JP2009267171A - Organic electric field light emitting element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a material for an organic electric field light emitting element, which is prominent in storing stability, and an organic electric field light emitting element, prominent in durability. <P>SOLUTION: The organic electric field light emitting element contains a compound shown by a Formula (I) in an organic layer. In the formula (I), Q<SP>1</SP>and Q<SP>4</SP>shows respectively and independently an aromatic hetero five membered ring. Q<SP>2</SP>shows aromatic hetero six membered ring. Q<SP>3</SP>shows benzene ring or aromatic hetero six membered ring. Y<SP>1</SP>and Z<SP>4</SP>shows carbon atom or nitrogen atom. X<SP>11</SP>-X<SP>13</SP>, X<SP>41</SP>-X<SP>43</SP>shows respectively and independently nitrogen atom, N-R<SP>N1</SP>, oxygen atom, sulfur atom, phosphor atom or C-R<SP>C1</SP>. X<SP>21</SP>-X<SP>23</SP>, X<SP>31</SP>-X<SP>33</SP>shows respectively and independently nitrogen atom, N-R<SP>N1</SP>, oxygen atom, sulfur atom or C-R<SP>C1</SP>. R<SP>N1</SP>shows hydrogen atom or a substituent. R<SP>C1</SP>shows hydrogen atom or a substituent. In Q<SP>1</SP>and Q<SP>4</SP>, a bond shown by an solid line and a double broken lines shows either one of a single bond or double bond. M shows bivalent metal ion. A broken line which shows the bond of M and nitrogen atom shows coordinate linkage while solid lines which show the bond of M and carbon atom as well as the connection of M and Z<SP>4</SP>show covalent bond. L shows bivalent linkage radical. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

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

  Organic electroluminescent elements (organic EL elements) are actively researched and developed because they can emit light with high brightness when driven at a low voltage. An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.

In recent years, the use of phosphorescent light emitting materials has led to higher efficiency of devices. Known phosphorescent materials include iridium complexes and platinum complexes (see, for example, Patent Document 1 and Patent Document 2).
Moreover, the technique regarding the organic electroluminescent element using the complex which has a tetradentate ligand for the purpose of improving durability and phosphorescence quantum yield of a complex is disclosed (for example, refer patent document 3 and patent document 4).

US Pat. No. 6,303,238 International Publication No. 00/57676 Pamphlet JP 2005-310733 A JP 2006-232784 A

However, there is a demand for an element that is practically more durable. In addition, in order to reduce manufacturing costs and improve productivity, a material that exhibits high performance regardless of storage conditions is required.
The objective of this invention is providing the organic electroluminescent element excellent in durability, and the organic electroluminescent element material excellent in storage stability.

  As a result of investigations to solve the above problems, the present inventors have found that an organic electroluminescent element containing a metal complex having a tetradentate ligand having a specific structure in an organic layer solves the above problems. That is, the above problem can be solved by the following means.

[1] An organic electroluminescent element having an organic layer including a light emitting layer between a pair of electrodes, wherein the organic layer contains a compound represented by the following general formula (I): Light emitting element.

(In general formula (I), Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero six-membered ring. Q ³ represents a benzene ring or an aromatic hetero six-membered ring. Y ¹ and Z ⁴ represent a carbon atom or a nitrogen atom, and the combination of [Y ¹ , Z ⁴ ] is any of [C, N], [C, C], [N, N] X ^{11 to} X ¹³ and X ^{41 to} X ⁴³ each independently represent a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom, a phosphorus atom or CRC ¹ , X ^{21 to} X ²³ , X ^{31 to} X ³³ are Each independently represents a nitrogen atom, NR ^N1 , oxygen atom, sulfur atom or CRC ¹ , R ^N1 represents a hydrogen atom or substituent, R ^C1 represents a hydrogen atom or substituent, and a solid line in Q ¹ and Q ⁴ A bond indicated by a broken double line represents either a single bond or a double bond, M represents a divalent metal ion, and a broken line indicating a bond between M and a nitrogen atom represents a coordinate bond. Represents M and carbon atom Solid line shows binding of micro M and Z ⁴ are, .L representing the covalent bond represents a divalent linking group.)

[2] The organic electroluminescence device as described in [1], wherein Y ¹ represents a carbon atom and Z ⁴ represents a carbon atom.
[3] The organic electroluminescent element as described in [1], wherein Y ¹ represents a carbon atom and Z ⁴ represents a nitrogen atom.
[4] The organic electroluminescent element as described in [1], wherein Y ¹ represents a nitrogen atom and Z ⁴ represents a nitrogen atom.
[5] The organic electroluminescent element as described in any one of [1] to [4], wherein M represents Pt.
[6] The organic electroluminescent element as described in any one of [1] to [5], wherein L is a disubstituted methylene linking group.
[7] The organic electroluminescent element as described in any one of [1] to [6], wherein the light-emitting layer contains a compound represented by the general formula (I).
[8] The organic electroluminescent element as described in 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 electric field according to [8], wherein the material having at least one deuterium atom is a material having either a carbazole skeleton or an indole skeleton having at least one deuterium atom. Light emitting element.

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element excellent in durability and the organic electroluminescent element material excellent in storage stability can be provided.

Hereinafter, preferred embodiments of the organic EL element according to the present invention will be described.
The organic EL device according to the present invention has an organic layer including at least a light emitting layer between a pair of electrodes. The organic layer may include 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 and the like in addition to the light emitting layer. Each layer may have other functions. Each layer may be formed of a plurality of layers.

  As an aspect of stacking the organic layers, an aspect in which the hole transport layer, the light emitting layer, and the electron transport layer are stacked in this order from the anode side is preferable. Furthermore, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer and / 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.

At least one of the organic layers contains the metal complex represented by the general formula (I).
The function of the metal complex represented by the general formula (I) is not limited, and can be used as a light-emitting material, a host material, an exciton block material, a charge block material, or a charge transport material. Of these, the use as a light emitting material, a host material, and a charge transport material is more preferable, the use as a light emitting material and a host material is still more preferable, and the use as a light emitting material is most preferable.

  In addition, the layer containing the metal complex represented by the general formula (I) can be contained in any of the organic layers described above, but is preferably contained in the light emitting layer. The host material is more preferably contained in the light emitting layer, the light emitting material is more preferably contained in the light emitting layer, and the light emitting layer is particularly preferably contained together with at least one kind of host material.

When the content of the metal complex represented by the general formula (I) is contained in the light emitting layer as a light emitting material, the content is in the range of 0.1% by mass or more and 50% by mass or less with respect to the total mass of the light emitting layer. Preferably, the range of 0.2 mass% or more and 30 mass% or less is more preferable, the range of 0.3 mass% or more and 20 mass% or less is more preferable, and the range of 0.5 mass% or more and 15 mass% or less is the most preferable.
When the metal complex represented by the general formula (I) is used for a layer other than the light emitting layer (for example, a charge transport layer), the layer is preferably contained in an amount of 10% by mass to 100% by mass, and 30% by mass. More preferably, it is contained in an amount of 100% by mass to 100% by mass.

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

(In general formula (I), Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero six-membered ring. Q ³ represents a benzene ring or an aromatic hetero six-membered ring. Y ¹ and Z ⁴ represent a carbon atom or a nitrogen atom, and the combination of [Y ¹ , Z ⁴ ] is any of [C, N], [C, C], [N, N] X ^{11 to} X ¹³ and X ^{41 to} X ⁴³ each independently represent a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom, a phosphorus atom or CRC ¹ , X ^{21 to} X ²³ , X ^{31 to} X ³³ are Each independently represents a nitrogen atom, NR ^N1 , oxygen atom, sulfur atom or CRC ¹ , R ^N1 represents a hydrogen atom or substituent, R ^C1 represents a hydrogen atom or substituent, and a solid line in Q ¹ and Q ⁴ A bond indicated by a broken double line represents either a single bond or a double bond, M represents a divalent metal ion, and a broken line indicating a bond between M and a nitrogen atom represents a coordinate bond. Represents M and carbon atom Solid line shows binding of micro M and Z ⁴ are, .L representing the covalent bond represents a divalent linking group.)

Y ¹ and Z ⁴ represent a carbon atom or a nitrogen atom, and the combination of [Y ¹ , Z ⁴ ] is any one of [C, N], [C, C], and [N, N].
^{X 11 ~X 13, X 41 ~X} 43 are each independently a nitrogen atom, NR ^N1, oxygen atom, sulfur atom, a phosphorus atom or CR ^{C1. X 21 ~X 23, X 31 ~X} 33 are each independently a nitrogen atom, NR ^N1, oxygen atom, a sulfur atom or CR ^C1.

Examples of R ^C1 include a hydrogen atom and a group selected from the following substituent group A.

(Substituent group A)
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, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, pentafluoroethyl, etc.), alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably carbon number). 2-10, for example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably carbon number). 2-10, for example, propargyl, 3-pentynyl, etc.), aryl groups (preferably Or 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl, and pentafluorophenyl. An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino; And alkoxy groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy) An aryloxy group (preferably having 6 to 30 carbon atoms, more preferred) Or having 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), a heterocyclic oxy group (preferably having 1 to 1 carbon atoms). 30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy etc. are mentioned, An acyl group (preferably C1-C30, more). Preferably it is C1-C20, Most preferably, it is C1-C12, for example, acetyl, a benzoyl, a formyl, pivaloyl etc. are mentioned, An alkoxycarbonyl group (Preferably C2-C30, More preferably, it is carbon. 2 to 20, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl Bonyl and the like can be mentioned. ), An aryloxycarbonyl group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, such as phenyloxycarbonyl), an acyloxy group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.), An acylamino group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, more preferably carbon atoms). 2 to 20, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as 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 having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms. Examples thereof include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably A prime number of 1-20, particularly preferably a carbon number of 1-12, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc., an alkylthio group (preferably having a carbon number of 1-30, more preferably a carbon number). 1 to 20, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio, etc.), arylthio groups (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably carbon atoms). And a heterocyclic thio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). Pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio Etc. ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms such as mesyl and tosyl), a sulfinyl group (preferably carbon). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), ureido group (preferably 1 to 30 carbon atoms, more Preferably it is C1-C20, Most preferably, it is C1-C12, for example, ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide group (preferably C1-C30, more preferably It has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms. Examples thereof include diethyl phosphoric acid amide and phenyl phosphoric acid amide. Hydroxy group, mercapto group, fluoro group, chloro group, bromo group, iodo group, cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (Preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and the hetero atom is, for example, a nitrogen atom, an oxygen atom, or a sulfur atom, specifically, imidazolyl, pyridyl, quinolyl, furyl, thienyl. , Piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl, triphenylsilyl, etc. ), A silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy and triphenylsilyloxy). , Phosphoryl group (for example, diphenylphosphoryl group, dimethylphosphoryl group, etc.)

R ^C1 is preferably a hydrogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, alkylthio group, heterocyclic thio group, fluoro group, chloro group, Cyano group, heterocyclic group, silyl group, silyloxy group, phosphoryl group, more preferably hydrogen atom, alkyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, alkylthio group, heterocyclic ring Thio group, fluoro group, cyano group, heterocyclic group and silyl group, more preferably hydrogen atom, alkyl group, aryl group, amino group, alkoxy group, fluoro group, cyano group, heterocyclic group and silyl group And more preferably a hydrogen atom, an alkyl group, an aryl group, a fluoro group, a cyano group, or a heterocyclic group. .

^Examples of R ^N1 include a group selected from the following substituent group B in addition to a hydrogen atom.

(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, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, pentafluoroethyl, etc.), alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably carbon number). 2-10, for example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably carbon number). 2-10, for example, propargyl, 3-pentynyl, etc.), aryl groups (preferably Or 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl, and pentafluorophenyl. 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 For example, phenyloxycarbonyl, etc.), acyloxy groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy). A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, And carbamoyl 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, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenyl Carbamoyl, etc.), heterocyclic groups (preferably Or a hetero atom, for example, a nitrogen atom, an oxygen atom, or a sulfur atom, specifically, imidazolyl, pyridyl, quinolyl, furyl, thienyl, Examples include piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group and the like. )

The group represented by R ^N1 is preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, more preferably a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, More preferably, they are a hydrogen atom, an alkyl group, an aryl group, and a heterocyclic group, More preferably, they are a hydrogen atom, an alkyl group, and an aryl group heterocyclic group.

Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero 6-membered ring. Q ³ represents a benzene ring or an aromatic hetero 6-membered ring. That is, the X ^{11 to} X ¹³ , X ^{21 to} X ²³ , X ^{41 to} X ⁴³ , Y ¹ , and Z ⁴ are selected so that Q ¹ , Q ² , and Q ⁴ are each an aromatic heterocycle, ³¹ to X ³³ is selected to Q ³ is a benzene ring or an aromatic hetero ring.

More specifically, Q ¹ represents an aromatic hetero five-membered ring and is coordinated to M with a nitrogen atom. Examples of Q ¹ include an imidazole ring, a pyrazole ring, a triazole ring, an oxazole ring, a thiazole ring, and a condensed ring containing them (for example, a benzimidazole ring). Q ¹ is preferably an imidazole ring, a pyrazole ring, a triazole ring, an oxazole ring, a thiazole ring and a condensed ring containing them, more preferably an imidazole ring, a pyrazole ring and a condensed ring containing them. Since Q ¹ is an imidazole ring, a pyrazole ring, a triazole ring, an oxazole ring, a thiazole ring and a condensed ring containing them (more preferably, an imidazole ring, a pyrazole ring and a condensed ring containing them), Stability is improved and durability of the element can be improved.

Q ² represents an aromatic hetero 6-membered ring, preferably a nitrogen-containing aromatic hetero 6-membered ring, and is coordinated to M with a nitrogen atom. Q ² is preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring or a condensed ring containing them (for example, a quinoline ring), and more preferably a pyridine ring, a pyrazine ring or a condensed ring containing them. It is a ring. Since Q ² is a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring and a condensed ring containing them (more preferably, a pyridine ring, a pyrazine ring and a condensed ring containing them), Stability is improved and durability of the element can be improved.

Q ³ represents a benzene ring or an aromatic hetero 6-membered ring, and is covalently bonded to M through a carbon atom. Examples of Q ³ include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and a condensed ring containing them (for example, a quinoline ring, a naphthalene ring, etc.), preferably a benzene ring, a pyridine ring, A pyrazine ring and a condensed ring containing them. When Q ³ is a benzene ring, a pyridine ring, a pyrazine ring or a condensed ring containing them, the stability of the complex itself can be improved, and the durability of the device can be improved.

Q ⁴ represents an aromatic hetero five-membered ring, and the aromatic hetero ring represented by Q ⁴ is covalently bonded to M at a carbon atom or a nitrogen atom.
Q ⁴ bonded to M by a carbon atom includes a furan ring, a thiophene ring, a thiazole ring, an oxazole ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, a silole ring, and a condensed ring containing them (for example, an indazole ring). And benzothiazole ring))).
Examples of Q ⁴ bonded to M through a nitrogen atom include a pyrazole ring, a pyrrole ring, an imidazole ring, a triazole ring, and condensed rings containing them (for example, an indole ring, a benzimidazole ring, etc.).
Q ⁴ is preferably a furan ring, a thiophene ring, a pyrazole ring, a pyrrole ring, an imidazole ring or a condensed ring containing them. When Q ⁴ is a furan ring, a thiophene ring, a pyrazole ring, a pyrrole ring, an imidazole ring or a condensed ring containing them, the stability of the complex itself can be improved, and the durability of the device can be improved.
Q ⁴ is preferably bonded to M by a carbon atom from the viewpoint of the stability of the material itself and the durability of the device.

In addition, when a plurality of X ^{11 to} X ¹³ , X ^{41 to} X ⁴³ , X ^{21 to} X ²³ , and X ^{31 to} X ³ are NR ^N1 and / or CRC ¹ , if possible, a plurality of R ^N1 and Alternatively, R ^C1 may be bonded to each other to form a ring.
In that case, Q ^{1 to} Q ⁴ are condensed rings. As specific examples in the case where Q ^{1 to} Q ⁴ are condensed rings, examples of Q ¹ and Q ⁴ include an indole ring, an indazole ring, an imidazole ring, and a triazole ring. Examples of Q ² include an isoquinoline ring. Examples of Q ³ include a naphthalene ring and a quinoline ring.

Examples of structures represented by Q ¹ , Q ² , Q ³ , and Q ⁴ in the general formula (I) are given below, but the present invention is not limited to these. In the following formulas, M, L corresponds to the M, L in the general formula (I), respectively, Q is, Q in the [partial structure represented by Q ^1] represents Q ^2, Table in [Q ² the Q of the partial structure] in which represents Q ^1, in which Q partial structure] in represented by Q ³ are represents Q ^4, and Q is Q ³ in the partial structure] represented by [Q ⁴ To express.

[Partial structure represented by Q ¹ ]

[Partial structure represented by Q ² ]

[Partial structure represented by Q ³ ]

[Partial structure represented by Q ^4]

M represents a divalent metal ion. M is preferably a divalent platinum ion, palladium ion, nickel ion, zinc ion or copper ion, more preferably a platinum ion or palladium ion, and still more preferably a platinum ion. When M is platinum ion, palladium ion, nickel ion, zinc ion, or copper ion (more preferably, platinum ion, palladium ion, and more preferably platinum ion), a complex having a high emission quantum yield can be obtained. The quantum efficiency of is also increased.
A broken line indicating a bond between M and a nitrogen atom represents a coordination bond, and a solid line indicating a bond between M and a carbon atom and M and Z ⁴ represents a covalent bond. Here, the coordinate bond means a bond between a neutral group having no charge and a metal ion, and the covalent bond means a bond between an anionic group and the metal ion.

L represents a divalent linking group. The divalent linking group is preferably a divalent linking group composed of atoms such as a carbon atom, a nitrogen atom, a silicon atom, a phosphorus atom, an oxygen atom, a sulfur atom, and a germanium atom. The divalent linking group may be composed of one of these atoms, or may be a group in which a plurality of atoms are bonded linearly or cyclically.
These atoms may have a substituent if possible. Examples of the substituent include the substituent group A. In the case of having a plurality of substituents, the substituents may be bonded to form a ring.
Hereinafter, although the specific example of L is shown, it is not limited to the following. In the following examples, Q represents either Q ² or Q ³ .

  L is preferably a disubstituted methylene linking group. The disubstituted methylene linking group is preferably a dialkylmethylene group, a diarylmethylene group or a diheteroarylmethylene group, more preferably a dimethylmethylene group or a diphenylmethylene group, and even more preferably a dimethylmethylene group.

  The compound represented by the general formula (I) is preferably a compound represented by the following general formula (I-a), (I-b), or (I-c).

(In general formula (Ia), Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero six-membered ring. Q ³ represents a benzene ring or an aromatic hetero six-membered ring. X ^{11 to} X ¹³ and X ^{41 to} X ⁴³ each independently represents a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom, a phosphorus atom or CRC ¹ .X ^{21 to} X ²³ , X ^{31 to} X ³³ each independently represents a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom or CRC ¹ , R ^N1 represents a hydrogen atom or a substituent, R ^C1 represents a hydrogen atom or a substituent, Q ¹ and Q ⁴ A bond described by a solid line and a broken double line represents either a single bond or a double bond, M represents a divalent metal ion, and a broken line indicating a bond between M and a nitrogen atom is (A solid line representing a coordinate bond and a bond between M and a carbon atom represents a covalent bond. L represents a divalent linking group.)

(In general formula (Ib), Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero six-membered ring. Q ³ represents a benzene ring or an aromatic hetero six-membered ring. X ^{11 to} X ¹³ and X ^{41 to} X ⁴³ each independently represents a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom, a phosphorus atom or CRC ¹ .X ^{21 to} X ²³ , X ^{31 to} X ³³ each independently represents a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom or CRC ¹ , R ^N1 represents a hydrogen atom or a substituent, R ^C1 represents a hydrogen atom or a substituent, Q ¹ and Q ⁴ A bond described by a solid line and a broken double line represents either a single bond or a double bond, M represents a divalent metal ion, and a broken line indicating a bond between M and a nitrogen atom is (A solid line representing a coordinate bond and a bond between M and a nitrogen atom and a bond between M and a carbon atom represents a covalent bond. L represents a divalent linking group.)

(In general formula (Ic), Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero six-membered ring. Q ³ represents a benzene ring or an aromatic hetero six-membered ring. X ^{11 to} X ¹³ and X ^{41 to} X ⁴³ each independently represents a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom, a phosphorus atom or CRC ¹ .X ^{21 to} X ²³ , X ^{31 to} X ³³ each independently represents a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom or CRC ¹ , R ^N1 represents a hydrogen atom or a substituent, R ^C1 represents a hydrogen atom or a substituent, Q ¹ and Q ⁴ A bond described by a solid line and a broken double line represents either a single bond or a double bond, M represents a divalent metal ion, and a broken line indicating a bond between M and a nitrogen atom is (A solid line representing a coordinate bond and a bond between M and a nitrogen atom and a bond between M and a carbon atom represents a covalent bond. L represents a divalent linking group.)

X ^{11 to} X ¹³ , X ^{21 to} X ²³ , X ^{31 to} X ³³ , X ^{41 to} X ⁴³ , M, and L in general formula (Ia), general formula (Ib), and general formula (Ic) It is synonymous with those in I), and the preferred range is also the same.

  Of the compounds represented by the general formula (Ia), the general formula (Ib), and the general formula (Ic), the compound represented by the general formula (Ia) has higher stability of the complex itself, and the emission quantum yield. This is particularly preferable because a complex having a high rate can be obtained.

As specific examples of the compound represented by the general formula (I), the partial structures represented by Q ¹ , Q ² , Q ³ and Q ⁴ are the following combinations 1 to 3 and the linkage represented by the L Any compound formed in combination with a group.

  Hereinafter, although the specific example of a metal complex represented by General formula (1) is illustrated, this invention is not limited to these.

The compound represented by the general formula (I) can be synthesized by a known synthesis method. Specifically, the compound represented by the general formula (I) can be synthesized by reacting a ligand compound with a metal salt according to a known method.
As a known method, Journal of Organic Chemistry 53, 786, (1988), GR Newkome et al.), Page 789, left line 53 to right line 7, line 790, left line 18 line The method described in line 38, page 790, the method described in lines 19-30 of the right column, Chemische Berichte 113, 2749 (1980), H. Lexy et al.), The method described in page 2752, lines 26-35. Etc.

  The reaction may be performed in the presence of a solvent or in the absence of a solvent. When using a solvent, for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, a sulfoxide solvent, water or the like is used. be able to.

In the reaction, the synthesis of the compound represented by the general formula (I) may be performed in the presence of a base or in the absence of a base.
When a base is used, various bases of inorganic compounds or organic compounds can be used. For example, sodium methoxide, t-butoxy potassium, triethylamine, potassium carbonate and the like can be used.

The reaction temperature of the reaction varies depending on the activity of the reaction, and can be performed in the range of −30 ° C. to 400 ° C. Preferably, it is 0 degreeC-350 degreeC, and 25 degreeC-250 degreeC is more preferable.
The reaction time varies depending on the activity of the reaction raw materials, and can usually be carried out in the range of 1 minute to 24 hours. Preferably, it is 1 minute to 2 hours, and more preferably 1 minute to 30 minutes.

It is preferable to use a material having at least one deuterium atom for the organic layer. The durability can be further improved by using a material having at least one deuterium atom.
A more preferred embodiment is an embodiment in which the same organic layer contains both the compound represented by the general formula (I) and a material having at least one deuterium atom, and a more preferred embodiment is the light emitting layer. In this embodiment, the compound represented by the general formula (I) and a material having at least one deuterium atom are contained.

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

An organic material having at least one deuterium atom is a ratio of a deuterium atom to a hydrogen atom at a position where the hydrogen atom or deuterium atom in the organic material can be bonded (the number of deuterium atoms: the number of hydrogen atoms). Is included in the range of 100: 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 organic material having at least one deuterium atom may be contained in any layer of the organic electroluminescent device, but a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, It is preferably contained in one or more of the exciton block layer and charge block layer, more preferably contained in one or more of the light emitting layer, exciton block layer and charge block layer, and the light emitting layer More preferably, it is contained as a host material in the light emitting layer.

  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 pamphlet.

  A preferable example of the organic material having at least one deuterium atom includes a material containing a nitrogen atom. Among materials containing a nitrogen atom, a material containing a tertiary amine skeleton, a carbazole skeleton, or an indole skeleton is preferred, a material containing a carbazole skeleton or an indole skeleton is more preferred, and a material containing a carbazole skeleton is particularly preferred.

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

  Next, each element constituting the organic EL element will be described.

<Organic layer>
The organic layer includes at least a light emitting layer and may be composed of a single layer or a plurality of layers. When composed of a plurality of layers, as the organic layer other than the light emitting layer, as described above, a hole transport layer, an electron transport layer, a hole block layer, an electron block layer, a hole injection layer, an electron injection layer, etc. Each layer is mentioned.

-Formation of organic layer-
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 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.
As the luminescent material, it is preferable to use a compound represented by the general formula (I).

  Examples of fluorescent light emitting materials 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, styrylamine derivatives, diketo Various complexes such as pyrrolopyrrole derivatives, 8-quinolinol derivative complexes and pyromethene derivative complexes, polythiophene, polyphenol Vinylene, polyphenylene vinylene polymer compounds include compounds such as organic silane derivatives.

Examples of the phosphorescent material include a complex containing a transition metal atom or a lanthanoid atom.
For example, the transition metal atom is not particularly limited, but preferably includes ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, gold, silver, copper, and platinum, and more preferably rhenium, iridium, And platinum, more preferably iridium and platinum.
Examples of the lanthanoid atom include lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. Among these lanthanoid atoms, neodymium, europium, and gadolinium are preferable.

  Examples of the ligand of the complex include G.I. Wilkinson et al., Comprehensive Coordination Chemistry, Pergamon Press, 1987, H.C. Examples include ligands described in Yersin's "Photochemistry and Photophysics of Coordination Compounds" published by Springer-Verlag 1987, Akio Yamamoto "Organic Metal Chemistry-Fundamentals and Applications-" .

The specific ligand is preferably a halogen ligand (preferably a chlorine ligand) or an aromatic carbocyclic ligand (for example, preferably 5 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 30 and more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as cyclopentadienyl anion, benzene anion, or naphthyl anion), nitrogen-containing heterocyclic ligand (for example, preferably Has 5 to 30 carbon atoms, more preferably 6 to 30 carbon atoms, still more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and phenylpyridine, benzoquinoline, quinolinol, bipyridyl, or phenanthroline. Etc.), diketone ligand (for example, acetylacetone, etc.), carboxylic acid ligand (for example, preferably 2-30 carbon atoms, and more) Preferably, it has 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, such as an acetic acid ligand), an alcoholate ligand (for example, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms). More preferably, it has 6 to 20 carbon atoms, such as phenolate ligand), silyloxy ligand (for example, preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, still more preferably 3 to 3 carbon atoms). 20 such as trimethylsilyloxy ligand, dimethyl-tert-butylsilyloxy ligand, triphenylsilyloxy ligand), carbon monoxide ligand, isonitrile ligand, cyano ligand, Phosphorus ligand (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, still more preferably 3 to 20 carbon atoms, and particularly preferably 6 to 20 carbon atoms. A rephenylphosphine ligand), a thiolato ligand (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, still more preferably 6 to 20 carbon atoms, such as a phenylthiolato ligand) ), A phosphine oxide ligand (preferably having 3 to 30 carbon atoms, more preferably 8 to 30 carbon atoms, still more preferably 18 to 30 carbon atoms, such as a triphenylphosphine oxide ligand). More preferably, it is a nitrogen-containing heterocyclic ligand.
The complex may have one transition metal atom in the compound, or may be a so-called binuclear complex having two or more. Different metal atoms may be contained at the same time.

Specific examples of the phosphorescent material include, for example, US Pat. No. 6,303,238, US Pat. No. 6,097,147, International Publication No. 00/57676, International Publication No. 00/70655, International Publication No. 01 / 08230 pamphlet, WO 01/39234 pamphlet, WO 01/41512 pamphlet, WO 02/02714 pamphlet, WO 02/15645 pamphlet, WO 02/44189 pamphlet, International JP 05/19373 pamphlet, JP 2001-247859 A, JP 2002-302671 A, JP 2002-117978 A, JP 2003-133074 A, JP 2002-235076 A, JP 2003 No. 123982, JP-A No. 2002-170684, European Patent Application Publication No. 12111257, JP-A No. 2002-226495, JP-A No. 2002-234894, JP-A No. 2001-247859, JP-A No. 2001-2001 No. 298470, JP-A No. 2002-173684, JP-A No. 2002-203678, JP-A No. 2002-203679, JP-A No. 2004-357799, JP-A No. 2006-256999, JP-A No. 2007-19462 And phosphorescent compounds described in patent documents such as JP-A No. 2007-84635 and JP-A No. 2007-96259.
Among the above, more preferable luminescent materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex, And Ce complexes. Particularly preferred 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. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity, etc., an Ir complex, a Pt complex, or a Re complex containing a tridentate or higher polydentate ligand is particularly preferable.

  Examples of such complexes include the following. It is particularly preferable to use the following compound and the general formula (I) in combination as a light emitting material.

  The light emitting material in the light emitting layer can usually be contained in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. It is preferable to contain 50 mass%, and it is more preferable to contain 2 mass%-40 mass%.

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. Examples of the host material used in the present invention include the following materials.
Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone , Stilbene, silazane, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, polythiophene and other conductive polymer oligomers , Organic silane, carbon film, pyridine, pyrimidine, triazine, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbon Metal complexes of heterocyclic tetracarboxylic anhydrides such as bodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, naphthaleneperylene, phthalocyanines, 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles, benzothiazo- Examples thereof include various metal complexes typified by a metal complex having ru as a ligand and derivatives thereof (which may have a substituent or a condensed ring).

The triplet lowest excitation energy (T ₁ ) of the host material is preferably higher than T _{1 of the} phosphorescent material, from the viewpoints of color purity, luminous efficiency, and driving durability.

  The content of the host material is not particularly limited, but is preferably 15% by mass or more and 95% by mass or less with respect to the total mass of the compound forming the light emitting layer, from the viewpoints of luminous efficiency and driving voltage. Only one type of host material may be used, or two or more types may be used in combination.

Although the thickness of a light emitting layer is not specifically limited, Usually, it is 2 nm-500 nm, and it is preferable that it is 3 nm-200 nm from a viewpoint of external quantum efficiency, and it is more preferable that it is 5 nm-100 nm.
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.

-Hole injection layer, hole transport layer-
The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side. The hole injection material and the hole transport material used for these layers may be a low molecular compound or a high molecular compound.
Specific examples of hole injection materials and hole transport materials include pyrrole derivatives, carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine. Derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, phthalocyanine compounds, porphyrin compounds, thiophene derivatives, A layer containing an organosilane derivative, carbon, or the like is preferable.

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

-Electron injection layer, electron transport layer-
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
Specifically, pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone Derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene, perylene and other aromatic ring tetracarboxylic acid anhydrides, phthalocyanine derivatives, 8-quinolinol derivative metal complexes, Metal phthalocyanines, various metal complexes represented by metal complexes with benzoxazole and benzothiazole as ligands, organosilane derivatives represented by siloles Body, or the like is preferably a layer containing.

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

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

-Electronic block layer-
The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As examples of the compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even 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 structure 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. Examples thereof include materials described in Japanese Patent Application Laid-Open No. 11-329748, Japanese Patent Application Laid-Open No. 2003-272860, and Japanese Patent Application Laid-Open No. 2004-39617.
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. The charge generation layer may include a material having a function of injecting charges into adjacent layers on the anode side and the cathode side. 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.

<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, but it 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 and ytterbium. These may be used alone, but two or more can be suitably used in combination from the viewpoint of achieving both stability and electron injection.

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

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

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

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

There is no restriction | limiting in particular in the cathode formation position, You may form in the whole on an organic layer, and may be formed in the part.
A dielectric layer made of an alkali metal or alkaline earth metal fluoride, oxide or the like may be inserted between the cathode and the organic layer in a thickness of 0.1 nm to 5 nm. This dielectric layer can also be regarded as a kind of electron injection layer. The dielectric layer can be formed by, for example, a vacuum deposition method, a sputtering method, an ion plating method, or the like.

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

<Board>
The electrode and the organic layer can be formed on a substrate.
The substrate 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. , Norbornene resins, and organic materials such as poly (chlorotrifluoroethylene).
For example, when glass is used as the substrate, alkali-free glass is preferably used as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what applied barrier coats, 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.

<Protective layer>
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.
As specific examples, In, Sn, Pb, Au , Cu, Ag, Al, TI, metals NI _{like, MgO, SIO, SIO 2,} Al 2 O 3, GeO, NIO, CaO, BaO, 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 organic EL device of the present invention may seal the entire device using a sealing container.
Further, a moisture absorbent or an inert liquid may be sealed in a space between the sealing container and the light emitting element. Although it does not specifically limit as a moisture absorber, For example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride Cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, magnesium oxide, and the like. The inert liquid is not particularly limited, and examples thereof include paraffins, liquid paraffins, fluorinated solvents such as perfluoroalkane, perfluoroamine, and perfluoroether, chlorinated solvents, and silicone oils. Can be mentioned.

<Resonator structure>
The organic EL element of the present invention may have a resonator structure. For example, a multilayer mirror made of a plurality of laminated films having different refractive indexes, a transparent or translucent electrode, a light emitting layer, and a metal electrode are superimposed on a transparent substrate. The light generated in the light emitting layer resonates repeatedly with the multilayer mirror and the metal electrode as a reflection plate.
In another preferred embodiment, a transparent or translucent electrode and a metal electrode each function as a reflector on a transparent substrate, and light generated in the light emitting layer repeats reflection and resonates between them.
In order to form a resonant structure, the optical path length determined from the effective refractive index of the two reflectors and the refractive index and thickness of each layer between the reflectors is adjusted to an optimum value to obtain the desired resonant wavelength. Is done. The calculation formula in the case of the first embodiment is described in JP-A-9-180883. The calculation formula in the case of the second aspect is described in JP-A-2004-127795.

<Driving method>
The organic EL device of the present invention obtains 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. be able to.
Regarding the driving method of the organic EL device of the present invention, each of JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in the publications, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6023308, and the like can be applied.

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

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

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

When an organic EL element is applied to a display, as a method of making a full color type display, for example, as described in “Monthly Display”, September 2000, pages 33 to 37, the three primary colors (blue) (B), green light (G), red light (R)) corresponding to the three-color light emission method in which organic EL elements that emit light respectively on the substrate are arranged on the substrate, white light emission by the white light emitting organic EL elements through the color filter There are known a white method that divides three primary colors, a color conversion method that converts blue light emitted by an organic EL element for blue light emission into red (R) and green (G) through a fluorescent dye layer, and the like.
Moreover, the planar light source of desired luminescent color can be obtained by using combining the organic EL element of different luminescent color obtained by the said method. For example, a white light-emitting light source that combines blue and yellow light-emitting elements, a white light-emitting light source that combines blue, green, and red light-emitting elements.

EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these.
The compounds used in this example are shown below.

[Examples 1-1 to 1-9, Comparative Examples 1-1 and 1-2]
[Production of organic EL elements]
(Comparative Example 1-1)
A glass substrate having a 2.5 cm square and 0.5 mm thick ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, and ultrasonically cleaned in 2-propanol for 30 minutes. UV-ozone treatment was performed. The following organic layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: HI-4: 10 nm
Second layer: HT-1: 30 nm
Third layer: H-1 (host material) and comparative compound T-1 (light emitting material) (weight ratio 95: 5): 50 nm
Fourth layer: HB-1: 40 nm
On top of this, 0.1 nm of lithium fluoride and 100 nm of metal aluminum were vapor-deposited in this order to form a cathode.
This laminated body is put in a glove box substituted with argon gas without being exposed to the atmosphere, and sealed with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). The organic EL element of Comparative Example 1-1 was produced.

(Comparative Example 1-2)
An organic EL device of Comparative Example 1-2 was produced in the same manner as Comparative Example 1-1 except that Comparative Compound T-1 in the third layer was changed to Comparative Compound T-2.

(Comparative Example 1-3)
An organic EL device of Comparative Example 1-3 was produced in the same manner as Comparative Example 1-1 except that Comparative Compound T-1 in the third layer was changed to Comparative Compound T-3.

(Comparative Example 1-4)
An organic EL device of Comparative Example 1-4 was produced in the same manner as Comparative Example 1-1 except that Comparative Compound T-1 in the third layer was changed to Comparative Compound T-4.

(Example 1-1)
An organic EL device of Example 1-1 was produced in the same manner as in Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to Compound J-1.

(Example 1-2)
An organic EL device of Example 1-2 was produced in the same manner as Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-2.

(Example 1-3)
An organic EL device of Example 1-3 was produced in the same manner as Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-3.

(Example 1-4)
An organic EL device of Example 1-4 was produced in the same manner as in Comparative Example 1-1 except that Compound J-4 was used as the third layer comparative compound T-1.

(Example 1-5)
An organic EL device of Example 1-5 was produced in the same manner as in Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-5.

(Example 1-6)
An organic EL device of Example 1-6 was produced in the same manner as in Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-6.

(Example 1-7)
An organic EL device of Example 1-7 was produced in the same manner as in Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-7.

(Example 1-8)
An organic EL device of Example 1-8 was produced in the same manner as in Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-8.

(Example 1-9)
An organic EL device of Example 1-9 was produced in the same manner as in Comparative Example 1-1 except that the third layer comparative compound T-1 was changed to compound J-9.

[Evaluation of organic electroluminescence device]
Each element was evaluated for the following items (a) and (b).
(a) Storage stability of luminescent material When each of the luminescent materials was synthesized and purified by sublimation, and immediately after the device was prepared (A), each of the luminescent materials was sublimated and placed in a glass bottle with a lid, and the humidity was 70%. The ratio of the maximum external quantum efficiency ((B) / (A)) of (B) when the device was fabricated after being stored in a constant temperature layer at 60 ° C. for 6 days was compared.
The external quantum efficiency was calculated from the luminance, emission spectrum, and emission wavelength using a luminance conversion method. The luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation by using a source measure unit 2400 manufactured by Toyo Technica to apply a DC voltage to each element to emit light. The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics.

(b) Driving durability The initial light emission luminance of each element was defined according to the light emission peak wavelength, a DC voltage was applied so as to achieve the set luminance, and the time until the luminance was reduced by half was measured. This luminance half time was used as an index for evaluating driving durability.
The above evaluation results are shown in the following table.

[Examples 2-1 to 2-9, Comparative examples 2-1 and 2-2]
[Production of organic EL elements]
(Comparative Example 2-1)
An organic EL device of Comparative Example 2-1 was produced in the same manner as Comparative Example 1-1 except that Compound H-1 in the third layer was changed to Compound H-2.

(Comparative Example 2-2)
An organic EL device of Comparative Example 2-2 was produced in the same manner as in Comparative Example 1-2 except that Compound H-1 in the third layer was changed to Compound H-2.

(Example 2-1)
An organic EL device of Example 2-1 was produced in the same manner as in Example 1-1 except that the compound H-1 in the third layer was changed to compound H-2.

(Example 2-2)
An organic EL device of Example 2-2 was produced in the same manner as in Example 1-2 except that the compound H-1 in the third layer was changed to compound H-2.

(Example 2-3)
An organic EL device of Example 2-3 was produced in the same manner as in Example 1-3, except that Compound H-1 in the third layer was changed to Compound H-2.

(Example 2-4)
An organic EL device of Example 2-4 was produced in the same manner as in Example 1-4 except that Compound H-1 in the third layer was changed to Compound H-2.

(Example 2-5)
An organic EL device of Example 2-5 was produced in the same manner as Example 1-5, except that Compound H-1 in the third layer was changed to Compound H-2.

(Example 2-6)
An organic EL device of Example 2-6 was produced in the same manner as in Example 1-6, except that Compound H-1 in the third layer was changed to Compound H-2.

(Example 2-7)
An organic EL device of Example 2-7 was produced in the same manner as in Example 1-7, except that Compound H-1 in the third layer was changed to Compound H-2.

(Example 2-8)
An organic EL device of Example 2-8 was produced in the same manner as in Example 1-8, except that Compound H-2 in the third layer was changed to Compound H-2.

(Example 2-9)
An organic EL device of Example 2-9 was produced in the same manner as in Example 1-9, except that Compound H-1 in the third layer was changed to Compound H-2.

[Evaluation of organic electroluminescence device]
Each element produced as described above was evaluated for the following items (a) and (b). The results are shown in the table below.

[Examples 3-1 to 3-6, Comparative example 3-1]
[Production of organic EL elements]
(Comparative Example 3-1)
A glass substrate having an ITO film of 0.5 mm thickness and 2.5 cm square (manufactured by Geomatek Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then treated with UV-ozone for 30 minutes. Went. The following organic layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: HI-3: 90 nm
Second layer: HT-2: 20 nm
Third layer: H-6, FFR1, T-1 (weight ratio 90: 9: 1): 40 nm
Fourth layer: ET-2: 30 nm
On top of this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
This is put in a glove box substituted with argon gas without being exposed to the atmosphere, and sealed with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). And the organic EL element of the comparative example 3-1 was produced.

(Example 3-1)
An organic EL device of Example 3-1 was produced in the same manner as in Comparative Example 3-1, except that the compound J-1 was used as the comparative compound T-1 in the third layer.

(Example 3-2)
An organic EL device of Example 3-2 was produced in the same manner as in Comparative Example 3-1, except that the compound J-3 was used as the third layer comparative compound T-1.

(Production of Example 3-3)
An organic EL device of Example 3-3 was produced in the same manner as in Comparative Example 3-1, except that the third layer comparative compound T-1 was changed to Compound J-4.

(Example 3-4)
An organic EL device of Example 3-4 was produced in the same manner as in Comparative Example 3-1, except that the compound J-5 in the third layer was changed to the compound J-5.

(Example 3-5)
An organic EL device of Example 3-5 was produced in the same manner as Comparative Example 3-1, except that Compound J-7 was used as the third layer comparative compound T-1.

(Example 3-6)
An organic EL device of Example 3-6 was produced in the same manner as in Comparative Example 3-1, except that the compound J-8 of the third layer was changed to the compound J-8.

[Evaluation of organic electroluminescence device]
Each element produced as described above was evaluated for the following items (a) and (b). The results are shown in the table below.

[Examples 4-1 to 4-2, Comparative Examples 4-1 to 4-2]
[Production of organic EL elements]
(Comparative Example 4-1)
A glass substrate having an ITO film of 0.5 mm thickness and 2.5 cm square (manufactured by Geomatek Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then treated with UV-ozone for 30 minutes. Went. The following organic layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: HI-3: 90 nm
Second layer: HT-2: 20 nm
Third layer: H-6, FFR1, T-1 (weight ratio 90: 9: 1): 40 nm
Fourth layer: ET-1: 30 nm
On top of this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
This is put in a glove box substituted with argon gas without being exposed to the atmosphere, and sealed with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). And the organic EL element of the comparative example 3-1 was produced.

(Comparative Example 4-2)
An organic EL device of Comparative Example 4-2 was produced in the same manner as Comparative Example 4-1, except that the compound ET-1D of the fourth layer was changed to the compound ET-1D.

(Example 4-1)
An organic EL device of Example 4-1 was produced in the same manner as in Comparative Example 4-1, except that the third layer comparative compound T-1 was changed to Compound J-3.

(Production of Example 4-2)
An organic EL device of Example 4-2 was produced in the same manner as in Comparative Example 4-2, except that Compound J-3 was used as the third layer comparative compound T-1.
[Evaluation of organic electroluminescence device]
Each element produced as described above was evaluated for the following items (a) and (b). The results are shown in the table below.

  From the above results, it can be seen that according to the present invention, an organic electroluminescent element material excellent in storage stability and an organic electroluminescent element excellent in durability can be provided.

Claims (9)

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

(In general formula (I), Q ¹ and Q ⁴ each independently represents an aromatic hetero five-membered ring. Q ² represents an aromatic hetero six-membered ring. Q ³ represents a benzene ring or an aromatic hetero six-membered ring. Y ¹ and Z ⁴ represent a carbon atom or a nitrogen atom, and the combination of [Y ¹ , Z ⁴ ] is any of [C, N], [C, C], [N, N] X ^{11 to} X ¹³ and X ^{41 to} X ⁴³ each independently represent a nitrogen atom, NR ^N1 , an oxygen atom, a sulfur atom, a phosphorus atom or CRC ¹ , X ^{21 to} X ²³ , X ^{31 to} X ³³ are Each independently represents a nitrogen atom, NR ^N1 , oxygen atom, sulfur atom or CRC ¹ , R ^N1 represents a hydrogen atom or substituent, R ^C1 represents a hydrogen atom or substituent, and a solid line in Q ¹ and Q ⁴ A bond represented by a broken double line represents either a single bond or a double bond, M represents a divalent metal ion, a broken line representing a bond between M and a nitrogen atom represents a coordination bond, and M And carbon atoms and M and Z ⁴ The solid line indicating the bond of represents a covalent bond, and L represents a divalent linking group.) The organic electroluminescent device according to claim 1, wherein Y ¹ represents a carbon atom and Z ⁴ represents a carbon atom. The organic electroluminescent device according to claim 1, wherein Y ¹ represents a carbon atom and Z ⁴ represents a nitrogen atom. The organic electroluminescent element according to claim 1, wherein Y ¹ represents a nitrogen atom and Z ⁴ represents a nitrogen atom.   M represents Pt, The organic electroluminescent element in any one of Claims 1-4 characterized by the above-mentioned.   L is a disubstituted methylene linking group, The organic electroluminescent element in any one of Claims 1-5 characterized by the above-mentioned.   The organic electroluminescent element according to any one of claims 1 to 6, wherein the light-emitting layer contains a compound represented by the general formula (I).   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.