JP6118036B2 - Organic electroluminescent device, organic electroluminescent device material, film, light emitting layer, and organic electroluminescent device manufacturing method - Google Patents

Description

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

An organic electroluminescent element is a self-luminous display device, and is used for displays and illumination. A display using an organic electroluminescent element has advantages in display performance such as high visibility and less viewing angle dependency compared to conventional CRTs and LCDs. There is also an advantage that the display can be reduced in weight and thickness.
In addition to the advantages of lighter weight and thinner layers, organic electroluminescent elements have the potential to realize illumination in a shape that could not be realized before by using a flexible substrate.

As described above, the organic electroluminescent device has excellent characteristics including the above-mentioned matters, but generally, the refractive index of each layer constituting the organic electroluminescent device including the light emitting layer is 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 to 2.1. For this reason, the emitted light is easily totally reflected at the interface, and its light extraction efficiency is less than 20%, and most of the light is lost.
For example, a generally known organic electroluminescent element is configured to include an organic layer disposed between a pair of electrode layers on a substrate. The organic layer includes a light emitting layer, and the organic electroluminescent element emits light emitted from the light emitting layer from the light extraction surface side. In this case, there is a problem that the light extraction efficiency is low because the total reflection component that is light having a critical angle or more cannot be extracted at the light extraction surface or the interface between the electrode layer and the organic layer.

  In order to solve such a problem, a condensing method using a microlens incorporated in the element (Non-Patent Document 1) and a method of forming a three-dimensional structure or an inclined surface on the substrate itself are approaches from the element structure. However, the device has a complicated structure and has many problems.

On the other hand, if a flat luminescent material having a transition dipole moment in the molecular plane can be arranged horizontally with respect to the substrate, the light emission component in the direction perpendicular to the substrate increases, and in principle the light extraction efficiency is improved. I can expect. However, there is a problem that the crystallinity of the obtained film becomes high when the light emitting materials are arranged.
In general, even in a two-component system such as a light-emitting layer, it is possible to make a horizontal alignment by using an intermolecular interaction such as π-π interaction or CH-π interaction. However, excimer, excimer, excimer Concentration quenching due to the formation of excited bimolecular aggregates such as plexes and a decrease in luminance due to Forster energy transfer were inevitable.
Accordingly, there has been a demand for the development of guest materials and host materials that do not form excited bimolecular aggregates and are less affected by Forster-type energy transfer.

  Patent Documents 1 and 2 describe using a pyrene derivative as a light emitting material.

JP 2008-127291 A JP 2004-204238 A

Journal of Applied Physics, 91, 3324 (2002), Journal of Applied Physics, 100, 073106 (2006)

An object of the present invention is to solve the above-described problems and achieve the following objects.
That is, an object of the present invention is to provide an organic electroluminescent device that can satisfy a high degree of orientation, a high external quantum efficiency, and a low driving voltage. Another object of the present invention is to provide a material for an organic electroluminescence device capable of forming a film in which intermolecular interaction is suppressed, energy transfer / transfer is excellent, excitation bimolecular aggregates are difficult to form, and crystallization is difficult to form. To do.

The present inventors believe that in a two-component system of a light emitting material and a host material, reducing the difference between the dipole moments reduces the intermolecular interaction and leads to improved compatibility. From this, it is considered that microphase separation is suppressed and crystallization is suppressed. In general, molecules having rigidity and high planarity are easily oriented, but on the other hand, π-π interaction is strong, and crystallization is likely to occur due to factors such as excluded volume effect. By applying the above-described concept of crystallization inhibition to such a plate-like molecule, a highly oriented material that has not been realized so far and is difficult to crystallize has been found.
That is, the present invention is as follows.

[1]
An organic electroluminescent device having a pair of electrodes including an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes,
A non-liquid crystalline flat luminescent material having an aspect ratio (molecular length / molecular thickness) of a molecular length and a molecular thickness greater than 3,
A non-liquid crystalline flat host material having an aspect ratio (molecular length / molecular thickness) of molecular length and molecular thickness of greater than 3;
An organic electroluminescent element in which the dipole moment Dg (unit: Debye) of the light emitting material and the dipole moment Dh (unit: Debye) of the host material satisfy the following formula (I).
| Dg-Dh | <1 (I)
[2]
The organic electroluminescent element according to [1], wherein a dipole moment Dg of the luminescent material is 5 debyes or less.
[3]
The organic electroluminescent element according to [1] or [2], wherein the dipole moment Dh of the host material is 5 Debye or less.
[4]
The organic electroluminescent element according to any one of [1] to [3], wherein the light emitting material is a condensed polycyclic aromatic compound formed of four or more condensed rings.
[5]
The organic electroluminescent element according to any one of [1] to [4], wherein the light emitting material is a pyrene derivative.
[6]
The organic electroluminescent element according to any one of [1] to [5], wherein the light emitting material is represented by the following general formula (1).

Wherein R _{1 to} R ₁₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{1 to} R ₁₀ are bonded to each other; A ring may be formed.)
[7]
The organic electroluminescent element according to any one of [1] to [6], wherein the light emitting material is represented by the following general formula (2).

Wherein R _{11 to} R ₂₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{11 to} R ₂₀ are bonded to each other; A ring may be formed.)
[8]
The organic electroluminescent element according to any one of [1] to [6], wherein the light emitting material is represented by the following general formula (3).

Wherein R _{21 to} R ₃₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{21 to} R ₃₀ are bonded to each other; A ring may be formed.)
[9]
The organic electroluminescent element according to any one of [1] to [6], wherein the light emitting material is represented by the following general formula (4).

Wherein R _{31 to} R ₄₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{31 to} R ₄₀ are bonded to each other; A ring may be formed.)
[10]
The organic electroluminescent element according to any one of [1] to [6], wherein the light emitting material is represented by the following general formula (5).

Wherein R _{41 to} R ₅₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{41 to} R ₅₀ are bonded to each other; A ring may be formed.)
[11]
The organic electroluminescent element according to any one of [1] to [4], wherein the light emitting material is represented by the following general formula (6).

(Wherein R _{51 to} R ₅₄ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, substituted or unsubstituted Unsubstituted silyl group, substituted or unsubstituted alkyloxycarbonyl group, substituted or unsubstituted aryloxycarbonyl group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group Represents a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, which may be bonded to each other to form a ring. And p each independently represents an integer of 0 to 3. When m, n, o, and p are 2 or more, 'S R ₅₁ to R ₅₄ may be bonded to each other to form a ring, respectively. Also, the hydrogen atom in the formula may be heavy hydrogen atoms.)
[12]
The organic electroluminescent element according to any one of [1] to [4], wherein the light emitting material is represented by the following general formula (7).

(Wherein R _{55 to} R ₆₄ are each independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, at least one hydrogen atom of R ₅₅ to R ₆₄ Substituents other than
[13]
The organic electroluminescent element according to any one of [1] to [12], wherein a ratio of a horizontal alignment component of a transition dipole moment of the light emitting material in the light emitting layer is greater than 85%.
[14]
A non-liquid crystalline flat light emitting material having an aspect ratio (molecular length / molecular thickness) between molecular length and molecular thickness greater than 3, and an aspect ratio (molecular length / molecular thickness) between molecular length and molecular thickness is greater than 3. An organic electric field containing at least a non-liquid crystalline flat host material, wherein the dipole moment Dg (unit: Debye) of the light emitting material and the dipole moment Dh (unit: Debye) of the host material satisfy the following formula (I) Material for light emitting elements.
| Dg-Dh | <1 (I)
[15]
The manufacturing method of an organic electroluminescent element including at least the process of forming a light emitting layer by the vacuum evaporation process using the material for organic electroluminescent elements as described in [14], or a wet process.
[16]
The film | membrane containing the organic electroluminescent element material as described in [14].
[17]
A light-emitting device using the organic electroluminescent element according to any one of [1] to [13].
[18]
The display apparatus using the organic electroluminescent element of any one of [1]-[13].
[19]
The illuminating device using the organic electroluminescent element of any one of [1]-[13].

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which can satisfy a high degree of orientation, a high external quantum efficiency, and a low drive voltage can be provided. In addition, it is possible to provide an organic electroluminescent element material capable of forming a film in which intermolecular interaction is suppressed, energy transfer / transfer is excellent, an excited bimolecular aggregate is difficult to form, and crystallization is difficult to form.

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 schematic diagram for demonstrating the molecular length of material.

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 is 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, t-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 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms). Particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms, and more. Preferably it is C1-C20, Most preferably, it is C1-C10, for example, a methoxy, an ethoxy, butoxy, 2-ethylhexyloxy etc. are mentioned), an aryloxy group (preferably C6-C30, More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl And 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.), an aryloxycarbonyl group (preferably having a carbon number) 7-30, More preferably, it is C7-20, Most preferably, it is C7-12, for example, phenyloxycarbonyl etc. are mentioned. ), 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 a carbon number). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Rufinyl 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, such as trimethylsilyloxy, triphenylsilyloxy, etc.), 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. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

[Materials for organic electroluminescent elements]
The material for an organic electroluminescent device of the present invention is a non-liquid crystalline flat light emitting material having an aspect ratio (molecular length / molecular thickness) of a molecular length and molecular thickness greater than 3, and an aspect ratio of molecular length to molecular thickness. A non-liquid crystalline flat host material having a (molecular length / molecular thickness) greater than 3, and the dipole moment Dg of the light emitting material and the dipole moment Dh of the host material satisfy the following formula (I): It is characterized by that.
| Dg-Dh | <1 (I)

  Conventionally, not only in the field of organic EL, but the approach for orienting molecules is generally “strengthening intermolecular interactions such as dipole-dipole interaction” or “using tabular molecules”. there were. However, since such a method also leads to an increase in crystallinity, it is difficult to use the above approach in an organic device in which a decrease in film quality due to crystallization leads to a decrease in performance. In the present invention, it was discovered that the crystallinity can be lowered while maintaining the orientation by using a combination of a flat light emitting material and a host material with a small difference in dipole moment while being non-liquid crystalline. . According to the present invention, high luminous efficiency, low voltage, and low crystallinity (improved film quality) can be established.

In the present invention, the “molecular length” of the light-emitting material and the host material is the average value of the two sides a and b in the closest rectangle when the material molecules are assumed to have a flat plate structure, as shown in FIG. Means. Here, the “closest quadrangle” is defined as a quadrangle in which the average value of a and b is the smallest among the quadrilaterals whose two sides are in contact with the molecule. This “molecular length” is defined as follows by theoretical calculation. That is, the density functional method is used. Specifically, using Gaussian 03 (Gaussian, USA), the basis optimization function is 6-31G ^* and the exchange correlation functional is B3LYP / LANL2DZ. Do. Using the optimized structure obtained by the structure optimization calculation, the average length of two sides in the closest rectangle in the ball and stick display is defined as the molecular length.

  Further, the “molecular thickness” refers to the flat plate portion of the flat plate structure as the x axis and the y axis (for example, the direction of the side of the length a in FIG. 2 is the y axis and the direction of the side of the length b is the x axis). It means the thickness of the molecule in the z-axis direction orthogonal to the x-axis and y-axis when assumed. The molecular thickness is also determined by the same method as the molecular length, and the length in the thickness direction of the molecule in ball and stick display is defined as the molecular thickness.

  The presence or absence of the liquid crystallinity of the material (the presence or absence of liquid crystallinity) can be determined by observing the DSC measurement and the polarization microscope.

  Hereinafter, the structure of the organic electroluminescent element material of the present invention will be described.

(Absolute value of the difference between the dipole moments of the luminescent material and the host material)
The absolute value of the difference between the dipole moment Dg (unit: Debye) of the light emitting material used for the organic electroluminescent element material of the present invention and the dipole moment Dh (unit: Debye) of the host material is expressed by the following general formula (I). Fulfill.
| Dg-Dh | <1 (I)
| Dg−Dh | is preferably 0 to 0.5 from the viewpoint of reducing the interaction between the light emitting material and the host material and improving the dispersibility of the material.
The dipole moment in the present invention is calculated by the above-described density functional method.

(Luminescent material)
The non-liquid crystalline and flat light emitting material used for the organic electroluminescent element material of the present invention will be described.
The light emitting material preferably has an aspect ratio (molecular length / molecular thickness) of greater than 3 and greater than 3 and less than or equal to 10 from the viewpoint of improving its orientation without disturbing the orientation of the non-liquid crystalline host material. More preferably, it is greater than 3 and 7 or less.
When the aspect ratio is 3 or less, the molecular fluctuation increases and the orientation may decrease.

The dipole moment (Dg) of the luminescent material is preferably 5 Debye or less, more preferably 0 to 3 Debye, and more preferably 0 to 1 Debye from the viewpoint of reducing the interaction between the luminescent materials. Is more preferable.
The light emitting material having the above dipole moment is preferably a condensed polycyclic aromatic compound formed from four or more condensed rings.

  The light-emitting materials include pyrene, fluoranthene, benzofluoranthene, dibenzofluoranthene, acephenanthrylene, aceanthrylene, triphenylene, acenaphthotriphenylene, chrysene, perylene, benzochrysene, naphthacene, preaden, picene, pentaphene, pentacene , Tetraphenylene, trinaphthylene, benzophenanthrene, dibenzonaphthacene, benzoanthracene, dibenzoanthracene, benzonaphthacene, naphthopyrene, benzopyrene, dibenzopyrene, benzocyclooctene, anthranaphthacene, acenaphthofluoranthene, and derivatives thereof From the viewpoint of symmetry, a pyrene derivative, a perylene derivative, a fluoranthene derivative, a triphenylene derivative, or a chrysene derivative is preferable. Emissions derivatives, perylene derivatives, and more preferably fluoranthene derivative or chrysene derivative.

[Pyrene derivatives]
A conventionally known pyrene derivative can be used as the pyrene derivative, but a compound represented by the following general formula (1) is preferably used.

Wherein R _{1 to} R ₁₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{1 to} R ₁₀ are bonded to each other; A ring may be formed.)

R _{1 to} R ₁₀ may be the same or different.
The alkyl group represented by R ₁ to R _10, preferably having 1 to 20 carbon atoms, and specific examples methyl, ethyl, i- propyl, t- butyl group, a cyclohexyl group.
The aralkyl group represented by R _{1 to} R ₁₀ is preferably one having 1 to 20 carbon atoms, and specific examples include benzyl group, phenethyl group, α-methylbenzyl group, α, α-dimethylbenzyl group, 1-naphthylmethyl. Group, 2-naphthylmethyl group, furfuryl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 4 -N-hexylbenzyl group, 4-nonylbenzyl group, 3,4-dimethylbenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n -Hexyloxybenzyl group, 4-nonyloxybenzyl group, 4-fluorobenzyl group, 3-fluorobenzyl group, 2-chloro Njiru group, 4-chlorobenzyl group and the like.
The aryl group represented by R _{1 to} R ₁₀ is preferably an aryl group having 6 to 20 carbon atoms, and specific examples thereof include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, and a fluorenyl group.
The heterocyclic group represented by R _{1 to} R ₁₀ is preferably one having 5 to 20 carbon atoms, and specific examples include pyridyl group, thienyl group, oxazole group, oxadiazole group, benzothienyl group, dibenzofuryl group, dibenzo group. Examples include thienyl group, pyrazyl group, pyrimidyl group, pyrazoyl group, imidazolyl group, phenylcarbazoyl group and the like.
The alkoxy group R ₁ to R ₁₀ represent preferably has 1 to 10 carbon atoms, and specific examples include a methoxy group, an ethoxy group.
The aryloxy group represented by R _{1 to} R ₁₀ is preferably an aryloxy group having 6 to 20 carbon atoms, and specific examples thereof include a phenyloxy group and a biphenyloxy group.
The amino group represented by R _{1 to} R ₁₀ is preferably an arylamino group having 12 to 30 carbon atoms, and specific examples thereof include a diphenylamino group, a carbazoyl group, and a phenylcarbazoyl group.
Examples of the halogen atom represented by R _{1 to} R ₁₀ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

Two adjacent R _{1 to} R ₁₀ may be bonded to each other to form a ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, a thiophene ring, and a furan ring.

When R _{1 to} R ₁₀ have a substituent, examples of the substituent include a halogen atom (preferably a fluorine atom), a cyano group, a perfluoroalkyl group (preferably a trifluoromethyl group), an alkoxy group, an aryl group, a complex Examples thereof include a cyclic group and an alkyl group. When R _{1 to} R ₁₀ represent an alkyl group having a substituent, the substituent is preferably a fluorine atom.

  The following [1] to [5] are mentioned as preferred embodiments.

[1] R ₁ , R ₃ , R ₆ and R ₈ represent a group other than a hydrogen atom (preferably a substituted or unsubstituted aryl group), and R ₂ , R ₄ , R ₅ , R ₇ , R ₉ , R _{When 10} represents a hydrogen atom.

[2] R ₄ , R ₅ , R ₉ and R ₁₀ represent a group other than a hydrogen atom (preferably a substituted or unsubstituted aryl group), and R ₂ and R ₇ represent a group other than a hydrogen atom (preferably a substituted or unsubstituted group). An unsubstituted alkyl group), and R ₁ , R ₃ , R ₆ , and R ₈ represent a hydrogen atom.

[3] R ₅ and R ₁₀ represent a group other than a hydrogen atom (preferably a substituted or unsubstituted aryl group), and R ₂ and R ₇ represent a group other than a hydrogen atom (preferably a substituted or unsubstituted alkyl group, A substituted or unsubstituted aryl group), R ₄ and R ₉ represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁ , R ₃ , R ₆ and R ₈ represent a hydrogen atom.

[4] R ₄ and R ₅ , and R ₉ and R ₁₀ form a ring, and R ₂ and R ₇ represent a group other than a hydrogen atom (preferably a substituted or unsubstituted alkyl group), R ₁ , When R ₃ , R ₆ and R ₈ represent a hydrogen atom. It is preferable to form a fluorene ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring together with the benzene ring to which R ₄ and R ₅ and R ₉ and R ₁₀ are bonded. These rings may have a substituent, and the substituent is preferably an alkyl group, an aryl group, a halogen atom, or a cyano group, and the alkyl group or aryl group may further have a substituent. As the further substituent, an alkyl group, a fluorine atom, a cyano group, and a perfluoroalkyl group are preferable.

[5] When R ₃ and R ₄ , and R ₈ and R ₉ are bonded to each other to form an aromatic ring, and R ₁ , R ₂ , R ₅ , R ₆ , R ₇ , and R ₁₀ represent a hydrogen atom .

  The light emitting material is more preferably represented by any one of the following general formulas (2) to (5).

Wherein R _{11 to} R ₂₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{11 to} R ₂₀ are bonded to each other; A ring may be formed.)

In the general formula (2), R _{11 to} R ₂₀ may be the same or different.
Specific examples and preferred ranges of the alkyl group, the aralkyl group, the aryl group, the heterocyclic group, the alkoxy group, the aryloxy group, the amino group, or the halogen atom represented by R _{11 to} R ₂₀ are R ₁ to R ₁ in the general formula (1). The specific examples of R ₁₀ and the preferred range are the same.
In the general formula (2), preferred examples of R _{11 to} R ₂₀ include a hydrogen atom, a halogen atom, a cyano group, a perfluoroalkyl group, an alkoxy group, an aryl group, a heterocyclic group, and an alkyl group.
In the general formula (2), R _{11 to} R _{14 each} represent a hydrogen atom, a halogen atom (preferably a fluorine atom), a cyano group, or a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group). preferable. The aryl group preferably has 6 to 20 carbon atoms, and specific examples thereof include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, and the like, and a phenyl group is particularly preferable. Examples of the substituent that the aryl group may have include a halogen atom (preferably a fluorine atom), a cyano group, a perfluoroalkyl group (preferably a perfluoroalkyl group having 1 to 5 carbon atoms, and a trifluoromethyl group. Is particularly preferred), an alkoxy group (preferably an alkoxy group having 1 to 10 carbon atoms, more preferably a methoxy group or an ethoxy group), an aryl group (an aryl group having 6 to 20 carbon atoms is preferred, and specific examples include: A phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group), a heterocyclic group (preferably a heterocyclic group having 5 to 20 carbon atoms, a pyridyl group, a thienyl group, an oxazole group, an oxadiazole group , Benzothienyl group, dibenzofuryl group, dibenzothienyl group, pyrazyl group, pyrimidyl group, pyrazoyl group, A midazoyl group and a phenylcarbazoyl group are more preferable, a pyridyl group is particularly preferable, and an alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms). And a methyl group, an ethyl group, an i-propyl group, a t-butyl group, and a cyclohexyl group). A halogen atom, a cyano group, a perfluoroalkyl group, and an alkyl group are more preferable.
_Further, R 11 _{to R 14} may be a plurality of presence, a plurality of _R 11 _{to R 14} may be the same or different. When there are a plurality of R _{11 to} R _14, they may be bonded to each other to form a ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, and an oxazole ring. , Thiazole ring, pyrazole ring, thiophene ring, furan ring and the like. When forming a ring, it is preferable to form a fluorene ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring together with the benzene ring to which R _{11 to} R ₁₄ are bonded. These rings may have a substituent, and the substituent is preferably an alkyl group, an aryl group, a halogen atom, or a cyano group, and the alkyl group or aryl group may further have a substituent. As the further substituent, an alkyl group, a fluorine atom, a cyano group, and a perfluoroalkyl group are preferable.
In the general formula _{(2), R} 15 ~R ₂₀ preferably represents a hydrogen atom.

Wherein R _{21 to} R ₃₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{21 to} R ₃₀ are bonded to each other; A ring may be formed.)

In the general formula (3), R _{21 to} R ₃₀ may be the same or different.
Specific examples and preferred ranges of the alkyl group, the aralkyl group, the aryl group, the heterocyclic group, the alkoxy group, the aryloxy group, the amino group, or the halogen atom represented by R _{21 to} R ₃₀ are R ₁ to R ₁ in the general formula (1). The specific examples of R ₁₀ and the preferred range are the same.
In the general formula (3), preferred examples of R _{21 to} R ₃₀ include a hydrogen atom, a halogen atom, a cyano group, a perfluoroalkyl group, an alkoxy group, an aryl group, a heterocyclic group, and an alkyl group.
In the general formula (3), R _{21 to} R ₂₄ are the same as R _{11 to} R _{14 in} the general formula (2), and the preferred range is also the same. R _{21 to} R ₂₄ more preferably represent a hydrogen atom or a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group).
In the general formula (3), R ₂₆ and R ₂₉ are preferably an alkyl group or an aryl group. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. Specific examples include a methyl group, an ethyl group, an i-propyl group, a t-butyl group, and a cyclohexyl group. Groups and the like. The aryl group is preferably an aryl group having 6 to 20 carbon atoms, and specific examples include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, and a fluorenyl group.
In the general formula (3), R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ preferably represent a hydrogen atom.

Wherein R _{31 to} R ₄₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{31 to} R ₄₀ are bonded to each other; A ring may be formed.)

In the general formula (4), R _{31 to} R ₄₀ may be the same or different.
Alkyl group represented by R ₃₁ to R _40, aralkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, or a specific example and preferred ranges of the halogen atom, _R 1 ~ in the general formula (1) The specific examples of R ₁₀ and the preferred range are the same.
In the general formula (4), preferred examples of R _{31 to} R ₄₀ include a hydrogen atom, a halogen atom, a cyano group, a perfluoroalkyl group, an alkoxy group, an aryl group, a heterocyclic group, and an alkyl group.
In the general formula _(4), R 31 _{to R 32} is the same as _R 11 _{to R 14} in the general formula (2), and preferred ranges are also the same. More preferably, R _{31 to} R ₃₂ represent a hydrogen atom or a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group).
In the general formula (4), R ₃₄ and R ₃₈ are preferably alkyl groups, preferably alkyl groups having 1 to 20 carbon atoms, more preferably alkyl groups having 1 to 10 carbon atoms, and specific examples include a methyl group. , Ethyl group, i-propyl group, t-butyl group, cyclohexyl group and the like.
In the general formula (4), R ₃₆ and R ₄₀ are preferably a hydrogen atom or an alkyl group, and the alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. Specific examples include a methyl group, an ethyl group, an i-propyl group, a t-butyl group, and a cyclohexyl group.
In the general formula _{(4), R 33, R} 35, R 37, R 39 preferably represents a hydrogen atom.

Wherein R _{41 to} R ₅₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{41 to} R ₅₀ are bonded to each other; A ring may be formed.)

In the general formula (5), R _{41 to} R ₅₀ may be the same or different.
Specific examples and preferred ranges of the alkyl group, the aralkyl group, the aryl group, the heterocyclic group, the alkoxy group, the aryloxy group, the amino group, or the halogen atom represented by R _{41 to} R ₅₀ include R ₁ to R ₁ in the general formula (1). The specific examples of R ₁₀ and the preferred range are the same.
In the general formula (5), preferred examples of R _{41 to} R ₅₀ include a hydrogen atom, a halogen atom, a cyano group, a perfluoroalkyl group, an alkoxy group, an aryl group, a heterocyclic group, and an alkyl group.
In the general formula (5), R ₄₃ , R ₄₆ , R ₄₇ and R ₅₀ preferably represent a hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group. The aryl group preferably has 6 to 20 carbon atoms, and specific examples thereof include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, and the like, and a phenyl group is particularly preferable. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples include a methyl group, an ethyl group, an i-propyl group, t- Examples include a butyl group and a cyclohexyl group. The substituent that the aryl group or alkyl group may have is the same as the substituent that R _{11 to} R ₁₄ of the general formula (2) may have.
It is particularly preferable that R ₄₃ and R ₄₇ represent a hydrogen atom, and R ₄₆ and R _{50 each} represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group.
In the general formula (5), R ₄₁ and R ₄₂ are the same as R _{11 to} R _{14 in} the general formula (2), and the preferred ranges are also the same. R ₄₁ and R ₄₂ more preferably represent a hydrogen atom or a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group).
In the general formula (5), R ₄₄ , R ₄₅ , R ₄₈ and R ₄₉ preferably represent a hydrogen atom.

  Specific examples of pyrene derivatives preferably used in the present invention are shown below using the following substituents a-1 to a-16, but are not limited thereto.

  Moreover, the following compounds are also mentioned as a specific example of a pyrene derivative.

As the perylene derivative, a conventionally known perylene derivative can be used, but a compound represented by the following general formula (6) is preferably used.
General formula (6)

(Wherein R _{51 to} R ₅₄ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, substituted or unsubstituted Unsubstituted silyl group, substituted or unsubstituted alkyloxycarbonyl group, substituted or unsubstituted aryloxycarbonyl group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group Represents a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, which may be bonded to each other to form a ring. And p each independently represents an integer of 0 to 3. When m, n, o, and p are 2 or more, 'S R ₅₁ to R ₅₄ may be bonded to each other to form a ring, respectively. Also, the hydrogen atom in the formula may be heavy hydrogen atoms.)

Specific examples and preferred ranges of the alkyl group, aralkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, amino group, or halogen atom represented by R _{51 to} R ₅₄ include R ₁ to R ₁ in the general formula (1). The specific examples of R ₁₀ and the preferred range are the same.
Examples of the silyl group represented by R _{51 to} R ₅₄ include an unsubstituted silyl group, an alkyl-substituted silyl group, and an aryl-substituted silyl group, and a trimethylsilyl group and a triphenylsilyl group are preferable.
Examples of the alkyloxycarbonyl group represented by R _{51 to} R ₅₄ include groups in which the alkoxy group is substituted with a carbonyl group, and the preferred range of the alkoxy group moiety is also the same.
Examples of the aryloxycarbonyl group represented by R _{51 to} R ₅₄ include groups in which the aryloxy group is substituted with a carbonyl group, and the preferred range of the aryloxy group moiety is also the same.
The carbamoyl group represented by R _{51 to} R ₅₄ is preferably a substituted carbamoyl group having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include a carbamoyl group, a methylcarbamoyl group, a diethylcarbamoyl group, and a phenylcarbamoyl group.
Examples of the heteroaryloxy group represented by R _{51 to} R ₅₄ include a group in which an oxygen atom is substituted for the heterocyclic group, and the preferred range is the same for the heterocyclic group moiety.
Examples of the alkylthio group represented by R _{51 to} R ₅₄ include a group in which a sulfur atom is substituted on the alkyl group, and the preferred range is the same for the alkyl group moiety.
Examples of the arylthio group represented by R _{51 to} R ₅₄ include a group in which a sulfur atom is substituted on the aryl group, and the preferred range of the aryl group portion is the same.

R _{51 to} R ₅₄ are preferably an alkyl group, an aryl group, a heterocyclic group, an amino group, a silyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthio group, or an arylthio group, and an alkyl group, an aryl group, or a hetero group. A cyclic group, an amino group, and a silyl group are more preferable. These groups may have a substituent, and examples of the substituent include the groups mentioned in the above-mentioned substituent group A, and an alkyl group and an aryl group are preferable. In the case of having a plurality of substituents, the substituents may be linked to form a ring.
In the formula, m, n, o, and p are preferably 0 to 2, and more preferably 0 to 1.

As the compound represented by the general formula (6), a compound represented by any one of the following general formulas (6a) to (6f) is preferable.
In general formulas (6a) to (6f), R _pe is independently an alkyl group, aryl group, heterocyclic group, amino group, silyl group, ester group, amide group, alkoxy group, aryloxy group, heteroaryl. An oxy group, an alkylthio group, or an arylthio group is represented. These may further have a substituent. Furthermore, R _pe in the general formulas (6d) to (6f) independently form a 5-membered or 6-membered ring, and the ring may further have a substituent.
Further, the hydrogen atoms in the general formulas (6a) to (6f) may be deuterium atoms.

_Rpe is preferably an alkyl group (such as a methyl group, a propyl group, or a butyl group), an aryl group (such as a phenyl group or a naphthyl group), a heterocyclic group (such as a pyridyl group), an amino group, a silyl group, or an amide group. It is.
_Examples of the substituent that the ring formed by R _pe and R _pe may have include an alkyl group (such as a methyl group and a butyl group) and an aryl group (such as a phenyl group).

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

  The perylene derivative represented by the general formula (6) can be synthesized according to the following scheme.

In the above scheme, R _pe has the same _{meaning as} R _{51 to} R ₅₄ in formula (6). X represents a halogen atom.

[Fluoranthene derivative]
As the fluoranthene derivative, a conventionally known fluoranthene derivative can be used, but a compound represented by the following general formula (7) is preferably used.
General formula (7)

(Wherein R _{55 to} R ₆₄ are each independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, at least one hydrogen atom of R ₅₅ to R ₆₄ Substituents other than

_<R 55 ~R _64>
(The type of the substituent _R 55 _{to R 64)}
R _{55 to} R ₆₄ are each independently a hydrogen atom, an aryl group which may have a substituent, an alkyl group which may have a substituent, a silyl group which may have a substituent, or a substituent. It represents a heterocyclic group which may have a group, an alkylamino group which may have a substituent, and an arylamino group which may have a substituent. These may be bonded to each other and condensed.
At least one of R ₅₅ to R ₆₄ is a substituent other than hydrogen atom.

If two or more R ₅₅ to R ₆₄ is a substituent other than a hydrogen atom, a substituent other than a 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.

The aryl group of R ₅₅ to R _64, preferably has 6 to 16 carbon atoms, and specific examples phenyl group, a biphenyl group, a phenanthryl group, a naphthyl group, an anthryl group, a fluorenyl group and the like.
The alkyl group represented by R ₅₅ to R _64, preferably has 1 to 10 carbon atoms, specific examples are i- propyl, t- butyl group, a cyclohexyl group.
The silyl group R ₅₅ to R ₆₄ represent preferably has 3 to 20 carbon atoms, a trimethylsilyl group and specific examples, dimethylphenyl silyl group, dimethylbutyl group, triisopropylsilyl group, such as methyl dibutyl silyl group Can be mentioned.
The heterocyclic group R ₅₅ to R ₆₄ represent preferably has 3 to 10 carbon atoms, a pyridyl group and specific examples include a thienyl group, oxazole group, oxadiazole group, benzothienyl group, dibenzofuryl group, dibenzo Examples include thienyl group, pyrazyl group, pyrimidyl group, pyrazoyl group, imidazolyl group, phenylcarbazoyl group and the like.
The alkylamino group represented by R ₅₅ to R _64, preferably has 1 to 10 carbon atoms, and specific examples, dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group and the like.
The arylamino group R ₅₅ to R ₆₄ represent preferably has 6 to 30 carbon atoms, and specific examples, diphenylamino group, carbazolyl group, and a phenyl naphthyl amino group.

  These substituents may further have a substituent. Further, the substituents that may be included are aryl group, arylamino group, alkyl group, perfluoroalkyl group, halide group, carboxyl group, cyano group, alkoxyl group, aryloxy group, carbonyl group, oxycarbonyl group, carboxyl group An acid group, a heterocyclic group, etc. are mentioned. 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.

Further, among the substituents that may be included, 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 5 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, and imidazoyl. Group and the like.
Among the substituents that R _{55 to} R ₆₄ and R _{55 to} R ₆₄ described above may have, an electron-donating group such as an arylamino group or an alkoxy group, or a heterocyclic ring such as a thienyl group or a benzothienyl group The group contributes to increasing the emission wavelength of the compound represented by the general formula (7). Thus the substituent that may have R ₅₅ to R ₆₄ and R ₅₅ to R ₆₄ is, by selecting these substituents, can be obtained that exhibit a green light emission.

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

  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.

(Host material)
The non-liquid crystalline and flat host material used in the present invention has an aspect ratio (molecular length / molecular thickness) larger than 3 from the viewpoint of improving its own orientation without disturbing the orientation of the light emitting material. It is more preferably 10 or less, and more preferably 3 or more and 7 or less.
When the aspect ratio is 3 or less, the molecular fluctuation increases and the orientation may decrease.

The dipole moment (Dh) of the host material is preferably 5 Debye or less, more preferably 0 to 3 Debye, and more preferably 0 to 1 Debye from the viewpoint of reducing the interaction between the host materials. Is more preferable.
The host material having the dipole moment as described above is preferably a non-condensed aromatic ring derivative, a torquecene derivative, a triphenylene derivative, or a pyrene derivative.

  The non-liquid crystalline host material used in the present invention has an aspect ratio larger than 3, is non-liquid crystalline, and has an absolute value of the dipole moment difference from the light emitting material satisfying the formula (I). Although not specifically limited, the compound represented by the following general formula (H1), (H2), (H3), or (H4) is preferable.

Wherein R _{50H to} R _52H are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, Substituted or unsubstituted condensed polycyclic aromatic group, substituted or unsubstituted condensed polycyclic heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted amino group Represents a halogen atom, a cyano group, or a perfluoroalkyl group.)

Specific examples of alkyl groups, aralkyl groups, aryl groups, heterocyclic groups, condensed polycyclic aromatic groups, condensed polycyclic heterocyclic groups, alkoxy groups, aryloxy groups, amino groups, and halogen atoms represented by R _{50H to} R _52H Examples and preferred ranges are the same as R _{1 to} R _{10 in} the general formula (1).
The perfluoroalkyl group represented by R _{50H to} R _52H is preferably a C 1-5 perfluoroalkyl group, and particularly preferably a trifluoromethyl group.

R _{50H to} R _52H are preferably a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. When the heterocyclic group has a substituent, the substituent is preferably an aryl group or an aromatic heterocyclic group.

  Specific examples of the compound represented by the general formula (H1) are shown below, but are not limited thereto.

  Next, general formula (H2) will be described.

(Wherein, R _{53H to} R _55H each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, Substituted or unsubstituted condensed polycyclic aromatic group, substituted or unsubstituted condensed polycyclic heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted amino group a halogen atom, a cyano group, or a perfluoroalkyl group _.R 53H _{to R 55H} may be a plurality of presence, a plurality of _R 53H _{to R 55H} good be bonded to each other to form a ring .X is Each independently represents a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom, and may have a substituent, and if possible, the substituents may be linked to form a condensed ring structure. Good.)

The alkyl group, aralkyl group, aryl group, heterocyclic group, condensed polycyclic aromatic group, condensed polycyclic heterocyclic group, alkoxy group, aryloxy group, amino group, halogen atom, peroxy group represented by R _{53H to} R _55H Specific examples and preferred ranges of the fluoroalkyl group are the same as R _{50H to} R _{52H in} formula (H1).

R _{53H to} R _55H are preferably a hydrogen atom or a substituted or unsubstituted aryl group. When the aryl group has a substituent, the substituent is preferably an alkyl group, a halogen atom, or a cyano group.
A plurality of R _{53H to} R _55H may be present, and a plurality of R _{53H to} R _55H may be bonded to each other to form a ring. The ring to be formed is the same as the specific example in the case where two of R _{1 to} R ₁₀ in the general formula (1) are bonded to each other to form a ring, and R _{53H to} R _55H are bonded to each other. It is preferable to form a fluorene ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring together with the benzene ring. These rings may have a substituent, and the substituent is preferably an alkyl group, an aryl group, a halogen atom, or a cyano group, and the alkyl group or aryl group may further have a substituent. As the further substituent, an alkyl group, a fluorine atom, a cyano group, and a perfluoroalkyl group are preferable.

In general formula (H2), X represents a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom each independently, and may have a substituent. If possible, the substituents may be linked to form a condensed ring structure.
X preferably represents a carbon atom having a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms. X particularly preferably represents a dimethylmethylene group.

  Although the specific example of a compound represented by general formula (H2) is shown below using the following substituent b-1 to b-10, it is not limited to these.

  Moreover, the following compounds are also mentioned as a specific example of a compound represented by general formula (H2).

  Next, general formula (H3) will be described.

( _Wherein R _{56H to} R _58H are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, Substituted or unsubstituted condensed polycyclic aromatic group, substituted or unsubstituted condensed polycyclic heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted amino group Represents a halogen atom, a cyano group, or a perfluoroalkyl group.)

The alkyl group, aralkyl group, aryl group, heterocyclic group, condensed polycyclic aromatic group, condensed polycyclic heterocyclic group, alkoxy group, aryloxy group, amino group, halogen atom, peroxy group represented by R _{56H to} R _58H Specific examples and preferred ranges of the fluoroalkyl group are the same as R _{50H to} R _{52H in} formula (H1). A plurality of R _{56H to} R _58H may be present.

R _{56H to} R _58H are preferably a hydrogen atom or a substituted or unsubstituted aryl group. When the aryl group has a substituent, the substituent is preferably an alkyl group, a halogen atom, or a cyano group.

The following [1] and [2] are mentioned as a preferable aspect of general formula (H3).
[1] A case in which R _{56H to} R _{58H have} substituted or unsubstituted phenyl groups on the carbon atoms at the 2-position, 3-position, 6-position, 7-position, 10-position and 11-position of the triphenylene skeleton.
[2] A case where it has an aryl group (preferably a terphenyl group, a _{quarterphenyl} group, or a _kinkphenyl group) in which three or more phenyl groups are connected as _{R56H to} the carbon atom at the 2-position of the triphenylene skeleton. When the aryl group has a substituent, the substituent is preferably an alkyl group, a halogen atom, or a cyano group.

  Specific examples of the compound represented by the general formula (H3) are shown below using the substituents b-1 to b-10, but are not limited thereto.

  Moreover, the following compounds are also mentioned as a specific example of a compound represented by general formula (H3).

  Next, general formula (H4) will be described.

_Wherein R _59H and R _60H are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, Substituted or unsubstituted condensed polycyclic aromatic group, substituted or unsubstituted condensed polycyclic heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted amino group Represents a halogen atom, a cyano group, or a perfluoroalkyl group.)

The alkyl group, aralkyl group, aryl group, heterocyclic group, condensed polycyclic aromatic group, condensed polycyclic heterocyclic group, alkoxy group, aryloxy group, amino group, halogen atom, peroxy group represented by R _59H and R _60H Specific examples and preferred ranges of the fluoroalkyl group are the same as R _{50H to} R _{52H in} formula (H1). A plurality of R _59H and R _60H may be present.

R _59H and R _60H are preferably a hydrogen atom or a substituted or unsubstituted aryl group. When the aryl group has a substituent, the substituent is preferably an alkyl group, a halogen atom, or a cyano group.
Preferred embodiments of formula (H4), if the carbon atom of the 2-position and 7-positions of pyrene skeleton having an aryl group as _{R 59H} and _{R 60H,} and _{R 59H} in the 4-position and 9-position carbon atom of the pyrene skeleton And R _60H has an aryl group.

  Specific examples of the compound represented by the general formula (H4) are shown below, but are not limited thereto.

  The content of the non-liquid crystalline host material in the organic electroluminescent element material is preferably 70% by mass to 99.9% by mass, more preferably 75% by mass to 99% by mass, and particularly preferably 80% by mass to 97% by mass. .

〔film〕
With the material for an organic electroluminescence device of the present invention, a non-liquid crystalline host material and a light emitting material having a high orientation and a good amorphous property can be obtained. The film is preferably formed by a vacuum deposition process from the viewpoint of orientation, but a film having both good orientation and amorphous properties can be obtained by a coating process (wet process). The film can be used as a light-emitting layer of an organic electroluminescence device, and has a high orientation, so that the light extraction efficiency is excellent, and since the amorphous property is good, a highly durable light-emitting layer can be obtained.

[Organic electroluminescence device]
The organic electroluminescent element in the present invention will be described in detail.
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, The aspect ratio (molecular length / molecular thickness) of a flat and non-liquid crystalline light emitting material with an aspect ratio (molecular length / molecular thickness) of molecular length to molecular thickness greater than 3, and the molecular length to molecular thickness. And at least a non-liquid crystalline host material larger than 3, a dipole moment Dg (unit: Debye) of the light emitting material, and a dipole moment Dh (unit: Debye) of the host material represented by the following formulas ( I) is satisfied.
| Dg-Dh | <1 (I)

In the organic electroluminescent element of the present invention, the light emitting layer is an organic layer, and further includes at least one organic layer between the light emitting layer and the anode, but 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 electroluminescence device of the present invention, each organic layer is subjected to a solution coating process (wet process) such as a dry film forming method such as a vacuum deposition method or a sputtering method, a transfer method, a printing method, a spin coating method, or a bar coating method. Either can be suitably formed. As a dry method, a vacuum deposition method, a sputtering method, etc. can be used. As a wet method (wet film forming method), a dipping method, a spin coating method, a dip coating method, a casting method, a die coating method, a roll coating method, a bar coating method, A gravure coating method, a spray coating method, 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, 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.
The light emitting layer can be formed by a vacuum deposition process or a wet process. 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 the present invention, the aforementioned non-liquid crystalline host material is contained. 70 mass%-99.9 mass% are preferable, as for content in the light emitting layer of this non-liquid crystalline host material, 75 mass%-99 mass% are more preferable, and 80 mass%-95 mass% are especially preferable.

  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.

  The ratio of the horizontal alignment component of the transition dipole moment of the luminescent material in the luminescent layer is preferably greater than 50%, more preferably greater than 70%, even more preferably greater than 85%, and greater than 90%. Particularly preferred.

(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. Can be obtained.

  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.

(Use of the organic electroluminescence device of the present invention)
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication. 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.

  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 example>
The pyrene compounds used in the examples and comparative examples can be synthesized through the halogenation and the coupling reaction using a metal catalyst using pyrene as a starting material. Specifically, in the case of a pyrene compound in which Ar ₁ is substituted at the ₁ , 3 and 6 positions and Ar ₂ is substituted at the 8 position, the compounds can be synthesized according to the following scheme. Ar ₁ and Ar ₂ each independently represents an aryl group.

Hereinafter, each reaction step shown in the above scheme will be described.
It is possible to obtain a brominated substrate mixture by dissolving or suspending 1 mol of a reaction substrate in a solvent and adding 1 to 30 mol of a brominating agent directly or dissolved in a polar or nonpolar solvent. it can.
The solvent is not particularly limited as long as it does not react with the brominating agent and dissolves the substrate and the brominating agent. For example, the reaction is preferably performed using a halogen-based solvent such as methylene chloride or chloroform, an amide-based solvent such as N, N-dimethylformamide or N, N-dimethylacetamide, or an acid solvent such as acetic acid or sulfuric acid. One of these may be used alone, or two or more may be used in any combination and ratio.

[Synthesis Example 1]

(Synthesis of 1a)
According to the method of Unexamined-Japanese-Patent No. 2009-35516, 1a was obtained by brominating pyrene (30g) (3.3g).
(Synthesis of 1b)
Coupling of 1a (3.3 g) and 4-biphenylboronic acid (4.7 g, manufactured by Tokyo Kasei Co., Ltd.) under basic conditions using a Pd catalyst according to the method described in JP2009-35516A as in 1a The reaction gave 1b (2.4 g).
(Synthesis of 1c)
1b (2.0 g) was brominated by the method described in JP-A-2008-101182 to obtain 1c (1.8 g).
(Synthesis of 1d)
As in 1b, 1c (1.5 g) and 4-fluorophenylboronic acid (0.3 g, manufactured by Tokyo Chemical Industry) were subjected to a coupling reaction using a Pd catalyst under basic conditions to obtain 1d (0.9 g). It was.

[Synthesis Example 2]

(Synthesis of 2a)
According to the method of Unexamined-Japanese-Patent No. 2008-101182, 2a was obtained by brominating pyrene (30g) (7.4g).
(Synthesis of 2b)
According to the method described in JP 2009-35516 A, 2b (7.2 g) and 4-biphenylboronic acid (8.3 g, manufactured by Tokyo Chemical Industry Co., Ltd.) were subjected to a coupling reaction using a Pd catalyst under basic conditions. Obtained (7.7 g).
(Synthesis of 2c)
Similarly to the synthesis of 2a, 2b (6.9 g) was brominated by the method described in JP-A-2008-101182 to give 2c (4.5 g).
(Synthesis of 2d)
Similar to the synthesis of 2b, 2c (1.5 g) and 4-fluorophenylboronic acid (0.66 g, manufactured by Tokyo Chemical Industry Co., Ltd.) were subjected to a coupling reaction using a Pd catalyst under basic conditions to give 2d (1.1 g). Got.

[Synthesis Example 3]

(Synthesis of 3d)
Using 2c (1.5 g) of Synthesis Example 2 as a raw material, 4-cyanophenylboronic acid (0.7 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was subjected to 3d (0.9 g) by a coupling reaction using a Pd catalyst under basic conditions. Got.

[Synthesis Example 4]

(Synthesis of 4a and 4b)
4a and 4b were synthesized according to the method described in JP-A-2008-101182.
(Synthesis of 4c)
4b (50 g) was brominated with bromine (manufactured by Tokyo Chemical Industry Co., Ltd., 60 g) and derived into 4c (48 g).
(Synthesis of 4d)
4d (43.2 g) was synthesized from 4c (40 g) by a coupling reaction similar to the synthesis of 1b.

[Synthesis Example 5]

(Synthesis of 5a)
Biphenyl (100 g, manufactured by Tokyo Chemical Industry) and 2-chloro-2-methylpropane (144 g, manufactured by Tokyo Chemical Industry) were subjected to Friedel-Crafts alkylation reaction in the presence of iron chloride to obtain 5a (152 g).
(Synthesis of 5b)
5a (150 g) was brominated with bromine (manufactured by Tokyo Chemical Industry Co., Ltd., 180 g) and derived into 5b (143 g).
(Synthesis of 5c)
By reacting 5b (140 g) with trimethylsilylacetylene (162 g, manufactured by Tokyo Chemical Industry) by the Sonogashira coupling reaction described in “Journal of Organic Chemistry, 2004, vol. 69, # 16 p. 5428-5432”, 5c (98 g) was obtained.
(Synthesis of 5d)
According to the Sonogashira coupling reaction described in “Journal of Organic Chemistry, 2001, vol. 66, # 23 p. 7804-7810”, 5c (32.2 g) and 4-iodobiphenyl (47.2 g, manufactured by Wako Pure Chemical Industries, Ltd.) 5d (30.8 g) was synthesized.
(Synthesis of 5e)
The pyrene derivative 5e (11.2 g) was obtained from 5d (30 g) using platinum chloride (1.1 g) as a catalyst by the method described in “Journal of Organic Chemistry, 2009, vol. 74, # 16 p6311-6314”.

[Synthesis Example 6]

(Synthesis of 6d)
A series of synthesis described in the above scheme using pyrene as a starting material was synthesized according to the method described in JP-A-2008-127291.

[Synthesis Example 7]

(Synthesis of 7a)
7a (156 g) was synthesized using 1-indanone (300 g, manufactured by Tokyo Chemical Industry) as a starting material by the method described in “Synthetic Communications, 1997, vol. 27, p. 2021”.
(Synthesis of 7b)
Under a nitrogen atmosphere at 0 ° C., 7a (50 g) was dissolved in THF (2 L), and 3 equivalents of t-BuOK (49 g) was added. After stirring at room temperature for 1 hour, MeI (104 g) was added dropwise. After cooling to 0 ° C. again and adding 3 equivalents of t-BuOK, MeI was added dropwise in the same procedure to complete the reaction. The reaction solution was poured into a large amount of water, and the precipitated solid was filtered to obtain 7b (43.6 g) as a white solid.
(Synthesis of 7c)
7b (40 g) was brominated with Br _{2 in} methylene chloride solvent to synthesize 7c (49.8 g).
(Synthesis of 7d)
Similar to the synthesis of 2b, 7c (10 g) and 3-fluorophenylboronic acid (4.5 g, manufactured by Tokyo Chemical Industry Co., Ltd.) were subjected to a coupling reaction using a Pd catalyst under basic conditions to obtain 7d (6.8 g). It was.
(Synthesis of 7e)
Similar to the synthesis of 2b, 7e (4.82 g) was obtained by coupling reaction of 7d (6 g) and 4-methylphenylboronic acid (1.23 g, manufactured by Tokyo Chemical Industry) using a Pd catalyst under basic conditions. It was.

[Synthesis Example 8]

  8b was synthesized in the same manner as in Synthesis Example 7.

[Synthesis Example 9]

  9b was synthesized in the same manner as in Synthesis Example 7.

[Synthesis Example 10]

  10a was synthesized in the same manner as in Synthesis Example 7.

[Synthesis of Host Material of Comparative Example 7]

(Synthesis of 11a)
Similar to the synthesis of 2b, 1,3,5-tribromobenzene (50 g, manufactured by Tokyo Chemical Industry) and 4-fluorophenylboronic acid (46.7 g, manufactured by Tokyo Chemical Industry) were used under basic conditions using a Pd catalyst. The coupling reaction gave 11a (36.7 g).
(Synthesis of 11b)
11b (35 g) and bis (pinacolato) diboron (30.9 g, manufactured by Tokyo Chemical Industry Co., Ltd.) were reacted with PdCl ₂ (dppf) in a N, N-dimethylacetamide solvent under basic conditions to obtain 11b (32.1 g). ) Was synthesized.
(Synthesis of 11c)
Triphenylene (70 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was brominated with bromine (160 g) to obtain 11c (59.8 g).
(Synthesis of 11d)
Similarly to the synthesis of 2b, 11d (12.5 g) was synthesized by a coupling reaction using a Pd catalyst under basic conditions of 11b (15.3 g) and 11c (10 g).

(Synthesis example of compounds described in Comparative Examples) (Guest)
The guest compounds described in Comparative Examples 1, 2, and 8 were synthesized using the same method as that described in Synthesis Example 2.
The guest compounds described in Comparative Examples 3, 4, 5, 6, and 7 were synthesized using the same method as that described in Synthesis Example 1.
The compound described in Comparative Example 12 is a compound described in Japanese Patent Application Laid-Open No. 2008-127291, and was synthesized using the method described in this document.
The compound described in Comparative Example 13 was a compound described in Japanese Patent Application Laid-Open No. 2007-27779 and was synthesized using the method described in this document.

(Synthesis example of compounds described in Comparative Examples) (Host)
The host compounds described in Comparative Examples 1, 9, 10 and 11 were synthesized using the same method as that described in Synthesis Example 7.
The host compound described in Comparative Example 4 was synthesized using the same method as that described in Comparative Example 7.
The host compound described in Comparative Example 12 was synthesized using the method described in Japanese Patent Application Laid-Open No. 2008-127291.
The host compound described in Comparative Example 13 was synthesized by the method described in US2009 / 227812, followed by the Suzuki coupling method (for example, Chem. Rev., 1995, vol. 95, p. 2457).

(Example 2)
<Evaluation of degree of orientation of deposited film and observation of crystallization>

(Film formation)
On a quartz glass substrate of 25 mm × 25 mm × 0.7 mm, a host material and a light emitting material shown below were vapor-deposited at a mass ratio (90:10) by vacuum vapor deposition to form a film.

(Orientation evaluation)
The degree of orientation of the light-emitting material was calculated as the degree of horizontal alignment order S by polarized ATR-IR analysis. The results are shown in Tables 1 and 2. S represents the ratio of the horizontal alignment component of the transition dipole moment of the luminescent material (when the horizontal alignment component is 100%, S = 1, and when 67%, S = 0, when 85%) S = 0.55).

(Confirm crystallinity)
The deposited film was checked for crystal precipitation by optical microscope observation (digital microscope, 1000 times).
○: No crystallization observed after 2 to 3 weeks Δ: No crystallization observed for 1 week ×: Crystallization observed within 2 to 3 days

  As can be seen from the results of Tables 1 and 2, the embodiment of the present invention in which the aspect ratio of the light emitting material and the host material is 3 or more and the difference between the dipole moments of the light emitting material and the host material is smaller than 1 is high horizontal alignment. It can be seen that a high-quality thin film having an ordering degree S and hardly crystallizing is obtained.

(Example 3)
(Organic electroluminescence device evaluation)
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. The “Ω / □” has the same meaning as “Ω / sq.”.
In addition, the vapor deposition rate in the following examples and comparative examples is 0.1 nm / second unless otherwise specified. The deposition rate was measured using a quartz resonator. The thickness of each layer below was measured using a quartz resonator.

First layer 2-TNATA and F4-TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm (deposition rate 0.5 nm / sec)
Second layer NPD: film thickness 10 nm (deposition rate 0.2 nm / sec)
Third layer Host materials and light emitting materials described below (mass ratio 90:10): film thickness 30 nm
Fourth layer BAlq: film thickness 40 nm

Further, on the fourth layer, 1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode. A patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was placed on the lithium fluoride layer, and metal aluminum was deposited.
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.

The compounds used are shown below.
2-TNATA: 4,4 ′, 4 ″ -tris (N, N- (2-naphthyl) -phenylamino) triphenylamine NPD: N, N′-dinaphthyl-N, N′-diphenyl- [1,1 '-Biphenyl] -4,4'-diamine BAlq: Bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolate) -aluminum (III)

<Element evaluation>
The following evaluation was performed about the obtained element. The evaluation results are shown in Tables 1 and 2.
(A) External quantum efficiency Using a source measure unit 2400 manufactured by KEITHLEY, 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. 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. The relative value when the external quantum efficiency of Comparative Example 2 was set to 1 was calculated for each element.

(B) Driving voltage Each element is caused to emit light by applying a DC voltage so that the luminance becomes 1000 cd / m ² . The applied voltage at this time was used as an index for driving voltage evaluation. The relative value when the driving voltage of Comparative Example 2 was 1 was calculated for each element.

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 (19)

An organic electroluminescent device having a pair of electrodes including an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes,
A non-liquid crystalline flat light emitting material having an aspect ratio (molecular length / molecular thickness) of a molecular length and a molecular thickness greater than 3 on the light emitting layer;
A non-liquid crystalline flat host material having an aspect ratio (molecular length / molecular thickness) of molecular length and molecular thickness of greater than 3;
Dipole moment Dg of the luminescent material (unit: Debye), dipole moment Dh (unit: Debye) of the host material meets the following formula (I), the
| Dg-Dh | <1 (I)
The light emitting material has a polycyclic aromatic ring;
An organic electroluminescence device , wherein the host material is a non-condensed aromatic ring derivative, torquesen derivative, triphenylene derivative or pyrene derivative .   The organic electroluminescent element according to claim 1, wherein a dipole moment Dg of the light emitting material is 5 Debye or less.   The organic electroluminescent element of Claim 1 or 2 whose dipole moment Dh of the said host material is 5 debyes or less.   The organic electroluminescent element of any one of Claims 1-3 whose said luminescent material is a condensed polycyclic aromatic compound formed from four or more condensed rings.   The organic electroluminescent element of any one of Claims 1-4 whose said luminescent material is a pyrene derivative. The organic electroluminescent element according to claim 1, wherein the light emitting material is represented by the following general formula (1).
Wherein R _{1 to} R ₁₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{1 to} R ₁₀ are bonded to each other; A ring may be formed.) The organic electroluminescent element according to claim 1, wherein the light emitting material is represented by the following general formula (2).
Wherein R _{11 to} R ₂₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{11 to} R ₂₀ are bonded to each other; A ring may be formed.) The organic electroluminescent element of any one of Claims 1-6 by which the said luminescent material is represented by following General formula (3).
Wherein R _{21 to} R ₃₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{21 to} R ₃₀ are bonded to each other; A ring may be formed.) The organic electroluminescent element of any one of Claims 1-6 by which the said luminescent material is represented by following General formula (4).
Wherein R _{31 to} R ₄₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{31 to} R ₄₀ are bonded to each other; A ring may be formed.) The organic electroluminescent element of any one of Claims 1-6 by which the said luminescent material is represented by following General formula (5).
Wherein R _{41 to} R ₅₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a halogen atom, or a cyano group, wherein two adjacent ones of R _{41 to} R ₅₀ are bonded to each other; A ring may be formed.) The organic electroluminescent element of any one of Claims 1-4 by which the said luminescent material is represented by following General formula (6).
(Wherein R _{51 to} R ₅₄ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, substituted or unsubstituted Unsubstituted silyl group, substituted or unsubstituted alkyloxycarbonyl group, substituted or unsubstituted aryloxycarbonyl group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group Represents a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, which may be bonded to each other to form a ring. And p each independently represents an integer of 0 to 3. When m, n, o, and p are 2 or more, 'S R ₅₁ to R ₅₄ may be bonded to each other to form a ring, respectively. Also, the hydrogen atom in the formula may be heavy hydrogen atoms.) The organic electroluminescent element according to claim 1, wherein the light emitting material is represented by the following general formula (7).
(Wherein R _{55 to} R ₆₄ are each independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, at least one hydrogen atom of R ₅₅ to R ₆₄ Substituents other than   The organic electroluminescent element according to any one of claims 1 to 12, wherein a ratio of a horizontal alignment component of a transition dipole moment of the light emitting material in the light emitting layer is larger than 85%. A non-liquid crystalline flat light emitting material having an aspect ratio (molecular length / molecular thickness) between molecular length and molecular thickness greater than 3, and an aspect ratio (molecular length / molecular thickness) between molecular length and molecular thickness is greater than 3. a non-liquid crystal tabular host material contains at least, dipole moment Dg of the luminescent material (unit: Debye), dipole moment Dh (unit: Debye) of the host material Shi satisfy the following formula (I) ,
| Dg-Dh | <1 (I)
The light emitting material has a polycyclic aromatic ring;
A material for an organic electroluminescent element , wherein the host material is a non-condensed aromatic ring derivative, torquesen derivative, triphenylene derivative or pyrene derivative .   The manufacturing method of an organic electroluminescent element at least including the process of forming a light emitting layer by the vacuum evaporation process using the organic electroluminescent element material of Claim 14, or a wet process.   The film | membrane containing the organic electroluminescent element material of Claim 14.   The light-emitting device using the organic electroluminescent element of any one of Claims 1-13.   The display apparatus using the organic electroluminescent element of any one of Claims 1-13. The illuminating device using the organic electroluminescent element of any one of Claims 1-13.