JP2001234159A - Luminous element material, luminous element using the same and amine compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a luminous element which enables luminescence with a high brightness and efficiency with a low voltage drive and shows an excellent stability when repetitively used. SOLUTION: The luminous element has an organic thin layer containing a compound of formula (I) (wherein Ar1 is a bivalent aryl group or a heterocyclic group; R2 and R3 are each independently an aryl group, a heterocyclic group or an aliphatic hydrocarbon group; Ar8 is an aryl group or a heterocyclic group which is not replaced with an amino group; R4a-R7a are each independently hydrogen atom or a monovalent group, wherein at least one of R4a-R7a is an electron-attractive group having a Hammett's σp value of 0.2; and L1 is a bivalent aryl group, a bivalent heterocyclic group or a bivalent group wherein an aryl group and a heterocyclic group are connected via a prescribed connected group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an amine compound, a light emitting device material using the same, and a light emitting device. The present invention relates to an amine compound usable as a dye, a laser dye, a medical diagnostic fluorescent agent, a light emitting device material, and the like, and a light emitting device material and a light emitting device using the same.

[0002]

2. Description of the Related Art Organic electroluminescence (E) using an organic substance is known.
L) The element is expected to be used as a solid-state light-emitting inexpensive large-area full-color display element, and various developments have been made. In general, an organic light-emitting device includes a light-emitting layer and a pair of opposed electrodes sandwiching the light-emitting layer. When an electric field is applied between both electrodes of the organic light emitting device, electrons are injected from the cathode and holes are injected from the anode, and the electrons and holes recombine in the light emitting layer, and the energy level is changed from the conduction band. Return to the valence band. At that time, energy is emitted as light, and the organic light emitting element emits light.

Meanwhile, an organic light emitting device is required to exhibit high light emission luminance and light emission efficiency at a low driving voltage. In recent years, an organic EL device that emits light at a low voltage of 10 V or less and has high fluorescence quantum efficiency has been reported (Applied Physics Letters, 51, 913, 1987).
Years), has attracted interest. This EL element has a structure in which a metal chelate complex is contained in an electron transporting layer, a fluorescent compound is contained in a light emitting layer, and an amine compound is contained in a hole transporting layer, and emits high-luminance green light. When an organic light emitting device is used as a light source for a full-color display, the light emitting device is required to emit light in three primary colors or white. However, when a conventional red light-emitting dye or the like is used alone as a light-emitting component in a light-emitting layer, concentration quenching is large, and high-efficiency light emission is often difficult. In recent years, a light emitting device capable of emitting a desired hue by doping a fluorescent dye has been reported (Journal of Applied Physics, Vol. 65, No. 36).
10, 1989). This method of doping with a fluorescent dye is particularly effective in a device using the red light-emitting dye, and achieves good color purity and high luminance. However, in order to manufacture a device doped with a fluorescent dye, it is necessary to co-evaporate a small amount of a fluorescent dye with a host material, which is problematic in that the operation is complicated and the performance of the device tends to vary. Even when used alone in the light-emitting layer, high-luminance light is emitted, and if a dye having excellent durability is used, an element having stabilized performance can be produced by a simple manufacturing process.
At present, a material that satisfies such performance has not been provided for a luminescent dye that emits orange to red light.

On the other hand, an organic EL device that achieves high-luminance light emission is a device in which organic substances are stacked by vacuum deposition. However, from the viewpoint of simplification of the manufacturing process, workability, enlargement of the area, and the like, it is desirable to manufacture the element by a coating method. However, an element manufactured by a conventional coating method is inferior to an element manufactured by a vapor deposition method in terms of luminous luminance and luminous efficiency, and high luminance and highly efficient luminescence are major issues. Further, as an element manufactured by a coating method, there is an element manufactured by dispersing and applying an organic low-molecular compound in an organic polymer medium, but when emitting light for a long time,
There is a problem that uniform planar light emission becomes difficult due to a cause such as aggregation of the organic low-molecular compound.

In recent years, substances having fluorescence in filter dyes, color conversion filters, photographic light-sensitive material dyes, sensitizing dyes, pulp dyeing dyes, laser dyes, fluorescent materials for medical diagnosis, and materials for organic light-emitting devices have been developed. Although it is used in various ways and its demand is increasing, it is desired that the fluorescent intensity is high and there are few fluorescent dyes capable of emitting long-wavelength light from orange to red.

[0006]

SUMMARY OF THE INVENTION A first object of the present invention is to enable high-luminance, high-efficiency light emission with low-voltage driving,
An object of the present invention is to provide an orange-red light-emitting element material and a light-emitting element which are excellent in stability upon repeated use and can emit uniform planar light. A second object of the present invention is to provide a light-emitting element having stable performance without variation in performance among the elements and a light-emitting element material which can be manufactured. A third object of the present invention is to provide a light-emitting element material capable of emitting light with high luminance and high efficiency even when manufactured by a coating method, and a light-emitting element using the same. A fourth object of the present invention is to provide an amine compound having fluorescence from orange to red with high fluorescence intensity.

[0007]

Means for Solving the Problems <1> A light emitting device material characterized by being a compound represented by the following general formula (I).

Formula (I)

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Wherein Ar¹Is a divalent aryl group or
Represents a telocyclic group, R^TwoAnd R^ThreeAre each independently
An aryl group, a heterocyclic group or an aliphatic hydrocarbon group;
¹, R^TwoAnd R^ThreeAt least two groups selected from
They may be linked to form a ring. Ar⁸Is an aryl group or
Represents a heterocyclic group, Ar⁸An aryl group represented by
Heterocyclic groups are not substituted with amino groups. R
^4a, R^5a, R^6aAnd R ^7aAre each independently a hydrogen atom
Or a monovalent group, R^4a, R^5a, R^6aAnd R^7aFew
At least one of the Hammett σp values is 0.2 or more.
Represents a child-withdrawing group. L¹Is a divalent aryl group, a divalent
Between heterocyclic groups, or between aryl groups, between heterocyclic groups,
Or a single bond between the aryl group and the heterocyclic group, a vinyl group,
C = X group, silyl group, aryl group and aromatic hetero 5
Or at least one member selected from a 6-membered ring group
Represents a divalent group. X is an oxygen atom, a sulfur atom, NR^X1Also
Is CR^X2R^X3And R^X1, R^X2And R^X3Are independent
Represents a hydrogen atom or a monovalent group.

<2> The light emitting device material according to <1>, wherein the compound represented by the general formula (I) is represented by the following general formula (II).

General formula (II)

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In the formula, Ar ¹ , R ² , R ³ and Ar ⁸ have the same meanings as those in formula (I). R ^4b , R ^5b , R ^6b and R ^7b each independently represent a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group; R ^4b , R ^5b , R ^6b and R ^7b are not all hydrogen atoms at the same time. L ² is a divalent aryl group, a divalent heterocyclic group, or a single bond between an aryl group, a heterocyclic group, or an aryl group and a heterocyclic group, a vinyl group, a C = X group, a silyl group. , An aryl group and a 5- or 6-membered aromatic heterocyclic group. X represents an oxygen atom, a sulfur atom, N-R ^X1 or CR ^X2 R ^X3 , and R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom or a monovalent group.
However, when L ² represents an aryl group having three or more rings, R ^4b ,
At least two selected from R ^5b , R ^6b and R ^7b are not hydrogen atoms.

<3> The light emitting device material according to <2>, wherein the compound represented by the general formula (II) is represented by the following general formula (III).

General formula (III)

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Wherein Ar ¹ , R ² , R ³ , Ar ⁸ and L ²
Is as defined for each of the general formulas (II). R ^4c represents a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group, and R ^5c , R ^6c and R ^7c each independently represent a hydrogen atom, Represents a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group.

<4> The light emitting device material according to <3>, wherein the compound represented by the general formula (III) is represented by the following general formula (IV).

Formula (IV)

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Wherein Ar ¹ , R ² , R ³ , Ar ⁸ and L ²
Is as defined for each of the general formulas (II). R ^4d and R ^7d
Are each independently a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group,
Represents a sulfonyl group, a sulfamoyl group or an acyl group.

<5> The light emitting device material according to <4>, wherein the compound represented by the general formula (IV) is represented by the following general formula (V).

Formula (V)

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Wherein Ar ¹ , R ² , R ³ and Ar ⁸ are
It has the same meaning as each of formula (I). R ^4e and R ^7e are
R ^4d and R ^{7d in} the general formula (IV) have the same ^meanings as each other, and L ³
Represents a divalent mono- or bicyclic aryl group or a divalent heterocyclic group.

<6> The light emitting device material according to <4>, wherein the compound represented by the general formula (IV) is represented by the following general formula (VI).

Formula (VI)

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In the formula, Ar ¹ , R ² and R ³ have the same meanings as those in formula (I). Ar ⁹ represents an aryl group or a heterocyclic group, and the aryl group or heterocyclic group represented by Ar ⁹ is not substituted with an amino group. R
^4f and R ^7f each independently represent a heterocyclic group, a perhalogenoalkyl group, an oxycarbonyl group, a carbamoyl group,
Represents a sulfonyl group, a sulfamoyl group or an acyl group. L ⁴ represents a divalent tricyclic or higher aryl group.

<7> A light emitting device material characterized by being a compound represented by the general formula (VII).

Formula (VII)

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In the formula, Ar ¹ represents a divalent aryl group or a heterocyclic group, and Ar ² and Ar ³ each independently represent an aryl group or a heterocyclic group. At least two members selected from Ar ¹ , Ar ² and Ar ³ may be linked to form a ring. Ar ⁸ represents an aryl group or a heterocyclic group, and the aryl group or heterocyclic group represented by Ar ⁸ is not substituted with an amino group. L ³ is divalent 1
Or a bicyclic aryl group or a divalent heterocyclic group, wherein R ^4g and R ^7g each independently represent a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group,
Represents a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group.

<8> A light emitting device having a pair of electrodes and an organic thin layer containing the light emitting device material according to any one of <1> to <7> sandwiched between the electrodes. <9> A light-emitting element including a pair of electrodes and a layer in which the light-emitting element material according to any one of <1> to <7> is dispersed in a polymer, sandwiched between the electrodes.

<10> An amine compound represented by the following general formula (VII).

Formula (VII)

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In the formula, Ar ¹ represents a divalent aryl group or a heterocyclic group, and Ar ² and Ar ³ each independently represent an aryl group or a heterocyclic group. At least two members selected from Ar ¹ , Ar ² and Ar ³ may be linked to form a ring. Ar ⁸ represents an aryl group or a heterocyclic group, and the aryl group or heterocyclic group represented by Ar ⁸ is not substituted with an amino group. L ³ is divalent 1
Or a bicyclic aryl group or a divalent heterocyclic group, wherein R ^4g and R ^7g each independently represent a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group,
Represents a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group.

[0032]

BEST MODE FOR CARRYING OUT THE INVENTION The light emitting device material of the present invention contains at least the compound represented by the above general formula (I). The amine compound represented by the general formula (I) exhibits orange to red fluorescence having a strong fluorescence intensity. Therefore, when the amine compound is used for a non-doped light-emitting element, that is, even when the amine compound is used alone in a light-emitting layer, the light-emitting element is driven at a low voltage and has high luminance and high efficiency. Light emission becomes possible.

In the general formula (I), Ar ¹ represents a divalent aryl group or a heterocyclic group. The divalent aryl group represented by Ar ¹ includes an aryl group having a substituent and an unsubstituted aryl group. Further, the aryl group is
It may have a monocyclic structure or a polycyclic structure in which two or more rings are fused. The aryl group has 6 to 3 carbon atoms.
A monocyclic to pentacyclic aryl group (e.g., phenyl, naphthyl, biphenyl, fluorenyl, etc.) is preferable, and a phenyl group having 6 to 20 carbon atoms and a naphthyl group are more preferable, and a phenyl group having 6 to 14 carbon atoms is preferable. Group,
A naphthyl group is more preferred.

The divalent heterocyclic group represented by Ar ¹ includes a substituted heterocyclic group and an unsubstituted heterocyclic group. Further, even if the heterocyclic group has a monocyclic structure,
It may have a polycyclic structure in which the above rings are fused. The heterocyclic group is a 3- to 10-membered saturated or unsaturated heterocyclic divalent group containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom. As the heterocyclic group, 5
A 6-membered aromatic heterocyclic group is preferable, and a nitrogen atom,
A 5- or 6-membered aromatic heterocyclic group containing an oxygen atom and a sulfur atom is more preferable.
A 5- or 6-membered aromatic heterocyclic group containing atoms is more preferred. Specific examples of the heterocyclic ring, for example, pyrrolidine,
Piperidine, piperazine, morpholine, thiophene,
Furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline,
Thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline,
Cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole,
Examples include benzoxazole, benzothiazole, benzotriazole, and tetrazaindene. Among them,
Thiophene, pyridine and quinoline are preferred.

When the aryl group and heterocyclic group represented by Ar ¹ have a substituent, examples of the substituent include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, Particularly preferably, it has 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, te
rt-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like, and an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably Has 2 to 8 carbon atoms, for example, vinyl, allyl,
2-butenyl, 3-pentenyl and the like), an alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, and particularly preferably having 2 to 8 carbon atoms, for example, propargyl, 3-pentynyl And the like; an aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 6 carbon atoms).
12, for example, phenyl, p-methylphenyl, naphthyl, and the like), an amino group (preferably having 0 to 20, more preferably 0 to 10, and particularly preferably 0 to 6, Examples thereof include amino, methylamino, dimethylamino, diethylamino, and dibenzylamino), and an alkoxy group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms. , For example, methoxy, ethoxy, butoxy, etc.),

An aryloxy group (preferably having 6 to 6 carbon atoms)
20, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example, phenyloxy, 2-naphthyloxy and the like, and an acyl group (preferably 1 to 20 carbon atoms, more preferably It has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, acetyl,
Benzoyl, formyl, pivaloyl and the like), alkoxycarbonyl group (preferably having 2 to 2 carbon atoms)
20, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl and the like, and aryloxycarbonyl group (preferably 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, particularly preferably 7 to 10 carbon atoms, for example, phenyloxycarbonyl and the like), acyloxy group (preferably 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably Carbon number 2
10 to 10, for example, acetoxy, benzoyloxy and the like), an acylamino group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, acetylamino , Benzoylamino and the like), an alkoxycarbonylamino group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, particularly preferably having 2 to 12 carbon atoms, for example, methoxycarbonylamino and the like. ),

An aryloxycarbonylamino group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 1 carbon atoms)
6, particularly preferably having 7 to 12 carbon atoms, such as phenyloxycarbonylamino, etc.), and a sulfonylamino group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, and particularly preferably having 1 to 16 carbon atoms). 1-12
And methanesulfonylamino, benzenesulfonylamino, etc.), and a sulfamoyl group (preferably having 0 to 20 carbon atoms, more preferably having 0 carbon atoms).
To 16, particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl and the like, a carbamoyl group (preferably 1 to 20 carbon atoms, more preferably Represents 1 to 16 carbon atoms, particularly preferably 1 to 1 carbon atoms.
12, for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.), an alkylthio group (preferably having 1 carbon atom).
-20, more preferably 1-16 carbon atoms, particularly preferably 1-12 carbon atoms, for example, methylthio, ethylthio, etc.), arylthio group (preferably 6-20 carbon atoms, more preferably 6 carbon atoms). To 16, particularly preferably having 6 to 12 carbon atoms, such as phenylthio, etc.), and a sulfonyl group (preferably having 1 carbon atom).
-20, more preferably 1-16 carbon atoms, particularly preferably 1-12 carbon atoms, for example, mesyl, tosyl, etc.), sulfinyl group (preferably 1-carbon
20, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl and benzenesulfinyl. ),

Ureido group (preferably having 1 to 20 carbon atoms;
More preferably, it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, ureide, methyl ureide, phenyl ureide and the like, and a phosphoric amide group (preferably 1 to 20 carbon atoms, more preferably Carbon number 1
To 16, particularly preferably 1 to 12 carbon atoms, for example, diethylphosphoramide, phenylphosphoramide, etc.), hydroxy group, mercapto group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine) Atoms), cyano, sulfo, carboxyl, nitro, hydroxamic acid, sulfino, hydrazino,
Imino group, heterocyclic group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically, for example, pyrrolidine, piperidine, Piperazine, morpholine, thiophene, furan, pyrrole, imidazole,
Pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline,
Isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetrazaindene, etc., and a silyl group (preferably having carbon atoms) 3 to 40, more preferably 3 to 30, particularly preferably 3 to 24, and examples thereof include trimethylsilyl and triphenylsilyl. These substituents may be further substituted with similar substituents. When there are two or more substituents, they may be the same or different. When possible, they may be connected to each other to form a ring.

The substituent is preferably an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an amino group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acylamino group, an alkoxycarbonylamino group, an aryloxy group. Carbonylamino group, sulfonylamino group, sulfamoyl group,
A carbamoyl group, a hydroxy group and a heterocyclic group, more preferably an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an amino group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, and a sulfonylamino group , A heterocyclic group. More preferably, an alkyl group, an alkenyl group,
An aryl group, an alkoxy group, and a substituted amino group. Here, the substituted amino group is a group represented by —NR _a (R _b ), and R _a and R _b may be the same or different and include an alkyl group, an alkenyl group, an aralkyl group, an aryl group or a hetero group. Represents a ring group, and the alkyl group, alkenyl group, aryl group or heterocyclic group is the same as those exemplified as the substituent of Ar ¹ , and the preferred range is also the same. The aralkyl group preferably has 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, and particularly preferably 7 to 10 carbon atoms, and examples thereof include a benzyl group and a phenethyl group.

In the general formula (I), R ² and R ³ each independently represent an aryl group, a heterocyclic group or an aliphatic hydrocarbon group. The aryl groups represented by R ² and R ³ each include a substituted aryl group and an unsubstituted aryl group. Further, the aryl group may have a monocyclic structure or a polycyclic structure in which two or more rings are fused.
The aryl group is preferably a monocyclic to pentacyclic aryl group having 6 to 30 carbon atoms (for example, phenyl, naphthyl, anthryl group, phenanthryl group, pyrenyl group, indenyl group, perylenyl group, etc.), 6 to 20 phenyl groups, naphthyl groups, anthryl groups,
A phenanthryl group and a pyrenyl group are more preferred, and a phenyl group having 6 to 14 carbon atoms, a naphthyl group and an anthryl group are more preferred.

The heterocyclic groups represented by R ² and R ³ include:
It includes a substituted heterocyclic group and an unsubstituted heterocyclic group. Further, the heterocyclic group may have a monocyclic structure or a polycyclic structure in which two or more rings are fused. The heterocyclic group is a monovalent group of a 3- to 10-membered saturated or unsaturated heterocyclic ring containing at least one atom of a nitrogen atom, an oxygen atom and a sulfur atom. The heterocyclic group is preferably a 5- or 6-membered aromatic heterocyclic group,
A 5- to 6-membered aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom is more preferable, and a 5- or 6-membered aromatic heterocyclic group containing at least one or two atoms of a nitrogen atom and a sulfur atom is more preferable. Groups are more preferred. Specific examples of the heterocycle include, for example, pyrrolidine, piperidine, piperazine, morpholine, thiophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole. , Oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetrazaindene, etc. No. Among them, thiophene, pyridine and quinoline are preferred.

The aliphatic hydrocarbon groups represented by R ² and R ³ include an aliphatic hydrocarbon group having a substituent and an unsubstituted aliphatic hydrocarbon group. As the aliphatic hydrocarbon group, a linear, branched or cyclic (including a monocyclic structure and a polycyclic structure) alkyl group (preferably having 1 to 2 carbon atoms)
0, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, Cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 carbon atoms)
-12, particularly preferably 2-8 carbon atoms, for example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably 2-8 carbon atoms).
0, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as propargyl and 3-pentynyl. Among them, the alkyl group is preferable as the aliphatic hydrocarbon group.

When the aryl group, heterocyclic group and aliphatic hydrocarbon group represented by R ² and R ³ have a substituent,
Examples of the substituent include those described as the substituent for Ar ¹ . In the general formula (I), A
Two or three groups selected from r ¹ , R ² and R ³ may be linked to each other to form a ring. The ring formed is preferably a 5- to 7-membered ring.

In the general formula (I), Ar ⁸ represents an aryl group or a heterocyclic group. The aryl group represented by Ar ⁸ includes an aryl group having a substituent (excluding an amino group) and an unsubstituted aryl group. Further, the aryl group may have a monocyclic structure or a polycyclic structure in which two or more rings are fused. As the aryl group,
A monocyclic to pentacyclic aryl group having 6 to 30 carbon atoms (for example, phenyl, naphthyl, anthryl group, phenanthryl group, pyrenyl group, indenyl group, perylenyl group and the like) is preferable, and phenyl having 6 to 20 carbon atoms is preferable. Groups, naphthyl groups and anthryl groups are more preferred.

The heterocyclic group represented by Ar ^{8 includes} a heterocyclic group having a substituent (excluding an amino group) and an unsubstituted heterocyclic group. Further, the heterocyclic group is
It may have a monocyclic structure or a polycyclic structure in which two or more rings are fused. The heterocyclic group contains 3 to 10 atoms containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom.
Membered saturated or unsaturated heterocyclic monovalent group.
The heterocyclic group is preferably a 5- or 6-membered aromatic heterocyclic group, more preferably a 5- or 6-membered aromatic heterocyclic group containing at least one atom of a nitrogen atom, an oxygen atom and a sulfur atom. And a 5- to 6-membered aromatic heterocyclic group containing 1 to 2 sulfur atoms is more preferred. Specific examples of the heterocycle include, for example, pyrrolidine, piperidine, piperazine, morpholine, thiophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole. , Oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetrazaindene, etc. No. As the heterocycle, thiophene, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole,
Quinoline, isoquinoline, phthalazine, naphthyridine,
Quinoxaline, quinazoline, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, and benzotriazole are preferred.

The aryl group or heterocyclic group represented by Ar ⁸ may have a substituent, and the substituent is Ar ¹
And those excluding the amino group among those shown as examples of the substituent. Examples of the substituent include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, and a sulfonylamino group. , A sulfamoyl group, a carbomoyl group, a sulfonyl group, a sulfinyl group, a ureido group, a halogen atom, a cyano group, and a heterocyclic group.

In the general formula (I), R ^4a , R ^5a , R ^6a and R ^7a each independently represent a hydrogen atom or a monovalent group. Examples of the monovalent group include those described as substituents for Ar ¹ . However, at least one of R ^4a , R ^5a , R ^6a and R ^7a represents an electron-withdrawing group having a Hammett σp value of 0.2 or more. Examples of the electron-withdrawing group having a Hammett's σp value of 0.2 or more include a halogen atom, a perhalogenoalkyl group (for example, a perfluoroalkyl group, a perchloroalkyl group, and a perbromoalkyl group), a cyano group, and formyl. Group, carboxyl group, carbamoyl group, sulfonylmethyl group, acyl group,
An oxycarbonyl group (preferably an oxycarbonyl group substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; an aliphatic hydrocarbon group, an aryl group or a heterocyclic group is represented by R ² and R ³ ; Each has the same meaning and the preferred range is also the same), pentahalophenyl group, carbonyloxy group, sulfonyloxy group, sulfonyl group, sulfinyl group, heterocyclic group, sulfamoyl group and the like. Among them, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, and an acyl group are preferable, and benzoxazole, benzothiazole,
Benzimidazole, cyano group, oxycarbonyl group,
Sulfonyl, sulfamoyl and acyl groups are particularly preferred.

In the formula (I), L ¹ represents a divalent aryl group, a divalent heterocyclic group, or a single bond between aryl groups, between heterocyclic groups, or between an aryl group and a heterocyclic group, It represents a divalent group linked by at least one selected from a vinyl group, a C = X group, a silyl group, an aryl group and an aromatic hetero 5- or 6-membered ring group. Here, the aryl group or the heterocyclic group (including each group when linked by a predetermined linking group) has the same meaning as the divalent aryl group or the heterocyclic group represented by Ar ¹ , respectively. It may have a condensed polycyclic (preferably 2 to 5 rings) structure. Examples of the heterocyclic group include thiophene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole,
Divalent groups of thiazole, thiadiazole, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole Is preferred. X is an oxygen atom, a sulfur atom, N—R ^X1 ,
Or CR ^X2 R ^X3 , and particularly preferably an oxygen atom, a sulfur atom, or CR ^X2 R ^X3 .

R^X1, R^X2And R^X3Are each independently water
Represents an elementary atom or a monovalent group. The monovalent group includes Ar¹
And the same substituents as those described above. R
^X1Is a hydrogen atom, an alkyl group, an aryl group or a heterocyclic ring
And R is^X2And R^X3Is a hydrogen atom, an alkyl
Group, aryl group, heterocyclic group, cyano group, oxycarbo
Nil group, carbamoyl group, sulfonyl group, sulfamoi
Or an acyl group;^X2And R^X3Is hydrogen at the same time
Preferably it is not an atom. R^X1, R^X2And R ^X3Represents
The alkyl group, the aryl group or the heterocyclic group is represented by Ar¹of
It has the same meaning as each of the substituents, and the preferred range is also the same.
You. Above all, R^X2And R^X3As an alkyl group represented by
Is preferably a perfluoroalkyl group,
Linear, branched or cyclic alkyl group having a substituent
(Preferably 1 to 30 carbon atoms, more preferably 1 to 2 carbon atoms
0, more preferably 1 to 12, for example, trifluoro
Or methyl group or pentafluoromethyl group)
No. R^X2And R^X3Oxycarbonyl each represented by
Group, carbamoyl group, sulfonyl group, sulfamoyl
Groups and acyl groups are aliphatic hydrocarbon groups, aryl groups
And at least one group selected from heterocyclic groups
It is preferably replaced. R^X2And R^X3Oki represented by
Sicarbonyl group, carbamoyl group, sulfonyl group, sulf
The famoyl group and the acyl group are represented by R^4a, R^5a, R^6aYou
And R^7aHas the same meaning as each group represented by
It is. Note that R^X2And R^X3May be linked to form a ring
No.

In the general formula (1), examples of L ¹ include the following. .

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Among the amine compounds represented by the general formula (I), the amine compound represented by the general formula (II) is preferable. In the general formula (II), Ar ¹ , R ² , R ³ and Ar ⁸ have the same meanings as those in the general formula (I), and the preferred ranges are also the same.

In the general formula (II), R ^4b , R ^5b , R ^6b ,
And R ^7b each independently represent a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, and R ^4b , R ^5b , R ^6b and R
All ^7b cannot be hydrogen atoms at the same time. R ^4b , R
^The heterocyclic group represented by ^5b , R ^6b and R ^7b is preferably the same as the heterocyclic group represented by the substituent of R ² and R ³ ,
Particularly preferred are benzoxazole, benzothiazole and benzimidazole. R ^4b , R ^5b , R ^6b , R
^The oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group and acyl group represented by ^7b are preferably substituted with at least one selected from aliphatic hydrocarbon groups, aryl groups and heterocyclic groups. The aliphatic hydrocarbon group which is a substituent of R ^4b , R ^5b , R ^6b , and R ^7b is preferably the same as the aliphatic hydrocarbon group represented by R ² or R ³ , and among them, an alkyl group , An alkenyl group, more preferably a methyl group, an ethyl group, a propyl group, a butyl group, a trifluoromethyl group, and an allyl group. R ^4b , R ^5b , R ^6b ,
The aryl group as a substituent of R ^7b is preferably the same as the aryl group represented by R ² and R ³ . R ^4b , R
^The heterocyclic group which is a substituent of ^5b , R ^6b and R ^7b includes R
Is preferably the same meaning as the heterocyclic group represented by ^2, R ^3, which may be a single ring or may form a condensed ring with another ring.

Among them, R ^4b , R ^5b , R ^6b and R ^7b represent a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group,
More preferably, it is an oxycarbonyl group, a sulfonyl group, or an acyl group.

In the general formula (II), L ² represents the general formula (I)
Of L ¹ as synonymous. However, when L ² is an aryl group having three or more rings, at least two selected from R ^4b , R ^5b , R ^6b and R ^7b are not hydrogen atoms.

Among the amine compounds represented by the general formula (II), the amine compounds represented by the general formula (III) are preferable. In the general formula (III), Ar ¹ , R ² , R ³ ,
Ar ⁸ and L ² have the same meanings as those in formula (II), and the preferred ranges are also the same.

In the general formula (II), R ^4c represents a heterocyclic group,
Represents a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, and R ^5c , R ^6c , and R ^7c each independently represent a hydrogen atom, a heterocyclic group, a perhalogeno group; Alkyl group, cyano group, oxycarbonyl group, carbamoyl group,
Represents a sulfonyl group, a sulfamoyl group, or an acyl group. The heterocyclic group, perhalogenoalkyl group, cyano group, oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, and acyl group represented by R ^4c , R ^5c , R ^6c , and R ^7c are represented by the general formula (II) ) R
It has the same meaning as each group represented by ^4b , R ^5b , R ^6b and R ^7b , and the preferred range is also the same.

Among the amine compounds represented by the general formula (III), the amine compound represented by the general formula (IV) is preferable.

In the general formula (IV), Ar ¹ , R ² , R ³ ,
Ar ⁸ and L ² have the same meanings as in each of the formulas (III), and the preferred ranges are also the same. The general formula (IV)
Wherein R ^4d and R ^7d are each independently a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group,
Represents a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group. The groups represented by R ^4d and R ^7d have the same ^{meanings as the} groups represented by R ^{4C in} formula (III), and the preferred ranges are also the same.

Among the amine compounds represented by the general formula (IV), the amine compound represented by the general formula (V) or the compound represented by the general formula (VI) is preferable.

In the general formula (V), Ar ¹ , R ² , R ³ and Ar ⁸ have the same meanings as the respective groups in the general formula (I),
The same applies to the preferred range. In the above general formula (V), R ^4e
And R ^7e each independently represent a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group. For each of the groups represented by R ^4e and R ^7e ,
It has the same meaning as each group represented by R ^{4C in} formula (III), and the preferred range is also the same. In the general formula (V), L ³ represents a divalent monocyclic or bicyclic aryl group or a divalent heterocyclic group, wherein the divalent aryl group or the heterocyclic group is represented by the general formula (I ) Has the same meaning as the divalent aryl group represented by Ar ¹ (however, a 1- or 2-ring aryl group) or a divalent heterocyclic group, and the preferred range is also the same.

In the general formula (VI), Ar ¹ , R ² and R
³ has the same meaning as each group in the formula (I), and the preferred range is also the same. In the general formula (VI), Ar ⁹ represents an aryl group or a heterocyclic group which may be substituted with a substituent other than an amino group. The aryl group and the heterocyclic group have the same meaning as each group represented by Ar ⁸ in the general formula (I). Examples of the substituent include those other than an amino group, and the groups described as the substituent of Ar ⁸ are preferable. Among them, Ham described in R4a to R7a is preferable.
An electron withdrawing group having a δp value of ett of 0.2 or more is preferred.

In formula (VI), R ^4f and R ^7f each independently represent a heterocyclic group, a perhalogenoalkyl group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group; Each of the groups represented by R ^{4C in} formula (III) has the same ^meaning as described above. In the above general formula (VI), L ⁴ represents a divalent tricyclic or more aryl group, and a C12 to C3 or more tricyclic aryl group (fluorenyl group, carbazolyl group, anthryl group, phenanthryl group, pyrenyl group) , A perylenyl group, etc.)
Is preferred.

Among the amine compounds represented by the general formula (V), the amine compound represented by the general formula (VII) is preferable. In the general formula (VII), Ar ¹ and Ar ⁸
Has the same meaning as each group in the formula (I), and the preferred range is also the same. In the general formula (VII), Ar ² and A
r ³ each independently represents an aryl group or a heterocyclic group, and has the same meaning as the aryl group or the heterocyclic group represented by R ² and R ^{3 in} Formula (I). The general formula (VI
In I), R ^4g and R ^7g are each independently a heterocyclic group,
Represents a perhalogenoalkyl group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, and has the same meaning as each group represented by R ^{4C in the} general formula (III).

The compounds represented by the general formulas (I) to (VII) may be low molecular weight compounds,
To (VII) in which a residue represented by the formula (VII) is connected to the polymer main chain (preferably a weight average molecular weight of 1,000 to
5,000,000, particularly preferably 5000 to 20,000
00, more preferably 10,000 to 1,000,000)
Alternatively, a high molecular weight compound having a skeleton of the general formulas (I) to (VII) in the main chain (preferably a weight average molecular weight of 1,000 to 1,000)
5,000,000, particularly preferably 5000 to 20,000
00, more preferably 10,000 to 1,000,000). In the case of a high molecular weight compound, it may be a homopolymer or a copolymer with another monomer.

The compounds represented by formulas (I) to (VII) are preferably low molecular weight compounds. In addition, the general formulas (I) to (VII) are represented by the limit structural formulas for convenience, but may be tautomers thereof.

Preferred combinations of the substituents of the compound represented by formula (I) will be described. In addition, among the compounds represented by the general formula (I), a compound in which at least one of various substituents is in the following preferable range is preferable from the viewpoint of luminescence characteristics, and more various substituents are preferable in the following. Compounds having the above range are more preferable in terms of light emission characteristics, and compounds having all the substituents in the following preferable ranges are most preferable in terms of light emission characteristics. The following general formula (II)
The same applies to preferred combinations of substituents of the compound represented by (VII). Ar ¹ is a divalent carbon number of 6 to 3
0 monocyclic to pentacyclic aryl group, or a divalent C 1-20 carbon atom containing a nitrogen atom, an oxygen atom or a sulfur atom
Represents a 6-membered aromatic heterocyclic group, which may be condensed. R ² and R ³ are each independently a monocyclic to tetracyclic aryl group having 6 to 30 carbon atoms, a 5- to 6-membered aromatic heterocyclic group having 1 to 20 carbon atoms containing a nitrogen atom, an oxygen atom or a sulfur atom. Represents a ring group or an alkyl group having 1 to 20 carbon atoms. Ar ⁸ represents a monocyclic or tetracyclic aryl group having 6 to 30 carbon atoms, or a 3 to 10-membered saturated or unsaturated heterocyclic group containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom, These may be a single ring or may form a condensed ring with another ring. Ar ¹ ,
R ² , R ³ and Ar ⁸ may have a substituent, and examples of the substituent include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an amino group, an acyl group, an alkoxycarbonyl group, and an aryloxycarbonyl group. Group, acylamino group, sulfonylamino group, sulfamoyl group,
A carbamoyl group, a hydroxy group and a heterocyclic group are preferable, and these substituents may be further substituted. A
r ¹ , R ² and R ³ may be linked to form a ring, and the formed ring is preferably a 5- to 7-membered ring.

R ^4a , R ^5a , R ^6a and R ^7a each independently represent a hydrogen atom or a substituent, and at least one of R ^4a , R ^5a , R ^6a and R ^7a has a σp value of 0.2 It represents the above electron-withdrawing group. Examples of the substituent represented by R ^4a , R ^5a , R ^6a and R ^7a include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an amino group, an acyl group, an oxycarbonyl group, a carbonylamino group and a sulfonylamino. Groups, sulfonyl groups, sulfamoyl groups, carbamoyl groups, cyano groups, and heterocyclic groups are preferred.

L ¹ represents a divalent aryl or heterocyclic group, or a single bond of an aryl or heterocyclic group, a vinyl group, a C ＝ X group, a silyl group, an aryl group and an aromatic hetero 5- to 6-membered ring group. Represents a divalent group linked by at least one selected from Here, a divalent aryl group (including an aryl group linked to a heterocyclic group) is a monocyclic to pentacyclic aryl group having 6 to 30 carbon atoms and a divalent heterocyclic group (linked to an aryl group). Including heterocyclic groups)
Is a carbon atom containing a nitrogen atom, an oxygen atom or a sulfur atom.
It preferably represents 〜20 divalent 5- or 6-membered aromatic heterocyclic group. The rings may be further condensed to form 2 to 5 rings. Among them, the heterocyclic group is thiophene, pyrrole, imidazole, pyrazole, pyridine, pyrazine,
Pyridazine, triazole, triazine, indole,
Indazole, thiazole, thiadiazole, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline,
Cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole,
More preferred are benzoxazole, benzothiazole and benzotriazole.

X in the C ＝ X group is an oxygen atom, a sulfur atom, N
-R^X1Or CR^X2R^X3And R ^X1, R^X2And R^X3
Each independently preferably represents a hydrogen atom or a substituent.
And more preferably an oxygen atom, a sulfur atom or CR^X2
R^X3Represents R^X1Are a hydrogen atom, an alkyl group,
Preferably represents a reel group or a heterocyclic group;^X2You
And R^X3Are each independently a hydrogen atom, an alkyl group,
, A heterocyclic group, a cyano group, an oxycarbonyl group,
Carbamoyl, sulfonyl, sulfamoyl or
Preferably represents an acyl group;^X2And R^X3Is water at the same time
Not an elementary atom. Above all, R^X1, R^X2And R^X3Represented by
Alkyl group, aryl group or heterocyclic group is Ar
¹An alkyl group, an aryl group or a
More preferably, it has the same meaning as the telocyclic group. R^X2And R
^X3An alkyl group represented by a perfluoroalkyl group,
That is, linear, branched or cyclic having fluorine as a substituent
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably
1-20, more preferably 1-12, for example
Trifluoromethyl group, pentafluoromethyl group, etc.)
It is preferred that R^X2, R^X3Oxycal represented by
Bonyl, carbamoyl, sulfonyl, sulfamo
Yl group, preferably an aliphatic hydrocarbon group as an acyl group,
Oxycarbo substituted with an aryl or heterocyclic group
Nil group, carbamoyl group, sulfonyl group, sulfamoi
And an acyl group;^4a, R^5a, R^6a, R^7aRepresented by
Oxycarbonyl group, carbamoyl group, sulfonyl
Group, a sulfamoyl group and an acyl group.

A more preferred combination of substituents of the compound represented by the formula (I) is represented by the formula (II). The preferred ranges of Ar ¹ , R ² , R ³ and Ar ⁸ are the same as the preferred ranges of the formula (I). R ^4b , R ^5b , R ^6b and R ^7b each independently represent a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group. Is preferred. R ^4b , R ^5b , R ^6b and R ^7b are not all hydrogen atoms at the same time. L ² has the same meaning as the aforementioned preferred range of L ¹ , but when L ² is an aryl group having three or more rings,
^At least two of ^4b , R ^5b , R ^6b and R ^7b are not hydrogen atoms.

R^4b, R^5b, R^6bAnd R^7bEach represents
Terocyclic groups contain nitrogen, oxygen or sulfur atoms
A 5- to 6-membered aromatic heterocyclic group having 1 to 20 carbon atoms
Preferably, R^4b, R^5b, R^6bAnd R^7bIs each table
Oxycarbonyl group, carbamoyl group, sulfonyl
Group, sulfamoyl group or acyl group is an aliphatic hydrocarbon
At least one selected from an aryl group, an aryl group and a heterocyclic group.
Both are preferably substituted by one. R^4b, R^5b,
R^6bAnd R^7bThe aliphatic hydrocarbon group as a substituent of
Is R^TwoAnd R^ThreeSynonymous with the aliphatic hydrocarbon group represented by
Yes, preferably an alkyl group, an alkenyl group,
More preferably methyl group, ethyl group, propyl group, butyl
Group, trifluoromethyl group, allyl group and the like.
R^4b, R^5b, R ^6bAnd R^7bAryl as a substituent of
The group is preferably R^Two, R^ThreeAnd an aryl group represented by
It is synonymous. R^4b, R^5b, R^6bAnd R^7bAs a substituent of
All heterocyclic groups are preferably R^Two, R^ThreeHete represented by
Synonymous with the ring group, these may be monocyclic,
Further, a condensed ring may be formed with another ring.

More preferred substituents of the above formula (II)
Are represented by the general formula (III). Ar¹, R
^Two, R^Three, Ar⁸And L^TwoIs preferably a group represented by the general formula (I
It has the same meaning as each preferred range of I). R^4cIs hetero
Ring group, perhalogenoalkyl group, cyano group, oxycal
Bonyl, carbamoyl, sulfonyl, sulfamo
Represents an yl group or an acyl group;^5c, R^6cAnd R^7cIs
Each independently represents a hydrogen atom, a heterocyclic group, a perhalogenoa
Alkyl, cyano, oxycarbonyl, carbamoy
Group, sulfonyl group, sulfamoyl group or acyl group
Represents R^4c, R^5c, R ^6cAnd R^7cEach represents a hetero
Ring group, perhalogenoalkyl group, cyano group, oxycal
Bonyl, carbamoyl, sulfonyl, sulfamo
The yl group and the acyl group are represented by the general formula (II)
Is synonymous with each of

A more preferred combination of the substituents of the above formula (III) is represented by the following formula (IV). Ar ¹ ,
Preferred ranges of R ² , R ³ , Ar ⁸ and L ² are the same as the preferred ranges of the above formula (II). Preferred ranges of R ^4d and R ^7d are each the same as defined for R ^{4c in} formula (III).

More preferred combinations of the substituents of the above formula (IV) are represented by the following formulas (V) and (VI). The preferred ranges of Ar ¹ , R ² , R ³ and Ar ^{8 in} the general formula (V) are the same as the respective preferred ranges in the general formula (I). R ^4e and R ^7e each represent R ^{4c of the} general formula (III)
Is the same as the preferred range. The divalent mono- or bicyclic aryl group and the divalent heterocyclic group represented by L ³ are preferably the same as the mono- or bicyclic aryl group and the heterocyclic group represented by Ar ^{1 in} formula (I). And more preferably a phenyl group, a naphthyl group, or a thiophene ring,
A pyrrole ring, an imidazole ring, a pyrazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, or a 2 to 4 ring in which these and a benzene ring form a condensed ring Represents a heterocyclic group. L ³ is particularly preferably a phenyl group, a naphthyl group, a monocyclic or condensed bicyclic or tricyclic heterocyclic group.

The preferred ranges of Ar ¹ , R ² , R ³ and Ar ^{9 in} the general formula (VI) are the same as those in the general formula (I). R ^4f and R ^7f are each independently preferably a heterocyclic group, a perhalogenoalkyl group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group, and the preferable range of each group is as described above. It is the same as each range described in R ^4c of the general formula (III). L ⁴ is a divalent aryl group having three or more rings, and preferably has the same meaning as the aryl group having three or more rings represented by Ar ^{1 in} formula (I).

A more preferred combination of the substituents in the general formula (V) is represented by the general formula (VII). A
The preferred ranges of r ¹ , Ar ⁸ and L ³ are the same as the preferred ranges of the above formula (V). Ar
² and Ar ³ are a phenyl group having 6 to 30 carbon atoms, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group,
It may be further condensed with an indenyl group, or may have 5 to 15 carbon atoms containing a nitrogen atom, an oxygen atom or a sulfur atom.
Or a 6-membered aromatic heterocyclic group, and the heterocyclic group may be condensed, and more preferably a 5- or 6-membered aromatic group containing 1 or 2 nitrogen and sulfur atoms. It is a heterocyclic group. Preferred ranges of R ^4g and R ^7g are each the same as defined for R ^{4c in} formula (III).

The specific examples D-1 to D42 of the compounds represented by formula (I) are shown below, but the invention is not restricted thereto.

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Next, some examples of the synthesis of the compound represented by the general formula (I) of the present invention are shown below. Synthesis Example-1 Synthesis of Exemplified Compound (D-20)

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26.8 g of terephthalaldehyde and 13.1 g of ethylene glycol were dissolved in 250 ml of toluene, and paratoluenesulfonic acid (PTS) was further dissolved.
0.2 g was added, and the mixture was heated and refluxed for 14 hours in the presence of molecular sieve. After completion of the reaction, toluene was distilled off to obtain Intermediate A as an oil. To the obtained Intermediate A, 39.2 g of 4-bromobenzyl cyanide was added, and t-
2.24 g of potassium butoxylate is 600 m in ethanol
and dissolved under reflux for 6 hours. After allowing the reaction solution to cool overnight, the precipitated crystals were collected by filtration and Intermediate B
49.2 g were obtained. Next, under a nitrogen atmosphere, 7.1 g of diphenylamine was dissolved in 150 ml of o-xylene, 4.6 g of sodium t-butoxide, 0.224 g of palladium acetate, 14.2 g of intermediate B,
0.8 g of t-butylphosphine was added sequentially, and
The mixture was heated and stirred at ℃ for 6 hours. After the reaction was completed, ethyl acetate was added to the reaction solution, and insoluble components were removed by filtration through Celite. The obtained ethyl acetate solution was washed with water, dehydrated and concentrated, and the obtained crystal was purified by silica gel chromatography to obtain 8.1 g of an intermediate C.

6.25 g of the obtained intermediate C was
To the solution dissolved in 1 l of acetone, 40 g of an aqueous solution of 0.5 g of paratoluenesulfonic acid was added, and the mixture was heated and stirred at 50 ° C. for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, dried and concentrated. Ethanol was added and stirred, and the crystals were collected by filtration and dried to obtain 5.4 g of Intermediate D. Intermediate D 0.2g
And 2-cyanomethylbenzoxazole 0.09 g
Was dissolved in 30 ml of ethanol.
Piperidine was added, and the mixture was refluxed for 6 hours. After standing to cool, the crystals were collected by filtration and purified by silica gel chromatography, and the obtained crystals were recrystallized from chloroform-ethanol to obtain 230 mg of the desired exemplified compound (D-20) (absorption spectrum λmax = 470 nm). In dichloroethane).

SYNTHESIS EXAMPLE 2 The desired exemplified compound (D-1) was prepared in the same manner as in Synthesis Example 1.
(Absorption spectrum λmax = 440 nm in dichloroethane). Synthesis Example-3 Target Exemplified Compound (D-2) in the Same Method as in Synthesis Example-1
(Absorption spectrum λmax = 442 nm in dichloroethane). Synthesis Example-4 Target Exemplified Compound (D-3) in the Same Method as in Synthesis Example-1
(Absorption spectrum λmax = 446 nm in dichloroethane). Synthesis Example-5 Target Exemplified Compound (D-6) in the Same Method as in Synthesis Example-1
(Absorption spectrum λmax = 445 nm in dichloroethane).

Next, the light emitting device of the present invention will be described. The light emitting device of the present invention has a pair of electrodes and an organic thin layer sandwiched between the electrodes and containing at least one of the amine compounds represented by any of the general formulas (I) to (VII). . Since the amine compound exhibits high-luminance light-emitting characteristics, the organic thin layer can function as a light-emitting layer. Further, the organic thin layer may contain a material other than the above-described compound to form a layer having the functions of the light emitting layer and other layers. Further, the light-emitting element of the present invention, in addition to the organic thin layer, may have other light-emitting layers, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a protective layer, and the like, Each of these layers may have another function. Various materials can be used for forming each layer.

The method for forming the organic thin layer is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, molecular lamination, coating (spin coating, casting, dip coating, etc.), and LB method. , An ink jet method, a printing method and the like are used. From the viewpoints of various characteristics of the light emitting element, ease of production, and the like, it is preferable to form the light emitting element by resistance heating evaporation or a coating method. In the case of using a coating method, the organic thin layer can be formed by applying a coating solution obtained by dissolving or dispersing the amine compound in a solvent to an anode or the like, followed by drying. In this case, the coating solution can be prepared by dissolving or dispersing the compound together with the resin component in a solvent. As the resin component used, for example, polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate,
Polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose,
Examples include vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin. Although the thickness of the organic thin layer is not particularly limited, it is usually 1 nm to 5 μm.
m, preferably 5 nm to 1 μm, more preferably 10 nm to 500 nm.

The organic thin layer may contain another luminescent material in addition to the amine compound. Examples of the light-emitting material include benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives,
Perinone derivatives, oxadiazole derivatives, aldazine derivatives, pyrazine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, aromatic dimethylidyne compounds, 8 And polymer compounds such as polythiophene, polyphenylene, and polyphenylenevinylene, and various metal complexes typified by metal complexes of quinolinol derivatives and rare earth complexes.

The light emitting device of the present invention has a pair of electrodes consisting of an anode and a cathode. The anode supplies holes to a hole injection layer, a hole transport layer, a light-emitting layer, and the like, and includes a metal,
It can be formed using an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof, and has a work function of 4
It is preferable to use a material having eV or more. In particular,
Conductive metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), or gold,
Silver, chromium, metals such as nickel, and mixtures or laminates of these metals and conductive metal oxides, copper iodide,
Examples include inorganic conductive substances such as copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO. Preferably, the conductive metal oxide is used. In particular, ITO is preferable in terms of productivity, high conductivity, transparency, and the like. The thickness of the anode can be appropriately selected depending on the material, but is usually from 10 nm to 5 μm.
m, and more preferably 50 nm to
1 μm, more preferably 100 nm to 500 nm
It is.

As the anode, one obtained by forming a layer made of the above-mentioned material on a substrate made of soda lime glass, non-alkali glass, transparent resin or the like is usually used. When glass is used as the substrate, it is preferable to use non-alkali glass for the material in order to reduce ions eluted from the glass. When soda lime glass is used, it is preferable to use a glass coated with a barrier coat such as silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain mechanical strength, but when glass is used, it is usually 0.2 mm or more, preferably 0.7 mm
Use the above. When a layer made of the above material is formed on a substrate, various methods are used depending on the material. For example, when an ITO electrode is formed, an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction A method such as a sol-gel method or a method of applying a dispersion of indium tin oxide can be used. On the prepared anode,
By performing a cleaning process or other processes, the driving voltage of the element can be reduced or the luminous efficiency can be improved. For example, in the case of an ITO electrode, UV-ozone treatment, plasma treatment, and the like are effective.

The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, and the like. The cathode has good adhesion and ionization potential between the negative electrode and the adjacent layers such as the electron injection layer, the electron transport layer, and the light emitting layer. , Stability and the like. As a material for the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specifically, an alkali metal (for example, L
i, Na, K, Cs, etc.) and their fluorides, alkaline earth metals (eg, Mg, Ca, etc.) and their fluorides, gold,
Silver, lead, alnium, sodium-potassium alloy or a mixed metal thereof, lithium-aluminum alloy or a mixed metal thereof, magnesium-silver alloy or a mixed metal thereof, rare earth metals such as indium, ytterbium and the like can be mentioned. Preferably, the material has a work function of 4 eV or less, and more preferably, aluminum or lithium-
Aluminum alloy or a mixed metal thereof, magnesium-silver alloy or a mixed metal thereof, and the like. The cathode is
The compound and the mixture may have a single-layer structure or a layered structure in which two or more layers of the compound and the mixture are stacked. The thickness of the cathode can be appropriately selected depending on the material,
Usually, it is preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 10 nm to 1 μm.
It is 0 nm to 1 μm. The electron beam method is used to make the cathode,
A method such as a sputtering method, a resistance heating evaporation method, and a coating method is used, and a metal can be evaporated alone, or two or more components can be simultaneously evaporated. Further, it is possible to form an alloy electrode by depositing a plurality of metals at the same time, or an alloy prepared in advance may be deposited. The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

The light emitting device of the present invention has at least one light emitting layer. The light emitting layer has a function of injecting holes from an anode, a hole injection layer or a hole transport layer when applying an electric field, and a function of injecting electrons from a cathode, an electron injection layer or an electron transport layer, The layer has a function of transferring injected charges and a function of providing a field for recombination of holes and electrons to emit light. In the present invention, the light emitting layer is preferably at least one of the amine compounds represented by any of the general formulas (I) to (VII), but other light emitting materials may be used in combination. Other light-emitting materials include, for example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives,
Naphthalimide derivative, coumarin derivative, perylene derivative, perinone derivative, oxadiazole derivative, aldazine derivative, pyrazine derivative, cyclopentadiene derivative, bisstyrylanthracene derivative, quinacridone derivative, pyrrolopyridine derivative, thiadiazolopyridine derivative, cyclopentadiene derivative, Polymer compounds such as polythiophene, polyphenylene, and polyphenylene vinylene, and various metal complexes such as styrylamine derivatives, aromatic dimethylidin compounds, and metal complexes of 8-quinolinol derivatives and rare earth complexes, and the like. Although the thickness of the light emitting layer is not particularly limited, it is usually 1 nm to
It is preferably in the range of 5 μm, more preferably 5 nm
１1 μm, more preferably 10 nm to 500 nm.
It is.

The light emitting device of the present invention comprises a hole injection layer and / or
Alternatively, it may have a hole transport layer. The material to be contained in the hole injection layer and the hole transport layer has a function of injecting holes from the anode, a function of transporting holes, or a function of blocking electrons injected from the cathode. Should be fine. Specific examples thereof include carbazole derivatives,
Triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives,
Fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds,
Porphyrin compounds, polysilane compounds, poly (N
-Vinylcarbazole) derivative, aniline-based copolymer,
Conductive polymer oligomers such as thiophene oligomers and polythiophenes are exemplified. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually 1
It is preferably in the range of nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 50 μm.
0 nm. The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. As described above, the amine compound is contained in the hole injection layer and / or the hole transport layer together with the material to form the light emitting layer, the hole injection layer and / or the hole injection layer.
Alternatively, the layer may also have a function as a hole transport layer.

The hole injecting layer and the hole transporting layer may be formed by a vacuum evaporation method, an LB method, an ink jet method, a printing method, or a method of coating by dissolving or dispersing the hole injecting and transporting agent in a solvent (spinning method). Coating method, casting method,
Dip coating method) is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate, ABS resins, polyurethanes, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins and the like.

The light emitting device of the present invention has an electron injection layer and / or
Alternatively, it may have an electron transport layer. The material of the electron injecting layer and the electron transporting layer may be a material having any of a function of injecting electrons from a cathode, a function of transporting electrons, and a function of blocking holes injected from an anode. Specific examples thereof include a triazole derivative, an oxazole derivative,
Heterocyclic tetracarboxylic acids such as oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbidimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, and naphthalene perylene Acid anhydrides, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives and metal phthalocyanines,
Various metal complexes represented by metal complexes having benzoxazole or benzothiazole as a ligand are exemplified. The charge transporting material used for the light emitting device of the present invention is preferably a compound having a condensed heterocyclic structure, and specifically, a compound described in the specification of Japanese Patent Application No. 11-207957 (more specifically, Preferably, a compound represented by the general formula (IX)) is preferable. The thickness of the electron injection layer and the electron transport layer is not particularly limited, but is usually 1 nm.
~ 5 μm, more preferably 5n
m to 1 μm, more preferably 10 nm to 500 n
m. The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. Examples of the method for forming the electron injecting layer and the electron transporting layer include a vacuum deposition method, an LB method, an inkjet method, a printing method, and a method of coating by dissolving or dispersing the electron injecting and transporting agent in a solvent (spin coating method, casting method,
A dip coating method or the like is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied. Note that, as described above, the amine compound and the material together with the electron injection layer and / or
Alternatively, the light-emitting layer may be contained in the electron-transporting layer to form a layer having the functions of the light-emitting layer, the electron-injecting layer, and / or the electron-transporting layer.

The light emitting device of the present invention may have a protective layer. As a material of the protective layer, the protective layer is a layer having a function of preventing a component such as moisture or oxygen that promotes element deterioration from entering the element. Specifically, In, Sn, Pb, Au, Cu, Ag, Al,
Metals such as Ti and Ni, MgO, SiO, SiO ₂ , Al ₂
O ₃ , GeO, NiO, CaO, BaO, Fe ₂ O ₃ , Y ₂
Metal oxides such as O ₃ and TiO ₂ , MgF ₂ , LiF, Al
Metal fluorides such as F ₃ and CaF ₂ , polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, and a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene. Polymer, copolymer obtained by copolymerizing a monomer mixture containing tetrafluoroethylene and at least one comonomer, fluorinated copolymer having a cyclic structure in the copolymer main chain, water absorption of 1% or more Sex substance,
Examples include a layer containing a moisture-proof substance having a water absorption of 0.1% or less. There is no particular limitation on the method of forming the protective layer,
For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency excitation ion plating), plasma CVD, laser CVD , A thermal CVD method, a gas source CVD method, a coating method, and an ink jet method can be applied.

[0107]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. [Example 1] A transparent support substrate made of ITO having a thickness of 150 nm formed on a glass substrate of 25 mm x 25 mm x 0.7 mm (manufactured by Tokyo Sanyo Vacuum Co., Ltd.) was used. After etching and washing this transparent support substrate, about 10 nm of copper phthalocyanine was deposited. Next, as the second layer, TPD (N,
N'-bis (3-methylphenyl) -N, N'-diphenylbenzidine) is about 40 nm, as a third layer, Exemplified Compound D-1 is about 40 nm, and as a fourth layer, Alq
(Tris (8-hydroxyquinolinato) aluminum)
Was deposited in a vacuum of about 20 nm and in the order of 10 ⁻³ to 10 ⁻⁴ Pa at a substrate temperature of room temperature. Next, a mask (light emitting area of 5 mm ×
5 mm), and magnesium: silver = 10: 1 is co-deposited at 250 nm in a vapor deposition apparatus.
0 nm was deposited to form a cathode. A light-emitting element was manufactured through the above steps.

Examples 2 to 4 Light emitting devices were produced in the same manner as in Example 1 except that the exemplified compound D-1 used in Example 1 was changed to the exemplified compounds shown in Table 1 below. Example 5 The exemplified compound D-1 used in Example 1 was replaced with D-
A light emitting device was prepared in the same manner as in Example 1, except that Aq was changed to Compound ET-1 represented by the following structural formula.

[0109]

Embedded image

[Comparative Examples 1 to 3] Light-emitting devices were produced in the same manner as in Example 1 except that Exemplified Compound D-1 used in Example 1 was replaced with comparative compounds shown in Table 1 below.

Each of the manufactured light emitting devices was applied with a DC constant voltage to the EL device using Toyo Technica Source Measure Unit Model 2400 to emit light, and the brightness, emission wavelength, and chromaticity coordinates were obtained. Luminance is a luminance meter BM of Topcon
Measured at -8. The emission waveform was measured with a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics, and chromaticity coordinates were obtained by calculation from the measured values. As the light emission from orange to red, the chromaticity coordinates (x, y) are x> 0.55 and y <
It is preferably 0.45. The luminance of the dark spot after 100 hours of light emission was evaluated according to the following criteria. The results are shown in Table 1 below. ：: Dark spots cannot be visually confirmed. ：: There are few dark spots. X: There are many dark spots.

[0112]

[Table 1]

[0113]

Embedded image

As is clear from the results in Table 1, the comparison compound A emitting green-blue light and the comparison compound C emitting green light showed
The compounds of the present invention used in the examples can emit orange to red light. When used alone as the light-emitting layer, Comparative Compound B exhibited low luminance, whereas the compound of the present invention used in the Examples was capable of emitting high luminance light. In addition, it was demonstrated that the light-emitting element of the example had a uniform surface state at the time of element production, less occurrence of dark spots due to driving, and excellent durability compared to the light-emitting element of the comparative example. Was. In addition, it was shown that, in particular, higher luminance emission can be achieved when combined with ET-1.

[Embodiments 6 to 8] In the same manner as in Embodiment 1, ITO
After etching and washing the substrate, TPD was deposited to a thickness of about 40 nm. Then, each compound and Alq shown in Table 2 below were used.
(Tris (8-hydroxyquinolinato) aluminum)
Were co-deposited at a deposition rate of 0.04 ° / sec and 4 ° / sec, respectively, to a film thickness of about 40 nm. Further, Alq was independently vapor-deposited in a thickness of 20 nm, and then a cathode was vapor-deposited in the same manner as in Example 1 to obtain light-emitting elements. About the obtained light emitting element, the same evaluation as Example 1 was performed. The results are shown in Table 2 below.

[0116]

[Table 2]

As is evident from the results in Table 2, when the compound of the present invention is used as a dope dye, high luminance emission is possible.
It was shown that a light-emitting material having excellent durability could be obtained.

[Embodiments 9 to 11] In the same manner as in Embodiment 1, the IT
After etching and washing the O substrate, 40 mg of poly (N-vinylcarbazole) and PBD (2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,
3,4-oxadiazole) and 0.5 mg of each compound shown in Table 3 below were added to 3 m of 1,2-dichloroethane.
1 and spin-coated on a washed ITO substrate. The thickness of the produced organic thin film was about 100 nm.
Next, a cathode was deposited in the same manner as in Example 1 to obtain light-emitting elements. About the obtained light emitting element, the same evaluation as Example 1 was performed. The results are shown in Table 3 below.

[0119]

[Table 3]

As is clear from the results shown in Table 3 below, in the light emitting devices of the examples using the compounds of the present invention, low voltage driving and high luminance light emission were possible even in the coating method in which the light emission luminance was low.

Example 12 After etching and washing an ITO substrate in the same manner as in Example 1, about 60 n of Exemplified Compound D-3 were added.
After m evaporation, Alq was evaporated to about 40 nm. Next, a cathode was deposited in the same manner as in Example 1 to produce a light-emitting element. As a result of evaluating the manufactured device, the luminance was 900 cd /
m ² . High-luminance light emission with λmax = 646 nm and CIE chromaticity (x, y) = (0.62, 0.34) was observed, indicating that the compound of the present invention is effective as a hole injection / transport agent and luminescent agent. Was.

Example 13 An NPD (N, N, N) was placed on an etched and cleaned ITO glass substrate in the same manner as in Example 1.
N'-bis (1-naphthyl) -N, N'-diphenylbenzidine) is about 40 nm, Exemplified compound D-20 is about 20 nm, bathocuproine is about 10 nm and Alq
(Tris (8-hydroxyquinolinato) aluminum)
About 30 nm was deposited. Next, a cathode was deposited in the same manner as in Example 1 to produce a light-emitting element. As a result of evaluating the fabricated device, it emitted high-brightness light with a luminance of 1000 cd / m ² at 16 V.

Example 14 On an ITO glass substrate etched and washed in the same manner as in Example 1, 40 mg of poly (N-vinylcarbazole) and 2,5-bis (1-naphthyl) -1,3,4 -Oxadiazole 12 mg, tetraphenylbutadiene 10 mg, and exemplary compound D
A solution of 0.1 mg of -1 in 3 ml of 1,2-dichloroethane was spin-coated. At this time, the thickness of the organic layer was about 120 nm. Next, a cathode was deposited in the same manner as in Example 1 to produce a light-emitting element. I
When a DC voltage was applied using the TO electrode as the anode and the Mg: Ag electrode as the cathode, and the light emission characteristics were examined, white light emission of (x, y) = (0.37, 0.34) on the CIE chromaticity diagram at 15 V was obtained. (A luminance of 1900 cd / m ² ), which proved to be effective for white light emission.

[0124]

The organic light-emitting device containing the amine compound of the present invention is capable of emitting light with high luminance. In particular, an undoped device (light-emitting layer formed of a single dye, which has conventionally been difficult to emit light with high luminance). Element) to provide high-luminance light emission and to provide an element with excellent durability. Therefore, by using the amine compound, it is possible to provide an element which has good emission characteristics and small variation in performance between elements, and is advantageous in terms of manufacturing cost and the like. Also, by using the amine compound, even when the light-emitting layer is formed by a coating method having a low emission luminance usually,
The light-emitting element shows good light-emitting characteristics.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07C 317/48 C07C 317/48 4C055 C07D 213/57 C07D 213/57 4C056 223/14 223/14 4C063 235 / 16 235/16 4C065 241/42 241/42 4C072 263/54 263/54 4H006 263/56 263/56 4H049 265/38 265/38 4H056 271/10 271/10 277/64 277/64 279/22 279 / 22 285/12 295/16 Z 295/16 307/54 307/54 307/91 307/91 333/24 333/24 403/06 403/06 409/06 409/06 409/10 409/10 413/10 413/10 417/06 417/06 417/12 417/12 471/04 107Z 471/04 107 498/04 101 498/04 101 C07F 7/10 J C07F 7/10 C09B 23/00 L C09B 23/00 J 57/00 S 57/00 V H05B 33/14 B H05B 33/14 C07D 285/12 A F term (see Consideration) 3K007 AB02 AB03 AB04 AB06 AB12 EB00 4C023 EA04 4C034 DM01 4C036 AA02 AA12 AD08 AD16 AD17 4C037 GA03 SA10 4C055 AA01 BA06 BA27 BA35 BB01 BB04 CA01 DA01 4C056 AA01 AA02 CA01 AC03 AD03 FA03 4C063 AA01 BB04 BB06 CC34 CC52 CC62 CC92 DD06 DD08 DD14 DD19 DD22 DD62 DD76 EE10 4C065 AA04 BB05 CC01 DD03 EE02 HH01 JJ01 KK03 KK09 LL01 PP03 4C072 AA01 AA07 BB03 BB06 CC02 CC12 EE01 FF01A014H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H04H01H01H01H01H01H01H04H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H01H) VW02 4H056 CA02 CA05 CC02 CE02 CE03 DA01 DA02 DA03 DB01 DB10 DB12 DC03 DD23 FA05

Claims (10)

[Claims] 1. A compound represented by the following general formula (I):
A light-emitting element material, characterized in that: General formula (I)(Wherein, Ar¹Represents a divalent aryl or heterocyclic group
Represents, R^TwoAnd R^ThreeAre each independently an aryl group,
A ring group or an aliphatic hydrocarbon group;¹, R^TwoAnd
And R^ThreeAt least two groups selected from are linked to form a ring
It may be formed. Ar⁸Is an aryl or heterocyclic group
Represents Ar⁸An aryl group or a heterocyclic group represented by
Is not substituted with an amino group. R^4a, R^5a,
R^6aAnd R ^7aAre each independently a hydrogen atom or a monovalent group
And R^4a, R^5a, R^6aAnd R^7aAt least one of
Is an electron-withdrawing group having a Hammett σp value of 0.2 or more
Represents L¹Is a divalent aryl group, a divalent heterocycle
Group, or between aryl groups, between heterocyclic groups, or
A single bond between the reel group and the heterocyclic group, a vinyl group, C = X
Group, silyl group, aryl group and aromatic hetero 5 to
Divalent group linked by at least one selected from 6-membered ring groups
Represents X is an oxygen atom, a sulfur atom, NR^X1Or CR
^X2R^X3And R^X1, R^X2And R^X3Are each independently
Represents a hydrogen atom or a monovalent group. ) 2. The light emitting device material according to claim 1, wherein the compound represented by the general formula (I) is represented by the following general formula (II).
General formula (II) (Wherein, Ar ¹ , R ² , R ³ and Ar ⁸ have the same meanings as those in formula (I). R ^4b , R ^5b , R ^6b and R ^7b each independently represent a hydrogen atom, a heterocyclic ring, Represents a group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group, and R ^4b , R ^5b , R ^6b and R ^7b are not all hydrogen atoms at the same time. L ² represents a divalent aryl group, 2
A single bond, a vinyl group, a C = X group, a silyl group, an aryl group, or an aromatic heterocyclic group having 5 to 6 members between a divalent heterocyclic group or an aryl group, between heterocyclic groups, or between an aryl group and a heterocyclic group. It represents a divalent group linked by at least one selected from a cyclic group. X is an oxygen atom, a sulfur atom, NR
^{X 1} or CR ^X2 represents R ^X3 , wherein R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom or a monovalent group. However, L ²
Represents an aryl group having three or more rings, R ^4b , R ^5b , R ^6b
And at least two selected from R ^7b are not hydrogen atoms. ) 3. The light emitting device material according to claim 2, wherein the compound represented by the general formula (II) is represented by the following general formula (III). General formula (III) (Wherein, Ar ¹ , R ² , R ³ , Ar ⁸ and L ² have the same meanings as those in formula (II). R ^4c represents a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group. , A carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group, wherein R ^5c , R ^6c and R ^7c are each independently a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group,
Represents a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group. ) 4. The light emitting device material according to claim 3, wherein the compound represented by the general formula (III) is represented by the following general formula (IV). General formula (IV) (Wherein, Ar ¹ , R ² , R ³ , Ar ⁸ and L ² have the same meanings as those in formula (II). R ^4d and R ^7d each independently represent a heterocyclic group, a perhalogenoalkyl Represents a group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group.) 5. The light emitting device material according to claim 4, wherein the compound represented by the general formula (IV) is represented by the following general formula (V). General formula (V) (In the formula, Ar ¹ , R ² , R ³ , and Ar ⁸ have the same meanings as in each of formulas (I). R ^4e and R ^7e are the same as R ^4d and R ^{7d in} formula (IV), respectively. Has the same meaning, and L ³ represents a divalent mono- or bicyclic aryl group or a divalent heterocyclic group.) 6. The light emitting device material according to claim 4, wherein the compound represented by the general formula (IV) is represented by the following general formula (VI).
General formula (VI) (Wherein, Ar ^1, R ² and R ^3, .Ar ⁹ is the same as the corresponding ones of the general formula (I) represents an aryl group or a heterocyclic group, an aryl group or a heterocyclic group represented by Ar ⁹ Is not substituted with an amino group R ^4f and R ^7f
Each independently represents a heterocyclic group, a perhalogenoalkyl group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group. L ⁴ is 2
It represents a trivalent or higher-valent aryl group. ) 7. A light emitting device material, which is a compound represented by the general formula (VII). General formula (VII) (Wherein, Ar ¹ represents a divalent aryl group or a heterocyclic group; Ar ² and Ar ³ each independently represent an aryl group or a heterocyclic group; selected from Ar ¹ , Ar ² , and Ar ³ .Ar ⁸ at least two may be linked to form a ring which represents an aryl group or a heterocyclic group, Ar ⁸
Is not substituted with an amino group. L ³ represents a divalent monocyclic or bicyclic aryl group or a divalent heterocyclic group, and R ^4g and R ^7g each independently represent a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, Represents a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group. ) 8. A light emitting device comprising a pair of electrodes and an organic thin layer containing the light emitting device material according to claim 1 sandwiched between the electrodes. 9. A light-emitting element comprising a pair of electrodes and a layer sandwiched between the electrodes, wherein the light-emitting element material according to claim 1 is dispersed in a polymer. 10. An amine compound represented by the following general formula (VII). General formula (VII) (In the formula, Ar ¹ represents a divalent aryl group or a heterocyclic group; Ar ² and Ar ³ each independently represent an aryl group or a heterocyclic group; selected from Ar ¹ , Ar ² , and Ar ³ .Ar ⁸ at least two may be linked to form a ring which represents an aryl group or a heterocyclic group, Ar ⁸
Is not substituted with an amino group. L ³ represents a divalent monocyclic or bicyclic aryl group or a divalent heterocyclic group, and R ^4g and R ^7g each independently represent a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, Represents a carbamoyl group, a sulfonyl group, a sulfamoyl group or an acyl group. )