JP4969086B2 - Organic electroluminescence device - Google Patents

Description

  The present invention provides an organic electroluminescent device that emits light by converting electrical energy into light. In particular, the present invention relates to an organic electroluminescent element that can be driven at a low voltage and has high driving durability.

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 general, an organic electroluminescent element is composed of an organic compound layer including at least a light emitting layer and a pair of electrodes sandwiching the organic compound layer. When an electric field is applied between both electrodes, electrons are injected from the cathode and holes are injected from the anode. These electrons and holes recombine in the light emitting layer to generate excitons and emit light.
However, this organic electroluminescent element has a problem that its luminous efficiency is lower than that of an inorganic LED element or a fluorescent tube. There is a strong demand for further improvement in luminous efficiency and luminance. Moreover, in order to use an organic light emitting element also for the display part of a portable apparatus, it is preferable to reduce power consumption. From this point of view, it is desired to further reduce the drive voltage.

  In order to solve the above-mentioned problem and improve durability, for example, in Patent Document 1, a plurality of carrier injection layers are inserted at either or both of the interface between the anode and the light-emitting layer and the interface between the cathode and the light-emitting layer. Thus, it is described that an organic thin film EL element having excellent durability can be achieved. Patent Document 2 mainly discloses provision of a protective layer made of an organic material between a charged particle conductive layer to which impurities are added and a light emitting layer.

As for the light emitting material, for example, Patent Document 3 discloses an element using a complex having a tetradentate ligand as the light emitting material.
JP-A-6-314594 JP-T-2004-514257 US Pat. No. 6,653,654 B1

  An object of the present invention is to provide an organic electroluminescence device having low voltage driving and / or high driving durability.

  As a result of intensive studies, the present inventors have used a metal complex having a tridentate or more ligand as a light emitting material, provided a light emitting layer and a plurality of charge transport layers, and further, a light emitting layer and a plurality of charge transport layers. It has been found that driving durability can be improved by controlling the ionization potential and / or electron affinity between the two so as to satisfy a predetermined relationship, and the present invention has been completed.

The above problems are solved by the following organic electroluminescent elements <1> to <21>.
<1> An organic electroluminescent device having a plurality of organic compound layers including at least a light emitting layer containing a light emitting material and a host material and a hole transport layer between a pair of electrodes,
The hole transport layer is composed of two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (2) as a light emitting material,
Further, the ionization potential of the light emitting layer is Ip0, and among the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the ionization potential of the hole transport layer located nth from the light emitting layer side is Ipn. The organic electroluminescent element characterized by satisfying the relationship represented by the following formula (1).
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)

(In General Formula (2), M ⁵¹ represents a metal ion. Q ⁵¹ and Q ⁵² each independently represent an atomic group that forms a nitrogen-containing heterocycle with an adjacent carbon atom. Q ⁵³ and Q ⁵⁴ represent independently, .Y ⁵¹ represents a group which forms a (ring containing coordinating nitrogen M ⁵¹⁾ nitrogen-containing heterocyclic ring, the linking group, a single bond, or .L ⁵⁵ representing a double bond, Represents a ligand coordinated to M ^51. n ⁵¹ represents an integer of 0 to 4. W ⁵¹ and W ⁵² each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom.

<2> An organic electroluminescence device having a plurality of organic compound layers including at least a light emitting layer including a light emitting material and a host material and a hole transport layer between a pair of electrodes,
The hole transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (3) as a light emitting material,
In addition, the ionization potential of the light emitting layer is Ip0, and among the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the ionization potential of the hole transport layer located nth from the light emitting layer side An organic electroluminescent element satisfying the relationship represented by the following formula (1), where Ipn is:
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)

(In General Formula (3), M ^A1 represents a metal ion. Q ^A1 and Q ^A2 each independently represent an atomic group that forms a nitrogen-containing heterocycle with adjacent carbon atoms. Y ^A1 represents a linking group. Y ^A2 and Y ^A3 each independently represents a single bond or a linking group, and R ^A1 , R ^A2 , R ^A3 and R ^A4 each independently represent a hydrogen atom or R ^A1 and R ^A2 , R ^A3 and R ^A4 may be bonded to each other to form a ring, L ^A5 represents a ligand coordinated to M ^A1 , and n ^A1 is 0 to 0. Represents an integer of 4.)

<3> An organic electroluminescent device having a plurality of organic compound layers including at least a light emitting layer including a light emitting material and a host material and a hole transport layer between a pair of electrodes,
The hole transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (4) as a light emitting material,
In addition, the ionization potential of the light emitting layer is Ip0, and among the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the ionization potential of the hole transport layer located nth from the light emitting layer side An organic electroluminescent element satisfying the relationship represented by the following formula (1), where Ipn is:
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)

(In the general formula (4), M ^B1 represents a metal ion. Y ^B1 represents a linking group. Y ^B2 and Y ^B3 each independently represent a single bond or a linking group. R ^B1 , R ^B2 , R ^{B3, R B4} each independently represent a hydrogen atom or a ^substituent, coordinated to ^{R B1} and ^{R B2} and ^{R B3} and ^{R B4} may form a ring each coupled to the ^{.L B5} is ^{M B1} N ^B1 and n ^B2 each independently represents an integer of 0 or 1, except that n ^B1 and n ^B2 both become 1. n ^B3 is 0 to 4 X ^B1 and X ^B2 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom.

<4> The organic electroluminescent element according to any one of <1> to <3>, wherein the hole transport layer comprises three or more layers including a layer adjacent to the light emitting layer.

<5> In the case where the relationship represented by the formula (1) is satisfied, Ip0−Ip1 ≦ 0.4 eV, Ip1−Ip2 ≦ 0.4 eV,..., And Ipn−1−Ipn ≦ 0. 4. The organic electroluminescence device according to any one of <1> to <4>, wherein the relationship of 4 eV is satisfied.

<6> The above-mentioned <1>, wherein at least one of the hole transport layers contains a compound selected from the group consisting of an azepine compound, an amine compound, a carbazole compound, a pyrrole compound, and an indole compound. The organic electroluminescent element according to any one of> to <5>.
<7> Of the hole transport layer, the layer adjacent to the light emitting layer contains a compound selected from the group consisting of an azepine compound, an amine compound, a carbazole compound, a pyrrole compound, and an indole compound. The organic electroluminescent element as described in <6> .

<8> Further, it has an electron transport layer composed of two or more layers including a layer adjacent to the light emitting layer, and the electron affinity of the light emitting layer is Ea0, and among the electron transport layers, adjacent to the light emitting layer. When the electron affinity of the electron transport layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam, the relationship represented by the following formula (2) is satisfied: The organic electroluminescent element according to any one of 1> to <7>.
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

  <9> The organic electroluminescent element as described in <8>, wherein the electron transport layer has three or more layers.

  <10> In the case where the relationship represented by the formula (2) is satisfied, Ea1-Ea0 ≦ 0.2 eV, or Ea2-Ea1 ≦ 0.2 eV,..., Or Eam-Eam-1 ≦ 0. The organic electroluminescence device according to <8> or <9>, wherein the relationship of 2 eV is satisfied.

<11> An organic electroluminescent device having a plurality of organic compound layers including a light emitting layer including a light emitting material and a host material, and an electron transport layer between a pair of electrodes,
The electron transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the general formula (2) as a light emitting material,
The electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam. An organic electroluminescent element satisfying the relationship represented by the following formula (2).
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

(In General Formula (2), M ⁵¹ represents a metal ion. Q ⁵¹ and Q ⁵² each independently represent an atomic group that forms a nitrogen-containing heterocycle with an adjacent carbon atom. Q ⁵³ and Q ⁵⁴ represent independently, .Y ⁵¹ represents a group which forms a (ring containing coordinating nitrogen M ⁵¹⁾ nitrogen-containing heterocyclic ring, the linking group, a single bond, or .L ⁵⁵ representing a double bond, Represents a ligand coordinated to M ^51. n ⁵¹ represents an integer of 0 to 4. W ⁵¹ and W ⁵² each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom.

  <12> An organic electroluminescence device having a plurality of organic compound layers including at least a light-emitting layer including a light-emitting material and a host material, and an electron transport layer between a pair of electrodes,
  The electron transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
  The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the general formula (3) as a light emitting material,
  The electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam. An organic electroluminescent element satisfying the relationship represented by the following formula (2).
  Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

  (In general formula (3), M ^A1 Represents a metal ion. Q ^A1 , Q ^A2 Each independently represents an atomic group that forms a nitrogen-containing heterocycle with adjacent carbon atoms. Y ^A1 Represents a linking group, a single bond, or a double bond. Y ^A2 , Y ^A3 Each independently represents a single bond or a linking group. R ^A1 , R ^A2 , R ^A3 , R ^A4 Each independently represents a hydrogen atom or a substituent; ^A1 And R ^A2 And R ^A3 And R ^A4 May be bonded to each other to form a ring. L ^A5 Is M ^A1 Represents a ligand coordinated to n ^A1 Represents an integer of 0-4. )

  <13> An organic electroluminescence device having a plurality of organic compound layers including at least a light emitting layer including a light emitting material and a host material, and an electron transport layer between a pair of electrodes,
  The electron transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
  The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (4) as a light emitting material,
  The electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam. An organic electroluminescent element satisfying the relationship represented by the following formula (2).
  Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

  (In general formula (4), M ^B1 Represents a metal ion. Y ^B1 Represents a linking group. Y ^B2 , Y ^B3 Each independently represents a single bond or a linking group. R ^B1 , R ^B2 , R ^B3 , R ^B4 Each independently represents a hydrogen atom or a substituent; ^B1 And R ^B2 And R ^B3 And R ^B4 May be bonded to each other to form a ring. L ^B5 Is M ^B1 Represents a ligand coordinated to n ^B1 , N ^B2 Each independently represents an integer of 0 or 1. However, n ^B1 , N ^B2 Excluding those where both are 1. n ^B3 Represents an integer of 0-4. X ^B1 , X ^B2 Each independently represents an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. )

  <14> In the case where the relationship represented by the formula (2) is satisfied, Ea1−Ea0 ≦ 0.4 eV, Ea2−Ea1 ≦ 0.4 eV, and Eam−Eam−1 ≦ 0. The organic electroluminescent element according to any one of <1> to <13>, wherein the relationship of 4 eV is satisfied.

  <15> The organic electroluminescence device according to any one of <11> to <14>, wherein the electron transport layer is three or more layers.

  <16> The metal ions in the metal complex are selected from the group consisting of platinum ions, iridium ions, rhenium ions, palladium ions, rhodium ions, ruthenium ions, and copper ions. The organic electroluminescent element of any one of 15>.

  <17> The light emitting layers are first and second light emitting layers containing a light emitting material and a host material,
  The hole transport layer is composed of two or more layers including a layer adjacent to the first light emitting layer, and the electron transport layer is composed of two or more layers including a layer adjacent to the second light emitting layer,
  Any of the above <1> to <16>, wherein each of the first and second light emitting layers contains a different host material and a metal complex having the tridentate or higher ligand as the light emitting material. Item 1 is an organic electroluminescent device.

ADVANTAGE OF THE INVENTION According to this invention, it can provide that an organic electroluminescent element with a low drive voltage and / or high drive durability is provided.
In the present invention, the color purity can be further improved and multicolor emission (red, green, and / or blue, etc.) can be achieved by appropriately selecting the type of metal complex having a tridentate or higher ligand. Thus, it is possible to provide an organic electroluminescent device excellent in low voltage driving, high driving durability, and luminous efficiency.

  Hereinafter, the organic electroluminescence device of the present invention (hereinafter also referred to as “organic EL device” or “light emitting device”) will be described in detail. In the present specification, a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.

A first aspect of the present invention is an organic electroluminescent device having a plurality of organic compound layers including a light emitting layer containing at least a light emitting material and a host material and a hole transport layer between a pair of electrodes, The hole transport layer is composed of two or more layers including a layer adjacent to the light emitting layer, and the light emitting layer is a metal represented by the following general formula (2), general formula (3), or general formula (4) as a light emitting material. It contains a metal complex having a tridentate or higher ligand as a complex, and the ionization potential of the light emitting layer is Ip _0. Of the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip ₁ , an organic electroluminescence device characterized by satisfying the relationship represented by the following formula (1) when the ionization potential of the _nth hole transport layer located from the light emitting layer side is Ipn.
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)
With the above configuration, an organic electroluminescence device having high driving durability can be obtained.

  In the first aspect of the present invention, a metal complex having a tridentate or higher ligand having high stability (chemical stability, particularly excellent properties such as being difficult to decompose) is used, and adjacent to the light emitting layer. By providing two or more hole transport layers including a layer, and further controlling the ionization potential relationship between the light emitting layer and the two or more hole transport layers, injection of charges (holes) is promoted. It is estimated that high driving durability is exhibited.

  Further, in the present invention, one of the features is that a layer having the highest ionization potential is provided among two or more hole transport layers adjacent to the light emitting layer. As a result, the charge injection barrier is lowered and the retention of charges at the layer interface is suppressed. As a result, the deterioration of the material is suppressed, and a metal complex having a tridentate or higher ligand is formed. Combined with the effect to be used, it is estimated that it contributes to the remarkable improvement in driving durability.

A second aspect of the present invention is an organic electroluminescent device having a plurality of organic compound layers including at least a light emitting layer including a light emitting material and a host material and a plurality of organic compound layers including an electron transport layer between a pair of electrodes, The transport layer is composed of two or more layers including a layer adjacent to the light emitting layer, and the light emitting layer is a metal complex represented by the following general formula (2), general formula (3), or general formula (4) as a light emitting material. containing a metal complex having a certain tridentate or higher-dentate ligand, and the electron affinity of the light emitting layer EA0, the electron affinity of the electron transport layer adjacent to the luminescent layer Ea1, electrons located m-th from the light emitting layer side When the electron affinity of the transport layer is Eam, the organic electroluminescence device satisfies the relationship represented by the following formula (2).
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)
With the above configuration, an organic electroluminescence device having high driving durability can be obtained.

  Although the action resulting from the above configuration is not necessarily clear, the above-described highly stable metal complex having a tridentate or higher ligand is used, and the electron affinity between the light emitting layer and the electron transport layer existing in two or more layers is reduced. By controlling the relationship, it is presumed that charge (electron) injection is promoted and high driving durability is exhibited.

The third aspect of the present invention is a preferred aspect of the first and second aspects of the present invention, in which a light-emitting layer including at least a light-emitting material and a host material is interposed between a pair of electrodes, and hole transport. An organic electroluminescence device having a plurality of organic compound layers including a layer and an electron transport layer, wherein the hole transport layer and the electron transport layer are each composed of two or more layers including a layer adjacent to the light emitting layer, and emit light The layer contains a metal complex having a tridentate or higher ligand as the light emitting material, and the ionization potential of the light emitting layer is Ip0. Of the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, the ionization potential of the nth hole transport layer located from the light emitting layer side is Ipn, the electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, the light emission Mth from the layer side The electron affinity of location for the electron transport layer when the Eam, an organic electroluminescent device and satisfies the relation represented by the following formula (1) and the following formula (2).
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)
As in the third embodiment, two or more hole transport layers and electron transport layers are adjacent to the light emitting layer, and further, the relationship between the ionization potential and the electron affinity in each layer is controlled to further enhance driving durability. can do.

Moreover, as an organic electroluminescent element of the present invention, from the viewpoint of further improving driving durability, in the first to third embodiments, the light emitting layer is composed of two light emitting layers having different host materials (first and second layers). It may be configured to be a light emitting layer) . Immediate Chi, in this embodiment, the first and second light-emitting layer and contains a respective different host materials, and a metal complex having a tridentate or higher-dentate ligand as a light emitting material.

  The ionization potential (Ip) of each layer in the light emitting device of the present invention means an ionization potential of a material having the lowest ionization potential among materials contained in the layer of 10% by mass or more. As the ionization potential in this specification, a value measured using AC-1 (manufactured by Riken Keiki Co., Ltd.) at room temperature (preferably in a range of 15 ° C. or more and 25 ° C. or less) and in the atmosphere is adopted. 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) of each layer in the light emitting device of the present invention means the electron affinity of the material having the highest electron affinity among the materials contained in the layer of 10% by mass or more. The electron affinity in the present invention was determined by measuring the ultraviolet-visible absorption spectrum of the film used for measuring the ionization potential (preferably in the range of 15 degrees to 25 degrees) and obtaining the excitation energy from the energy at the long wavelength end of the absorption spectrum. The electron affinity was calculated from the excitation energy and the value of the ionization potential. In this specification, a value obtained by measuring a UV-visible absorption spectrum with a UV3100 spectrophotometer manufactured by Shimadzu Corporation was adopted.

In each light-emitting element according to the state like the present invention, the light emitting layer, a hole transport layer adjacent to the light-emitting layer, the relation of the ionization potentials of other hole-transporting layer (Ip), and / or, the light emitting layer, the light emitting It is necessary that the relationship between the electron transport layer adjacent to the layer and the electron affinity (Ea) of the other electron transport layer satisfy a predetermined relationship. That is, the first aspect satisfies the relationship represented by the following formula (1), the second aspect satisfies the relationship represented by the following formula (2), and the third aspect: It is necessary to satisfy the relationship represented by the formula (1) and the following formula (2).
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

Light emitting device of the present invention, an electron transport layer and / or hole transporting layer, it is necessary to have two or more layers. The hole transport layer is preferably 3 layers or more from the viewpoint of reducing the potential barrier between the layers, and preferably 4 layers or less from the viewpoint of ease of production. Also, the electron transport layer is preferably 3 layers or more from the viewpoint of reducing the potential barrier between the layers, and preferably 4 layers or less from the viewpoint of ease of production.

In the light-emitting element of the present invention, when emitting light layer is one layer, the ionization potential of the light-emitting layer (Ip0) is preferably at most 6.4 eV, more preferably at most 6.3 eV, and particularly preferably 6.2 eV. The electron affinity (Ea0) of the light emitting layer is preferably 2.1 eV or more, more preferably 2.2 eV or more, and particularly preferably 2.3 eV or more.

The ionization potential (Ip1) of the hole transport layer adjacent to the light emitting layer is preferably 6.2 to 5.3 eV, more preferably 6.1 to 5.4 eV, and particularly preferably 6.0 to 5.5 eV.
The ionization potential (Ip2, 3,...) Of the other hole transport layer is preferably 5.8 eV or less, more preferably 5.7 eV or less, and particularly preferably 5.6 eV or less.

The electron affinity (Ea1) of the electron transport layer adjacent to the light emitting layer is preferably 2.2 to 3.1 eV, more preferably 2.3 to 3.0 eV, and particularly preferably 2.4 to 2.9 eV.
The electron affinity (Ea2, 3,...) Of the other electron transport layer is preferably 2.6 eV or more, more preferably 2.7 eV or more, and particularly preferably 2.8 eV or more.

  The relationship between the ionization potential or the electron affinity in the present invention is controlled by selecting and combining the materials showing the above ionization potential or electron affinity from the materials constituting each layer.

In addition, regarding the relationship of electron affinity between each layer in the electron transport layer existing between two layers between the cathode and the light emitting layer, the difference in electron affinity between adjacent layers is 0.4 eV or less from the viewpoint of driving voltage reduction. It is preferable that it is 0.2 eV or less.
Specifically, in the case where the relationship of the formula (2) is satisfied, the relationship of the electron affinity between each layer of the light emitting layer and the electron transport layer is Ea1-Ea0 ≦ 0.4 eV and Ea2-Ea1 ≦ 0.4 eV. It is preferable that the relationship of Eam-Eam-1 ≦ 0.4 eV is satisfied, and Ea1-Ea0 ≦ 0.2 eV, or Ea2-Ea1 ≦ 0.2 eV, or Eam-Eam- It is preferable to satisfy the relationship of 1 ≦ 0.2 eV.

  If the difference in electron affinity between all adjacent layers in the electron transport layer is 0.2 eV or less, the number of layers of the electron transport layer may increase depending on the combination of the host material and the electrode material. In such a case, it is necessary to determine the configuration of the light emitting element so as to obtain a desired effect while paying attention to both the number of electron transport layers and the difference in electron affinity between layers.

On the other hand, regarding the relationship between the ionization potentials of each layer in the hole transport layer existing between two or more layers between the anode and the light emitting layer, the difference in ionization potential between adjacent layers is 0.4 eV or less from the viewpoint of driving voltage reduction. It is preferable that it is 0.2 eV or less.
Specifically, in the case where the relationship of the above formula (1) is satisfied, the relationship between the ionization potentials of the light emitting layer and the hole transport layer is Ip0−Ip1 ≦ 0.4 eV and Ip1−Ip2 ≦ 0. 4 eV,..., And Ipn-1-Ipn ≦ 0.4 eV, and Ip0-Ip1 ≦ 0.2 eV, or Ip1-Ip2 ≦ 0.2 eV,. It is preferable to satisfy the relationship of −Ipn ≦ 0.2 eV.

  If the difference in ionization potential between all adjacent layers in the hole transport layer is 0.2 eV or less, the number of hole transport layers may increase depending on the combination of the host material and the electrode material. In such a case, it is necessary to determine the configuration of the light emitting element so as to obtain a desired effect while paying attention to both the number of hole transport layers and the difference in ionization potential between the layers.

The light-emitting element of the present invention is characterized in that the light-emitting layer contains a metal complex having a tridentate or higher ligand (hereinafter sometimes simply referred to as “metal complex”). The light emitting layer in the present invention essentially includes a metal complex represented by the following general formula (2), general formula (3), or general formula (4) among metal complexes having a tridentate or higher ligand. contains. Hereinafter, a metal complex having a tridentate or higher ligand that can be applied to the present invention, including a metal complex represented by the following general formula (2), general formula (3), or general formula (4) will be described. To do.
The metal complex in the present invention may have either a chain ligand or a cyclic ligand, but a metal complex having a chain ligand of 3 or more and 8 or less is preferable, and 3 More preferred are metal complexes having a chain ligand of from 6 to 6 seats, more preferred are metal complexes having a tridentate or tetradentate chain ligand, and metal complexes having a tetradentate chain ligand Is particularly preferred.
The chain ligand is a nitrogen-containing heterocyclic ring (for example, for example, M ¹¹ in the case of a compound represented by the general formula (I) described below) coordinated with nitrogen. It preferably has at least one pyridine ring, quinoline ring, pyrrole ring and the like. The nitrogen-containing heterocycle is more preferably a nitrogen-containing 6-membered heterocycle.
In addition, as a tridentate or more ligand which the said metal complex has, it is preferable that it is an at least tridentate ligand except the ligand which consists of the following group A.
Group A: Tetradentate ligand containing bipyridyl or phenanthroline in the partial structure, Schiff base type tetradentate ligand, phenylbipyridyl tridentate ligand, diphenylpyridine tridentate ligand, and terpyridine tridentate ligand.

Here, 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 compound represented by the general formula (I) described later in detail, which is a metal complex having a chain ligand, will be described as an example. L ¹¹ and L ¹⁴ are Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and a ligand that is not linked without interposing M ¹¹ . Even if L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and L ¹⁴ contain a ring structure (eg, benzene, pyridine, quinoline, etc.), L ¹¹ and L ¹⁴ are Y ¹² , L If they are not linked via ¹² , Y ¹¹ , L ¹³ , Y ¹³ , or M ¹¹ , the ligand is called a chain ligand. Between L ¹¹ and Y ^12, Y ¹² and between the L ^12, L ¹² and between Y ^11, between Y ¹¹ and L ^13, L ¹³ and Y ^13, further atoms between Y ¹³ and L ¹⁴ Groups may be present to form a ring.
Further, that the ligand of the metal complex is cyclic means that a plurality of ligands in the metal complex are bonded to each other to form a closed structure (for example, phthalocyanine ligand, crown ether coordination). Etc.).

  The 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 Is more preferable.

  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 may be used alone or in combination of two or more.
Further, when two or more kinds of light emitting materials are used, a metal complex having a tridentate or higher ligand and other light emitting materials may be used in combination. Examples of other light-emitting materials that can be used in the present invention (light-emitting materials other than metal complexes having a tridentate or higher ligand) include fluorescent light-emitting materials and / or phosphorescent light-emitting materials. In the present invention, at least one of the light emitting materials may be a metal complex having a tridentate or higher ligand, and all of the light emitting materials are metal complexes having a tridentate or higher ligand. Preferably there is.

  The light-emitting material in the present invention may be a fluorescent compound or a phosphorescent compound, but is preferably a phosphorescent compound. (More preferably, phosphorescence is emitted at −30 ° C. or more, more preferably phosphorescence is emitted at −10 ° C. or more, more preferably phosphorescence is emitted at 0 ° C. or more, particularly preferably phosphorescence is emitted at 10 ° C. or more. .) In the case of using a phosphorescent compound, it may be one that emits fluorescence at the same time, but a compound having a phosphorescence intensity at 20 ° C. of 2 times or more is preferable, and a compound having 10 times or more is more preferable. A compound that is twice or more is more preferable.

  The light emitting material in the present invention is preferably a material having an emission quantum yield (phosphorescence or fluorescence) at 20 ° C. of 10% or more, more preferably an emission quantum yield at 20 ° C. of 15% or more, and light emission at 20 ° C. A material having a quantum yield of 20% or more is more preferable.

  The total content of the light emitting material in the present invention is preferably 0.1% by mass to 50% by mass, and more preferably 0.3% by mass to 40% by mass with respect to the mass of the light emitting layer. More preferably, it is 0.5 mass%-20 mass%.

  The content ratio in the case where at least two kinds of light emitting materials are contained in the light emitting layer is not particularly limited, but the ratio of the light emitting material / other light emitting materials from which the emission spectrum is derived is 100/1 to 1/10. Preferably, 20/1 to 1/5 is more preferable, and 5/1 to 1/2 is still more preferable. In this case, both the light emitting material from which the emission spectrum is derived / the other light emitting material may be a metal complex having a tridentate or higher ligand, and either one of them has a tridentate or higher ligand. It may be a metal complex.

  Hereinafter, the metal complex having a tridentate or higher ligand in the present invention will be described in detail. Note that other components in the light-emitting element of the present invention will be described in detail after the description of the metal complex having a tridentate or higher ligand.

  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 ⁶¹ , Y ⁶² , and Y ⁶³ in the general formula (3-A), and the preferred ranges are also the same.

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

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

Z ⁷¹ , Z ⁷² , Z ⁷³ , Z ⁷⁴ , Z ⁷⁵ , and Z ⁷⁶ each independently represent a substituted or unsubstituted carbon atom or a nitrogen atom, preferably a substituted or unsubstituted carbon atom. Examples of the substituent on carbon include the group described for R ²¹ in the general formula (1). 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. However, the case where both n ^B1 and n ^B2 are 1 is excluded.

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. The bond between M ^X3 and Y ^X31 to Y ^X36 may be a coordination bond, an ionic bond, or a covalent bond, respectively.

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.

Formula light emitting layer contains mandatory in the organic electroluminescent device of the present invention (1), the general formula (2), including the metals complex represented by the general formula (3), Formula (I), Specific examples of the compounds represented by the general formula (II) and the general formula (5) include compounds (1) to (242) and compounds (243) to (243) described in Japanese Patent Application No. 2004-162849. 246) (the structure is shown below) and the like, 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 represents a partial structure containing an atom bonded to M ^A1 .

The compound represented by formula (A-1) will be described in detail.
M ^A1 represents a metal ion. Although it does not specifically limit as a metal ion, A bivalent metal ion is preferable, Pt ^<2+> , Pd ^<2+> , Cu ^<2+> , Ni ^<2+> , Co ^<2+> , Zn ^<2+> , Mg ^<2+> , Pb <^2+> is preferable, Pt ^<2+> , 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 represents a partial structure containing an atom bonded to M ^A1 . 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 represents a partial structure containing an atom bonded to M ^B1 .

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 represent a partial structure containing an atom 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 .

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 represent a partial structure containing an atom bonded to M ^F1 .

The compound represented by formula (F-1) will be described in detail.
In General Formula (F-1), M ^F1 , L ^F11 , L ^F12 , L ^F13 , Q ^F11 , and Q ^F12 correspond to M ^A1 , L ^A11 , L ^A12 , and L ^{A13 in} General Formula (A-1), respectively. , Q ^A11 and Q ^A12 , and the preferred range is also the same. R ^F11 , R ^F12 , R ^F13 and R ^F14 each independently represent a hydrogen atom or a substituent, and R ^F11 and R ^F12 , R ^F12 and R ^F13 , 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.

  The organic electroluminescent element of the present invention is an element in which a plurality of organic compound layers including a light emitting layer and two or more hole transport layers and / or electron transport layers are formed between a pair of electrodes of an anode and a cathode. In addition to these layers, in addition to the light emitting layer, a hole injection layer, an electron injection layer, a protective layer, and the like may be included. Each of these layers may have other functions. Various materials can be used for forming each layer.

The elements constituting the organic electroluminescent element of the present invention will be further described.
Organic electroluminescence devices are roughly classified into a bottom emission method and a top emission method. The present invention can be preferably applied to any method. Hereinafter, the present invention will be described in detail by taking a bottom emission method as an example. A bottom emission type organic electroluminescent device usually has an anode / hole transport layer / light emitting layer / cathode configuration from the substrate side, or an anode / hole transport layer / light emitting layer / electron transport layer / cathode from the substrate side. It has a configuration. In the present invention, the light-emitting layer has a plurality of hole transport layers including a layer adjacent to the light-emitting layer, and / or a plurality of electrons including a light-emitting layer and a layer adjacent to the light-emitting layer. It is necessary to have a configuration having a transport layer. Furthermore, each layer may be divided into a plurality of secondary layers.
Moreover, it is preferable that at least one electrode of an anode and a cathode is transparent from the property of a light emitting element. Usually, the anode is transparent.

A typical configuration of the bottom emission light-emitting device of the present invention includes, from the substrate side, (1) a configuration of a transparent anode / a plurality of hole transport layers / light-emitting layers / electron transport layers / cathodes (first embodiment), ( 2) Configuration of transparent anode / hole transport layer / light emitting layer / multiple electron transport layers / cathode (second embodiment) or (3) transparent anode / multiple hole transport layers / single layer or two layers A configuration of a light emitting layer / a plurality of electron transport layers / cathodes ( third aspect) is adopted.

<Board>
The substrate used in the present invention preferably does not scatter or attenuate light emitted from the organic compound layer. Specific examples include inorganic materials such as yttrium-stabilized zirconia (YSZ), 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). 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. Generally, the shape is a plate shape. The structure may be a single layer structure, a laminated structure, may be formed of a single member, or may be formed of two or more members.
The substrate may be colorless and transparent or colored and transparent, but is preferably colorless and transparent in that it does not scatter or attenuate light emitted from the light emitting layer.

  The substrate can be provided with a moisture permeation preventive layer (gas barrier layer) on the front surface or back surface (transparent electrode side). 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. The thermoplastic substrate may be further provided with a hard coat layer, an undercoat layer or the like as necessary.

<Anode>
The anode usually has a function as an anode 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. Thus, it can be appropriately selected from known electrodes. 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, an organic conductive compound, or a mixture thereof can be preferably cited, and a material having a work function of 4.0 eV or more is preferable. Specific examples include semiconducting metal oxides such as tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metals such as gold, silver, chromium and nickel, and mixtures or laminates of these metals and conductive metal oxides, inorganic conductive materials such as copper iodide and copper sulfide, organic materials such as polyaniline, polythiophene and polypyrrole Examples thereof include conductive materials and laminates of these with ITO.

  For example, the anode is a wet method such as a printing method, a coating method, a physical method such as a vacuum deposition method, a sputtering method, an ion plating method, a chemical method such as a CVD method, a plasma CVD method, and the like. It can be formed on the substrate according to a method appropriately selected in consideration of suitability. For example, when ITO is selected as the material for the transparent anode, the transparent 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. Moreover, when selecting an organic electroconductive compound as a material of a transparent anode, it can carry out according to the wet film-forming method.

  There is no restriction | limiting in particular as a formation position of the anode in a light emitting element, Although it can select suitably according to the use and purpose of a light emitting element, forming on a board | substrate is preferable. In this case, the anode may be formed on the entire one surface of the substrate or may be formed on a part thereof. The patterning of the anode may be performed by chemical etching such as photolithography, or may be performed by physical etching using a laser or the like, or may be performed by 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, and is usually 10 nm to 50 μm, preferably 50 nm to 20 μm. The resistance value of the transparent anode is preferably 10 ³ Ω / □ or less, and more preferably 10 ² Ω / □ or less.

  When the anode is provided as a transparent anode and light emission is taken out from the anode side, the transmittance is preferably 60% or more, more preferably 70% or more. This transmittance can be measured according to a known method using a spectrophotometer. In this case, the anode may be colorless and transparent or colored and transparent. The anode is described in detail in “New Development of Transparent Electrode Film”, published by CMC (1999), supervised by Yutaka Sawada, and these can be applied to the present invention. When using a plastic substrate having low heat resistance, an anode formed using ITO or IZO at a low temperature of 150 ° C. or less is preferable.

<Cathode>
The cathode usually has a function as a cathode 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. , Can be appropriately selected from known electrodes.

  Examples of the material for 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-silver alloys, rare earth metals such as indium and 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, alkali metals and alkaline earth metals are preferable from the viewpoint of electron injection properties, and materials mainly composed of aluminum are preferable from the viewpoint of excellent storage stability. The material mainly composed of aluminum is aluminum alone, or an alloy or mixture of aluminum and 0.01 to 10% by mass of an alkali metal or alkaline earth metal (for example, lithium-aluminum alloy, magnesium-aluminum alloy, etc.). Say. The cathode material is described in detail in JP-A-2-15595 and JP-A-5-121172.

  There is no restriction | limiting in particular in the formation method of a cathode, It can carry out according to a well-known method. For example, suitability with the above materials from among wet methods such as printing methods, coating methods, physical methods such as vacuum deposition methods, sputtering methods and ion plating methods, chemical methods such as CVD and plasma CVD methods, etc. It can be formed according to a method appropriately selected in consideration. 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.

  The patterning of the cathode may be performed by chemical etching such as photolithography, may be performed by physical etching using a laser, etc., may be performed by vacuum deposition or sputtering with a mask overlapped, lift-off method, You may carry out by the printing method.

  There is no restriction | limiting in particular as a formation position of the cathode in the laminated body (light-emitting laminated body) obtained by laminating | stacking an electrode and an organic compound layer, It may be formed in the whole on an organic compound layer, and the part It may be formed.

  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 and cannot be generally defined, but is usually 10 nm to 5 μm, and preferably 50 nm to 1 μm.

  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.

<Organic compound layer>
-Formation of organic compound layer-
The method for forming the organic compound layer in the present invention is not particularly limited, but resistance heating vapor deposition, electrophotography, electron beam method, sputtering method, molecular lamination method, coating method (spray coating method, dip coating method, impregnation method, roll) Coating method, gravure coating method, reverse coating method, roll brush method, air knife coating method, curtain coating method, spin coating method, flow coating method, bar coating method, micro gravure coating method, air doctor coating, blade coating method, squeeze Coating methods, transfer roll coating methods, kiss coating methods, cast coating methods, extrusion coating methods, wire bar coating methods, screen coating methods, etc.), ink jet methods, printing methods, transfer methods and the like are possible. Among these, the resistance heating vapor deposition method, the coating method, and the transfer method are preferable in consideration of the characteristics of the element, the ease of manufacture, the cost, and the like. When the light-emitting element has a stacked structure of two or more layers, it can be manufactured by combining the above methods.

  In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N-vinylcarbazole). , Hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicon resin and the like.

-Hole transport layer, hole injection layer-
The material of the hole transport layer or the hole injection layer has any one of the function of injecting holes from the anode, the function of transporting holes, and the function of blocking electrons injected from the cathode. That's fine. The hole transport layer in the present invention includes a layer generally referred to as a hole injection layer.
Specific examples of the material of the hole transport layer or the hole injection layer include carbazole, imidazole, dibenzoazepine, tribenzoazepine, triazole, oxazole, oxadiazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, Amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compounds, styrylamine, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline compounds Examples thereof include polymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organometallic complexes, transition metal complexes, and derivatives of the above compounds.

  In the present invention, from the viewpoint of reducing driving voltage and improving durability, at least one of the hole transport layers is formed of an azepine compound, an amine compound, a carbazole compound, a pyrrole compound, and an indole compound. It is preferred to include any of the selected compounds. Of the hole transport layer, the layer adjacent to the light emitting layer preferably contains a compound selected from the group consisting of an azepine compound, an amine compound, a carbazole compound, a pyrrole compound, and an indole compound.

In the present invention, as the material for the hole transport layer adjacent to the light emitting layer, carbazole, phenylenediamine, arylamine, aromatic tertiary amine compound, dibenzoazepine, and tribenzoazepine are preferable among the above, and carbazole, aromatic More preferred are group III tertiary amine compounds and tribenzazepine.
Among the above hole transport layers, carbazole, phenylenediamine, arylamine, aromatic tertiary amine compounds, dibenzoazepine, and tribenzoazepine are preferable among the above materials, and carbazole, aromatic tertiary amine. More preferred is the compound, tribenzoazepine.

In the first and third aspects of the present invention, as described above, the ionization potential of the light emitting layer is Ip0, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the positive position is nth from the light emitting layer side. When the ionization potential of the hole transport layer is Ipn, it is necessary to satisfy the relationship represented by the following formula (1).
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)
In selecting the material constituting the hole transport layer present in two or more layers, the relationship with the material contained in the light emitting layer is considered.

  The film 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 transport layer may have a single-layer structure composed of one or more of the above-described materials, or a multilayer structure composed of a plurality of layers having the same composition or different compositions.

  Moreover, an electron-accepting dopant can be contained in the hole injection layer and the hole transport layer. The electron-accepting dopant introduced into the hole-injecting layer and the hole-transporting layer can be either an inorganic compound or an organic compound as long as it has an electron-accepting property and oxidizes an organic compound. Can be suitably used Lewis acid compounds such as ferric chloride, aluminum chloride, gallium chloride, indium chloride, and antimony pentachloride.

  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. The amount of the electron-accepting dopant used varies depending on the type of material, but is preferably 0.01% by mass to 50% by mass with respect to the material contained in the hole transport layer or the hole injection layer. It is more preferable that it is 05 mass%-20 mass%, and it is especially preferable that it is 0.1 mass%-10 mass%.

-Electron transport layer, electron injection layer-
The material of the electron transport layer or the electron injection layer may be any material having any one of the function of injecting electrons from the cathode, the function of transporting electrons, and the function of blocking holes injected from the anode. . The electron transport layer in the present invention includes a layer generally referred to as an electron injection layer.
Specific examples of the material for the electron transport layer or the electron injection layer include, for example, pyridine, pyrimidine, triazole, triazine, oxazole, phenanthroline, oxadiazole, imidazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandi. Aromatic tetracarboxylic anhydrides such as oxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, silole, imidazopyridine, naphthaleneperylene, metal complexes of phthalocyanine and 8-quinolinol derivatives, metal phthalocyanine, benzoxazole and benzothiazole Examples include various metal complexes represented by metal complexes as ligands, and derivatives of the above compounds.

In the present invention, as the material for the electron transport layer adjacent to the light emitting layer, among the above, pyridine, pyrimidine, triazine, phenanthroline, oxadiazole, imidazole, silole, and imidazopyridine are preferable, and triazine, oxadiazole, imidazole, More preferred is imidazopyridine.
Among the above-mentioned materials for the other electron transport layers, pyridine, pyrimidine, triazine, phenanthroline, oxadiazole, imidazole, silole, and imidazopyridine are preferable, and triazine, phenanthroline, oxadiazole, imidazole, silole, and imidazo Pyridine is more preferred.

In the second and third aspects of the present invention, as described above, the electron affinity of the light emitting layer is Ea0, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron located at the mth position from the light emitting layer side. When the electron affinity of the transport layer is Eam, it is necessary to satisfy the relationship represented by the following formula (2).
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)
In selecting the material constituting the electron transport layer that is present in two or more layers, the relationship with the material contained in the light emitting layer is considered.

  The film thicknesses of the electron injection layer and the electron 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. The electron injection layer and the electron transport layer may have a single-layer structure made of one or more of the materials described above, or may have a multilayer structure made up of a plurality of layers having the same composition or different compositions.

  Moreover, an electron donating dopant can be contained in the electron injection layer and the electron transport layer. The electron-donating dopant introduced into the electron-injecting layer and 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, 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. Although the usage-amount of an electron-donating dopant changes with kinds of material, it is preferable that it is 0.1 mass%-99 mass% with respect to the material contained in an electron carrying layer or an electron injection layer, and 1.0 mass% It is more preferable that it is -80 mass%, and it is especially preferable that it is 2.0 mass%-70 mass%.

-Light emitting layer-
The light emitting layer in the present invention is a layer containing a light emitting material and a host material.
The host material receives holes from the hole transport layer or hole injection layer when a voltage is applied, and also receives electrons from the electron injection layer or electron transport layer, functions to move injected charges, holes and electrons. It is a material that has a function of providing a recombination field to generate excitons and a function of transferring excitation energy.

  Examples of host materials that can be used in the present invention include, for example, benzoxazole, benzimidazole, benzothiazole, polyphenyl, coumarin, oxadiazole, pyralidine, pyrrolopyridine, thiadiazolopyridine, aromatic dimethylidin compounds, carbazole, imidazole. , Triazole, oxazole, oxadiazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, fluorenone, hydrazone, silazane, aromatic tertiary amine compound, aromatic dimethylidin compound, porphyrin compound, Various metal complexes represented by polysilane compounds, poly (N-vinylcarbazole), metal complexes having benzoxazole or benzothiazole as a ligand, or the above compounds Conductor, and the like. The host material may be a single material or a mixture of a plurality of types.

  The total content of the host material in the light emitting layer is preferably 50% by mass to 99.9% by mass, more preferably 60% by mass to 99.7% by mass with respect to the mass of the light emitting layer. 80% by mass to 99.5% by mass is even more preferable.

Incidentally, In no event luminescent layer is composed of the first light-emitting layer and the second light-emitting layer in the present invention, each of the first light-emitting layer and the second light-emitting layer, to contain different specific host materials is necessary.

  The preferred materials for the light emitting material contained in the light emitting layer are as described above.

Although the thickness of a light emitting layer is not specifically limited, Usually, it is preferable that they are 1 nm-500 nm, it is more preferable that they are 5 nm-200 nm, and it is still more preferable that they are 10 nm-100 nm.
In addition, as in the fourth or fifth aspect, the thickness of each light emitting layer is not particularly limited in the case of providing a plurality of light emitting layers, but is preferably 1 nm to 250 nm, It is more preferably 2 nm to 100 nm, and further preferably 5 nm to 50 nm.
Moreover, when a light emitting layer is a several layer, the light emitting material contained in each light emitting layer may be the same, or may differ. Although the number of the light emitting layers laminated | stacked is not specifically limited, 2-3 layers are preferable.
Furthermore, by using two or three or more different light emitting materials, light emitting elements of any color can be obtained. For example, white light can be emitted using a light emitting material that emits a complementary color such as blue light emission / yellow light emission, light blue light emission / orange light emission, and green light emission / purple light emission. Further, white light can be emitted using a light emitting material of blue light emission / green light emission / red light emission.
Note that the host material may function as a light emitting material to emit light. For example, the element may emit white light by light emission of the host material and light emission of the light emitting material.

  Furthermore, two or more kinds of different light emitting materials may be included in the same light emitting layer, and for example, blue light emitting layer / green light emitting layer / red light emitting layer or blue light emitting layer / yellow light emitting layer, respectively. A structure in which layers containing the light emitting material are stacked may be used.

In order to improve the light emission efficiency, the organic electroluminescence device of the present invention can have a configuration in which a charge generation layer is provided when there are a plurality of light emitting layers.
The charge generation layer is a layer having a function of generating charges (holes and electrons) when an electric field is applied and a function of injecting the generated charges into an adjacent layer.
The material for forming the charge generation layer is not particularly limited as long as the material has the above function, and may be a single compound or a plurality of compounds.
Specifically, even if it has electroconductivity, it may have semiconductivity like a doped organic compound layer. Moreover, you may have electrical insulation. Examples thereof include materials described in JP-A-11-329748, JP-A-2003-272860, and JP-A-2004-39617.
When the organic electroluminescent device of the present invention is a device having a charge generation layer or the like between the anode and the cathode, the unit between the electrode and the charge generation layer, or each unit between the charge generation layers, It is preferable to apply the configuration of the present invention.

<Protective layer>
In the present invention, the entire light emitting element may be protected by a protective layer. As a material for the protective layer, any material may be used as long as it has a function of suppressing the entry of elements that promote element deterioration such as moisture and oxygen into the element. 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 SiNx and SiNxOy, metal fluorides such as MgF ₂ , LiF, AlF ₃ and CaF ₂ , polyethylene, polypropylene, polymethyl methacrylate, polyimide, Copolymerizing polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, and a monomer mixture containing tetrafluoroethylene and at least one comonomer. Copolymer obtained, and a fluorine-containing copolymer having a cyclic structure in the copolymer main chain. Examples thereof include an elemental copolymer, a water-absorbing substance having a water absorption of 1% or more, and a moisture-proof substance having a water absorption of 0.1% or less.

  There is no particular limitation on the method for forming the protective layer. For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency excitation ions) Plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, and transfer method can be applied.

<Sealing>
Furthermore, in this invention, you may seal the whole element of this invention 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. The moisture absorbent is not particularly limited, but for example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride, fluorine Examples thereof include cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, and magnesium oxide. The inert liquid is not particularly limited, and examples thereof include paraffins, liquid paraffins, fluorinated solvents such as perfluoroalkane, perfluoroamine, and perfluoroether, chlorinated solvents, and silicone oils. .

<Element drive>
The light-emitting element of the present invention obtains light emission by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 40 volts) or a direct current between the transparent anode and the cathode. be able to. Regarding the driving of the light emitting device of the present invention, each publication of JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, JP-A-8-2441047 and the like. US Pat. Nos. 5,828,429, 6,023,308, and Japanese Patent No. 2,784,615 can be used.

  Hereinafter, the organic electroluminescence device of the present invention will be described with reference to examples, but the present invention is not limited to these examples.

1. Preparation of organic electroluminescent element (1) Preparation of organic electroluminescent element of comparative example (element 1) A glass substrate having a 0.5 mm thickness and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) After putting into a washing container and ultrasonically washing in 2-propanol, UV-ozone treatment was performed for 30 minutes. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
The vapor deposition rate in the examples of the present invention is 0.2 nm / second unless otherwise specified. The deposition rate was measured using a quartz resonator. The film thicknesses described below were also measured using a crystal resonator.
The ionization potential and electron affinity value of each organic compound layer in the element 1 are also shown in the configuration of each layer.

(Hole transport layer)
NPD: film thickness 40nm
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
(Electron transport layer)
BAlq: film thickness 45 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV

  The structures of NPD, mCP, BPM-1 and BAlq are shown below.

Finally, metal aluminum was deposited to a thickness of 100 nm to form a cathode.
This is put in a glove box substituted with argon gas without being exposed to the atmosphere, and sealed with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). And the organic electroluminescent element (element 1) of the comparative example was obtained.

(2) Preparation of organic electroluminescent element (element 2) of Example In the same manner as the organic electroluminescent element (element 1) of the comparative example, except that the configuration of the organic compound layer was changed as follows, the example An organic electroluminescent element (element 2) was prepared. The ionization potential and the electron affinity value of each organic compound layer in the element 2 are shown together in the configuration of each layer.

(First hole transport layer)
CuPc: film thickness 10 nm
Ionization potential: 5.1 eV, electron affinity: 3.4 eV
(Second hole transport layer)
NPD: film thickness 30nm
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
(First electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Second electron transport layer)
Alq: film thickness 40 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

  The structures of NPD, mCP, BPM-1 and BAlq are as described above. The structures of CuPc and Alq are shown below.

(3) Preparation of Organic Electroluminescent Element (Element 3) of Example The organic electric field of the example was prepared in the same manner as the organic electroluminescent element (element 1) of the comparative example, except that the organic compound layer configuration was changed as follows. A light emitting element (element 3) was manufactured. The ionization potential and electron affinity value of each organic compound layer in the element 3 are shown together in the configuration of each layer.

(First hole transport layer)
m-MTDATA: film thickness 10 nm
Ionization potential: 5.1 eV, electron affinity: 1.9 eV
(Second hole transport layer)
NPD: film thickness 30nm
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
(First electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Second electron transport layer)
Alq: film thickness 40 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

  The structures of NPD, mCP, BPM-1, BAlq, and Alq are as described above. The structure of m-MTDATA is shown below.

(4) Preparation of organic electroluminescent element (element 4) of Example The present invention was prepared in the same manner as the organic electroluminescent element (element 1) of the comparative example, except that the configuration of the organic compound layer was changed as follows. An organic electroluminescent element (element 4) was produced. The ionization potential and the electron affinity value of each organic compound layer in the element 4 are shown together in the configuration of each layer.

(First hole transport layer)
Copper phthalocyanine: film thickness 10nm
Ionization potential: 5.1 eV, electron affinity: 3.4 eV
(Second hole transport layer)
NPD: 25 nm film thickness
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Third hole transport layer)
HTM-1: 5 nm
Ionization potential: 5.8 eV, electron affinity: 2.2 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
(First electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Second electron transport layer)
Alq: film thickness 40 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

  The structures of copper phthalocyanine, NPD, mCP, BPM-1, BAlq, and Alq are as described above. The structure of HTM-1 is shown below.

(5) Preparation of organic electroluminescent element (element 5) of Example The present invention was prepared in the same manner as the organic electroluminescent element (element 1) of the comparative example, except that the configuration of the organic compound layer was changed as follows. An organic electroluminescent element (element 5) was produced. The ionization potential and electron affinity value of each organic compound layer in the element 5 are shown together in the configuration of each layer.

(First hole transport layer)
Copper phthalocyanine: film thickness 10nm
Ionization potential: 5.1 eV, electron affinity: 3.4 eV
(Second hole transport layer)
NPD: 25 nm film thickness
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Third hole transport layer)
HTM-1: 5 nm
Ionization potential: 5.8 eV, electron affinity: 2.2 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
(First electron transport layer)
ETM-1: film thickness 5nm
Ionization potential: 6.1 eV, electron affinity: 2.5 eV
(Second electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Third electron transport layer)
Alq: film thickness 35 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

  The structures of the copper phthalocyanine, NPD, HTM-1, mCP, BPM-1, BAlq, and Alq are as described above. The structure of ETM-1 is shown below.

(6) Preparation of organic electroluminescent element (element 6) of Example The present invention was prepared in the same manner as the organic electroluminescent element (element 1) of the comparative example, except that the configuration of the organic compound layer was changed as follows. An organic electroluminescent element (element 6) was produced. The ionization potential and the electron affinity value of each organic compound layer in the element 6 are shown together in the configuration of each layer.

(First hole transport layer)
Copper phthalocyanine: film thickness 10nm
Ionization potential: 5.1 eV, electron affinity: 3.4 eV
(Second hole transport layer)
NPD: 25 nm film thickness
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Third hole transport layer)
HTM-2: 5 nm
Ionization potential: 5.7 eV, electron affinity: 2.3 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
(First electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Second electron transport layer)
Alq: film thickness 40 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

  The structures of copper phthalocyanine, NPD, mCP, BPM-1, BAlq, and Alq are as described above. The structure of HTM-2 is shown below.

(7) Preparation of organic electroluminescent element (element 7) of Example The present invention was prepared in the same manner as the organic electroluminescent element (element 1) of the comparative example, except that the configuration of the organic compound layer was changed as follows. An organic electroluminescent element (element 7) was produced. The ionization potential and the electron affinity value of each organic compound layer in the element 7 are shown together in the configuration of each layer.

(First hole transport layer)
Copper phthalocyanine: film thickness 10nm
Ionization potential: 5.1 eV, electron affinity: 3.4 eV
(Second hole transport layer)
NPD: 25 nm film thickness
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Third hole transport layer)
HTM-2: Film thickness 5nm
Ionization potential: 5.7 eV, electron affinity: 2.3 eV
(Light emitting layer)
Mixed layer of mCP = 95 mass%, BPM-1 = 5 mass%: film thickness 35 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
(First electron transport layer)
ETM-1: film thickness 5nm
Ionization potential: 6.1 eV, electron affinity: 2.5 eV
(Second electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Third electron transport layer)
Alq: film thickness 35 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

  The structures of copper phthalocyanine, NPD, HTM-2, mCP, BPM-1, ETM-1, BAlq, and Alq are as described above.

(8) Preparation of organic electroluminescent element (element 8 and element 9) of Example Organic electroluminescent element (element 7) of Example except that HTM-2 used in element 6 was replaced with HTM-3 shown below. The organic electroluminescent element (element 8) of the present invention was produced by the same method as that described above.
Moreover, the organic electroluminescent element (element 9) of the present invention was produced in the same manner as the organic electroluminescent element (element 7) of the example except that HTM-2 used for the element 7 was replaced with HTM-3 shown below. Was made.
HTM-3 has an ionization potential of 5.8 eV and an electron affinity of 2.5 eV.

(9) Preparation of organic electroluminescent element (element 10 to element 15) of Reference Example The organic electric field of the example except that BPM-1 used for element 4 to element 9 was replaced with BPM-2 shown below, respectively. Organic electroluminescent elements (elements 10 to 15) of reference examples were produced in the same manner as the light emitting elements (elements 4 to 9).

(10) Preparation of Organic Electroluminescent Element (Element 16) of Comparative Example The organic electroluminescent element (element 16) of the comparative example was fabricated in the same manner as element 1, except that the configuration of the organic compound layer was changed as follows. Produced. The ionization potential and the electron affinity value of each organic compound layer in the element 16 are shown together in the configuration of each layer.

(First hole transport layer)
Copper phthalocyanine: film thickness 10nm
Ionization potential: 5.1 eV, electron affinity: 3.4 eV
(Second hole transport layer)
NPD: 25 nm film thickness
Ionization potential: 5.4 eV, electron affinity: 2.4 eV
(Third hole transport layer)
HTM-1: 5 nm
Ionization potential: 5.8 eV, electron affinity: 2.2 eV
(Light emitting layer)
Mixed layer of mCP = 95% by mass, Ir (ppy) ₃ = 5% by mass: film thickness 30 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
Mixed layer of CBP = 95 mass%, Ir (ppy) ₃ = 5 mass%: film thickness 30 nm
Ionization potential: 6.1 eV, electron affinity: 2.7 eV
(First electron transport layer)
BAlq: film thickness 5 nm
Ionization potential: 5.9 eV, electron affinity: 2.9 eV
(Second electron transport layer)
Alq: film thickness 40 nm
Ionization potential: 5.8 eV, electron affinity: 3.0 eV

The structures of NPD, mCP, BAlq, and Alq are as described above. The structures of CBP and Ir (ppy) ₃ are shown below.

(11) Preparation of organic electroluminescent element (element 17) of Example In the organic electroluminescent element (element 16) of the comparative example, the organic electroluminescent element (element 16) of the comparative example was changed except that the light emitting layer was changed to the following. The organic electroluminescent element (element 17) of the present invention was produced in the same manner as described above.
(Light emitting layer)
Mixed layer of mCP = 95 mass%, GPM-1 = 5 mass%: film thickness 30 nm
Ionization potential: 6.0 eV, electron affinity: 2.4 eV
CBP = 95 mass%, GPM-1 = 5 mass% mixed layer: film thickness 30 nm
Ionization potential: 6.1 eV, electron affinity: 2.7 eV
The structure of GPM-1 is shown below.

In addition, in the element 17, the white light emitting element of this invention can also be obtained by changing a light emitting layer into the following.
(Light emitting layer)
CBP = 90 mass%, BPM-1 = 10 mass% mixed layer: film thickness 20 nm
CBP = 95 mass%, RPM-1 = 5 mass% mixed layer: film thickness 20 nm
The structure of RPM-1 is shown below.

2. Evaluation of material properties (1) Ionization potential Each compound used in the organic compound layer was deposited on a glass substrate so as to have a thickness of 50 nm. The ionization potential of this membrane was measured with an ultraviolet photoelectron analyzer AC-1 manufactured by Riken Keiki Co., Ltd. under normal temperature and normal pressure. The results are shown in Table 1.

(2) Electron affinity The ultraviolet-visible absorption spectrum of the film used for measuring the ionization potential was measured with a UV3100 spectrophotometer manufactured by Shimadzu Corporation, and the excitation energy was determined from the energy at the long wavelength end of the absorption spectrum. The electron affinity was calculated from the excitation energy and the value of the ionization potential. The results are shown in Table 1.

3. Evaluation of organic electroluminescent element The driving durability of the organic electroluminescent elements (elements 1 to 17) obtained above was evaluated by the following method.
The obtained organic electroluminescent elements (elements 1 to 17) were driven at a constant current at an initial luminance of 300 cd / m ² , and the time (t _0.5 ) required for the luminance to reach 150 cd / m ² was measured. It was used as an index of sex.

For element 1 to element 15, when t _0.5 of element 1 is 1, 3.5 times or more is A, 1.5 times or more and less than 3.5 times B, 1.5 times The following were evaluated as C. The results are shown in Table 2.
Further, with respect to the element 16 and the element 17, when the t _0.5 for element 16 and 1, those of not less than 3.5 times A, of less than 1.5 times 3.5 times B, 1. A value of 5 times or less was evaluated as C. The results are shown in Table 3.

As shown in Table 2, it can be seen that the organic electroluminescent elements (elements 2 to 9 ) of the examples have higher driving durability than the organic electroluminescent elements (element 1) of the comparative example.
Further, as shown in Table 3, it can be seen that the organic electroluminescent element (element 17) of the example has higher driving durability than the organic electroluminescent element (element 16) of the comparative example.

Moreover, in each element obtained above, a similar element was prepared except that BPM-1, BPM-2, or GPM-1 was replaced with the compound represented by the general formula (II) or the general formula (III). As a result, an element excellent in driving durability was obtained.

Claims (17)

An organic electroluminescent device having a plurality of organic compound layers including a light emitting layer containing at least a light emitting material and a host material and a hole transport layer between a pair of electrodes,
The hole transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (2) as a light emitting material,
In addition, the ionization potential of the light emitting layer is Ip0, and among the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the ionization potential of the hole transport layer located nth from the light emitting layer side An organic electroluminescent element satisfying the relationship represented by the following formula (1), where Ipn is:
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)

(In General Formula (2), M ⁵¹ represents a metal ion. Q ⁵¹ and Q ⁵² each independently represent an atomic group that forms a nitrogen-containing heterocycle with an adjacent carbon atom. Q ⁵³ and Q ⁵⁴ represent independently, .Y ⁵¹ represents a group which forms a (ring containing coordinating nitrogen M ⁵¹⁾ nitrogen-containing heterocyclic ring is communicating Yuimoto a single bond, or .L ⁵⁵ representing a double bond , ^{.n 51} representing a ligand coordinated to ^{M 51} is ^{.W 51, W 52} represents an integer of 0 to 4 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom.) An organic electroluminescent device having a plurality of organic compound layers including a light emitting layer containing at least a light emitting material and a host material and a hole transport layer between a pair of electrodes,
The hole transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (3) as a light emitting material,
In addition, the ionization potential of the light emitting layer is Ip0, and among the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the ionization potential of the hole transport layer located nth from the light emitting layer side An organic electroluminescent element satisfying the relationship represented by the following formula (1), where Ipn is:
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)

(In General Formula (3), M ^A1 represents a metal ion. Q ^A1 and Q ^A2 each independently represent an atomic group that forms a nitrogen-containing heterocycle with adjacent carbon atoms. Y ^A1 represents a linking group. Y ^A2 and Y ^A3 each independently represents a single bond or a linking group, and R ^A1 , R ^A2 , R ^A3 and R ^A4 each independently represent a hydrogen atom or R ^A1 and R ^A2 , R ^A3 and R ^A4 may be bonded to each other to form a ring, L ^A5 represents a ligand coordinated to M ^A1 , and n ^A1 is 0 to 0. Represents an integer of 4.) An organic electroluminescent device having a plurality of organic compound layers including a light emitting layer containing at least a light emitting material and a host material and a hole transport layer between a pair of electrodes,
The hole transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (4) as a light emitting material,
In addition, the ionization potential of the light emitting layer is Ip0, and among the hole transport layers, the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip1, and the ionization potential of the hole transport layer located nth from the light emitting layer side An organic electroluminescent element satisfying the relationship represented by the following formula (1), where Ipn is:
Formula (1): Ip0>...>Ipn-1> Ipn (n is an integer of 2 or more)

(In the general formula (4), M ^B1 represents a metal ion. Y ^B1 represents a linking group. Y ^B2 and Y ^B3 each independently represent a single bond or a linking group. R ^B1 , R ^B2 , R ^{B 3} and R ^B4 each independently represent a hydrogen atom or a substituent, and R ^B1 and R ^B2 and R ^B3 and R ^B4 may be bonded to each other to form a ring, and L ^B5 is coordinated to M ^B1 . N ^B1 and n ^B2 each independently represents an integer of 0 or 1, except that n ^B1 and n ^B2 both become 1. n ^B3 is 0 to 4 X ^B1 and X ^B2 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. The organic electroluminescence device according to any one of claims 1 to 3 wherein the hole-transporting layer is characterized by three or more layers der Rukoto including a layer adjacent to the light emitting layer. In the case where the relationship represented by the formula (1) is satisfied, a relationship of Ip0−Ip1 ≦ 0.4 eV, Ip1−Ip2 ≦ 0.4 eV,..., And Ipn−1−Ipn ≦ 0.4 eV The organic electroluminescent element according to claim 1, wherein: Among the hole transport layer, at least one layer, azepine compounds, amine compounds, carbazole compounds, pyrrole compounds, and claims 1, characterized in that it comprises a compound selected from the group consisting of indole compound 6. The organic electroluminescent element according to any one of 5 above. 7. The compound according to claim 6 , wherein the hole transport layer includes a compound selected from the group consisting of an azepine compound, an amine compound, a carbazole compound, a pyrrole compound, and an indole compound in a layer adjacent to the light emitting layer. The organic electroluminescent element as described.   Furthermore, it has an electron transport layer composed of two or more layers including a layer adjacent to the light emitting layer, and the electron affinity of the light emitting layer is Ea0, and of the electron transport layers, the electron transport layer adjacent to the light emitting layer The relationship represented by the following formula (2) is satisfied, where Ea1 is the electron affinity of the light-emitting layer and Eam is the electron affinity of the m-th electron transport layer from the light emitting layer side. Item 8. The organic electroluminescent device according to any one of Items 7.
  Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more) The organic electroluminescent device according to claim 8 , wherein the electron transport layer has three or more layers. In the case where the relationship represented by the formula (2) is satisfied, a relationship of Ea1-Ea0 ≦ 0.4 eV, Ea2-Ea1 ≦ 0.4 eV,..., And Eam-Eam-1 ≦ 0.4 eV The organic electroluminescent element according to claim 8, wherein: An organic electroluminescence device having a plurality of organic compound layers including a light emitting layer including at least a light emitting material and a host material and an electron transport layer between a pair of electrodes,
The electron transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (2) as a light emitting material,
The electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam. An organic electroluminescent element satisfying the relationship represented by the following formula (2).
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

(In General Formula (2), M ⁵¹ represents a metal ion. Q ⁵¹ and Q ⁵² each independently represent an atomic group that forms a nitrogen-containing heterocycle with an adjacent carbon atom. Q ⁵³ and Q ⁵⁴ represent independently, .Y ⁵¹ represents a group which forms a (ring containing coordinating nitrogen M ⁵¹⁾ nitrogen-containing heterocyclic ring is communicating Yuimoto a single bond, or .L ⁵⁵ representing a double bond , ^{.n 51} representing a ligand coordinated to ^{M 51} is ^{.W 51, W 52} represents an integer of 0 to 4 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom.) An organic electroluminescence device having a plurality of organic compound layers including a light emitting layer including at least a light emitting material and a host material and an electron transport layer between a pair of electrodes,
The electron transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (3) as a light emitting material,
The electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam. An organic electroluminescent element satisfying the relationship represented by the following formula (2).
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

(In General Formula (3), M ^A1 represents a metal ion. Q ^A1 and Q ^A2 each independently represent an atomic group that forms a nitrogen-containing heterocycle with adjacent carbon atoms. Y ^A1 represents a linking group. Y ^A2 and Y ^A3 each independently represents a single bond or a linking group, and R ^A1 , R ^A2 , R ^A3 and R ^A4 each independently represent a hydrogen atom or R ^A1 and R ^A2 , R ^A3 and R ^A4 may be bonded to each other to form a ring, L ^A5 represents a ligand coordinated to M ^A1 , and n ^A1 is 0 to 0. Represents an integer of 4.) An organic electroluminescence device having a plurality of organic compound layers including a light emitting layer including at least a light emitting material and a host material and an electron transport layer between a pair of electrodes,
The electron transport layer comprises two or more layers including a layer adjacent to the light emitting layer,
The light emitting layer contains a metal complex having a tridentate or higher ligand which is a metal complex represented by the following general formula (4) as a light emitting material,
The electron affinity of the light emitting layer is Ea0, and among the electron transport layers, the electron affinity of the electron transport layer adjacent to the light emitting layer is Ea1, and the electron affinity of the electron transport layer located mth from the light emitting layer side is Eam. An organic electroluminescent element satisfying the relationship represented by the following formula (2).
Formula (2): Ea0 <... <Eam-1 <Eam (m is an integer of 2 or more)

(In the general formula (4), M ^B1 represents a metal ion. Y ^B1 represents a linking group. Y ^B2 and Y ^B3 each independently represent a single bond or a linking group. R ^B1 , R ^B2 , R ^{B 3} and R ^B4 each independently represent a hydrogen atom or a substituent, and R ^B1 and R ^B2 and R ^B3 and R ^B4 may be bonded to each other to form a ring, and L ^B5 is coordinated to M ^B1 . N ^B1 and n ^B2 each independently represents an integer of 0 or 1, except that n ^B1 and n ^B2 both become 1. n ^B3 is 0 to 4 X ^B1 and X ^B2 each independently represent an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom. In the case where the relationship represented by the formula (2) is satisfied, a relationship of Ea1-Ea0 ≦ 0.4 eV, Ea2-Ea1 ≦ 0.4 eV,..., And Eam-Eam-1 ≦ 0.4 eV The organic electroluminescent element according to claim 11, wherein: The organic electroluminescent element according to any one of claims 11 to 14, wherein the electron transport layer has three or more layers. Any metal ion of the metal complex is a platinum ion, iridium ion, a rhenium ion, a palladium ion, a rhodium ion, of claims 1 to 15, wherein the ruthenium ion, and be selected from the group consisting of copper ions 2. The organic electroluminescent element according to item 1.   The light emitting layer is a first and second light emitting layer including a light emitting material and a host material,
  The hole transport layer is composed of two or more layers including a layer adjacent to the first light emitting layer, and the electron transport layer is composed of two or more layers including a layer adjacent to the second light emitting layer,
  The first and second light-emitting layers each contain a different host material and a metal complex having the tridentate or higher ligand as the light-emitting material. Item 1 is an organic electroluminescent device.