JP2009266943A - Organic field light-emitting element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a light-emitting element having a satisfactory durability in high intensity use. <P>SOLUTION: An organic field light-emitting element includes an organic layer including at least a light-emitting layer between a pair of electrodes. A bivalent metal ion complex having a specifically configured acyclic 4-dentate ligand comprising two 6-membered rings and two 5-membered rings is contained in the organic layer of the organic field light-emitting element. A material having at least one deuterium atom is contained in at least either layer of the organic layer of the organic field light-emitting element. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent element (hereinafter also referred to as “element” or “organic EL element”).

  In recent years, organic electroluminescence devices have been actively researched and developed because they can emit light with high luminance when driven at a low voltage. In general, an organic EL element is composed of an organic layer including a light emitting layer and a pair of electrodes sandwiching the layer, and the electrons injected from the cathode and the holes injected from the anode are recombined in the light emitting layer. The energy of the excitons is used for light emission.

  By using a phosphorescent material, the efficiency of the device is increasing. Known phosphorescent materials include iridium complexes and platinum complexes (Patent Document 1).

  The use of a platinum complex having a tetradentate ligand has already been reported to improve the luminous efficiency and durability of the organic EL device (Patent Document 2). Among these platinum complexes, complexes having an arylazole skeleton can shorten the emission wavelength compared to complexes having a phenylpyridine skeleton, and are particularly promising as light blue to blue light emitting materials. No excellent luminescent material has been reported.

In addition, light-emitting materials having an arylazole skeleton and organic EL devices using the same have been reported (Patent Documents 3 and 4). Patent Document 3 discloses a novel light-emitting element material that is useful for light-emitting element materials and the like. Platinum complexes and light-emitting elements using the complexes are described. Further, Patent Document 4 describes an organic electroluminescence device having good light emission characteristics (emission wavelength, luminance, quantum yield, driving voltage, etc.) and durability.
JP 2005-220136 A International Publication No. 04/108857 Pamphlet JP 2007-96255 A JP 2008-37848 A

However, there is a demand for development of an element that achieves both higher efficiency and durability. In addition, considering the development of organic EL elements in displays and lighting equipment, it is desired to develop a light-emitting material having excellent durability particularly when using high luminance.
An object of the present invention is to provide an organic electroluminescence device excellent in durability at the time of high luminance use by using a metal complex having a specific structure of an acyclic tetradentate ligand.

As a result of investigations to solve the above problems, the present inventors have used a metal complex having a specific tetradentate ligand composed of two six-membered rings and two five-membered rings, so that a known light-emitting material is obtained. It was found that the durability of the organic EL device was improved particularly when using high luminance, and further improved by using a deuterated material together in the organic layer.
Furthermore, it has been found that the durability is further improved by using a material having at least one deuterium atom in the organic layer.
That is, the present invention has been achieved by the following means.

[1]
An organic electroluminescent device having an organic layer including at least a light emitting layer between a pair of electrodes, wherein the organic layer contains a compound represented by the following general formula (1) .
General formula (1)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Y ¹ and Y ² each independently represent a carbon atom or a nitrogen atom. Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from Y ¹ , X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from Y ² , X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. When Y ¹ and Y ² are carbon atoms, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. When Y ¹ is a nitrogen atom and Y ² is a carbon atom, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. For Y ^{1, Y 2} are both nitrogen ^{atoms, Z 1, Z 2, Z} 3, the combination of ^{Z 4 are, Z 1, Z 2, Z} 3, ^{Z 4} order (carbon atoms of a carbon atom, a carbon atom , Nitrogen atom), (carbon atom, carbon atom, phosphorus atom, nitrogen atom), (carbon atom, carbon atom, carbon atom, phosphorus atom), (carbon atom, carbon atom, phosphorus atom, phosphorus atom), (carbon atom , Nitrogen atom, carbon atom, carbon atom), (carbon atom, phosphorus atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, phosphorus atom, carbon atom), (carbon atom, phosphorus atom, phosphorus atom, carbon atom) Atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom), (carbon atom, phosphorus atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, phosphorus atom), (carbon atom, phosphorus atom) Atoms, carbon atoms, phosphorus atoms). The bond between Z ¹ , Z ² , Z ³ and Z ⁴ and M represents a coordination bond or a covalent bond. L represents a divalent linking group. M represents a divalent metal ion.
[2]
[1] The organic electroluminescent element as described in [1], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).
General formula (2)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Y ¹ and Y ² each independently represent a carbon atom or a nitrogen atom. Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from Y ¹ , X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from Y ² , X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. When Y ¹ and Y ² are carbon atoms, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. When Y ¹ is a nitrogen atom and Y ² is a carbon atom, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. For Y ^{1, Y 2} are both nitrogen ^{atoms, Z 1, Z 2, Z} 3, the combination of ^{Z 4 are, Z 1, Z 2, Z} 3, ^{Z 4} order (carbon atoms of a carbon atom, a carbon atom , Nitrogen atom), (carbon atom, carbon atom, phosphorus atom, nitrogen atom), (carbon atom, carbon atom, carbon atom, phosphorus atom), (carbon atom, carbon atom, phosphorus atom, phosphorus atom), (carbon atom , Nitrogen atom, carbon atom, carbon atom), (carbon atom, phosphorus atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, phosphorus atom, carbon atom), (carbon atom, phosphorus atom, phosphorus atom, carbon atom) Atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom), (carbon atom, phosphorus atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, phosphorus atom), (carbon atom, phosphorus atom) Atoms, carbon atoms, phosphorus atoms). The bond between Z ¹ , Z ² , Z ³ and Z ⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group.
[3]
The compound represented by the general formula (2) is a compound represented by the following general formula (3), [1] or [2].
General formula (3)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ³¹ , Z ² , Z ³ , and Z ³⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. At least one of Z ³¹ and Z ³⁴ represents a nitrogen atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a carbon atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a carbon atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ³¹ , Z ² , Z ³ and Z ³⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group.
[4]
The compound represented by the general formula (2) is a compound represented by the following general formula (4), [1] or [2].

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ³¹ , Z ² , Z ³ , and Z ³⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. At least one of Z ³¹ and Z ³⁴ represents a nitrogen atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a nitrogen atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a carbon atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ³¹ , Z ² , Z ³ and Z ³⁴ and M represents a coordinate bond or a covalent bond. L represents a divalent linking group.
[5]
The compound represented by the general formula (2) is a compound represented by the following general formula (5), [1] or [2].
General formula (5)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ each independently represent a nitrogen atom or a carbon atom. Bonds between atoms in a 5-membered ring formed from a nitrogen atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a nitrogen atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. ^However, the combination of ^{Z 51, Z 52, Z 53} , Z 54 ^is in the order of ^{Z 51, Z 52, Z 53} , Z 54 , (carbon atom, a carbon atom, a carbon atom, a nitrogen atom), (carbon atom, a nitrogen Atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom). The bond between Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group.
[6]
The compound represented by the general formula (2) is a compound represented by the following general formula (6), [1] or [2].
General formula (6)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ⁶¹ , Z ² , Z ³ and Z ⁶⁴ each independently represent a nitrogen atom, a carbon atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a carbon atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a nitrogen atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ⁶¹ , Z ² , Z ³ and Z ⁶⁴ and platinum represents a coordinate bond or a coordinate bond, respectively. L represents a divalent linking group.
[7]
The organic electroluminescent element according to any one of [1] to [6], wherein the light-emitting layer contains a compound represented by the general formula.
[8]
The organic electroluminescent element according to any one of [1] to [7], wherein a material having at least one deuterium atom is contained in at least one of the organic layers.
[9]
The organic electroluminescence device as described in [8], wherein the material having at least one deuterium atom is a material having at least one deuterium atom and containing either a carbazole skeleton or an indole skeleton.

According to the present invention, by including the metal complex represented by the general formula (1) in the organic layer, an organic electroluminescence device having excellent durability can be provided particularly when using high luminance.
In addition, by including the platinum complex represented by the general formulas (2) to (6) in at least one of the organic layers, an organic electroluminescent device having more durability is provided, particularly when using high luminance. it can.
By including a material having at least one deuterium atom in at least one of the organic layers, an organic electroluminescence device having further excellent durability can be provided, particularly when using high luminance.

  In the present invention, the substituent group B is defined as follows.

(Substituent group B)
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n- Decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, For example, propargyl, 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferably A prime number of 6 to 20, particularly preferably a carbon number of 6 to 12, such as phenyl, p-methylphenyl, naphthyl, anthranyl, etc., an amino group (preferably a carbon number of 0 to 30, more preferably a carbon number). 0 to 20, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably 1 to 1 carbon atoms). 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like, and aryloxy groups (preferably 6 carbon atoms). -30, more preferably 6-20 carbons, particularly preferably 6-12 carbons, Phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), 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, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.)

  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 has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino).

  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) Preferably it is C1-C20, Most preferably, it is C1-C12, for example, methylthio, ethylthio etc. are mentioned, for example, An arylthio group (Preferably C6-C30, More preferably C6-C20, Particularly preferably, it has 6 to 12 carbon atoms, and examples thereof include phenylthio.), A heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 carbon atom). To 20, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl).

  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 methanesulfinyl, benzenesulfinyl, etc.), ureido group (preferably carbon 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid amide group (preferably having 1 carbon atom) To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphate amide and phenyl phosphate 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 (heteroaryl) group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Examples of the hetero atom include nitrogen atom, oxygen Atom, sulfur atom, and specifically imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group and the like. (Preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyl, triphenylsilyl, etc.), silyloxy group (preferably 3 carbon atoms) To 40, more preferably 3 to 30 carbon atoms, particularly preferably carbon 3 to 24, for example trimethylsilyloxy, etc. triphenylsilyl oxy and the like.) And the like. These substituents may be further substituted.

  The device of the present invention will be described in detail.

[Organic electroluminescence device]
The organic electroluminescent element of the present invention is an organic electroluminescent element having an organic layer including at least a light emitting layer between a pair of electrodes, and contains the compound represented by the following general formula (1) in the organic layer. .
When the organic layer is a single layer, the organic layer has a light emitting layer. From the property of the element, at least one of the anode and the cathode is preferably transparent or translucent.

  The element of the present invention is characterized in that the organic layer contains a complex having a tetradentate ligand having a specific structure. Although it does not specifically limit as an organic layer, In addition to a light emitting layer, it has a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole block layer, an electron block layer, an exciton block layer, etc. It may be. Each of these layers may have other functions.

  As an aspect of lamination of the organic layer in the present invention, an aspect in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated in this order from the anode side is preferable. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. A hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Each layer may be divided into a plurality of secondary layers.

The function of the metal complex having the specific structure is not limited, and when the organic layer is composed of a plurality of layers, it can be contained in any layer. It is preferably used as a light emitting material, host material, exciton block material, charge blocking material or charge transport material, more preferably used as a light emitting material, host material or charge transport material, and used as a light emitting material or host material. The case is more preferable, and the case where it is used as a light emitting material is most preferable.
The metal complex having the specific structure is preferably contained in the light emitting layer, more preferably contained in the light emitting layer as the light emitting material or host material, and further contained in the light emitting layer as the light emitting material. It is particularly preferable that it is contained in the light emitting layer together with at least one kind of host material.

The content of the phosphorescent material (the complex of the present invention and / or the phosphorescent material used together) that can be used in the present invention is in the range of 0.1% by mass to 60% by mass with respect to the total mass of the light emitting layer. Is preferable, a range of 0.2% by mass to 50% by mass is more preferable, a range of 0.3% by mass to 40% by mass is further preferable, and a range of 0.5% by mass to 30% by mass is most preferable. .
When another phosphorescent material is used in combination with the complex of the present invention, the content of the complex of the present invention is preferably in the range of 0.1% by mass to 60% by mass with respect to the total mass of the phosphorescent light emitting material. The range of 0.2% to 50% by mass is more preferable, the range of 0.3% to 40% by mass is more preferable, and the range of 0.5% to 35% by mass is most preferable.

  The compound represented by the general formula (1) of the present invention is contained in a layer located between the light emitting layer and the cathode, that is, an electron transport layer, an electron injection layer, an exciton block layer, and a hole block layer. Also good. When included in the electron transport layer and the electron injection layer, it can be used together with an electron transport material described later, and is contained in an amount of 0.1% by mass to 99% by mass with respect to the total compound mass forming the layer, From the viewpoint of durability and external quantum efficiency, it is preferably contained in an amount of 5% by mass to 70% by mass, and more preferably 5% by mass to 45% by mass. Even when used as an exciton block layer or a hole block layer, it can be used together with an electron transporting material described later, and is contained in an amount of 30% by mass to 100% by mass with respect to the total mass of the compound forming the layer. From the viewpoint of external quantum efficiency, the content is preferably 50% by mass to 100% by mass, and more preferably 70% by mass to 100% by mass.

  The compound represented by the general formula (1) of the present invention is contained in a layer located between the light emitting layer and the anode, that is, a hole injection layer, a hole transport layer, an exciton block layer, and an electron block layer. May be. When it is contained in the hole injection layer and the hole transport layer, it can be used together with a hole (hole) transporting material described later, and 0.1% by mass to 99% by mass with respect to the total compound mass forming the layer. Although contained in an amount of 5% by mass, it is preferably contained in an amount of 5% by mass to 70% by mass, more preferably 5% by mass to 45% by mass from the viewpoint of durability and external quantum efficiency. Also when used as an exciton block layer or an electron block layer, it can be used together with a hole (hole) transporting material described later, and is 30% by mass to 100% by mass with respect to the total compound mass forming the layer. Although contained, it is preferable to contain 50 mass%-100 mass% from a viewpoint of external quantum efficiency, and it is more preferable that 70 mass%-100 mass% are contained.

  Hereinafter, the compounds represented by the general formulas (1) to (6) will be described.

The hydrogen atom in the general formulas (1) to (6) includes isotopes (deuterium and the like), and the atoms constituting the substituent further include the isotopes.
In the above general formula, the coordinate bond is a bond formed by coordination of a lone pair of neutral atoms to a metal. In the present specification, when distinction is necessary, a dotted line To express. A covalent bond is a bond formed by coordination of a monovalent anion to a metal. In the present specification, a distinction is indicated by a solid line.

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

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Y ¹ and Y ² each independently represent a carbon atom or a nitrogen atom. Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from Y ¹ , X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from Y ² , X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. When Y ¹ and Y ² are carbon atoms, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. When Y ¹ is a nitrogen atom and Y ² is a carbon atom, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. For Y ^{1, Y 2} are both nitrogen ^{atoms, Z 1, Z 2, Z} 3, the combination of ^{Z 4 are, Z 1, Z 2, Z} 3, ^{Z 4} order (carbon atoms of a carbon atom, a carbon atom , Nitrogen atom), (carbon atom, carbon atom, phosphorus atom, nitrogen atom), (carbon atom, carbon atom, carbon atom, phosphorus atom), (carbon atom, carbon atom, phosphorus atom, phosphorus atom), (carbon atom , Nitrogen atom, carbon atom, carbon atom), (carbon atom, phosphorus atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, phosphorus atom, carbon atom), (carbon atom, phosphorus atom, phosphorus atom, carbon atom) Atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom), (carbon atom, phosphorus atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, phosphorus atom), (carbon atom, phosphorus atom) Atoms, carbon atoms, phosphorus atoms). The bond between Z ¹ , Z ² , Z ³ and Z ⁴ and M represents a coordination bond or a covalent bond. L represents a divalent linking group. M represents a divalent metal ion.

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. When X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ can be further substituted, they may each independently have a substituent. When X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ have a substituent, the substituent is a substituent represented by the above substituent group B. Groups. The preferred substituent is an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a halogen atom, more preferably an alkyl group, A perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, and a fluorine atom, and more preferably an alkyl group, a trifluoromethyl group, and a fluorine atom. Further, if possible, the substituents may be linked to form a condensed ring structure.

In general formula (1), a 6-membered ring formed from a carbon atom, X ⁴ , X ³ , X ² , X ¹ , Z ¹ and a carbon atom, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ⁴ Examples of the 6-membered ring formed from benzene ring, phosphinine ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring and triazine ring, more preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, A pyridazine ring, particularly preferably a benzene ring and a pyridine ring. 6-membered ring formed from carbon atoms, X ⁴ , X ³ , X ² , X ¹ , Z ¹ and 6-membered ring formed from carbon atoms, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ⁴ Is a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or a pyridazine ring (particularly preferably a benzene ring or a pyridine ring), it is preferable because the thermal stability of the metal complex is improved.

In general formula (1), a 6-membered ring formed from a carbon atom, X ⁴ , X ³ , X ² , X ¹ , Z ¹ and a carbon atom, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ⁴ As the condensed ring structure formed by connecting substituents on a 6-membered ring formed from the following, a naphthalene ring, a quinoline ring, an isoquinoline ring, a benzofuran ring, a dibenzofuran ring, an isobenzofuran ring, a thianaphthene ring, a dibenzothiophene ring, Examples include isothianaphthene ring, indole ring, carbazole ring, isoindole ring, benzoxazole ring, benzoisoxazole ring, benzoxazole ring, benzoisothiazole ring, indazole ring, and benzimidazole ring. Among them, naphthalene ring, quinoline ring, isoquinoline ring, dibenzofuran ring, dibenzothiophene ring, indole ring, carbazole ring, benzoxazole ring, benzoisoxazole ring, benzoxazole ring, benzoisothiazole ring, indazole ring, benzimidazole ring are included. Preferably, a naphthalene ring, a quinoline ring, an isoquinoline ring, an indole ring, a carbazole ring, a benzoisothiazole ring, an indazole ring, and a benzimidazole ring are more preferable, and a naphthalene ring, a quinoline ring, an isoquinoline ring, an indole ring, and a carbazole ring are more preferable. 6-membered ring formed from carbon atoms, X ⁴ , X ³ , X ² , X ¹ , Z ¹ and 6-membered ring formed from carbon atoms, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ⁴ It is preferable that the condensed ring structure formed by linking the above substituents is a naphthalene ring, a quinoline ring, an isoquinoline ring, an indole ring, or a carbazole ring, since chemical stability is improved.

X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent an unsubstituted or optionally substituted carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom, and X ⁷ And X ⁸ each independently represents an unsubstituted or optionally substituted carbon atom or nitrogen atom. When any of X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ has a substituent, examples of the substituent include the substituents represented by the above substituent group B. It is done. The preferred substituent is an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a halogen atom, more preferably an alkyl group. , A perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, and a fluorine atom, and more preferably an alkyl group, a cyano group, a trifluoromethyl group, and a fluorine atom. Further, if possible, the substituents may be linked to form a condensed ring structure.

The bond in the 5-membered ring formed by X ⁵ , X ⁶ , X ⁷ , Z ² and Y ¹ and the 5-membered ring formed by X ¹⁰ , X ⁹ , X ⁸ , Z ³ and Y ² is a single bond, Any combination of double bonds may be used. As the 5-membered ring formed by X ⁵ , X ⁶ , X ⁷ , Z ² and Y ¹ and the 5-membered ring formed from X ¹⁰ , X ⁹ , X ⁸ , Z ³ and Y ² , a pyrrole ring, A pyrazole ring, an imidazole ring, a furan ring, a thiophene ring, etc. are mentioned, More preferably, they are a pyrrole ring, a pyrazole ring, an imidazole ring, and a thiophene, More preferably, they are a pyrrole ring, a pyrazole ring, and an imidazole ring. A 5-membered ring formed by X ⁵ , X ⁶ , X ⁷ , Z ² and Y ¹ and a 5-membered ring formed from X ¹⁰ , X ⁹ , X ⁸ , Z ³ and Y ² are a pyrrole ring and a pyrazole ring. In the case of imidazole ring and thiophene (more preferably pyrrole ring, pyrazole ring and imidazole ring), the chemical stability is improved.

Substituents on the 5-membered ring formed by X ⁵ , X ⁶ , X ⁷ , Z ² and Y ¹ and the 5-membered ring formed by X ¹⁰ , X ⁹ , X ⁸ , Z ³ and Y ² are substituted. Examples of the condensed ring structure formed by linking groups include indole ring, isoindole ring, indazole ring, benzimidazole ring, etc., indole ring, indazole ring, benzimidazole ring are more preferable, indole, benzimidazole ring Is more preferable.

Y ¹ and Y ² each independently represent a carbon atom or a nitrogen atom.

Z ¹ and Z ⁴ each independently represent a nitrogen atom, a carbon atom or a phosphorus atom.

Z ² and Z ³ each independently represent a nitrogen atom, a carbon atom or a phosphorus atom.

When Y ¹ and Y ² are carbon atoms, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom.

When Y ¹ is a nitrogen atom and Y ² is a carbon atom, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom.

For Y ^{1, Y 2} are both nitrogen ^atoms, Z ^1, Z ^2, a combination of Z 3, ^{Z 4 is,} Z ^1, Z ^2, Z 3, sequentially to a carbon atom of ^{Z 4,} carbon atoms, carbon atoms, (Nitrogen atom), (carbon atom, carbon atom, phosphorus atom, nitrogen atom), (carbon atom, carbon atom, carbon atom, phosphorus atom), (carbon atom, carbon atom, phosphorus atom, phosphorus atom), (carbon atom, (Nitrogen atom, carbon atom, carbon atom), (carbon atom, phosphorus atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, phosphorus atom, carbon atom), (carbon atom, phosphorus atom, phosphorus atom, carbon atom) ), (Carbon atom, nitrogen atom, carbon atom, nitrogen atom), (carbon atom, phosphorus atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, phosphorus atom), (carbon atom, phosphorus atom) , Carbon atom, phosphorus atom).

Considering the stability of the metal complex ^formed, those preferred in combination ^{Z 1, Z 2, Z 3} , Z 4, in the order of ^{Z 1, Z 2, Z 3} , Z 4, ( carbon atom, Carbon atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom), among them (carbon atom, carbon atom, carbon atom) Atom, nitrogen atom) and (carbon atom, nitrogen atom, carbon atom, carbon atom) are more preferred.

The bond between Z ¹ , Z ² , Z ³ and Z ⁴ and M represents a coordination bond or a coordination bond, respectively.

  L represents a divalent linking group. Although it does not specifically limit as a bivalent coupling group, The coupling group which consists of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom is preferable. Specific examples of the divalent linking group are shown below, but the present invention is not limited thereto.

  Ro represents a substituent selected from the substituent group B. Ro is preferably an alkyl group, and more preferably an alkyl group having 1 to 6 carbon atoms. m represents an integer of 1 to 5. m is preferably 2 to 5, more preferably 2 to 3.

  L is preferably a dialkylmethylene group, a diarylmethylene group or a diheteroarylmethylene group, more preferably a dimethylmethylene group, a methylphenylmethylene group or a diphenylmethylene group, still more preferably a dimethylmethylene group or a diphenylmethylene group. .

  M represents a divalent metal ion. Examples of the metal species include zinc ion, copper ion, nickel ion, palladium ion and platinum ion, more preferably copper ion, palladium ion and platinum ion, still more preferably copper ion and platinum ion, particularly preferably. Is platinum.

  The metal complex represented by the general formula (1) is preferably represented by the general formula (2).

The general formula (2) will be described. X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ , X ¹⁰ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Y ¹ , Y ² , Z ¹ , Z ² , Z ³ , Z ⁴ , and L are X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Y ¹ , Y ² , Z in the general formula (1). ¹ , Z ² , Z ³ , Z ⁴ , and L are synonymous, and the preferred range is also the same.

  The platinum complex represented by the general formula (2) is preferably represented by the general formula (3).

General formula (3)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ³¹ , Z ² , Z ³ , and Z ³⁴ each independently represent a nitrogen atom or a carbon atom. At least one of Z ³¹ and Z ³⁴ represents a nitrogen atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a carbon atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a carbon atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ³¹ , Z ² , Z ³ and Z ³⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group.

The general formula (3) will be described. X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ² , Z ³ , and L are X ¹ , X ² , X ³ , X ^{4 in the} general formula (2) , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ² , Z ³ , and L, and the preferred range is also the same.

Z ³¹ and Z ³⁴ each represent a carbon atom or a nitrogen atom, and at least one of them represents a nitrogen atom.

In general formula (3), a 6-membered ring formed from a carbon atom, X ⁴ , X ³ , X ² , X ¹ , Z ³¹ and a carbon atom, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ³⁴ Examples of the 6-membered ring formed from benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, and triazine ring include, and more preferably, benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring. Particularly preferred are a benzene ring and a pyridine ring.

6-membered ring formed from carbon atom, X ⁴ , X ³ , X ² , X ¹ , Z ³¹ and 6-membered ring formed from carbon atom, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ³⁴ The condensed ring structure formed by linking the above substituents includes naphthalene ring, quinoline ring, isoquinoline ring, benzofuran ring, dibenzofuran ring, isobenzofuran ring, thianaphthene ring, dibenzothiophene ring, isothianaphthene ring, indole ring Carbazole ring, isoindole ring, benzoxazole ring, benzoisoxazole ring, benzoxazole ring, benzoisothiazole ring, indazole ring, and benzimidazole ring. Among them, naphthalene ring, quinoline ring, isoquinoline ring, dibenzofuran ring, dibenzothiophene ring, indole ring, carbazole ring, benzoxazole ring, benzoisoxazole ring, benzoxazole ring, benzoisothiazole ring, indazole ring, benzimidazole ring are included. Preferably, a naphthalene ring, a quinoline ring, an isoquinoline ring, an indole ring, a carbazole ring, a benzoisothiazole ring, an indazole ring, and a benzimidazole ring are more preferable, and a naphthalene ring, a quinoline ring, an isoquinoline ring, an indole ring, and a carbazole ring are more preferable.

The platinum complex represented by the general formula (2) is preferably represented by the general formula (4).
General formula (4):

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ³¹ , Z ² , Z ³ , and Z ³⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. At least one of Z ³¹ and Z ³⁴ represents a nitrogen atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a nitrogen atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a carbon atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ³¹ , Z ² , Z ³ and Z ³⁴ and M represents a coordinate bond or a covalent bond. L represents a divalent linking group.

The general formula (4) will be described. X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ³¹ , Z ² , Z ³ , Z ³⁴ , and L are X ¹ , X ^{2 in the} general formula (3) , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ³¹ , Z ² , Z ³ , Z ³⁴ , and L, and the preferred ranges are also the same.

The platinum complex represented by the general formula (2) is preferably represented by the general formula (5).
General formula (5)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ each independently represent a nitrogen atom or a carbon atom. Bonds between atoms in a 5-membered ring formed from a nitrogen atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a nitrogen atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. ^However, the combination of ^{Z 51, Z 52, Z 53} , Z 54 ^is in the order of ^{Z 51, Z 52, Z 53} , Z 54 , (carbon atom, a carbon atom, a carbon atom, a nitrogen atom), (carbon atom, a nitrogen Atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom). The bond between Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group.

The general formula (5) will be described. X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , and L are represented by the general formula (2) X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , ^{X 13,} X ^14, and has the same meaning as L, and preferred ranges are also the same.

Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ each independently represent a nitrogen atom or a carbon atom.

Z ⁵¹ , Z ⁵² , Z ⁵³ , and the bond between Z ⁵⁴ and platinum each represent a coordinate bond or a covalent bond.

The combination of ^{Z 51, Z 52, Z 53} , Z 54 ^is sequentially of ^{Z 51, Z 52, Z 53} , Z 54 (carbon atom, a carbon atom, a carbon atom, a nitrogen atom), (carbon atom, a nitrogen atom, carbon Atom, carbon atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom).

The combination of ^{Z 51, Z 52, Z 53} , Z 54, in the order of ^{Z 51, Z 52, Z 53} , Z 54, (carbon atom, a carbon atom, a carbon atom, a nitrogen atom), (carbon atom, a nitrogen atom , Carbon atom, carbon atom), and (carbon atom, nitrogen atom, carbon atom, carbon atom) are more preferable.

In the general formula (5), a carbon atom, a 6-membered ring formed from X ⁴ , X ³ , X ² , X ¹ , Z ⁵¹ and a carbon atom, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ⁵⁴ Examples of the 6-membered ring formed from benzene ring, phosphinine ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring and triazine ring, more preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, A pyridazine ring, particularly preferably a benzene ring and a pyridine ring.

A bond in a 5-membered ring formed by X ⁵ , X ⁶ , X ⁷ , Z ⁵² and a nitrogen atom, and a 5-membered ring formed by X ¹⁰ , X ⁹ , X ⁸ , Z ⁵³ and a nitrogen atom are single bonds, Any combination of double bonds may be used. As a 5-membered ring formed by X ⁵ , X ⁶ , X ⁷ , Z ⁵² and a nitrogen atom, and a 5-membered ring formed from X ¹⁰ , X ⁹ , X ⁸ , Z ⁵³ and a nitrogen atom, a pyrrole ring, Examples include a pyrazole ring, an imidazole ring, a furan ring, and a thiophene ring, and more preferred are a pyrrole ring, a pyrazole ring, an imidazole ring, and a thiophene.

The platinum complex represented by the general formula (2) is preferably represented by the general formula (6).
General formula (6)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ⁶¹ , Z ² , Z ³ and Z ⁶⁴ each independently represent a nitrogen atom or a carbon atom. Bonds between atoms in a 5-membered ring formed from a carbon atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a nitrogen atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ⁶¹ , Z ² , Z ³ and Z ⁶⁴ and platinum represents a coordinate bond or a coordinate bond, respectively. L represents a divalent linking group.

The general formula (6) will be described. X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ² , Z ³ , and L are represented by the general formula (2) X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ² , Z ³ , and L have the same meaning, and the preferred range is also the same.

Z ⁶¹ and Z ⁶⁴ each independently represent a carbon atom or a nitrogen atom.

In General Formula (6), a 6-membered ring formed from a carbon atom, X ⁴ , X ³ , X ² , X ¹ , Z ⁶¹ and a carbon atom, X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ⁶⁴ Examples of the 6-membered ring formed from benzene ring, phosphinine ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring and triazine ring, more preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, A pyridazine ring, particularly preferably a benzene ring and a pyridine ring.

The bond between Z ⁶¹ , Z ⁶⁴ and platinum represents a coordinate bond or a covalent bond, respectively.

A partial structure that can be used for Q ¹ , Q ² , Q ³ , Q ⁴ , and L when the compound (1) of the present invention is represented by the following general formula (7) is shown below. M of M partial structure ^Q 1 to Q in ^4, L respectively general formula (7) corresponds to L, and if Q is the respective partial structure of ^Q 2, ^{Q 2} in the case of ^{Q 1, Q 1} , Q ³ represents Q ⁴ , and Q ⁴ represents Q ³ . M and L are synonymous with the said General formula (1), and their preferable range is also the same.

The following [QB60CN], [QB61CC], [QT50CN], [QT50NC], [QT50NN], [QT51CC], [QT51CN], [QT51NC] represent a group of partial structures, ^Four partial structures selected from the group of each partial structure so that the combinations of structures Q ^{1 to} Q ⁴ (Q ¹ , Q ² , Q ³ , Q ⁴ ) are the combinations shown in Table 1 below. It can be represented by any combination selected from the group of the linking group [L] shown and the divalent metal ion M.

A partial structure that can be used for Q ¹ and Q ⁴ is a partial structure group represented by [QB60CN] or [QB61CC].
A partial structure which can be used in the Q ² and ^{Q 3} [QT50CN] is a partial structure group represented by [QT50NC], [QT50NN], [QT51CC], [QT51CN] or [QT51NC].
The partial structure that can be used for L is a partial structure group represented by [L].
Two Qs in the partial structure of [L], Q on the left side represents Q ² and Q on the right side represents Q ³ .

  Forms a coordinate bond or a covalent bond with a metal ion in the chemical structural formula in the partial structure group represented by the following [QT50CN], [QT50NC], [QT50NN], [QT51CC], [QT51CN] or [QT51NC] The 6-membered ring or the substituent on the 5-membered ring is an example, and is not limited thereto.

  A group of partial structures [QB60CN] is shown below.

  A group of partial structures [QB61CC] is shown below.

  The partial structure group [QT50CN] is shown below.

  A group of partial structures [QT50NC] is shown below.

  A group of partial structures [QT50NN] is shown below.

部分構造の群〔ＱＴ５１ＣＣ〕を以下に示す。

A group of partial structures [QT51CC] is shown below.

  A group of partial structures [QT51CN] is shown below.

  A group of partial structures [QT51NC] is shown below.

The partial structure that can be used for L is a partial structure group represented by the following. As for two Qs in the partial structure represented by the linking group L, the left Q represents Q ² and the right Q represents Q ³ .

  A group of linking groups L is shown below.

As a compound represented by General formula (1), the compound of following Table 1 can be illustrated.
In Table 1, for example, compounds 1-1 Q ¹ in the following general formula (7) represents QB60CN-1, Q ² represents QT50CN-37, Q ³ represents QT51CC-62, Q ⁴ is QB61CC- 1, M means Pt, L means L-1.

Examples of the combination of Q ^{1 to} Q ⁴ , M, and L in the general formula (7) include the combinations in Table 1, but are not limited thereto.

  The metal complex represented by the general formula (1) may be a low molecular weight compound, or a high molecular weight compound in which a residue is connected to a polymer main chain (preferably a mass average molecular weight of 1000 to 5000000, more preferably 5000 to 20000, more preferably 10,000 to 1,000,000) or a high molecular weight compound having the structure of the metal complex of the present invention in the main chain (preferably a mass average molecular weight of 1,000 to 5,000,000, more preferably 5,000 to 2,000,000, still more preferably 10,000 to 1,000,000) It may be. In the case of a high molecular weight compound, it may be a homopolymer, may be a copolymer with another polymer, and if it is a copolymer, it may be a random copolymer or a block copolymer. There may be. Further, in the case of a copolymer, a compound having a light emitting function and / or a compound having a charge transport function may be included in the polymer.

  Although the example of a compound represented with General formula (1) below is enumerated below, this invention is not limited to these compounds.

  In the following exemplary compound examples, M represents a divalent ion of zinc (Zn), copper (Cu), nickel (Ni), palladium (Pd), or platinum (Pt). In the present specification, the compound numbers described in “Metal species—compound examples” are used as the numbers in the case of describing these compounds. For example, in the following compound examples, the compound number “1” and the metal species is “Pt”. In this case, it is expressed as “Pt−1”.

  Next, a method for producing the compound of the present invention (or also referred to as “complex” or “metal complex”) will be described.

  The metal complex represented by the general formula (1) can be obtained by reacting a compound represented by the general formula (C-0) (hereinafter also referred to as a ligand) with a metal salt in the presence of a solvent. it can.

In formula ^{(C-0), X 1} , X 2, X 3, X 4, X 5, X 6, X 7, X 8, X 9, X 10, X 11, X 12, X 13, X 14 , Z ¹ , Z ² , Z ³ , Z ⁴ , Y ¹ , Y ² , L are the general formula (1) X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ , X ¹⁰ , X ¹¹ , X ¹² , X ¹³ , X ¹⁴ , Z ¹ , Z ² , Z ³ , Z ⁴ , Y ¹ , Y ² , L, and M It is the same.

  The compound represented by the general formula (C-0) is a compound in Palladium in Heterocyclic Chemistry, 2nd edition, written by Gie Jack Lee and Gordon W. Gribble. ), ELSEVIER, (2006), etc. Suzuki-Miyaura coupling, Stille coupling, Negishi coupling, Sonogashira coupling carbon-carbon bond reaction and copper catalyst using palladium catalyst Carbon-nitrogen bond formation reaction, alkylation reaction using base-alkyl halide, condensation reaction, dehydration reaction, oxidation reaction, reduction reaction, elimination reaction, nucleophilic substitution reaction, electrophilic substitution reaction, rearrangement reaction, etc. Can be synthesized by combining is there. For example, it can synthesize | combine using the method of Unexamined-Japanese-Patent No. 2005-310733, Unexamined-Japanese-Patent No. 2007-96255, etc.

  In the production of a metal complex, dichloro (N, N, N ′, N′-tetramethylenediamine) zinc, zinc acetate, copper acetylacetate is included as containing divalent zinc used in the complex formation reaction with the ligand. Examples thereof include narate, zinc bromide, zinc chloride, zinc fluoride, and more preferable copper salts include zinc halides such as zinc bromide and zinc chloride.

  In the production of metal complexes, copper acetate, copper acetylacetonate, copper bromide, copper chloride, copper fluoride, copper carbonate, cyanide are used as those containing divalent copper used in the complex formation reaction with the ligand. Copper, copper hydroxide, copper oxide, copper sulfate, copper trifluoroacetate and the like can be mentioned, and more preferable copper salts include copper halides such as copper bromide, copper chloride and copper fluoride.

  In the production of a metal complex, those containing divalent nickel used in a complex formation reaction with a ligand include nickel acetate, nickel acetylacetonate, nickel chloride, nickel bromide, nickel fluoride, nickel iodide, Examples thereof include nickel nitrate and nickel sulfate, and more preferable nickel salts include nickel halides such as nickel chloride and nickel bromide.

  In the production of metal complexes, those containing divalent palladium used in the complex formation reaction with the ligand include palladium chloride, palladium bromide, palladium iodide, palladium acetate, palladium acetylacetonate, palladium hexafluoroacetylacetate. Narate, palladium trifluoroacetate, allyl palladium chloride-dimer, (2,2′-bipyridine) dichloropalladium, bis (benzonitrile) dichloropalladium, bis (acetonitrile) dichloropalladium, (bicyclo [2.2.1] hepta 2,5-diene) dichloropalladium, dichloro (1,5-cyclooctadiene) palladium, dibromobis (triphenylphosphine) palladium, dichloro (N, N, N ′, N′-tetramethylethylenediamine) Radium, dichloro (1,10-phenanthroline) palladium, dichlorobis (triphenylphosphine palladium), ammonium tetrachloroparadate, diammine dibromopalladium, diammine dichloropalladium, diammine diiodopalladium, potassium tetrabromoparadate, potassium tetrachloro Examples of compounds containing zero-valent palladium such as paradate and sodium tetrachloroparadate include tetrakis (triphenylphosphine) palladium and tris (dibenzylideneacetone) dipalladium.

  More preferable palladium salts include palladium halides such as palladium chloride and palladium bromide, nitrile complexes such as bis (benzonitrile) dichloropalladium and bis (acetonitrile) dichloropalladium, (bicyclo [2.2.1] hepta-2 Olefin complexes such as, 5-diene) dichloropalladium and dichloro (1,5-cyclooctadiene) palladium, among which palladium halides such as platinum chloride and platinum bromide, bis (benzonitrile) dichloropalladium, bis Nitrile complexes such as (acetonitrile) dichloropalladium are more preferred.

  In the production of the metal complex, the platinum salt used in the complex formation reaction with the ligand includes platinum chloride, platinum bromide, platinum iodide, platinum acetylacetonate, bis ( Benzonitrile) dichloroplatinum, bis (acetonitrile) dichloroplatinum, dichloro (1,5-cyclooctadiene) platinum, dibromobis (triphenylphosphine) platinum, dichloro (1,10-phenanthroline) platinum, dichlorobis (triphenylphosphine) platinum , Ammonium tetrachloroparadate, diammine dibromopalladium, diammine dichloroplatinum, diammine diiodoplatinum, potassium tetrabromoplatinate, potassium tetrachloroplatinate, sodium tetrachloroplatinum DOO, dimethyl bis (dimethyl sulfoxide) platinum, dimethyl bis (dimethyl sulfide) platinum, dimethyl (bicyclo [2.2.1] hepta-2,5-diene) platinum, and the like.

  More preferable platinum salts include platinum halides such as platinum chloride, platinum bromide and platinum iodide, nitrile complexes such as bis (benzonitrile) dichloroplatinum, bis (benzonitrile) and dichloroplatinumbis (acetonitrile) dichloroplatinum, Olefin complexes such as dichloro (1,5-cyclooctadiene) platinum, platinum halides such as platinum chloride and platinum bromide, bis (benzonitrile) dichloroplatinum, bis (acetonitrile) dichloroplatinum and the like. Nitrile complexes are more preferred.

  The metal salt used in the production of the metal complex may contain crystal water, a crystal solvent, and a coordination solvent. The valence of the metal is not particularly limited, but the metal is preferably divalent or zero-valent, more preferably divalent.

  In the production of a metal complex, the amount of the metal salt used in the complex formation reaction between the metal salt and the ligand is usually the ligand 1 when the metal salt contains one metal atom forming the complex. It is 0.1-10 mol with respect to mol, Preferably it is 0.5-5 mol, More preferably, it is 1-3 mol. When n metal atoms forming a complex are contained in the metal salt, the amount used may be 1 / n times.

  In the production of the metal complex, examples of the solvent used in the complex formation reaction between the metal salt and the ligand include amides such as N, N-dimethylformamide, formamide, N, N-dimethylacetamide, acetonitrile, propio Nitriles such as nitrile, butyronitrile, benzonitrile, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, o-dichlorobenzene, aliphatics such as pentane, hexane, octane, decane Hydrocarbons, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, ethers such as diethyl ether, diisopropyl ether, butyl ether, tert-butyl methyl ether, 1,2-dimethoxyethane, tetrahydrofuran and 1,4-dioxane Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, alcohols such as methanol, ethanol, 1-propanol, 2-propanol, tert-butyl alcohol, 2-methoxyethanol, 2-ethoxyethanol, ethylene glycol, glycerin, Water etc. are mentioned.

  More preferable solvents include acetonitrile, propionitrile, butyronitrile, nitriles such as benzonitrile, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, methanol, ethanol, 1-propanol, 2-propanol, tert- Examples include alcohols such as butyl alcohol, 2-methoxyethanol, 2-ethoxyethanol, ethylene glycol, and glycerin. Among these, nitriles such as acetonitrile, propionitrile, butyronitrile, and benzonitrile, benzene, toluene, xylene, mesitylene, and the like The aromatic hydrocarbons are more preferred.

  These solvents may be used alone or in combination of two or more.

  In the production of the metal complex, the amount of the solvent used in the complex formation reaction between the metal salt and the ligand is not particularly limited as long as the reaction can proceed sufficiently, but usually with respect to the ligand to be used. 1 to 200 times volume, preferably 5 to 100 times volume.

  In the production of a metal complex, when an acidic substance such as hydrogen halide is produced during the complex formation reaction between a metal salt and a ligand, the reaction may be performed in the presence of a basic substance. Basic substances include tertiary amines such as triethylamine, diisopropylethylamine, pyridine, 1,8-dimethylaminonaphthalene, metal alkoxides such as sodium methoxide and sodium ethoxide, sodium hydroxide, potassium hydroxide and potassium carbonate. And inorganic bases such as sodium hydrogen carbonate.

  In the production of the metal complex, the complex formation reaction between the metal salt and the ligand is preferably performed in an inert gas atmosphere. Examples of the inert gas include nitrogen and argon.

  In the production of the metal complex, the reaction temperature, reaction time, and reaction pressure during the complex formation reaction between the metal salt and the ligand vary depending on the raw materials, the solvent, etc., but are usually 20 ° C to 300 ° C, preferably 50 ° C to 250 ° C. ° C, more preferably in the range of 80 ° C to 220 ° C. The reaction time is usually 30 minutes to 24 hours, preferably 1 to 12 hours, more preferably 2 to 10 hours, and the reaction pressure is usually atmospheric pressure, but under pressure as necessary. But it can be under reduced pressure.

  In the production of the metal complex of the present invention, the heating means during the complex formation reaction between the metal salt and the ligand is not particularly limited. Specifically, heating by an oil bath or a mantle heater or heating by microwave irradiation can be used.

  The metal complex of the present invention thus obtained can be isolated and purified as necessary. Examples of isolation and purification methods include column chromatography, recrystallization, reprecipitation, sublimation and the like. These may be used alone or in combination.

  In the production methods shown above, when the defined substituents change under the conditions of a certain synthesis method or are inappropriate for carrying out the method, the functional groups are protected and deprotected (for example, Protective Groups in Organic Synthesis, by TW Greene, John Wiley & Sons Inc. (198) ) Etc.) and the like can be easily manufactured. Moreover, it is also possible to change the order of reaction steps such as introduction of substituents as necessary.

  When the complex of the present invention is introduced into a layer other than the light emitting layer (for example, a charge transport layer), it is preferably contained in the layer in an amount of 10% by mass to 100% by mass, more preferably 30% by mass to 100% by mass. % Is preferably included.

  As described above, the metal complex having the specific structure is particularly preferably contained in the light emitting layer together with at least one kind of host material.

  The host material is a material other than the light emitting material among the materials constituting the light emitting layer, the function of dispersing the light emitting material and holding it in the layer, the function of receiving holes from the anode, the hole transport layer, etc., the cathode The function of receiving electrons from the electron transport layer, the function of transporting holes and / or electrons, the function of providing a recombination field of holes and electrons, and the exciton energy generated by the recombination transferred to the light emitting material It means a material having at least one of a function of transporting holes and / or electrons to a light-emitting material.

  The host material is preferably a charge transport material. The host material may be one type or two or more types, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Further, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.

  The concentration of the host material in the light emitting layer is not particularly limited, but is preferably the main component (the component having the largest content) in the light emitting layer, more preferably 50% by mass or more and 99.9% by mass or less, 70 mass% or more and 99.8 mass% or less are more preferable, 80 mass% or more and 99.7 mass% or less are especially preferable, and 90 mass% or more and 99.5 mass% or less are the most preferable.

  The glass transition point of the host material is preferably 100 ° C. or higher and 500 ° C. or lower, more preferably 110 ° C. or higher and 300 ° C. or lower, and further preferably 120 ° C. or higher and 250 ° C. or lower.

  In the present invention, the fluorescence wavelength in the film state of the host material contained in the light emitting layer is preferably in the range of 400 nm to 650 nm, more preferably in the range of 420 nm to 600 nm, and in the range of 440 nm to 550 nm. More preferably.

  As the host material used in the present invention, the compounds described in paragraphs 0113 to 0161 of JP-A No. 2002-1000047 and the compounds described in paragraphs of 0087 to 0098 of JP-A No. 2004-214179 can be suitably used. It is not limited to.

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

  The material having at least one deuterium atom may be an organic material, an inorganic material, or both, but is preferably an organic material.

The organic material having at least one deuterium atom has a ratio of deuterium atoms to hydrogen atoms (the number of deuterium atoms: the number of hydrogen atoms) at a position where hydrogen atoms or deuterium atoms can be combined. : Means in the range of 0 to 1:99. Here, the position at which a hydrogen atom or deuterium atom can be bonded may be in any range from at least one specific position to the entire position in one molecule. In other words, the said ratio is synonymous with the ratio (deuteration rate) which a deuterium atom occupies in the sum total of the position where a hydrogen atom or a deuterium atom can couple | bond together.
Therefore, the state of the above ratio can be realized by simultaneously using a compound containing deuterium at the position and a compound not containing deuterium at an appropriate ratio.

  The composition range of deuterium atoms and hydrogen atoms is preferably 100: 0 to 5:95, more preferably 100: 0 to 50:50, and particularly preferably 100: 0 to 80:20.

  The material having at least one deuterium atom may be contained in any layer of the organic electroluminescent device, but is not limited to a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an exciton. It is preferably contained in one or more of the block layer and the charge blocking layer, more preferably contained in one or more of the light emitting layer, exciton blocking layer and charge blocking layer, and contained in the light emitting layer. More preferably, it is preferably contained as a host material in the light emitting layer. When used as a host material, the usage amount of the material having at least one deuterium atom is the same as the usage amount described for the host material.

  Examples of the organic material having at least one deuterium atom include, but are not limited to, compounds described in International Publication No. 02-47440.

  As an example of a particularly preferable organic material having at least one deuterium atom, a material including a nitrogen atom is preferable, and a material including a tertiary amine skeleton, a carbazole skeleton, or an indole skeleton is preferable, and a carbazole skeleton, Alternatively, a material including an indole skeleton is more preferable, and a material including a carbazole skeleton is particularly preferable.

  Examples of materials including a carbazole skeleton having at least one deuterium atom or an indole skeleton include the following.

  A material having at least one deuterium atom can be synthesized by various known synthesis methods. For example, by using the methods described in JP-A-2004-11400 and JP-A-2004-46066, hydrogen atoms of the corresponding compounds can be converted into deuterium atoms. In addition, a material having at least one deuterium atom can be synthesized using a raw material containing a deuterium atom. Specific examples of raw materials containing deuterium atoms include deuterated bromobenzene-d5 (CAS No. 4165-57-5), deuterated methyl iodide-d3 (CAS No. 865-50-9), and J. Am. Chem. Soc. Vol. 126, No. 40, 13033-03043 (2004), resorcinol-d6 which can be synthesized by the method described in 2004, and sulfonic acid ester derivatives thereof.

  Each element constituting the element of the present invention will be described in detail.

<Board>
The electrode and the organic layer can be formed on a substrate.
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. Specific examples include yttria-stabilized zirconia (YSZ), inorganic materials such as glass, polyesters such as polyethylene terephthalate, polybutylene phthalate, and polyethylene naphthalate, polystyrene, polycarbonate, polyethersulfone, polyarylate, polyimide, and polycycloolefin. , Organic materials such as norbornene resin and poly (chlorotrifluoroethylene).

  For example, when glass is used as the substrate, alkali-free glass is preferably used as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

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

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

  The substrate can be provided with a moisture permeation preventing layer (gas barrier layer) on the front surface or the back surface.

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

<Anode>
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.

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

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

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

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

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

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

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

<Cathode>
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.

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

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

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

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

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

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

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

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

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

-Light emitting layer-
The light-emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer which has the function to provide and to emit light.

  The light emitting layer in the present invention may be composed of only a light emitting material, or may be a mixed layer of a host material and a light emitting material. The light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the light emitting material may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Further, the light emitting layer may include a material that does not have charge transporting properties and does not emit light. The light emitting layer is preferably a light emitting material and a host material using the complex of the present invention.

  In addition, the light emitting layer may be a single layer or two or more layers, and each layer may emit light in different emission colors.

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

  Examples of the phosphorescent material that can be used in the present invention include, in addition to the compounds of the present invention, US Pat. , WO02 / 44189A1, WO05 / 19373A2, JP2001-247859, JP2002-302671, JP2002-117978, JP2003-133074, JP2002-235076, JP2003-123982, JP2002-170684. EP12111257, JP2002-226495, JP2002-234894, JP2001247478, JP2001-298470, JP20. 2-136774, JP 2002-203678, JP 2002-203679, JP 2004-357799, JP 2006-256999, JP 2007-19462, JP 2007-84635, JP 2007-96259, etc. The phosphorescent light-emitting compounds described above and the like are preferable. Among them, more preferable light-emitting materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb. Examples include complexes, Gd complexes, Dy complexes, and Ce complexes. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or a Re complex. Further, from the viewpoints of luminous efficiency, driving durability, chromaticity, etc., Ir complexes, Pt complexes, and Re complexes containing a tridentate or higher polydentate ligand are preferable, and Pt complexes having a tetradentate ligand are particularly preferable. .

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

-Hole injection layer, hole transport layer-
The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side. Specifically, the hole injection layer and the hole transport layer are carbazole derivatives, azacarbazole derivatives, indole derivatives, azaindole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamines. Derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, organosilane derivatives, carbon In addition, a layer containing various metal complexes represented by an Ir complex having phenylazole or phenylazine as a ligand is preferable.
An electron-accepting dopant can be contained in the hole injection layer or the hole transport layer of the organic EL device of the present invention. As the electron-accepting dopant introduced into the hole-injecting layer or the hole-transporting layer, any inorganic compound or organic compound can be used as long as it has an electron-accepting property and oxidizes an organic compound.

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

As the organic compound, a compound having a nitro group, halogen, cyano group, trifluoromethyl group or the like as a substituent, a quinone compound, an acid anhydride compound, fullerene, or the like can be preferably used.
In addition, JP-A-6-212153, JP-A-11-111463, JP-A-11-251067, JP-A-2000-196140, JP-A-2000-286054, JP-A-2000-315580, JP-A-2001-102175, JP-A-2001-2001. -160493, JP2002-252085, JP2002-56985, JP2003-157981, JP2003-217862, JP2003-229278, JP2004-342614, JP2005-72012, JP20051666667 The compounds described in JP-A-2005-209643 and the like can be preferably used.
Among these, hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane, tetrafluorotetracyanoquinodimethane, p-fluoranyl, p-chloranil, p-bromanyl, p-benzoquinone, 2,6-dichlorobenzoquinone, 2 , 5-dichlorobenzoquinone, 1,2,4,5-tetracyanobenzene, 1,4-dicyanotetrafluorobenzene, 2,3-dichloro-5,6-dicyanobenzoquinone, p-dinitrobenzene, m-dinitrobenzene, o-dinitrobenzene, 1,4-naphthoquinone, 2,3-dichloronaphthoquinone, 1,3-dinitronaphthalene, 1,5-dinitronaphthalene, 9,10-anthraquinone, 1,3,6,8-tetranitrocarbazole, 2,4,7-trinitro-9- Luenone, 2,3,5,6-tetracyanopyridine or fullerene C60 is preferred, and hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane, tetrafluorotetracyanoquinodimethane, p-fluoranyl, p- Chloranil, p-bromanyl, 2,6-dichlorobenzoquinone, 2,5-dichlorobenzoquinone, 2,3-dichloronaphthoquinone, 1,2,4,5-tetracyanobenzene, 2,3-dichloro-5,6-dicyano Benzoquinone or 2,3,5,6-tetracyanopyridine is more preferred, and tetrafluorotetracyanoquinodimethane is particularly preferred.

  These electron-accepting dopants may be used alone or in combination of two or more. Although the usage-amount of an electron-accepting dopant changes with kinds of material, it is preferable that it is 0.01 mass%-50 mass% with respect to hole transport layer material, and it is 0.05 mass%-20 mass%. It is further more preferable and it is especially preferable that it is 0.1 mass%-10 mass%.

  The thicknesses of the hole injection layer and the hole transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.

  The thickness of the hole transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the hole injection layer is preferably 0.1 nm to 200 nm, more preferably 0.5 nm to 100 nm, and still more preferably 1 nm to 100 nm.

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

-Electron injection layer, electron transport layer-
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. Specifically, the electron injection layer and the electron transport layer are triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, Carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol derivative complexes, metal phthalocyanines, benzoxazoles and benzothiazoles as ligands It is preferably a layer containing various complexes typified by the complex to be prepared, an organosilane derivative, and the like.

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

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

The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and still more preferably 0.5 nm to 50 nm.
The electron injection layer and the electron transport layer may have a single-layer structure 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.

-Hole blocking layer-
The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
Examples of organic compounds constituting the hole blocking layer include aluminum complexes such as Aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as BAlq), triazole derivatives, and 2,9-dimethyl. And phenanthroline derivatives such as -4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP). The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm.
The hole blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

-Charge generation layer-
The organic EL device of the present invention can have a configuration in which a charge generation layer is provided between a plurality of light emitting layers in order to improve luminous efficiency.
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 a layer adjacent to the charge generation layer.

The material for forming the charge generation layer may be any material having the above functions, and may be formed of a single compound or a plurality of compounds.
Specifically, it may be a conductive material, a semiconductive material such as a doped organic layer, or an electrically insulating material. 11-329748, Unexamined-Japanese-Patent No. 2003-272860, and the material of Unexamined-Japanese-Patent No. 2004-39617 are mentioned.
More specifically, transparent conductive materials such as ITO and IZO (indium zinc oxide), fullerenes such as C60, conductive organic materials such as oligothiophene, metal phthalocyanines, metal-free phthalocyanines, metal porphyrins, metal-free Conductive organic materials such as porphyrins, metal materials such as Ca, Ag, Al, Mg: Ag alloy, Al: Li alloy, Mg: Li alloy, hole conductive material, electron conductive material, and a mixture thereof May be used.
The hole conductive material is, for example, a material in which a hole transporting organic material such as 2-TNATA or NPD is doped with an oxidant having an electron withdrawing property such as F4-TCNQ, TCNQ, or FeCl ₃ , or a P-type conductive material. The electron conductive material includes an electron transporting organic material doped with a metal or a metal compound having a work function of less than 4.0 eV, an N type conductive polymer, N type Type semiconductors. Examples of the N-type semiconductor include N-type Si, N-type CdS, and N-type ZnS. Examples of the P-type semiconductor include P-type Si, P-type CdTe, and P-type CuO.
Further, an electrically insulating material such as V ₂ O ₅ can be used for the charge generation layer.

  The charge generation layer may be a single layer or a stack of a plurality of layers. A structure in which a plurality of layers are stacked includes a conductive material such as a transparent conductive material and a metal material and a hole conductive material, or a structure in which an electron conductive material is stacked, and the above hole conductive material and electron conductive And a layer having a structure in which a functional material is laminated.

In general, it is preferable to select a film thickness and a material for the charge generation layer so that the visible light transmittance is 50% or more. The film thickness is not particularly limited, but is preferably 0.5 to 200 nm, more preferably 1 to 100 nm, still more preferably 3 to 50 nm, and particularly preferably 5 to 30 nm.
The method for forming the charge generation layer is not particularly limited, and the organic layer formation method described above can be used.

The charge generation layer is formed between the two or more light emitting layers, and the anode side and the cathode side of the charge generation layer may contain a material having a function of injecting charges into adjacent layers. In order to improve the electron injection property to the layer adjacent to the anode side, for example, an electron injection compound such as BaO, SrO, Li ₂ O, LiCl, LiF, MgF ₂ , MgO, and CaF _{2 is} added to the anode side of the charge generation layer. May be laminated.
In addition to the contents mentioned above, the material for the charge generation layer should be selected based on the descriptions in JP-A-2003-45676, US Pat. Nos. 6,337,492, 6,107,734, 6,872,472, and the like. Can do.

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

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

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

<Driving method>
The element of the present invention can obtain light emission by applying a direct current (which may include an alternating current component if necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. it can.

  Regarding the driving method of the element of the present invention, JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234665, and JP-A-8-214447, The driving methods described in Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6023308, etc. can be applied.

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

  Hereinafter, the present invention will be described in detail based on examples, but the embodiment of the present invention is not limited thereto.

(Comparative Examples 1 and 2 and Examples 1 to 12)
The cleaned ITO substrate was put into a vapor deposition apparatus, and copper phthalocyanine was vapor-deposited by 10 nm, and NPD ((N, N′-di-α-naphthyl-N, N′-diphenyl) -benzidine) was vapor-deposited thereon by 40 nm. On top of this, the host material and the light-emitting material described in Table 21 were vapor-deposited at a ratio of 97: 3 (mass ratio) of 40 nm, on which BAlq was vapor-deposited at 10 nm, and further Alq was vapor-deposited at 30 nm. On top of this, lithium fluoride was deposited to 3 nm, and then 60 nm of aluminum was deposited to produce a device. As a result of applying a DC constant voltage to the EL element to emit light using a source measure unit 2400 type manufactured by Toyo Technica, light emission derived from the light emitting material was obtained. Furthermore, the luminance half-life of the element driven at 360 cd / m ² (light emitting area 4 mm ² ) and 1000 cd / m ² (light emitting area 4 mm ² ), which is a higher luminance condition, was measured. In Examples 11 and 12, elements were similarly fabricated using deuterated Alq (D-Alq) instead of Alq. The results are shown in Table 21.

(Comparative Example 3)
The cleaned ITO substrate was put into a vapor deposition apparatus, and copper phthalocyanine was vapor-deposited by 10 nm, and NPD ((N, N′-di-α-naphthyl-N, N′-diphenyl) -benzidine) was vapor-deposited thereon by 40 nm. On top of this, a host material described in Table 22 and Ir (ppy) ₃ were deposited at a ratio (mass ratio) of 97: 3 of 40 nm, and BAlq was deposited thereon at 10 nm, and further Alq was deposited thereon at 30 nm. On top of this, lithium fluoride was deposited to 3 nm, and then 60 nm of aluminum was deposited to produce a device. As a result of applying a DC constant voltage to the EL element to emit light using a source measure unit 2400 type manufactured by Toyo Technica, light emission derived from the light emitting material was obtained. Furthermore, the luminance half-life of the element driven at 360 cd / m ² (light emitting area 4 mm ² ) and 1000 cd / m ² (light emitting area 4 mm ² ), which is a higher luminance condition, was measured. Similarly, an element was manufactured. The results are shown in Table 22.

(Examples 13 and 14)
The cleaned ITO substrate was put into a vapor deposition apparatus, and copper phthalocyanine was vapor-deposited by 10 nm, and NPD ((N, N′-di-α-naphthyl-N, N′-diphenyl) -benzidine) was vapor-deposited thereon by 40 nm. On top of this, a host material described in Table 22 and Ir (ppy) ₃ were deposited at a ratio (mass ratio) of 97: 3 by 40 nm, BAlq was 10 nm thereon, and Alq and an exemplified compound were further added to 90 nm. : Deposited at a ratio of 10 to 30 nm. On top of this, lithium fluoride was deposited to 3 nm, and then 60 nm of aluminum was deposited to produce a device. As a result of applying a DC constant voltage to the EL element to emit light using a source measure unit 2400 type manufactured by Toyo Technica, light emission derived from the light emitting material was obtained. Furthermore, the luminance half-life of the element driven at 360 cd / m ² (light emitting area 4 mm ² ) and 1000 cd / m ² (light emitting area 4 mm ² ), which is a higher luminance condition, was measured. Similarly, an element was manufactured. The results are shown in Table 22.

  Copper phthalocyanine, NPD, Compound I (Compound 114 described in JP-A-2006-96255), Compound II (Compound 10-1 described in JP-A-2008-37848), host material used in Examples, The chemical structure of BAlq is shown below.

  Even when the other metal complex of the present invention is used, an organic electroluminescent element excellent in durability at high luminance can be obtained as described above.

Claims (9)

An organic electroluminescent device having an organic layer including at least a light emitting layer between a pair of electrodes, wherein the organic layer contains a compound represented by the following general formula (1) .
General formula (1)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Y ¹ and Y ² each independently represent a carbon atom or a nitrogen atom. Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from Y ¹ , X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from Y ² , X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. When Y ¹ and Y ² are carbon atoms, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. When Y ¹ is a nitrogen atom and Y ² is a carbon atom, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. For Y ^{1, Y 2} are both nitrogen ^{atoms, Z 1, Z 2, Z} 3, the combination of ^{Z 4 are, Z 1, Z 2, Z} 3, ^{Z 4} order (carbon atoms of a carbon atom, a carbon atom , Nitrogen atom), (carbon atom, carbon atom, phosphorus atom, nitrogen atom), (carbon atom, carbon atom, carbon atom, phosphorus atom), (carbon atom, carbon atom, phosphorus atom, phosphorus atom), (carbon atom , Nitrogen atom, carbon atom, carbon atom), (carbon atom, phosphorus atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, phosphorus atom, carbon atom), (carbon atom, phosphorus atom, phosphorus atom, carbon atom) Atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom), (carbon atom, phosphorus atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, phosphorus atom), (carbon atom, phosphorus atom) Atoms, carbon atoms, phosphorus atoms). The bond between Z ¹ , Z ² , Z ³ and Z ⁴ and M represents a coordination bond or a covalent bond. L represents a divalent linking group. M represents a divalent metal ion. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).
General formula (2)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Y ¹ and Y ² each independently represent a carbon atom or a nitrogen atom. Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from Y ¹ , X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from Y ² , X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. When Y ¹ and Y ² are carbon atoms, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. When Y ¹ is a nitrogen atom and Y ² is a carbon atom, at least one of Z ¹ and Z ⁴ represents a nitrogen atom or a phosphorus atom. For Y ^{1, Y 2} are both nitrogen ^{atoms, Z 1, Z 2, Z} 3, the combination of ^{Z 4 are, Z 1, Z 2, Z} 3, ^{Z 4} order (carbon atoms of a carbon atom, a carbon atom , Nitrogen atom), (carbon atom, carbon atom, phosphorus atom, nitrogen atom), (carbon atom, carbon atom, carbon atom, phosphorus atom), (carbon atom, carbon atom, phosphorus atom, phosphorus atom), (carbon atom , Nitrogen atom, carbon atom, carbon atom), (carbon atom, phosphorus atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, phosphorus atom, carbon atom), (carbon atom, phosphorus atom, phosphorus atom, carbon atom) Atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom), (carbon atom, phosphorus atom, carbon atom, nitrogen atom), (carbon atom, nitrogen atom, carbon atom, phosphorus atom), (carbon atom, phosphorus atom) Atoms, carbon atoms, phosphorus atoms). The bond between Z ¹ , Z ² , Z ³ and Z ⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group. The organic electroluminescent element according to claim 1 or 2, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (3).
General formula (3)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ³¹ , Z ² , Z ³ , and Z ³⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. At least one of Z ³¹ and Z ³⁴ represents a nitrogen atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a carbon atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a carbon atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ³¹ , Z ² , Z ³ and Z ³⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group. The organic electroluminescent element according to claim 1 or 2, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (4).

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ³¹ , Z ² , Z ³ , and Z ³⁴ each independently represent a nitrogen atom, a carbon atom, or a phosphorus atom. At least one of Z ³¹ and Z ³⁴ represents a nitrogen atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a nitrogen atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a carbon atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ³¹ , Z ² , Z ³ and Z ³⁴ and M represents a coordinate bond or a covalent bond. L represents a divalent linking group. The organic electroluminescent element according to claim 1 or 2, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (5).
General formula (5)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ each independently represent a nitrogen atom or a carbon atom. Bonds between atoms in a 5-membered ring formed from a nitrogen atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a nitrogen atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. ^However, the combination of ^{Z 51, Z 52, Z 53} , Z 54 ^is in the order of ^{Z 51, Z 52, Z 53} , Z 54 , (carbon atom, a carbon atom, a carbon atom, a nitrogen atom), (carbon atom, a nitrogen Atom, carbon atom, carbon atom), (carbon atom, nitrogen atom, carbon atom, nitrogen atom). The bond between Z ⁵¹ , Z ⁵² , Z ⁵³ and Z ⁵⁴ and platinum represents a coordinate bond or a covalent bond, respectively. L represents a divalent linking group. The organic electroluminescent element according to claim 1 or 2, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (6).
General formula (6)

In the formula, X ¹ , X ² , X ³ , X ⁴ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ each independently represent a carbon atom or a nitrogen atom. X ⁵ , X ⁶ , X ⁹ and X ¹⁰ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. X ⁷ and X ⁸ each independently represent a carbon atom or a nitrogen atom. Z ⁶¹ , Z ² , Z ³ and Z ⁶⁴ each independently represent a nitrogen atom, a carbon atom or a phosphorus atom. Bonds between atoms in a 5-membered ring formed from a carbon atom, X ⁵ , X ⁶ , X ⁷ , Z ² and a 5-membered ring formed from a nitrogen atom, X ¹⁰ , X ⁹ , X ⁸ , Z ³ are Represents a single bond or a double bond. The bond between Z ⁶¹ , Z ² , Z ³ and Z ⁶⁴ and platinum represents a coordinate bond or a coordinate bond, respectively. L represents a divalent linking group.   The organic electroluminescent element according to claim 1, wherein the light emitting layer contains a compound represented by the general formula.   8. The organic electroluminescent element according to claim 1, wherein a material having at least one deuterium atom is contained in at least one of the organic layers.   9. The organic electroluminescent device according to claim 8, wherein the material having at least one deuterium atom is a material containing either a carbazole skeleton or an indole skeleton having at least one deuterium atom.