JP2012079899A - Material for organic electroluminescent element, film, luminescent layer, organic electroluminescent element, and manufacturing method for organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a material for an organic electroluminescent element which can form a film having a high orientation without crystallization.SOLUTION: This is a material for an organic electroluminescent element which comprises: a host material which has at least 3 or more substituent groups with molecular width of 4.4 Å or more per one molecular and does not substantially crystallize on its own; and a flat sheet luminescent material. The material crystallizes when the host material is mixed with the flat sheet luminescent material.

Description

  The present invention relates to a material for an organic electroluminescent element, a film, a light emitting layer, an organic electroluminescent element, and a method for producing the organic electroluminescent element.

  As a device using organic materials, organic electroluminescent elements (hereinafter also referred to as organic EL elements) are expected to develop as lighting applications such as solid-state large-area full-color display elements and inexpensive large-area surface light sources. Has been. In general, an organic electroluminescent element is composed of an organic layer including a light emitting layer and a pair of counter electrodes sandwiching the organic layer. When a voltage is applied to such an organic electroluminescence device, electrons are injected from the cathode and holes are injected from the anode into the organic layer. The electrons and holes recombine in the light emitting layer, and light is emitted by releasing energy as light when the energy level returns from the conduction band to the valence band.

In an organic EL element, the refractive index of each layer constituting the element including the light emitting layer and the substrate of the element (glass substrate) is usually higher than that of air. For example, in an organic electroluminescent element, the refractive index of an organic layer such as a light emitting layer is 1.6-2.1. For this reason, most of the emitted light is totally reflected at the interface, so that only about 20% of the light emitted from the light emitting layer can be extracted outside the device. In order to obtain high luminance in this state, it is necessary to emit light excessively. As a result, there is a problem that the durability of the element is lowered.
On the other hand, it is known that the light extraction efficiency is improved in principle by orienting the light emitting material horizontally with respect to the substrate and increasing the light emitting component in the direction perpendicular to the substrate surface. In order to horizontally align the light emitting material, a host material or a light emitting material having high planarity is used.

However, there is a problem in that a highly planar material (flat plate material) is easily crystallized because it is likely to cause packing between molecules when oriented. Crystallization can be prevented by introducing a steric hindrance group into the flat plate material and increasing the intermolecular distance between the flat plate portions (core parts) by steric repulsion, but at the same time the liquid crystallinity (orientation) of the material is also reduced. I will let you.
On the other hand, Non-Patent Document 1 exhibits liquid crystallinity by adding triphenylene (hexaalkoxytriphenylene) having no steric hindrance group to triphenylene having a steric hindrance group (such as hexaphenyltriphenylene). It is described that the triphenylene molecules are oriented.
Non-Patent Document 1 does not describe an organic EL element, but Patent Document 1 describes an organic EL element that includes an iridium complex that is a phosphorescent material and hexaphenyltriphenylene in a light-emitting layer. However, in Patent Document 1, hexatriphenylene does not exhibit orientation.

International Publication No. 2006/130598

Liquid crystals, Vol. 33, no. 6,653-664

As described above, in order to improve the light extraction efficiency of the organic EL element, it is known that it is effective to perform horizontal alignment that crystallizes the flat plate material. Non-Patent Document 1 describes that alignment is exhibited by adding triphenylene having no steric hindrance group to triphenylene having a steric hindrance group, but it is used as a light-emitting material in an organic EL element. No knowledge is shown when a material having a molecular skeleton different from triphenylene such as a luminescent material is added.
In the organic EL element, an iridium complex or a platinum complex is often used as a phosphorescent material, but the platinum complex has high planarity and is advantageous for horizontal alignment. However, platinum complexes tend to aggregate due to platinum-platinum interactions, and it may be difficult to make the platinum complex molecules compatible with the host material without associating the platinum complex molecules.
Therefore, a material capable of exhibiting high orientation without being crystallized is demanded as a material for an organic electroluminescent element including a flat material.

  An object of the present invention is to provide a material for an organic electroluminescent element capable of forming a highly oriented film without being crystallized. Another object of the present invention is to provide a film and a light emitting layer using the organic electroluminescent element material. Furthermore, the objective of this invention is providing the organic electroluminescent element excellent in light extraction efficiency, and providing the manufacturing method of this organic electroluminescent element.

  When a steric hindrance group is introduced into the flat host material for suppressing crystallization, the orientation is lowered. However, as a result of investigation, the present inventors have found that when a light emitting material having high planarity is added to the host material, liquid crystallinity is exhibited and aggregation of the light emitting material can be suppressed. These organic electroluminescent device materials, which are a mixture of a flat host material having a steric hindrance group and a flat light emitting material, provide a highly oriented film without crystallization, and an organic electric field with excellent light extraction efficiency. A light emitting element can be obtained.

That is, the means for solving the above problems are as follows.
[1]
A host material having at least three substituents in a molecule having a molecular width of 4.4 mm or more and having substantially no liquid crystal properties alone;
A flat light emitting material;
A material for an organic electroluminescent element, which exhibits liquid crystallinity when the host material is mixed with the flat light emitting material.
[2]
The material for an organic electroluminescent element according to the above [1], wherein the flat luminescent material is a platinum complex.
[3]
The organic electroluminescent element material according to the above [1] or [2], wherein the host material is a compound represented by the following general formula (I).
Formula (I)
In general formula (I), A is a condensed ring structure having a conjugated structure of 16 electrons or more and 4 or more rings condensed. y represents the number of L substituted with A, and is an integer of 3-8. L represents the following group.
** represents a position that binds to A. Z represents a divalent linking group, Ar _I represents an aromatic ring which may have a substituent, T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, perfluoro An alkyl group or a perfluoroalkoxy group is represented. n is 0 or 1, m is 0 or 1, x is 0 or 1, r is 0 or 1, and when r = 0, m = 1 and x = 0. However, L has a site | part with a molecular width of 4.4 mm or more.
[4]
The material for an organic electroluminescent element according to any one of [1] to [3], wherein the condensed ring structure A is pyrene, perylene, or triphenylene.
[5]
The material for organic electroluminescent elements according to any one of [1] to [4], wherein the host material is a compound represented by the following general formula (II).
Formula (II)
In general formula (II), y represents the number of L substituted to a triphenylene skeleton, and is an integer of 3-6. * Represents a substitution position where L substitutes. L represents the following group.
** represents a position bonded to the triphenylene skeleton. Z represents a divalent linking group, Ar _I represents an aromatic ring which may have a substituent, T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, perfluoro An alkyl group or a perfluoroalkoxy group is represented. n is 0 or 1, m is 0 or 1, x is 0 or 1, r is 0 or 1, and when r = 0, m = 1 and x = 0. However, L has a site | part with a molecular width of 4.4 mm or more.
[6]
The organic electroluminescent element material according to [1] to [4], wherein the host material is a compound represented by the following general formula (III).
Formula (III)
In the general formula (III), T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, a perfluoroalkyl group, or a perfluoroalkoxy group. x is 0 or 1, r is 0 or 1, w represents an integer of 0 to 2, and when r = 0, x = 0. The substituent-(T) _x- (R _I ) _r is bonded to the phenyl group at the meta position or para position with respect to triphenylene.
[7]
The organic electroluminescence according to any one of [1] to [6], wherein the platinum complex is at least one selected from phosphorescent compounds represented by the following general formulas (1) to (5): Element material.
General formula (1)
(In the general formula (1), X, Y, and Z represent a carbon atom or a nitrogen atom, and 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 represents an integer of 0 to 3. Ar represents an aryl group, and R _{1 to} R ₄ each independently represents an alkyl group, an aryl group, an alkoxy group or an aryloxy group. Group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group, and when m, n, p, and q are 2 or more, a plurality of R _{1 to} R ₄ are connected to each other to form a cyclic structure. It may be formed.)
General formula (2)
(In General Formula (2), X, Y, and Z represent a carbon atom or a nitrogen atom, and either Z or Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. R, s, t and u each independently represents 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 or a cyano group. , A silyl group, or a heterocyclic group, and when r, s, t, and u are 2 or more, a plurality of R _{5 to} R ₈ may be connected to each other to form a cyclic structure. ₁ and W ₂ represent an alkyl group and may be bonded to each other to form a cyclic structure.
General formula (3)
(In General Formula (3), R _{9 to} R ₁₆ each independently represent a hydrogen atom, an alkyl group, an aryl group, a silyl group, or a heterocyclic group, and R ₉ and R ₁₁ , R ₁₁ and R ₁₂ , R ₁₂ and R ₁₀ , R ₁₄ and R ₁₅ , R ₁₃ and R ₁₆ may combine with each other to form a cyclic structure.)
General formula (4)
(In General Formula (4), X, Y, and Z represent a carbon atom or a nitrogen atom, and either Z or Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. M, n, p and g each independently represents an integer of 0 to _3. Ar represents an aryl group, R _{1 to} R ₃ and R ₃₀ , each independently 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 when m, n, p, and g are 2 or more, a plurality of R _{1 to} R ₃ and R ₃₀ are connected to each other adjacent to each other. A cyclic structure may be formed, and M and Q are each independently a carbon atom or a nitrogen atom.)
General formula (5)
(In General Formula (5), Z represents a carbon atom or a nitrogen atom. M, n, and g each independently represents an integer of 0 to _3. Ar represents an aryl group. R ₁ , R _2, and R ₃₀ 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 when m, n, or g is 2 or more, a plurality of R ₁ , R ₂ and R ₃₀ may be linked to each other to form a cyclic structure, and M and Q are each independently a carbon atom or a nitrogen atom.)
[8]
The film | membrane containing the organic electroluminescent element material of any one of [1]-[7].
[9]
The light emitting layer containing the material for organic electroluminescent elements of any one of [1]-[7].
[10]
An organic electroluminescent element having a pair of electrodes including an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on a substrate, wherein the light emitting layer is any one of [1] to [7] An organic electroluminescent element comprising the organic electroluminescent element material according to claim 1 in a light emitting layer.
[11]
[10] The method for producing an organic electroluminescent element according to [10], wherein the organic electroluminescent element material according to any one of [1] to [7] is prepared by a wet method. Manufacturing method of electroluminescent element.
[12]
It is a manufacturing method of the organic electroluminescent element as described in [10], Comprising: The layer containing the organic electroluminescent element material as described in any one of [1]-[7] is produced in a vacuum evaporation process. Manufacturing method of organic electroluminescent element.

  ADVANTAGE OF THE INVENTION According to this invention, the material for organic electroluminescent elements which can form a highly oriented film | membrane without crystallizing can be provided. Moreover, according to this invention, the organic electroluminescent element excellent in light extraction efficiency can be provided.

It is the schematic which shows an example of the layer structure of the organic electroluminescent element which concerns on this invention. It is a figure explaining the relationship between the molecules of the host material used for 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.

[Materials for organic electroluminescent elements]
The material for an organic electroluminescent element of the present invention has at least three substituents having a molecular width of 4.4 mm or more in one molecule, and a host material that does not substantially exhibit liquid crystal properties alone, and a flat light emitting material When the host material is mixed with the flat light emitting material, liquid crystallinity is exhibited.
When the organic electroluminescent device material of the present invention is used, a substituent having a molecular width of 4.4 mm or more acts as a steric hindrance group, and by having three or more substituents in one molecule, the steric repulsion between molecules. Therefore, crystallization is suppressed and liquid crystallinity is not substantially exhibited. Furthermore, the presence of a flat light-emitting material allows the host material to exhibit liquid crystallinity without crystallization, thereby increasing the orientation of the light-emitting material and improving the light extraction efficiency when applied to an organic electroluminescent device. Can do.

The reason why liquid crystallinity is manifested by mixing the host material and the flat light emitting material is presumed as follows.
FIG. 2 schematically shows the relationship between the molecules of the host material used in the present invention and the molecules of the flat light emitting material.
In the case of only the host material (in the case of (a) in FIG. 2), a substituent having a molecular width of 4.4 mm or more (steric hindrance group) is sterically repelled by the steric hindrance group of the adjacent molecule, so the distance between the molecules is Leave. For this reason, although crystallization is suppressed, since the orientation is also suppressed at the same time, liquid crystallinity is not substantially exhibited.
On the other hand, when a flat luminescent material is added (in the case of FIG. 2B), the luminescent material is arranged between the molecules of the host material, and the molecular core portions of the flat luminescent material and the host material are located between each other. Since the distance becomes close and appropriate interaction works, the host material molecules are aligned, and liquid crystallinity is exhibited. Furthermore, since the light emitting material is sandwiched between the host materials, aggregation of the light emitting material is also suppressed.

Whether the host material exhibits liquid crystallinity can be determined by thermal analysis (DSC) and observation with a polarizing microscope.
Regarding the host material used in the present invention, “single substantially no liquid crystallinity” means that a film formed using only the host material was observed using a polarizing microscope with temperature modulation under crossed Nicol conditions. Sometimes it means that no molecular orientation and phase change is observed.
On the other hand, when a flat light emitting material is added to the host material, a liquid crystal phase is developed. That is, when a film formed using a host material and a flat light-emitting material is observed with a polarizing microscope under temperature modulation under crossed Nicol conditions, the orientation and phase change of host material molecules are observed.

In an organic electroluminescent device of the present invention, the liquid crystal phase host material is expressed, columnar liquid crystal phase, discotic nematic liquid crystal phase (N _D phase), and the like. The discotic liquid crystal phase-isotropic phase transition temperature is preferably 50 to 300 ° C, more preferably 70 to 300 ° C, and particularly preferably 100 ° C to 300 ° C.
Hereinafter, the structure of the organic electroluminescent element material of the present invention will be described.

(Host material)
The host material used in the present invention is a material that has at least three or more substituents in a molecule having a molecular width of 4.4 mm or more and does not substantially exhibit liquid crystallinity by itself.
The host material is preferably a highly planar material, preferably has an aspect ratio of 2.5 or more, more preferably 2.5 to 30, and still more preferably 3 to 20.
The aspect ratio is the ratio (molecular diameter / molecular thickness) between the molecular diameter and the molecular thickness of the host material.
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.

  The host material is preferably a material made of discotic molecules with high planarity.

The substituent having a molecular width of 4.4 mm or more is not particularly limited as long as the molecular width is 4.4 mm or more, and examples thereof include a condensed or non-condensed benzene ring, a pyridine ring, a condensed ring or a non-condensed thiophene ring. A benzene ring is preferred.
The number of substituents having a molecular width of 4.4 mm or more in one molecule of the host material is 3 or more, but is preferably 4 or more from the viewpoint of suppressing crystallization by increasing steric hindrance. It is more preferable that The upper limit depends on the number of positions that can be substituted depending on the structure of the host material, but is preferably 8 or less, and more preferably 6 or less, from the viewpoint of obtaining an appropriate energy level as the host material.
The direction in which the molecular width of the substituent is 4.4 mm or more is not particularly limited, but is preferably a direction perpendicular to the bond axis between the portion to which the substituent is bonded and the substituent in the host material, The molecular width of the substituent is the longest molecular length in this direction.
The molecular width may be 4.4 mm or more, and the size is not particularly limited. However, because the intermolecular distance between the flat light-emitting material and the host material is set to a distance at which an appropriate interaction works, the molecular width is 8. It is desirable that it is 0 mm or less.
Further, when the host material is a material having high planarity, the width of the substituent in a direction substantially perpendicular to the planar portion is preferably 3.0 mm or more.

As the host material, a compound represented by the following general formula (I) is preferable.
Formula (I)

  In general formula (I), A is a condensed ring structure having a conjugated structure of 16 electrons or more and 4 or more rings condensed. y represents the number of L substituted with A, and is an integer of 3-8. L represents the following group.

** represents a position that binds to A. Z represents a divalent linking group, Ar _I represents an aromatic ring which may have a substituent, T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, perfluoro An alkyl group or a perfluoroalkoxy group is represented. n is 0 or 1, m is 0 or 1, x is 0 or 1, r is 0 or 1, and when r = 0, m = 1 and x = 0. However, L has a site | part with a molecular width of 4.4 mm or more.

In the general formula (I), A is a condensed ring structure having a conjugated structure of 16 electrons or more and 4 or more rings condensed. Specific examples include pyrene, perylene, triphenylene, chrysene, benzophenanthrene, and fluoranthene. Pyrene, perylene, and triphenylene are preferable, and triphenylene is more preferable.
y represents the number of L substituted to the condensed structure A, and is an integer of 3-8. y is preferably an integer of 3 to 6, and more preferably 6.
Z and T each independently represent a divalent linking group. Specific examples include an alkylene group, —O—, —COO—, —OCO—, or a group formed of a combination thereof. Carbon number of an alkylene group becomes like this. Preferably it is the range of 1-20, More preferably, it is the range of 1-15, More preferably, it is the range of 3-10.
Ar _I represents an aromatic ring which may have a substituent. Examples of the aromatic ring include a condensed or non-condensed benzene ring, a pyridine ring, a condensed ring or a non-condensed thiophene ring, and a benzene ring is preferable. Examples of the substituent that Ar _I may have include a fluorine atom, a cyano group, an alkyl group, and an alkoxy group, and an alkyl group and an alkoxy group are preferable. Carbon number of the alkyl group and alkoxy group as a substituent is preferably in the range of 1 to 5, more preferably in the range of 1 to 4, and still more preferably in the range of 1 to 3.

R _I represents an alkyl group, an alkoxy group, a cyano group, a perfluoroalkyl group, or a perfluoroalkoxy group, preferably an alkyl group or an alkoxy group, and more preferably an alkyl group. Preferably the number of carbon atoms R _I has a range of 1 to 20, more preferably in the range of 1 to 15, more preferably in the range of 3-10.

n is 0 or 1, m is 0 or 1, x is 0 or 1, and r is 0 or 1. However, when r is 0, m = 1 and x = 0. r is preferably 1.
When n, m, and x are 0, Z, Ar _I , and T each represent a single bond.

The L, _{specifically, R I -, R I -O} -Ph-, R I -Ph-, R I - (O-R T 3) nT -O-, R l -O-Ph-COO -, R _1- (O-R _T ³ ) _nT -O-Ph-COO-, R ₁ -O-Ph-CH = CH-COO-, R ₁ -COO-R _T ³ -O-Ph-COO- Is mentioned. Here, R _T ³ represents an alkylene group, Ph represents a phenylene group which may have a substituent, n _T is a repeating number of — (O—R _T ³ ) — Represents an integer.
The number of carbon atoms of the alkylene group represented by R _T ³ is preferably in the range of 1 to 10, more preferably in the range of 1 to 8, and still more preferably in the range of 2 to 6.
Ph represents a phenylene group which may have a substituent. Examples of the substituent which may have a substituent are the same as the substituent which Ar _I may have, and the preferred range is also the same. .
n _T is preferably an integer of 1 to 10, more preferably an integer from 1 to 6, more preferably an integer of 1 to 3.

The _{L, R I -O-Ph-,} R I -Ph-, R l -O-Ph-COO- are _{preferred, R I -O-Ph-, R} I -Ph- is more preferable.

As the host material, a compound represented by the general formula (II) is preferable.
Formula (II)

  In general formula (II), y represents the number of L substituted to a triphenylene skeleton, and is an integer of 3-6. * Represents a substitution position where L substitutes. L represents the following group.

** represents a position bonded to the triphenylene skeleton. Z represents a divalent linking group, Ar _I represents an aromatic ring which may have a substituent, T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, perfluoro An alkyl group or a perfluoroalkoxy group is represented. n is 0 or 1, m is 0 or 1, x is 0 or 1, r is 0 or 1, and when r = 0, m = 1 and x = 0. However, L has a site | part with a molecular width of 4.4 mm or more.

In general formula (II), Z, Ar _I , T, R _I , n, m, x, and r are as defined in general formula (I), and the preferred ranges are also the same.
y represents an integer of 3 to 6, preferably an integer of 3 or 6, and more preferably 6.

As the host material, a compound represented by the general formula (III) is more preferable.
Formula (III)

In the general formula (III), T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, a perfluoroalkyl group, or a perfluoroalkoxy group. x is 0 or 1, r is 0 or 1, w represents an integer of 0 to 2, and when r = 0, x = 0. The substituent-(T) _x- (R _I ) _r is bonded to the phenyl group at the meta position or para position with respect to triphenylene.

In general formula (III), T, R _I , x, and r are synonymous with general formula (I), and their preferred ranges are also the same.
Furthermore, T is preferably -O-. When x = 0, T represents a single bond.
w represents an integer of 0 to 2, more preferably 1 or 2, and still more preferably 1.
The substituent-(T) _x- (R _I ) _r is bonded to the phenyl group at the meta position or para position with respect to triphenylene. From the viewpoint of improving the orientation by the combined use with the flat light emitting material, it is preferably bonded to the phenyl group at the meta position.

  Specific examples of the host material represented by the general formulas (I) to (III) are shown below, but the present invention is not limited to these compounds.

The host material is also preferably a compound represented by the general formula (IV).
Formula (IV)

In the general formula (IV), T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, a perfluoroalkyl group, or a perfluoroalkoxy group. x is 0 or 1, r is 0 or 1, w represents an integer of 0 to 2, and when r = 0, x = 0. The substituent-(T) _x- (R _I ) _r is bonded to the phenyl group at the meta position or para position with respect to pyrene.

In general formula (IV), T, R _I , x, r, and w are as defined in general formula (III), and the preferred ranges are also the same.

The host material is also preferably a compound represented by the general formula (V).
General formula (V)

In the general formula (V), T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, a perfluoroalkyl group, or a perfluoroalkoxy group. x is 0 or 1, r is 0 or 1, w represents an integer of 0 to 2, and when r = 0, x = 0. The substituent-(T) _x- (R _I ) _r is bonded to the phenyl group at the meta position or para position with respect to perylene.

In general formula (V), T, R _I , x, r, and w have the same meaning as in general formula (III), and the preferred range is also the same.

The molecular radius of the host material is preferably 0.4 nm to 3 nm, more preferably 1.0 nm to 2.5 nm, and particularly preferably 1.0 nm to 2.0 nm.
The molecular radius of the host material is defined as the radius when the entire molecule including the side chain is a disk.
The molecular radius is defined as follows by theoretical calculation. The theoretical calculation here is performed using a density functional method. Specifically, using Gaussian 03 (Gaussian, USA), the basis function is 6-31G ^* and the exchange correlation functional is B3LYP / LANL2DZ. Perform optimization calculations. The molecular radius of the host material is obtained using the optimized structure obtained by the structure optimization calculation.

  60 mass%-99 mass% are preferable, as for content of the host material in an organic electroluminescent element material, 65 mass%-95 mass% are more preferable, and 70 mass%-90 mass% are especially preferable.

(Luminescent material)
The light emitting material used for the organic electroluminescent element material of the present invention will be described.
The light emitting material used in the present invention is a flat light emitting material. Here, “flat form” means that the aspect ratio is 3 or more, and the aspect ratio is more preferably 3 to 30, and particularly preferably 4 to 20.
Here, the aspect ratio is a ratio of molecular core diameter to molecular core thickness (molecular core diameter / molecular core thickness).
The molecular core diameter means the longest molecular length of a chromophore (a chromophore linked by a conjugated system, a luminescent skeleton).
The molecular core diameter 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
Then, the structure optimization calculation is performed. Using the optimized structure obtained by the structure optimization calculation, the length of the longest molecular length in the ball and stick display is defined as the molecular core diameter of the phosphorescent compound.
The molecular core thickness means the thickness of the molecule when the chromophore is a plane.
The molecular core thickness is also determined by the same method as the molecular core diameter, and the length in the thickness direction of the molecule in the ball and stick display is defined as the molecular core thickness.

The molecular radius of the light emitting material is preferably 0.40 nm to 3.0 nm, more preferably 0.80 nm to 2.5 nm, and particularly preferably 1.20 nm to 2.0 nm. This range is preferable from the viewpoints of improving the orientation, ease of controlling the emission intensity and emission wavelength, and the like.
Here, the molecular radius of the luminescent material is defined as the radius when the entire molecule including the side chain is a disk.
As with the molecular core diameter, the molecular radius is defined as follows by theoretical calculation. The theoretical calculation here is performed using a density functional method. Specifically, using Gaussian 03 (Gaussian, USA), the basis function is 6-31G ^* and the exchange correlation functional is B3LYP / LANL2DZ. Perform optimization calculations. Using the optimized structure obtained by the structure optimization calculation, the molecular radius of the light emitting material is obtained.
The molecular core thickness means the molecular thickness when the chromophore is a plane. The molecular core thickness is also obtained by the same method as the molecular core diameter, and the length in the thickness direction of the molecule in the ball and stick display is defined as the molecular core thickness.

  The size ratio between the molecular radius of the light emitting material and the molecular radius of the host material (molecular radius of the light emitting material / molecular radius of the host material) is preferably 0.8 to 1.2, more preferably 0.85 to 1.15. 0.9 to 1.1 is preferable and particularly preferable. When the size ratio is within this range, the luminance in the front direction of the organic electroluminescent element increases. This is because even when a luminescent material is mixed with the host material, the orientation order (order parameter) of the host material is not lowered. Therefore, after film formation, the average of the monodomain and the whole molecule becomes horizontal orientation, and the orientation of the luminescent material molecules I guess it is because the direction becomes uniform. Note that the front direction of the organic electroluminescent element refers to a direction viewed from this direction, in which the organic electroluminescent element is placed upright and a perpendicular line is drawn from the substrate side to the light emitting layer.

Examples of the light emitting material include a complex containing a transition metal atom. These may be used alone or in combination of two or more.
The complex may have one transition metal atom in the compound, or may be a so-called binuclear complex having two or more. Different metal atoms may be contained at the same time.

Examples of the ligand of the complex include G.I. Wilkinson et al., Comprehensive Coordination Chemistry, Pergamon Press, 1987, H.C. Listed by Yersin, “Photochemistry and Photophysics of Coordination Compounds”, published by Springer-Verlag, 1987, Akio Yamamoto, “Organic Metal Chemistry-Fundamentals and Applications,” published by Soukabo, 1982, etc. It is done.
Examples of the ligand include aromatic carbocyclic ligand, nitrogen-containing heterocyclic ligand, diketone ligand, carboxylic acid ligand, alcoholate ligand, carbon monoxide ligand, isonitrile coordination Child, cyano ligand and the like. Among these, a nitrogen-containing heterocyclic ligand is particularly preferable.
Examples of the aromatic carbocyclic ligand include a cyclopentadienyl anion, a benzene anion, and a naphthyl anion.
Examples of the nitrogen-containing heterocyclic ligand include phenylpyridine, benzoquinoline, quinolinol, bipyridyl, phenanthroline and the like.
Examples of the diketone ligand include acetylacetone.
Examples of the carboxylic acid ligand include an acetic acid ligand.
Examples of the alcoholate ligand include a phenolate ligand.

  Examples of the transition metal atom include ruthenium, rhodium, palladium, osmium, platinum and the like.

  The light emitting material is not particularly limited and may be appropriately selected depending on the intended purpose. However, a phosphorescent light emitting material is preferable, and a tetradentate structure having a planar coordination structure is preferable in that the aspect ratio is 3 or more. Platinum (platinum complex) is preferable, and platinum complexes having a salen or porphyrin skeleton are more preferable.

The platinum complex is preferably selected from phosphorescent compounds represented by the following general formulas (1) to (5).
General formula (1)

(In general formula (1), X, Y, and Z represent a carbon atom or a nitrogen atom, and when either Z or Y is a nitrogen atom and Y is a nitrogen atom, X is a carbon atom. M, n, p and q each independently represents an integer of 0 to 3. Ar represents an aryl group, R _{1 to} R ₄ each independently represents an alkyl group, an aryl group, an alkoxy group, Represents an aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group, and when m, n, p, and q are 2 or more, a plurality of R _{1 to} R ₄ are connected to each other to form a cyclic structure May be formed.)

In general formula (1), X, Y, and Z represent a carbon atom or a nitrogen atom, and when either Z or Y is a nitrogen atom and 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. 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 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, from the viewpoint of aspect ratio, 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 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. 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, 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.
General formula (2)

(In General Formula (2), X, Y, and Z represent a carbon atom or a nitrogen atom, and either Z or Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. R, s, t and u each independently represents 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 or a cyano group. , A silyl group, or a heterocyclic group, and when r, s, t, and u are 2 or more, a plurality of R _{5 to} R ₈ may be connected to each other to form a cyclic structure. ₁ and W ₂ represent an alkyl group and may be bonded to each other to form a cyclic structure.

  In the general formula (2), X, Y, and Z are synonymous with X, Y, and Z in the general formula (1), and preferred ranges are also the same.

R < ₅ > -R < ₈ > is synonymous with R < ₁ > -R < ₄ > of General formula (1).
R ₅ and R ₆ are preferably an alkyl group, an alkoxy group, an aryl group, a fluorine atom, or a cyano group.
As the alkyl group represented by R ₅ and R ₆ , an optionally substituted methyl group, butyl group, octyl group, decyl group, dodecyl group and the like are preferable, and a butyl group, a trifluoromethyl group, an octyl group, A decyl group is more preferred.
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, and more preferably a phenyl group which may have a substituent. The substituent is preferably an alkyl group, and more preferably a methyl 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 benzofuran ring.

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.
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 a methyl group or a cyclohexyl cyclic structure from the viewpoint of a high aspect ratio.
General formula (3)

(In General Formula (3), R _{9 to} R ₁₆ each independently represent a hydrogen atom, an alkyl group, an aryl group, a silyl group, or a heterocyclic group, and R ₉ and R ₁₁ , R ₁₁ and R ₁₂ , R ₁₂ and R ₁₀ , R ₁₄ and R ₁₅ , R ₁₃ and R ₁₆ may combine with each other to form a cyclic structure.)

In General Formula (3), R _{9 to} R ₁₆ represent a hydrogen atom, an alkyl group, an aryl group, a silyl group, or a heterocyclic group, and R ₉ and R ₁₁ , R ₁₁ and R ₁₂ , R ₁₂ and R ₁₀ , R ₁₄ and R ₁₅ , 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, an octyl group, a decyl group, a dodecyl group, n-butyl group, t-butyl group, t-amyl group, s-butyl group etc. are mentioned. It is done.
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 specifically includes, for example, methoxy group, pentyloxy group, octyloxy group, decyloxy group, dodecyloxy group, s-octyloxy group, benzyloxy group, and the like. Can be mentioned.
The aryloxy group represents a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, and may be condensed. Specifically, for example, a phenyloxy group, a toluyloxy group, a naphthyloxy group Etc.
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 _{9 to} R ₁₀ are preferably a hydrogen atom or a heteroaromatic ring in which R ₉ and R ₁₁ , and R ₁₀ and R ₁₂ are bonded to each other. Examples of the heteroaromatic ring include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a triazole ring, an oxadiazole ring, and a thiadiazole ring. Preferably, it is a pyridine ring.
R _{13, R 14,} R _{15, R 16 is} preferably _{R 13} and _{R 16, R 14} and _{R 15} is an aromatic ring bonded respectively. Examples of the aromatic ring include a benzene ring.
R ₁₁ and R ₁₂ preferably represent a hydrogen atom, an alkyl group, or an aromatic ring in which R ₁₁ and R ₁₂ are bonded. Examples of the aromatic ring to which R ₁₁ and R ₁₂ are bonded include a benzene ring or a naphthalene ring.
Heteroaromatic ring in which R ₉ and R ₁₁ , R ₁₀ and R ₁₂ are bonded, and R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ are aromatic rings in which R ₁₃ and R ₁₆ , R ₁₄ and R ₁₅ are bonded, respectively. May have a substituent, and examples of the substituent include an alkyl group, an alkoxy group, and a fluorine atom, and include a methyl group, an n-butyl group, a t-butyl group, an s-butyl group, and an undecyl group. , Butoxy group, pentyloxy group, decyloxy group, dodecyloxy group and fluorine atom are preferred.
Among these, an aromatic ring in which R ₁₃ and R ₁₆ , R ₁₄ and R ₁₅ , and R ₁₁ and R ₁₂ are bonded from the viewpoint of aspect ratio and molecular size is preferable.

As a more preferable aspect of the compound represented by General formula (3), the compound of following General formula (6) is mentioned.
General formula (6)

In general formula (6), B may form either an aromatic or non-aromatic 6-membered ring.
R _{17 to} R ₂₆ represent 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.
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.
B is preferably a non-aromatic 6-membered ring, more preferably a pyridine ring. The ring may have a substituent, and examples of the substituent include an alkyl group (methyl group, butyl group).
From the viewpoint of the aspect ratio, R _{17 to} R ₂₆ are preferably chain alkyl groups or, in the case of substituents other than alkyl groups, preferably have alkyl groups as substituents.
General formula (4)

(In General Formula (4), X, Y, and Z represent a carbon atom or a nitrogen atom, and either Z or Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. M, n, p, and g each independently represents an integer of 0 to _3. Ar represents an aryl group, and R _{1 to} R ₃ and R ₃₀ each independently represents an alkyl group, an aryl group, or an alkoxy group. , An aryloxy group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group, and when m, n, p, and g are 2 or more, a plurality of R _{1 to} R ₃ and R ₃₀ are adjacent to each other. (It may be linked to form a cyclic structure. M and Q are each independently a carbon atom or a nitrogen atom.)

In General Formula (4), R _{1 to} R ₃ , Ar, X, Y, Z, m, n, and p have the same meanings as in General Formula (1), and preferred ranges are also the same.
M and Q are each independently a carbon atom or a nitrogen atom. M is preferably a carbon atom. Q is preferably a nitrogen atom.
g 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 the aspect ratio, R ₃₀ is preferably a chain alkyl group or, in the case of a substituent other than an alkyl group, preferably has an alkyl group as a substituent.
General formula (5)

(In General Formula (5), Z represents a carbon atom or a nitrogen atom. M, n, and g each independently represents an integer of 0 to _3. Ar represents an aryl group. R ₁ , R _2, and R ₃₀ 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 when m, n, or g is 2 or more, a plurality of R ₁ , R ₂ and R ₃₀ may be linked to each other to form a cyclic structure, and M and Q are each independently a carbon atom or a nitrogen atom.)

In general formula (5), R ₁ , R ₂ , Ar, Z, m, and n have the same meanings as in general formula (1), and the preferred ranges are also the same. Furthermore, M, _{Q, R 30,} g is the general formula (4) synonymous, and their preferable ranges are also the same.

  Examples of the phosphorescent compounds represented by the general formulas (1) to (5) include, but are not limited to, the following compounds.

The platinum complexes represented by the general formulas (1) to (5) are described in, for example, Journal of Organic Chemistry 53,786, (1988), G.A. R. Newkome et al. ), Page 789, method described in left line 53 to right line 7, line 790, method described in left line 18 to line 38, method 790, method described in right line 19 line to line 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).

  The content of the light emitting material in the organic electroluminescent element material is preferably 0.1% by mass to 30% by mass, more preferably 1% by mass to 25% by mass, and particularly preferably 5% by mass to 20% by mass.

In the organic electroluminescent element, it is preferable to orient the transition dipole moment of the luminescent material horizontally with respect to the anode. The transition dipole moment of the luminescent material is oriented horizontally with respect to the anode, which is advantageous in that the light emission component in the direction perpendicular to the anode is increased and the light extraction efficiency is improved.
The direction of the transition dipole moment is defined as follows by theoretical calculation. The theoretical calculation here is performed using Gaussian 03 (Gaussian, USA). As the molecular structure used for the calculation, the direction of the transition dipole moment can be obtained by performing the structure optimization calculation and using the structure having the minimum generation energy.
Or after forming a light emitting layer, it can also measure by an ATR-IR measuring method or a grazing incidence UV measuring method.

〔film〕
With the organic electroluminescent element material of the present invention, a film having a high orientation of the host material and the light emitting material can be obtained. The film is preferably formed by a wet method such as a coating process or a vacuum deposition process. The film can be used as a light emitting layer of an organic electroluminescent element, and can be a light emitting layer having excellent light extraction efficiency due to high orientation.

[Organic electroluminescence device]
The organic electroluminescent element in the present invention will be described in detail.
A preferred embodiment of the organic electroluminescent element in the present invention is an organic electroluminescent element having a pair of electrodes including an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on a substrate.

In the organic electroluminescent device of the present invention, the light emitting layer is an organic layer, and may further include at least one organic layer between the light emitting layer and the anode, and may further have an organic layer in addition to these.
In view of the properties of the light-emitting element, at least one of the anode and the cathode is preferably transparent or translucent.
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.

<Structure of organic layer>
There is no restriction | limiting in particular as a layer structure of the said organic layer, Although it can select suitably according to the use and objective of an organic electroluminescent element, It is preferable to form on an anode or a cathode. 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 / 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 electroluminescent device of the present invention, each organic layer is suitable for any of dry deposition methods such as vacuum deposition and sputtering, and solution coating processes such as transfer, printing, spin coating, and bar coating. Can be formed. Vacuum 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. Method, ink jet method and 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, it may be dried after the film is formed. 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. Specific examples of the solvent include halogen solvents (chloroform, carbon tetrachloride, dichloromethane, 1,2-dichloroethane, chlorobenzene, etc.), ketone solvents (acetone, methyl ethyl ketone, diethyl ketone, n-propyl methyl ketone, cyclohexanone, etc.), Aromatic solvents (benzene, toluene, xylene, etc.), ester solvents (ethyl acetate, n-propyl acetate, n-butyl acetate, methyl propionate, ethyl propionate, γ-butyrolactone, diethyl carbonate, etc.), ether solvents (Tetrahydrofuran, dioxane, etc.), amide solvents (dimethylformamide, dimethylacetamide, etc.), dimethyl sulfoxide, alcohol solvents (methanol, propanol, butanol, etc.), water and the like.
The solid content with respect to the solvent in the coating solution is not particularly limited, and the viscosity of the coating solution can be arbitrarily selected according to the film forming method.

[Light emitting layer]
In the organic electroluminescent element of the present invention, the light emitting layer contains the aforementioned organic electroluminescent element material of the present invention.
As the light emitting material, from the viewpoint of orientation, the light emitting material having high planarity described above is preferable, a phosphorescent light emitting material is preferable, and a platinum complex is more preferable. A luminescent material may be used independently or may use 2 or more types together.
From the viewpoint of orientation, the light emitting layer is preferably formed by a vacuum deposition process.

  Although content in particular of the luminescent material in a light emitting layer is not restrict | limited, For example, it is preferable that it is 0.1-30 mass%, it is more preferable that it is 1-25 mass%, and it is 5-20 mass%. Particularly preferred.

The host compound is a compound that causes energy transfer from the excited state to the light-emitting material, and as a result, emits the emitted light.
In this invention, the host material mentioned above is contained. 70 mass%-99.9 mass% are preferable, as for content in the light emitting layer of this host material, 75 mass%-99 mass% are more preferable, and 80 mass%-95 mass% are especially preferable.

  As the host material, materials other than the above-described host materials may be included. Specific examples thereof include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, Pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives Bodies, distyrylpyrazine derivatives, heterocyclic tetracarboxylic anhydrides such as naphthalene perylene, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as a ligand, polysilane compounds , Conductive polymers such as poly (N-vinylcarbazole) derivatives, aniline copolymers, thiophene oligomers, polythiophenes, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, polyfluorene derivatives, and the like. A host compound may be used individually by 1 type, or may use 2 or more types together.

  The thickness of the light emitting layer is preferably 10 to 200 nm, more preferably 20 to 80 nm, from the viewpoint of suppressing an increase in driving voltage and preventing a short circuit.

(Hole injection layer, hole transport layer)
The organic electroluminescent element of the present invention may have a hole injection layer and a hole transport layer. The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
The hole injection layer and the hole transport layer are described in detail, for example, in JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications can be applied to the present invention.

(Electron injection layer, electron transport layer)
The organic electroluminescent element of the present invention may have an electron injection layer and an electron transport layer. The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
The electron injection layer and the electron transport layer are described in detail, for example, in JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications 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 the organic compound constituting the hole blocking layer, aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as BAlq), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-Dimethyl-4,7-diphenyl-1,10-) phenanthroline derivatives such as phenanthroline (abbreviated as BCP), triphenylene derivatives, carbazole derivatives, 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.

[Other organic layers]
The organic electroluminescent device of the present invention has a protective layer described in JP-A-7-85974, 7-192866, 8-22891, 10-275682, 10-106746, etc. Also good. The protective layer is formed on the uppermost surface of the light emitting element. Here, when the base material, the transparent electrode, the organic layer, and the back electrode are laminated in this order, the top surface refers to the outer surface of the back electrode, and the base material, the back electrode, the organic layer, and the transparent electrode are laminated in this order. In some cases, it refers to the outer surface of the transparent electrode. The shape, size, thickness and the like of the protective layer are not particularly limited. The material for forming the protective layer is not particularly limited as long as it has a function of suppressing intrusion or permeation of a light-emitting element such as moisture or oxygen into the element. Silicon, germanium oxide, germanium dioxide or the like can be used.

  The method for forming the protective layer is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, molecular sensing epitaxy, cluster ion beam, ion plating, plasma polymerization, plasma CVD, laser CVD Thermal CVD method, coating method, etc. can be applied.

[Sealing]
The organic electroluminescent element is preferably provided with a sealing layer for preventing moisture and oxygen from entering. As a material for forming the sealing layer, a copolymer of tetrafluoroethylene and at least one comonomer, a fluorinated copolymer having a cyclic structure in the copolymer main chain, polyethylene, polypropylene, polymethyl methacrylate, polyimide, Polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, chlorotrifluoroethylene or a copolymer of dichlorodifluoroethylene and another comonomer, a water-absorbing substance having a water absorption of 1% or more, a water absorption of 0. 1% or less moisture-proof material, metal (In, Sn, Pb, Au, Cu, Ag, Al, Tl, Ni, etc.), metal oxide (MgO, SiO, SiO ₂ , Al ₂ O ₃ , GeO, NiO, _{CaO, BaO, Fe 2 O 3} , Y 2 O 3, TiO 2 , etc.), metal fluorides (M _{F 2, LiF, AlF 3,} CaF 2 , etc.), liquid fluorinated carbon (perfluoroalkane, perfluoro amines, perfluoroether, etc.), the liquid fluorinated carbon as dispersed adsorbent moisture or oxygen, etc. Can be used.

  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 electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429, 6023308, and the like can be applied.

The present invention will be described more specifically with reference to the following examples. The materials, reagents, substance amounts and ratios, operations, and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention is not limited to the following specific examples.
Hereinafter, the mixing ratio of the solvent represents a volume ratio.

Example 1
(Synthesis of host materials 1 to 6)
Host materials 1 to 6 were synthesized according to the following scheme.

In the above scheme, R- represents that the host material 1 is (4-n-C ₆ H ₁₃ O-), the host material 2 is (3-n-C ₆ H ₁₃ O-), and the host material 3 is (3-CH ₃ −), the host material 4 represents (4-nC ₅ H ₁₁ —), the host material 5 represents (4-CH ₃ —), and the host material 6 represents (3,4-diCH ₃ —).

To a xylene / water = 1/1 solution (20 ml / 20 ml) of hexabromotriphenylene (1 g), substituted phenylboric acid (10 equivalents, R is a substituent), Pd (PPh ₃ ) ₄ (0.17 g) and potassium carbonate ( 1.2 g) was added and stirred at 120 ° C. for 12 hours under a nitrogen atmosphere. The reaction solution was poured into ethyl acetate / dilute hydrochloric acid (mixing ratio: ethyl acetate / dilute hydrochloric acid = 1/1), and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / hexane = 1/98) and recrystallized with ethanol / normal hexane = 95/5 to give host materials 1 to 6 (yield 65% to 85). %). The compound was identified by elemental analysis, NMR and MASS spectrum. The appearance was a white solid.
In addition to the host materials 1 to 6, host materials having different R can be synthesized in the same manner. In the above scheme, R may be a hydrogen atom. In that case, a host material having R as a hydrogen atom can be obtained by using unsubstituted phenylboric acid instead of substituted phenylboric acid.

(Example 2)

(Preparation of coating solution)
Tetrahydrofuran (THF) (99% by mass) was mixed with the host material (0.9% by mass) and the light emitting material (0.1% by mass) shown in Table 1 to prepare a coating solution.
(Film formation)
A quartz glass substrate of 25 mm × 25 mm × 0.7 mm was washed and treated with UV ozone, and then an alignment film (horizontal alignment film SE-130 manufactured by Nissan Chemical Industries) was spin-coated and applied at 100 ° C. for 10 minutes, and then at 180 ° C. The base substrate (film thickness 200nm) was obtained by heating for 1 hour.
On the base substrate, the coating solution was formed by spin coating.
(Evaluation)
Each sample after film formation was observed with a polarizing microscope (under crossed Nicols condition) and examined for the presence of a liquid crystal phase. Since the host material used here does not have anisotropy in the refractive index in the molecular plane, it becomes a dark field when the liquid crystal phase is expressed by horizontal alignment under the above conditions, and the liquid crystal without horizontal alignment. When the phase is not expressed, it becomes a bright field. Further, when it is crystallized, it becomes a bright field and low fluctuation structure.

  From the results in Table 1, liquid crystallinity is manifested by coating and film-forming a mixture of a host material having at least three substituents having a molecular width of 4.4 mm or more in one molecule and a flat light emitting material. I understand.

(Example 3)
(Film formation)
A quartz glass substrate of 25 mm × 25 mm × 0.7 mm was washed and treated with UV ozone, and then an alignment film (horizontal alignment film SE-130 manufactured by Nissan Chemical Industries) was spin-coated and applied at 100 ° C. for 10 minutes, and then at 180 ° C. The base substrate (film thickness 200nm) was obtained by heating for 1 hour.
On this base substrate, a host material and a light emitting material shown in Table 2 were formed by a vacuum deposition method so as to have a mass ratio (90:10) (film thickness: 300 nm).
(Evaluation)
Each sample after film formation was observed with a polarizing microscope (under crossed Nicols condition) and examined for the presence of a liquid crystal phase. Since the host material used here does not have anisotropy in the refractive index in the molecular plane, it becomes a dark field when the liquid crystal phase is expressed by horizontal alignment under the above conditions, and the liquid crystal without horizontal alignment. When the phase is not expressed, it becomes a bright field. Further, when it is crystallized, it becomes a bright field and low fluctuation structure.

  From the results shown in Table 2, it can be seen that liquid crystallinity is manifested by vapor deposition from a host material having at least three substituents having a molecular width of 4.4 mm or more in one molecule and a flat light emitting material.

Example 4
(Production of organic electroluminescence device)
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 the transparent anode (ITO film) by vacuum deposition.
First layer: NPD: film thickness 40 nm
Second layer: Host material and light emitting material described in Table 3 (mass ratio 90:10): film thickness 30 nm
Third layer: CBP: film thickness 5 nm
Fourth layer: BAlq: film thickness 45 nm
On this, 1 nm of lithium fluoride and 100 nm of metal aluminum were vapor-deposited in this order, and it was set as the 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.
As a result of light emission of these elements, light emission derived from the light emitting material was obtained for each element.

(Evaluation)
The following evaluation was performed about the obtained element. The evaluation results are shown in Table 3.
(A) External quantum efficiency Using a source measure unit 2400 manufactured by Toyo Technica, a direct current voltage was applied to each element to emit 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. For the elements 1 to 3, relative values were calculated when the external quantum efficiency of the element 3 of the comparative example using the light-emitting material A-1 was 1. Similarly, the external quantum efficiencies of the elements 4 to 6 are relative values when the external quantum efficiency of the element 6 of the comparative example is 1, and the external quantum efficiencies of the elements 7 to 9 are the external quantum efficiencies of the element 9 of the comparative example. Is a relative value when.

  From Table 3, it can be seen that the device using the organic electroluminescent device material of the present invention for the light emitting layer has an external quantum efficiency that is 1.5 times or more superior to the comparative device, and the light extraction efficiency is improved.

  Hereafter, the structure of the compound used for the Example is shown.

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 device

Claims (12)

A host material having at least three substituents in a molecule having a molecular width of 4.4 mm or more and having substantially no liquid crystal properties alone;
A flat light emitting material;
A material for an organic electroluminescent element, which exhibits liquid crystallinity when the host material is mixed with the flat light emitting material.   The organic electroluminescent element material according to claim 1, wherein the flat light emitting material is a platinum complex. The organic electroluminescent element material according to claim 1 or 2, wherein the host material is a compound represented by the following general formula (I).
Formula (I)
In general formula (I), A is a condensed ring structure having a conjugated structure of 16 electrons or more and 4 or more rings condensed. y represents the number of L substituted with A, and is an integer of 3-8. L represents the following group.
** represents a position that binds to A. Z represents a divalent linking group, Ar _I represents an aromatic ring which may have a substituent, T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, perfluoro An alkyl group or a perfluoroalkoxy group is represented. n is 0 or 1, m is 0 or 1, x is 0 or 1, r is 0 or 1, and when r = 0, m = 1 and x = 0. However, L has a site | part with a molecular width of 4.4 mm or more.   The organic electroluminescent element material according to claim 1, wherein the condensed ring structure A is pyrene, perylene, or triphenylene. The organic electroluminescent element material according to any one of claims 1 to 4, wherein the host material is a compound represented by the following general formula (II).
Formula (II)
In general formula (II), y represents the number of L substituted to a triphenylene skeleton, and is an integer of 3-6. * Represents a substitution position where L substitutes. L represents the following group.
** represents a position bonded to the triphenylene skeleton. Z represents a divalent linking group, Ar _I represents an aromatic ring which may have a substituent, T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, perfluoro An alkyl group or a perfluoroalkoxy group is represented. n is 0 or 1, m is 0 or 1, x is 0 or 1, r is 0 or 1, and when r = 0, m = 1 and x = 0. However, L has a site | part with a molecular width of 4.4 mm or more. The organic electroluminescent element material according to claim 1, wherein the host material is a compound represented by the following general formula (III).
Formula (III)
In the general formula (III), T represents a divalent linking group, R _I represents an alkyl group, an alkoxy group, a cyano group, a perfluoroalkyl group, or a perfluoroalkoxy group. x is 0 or 1, r is 0 or 1, w represents an integer of 0 to 2, and when r = 0, x = 0. The substituent-(T) _x- (R _I ) _r is bonded to the phenyl group at the meta position or para position with respect to triphenylene. 7. The organic electroluminescence device according to claim 1, wherein the platinum complex is at least one selected from phosphorescent compounds represented by the following general formulas (1) to (5). material.
General formula (1)
(In the general formula (1), X, Y, and Z represent a carbon atom or a nitrogen atom, and 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 represents an integer of 0 to 3. Ar represents an aryl group, and R _{1 to} R ₄ each independently represents an alkyl group, an aryl group, an alkoxy group or an aryloxy group. Group, a fluorine atom, a cyano group, a silyl group, or a heterocyclic group, and when m, n, p, and q are 2 or more, a plurality of R _{1 to} R ₄ are connected to each other to form a cyclic structure. It may be formed.)
General formula (2)
(In General Formula (2), X, Y, and Z represent a carbon atom or a nitrogen atom, and either Z or Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. R, s, t and u each independently represents 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 or a cyano group. , A silyl group, or a heterocyclic group, and when r, s, t, and u are 2 or more, a plurality of R _{5 to} R ₈ may be connected to each other to form a cyclic structure. ₁ and W ₂ represent an alkyl group and may be bonded to each other to form a cyclic structure.
General formula (3)
(In General Formula (3), R _{9 to} R ₁₆ each independently represent a hydrogen atom, an alkyl group, an aryl group, a silyl group, or a heterocyclic group, and R ₉ and R ₁₁ , R ₁₁ and R ₁₂ , R ₁₂ and R ₁₀ , R ₁₄ and R ₁₅ , R ₁₃ and R ₁₆ may combine with each other to form a cyclic structure.)
General formula (4)
(In General Formula (4), X, Y, and Z represent a carbon atom or a nitrogen atom, and either Z or Y is a nitrogen atom. When Y is a nitrogen atom, X is a carbon atom. M, n, p and g each independently represents an integer of 0 to _3. Ar represents an aryl group, R _{1 to} R ₃ and R ₃₀ , each independently 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 when m, n, p, and g are 2 or more, a plurality of R _{1 to} R ₃ and R ₃₀ are connected to each other adjacent to each other. A cyclic structure may be formed, and M and Q are each independently a carbon atom or a nitrogen atom.)
General formula (5)
(In General Formula (5), Z represents a carbon atom or a nitrogen atom. M, n, and g each independently represents an integer of 0 to _3. Ar represents an aryl group. R ₁ , R _2, and R ₃₀ 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 when m, n, or g is 2 or more, a plurality of R ₁ , R ₂ and R ₃₀ may be linked to each other to form a cyclic structure, and M and Q are each independently a carbon atom or a nitrogen atom.)   The film | membrane containing the organic electroluminescent element material of any one of Claims 1-7.   The light emitting layer containing the organic electroluminescent element material of any one of Claims 1-7.   An organic electroluminescent element comprising a substrate and a pair of electrodes including an anode and a cathode, and at least one organic layer including a light emitting layer between the electrodes, wherein the light emitting layer is any one of claims 1 to 7. The organic electroluminescent element which contains the organic electroluminescent element material as described in an item in a light emitting layer.   It is a manufacturing method of the organic electroluminescent element of Claim 10, Comprising: The organic electroluminescent which produces the layer containing the organic electroluminescent element material of any one of Claims 1-7 with a wet method Device manufacturing method.   It is a manufacturing method of the organic electroluminescent element of Claim 10, Comprising: The organic electric field which produces the layer containing the organic electroluminescent element material of any one of Claims 1-7 by a vacuum evaporation process. Manufacturing method of light emitting element.