JP3855999B2 - Material for organic electroluminescence device and organic electroluminescence device using the same - Google Patents

Description

  The present invention relates to a material for an organic electroluminescence (EL) element used for a flat light source and display, and an organic EL element using the same. More specifically, the present invention relates to a material for an organic EL element having a long life and capable of obtaining yellow-red high luminance light emission and an organic EL element using the same.

  An EL element using an organic substance is considered to be promising for use as an inexpensive large-area full-color display element of a solid light emitting type, and many developments have been made. In general, an EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side, holes are injected from the anode side, these electrons recombine with holes in the light emitting layer, and the energy level is in the conduction band. This is a phenomenon in which energy is released as light when returning from the valence band to the valence band.

Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic EL elements. Further, the characteristic deterioration has been remarkably not put into practical use. In recent years, an organic EL device in which a thin film containing an organic compound having a high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less has been reported and attracted attention (Appl. Phys. Lett., Vol. 51, (See page 913, published in 1987). This method, the light emitting layer metal chelate complex and an amine compound in the hole injection layer, and obtaining a green light emission with high luminance, the number luminance at a DC voltage of 6~10V 1000 (cd / m ² ), The maximum luminous efficiency is 1.5 (lm / W), and the performance is close to the practical range.

  Among organic EL elements, the light-emitting material for organic EL elements for obtaining yellow to red light emission is particularly described in C.I. H. Chen et al., Macromol. Symp. 125, 34-36 and 49-58, published in 1997, 4H-pyran derivatives such as DCM, DCJ, DCJT, and DCJTB emit light from yellow to red light for organic EL devices. Although reported as a material, there was a problem of low emission luminance.

On the other hand, with respect to the light-emitting material for organic EL elements having a perylene structure, for example, mono- and diaminoperylene compounds described in JP-A Nos. 11-144869, 2001-11031, and 2001-176664 Etc. are known.

Appl. Phys. Lett. 51, page 913, published in 1987. C. H. Chen et al., Macromol. Symp. 125, 34-36, 1997 Japanese Patent Laid-Open No. 11-144869 JP 2001-11031 A JP 2001-176664 A

  None of the light-emitting materials for organic EL devices for obtaining yellow to red high-luminance emission described in the prior art has a drawback that it does not have sufficient emission luminance and has a short lifetime. On the other hand, since perylene has a highly planar molecular structure, undesirable phenomena such as concentration quenching tend to occur when it is used as a light emitting material for organic EL elements. Therefore, as described in the prior art, improvements such as increasing the number of amino groups bonded to perylene or introducing a sterically bulky substituent have been attempted, but with the accompanying increase in molecular weight, There is a concern that workability deteriorates, such as a decrease in solubility in a solvent and poor vapor deposition at the time of device preparation. Therefore, there has been a demand for a material for an organic EL element having a much higher light emission luminance and a longer lifetime.

［式中、Ａｒ¹は、３−ペリレニル基、Ｒ¹およびＲ²は、置換もしくは未置換の１価の芳香族炭化水素基、または、置換もしくは未置換の１価の含窒素芳香族複素環基であって、Ｒ¹およびＲ²の少なくとも一つは、置換もしくは未置換の１価の含窒素芳香族複素環基である。］ As a result of intensive studies to solve the above problems, the present inventors have arrived at the present invention.
That is, this invention relates to the material for organic electroluminescent elements characterized by being a compound represented by the following general formula [1].
General formula [1]

[In the formula, Ar ¹ represents a 3-perylenyl group, R ¹ and R ² represent a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic ring. And at least one of R ¹ and R ² is a substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic group. ]

The present invention also relates to the above-mentioned material for an organic electroluminescence device, wherein R ¹ and R ² are both substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic groups.

  Further, the present invention provides an organic electroluminescence device in which a single layer or a multilayer organic layer is formed between a pair of electrodes composed of an anode and a cathode, and at least one layer is a layer containing the organic electroluminescence device material. The present invention relates to an organic electroluminescence element.

  Further, the present invention provides an organic electroluminescent device in which at least one light emitting layer is formed between a pair of electrodes composed of an anode and a cathode, wherein the light emitting layer is a layer containing the material for an organic electroluminescent device. The present invention relates to an electroluminescence element.

  The present invention further relates to the above-mentioned organic electroluminescence device, wherein at least one electron injection layer is formed between the light emitting layer and the cathode.

  Since the organic EL element produced using the material for the organic EL element of the present invention has higher luminance and longer life than conventional ones, it can be suitably used as a flat panel display such as a wall-mounted television or a flat light emitter. It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights.

  Hereinafter, the present invention will be described in detail. First, the monoamine compound represented by the general formula [1], which is a material for an organic EL device of the present invention, will be described.

First, Ar ¹ in the general formula [1] includes a 3-perylenyl group. The perylenyl group may be further substituted with another substituent. Examples of such a substituent include a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aliphatic heterocyclic group, a monovalent aromatic heterocyclic group, a halogen atom, a cyano group, Examples include an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, and an arylsulfonyl group.

  Here, the monovalent aliphatic hydrocarbon group refers to a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, such as an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group. Can be given.

  Therefore, as the alkyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, C1-C18 alkyl groups, such as a decyl group, a dodecyl group, a pentadecyl group, and an octadecyl group, are mentioned.

  Examples of the alkenyl group include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-octenyl group, 1-decenyl group, 1 -An alkenyl group having 2 to 18 carbon atoms such as an octadecenyl group.

  Examples of the alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-octynyl group, 1-decynyl group and 1-octadecynyl group. Examples thereof include alkynyl groups having 2 to 18 carbon atoms.

  In addition, the cycloalkyl group has a carbon number such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-bornyl group, 2-isobornyl group, 1-adamantyl group. Examples thereof include 3 to 18 cycloalkyl groups.

  Furthermore, examples of the monovalent aromatic hydrocarbon group include monovalent monocyclic, condensed ring, and ring-aggregated aromatic hydrocarbon groups having 6 to 30 carbon atoms. Here, as a monovalent monocyclic aromatic hydrocarbon group having 6 to 30 carbon atoms, phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl And monovalent monocyclic aromatic hydrocarbon groups having 6 to 30 carbon atoms such as a group and a mesityl group.

  Examples of the monovalent condensed ring aromatic hydrocarbon group include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, 1-acenaphthyl group, 2-azurenyl group, 1-pyrenyl group, 2-triphenylyl group, 1-pyrenyl group, 2-pyrenyl group, 1-perylenyl group, 2-perylenyl group, 3-perenylenyl group, 2-trephenylenyl group, Examples thereof include monovalent condensed ring hydrocarbon groups having 10 to 30 carbon atoms such as 2-indenyl group, 1-acenaphthylenyl group, 2-naphthacenyl group, and 2-pentacenyl group.

  The monovalent ring-aggregated aromatic hydrocarbon group has 12 carbon atoms such as o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, terphenylyl group, 7- (2-naphthyl) -2-naphthyl group and the like. To 30 monovalent ring-assembled hydrocarbon groups.

  Examples of the monovalent aliphatic heterocyclic group include monovalent aliphatic heterocyclic groups having 3 to 18 carbon atoms such as 3-isochromanyl group, 7-chromanyl group, and 3-coumarinyl.

  Examples of the monovalent aromatic heterocyclic group include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-benzofuryl group, 2-benzothienyl group, 2-pyridyl group, 3 -Pyridyl group, 4-pyridyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3 -Isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 2-quinazolinyl group, 2-quinoxalinyl group, 2 -C3-C30 monovalent | monohydric aromatic heterocyclic groups, such as oxazolyl group and 2-thiazolyl group, are mention | raise | lifted.

  In addition, examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

The alkoxyl group includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a tert-butoxy group, an octyloxy group, a tert-octyloxy group, a 2-bornyloxy group, a 2-isobornyloxy group, and a 1-adamantyl group. C1-C18 alkoxyl groups, such as an oxy group, are mention | raise | lifted.

  Examples of the aryloxy group include aryloxy groups having 6 to 30 carbon atoms such as a phenoxy group, a 4-tert-butylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and a 9-anthryloxy group. .

  Examples of the alkylthio group include C1-C18 alkylthio groups such as a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group.

  Examples of the arylthio group include arylthio groups having 6 to 30 carbon atoms such as a phenylthio group, a 2-methylphenylthio group, and a 4-tert-butylphenylthio group.

  Examples of the acyl group include C2-C18 acyl groups such as an acetyl group, a propionyl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a toluoyl group, an anisoyl group, and a cinnamoyl group.

  Moreover, as an alkoxycarbonyl group, C2-C18 alkoxycarbonyl groups, such as a methoxycarbonyl group, an ethoxycarbonyl group, a benzyloxycarbonyl group, are mention | raise | lifted.

  Examples of the aryloxycarbonyl group include C2-C18 aryloxycarbonyl groups such as a phenoxycarbonyl group and a naphthyloxycarbonyl group.

  Moreover, as an alkylsulfonyl group, C2-C18 alkylsulfonyl groups, such as a mesyl group, an ethylsulfonyl group, a propylsulfonyl group, are mention | raise | lifted.

  Examples of the arylsulfonyl group include C2-C18 arylsulfonyl groups such as a benzenesulfonyl group and a p-toluenesulfonyl group.

  The substituents described above may be further substituted with other substituents, and these substituents may be bonded to each other to form a ring.

As Ar ¹ in the general formula [1] described above, a substituted or unsubstituted 3-perylenyl group is preferable, and an unsubstituted 3-perylenyl group is particularly preferable. The reason for this is that when the amino group is bonded to the 3-position of perylene, the angle between the perylene ring and the amino group is kept relatively on the same plane, so that the fluorescence becomes strong and the organic electroluminescence device This is because it is considered that the light emission luminance when used as is improved.

  Among the substituted 3-perylenyl groups, preferred substituents include alkyl groups, monovalent aromatic hydrocarbon groups, monovalent aromatic heterocyclic groups, aryloxy groups, and arylthio groups, and particularly preferred substitutions. Examples of the group include an alkyl group, a monovalent monocyclic aromatic hydrocarbon group, a monovalent condensed ring aromatic hydrocarbon group, a monovalent ring assembly aromatic hydrocarbon group, and a monovalent aromatic heterocyclic group. It is done.

  Moreover, 1-18 are preferable as a carbon number of a substituent among the preferable substituents described above, and 1-12 are more preferable. The reason for this is that if the carbon number of these substituents increases, the solubility in the solvent becomes poor, so that not only purification becomes difficult, but also the workability at the time of device creation deteriorates, and an attempt is made to create a device by vapor deposition. This is because there may be a concern that the vapor deposition property is deteriorated.

Next, R ¹ and R ² in the general formula [1] will be described. R ¹ and R ² are a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic group, and at least one of R ¹ and R ² One is a substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic group. It is synonymous with the substituted or unsubstituted monovalent | monohydric aromatic hydrocarbon group here and a substituted or unsubstituted monovalent | monohydric aromatic heterocyclic group. Among examples, the nitrogen-containing aromatic heterocyclic group includes 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6- Quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2- A pyrimidinyl group and a 2-pyrazinyl group.

  The monoamine compound represented by the general formula [1] of the present invention has been described above. The molecular weight of the monoamine compound of the present invention is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. The reason for this is that, if the molecular weight is large, the solubility in the solvent becomes poor, so not only purification becomes difficult, but the workability at the time of device creation is deteriorated, and the vapor deposition property when the device is created by vapor deposition This is because there is a concern that it will worsen.

  The element created by using the organic EL element material of the present invention alone in the light emitting layer usually exhibits yellow to orange high-intensity light emission, but when used with an appropriate doping material as described later, It is possible to extend the emission color to red while maintaining high luminance.

  Table 1 shows typical examples of compounds that can be used as the organic EL device material of the present invention. However, the present invention is not limited to these.

  By the way, an organic EL element is an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode. Here, a single layer type organic EL element has a light emitting layer made of a light emitting material between an anode and a cathode. Have. On the other hand, the multilayer organic EL device has (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole injection layer / light emitting layer / electron injection layer). / Cathode) is an organic EL element laminated in a multilayer structure. The organic EL device material of the present invention can be used in any of the above-mentioned layers, but can be suitably used as a light-emitting material for these single-layer or multilayer organic EL devices. In particular, when a single-layer organic EL device is prepared using the light emitting material for the organic EL device, a hole injection material or an electron for efficiently transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. An injection material can be included.

  Here, the hole injection material indicates an excellent hole injection effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and It means a compound excellent in thin film forming property. Examples of such hole injection materials include phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazoles, triazoles, imidazoles, imidazolones, imidazolethiones, pyrazolines, pyrazolones, tetrahydroimidazoles, oxazoles, oxadiazoles Hydrazone, acyl hydrazone, polyarylalkane, stilbene, butadiene, benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and their derivatives, and polyvinylcarbazole, polysilane, conductive polymer, etc. The present invention is not limited to these examples.

Among the above hole injection materials, particularly effective hole injection materials include aromatic tertiary amine derivatives or phthalocyanine derivatives. Examples of aromatic tertiary amine derivatives include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′- Diamine, N, N, N ', N'-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N ', N'-(4-methylphenyl)- 1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-(methylphenyl) ) -N, N ′-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, or these An oligomer having an aromatic tertiary amine skeleton or Rimmer, and the like. Examples of the phthalocyanine (Pc) derivative include H ₂ Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl ₂ SiPc, (HO) AlPc, (HO) GaPc, Examples thereof include phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc-O-GaPc. The hole injection material described above can be further sensitized by adding an electron accepting material.

  On the other hand, the electron injection material shows an excellent electron injection effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the hole injection layer or the hole injection material, and is a thin film. It means a compound excellent in formability. Examples of such electron injection materials include quinoline metal complexes, oxadiazoles, benzothiazole metal complexes, benzoxazole metal complexes, benzimidazole metal complexes, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadioxide. Examples thereof include azole, thiadiazole, tetrazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone and the like. An inorganic / organic composite material doped with a metal such as cesium in bathophenanthroline (for example, Proceedings of the Society of Polymer Science, Vol. 50, No. 4, page 660, issued in 2001) is an example of an electron injection material. However, the present invention is not limited to these.

Among the electron injection materials, particularly effective electron injection materials include metal complex compounds and nitrogen-containing five-membered ring derivatives. Here, among the metal complex compounds, the compound represented by the following general formula [3] can be preferably used.

General formula [3]

[Wherein, Q ¹ and Q ² each independently represent a substituted or unsubstituted hydroxyquinoline derivative or a substituted or unsubstituted hydroxybenzoquinoline derivative, and L represents a halogen atom, a substituted or unsubstituted alkyl group, A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group, -OR (where R is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted group, A cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.), —O—Ga—Q ³ (Q ⁴ ) (Q ³ and Q ⁴ are Q Represents the same meaning as ¹ and Q ² ). ]

Here, the general formula [3] will be described. Q ^{1 to} Q ⁴ of the compound represented by the general formula [3] are substituted or unsubstituted hydroxyquinoline derivatives or substituted or unsubstituted hydroxybenzoquinoline derivatives. The substituent here is synonymous with the substituent in R ¹ and R ² in the general formula [1].

L represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. The substituent here is synonymous with the substituent in R ¹ and R ² in the general formula [1]. Examples of the substituted or unsubstituted cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecanyl group.

Therefore, specific examples of the compound represented by the general formula [3] include bis (2-methyl-8-hydroxyquinolinate) (1-naphtholate) gallium complex, bis (2-methyl-8-hydroxyquinolinate). ) (2-Naphtholate) gallium complex, bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex, bis (2-methyl-8-hydroxyquinolinate) (4-cyano-1-naphtholate) Gallium complex, bis (2,4-dimethyl-8-hydroxyquinolinato) (1-naphtholato) gallium complex, bis (2,5-dimethyl-8-hydroxyquinolinato) (2-naphtholato) gallium complex, bis (2-Methyl-5-phenyl-8-hydroxyquinolinate) (phenolate) gallium complex, bis (2-methyl- -Cyano-8-hydroxyquinolinate) (4-cyano-1-naphtholate) gallium complex, bis (2-methyl-8-hydroxyquinolinato) chlorogallium complex, bis (2-methyl-8-hydroxyquinolinate) (Nato) (o-cresolate) gallium complex and the like, but the present invention is not limited thereto. The compound represented by the general formula [3] can be synthesized by the method described in JP-A-10-88,121.

  In addition, among the electron injection materials that can be used in the present invention, preferred metal complex compounds include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, Bis (8-hydroxyquinolinate) manganese, Tris (8-hydroxyquinolinato) aluminum, Tris (2-methyl-8-hydroxyquinolinato) aluminum, Tris (8-hydroxyquinolinato) gallium, Bis ( 10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc and the like.

  Among the electron injecting materials that can be used in the present invention, preferable nitrogen-containing five-membered derivatives include oxazole, thiazole, oxadiazole, thiadiazole, and triazole derivatives. Specifically, 2,5-bis ( 1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) -1,3, 4-oxadiazole, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1,3 , 4-oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene] 2 -(4'-tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) -1,3,4-thiadiazole, 1,4 -Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene, etc. The electron injecting material described above further includes an electron donating material. Can be sensitized.

  Moreover, the organic EL device material of the present invention can be used by doping into the light emitting layer. In this case, the organic EL device material is preferably contained in the range of 0.001 to 50% by weight, and more preferably in the range of 0.01 to 10% by weight with respect to the host material described below. More preferably.

Host materials that can be used together with the organic EL device material of the present invention as a doping material include quinoline metal complexes, benzoquinoline metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, benzimidazole metal complexes, and benzotriazole metals. Electron transport materials such as complexes, imidazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and triazole derivatives. Or hole transporting materials such as stilbene derivatives, butadiene derivatives, benzidine type triphenylamine derivatives, styrylamine type triphenylamine derivatives, diaminoanthracene type triphenylamine derivatives, diaminophenanthrene type triphenylamine derivatives, and polyvinylcarbazole, Examples thereof include polymer materials of conductive polymers such as polysilane.

  Moreover, in the light emitting layer in this organic EL element, in addition to the material for organic EL elements of the present invention, two or more kinds of other light emitting materials and doping materials can be used in combination. In this case, the organic EL element material of the present invention may function as a host material. Other light-emitting materials and doping materials that can be used with the organic EL device material of the present invention include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenyl Butadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, Polymethine, merocyanine, imidazole chelating oxinoid compounds, quinacridone, rubrene, etc. and their derivatives It is below.

  In the light emitting layer of the present organic EL device, in addition to the organic EL device material of the present invention, not only other light emitting materials and doping materials, but also the above-described hole injection materials and electron injection materials are used. Two or more kinds of materials can be used in combination. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed with a layer configuration of two or more layers.

  Furthermore, the conductive material used for the anode of the organic EL element of the present invention is suitably one having a work function larger than 4 eV, such as carbon, aluminum, vanadium, iron, cobalt, nickel. , Tungsten, silver, gold, platinum, palladium and the like and alloys thereof, ITO substrates, metal oxides such as tin oxide and indium oxide called NESA substrates, and organic conductive polymers such as polythiophene and polypyrrole.

  Further, the conductive material used for the cathode of the organic EL device of the present invention is suitably one having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium. Lithium, lithium fluoride, ruthenium, manganese and the like and alloys thereof. Here, examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. Since the ratio of the alloy can be controlled by the heating temperature, atmosphere, and degree of vacuum at the time of preparation, an alloy having an appropriate ratio can be prepared. These anodes and cathodes may be formed with a layer structure of two or more layers if necessary.

  In order for the organic EL device of the present invention to emit light efficiently, the material constituting the device is preferably sufficiently transparent in the light emission wavelength region of the device, and at the same time, the substrate is preferably transparent. The transparent electrode can be prepared by a method such as vapor deposition or sputtering using the above conductive material. In particular, it is desirable that the light transmission surface electrode has a light transmittance of 10% or more. The substrate is not particularly limited as long as it has mechanical and thermal strength and is transparent. For example, a transparent polymer such as a glass substrate, polyethylene, polyethersulfone, and polypropylene is recommended.

  In addition, as a method for forming each layer of the organic EL element of the present invention, any one of a dry film forming method such as vacuum deposition, sputtering, plasma, and ion plating, or a wet film forming method such as spin coating, dipping, and flow coating is used. The method can be applied. The thickness of each layer is not particularly limited, but must be set to an appropriate thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. On the other hand, if the film thickness is too thin, pinholes and the like are generated, and it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied. Accordingly, the normal film thickness is suitably in the range of 1 nm to 1 μm, but more preferably in the range of 10 nm to 0.2 μm.

  In the case of a wet film forming method, each layer forms a thin film by dissolving or dispersing the material constituting it in an appropriate solvent such as toluene, chloroform, tetrahydrofuran, dioxane or the like. The solvent used here may be either a single solvent or a mixed solvent. In any wet film forming method, an appropriate polymer or additive may be used for improving the film forming property and preventing pinholes in the film. Examples of such polymers include insulating polymers such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and photoconductive materials such as poly-N-vinylcarbazole and polysilane. And conductive polymers such as conductive polymer, polythiophene, and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer. When the material of the present invention is wet-formed, the affinity between the molecules of each compound is good, so even if the compound alone is highly cohesive and the film tends to be non-uniform, it is mixed with a derivative with low cohesiveness. A good film can be obtained by using the material.

  In addition, in order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., a protective layer may be further provided on the surface of the device, or the entire device may be covered with silicon oil, polymer, etc. good.

As described above, an organic EL element produced using the material for an organic EL element can improve characteristics such as light emission efficiency and maximum light emission luminance. In addition, since the organic EL element can emit light that can be practically used at a low driving voltage, it is possible to reduce deterioration that has been a major problem until now. Therefore, this organic EL device can be applied to flat panel displays such as wall-mounted televisions and flat light emitters, as well as light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. Can be considered.

  EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example at all. First, prior to examples, a synthesis example of the organic EL element material of the present invention will be described.

  Bromo compound, 3-aminoperylene 1, sodium-t-butoxide, palladium acetate and tri-t-butylphosphine were added to toluene, and the mixture was heated to reflux for 2 hours with stirring in a nitrogen atmosphere. The mixture is allowed to cool and then filtered, and the filtrate is concentrated and purified by column chromatography using silica gel to obtain the organic EL device material of the present invention.

Examples using the compounds of the present invention are shown below. In this example, all mixing ratios indicate weight ratios unless otherwise specified. Moreover, the characteristic of the organic EL element with an electrode area of 2 mm × 2 mm was measured. In the implementation, the following known materials were used.
(Comparative Compound A)

  (Comparative Compound B)

  (Comparative Compound C)

  (Comparative Compound D)

Examples 1-2 and Comparative Examples 1-4
On a cleaned glass plate with an ITO electrode, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NPD) was vacuum-deposited to form a hole injection layer having a thickness of 30 nm. Formed. Subsequently, the compound of Table 1 was vacuum-deposited and the light emitting layer with a film thickness of 30 nm was obtained. Further, a bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex was vacuum-deposited to prepare an electron injection layer having a film thickness of 30 nm, and magnesium and silver were further added at a ratio of 10: 1 (weight ratio). ) Was used to form an electrode having a film thickness of 100 nm to obtain an organic EL device. Each layer was deposited in a vacuum of 10 ⁻⁶ Torr at a substrate temperature of room temperature. The light emission characteristics of this element are shown in Table 2. All the organic EL elements of this example exhibited high luminance characteristics with a maximum light emission luminance of 35000 (cd / m ² ) or more. Similarly, as a comparative example, an organic EL device was produced in the same manner as in Example 1 except that the comparative compounds A to D were formed and used. The light emission characteristics of this device are also shown in Table 2. In any case, it is apparent that both the maximum light emission luminance and the maximum light emission efficiency are inferior to those of the device prepared in this example.

  As is clear from the above-described embodiments, the organic EL device of the present invention achieves improvement in luminous efficiency, luminous luminance, and long life, and the luminescent material, doping material, and hole injection used together. The material, the electron injection material, the sensitizer, the resin, the electrode material, and the like and the device manufacturing method are not limited.

Claims (5)

A material for an organic electroluminescence device, which is a monoamine compound represented by the following general formula [1].
General formula [1]

[In the formula, Ar ¹ represents a 3-perylenyl group, R ¹ and R ² represent a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic ring. And at least one of R ¹ and R ² is a substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic group. ] ^2. The organic electroluminescent element material according to claim 1, wherein R ¹ and R ² are both substituted or unsubstituted monovalent nitrogen-containing aromatic heterocyclic groups. 3. An organic electroluminescence device comprising a single layer or a multi-layer organic layer formed between a pair of electrodes comprising an anode and a cathode, wherein at least one layer is a layer containing the material for an organic electroluminescence device according to claim 1 or 2. Organic electroluminescence device. 3. An organic electroluminescent device comprising at least one light emitting layer formed between a pair of electrodes consisting of an anode and a cathode, wherein the light emitting layer is a layer containing the material for an organic electroluminescent device according to claim 1 or 2. Electroluminescence element. The organic electroluminescence device according to claim 4, further comprising at least one electron injection layer formed between the light emitting layer and the cathode.