JP2002356462A - Arylbenzidiene derivative compound, organo- electroluminescent element material and organo- electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organo-electroluminescent element having a good ultimate brightness, excellently emitting light in blue violet to near ultraviolet and having a high brightness and a long life by using a novel luminescent compound. SOLUTION: This arylbenzidine derivative compound is expressed by general formula (I) (wherein R1 to R28 express each H or a substituent; at least one of R14 to R18 express a phenyl which may have a substituent; at least one of R19 to R23 express a phenyl which may have a substituent; further, the sum total of stereo parameters Es of the substituents of R1 , R2 , R3 and R4 is -7 to -2.5.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence (hereinafter abbreviated as organic EL) element, an organic electroluminescence element material, and a light-emitting compound. The present invention relates to an organic electroluminescence element, an organic electroluminescence element material, and a material thereof suitably used for consumer or industrial display devices such as panels.

[0002]

2. Description of the Related Art Electroluminescent displays (ELD) are used as light-emitting electronic display devices.
There is. ELD components include inorganic electroluminescent elements and organic electroluminescent elements. Inorganic electroluminescence elements have been used as flat light sources, but high voltage AC is required to drive the light emitting elements. An organic electroluminescence element has a configuration in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. Electrons and holes are injected into the light-emitting layer and recombination causes exciton (exciton) to be generated. An element that emits light by utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated and emits light at a voltage of about several V to several tens of volts. Because of this, it is rich in viewing angle dependence, has high visibility, and is a thin-film type completely solid-state device, and thus has attracted attention from the viewpoint of space saving and portability.

[0003] However, organic EL devices for practical use in the future include more efficient and higher brightness with lower power consumption.
There is a demand for the development of an organic EL device that emits light for a long life.

[0004] Various organic EL devices have been reported so far, but at present, only a monocolor or an area color has been put to practical use.

One of the conventional full-color organic EL devices is a system in which blue (B), green (G), and red (R) pixels are directly patterned. Since it is necessary to apply different colors, the yield at the time of manufacture is low, and the fact that a red light-emitting material having high color purity has not been found is an obstacle to practical use.

Further, the method of combining white light emission and a color filter described in Japanese Patent Application Laid-Open No. H7-220871 has disadvantages in that the light use efficiency is low and that the white light emitting element has a short life and low luminous efficiency. ing.

Further, in a system in which a blue light emitting material described in JP-A-3-152897 is used and a color conversion layer that absorbs the blue light and emits green or red light is applied, a light emitting element having three colors is used. It is not necessary to apply different colors to each other, and the production yield is improved. Further, in principle, the light use efficiency is also high.
However, using a material that emits blue EL light and attempting to emit red light by color conversion has the disadvantage that the color purity is poor. This is presumed to be because a plurality of organic compounds having a small Stokes shift are used as the compounds for color conversion, so that it is necessary to perform the color conversion a plurality of times when converting the color from blue to red.

[0008] In order to solve such a problem at the time of full color conversion, we have intensively studied a new full color conversion system. For example, EP1,067,16
No. 5, A, JP-A-2001-143869, a method has been devised in which blue light to near-ultraviolet EL light is used, the light is wavelength-converted by a phosphor, and BGR light is extracted.

In this method, since the light emission is blue-violet to near-ultraviolet, there is a possibility that an inorganic compound having a large Stokes shift, such as an Eu ³⁺ complex or an inorganic phosphor containing Eu ³⁺ , can be used. It is expected that red color can be obtained by the conversion, and that the color purity and luminous efficiency of red can be increased as compared with other methods.

When this method is adopted, a material that emits light in the blue-violet to near-ultraviolet range is required. However, a material that emits light with high luminance and long life in the blue-violet to near-ultraviolet range has not been found. Japanese Patent Application Laid-Open No. 3-152897 discloses that an organic electroluminescence device containing p-quarterphenyl is composed of 420 n
m, but the emission luminance was low and not sufficient.

[0011] When a polysilane compound disclosed in JP-A-11-26159 or the like is used, ultraviolet to near-ultraviolet light can be obtained relatively easily, but the polysilane compound is generally unstable. It is difficult to maintain this light emission at room temperature, and light emission at room temperature has recently been discovered, but the light emission efficiency is low, and when used as an organic EL device, the light emission lifetime is extremely short. Had.

In addition, simply using a material having fluorescence emission in the blue-violet to near-ultraviolet region as an organic EL device and laminating a conventionally known hole injection layer or hole transport layer,
It was found that desired blue-violet to near-ultraviolet light emission could not be obtained.

In the hole injection layer, 4,4 ', 4 "-tris [N- (3-methylphenyl) -N-phenylamino]
N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] -4,4 'is added to a hole transport layer such as triphenylamine (m-MTDATA).
-Diamine (TPD), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NP
D) etc., using a conventionally known material such as a hole injection layer,
Alternatively, when the organic EL device is used as a hole transporting layer, light emission from a compound of a hole injection layer or a hole transporting layer can be obtained even when a material having a shorter wavelength of blue violet to near ultraviolet is used for a light emitting layer. It was found that only blue light emission was obtained.

[0014] TPD is conventionally known as a material for the hole transporting layer, but has a fluorescent light emission, so that it can be used as a light emitting material. However, the emission color was blue and the emission wavelength was too long for our purpose and was not suitable.

Furthermore, JP-A-10-88119, which describes a compound similar to TPD, discloses a benzidine derivative in which a methyl group or a chlorine atom is introduced into the central biphenyl site of tetraarylbenzidine. JP-A-8-48656 discloses a benzidine derivative in which a dimethylamino group or a chlorine atom is similarly introduced.
However, these benzidine derivatives each have 2
Since the four outer aryl groups are replaced by biphenyl groups, the emission color becomes longer and the emission color changes from blue to blue-green, which is incompatible with our purpose because the emission wavelength is too long. Yes, means for further shortening the wavelength are required. In addition, these benzidine derivatives have poor thermal stability and thus have poor durability as an organic EL device.

[0016]

As described above, as an organic electroluminescence device, a long-life, high-brightness organic EL device that emits light in the blue-violet to near-ultraviolet wavelength range is used.
There is a need for an L element. In addition, there is a need for a new luminescent compound that can be adapted thereto.

The present invention has been made in view of the above situation. An object of the present invention is to provide a novel compound that emits light with high luminance and a long life from blue violet to near ultraviolet, an organic electroluminescent element that emits light with a high luminance, an organic electroluminescent element that has a long life, and an organic electroluminescent element that is easy to manufacture. At least one of the following.

[0018]

The object of the present invention is attained by the invention as described below.

1. A compound represented by the general formula (I).

[0020]

Embedded image

In the formula, R _{1 to} R ₂₈ each represent a hydrogen atom or a substituent, at least one of R _{14 to} R ₁₈ is a phenyl group which may have a substituent, and R _{19 to} R ₂₃ at least one is a phenyl group having a substituent, further the sum of R _1, R _2, R _3, and steric parameter E _S values of the substituents R ₄ are -7 or more, -2.5 It is as follows.

2. In the general formula (I), R ₁ ,
_2. The compound according to the above 1, wherein the substituent of R ₂ , R ₃ and R ₄ is a hydrogen atom or an alkyl group.

3. In the general formula (I), R ₁ ,
Compounds sum of R _2, steric parameter E _S values of the substituents R ₃ and R _4, -7 or more, characterized in that it is -3.7 or less.

4. In the general formula (I), R ₁ ,
The substituent of R ₂ , R ₃ and R ₄ is a hydrogen atom or an alkyl group, and the total number of carbon atoms contained in the substituents of R ₁ , R ₂ , R ₃ and R ₄ is 3 or more. 4. The luminescent compound as described in 3 above, wherein

[5] A compound represented by the following general formula (II):

[0026]

Embedded image

In the formula, R _{51 to} R ₇₈ each represent a hydrogen atom or a substituent, and at least one of R ₅₁ , R ₅₂ , R ₅₃ and R ₅₄ is an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group, It is a carboxyl group, an amide group, a trifluoromethyl group or an alkoxycarbonyl group.

6. In the general formula (II), R ₅₁ , R
Wherein at least two of ₅₂ , R ₅₃ and R ₅₄ are an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group, a carboxyl group, an amide group, a trifluoromethyl group, or an alkoxycarbonyl group. 5. The compound according to 5.

7. In the general formula (II), R ₅₁ , R
₅₂ , at least one of R ₅₃ and R ₅₄ is an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group, a carboxyl group, an amide group, a trifluoromethyl group or an alkoxycarbonyl group, and at least one of R _{59 to} R ₆₃ 6. The compound according to the above item 5, wherein one is a phenyl group which may have a substituent, and at least one of R _{69 to} R _{73 is} a phenyl group which may have a substituent.

8. In the general formula (II), R ₅₁ , R
_At least two of ₅₂ , R ₅₃ and R ₅₄ are an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group, a carboxyl group, an amide group, a trifluoromethyl group or an alkoxycarbonyl group, and at least one of R _{59 to} R ₆₃ 6. The compound according to the above item 5, wherein one is a phenyl group which may have a substituent, and at least one of R _{69 to} R _{73 is} a phenyl group which may have a substituent.

9. The compound according to any one of claims 1 to 8, wherein the compound is a fluorescent compound.

10. An organic electroluminescent device material comprising the compound according to any one of the above items 1 to 9.

11. An organic electroluminescent device comprising the compound according to any one of the above items 1 to 9.

12. 10. An organic electroluminescence device, comprising the compound according to any one of 1 to 9 above in a light-emitting layer.

13. 10. An organic electroluminescence device comprising the compound according to any one of 1 to 9 above in a hole transport layer.

14. Purplish of CIE chromaticity coordinates
14. The organic electroluminescent device according to the above item 11, 12 or 13, wherein the device emits light in a Blue (purple-blue), BluePurple (blue-violet) or Purple (purple) region.

15. A conversion layer containing at least one phosphor having a maximum emission wavelength in the range of 400 to 500 nm, and a conversion layer containing at least one phosphor having a maximum emission wavelength in the range of 501 to 600 nm. Layers and 601
15. The organic electroluminescence device according to the above 11, 12, 13 or 14, further comprising a conversion layer containing at least one kind of phosphor having a maximum emission wavelength in a range of from 700 to 700 nm.

Hereinafter, the present invention will be described in detail. The structure of the organic EL device will be described with reference to FIG.

The organic EL device comprises a light-emitting layer 1, an electrode composed of an anode 2 and a cathode 3, a hole transport layer 7 between the light-emitting layer and the anode, and an electron transport layer 6 between the light-emitting layer and the cathode. Are arranged and the light emitting layer 1 is sandwiched between the anode 2 and the cathode 3. Reference numeral 5 denotes a glass substrate. When an electric current is passed through the electrode, the organic compound contained in the light emitting layer 1 emits light. This is because positive and negative carriers are injected from the cathode 3 and the anode 2, and the carriers move and recombine in the organic layer, thereby forming a singlet excited state of the compound. It is considered that the compound emits light during the deactivation process. Organic EL
The device is further provided with a color conversion layer 4, which can convert the light of the compound contained in the light emitting layer into light having different wavelengths. As shown in FIG. 1, full color can be realized by providing three color conversion layers having different wavelength ranges.

We paid attention to TPD as a material having fluorescence emission from blue-violet light to near-ultraviolet light, and made intensive studies on shortening the wavelength by twisting the biphenyl site of tetraphenylbenzidine. As a result, by using the compound of the present invention, it was possible to produce an organic electroluminescence device that emits light with high luminance and a long life from blue violet to near ultraviolet.

The effect of the compound of the present invention was particularly remarkable when used as a hole transporting material and when used as a light emitting material.

When a material having fluorescent emission in blue-violet to near-ultraviolet light as in the present invention is used as a hole transport material in an organic EL device, if the fluorescent emission of the material of the light-emitting layer is blue-violet to near-ultraviolet light, , As it is, blue-violet to near-ultraviolet light emission can be obtained, and the fluorescent emission of the material of the light-emitting layer is longer blue-
In the case of red, the emission color is basically obtained.

The light-emitting layer in this specification refers to a layer that emits light when a current is applied to an electrode composed of a cathode and an anode in a broad sense. Specifically, it refers to a layer containing an organic compound that emits light when an electric current is applied to an electrode composed of a cathode and an anode. Usually, the light emitting layer has a structure in which the light emitting layer is sandwiched between a pair of electrodes. The organic EL device of the present invention has a hole injection layer, an electron injection layer, a hole transport layer, and an electron transport layer in addition to the light emitting layer, if necessary, and has a structure sandwiched between a cathode and an anode.

Specifically, (i) anode / light emitting layer / cathode (ii) anode / hole injection layer / light emitting layer / cathode (iii) anode / light emitting layer / electron injection layer / cathode (iv) anode / positive Hole injection layer / light emitting layer / electron injection layer / cathode (v) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode.

Further, a cathode buffer layer (for example, lithium fluoride) may be inserted between the electron injection layer and the cathode. Further, an anode buffer layer (for example, copper phthalocyanine, etc.) may be inserted between the anode and the hole injection layer.

In the light emitting layer, a hole injection layer, an electron injection layer, a hole transport layer, an electron transport layer, and the like may be provided on the light emitting layer itself. That is, (1) an injection function capable of injecting holes from an anode or a hole injection layer and injecting electrons from a cathode or an electron injection layer when an electric field is applied to the light emitting layer; (3) a light-emitting function that provides a field for the recombination of electrons and holes within the light-emitting layer and causes the light-emission to transfer light (electrons and holes) by an electric field;
In this case, at least one of a hole injection layer, an electron injection layer, a hole transport layer, and an electron transport layer needs to be provided separately from the light emitting layer. Will disappear. Further, a function as a light emitting layer may be imparted by including a compound that emits light in the hole injection layer, the electron injection layer, the hole transport layer, the electron transport layer, and the like. The light-emitting layer may have a difference between the ease of injecting holes and the ease of injecting electrons, and may have a large or small transport function represented by the mobility of holes and electrons. It is preferable to have a function of transferring at least one of the charges.

As a method for forming a light emitting layer using the above materials, for example, a vapor deposition method, a spin coating method, a casting method,
Although it can be formed by thinning by a known method such as the LB method, it is particularly preferably a molecular deposition film. Here, the molecular deposition film refers to a thin film formed by depositing the compound from a gaseous state or a film formed by solidifying the compound from a molten state or a liquid state. Usually, this molecular deposited film can be distinguished from a thin film (molecule accumulation film) formed by the LB method by a difference in an aggregated structure and a higher-order structure, and a functional difference caused by the difference.

This light emitting layer is disclosed in JP-A-57-517.
As described in No. 81, the light emitting material can be formed into a solution by dissolving the light emitting material in a solvent together with a binder such as a resin, and then thinning the solution by spin coating or the like. The thickness of the light emitting layer formed in this way is not particularly limited and can be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 μm.

The luminescent compound according to claim 1 of the present specification will be described. An E _S value defined by Tuft et al. Is known as a numerical value of the magnitude of steric hindrance of a substituent [American Chemical Society]
y Professional Reference
Book, 'Exploring QSAR', C.I. Ha
nsh A. Leo et al. R. [Hell Edit]. As a result of intensive studies on various benzidine derivatives, we have found that shortening can be achieved by introducing a substituent having this E _S value within a specific range into the central biphenyl site of the benzidine derivative.

Hereinafter, the E _S value will be described. R ₁ ,
The sum of R _2, R _3, steric parameter E _S values of the substituents R ₄ is -7 least -2.5 or less. Here, a three-dimensional parameter which is derived from the chemical reactivity and E _S values, it can be said that sterically bulky substituents smaller if this value is small.

Further, it has been found that even when the E _S value does not fall within this range, sufficiently high luminance and long life can be achieved by the specific substituent. The effect of the specific substituent can be presumed to be a case where the electronic effect is larger as well as the steric effect of the substituent.

Hereinafter, the E _S value will be described. In general,
It is known that in the hydrolysis reaction of an ester under acidic conditions, the effect of the substituent on the progress of the reaction may be considered to be only steric hindrance. Is a numerical value of the E _S value.

The E _S value of the substituent X is calculated by the following chemical reaction formula: X—CH ₂ COORx + H ₂ O → X—CH ₂ COOH + R
A reaction rate constant kX for hydrolyzing an α-monosubstituted acetic ester derived from α-monosubstituted acetic acid obtained by substituting one hydrogen atom of a methyl group of acetic acid with a substituent X represented by xOH 2 under acidic conditions. And the following chemical reaction formula: CH ₃ COORy + H ₂ O → CH ₃ COOH + RyOH (Ry is the same as Rx). From the reaction rate constant kH at this time, it can be obtained by the following equation.

E _S = log (kX / kH) The steric hindrance of the substituent X reduces the reaction rate, and as a result kX <kH, the E _S value is usually negative.

When the E _S value is actually obtained, the above two reaction rate constants kX and kH are obtained and calculated by the above formula.

[0056] Specific examples of E _S values, Unger, S.
H. Hansch, C .; Prog. Phys. Or
g. Chem. , 12, 91 (1976). In addition, "Structure-activity relationship of drugs" (Chemical field special issue No. 122, Nankodo), "American Ch
electronic Society Professional
al Reference Book, 'Explor
ing QSAR'p. 81 Table 3-3 "also has specific numerical values. The following is a part of it.

[0057]

[Table 1]

Here, it should be noted that the Es value as defined in the present specification is not defined as that of a methyl group as 0, but assuming that a hydrogen atom is 0 and that a methyl group is 0. is that in which minus 1.24 from the the E _S values.

In the general formula (I), R ₁ , R ₂ , R ₃ ,
_{R 4, R 5, R 6} , R 7, R 8, R 9, R 1 0, R 11, R 12, R
_{13, R 14, R 15,} R 16, R 17, R 18, R 19, R 20,
_{R 21, R 2 2, R} 23, R 24, R 25, R 26, R 27 and R ₂₈ each represents a hydrogen atom or a substituent.

R₁, R_Two, R_Three, R_Four, R_Five, R₆, R₇,
R₈, R₉, R_Ten, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅,
R₁₆, R₁₇, R₁₈, R₁₉, R₂₀, R_{twenty one}, R_{twenty two}, R_{twenty three}, R
_{twenty four}, R_{twenty five}, R₂₆, R₂₇And R₂₈Is each independently hydrogen
Represents an atom or a substituent; ₁~ R₂₈Represented by
As the substituent, an alkyl group (for example, a methyl group, an ethyl group
Group, isopropyl group, hydroxyethyl group,
Tyl group, trifluoromethyl group, perfluoropropyl
Group, perfluoro-n-butyl group, perfluoro-t-
Butyl group, t-butyl group, etc.), cycloalkyl group (eg,
Such as cyclopentyl and cyclohexyl), aralkyl
Group (for example, benzyl group, 2-phenethyl group, etc.), ant
Phenyl group, naphthyl group, p-tolyl group
Group, p-chlorophenyl group, etc.), alkoxy group (for example,
Ethoxy, isopropoxy, butoxy, etc.)
Oxy group (for example, phenoxy group and the like) and the like.
You. These groups may be further substituted, as described above.
As the substituent, a halogen atom, a hydrogen atom, trifluoro
Methyl group, cyano group, nitro group, alkyl group, aryl
Group, alkoxy group, aryloxy group, alkylthio
Group, dibenzylamino group, diarylamino group, etc.
Can be R₁₄Or R₁₈At least one of has a substituent
A phenyl group and R₁₉Or R_{twenty three}At least
One is a phenyl group which may have a substituent, and
₁, R_Two, R_ThreeAnd R_FourSteric parameter E of the substituent of _Svalue
Are −7 or more and −2.5 or less.

In the general formula (I), R ₁ , R ₂ , R ₃ ,
As R ₄ , an alkyl group is preferable, and among them, R ₁ , R
Most preferably, four of ₂ , R ₃ and R ₄ are methyl groups.

In the compound described in claim 2 of the present specification, in the general formula (I), the substituents of R ₁ , R ₂ , R ₃ and R ₄ are a hydrogen atom or an alkyl group, _1, R _2,
Most preferably, four of R ₃ and R ₄ are methyl groups.

[0063] In compounds according to claim 3 of the present specification, the general formula in (I), the sum of R _1, R _2, R _3, steric parameter E _S values of the substituents R ₄ are, -7 or more -3.
It is preferably 7 or less.

In the compound according to claim 4 of the present specification, in the general formula (I), the substituents of R ₁ , R ₂ , R ₃ and R ₄ are a hydrogen atom or an alkyl group; _1, R _2,
The sum of R _3, carbon atoms contained in the substituent R ₄ is a three or more, the sum of E _S values, -7 or more and -3.7 or less.

In the compound according to claim 5 of the present specification,
In general formula (II), R₅₁, R₅₂, R₅₃, R₅₄, R₅₅,
R₅₆, R₅₇, R₅₈, R ₅₉, R₆₀, R₆₁, R₆₂, R₆₃, R
₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, R ₇₁,
R₇₂, R₇₃, R₇₄, R₇₅, R₇₆, R₇₇And R₇₈Each
Represents a hydrogen atom or a substituent.
Then R₁~ R₃₈And those having the same meanings as the substituent represented by
Can be In the general formula (II), R₅₁, R
₅₂, R₅₃, R ₅₄At least one of the substituents is aryl
Amino group (for example, diphenylamino group, 3-methyldi
Phenylamino group, etc.), phenyl group, cycloalkyl
Groups (for example, cyclopentyl group, cyclohexyl group, etc.),
Alkenyl group (for example, vinyl group, propenyl group, etc.),
Ruboxyl group, amide group (for example, methylamide group,
Amide group, acetamido group, etc.), trifluoromethyl
Or an alkoxycarbonyl group (for example,
Xycarbonyl group, ethoxycarbonyl group, etc.)
You.

Among these substituents, an arylamino group and a phenyl group are preferred. In particular, an arylamino group is preferable, and among the arylamino groups, a diarylamino group is most preferable.

These groups may further have a substituent, and specifically include a halogen atom, a hydrogen atom, a trifluoromethyl group, a cyano group, a nitro group, an alkyl group, an aryl group, an alkoxy group, Preferred are an aryloxy group, an alkylthio group, a dibenzylamino group, a diarylamino group and the like.

In the general formula (II), R₅₁, R₅₂,
R₅₃, R₅₄, R₅₅, R₅₆, R₅₇, R ₅₈, R₅₉, R₆₀, R
₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈,
R₆₉, R ₇₀, R₇₁, R₇₂, R₇₃, R₇₄, R₇₅, R₇₆, R
₇₇And R₇₈Is a hydrogen atom, or the above substituent
Yes, R₅₁, R₅₂, R₅₃, And R₅₄At least two of
Is an arylamino group, a phenyl group, a cycloalkyl
Group, alkenyl group, carboxyl group, amide group, trif
A fluoromethyl group or an alkoxycarbonyl group
Is preferred.

In the general formula (II), R₅₁, R₅₂,
R₅₃, R₅₄, R₅₅, R₅₆, R₅₇, R₅₈, R₅₉, R₆₀, R
₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈,
R₆₉, R₇₀, R₇₁, R₇₂, R₇₃, R₇₄, R₇₅, R₇₆, R
₇₇And R₇₈Are each independently a hydrogen atom or R₁~
R₂₈Represents the same thing as the substituent represented by, preferably
Is R₅₉Or R₆₃At least one of may have a substituent
A phenyl group and R₆₉Or R₇₃At least one of
Is a phenyl group which may have a substituent;₅₁, R
₅₂, R₅₃, And R₅₄At least one of the substituents
Amino group, phenyl group, cycloalkyl group, alk
Nil group, carboxyl group, amide group, trifluoromethyl
Or an alkoxycarbonyl group.

Further, at least two of R ₅₁ , R ₅₂ , R ₅₃ and R ₅₄ are an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group, a carboxyl group, an amide group,
A trifluoromethyl group or an alkoxycarbonyl group is preferred.

The compounds represented by formulas (I) and (II) may or may not have fluorescence.
It is preferable to have fluorescence. In the present invention, a fluorescent compound is a compound that emits fluorescence when excited by irradiation with light having a wavelength within the absorption spectrum of the compound or by application of an electric field, and has a fluorescence quantum yield measured in a solution. The rate is 0.001 or more. Although the solution is not particularly limited, tetrahydrofuran, acetonitrile, toluene, ethyl acetate, methanol, ethanol,
Dimethylformamide and the like.

The color emitted by the organic compound of the present specification is as follows.
In Figure 4.16 on page 108 of the “New Color Science Handbook” (edited by The Japan Society of Color Science, The University of Tokyo Press, 1985), the results measured with a spectral radiance meter CS-1000 (manufactured by Minolta) were converted to CIE chromaticity coordinates. It is determined by the color at the time of fitting, and the measurement result enters “Purple Blue”, which is a purple-blue region of the CIE chromaticity coordinates, “Bluish Purple”, which is a blue-violet region, or “Purple”, which is a purple region. Say that.

The compounds represented by the general formulas (I) and (II) have a high glass transition temperature (Tg), and therefore have a sufficient thermal stability as a material for an organic electroluminescence device. Tg is preferably 100 degrees or more.

The compounds represented by the general formulas (I) and (II) are compounds emitting light with high luminance, and therefore, are naturally useful as compounds emitting light contained in a light emitting layer of an organic electroluminescence device. In addition, it can also be used as a material such as a labeling compound for medicines utilizing fluorescence by utilizing the above properties.

The molecular weight of the compounds represented by formulas (I) and (II) is preferably in the range of 500 to 2,000. When the molecular weight is within this range, the light emitting layer can be easily produced by a vacuum deposition method, and the production of the organic EL device becomes easy. Further, the thermal stability of the organic compound in the organic EL device is improved.

The compounds represented by the general formulas (I) and (II) may be any one of a hole injection layer, an electron injection layer, a hole transport layer and an electron transport layer, in addition to the light emitting layer of the organic EL device. Can also be used. Preferably, it is a light emitting layer, a hole injection layer, or a hole transport layer.

The specific examples of the compounds represented by formulas (I) and (II) of the present invention are shown below, but the present invention is not limited thereto.

Specific examples of the compound of the general formula (I)

[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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Specific examples of the compound of the general formula (II)

[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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[0095]

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[0096]

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[0097]

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[0098]

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[0099]

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[0100]

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Next, the hole injection layer and the electron injection layer will be described. The hole injection layer has a function of transmitting holes injected from the anode to the light emitting layer. By interposing the hole injection layer between the anode and the light emitting layer, a large number of holes can be formed at a lower electric field. Is injected into the light emitting layer, and the electrons injected from the cathode or the electron injection layer into the light emitting layer are accumulated at the interface in the light emitting layer due to the electron barrier existing at the interface between the light emitting layer and the hole injection layer. An element having excellent light emission performance such as improved efficiency is obtained. The material of the hole injection layer (hereinafter, referred to as a hole injection material) is not particularly limited as long as it has the above preferable properties.
Materials commonly used as charge injection / transport materials for holes and E
Any of the known materials used for the hole injection layer of the L element can be selected and used.

The hole injecting material has either hole injecting or electron barrier properties, and may be either an organic or inorganic material. As this hole injection material,
For example, triazole derivatives, oxadiazole derivatives,
Imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers And a conductive polymer oligomer, particularly a thiophene oligomer. As the hole injecting material, those described above can be used, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.

Representative examples of the above aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'
-Tetraphenyl-4,4'-diaminophenyl;
N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine (TPD); 2,2-bis (4-di-p-tolyl Aminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ',
N'-tetra-p-tolyl-4,4'-diaminobiphenyl; 1,1-bis (4-di-p-tolylaminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl ) Phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N'-di (4-methoxyphenyl) -4,4'-diaminobiphenyl;
N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) biphenyl; N, N, N-tri (p-tolyl) amine; 4- (di- p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene; 4-N,
N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4'-N, N-diphenylaminostilbenzene; N-phenylcarbazole, and further described in U.S. Pat. No. 5,061,569. Having two fused aromatic rings in the molecule, for example, 4,
4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), 4, in which three triphenylamine units described in JP-A-4-308688 are connected in a star-burst form; 4 ', 4 "-tris [N- (3-methylphenyl) -N-phenylamino]
Triphenylamine (MTDATA) and the like.

Further, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.
This hole injection layer can be formed by thinning the above hole injection material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, and an LB method. The thickness of the hole injection layer is not particularly limited,
Usually, it is about 5 nm to 5 μm. This hole injection layer is
It may have a single-layer structure composed of one or more of the above materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

The electron injecting layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and any material may be selected from conventionally known compounds. it can. Examples of a material used for the electron injection layer (hereinafter, referred to as an electron injection material) include heterocyclic tetracarboxylic anhydrides such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, and naphthalene perylene; carbodiimide; Examples include fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like. Further, a series of electron-transporting compounds described in JP-A-59-194393 are disclosed as materials for forming a light-emitting layer in the publication. It has been found that it can be used as a material. Further, in the oxadiazole derivative, a thiadiazole derivative in which an oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as the electron injecting material. Also, a metal complex of an 8-quinolinol derivative, for example, tris (8-quinolinol)
Aluminum (Alq), Tris (5,7-dichloro-
8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, tris (2
-Methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metal of these metal complexes is In, Mg, Cu, Ca, S
A metal complex replaced with n, Ga or Pb can also be used as an electron injection material. In addition, metal-free or metal phthalocyanine, or those whose terminals are substituted with an alkyl group, a sulfonic acid group, or the like, can also be preferably used as an electron injection material. In addition, a distyrylpyrazine derivative exemplified as a material for the light emitting layer can also be used as an electron injecting material, and an inorganic semiconductor such as n-type Si or n-type SiC is also used as an electron injecting material like the hole injecting layer. be able to.

The electron injection layer can be formed by forming the above compound by a known thinning method such as a vacuum evaporation method, a spin coating method, a casting method, and an LB method. The thickness of the electron injection layer is not particularly limited, but is usually selected in the range of 5 nm to 5 μm. The electron injection layer may have a single-layer structure composed of one or two or more of these electron injection materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

Next, a preferred example of manufacturing an organic EL device will be described. As an example, a method of manufacturing an EL device comprising the above-mentioned anode / hole injection layer / light-emitting layer / electron injection layer / cathode will be described. First, a thin film made of a desired electrode material, for example, a material for an anode, is formed on a suitable substrate. Is formed to a thickness of 1 μm or less, preferably in the range of 10 nm to 200 nm by a method such as vapor deposition or sputtering to produce an anode. Next, a hole injection layer, which is a device material,
A thin film made of a material for the light emitting layer and the electron injection layer is formed.

Further, a buffer layer (electrode interface layer) may be present between the anode and the light emitting layer or the hole injection layer and between the cathode and the light emitting layer or the electron injection layer.

The buffer layer is a layer provided between an electrode and an organic layer for lowering the driving voltage and improving the luminous efficiency.
The details are described in Vol. 2, Chapter 2, "Electrode Materials" (pages 123 to 166) of Vol. is there.

The anode buffer layer is described in JP-A-9-4547.
No. 9, No. 9-260062, No. 8-288680, etc., the details thereof are also described. Specific examples thereof include a phthalocyanine buffer layer represented by copper phthalocyanine,
Examples thereof include an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.

The cathode buffer layer is described in JP-A-6-3258.
No. 71, No. 9-17574, No. 10-74586, and the like, and the details thereof are specifically described. Specifically, a metal buffer layer represented by strontium, aluminum, or the like;
Examples thereof include an alkali metal compound buffer layer represented by lithium fluoride, an alkaline earth metal compound buffer layer represented by magnesium fluoride, and an oxide buffer layer represented by aluminum oxide.

It is desirable that the buffer layer is a very thin film.
A range of 0 nm is preferred.

Further, layers having other functions may be laminated as necessary in addition to the above-mentioned basic constituent layers. For example, JP-A-11-204258 and JP-A-11-204359, and "Organic EL devices and their industrialization" The forefront (January 1998
No. 237 of January 30 (published by NTT Systems Corporation)
It may have a functional layer such as a hole blocking (hole blocking) layer described on a page or the like.

In the buffer layer, at least one of the compounds of the present invention may be present in at least one of the cathode buffer layer and the anode buffer layer, and may function as a light emitting layer.

Next, the electrodes of the organic EL device will be described. The electrodes of the organic EL element are composed of a cathode and an anode.

As the anode in this organic EL device,
A metal, an alloy, an electrically conductive compound, or a mixture thereof having a large work function (4 eV or more) as an electrode material is preferably used. Specific examples of such an electrode material include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ , and ZnO.

The above-mentioned anode may be formed by forming a thin film of these electrode substances by a method such as vapor deposition or sputtering, and forming a pattern of a desired shape by a photolithography method. (About 100 μm or more), a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material. When light is extracted from the anode, the transmittance is desirably greater than 10%, and the sheet resistance of the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually 10 nm to 1 μm.
m, preferably in the range of 10 nm to 200 nm.

On the other hand, as the cathode, a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are used as an electrode material. Specific examples of such an electrode material include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum /
Examples include an aluminum oxide (Al ₂ O ₃ ) mixture, indium, a lithium / aluminum mixture, and a rare earth metal. Among them, a mixture of an electron-injecting metal and a second metal which is a metal having a large work function and a stable work function, such as a magnesium / silver mixture, magnesium, / Aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, lithium / aluminum mixture, and the like are preferable. The cathode is
These electrode substances can be manufactured by forming a thin film by a method such as evaporation or sputtering. Further, the sheet resistance as the cathode is preferably several hundreds Ω / □ or less, and the film thickness is usually selected in the range of 10 nm to 1 μm, preferably 50 to 200 nm. In order to transmit light, if either the anode or the cathode of the organic EL element is transparent or translucent, the luminous efficiency is advantageously improved.

Next, a method for manufacturing an organic EL device will be described. Examples of the method for thinning include the spin coating method, the casting method, and the vapor deposition method as described above, but the vacuum vapor deposition method is preferable because a uniform film is easily obtained and pinholes are hardly generated. When adopting a vacuum evaporation method for thinning, the evaporation conditions include the type of compound used,
In general, the boat heating temperature is 50 to 450 ° C., the degree of vacuum is 10 ⁻⁶ to 10 ⁻³ Pa, and the deposition rate is 0.01 to 50 nm / depending on the target crystal structure and association structure of the molecular deposition film.
It is desirable that the temperature is appropriately selected within a range of seconds, a substrate temperature of −50 to 300 ° C., and a film thickness of 5 nm to 5 μm.

After forming these layers, a thin film made of a material for a cathode is formed thereon with a thickness of 1 μm or less, preferably 50 to 200 nm.
A desired organic EL device can be obtained by forming a film having a thickness in the range of m by, for example, a method such as vapor deposition or sputtering and providing a cathode. In the production of this organic EL device, it is preferable to produce from the hole injection layer to the cathode consistently by one evacuation, but the production order is reversed,
A cathode, an electron injection layer, a light emitting layer, a hole injection layer, and an anode can be formed in this order. When a DC voltage is applied to the organic EL device thus obtained, the anode is set to +,
When a voltage of about 5 to 40 V is applied with the negative polarity of the cathode, light emission can be observed. Also, even if a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state. The waveform of the applied alternating current may be arbitrary.

Next, the color conversion layer will be described. In a broad sense, the color conversion layer referred to in this specification refers to a layer that converts light emitted from a light emitting layer of an organic EL element into light of a different wavelength. Specifically, it refers to a layer containing a substance that absorbs light emitted from the light-emitting layer and emits light of different wavelengths.

In the organic EL device according to the twelfth aspect of the present invention, the color conversion layer emits light having a maximum emission wavelength in the range of 400 to 500 nm when excited by the emission wavelength of the compound in the emission layer. A color conversion layer containing an inorganic compound, a color conversion layer containing an inorganic compound which emits light having a maximum emission wavelength within the range of 501 to 600 nm when excited by the emission wavelength of the compound in the emission layer. It is preferable to have at least one color conversion layer containing an inorganic compound that emits light having a maximum emission wavelength within the range of 601 to 700 nm when excited by the emission wavelength of the compound.

By making all the color conversion materials contained in the color conversion layer an inorganic compound, a full-color organic E
In the L element, an organic EL element having a long life and low power consumption can be provided.

Further, as long as efficient full-color printing can be achieved, four or more color conversion layers may be provided.

The inorganic compound contained in the color conversion layer of the organic EL device of the present invention is preferably an inorganic phosphor or a rare earth complex phosphor.

Although the composition of the inorganic phosphor is not particularly limited,
Y ₂ O ₂ S, Zn ₂ SiO ₄ , Ca ₅ (P
O ₄ ) ₃ Cl and other metal oxides and ZnS, Sr
Sulfides represented by S, CaS, etc. include Ce, Pr, N
d, Pm, Sm, Eu, Gd, Tb, Dy, Ho, E
ions of rare earth metals such as r, Tm, Yb, Ag, Al,
It is preferable to combine metal ions such as Mn, In, Cu, and Sb as activators or co-activators.

The crystal matrix will be described in more detail. As the crystal matrix, a metal oxide is preferable. For example, (X) ₃ Al
₁₆ O ₂₇ , (X) ₄ Al ₁₄ O ₂₅ , (X) ₃ Al ₂ Si ₂ O ₁₀ ,
(X) ₄ Si ₂ O ₈ , (X) ₂ Si ₂ O ₆ , (X) ₂ P ₂ O ₇ ,
(X) ₂ P ₂ O ₅ , (X) ₅ (PO ₄ ) ₃ Cl, (X) ₂ Si ₃
O ₈ -2 (X) Cl ₂ [wherein, X represents an alkaline earth metal. The alkaline earth metal represented by X may be a single component or a mixture of two or more components, and the mixing ratio thereof may be arbitrary.) Phosphoric acid, halophosphoric acid and the like are mentioned as typical crystal bases.

Other preferable crystal bases include oxides and sulfides of zinc, oxides of rare earth metals such as yttrium, gadolinium and lanthanum, and a part of oxygen of the oxides converted to sulfur atoms (sulfides). And sulfides of rare-earth metals, and oxides and sulfides thereof mixed with an arbitrary metal element.

Preferred examples of the crystal base are listed below.
Mg_FourGeO_5.5F, Mg_FourGeO₆, ZnS, Y_TwoO_TwoS,
Y_ThreeAl_FiveO₁₂, Y_TwoSiO_Ten, Zn_TwoSiO_Four, Y_TwoO_Three,
BaMgAl_TenO₁₇, BaAl₁₂O₁₉, (Ba, Sr,
Mg) O ・ aAl_TwoO_Three, (Y, Gd) BO_Three, (Zn,
Cd) S, SrGa_TwoS_Four, SrS, GaS, SnO_Two,
Ca_Ten(PO_Four)₆(F, Cl)_Two, (Ba, Sr) (M
g, Mn) Al_TenO₁₇, (Sr, Ca, Ba, Mg)_Ten
(PO_Four)₆Cl_Two, (La, Ce) PO_Four, CeMgAl
₁₁O₁₉, GdMgB_FiveO_Ten, Sr_TwoP _TwoO₇, Sr_FourAl₁₄
O_{twenty five}, Y_TwoSO_Four, Gd_TwoO_TwoS, Gd_TwoO_Three, YVO_Four, Y
(P, V) O_FourAnd so on.

The above-mentioned crystal base and activator or co-activator may be partially replaced with homologous elements.
There is no particular limitation on the elemental composition, as long as it absorbs light in the ultraviolet region or light in the purple region and emits visible light.

In the present invention, La, Eu, Tb and C are preferred as activators and coactivators of the inorganic phosphor.
e, ions of lanthanoid elements typified by Yb, Pr, and the like, and ions of metals such as Ag, Mn, Cu, In, and Al.
Mol% is preferable, and 0.01 to 50 mol% is more preferable.

The activator and co-activator are doped into the crystal by replacing some of the ions constituting the crystal matrix with ions such as the lanthanoid.

The actual composition of the phosphor crystal is strictly described.
Then the composition formula is as follows, but the amount of activator is
Often does not affect the intrinsic fluorescence properties,
Unless otherwise specified, the values of x and y below are described.
No. For example, Sr _4-xAl₁₄O_{twenty five}: Eu
²⁺ _xIs Sr in the present invention._FourAl₁₄O_{twenty five}: Eu²⁺And table
Write.

The representative inorganic phosphors (crystal matrix and
Composition formula of inorganic phosphor composed of activator)
However, the present invention is not limited to these.
(Ba _zMg_1-z)_3-xyAl₁₆O₂₇: Eu²⁺ _x, M
n²⁺ _y, Sr_4-xAl₁₄O_{twenty five}: Eu²⁺ _x, (Sr_1-zB
a_z)_1-xAl_TwoSi_TwoO₈: Eu²⁺ _x, Ba_2-xSiO_Four: E
u²⁺ _x, Sr_2-xSiO_Four: Eu²⁺ _x, Mg_2-xSiO_Four: E
u²⁺ _x, (BaSr)_1-xSiO_Four: Eu²⁺ _x, Y_2-xyS
iO_Five: Ce³⁺ _x, Tb³⁺ _y, Sr_2-xP_TwoO_Five: Eu²⁺ _x,
Sr_{Two -x}P_TwoO₇: Eu²⁺ _x, (Ba_yCa_zMg_1-yz)_5-x
(PO_Four)_ThreeCl: Eu_{2 + x}, Sr_2-xSi_ThreeO₈-2SrC
l_Two: Eu²⁺ _x[X, y and z are arbitrary 1 or less
Represents the number of The following shows the inorganic phosphor preferably used in the present invention.
However, the present invention is not limited to these compounds.
No. [Blue light emitting inorganic phosphor] (BL-1) Sr_TwoP_TwoO₇: Sn⁴⁺ (BL-2) Sr_FourAl₁₄O_{twenty five}: Eu²⁺ (BL-3) BaMgAl_TenO₁₇: Eu²⁺ (BL-4) SrGa_TwoS_Four: Ce³⁺ (BL-5) CaGa_TwoS_Four: Ce³⁺ (BL-6) (Ba, Sr) (Mg, Mn) Al_Ten
O₁₇: Eu²⁺ (BL-7) (Sr, Ca, Ba, Mg)_Ten(PO
_Four)₆Cl_Two: Eu²⁺ (BL-8) BaAl_TwoSiO₈: Eu²⁺ (BL-9) Sr_TwoP_TwoO₇: Eu²⁺ (BL-10) Sr_Five(PO_Four)_ThreeCl: Eu²⁺ (BL-11) (Sr, Ca, Ba)_Five(PO_Four)_ThreeC
l: Eu²⁺ (BL-12) BaMg_TwoAl₁₆O₂₇: Eu²⁺ (BL-13) (Ba, Ca)_Five(PO_Four)_ThreeCl: E
u²⁺ (BL-14) Ba_ThreeMgSi_TwoO₈: Eu²⁺ (BL-15) Sr_ThreeMgSi_TwoO₈: Eu²⁺ [Green-emitting inorganic phosphor] (GL-1) (Ba, Mg) Al₁₆O₂₇: Eu²⁺,
Mn²⁺ (GL-2) Sr_FourAl₁₄O_{twenty five}: Eu²⁺ (GL-3) (Sr, Ba) Al_TwoSi_TwoO₈: Eu
²⁺ (GL-4) (Ba, Mg)_TwoSiO_Four: Eu²⁺ (GL-5) Y_TwoSiO_Five: Ce³⁺, Tb³⁺ (GL-6) Sr_TwoP_TwoO₇-Sr_TwoB_TwoO_Five: Eu²⁺ (GL-7) (Ba, Ca, Mg)_Five(PO_Four)_ThreeC
l: Eu²⁺ (GL-8) Sr_TwoSi_ThreeO₈-2SrCl_Two: Eu²⁺ (GL-9) Zr_TwoSiO_Four, MgAl₁₁O₁₉: Ce
³⁺, Tb³⁺ (GL-10) Ba_TwoSiO_Four: Eu²⁺ (GL-11) Sr_TwoSiO_Four: Eu²⁺ (GL-12) (Ba, Sr) SiO_Four: Eu²⁺ (GL-13) SrGa_TwoS_Four: Eu²⁺ [Red-Emitting Inorganic Phosphor] (RL-1) Y_TwoO_TwoS: Eu³⁺ (RL-2) YAlO_Three: Eu³⁺ (RL-3) Ca_TwoY_Two(SiO_Four)₆: Eu³⁺ (RL-4) LiY₉(SiO_Four)₆O_Two: Eu³⁺ (RL-5) YVO_Four: Eu³⁺ (RL-6) CaS: Eu³⁺ (RL-7) Gd_TwoO_Three: Eu³⁺ (RL-8) Gd_TwoO_TwoS: Eu³⁺ (RL-9) Y (P, V) O_Four: Eu³⁺ (RL-10) Mg_FourGeO_5.5F: Mn⁴⁺ (RL-11) Mg_FourGeO₆: Mn⁴⁺ The inorganic phosphor is subjected to a surface modification treatment as necessary.
As a method, use of a silane coupling agent
By chemical treatment or fine particles of submicron order
By physical treatment by the addition of
And the like in combination.

Examples of the silane coupling agent used in the present invention include “NUC silicone silane coupling agent” issued by Nippon Unicar Co., Ltd. (August 2, 1997).
Those described in the catalog can be used as they are, and specific examples thereof include, for example, β- (3,4-epoxycyclohexyl) -ethyl trialkoxysilane, glycidyloxyethyltriethoxysilane, and γ-acryloyloxy-n-propyl. Tri-n-propyloxysilane,
γ-methacryloyloxy-n-propyl-n-propyloxysilane, di (γ-acryloyloxy-n-propyl) di-n-propyloxysilane, acryloyloxydimethoxyethylsilane, N-β (aminoethyl) γ-amino Propyltrimethoxysilane, N-β
(Aminoethyl) γ-aminopropylmethyldimethoxysilane, γ-aminopropyltriethoxysilane, N-
Phenyl-γ-aminopropyltrimethoxysilane, γ
-Mercaptopropyltrimethoxysilane and the like.

The fine particles used in the present invention are preferably inorganic fine particles, for example, fine particles of silica, titania, zirconia, zinc oxide and the like.

As the rare earth complex phosphor, Ce, Pr, Nd, Pm, Sm, Eu, Gd, T
Examples include those having b, Dy, Ho, Er, Tm, Yb, and the like. The organic ligand forming the complex may be either aromatic or non-aromatic, and is represented by the following general formula (B). The compounds represented are preferred.

[0138] Formula _{(B) Xa- (L x)} - (L y) n - in (L _z) -Ya _{Formula, L x, L y, L} z has two or more bonding hands independently X represents an atom; n represents 0 or 1;
Represents a substituent having an atom capable of coordination adjacent to L _x , and Ya represents a substituent having an atom capable of coordination adjacent to L _Z. Further may form a ring condensed with each other with any part and L _x of Xa, any portion of Ya and L _z
May be condensed with each other to form a ring, L _x and L _z may be condensed with each other to form a ring, and at least one aromatic hydrocarbon ring or aromatic hetero ring is present in the molecule. Exist. Where Xa− (L _x ) − (L _y ) _n − (L _z ) −
Ya is a β-diketone derivative or a β-ketoester derivative,
The oxygen atom of the β-keto amide derivative or the ketone is replaced with a sulfur atom or —N (R ₂₀₁ ) —, where R ₂₀₁ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. In the case where crown ether, aza crown ether, thia crown ether or crown ether in which crown oxygen is replaced by an arbitrary number of sulfur atoms or —N (R ₂₀₁ ) —, an aromatic hydrocarbon ring or The aromatic heterocyclic ring may not be present.

In the general formula (B), the coordinating atoms represented by Xa and Ya are specifically oxygen, nitrogen, sulfur, selenium and tellurium, especially oxygen, It is preferably a nitrogen atom or a sulfur atom.

In the general formula (B), the atom having two or more bonds represented by L _x , L _y , and L _z is not particularly limited, but is typically a carbon atom, an oxygen atom, Examples thereof include a nitrogen atom, a silicon atom, and a titanium atom, and a preferable one is a carbon atom.

Specific examples of the rare earth complex phosphor represented by the general formula (B) are shown below, but the present invention is not limited to these. Specifically, Japanese Patent Application Laid-Open No. 2001-14386
RE-1 to RE-29 and RF-1 to R described in 9 above
F-21.

[0142]

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[0143]

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[0147]

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[0148]

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[0149]

EXAMPLES The present invention will be described below in detail with reference to examples, but embodiments of the present invention are not limited thereto.

Example 1 Synthesis of Compound Synthesis Example 1-1 Synthesis of Compound (1) After degassing, under nitrogen atmosphere, 0.20 g of bisdibenzylideneacetone palladium and 0.1 ml of tri-tert-butylphosphine were dehydrated with toluene. Dissolved in 40 ml. Then, 3.6 g of m-toluidine and bromobiphenyl 8.
4 g and 4.8 g of sodium tert-butoxide were added, and the mixture was stirred with heating at room temperature for 4 hours. Then, in the reaction solution,
After adding tetrahydrofuran, ethyl acetate and water, the mixture was filtered through diatomaceous earth, and the organic layer was extracted. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography at a ratio of ethyl acetate and hexane of 1:14, and then recrystallized from acetonitrile to obtain 4.7 g of compound (1-1). (60% yield).

[0151]

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20 g of 3,5-dimethylnitrobenzene,
50 g of zinc powder was heated in 100 ml of ethanol, and when refluxed, the heating was stopped and then 30% NaOH
100 ml of an aqueous solution was added dropwise. When the boiling stopped, the heating was resumed, and the mixture was refluxed for 5 hours. After filtration of the insoluble matter, another 50 ml of ethanol was added to the insoluble matter and the mixture was refluxed, and the filtrates were collected and ethanol was distilled off. 100 ml of ethyl acetate and 30% acetic acid-0.
A 50 mol / L aqueous sodium bisulfite solution (50 ml) was added, and the mixture was separated. After washing with water (50 ml) three times, ethyl acetate was distilled off to obtain 14.0 g of an orange crude product. Further recrystallization in hexane gave 11.0 g of the compound (1
A-2) was obtained.

Compound (1A-2) (11.0 g) was dissolved in degassed 10% hydrochloric acid (500 ml) and refluxed for 6 hours. After cooling, the suspension was filtered, and a 20% sodium hydroxide solution was added until the solution became cloudy, and neutralized. Ethyl acetate (200 ml) was added for extraction, the organic phase was dehydrated with magnesium sulfate, and ethyl acetate was distilled off to obtain 10.0 g of a red-purple crude product. Recrystallization was performed with a hexane: toluene = 2: 1 solution,
7.1 g of a dark red powder was obtained (65% yield). NMR,
The compound (1) was analyzed by mass spectrum and amine coloring reagent.
A-3) was confirmed.

Compound (1A-3) (3.4 g) was added to 30 ml
Dissolved in 10% hydrochloric acid and sodium nitrite in an ice bath.
A solution of 14 g dissolved in 21 ml of water was added dropwise with stirring. After stirring for 1 hour after dropping, 10% copper (I) bromide-
Poured into 214 ml of 48% hydrogen bromide solution. 50 more
C. and stirred for 4 hours. After cooling, ethyl acetate 15
After extracting with 0 ml and drying with magnesium sulfate, the solvent was distilled off, and the residue was purified by column chromatography in a ratio of ethyl acetate and hexane of 1: 5 to give compound (1A-4) as 2.4.
g (yield 53%).

After degassing, 0.23 g of palladium acetate and 1.0 g of tri-tert-butylphosphine were added under a nitrogen atmosphere.
ml was dissolved in 20 ml of dehydrated xylene. Then, (1
2 g of A-4), 3 g of compound (1-1), and 1.2 g of sodium tert-butoxide were added, and the mixture was heated and stirred at 120 degrees for 4 hours. Thereafter, tetrahydrofuran, ethyl acetate and water were added to the reaction solution, and the mixture was filtered through diatomaceous earth, and the organic layer was extracted. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the ratio of toluene to cyclohexane was 1: 1.
After purification by column chromatography of No. 4, recrystallization from toluene yielded 1.8 g of the desired compound (1) (46% yield).

The product was identified as the target compound (1) by NMR and mass spectrum.

[0157]

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Synthesis Example 1-2 Synthesis of Compound (2) After degassing, 2.6 g of iododulene was dissolved in 20 ml of dehydrated xylene under a nitrogen atmosphere, and 1.6 g of copper powder and 6 g of potassium carbonate were added. This reaction solution was heated and stirred at 250 ° C. for 6 hours. After completion of the reaction, 1 mol /
Hydrochloric acid was added to carry out liquid separation, and an organic layer was extracted. After dehydration with magnesium sulfate, the solvent was distilled off to remove bididelen (2A-
0.8 g of 1) was obtained.

0.8 g of bidediene was added to 20 m of methylene chloride.
and a solution of 0.4 ml of bromine diluted 10-fold with methylene chloride was added dropwise under ice-cooling. After stirring for 2 hours under ice-cooling, methylene chloride was distilled off to obtain a pale yellow crude product. This was recrystallized from acetonitrile to obtain 0.8 g of the compound (2A-2) (yield: 62).
%).

0.1 g of palladium acetate and tri-tert
-0.3 ml of butylphosphine in 15 ml of dehydrated xylene
Was dissolved. Thereafter, 0.8 g of (2A-2), 1.0 g of compound (1-1), and 0.4 g of sodium tert-butoxide were added, and the mixture was heated and stirred at 120 ° C. for 4 hours. Thereafter, tetrahydrofuran, ethyl acetate and water were added to the reaction solution, and the mixture was filtered through diatomaceous earth, and the organic layer was extracted. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure.
After purification by column chromatography with a ratio of toluene to cyclohexane of 1: 7, recrystallization from toluene yielded 0.7 g of compound (2) (yield 45%).

The product was identified as the target compound (2) by NMR and mass spectrum.

[0162]

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Synthesis Example 1-3 Synthesis of Compound (5-9) 12 g of 2,5-dibromonitrobenzene and 6 g of copper powder were added to 8
Dissolved in 0 ml of dimethylformamide for 2 hours,
The mixture was heated and stirred at ℃. After cooling, the reaction solution was filtered through diatomaceous earth. Water was poured into the filtrate, which was filtered again. An organic layer was extracted by adding tetrahydrofuran, ethyl acetate and water to the obtained crystals, and dried over magnesium sulfate. After distilling off the solvent, the residue was recrystallized from ethanol to obtain 6 g of 4,4'-dibromo-2,2'-dinitrobiphenyl (yield 70).
%).

To a 50 ml ethanol solution in which 4 g of 4,4'-dibromo-2,2'-dinitrobiphenyl and 20 ml of concentrated hydrochloric acid were dissolved, 4.7 g of tin was gradually added. After heating the reaction solution to reflux for 30 minutes, it is poured into ice water and
Neutralized with 0% aqueous sodium hydroxide. After adding ethyl acetate, the organic layer was extracted and dried over magnesium sulfate. Evaporate the solvent and recrystallize with ethanol 3g
4,4'-dibromo-2,2'-diaminobiphenyl was obtained (yield 95%).

After degassing, 2 g of 4,4'-dibromo-2,2'-diaminobiphenyl, 10 g of iodobenzene, 2 g of copper and 6.4 g of potassium carbonate were added under a nitrogen atmosphere. The mixture was heated and stirred for an hour. Thereafter, tetrahydrofuran, ethyl acetate and water were added to the reaction solution, and the mixture was filtered through diatomaceous earth, and the organic layer was extracted. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was recrystallized from tetrahydrofuran to obtain 1.9 g of compound (5A-1) (yield: 51%).

After degassing, under nitrogen atmosphere, 0.08 g of palladium acetate and 0.3 of tri-tert-butylphosphine were added.
ml was dissolved in 30 ml of dehydrated xylene. Thereafter, 1 g of the compound (5A-1), 1.0 g of the compound (1-1),
0.4 g of sodium-tert-butoxide are added,
The mixture was heated and stirred at 120 ° C. for 4 hours. Thereafter, tetrahydrofuran, ethyl acetate and water were added to the reaction solution, and the mixture was filtered through diatomaceous earth, and the organic layer was extracted. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography with a toluene / hexane ratio of 1: 3, and then recrystallized from ethyl acetate to obtain 0.8 g of the desired compound (5-9).
Was obtained (yield 61%).

[0167]

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The product was identified as the target compound (5-9) by NMR and mass spectrum.

Synthesis Example 1-4 Synthesis of Compound (5-21) The same procedure as in Synthesis Example 1-3 was repeated except that compound (1-1) was replaced with 3-methyldiphenylamine. ) Got. After distilling off the solvent under reduced pressure,
After purification by column chromatography with a ratio of toluene to hexane of 1: 3, recrystallization from ethyl acetate gave 0.8 g of compound (5-21).

According to NMR and mass spectrum, it was confirmed to be compound (5-21). Melting point 175-
177 ° C.

Example 2 The electroluminescent element No. Preparation of 2-1 to 2-18 <Preparation of organic EL element> 100 mm × 100 as anode
After patterning a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which 150 nm of ITO (indium tin oxide) was formed on a glass substrate of mm × 1.1 mm, a transparent support substrate provided with the ITO transparent electrode was placed on a substrate. Ultrasonic cleaning with isopropyl alcohol, drying with dry nitrogen gas,
V ozone cleaning was performed for 5 minutes.

This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of m-MTDATXA was put in a molybdenum resistance heating boat, and the comparative compound (1) was placed in another molybdenum resistance heating boat. 20
0 mg, and 200 mg of bathocuproine (BC) was further placed in another molybdenum resistance heating boat, and attached to a vacuum evaporation apparatus. Next, after reducing the pressure in the vacuum chamber to 4 × 10 ⁻⁴ Pa, the heating boat containing m-MTDATXA was energized and heated to 220 ° C., and the deposition rate was 0.1 to
Deposited on a transparent support substrate at 0.3 nm / sec.
nm hole transport layer was provided. Furthermore, the comparative compound (1)
Was supplied to the heating boat and heated to 220 ° C., and was vapor-deposited on the hole transport layer at a vapor deposition rate of 0.1 to 0.3 nm / sec to provide a light-emitting layer having a thickness of 33 nm. In addition, the substrate temperature at the time of vapor deposition was room temperature. Furthermore, the heating boat containing BC is energized and heated to 250 ° C.
An electron injection layer having a thickness of 33 nm was formed by vapor deposition on the light emitting layer at a vapor deposition rate of 0.1 nm / sec. In addition, the substrate temperature at the time of vapor deposition was room temperature.

Next, a vacuum chamber was opened, a stainless steel rectangular perforated mask was placed on the electron injection layer, and 3 g of magnesium was put into a molybdenum resistance heating boat.
0.5 g of silver was put into a tungsten evaporation basket, and the pressure in the vacuum chamber was reduced again to 2 × 10 ⁻⁴ Pa.
At 0 nm / sec, magnesium was vapor-deposited. At this time, the silver basket was heated at the same time, and the vapor deposition rate was 0.1 nm / sec.
The organic EL element 2-1 for comparison was manufactured by depositing silver by using c to form a counter electrode made of a mixture of magnesium and silver.

M-MTDATXA, B used above
C and the structure of the comparative compound (1) are shown below.

[0175]

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In the above, the comparative compound (1) of the light emitting layer
Were replaced with the compounds shown in Table 2 in exactly the same manner, and the comparative organic EL devices 2-2 to 2-6 and 2-15
And the organic EL devices 2-7 to 2-14 and 2 of the present invention.
-16 to 2-18 were produced.

The organic EL devices 2-1 to 2-18 were evaluated for maximum radiant energy and light emission lifetime using the ITO electrode of the device as an anode and the counter electrode made of magnesium and silver as a cathode.

Comparative Organic EL Devices 2-1 to 2-6 and 2
At -15, blue or purple-blue light emission from the compound in the light-emitting layer was observed.

In the organic EL device 2-7 of the present invention, a current started to flow at an initial driving voltage of 5 V, and blue-violet light was emitted from the compound in the light emitting layer. At a maximum radiant energy of 9 V, it was 6.7 W / Sr · m ² . Table 2 shows the ratio (relative value) of the ratio of the maximum radiant energy of each organic EL element sample when the maximum radiant energy of 2-7 is set to 100.

Further, as a result of performing a life test on the element 2-7 in a nitrogen gas atmosphere, an initial radiant energy of 1 W / S
The half life of rm ² was 1320 hours.

The organic EL element No. 2-7 emission lifetime
Table 2 shows the values (relative values) of the ratios of the light emission lifetimes of the respective organic EL element samples when 00 was set.

[0182]

[Table 2]

[0183]

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[0184]

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As is clear from Table 2, the electroluminescent device using the compound of the present invention in the light-emitting layer has a high maximum radiant energy and a long light-emitting life, and is therefore very useful as an organic EL device. found.

Since the luminous efficiency greatly differs depending on the emission color, the comparison was made not with the luminance but with the maximum radiant energy.

Example 3 The compound used in Example 2 was changed to DMPh
en, and the compounds used in the hole transport layer were the compounds shown in Table 3 in the same manner as in Example 2, except that the organic electroluminescent device No. 3-1 to 3-15 were produced.

[0188]

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In the organic EL element 3-7 of the present invention, a current started to flow at an initial drive voltage of 5 V, and emitted blue-violet light.
When the maximum radiation energy is 11 V, 18.3 W / S
r · m ² . The maximum radiant energy of 3-7 is 10
Table 3 shows the values (relative values) of the ratios of the maximum radiant energies of the respective organic EL element samples when 0 was set.

Further, as a result of performing a life test on the element of 3-7 in a nitrogen gas atmosphere, an initial radiant energy of 1 W / S
The half life of rm ² was 440 hours.

The maximum radiant energy and emission life are organic EL
The value was expressed as a relative value when the value of the element 3-7 was 100. Table 3 shows the results.

[0192]

[Table 3]

As is clear from Table 3, the electroluminescent device using the compound of the present invention for the hole transporting layer is very useful as an organic EL device because it has a high maximum radiant energy and a long emission life. It has been found.

Example 4 Evaluation of Maximum Achieved Luminance of Organic Electroluminescent Elements 4-1 to 4-33 and Half-Time of Luminance after Continuous Light Emission <Preparation of Color Conversion Filter Using Inorganic Phosphor> Aerosil 0.16g to ethanol 15g
And 0.22 g of γ-glycidoxypropyltriethoxysilane were added, and the mixture was stirred for 1 hour at room temperature in an open system. The mixture and 20 g of (RL-10) were transferred to a mortar, mixed well, and then heated in an oven at 70 ° C. for 2 hours, and further dried for 120 hours.
(RL-1)
0) was obtained.

Similarly, (GL-13), (BL-
The surface modification of 3) was also performed. The above surface modification (R
L-10) Butyral (BX-) dissolved in 10 g of a mixed solution (300 g) of toluene / ethanol = 1/1
1) After adding 30 g and stirring, a wet film thickness of 200 μm was added.
m on glass. Apply the obtained coated glass to 1
The resultant was dried by heating in an oven at 00 ° C. for 4 hours to prepare a color conversion filter (FR) of the present invention.

In the same manner (GL-13),
A color conversion filter (FG) coated with (BL-3),
(FB) was produced.

The organic EL devices 2-1 to 2-1 produced in Example 2
2-18 and the organic EL devices 3-1 to 3-1 produced in Example 3.
On the substrate of No. 3-15, a color conversion filter (FB) as a blue conversion layer, a color conversion filter (FG) as a green conversion layer, and a color conversion filter (F-G) as a red conversion layer.
R) at 1.5mm intervals,
Organic EL element No. 4-1 to 4-33 were produced.

For each of the organic EL elements 4-1 to 4-33,
A 9 V DC voltage was applied under a dry nitrogen gas atmosphere at a temperature of 23 ° C., and the emission luminance, chromaticity coordinates, and time required to reduce the luminance of each of the blue, green, and red lights by half were measured using CS-1000 manufactured by Minolta. The highest attainable luminance and luminous life are 4-7 of the organic EL element.
And the relative luminance when the maximum attainable luminance and the light emission life were taken as 100. Table 4 shows the results.

The maximum emission wavelengths of red, green, and blue of the organic EL elements 4-1 to 4-33 are 66, respectively.
0 nm, 515 nm, and 432 nm.

[0200]

[Table 4]

As is clear from Table 4, the electroluminescent device of the present invention has the highest attainable luminance and emission lifetime, and is extremely desirable in terms of color. Therefore, it is very useful as an organic EL device. found.

[0202]

According to the present invention, a high-luminance, long-life organic EL device emitting light in the blue-violet to near-ultraviolet range can be obtained.

[Brief description of the drawings]

FIG. 1 is a diagram showing a configuration of an organic electroluminescence element.

[Explanation of symbols]

 Reference Signs List 1 light emitting layer 2 anode 3 cathode 4 color conversion layer 5 glass substrate 6 electron transport layer 7 hole transport layer

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07C 233/43 C07C 233/43 C09K 11/06 620 C09K 11/06 620 H05B 33/14 H05B 33/14 B (72) Inventor Hiroshi Kita 1 Konica Corporation, Hino-shi, Tokyo Konica Stock Company In-house F-term (reference) 3K007 AB02 AB04 AB11 EB00 4H006 AA01 AA03 AB91

Claims (15)

[Claims] 1. A compound represented by the following general formula (I). Embedded image [Wherein, R _{1 to} R ₂₈ each represent a hydrogen atom or a substituent, at least one of R _{14 to} R ₁₈ is a phenyl group which may have a substituent, and at least one of R _{19 to} R ₂₃ One is a phenyl group which may have a substituent, and the steric parameter E of the substituent of R ₁ , R ₂ , R ₃ and R ₄ is also
The sum of the _S values is −7 or more and −2.5 or less. ] 2. In the general formula (I), R ₁ , R ₂ ,
Substituents R ₃ and R ₄ A compound according to claim 1, which is a hydrogen atom or an alkyl group. 3. In the general formula (I), R ₁ , R ₂ ,
Compounds sum of steric parameter E _S values of the substituents R ₃ and R _4, -7 or more, characterized in that it is -3.7 or less. 4. In the general formula (I), R ₁ , R ₂ ,
The substituent of R ₃ and R ₄ is a hydrogen atom or an alkyl group, and the total number of carbon atoms contained in the substituents of R ₁ , R ₂ , R ₃ and R ₄ is 3 or more. The luminescent compound according to claim 3, characterized in that: 5. A compound represented by the following general formula (II). Embedded image [Wherein, R _{51 to} R ₇₈ each represent a hydrogen atom or a substituent, and at least one of R ₅₁ , R ₅₂ , R ₅₃ and R ₅₄ is an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group, a carboxyl group. , An amide group, a trifluoromethyl group or an alkoxycarbonyl group. ] 6. In the general formula (II), R ₅₁ ,
At least two of R ₅₂ , R ₅₃ and R ₅₄ are an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group,
The compound according to claim 5, which is a carboxyl group, an amide group, a trifluoromethyl group, or an alkoxycarbonyl group. 7. In the general formula (II), R ₅₁ ,
At least one of R ₅₂ , R ₅₃ and R ₅₄ is an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group,
A carboxyl group, an amide group, a trifluoromethyl group or an alkoxycarbonyl group, at least one of R _{59 to} R ₆₃ is a phenyl group which may have a substituent, and at least one of R _{69 to} R ₇₃ The compound according to claim 5, which is a phenyl group which may have a substituent. 8. In the general formula (II), R ₅₁ ,
At least two of R ₅₂ , R ₅₃ and R ₅₄ are an arylamino group, a phenyl group, a cycloalkyl group, an alkenyl group,
A carboxyl group, an amide group, a trifluoromethyl group or an alkoxycarbonyl group, at least one of R _{59 to} R ₆₃ is a phenyl group which may have a substituent, and at least one of R _{69 to} R ₇₃ The compound according to claim 5, which is a phenyl group which may have a substituent. 9. The compound according to claim 1, which is a fluorescent compound. 10. An organic electroluminescent device material comprising the compound according to claim 1. Description: 11. An organic electroluminescence device comprising the compound according to claim 1. Description: 12. An organic electroluminescence device comprising the compound according to claim 1 in a light-emitting layer. 13. An organic electroluminescence device comprising the compound according to claim 1 in a hole transport layer. 14. Purplish of CIE chromaticity coordinates
The organic electroluminescence device according to claim 11, 12 or 13, wherein the organic electroluminescence device emits light in a Blue (purple-blue), Blue Purple (blue-violet), or Purple (purple) region. 15. A conversion layer containing at least one phosphor having a maximum emission wavelength in a range of 400 to 500 nm, and a conversion layer containing at least one phosphor having a maximum emission wavelength in a range of 501 to 600 nm. Layers and 601-
15. The organic electroluminescence device according to claim 11, further comprising a conversion layer containing at least one kind of phosphor having a maximum emission wavelength in a range of 700 nm.