JP4903416B2 - Organic electroluminescence device - Google Patents

Description

  The present invention relates to an organic electroluminescent element (hereinafter also referred to as “organic EL element”, “light emitting element”, or “EL element”) that can emit light by converting electric energy into light.

Today, research and development on various display elements are active. Among them, organic electroluminescence (EL) elements are attracting attention as promising display elements because they can emit light with high luminance at a low voltage. In this organic EL element, improvement in luminous efficiency, reduction in power consumption, and improvement in driving durability are problems.
As a technique for improving the light emission efficiency, an octaethylporphine platinum complex having a cyclic tetradentate ligand (for example, see Patent Document 1) or a platinum complex having a bipyridine or phenanthroline-based chain tetradentate ligand (for example, , See Patent Document 2). However, the elements disclosed in these patents are not satisfactory in terms of durability, and further improvements have been demanded.
In addition, it is disclosed that a plurality of compounds are used as a host material of the light emitting layer to reduce power consumption and improve driving durability (see, for example, Patent Documents 3 and 4). These conventional techniques show that the carriers injected into the light emitting layer are trapped by the light emitting dopant and recombined to emit light, thereby obtaining high light emission efficiency.
However, in this method, since the luminescent dopant traps carriers, deterioration of the luminescent dopant due to carriers is unavoidable, and it is difficult to obtain sufficient driving durability.
Furthermore, although a drive voltage reduction is required from the viewpoint of power consumption, the conventional technique cannot achieve a sufficient voltage drop, and an improvement is desired.
US Pat. No. 6,303,238 B1 US Pat. No. 6,653,564B1 JP 2002-313583 A JP 2002-324673 A

  An object of the present invention is to provide an organic electroluminescent device which can be driven at a low voltage and has excellent light emission characteristics and driving durability.

In light of the above circumstances, the present inventors have conducted extensive research and found that the light emitting layer contains a metal complex having a tridentate or higher ligand and a plurality of host compounds, which is a low voltage which is the above problem. It has been found that driving is possible, and that light emission efficiency and driving durability can be improved. The inventors have found that this effect is more markedly manifested by setting the energy level such as the electron affinity and ionization potential of the host material and the luminescent dopant in the luminescent layer within a certain range, thereby completing the present invention.
That is, the present invention is achieved by the following means.

<1> An organic electroluminescence device having an organic compound layer including at least one light emitting layer between a pair of electrodes, wherein the light emitting layer has at least one kind of tridentate or more metal complex and a plurality of metal complexes. An organic electroluminescent device comprising: a host compound.

<2> The organic electroluminescent element as described in <1> above, wherein the metal complex is a phosphorescent compound.

<3> The organic electroluminescent element as described in <1> or <2> above, wherein the ligand of the metal complex is a chain ligand.

<4> The organic electroluminescent element according to any one of <1> to <3>, wherein the metal complex is represented by the following general formula (I).

In the general formula ^{(I), M 11} represents a metal ^ion, L 11 ^{~L 15} represents a ligand coordinated to ^{M 11,} respectively. There is no further group of atoms between L ^{11 and} L ¹⁴ to form a cyclic ligand. L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand. Y ¹¹ , Y ¹² and Y ¹³ each represent a linking group, a single bond or a double bond. When Y ¹¹ , Y ¹² , or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and L ¹³ , L ¹³ and Y ¹³ , Y ¹³ And the bond between L ¹⁴ each independently represents a single bond or a double bond. n ¹¹ represents the 0-4.

<5> The organic electroluminescent element according to any one of <1> to <3>, wherein the metal complex is represented by the following general formula (II).

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

<6> The organic electroluminescent element as described in <1> or <2> above, wherein the ligand of the metal complex is a cyclic ligand.

<7> The organic electroluminescent element as described in <6> above, wherein the metal complex is represented by the following general formula (III).

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

<8> When the ionization potential of the metal complex is Ip (D) and the minimum ionization potential of the plurality of host compounds is Ip (H) min, ΔIp = Ip (D) −Ip (H The organic electroluminescent element according to any one of <1> to <7>, wherein ΔIp defined by min satisfies a relationship of ΔIp> 0 eV.

<9> When the electron affinity of the metal complex is Ea (D) and the maximum electron affinity of the plurality of host compounds is Ea (H) max, ΔEa = Ea (H) max−Ea (D The organic electroluminescent element according to any one of <1> to <8>, wherein ΔEa defined by (1) satisfies a relationship of ΔEa> 0 eV.

<10> The organic electroluminescent element according to any one of <1> to <9>, wherein ΔIp satisfies a relationship of 1.2 eV> ΔIp ≧ 0.2 eV.

<11> The organic electroluminescent element according to any one of <1> to <10>, wherein the ΔEa satisfies a relationship of 1.2 eV> ΔEa> 0.2 eV.

<12> The organic electroluminescence device according to any one of <1> to <11>, wherein the Ip (H) min is 5.1 eV or more.

<13> The organic electroluminescent element according to any one of <1> to <12>, wherein Ea (H) max is 3.0 eV or less.

<14> When the fluorescent phosphorescence spectrum is measured with a single layer film in which only the plurality of host compounds are formed, no luminescence that is not attributed to each single emission spectrum of the plurality of host compounds is observed. The organic electroluminescent element as described in any one of <1>-<13>.

<15> The organic electroluminescent element according to any one of <1> to <14>, wherein the organic compound layer has a carrier transport layer adjacent to the light emitting layer.

<16> The carrier transport layer is an electron transport layer, and the electron affinity Ea (ETL) of the electron transport layer is larger than the electron affinity Ea (D) of the dopant contained in the light emitting layer. The organic electroluminescent element as described in <15>.

<17> The above <16>, wherein carrier mobility of the electron transport layer and the light emitting layer satisfies a relationship of (carrier mobility in the electron transport layer)> (carrier mobility in the light emitting layer) The organic electroluminescent element of description.

<18> The carrier transport layer is a hole transport layer, and the ionization potential Ip (HTL) of the hole transport layer is smaller than the ionization potential Ip (D) of the dopant contained in the light emitting layer. The organic electroluminescent element as described in <15> above.

<19> The carrier mobility between the hole transport layer and the light emitting layer satisfies a relationship of (carrier mobility in the hole transport layer)> (carrier mobility in the light emitting layer). The organic electroluminescent element as described in <18>.

<20> Among the lowest excited triplet energies of a plurality of host compounds, the minimum one is T ₁
When (H) min, the minimum triplet excitation energy T ₁ (D) of the dopant,
The organic electroluminescent element according to any one of <1> to <19>, wherein the relationship of T ₁ (H) min> T ₁ (D) is satisfied.

<21> Any one of the above <1> to <20>, wherein the content of the plurality of host compounds is 15% by mass or more and 85% by mass or less with respect to the total compound mass forming the light emitting layer. The organic electroluminescent element according to one item.

  According to the present invention, it is possible to provide an organic electroluminescence device that can emit light with high brightness and high efficiency, can be driven at a low voltage, and has excellent driving durability.

[Organic electroluminescence device]
The organic electroluminescent device of the present invention is an organic electroluminescent device having an organic compound layer including at least one light emitting layer between a pair of electrodes, and at least one tridentate or higher ligand in the light emitting layer. And a plurality of host compounds.
The organic electroluminescent element of the present invention can be an element excellent in reduction of driving voltage, excellent light emission characteristics, and driving durability by adopting the above configuration.

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

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

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

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

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

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

  First, the compound represented by formula (I) will be described.

In the general formula ^{(I), M 11} represents a metal ^ion, L 11 ^{~L 15} represents a ligand coordinated to ^{M 11,} respectively. There is no further atomic group between L ¹¹ and L ¹⁴ to form a cyclic ligand. L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand. Y ¹¹ , Y ¹² and Y ¹³ each represent a linking group, a single bond or a double bond. When Y ¹¹ , Y ¹² , or Y ¹³ is a linking group, L ¹¹ and Y ¹² , Y ¹² and L ¹² , L ¹² and Y ¹¹ , Y ¹¹ and L ¹³ , L ¹³ and Y ¹³ , Y ¹³ And the bond between L ¹⁴ each independently represents a single bond or a double bond. n ¹¹ represents the 0-4. The bond between M ¹¹ and L ^{11 to} L ¹⁵ may be any of a coordination bond, an ionic bond, and a covalent bond.

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

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

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

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

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

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ with an oxygen atom are not particularly limited, but are independently an alkoxy ligand (preferably having 1 to 30 carbon atoms, more preferably having carbon atoms). 1 to 20, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy), aryloxy ligands (preferably 6 to 30 carbon atoms, more preferably Has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like, and a heterocyclic oxy ligand (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, Noryloxy, etc.), acyloxy ligands (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy and the like. ), A silyloxy ligand (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy and triphenylsilyloxy). , Carbonyl ligands (eg, ketone ligands, ester ligands, amide ligands, etc.), ether ligands (eg, dialkyl ether ligands, diaryl ether ligands, furyl ligands, etc.) Can be mentioned.

Although it does not specifically limit as L < ¹¹ >, L < ¹² >, L <^13> , and L < ¹⁴ > coordinated to M < ¹¹ > by a sulfur atom, Each is independently alkylthio ligand (preferably C1-C30, More preferably, carbon number. 1 to 20, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio, etc.), an arylthio ligand (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably Has 6 to 12 carbon atoms, for example, phenylthio and the like, and a heterocyclic thio ligand (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). And, 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 includes a dialkylphosphino group, a diarylphosphino group, a trialkylphosphine, a triarylphosphine, And phosphinine group. These groups may be further substituted.

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

In the general formula (I), L ¹⁵ represents a ligand coordinated to M ¹¹ . L ¹⁵ is preferably a 1-4-dentate ligand, 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. The linking group is not particularly limited. For example, carbonyl linking group, thiocarbonyl linking group, alkylene group, alkenylene group, arylene group, heteroarylene group, oxygen atom linking group, nitrogen atom linking group, silicon atom linking group, sulfur Examples thereof include an atomic linking group or a linking group composed of a combination thereof. 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.
Specific examples of such a linking group include the following.

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

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

In the general formula ^{(I), n 11} represents 0 to 4. If M ¹¹ is a metal coordination number ^{4, n 11} is ^0, when ^{M 11} is a metal coordination number ^{6, n 11} is 1, 2 is preferable, and more preferably 1. When M ¹¹ is coordination number 6 and n ¹¹ is 1, L ¹⁵ represents a bidentate ligand, and when M ¹¹ is coordination number 6 and n ¹¹ is 2, L ¹⁵ represents a monodentate ligand. When M ¹¹ is a metal having a coordination number of 8, n ¹¹ is preferably 1 to 4, more preferably 1, 2, and more preferably 1. When M ¹¹ is coordination number 8 and n ¹¹ is 1, L ¹⁵ represents a tetradentate ligand, and when M ¹¹ is coordination number 8 and n ¹¹ is 2, L ¹⁵ represents a bidentate ligand. When n ¹¹ is plural, a plurality of L ¹⁵ may be different even in the same.
Preferred forms of the compound represented by the general formula (I) are the compounds represented by the following general formula (1), general formula (2), general formula (3), and general formula (4). is there.

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

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

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

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

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

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

Y ²² and Y ²³ each independently represent a single bond or a linking group, and preferably a single bond. The linking group is not particularly limited. For example, a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, a silicon linking group, and these And a linking group comprising a combination of the above.

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 a tautomer of a pyrrole derivative or a tautomer of an imidazole derivative (for example, a hetero 5-membered ring of the following exemplified compound (29) Ligands, etc.), tautomers of thiazole derivatives (eg, hetero 5-membered ring ligands of the following exemplified compound (30)), tautomers of oxazole derivatives (eg, heterocycles of the exemplified compound (31) below) 5-membered ring ligands etc.) are preferred, tautomers of pyrrole derivatives, tautomers of imidazole derivatives, and tautomers of thiazole derivatives are more preferred, tautomers of pyrrole derivatives, and tautomers of imidazole derivatives. Mutants are more preferred, and tautomers of pyrrole derivatives are particularly preferred.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

n ⁶¹ has the same meaning as ^{n 11} in the general formula (I), and their preferable ranges are also the same.

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

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

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

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

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

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

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

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

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

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

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

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

Y ^B1 represents a linking group and is the same as Y ²¹ in 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.

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

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

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

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

L ⁸⁵ represents a ligand coordinated to M ⁸¹ . L ⁸⁵ is preferably 1 to 3 bidentate ligand, and more preferably anionic ligands 1-3 seat. The tridentate anionic ligand is not particularly limited, but a tridentate ligand formed by a halogen ligand, L ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² , L ⁸³ is preferable, and L ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² and L ⁸³ are more preferable. Never L ⁸⁵ is connected to the ^{L 81, L 83} without passing through the metal. The number of coordination sites and the number of ligands do not exceed the coordination number of the metal.

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

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

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

Q ⁹¹ and Q ⁹² represent a group forming a nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ⁹¹ ). The nitrogen-containing heterocycle formed by Q ⁹¹ and Q ⁹² is not particularly limited. For example, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, thiazole ring, oxazole ring, pyrrole ring, pyrazole ring, imidazole 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 as ^{L 85} in Formula (5), and their preferable ranges are also the same. n ⁹¹ has the same meaning as ^{n 81} in Formula (5), and their preferable ranges are also the same.

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

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

Q ¹⁰² 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 (5-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, and condensed rings containing these (e.g., naphthalene ring), more preferably a benzene ring and a benzene ring Are more preferable, and a benzene ring is particularly preferable.

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

L ¹⁰⁵ has the same meaning as ^{L 85} in Formula (5), and their preferable ranges are also the same. n ¹⁰¹ has the same meaning as ^{n 81} in Formula (5), and their preferable ranges are also the same. X ¹⁰¹ has the same meaning as X ²¹ in formula (1), and the preferred range is also the same.

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

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

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

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

Examples of those coordinated with M ^X1 by a nitrogen atom include nitrogen-containing heterocyclic groups (pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, triazole, etc.), amino groups (alkylamino) A group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as methylamino), an arylamino group (such as phenylamino), and the like. An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, especially Preferably it is C2-C12, for example, methoxycarbonylamino etc. are mentioned), an aryloxycarbonylamino group (Preferably C7-30, More preferably C7-20, Especially preferably C7 -12, for example, phenyloxycarbonylamino, etc.), sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, And methanesulfonylamino, benzenesulfonylamino, etc.) and imino groups. These groups may be further substituted.

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

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

As the one coordinated to M ^X1 with a sulfur atom, an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.) An arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenylthio), a heterocyclic thio group ( Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio. ), A thiocarbonyl group (for example, a thioketone group, a thioester group, etc.), a thioether group (for example, a dialkyl group). Luthioether group, diarylthioether group, thiofuryl group, etc.).

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

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

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

These linking groups may be further substituted, and as the substituent, those exemplified as the substituents represented by R ^{21 to} R ²⁴ in the general formula (1) can be applied, and the preferred ranges are also the same. L ^{X11 to} L ^X14 are preferably a single bond, a dimethylmethylene group, or a dimethylsilylene group.

Of the compounds represented by the general formula (II), more preferred are compounds represented by the following general formula (X2), and still more preferred are compounds represented by the following general formula (X3).
First, the compound represented by general formula (X2) is demonstrated.

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

The compound represented by formula (X2) will be described in detail.
In general formula (X2), M ^X2 has the same meaning as M ^X1 in general formula (II), and the preferred range is also the same. Y ^X21 to Y ^X26 represent an atom coordinating to ^{M X2.} The bond between Y ^{X21 to} Y ^X26 and M ^X2 may be 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, furan ring, preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyrazole ring, imidazole ring, triazole ring, more preferably benzene. A ring, a pyridine ring, a pyrazine ring, a pyrazole ring and a triazole ring, and particularly preferably a benzene ring and a pyridine ring. These may further have a condensed ring or a substituent.

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

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

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

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

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

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

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

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

The metal complex of the present invention is appropriately selected from the ligands that form the partial structure of the target complex, whereby the general formulas (I), (1), (1-A), (2), (3), (3-A), (3-B), (3-C), (4), (4-A), (5), (5-A), and (5-B), and The general formulas (II), (X2), and (X3) can be synthesized.
For example, when synthesizing the compound represented by the general formula (1-A), 6,6′-bis (2-hydroxyphenyl) -2,2′-bipyridyl ligand or a derivative thereof (for example, 2, 9-
Bis (2-hydroxyphenyl) -1,10-phenanthroline ligand, 2,9-bis (2-hydroxyphenyl) -4,7-diphenyl-1,10-phenanthroline ligand, 6,6′-bis (2-hydroxy-5-tert-butylphenyl) -2,2′-bipyridyl ligand, etc.) is preferably 0.1 equivalent to 10 equivalents, more preferably 0.3 equivalents to the metal compound. It can be synthesized by adding 6 equivalents, more preferably 0.5 to 4 equivalents. In the method for synthesizing the compound represented by the general formula (1-A), each of the reaction solvent, the reaction time, and the reaction temperature is the same as that described in the method for synthesizing the metal complex of the present invention.

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

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

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

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

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

  An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl and the like), amino. Group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc. An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc. An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy, and the like, and heterocyclic oxy groups (preferably having 1 to 30 carbon atoms, more preferably ) Has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, and the like.

An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group ( Preferably it has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably having a carbon number). 7 to 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl, and acyloxy groups (preferably 2 to 30 carbon atoms, more preferably carbon atoms). 2 to 20, particularly preferably 2 to 10 carbon atoms, for example, acetoxy, benzoyloxy An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino). ,

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

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like), alkylthio. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 to 6 carbon atoms). 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like, and a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 carbon atom). To 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazoli Thio, 2-benzoxazolyl thio, and 2-benzthiazolylthio the like.),

A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), a sulfinyl group (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), ureido groups (preferably 1 to 30 carbon atoms, more preferably C1-C20, Most preferably, it is C1-C12, for example, a ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide groups (preferably C1-C30, more preferably carbon number) 1 to 20, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide That.), Hydroxy group, a mercapto group, a halogen atom (e.g. fluorine atom, chlorine atom, bromine atom, iodine atom),

Cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, As, for example, nitrogen atom, oxygen atom, sulfur atom, specifically 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 that may further have a ligand, and a metal ion having no other ligand is more preferable.

The metal ion represented by ^MY1 is not particularly limited, but a divalent or trivalent metal ion is preferable. As the divalent or trivalent metal ion, cobalt ion, magnesium ion, zinc ion, palladium ion, nickel ion, copper ion, platinum ion, lead ion, aluminum ion, iridium ion, and europium ion are preferable, cobalt ion, magnesium ion Ions, zinc ions, palladium ions, nickel ions, copper ions, platinum ions, and lead ions are more preferable, copper ions and platinum ions are more preferable, and platinum ions are particularly preferable. M ^Y1 may 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 even more preferably an oxygen atom or a nitrogen atom.

Preferable examples of the compound represented by the general formula (III) are compounds represented by the following general formulas (a) to (j), or tautomers thereof.
The compound represented by the general formula (III) is more preferably a compound represented by the general formula (a) and 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 , and Z in the corresponding general formula (III), respectively. ^{Z 12,} Z 13, have the same meaning as ^{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 (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 tyrosine pyrrole), preferably a pyrrole ring And a condensed ring containing a pyrrole ring (for example, benzpyrrole) is more preferable.

X ²¹ , X ²² , X ²³ and X ²⁴ each independently represent a substituted or unsubstituted carbon atom or nitrogen atom, preferably an unsubstituted carbon atom or nitrogen atom, and 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 the same as Z ²¹ in the general formula (a), Z ²² , Z ²³ , Z ²⁴ , Z ²⁵ , Z ²⁶ , X ²¹ , X ²² , X ²³ , X ²⁴ , M ²¹ are synonymous, and the preferred range is also the same.

R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ are each independently a hydrogen atom, or an alkyl group, an aryl group, R ⁴³ and R ^44, or the examples of substituents on Z ¹¹ or Z ¹² in the general formula (III). A group in which R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) is preferable, and an alkyl group, an aryl group, R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded. And more preferably a group forming a ring structure (for example, benzo-fused ring, pyridine-fused ring, etc.), and R ⁴³ and R ⁴⁴ or R ⁴⁵ and R ⁴⁶ are bonded to form a ring structure (for example, benzo-fused ring, pyridine-fused ring). Etc.) are more preferred.

R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ each independently 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 the 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 linking group is not particularly limited.For example, a carbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, a nitrogen-containing heterocyclic linking group, an oxygen atom linking group, a sulfur atom linking group, a silicon atom linking group, Examples thereof include an amino linking group, an imino linking group, a carbonyl linking group, and a linking group composed of a combination thereof.

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

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

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

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

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

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

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

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

Q ¹⁰² represents a group coordinated to M ¹⁰¹ by a nitrogen atom, a group coordinated by a phosphorus atom, a group coordinated by an oxygen atom, or a group coordinated by a sulfur atom, and a group coordinated by a nitrogen atom is More preferred.

M ¹⁰¹ has the same meaning as M ¹¹ in formula (I), and the preferred range is also the same.

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

In general formula (d), Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , L ²⁰¹ , L ²⁰² , L ²⁰³ , L ²⁰⁴ , and M ²⁰¹ are respectively in the corresponding general formula (c). Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , M ¹⁰¹ are synonymous, and the preferred range is also the same. ^Z204 , ^Z205 , ^Z206 , ^Z210 , ^Z211 and ^Z212 each represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom is preferred.

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

In general formula (e), ^Z301 , ^Z302 , ^Z303 , ^Z304 , ^Z305 , ^Z306 , ^Z307 , ^Z308 , ^Z309 , ^Z310 , ^L301 , ^L302 , ^L303 , ^L304 , M ³⁰¹ denotes Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁴ , Z ²⁰⁶ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , Z ²¹⁰ , Z ²¹² , L ¹⁰¹ , respectively in the corresponding general formulas (d) and (c). ^{L 102, L 103, L 104} , has the same meaning as ^{M 101,} and the preferred range is also the same.

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

In 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 , and the like in the corresponding general formulas (d) and (c), respectively. It is synonymous with Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , 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 correspond to the corresponding general formula (c). Are the same as Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , Q ¹⁰¹ , Q ¹⁰³ , Q ¹⁰² , M ¹⁰¹ , and the preferred range is also the same.

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

In 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 , respectively in the corresponding general formulas (d) and (c). It is synonymous with Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , M ¹⁰¹ , and the preferred range is also the same.

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

In general formula (i), Z ⁷⁰¹ , Z ⁷⁰² , Z ⁷⁰³ , Z ⁷⁰⁴ , Z ⁷⁰⁵ , Z ⁷⁰⁶ , Z ⁷⁰⁷ , Z ⁷⁰⁸ , Z ⁷⁰⁹ , Z ⁷¹⁰ , L ⁷⁰¹ , L ⁷⁰² , L ⁷⁰³ , L ⁷⁰⁴ , M ⁷⁰¹ denotes Z ²⁰¹ , Z ²⁰² , Z ²⁰³ , Z ²⁰⁷ , Z ²⁰⁸ , Z ²⁰⁹ , Z ²⁰⁴ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹² , L ¹⁰¹ , L in the corresponding general formulas (d) and (c), respectively. ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , and M ¹⁰¹ are the same, 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 ^{209 in the} corresponding general formulas (d), (c), and (f), respectively ^. , Z ²⁰⁴ , Z ²⁰⁵ , Z ²⁰⁶ , Z ²¹⁰ , Z ²¹¹ , Z ²¹² , L ¹⁰¹ , L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ , M ¹⁰¹ , X ⁴⁰¹ , X ⁴⁰² , and the preferred range is also the same. .

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

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

In general formula (A-1), M ^A1 represents a metal ion. Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 each independently represent a carbon atom or a nitrogen atom. Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group, and these linking groups may have the same structure or different structures. Q ^A11 and Q ^A12 each represent a partial structure containing an atom bonded to M ^A1 through 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+> , 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 , L ^A14 is independently a single bond, or a linkage composed of carbon, nitrogen, silicon, sulfur, oxygen, germanium, phosphorus, etc. More preferably a single bond, a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, a substituted silicon atom, an oxygen atom, a sulfur atom, a divalent aromatic hydrocarbon ring group, a divalent aromatic hydrocarbon group An aromatic heterocyclic group, more preferably a single bond, a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, a substituted silicon atom, a divalent aromatic hydrocarbon ring group, a divalent aromatic hetero group Examples of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 , which is a cyclic group, particularly preferably a single bond, a substituted or unsubstituted methylene group, include the following: Can be mentioned.

The divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , or L ^A14 may further have a substituent. Examples of the substituent that can be introduced include alkyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms. For example, methyl, ethyl, iso-propyl, tert- Butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl).

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl and the like), amino. Group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc. An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc. An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably carbon 6-20, especially preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy.),

Heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyl A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably 7 carbon atoms). To 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 1 carbon atoms. , And the like such as phenyloxycarbonyl.),

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

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

An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 carbon atoms). To 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), sulfonyl group (preferably carbon Number 1-30, more preferably number 1-20, particularly preferably number 1-12, such as mesyl, tosyl, etc. And the like.), A sulfinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methane sulfinyl, and the like benzenesulfinyl.),

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

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

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

Q ^A11 and Q ^A12 each represent a partial structure containing an atom bonded to M ^A1 through 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 more preferable, and a group bonded to a carbon atom is particularly preferable.

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

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

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

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

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

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

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

The compound represented by formula (A-2) will be described in detail.
M ^A2 , Y ^A21 , Y ^A24 , Y ^A25 , Y ^A28 , Y ^A22 , Y ^A23 , Y ^A26 , Y ^A27 , L ^A21 , L ^A22 , L ^A23 , L ^A24 correspond to the general formula (A-1), respectively. M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , L ^A14, and preferred ranges are also the same. It is.
Z ^A21 , Z ^A22 , Z ^A23 , Z ^A24 , Z ^A25 and Z ^A26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^A21 , Z ^A22 , Z ^A23 , Z ^A24 , Z ^A25 and Z ^A26 are preferably each independently a substituted or unsubstituted carbon atom, 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 , L ^A34 correspond to the general formula (A-1). M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , L ^A14, and preferred ranges are also the same. It is.
Z ^A31 , Z ^A32 , Z ^A33 and Z ^A34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^A31 , Z ^A32 , Z ^A33 and Z ^A34 are preferably substituted or unsubstituted carbon atoms, 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 , L ^A44 correspond to the general formula (A-1). M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L ^A12 , L ^A13 , L ^A14, and preferred ranges are also the same. It is.
Z ^A41 , Z ^A42 , Z ^A43 , Z ^A44 , Z ^A45 and Z ^A46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^A41 , Z ^A42 , Z ^A43 , Z ^A44 , Z ^A45 and Z ^A46 are preferably substituted or unsubstituted carbon atoms, more preferably unsubstituted carbon atoms. As the substituent substituted with the carbon atom, those exemplified as the substituents of the divalent linking group represented by L ^A11 , L ^A12 , L ^A13 , and L ^A14 in formula (A-1) can be applied.
X ^A41 and X ^A42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. X ^A41 and X ^A42 are preferably each independently an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

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

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

In formula (B-1), M ^B1 represents a metal ion. Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom. Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom. L ^B11 , L ^B12 , L ^B13 and L ^B14 each represent a linking group. Q ^B11 and Q ^B12 each 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 , Q ^B12 are respectively corresponding to M ^A1 , Y ^A11 , Y ^A14 , Y ^A15 , Y ^A18 , Y ^A12 , Y ^A13 , Y ^A16 , Y ^A17 , L ^A11 , L in the general formula (A-1). It is synonymous with ^A12 , L ^A13 , L ^A14 , Q ^A11 , Q ^A12 , and the preferred range is also the same.

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

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

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

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

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

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

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

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

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

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

The general formula (C-1) will be described in detail.
In the general formula (C-1), M ^C1 , L ^C11 , L ^C12 , Q ^C11 , and QC ¹² are M ^A1 , L ^A11 , L ^A12 , Q ^A11 , Q in the corresponding general formula (A-1), respectively. ^It is synonymous with ^A12 , and its preferable range is also the same.
G ^C11 and G ^C12 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, preferably a nitrogen atom or an unsubstituted carbon atom, and more preferably a nitrogen atom.
R ^C11 and R ^C12 each independently represent a hydrogen atom or a substituent. R ^C11 and R ^C12 may ^combine with each other to form a five-membered ring. R ^C13 and R ^C14 each independently represent a hydrogen atom or a substituent. R ^C13 and R ^C14 may ^combine with each other to form a five-membered ring.

The substituent represented by R ^C11 , R ^C12 , R ^C13 and R ^C14 is an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms). , For example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl and 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, anthranyl and the like), amino. Group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc. An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc. An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably carbon 6-20, especially preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy.),

Heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyl A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably 7 carbon atoms). To 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 1 carbon atoms. , And the like such as phenyloxycarbonyl.),

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

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

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

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

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

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

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

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

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

The compound represented by formula (C-3) will be described in detail.
In the general formula (C-3), M ^C3 , L ^C31 , L ^C32 , G ^C31 , and G ^C32 correspond respectively to M ^C1 , L ^C11 , L ^C12 , G ^C11 , G in the general formula (C-1). ^It is synonymous with ^C12 , and its preferable 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 , G in the corresponding general formula (C-1), respectively. ^It is synonymous with ^C12 , and its preferable range is also the same.
Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. Z ^C41 , Z ^C42 , Z ^C43 and Z ^C44 are preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom.

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

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

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

In formula (D-1), M ^D1 represents a metal ion.
G ^D11 and G ^D12 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. J ^D11 , J ^D12 , J ^D13 and J ^D14 represent an atomic group necessary for forming a five-membered ring. L ^D11 and L ^D12 each represent a linking group.

The general formula (D-1) will be described in detail.
In the general formula (D-1), M ^D1 , L ^D11 , and L ^D12 have the same ^meanings as M ^A1 , L ^A11 , and L ^{A12 in the} corresponding general formula (A-1), respectively, and preferred ranges thereof are also the same. is there.
G ^D11 and G ^D12 have the same ^meanings as G ^C11 and G ^C12 in the corresponding general formula (C-1), respectively, and preferred ranges thereof are also the same.
J ^D11 , J ^D12 , J ^D13 and J ^D14 represent an atomic group necessary for forming a nitrogen-containing hetero five-membered ring together with the atomic group to which these are bonded.

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

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

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

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

General formula (D-2) is demonstrated in detail.
M ^D2 , L ^D21 , L ^D22 , G ^D21 , and G ^D22 are synonymous with M ^D1 , L ^D11 , L ^D12 , G ^D11 , and G ^D12 in the general formula (D-1), and preferred ranges are also the same. .
Y ^D21 , Y ^D22 , Y ^D23 and Y ^D24 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, preferably a substituted or unsubstituted carbon atom, more preferably an unsubstituted carbon atom. is there.
X ^D21 , X ^D22 , X ^D23 and X ^D24 each independently represent an oxygen atom, a sulfur atom, —NR ^D21 —, —C (R ^D22 ) R ^D23 —, preferably a sulfur atom, —NR ^D21 —, — C (R ^D22 ) R ^D23 —, more preferably —NR ^D21 —, —C (R ^D22 ) R ^D23 —, and still more preferably —NR ^D21 —.
R ^D21 , R ^D22 and R ^D23 each independently represent a hydrogen atom or a substituent. As the substituent represented by R ^D21 , R ^D22 and R ^D23 , an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, , Ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably It has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl).

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

Heterocyclic group (there is an aliphatic heterocyclic group or an aromatic heterocyclic group. Preferably, it contains any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to carbon atoms. 30 and particularly preferably 2 to 12 carbon atoms, and examples thereof include imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl group, and the like. R ^D21 , R ^D22 and R ^D23 are preferably an alkyl group, an aryl group or an aromatic heterocyclic group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.

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

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

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

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

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

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

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

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

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

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

The general formula (E-3) will be described in detail.
In General Formula (E-3), M ^E3 , G ^E31 , G ^E32 , G ^E33 , G ^E34 , Y ^E31 , Y ^E32 , Y ^E33 , and Y ^E34 correspond to M in General Formula (E-1), respectively. ^{E 1} , G ^E11 , G ^E12 , G ^E13 , G ^E14 , Y ^E11 , Y ^E12 , Y ^E13 , Y ^E14 have the same meanings, and preferred ranges are also the same. X ^E31 and X ^E32 have the same meaning as X ^E21 and X ^E22 in the corresponding general formula (E-2), and preferred ranges are also the same.

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

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

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

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

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

In general formula (F-2), ^MF2 represents a metal ion. L ^F21 , L ^F22 and L ^F23 represent a linking group. R ^F21 , R ^F22 , R ^F23 and R ^F24 represent substituents, and R ^F21 and R ^F22 , R ^F22 and R ^F23 , and R ^F23 and R ^F24 may be linked to each other to form a ring, if possible. However, the ring formed by R ^F21 and R ^F22 , R ^F23 and R ^F24 is a five-membered ring. Z ^F21 , Z ^F22 , Z ^F23 , Z ^F24 , Z ^F25 and Z ^F26 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In general formula (F-3), ^MF3 represents a metal ion. L ^F31 , L ^F32 and L ^F33 represent a linking group. R ^F31 , R ^F32 , R ^F33, and R ^F34 represent a substituent, and R ^F31 and R ^F32 , R ^F32 and R ^F33 , and R ^F33 and R ^F34 may ^combine with each other to form a ring if possible. However, the ring formed by R ^F31 and R ^F32 , R ^F33 and R ^F34 is a five-membered ring. Z ^F31 , Z ^F32 , Z ^F33 and Z ^F34 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

In general formula (F-4), ^MF4 represents a metal ion. L ^F41 , L ^F42 and L ^F43 represent a linking group. R ^F41 , R ^F42 , R ^F43 and R ^F44 represent a substituent, and R ^F41 and R ^F42 , R ^F42 and R ^F43 , and R ^F43 and R ^F44 may be linked to each other to form a ring, if possible. However, the ring formed by R ^F41 and R ^F42 and R ^F43 and R ^F44 is a five-membered ring. Z ^F41 , Z ^F42 , Z ^F43 , Z ^F44 , Z ^F45 , and Z ^F46 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom. X ^F41 and X ^F42 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

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

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

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

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

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

Next, the host compound used in the present invention will be described.
In the organic electroluminescent device of the present invention, a metal complex having at least one tridentate or higher ligand as a light emitting dopant in the light emitting layer (hereinafter, also simply referred to as “metal complex” or “light emitting dopant”). .) And a plurality of host compounds, (1) when the ionization potential of the metal complex is Ip (D), and the minimum of the ionization potentials of the plurality of host compounds is Ip (H) min ΔIp = Ip (D) −Ip (H) It is preferable in terms of light emission characteristics and driving durability that ΔIp defined by min satisfies the relationship of ΔIp> 0 eV.

The organic electroluminescent device of the present invention is (2) when the electron affinity of the metal complex is Ea (D) and the maximum of the electron affinity of the plurality of host compounds is Ea (H) max. It is also preferable in terms of light emission characteristics and driving durability that ΔEa defined by ΔEa = Ea (H) max−Ea (D) satisfies the relationship of ΔEa> 0 eV.
Furthermore, it is more preferable in terms of light emission characteristics and driving durability that the above (1) and (2) are satisfied.

  Further, the organic electroluminescent device of the present invention is any one of (3) ΔIp of 1.2 eV> ΔIp ≧ 0.2 eV and / or (4) ΔEa of 1.2 eV> ΔEa> 0.2 eV. When the relationship is satisfied, holes and / or electrons tend to be less likely to be trapped by the dopant, which is preferable from the viewpoint of driving durability. In particular, the ΔIp is 1.2 eV> ΔIp> 0.4 eV and / or the ΔEa. Preferably satisfies any one relationship of 1.2 eV> ΔEa> 0.4 eV.

Furthermore, in the organic electroluminescent element of the present invention, (5) the Ip (H) min is 5.1 eV or more and / or (6) Ea (H) max is 3.0 eV or less. From the viewpoint of color purity and driving durability, a more preferable range is that Ip (H) min is 5.4 eV or more and / or Ea (H) max is 2.8 eV or less.
This leads to suppression of interaction between a plurality of host compounds in the light emitting layer. When a charge transfer complex or exciplex having a lower excitation energy state is formed as a result of the interaction between a plurality of host compounds, the excited state that should originally be possible for any host compound is the charge transfer complex or exciplex. Formed on a plex. As a result, energy transfer to the metal complex (dopant) in the present invention is insufficient, and predetermined light emission may not be obtained. Moreover, it is because there exists a concern about a drive durability fall by decomposition | disassembly from an excited state on a charge transfer complex and an exciplex.
Whether or not there is an interaction between a plurality of host compounds in the light emitting layer is determined by producing a single layer film of only the plurality of host compounds contained in the light emitting layer in the same manner as the formation conditions of the light emitting layer. It can be judged by measuring the film and measuring the fluorescence phosphorescence spectrum and comparing it with the emission spectrum of each individual host compound.
That is, when a long-wave emission spectrum component that cannot be attributed to each emission spectrum contained in a plurality of host compounds is observed in the fluorescent phosphorescence spectrum, an interaction is considered to have occurred. In particular, each emission spectrum component is preferably not more than 1/100 with respect to the maximum emission intensity of the main peak of the emission spectrum on the longer wave side of 15 nm or more than any of the main peaks in the emission spectrum of a plurality of host compounds alone. More preferably, an emission spectrum component having an emission intensity of 1/1000 or less, more preferably 1 / 10,000 or less is not observed.
For the measurement of the fluorescence phosphorescence spectrum, for example, RF-5300PC manufactured by Shimadzu Corporation can be used, and the excitation light can be performed using light having a wavelength that each contained host compound has absorption alone.

Here, the ionization potential (Ip), the electron affinity (Ea), and the triplet state level (T ₁ ) described later in the present invention will be described.

The ionization potential (Ip), the electron affinity (Ea), and the triplet state level (T ₁ ) to be described later can be obtained by depositing each material on quartz by a vacuum deposition method (vacuum degree: about 10 ⁻⁴ Pa). It is a value obtained by measuring a single layer film formed to be

  The ionization potential (Ip) is defined by a value measured at room temperature (about 25 ° C.) and in the atmosphere with an ultraviolet photoelectron analyzer AC-1 (manufactured by Riken Keiki Co., Ltd.). The measurement principle of AC-1 is described in Chiyaya Adachi et al., “Organic thin film work function data collection” issued by CMC Publishing Co., Ltd. 2004.

  The electron affinity (Ea) is defined by a value obtained by calculating the band gap from the long wave end of the absorption spectrum of the single layer film and calculating the electron affinity (Ea) from the value of the ionization potential.

The lowest triplet excitation energy (triplet state level T ₁ ) is defined by a value calculated from the short wave end of a phosphorescence emission spectrum measured at room temperature. The temperature can also be performed at the nitrogen cooling temperature.

The fact that the light emitting device of the present invention is remarkably excellent in driving durability and light emitting characteristics (external light emission efficiency) is presumed to function by the following light emission mechanism, but the details are unknown. is there.
That is, most of the holes injected from the anode are injected into the hole transporting host (the host compound in the present invention) in the light emitting layer via the hole injection layer and the hole transport layer. On the other hand, most of the electrons injected from the cathode are injected into the electron transporting host (host compound in the present invention) in the light emitting layer via the electron injection layer and the electron transport layer. Holes are injected from the hole transporting host in the light emitting layer into the HOMO of the electron transporting host, and excitons are generated on the electron transporting host. Alternatively, electrons are injected from the electron transporting host into the LUMO of the hole transporting host, and excitons are generated on the hole transporting host. The excited state energy of these host compounds moves to the metal complex (dopant) in the present invention, and light is emitted from the singlet and / or triplet state of the dopant.
Here, when holes and electrons are injected into the light emitting layer, holes are injected into the hole transporting host and electrons are injected into the electron transporting host. As a result, the hole transporting host can be released from the anionic state and the electron transporting host from the cationic state, and as a result, driving durability can be improved. In addition, when holes and electrons are injected into the light emitting layer, since the HOMO and LUMO of the metal complex (dopant) in the present invention are outside the host compound, almost all carriers are injected into the metal complex (dopant) in the present invention. It is thought that durability can be improved with respect to the metal complex (dopant) in this invention with low tolerance to a cation or an anion state.

Next, the structure in the organic electroluminescent element of this invention is demonstrated.
The organic electroluminescent element of the present invention preferably has an organic compound layer including at least a light emitting layer between a pair of electrodes, and further has a carrier transport layer adjacent to the light emitting layer. More preferably, the carrier transport layer is an electron transport layer and / or a hole transport layer.
From the nature of the light emitting element, it is preferable that at least one of the pair of electrodes is transparent.

  In the present invention, the organic compound layer is preferably laminated in the order of the hole transport layer, the light emitting layer, and the electron transport layer from the anode side. Further, an electron blocking layer or the like may be provided between the hole transport layer and the light emitting layer, or a hole blocking layer or the like may be provided between the light emitting layer and the electron transport layer. Further, a hole injection layer may be provided between the anode and the hole transport layer, and similarly, an electron injection layer may be provided between the cathode and the electron transport layer.

  A preferred embodiment of the organic compound layer in the organic electroluminescent device of the present invention is at least a hole injection layer, a hole transport layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer in order from the anode side. It is the aspect which has.

When the hole blocking layer is provided between the light emitting layer and the electron transporting layer, the organic compound layer adjacent to the light emitting layer is the hole transporting layer on the anode side and the hole blocking layer on the cathode side. .
Each layer may be divided into a plurality of secondary layers.

  Next, elements constituting the light emitting device of the present invention will be described in detail.

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

The organic compound layer preferably has a single layer thickness of 500 nm or less, more preferably 5 to 200 nm, and particularly preferably 10 to 100 nm, from the viewpoint of lowering the driving voltage.
The layer adjacent to the light emitting layer on the anode side may be a hole injection layer, and the layer adjacent to the light emitting layer on the cathode side may be an electron injection layer or a hole blocking layer. Details of these layers will be described later.

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

(Light emitting layer)
The light-emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer which has the function to provide and to emit light.
The light emitting layer in the present invention contains at least one metal complex having a tridentate or higher ligand and a plurality of host compounds.
Further, the light emitting layer may be a single layer or two or more layers, and each layer may emit light in different emission colors. Even when there are a plurality of light emitting layers, it is preferable that each layer of the light emitting layer contains at least one metal complex having a tridentate or higher ligand and a plurality of host compounds.

As described above, the metal complex and the plurality of host compounds contained in the light emitting layer in the present invention are (1) ΔIp (= Ip (D) −Ip (H) min)> 0 eV and / or (2 As long as the relationship of ΔEa (= Ea (H) max−Ea (D))> 0 eV is satisfied, it can be used without particular limitation.
That is, even when a metal complex that can emit light (fluorescence) from singlet excitons (hereinafter also referred to as “fluorescent dopant”) and a plurality of host compounds are combined, light emitted from triplet excitons (phosphorescence). May be a combination of a metal complex (hereinafter also referred to as “phosphorescent dopant”) and a plurality of host compounds, but from the viewpoint of luminous efficiency, light emission from triplet excitons (phosphorescence) is also possible. ) Is preferably a combination of a metal complex obtained with a plurality of host compounds.
The light emitting layer in the present invention can contain two or more kinds of metal complexes for the purpose of improving the light emission efficiency and color purity, or extending the light emission wavelength range.

In the present invention, a metal complex (luminescent dopant) that satisfies the relationship (1) and / or (2) and a plurality of host compounds will be described below as an example, but the present invention is not limited thereto.
When a single luminescent dopant is used and a plurality of host compounds are used, the Ip (D) of the luminescent dopant is larger than the ionization potential Ip (H) min of the host compound having the minimum Ip, that is, Ip (D)> Ip (H) min is preferred. Moreover, it is preferable that the host compound having the maximum Ea has a metal complex such that Ea (D) is smaller than the electron affinity Ea (H) max, that is, Ea (H) max> Ea (D). It is further preferred that these are metal complexes that are filled together.
The host compound used as Ip (H) min at this time includes a hole transporting host, and the host compound used as Ea (H) max includes an electron transporting host.
When a light emitting dopant is used, Ip (D) means the light emitting dopant with the smallest Ip, and Ea (D) means the light emitting dopant with the largest Ea.

-Luminescent dopant-
As the luminescent dopant in the present invention, in addition to the metal complex having a tridentate or higher ligand, any of conventionally known phosphorescent luminescent materials and fluorescent luminescent materials can be used as the dopant. It is more preferable if the relationship (1) and / or (2) is satisfied between the dopant and the plurality of host compounds.
The luminescent dopant in the present invention further satisfies the relationship of (3) 1.2 eV> ΔIp ≧ 0.2 eV and / or (4) 1.2 eV>ΔEa> 0.2 eV with the host compound. A dopant is preferable from the viewpoint of driving durability.

= Phosphorescent dopant =
In general, examples of the phosphorescent light-emitting dopant include complexes containing a transition metal atom or a lanthanoid atom.
For example, the transition metal atom is not particularly limited, but preferably includes ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, and platinum, and more preferably rhenium, iridium, and platinum.
Examples of lanthanoid atoms include lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. Among these lanthanoid atoms, neodymium, europium, and gadolinium are preferable.

Examples of the ligand of the complex include G.I. Wilkinson et al., Comprehensive Coordination Chemistry, Pergamon Press, 1987, H.C. By Yersin, “Photochemistry and
Photophysics of Coordination Compounds "
Examples include the ligands described in Springer-Verlag, Inc., published in 1987, Akio Yamamoto, “Organic Metal Chemistry: Fundamentals and Applications,” published in 1982, published by Soukabo, Inc.
Specific ligands are preferably halogen ligands (preferably chlorine ligands), nitrogen-containing heterocyclic ligands (eg, phenylpyridine, benzoquinoline, quinolinol, bipyridyl, phenanthroline, etc.), diketones Ligand (for example, acetylacetone), carboxylic acid ligand (for example, acetic acid ligand), carbon monoxide ligand, isonitrile ligand, cyano ligand, more preferably nitrogen-containing Heterocyclic ligand.
The complex may have one transition metal atom in the compound, or may be a so-called binuclear complex having two or more. Different metal atoms may be contained at the same time.

  Among these, specific examples of the luminescent dopant satisfying the relationship (1) and (2) above include, for example, US 6303238 B1, US 6097147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01. / 39234 A2, WO 01/41512 A1, WO 02/02714 A2, WO 02/15645 A1, WO 02/44189 A1, JP 2001-247859, Japanese Patent Application 2000-33561, JP 2002-117978, Japanese Patent Application 2001- 248165, Japanese Patent Application Laid-Open No. 2002-235076, Japanese Patent Application No. 2001-239281, Japanese Patent Application Laid-Open No. 2002-170684, EP 12111257, Japanese Patent Application Laid-Open No. 2002-226495, Japanese Patent Application Laid-Open No. 2002-234894, Japanese Patent Application Laid-Open No. 98470, JP-A-2002-173675, JP-A-2002-203678, JP-A-2002-203679, and Japanese Patent Application No. 2003-157066, and the like. Among these, phosphorescent compounds are more preferable (3) and ( As the luminescent dopant satisfying the relationship 4), Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex And Ce complexes. Particularly preferred are Ir complexes, Pt complexes, and Re complexes. Among them, Ir complexes, Pt complexes, which include at least one coordination mode of metal-carbon bond, metal-nitrogen bond, metal-oxygen bond, and metal-sulfur bond, Re complexes are preferred.

= Fluorescent dopant =
As the fluorescent light-emitting dopant, generally, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, pyran, perinone, oxadiazole, aldazine, Pyraridin, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, aromatic dimethylidin compounds, condensed polycyclic aromatic compounds (anthracene, phenanthroline, pyrene, perylene, rubrene, pentacene, etc.) , 8-quinolinol metal complexes, various metal complexes represented by pyromethene complexes and rare earth complexes, polythiophene, polyphenylene, polyphenylene vinyle Polymeric compounds such as organosilanes, and the like, and their derivatives.

  Among these, the following compounds are mentioned as a specific example of the luminescent dopant which satisfy | fills the relationship of said (1) and (2), for example.

  Among the above, the luminescent dopant satisfying the more preferable relationships (3) and (4) is D-2, D-3, D-4, D-5, D-6, D-9, D-10. , D-11, D-12, D-13, and D-14.

The light-emitting dopant in the light-emitting layer is contained in an amount of 0.1 to 20% by mass based on the total mass of the compound generally forming the light-emitting layer in the light-emitting layer. It is preferable to contain 15 mass%, and it is more preferable to contain 2-12 mass%.
In the present invention, the light emitting layer has a metal complex having a tridentate or higher ligand in the light emitting layer. When a plurality of light emitting dopants are contained, the total amount of the plurality of light emitting dopants is within the above range. It is preferable that

  The thickness of the light emitting layer is not particularly limited, but is usually preferably 1 nm to 500 nm, and more preferably 5 nm to 200 nm from the viewpoint of light emission efficiency, among which 10 nm to 100 nm. Is more preferable.

-Host compound-
The host compound used in the light-emitting layer needs to use at least a plurality of host compounds, but can be used without any particular limitation. Similar to the above-described metal complex in the present invention, (1) ΔIp (= Ip (D) −Ip (H) min)> 0 eV and / or (2) ΔEa (= Ea (H) max−Ea (D))> 0 eV is more preferable if it satisfies the relationship.
Among the above ranges, it is more preferable that the host compound satisfy the relationship of (3) 1.2 eV> ΔIp ≧ 0.2 eV and / or (4) 1.2 eV>ΔEa> 0.2 eV.
As the plurality of host compounds, a hole transporting host compound (hole transporting host) excellent in hole transporting property and an electron transporting host compound (electron transporting host) excellent in electron transporting property can be used.

= Hole-transporting host =
The hole transporting host in the light emitting layer used in the present invention is not particularly limited as long as it is a known hole transporting material, but depending on the relationship with the light emitting dopant, From the viewpoint of durability and color purity, those satisfying the relationship (1) and / or (2) are preferable, and the electron affinity Ea is preferably in the range of 1.2 to 4.0 eV, and 1.2. -3.4 eV is more preferable, 1.2-3.0 eV is still more preferable, 1.2-2.8 eV is especially preferable.
As with the electron affinity Ea, although depending on the relationship with the luminescent dopant, the ionization potential Ip is, in particular, in the range of 5.0 to 6.2 eV from the viewpoint of durability and color purity. Preferably, 5.1 to 6.1 eV is more preferable, 5.4 to 6.0 eV is further preferable, and 5.4 to 5.8 eV is particularly preferable.
Specific examples of such a hole transporting host include the following materials.
Pyrrole, carbazole, triazole, oxazole, oxadiazole, imidazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound , Styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films And derivatives thereof.
Among them, it is more preferable to satisfy the above (3) and (4), and as the hole transport layer host, a carbazole derivative, an aromatic tertiary amine compound, or a thiophene derivative is preferable, and in particular, the carbazole skeleton and / or aromatic in the molecule. Those having a plurality of group III tertiary amine skeletons are preferred.
Specific examples of such a hole transport layer host include the following compounds.

= Electron transporting host =
The electron-transporting host in the light-emitting layer used in the present invention is not particularly limited as long as it is a known electron-transporting material, but depending on the relationship with the light-emitting dopant, it is particularly durable. From the viewpoints of color and color purity, it is preferable if it satisfies the relationship (1) and / or (2), and the ionization potential Ip is more preferably in the range of 4.6 to 7.5 eV. 0.1 to 7.1 eV is more preferable, and 5.4 to 7.1 eV is particularly preferable.
As with the ionization potential Ip, although depending on the relationship with the luminescent dopant, the electron affinity Ea has an electron affinity Ea of 2.4 to 3.6 eV from the viewpoint of durability and color purity. The range is preferable, 2.6 to 3.4 eV is more preferable, 2.8 to 3.3 eV is further preferable, and 2.9 to 3.2 eV is particularly preferable.
Specifically, the following materials can be mentioned, for example. Pyridine, pyrimidine, triazine, imidazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine substitution Aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanines, and derivatives thereof (which may form condensed rings with other rings), metal complexes of 8-quinolinol derivatives and metal phthalocyanines, Examples include various metal complexes represented by metal complexes having benzoxazole or benzothiazol as a ligand.

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

  There are various known ligands contained in the metal complex. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Examples include ligands described in Yersin's 1987 issue, “Organometallic Chemistry: Fundamentals and Applications”, Hankabo Publishing Company, Akio Yamamoto, 1982 issue, etc.

  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. Or a bidentate or higher ligand, preferably a bidentate ligand such as a pyridine ligand, a bipyridyl ligand, a quinolinol ligand, a hydroxyphenylazole ligand (hydroxyphenyl) Benzimidazole, hydroxyphenylbenzoxazole ligand, hydroxyphenylimidazole ligand)), alkoxy ligand (preferably 1-30 carbon atoms, more preferably 1-20 carbon atoms, particularly preferably carbon 1-10, for example, methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), aryloxy ligands Preferably it has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy, 2,4,6-trimethylphenyl Oxy, 4-biphenyloxy, etc.),

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, quinolyloxy, etc.) 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 ligand ( 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 phenylthio, etc., a heteroarylthio ligand (preferably 1 to 1 carbon atoms). 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.), siloxy ligands (preferably having 1 to 30 carbon atoms, more preferably 3 to 25 carbon atoms, particularly preferably carbon atoms). 6 to 20, for example, a triphenylsiloxy group, a triethoxysiloxy group, a triisopropylsiloxy group, etc.), more preferably a nitrogen-containing heterocyclic ligand, an aryloxy ligand, a heteroaryl. An oxy group and a siloxy ligand are preferable, and a nitrogen-containing heterocyclic ligand, an aryloxy ligand, and a siloxy ligand are more preferable.

  Specific examples of such an electron transporting host include the following materials.

  Among them, E-1 to E-7 are preferable as the electron transport layer host satisfying (3) and (4), and E-3 to E-5 are particularly 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 T ₁ (D) of the phosphorescent dopant and the minimum lowest triple among the plurality of host compounds. It is preferable in terms of color purity and light emission efficiency that the term excitation energy T ₁ (H) min satisfies the relationship of T ₁ (H) min and> T ₁ (D).

  In addition, the content of the plurality of host compounds of the present invention is not particularly limited, but from the viewpoints of luminous efficiency, driving voltage, and durability, 10 masses per mass of the total compound forming the light emitting layer. % To 90% by mass, more preferably 15% to 85% by mass, and particularly preferably 20% to 80% by mass.

Further, the carrier mobility in the light emitting layer is generally 10 ⁻⁷ cm ² / V / s or more and 10 ^−1.
cm ² / V / s or less, among others, preferably ¹⁰ -5 ^cm 2 / V / s or more ¹⁰ -1 ^cm 2 / V / s or less from the standpoint of emission ^{efficiency, 10 -4 cm 2 / V /} s or more 10 < ^-1 > cm < ² > / V / s or less is still more preferable, and 10 < ^-3 > cm < ² > / V / s or more and 10 < ^-1 > cm < ² > / V / s or less are especially preferable.
The carrier mobility of the light emitting layer is preferably smaller than the carrier mobility of the carrier transport layer described later from the viewpoint of driving durability.
The carrier mobility was measured by the Time of Flight method, and the obtained value was defined as the carrier mobility.

(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.
Specifically, the hole injection layer and the hole transport layer are carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamines. Derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, organosilane derivatives, carbon , Etc. are preferable.

The thicknesses of the hole injection layer and the hole transport layer are not particularly limited, but are usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 nm. is there.
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. .

When the carrier transport layer adjacent to the light emitting layer is a hole transport layer, the driving durability is such that the Ip (HTL) of the hole transport layer is smaller than the Ip (D) of the dopant contained in the light emitting layer. This is preferable.
Ip (HTL) in the hole transport layer is defined by a value measured by the Ip measuring method.

The carrier mobility in the hole transport layer is generally 10 ⁻⁷ cm ² / V / s or more and 1
0 ⁻¹ cm ² / V / s or less, among which 10 ⁻⁵ cm ² / V / s or more and 10 ⁻¹ cm ² / V / s or less is preferable from the viewpoint of light emission efficiency, and 10 ⁻⁴ cm ² / V. / S to 10 ⁻¹ cm ² / V / s is more preferable, and 10 ⁻³ cm ² / V / s to 10 ⁻¹ cm ² / V / s is particularly preferable.
The carrier mobility is defined by a value measured by a method similar to the method for measuring the carrier mobility of the light emitting layer.
The carrier mobility of the hole transport layer is preferably greater than the carrier mobility of the light emitting layer from the viewpoint of driving durability.

  The hole injection layer or hole transport layer of the organic EL device of the present invention can contain an electron accepting dopant. As the electron-accepting dopant introduced into the hole-injecting layer or the hole-transporting layer, an inorganic compound or an organic compound can be used as long as it has an electron-accepting property and oxidizes an organic compound. As the compound, Lewis acid compounds such as ferric chloride, aluminum chloride, gallium chloride, indium chloride, and antimony pentachloride can be suitably used.

  In the case of an organic compound, a compound having a nitro group, a halogen, a cyano group, a trifluoromethyl group, or the like as a substituent, a quinone compound, an acid anhydride compound, or fullerene can be preferably used.

  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%.

(Electron injection layer, electron transport layer)
The electron injection layer and the electron transport layer are layers having any one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes that can be injected from the anode.
Specific examples of the material for the electron injection layer and the electron transport layer include pyridine, pyrimidine, triazine, imidazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiol. Heterocyclic tetracarboxylic anhydrides such as pyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, naphthaleneperylene, phthalocyanines, and their derivatives (form condensed rings with other rings) Or metal complexes of 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazol as ligands, and the like.

The thicknesses of the electron injection layer and the electron transport layer are not particularly limited, but from the viewpoint of lowering the driving voltage, those in the range of usually 1 nm to 5 μm are preferable, more preferably 5 nm to 1 μm. Preferably it is 10 nm-500 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
When the carrier transport layer adjacent to the light emitting layer is an electron transport layer, the Ea (ETL) of the electron transport layer is greater than the dopant Ea (D) contained in the light emitting layer. Is preferable.
The Ea (ETL) uses a value measured by the same method as the Ea measuring method.

Further, the carrier mobility in the electron transport layer is generally 10 ⁻⁷ cm ² / V / s or more and 10 ⁻¹ cm ² / V / s or less, and above all, from the viewpoint of light emission efficiency, 10 ⁻⁵ cm ^2. / V / s or more and 10 ⁻¹ cm ² / V / s or less is preferable, 10 ⁻⁴ cm ² / V / s or more and 10 ⁻¹ cm ² / V / s or less is more preferable, and 10 ⁻³ cm ² / V / s s to 10 ⁻¹ cm ² / V / s is particularly preferable.
The carrier mobility of the electron transport layer is preferably larger than the carrier mobility of the light emitting layer from the viewpoint of driving durability. The carrier mobility was measured in the same manner as the hole transport layer measurement method.
In the carrier mobility of the light-emitting element in the present invention, the carrier mobility in the hole transport layer, electron transport layer, and light-emitting layer is (electron transport layer ≧ hole transport layer)> light-emitting layer. From the viewpoint of sex.

  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.

  These electron donating dopants may be used alone or in combination of two or more. The amount of the electron donating dopant varies depending on the type of material, but is preferably 0.1% by mass to 99% by mass, and 1.0% by mass to 80% by mass with respect to the electron transport layer material. Is more preferable, and 2.0 mass% to 70 mass% is particularly preferable.

(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.
Although a hole block layer is not specifically limited, Specifically, aluminum complexes, such as BAlq, a triazole derivative, a pyraza ball derivative, etc. can be contained.
Further, the thickness of the hole blocking layer is generally preferably 50 nm or less, preferably 1 to 50 nm, and more preferably 5 to 40 nm in order to lower the driving voltage.

(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. The anode may be formed on the entire one surface of the substrate, or may be formed on a part thereof.

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

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

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

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

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

  Examples of the material constituting the cathode include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof, 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 to 10% by mass of alkali metal or alkaline earth metal, or a mixture thereof (for example, lithium-aluminum alloy, magnesium-aluminum alloy, etc.) Say.

  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 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 to 10 nm and further laminating a transparent conductive material such as ITO or IZO.

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

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

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

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

(Protective layer)
In the present invention, the entire organic EL element may be protected by a protective layer.
As a material contained in the protective layer, any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni, MgO, SiO, SiO ₂ , Al ₂ O ₃ , GeO, NiO, CaO, BaO, and Fe ₂ O. ₃
, Metal oxides such as Y ₂ O ₃ and TiO ₂ , metal nitrides such as SiN _x and SiN _x O _y , metal fluorides such as MgF ₂ , LiF, AlF ₃ and CaF ₂ , polyethylene, polypropylene, polymethyl methacrylate A monomer mixture comprising polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and at least one comonomer Examples include copolymers obtained by copolymerization, fluorine-containing copolymers having a cyclic structure in the copolymer main chain, water-absorbing substances having a water absorption of 1% or more, moisture-proof substances having a water absorption of 0.1% or less, and the like. .

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

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

The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving durability of the organic electroluminescent element in the present invention can be measured by the luminance half time at a specific luminance. For example, using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage is applied to the organic EL element to emit light, and an initial luminance of 2000 cd / m ^{2 is obtained.}
The continuous driving test is performed under the conditions, and the luminance half time T (1/2) is defined as the time when the luminance becomes 1000 cd / m ² , and the luminance half time can be obtained by comparing with a conventional light emitting element. In the present invention, this value is used.
An important characteristic value of this organic electroluminescence device is external quantum efficiency. The external quantum efficiency is calculated by “external quantum efficiency φ = number of photons emitted from the device / number of electrons injected into the device”, and it can be said that the larger this value, the more advantageous the device in terms of power consumption.

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

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

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

  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 methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429, 6023308, and the like can be applied.

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

  Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

Example 1
Using an ITO target having an In ₂ O ₃ content of 95% by mass on a glass substrate having a thickness of 0.7 mm and a 2.5 cm square, DC magnetron sputtering (conditions: substrate temperature 100 ° C., oxygen pressure 1 × 10 ⁻³ Pa), an ITO thin film (thickness 0.2 μm) was formed as a transparent anode. The surface resistance of the ITO thin film was 10Ω / □.
Next, the substrate on which the transparent anode was formed was placed in a cleaning container and subjected to IPA cleaning, and then UV-ozone treatment was performed for 30 minutes. On this transparent anode, a copper phthalocyanine was provided with a 10 nm-thickness hole injection layer at a rate of 0.5 nm / second by vacuum deposition.
Further, 4,4 ′, 4 ″ -tris (2-methylphenylphenylamino) triphenylamine (m-MTDATA) is transported by a vacuum deposition method at a rate of 0.5 nm / sec. A layer was provided.
On this, the compound H-5 as a hole transporting host compound in the light emitting layer, the compound E-3 as an electron transporting host compound in the light emitting layer, and the following platinum complex EM-1 (tetradentate coordination) as the light emitting material. Child complex) was co-evaporated at a ratio of 50/42/8 by a vacuum evaporation method to provide a light emitting layer having a thickness of 30 nm.

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

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

[Evaluation]
The hole injection layer used above, a hole transport layer, a hole transport material in the hole transport layer, a hole transport host compound in the light emitting layer, an electron transport host compound in the light emitting layer, an electron transport layer, The ion transport potential in the electron transport layer, the ionization potential (Ip) and the electron affinity (Ea) in the electron injection layer were each measured as a single layer film (single layer) by the following method. The results are shown in Table 1 below.

-Ionization potential (Ip)-
The ionization potential (Ip) was measured at room temperature and in the atmosphere using an ultraviolet photoelectron analyzer AC-1 (manufactured by Riken Keiki Co., Ltd.).

-Electron affinity (Ea)-
For the electron affinity (Ea), the band gap was calculated from the long wave end of the absorption spectrum of the single layer film, and the electron affinity (Ea) was calculated from the value of the ionization potential (Ip).

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

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

-Driving durability test-
Using a source measure unit 2400 made by KEITHLEY, a direct voltage was applied to the light emitting element so that the initial luminance was 300 cd / m ² , and a continuous driving test was performed.
The time when it became 0 cd / m ² was defined as the luminance half time T (1/2). The luminance half time was evaluated according to the following evaluation criteria.

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

( Reference Example 2)
In Example 1, instead of the metal complex (luminescent dopant) EM-1 in the present invention, a light emitting device was obtained in the same manner as in Example 1 except that the metal complex EM-2 was changed to the following, and the same evaluation was performed. A test was conducted. The results are shown in Table 1 below.

(Comparative Example 1)
Example 1 except that Example 1 was changed to FIrpic (bidentate ligand type complex) instead of metal complex (luminescent dopant) EM-1 (tetradentate ligand type complex) in the present invention. A light emitting device was obtained in the same manner as in No. 1, and the same evaluation test was performed. The results are shown in Table 1 below.

(Comparative Example 2)
In Example 1, without using the electron-transporting host material E-3, the hole-transporting host material H-5 and the metal complex (luminescent dopant) EM-1 in the present invention were applied by vacuum evaporation to 92/8. A light-emitting element was obtained in the same manner as in Example 1 except that the co-evaporation was performed at the ratio, and a similar evaluation test was performed. The results are shown in Table 1 below.

(Comparative Example 3)
In Example 1, the hole transporting host material H-5 was not used, the light emitting layer was formed of the electron transporting host material E-3, and the metal complex (light emitting dopant) EM-1 in the present invention was formed by a vacuum deposition method. A light emitting device was obtained in the same manner as in Example 1 except that co-evaporation was performed at a ratio of / 8, and the same evaluation test was performed. The results are shown in Table 1 below.

As is clear from Table 1, the device of the present invention (Example 1 and Reference Example 2) containing a metal complex having at least one tridentate or higher ligand and a plurality of host compounds in the light emitting layer is a comparative example. It turns out that it is excellent in luminous efficiency and durability with respect to 1-3.
The driving voltage can be lowered by the present invention, and an element excellent in power consumption can be provided.

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

Claims (6)

An organic electroluminescent element having an organic compound layer including at least one light emitting layer between a pair of electrodes, wherein the metal complex represented by the following general formula (1-A) and a hole transport property in the light emitting layer An organic electroluminescent device comprising a host compound and an electron transporting host compound.

(In General Formula (1-A), M ³¹ represents a platinum ion, X ³¹ and X ³² represent an oxygen atom, and Z ³¹ , Z ³² , Z ³³ , Z ³⁴ , Z ³⁵ , and Z ³⁶ are each independent. Represents a substituted or unsubstituted carbon atom, and the substituent on the carbon represents an alkyl group, an aryl group, a group that forms a condensed ring, or a halogen atom, and 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, and examples of the substituent on the carbon include an alkyl group, an aryl group, a group that forms a condensed ring, or Represents a halogen atom.) When the ionization potential of the metal complex is Ip (D) and the minimum of the ionization potentials of the hole transporting host compound and the electron transporting host compound is Ip (H) min, ΔIp = Ip ( D) -Ip (H) ΔIp defined by min the organic electroluminescent device according to claim 1, characterized by satisfying the relation Delta] Ip> 0 eV. When the electron affinity of the metal complex is Ea (D) and the maximum electron affinity of the hole transporting host compound and the electron transporting host compound is Ea (H) max, ΔEa = Ea (H ) DerutaEa defined by max-Ea (D) the organic electroluminescent device according to claim 1 or 2, characterized by satisfying the relation ΔEa> 0eV. 4. The organic electroluminescent element according to claim 2, wherein the ΔIp satisfies a relationship of 1.2 eV> ΔIp ≧ 0.2 eV. 5. The organic electroluminescent element according to claim 3, wherein the ΔEa satisfies a relationship of 1.2 eV>ΔEa> 0.2 eV. The organic electroluminescent element according to any one of claims 2 to 5 , wherein the Ip (H) min is 5.1 eV or more.