present invention is preferably a phosphorescent light emitting material.
Examples of the electron-transporting phosphorescent material include orthometalated metal complexes and porphyrin metal complexes.
Ortho metalated metal complexes include, for example, Akio Yamamoto "Organic Metal Chemistry-Fundamentals and Applications", pages 150, 232, Hankabosha (published in 1982) and H.C. Yersin's “Photochemistry and Photophysics of Coordination Compounds”, pages 71-77, pages 135-146, Springer-Verlag (published in 1987), etc.

There are various ligands that form the ortho-metalated metal complex, which are also described in the above documents. Among them, preferred ligands include 2-phenylpyridine derivatives, 7,8- Examples include benzoquinoline derivatives, 2- (2-thienyl) pyridine derivatives, 2- (1-naphthyl) pyridine derivatives, and 2-phenylquinoline derivatives. These derivatives may have a substituent if necessary. The orthometalated metal complex may have other ligands in addition to the above ligands.
Orthometalated metal complexes are described in Inorg Chem. 1991, 30, 1685, 1988, 27, 3464, 1994, 33, 545, Inorg. Chim. Acta, 1991, No. 181, page 245; Organomet. Chem. 1987, No. 335, 293, J. Am. Am. Chem. Soc. 1985, No. 107, pages 14-31, etc., can be synthesized by various known methods.

Of the porphyrin metal complexes, a porphyrin platinum complex is preferred.
The electron-transporting phosphorescent material used in the present invention may be used alone or in combination of two or more. Further, a fluorescent material and a phosphorescent material may be used at the same time.

  The electron-transporting phosphorescent material used in the present invention is particularly preferably a metal complex having a tridentate or higher ligand.

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

  The metal ion in the metal complex is not particularly limited, but is preferably a transition metal ion or a rare earth metal ion, more preferably an iridium ion or a platinum ion, from the viewpoints of improving luminous efficiency, improving durability, and reducing driving voltage. , Gold ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, palladium ion, silver ion, copper ion, cobalt ion, zinc ion, nickel ion, lead ion, aluminum ion, gallium ion, rare earth metal ion ( For example, a europium ion, a gadolinium ion, or a terbium ion is preferable, and more preferably, an iridium ion, a platinum ion, a gold ion, a rhenium ion, a tungsten ion, a palladium ion, a zinc ion, or an aluminum ion. , Gallium ion, europium ion, cadolinium ion, or terbium ion, and when the metal complex is used as a light emitting material, iridium ion, platinum ion, rhenium ion, tungsten ion, europium ion, gadolinium ion, or terbium ion In particular, when the metal complex is used as a charge transport material or a host material in the light emitting layer, iridium ion, platinum ion, palladium ion, zinc ion, aluminum ion, or gallium ion is 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 chain-like means that the ligand of the metal complex does not have a cyclic structure (for example, terpyridyl ligand, 2,6-diphenylpyridine ligand, etc.). . 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 and Y ¹³ each represent a linking group, a single bond or a double bond. When Y ¹¹ , Y ¹² , or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and L ¹³ , L ¹³ and Y ¹³ , Y ¹³ And the bond between L ¹⁴ each independently represents a single bond or a double bond. n ¹¹ represents the 0-4. The bond between M ¹¹ and L ^{11 to} L ¹⁵ may be any of a coordination bond, an ionic bond, and a covalent bond.

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

In general formula (I), L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ each independently represent a ligand that coordinates to M ¹¹ . 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 furan ligand, thiophene ligand, pyridine ligand, pyrazine ligand, pyrimidine coordination) Children, thiazole ligands, oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, and condensed rings containing them (eg, quinoline ligands, benzothiazole ligands, etc.) and These tautomers).

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, exemplified compounds described in Japanese Patent Application Laid-Open No. 2007-103493 “No. 24” (24). 5-membered heterocyclic ligand of Example Compound (64) described in Compound No. “Chemical 28” and a 5-membered heterocyclic ligand of Compound No. “145” described in Compound No. “Chemical Formula 37” Heterocyclic ligands are also defined as pyrrole tautomers.) Amino ligands (alkylamino ligands (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably carbon atoms). 2-10, for example, methylamino etc.), arylamino ligands (eg phenylamino etc.), acylamino ligands (preferably 2-30 carbons, more preferably carbons) 2 to 20, particularly preferably 2 to 10 carbon atoms such as acetylamino and benzoylamino), alkoxycarbonylamino ligand (preferably having 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), an aryloxycarbonylamino ligand (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino, etc.), sulfonylamino ligand (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably having 1 to 12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc.), imino ligands, etc. These ligands may be further substituted. Good.

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. These ligands may be further substituted.

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, for example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like. Cycloalkenyl 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 with a phosphorus atom are not particularly limited, but each independently represents a dialkylphosphino ligand, a diarylphosphino ligand, a trialkylphosphine coordination. Examples thereof include ligands, triarylphosphine ligands, and phosphinine ligands. These ligands may be further substituted.

L ¹¹ and L ¹⁴ are each independently an aromatic carbocyclic ligand, alkyloxy ligand, aryloxy ligand, ether ligand, alkylthio ligand, arylthio ligand, alkylamino coordination Ligand, arylamino ligand, acylamino ligand, nitrogen-containing heterocyclic ligand (eg pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand) Ligands, oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands, oxadiazole ligands, thiadiazole ligands, or fused ring ligands containing them (Eg, quinoline ligand, quinoxaline ligand, phthalazine ligand, benzoxazole ligand, benzimidazole ligand, etc.), or tautomers thereof Preferred), aromatic carbocyclic ligand, aryloxy ligand, arylthio ligand, arylamino ligand, pyridine ligand, pyrazine ligand, pyrazole ligand, imidazole coordination Or a condensed ring ligand containing the same (for example, quinoline ligand, quinoxaline ligand, phthalazine ligand, benzimidazole ligand, etc.) or a tautomer thereof. , Aromatic carbocyclic ligand, aryloxy ligand, arylthio ligand, arylamino ligand, as well as pyridine ligand, pyrazine ligand, pyrazole ligand, imidazole ligand or Are more preferable, and aromatic carbocyclic ligands, aryloxy ligands, as well as pyridine ligands, pyrazine ligands, pyrazole ligands, imidazole ligands. Ligands or condensed ring ligands containing them are particularly preferred.

L ¹² and ^{L 13} each ^{independently} ligands preferably form a coordinate bond with ^{M 11,} as ligands forming a coordination bond with ^{M 11,} a pyridine ring, a pyrazine ring, a pyrimidine ring, Triazine ring, thiazole ring, oxazole ring, pyrrole ring, triazole ring, and condensed ring containing them (for example, quinoline ring, quinoxaline ligand, phthalazine ligand, benzoxazole ring, benzimidazole ring, indolenine ring) And tautomers thereof are preferable, and pyridine ring, pyrazine ring, pyrimidine ring, pyrrole ring, and condensed ring containing them (for example, quinoline ring, quinoxaline ring, phthalazine ring, indole ring, etc.), And tautomers thereof are more preferable, pyridine ring, pyrazine ring, pyrimidine ring, and condensed ring containing them. (For example, a quinoline ring) is more preferable, and a pyridine ring and a condensed ring containing a pyridine ring (for example, a quinoline ring) are particularly preferable.

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

In general formula (I), Y ¹¹ , Y ¹² , and Y ¹³ each independently represent a linking group, a single bond, or a double bond. 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, an alkenylene group, or an amino linking group. Y ¹¹ is more preferably a single bond, an alkylene group, or an amino linking group, and further 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 general formula (1), general formula (2), general formula (3), general formula (4), and general formula (5). Each compound represented.
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. For example, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrazole ring, imidazole ring, thiazole ring, oxazole ring, pyrrole Ring, triazole ring, and condensed ring containing them (for example, quinoline ring, quinoxaline ring, phthalazine ring, indole ring, benzoxazole ring, benzimidazole ring, indolenine ring) and their tautomers Can be mentioned.

The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is preferably a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrazole ring, imidazole ring, oxazole ring, pyrrole ring, and Condensed ring containing (eg, quinoline ring, quinoxaline ring, phthalazine ring, indole ring, benzoxazole ring, benzimidazole ring, etc.) and tautomers thereof, more preferably pyridine ring, pyrazine ring, pyrimidine ring Imidazole ring, pyrrole ring, condensed ring containing them (for example, quinoline ring and the like) and tautomers thereof, more preferably pyridine ring and condensed ring thereof (for example, quinoline). Ring), and particularly preferably 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. Although it is not particularly limited as the linking group, for example, carbonyl linking group, thiocarbonyl linking group, alkylene group, alkenylene group, arylene group, heteroarylene group, oxygen atom linking group, nitrogen atom linking group, sulfur atom linking group, and Examples thereof include a linking group composed of these combinations.

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, it is an alkyl group (preferably C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, methyl, ethyl, iso-propyl. , Tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl. Preferably it has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl and the like, and an amino group (preferably). Has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms. Examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino. ),

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

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

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

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

R ²¹ , R ²² , R ²³ , and R ²⁴ are each independently an alkyl group, an aryl group, R ²¹ and R ^22, or R ²³ and R ²⁴ bonded to form a ring structure (for example, 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 , T ³⁷ and T ³⁸ may be bonded via a linking group to form a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.).

  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 is a tautomer of a pyrrole derivative (for example, the exemplified compound (24) described in Japanese Patent Application Laid-Open No. 2007-103493, Compound No. 24). 5-membered heterocyclic ligand, terminal 5-membered heterocyclic ligand of exemplary compound (64) described in compound number “Chemical 28”, and 5-membered heterocycle of exemplary compound (145) described in compound number “Chemical 37” Ring ligands, etc.), tautomers of imidazole derivatives (eg, hetero 5-membered ring ligands of the exemplified compound (29) described in Japanese Patent Application Laid-Open No. 2007-103493 Compound No. 24), thiazole derivatives Tautomers (for example, hetero 5-membered ring ligands of the exemplary compound (30) described in Japanese Patent Application Laid-Open No. 2007-103493, compound number 24), tautomers of oxazole derivatives (for example, And a hetero 5-membered ring ligand of Exemplified Compound (31) described in Compound No. “Chemical Formula 24” described in Compound No. 2007-103493 is preferable, and a tautomer of a pyrrole derivative, a tautomer of an imidazole derivative, a thiazole derivative of Tautomers are more preferable, tautomers of pyrrole derivatives and tautomers of imidazole derivatives are more preferable, and tautomers of pyrrole derivatives are particularly preferable.

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 preferred form of the compound represented by the general formula (3) is a compound represented by the following general formula (3-B).

  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 synonymous with Y ²¹ , Y ²² , and Y ²³ in the general formula (1), respectively, and preferred ranges are 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). R ⁷¹ and R ⁷² , R ⁷³ and R ⁷⁴ may be bonded via a linking group to form a ring (for example, a benzene ring or a pyridine ring). R ^{71 to} R ⁷⁴ are synonymous with the substituents of R ^{21 to} R ²⁴ in the general formula (1), and the preferred 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). Alkyl groups, aryl groups, and heterocyclic groups (these groups may be further substituted. In this case, examples of the substituent include those exemplified as the substituent represented by R ²¹ in the general formula (1)). Represents a halogen atom. 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, a cyano 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 an alkylene 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 substituted at the 1,2-position, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or an alkylene group having 1 to 8 carbon atoms.

  The compound represented by the general formula (5) will be described.

Formula (5) ^{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 a combination 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.

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

In the general formula ^{(II), 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 their preferred ranges are also the same.

Y ⁸¹ and Y ⁸² are each independently synonymous with Y ¹² and Y ¹³ in the general formula (I), and their preferred ranges are also the same.

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

n ⁸¹ represents 0 to 5. When M ⁸¹ is a metal having a coordination number of 4, n ⁸¹ is 1, and L ⁸⁵ represents a monodentate ligand. 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 (II) is an aromatic carbocyclic or heterocyclic ring in which L ⁸¹ , L ⁸² , and L ^{83 of the} general formula (II) are coordinated to M ⁸¹ with a carbon atom, or M with 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 (II) are a compound represented by the following general formula (II-A) and a compound represented by the following general formula (II-B).
First, the compound represented by general formula (II-A) is demonstrated.

In the general formula ^{(II-A), M 91} has the same meaning that of ^{M 81} in Formula (II), and preferred 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 Examples thereof include a ring, a triazole ring, and a condensed ring containing them (for example, a quinoline ring, a benzoxazole ring, a benzimidazole ring, an indolenine ring, and the like) and tautomers thereof.

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

Q ⁹³ represents a group forming a 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, tautomers of the triazole ring, and a condensed ring body thereof (for example, benzopyrrole, etc.) are preferred, a pyrrole ring And tautomers of condensed rings containing a pyrrole ring (for example, benzpyrrole) are more preferable.

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

L ⁹⁵ has the same meaning that ^{of L 85} in Formula (II), and preferred ranges are also the same.

n ⁹¹ has the same meaning that of ^{n 81} in Formula (II), and preferred ranges are also the same.

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

In the general formula ^{(II-B), M 101} has the same meaning as ^{M 81} in Formula (II), it is also preferable range same.

Q ¹⁰² has the same meaning as Q ²¹ in formula (1), and the preferred range is also the same.

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

Q ¹⁰³ represents a group forming an aromatic ring. No particular limitation is imposed on the aromatic ring formed by Q ^103, a benzene ring, furan ring, thiophene ring, pyrrole ring, a condensed ring body thereof (for example, a naphthalene ring, benzofuran ring, benzothiophene ring, indole ring Etc.), a benzene ring and a condensed ring containing a benzene ring (such as a naphthalene ring) are more preferable, and a benzene ring is particularly preferable.

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

L ¹⁰⁵ has the same meaning that ^{of L 85} in Formula (II), and preferred ranges are also the same.

n ¹⁰¹ is the same meaning that of ^{n 81} in Formula (II), and preferred 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-C).

In general formula (II-C), 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-C) will be described in detail.
In general formula (II-C), 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 ions, iridium ions, rhenium ions, palladium ions, rhodium ions, ruthenium ions, copper ions, europium ions, gadolinium ions, or terbium ions are preferable, iridium ions, europium ions are more preferable, and iridium ions are preferable. Further preferred.

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

Examples of 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 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, methylamino), an arylamino group (for example, phenylamino) and the like. An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group ( Preferably 2-30 carbons, more preferably 2-20 carbons, Particularly preferably, it has 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino, etc.), an aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably carbon atoms). 7-12, for example, phenyloxycarbonylamino, etc.), sulfonylamino groups (preferably 1-30 carbon atoms, more preferably 1-20 carbon atoms, particularly preferably 1-12 carbon atoms, Examples thereof include methanesulfonylamino, benzenesulfonylamino, etc.), imino group and the like. These groups may be further substituted.

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 And 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, etc.), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, For example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyloxy group (preferably having 2 carbon atoms) To 30, more preferably 2 to 20, and particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably carbon atoms). 3 to 30, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy and triphenylsilyloxy), a carbonyl group (for example, a ketone group, an ester group, or an amide group), an ether group ( For example, a dialkyl ether group, a diaryl ether group, or 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, and particularly preferably 1 to 12 carbon atoms. For example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, and 2-benzthiazolyl Thiocarbonyl group (for example, thioketone group, thioester group, etc.), thioether group (for example, dia). Alkylthioether group, diarylthioether group, or thiofuryl group).

Examples of the group coordinated to M ^X1 with a phosphorus atom include a dialkylphosphino group, a diarylphosphino group, a trialkylphosphine group, a triarylphosphine group, and a phosphinin group. 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 a coordinate bond, an ionic bond, or a covalent bond, respectively.

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

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

Of the compounds represented by the general formula (II-C), 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 ~L ^X24 represents a single bond, a double bond or a linking group. Binding of M ^X2 and ^Y X21 ^{to Y X26} may be a covalent bond, and each of coordination bond.

The compound represented by formula (X2) will be described in detail.
In general formula (X2), M ^X2 has the same meaning as M ^X1 in general formula (II-C), and the preferred range is also the same. Y ^X21 to Y ^X26 represent an atom coordinating to ^{M X2.} The bond between Y ^{X21 to} Y ^X26 and M ^X2 may be a coordinate bond, an ionic bond, or 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, or triazole ring, more preferably Is 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-C), and preferred ranges thereof are also the same.

The compound represented by the general formula (II-C) 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 either a coordination bond or an ionic bond covalent bond.

M ^X3 has the same meaning as M ^X1 in formula (II-C), and the preferred range is also the same. Y ^{X31 to} Y ^X36 each represents an atom coordinated to M ^X3 . ^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-C), and preferred ranges thereof are also the same.

  Specific examples of the compounds represented by the general formula (I) and the general formula (II) include compounds (1) to (247) described in JP-A-2007-103493, for example. It is not limited to these.

  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-B), (3-C), (4), (4- The compounds represented by A), (5), (II), (II-A), (II-B), (II-C), (X2), and (X3) can be synthesized by various methods. .
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

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

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

The metal complex of the present invention is appropriately selected from the ligands that form the partial structure of the target complex, whereby the general formulas (I), (1), (1-A), (2), (3), (3-B), (3-C), (4), (4-A), (5), (II), (II-A), (II-B), (II-C) ), (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 (a method described in Journal of Organic Chemistry, 741, 11, (1946), a method such as heating in pyridine hydrochloride, etc. Can be synthesized. In addition, 2,2′-bipyridylboronic acid derivatives (eg, 6,6′-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolyl) -2,2′-bipyridyl) and halogens A methyl group is deprotected after a Suzuki coupling reaction using a modified anisole derivative (for example, 2-bromoanisole and the like) as a starting material (Journal of Organic Chemistry, 741, 11, (1946), Alternatively, it can also be synthesized by using a method such as heating in pyridine hydrochloride.

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

In 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, and 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 2 carbon atoms). 20, particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl).

  An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, 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.),

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-benzimidazole Riruchio, 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, iodine atom),

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

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

In general formula (III), ^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 ions, cobalt ions, magnesium ions, zinc ions, palladium ions, nickel ions, copper ions, platinum ions, lead ions, aluminum ions, iridium ions, or europium ions are preferable, cobalt ions, Magnesium ions, zinc ions, palladium ions, nickel ions, copper ions, platinum ions, or lead ions are more preferable, copper ions and platinum ions are more preferable, and platinum ions are particularly preferable. M ^Y1 may 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 ²¹ and Q ²² each represent a group that forms a nitrogen-containing heterocycle. Q ^21, it is not particularly restricted but includes nitrogen-containing heterocyclic ring formed by Q ^22, a pyrrole ring, an imidazole ring, a triazole ring, a condensed ring body thereof (for example, benzopyrrole), and these tautomeric 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 are each independently a hydrogen atom, or an alkyl group, aryl group, R ⁴³ and R ⁴⁴ exemplified as a substituent on Z ¹¹ or Z ¹² in the general formula (III). Or a group in which R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (for example, benzo-fused ring, pyridine-fused ring, etc.), and an alkyl group, aryl group, R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded. To form a ring structure (eg, benzo-fused ring, pyridine-fused ring, etc.), and R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (eg, benzo-fused ring, pyridine-fused ring). And more preferably a group that forms a ring).

R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ each independently 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).

  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.

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

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

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

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

Q ¹⁰² represents a 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), and compound (27) described in JP-T-2006-526278. -Compound (32), Compound (36)-Compound (38), Compound (42)-Compound (44), Compound (50)-Compound (52), and Compound (57)-Compound (154). However, it is not limited to these.

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 group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 is independently composed of a single bond, carbon, nitrogen, silicon, sulfur, oxygen, germanium, phosphorus, etc. A linking group, more preferably a single bond, a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, a substituted silicon atom, an oxygen atom, a sulfur atom, a divalent aromatic hydrocarbon ring group, a divalent group More preferably a single bond, a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, a substituted silicon atom, a divalent aromatic hydrocarbon ring group, or a divalent aromatic group. Examples of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 that are heterocyclic groups, particularly preferably single bonds, substituted or unsubstituted methylene groups include the following: Things That.

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, such as methyl, ethyl, iso-propyl, tert. -Butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, especially Preferably it is C2-C10, for example, vinyl, allyl, 2-butenyl, 3-pentenyl etc.), an alkynyl group (preferably C2-C30, more preferably C2-C20, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl.

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, and anthranyl). An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, 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, 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, phenylcarbamoyl and the like.) ,

An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 carbon atoms). To 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, 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, phenylureido), phosphoric acid amide group (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), hydroxy group, mercapto Group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom or iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group,

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

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

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

In general formula (A-2), M ^A2 represents a metal ion. Y ^A21 , Y ^A24 , Y ^A25 and Y ^A28 each independently represent a carbon atom or a nitrogen atom. ^{Y A22,} Y A23, Y ^A26 and ^{Y A27} each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, 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 formula ^{(A4), 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 the general formula (A-1) include compounds (A1) to (A80) described in JP-A-2007-103493, but the present invention is limited to these compounds. There is nothing.

  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 represent a partial structure containing an atom bonded to M ^B1 through a covalent bond.

General formula (B-1) is demonstrated in detail.
In the general formula (B-1), M ^B1 , Y ^B11 , Y ^B14 , Y ^B15 , Y ^B18 , Y ^B12 , Y ^B13 , Y ^B16 , Y ^B17 , L ^B11 , L ^B12 , L ^B13 , L ^B14 , Q ^B11 , And Q ^B12 respectively correspond to M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , 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} represents a carbon atom or a nitrogen atom independently. 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 ^{(B4), 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.

  Examples of the compound represented by the general formula (B-1) include compounds (B1) to (B55) described in JP-A-2007-103493. However, the present invention is not limited to these compounds. Absent.

  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 represent 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.

Examples of the substituent represented by R ^C11 , R ^C12 , R ^C13 and R ^C14 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 2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably 2 carbon atoms) To 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl, 3 Pentynyl, 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, 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.),

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, and 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, 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} are 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 the general formula (C-1) include compounds (C1) to (C63) described in JP2007-103493A, but the present invention is limited to these compounds. Never happen.
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 the general formula (D-1), M ^D1 , L ^D11 , and L ^D12 have the same ^meanings as M ^A1 , L ^A11 , and L ^{A12 in the} corresponding general formula (A-1), respectively, and preferred ranges are also the same. It is.
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 an 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. .
Y ^D21 , Y ^D22 , Y ^D23 and Y ^D24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom. is there.
X ^D21 , X ^D22 , X ^D23 and X ^D24 each independently represent an oxygen atom, a sulfur atom, —NR ^D21 —, —C (R ^D22 ) R ^D23 —, preferably a sulfur atom, —NR ^D21 —, — C (R ^D22 ) R ^D23 —, more preferably —NR ^D21 —, —C (R ^D22 ) R ^D23 —, and still more preferably —NR ^D21 —.
R ^D21 , R ^D22 and R ^D23 each independently represent a hydrogen atom or a substituent. Examples of the substituent represented by R ^D21 , R ^D22 and R ^D23 include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms. Methyl, 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, and more). Preferably it is C2-C12, Most preferably, it is C2-C8, for example, vinyl, allyl, 2-butenyl, 3-pentenyl etc. are mentioned), an alkynyl group (preferably C2-C20, More preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl, 3-pentynyl 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, 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 one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to carbon atoms. 30 and particularly preferably 2 to 12 carbon atoms, and examples thereof include imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, and triazolyl groups. R ^D21 , R ^D22 and R ^D23 are preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.

General formula (D-3) is demonstrated in detail.
In the general formula (D-3), M ^D3 , L ^D31 , L ^D32 , G ^D31 , and G ^D32 are M ^D1 , L ^D11 , L ^D12 , G ^D11 , and G ^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 general formula (D-4), M ^D4 , L ^D41 , L ^D42 , G ^D41 , and G ^D42 correspond to M ^D1 , L ^D11 , L ^D12 , G ^D11 , and G ^D11 in general formula (D-1), respectively. and have the same meaning as G ^D12, the preferred ranges are also the same.
X ^D41 , X ^D42 , X ^D43 and X ^D44 are synonymous with X ^D21 , X ^D22 , X ^D23 and X ^{D24 in the} corresponding general formula (D-2), respectively, and preferred ranges are also the same. Y ^D41 , Y ^D42 , Y ^D43 and Y ^D44 have the same ^{meanings as} Y ^D21 , Y ^D22 , Y ^D23 and Y ^{D24 in the} corresponding general formula (D-2), and preferred ranges are also the same.

  Specific examples of the compound represented by the general formula (D-1) include compounds (D1) to (D24) described in JP-A-2007-103493, but the present invention is limited to these compounds. Never happen.

  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. 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. 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) include compounds (E1) to (E15) described in JP-A-2007-103493, but the present invention is limited to these compounds. Never happen.

  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 by a coordination bond, an ionic bond, or 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 the general formula (F-1) include compounds (F1) to (F52) described in JP-A-2007-103493, but the present invention is limited to these compounds. Never happen.

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

(Hole-transporting light-emitting material)
The hole transporting luminescent material in the present invention will be described.
The hole transporting light emitting material used for the light emitting layer of the present invention preferably has an ionization potential (Ip) of 5.1 eV or more and 6.4 eV or less from the viewpoint of improving durability and lowering driving voltage. It is more preferably 4 eV or more and 6.2 eV or less, and further preferably 5.6 eV or more and 6.0 eV or less. Further, from the viewpoint of improving durability and lowering driving voltage, the electron affinity (Ea) is preferably 1.2 eV or more and 3.1 eV or less, more preferably 1.4 eV or more and 3.0 eV or less. More preferably, it is 8 eV or more and 2.8 eV or less.

Specific examples of such hole transporting light emitting materials include the following materials.
In addition to pyrrole compounds, indole compounds, carbazole compounds, imidazole compounds, polyarylalkane compounds, arylamine compounds, styryl compounds, styrylamine compounds, thiophene compounds, aromatic polycyclic condensation compounds, etc. And metal complexes.
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 platinum, from the viewpoints of improving luminous efficiency, durability, and driving voltage. Ion, gold ion, rhenium ion, tungsten ion, rhodium ion, ruthenium ion, osmium ion, palladium ion, silver ion, copper ion, cobalt ion, nickel ion, lead ion, rare earth metal ion (for example, europium ion, gadolinium ion, Terbium ions, etc.) are preferred, more preferably iridium ions, platinum ions, gold ions, rhenium ions, tungsten ions, europium ions, cadolinium ions, terbium ions, and particularly preferably iridium ions. Platinum ion, a rhenium ion, europium ion, gadolinium ion, terbium ion, most preferably iridium ion. Among metal complexes having iridium ions, particularly preferred are metal complexes having a carbon-Ir bond and a nitrogen-Ir bond (in this case, the bond may be a coordination bond, an ionic bond or a covalent bond). is there.

  Specific examples of such hole-transporting light-emitting materials include, but are not limited to, the following materials.

(Electron transporting host material)
The electron transporting host material used in the present invention preferably has an electron affinity Ea of 2.5 eV or more and 3.5 eV or less, from the viewpoint of improving durability and lowering driving voltage, and 2.6 eV or more and 3.4 eV or less. It is more preferable that it is 2.8 eV or more and 3.3 eV or less. Further, from the viewpoint of improving durability and reducing driving voltage, the ionization potential Ip is preferably 5.7 eV or more and 7.5 eV or less, more preferably 5.8 eV or more and 7.0 eV or less, and 5.9 eV or more. More preferably, it is 6.5 eV or less.

Specific examples of such an electron transporting host include the following materials.
Pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, Fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanines, and derivatives thereof (may form condensed rings with other rings), metal complexes and metals of 8-quinolinol derivatives Examples thereof include various metal complexes represented by metal complexes having phthalocyanine, benzoxazole or benzothiazol as a ligand.

Preferred examples of the electron transporting host include metal complexes, azole derivatives (benzimidazole derivatives, imidazopyridine derivatives, etc.), and azine derivatives (pyridine derivatives, pyrimidine derivatives, triazine derivatives, etc.). To metal complex compounds are preferred. The metal complex compound is more preferably a metal complex having a ligand having at least one nitrogen atom, oxygen atom or sulfur atom coordinated to the metal.
The metal ion in the metal complex is not particularly limited, but is preferably beryllium ion, magnesium ion, aluminum ion, gallium ion, zinc ion, indium ion, tin ion, platinum ion, or palladium ion, more preferably beryllium ion, Aluminum ion, gallium ion, zinc ion, platinum ion, or palladium ion, and more preferably aluminum ion, zinc ion, or palladium ion.

  There are various known ligands contained in the metal complex. For example, “Photochemistry and Photophysics of Coordination Compounds”, Springer-Verlag, H.C. Examples include the ligands described in Yersin, published in 1987, “Organometallic Chemistry: Fundamentals and Applications”, Sakai Hanafusa, Yamamoto Akio, published in 1982, and the like.

The ligand is preferably a nitrogen-containing heterocyclic ligand (preferably having 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and a monodentate ligand. Alternatively, it may be a bidentate or higher ligand, preferably a bidentate or higher and a hexadentate or lower ligand, or a bidentate or higher and lower 6 or lower ligand and a monodentate mixed ligand. preferable.
Examples of the ligand include an azine ligand (for example, pyridine ligand, bipyridyl ligand, terpyridine ligand, etc.), a hydroxyphenylazole ligand (for example, hydroxyphenylbenzimidazole coordination). And a hydroxyphenyl benzoxazole ligand, a hydroxyphenyl imidazole ligand, a hydroxyphenylimidazopyridine ligand, etc.), an alkoxy ligand (preferably having 1 to 30 carbon atoms, more preferably 1 carbon atom). 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 6-20 carbon atoms, particularly preferably 6-12 carbon atoms, for example phenyl Carboxymethyl, 1-naphthyloxy, 2-naphthyloxy, 2,4,6-trimethylphenyl oxy, and 4-biphenyloxy and the like.),

Heteroaryloxy ligand (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy. ), An alkylthio ligand (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), arylthio ligands (Preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio), heteroarylthio ligand (preferably 1 carbon atom) To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridylthio , 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), a siloxy ligand (preferably having 1 to 30 carbon atoms, more preferably 3 to 25 carbon atoms). Particularly preferably, it has 6 to 20 carbon atoms, and examples thereof include a triphenylsiloxy group, a triethoxysiloxy group, and a triisopropylsiloxy group.), An aromatic hydrocarbon anion ligand (preferably having 6 carbon atoms) To 30, more preferably 6 to 25 carbon atoms, particularly preferably 6 to 20 carbon atoms, such as a phenyl anion, a naphthyl anion, an anthranyl anion, etc.), an aromatic heterocyclic anion ligand (preferably Has 1 to 30 carbon atoms, more preferably 2 to 25 carbon atoms, and particularly preferably 2 to 20 carbon atoms. Pyrrole anion, pyrazole anion, pyrazole anion, triazole anion, oxazole anion, benzoxazole anion, thiazole anion, benzothiazole anion, thiophene anion, benzothiophene anion, etc.), indolenine anion ligand, etc. , Preferably a nitrogen-containing heterocyclic ligand, aryloxy ligand, heteroaryloxy group, or siloxy ligand, more preferably a nitrogen-containing heterocyclic ligand, aryloxy ligand, siloxy coordination Or an aromatic hydrocarbon anion ligand or an aromatic heterocyclic anion ligand.

  Examples of the metal complex electron transporting host are described in, for example, JP-A No. 2002-235076, JP-A No. 2004-214179, JP-A No. 2004-221106, JP-A No. 2004-221665, JP-A No. 2004-221068, JP-A No. 2004-327313, and the like. The compound of this is mentioned.

  Specific examples of such an electron transporting host include, but are not limited to, the following materials.

  As the electron transport layer host, E-1 to E-6, E-8, E-9, E-10, E-21, or E-22 are preferable, and E-3, E-4, E-6, E-8, E-9, E-10, E-21, or E-22 is more preferable, and E-3, E-4, E-21, or E-22 is still more preferable.

  In the light emitting layer of the present invention, when a phosphorescent dopant is used as the luminescent dopant, the lowest triplet excitation energy T1 (D) of the phosphorescent dopant and the lowest excited triplet energy of the plurality of host compounds. It is preferable in terms of color purity, external quantum efficiency, and driving durability that the above T1 (H) min satisfies the relationship of T1 (H) min> T1 (D).

(Hole-transporting host material)
The hole transporting host material used in the light emitting layer of the present invention preferably has an ionization potential Ip of 5.1 eV or more and 6.4 eV or less from the viewpoint of improving durability and lowering driving voltage. It is more preferably 6.2 eV or less, and further preferably 5.6 eV or more and 6.0 eV or less. Further, from the viewpoint of improving durability and lowering driving voltage, the electron affinity Ea is preferably 1.2 eV or more and 3.1 eV or less, more preferably 1.4 eV or more and 3.0 eV or less, and 1.8 eV or more. More preferably, it is 2.8 eV or less.

Specific examples of such a hole transporting host material include the following materials.
Pyrrole, carbazole, indole, pyrazole, imidazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound , Aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomer thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films, and Examples thereof include derivatives thereof.
Among these, carbazole derivatives, indole derivatives, aromatic tertiary amine compounds, and thiophene derivatives are preferable, and those having a plurality of carbazole skeleton, indole skeleton, and aromatic tertiary amine skeleton in the molecule are particularly preferable. Further, those having at least one of a carbazole skeleton and an indole skeleton are preferable.
Specific examples of such a hole transporting host material include, but are not limited to, the following compounds.

<Mixing ratio of luminescent material and host material>
-Mixing ratio of host material and light emitting material-
The mixing ratio of the host material and the light emitting material in the present invention is preferably 0.1% by mass to 50% by mass, and more preferably 1% by mass to 30% by mass, in terms of the average mass ratio of the light emitting layer. If it is less than 0.1% by mass, it is not preferable because optimization of device characteristics becomes difficult or the influence of manufacturing variation becomes large, and if it exceeds 50% by mass, the concentration quenching phenomenon of the luminescent material occurs and the luminous efficiency is reduced. It is not preferable because it tends to decrease.

<Film thickness>
The thickness of the light emitting layer is preferably 10 nm or more and 500 nm or less, and more preferably 20 nm or more and 100 nm or less from the viewpoints of luminance unevenness, driving voltage, and luminance. If the thickness of the light emitting layer is small, charge leakage is likely to occur and the light emission efficiency may be lowered, which is not preferable. If the thickness of the light emitting layer is large, the drive voltage increases, leading to a decrease in light emission efficiency and limiting the application.

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

3. Carbene Compound-Containing Layer The carbene compound-containing layer in the present invention is disposed between the anode and the light emitting layer, preferably between the hole injection layer or the hole transport layer and the light emitting layer.
The carbene-containing layer in the present invention is arranged adjacent to the light emitting layer in which the electron transporting material in the present invention is contained in a concentration gradient, thereby having high hole transportability and lowering the driving voltage, Luminous efficiency can be improved and high driving durability can be realized.

  The carbene compound-containing layer in the present invention is preferably in direct contact with the light emitting layer.

The carbene compound-containing layer preferably contains a carbene compound in an amount of 20% by mass to 100% by mass, more preferably 50% by mass to 100% by mass.
Examples of materials other than the carbene compound contained in the carbene compound-containing layer include hole transport materials such as a material described in the hole injection layer and hole transport layer described later, and a material of the light emitting layer described above. is there.

(Carbene compound)
The carbene compound in the present invention is a compound having a bond between carbon and transition metal in which two or more hydrogen atoms are removed from the same element.

  The carbene compound in the present invention is preferably a compound represented by the following general formula (C1).

In the formula, M represents a transition metal atom or a transition metal ion. R ¹¹ and R ¹² represent a hydrogen atom or a substituent, and R ¹¹ and R ¹² may be independently bonded to M. R ¹¹ and R ¹² may be bonded to each other to form a ring structure. L ¹¹ represents a ligand and may be bonded to at least one of R ¹¹ and R ¹² . X ¹¹ represents a counter ion. n ¹¹ represents an integer of 0 to ^{5, n 12} represents an integer of 1 to ^{6, n 13} represents an integer of 0 to 3. C represents a carbene carbon, which binds to R ¹¹ and R ¹² and coordinates to M.

  More preferably, the carbene compound represented by the general formula (C1) is a compound represented by the following general formula (C2).

In the formula, M represents a transition metal atom or a transition metal ion. R ²¹ , R ²² , R ²³ , and R ²⁴ represent a hydrogen atom or a substituent, and R ²¹ , R ²² , R ²³ , and R ²⁴ may be independently bonded to M. R ²¹ , R ²² , R ²³ , and R ²⁴ may be bonded to form a ring structure. L ²¹ represents a ligand and may be bonded to at least one of R ²¹ , R ²² , R ²³ , and R ²⁴ . X ²¹ represents a counter ion. n ²¹ represents an integer of 0 to 5, n ²² represents an integer of 1 to 6, and n ²³ represents an integer of 0 to 3. C represents a carbene carbon, which binds to two nitrogen atoms and coordinates to M.

  More preferably, the general formula (C2) is a compound represented by the general formula (C3).

In the formula, M represents a transition metal atom or a transition metal ion. R ³¹ , R ³² , and R ³³ represent a hydrogen atom or a substituent, and R ³⁴ represents a substituent. R ³¹ , R ³² , and R ³³ may be bonded to each other to form a ring structure, and may be coordinated to M by an atom on R ³¹ , R ³² , and R ³³ .

If R ³⁴ is plural, plural R ³⁴ may be the same or may be different. The may form a ring structure bonded respectively may be coordinated to M on R ^34. L ³¹ represents a ligand, and X ³¹ represents a counter ion. n ³¹ denotes an integer 0 to ^{4, n 32} represents an integer of 1 to ^{3, n 33} represents an integer of 0 to 2. m ³¹ represents an integer of 0 to 4. C represents a carbene carbon. The carbene carbon is bonded to two nitrogen atoms and is coordinated to M by two electrons on the carbon.
More preferably, the general formula (C3) is a compound represented by the general formula (C4).

In the formula, R ⁴¹ , R ⁴² , and R ⁴³ represent a hydrogen atom or a substituent, and R ⁴⁴ , R ⁴⁵ , and R ⁴⁶ represent a substituent. R ⁴¹ , R ⁴² , and R ⁴³ may be bonded to each other to form a ring structure, and may be coordinated to M by an atom on R ⁴¹ , R ⁴² , and R ⁴³ .

If R ⁴⁴ is plural, the plurality of R ⁴⁴ may be the same or different. The may form a ring structure bonded respectively may be coordinated to M on R ^44. If R ⁴⁵ is plural, the plurality of R ⁴⁵ may be the same or different. The may form a ring structure bonded respectively may be coordinated to M on R ^45. If R ⁴⁶ is plural, plural R ⁴⁶ may be the same or may be different. The may form a ring structure bonded respectively may be coordinated to M on R ^46. n ⁴¹ is an integer of 0 to ^{2, n 42} represents an integer of 1 to 3. ^{m 41,} m ^42, and ^{m 43} represents an integer of 0-4.
Preferably, the ligand containing a carbene carbon is a tridentate to hexadentate ligand.

  More preferably, the general formula (C1) is a compound represented by the general formula (C5).

In the formula, R ⁵² and R ⁵³ represent a hydrogen atom or a substituent, and R ⁵⁴ , R ⁵⁵ , and R ⁵⁶ represent a substituent. R ⁵² and R ⁵³ may be bonded to each other to form a ring structure. When there are a plurality of R ⁵⁴ , R ⁵⁵ , and R ⁵⁶ , a plurality of R ^{54 s} , a plurality of R ^{55 s} , and a plurality of R ⁴⁶ may be bonded to each other to form a ring structure. Y ⁵¹ and Y ⁵² represent a single bond or a linking group. n ⁵¹ represents 0 or 1, and m ⁵¹ , m ⁵² , and m ⁵³ represent an integer of 0 to 4.

  The general formula (C1) will be described.

M represents a transition metal atom or a transition metal ion. R ¹¹ and R ¹² each independently represents a hydrogen atom or a substituent. You may coordinate to M by the atom on both of R <^11> , R < ¹² > or any one. L ¹¹ represents a ligand, and X ¹¹ represents a counter ion. n ¹¹ represents an integer of 0 to ^{5, n 12} represents an integer of 1 to ^{6, n 13} represents an integer of 0 to 3. C represents a carbene carbon. This carbene carbon is bonded to R ¹¹ and R ¹² (preferably a covalent bond), and is coordinated to M by two electrons on the carbon.

  The transition metal atom used in the present invention is not particularly limited, but is preferably ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, or platinum, more preferably palladium, rhenium, rhodium, iridium, or Platinum is more preferable, and palladium, rhodium, iridium, or platinum is more preferable.

Examples of the substituent represented by R ¹¹ and R ¹² include an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably having 2 to 30 carbon atoms, more preferably carbon number) 2 to 20, particularly preferably 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, and 3-pentynyl), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably carbon The number is 2 to 20, particularly preferably 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl.

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, and anthranyl). A substituted or unsubstituted amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino; , Diphenylamino, and ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy And 2-ethylhexyloxy), an aryloxy group (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy, and the like. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy).

An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), aryloxycarbonyl group (preferably carbon 7 to 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl, etc.), an acyloxy group (preferably 2 to 30 carbon atoms, more preferably Having 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoy Oxy, etc.), an acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino. ),

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

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl). An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 carbon atoms). To 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimid Riruchio, 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, iodine atom),

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

R ¹¹ and R ¹² may be bonded to each other to form a ring structure. Moreover, you may coordinate to M by the atom on R < ¹¹ >, R < ¹² >. At least one of R ¹¹ and R ¹² may combine with L ¹¹ to form a chelate ligand. R ¹¹ and R ¹² are preferably an alkoxy group, an aryloxy group, a heteroaryloxy group or a substituted amino group, more preferably an alkoxy group or a substituted amino group.

L ¹¹ represents a ligand. Examples of the ligand include “Photochemistry and Photophysics of Coordination Compounds”, Springer-Verlag H. The ligands described in Yersin's 1987 issue, “Organometallic Chemistry-Fundamentals and Applications”, Akio Yamamoto's 1982 issue, etc. are preferred, preferably halogen ligands (preferably chlorine coordination) , Fluorine ligands), nitrogen-containing heterocyclic ligands (eg bipyridyl, phenanthroline, phenylpyridine, pyrazolylpyridine, benzimidazolylpyridine, phenylpyrazole, picolinic acid or dipicolinic acid), diketone ligands, nitrile ligands A ligand, a CO ligand, an isonitrile ligand, a phosphorus ligand (for example, a phosphine derivative, a phosphite derivative, or a phosphine derivative), a carboxylic acid ligand (for example, an acetic acid ligand) More preferably, a nitrogen-containing heterocyclic ligand (for example, bipyridyl, phenanthroline, phenylpyridine, Pyrazolylpyridine, benzimidazolylpyridine, or phenylpyrazole).

The nitrogen-containing hetero ring in the nitrogen-containing hetero ligand includes pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, pyrrole ring, pyrazole ring, imidazole ring, triazole ring, thiazole ring, oxazole ring, oxadiazole ring , A thiadiazole ring or an azaphosphinine ring is preferred, a pyridine ring, a pyrrole ring, a pyrazole ring or an imidazole ring is more preferred, and a pyridine ring, a pyrazole ring or an imidazole ring is more preferred.
The nitrogen-containing heterocyclic ligand may have a substituent. Examples of the substituent include the groups described in the above R ^11. For example, an alkyl group, an aryl group, an alkoxy group, a fluorine atom, a cyano group, or a substituted amino group is preferable.

X ¹¹ represents a counter ion. The counter ion is not particularly limited, but is preferably an alkali metal ion, alkaline earth metal ion, halogen ion, perchlorate ion, PF ₆ ion, ammonium ion (for example, tetramethylammonium ion, etc.), borate ion, or phosphonium ion. More preferably, it is a perchlorate ion or a PF ₆ ion.

n ¹¹ represents an integer of 0 to 5, preferably 1 to 4, 1 and 2 are more preferred. When n ¹¹ is plural, a plurality of L ¹¹ may be different even in the same. n ¹² represents an integer of 1 to 6, preferably 1 to 4, 1 to 3 is more preferable. When n ¹² is plural, the plural carbene ligands represented by R ¹¹ —C—R ¹² may be the same or different. n ¹³ represents an integer of 0 to 3, 0, 1 are preferred, more preferably 0. When n ¹³ is plural, the plural X ¹¹ may be the same or different.

  General formula (C2) is demonstrated.

M, L ²¹ , X ²¹ , n ²¹ , n ²² , and n ²³ are synonymous with M, L ¹¹ , X ¹¹ , n ¹¹ , n ¹² , and n ^{13 in the} general formula (C1), respectively, and a preferred range Is the same. R ²¹ , R ²² , R ²³ , and R ²⁴ represent a hydrogen atom or a substituent, and examples of the substituent include the groups described for R ¹¹ . R ²¹ , R ²² , R ²³ , and R ²⁴ may be bonded to each other to form a ring structure, and are coordinated to M by an atom on R ²¹ , R ²² , R ²³ , and R ^24. May be. Furthermore, R ²¹ , R ²² , R ²³ , and R ²⁴ may be combined with L ²¹ to form a chelate ligand. R ²¹ , R ²² , R ²³ , and R ²⁴ are preferably an alkyl group, an aryl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkylamino group, an arylamino group, or a heterocyclic amino group, An alkyl group, an aryl group, a heteroaryl group, an alkoxy group, or an aryloxy group is more preferable, and an alkyl group, an aryl group, or a heteroaryl group is further preferable.
The carbene ligand formed from a carbene carbon and two nitrogen atoms, R ²¹ , R ²² , R ²³ , and R ²⁴ is preferably a cyclic structure containing a carbene carbon and two nitrogen atoms. A ring structure is more preferable, and a 5-membered ring structure represented by the general formula (Z-1) is most preferable.

In the formula, R ⁶¹ , R ⁶² , R ⁶³ and R ⁶⁴ represent a hydrogen atom or a substituent. C represents a carbene carbon. This carbene carbon is bonded to two nitrogen atoms and has two electrons that can coordinate to a transition metal on the carbon.

General formula (Z-1) is demonstrated. R ⁶¹ , R ⁶² , R ⁶³ , and R ⁶⁴ are synonymous with R ²¹ , R ²² , R ²³ , and R ^{24 in the} general formula (2), and preferred ranges are also the same.

  General formula (C3) is demonstrated.

M, R ³¹ , R ³² , R ³³ , L ³¹ , and X ³¹ are synonymous with M, R ²¹ , R ²² , R ²³ , L ²¹ , and X ^{21 in the} general formula (2), respectively. Is the same. R ³⁴ represents a substituent, and examples of the substituent include the groups described above for R ¹¹ . The plurality of R ³⁴ may be the same or different. Each may be bonded to form a ring structure, and may be coordinated to M by an atom on R ³⁴ . R ³⁴ is preferably an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, or a substituted amino group, and more preferably an alkyl group, an aryl group, a fluorine atom, or a cyano group. , A fluorine atom, or a cyano group is more preferable. n ³¹ represents an integer of 0 to 4, 1 to 4 are preferred. n ³² represents an integer of 1 to 3, preferably 1 or 2. n ³³ represents an integer of 0 to 2, and 0 or 1 is preferable. m ³¹ represents an integer of 0 to 4, 0 to 2 are preferred. When there are a plurality of m ³¹ , the plurality of R ³⁴ may be the same or different.

  General formula (C4) is demonstrated.

R ⁴¹ , R ⁴² , R ⁴³ , R ⁴⁴ , n ⁴² , and m ⁴¹ are respectively synonymous with R ³¹ , R ³² , R ³³ , R ³⁴ , n ³² , and m ^{31 in the} general formula (3), The preferred range is also the same. R ⁴⁵ and R ⁴⁶ represent a substituent, and examples of the substituent include the groups described in the above R ¹¹ . If m ⁴² is plural, plural R ⁴⁵ may be the same or may be different. The bonded respectively may form a ring structure, it may be coordinated to the iridium atom in the atom on R ^45. R ⁴⁵ is preferably an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, or a substituted amino group, more preferably an alkyl group, an aryl group, an alkoxy group, or a substituted amino group. And an alkoxy group and a substituted amino group are more preferable. m ⁴² represents an integer of 0 to 4, 0 to 2 are preferred. When there are a plurality of m ⁴³ , the plurality of R ⁴⁶ may be the same or different. The bonded respectively may form a ring structure, it may be coordinated to the iridium atom in the atom on R ^46. R ⁴⁶ is preferably an alkyl group, aryl group, heteroaryl group, alkoxy group, fluorine atom, cyano group, or substituted amino group, more preferably an alkyl group, aryl group, fluorine atom, or cyano group. And a fluorine atom and a cyano group are more preferable. m ⁴³ represents an integer of 0 to 4, 0 to 2 are preferred. n ⁴¹ represents an integer of 0 to 2, and 1 or 2 is preferable.

  In the compounds represented by the general formulas (C1) to (C4), the ligand containing a carbene carbon is preferably 3 or more and 6 or less, and more preferably 3 or more and 4 or less. .

  General formula (C5) is demonstrated.

R ⁵² and R ⁵³ represent a hydrogen atom or a substituent. Examples of the substituent include the groups described for R ¹¹ . R ⁵² and R ⁵³ may be bonded to each other to form a ring structure, and may be an alkyl group, an aryl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkylamino group, an arylamino group, or a heterogeneous group. A ring amino group is preferable, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, or an aryloxy group is more preferable, and an alkyl group, an aryl group, or a heteroaryl group is further preferable.
The carbene ligand formed from a carbene carbon and two nitrogen atoms, R ⁵² and R ⁵³ is preferably a cyclic structure containing a carbene carbon and two nitrogen atoms, more preferably a 5-membered ring or a 6-membered ring structure, Most preferably, it is a 5-membered ring structure represented by the general formula (Z-2).

In the formula, R ⁹² and R ⁹³ represent a hydrogen atom or a substituent, and R ⁹⁴ , R ⁹⁵ , and R ⁹⁶ represent a substituent. Y ⁹¹ and Y ⁹² represent a single bond or a linking group. n ⁹¹ represents 0 or ^{1, m 91, m 92,} m 93 represents an integer of 0-4. C represents a carbene carbon. This carbene carbon is bonded to two nitrogen atoms and has two electrons that can coordinate to a transition metal on the carbon.

R ⁵⁴ and R ⁵⁶ represent a substituent, and examples of the substituent include the groups described for R ¹¹ . When there are a plurality of m ⁵¹ and m ⁵³ , the plurality of R ⁵⁴ and R ⁵⁶ may be the same or different, and may be bonded to each other to form a ring structure. R ⁵⁴ and R ⁵⁶ are preferably an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, or a substituted amino group, and more preferably an alkyl group, an aryl group, a fluorine atom, or It is a cyano group, more preferably a fluorine atom or a cyano group. m ⁵¹ and m ⁵³ represent an integer of 0 to 4, and 0 to 2 are preferable.
R ⁵⁵ represents a substituent, and examples of the substituent include the groups described for R ¹¹ . The plurality of R ⁵⁵ may be the same or different. Each may be bonded to form a ring structure. R ⁵⁵ is preferably an alkyl group, aryl group, heteroaryl group, alkoxy group, fluorine atom, cyano group, or substituted amino group, more preferably an alkyl group, aryl group, alkoxy group, or substituted amino group. And an alkoxy group and a substituted amino group are more preferable. m ⁵² represents an integer of 0 to 4, and preferably 0 to 2. Y ⁵¹ and Y ⁵² represent a single bond or a linking group. Although it does not specifically limit as a coupling group, The coupling group which consists of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom is preferable, Although a specific example is shown below, it is not limited to these.

These linking groups may be further substituted, and as the substituent, those exemplified as the substituent represented by R ¹¹ in the general formula (C1) can be applied, and an alkyl group, an aryl group, a heteroaryl group, an alkenyl group can be used. Group, alkoxy group, aryloxy group, alkylamino group, arylamino group, or heterocyclic amino group are preferable, alkyl group, aryl group, heteroaryl group, alkoxy group, or aryloxy group are more preferable, alkyl group, aryl A group or a heteroaryl group is more preferable. Y ⁵¹ and Y ⁵² are preferably a single bond, an alkyl group, an aryl group, or a silyl group, and more preferably a single bond, a dimethylmethylene group, or an ethylene group. n ⁵¹ represents 0 or 1, and 0 is more preferable.

General formula (Z-2) is demonstrated. R ⁹² , R ⁹³ , R ⁹⁴ , R ⁹⁵ , R ⁹⁶ , Y ⁹¹ , Y ⁹² , m ⁹¹ , m ⁹² , m ⁹³ , and n ⁹¹ are R ⁵² , R ⁵³ , R ^{54 in the} general formula (5). , R ⁵⁵ , R ⁵⁶ , Y ⁵¹ , Y ⁵² , m ⁵¹ , m ⁵² , m ⁵³ , and n ⁵¹ , and the preferred range is also the same.

  The compounds represented by the general formulas (C1) to (C5) may be low molecular compounds, and oligomer compounds and polymer compounds (weight average molecular weight (polystyrene conversion) is preferably 1000 to 5000000, more preferably 2000. ˜1000000, more preferably 3000 to 100,000. In the case of a polymer compound, structures represented by the general formulas (C1) to (C5) may be included in the polymer main chain, or may be included in the polymer side chain. In the case of a polymer compound, it may be a homopolymer compound or a copolymer. The compound of the present invention is preferably a low molecular compound.

  Next, examples of the carbene compound used in the present invention are shown, but the present invention is not limited thereto.

  The compounds represented by the general formulas (C1) to (C5) used in the present invention can be synthesized by various methods. For example, it can be obtained by mixing a ligand or a dissociated product thereof with a transition metal compound at room temperature or lower or while heating. In the case of heating, in addition to normal heating, a method of heating with microwaves is also effective. If necessary, a solvent (halogen solvent, alcohol solvent, ether solvent, water, etc.) or a base (may be an inorganic base or an organic base such as sodium methoxide, t-butoxy potassium, Triethylamine, potassium carbonate, etc.) may be used.

  For example, the synthesis of compound (1) can be performed by the following method. The iridium chlorine-bridged complex A-1 can be synthesized by the method described in Reference 1 (J. Am. Chem. Soc. 1984, 106, 6647) and the like. This complex A-1 and an imidazolium salt A-2 which is a precursor of a carbene ligand are complexed using the reaction conditions described in Reference 2 (Inorg. Chem. 2004, 43, 6896) and the like. Thus, compound (1) can be synthesized.

  Synthesis of the compound (113) which is a tetradentate platinum complex can be performed by the following method. The imidazolium salt A-3, which is a precursor of a tetradentate carbene ligand, can be synthesized by the method described in Reference 3 (Tetrahedron, 2004, 60, 5807). Compound (113) is synthesized by complexing this imidazolium salt A-3 with a platinum salt using the reaction conditions described in Reference 4 (Coordination Chemistry Reviews, 2004, 248, 2247) and the like. be able to.

  The carbene compounds used in the present invention are described in Reference 5 (Angew. Chem. Int. Ed. 2002, 41, 1290), Reference 6 (“Metal Complex Chemistry”, Yodogawa Shoten, Hiroshi Sugano, Gengo Matsubayashi and Yoshihisa Yamamoto. , 1990)), and the like.

  The carbene compound-containing layer used in the present invention can be suitably formed by any of dry film forming methods such as vapor deposition and sputtering, transfer methods, printing methods, coating methods, ink jet methods, and spray methods. it can.

4). 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 injecting material and hole transporting material used for these layers may be a low molecular compound or a high molecular compound.
Specifically, pyrrole derivatives, carbazole derivatives, azacarbazole derivatives, indole derivatives, azaindole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styryl Anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, phthalocyanine compounds, porphyrin compounds, thiophene derivatives, organosilane derivatives, carbon, And the like.

  An electron-accepting dopant can be contained in the hole injection layer or the hole transport layer of the organic EL device of the present invention. 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.

  Specifically, examples of the inorganic compound include metal halides such as ferric chloride, aluminum chloride, gallium chloride, indium chloride, and antimony pentachloride, metal oxides such as vanadium pentoxide, and molybdenum trioxide.

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.
In addition, JP-A-6-212153, JP-A-11-111463, JP-A-11-251067, JP-A-2000-196140, JP-A-2000-286054, JP-A-2000-315580, JP-A-2001-102175, JP-A-2001-2001. -160493, JP2002-252085, JP2002-56985, JP2003-157981, JP2003-217862, JP2003-229278, JP2004-342614, JP2005-72012, JP20051666667 The compounds described in JP-A-2005-209643 and the like can be preferably used.

  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%.

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 500 nm, more preferably 0.5 nm to 300 nm, and still more preferably 1 nm to 200 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. .

5). 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 injecting material and the electron transporting material used for these layers may be a low molecular compound or a high molecular compound.
Specifically, pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone Derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene, perylene and other aromatic ring tetracarboxylic acid anhydrides, phthalocyanine derivatives, 8-quinolinol derivative metal complexes, Metal phthalocyanines, various metal complexes represented by metal complexes with benzoxazole and benzothiazole as ligands, organosilane derivatives represented by siloles Body, or the like is preferably a layer containing.

The electron injection layer or the electron transport layer of the organic EL device of the present invention can contain an electron donating dopant. 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 nitrogen-containing compounds, sulfur-containing compounds, and phosphorus-containing compounds.
In addition, materials described in JP-A-6-212153, JP-A-2000-196140, JP-A-2003-68468, JP-A-2003-229278, JP-A-2004-342614, and the like can be used.

These electron donating dopants may be used alone or in combination of two or more.
Although the usage-amount of an electron donating dopant changes with kinds of material, it is preferable that it is 0.1 mass%-99 mass% with respect to electron transport layer material, and it is 1.0 mass%-80 mass%. Is more preferable, and 2.0 mass% to 70 mass% is particularly preferable.

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.

6). 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 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.

7). Substrate 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 thereof 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 substrate structure 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.

8). Electrode (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.

  As a material of the anode, for example, a metal, an alloy, a metal oxide, a conductive compound, or a mixture thereof can be suitably cited, and a material having a work function of 4.0 eV or more is preferable. 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, nickel, and mixtures or laminates of these metals and conductive metal oxides, inorganic conductive materials such as copper iodide and copper sulfide, polyaniline, polythiophene, polypyrrole, etc. Organic conductive materials, 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.

  Note that the transparent anode is described in detail in Yutaka Sawada's “New Development of Transparent Electrode Film” published by CMC (1999), 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, and those having a work function of 4.5 eV or less are preferable. Specific examples include alkali metals (eg, Li, Na, K, Cs, etc.), alkaline earth metals (eg, Mg, Ca, etc.), gold, silver, lead, aluminum, sodium-potassium alloys, lithium-aluminum alloys, magnesium. -Rare earth metals such as silver alloys, indium, ytterbium, and the like. 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.

9. Protective layer In the present invention, the entire organic EL device 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 O. ₃ , metal oxides such as Y ₂ O ₃ , TiO ₂ , metal nitrides such as SiN _x , SiN _x O _y , metal fluorides such as MgF ₂ , LiF, AlF ₃ , CaF ₂ , polyethylene, polypropylene, polymethyl Monomer mixture containing methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and at least one comonomer Copolymer obtained by copolymerization, cyclic in the copolymer main chain Examples thereof include a fluorine-containing copolymer having a structure, 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. 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, transfer method can be applied.

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

11. Driving 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. Can be obtained.
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.

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

  Examples of the organic EL device of the present invention will be described below, but the present invention is not limited to these examples.

(Measurement of Ip value, Ea value, Eg value)
First, measurement methods and measurement results of the Ip value, Ea value, and Eg value of the luminescent material and host material used in the examples will be described.
Measurement method of Ip value: A sample thin film deposited on a glass substrate with a thickness of 100 nm was prepared on a glass substrate by a vacuum deposition method. The Ip value of the obtained thin film was measured at an amount of light of 20 nW using an atmospheric photoelectron spectrometer AC-2 (manufactured by Riken Keiki Co., Ltd.).
Calculation method of Ea value: A sample thin film having a thickness of 100 nm of each measurement material deposited on a quartz substrate by vacuum deposition was prepared, and a spectrophotometer U3310 (manufactured by Hitachi, Ltd.) was used for spectroscopy from 180 nm to 700 nm. Absorption spectrum was measured. The energy gap value (Eg (eV)) was calculated from the absorption edge on the longest wavelength side. From the obtained Eg value and Ip value, the Ea value was calculated by the following formula (1).
Ea (eV) = Ip (eV) −Eg (eV) Formula (1)

  The structures of the compounds used in the examples are shown below.

Example 1
1. Production of organic EL element (production of comparative organic EL element 1A)
A glass substrate (manufactured by Geomatic Co., Ltd., surface resistance 10Ω / □) on which 0.5 mm thick and 2.5 cm square indium tin oxide (denoted as ITO) is vapor-deposited is placed in a cleaning container and ultrasonically cleaned in 2-propanol. Then, UV-ozone treatment was performed for 30 minutes. The following layers were deposited on this transparent anode by vacuum deposition. The vapor deposition rate in the examples of the present invention is 0.2 nm / second unless otherwise specified. The deposition rate was measured using a quartz resonator. The film thicknesses described below were also measured using a crystal resonator.

Hole injection layer: 4,4 ′, 4 ″ -tris (2-naphthylphenylamino) triphenylamine (abbreviated as 2-TNATA) and 2,3,5,6-tetrafluoro-7,7,8, 8-tetracyanoquinodimethane (abbreviated as F4-TCNQ) was co-deposited so that F4-TCNQ was 1.0 mass% with respect to 2-TNATA, and the thickness was 160 nm.
Hole transport layer: N, N′-dinaphthyl-N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviated as α-NPD), thickness 10 nm.

  Light emitting layer: 1,3-bis (carbazol-9-yl) benzene (abbreviated as mCP) and an electron transporting light emitting material Pt-1 were co-evaporated. The mixing ratio of Pt-1 with respect to mCP was adjusted to be 13% by mass uniformly throughout the light emitting layer. The thickness of the light emitting layer was 60 nm. Since the Ea value of Pt-1 is 3.0 eV and the Ea value of mCP is 2.5 eV, the electron transporting material in this light emitting layer is Pt-1.

Subsequently, the following electron transport layer and electron injection layer were provided on the light emitting layer.
Electron transport layer: bis- (2-methyl-8-quinolate) -4-phenyl-phenolium aluminum (abbreviated as BAlq), thickness 40 nm.
Electron injection layer: LiF, thickness 1 nm.

Furthermore, patterning was performed using a shadow mask to provide Al having a thickness of 100 nm as a cathode.
Each layer was provided by resistance heating vacuum deposition.

  The produced laminate was put in a glove box substituted with nitrogen gas, and sealed using a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by CHI Nagase).

(Production of Comparative Organic EL Element 1B)
In the comparative organic EL element 1A, the light emitting layer was changed to the following light emitting layer, and the others were similarly fabricated to produce a comparative organic EL element 1B.

  Light emitting layer: mCP and electron transporting light emitting material Pt-1 were co-evaporated, and the co-evaporation ratio was changed with the progress of vapor deposition. The deposition rate of each component was adjusted so that the mixing ratio of Pt-1 was 0% by mass at the anode-side interface at the initial stage of vapor deposition, and the mixing ratio of Pt-1 was 26% by mass at the cathode-side interface at the end of deposition. The mixing ratio of each component was continuously changed between these interfaces. The thickness of the light emitting layer was 60 nm. The concentration of each material in the region near the anode side interface is 1.3% by mass for Pt-1 and 98.7% by mass for mCP, and 24.7% by mass for Pt-1 in the region near the cathode side interface. , MCP was 75.3 mass%.

(Production of Comparative Organic EL Element 1C)
In the comparative organic EL device 1A, the light emitting layer was further changed to the following using a layer containing the following carbene compound (1) instead of the hole transport layer. Other than that, a comparative organic EL element 1C was produced in the same manner as the comparative organic EL element 1A.

Carbene compound-containing layer: A 10-nm thick layer of carbene compound (1) was provided by vapor deposition.
Light emitting layer: mCP and Pt-1 were co-evaporated. The mixing ratio of Pt-1 with respect to mCP was adjusted to be 13% by mass uniformly throughout the light emitting layer. The film thickness of the light emitting layer was 60 nm.

(Production of comparative organic EL element 1D)
In the comparative organic EL element 1C, as the carbene compound-containing layer, the carbene compound (2) is used in place of the carbene compound (1), and the others are the same as the comparative organic EL element 1C. Produced.

(Production of Comparative Organic EL Element 1E)
In the comparative organic EL element 1C, as the carbene compound-containing layer, the carbene compound (3) is used instead of the carbene compound (1), and the others are the same as in the comparative organic EL element 1C. Produced.

(Preparation of the organic EL device 1 of the present invention)
In the comparative organic EL device 1A, the light emitting layer was further changed to the following using a layer containing the following carbene compound (1) instead of the hole transport layer. Otherwise, the organic EL element 1 of the present invention was produced in the same manner as the comparative organic EL element 1A.

Carbene compound-containing layer: A 10-nm thick layer of carbene compound (1) was provided by vapor deposition.
Light-emitting layer: mCP and electron-transporting light-emitting material Pt-1 were co-evaporated, and the co-evaporation ratio was changed as the deposition progressed. The deposition rate of each component was adjusted so that the mixing ratio of Pt-1 was 0% by mass at the anode-side interface at the initial stage of vapor deposition, and the mixing ratio of Pt-1 was 26% by mass at the cathode-side interface at the end of deposition. The mixing ratio of each component was continuously changed between these interfaces. The film thickness of the light emitting layer was 60 nm. The concentration of each material in the region near the anode side interface is 1.3% by mass for Pt-1 and 98.7% by mass for mCP, and 24.7% by mass for Pt-1 in the region near the cathode side interface. , MCP was 75.3% by mass.

(Preparation of the organic EL element 2 of the present invention)
In the organic EL device 1 of the present invention, the carbene compound-containing layer uses the carbene compound (2) instead of the carbene compound (1), and the others are the same as the organic EL device 1 of the present invention, and the organic EL of the present invention. Element 2 was produced.

(Preparation of the organic EL device 3 of the present invention)
In the organic EL device 1 of the present invention, as the carbene compound-containing layer, the carbene compound (3) is used instead of the carbene compound (1), and the others are the same as the organic EL device 1 of the present invention, and the organic EL of the present invention. Element 3 was produced.

2. Performance Evaluation Results External quantum efficiency and driving durability of the obtained comparative organic EL device and the organic EL device of the present invention were measured under the same conditions by the following means.

<Drive voltage>
A DC voltage reaching a luminance of 360 cd / m ² was used as a driving voltage.

<Method for measuring external quantum efficiency>
The produced light emitting element was made to emit light by applying a DC voltage to the light emitting element using a source measure unit 2400 type manufactured by KEITHLEY. All the elements showed blue light emission. The voltage is adjusted to emit light so that the luminance is 360 cd / m ² , the emission spectrum and the amount of light are measured using a luminance meter SR-3 manufactured by Topcon Corporation, and the external quantum is calculated from the emission spectrum, the amount of light, and the current at the time of measurement. Efficiency was calculated.

<< Measurement method of driving durability ratio >>
A direct current voltage was applied to each element so as to have a luminance of 360 cd / m ^2, and the device was continuously driven to measure the luminance half time until the luminance reached 180 cd / m ² . The relative luminance half time when the luminance half time of the comparative element 1A was set to 1 was used as an index of driving durability.

The obtained results are shown in Table 1.
With respect to the comparative devices 1C, 1D, and 1E, each of the devices 1, 2, and 3 of the present invention in which the concentration of the electron-transporting light-emitting material Pt-1 in the light-emitting layer is inclined has a reduced driving voltage. The external quantum efficiency was increased and the luminance half-life time was significantly increased.
On the other hand, the devices 1, 2 and 3 of the present invention containing a carbene compound with respect to the comparative device 1A or 1B containing no carbene compound showed low driving voltage and high external light emission efficiency.
As described above, the organic EL element of the present invention was superior in driving voltage reduction, external quantum efficiency improvement, and driving durability compared to the comparative element.

Example 2
1. Production of organic EL element (production of comparative organic EL element 2A)
In the comparative organic EL element 1A of Example 1, the light emitting layer was changed to the following, and the others were produced in the same manner as the comparative organic EL element 1A, to produce a comparative organic EL element 2A.

Light-emitting layer: 4,4′-di- (N-carbazole) -biphenyl (abbreviated as CBP) as a hole-transporting host material, ETH-1 as an electron-transporting host material, and fac- as a hole-transporting light-emitting material Tris (2-phenylpyridinate-N, C2 ′) iridium (III) (abbreviated as Ir (ppy) ₃ ) was co-deposited in three ways. The mixing ratio of ETH-1 was adjusted to be 20% by mass uniformly throughout the light emitting layer. Further, the mixing ratio of Ir (ppy) ₃ was adjusted to be 6% by mass uniformly throughout the light emitting layer. The thickness of the light emitting layer was 30 nm. Since the Ea value of CBP is 2.8 eV, the Ea value of ETH-1 is 3.2 eV, and the Ea value of Ir (ppy) 3 is 2.8 eV, the electron transporting material in this light emitting layer is ETH-1.

(Production of Comparative Organic EL Element 2B)
In the comparative organic EL element 2A, the light emitting layer was changed to the following, and the others were produced in the same manner as in the comparative organic EL element 2A.

Luminescent layer: CBP, ETH-1 and Ir (ppy) ₃ were co-deposited in three elements, and the co-evaporation ratio was changed as the deposition progressed. The deposition rate was adjusted so that the mixing ratio of ETH-1 was 0% by mass at the anode side interface at the initial stage of vapor deposition, and the mixing ratio of ETH-1 was 40% by mass at the cathode side interface at the end of vapor deposition. Further, the mixing ratio of Ir (ppy) ₃ is 12% by mass at the anode side interface at the initial stage of vapor deposition, and the mixing ratio of Ir (ppy) ₃ is 0% by mass in the cathode side interface region at the end of the vapor deposition. The deposition rate was adjusted. The mixing ratio of each component was continuously changed between these interfaces. The thickness of the light emitting layer was 30 nm. The concentration of each material in the region near the anode side interface is 11.4% by mass for Ir (ppy) _3, 2.0% by mass for ETH-1, and 86.6% by mass for CBP. In the region, Ir (ppy) ₃ was 0.6 mass%, ETH-1 was 38.0 mass%, and CBP was 61.4 mass%.

(Production of Comparative Organic EL Element 2C)
In the comparative organic EL element 2A, a layer containing the following carbene compound (1) was used instead of the hole transport layer, and the light emitting layer was further changed to the following. Other than that, a comparative organic EL element 2C was fabricated in the same manner as the comparative organic EL element 2A.

Carbene compound-containing layer: A 10-nm thick layer of carbene compound (1) was provided by vapor deposition.
Light-emitting layer: CBP, ETH-1, and Ir (ppy) ₃ were co-deposited in three elements. The mixing ratio of ETH-1 was adjusted to be 20% by mass uniformly throughout the light emitting layer. Further, the mixing ratio of Ir (ppy) ₃ was adjusted to be 6% by mass uniformly throughout the light emitting layer. The thickness of the light emitting layer was 30 nm.

(Production of comparative organic EL element 2D)
In the comparative organic EL element 2C, as the carbene compound-containing layer, the carbene compound (2) is used instead of the carbene compound (1), and the others are the same as the comparative organic EL element 2C. Produced.

(Production of comparative organic EL element 2E)
In the comparative organic EL element 2C, as the carbene compound-containing layer, the carbene compound (3) is used instead of the carbene compound (1), and the others are the same as in the comparative organic EL element 2C. Produced.

(Preparation of the organic EL element 11 of the present invention)
In the comparative organic EL element 2A, a layer containing the following carbene compound (1) was used instead of the hole transport layer, and the light emitting layer was further changed to the following. Otherwise, the organic EL element 11 of the present invention was produced in the same manner as the comparative organic EL element 2A.

Carbene compound-containing layer: A 10-nm thick layer of carbene compound (1) was provided by vapor deposition.
Luminescent layer: CBP, ETH-1 and Ir (ppy) ₃ were co-deposited in three elements, and the co-evaporation ratio was changed as the deposition progressed. The deposition rate was adjusted so that the mixing ratio of ETH-1 was 0% by mass at the anode-side interface at the initial stage of vapor deposition, and the mixing ratio of ETH-1 was 40% by mass in the cathode-side interface region at the end of vapor deposition. The mixing ratio of 12 wt% of Ir (ppy) ₃ at a deposition initial anode side interface, the deposition of the respective components as the mixing ratio of Ir (ppy) ₃ is 0 mass% in the cathode side interface of the deposition termination step The speed was adjusted. The mixing ratio of each component was continuously changed between these interfaces. The thickness of the light emitting layer was 30 nm. The concentration of each material in the region near the anode side interface is 11.4% by mass for Ir (ppy) _3, 2.0% by mass for ETH-1, and 86.6% by mass for CBP. In the region, Ir (ppy) ₃ was 0.6 mass%, ETH-1 was 38.0 mass%, and CBP was 61.4 mass%.

(Preparation of the organic EL device 12 of the present invention)
In the organic EL device 11 of the present invention, as the carbene compound-containing layer, the carbene compound (2) is used instead of the carbene compound (1), and the others are the same as the organic EL device 11 of the present invention, and the organic EL of the present invention. Element 12 was produced.

(Preparation of the organic EL device 13 of the present invention)
In the organic EL device 11 of the present invention, as the carbene compound-containing layer, the carbene compound (3) is used instead of the carbene compound (1), and the others are the same as the organic EL device 11 of the present invention, and the organic EL of the present invention. Element 3 was produced.

2. Performance Evaluation All of the devices emitted green light. The obtained device was evaluated in the same manner as in Example 1. However, the driving voltage was a DC voltage with a luminance of 2000 cd / m ² , and the external quantum efficiency was measured and the initial luminance of the luminance half time was also evaluated at a luminance of 2000 cd / m ² . The driving durability was determined by using the relative luminance half time when the luminance half time of the comparative organic EL element 2A was 1, as an index.
The obtained results are shown in Table 2.
In the devices 11, 12 and 13 of the present invention in which the concentration of the electron transporting material ETH-1 in the light emitting layer is inclined with respect to the comparative devices 2C, 2D and 2E, respectively, the driving voltage is reduced, The quantum efficiency is increased, and the luminance half time is significantly increased.
On the other hand, the devices 11, 12 and 13 of the present invention containing a carbene compound with respect to the comparative device 2A or 2B containing no carbene compound showed a low driving voltage and a high external light emission efficiency.
As described above, the organic EL element of the present invention was superior in driving voltage reduction, external quantum efficiency improvement, and driving durability compared to the comparative element.

Claims (9)

  An organic electroluminescent element having at least one organic layer including a light emitting layer between a pair of electrodes, the organic electroluminescent element having a layer containing a carbene compound between the light emitting layer and the anode, wherein the light emitting layer is at least one kind An electron transporting material and at least one hole transporting material, wherein at least one of the electron transporting material and the hole transporting material is a light emitting material, and the concentration of the electron transporting material in the light emitting layer is An organic electroluminescence device characterized by decreasing from the cathode side toward the anode side.   The organic electroluminescent element according to claim 1, wherein the electron transporting material is a light emitting material.   The organic electroluminescent element according to claim 1, wherein the hole transporting material is a light emitting material.   The organic electroluminescent element according to any one of claims 1 to 3, wherein the layer containing the carbene compound is in contact with the light emitting layer.   The concentration of the electron transporting material in a region near the anode side interface of the light emitting layer is 0% or more and 50% or less with respect to the concentration of the electron transporting material in a region near the cathode side interface of the light emitting layer. The organic electroluminescent element according to claim 1, wherein the organic electroluminescent element is provided. The density | concentration of the said electron transport material in the said light emitting layer is 0% or more and 30% or less in the area | region near the said anode side interface, The any one of Claims 1-5 characterized by the above-mentioned. Organic electroluminescent device. The organic luminescence device according to any one of claims 1 to 6, wherein the carbene compound is a compound represented by the following general formula (C1):

(In the formula, M represents a transition metal atom or a transition metal ion. R ¹¹ and R ¹² represent a hydrogen atom or a substituent, and R ¹¹ and R ¹² may be independently bonded to M. R ¹¹ , R ¹² may be bonded to each other to form a ring structure, L ¹¹ represents a ligand and may be bonded to at least one of R ¹¹ and R ^12. X ¹¹ represents a counter ion. n ¹¹ represents an integer of 0 to 5, n ¹² represents an integer of 1 to 6, and n ¹³ represents an integer of 0 to 3. C represents a carbene carbon, and the carbene carbon is represented by R ¹¹ and R ¹² . Bind and coordinate to M.). The organic electroluminescent device according to claim 7, wherein the carbene compound represented by the general formula (C1) is a compound represented by the following general formula (C2):

(In the formula, M represents a transition metal atom or a transition metal ion. R ²¹ , R ²² , R ²³ , and R ²⁴ represent a hydrogen atom or a substituent, and R ²¹ , R ²² , R ²³ , and R ²⁴⁾ May be independently bonded to M. R ²¹ , R ²² , R ²³ , and R ²⁴ may be bonded to each other to form a ring structure, L ²¹ represents a ligand, R ²¹ , It may be bonded to at least one of R ²² , R ²³ , and R ^24. X ²¹ represents a counter ion, n ²¹ represents an integer of 0 to 5, n ²² represents an integer of 1 to 6, and n ²³ represents an integer of 0 to 3. C represents a carbene carbon, which binds to two nitrogen atoms and coordinates to M). The organic light-emitting device according to claim 1, wherein the light-emitting layer contains a phosphorescent material.