JP2002220586A - Material for light emitting element and light emitting element containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain both a material for a light emitting element and a light emitting element having high-luminance and high-efficiency luminescence at a low-voltage drive and excellent stability in repeated use. SOLUTION: This material for a light emitting element [e.g. formula (D-16)] is represented by general formula I [R1 and R2 are the same or different and each H, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Ar1 is a connecting group composed of a conjugated bond containing a heterocyclic group; R1, R2 and Ar1 maybe bonded to form a ring, respectively; R3 to R5 are the same or different and each H or a substituent group; Y is O, S or N-RY1 (RY1 is H or a substituent group); RX and RY are each H or a substituent group and at least one is an electron attractive group]. This light emitting element comprises the material for a light emitting element at least in one layer.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to fields such as backlights, flat panel displays, illumination light sources, display elements, electrophotography, organic semiconductor lasers, recording light sources, exposure light sources, reading light sources, signs, signboards, and optical communication devices. The present invention relates to a light emitting device that can be used for a light emitting device.

[0002]

2. Description of the Related Art At present, research and development of a variety of light emitting devices are being actively conducted. Among them, organic electroluminescent (EL) devices are ultra-thin, lightweight, high-speed response, and have a wide viewing angle. It has features such as low-voltage driving and is attracting attention as a promising light emitting element. Generally, an organic EL element is composed of a light emitting layer and a pair of opposed electrodes sandwiching the layer, and electrons injected from a cathode and holes injected from an anode are recombined,
It utilizes light emission from generated excitons.

[0003] At present, an organic EL which emits light at high luminance at low voltage
The device has a laminated structure shown by Tang et al. (Applied Physics Letters., 51
Vol., 913, 1987). This device emits high-luminance green light by laminating an electron-transporting / light-emitting material and a hole-transporting material, and reaches a luminance of several thousand cd / m ² at a DC voltage of 6 to 7 V. However, considering use as a full-color display and a light source, three primary colors or white light emission is necessary for practical use. However, in the above-mentioned element, an aluminum complex of 8-quinolinol is used as a light-emitting material, and the light emission color is limited to green. Therefore, development of a light emitting element of another emission color is desired. Heretofore, 4- (dicyanomethylene) -2-methyl- (4-dimethylaminostyryl) -4H-pyran (DCM), a derivative thereof, a Nile red derivative, Eu
(III) Although light-emitting materials such as complexes have been developed, there have been problems such as poor color purity, low luminance, low luminous efficiency, and low durability.

[0004] Therefore, after various studies, a device using a compound containing a cyclic acidic nucleus such as the compound described in JP-A-11-335661 was prepared and evaluated. It has been found that it has excellent efficiency and durability. However, when a light-emitting material is used at a relatively high concentration, the drive voltage increases, and a reduction in the drive voltage has been desired in order to achieve high efficiency and to obtain the same voltage-current characteristics as those of blue and green light-emitting elements.

[0005]

SUMMARY OF THE INVENTION It is a first object of the present invention to provide a light emitting device having good initial response during pulse driving. A second object of the present invention is to provide a light emitting device having a low driving voltage.

[0006]

The present invention has been achieved by the following means. (1) A light emitting device material represented by the following general formula (I). General formula (I)

[0007]

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In the formula, R ¹ and R ² may be the same or different and represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Ar ¹ represents a linking group comprising a conjugated bond containing a heterocyclic group, and R ¹ , R ² , and Ar ¹ may be bonded to each other to form a ring. R ³ , R ⁴ , R ⁵
May be the same or different and each represents a hydrogen atom or a substituent. Y is an oxygen atom, a sulfur atom, N-R ^Y1
And R ^Y1 represents a hydrogen atom or a substituent. Rx and Ry each represent a hydrogen atom or a substituent, and at least one of them represents an electron-withdrawing group. (2) In a light-emitting element in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of electrodes, at least one layer is a layer containing at least one compound represented by the general formula (I). A light emitting element characterized by the above-mentioned. General formula (I)

[0009]

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In the formula, R ¹ and R ² may be the same or different and represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Ar ¹ represents a linking group comprising a conjugated bond containing a heterocyclic group, and R ¹ , R ² , and Ar ¹ may be bonded to each other to form a ring. R ³ , R ⁴ , R ⁵
May be the same or different and each represents a hydrogen atom or a substituent. Y is an oxygen atom, a sulfur atom, N-R ^Y1
And R ^Y1 represents a hydrogen atom or a substituent. Rx and Ry each represent a hydrogen atom or a substituent, and at least one of them represents an electron-withdrawing group. (3) In a light-emitting element in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of electrodes, the light-emitting layer has at least one compound represented by the general formula (I) dispersed in a polymer. The light-emitting device according to the above (2), which is a layer. General formula (I)

[0011]

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In the formula, R ¹ and R ² may be the same or different and represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Ar ¹ represents a linking group comprising a conjugated bond containing a heterocyclic group, and R ¹ , R ² , and Ar ¹ may be bonded to each other to form a ring. R ³ , R ⁴ , R ⁵
May be the same or different and each represents a hydrogen atom or a substituent. Y is an oxygen atom, a sulfur atom, N-R ^Y1
And R ^Y1 represents a hydrogen atom or a substituent. Rx and Ry each represent a hydrogen atom or a substituent, and at least one of them represents an electron-withdrawing group.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, a compound represented by the general formula (I) of the present invention will be described.
Will be described. R¹And R^TwoAre the same
Or may be different, such as a hydrogen atom, an aliphatic hydrocarbon group,
Represents a reel group or a heterocyclic group. Also, if possible
R¹And R^Two, R¹And Ar ¹, R^TwoAnd Ar¹Are each other
They may be linked together to form a ring.

The aliphatic hydrocarbon group represented by R ¹ and R ² is a linear, branched or cyclic alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably The number is 1 to 12, and examples thereof include methyl, ethyl, iso-propyl, n-butyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl. An alkenyl group (preferably having 2 to 2 carbon atoms)
30, more preferably 2 to 20 carbon atoms, still more preferably 2 to 12 carbon atoms, for example, vinyl, allyl, 2-
Butenyl, 3-pentenyl and the like. ), An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, still more preferably having 2 to 12 carbon atoms,
For example, propargyl, 3-pentynyl and the like can be mentioned. ), Preferably an alkyl group or an alkenyl group, more preferably a methyl group, an ethyl group, a propyl group, a butyl group, or an allyl group. R ¹ , R ² , and Ar ¹ may be combined with each other to form a condensed ring. Examples of the ring formed by linking R ¹ and R ² include a pyrrolidine ring, a piperidine ring, and a morpholine ring. .

The aryl group represented by R ¹ and R ² is preferably a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms (for example, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl and the like). And more preferably a phenyl group having 6 to 20 carbon atoms or 1 carbon atom.
A naphthyl group having 0 to 24 carbon atoms; an anthryl group having 14 to 30 carbon atoms; and a phenanthryl group, and more preferably 6 carbon atoms.
Phenyl group of 12 to 12, naphthyl group of 10 to 16 carbon atoms,
They are an anthryl group and a phenanthryl group having 14 to 20 carbon atoms. R ¹ and R ² may be linked to form a 5- to 7-membered ring (eg, carbazole, phenoxazine, phenothiazine, azepine, benzazepine, etc.), and preferably carbazole, azepine, and benzazepine. .

The heterocyclic group represented by R ¹ and R ² is
3- to 10-membered saturated or unsaturated heterocyclic group containing at least one nitrogen atom, oxygen atom or sulfur atom, which may be a single ring or form a condensed ring with another ring May be. The heterocyclic group is preferably a 3- to 10-membered aromatic heterocyclic group, more preferably a 5- to 6-membered aromatic heterocyclic group. Specific examples of the heterocycle include, for example, pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine,
Triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole,
Quinoline, isoquinoline, phthalazine, naphthyridine,
Quinoxaline, quinazoline, cinnoline, pteridine,
Examples include acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, and tetrazaindene. The heterocycle is preferably thiophene, triazole, oxazole, pyridine, pyrimidine, pyrazine, triazine, quinoline, more preferably thiophene, pyridine, pyrimidine, triazine, quinoline, and further preferably thiophene.

An aliphatic hydrocarbon group represented by R ¹ or R ² ;
The aryl group and the heterocyclic group may 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, and particularly preferably 1 to 12 carbon atoms). 8, for example, methyl, ethyl,
iso-propyl, tert-butyl, n-octyl,
n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An alkenyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms,
For example, vinyl, allyl, 2-butenyl, 3-pentenyl and the like can be mentioned. ), An alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl), and an aryl group (preferably). Has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example, phenyl, p
-Methylphenyl, naphthyl and the like. ), An amino group (preferably having 0 to 20 carbon atoms, more preferably 0 to 12 carbon atoms, particularly preferably 0 to 6 carbon atoms, for example, amino, methylamino, dimethylamino, diethylamino, diphenylamino, dibenzylamino) Etc.), an alkoxy group (preferably having 1 to 20 carbon atoms,
More preferably, it has 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methoxy, ethoxy, butoxy and the like. ), An aryloxy group (preferably having 6 to 20 carbon atoms, more preferably having 6 to 16 carbon atoms, particularly preferably having 6 to 12 carbon atoms, for example, phenyloxy,
2-naphthyloxy and the like. ), An acyl group (preferably having 1 to 20 carbon atoms,

More preferably, it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl and the like. ), An alkoxycarbonyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, and particularly preferably having 2 to 2 carbon atoms.
12, for example, methoxycarbonyl, ethoxycarbonyl and the like. ), An aryloxycarbonyl group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms, particularly preferably having 7 to 10 carbon atoms, such as phenyloxycarbonyl, etc.), and an acyloxy group (preferably Has 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy, etc.), an acylamino group (preferably 2 to 2 carbon atoms).
It has 0, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, and includes, 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 can be mentioned. ),
An aryloxycarbonylamino group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms, particularly preferably having 7 to 12 carbon atoms, such as phenyloxycarbonylamino, etc.), and a sulfonylamino group ( Preferably it has 1 to 20 carbon atoms, more preferably 1 carbon atom
To 16, particularly preferably 1 to 12 carbon atoms, for example, methanesulfonylamino, benzenesulfonylamino and the like. ), A sulfamoyl group (preferably having 0 to 20 carbon atoms, more preferably 0 to 16 carbon atoms, particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl,
Methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl and the like can be mentioned. ), A carbamoyl group (preferably having 1 to 20 carbon atoms,

More preferably, it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl and phenylcarbamoyl. ), An alkylthio group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 1 carbon atoms)
6, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio and the like. ), An arylthio group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably having 6 to 12 carbon atoms, such as phenylthio, etc.), and a sulfonyl group (preferably having 1 carbon atom). -20, more preferably 1-1.
6, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl. ), A sulfinyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 1 carbon atoms)
6, particularly preferably 1 to 12 carbon atoms, for example, methanesulfinyl, benzenesulfinyl and the like. ), Ureido group (preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 1 carbon atoms)
12, for example, ureide, methylureide, phenylureide and the like. ), A phosphoric amide group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 1 carbon atoms)
6, particularly preferably 1 to 12 carbon atoms, for example, diethylphosphoramide, phenylphosphoramide and the like. ), Hydroxy, mercapto, halogen (eg, fluorine, chlorine, bromine, iodine), cyano, sulfo, carboxyl, nitro, hydroxamic acid, sulfino, hydrazino,
Imino group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 12 carbon atoms, and the hetero atom includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom. Imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, azepinyl and the like; and a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 carbon atoms). -30, particularly preferably 3-24 carbon atoms,
For example, trimethylsilyl, triphenylsilyl and the like can be mentioned. ) And the like. These substituents may be further substituted. 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.

When R ¹ and R ² are an aliphatic hydrocarbon group, an aryl group, or a heterocyclic group, the substituent is preferably an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an alkoxy group. Carbonyl group,
Aryloxycarbonyl group, acylamino group, sulfonylamino group, sulfonyl group, silyl group, aromatic heterocyclic group, more preferably alkyl group, alkenyl group, aryl group, alkoxy group, aryloxy group, silyl group, aromatic group A heterocyclic group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a silyl group, or an aromatic heterocyclic group.

R¹, R^TwoIs preferably an alkyl group,
An aryl group and an aromatic heterocyclic group. In general formula (I)
The compound represented by the formula is used as a charge transport material and a luminescent material (undoped)
When used as¹, R^TwoPreferably
A reel group or an aromatic heterocyclic group, more preferably
Reel group (preferably monocyclic or polycyclic having 6 to 30 carbon atoms)
And more preferably an aryl group having 6 to 20 carbon atoms.
Phenyl group, naphthyl group having 10 to 24 carbon atoms, 1 carbon atom
4 to 30 anthryl groups and phenanthryl groups;
Preferably a phenyl group having 6 to 12 carbon atoms or carbon number
A naphthyl group of 10 to 16;
And a phenanthryl group. ), R ¹And R^TwoGa
Carbazolyl group, azepinyl group, benzoazepini
In which a hydroxyl group is formed. Formula represented by the general formula (I)
When a compound is used as a doped light emitting material, R¹, R^Two
Is preferably an alkyl group, Ar¹To form a ring
Alkylene group, more preferably 1 to 1 carbon atoms
8 alkyl groups, Ar¹To form a 6-membered ring
A alkylene group, particularly preferably a methyl group or ethyl
Group, Ar¹To form a 5- or 6-membered ring
Len group (dimethylene group, trimethylene group, 3,3-dimethyl
Tyl trimethylene group).

R^Three, R^FourAnd R^FiveIs the hydrogen source
Represents a child or a substituent. R^Three~ R ^FiveA substituent represented by
Is, for example, R¹, R^TwoAs the substituents of
Can be applied. R^Three~ R^FivePreferred as a substituent represented by
Preferably, an alkyl group, an alkenyl group, an aryl group,
Alkoxy group, aryloxy group, acyl group, alkoxy
Carbonyl group, aryloxycarbonyl group, acylua
Mino group, sulfonylamino group, sulfonyl group, cyano
Group, halogen atom, hydroxy group, silyl group, aromatic group
A telocyclic group, more preferably an alkyl group, an alkenyl
Group, aryl group, alkoxy group, aryloxy group,
A silyl group and an aromatic heterocyclic group, more preferably
Alkyl group, aryl group, alkoxy group, aryloxy
Group, silyl group and aromatic heterocyclic group.

Rx and Ry are each a hydrogen atom or
Represents a substituent, and at least one represents an electron-withdrawing group.
You. As the substituent represented by Rx and Ry, for example, R
¹, R ^TwoThe substituents mentioned above can be applied. R
The substituent represented by x and Ry is preferably an alkyl
Group, alkenyl group, aryl group, alkoxy group, aryl
Luoxy group, carbonyl group, thiocarbonyl group, oxy
Carbonyl group, acylamino group, carbamoyl group, sulf
Phonylamino group, sulfamoyl group, sulfonyl group,
Rufinyl group, phosphoryl group, imino group, cyano group, ha
A halogen atom, a silyl group, an aromatic heterocyclic group,
Preferably, an alkyl group, an alkenyl group, an aryl group,
Rubonyl group, thiocarbonyl group, carbamoyl group, sulf
Famoyl, sulfonyl, imino, cyano,
An aromatic heterocyclic group, more preferably an alkyl group,
Lucenyl group, aryl group, carbonyl group, thiocarboni
Group, oxycarbonyl group, carbamoyl group, sulfa
Moyl group, sulfonyl group, imino group, cyano group, aromatic
It is an azole group. Electron-withdrawing groups represented by Rx and Ry
Preferably, the Hammett's σp value is 0.2
The above electron-withdrawing group, more preferably aryl
Group, aromatic heterocyclic group, cyano group, carbonyl group, thio group
Carbonyl group, oxycarbonyl group, carbamoyl group,
Sulfamoyl group, sulfonyl group, imino group, halogen
Atoms and Rx and Ry are linked to form an electron-withdrawing group ring
Formed, more preferably an aromatic heterocycle
Group, carbonyl group, cyano group, imino group, Rx and Ry
Linked to form an electron-withdrawing group ring, especially
Preferably, a cyano group, Rx and Ry are linked to form an electron withdrawing property.
And most preferably Rx and R
and y are linked to form a ring of an electron-withdrawing group.

As Rx and Ry and the carbon atom to which Rx and Ry are bonded to form a ring, those usually used as an acidic nucleus of a general merocyanine dye represented by formula (A) can be applied. * Corresponds to methylene in which Rx and Ry are linked. General formula (A)

[0025]

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X ^A is an oxygen atom, a sulfur atom, N—R ^A1 , C
R ^A2 represents R ^A3 , R ^A1 , R ^A2 , and R ^A3 each represent a hydrogen atom or a substituent, and Z ^A represents a group of atoms forming a 5- to 7-membered ring, and is preferably a carbon atom, a nitrogen atom, or an oxygen atom. atom,
A group of atoms that form a 5- to 7-membered ring composed of any of sulfur atoms. ^RA1 preferably represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. The aliphatic hydrocarbon group represented by R ^A1 is a linear, branched or cyclic alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms).
20, more preferably 1 to 12, for example methyl,
Examples include ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, and the like. ), An alkenyl group (preferably having 2 to 30, more preferably 2 to 20, and still more preferably 2 to 12, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl), and an alkynyl group. (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20, and still more preferably 2 to 12, and examples thereof include propargyl and 3-pentynyl.), Preferably an alkyl group and an alkenyl group, More preferred are a methyl group, an ethyl group, a propyl group, a butyl group and an allyl group.

The aryl group represented by R ^A1 is preferably a monocyclic or bicyclic aryl group having 6 to 30 carbon atoms (for example, phenyl, naphthyl, etc.), and more preferably 6 carbon atoms. To 20 phenyl groups, more preferably 6 to 12 phenyl groups. The heterocyclic group represented by R ^A1 is the same as that described for the heterocyclic group represented by R ¹ and R ² , and is preferably a pyrrole, imidazole, pyrazole, pyridine, or pyrazine. , Pyridazine, triazole, triazine, indole, indazole, thiadiazole, oxadiazole, quinoline, phthalazine, quinoxaline, quinazoline, cinnoline, tetrazole, thiazole, oxazole benzimidazole, benzoxazole, benzothiazole, benzotriazole,
More preferred are imidazole, pyridine, quinoline, thiazole, oxazole, benzimidazole, benzoxazole, benzothiazole and benzotriazole, and still more preferred are pyridine and quinoline.

The aliphatic hydrocarbon group, aryl group and heterocyclic group represented by R ^A1 may have a substituent, and the substituents described above as the substituents for R ¹ and R ² can be applied. . R ^A1 is preferably an alkyl group, an alkenyl group,
An aryl group, more preferably an alkyl group or a phenyl group.

The substituents represented by R ^A2 and R ^A3 include R
^1, can be applied those exemplified as the substituents of R ^2.
R ^A2 and R ^A3 each preferably represent a hydrogen atom, a cyano group, an oxycarbonyl group, an acyl group, a sulfonyl group, a thioether group, a carbamoyl group or a sulfamoyl group (provided that both R ^A2 and R ^A3 are hydrogen atoms; No). The oxycarbonyl group, acyl group, sulfonyl group and thioether group represented by R ^A2 and R ^A3 are an oxycarbonyl group, acyl group, sulfonyl group and thioether substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. And the aliphatic hydrocarbon group, the aryl group and the heterocyclic group in this case have the same meaning as the aliphatic hydrocarbon group, the aryl group and the heterocyclic group represented by R ^A1 . The carbamoyl group and sulfamoyl group represented by R ^A2 and R ^A3 are a carbamoyl group and a sulfamoyl group which are unsubstituted or substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. In this case, the aliphatic hydrocarbon group Wherein the aryl group and the heterocyclic group part are the same as the aliphatic hydrocarbon group, the aryl group and the heterocyclic group represented by R ^A1 , and the group represented by the general formula (A) is more preferably Formulas (B), (C), (D), (E), (F)
Or (G). General formula (B)

[0030]

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X ^B1 and X ^{B2 each} represent an oxygen atom, a sulfur atom, NR
^{B 1} , CR ^B2 R ^B3 , R ^B1 , R ^B2 , and R ^B3 each represent a hydrogen atom or a substituent, and Z ^B represents an atom group forming a 5- to 7-membered ring, and is preferably a carbon atom or a nitrogen atom. , An oxygen atom and a sulfur atom to form a 5- to 7-membered ring. R ^B1 , R ^B2 , and R ^B3 represent the above R ^A1 , R ^A2 , R
Synonymous with ^A3 . Specific examples of the acidic nucleus represented by the general formula (B) include the following examples. For example, 1,3-
Indandione nucleus, 3,5-pyrazolinedione nucleus, 1,
3-cyclohexanedione nucleus, 1,3-dioxane-
4,6-dione nucleus, 2,4,6-triketohexahydropyrimidine nucleus (for example, barbituric acid or 2-thiobarbituric acid and derivatives thereof. Examples of derivatives include 1-alkyl derivatives such as 1-methyl and 1-ethyl) , 1,3-
1,3-dialkyl such as dimethyl, 1,3-diethyl, 1,3-dibutyl, 1,3-diphenyl, 1,3-
1,3-diaryl compounds such as di (p-chlorophenyl) and 1,3-di (p-ethoxycarbonylphenyl);
1-alkyl-1-aryls such as ethyl-3-phenyl, and 1,3-diheterocyclic substituents such as 1,3-di (2-pyridyl), etc.), and more specifically, The examples shown and derivatives thereof are mentioned.

[0032]

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Formula (C)

[0034]

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X^CIs an oxygen atom, a sulfur atom, NR^C1, C
R^C2R^C3And R^C1, R^C2, R^C3Is a hydrogen atom
Or a substituent. Y^C1, Y^C2Are each a nitrogen atom,
C-R^C4And R^C4Represents a hydrogen atom or a substituent,
R is a substituent¹, R^Two, R^ThreeAs a substituent of
Things can be applied. Z^CIs a group of atoms forming a 5- to 7-membered ring
Represents preferably a carbon atom, a nitrogen atom, an oxygen atom,
A group of atoms forming a 5- to 7-membered ring consisting of any of the yellow atoms
is there. R^C1, R^C2, R^C3Is R^A1, R^A2, R ^A3Synonymous with
It is. Specific examples of the acidic nucleus represented by the general formula (C)
Examples include the following. For example, pyrazolone nucleus, i
Soxazolinone nucleus, oxazolinone nucleus, furanone nucleus,
Oxindole nucleus, imidazolidone nucleus, 1,2,3
6-tetrahydropyridine-3,6-dione nucleus and the like
More specifically, such as the examples shown below and their derivatives
And so on.

[0036]

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Formula (D)

[0038]

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X ^D is an oxygen atom, a sulfur atom, N—R ^D1 , C
R ^D2 represents R ^D3 , R ^D1 , R ^D2 , and R ^D3 each represent a hydrogen atom or a substituent, and Z ^D represents an atom group forming a 5- to 7-membered ring, and is preferably a carbon atom, a nitrogen atom, or an oxygen atom. atom,
A group of atoms that form a 5- to 7-membered ring composed of any of sulfur atoms. R ^D1 , R ^D2 and R ^D3 have the same meanings as R ^A1 , R ^A2 and R ^A3 described above. Specific examples of the acidic nucleus represented by the general formula (D) include the following examples and derivatives thereof.

[0040]

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Formula (E)

[0042]

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X^EIs an oxygen atom, a sulfur atom, NR^E1, C
R^E2R^E3And R^E1, R^E2, R^E3Is a hydrogen atom
Or a substituent. Y^E1, Y^E2Are each a nitrogen atom,
C-R^E4And R^E4Represents a hydrogen atom or a substituent,
R is a substituent¹, R^Two, R^ThreeAs a substituent of
Things can be applied. Z^EIs a group of atoms forming a 5- to 7-membered ring
Represents preferably a carbon atom, a nitrogen atom, an oxygen atom,
A group of atoms forming a 5- to 7-membered ring consisting of any of the yellow atoms
is there. R^E1, R^E2, R^E3Is R^A1, R^A2, R ^A3Synonymous with
It is. Specific examples of the acidic nucleus represented by the general formula (E)
Examples include the following examples and derivatives thereof.

[0044]

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General formula (F)

[0046]

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X^F1, X^F2Is an oxygen atom, a sulfur atom, N-
R^F1, CR^F2R^F3And R^F1, R ^F2, R^F3Are each
Represents a hydrogen atom or a substituent. Y^F1, Y^F2Each acid
Elemental atom, sulfur atom, NR^F5Represents R^F1, R^F5Is above
R^A1Is synonymous with^F2, R ^F3Is R^A2, R^A3Synonymous with
You. Specific examples of the acidic nucleus represented by the above general formula (F)
Examples include the following. 2-thio-2,4-thiazoli
Zindione nuclei (e.g., rhodine and its derivatives)
And so on. As derivatives, for example, 3-methylrhodanine, 3-
3-Al such as ethyl rhodanine and 3-allyl rhodanine
3-ants such as killrhodanine and 3-phenylrhodanine
Oolordanine, 3- (2-pyridyl) rhodanine and the like
3-position heterocyclic-substituted rhodanine, etc.), 2-thio-2,4-
Oxazolidinedione nucleus, 2-thio-2,4- (3H,
5H) -oxazoledione nucleus, 2-thio-2,5-thio
Ozolidinedione nucleus, 2,4-thiozolidinedione nucleus,
Thiazolin-4-one nucleus, 4-thiazolidinone nucleus, 2,
4-imidazolidinedione (hydantoin) nucleus, 2-thio
O-2,4-Imidazolidinedione (2-thiohydanto
In) nucleus, imidazolin-5-one nucleus, etc.
Represents an analog. More specifically, for example,
Examples are as follows.

[0048]

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General formula (G)

[0050]

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X ^G is an oxygen atom, a sulfur atom, N—R ^G1 , C
R ^G2 represents R ^G3 , and R ^G1 , R ^G2 , and R ^G3 each represent a hydrogen atom or a substituent. Y ^G1 and Y ^G2 are each a nitrogen atom,
^Represents C—R ^G4 , R ^G4 represents a hydrogen atom or a substituent,
As the substituent, those exemplified as the substituents for R ¹ , R ² and R ³ can be applied. n represents 1, 2 or 3. Z ^G represents an atomic group forming a 5- to 7-membered ring, preferably comprising any carbon atom, a nitrogen atom, oxygen atom, sulfur atom 5
A group of atoms forming a 7-membered ring. R ^G1 , R ^G2 and R ^G3 have the same meanings as R ^A1 , R ^A2 and R ^A3 described above. The above general formula (G)
Specific examples of the acid nucleus represented by are, for example, the following examples.

[0052]

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Further, = X ^A in the above general formula (A) may be further condensed with an acidic nucleus represented by the general formula (A). For example, the following example is given as an example of the rhodanine nucleus represented by the general formula (F).

[0054]

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As the ring formed by Rx, Ry and the carbon atom to which they are bonded, preferably a 1,3-indandione nucleus, a 2,4,6-triketohexahydropyrimidine nucleus (including a thioketone), a pyrazolone nucleus , Isoxazolinone nucleus, oxazolinone nucleus, furanone nucleus, oxindole nucleus, imidazolidone nucleus, 1,2,3,6-tetrahydropyridine-2,6-dione nucleus, benzothiophen-3-one nucleus, oxobenzothiophene- 3-one nucleus, dioxobenzothiophen-3-one nucleus, coumaranone nucleus, oxindole nucleus, 2-thio-2,4-thiazolidinedione nucleus, 2-thio-2,4-oxazolidinedione nucleus, 2-thio- 2,5-thiazolidinedione nucleus,
A 2,4-thiazolidinedione nucleus, more preferably a 1,3-indandione nucleus, a barbituric acid derivative,
-Thiobarbituric acid derivative, pyrazolone nucleus, isoxazolinone nucleus, oxazolinone nucleus, furanone nucleus, imidazolidone nucleus, 1,2,3,6-tetrahydropyridine-
2,6-dione nucleus, oxobenzothiophen-3-one nucleus, dioxobenzothiophen-3-one derivative 2-thio-2,4-thiazolidinedione nucleus, 2-thio-2,4
-Oxazolidinedione nucleus, particularly preferably
It is a 1,3-indandione nucleus.

Ar ¹ represents a linking group comprising a conjugated bond containing a hetero ring. The hetero ring is the same as the hetero ring used for the hetero ring group described for R ¹ and R ² . The linking group represented by Ar ¹ is preferably a divalent hetero ring (which may further form a condensed ring, and is preferably an aromatic hetero ring or a coumarin ring formed from an azine, azole, thiophene, or furan ring) And a group consisting of a combination of a divalent aromatic heterocycle and alkenylene, alkynylene, and arylene, and more preferably a group consisting of a combination of a heterocycle having 2 to 30 carbon atoms and a divalent aromatic heterocycle and vinylene. And particularly preferably a monocyclic or bicyclic divalent aromatic heterocycle, or a monocyclic or benzo-fused heterocycle combined with vinylene (preferably benzothiazole, indole, benzoxazole, benzothiazole). Specific examples of the linking group represented by Ar ¹ include, for example, the following.

[0057]

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The linking group represented by Ar ¹ may have a substituent. As the substituent, for example, those exemplified as the substituents for the groups represented by R ¹ and R ² can be applied. As a substituent of Ar ¹ is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, a halogen atom, a cyano group, a heterocyclic group,
A silyl group, more preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyano group, or an aromatic heterocyclic group, and still more preferably an alkyl group or an aryl group. ,
An alkoxy group, an aryloxy group, and an aromatic heterocyclic group.

Y represents an oxygen atom, a sulfur atom or N—R ^Y1 , and R ^Y1 represents a hydrogen atom or a substituent. The substituent is the same as the substituent represented by R ^A1 . Y is preferably an oxygen atom or a sulfur atom, and particularly preferably an oxygen atom. Among the compounds represented by the general formula (I), a compound represented by the general formula (II) is preferable. General formula (II)

[0060]

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Where R¹, R^Two, R^Three, R^Four, R^Five, A
r¹And Y are each the same as those in the general formula (I)
The same applies, and the preferred range is also the same. Z^APassing
And X ^AThe portion represented by represents the general formula (A). General
Ar in the compound represented by the formula (II)¹Is represented by the general formula (I
The chemical formulas represented by II) to (V) are more preferable.
No.

[0062]

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Z ¹ is an atom or an atomic group selected from a carbon atom, an oxygen atom, a nitrogen atom and a sulfur atom, and represents an atomic group forming a 5- or 6-membered heterocyclic ring, and Z ² , Z ³
Each represents an atom group consisting of an atom or an atom group selected from a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom to form a 5- or 6-membered condensed heterocyclic group. Ar ² represents a monocyclic or plural (preferably two-ring) aromatic heterocyclic group, and more preferable specific examples are the same as those described in the specific examples of Ar ¹ .

The compound represented by the general formula (I) may be a low molecular weight compound or a high molecular weight compound having a residue connected to the polymer main chain (preferably a mass average molecular weight of 1,000 to 50).
00000, more preferably 5,000 to 200,000
0, more preferably 10,000 to 1,000,000) or a high molecular weight compound having a compound represented by the general formula (I) in the main chain (preferably, a mass average molecular weight of 1,000 to 50)
00000, more preferably 5,000 to 200,000
0, more preferably 10,000 to 1,000,000). In the case of a high molecular weight compound, it may be a homopolymer, or may be a copolymer with another polymer.If it is a copolymer, it may be a random copolymer or a block copolymer. There may be. The compound used in the present invention is preferably a low molecular weight compound. Further, the compounds represented by the general formulas (I) to (V) may be contained in a state where a metal chelate is formed. Hereinafter, specific examples of the compound represented by formula (I) of the present invention are shown, but the present invention is not limited thereto.

[0065]

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[0066]

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[0067]

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[0068]

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[0069]

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The above compound may be a tautomer thereof.

Next, some examples of the synthesis of the compound represented by formula (I) of the present invention are shown below. The compound represented by the general formula (I) can be synthesized by various synthesis methods. For example, a method in which an aryl group of a triarylamine is formylated and then reacted with an active methylene compound in the absence or presence of a base. Etc. can be applied. Synthesis Example-1 Synthesis of Exemplified Compound (D-1)

[0072]

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1.7 g of synthetic intermediate A and 1.g of intermediate B
0 g was dissolved in 50 ml of ethanol.
16 ml was added, and the mixture was heated under reflux for 6 hours. The reaction solution was allowed to cool, and the precipitated crystals were collected by filtration. The obtained crude crystals were purified by silica gel chromatography, and crystallized with ethanol-chloroform to give 1.0 g of the desired exemplary compound (D-1)
I got Synthesis Example-2 Synthesis of Exemplified Compound (D-2)

[0074]

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Synthetic intermediate C (JP-A-11-335661)
1.9 g of the synthetic intermediate d) and the intermediate B described in
0 g was dissolved in 50 ml of ethanol, and piperidine 0.1
6 ml was added, and the mixture was heated under reflux for 6 hours. The reaction solution was allowed to cool, and the precipitated crystals were collected by filtration. The obtained crude crystals were purified by silica gel chromatography, and crystallized from ethanol-chloroform to obtain 1.2 g of the desired exemplary compound (D-2).

Next, an EL device containing the compound represented by formula (I) of the present invention will be described. The method for forming the organic layer of the EL device containing the compound of the general formula (I) of the present invention is not particularly limited.
Methods such as electron beam, sputtering, molecular lamination, coating, inkjet, printing, and transfer are used, and resistance heating evaporation and coating are preferred in view of characteristics and production. When the compound of the present invention is used as a material for a light emitting device, it may be used for any of a hole injection / transport layer, an electron injection / transport layer, and a light emitting layer, but is preferably used for a light emitting layer. The light-emitting element of the present invention is an element in which a light-emitting layer or a plurality of organic compound thin films including a light-emitting layer is formed between a pair of electrodes of an anode and a cathode, and in addition to the light-emitting layer, a hole injection layer, a hole transport layer, An electron injection layer, an electron transport layer, a protective layer, and the like may be provided, and each of these layers may have another function. Various materials can be used for forming each layer.

The anode supplies holes to the hole injection layer, the hole transport layer, the light emitting layer, and the like. A metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof is used. It is possible to use a material having a work function of 4 eV or more. Specific examples thereof include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO), and metals such as gold, silver, chromium, and nickel, and furthermore, these metals and conductive metal oxides. Or a laminate, copper iodide, an inorganic conductive substance such as copper iodide, an organic conductive material such as polyaniline, polythiophene, and polypyrrole, and a laminate of these with ITO, and the like. Metal oxides, especially from the viewpoints of productivity, high conductivity, transparency, etc.
TO is preferred. The thickness of the anode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm to 500 nm.

As the anode, a layer formed on a soda lime glass, an alkali-free glass, a transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass in order to reduce ions eluted from the glass. Further, 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 the thickness is sufficient to maintain the mechanical strength. When glass is used, the thickness is usually 0.2 mm or more, preferably 0.7 mm or more. Various methods are used to produce the anode depending on the material.
In the case of O, a film is formed by a method such as an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction method (such as a sol-gel method), and the application of an ITO dispersion. The anode can be washed or otherwise treated to lower the driving voltage of the device or increase the luminous efficiency. For example, in the case of ITO, UV
-Ozone treatment, plasma treatment, etc. 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 to the adjacent layers such as the electron injection layer, the electron transport layer, and the light-emitting layer. It is selected in consideration of stability and the like. As a material of the cathode, a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples thereof include alkali metals (eg, Li, Na, K, Cs
Or a fluoride thereof, an alkaline earth metal (eg, Mg, Ca, etc.) or a fluoride thereof, gold, silver, lead, aluminum, a sodium-potassium alloy, or a mixed metal thereof, a lithium-aluminum alloy, or a mixture thereof. Mixed metals, magnesium-silver alloys, or mixed metals thereof, indium, rare earth metals such as ytterbium, and the like, preferably a material having a work function of 4 eV or less, more preferably aluminum, a lithium-aluminum alloy, or a mixture thereof It is a mixed metal, a magnesium-silver alloy, or a mixed metal thereof. The thickness of the cathode can be appropriately selected depending on the material, but is usually 10 nm.
-5 μm is preferable, and more preferably 50 μm.
nm to 1 μm, and more preferably 100 nm to 1 μm.
m. A method such as an electron beam method, a sputtering method, a resistance heating evaporation method, or a coating method is used for manufacturing the cathode, and a metal can be evaporated alone or two or more components can be simultaneously evaporated. Furthermore, 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 material of the light emitting layer is capable of injecting holes from an anode, a hole injection layer, or a hole transport layer and applying electrons from a cathode, an electron injection layer, or an electron transport layer when an electric field is applied. Any material can be used as long as it can form a layer having a function, a function of transferring injected charges, and a function of providing a field of recombination of holes and electrons and emitting light. The compound used for the light-emitting layer may be any of those emitting light from an excited singlet and those emitting light from an excited triplet.For example, in addition to the compound of the present invention, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenyl Butadiene, tetraphenylbutadiene, naphthalimide, coumarin, perylene, perinone, oxadiazole, aldazine, pyrazine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, styrylamine, aromatic dimethylidin compound, 8- Metal complexes of quinolinol, various metal complexes typified by organometallic complexes and rare earth complexes, the above derivatives, and polymer compounds such as polythiophene, polyphenylene, and polyphenylenevinylene It is below. Although the thickness of the light emitting layer is not particularly limited, it is usually 1 nm.
~ 5 μm, more preferably 5n
m to 1 μm, more preferably 10 nm to 500 n
m.

The method of forming the light-emitting layer is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, molecular lamination, coating (spin coating, casting, dip, etc.), LB, and ink jet. A method such as a printing method, a printing method, and a transfer method is used, and a resistance heating evaporation method and a coating method are preferable.

The material of the hole injection layer and the hole transport layer has one of a function of injecting holes from the anode, a function of transporting holes, and a function of blocking electrons injected from the cathode. Anything is fine. Specific examples thereof include carbazole, imidazole, triazole, oxazole, oxadiazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styryl anthracene, fluorenone, hydrazone, stilbene, silazane, and aromatic Tertiary amine compounds, styrylamines, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds,
Examples include poly (N-vinylcarbazole), aniline-based copolymers, thiophene oligomers and polymers, conductive polymer oligomers and polymers such as polythiophene, carbon films, and the above derivatives. The thickness of the hole injection layer and the hole transport layer is not particularly limited by the material, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 nm. It is. 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 a method for forming the hole injection layer and the hole transport layer, a vacuum deposition method, an LB method, an ink jet method, a printing method,
A transfer method, and a method of dissolving or dispersing the hole injecting material or the hole transporting material in a solvent and coating the solution (a spin coating method, a casting method, a dip coating method, or the like) are 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, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N-vinylcarbazole). , Hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin and the like.

The material of the electron injection layer and the electron transport layer has a function of injecting electrons from a cathode, a function of transporting electrons, and a function of blocking holes injected from an anode. I just want it. Specific examples thereof include aromatic rings such as triazole, triazine, oxazole, oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, and naphthaleneperylene. Examples include metal complexes of tetracarboxylic anhydrides, phthalocyanines, and 8-quinolinol derivatives, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole or benzothiazole as ligands, and the above derivatives. The thickness of the electron injecting layer and the electron transporting layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 1 μm.
nm to 500 nm. The electron injection layer and the electron 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. Examples of the method for forming the electron injection layer and the electron transport layer include a vacuum deposition method, an LB method, an ink jet method, a printing method, a transfer method, and a method of coating by dissolving or dispersing the electron injection material and the electron transport material in a solvent ( Spin coating, casting, dip coating, etc.) are 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 for the hole injection / transport layer can be applied.

As a material for the protective layer, a material such as moisture or oxygen is used.
Function to prevent elements that promote element degradation from entering the element
What is necessary is just to have what has. As a specific example,
In, Sn, Pb, Au, Cu, Ag, Al, Ti, N
metal such as i, MgO, SiO, SiO_Two, Al
_TwoO_Three, GeO, NiO, CaO, BaO, Fe
_TwoO_Three, Y _TwoO_Three, TiO_TwoMetal oxides such as MgF
_Two, LiF, AlF_Three, CaF_TwoMetal fluorides, such as
Polyethylene, polypropylene, polymethyl methacrylate
Sheet, polyimide, polyurea, polytetrafluoroe
Tylene, polychlorotrifluoroethylene, polydichloro
Rodifluoroethylene, chlorotrifluoroethylene and
Dichlorodifluoroethylene copolymer, tetrafluoro
Monomer containing ethylene and at least one comonomer
-A copolymer obtained by copolymerizing a mixture, copolymer main chain
Fluorine-containing copolymer having a cyclic structure, water absorption of 1% or more
Water-absorbing substances, moisture-absorbing substances with a water absorption of 0.1% or less, etc.
No. There is no particular limitation on the method of forming the protective layer.
For example, vacuum deposition method, sputtering method, reactive spa
Cutter method, MBE (molecular beam epitaxy) method,
Star ion beam method, ion plating method, plastic
Zuma polymerization method (high frequency excitation ion plating method)
Plasma CVD, laser CVD, thermal CVD, gas
Source CVD method, coating method, inkjet method,
Printing method and transfer method can be applied.

[0086]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. Example 1 IT was placed on a 25 mm × 25 mm × 0.7 mm glass substrate.
A film formed of O with a thickness of 150 nm (manufactured by Tokyo Sanyo Vacuum Co., Ltd.) was used as a transparent support substrate. After etching and washing this transparent support substrate, TPD (N, N'-bis (3-methylphenyl) -N, N'-diphenylbenzidine) about 40 nm, the compound shown in Table 1 and Alq (Tris (8
-Hydroxyquinolinato) aluminum) at a deposition rate of 0.004 nm / sec and 0.4 nm / sec,
Co-evaporation was performed to a thickness of 0 nm. Alq (tris (8-hydroxyquinolinato) aluminum) about 20 n
m were sequentially deposited in a vacuum of 10 ⁻³ to 10 ⁻⁴ Pa at a substrate temperature of room temperature. A mask (a mask having a light emitting area of 5 mm × 5 mm) patterned on an organic thin film is provided, and magnesium: silver = 10: 1 is added to 250 in a vapor deposition apparatus.
After co-evaporation of 300 nm, 300 nm of silver was evaporated. Subsequently, the device was sealed. Using a source measure unit 2400 manufactured by Toyo Technica, a DC constant voltage is applied to the EL element to emit light, and the brightness is measured by a luminance meter BM-8 manufactured by Topcon Corporation, and the emission wavelength is measured by a spectrum analyzer P manufactured by Hamamatsu Photonics.
It was measured using MA-11. In addition, the device was
After standing for a day, the device was driven and stored at the same current value as the current value of the initial luminance of 200 cd / m ² , and the luminance maintenance ratio ((luminance after storage / initial luminance) × 100 (%)) was measured. Table 1 shows the results.

[0087]

[Table 1]

[0088]

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As is clear from the results shown in Table 1, when the compound of the present invention is used as a dope dye, the compound has excellent color purity as red, can emit light with high luminance, and can be a light emitting material having excellent surface properties. Was. And it turns out that it is excellent in storage durability.

Embodiment 2 After etching and cleaning the ITO substrate in the same manner as in Embodiment 1,
After depositing PD with a thickness of about 40 nm, the compound of the present invention (D-16)
Was evaporated to a thickness of about 40 nm and Alq alone was evaporated to a thickness of 20 nm, and then a cathode was evaporated and evaluated in the same manner as in Example 1. As a result, red light emission having a maximum luminance of 1200 cd / m ² was obtained. As a comparative example, a similar device was prepared using Comparative Compound A and evaluated. As a result, the device emitted red light with a maximum luminance of 850 cd / m ² . It was shown that when the compound of the present invention is used alone as a light-emitting layer, it has good color purity, can emit light with high luminance, and can be a light-emitting material having excellent planarity. Moreover, even after long-time light emission, the number of dark spots was small and the durability was excellent. Further, the current density of each element is 100 mA / c.
The driving voltage at m ² was 8.1 V for the device of the present invention and 9.0 V for the comparative device, and the use of the compound of the present invention enabled lower voltage driving.

Example 3 An ITO substrate was etched and washed in the same manner as in Example 1, and then poly (N-vinylcarbazole) 40 mg and PBD (2-
(4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole) 12 m
g, 0.5 mg of the compound of the present invention (D-16) was dissolved in 3 ml of 1,2-dichloroethane and spin-coated on a washed ITO substrate. The thickness of the formed organic thin film is about 12
It was 0 nm. Next, a cathode was deposited and evaluated in the same manner as in Example 1. The maximum luminance was 650 cd / m ^{2 at} 20 V.
Of red light emission. As a comparative example, a similar device was manufactured using DCM instead of (D-16).
At 2 V, the maximum luminance was 350 cd / m ² . In the device using the compound of the present invention, low-voltage driving and high-luminance light emission were possible even in a coating method in which light emission luminance was usually low.

[0092]

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Example 4 On an ITO glass substrate etched and washed in the same manner as in Example 1, 40 mg of poly (N-vinylcarbazole) was added.
2,5-bis (1-naphthyl) -1,3,4-oxadiazole 12 mg, tetraphenylbutadiene 10 mg
And 0.1 mg of Exemplified Compound (D-1) of the present invention in 1,
A solution dissolved in 3 ml of 2-dichloroethane was spin-coated. Next, a cathode was deposited in the same manner as in Example 1. When a direct current voltage was applied to this device using an ITO electrode as an anode and a Mg: Ag electrode as a cathode, the light emission characteristics were examined. Was obtained (luminance: 1100 cd / m ² ), which proved to be effective for white light emission.

[0094]

According to the present invention, the organic EL device containing the compound represented by the general formula (I) can emit red EL with low voltage driving, high luminance and high color purity as compared with the prior art,
An element having excellent surface properties and excellent durability is provided. In addition, a film formed of a dye alone can emit light with high luminance, and a non-doped element has a small variation in performance between elements, and enables an element to be manufactured which is advantageous in terms of manufacturing cost and the like. Also. Good light-emitting characteristics can be obtained even with a coating method with low light emission luminance.

Claims (3)

[Claims] 1. A light emitting device material represented by the following general formula (I). General formula (I) Wherein R ¹ and R ² may be the same or different;
Represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Ar ¹ represents a linking group consisting of a conjugated bond containing a heterocyclic group, and R ¹ , R ² and Ar ¹ may be bonded to each other to form a ring. R ³ , R ⁴ and R ⁵ may be the same or different and each represent a hydrogen atom or a substituent. Y represents an oxygen atom, a sulfur atom, N—R ^Y1 , R ^Y1
Represents a hydrogen atom or a substituent. Rx and Ry each represent a hydrogen atom or a substituent, and at least one of them represents an electron-withdrawing group. 2. A light-emitting element in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of electrodes,
At least one layer is a layer containing at least one compound represented by the general formula (I). Formula (I) Wherein R ¹ and R ² may be the same or different;
Represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Ar ¹ represents a linking group comprising a conjugated bond including a heterocyclic group, and R ¹ , R ² and Ar ¹ may be bonded to each other to form a ring. R ³ , R ⁴ and R ⁵ may be the same or different and each represent a hydrogen atom or a substituent. Y represents an oxygen atom, a sulfur atom, N—R ^Y1 , R ^Y1
Represents a hydrogen atom or a substituent. Rx and Ry each represent a hydrogen atom or a substituent, and at least one of them represents an electron-withdrawing group. 3. A light-emitting element in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of electrodes,
The light emitting device according to claim 2, wherein the light emitting layer is a layer in which at least one compound represented by the general formula (I) is dispersed in a polymer. General formula (I) Wherein R ¹ and R ² may be the same or different;
Represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Ar ¹ represents a linking group consisting of a conjugated bond containing a heterocyclic group, and R ¹ , R ² and Ar ¹ may be bonded to each other to form a ring. R ³ , R ⁴ and R ⁵ may be the same or different and each represent a hydrogen atom or a substituent. Y represents an oxygen atom, a sulfur atom, N—R ^Y1 , and R ^Y1
Represents a hydrogen atom or a substituent. Rx and Ry each represent a hydrogen atom or a substituent, and at least one of them represents an electron-withdrawing group.