JP2012221856A - Method for manufacturing organic electroluminescent element, organic electroluminescent element, display and lighting apparatus - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for manufacturing an organic electroluminescent element having high luminous efficiency and capable of suppressing deterioration of the luminous efficiency even when driven by a high voltage, and an organic electroluminescent element manufactured by the method, and a display and a lighting apparatus having the element.SOLUTION: In a method for manufacturing an organic electroluminescent element having an anode, a luminescent layer, an organic layer adjacent to the luminescent layer and a cathode in this order, when a glass-transition temperature of a main component in the luminescent layer is defined as Tem(°C) during forming the organic layer by vapor deposition on the luminescent layer, a sublimation-initiation temperature Tb(°C) of a component having the highest sublimation-initiation temperature at 1×10Pa among components constituting the organic layer, satisfies 0.60≥Tem/Tb≥0.30. When a distance between a vapor deposition source for forming the organic layer and a surface of the luminescent layer is defined as L(cm), the vapor deposition of the organic layer is performed under a condition satisfying 2.0≤Tb/L≤80.

Description

  The present invention relates to a method for manufacturing an organic electroluminescent element.

  Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they emit light with high luminance 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.

When forming an organic layer by vapor deposition in the production of an organic electroluminescent element, there are problems such as uniform film formation and prevention of decomposition of organic materials, and various studies have been made.
Patent Document 1 discusses a vapor deposition apparatus such as a means for providing a relative linear movement between a vapor deposition source and a deposition target structure in the vapor deposition apparatus. Patent Document 2 describes alteration of an organic material due to high temperature and high pressure. In order to prevent this, the discharge hole in the case of a predetermined distance between the substrate and the vapor deposition source and the vapor deposition rate has been studied. Further, in Patent Document 3, in order to form a composite film satisfactorily, two or more vapor deposition sources are used so as to improve the controllability at a low film-forming speed during vapor deposition and not expose the organic material to a high temperature. In No. 4, studies have been made such as vapor deposition of the vapor deposition material below its thermal decomposition temperature.

  On the other hand, it has been known that the conventional organic electroluminescence device generally has a reduced luminous efficiency when driven at a high voltage, but there has been no discussion about the relevance to the vapor deposition method.

JP 2003-7464 A JP 2004-27251 A JP 2008-108611 A JP 2003-257463 A

  The present invention provides a method for manufacturing an organic electroluminescent element that has high luminous efficiency and suppresses a decrease in luminous efficiency even when driven at a high voltage. In addition, an organic electroluminescent element manufactured by the manufacturing method, a display device including the element, and a lighting device are provided.

As a result of intensive studies, the present inventors have found that the above-described problem can be achieved by the following means.
[1]
A method for producing an organic electroluminescent device comprising an anode, a light emitting layer, an organic layer adjacent to the light emitting layer, and a cathode in this order,
In forming the organic layer by vapor deposition on the light emitting layer,
Among the components constituting the organic layer, for the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa, the sublimation start temperature Tb (° C.) is the glass transition temperature of the component most contained in the light emitting layer. When Tem (° C.) is satisfied, 0.60 ≧ Tem / Tb ≧ 0.30 is satisfied,
When the distance between the vapor deposition source when forming the organic layer and the surface of the light emitting layer is L (cm), the condition of 2.0 ≦ Tb / L ² ≦ 80 is satisfied. A method for manufacturing an organic electroluminescent element, characterized by performing vapor deposition.
[2]
The method for producing an organic electroluminescent element as described in [1], wherein a vapor deposition rate at the time of depositing the organic layer is 0.2 to 1.5 Å / s.
[3]
The method for producing an organic electroluminescent element as described in [1] or [2], wherein the light emitting layer contains a phosphorescent material as a light emitting material.
[4]
The method for producing an organic electroluminescent element according to any one of [1] to [3], wherein the light emitting layer contains a flat material as a light emitting material.
[5]
The method for producing an organic electroluminescent element according to any one of [1] to [4], wherein the light emitting layer further includes a flat material as a host material.
[6]
The method for producing an organic electroluminescent element according to any one of [1] to [5], wherein an orientation degree of the light emitting material in the light emitting layer is 0.6 or more.
[7]
The method for producing an organic electroluminescent element according to any one of [1] to [6], wherein the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa is an electron transport material.
[8]
The method for producing an organic electroluminescent element according to any one of [1] to [7], wherein the most contained component in the light emitting layer is a host material.
[9]
The organic electroluminescent element produced by the production method according to any one of [1] to [8].
[10]
[9] A display device using the element according to [9].
[11]
[9] A lighting device using the element according to [9].

According to the method for producing an organic electroluminescent element of the present invention, an organic layer having good adhesion as an upper layer of the light emitting layer is formed while maintaining a good light emitting layer with little damage to the light emitting layer even by vapor deposition. Thus, it is possible to provide an organic electroluminescence device having excellent performance such as high luminous efficiency and suppression of a decrease in efficiency even at high voltage. Furthermore, a display device and an illumination device including the organic electroluminescent element can be provided.
In conventional devices, even when the efficiency is increased, the efficiency generally decreases as the drive voltage becomes higher. The present invention provides an element that can maintain good efficiency even when driven on the high voltage side by the method of the present invention, and has an effect that is essentially different from the improvement of the general efficiency of the element. It is.

It is the schematic which shows an example of a structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example of the light-emitting device which concerns on this invention. It is the schematic which shows an example of the illuminating device which concerns on this invention.

  Hereinafter, the present invention will be described in detail. In the present specification, “to” indicates a range including the numerical values described before and after the minimum and maximum values, respectively.

In the present invention, the substituent group A and the substituent group B are defined as follows.
(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, 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 groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, including, for example, phenyl, p-methylphenyl, naphthyl, anthryl, etc.), amino group (preferably 0 to 30 carbon atoms, more preferably 0 carbon atoms). -20, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms). More preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably 6 to 6 carbon atoms). 30 and more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. Ruoxy, 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 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, acetyl , Benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms such as methoxycarbonyl, ethoxy Carbonyl, etc.), aryloxycarbonyl group (preferably carbon It has 7 to 30 primes, more preferably 7 to 20 carbons, and particularly preferably 7 to 12 carbons, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and an alkoxycarbonylamino group (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and 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, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), a carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like, and an arylthio group (preferably 6 to 30 carbon atoms). , More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Sulfinyl 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 methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid. An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( An aromatic heterocyclic group is also included, preferably 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, Is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like. A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). Ryloxy 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, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

(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, 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 groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, including phenyl, p-methylphenyl, naphthyl, anthryl, etc.), cyano group, heterocyclic group (including aromatic heterocyclic group, Has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, and a tellurium atom. Is pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolid Le, benzimidazoli , Benzothiazolyl, carbazolyl, azepinyl group,. Etc. Shiroriru group) can be mentioned. These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A.

[Method for producing organic electroluminescent element]
The present invention is based on the sublimation start temperature Tb of the component having the highest sublimation start temperature among the components constituting the organic layer in the formation of the organic layer on the light emitting layer in the production of the organic electroluminescent element. The distance L between the light emitting layer and the surface of the light emitting layer (2.0 ≦ Tb / L ² ≦ 80), and the sublimation in the organic layer in relation to the glass transition point Tem of the most abundant component in the light emitting layer. For components having the highest start temperature, the sublimation start temperature Tb satisfying a predetermined relationship (0.60 ≧ Tem / Tb ≧ 0.30) is used, so that the luminous efficiency is reduced even when driven at a high voltage. Has been found to be suppressed. The driving at a high voltage is, for example, driving at a current density of 25 mA · cm ² .
Regarding the reason for such an effect, as described above, the distance L between the vapor deposition source and the surface of the light emitting layer is set based on the sublimation start temperature of the component in the organic layer, and most frequently in the light emitting layer. Considering the glass transition point Tem of the contained component, by setting the sublimation start temperature of the component in the organic layer within a predetermined range, damage to the light emitting layer due to thermal shock is suppressed, and a good light emitting layer is formed. It is presumed that an organic layer having good adhesion to the light emitting layer can be formed while maintaining.
The decrease in efficiency of a conventional device at a high voltage load is caused by damage to the light emitting layer during formation by vapor deposition of the upper layer, and the damage becomes more apparent as the efficiency decreases as the condition of the high voltage load is reached. I'm guessing.

The relational expression of 2.0 ≦ Tb / L ² ≦ 80 is found based on the following knowledge.
In general, when light is a point light source, a surface having an area of 4πr ² is illuminated on a surface separated by a distance r. Therefore, the light amount (= energy amount) received by an arbitrary point on the surface with respect to the light amount of the point light source is the light source. It is known that it is inversely proportional to the square of the distance between and.
It is estimated that the probability that a certain area of the deposition surface on the substrate is subjected to the collision of the organic material within an arbitrary time also becomes smaller in inverse proportion to the square of the distance, as in the above example of the point light source.
Therefore, it is possible that the molecules on the surface of the light emitting layer interface are subjected to the collision of the organic material for further organic layer formation, and the next molecule collides before relaxing the energy by heat conduction etc. However, it is estimated that this collision is reduced in inverse proportion to the square of the distance, and the damage to the deposition surface due to this collision is also inversely proportional to the square of the distance.
Note that an organic material sublimated from an evaporation source such as a crucible reaches the substrate with a certain thermal energy, and the energy in the vicinity of the substrate is almost the same as that immediately after sublimation. This is because there is almost no chance that the remaining gas molecules and organic material molecules collide with each other and are cooled under conditions in which normal vacuum deposition is performed (10 ⁻³ Pa or less).
In the production method of the present invention, the range of the square of the distance is set to a predetermined range according to the sublimation start temperature of the organic material to be deposited, thereby reducing the damage to the deposition surface and improving the adhesion of the deposited layer. We were able to plan.
In addition, about the improvement of adhesiveness, it is further light-emitted by making sublimation start temperature Tb of the component of an organic layer into a predetermined range with respect to the glass transition point Tem of the material which comprises a light emitting layer with the said relational expression. It is speculated that the adhesion between the layer and the organic layer can be improved and contributes to the effect of the present invention. When the glass transition point of the light emitting layer material is too high with respect to the thermal shock caused by the vapor deposition of the organic layer, the formation of an interface with high adhesion effective for charge transport is inhibited, and the effect of the present invention is inhibited.

In addition, when the deposition rate (deposition rate) was made smaller than a certain value, the molecular concentration in the vicinity of the substrate became thin as in the above estimation mechanism, and it seemed that the same effect was obtained.
The deposition rate is a numerical value obtained by converting the weight of the organic material adhering to the crystal placed near the substrate into an appropriate film thickness value. When increasing the deposition rate, the current flowing through the crucible or boat is usually used. It is common to increase the amount of evaporation by increasing the value and applying more heat.
However, it has been found that the effect of the present invention cannot be obtained simply by changing the deposition rate without changing the distance between the substrate and the deposition source. This is because, if the deposition rate is simply reduced, the heat applied to the boat is reduced, and the sublimated molecules are also reduced to the radiant heat received from the boat, so an interface with good adhesion can be obtained even at the same molecular concentration. The reason is that it is not.
On the other hand, according to the production method of the present invention, after satisfying the distance to the deposition surface and the sublimation start temperature, further vapor deposition is performed so that the deposition rate is in a certain range, a higher effect can be obtained. all right.

The method for producing the organic electroluminescent element of the present invention will be described in more detail.
The present invention provides a method for producing an organic electroluminescent element including an anode, a light emitting layer, an organic layer adjacent to the light emitting layer, and a cathode in this order. The method for producing an organic electroluminescent device of the present invention is characterized in that when an organic layer is formed by vapor deposition on a light emitting layer that is an organic layer, vapor deposition is performed under specific conditions. Other configurations of the electroluminescent element to be performed are arbitrary, and for example, in addition to the light emitting layer and the organic layer formed adjacent to the light emitting layer, an organic layer may be included.

In the production method of the present invention, the sublimation start temperature of the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa among the components constituting the organic layer when forming the organic layer on the light emitting layer by vapor deposition. Tb (° C.) satisfies 0.60 ≧ Tem / Tb ≧ 0.30 when the glass transition temperature of the component most contained in the light emitting layer is Tem (° C.),
Deposition of the organic layer under conditions satisfying 2.0 ≦ Tb / L ² ≦ 80, where L (cm) is the distance between the deposition source when forming the organic layer and the surface of the light emitting layer. It is characterized by performing.

The sublimation start temperature is determined by measuring the weight loss curve under reduced pressure with a sample amount of 20 mg, and the weight loss rate is -5% point (the -5% point is regarded as the temperature at which the material starts sublimation / evaporation) ( By measuring T (−5%)), the sublimation start temperature of the material can be obtained.
The glass transition temperature can be measured using a differential scanning calorimeter. By heating the glassy sample, the peak corresponding to the glass transition point and its temperature are measured.

The distance L (cm) between the vapor deposition source and the surface of the light emitting layer means the distance between the opening of the vapor deposition source and the surface of the light emitting layer.
As the vapor deposition source, any material used for vapor deposition can be used. Generally, the vapor deposition source has an organic material in its cavity and is heated by an arbitrary heating means such as a heater arranged around the cavity. Then, the organic material is sublimated, introduced into the deposition surface from the opening at the top of the cavity, and vapor deposition is performed.

Tem is generally desired to be high in order to impart film quality stability of the material film. The glass transition temperature of the material used as the material for the organic electroluminescence device is 20 to 350 ° C., and 70 to 250 ° C. is preferable in the material used in the present invention.
In general, Tb is appropriately selected within a range not exceeding the decomposition temperature of the material, and is 120 to 500 ° C. In the material used in the present invention, it is preferably 170 to 400 ° C.
L is generally selected from 2 to 100 cm depending on the substrate size and vapor deposition rate.

The deposition rate is generally 0.05 to 50 Å / s, and is preferably 0.05 to 10 Å / s from the viewpoint of forming a uniform film or not applying an excessive temperature load to the deposition source. 1 to 5 Å / s is more preferable, and 0.2 to 1.5 Å / s is particularly preferable.
In addition, it is preferable that the said organic layer contains 5-100 mass% of components with the highest sublimation start temperature in 1 * 10 ^<-2 > Pa, and it is more preferable to contain 50-100 mass%.

In the production method of the present invention, it was found that when a flat plate material is used as the light emitting material and / or the host material in the light emitting layer, the effect is remarkable for suppressing the efficiency decrease under a high voltage.
When a phosphorescent material is used for the light-emitting layer, the phosphorescent material has a tendency to decrease efficiency at high voltage because the distance between excitons decreases and triplet annihilation occurs as the concentration of excitons increases. However, according to the manufacturing method of the present invention, this can be suppressed and the efficiency can be improved under a high voltage.
In addition, when the orientation degree of the light emitting material in the light emitting layer is high (for example, an orientation degree of 0.6 or more), it is considered that the organic film is easily damaged during the formation of an organic film by vapor deposition on the light emitting layer, It can be said that the vapor deposition method in the present invention has a particularly beneficial effect on the light emitting layer having a high degree of orientation of the light emitting material.
The upper limit of the degree of orientation is generally 1.0.
The degree of orientation is preferably 0.4 to 1.0 in terms of improving the light emission efficiency of the device and facilitating charge transport.
The degree of orientation of the light emitting material in the light emitting layer means the degree of orientation of the film deposited on quartz with the same composition as the light emitting layer, and the degree of orientation is the film formed as described above (light emitting layer). Was calculated by measuring the angle change of ATR-IR.

FIG. 1 shows an example of the configuration of an organic electroluminescent device according to the present invention. In the organic electroluminescent element 10 according to the present invention shown in FIG. 1, a light emitting layer 6 is sandwiched between an anode 3 and a cathode 9 on a support substrate 2. Specifically, a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7, and an electron transport layer 8 are laminated in this order between the anode 3 and the cathode 9.
In view of the properties of the light-emitting element, at least one of the anode and the cathode is preferably transparent or translucent.

<Layer structure of organic electroluminescent element>
There is no restriction | limiting in particular as a structure of the organic layer which an organic electroluminescent element has, Although it can select suitably according to the use and purpose of an organic electroluminescent element, it forms on the said anode or the said cathode. Is preferred. In this case, the organic layer is formed on the front surface or one surface on the anode or the cathode.
There is no restriction | limiting in particular about the shape of a organic layer, a magnitude | size, thickness, etc., According to the objective, it can select suitably.

Specific examples of the layer configuration include the following, but the present invention is not limited to these configurations.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.

<Board>
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. 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.

<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.

<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.

  Regarding the substrate, anode, and cathode, the matters described in paragraphs [0070] to [0089] of JP-A-2008-270736 can be applied to the present invention.

<Organic layer>
The organic layer in the present invention will be described.

-Formation of organic layer-
In the organic electroluminescence device of the present invention, each organic layer other than the organic layer formed adjacent to the light emitting layer on the cathode side is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, a printing method, a spin coating method. It can also be suitably formed by a solution coating process such as a method, a bar coating method, an ink jet method, or a spray method. By using the liquid coating process, it is considered that productivity can be improved and the area of the organic EL element can be increased.

Vapor deposition, sputtering, etc. can be used as dry methods, and dipping, spin coating, dip coating, casting, die coating, roll coating, bar coating, gravure coating, and spray coating as wet methods. An ink jet method or the like can be used.
These film forming methods can be appropriately selected according to the material of the organic layer. When the film is formed by a wet method, the film may be dried after film formation. Drying is performed by selecting conditions such as temperature and pressure so that the coating layer is not damaged.

  The coating solution used in the wet film-forming method (coating process) usually comprises an organic layer material and a solvent for dissolving or dispersing it. A solvent is not specifically limited, What is necessary is just to select according to the material used for an organic layer.

  When the organic electroluminescent element material is used as a coating solution, the content in the coating solution is preferably 0.1 to 50% by mass, more preferably 0.3 to 40% by mass, based on the total solid content. Preferably it is 0.3-30 mass%. The viscosity is generally 1 to 30 mPa · s, more preferably 1.5 to 20 mPa · s, and still more preferably 1.5 to 15 mPa · s.

  The coating solution is preferably used by dissolving the organic electroluminescent element material in a predetermined organic solvent, filtering the solution, and applying the solution on a predetermined support or layer. The pore size of the filter used for filter filtration is preferably 2.0 μm or less, more preferably 0.5 μm or less, and still more preferably 0.3 μm or less made of polytetrafluoroethylene (PTFE), polyethylene, or nylon.

  Examples of the solvent include known organic solvents such as aromatic hydrocarbon solvents, alcohol solvents, ketone solvents, aliphatic hydrocarbon solvents, amide solvents, and the like.

  Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, trimethylbenzene, tetramethylbenzene, cumeneethylbenzene, methylpropylbenzene, methylisopropylbenzene, and the like, and toluene, xylene, cumene, and trimethylbenzene are more preferable. preferable. The relative dielectric constant of the aromatic hydrocarbon solvent is usually 3 or less.

  Examples of the alcohol solvent include methanol, ethanol, butanol, benzyl alcohol, cyclohexanol, and the like, butanol, benzyl alcohol, and cyclohexanol are more preferable. The relative dielectric constant of the alcohol solvent is usually 10-40.

  Examples of ketone solvents include 1-octanone, 2-octanone, 1-nonanone, 2-nonanone, acetone, 4-heptanone, 1-hexanone, 2-hexanone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, phenylacetone, methylethylketone, methyl Examples include isobutyl ketone, acetyl acetone, acetonyl acetone, ionone, diacetonyl alcohol, acetyl carbinol, acetophenone, methyl naphthyl ketone, isophorone, propylene carbonate, and the like, and methyl ethyl ketone, methyl isobutyl ketone, and propylene carbonate are preferable. The relative permittivity of the ketone solvent is usually 10 to 90.

  Examples of the aliphatic hydrocarbon solvent include pentane, hexane, octane, decane and the like, and octane and decane are preferable. The relative dielectric constant of the aliphatic hydrocarbon solvent is usually 1.5 to 2.0.

  Examples of amide solvents include N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethyl hole muamide, 1,3-dimethyl-2-imidazolidinone, and the like. N-methyl-2-pyrrolidone and 1,3-dimethyl-2-imidazolidinone are preferable. The relative dielectric constant of the amide solvent is usually 30-40.

  The said solvent may be used independently and may use 2 or more types together.

In addition, an aromatic hydrocarbon solvent (hereinafter also referred to as “first solvent”) and a second solvent having a relative dielectric constant higher than that of the first solvent may be mixed and used.
As the second solvent, an alcohol solvent, an amide solvent, or a ketone solvent is preferably used, and an alcohol solvent is more preferably used.
The mixing ratio (mass) of the first solvent and the second solvent is 1/99 to 99/1, preferably 10/90 to 90/10, and more preferably 20/80 to 70/30. A mixed solvent containing 60% by mass or more of the first solvent is preferable.

When the organic layer-forming coating solution contains a compound having a polymerizable group and forms a polymer that forms an organic layer by a polymerization reaction of the compound having a polymerizable group, By light irradiation, the polymerization reaction proceeds and a polymer can be formed.
The heating temperature and time after coating are not particularly limited as long as the polymerization reaction proceeds, but the heating temperature is generally 100 ° C to 200 ° C, and more preferably 120 ° C to 160 ° C.
The heating time is generally 1 minute to 120 minutes, preferably 1 minute to 60 minutes, and more preferably 1 minute to 30 minutes.

  Moreover, the polymerization reaction by UV irradiation, the polymerization reaction by a platinum catalyst, the polymerization reaction by iron catalysts, such as iron chloride, etc. are mentioned. These polymerization methods may be used in combination with a polymerization method by heating.

(Light emitting layer)
<Light emitting material>
The light emitting material contained in the light emitting layer in the present invention is not particularly limited, and examples thereof include a fluorescent light emitting material and a phosphorescent light emitting material, and a phosphorescent light emitting material is preferable.

(Fluorescent material)
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 represented by pyrrolopyrrole derivatives, aromatic dimethylidin compounds, complexes of 8-quinolinol derivatives and complexes of pyromethene derivatives Etc, polythiophene, polyphenylene, polyphenylene vinylene polymer compounds such as organic silane derivatives, compounds such as pyrene derivatives.

(Phosphorescent material)
Examples of phosphorescent materials include US6303238B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234A2, WO01 / 41512A1, WO02 / 02714A2, WO02 / 15645A1, WO02 / 44189A1, WO05 / 19373A2, and WO05 / 19373A2. 2001-247859, JP2002-302671, JP2002-117978, JP2003-133074, JP2002-2335076, JP2003-123982, JP2002170684, EP121257, JP2002226495, JP 2002-234894, JP 2001-247659, JP 2001-298470, JP 2002-173684, JP 2002-2002 And phosphorescent compounds described in patent documents such as JP-A No. 03678, JP-A No. 2002-203679, JP-A No. 2004-357991, JP-A No. 2006-256999, JP-A No. 2007-19462, JP-A No. 2007-84635, and JP-A No. 2007-96259. Among these, more preferable luminescent dopants 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 Re complexes are preferred. 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.

Further, the light emitting material is preferably a flat material, and in the single molecule calculation structure of the material, assuming a rectangular parallelepiped with the smallest volume inscribed by the molecule, the lengths of these three sides are x, y, A material having x> 3z and y> 2z, where z is defined, is defined as a flat plate material.
Examples of the light-emitting material that is a flat material include a platinum complex described later.

  Although the thickness of the light emitting layer is not particularly limited, it is usually preferably 2 nm to 500 nm, more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.

The light emitting layer in the element of 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 dopant 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.
Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
The light emitting layer may be a single layer or a multilayer of two or more layers. In addition, each light emitting layer may emit light with different emission colors.
In the light emitting layer, the host material other than the light emitting material is preferably a flat plate material from the viewpoint of further increasing the degree of orientation of the light emitting material.

Moreover, as a luminescent material which the light emitting layer in this invention contains, a platinum complex, an iridium complex, or a pyrene derivative as described below is preferable.
The content of the platinum complex or iridium complex in the light emitting layer is preferably 0.1% by mass to 30% by mass, and more preferably 1% by mass to 20% by mass with respect to the mass of all the compounds forming the light emitting layer. 5 mass%-15 mass% are especially preferable.
The pyrene derivative in the light emitting layer is preferably contained in an amount of 0.1% by mass to 30% by mass with respect to the mass of all the compounds forming the light emitting layer. More preferably, it is contained in an amount of 2% by mass to 10% by mass.
* Luminescent materials were separated from metal complexes and others.

  The platinum complex is preferably a platinum complex represented by the general formula (C-1).

In the formula, Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to Pt. L ¹ , L ² and L ³ each independently represents a single bond or a divalent linking group.

General formula (C-1) is demonstrated.
Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to Pt. At this time, the bond between Q ¹ , Q ² , Q ³ and Q ⁴ and Pt may be any of a covalent bond, an ionic bond, a coordinate bond, and the like.
As an atom couple | bonded with Pt in Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ >, a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ > Of the atoms bonded to Pt, at least one is preferably a carbon atom, more preferably two are carbon atoms, particularly preferably two are carbon atoms and two are nitrogen atoms.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand), heterocyclic ligand (eg furan ligand, thiophene ligand, pyridine) Ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole A ligand, an oxadiazole ligand, a thiadiazole ligand, and a condensed ring containing them (for example, a quinoline ligand, a benzothiazole ligand, etc.). A carbene ligand is mentioned as a neutral ligand.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a nitrogen atom may be neutral ligands or anionic ligands, and as neutral ligands, nitrogen-containing aromatic hetero Ring ligand (pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxazole ligand, Examples include thiazole ligands and condensed rings containing them (for example, quinoline ligands, benzimidazole ligands), amine ligands, nitrile ligands, and imine ligands. Examples of anionic ligands include amino ligands, imino ligands, nitrogen-containing aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands and condensed rings containing them) (For example, indole ligand, benzimidazole ligand, etc.)).
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with an oxygen atom may be neutral ligands or anionic ligands, and neutral ligands are ether ligands, Examples include ketone ligands, ester ligands, amide ligands, oxygen-containing heterocyclic ligands (furan ligands, oxazole ligands and condensed rings containing them (benzoxazole ligands, etc.)). It is done. Examples of the anionic ligand include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, and the like.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a sulfur atom may be neutral ligands or anionic ligands, and neutral ligands include thioether ligands, Examples include thioketone ligands, thioester ligands, thioamide ligands, sulfur-containing heterocyclic ligands (thiophene ligands, thiazole ligands and condensed rings containing them (such as benzothiazole ligands)). It is done. Examples of the anionic ligand include an alkyl mercapto ligand, an aryl mercapto ligand, and a heteroaryl mercapto ligand.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a phosphorus atom may be neutral ligands or anionic ligands, and neutral ligands include phosphine ligands, Examples include phosphate ester ligands, phosphite ester ligands, and phosphorus-containing heterocyclic ligands (phosphinin ligands, etc.). Anionic ligands include phosphino ligands and phosphinyl ligands. And phosphoryl ligands.
The ligands represented by Q ¹ , Q ² , Q ^3, and Q ⁴ may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other. When the substituents of Q ³ and Q ⁴ are linked to each other, the platinum complex represented by the general formula (C-1) becomes a Pt complex of a cyclic tetradentate ligand.

The ligand represented by Q ¹ , Q ² , Q ³ and Q ⁴ is preferably an aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, or an aromatic heterocyclic ring bonded to Pt with a carbon atom. A ligand, a nitrogen-containing aromatic heterocyclic ligand bonded to Pt with a nitrogen atom, an acyloxy ligand, an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, a silyloxy ligand, More preferably, an aromatic hydrocarbon ring ligand bonded to Pt by a carbon atom, an aromatic heterocyclic ligand bonded to Pt by a carbon atom, a nitrogen-containing aromatic heterocyclic coordination bonded to Pt by a nitrogen atom An aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, an aromatic heterocyclic ligand bonded to Pt with a carbon atom, nitrogen Containing atoms bonded to Pt Containing aromatic heterocyclic ligand, an acyloxy ligand.

L ¹ , L ² and L ³ represent a group consisting of a single bond, a double bond, a divalent linking group, or a combination thereof. Examples of the divalent linking group represented by L ¹ , L ² and L ³ include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR—) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (such as phenylphosphinidene group), silylene group (-SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), a carbonyl group, or a combination thereof. These linking groups may further have a substituent. R and R ′ each independently represents a substituent. As these substituents, those mentioned as the substituent group A can be applied. When there are a plurality of the substituents, the substituents may be connected to each other to form a ring.
From the viewpoint of the stability of the complex and the emission quantum yield, L ² and L ³ are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group, or a silylene group, and more preferably. Is a single bond, an alkylene group, an arylene group or an imino group, more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably a single bond. A methylene group in which two hydrogen atoms are substituted, particularly preferably a single bond, a dimethylmethylene group, and most preferably a single bond.

L ¹ is preferably an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group, a silylene group or a carbonyl group, more preferably an alkylene group, an arylene group or an imino group, still more preferably an alkylene group Group and imino group, particularly preferably methylene group and imino group. These may have a substituent, and as the substituent, those exemplified as the substituent group A can be applied. When there are a plurality of the substituents, the substituents may be connected to each other to form a ring.
L ¹ is more preferably a single bond, a methylene group in which two hydrogen atoms are substituted, or an arylimino group which may be substituted, and more preferably a dimethylmethylene group, an ethylmethylmethylene group, a methylpropylmethylene group, isobutylmethyl. A methylene group, a cyclohexanediyl group, a cyclopentanediyl group, a fluoromethylmethylene group and a phenylimino group, particularly preferably a dimethylmethylene group and a phenylimino group. If possible, these groups may be further substituted with the groups mentioned in the substituent group A.

  Among the platinum complexes represented by the general formula (C-1), a preferable embodiment includes a platinum complex represented by the following general formula (C-2).

In the formula, L ²¹ represents a single bond or a divalent linking group. A ²¹ , A ²² , B ²¹ , and B ²² each independently represent a carbon atom or a nitrogen atom. However, two or more of A ²¹ , A ²² , B ²¹ , and B ²² represent a nitrogen atom. Z ²¹ , Z ²² , Z ²³ , and Z ²⁴ each independently represent a benzene ring or a nitrogen-containing aromatic heterocycle.

General formula (C-2) is demonstrated.
L ²¹ represents a single bond or a divalent linking group, and the preferred range is the same as L ¹ in the general formula (C-1).

A ²¹ , A ²² , B ²¹ and B ²² each independently represent a carbon atom or a nitrogen atom, and two or more of them represent a nitrogen atom. Furthermore, it is preferable that two or three of A ²¹ , A ²² , B ²¹ and B ²² represent a nitrogen atom, more preferably two represent a nitrogen atom. From the viewpoint of the stability of the complex, it is preferable that A ²¹ and A ²² represent a nitrogen atom, or that B ²¹ and B ²² represent a nitrogen atom.

Z ²¹ , Z ²² , Z ²³ and Z ²⁴ each independently represent a benzene ring or a nitrogen-containing aromatic heterocycle.
Examples of the nitrogen-containing aromatic heterocycle represented by Z ²¹ , Z ²² , Z ²³ , and Z ²⁴ include a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, and a thiazole ring. , Triazole ring, oxadiazole ring, thiadiazole ring and the like.
From the viewpoint of orientation and stability as a material for an organic electroluminescence device, the ring represented by Z ²¹ and Z ²² is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole ring, and more preferably. Are a benzene ring, a pyridine ring, and a pyrazole ring.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²³ or Z ²⁴ is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably Is a benzene ring, a pyridine ring or a pyrazole ring, more preferably a benzene ring or a pyridine ring.

The benzene ring and nitrogen-containing aromatic heterocycle represented by Z ²¹ , Z ²² , Z ²³ , and Z ²⁴ may have a substituent, and examples of the substituent on the carbon atom include the substituent group A. The substituent group B is applicable as a substituent on the nitrogen atom.

  The substituent on the carbon atom is preferably an alkyl group, a fluoroalkyl group, an aryl group, a heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, an aryloxy group, a silyl group, a cyano group, or a halogen atom. An alkyl group, a fluoroalkyl group, an aryl group, an aryloxy group, a heterocyclic group, a diarylamino group, an alkoxy group, a cyano group, or a halogen atom, more preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, A fluorine atom or a cyano group is more preferable.

The alkyl group represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. As said alkyl group, C1-C12 is preferable, For example, a methyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group etc. are mentioned.
The aryl group represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyl group, a toluyl group, and a naphthyl group.
The fluoroalkyl group is preferably a trifluoromethyl group.
The alkoxy group represents a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The alkoxy group preferably has 1 to 12 carbon atoms, and examples thereof include a methoxy group, a butyloxy group, an octyloxy group, a decyloxy group, a dodecyloxy group, an s-octyloxy group, and a benzyloxy group.
The hetero ring group represents a substituted or unsubstituted nitrogen-containing aromatic hetero ring group having 6 to 10 carbon atoms, which may be condensed, such as a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, Examples thereof include a triazine ring and a carbazole ring, and a carbazole ring is preferable.
The diarylamino group represents a substituted or unsubstituted diarylamino group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a diphenylamino group, a ditoluylamino group, and a dinaphthylamino group.
The dialkylamino group represents a substituted or unsubstituted dialkylamino group having 2 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The dialkylamino group preferably has 2 to 12 carbon atoms. Specifically, for example, a dimethylamino group, a diethylamino group, a dioctylamino group, a didecylamino group, a didodecylamino group, a dit-butylamino group, a dit -An amylamino group, a di s-butylamino group, etc. are mentioned.
The aryloxy group represents a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyloxy group, a toluyloxy group, and a naphthyloxy group.
The silyl group represents a silyl group substituted with a carbon atom having 3 to 24 carbon atoms, and may be any of a trialkylsilyl group, an aryldialkylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. The silyl group preferably has 3 to 18 carbon atoms. Specific examples include a trimethylsilyl group, a t-butyldimethylsilyl group, a triphenylsilyl group, and a t-butyldiphenylsilyl group.
As the halogen atom, a fluorine atom is preferable.

Among these, the said substituent which has a linear alkyl group and a linear alkyl group as a substituent is preferable.
The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a trifluoroalkyl group, and the like are selected.

  The substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.

The substituents on Z ²¹ , Z ²² , Z ²³ , and Z ²⁴ may be linked to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, and a pyrimidine. And a ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, a thiophene ring, and a furan ring. When the substituents of Z ²³ and Z ²⁴ are linked to each other, the platinum complex represented by the general formula (C-2) becomes a Pt complex of a cyclic tetradentate ligand.

Of the platinum complexes represented by the general formula (C-2), one of the more preferable embodiments is a platinum complex represented by the following general formula (C-3).
(C-3)

In the formula, A ^{301 to} A ³¹³ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ³¹ represents a single bond or a divalent linking group. Y, Z, and M each independently represent a carbon atom or a nitrogen atom, and either one of Z and Y is a nitrogen atom.

General formula (C-3) is demonstrated.
L ³¹ has the same meaning as L ²¹ in formula (C-2), and the preferred range is also the same.

A ^{301 to} A ³⁰⁶ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied.
A ^{301 to} A ³⁰⁶ are preferably C—R, and Rs may be connected to each other to form a ring. When A ^{301 to} A ³⁰⁶ are C—R, R in A ³⁰² and A ³⁰⁵ is preferably a hydrogen atom, alkyl group, trifluoroalkyl group, aryl group, heterocyclic group, dialkylamino group, diarylamino group , An alkoxy group, an aryloxy group, a silyl group, a cyano group, or a halogen atom, a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, a heterocyclic group, a diarylamino group, an alkoxy group, a cyano group, or A halogen atom is more preferable, a hydrogen atom, an alkyl group, an alkoxy group, or a cyano group is further preferable, and a hydrogen atom is particularly preferable. The alkyl group and aryl group may further have a substituent, and examples of the substituent include an alkyl group, an aryl group, a cyano group, an amino group, a halogen atom, and a fluoroalkyl group. -6 alkyl group, cyano group, amino group, halogen atom, fluoroalkyl group (preferably trifluoromethyl group), more preferably C1-6 alkyl group, halogen atom (preferably fluorine atom). is there. In the case where A ³⁰² and A ³⁰⁵ are C—R, R in the A ³⁰² and A ³⁰⁵ is preferably an aryl group from the viewpoint of improving the durability of the device, and a hydrogen atom or an alkyl group from the viewpoint of a short emission wavelength. An amino group, an alkoxy group, a fluorine atom, and a cyano group are preferable.
R in A ³⁰¹ , A ³⁰³ , A ³⁰⁴ and A ³⁰⁶ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or an amino group. Group, an alkoxy group, an aryloxy group and a fluorine atom, and particularly preferably a hydrogen atom.

A ³⁰⁷ , A ³⁰⁸ , A ³⁰⁹ and A ³¹⁰ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied. When A ³⁰⁷ , A ³⁰⁸ , A ³⁰⁹ and A ³¹⁰ are C—R, R is preferably a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diaryl. An amino group, an alkyloxy group, a cyano group, and a halogen atom, more preferably a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, a fluorine atom, still more preferably a hydrogen atom, An alkyl group, a trifluoromethyl group, and a fluorine atom; If possible, the substituents may be linked to form a condensed ring structure. When shifting the emission wavelength to the short wavelength side, A ³⁰⁸ is preferably a nitrogen atom.

In the general formula (C-3), the 6-membered ring formed from two carbon atoms and A ³⁰⁷ , A ³⁰⁸ , A ³⁰⁹ and A ³¹⁰ includes a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and a triazine. A ring, more preferably a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring and a pyridazine ring, and particularly preferably a benzene ring and a pyridine ring. When the 6-membered ring is a pyridine ring, a pyrazine ring, a pyrimidine ring, or a pyridazine ring (particularly preferably a pyridine ring), a hydrogen atom present at a position where a metal-carbon bond is formed as compared with a benzene ring. Since acidity improves, it is advantageous at the point which becomes easier to form a metal complex.

A ³¹¹ , A ³¹² and A ³¹³ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied. When A ³¹¹ , A ³¹² and A ³¹³ are C—R, R is preferably a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, a heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group. , Aryloxy group, cyano group, halogen atom, more preferably hydrogen atom, alkyl group, trifluoroalkyl group, aryl group, dialkylamino group, cyano group, fluorine atom, more preferably hydrogen atom, alkyl group , A trifluoromethyl group and a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure.
At least one of A ³¹¹ , A ³¹² and A ³¹³ is preferably a nitrogen atom, and particularly preferably A ³¹¹ is a nitrogen atom.

  Of the platinum complexes represented by the general formula (C-3), one of more preferable embodiments is a platinum complex represented by the following general formula (C-3-1).

In the formula, X, Y, Z and M each independently represent a carbon atom or a nitrogen atom. However, one of Z and Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. m, n, p, and q each independently represent an integer of 0 to 3. Ar represents a substituted or unsubstituted aryl group. R _{1 to} R ₃ and R ₃₀ each independently represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group. When m, n, p, and q are 2 or more, a plurality of R ₁ , R ₂ , R _3, and R ₃₀ may be connected to each other to form a cyclic structure. Q is a carbon atom or a nitrogen atom.

General formula (C-3-1) is demonstrated.
X, Y, and Z represent a carbon atom or a nitrogen atom, and any one of Z and Y is a nitrogen atom, and when Y is a nitrogen atom, X is a carbon atom. Preferably, Z is a carbon atom, Y is a nitrogen atom, and X is a carbon atom.
m, n and p each independently represents an integer of 0 to 3. Among these, m is preferably 0 to 2, and more preferably 0 to 1. n is preferably 0 to 2, and more preferably 0 to 1. p is preferably 0 to 2, and more preferably 0 to 1.

R _{1 to} R ₃ each independently represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group.
The alkyl group represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The alkyl group preferably has 1 to 12 carbon atoms, and specific examples include a methyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, and a dodecyl group.
The aryl group represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyl group, a toluyl group, and a naphthyl group.
The alkoxy group represents a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The alkoxy group preferably has 1 to 12 carbon atoms, and specific examples include a methoxy group, an octyloxy group, a decyloxy group, a dodecyloxy group, an s-octyloxy group, and a benzyloxy group.
The aryloxy group represents a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyloxy group, a toluyloxy group, and a naphthyloxy group.
The silyl group represents a silyl group substituted with a hydrocarbon group having 3 to 24 carbon atoms, and may be any of a trialkylsilyl group, an aryldialkylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. . The silyl group preferably has 3 to 18 carbon atoms. Specific examples include a trimethylsilyl group, a t-butyldimethylsilyl group, a triphenylsilyl group, and a t-butyldiphenylsilyl group.
Examples of the heterocyclic group include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan A ring etc. are mentioned.
Among these, in the case of a linear alkyl group or a group other than an alkyl group, it is preferable to have an alkyl group as a substituent.
R ₁ and R ₂ are preferably an alkyl group, an aryl group, a fluorine atom, a cyano group or a silyl group, more preferably an alkyl group or an aryl group, and a phenyl group.
R ₃ is preferably an alkyl group or an aryl group, more preferably a methyl group, a trifluoromethyl group, or a phenyl group, and even more preferably a methyl group or a trifluoromethyl group.

Examples of the aryl group represented by Ar include a phenyl group and a naphthyl group, and a phenyl group is preferable. The aryl group represented by Ar may further have a substituent, and examples of the substituent include an alkyl group, an aryl group, a cyano group, an amino group, a fluorine atom, and a fluoroalkyl group, preferably 1 to 6 carbon atoms. Are an alkyl group, a cyano group, an amino group, a fluorine atom, and a fluoroalkyl group (preferably a trifluoromethyl group), and more preferably an alkyl group having 1 to 6 carbon atoms and a fluorine atom. Ar is more preferably a phenyl group having a substituent, and the substituent is preferably a methyl group, a t-butyl group, a 4-pentyl-cyclohexyl group, a 4-pentyl-cyclohexylmethoxy group, or the like.
When m, n, and p are 2 or more, a plurality of R _{1 to} R ₃ may be connected to each other next to each other to form a cyclic structure.
M and Q are each independently a carbon atom or a nitrogen atom.
q represents an integer of 0 to 3, and an integer of 0 to 2 is preferable.

R ₃₀ represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group.
The alkyl group represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The alkyl group preferably has 1 to 12 carbon atoms. Specifically, for example, methyl group, octyl group, decyl group, dodecyl group, n-butyl group, t-butyl group, t-amyl group, s- A butyl group etc. are mentioned.
The aryl group represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyl group, a toluyl group, and a naphthyl group.
The alkoxy group represents a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The alkoxy group preferably has 1 to 12 carbon atoms, and specific examples include a methoxy group, an octyloxy group, a decyloxy group, a dodecyloxy group, an s-octyloxy group, and a benzyloxy group.
The aryloxy group represents a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, and may be condensed, and specifically includes a phenyloxy group, a toluyloxy group, a naphthyloxy group, and the like. Can be mentioned.
The silyl group represents a silyl group substituted with a carbon atom having 3 to 24 carbon atoms, and may be any of a trialkylsilyl group, an aryldialkylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. The silyl group preferably has 3 to 18 carbon atoms. Specific examples include a trimethylsilyl group, a t-butyldimethylsilyl group, a triphenylsilyl group, and a t-butyldiphenylsilyl group.
Examples of the heterocyclic group include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan A ring etc. are mentioned.
R ₃₀ is preferably a fluorine atom.
From the viewpoint of aspect ratio, R ₃₀ preferably has an alkyl group as a substituent in the case of a chain alkyl group or a group other than an alkyl group.

  Among the platinum complexes represented by the general formula (C-2), one of more preferable embodiments is a platinum complex represented by the following general formula (C-4).

In the formula, A ^{401 to} A ⁴¹⁴ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁴¹ represents a single bond or a divalent linking group.

General formula (C-4) is demonstrated.
A ^{401 to} A ⁴¹⁴ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied.
A ^{401 to} A ⁴⁰⁶ are preferably C—R, and Rs may be connected to each other to form a ring. When A ^{401 to} A ⁴⁰⁶ are C—R, R in A ⁴⁰² and A ⁴⁰⁵ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group. More preferred are a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, and a fluorine atom, and particularly preferred are a hydrogen atom and an alkyl group. R in A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ and A ⁴⁰⁶ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or an amino group. Group, an alkoxy group, an aryloxy group and a fluorine atom, and particularly preferably a hydrogen atom.
L ⁴¹ has the same meaning as L ²¹ in formula (C-2), and the preferred range is also the same.

As A ^{407 to} A ⁴¹⁴ , the number of nitrogen atoms in each of A ^{407 to} A ⁴¹⁰ and A ^{411 to} A ⁴¹⁴ is preferably 0 to 2, and more preferably 0 to 1.
When A ^{407 to} A ⁴¹⁴ represent C—R, R in A ⁴⁰⁸ and A ⁴¹² is preferably a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom. A cyano group, more preferably a hydrogen atom, a trifluoroalkyl group, an alkyl group, an aryl group, a fluorine atom or a cyano group, and particularly preferably a hydrogen atom, a phenyl group, a trifluoroalkyl group or a cyano group. . R in A ⁴⁰⁷ , A ⁴⁰⁹ , A ⁴¹¹ and A ⁴¹³ is preferably a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably Is a hydrogen atom, a trifluoroalkyl group, a fluorine atom or a cyano group, particularly preferably a hydrogen atom, a phenyl group or a fluorine atom. R in A ⁴¹⁰ and A ⁴¹⁴ is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom. When any of A ^{407 to} A ⁴⁰⁹ and A ^{411 to} A ⁴¹³ represents C—R, Rs may be connected to each other to form a ring. Examples of the ring formed include a benzene ring and pyridine. A ring is mentioned.

  Of the platinum complexes represented by the general formula (C-2), one of more preferable embodiments is a platinum complex represented by the following general formula (C-5).

In the formula, A ^{501 to} A ⁵¹² each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁵¹ represents a single bond or a divalent linking group. Y and Z each independently represent a carbon atom or a nitrogen atom, and at least one is a nitrogen atom.

General formula (C-5) is demonstrated. A ^{501 to} A ⁵⁰⁶ and L ⁵¹ have the same meanings as A ^{401 to} A ⁴⁰⁶ and L ⁴¹ in the general formula (C-4), and preferred ranges thereof are also the same.

A ⁵⁰⁷ , A ⁵⁰⁸ , A ⁵⁰⁹ , A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied. When A ⁵⁰⁷ , A ⁵⁰⁸ , A ⁵⁰⁹ , A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² are C—R, R is preferably a hydrogen atom, an alkyl group, a trifluoroalkyl group, an aryl group, an aromatic heterocyclic group. , Dialkylamino group, diarylamino group, alkyloxy group, cyano group, halogen atom, more preferably hydrogen atom, alkyl group, trifluoroalkyl group, aryl group, dialkylamino group, cyano group, fluorine atom, Preferably, they are a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure.
An embodiment in which at least one of A ⁵⁰⁷ , A ⁵⁰⁸ , and A ⁵⁰⁹ , and at least one of A ⁵¹⁰ , A ^511, and A ⁵¹² is a nitrogen atom is also preferable. In this embodiment, A ⁵¹⁰ or A ⁵⁰⁷ is A nitrogen atom is preferred.

  Of the platinum complexes represented by the general formula (C-5), one of more preferable embodiments is a platinum complex represented by the following general formula (C-5-1).

In the formula, X, Y, and Z each independently represent a carbon atom or a nitrogen atom. However, one of Z and Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. m, n, p, and q each independently represent an integer of 0 to 3. Ar represents a substituted or unsubstituted aryl group. R _{1 to} R ₄ each independently represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group. When m, n, p, and q are 2 or more, the plurality of R _{1 to} R ₄ may be connected to each other to form a cyclic structure.

General formula (C-5-1) is demonstrated.
X, Y, and Z represent a carbon atom or a nitrogen atom, and any one of Z and Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. Preferably, Z is a carbon atom, Y is a nitrogen atom, and X is a carbon atom.
m, n, p, and q each independently represents an integer of 0 to 3. Among these, m is preferably 0 to 2, and more preferably 0 to 1. n is preferably 0 to 2, and more preferably 0 to 1. p is preferably 0 to 2, and more preferably 0 to 1. q is preferably 0 to 2, and more preferably 0 to 1.

R _{1 to} R ₄ each independently represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group.
The alkyl group represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. As said alkyl group, C1-C12 is preferable, and, specifically, a methyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group etc. are mentioned, for example.
The aryl group represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyl group, a toluyl group, and a naphthyl group.
The alkoxy group represents a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. The alkoxy group preferably has 1 to 12 carbon atoms, and specific examples include a methoxy group, an octyloxy group, a decyloxy group, a dodecyloxy group, an s-octyloxy group, and a benzyloxy group.
The aryloxy group represents a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyloxy group, a toluyloxy group, and a naphthyloxy group.
The silyl group represents a silyl group substituted with a hydrocarbon group having 3 to 24 carbon atoms, and may be any of a trialkylsilyl group, an aryldialkylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. . The silyl group preferably has 3 to 18 carbon atoms. Specific examples include a trimethylsilyl group, a t-butyldimethylsilyl group, a triphenylsilyl group, and a t-butyldiphenylsilyl group.
Examples of the heterocyclic group include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan A ring etc. are mentioned.
Among these, in the case of a linear alkyl group or a group other than an alkyl group, it is preferable to have an alkyl group as a substituent.
R ₁ and R ₂ are preferably an alkyl group, an aryl group, a fluorine atom, a cyano group, or a silyl group, and more preferably an alkyl group or an aryl group.
R ₃ and R ₄ are preferably an alkyl group or an aryl group, more preferably a methyl group, a trifluoromethyl group, or a phenyl group, and even more preferably a methyl group or a trifluoromethyl group.

Examples of the aryl group represented by Ar include a phenyl group and a naphthyl group, and a phenyl group is preferable. The aryl group represented by Ar may further have a substituent, and examples of the substituent include an alkyl group, an aryl group, a cyano group, an amino group, a fluorine atom, and a fluoroalkyl group, preferably 1 to 6 carbon atoms. Alkyl group, cyano group, amino group, fluorine atom and fluoroalkyl group (preferably trifluoromethyl group), more preferably an alkyl group having 1 to 6 carbon atoms and a fluorine atom. Ar is more preferably a phenyl group having a substituent, and the substituent is preferably a methyl group, a t-butyl group, a 4-methyl-cyclohexyl group, or the like.
When m, n, p, q is 2 or more, a plurality of R _{1 to} R ₄ may be connected to each other adjacent to each other to form a cyclic structure.

  Of the platinum complexes represented by the general formula (C-2), one of more preferable embodiments is a platinum complex represented by the following general formula (C-6).

In the formula, X, Y, and Z each independently represent a carbon atom or a nitrogen atom. However, one of Z and Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. r, s, t, and u each independently represent an integer of 0 to 3. R _{5 to} R ₈ each independently represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group. When r, s, t, and u are 2 or more, the plurality of R _{5 to} R ₈ may be linked to each other to form a cyclic structure. W ₁ and W ₂ each independently represent an alkyl group, and may be bonded to each other to form a cyclic structure.

General formula (C-6) is demonstrated.
X, Y, and Z are synonymous with X, Y, and Z of general formula (C-5-1), and their preferable ranges are also the same.

R < ₅ > -R < ₈ > is synonymous with R < ₁ > -R < ₄ > of general formula (C-5-1).
R ₅ and R ₆ are preferably an alkyl group, an alkoxy group, an aryl group, a fluorine atom, or a cyano group.
The alkyl group represented by R ₅ and R ₆ is preferably a methyl group, a butyl group, an octyl group, a decyl group, a dodecyl group or the like, which may have a substituent.
The alkoxy group represented by R ₅ and R ₆ is preferably a decyloxy group.
The aryl group represented by R ₅ and R ₆ is preferably a phenyl group which may have a substituent, and the substituent is preferably an alkyl group, more preferably a propyl group or a butyl group.
R ₇ and R ₈ are preferably an alkyl group or an aryl group.

r, s, t, and u each independently represent an integer of 0 to 3. Among these, r is preferably 0 to 2, and more preferably 0 or 1. s is preferably 0 to 2, more preferably 0 or 1. t is preferably 0 or 1, and u is preferably 0 or 1.
When r, s, t, u is 2 or more, the plurality of R _{5 to} R ₈ may be connected to each other adjacent to each other to form a cyclic structure. Examples of the cyclic structure include a structure that forms a fluorene ring together with a benzene ring, a benzofuran ring, and a 6-membered ring having Z.

W ₁ and W ₂ represent an alkyl group having 1 to 10 carbon atoms and may be bonded to each other to form a cyclic structure.
Examples of the alkyl group represented by W ₁ and W ₂ include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a pentyl group, and a methyl group is preferable.
Examples of the cyclic structure formed by combining W ₁ and W ₂ include a cyclohexyl cyclic structure.
W ₁ and W ₂ are preferably methyl groups or bonded to each other to form a cyclohexyl ring structure.

  Among the platinum complexes represented by the general formula (C-1), another more preferable embodiment is a platinum complex represented by the following general formula (C-7).

In the formula, L ⁶¹ represents a single bond or a divalent linking group. A ⁶¹ represents a carbon atom or a nitrogen atom. Z ⁶¹ and Z ⁶² each independently represent a nitrogen-containing aromatic heterocycle. Z ⁶³ represents a benzene ring or an aromatic heterocycle. Q is an anionic acyclic ligand that binds to Pt.

General formula (C-7) is demonstrated.
L ⁶¹ represents a single bond or a divalent linking group, and a preferred range is the same as L ¹ in the general formula (C-1).

A ⁶¹ represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A ⁶¹ is preferably a carbon atom.

Z ⁶¹ and Z ⁶² are synonymous with Z ²¹ and Z ²² in the general formula (C-2), respectively, and preferred ranges thereof are also the same. Z ⁶³ has the same meaning as Z ²³ in formula (C-2), and the preferred range is also the same.

Q is an anionic acyclic ligand that binds to Pt. An acyclic ligand is one in which atoms bonded to Pt do not form a ring in the form of a ligand. As an atom couple | bonded with Pt in Q, a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
Examples of Q bonded to Pt by a carbon atom include a vinyl ligand. Examples of Q bonded to Pt with a nitrogen atom include an amino ligand and an imino ligand. Q bonded to Pt with an oxygen atom includes an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphate ligand, Examples thereof include sulfonic acid ligands. Examples of Q bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.
The ligand represented by Q may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.

  The ligand represented by Q is preferably a ligand bonded to Pt with an oxygen atom, more preferably an acyloxy ligand, an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, It is a silyloxy ligand, and more preferably an acyloxy ligand.

Of the platinum complexes represented by the general formula (C-7), one of more preferred embodiments is a platinum complex represented by the following general formula (C-8).
(C-8)

In the formula, A ^{701 to} A ⁷¹⁰ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁷¹ represents a single bond or a divalent linking group. Q is an anionic acyclic ligand that binds to Pt.

General formula (C-8) is demonstrated.
L ⁷¹ has the same meaning as L ^{61 in} formula (C-6), and the preferred range is also the same. A ^{701 to} A ⁷¹⁰ have the same meanings as A ^{401 to} A ⁴¹⁰ in formula (C-4), and preferred ranges thereof are also the same. Y has the same meaning as that in formula (C-6), and the preferred range is also the same.

Among the platinum complexes represented by the general formula (C-1), one of other preferable embodiments is a platinum complex represented by the following general formula (C-9).
(C-9)

In the formula, A and B represent a cyclic structure, A represents an aromatic ring, and B represents an aromatic heterocycle. When one of A and B forms a ring, the other may not form a ring. R _{13 to} R ₁₆ each independently represent a hydrogen atom, an alkyl group, an aryl group, a silyl group, or a heterocyclic group, and R ₁₄ and R ₁₅ , R ₁₃ and R ₁₆ are bonded to each other to form a cyclic structure. It may be formed.

General formula (C-9) is demonstrated.
A represents an aromatic ring. Examples of the aromatic ring include an aromatic hydrocarbon ring and an aromatic heterocycle, and an aromatic hydrocarbon ring is preferable. As the aromatic hydrocarbon ring represented by A, a benzene ring and a naphthalene ring are preferable. As the aromatic heterocycle represented by A, a pyridine ring, a pyrazine ring, a pyrimidine ring and a quinoline ring are preferable.
B represents an aromatic heterocycle. The aromatic heterocycle represented by B is preferably a pyridine ring or a pyrimidine ring.
As a combination of A and B, it is preferable that A is a benzene ring and B is a non-ring (does not form a ring), A is a naphthalene ring and B is a non-ring, and A is a benzene ring and B is a pyridine ring, or More preferably, A is a non-ring and B is a pyridine ring.
R _{13 to} R ₁₆ represent a hydrogen atom, an alkyl group, an aryl group, a silyl group, or a heterocyclic group, and R ₁₄ and R ₁₅ , or R ₁₃ and R ₁₆ may be bonded to each other to form a cyclic structure. .
The alkyl group represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and may have a linear, branched, or cyclic structure. As said alkyl group, C1-C12 is preferable, for example, a methyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group etc. are mentioned.
The aryl group represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms and may be condensed, and examples thereof include a phenyl group, a toluyl group, and a naphthyl group.
The silyl group represents a silyl group substituted with a carbon atom having 3 to 24 carbon atoms, and may be any of a trialkylsilyl group, an aryldialkylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. As said silyl group, C3-C18 is preferable and a trimethylsilyl group, t-butyldimethylsilyl group, a triphenylsilyl group, t-butyldiphenylsilyl group, etc. are mentioned.
Examples of the heterocyclic group include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan A ring etc. are mentioned.

R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ are each preferably a substituted or unsubstituted aryl group, or an aromatic ring in which R ₁₃ and R ₁₆ , and R ₁₄ and R ₁₅ are bonded to each other. Examples of the aromatic ring include a benzene ring. The aromatic ring may further have a substituent, for example, an alkyl group (methyl group, butyl group, pentyl group, hexyl group, octyl group, decyl group), alkoxy group (methoxy group, ethoxy group, butoxy group). Etc.).
Among these, an aromatic ring in which R ₁₃ and R ₁₆ , R ₁₄ and R ₁₅ are bonded from the viewpoint of molecular size is preferable.

  As a more preferable aspect of the compound represented by general formula (C-9), the compound of the following general formula (C-9-1) is mentioned.

In the formula, B may form an aromatic 6-membered heterocycle.
R _{17 to} R ₂₆ each independently represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group, and R ₁₇ and R ₁₈ , R ₁₈ and R ₁₉ , R ₁₉ and R ₂₀ , R ₂₁ and R ₂₂ , R ₂₂ and R ₂₃ , R ₂₃ and R ₂₄ , and R ₂₅ and R ₂₆ may be bonded to each other to form a cyclic structure. Preferred examples of the alkyl group, aryl group, alkoxy group, aryloxy group, cyano group, silyl group, and heterocyclic group represented by R _{17 to} R ₂₆ are the same as the examples of each group represented by R _{13 to} R _26. .
R ₁₇ , R ₂₀ , R ₂₁ and R ₂₄ are preferably a hydrogen atom or an alkyl group.
R ₁₈ , R ₁₉ , R ₂₂ and R ₂₃ are preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a fluorine atom, a cyano group or a silyl group, more preferably an alkyl group or an alkoxy group, a decyloxy group or a dodecyl group. An oxy group is more preferable.
R _{25 to} R ₂₆ are preferably a hydrogen atom, an alkyl group, a fluorine atom, or an aromatic ring in which R ₂₅ and R ₂₆ are bonded.
The aromatic 6-membered heterocycle represented by B is preferably a pyridine ring or a pyrimidine ring, and more preferably a pyridine ring. The ring may have a substituent, and examples of the substituent include an alkyl group (methyl group and butyl group) and an aryl group (phenyl group).
From the viewpoint of the aspect ratio, R _{17 to} R ₂₆ preferably have an alkyl group as a substituent in the case of a chain alkyl group or a group other than an alkyl group.

  The platinum complex represented by the general formula (C-1) is preferably a platinum complex represented by any one of the general formulas (C-2), (C-7), and (C-9). The platinum complex represented by formula (C-2) or (C-9) is more preferable. The platinum complex represented by the general formula (C-2) is a platinum complex represented by any one of the general formulas (C-3), (C-4), (C-5), and (C-6). The platinum complex is more preferably a platinum complex represented by any one of the general formulas (C-3-1), (C-5-1), and (C-6). A platinum complex represented by -5-1) or (C-6) is particularly preferable.

Specific examples of the platinum complex represented by the general formula (C-1) include [0143] to [0152], [0157] to [0158], and [0162] to [0168] of JP-A-2005-310733. The compounds described in JP-A-2006-256999, [0065] to [0083], the compounds described in JP-A-2006-93542, [0065] to [0090], JP-A-2007-73891 Nos. [0063] to [0071], No. 2007-324309, No. 0079 to [0083], No. 2006-93542 No. [0065] to [0090] Compounds described in JP-A-2007-96255, [0055] to [0071], JP-A-2006-313796 0043] include compounds described in ~ [0046].
Examples of the platinum complex represented by the general formula (C-1) and other platinum complexes are given below. In addition, the alkyl group and the alkyl group in the exemplary compound include a linear alkyl group, a branched alkyl group, and a cycloalkyl group, and preferably a linear alkyl group.

Examples of the platinum complex represented by the general formula (C-1) include Journal of Organic Chemistry 53,786, (1988), G.S. R. Newkome et al. ), Page 789, method described in left column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26-35, and the like.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

[Iridium Complex]
As the iridium complex, an iridium complex represented by the following general formula (E-1) is preferably used.

  General formula (E-1) is demonstrated.

In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.
A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom.
B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of ₁ to 3.

n _E1 represents an integer of 1 to 3, and is preferably 2 or 3.
Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom. Examples of the 5- or 6-membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the 5- or 6-membered heterocycle formed by A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole. A ring, more preferably a pyridine ring, an imidazole ring and a pyrazine ring, still more preferably a pyridine ring and an imidazole ring, and most preferably a pyridine ring.

The 5- or 6-membered heterocycle formed by A ₁ , Z ¹ and a nitrogen atom may have a substituent. As the substituent on the carbon atom, the substituent group A is on the nitrogen atom. The substituent group B can be applied as the substituent. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

  The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.

B ₁ represents a 5- or 6-membered ring containing Z ² and a carbon atom. Examples of the 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom include a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
From the viewpoint of complex stability, emission wavelength control, and emission quantum yield, a 5- or 6-membered ring formed of B ₁ , Z ² and a carbon atom is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole. A ring and a thiophene ring, more preferably a benzene ring, a pyridine ring and a pyrazole ring, and still more preferably a benzene ring and a pyridine ring.

The 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as the substituent on the carbon atom. As the above, the substituent group B can be applied. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

  The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
In addition, a 5- or 6-membered heterocyclic substituent formed by A ₁ , Z ¹ and a nitrogen atom and a 5- or 6-membered ring substituent formed by B ₁ , Z ² and a carbon atom are linked. Then, the same condensed ring as described above may be formed.

  Examples of the ligand represented by (XY) include various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Published by Yersin, 1987, “Organometallic Chemistry-Fundamentals and Applications-” Liu Huabosha, Akio Yamamoto, published by 1982, etc. (for example, halogen ligands (preferably chlorine ligands), Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.), diketone ligands (for example, acetylacetone, etc.) The ligand represented by (XY) is preferably a diketone or a picolinic acid. The derivative is most preferably acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency.

* Represents a coordination position to iridium.
As the ligand represented by (X—Y), the following general formulas (l-1) to (1-15) are preferable, but the present invention is not limited thereto.

  * Represents a coordination position to iridium in the general formula (E-1). Rx, Ry and Rz each independently represents a hydrogen atom or a substituent.

  When Rx, Ry, and Rz represent a substituent, examples of the substituent include a substituent selected from the substituent group A. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect.

In formula (I-15), R ^{I1 to} R ^I4 represent a substituent selected from the substituent group A, and B represents CR or a nitrogen atom. R represents a hydrogen atom or a substituent selected from substituent group A. R ^{I5 to} R ^I7 are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R ′, —C (O) R. ', —NR ′ ₂ , —NO ₂ , —OR ′, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent A. R ′ each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. * Represents a coordination position to iridium in the general formula (E-1).
Any one of R ^I1 , R ^I5 , R ^I6 , and R ^I7 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl And the condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
The preferable range of R ^{I1 to} R ^{I7 is the same as} the preferable range of R ^{T1 to} R ^T7 in the general formula (E-3) described later. B is preferably CR, and R is preferably a hydrogen atom or an aryl group, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (for example, a phenyl group, a tolyl group, a naphthyl group). And particularly preferably a hydrogen atom or a phenyl group.

  (X-Y) is more preferably (I-1), (I-4), or (I-15), and particularly preferably (I-1) or (I-15). Complexes having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, it can synthesize | combine by the method shown below using commercially available difluoro acetylacetone similarly to the method of international publication 2009-073245 page 46.

  A preferred embodiment of the Ir complex represented by the general formula (E-1) is an Ir complex represented by the general formula (E-2).

In General Formula (E-2), A ^{E1 to} A ^E8 each independently represent a nitrogen atom or C—R ^E.
R ^E represents a hydrogen atom or a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E2 represents an integer of 1 to 3.

A ^{E1 to} A ^E8 each independently represent a nitrogen atom or C—R ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. Examples of the ring formed include the same condensed rings described in the general formula (E-1). Examples of the substituent represented by R ^E, we are the same as those mentioned above substituent group A.
A ^E1 is preferably a to A ^E4 is ^{C-R E,} if A E1 ^{to A E4} is ^{C-R E,} preferably a hydrogen atom ^{R E} of ^{A E3,} alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. And R ^E in A ^E1 , A ^E2 and A ^E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom, An alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.

A ^{E5 to} A ^E8 are preferably C-R ^E , and when A ^{E5 to} A ^E8 are C-R ^E , R ^E is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic group A heterocyclic group, a dialkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, more preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, Or a fluorine atom, and more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. In the case where the emission wavelength is shifted to the short wavelength side, A ^E6 is preferably a nitrogen atom.
(X-Y), and _{n E2} of the general formula in (E1) (X-Y) , and has the same meaning as _{n E1} preferable ranges are also the same.

  A more preferable form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).

In general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R ′ ″, —C (O) R ′ ″, —NR ′ ″ ₂ , —NO ₂ , —OR ′ ″, halogen atom, Represents an aryl group or a heteroaryl group, and may further have a substituent Z; R ′ ″ each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
A represents CR ″ ″ or a nitrogen atom, and R ″ ″ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO _2. R ′ ″ ″, —C (O) R ′ ″ ″, —NR ′ ″ ″ ₂ , —NO ₂ , —OR ″ ″ ′, a halogen atom, an aryl group or a heteroaryl group And may further have a substituent Z. R ′ ″ ″ each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^{T1 to} R ^T7 and R ″ ″ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent Z. Among these, a case where a ring is condensed with R ^T1 and R ^T7 , or R ^T5 and R ^T6 to form a benzene ring is preferable, and a case where a ring is condensed with R ^T5 and R ^T6 to form a benzene ring is particularly preferable.
The substituents Z are each independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C ( O) represents N (R ″) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ″, —SO ₂ R ″, or —SO ₃ R ″, and each R ″ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
(X—Y) represents a monoanionic bidentate ligand. n _E3 represents an integer of 1 to 3.

The alkyl group represented by R ^{T1 to} R ^T7 and R ″ ″ may have a substituent, may be saturated or unsaturated, and may be substituted. As mentioned above, the aforementioned substituent Z can be exemplified. The alkyl group represented by R ^{T1 to} R ^T7 and R ″ ″ is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples include a methyl group, an ethyl group, an i-propyl group, a cyclohexyl group, a t-butyl group, and the like, and a methyl group is particularly preferable.
The cycloalkyl group represented by R ^{T1 to} R ^T7 and R ″ ″ may have a substituent, may be saturated or unsaturated, and may be substituted. Examples of the group include the substituent Z described above. The cycloalkyl group represented by R ^{T1 to} R ^T7 and R ″ ″ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total. For example, a cyclopentyl group, a cyclohexyl group, etc. are mentioned.
The alkenyl group represented by R ^{T1 to} R ^T7 and R ″ ″ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. , Allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
The alkynyl group represented by R ^{T1 to} R ^T7 and R ″ ″ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples include ethynyl, propargyl, 1-propynyl, 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^{T1 to} R ^T7 and R ″ ″ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

The aryl group represented by R ^{T1 to} R ^T7 and R ″ ″ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms such as a phenyl group, a tolyl group, and a naphthyl group. And a phenyl group is particularly preferable.

The heteroaryl group represented by R ^{T1 to} R ^T7 and R ″ ″ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted group. For example, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group, furyl group , Benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group , Isoxazolyl group Benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, dibenzothienyl group, such as 7 pyrido-indolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^{T1 to} R ^T7 and R ″ ″ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group or a heteroaryl group, More preferred are a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluorine atom, and an aryl group, and further preferred are a hydrogen atom, an alkyl group, and an aryl group. As the substituent Z, an alkyl group, an alkoxy group, a fluorine atom, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.

Any one of R ^{T1 to} R ^T7 and R ″ ″ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl; And the condensed 4- to 7-membered ring may further have a substituent Z. The definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R ^{T1 to} R ^T7 and R ″ ″.

n _E3 is preferably 2 or 3. The type of ligand in the complex is preferably composed of 1 to 2 types.
(XY) is synonymous with (XY) in general formula (E-1), and its preferable range is also the same.

  One of the preferable forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).

R ^{T1 to} R ^T4 , A, (X—Y) and n _E4 in General Formula (E-4) are R ^{T1 to} R ^T4 , A, (XY) and n _{E3 in} General Formula (E-3). The preferred range is also the same. R ₁ ′ to R ₅ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R ′ ″ ″, — C (O) R ′ ″ ″, —NR ′ ″ ″ ₂ , —NO ₂ , —OR ′ ″ ″, a halogen atom, an aryl group or a heteroaryl group, and further having a substituent Z You may do it. R ′ ″ ″ each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any _{one of} R ₁ ′ to R ₅ ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
Moreover, the preferable range in R < ₁ >'-R< ₅ >' is the same as R ^{< T1} > -R <^T7> , R '''' in general formula (E-3). A represents CR ″ ″, and among R ^{T1 to} R ^T4 , R ″ ″, and R ₁ ′ to R ₅ ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. In particular, among R ^{T1 to} R ^T4 , R ″ ″, and R ₁ ′ to R ₅ ′, 0 to 2 are alkyl groups and the rest are all hydrogen atoms.

  Another preferable form of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-5).

R ^{T2 to} R ^T6 , A, (X—Y) and n _E5 in General Formula (E-5) are R ^{T2 to} R ^T6 , A, (XY) and n _{E3 in} General Formula (E-3). The preferred range is also the same. R ₆ ′ to R ₈ ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R ′ ″ ″, — C (O) R ′ ″ ″, —NR ′ ″ ″ ₂ , —NO ₂ , —OR ′ ″ ″, a halogen atom, an aryl group or a heteroaryl group, and further having a substituent Z You may do it. R ′ ″ ″ each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^T5 , R ^T6 , R ₆ ′ to R ₈ ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or It is heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
Moreover, the preferable range in R < ₆ >'-R< ₈ >' is the same as R ^{< T1} > -R <^T7> , R '''' in general formula (E-3). A represents CR ″ ″, and among R ^{T2 to} R ^T6 , R ″ ″, and R ₆ ′ to R ₈ ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. Is particularly preferable, and among R ^{T2 to} R ^T6 , R ″ ″, and R ₆ ′ to R ₈ ′, 0 to 2 are alkyl groups and the rest are all hydrogen atoms.

  When the phosphorescent material represented by the general formula (E-4) or (E-5) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the electron transport layer. More preferably, it is contained in the light emitting layer.

  Although the preferable specific example of a compound represented by general formula (E-1) is enumerated below, it is not limited to the following.

  The compound illustrated as a compound represented by the said general formula (E-1) is compoundable by the method as described in Unexamined-Japanese-Patent No. 2009-99783, the various method as described in US Patent 7279232, etc. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

  Although it is preferable that the compound represented by general formula (E-1) is contained in a light emitting layer, the use is not limited and may further be contained in any layer in the organic layer. .

[Pyrene derivatives]
Conventionally known pyrene derivatives can be used as the pyrene derivative, but a compound represented by the following general formula (P-1) (hereinafter also referred to as “compound (P-1)”) is preferably used. .

In the formula, R _P ^{1 to} R _P ¹⁰ each independently have a hydrogen atom, an aromatic hydrocarbon group which may have a substituent, an alkyl group which may have a substituent, or a substituent. A silyl group which may have, a heterocyclic group which may have a substituent, an alkylamino group which may have a substituent, or an arylamino group which may have a substituent, At least one of R _P ^{1 to} R _P ¹⁰ is a group other than a hydrogen atom.

_<R ^P 1 ~R ^{P 10>}
(Types of substituents R _P ^{1 to} R _P ¹⁰ )
R _P ^{1 to} R _P ¹⁰ may each independently have a hydrogen atom, an aromatic hydrocarbon group that may have a substituent, an alkyl group that may have a substituent, or a substituent. A good silyl group, a heterocyclic group which may have a substituent, an alkylamino group which may have a substituent, and an arylamino group which may have a substituent are represented. These may be bonded to each other and condensed.
At least one of R _P ^{1 to} R _P ¹⁰ is a group other than a hydrogen atom.

When two or more of R _P ^{1 to} R _P ¹⁰ are groups other than hydrogen atoms, the groups other than the plurality of hydrogen atoms may be the same or different. It is preferable that they are the same in terms of ease of synthesis, and are preferably different in that the emission wavelength can be tuned.

In addition, in terms of obtaining high luminous efficiency, the groups other than the hydrogen atoms of R _P ^{1 to} R _P ¹⁰ may have an aromatic hydrocarbon group which may have a substituent or a substituent. A silyl group is preferable, and an aromatic hydrocarbon group which may have a substituent is particularly preferable. Moreover, in terms of obtaining light emission with a narrow half width, groups other than the hydrogen atoms of R _P ^{1 to} R _P ¹⁰ are an alkyl group which may have a substituent, and an arylamino which may have a substituent. Group, a heterocyclic group which may have a substituent is preferable, and R _P ¹ , R _P ^{3 to} R _P ⁶ , and R _P ^{8 to} R _P ¹⁰ are hydrogen atoms in that a long emission wavelength is obtained. As other groups, an aromatic hydrocarbon which may have a substituent and a heterocyclic group which may have a substituent are preferable.

The aromatic hydrocarbon group represented by R _P ^{1 to} R _P ¹⁰ is preferably an aromatic hydrocarbon group having 6 to 16 carbon atoms, and is not limited to a monocyclic group, and may be a condensed polycyclic hydrocarbon group. . Specific examples of the aromatic hydrocarbon group include phenyl group, biphenyl group, phenanthryl group, naphthyl group, anthryl group, and fluorenyl group.

As the alkyl group represented by R _P ^{1 to} R _P ¹⁰ , an alkyl group having 1 to 10 carbon atoms is preferable, and specific examples include i-propyl group, t-butyl group, cyclohexyl group and the like.
The silyl group preferably has 3 to 20 carbon atoms, and specific examples include trimethylsilyl group, dimethylphenylsilyl group, dimethylbutylsilyl group, triisopropylsilyl group, and methyldibutylsilyl group.
As the heterocyclic group represented by R _P ^{1 to} R _P ¹⁰ , those having 3 to 10 carbon atoms are preferable, and specific examples include pyridyl group, thienyl group, oxazole group, oxadiazole group, benzothienyl group, dibenzofuryl group. , Dibenzothienyl group, pyrazyl group, pyrimidyl group, pyrazoyl group, imidazolyl group, phenylcarbazoyl group and the like.
The alkylamino group represented by R _P ^{1 to} R _P ¹⁰ is preferably an alkylamino group having 1 to 10 carbon atoms, and specific examples include a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, and the like.
The arylamino group represented by R _P ^{1 to} R _P ¹⁰ is preferably an arylamino group having 6 to 30 carbon atoms, and specific examples thereof include a diphenylamino group, a carbazoyl group, and a phenylnaphthylamino group.

  The substituents that these groups may have include aryl groups, arylamino groups, alkyl groups, perfluoroalkyl groups, halide groups, carboxyl groups, cyano groups, alkoxyl groups, aryloxy groups, carbonyl groups, oxycarbonyls. Group, carboxylic acid group, heterocyclic group and the like. Preferably, an aryl group having 6 to 16 carbon atoms, an arylamino group having 12 to 30 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a perfluoroalkyl group having 1 to 12 carbon atoms, a fluoride group, and 1 to 10 carbon atoms. Oxycarbonyl groups, cyano groups, alkoxy groups having 1 to 10 carbon atoms, aryloxy groups having 6 to 16 carbon atoms, carbonyl groups having 2 to 16 carbon atoms, heterocyclic groups having 5 to 20 carbon atoms, and the like.

Among the substituents, examples of the aryl group having 6 to 16 carbon atoms include a phenyl group, a naphthyl group, and a phenanthryl group.
Examples of the arylamino group having 12 to 30 carbon atoms include a diphenylamino group, a carbazoyl group, and a phenylcarbazoyl group.
Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a butyl group, an i-propyl group, a neopentthiol group, and a t-butyl group.
A trifluoromethyl group etc. are mentioned as an example of a C1-C12 perfluoroalkyl group.
Examples of the oxycarbonyl group having 1 to 10 carbon atoms include a methoxycarbonyl group and an ethoxycarbonyl group.
Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group and an ethoxy group.
Examples of the aryloxy group having 6 to 16 carbon atoms include a phenyloxy group.
Examples of the carbonyl group having 2 to 16 carbon atoms include an acetyl group and a phenylcarbonyl group.
Examples of the heterocyclic group having 3 to 20 carbon atoms include pyridyl group, thienyl group, oxazole group, oxadiazole group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, pyrazyl group, pyrimidyl group, pyrazoyl group, imidazoyl Group and the like.
Among the substituents that R _P ^{1 to} R _P ¹⁰ and R _P ^{1 to} R _P ^{10 described above} may have, an electron donating group such as an arylamino group and an alkoxy group, a thienyl group, and a benzothienyl group And the like contribute to the increase in the emission wavelength of the compound (P-1). Thus the substituent that may be _R ^P 1 _~R ^{P 10} and _R ^P 1 _~R ^{P 10} has, by selecting these substituents, can be obtained that exhibit a green light emission.

Of the compounds (P-1), particularly preferred are the following general formulas (P-1a), (P-1b), (P-1c), (P-1d), or (P-1e). It is a compound represented by these. In the general formulas (P-1a), (P-1b), (P-1c), (P-1d), and (P-1e), R _P ^{1 to} R _P ¹⁰ are R in the general formula (P-1). it is synonymous with _P ¹ _{~R P} ^10. Further, R _P ¹ and R _P ² , R _P ⁶ and R _P ⁷ in the general formula (P-1c), R _P ¹ and R _P ¹⁰ , R _P ⁵ and R _P ⁶ in the general formula (P-1d), R _P ⁹ and R _P ¹⁰ , R _P ⁴ and R _P ⁵ in the general formula (P-1e) are bonded to each other to form a ring. The ring formed here is preferably a 5- or 6-membered ring.

  Specific examples of pyrene derivatives that can be used in the present invention are shown below, but the present invention is not limited thereto.

  The pyrene derivatives represented by the general formulas (P-1a) to (P-1e) can be synthesized according to the following scheme.

In the above scheme, R P 1 ~R P 10 has the same meaning as R P 1 ~R P 10 in the general formula (P-1). X represents a halogen atom.

<Host material>
The light emitting layer preferably further contains a host material. The component most contained in the light emitting layer is preferably a host material. The host material may be a hole transporting host material or an electron transporting host material, but a hole transporting host material can be used.
The host material used in the present invention may contain the following compounds. For example, pyrrole, indole, carbazole (eg, CBP (4,4′-di (9-carbazoyl) biphenyl)), azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, Pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinyl) Carbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazo , Pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds , Metal complexes of heterocyclic tetracarboxylic anhydrides such as naphthalene and perylene, metal complexes of phthalocyanine and 8-quinolinol derivatives and metal complexes having metal phthalocyanine, benzoxazole and benzothiazole as ligands Examples thereof include complexes and derivatives thereof (which may have a substituent or a condensed ring).
In the production method of the present invention, a carbazole compound and a triphenylene compound as described later are preferable as the host material, and a triphenylene compound is more preferable.
The host material is also preferably a flat material as in the light emitting material, and examples thereof include a triphenylene compound described later.

In the light emitting layer of the present invention, the host material triplet lowest excitation energy (T ₁ energy) is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability.

  Further, the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass to 95% by mass with respect to the total compound mass forming the light emitting layer. Preferably there is.

  In the present invention, the host material preferably contains at least one compound represented by the general formula (4-1) or (4-2) which is a carbazole compound.

  The compound represented by the general formula (4-1) or (4-2) is preferably contained in the light emitting layer in an amount of 30 to 99% by mass, preferably 40 to 97% by mass, and 50 to 95% by mass. It is particularly preferred that it be included. Moreover, when using the compound represented by general formula (4-1) or (4-2) for a some organic layer, it is preferable to contain in said layer in each layer.

  The compound represented by the general formula (4-1) or (4-2) may contain only one kind in any organic layer, and a plurality of general formulas (4-1) or (4 The compound represented by -2) may be contained in combination at any ratio.

  The host material is preferably a compound represented by the following general formula (4-1) or (4-2).

(In General Formulas (4-1) and (4-2), d and e each represent an integer of 0 to 3, at least one of which is 1 or more. F represents an integer of 1 to 4. R ⁸ is substituted. When a plurality of R ₈ are present, R ₈ may be different or the same, and at least one of R ⁸ represents a carbazole group represented by the following general formula (5).

(In General Formula (5), each R ₉ independently represents a substituent. G represents an integer of 0 to 8.)

R ₈ each independently represents a substituent, specifically, a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, or a substituent represented by the general formula (5). is there. When R ₈ does not represent the general formula (5), it is preferably an alkyl group having 10 or less carbon atoms, a substituted or unsubstituted aryl group having 10 or less carbon atoms, and more preferably an alkyl group having 6 or less carbon atoms. is there.

R ₉ each independently represents a substituent, specifically a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, or a heterocyclic group, preferably an alkyl group having 10 or less carbon atoms, a carbon group It is a substituted or unsubstituted aryl group having several tens or less, and more preferably an alkyl group having six or fewer carbon atoms.
g represents an integer of 0 to 8, and is preferably 0 to 4 from the viewpoint of not excessively shielding the carbazole skeleton responsible for charge transport. From the viewpoint of ease of synthesis, when carbazole has a substituent, those having a substituent so as to be symmetric with respect to the nitrogen atom are preferable.

In the general formula (4-1), the sum of d and e is preferably 2 or more from the viewpoint of maintaining the charge transport ability. Further, R ₈ is preferably substituted with meta for the other benzene ring. The reason for this is that in ortho substitution, the steric hindrance between adjacent substituents is large, so that the bond is easily cleaved, and the durability is lowered. In addition, in para substitution, the molecular shape approaches a rigid rod shape and is easily crystallized, so that element degradation is likely to occur under high temperature conditions. Specifically, a compound represented by the following structure is preferable.

In the above formula, ^{R 8} has the same meaning as ^{R 8} in the general formula (4-1), h and i are each independently 0 or 1, 0 is preferable.
R ₉ each independently represents a substituent. g represents an integer of 0 to 8.

In the general formula (4-2), f is preferably 2 or more from the viewpoint of maintaining the charge transport ability. When f is 2 or 3, it is preferable that R ⁸ is mutually substituted with meta from the same viewpoint. Specifically, a compound represented by the following structure is preferable.

In the above formula, each R ₉ independently represents a substituent. g represents an integer of 0 to 8.

When the general formulas (4-1) and (4-2) have a hydrogen atom, an isotope of hydrogen (such as a deuterium atom) is also included. In this case, all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used. R ⁹ in the general formula (5) is preferably substituted with deuterium, and the following structures are particularly preferable.

  Furthermore, the atom which comprises a substituent represents that the isotope is also included.

  The compounds represented by the general formulas (4-1) and (4-2) can be synthesized by combining various known synthesis methods. Most commonly, carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo). Regarding the coupling reaction of the obtained carbazole compound and halogenated aryl compound using a palladium catalyst, Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40: 6393 (1999) and the like. The reaction temperature and reaction time are not particularly limited, and the conditions described in the above literature can be applied. Some compounds such as mCP which are commercially available can be preferably used.

The compounds represented by the general formulas (4-1) and (4-2) of the present invention preferably form a thin layer by a vacuum deposition process, but a wet process such as solution coating can also be suitably used. . The molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility.
Also, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Particularly preferred.

  General formulas (4-1) and (4-2) are preferably the following structures or compounds in which one or more hydrogen atoms are substituted with deuterium atoms.

In the above formula, R ₈ and R ₉ each independently represents a substituent.

  Specific examples of the compounds represented by formulas (4-1) and (4-2) in the present invention are illustrated below, but the present invention is not limited to these.

As the host material, an aromatic hydrocarbon compound is also preferable, and a hydrocarbon compound represented by the following general formula (Tp-1) which is a triphenylene compound (hereinafter sometimes simply referred to as “hydrocarbon compound”) is preferable.
The hydrocarbon compound represented by the general formula (Tp-1) is composed of only carbon atoms and hydrogen atoms and is excellent in terms of chemical stability. Therefore, the driving durability is high, and various changes are difficult to occur during high luminance driving. There is an effect.

  The hydrocarbon compound represented by the general formula (Tp-1) preferably has a molecular weight in the range of 400 to 1200, more preferably 400 to 1000, and still more preferably 400 to 800. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1200 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.

  The use of the hydrocarbon compound represented by the general formula (Tp-1) is not limited, and the hydrocarbon compound may be further contained in any layer within the organic layer as well as the organic layer adjacent to the light emitting layer.

(In the general formula (Tp-1), R ^{12 to} R ²³ are each independently substituted with a hydrogen atom, an alkyl group, or a cyano group, an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group. A phenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, or a group formed by a combination thereof, provided that R ^{12 to} R ²³ are not all hydrogen atoms.)

Examples of the alkyl group represented by R ^{12 to} R ²³ include a substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group and the like can be mentioned, preferably methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, more preferably methyl group, ethyl group, or A tert-butyl group.

R ^{12 to} R ²³ are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, and a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
A benzene ring that may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (which may be further substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group); It is particularly preferred.

  The total number of aryl rings in the general formula (Tp-1) is preferably 2 to 8, and preferably 3 to 5. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.

R ^{12 to} R ²³ each independently preferably has a total carbon number of 20 to 50, and more preferably a total carbon number of 20 to 36. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.

  In one embodiment of the present invention, the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-2).

(In General Formula (Tp-2), a plurality of Ar ¹ are the same, and a phenyl group, a fluorenyl group, which may be substituted with a cyano group, an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, A naphthyl group, a triphenylenyl group, or a group formed by combining these is represented.)

As the alkyl group and alkyl group represented by Ar ¹ , a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group that may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, R ^{12 to} R ²³ It is synonymous with what was mentioned, and a preferable thing is also the same.

  In another aspect of the present invention, the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-3).

(In the general formula (Tp-3), L represents a cyano group, an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group optionally substituted with a triphenylenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, or (It represents an n-valent linking group formed by combining these, and n represents an integer of 1 to 6.)

The alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group that forms the n-valent linking group represented by L has the same meaning as that described for R ^{12 to} R ²³ .
L is preferably an alkyl group or an n-valent linking group formed by combining a benzene ring, a fluorene ring, or a combination thereof, which may be substituted with a benzene ring.
Although the preferable specific example of L is given to the following, it is not limited to these. In the specific examples, it is bonded to the triphenylene ring by *.

  n is preferably 1 to 5, and more preferably 1 to 4.

  In another embodiment of the present invention, the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-4).

(In General Formula (Tp-4), Ar ² in the case where a plurality of Ar ² are the same, Ar ² represents a cyano group, an alkyl group, a phenyl group, a naphthyl group, a triphenylenyl group, or a group formed by combining these. p and q each independently represents 0 or 1, but p and q are not simultaneously 0. When p and q represent 0, Ar ² represents a hydrogen atom.)

Ar ² is preferably a group formed by combining an alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group, or a triphenylenyl group, and more preferably a combination of a methyl group, a t-butyl group, a phenyl group, or a triphenylenyl group. It is a group consisting of
Ar ² is particularly preferably a benzene ring substituted at the meta position with an alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group, a triphenylenyl group, or a combination thereof.

When the hydrocarbon compound according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent device or a charge transport material of a layer adjacent to the light emitting layer, the energy gap in a thin film state than the light emitting material (the light emitting material is a phosphorescent light emitting material) In the case of ( ₂ ), when the lowest excited triplet (T ₁ ) energy in the thin film state is large, the emission is prevented from being quenched, which is advantageous for improving the efficiency. On the other hand, from the viewpoint of chemical stability of the compound, it is preferable that the energy gap and T ₁ energy are not too large. The T ₁ energy in the film state of the hydrocarbon compound represented by the general formula (Tp-1) is preferably 52 kcal / mol or more and 80 kcal / mol or less, and 55 kcal / mol or more and 68 kcal / mol or less. Is more preferable, and it is still more preferable that they are 58 kcal / mol or more and 63 kcal / mol or less. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T ₁ energy is preferably in the above range.

The T ₁ energy can be obtained from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a film thickness of about 50 nm by a vacuum deposition method, and the phosphorescence emission spectrum of the thin film is F-7000 Hitachi Spectrofluorimeter (Hitachi High-Technologies) under liquid nitrogen temperature. Use to measure. The T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

  Although the specific example of the aromatic hydrocarbon compound concerning this invention is illustrated below, this invention is not limited to these.

The compounds exemplified as the aromatic hydrocarbon compounds according to the present invention can be synthesized by the methods described in WO05 / 013388 pamphlet, WO06 / 130598 pamphlet, and WO09 / 021107 pamphlet.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

In addition to the light emitting layer, the aromatic hydrocarbon compound is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the cathode. You may further contain in any layer in a layer. As the introduction layer of the aromatic hydrocarbon compound according to the present invention, any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer are used. It can contain.
The organic layer adjacent to the light emitting layer between the light emitting layer and the cathode and containing the aromatic hydrocarbon compound is preferably a charge blocking layer or an electron transporting layer, and more preferably a charge blocking layer.
By containing the aromatic hydrocarbon compound in the layer adjacent to the light emitting layer, the efficiency and durability of the device are improved. When the light-emitting layer is excited, excitons are biased to the interface between the light-emitting layer and the adjacent layer, and the phenomenon of destroying the adjacent layer occurs, but the aromatic hydrocarbon compound has a highly durable structure. Therefore, it is considered that the above effects can be obtained.

The aromatic hydrocarbon compound preferably comprises only carbon atoms and hydrogen atoms from the viewpoint of ease of synthesis.
When the aromatic hydrocarbon compound is contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass. When the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably included in an amount of 0.1 to 99% by mass, more preferably 1 to 95% by mass, and more preferably 10 to 95%, based on the total mass of the light emitting layer. More preferably, it is contained by mass%.

In the light-emitting device of the present invention, the aromatic hydrocarbon compound is contained in an organic layer adjacent to the light-emitting layer between the light-emitting layer and the cathode, but its use is not limited, and any layer in the organic layer It may be further contained. The introduction layer of the aromatic hydrocarbon compound should be contained in the light emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, exciton block layer, charge block layer or a plurality of layers. Can do.
The organic layer adjacent to the light emitting layer between the light emitting layer and the cathode containing the aromatic hydrocarbon compound is preferably a charge blocking layer or an electron transport layer, and more preferably an electron transport layer.

  The glass transition temperature (Tg) of the aromatic hydrocarbon compound according to the present invention is 60 ° C. or higher and 400 ° C. or lower from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device. It is preferably 65 ° C. or higher and 300 ° C. or lower, more preferably 80 ° C. or higher and 180 ° C. or lower.

  The host material is preferably a highly planar host material (hereinafter also referred to as “flat plate host compound”) because the regularity of the arrangement state becomes higher. Specifically, the aspect ratio is A compound having a shape of 3 or more is more preferable.

The aspect ratio is the ratio (molecular diameter / molecular thickness) between the molecular diameter and the molecular thickness of the compound.
From the viewpoint of orientation, the host material used in the present invention preferably has an aspect ratio of 3 or more, and more preferably has an aspect ratio of 3.5 or more.
Here, the molecular diameter means the longest molecular length, and is defined as follows by theoretical calculation. The theoretical calculation here is performed using a density functional method. Specifically, using Gaussian 03 (US Gaussian), basis function: 6-31G ^* , exchange correlation functional: B3LYP / LANL2DZ, Perform structural optimization calculations. Using the optimized structure obtained by the structure optimization calculation, the length in the ball and stick display of the longest molecular length is defined as the molecular diameter of the host material.
In addition, the molecular thickness is assumed to be the above-mentioned molecular diameter as the x-axis, the y-axis is taken so that the molecular length in the y-axis direction becomes the maximum in this state, and the direction perpendicular to the x and y axes is taken as the z-axis. Means the thickness of the molecule in the z-axis direction. The molecular thickness is also obtained by the same method as the molecular diameter, and the length in the thickness direction of the molecule in the ball and stick display is defined as the molecular thickness.

[Location and concentration of host material]
In the present invention, the triphenylene derivative represented by the above general formula (TI) is preferably contained in the light emitting layer, but its application is not limited, and any layer in the organic layer may be further added. For example, as an introduction layer of a triphenylene derivative represented by the general formula (TI), a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton blocking layer, a charge Any of the block layers can be mentioned.
When the triphenylene derivative represented by the general formula (TI) is further contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, more preferably 85 to 100% by mass.

(Charge transport layer)
The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element.
Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a hole block layer, an electron transport layer, and an electron injection layer.

-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.
In the present invention, the organic layer preferably includes a hole injection layer or a hole transport layer containing an electron-accepting dopant.

-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.

  Regarding the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention. .

-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.
As an example of an organic compound constituting the hole blocking layer, aluminum (III) bis (2-methyl-8-quinolinolato) 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 made of one or more of the materials described above, or may have a multilayer structure made 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 an example of the organic 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 electron 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.

In the method for producing an organic electric field element of the present invention, for the organic layer formed by vapor deposition on the light emitting layer, among the components constituting the organic layer, the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa. As long as the sublimation start temperature Tb (° C.) satisfies 0.60 ≧ Tem / Tb ≧ 0.30 when the glass transition temperature of the component most contained in the light emitting layer is Tem (° C.). Although not particularly limited, the organic layer is preferably a charge transport layer such as an electron transport layer or an electron injection layer, and preferably contains an electron transport material or an electron injection material. It is more preferable that it contains an electron transport material.
The component having the highest sublimation start temperature at 1 × 10 ⁻² Pa is preferably an electron transport material.
Among the components constituting the layer, the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa is represented by the following general formula (O-1) including, for example, a carbazole compound, a triphenylene compound, and an imidazopyridine compound. The compound represented by formula (O-1) is more preferable.
Examples of the carbazole compound and the triphenylene compound include those described above as the host material.

[Compound represented by formula (O-1)]

In general formula (O-1), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group.
A ^{O1 to} A ^O4 each independently represent C—R ^A or N.
R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different.
L ^O1 represents a divalent to hexavalent linking group composed of an aryl ring or a heteroaryl ring.
^nO1 represents an integer of 2-6.
A plurality of R ^O1 and A ^{O1 to} A ^O4 may be the same or different.

R ^O1 represents an alkyl group (preferably having a carbon number of 1 to 8), an aryl group (preferably having a carbon number of 6 to 30), or a heteroaryl group (preferably having a carbon number of 4 to 12). Z may be included. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. A preferable substituent when the aryl group of R ^O1 has a substituent includes an alkyl group or an aryl group, and an aryl group is more preferable. When the aryl group of R ^O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent Z, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, and even more preferably an unsubstituted group. A phenyl group or a 2-phenylphenyl group.

A ^{O1 to} A ^O4 each independently represent C—R ^A or N. Of A ^{O1 to} A ^O4 , 0 to 2 are preferably N atoms, more preferably 0 or 1 are N atoms. It is preferable that all of A ^{O1 to} A ^O4 are C—R ^A , or A ^O1 is an N atom, and A ^{O2 to} A ^O4 are C—R ^A , A ^O1 is an N atom, and A ^O2 to More preferably, A ^O4 is C—R ^A , A ^O1 is an N atom, A ^{O2 to} A ^O4 are C—R ^A , and R ^A is all preferably a hydrogen atom.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent Z. The plurality of ^RA may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group composed of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group. L ^O1 may have the above-described substituent Z, and when it has a substituent, the substituent is preferably an alkyl group, an aryl group, or a cyano group. Specific examples of L ^O1 include the following.

^nO1 represents an integer of 2 to 6, preferably an integer of 2 to 4, and more preferably 2 or 3. The most preferable value is 3 from the viewpoint of device efficiency, and the most preferable value is 2 from the viewpoint of device durability.

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

In general formula (O-2), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group.
R ^{O2 to} R ^O4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
A ^{O1 to} A ^O4 each independently represent C—R ^A or N.
R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different.
A plurality of R ^O1 and A ^{O1 to} A ^O4 may be the same or different.

R ^O1 and ^A O1 ^{to A O4,} the general formula (O1) in the same meaning as ^{R O1} and ^A O1 ^{to A O4} of, also the same preferable ranges thereof.
R ^{02 to} R ⁰⁴ are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). Which may have the aforementioned substituent Z. R ^{02 to} R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

  Specific examples of the compound represented by the general formula (O-1) are shown below, but the present invention is not limited thereto.

Although the compound represented by the said general formula (O-1) is preferable as an electron transport material, the use is not limited and may be further contained in any layer in an organic layer. As the introduction layer of the compound represented by the general formula (O-1) according to the present invention, a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block It can be contained in any or a plurality of layers.
The organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, containing the compound represented by the general formula (O-1), is preferably a charge blocking layer or an electron transporting layer, and is an electron transporting layer. It is more preferable.

  When the compound represented by the general formula (O-1) is contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass. When the compound represented by the general formula (O-1) is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99% by mass, and 1 to 95% by mass with respect to the total mass of the light emitting layer. Is more preferable, and it is more preferable to include 10 to 95% by mass.

  The compound represented by the general formula (O-1) preferably has a molecular weight in the range of 400 to 2000, more preferably 500 to 1500, and still more preferably 600 to 1000. If the molecular weight is 400 or more, a film having good film quality can be obtained, and if the molecular weight is 2000 or less, it is preferable in terms of vapor deposition suitability and solubility.

When the compound represented by the general formula (O-1) according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent element or a charge transport material of a layer adjacent to the light emitting layer, it is in a thin film state than the light emitting material. When the energy gap (the light emitting material is a phosphorescent light emitting material) is large, the minimum excited triplet (T ₁ ) energy in a thin film state is large, which prevents the light emission from being quenched and is advantageous for improving the efficiency. On the other hand, from the viewpoint of chemical stability of the compound, it is preferable that the energy gap and T ₁ energy are not too large. The T ₁ energy in the film state of the compound represented by the general formula (O-1) is preferably 52 kcal / mol to 80 kcal / mol, and more preferably 55 kcal / mol to 68 kcal / mol). Preferably, it is 58 kcal / mol or more and 63 kcal / mol or less. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T ₁ energy is preferably in the above range.

  The glass transition temperature (Tg) of the compound represented by the general formula (O-1) is 80 ° C. or higher and 400 ° C. from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device. The temperature is preferably 100 ° C. or higher and 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower.

The compounds exemplified as the compound represented by the general formula (O-1) are WO05 / 013388 pamphlet, WO06 / 130598 pamphlet, WO09 / 021107 pamphlet, US2009 / 0009065, International It can be synthesized by the methods described in the Publication No. 09/008311 pamphlet and the International Publication No. 04/018587 pamphlet.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

<Protective layer>
In the present invention, the entire organic EL element may be protected by a protective layer.
Regarding the protective layer, the matters described in paragraph numbers [0169] to [0170] of JP-A-2008-270736 can be applied to the present invention.

<Sealing container>
The element of this invention may seal the whole element using a sealing container.
Regarding the sealing container, the matters described in paragraph No. [0171] of JP-A-2008-270736 can be applied to the present invention.

(Drive)
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving method of the organic electroluminescent device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

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

The organic EL element in the present invention may have a resonator structure. For example, a multilayer mirror made of a plurality of laminated films having different refractive indexes, a transparent or translucent electrode, a light emitting layer, and a metal electrode are superimposed on a transparent substrate. The light generated in the light emitting layer resonates repeatedly with the multilayer mirror and the metal electrode as a reflection plate.
In another preferred embodiment, a transparent or translucent electrode and a metal electrode each function as a reflecting plate 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 Japanese Patent Application Laid-Open No. 2004-127795.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 5% or more, more preferably 7% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency near 100 to 300 cd / m ² when the device is driven at 20 ° C. Can do.

  The internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%. However, the substrate shape, electrode shape, organic layer thickness, inorganic layer thickness, organic layer refractive index, inorganic layer refractive index, etc. By devising it, it is possible to increase the light extraction efficiency to 20% or more.

  The organic electroluminescent element of the present invention preferably has a maximum emission wavelength (maximum intensity wavelength of emission spectrum) of 350 nm to 700 nm, more preferably 350 nm to 600 nm, still more preferably 400 nm to 520 nm, particularly preferably. It is 400 nm or more and 470 nm or less.

(Use of light-emitting element of the present invention)
The light-emitting element of the present invention is a light-emitting device, pixel, display element, display device, display, backlight, electrophotography, illumination light source, illumination device, recording light source, exposure light source, reading light source, sign, signboard, interior, or optical communication It can utilize suitably for etc. In particular, it is preferably used for a device that is driven in a region where light emission luminance is high, such as a light emitting device, a lighting device, and a display device.

Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
The light emitting device 20 in FIG. 2 includes a transparent substrate (supporting substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.

The organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. A protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween. In addition, a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate | omitted.
Here, as the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.

  The use of the light-emitting device of the present invention is not particularly limited, and for example, in addition to a lighting device, a display device such as a television, a personal computer, a mobile phone, and electronic paper can be used.

(Lighting device)
Next, an illumination device according to an embodiment of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of a lighting device according to an embodiment of the present invention.
As shown in FIG. 3, the illumination device 40 according to the embodiment of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 3, the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31. As the transparent substrate 31, for example, a glass substrate can be preferably cited. As the fine particles 32, transparent resin fine particles can be preferably exemplified. As the glass substrate and the transparent resin fine particles, known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.

  EXAMPLES The present invention will be described more specifically with reference to the following examples. However, the scope of the present invention is not limited to the following examples.

<Synthesis of Luminescent Material E-4>
A light emitting material E-4 was synthesized according to the following scheme.

(Synthesis of Compound 1a)
5 drops of acetic acid was added dropwise to an ethanol solution (30 ml) of 2-hydroxy-4-methoxybenzaldehyde (1.6 g) and 4,5-dimethyl-1,2-phenylenediamine (0.73 g) with a 1 ml Komagome pipette. The reaction was carried out at 6 ° C. for 6 hours. The precipitated solid was collected by filtration and recrystallized with ethanol to obtain Compound 1a (2.0 g).

(Synthesis of luminescent material E-4)
To a solution of compound 1a (0.9 g) and sodium acetate (0.19 g) in acetonitrile (30 ml), a DMSO solution (15 ml) of PtCl ₂ (0.61 g) was added dropwise at 80 ° C. and reacted for 7 hours. The reaction solution was filtered and recrystallized with THF to obtain a luminescent material E-4 (1.04 g). The compound was identified by elemental analysis, NMR and MASS spectrum, and it was confirmed that the desired compound was obtained. The appearance was a yellow solid.

(Examples 1-1 to 1-34 and Comparative Examples 1-1 to 1-21)
1. Preparation of organic electroluminescent element All materials used for the preparation of organic electroluminescent element were purified by sublimation, and the purity (absorption intensity area ratio of 254 nm) was 99.9% or higher by high performance liquid chromatography (Tosoh TSKgel ODS-100Z). I confirmed that there was.
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on this transparent anode (ITO film: film thickness 70 nm) by vacuum deposition.
First layer: 2-TANTA and F ₄ -TCNQ (mass ratio 99.7: 0.3); film thickness 160 nm
Second layer: NPD; film thickness 30 nm
Third layer (light emitting layer): Light emitting layer materials 1 and 2 shown in Table 1 (ratio (% by mass) of light emitting layer material 2 with respect to the total of light emitting layer materials 1 and 2 shown in Table 1); film thickness 30 nm
Fourth layer (electron transport layer): electron transport material shown in Table 1; film thickness 5 nm
Fifth layer: Alq; film thickness 35 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 laminated body is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Then, an organic electroluminescent element was obtained.

In addition, about vapor deposition of the electron carrying layer, vapor deposition was performed in the distance L of the vapor deposition source shown in Table 1, and a to-be-deposited surface (light emitting layer surface).
Further, at 1 × 10 ⁻² Pa of the electron transport material shown in Table 1 which is the component having the highest sublimation start temperature in the electron transport layer, the glass transition temperature Tem of the light emitting layer material 1 which is the most contained component in the light emitting layer. Table 1 shows the sublimation start temperature Tb.
The glass transition temperature Tem and the sublimation start temperature Tb were measured as follows.
The glass transition temperature was measured by heating a sample with a differential scanning calorimeter (SII Nano Technology Co., Ltd .: DSC 6220), and the temperature of the obtained glass transition peak on the low temperature side was read.
The sublimation start temperature was measured with a weight reduction curve at 1 × 10 ⁻² Pa at a sample amount of 20 mg, and the weight reduction rate was −5% (all samples had a purity of 97% by HPLC area ratio, so −5 The% point was regarded as the temperature at which the material started sublimation and evaporation.) Note that all measurements were performed by raising the temperature at a rate of 1 ° C. per minute.
As shown in Table 1, the light emitting layer uses the light emitting layer material 1 (H-1 to H-5) and the light emitting layer material 2 (E-1 to E-5), and the electron transport layer is an electron transport material A. ~ H was used.

(Comparative Example 2-1)
<Preparation of Coating Solution A for Hole Transport Layer Formation>
The following compound A1 is dissolved in xylene for electronic industry to obtain a total solid concentration of 0.4% by mass, and this is filtered through a PTFE filter having a pore size of 0.22 μm to prepare a coating liquid A for forming a hole transport layer. did.

<Preparation of light emitting layer forming coating solution A>
91% by mass of the host compound H-1 and 9% by mass of the luminescent material E-1 are dissolved in methyl ethyl ketone (MEK) to a solid content concentration of 1.0% by mass, which has a pore size of 0.22 μm. It filtered with the PTFE filter and the coating liquid A for light emitting layer formation was prepared.

<Element fabrication>
A transparent support substrate was obtained by depositing ITO with a thickness of 150 nm on a glass substrate of 25 mm × 25 mm × 0.7 mm.
This transparent support substrate was put in a cleaning container and subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes.
On this ITO-attached glass substrate, PTPDES represented by the following structural formula (weight average molecular weight Mw = 13,100, manufactured by Chemipro Kasei Co., Ltd., n represents the number of repetitions of the structure in parentheses and is an integer) 2 mass Part was dissolved in 98 parts by mass of cyclohexanone for electronics industry (manufactured by Kanto Chemical), spin-coated (2500 rpm, 20 seconds) to a thickness of about 40 nm, then dried at 120 ° C. for 10 minutes and annealed at 160 ° C. for 60 minutes By processing, a hole injection layer was formed.

  On the hole injection layer, the hole transport layer forming coating liquid A prepared as described above is spin-coated (1500 rpm, 20 seconds) so as to have a thickness of about 10 nm, and then dried at 120 ° C. for 30 minutes. As a result, a hole transport layer was formed.

  The light emitting layer forming coating solution A prepared as described above is spin-coated on the hole transport layer in a glove box (dew point -68 degrees, oxygen concentration 10 ppm) to a thickness of about 30 nm (1500 rpm, 20 seconds). And a light emitting layer.

  Next, on the light emitting layer, as an electron transport layer, the distance L between the deposition source shown in Table 2 and the surface to be vapor-deposited (light emitting layer surface) is set to a film thickness of 5 nm by vacuum deposition. It formed so that it might become.

Lithium fluoride (LiF) was formed as an electron injection layer on the electron transport layer by a vacuum deposition method so as to have a thickness of 1 nm. Furthermore, 70 nm of metal aluminum was vapor-deposited to make a cathode.
The laminate produced as described above is put in a glove box substituted with argon gas, and sealed with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, an organic electroluminescent element of Comparative Example 2-1 was produced.

(Examples 2-1 to 2-12 and Comparative Examples 2-2 to 2-6)
In the preparation of the light emitting layer forming coating solution A in Comparative Example 2-1, the light emitting material and the host material shown in Table 2 below were used instead of the light emitting material E-1 and the host compound H-1, and an electron transport layer was used. As for the vapor deposition, Examples 2-1 to 2--2 were performed in the same manner as Comparative Example 2-1, except that vapor deposition was performed at a distance L between the vapor deposition source and the deposition surface (light emitting layer surface) shown in Table 2. 12 and Comparative Examples 2-2 to 2-6 were obtained.
In addition, the glass transition temperature of the light emitting layer material 1 which is the most contained component in the light emitting layer and the sublimation at 1 × 10 ⁻² Pa of the electron transporting material shown in Table 2 which is the component having the highest sublimation start temperature in the electron transporting layer. The starting temperature is shown in Table 2.

(Examples 3-1 to 3-6)
In the preparation of the light emitting layer forming coating solution A in Comparative Example 2-1, the light emitting material and the host material shown in Table 3 below were used in place of the light emitting material E-1 and the host compound H-1, and an electron transport layer was used. As for the vapor deposition, Examples 3-1 to 3-3 were performed in the same manner as Comparative Example 2-1, except that vapor deposition was performed at a distance L between the vapor deposition source and the deposition surface (light emitting layer surface) shown in Table 3. 6 organic electroluminescent elements were obtained.
In addition, the glass transition temperature of the light emitting layer material 1 which is the most contained component in the light emitting layer and the sublimation at 1 × 10 ⁻² Pa of the electron transporting material shown in Table 1 which is the component having the highest sublimation start temperature in the electron transporting layer. Table 3 shows the starting temperature and the degree of orientation of the light emitting material in the light emitting layer.
For the degree of orientation, the cleaned quartz substrate is placed in a vapor deposition apparatus, a film is formed by co-evaporation of a light emitting material and a host material having the same material and composition as the light emitting layer described above, and this is transformed using ATR-IR. Table 3 shows the values of the order parameter (degree of orientation) of the light emitting material in the film calculated by measurement.

2. Evaluation <EQE (relative value)>
The external quantum efficiency was measured by applying a direct current voltage to each element using a source measure unit 2400 manufactured by Toyo Technica, and emitting light, and the luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these, the external quantum efficiency at a luminance of around 1000 cd / m ² was calculated by the luminance conversion method.
In Table 1, the value for the element of Comparative Example 1-1 and in Table 2 for the element of Comparative Example 2-1, the relative value is shown as 1.
In Table 3, the value of the element of Example 3-1 was set to 1 and indicated as a relative value.

<EQE ratio>
The ratio of the lowest efficiency E1 to the highest efficiency E2 (external quantum efficiency when the current density is changed from 0.025 to 25 mA / cm ² by changing the DC voltage applied to the device from a low voltage to a high voltage ( E1 / E2) was determined and the results are shown in Tables 1-3. The higher the EQE ratio, the better the light emission efficiency even when driving at a high voltage.

From the results of Tables 1 to 3, when the light emitting layer and the organic layer thereabove have the same composition, the Example according to the method for producing the organic electroluminescent element of the present invention shows a higher EQE than the Comparative Example. It can be seen that the luminous efficiency is excellent even when driven at a high voltage.
Moreover, it turned out that EQE shows a high value, so that the density | concentration of a luminescent material is low like Examples 1-4 to 1-6 and Examples 1-23 to 1-25.
When the sublimation start temperature of the upper organic layer is substantially the same, EQE is higher when E or G is used than with the electron transport material C or F (Examples 1-13 to 1-18). This shows that the skeleton of the electron transport material preferably has a triphenylene structure.
As can be seen from a comparison between Examples 1-21 and 1-22, an element using a phosphorescent metal complex as the light-emitting material greatly improves EQE.
The element using E-4 having a flat skeleton as the light emitting material has a high EQE ratio at high luminance and low luminance compared to the element using the light emitting material E-2 which is not so, and the efficiency in a wide range. It is excellent in maintenance (Examples 1-22, 1-28). Further, by using H-5 having a flat skeleton as the host material of the light emitting layer, it is possible to achieve a high EQE and a high EQE ratio (Examples 1-32 and 1-33).

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ... -Cathode 10 ... Organic electroluminescent element 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 30A ..Light incident surface 30B ... Light exit surface
31 ... Transparent substrate 32 ... Fine particles 40 ... Illumination device

Claims (11)

A method for producing an organic electroluminescent device comprising an anode, a light emitting layer, an organic layer adjacent to the light emitting layer, and a cathode in this order,
In forming the organic layer by vapor deposition on the light emitting layer,
Among the components constituting the organic layer, for the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa, the sublimation start temperature Tb (° C.) is the glass transition temperature of the component most contained in the light emitting layer. When Tem (° C.) is satisfied, 0.60 ≧ Tem / Tb ≧ 0.30 is satisfied,
When the distance between the vapor deposition source when forming the organic layer and the surface of the light emitting layer is L (cm), the condition of 2.0 ≦ Tb / L ² ≦ 80 is satisfied. A method for manufacturing an organic electroluminescent element, characterized by performing vapor deposition.   The method for producing an organic electroluminescent element according to claim 1, wherein a deposition rate when depositing the organic layer is 0.2 to 1.5 Å / s.   The method for manufacturing an organic electroluminescent element according to claim 1, wherein the light emitting layer contains a phosphorescent light emitting material as a light emitting material.   The said light emitting layer contains a flat material as a light emitting material, The manufacturing method of the organic electroluminescent element as described in any one of Claims 1-3 characterized by the above-mentioned.   The method for producing an organic electroluminescent element according to claim 1, wherein the light emitting layer further includes a flat plate material as a host material.   The method for manufacturing an organic electroluminescent element according to claim 1, wherein the degree of orientation of the light emitting material in the light emitting layer is 0.6 or more. The method for producing an organic electroluminescent element according to claim 1, wherein the component having the highest sublimation start temperature at 1 × 10 ⁻² Pa is an electron transport material.   The method for producing an organic electroluminescent element according to claim 1, wherein a component contained most in the light emitting layer is a host material.   The organic electroluminescent element produced by the preparation method as described in any one of Claims 1-8.   A display device using the element according to claim 9.   An illumination device using the element according to claim 9.

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