JP2009249551A - Material for organic electroluminescent element and element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a long-lived organic EL element with high luminous efficiency and a luminescent material materializing it. <P>SOLUTION: A material for an organic electroluminescent element is represented by the general formula [1], wherein X<SP>1</SP>and X<SP>2</SP>are alkyl or aryl. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a material for an organic electroluminescence element used for a planar light source and a display, and an organic electroluminescence element. More specifically, a novel organic electroluminescence device material that exhibits high fluorescence emission characteristics and excellent thermal and light stability, and a long-life organic material for obtaining blue light emission exhibiting high color purity and luminance at a low driving voltage. The present invention relates to an electroluminescence element.

  An organic electroluminescence element that emits light when an electron injected from a cathode and a hole injected from an anode are recombined in an organic phosphor sandwiched between these two electrodes (hereinafter abbreviated as EL) is an element. The use as a solid-state light-emitting display element is considered promising, and research and development has been actively conducted in recent years.

  An organic EL element is a self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. Eastman Kodak's C.I. W. Since Tang et al. Reported a low-voltage driven organic EL element using a stacked element (Non-patent Document 1), research on organic EL elements using organic materials as constituent materials has been actively conducted. Tang et al. Use tris (8-quinolinolato) aluminum for the light emitting layer and a triphenyldiamine derivative for the hole transporting layer. The advantages of the stacked structure are that it increases the efficiency of hole injection into the light-emitting layer, blocks the electrons injected from the cathode, increases the generation efficiency of excitons generated by recombination, and generates in the light-emitting layer For example, confining excitons. As in this example, the device structure of the organic EL device includes a hole transport (injection) layer, a two-layer type of an electron transport light-emitting layer, or a hole transport (injection) layer, a light-emitting layer, and an electron transport (injection) layer. A three-layer type is well known. In such a stacked structure element, the element structure and the formation method are devised in order to increase the recombination efficiency of injected holes and electrons. In addition, chelating complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, and the like are known as light emitting materials. It is reported that light emission in the visible region from red to red can be obtained, and realization of a color display element is expected (Patent Documents 1, 2, and 3).

    Further, an element using a phenylanthracene derivative as a light emitting material is disclosed (Patent Document 4). Such anthracene derivatives are used as blue light-emitting materials. However, these organic EL elements cannot be said to have sufficient performance in terms of performance such as efficiency, driving voltage, and lifetime, and are further enhanced. Development of materials that can realize organic EL elements with high efficiency, low drive voltage, and long life is required. In addition, an element material having a fluoranthene group at the 9th and 10th positions of anthracene is disclosed (Patent Document 5). Such anthracene derivatives are also used as blue light-emitting materials, but there has been a demand for improved performance such as efficiency, drive voltage, and lifetime.

Appl. Phys. Lett. 51, 913, 1987 JP-A-8-239655 JP 7-138561 A JP-A-3-200289 JP-A-8-012600 JP 2001-257074 A

  An object of the present invention is to provide an organic EL element having high luminous efficiency and a long lifetime, and to provide a light emitting material for an organic EL element that realizes the organic EL element.

  As a result of intensive studies to solve the above problems in consideration of the above problems, the present inventor uses a compound having an anthracene structure having a specific structure represented by the following general formula [1] as a light emitting material of an organic EL element. The present inventors have found that an organic EL device having high luminous efficiency and a long lifetime can be obtained, and the present invention has been achieved.

  That is, the present invention relates to an organic EL element material represented by the following general formula [1].

General formula [1]

[Wherein, X ¹ and X ² are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
R ^{1 to} R ¹⁶ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy Group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted It represents a substituted acyl group, and adjacent substituents may form a cyclic structure. However, at least one of R ^{9 to} R ¹⁶ is a substituted or unsubstituted amino group, or a group represented by the following general formula [2]. ]

General formula [2]

[Wherein, R ^{17 to} R ²¹ are each independently a fluorine atom, a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, substituted or Unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted acyl group And adjacent substituents may form a cyclic structure.
Y represents a sulfur atom or an oxygen atom. ]

The present invention also relates to the above organic EL device material, wherein X ¹ and X ² are each independently a substituted or unsubstituted alkyl group.

  Moreover, this invention relates to the light emitting layer material for organic EL elements which comprises the organic EL element material as described above.

  Moreover, this invention relates to the organic EL element material as described above which is a light emitting layer dopant material for an organic EL element.

  Further, the present invention provides an organic EL device 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 composed of an anode and a cathode. The present invention relates to an organic EL element comprising an organic EL element material.

  Further, the present invention provides an organic EL device 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 composed of an anode and a cathode, wherein the light emitting layer is the organic EL device described above. Further, the present invention relates to an organic EL device in which the light emitting layer comprises the light emitting layer material for an organic EL device described above.

  Further, the present invention provides an organic EL device 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 composed of an anode and a cathode, wherein the light emitting layer is the organic EL device described above. The present invention relates to an organic EL device, wherein the light emitting layer comprises the above-described light emitting layer dopant material for organic EL devices.

  The present invention also relates to the organic EL element described above, wherein the light emitting layer comprises a compound represented by the following general formula [3] as a host material.

General formula [3]

[Wherein, R ^{22 to} R ³¹ each independently represents a fluorine atom, a hydrogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or An unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, Alternatively, it represents a substituted or unsubstituted acyl group, and adjacent substituents may form a cyclic structure. ]

  Since the organic EL element produced using the organic EL element material of the present invention emits light at a lower driving voltage and has a longer life than conventional ones, it is preferably 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 anthracene compound represented by the general formula [1] will be described.

In the general formula [1], X ¹ and X ² are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

In X ¹ and X ² , the substituted or unsubstituted alkyl group is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, more preferably a substituted or unsubstituted group having 1 to 10 carbon atoms. Specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl In addition to unsubstituted linear or branched alkyl groups such as groups, ethoxyethyl group, ethoxymethyl group, methoxymethyl group, methoxyethyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group , Α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoro B methylbenzyl group and a substituted alkyl group such as a triphenylmethyl group.

In X ¹ and X ² , the substituted or unsubstituted aryl group is preferably a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, more preferably a substituted or unsubstituted group having 6 to 18 carbon atoms. Specifically, a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,4,6-trimethylphenyl group, 4-ethylphenyl group, biphenyl group 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group and the like.

In the general formula [1], R ^{1 to} R ¹⁶ are each independently a hydrogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or An unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, Alternatively, it represents a substituted or unsubstituted acyl group, and adjacent substituents may form a cyclic structure. However, at least one of R ^{9 to} R ¹⁶ is a substituted or unsubstituted amino group or a group represented by the following general formula [2].

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted amino group is preferably a substituted or unsubstituted amino group having 1 to 40 carbon atoms, specifically, an amino group, a dimethylamino group, a diethylamino group , Dipropylamino group, diisopropylamino group, di (n-butyl) amino group, di (sec-butyl) amino group, di (tert-butyl) amino group, dipentylamino group, diisopentylamino group, dineopentyl Amino group, di (tert-pentyl) amino group, dihexylamino group, diisohexylamino group, diheptylamino group, dioctylamino group, dinonylamino group, didecylamino group, diphenylamino group, dibiphenylylamino group, di (o -Tolyl) amino group, di (m-tolyl) amino group, di (p-tolyl) amino group, dixylylamino group, di ( o-cumenyl) amino group, di (m-cumenyl) amino group, di (p-cumenyl) amino group, diphenanthrylamino group, dipyrenylamino group, dicricenylamino group, dinaphthacenylamino group, methylethyl Amino group, methylpropylamino group, methylbutylamino group, methylpentylamino group, methylhexylamino group, ethylpropylamino group, ethylbutylamino group, ethylpentylamino group, ethylhexylamino group, propylbutylamino group, propylpentylamino Group, propylhexylamino group, butylpentylamino group, butylhexylamino group, pentylhexylamino group, phenylbiphenylylamino group, phenylterphenylylamino group, dinaphthylamino group, phenylnaphthylamino group, phenylanthrylamino group , Biff Nylylnaphthylamino group, biphenylylanthrylamino group, biphenylylphenanthrylamino group, naphthylanthrylamino group, naphthylphenanthrylamino group, naphthylterphenylylamino group, anthrylphenanthrylamino group, anne Tolylterphenylylamino group, methylphenylamino group, methylbiphenylylamino group, methylnaphthylamino group, methylanthrylamino group, methylphenanthrylamino group, methylterphenylylamino group, ethylphenylamino group, ethylbiphenyl Rylamino group, ethylnaphthylamino group, ethylanthrylamino group, ethylphenanthrylamino group, ethylterphenylylamino group, propylphenylamino group, propylbiphenylylamino group, propylnaphthylamino group, propyl Anthrylamino group, propylphenanthrylamino group, propylterphenylylamino group, butylphenylamino group, butylbiphenylylamino group, butylnaphthylamino group, butylanthrylamino group, butylphenanthrylamino group, butylter Phenylylamino group, pentylphenylamino group, pentylbiphenylylamino group, pentylnaphthylamino group, pentylanthrylamino group, pentylphenanthrylamino group, pentylterphenylylamino group, hexylphenylamino group, hexylbiphenylylamino Group, hexylnaphthylamino group, hexylanthrylamino group, hexylphenanthrylamino group, hexylterphenylylamino group, dipyridylamino group, diquinolylamino group, phenylpyridylamino group, etc. It is.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted alkenyl group is preferably a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, specifically, a vinyl group, a propenyl group, a butenyl group, Examples include oleyl group, eicosapentaenyl group, docosahexaenyl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, 2-phenyl-2-propenyl group and the like.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted alkoxy group is preferably a substituted or unsubstituted alkoxy group having 2 to 40 carbon atoms, more preferably a substituted or unsubstituted group having 2 to 10 carbon atoms. Specifically, methoxy group, ethoxy group, propoxy group, isopropoxy group, isobutoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, iso Examples include alkoxyl groups such as a pentyloxy group.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted aryloxy group is preferably a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, and specifically includes a phenoxy group and p-nitrophenoxy group. And aryloxy groups such as p-tert-butylphenoxy group, 3-fluorophenoxy group, pentafluorophenyl group, 3-trifluoromethylphenoxy group, naphthyloxy group, anthryloxy group.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted aromatic heterocyclic group is a 5-membered or 6-membered aromatic heterocyclic group containing O, N, or S as a hetero atom, or a condensed polycyclic aromatic group. A heterocyclic group is mentioned. The condensed polycyclic aromatic heterocyclic group preferably has 4 to 40 carbon atoms, and more preferably 4 to 20 carbon atoms. Examples of the aromatic heterocyclic group and the condensed polycyclic aromatic heterocyclic group include thienyl group, furyl group, pyrrolyl group, pyridyl group, quinolyl group, quinoxalyl group, imidazopyridyl group, benzothiazole group, furanyl group, thiophenyl group, Examples include pyrrole group, pyranyl group, thiopyranyl group, thiazolyl group, imidazole group, pyrimidinyl group, triazinyl group, indolinyl group, purinyl group, dioxanyl group, dioxolanyl group and the like.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted arylthio group is preferably a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms, more preferably a substituted or unsubstituted group having 6 to 20 carbon atoms. Specifically, phenylthio group, p-nitrophenylthio group, p-tert-butylphenylthio group, 3-fluorophenylthio group, pentafluorophenylthio group, 3-trifluoromethylphenylthio group And arylthio groups such as groups.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted alkylthio group is preferably a substituted or unsubstituted alkylthio group having 2 to 40 carbon atoms, and more preferably a substituted or unsubstituted group having 2 to 10 carbon atoms. Specific examples thereof include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, and a decylthio group.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted acyl group is preferably a substituted or unsubstituted acyl group having 1 to 40 carbon atoms, and more preferably a substituted or unsubstituted group having 1 to 10 carbon atoms. Specific examples of the acyl group include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, cyclohexylcarbonyl group, benzoyl group, and phenylacetyl group.

In R ^{1 to} R ¹⁶ , the substituted or unsubstituted alkyl group and the substituted or unsubstituted aryl group are the substituted or unsubstituted alkyl group and substituted or unsubstituted aryl described for X ¹ and X ² , respectively. Synonymous with group.

R ^{1 to} R ¹⁶ may form a cyclic structure with adjacent substituents.

  Examples of the ring formed by bonding the adjacent substituents to each other include, for example, indene, naphthalene, anthracene, phenanthrene, quinoline, iso-quinoline, quinoxaline, phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine, benzo Examples include thiazole, benzothiophene, benzofuran, acridone, benzimidazole, coumarin, and flavone.

At least one of R ^{9 to} R ¹⁶ is a substituted or unsubstituted amino group or a group represented by the general formula [2]. In the general formula [2], R ^{17 to} R ²¹ are each independently , Hydrogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or It represents an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted acyl group, and adjacent substituents may form a cyclic structure. . Y represents a sulfur atom or an oxygen atom.

In R ^{17 to} R ²¹ , a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, substituted or The unsubstituted aromatic heterocyclic group, the substituted or unsubstituted arylthio group, the substituted or unsubstituted alkylthio group, and the substituted or unsubstituted acyl group are each substituted or unsubstituted as described in R ^{1 to} R ¹⁶ . Alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted Substituted arylthio groups, substituted or unsubstituted alkylthio groups, and substituted or unsubstituted It is synonymous with a substituted acyl group.

  The anthracene compound represented by the general formula [1] that can be used in the present invention has been described above. The molecular weight of these anthracene compounds is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. This is because it is considered that the higher the molecular weight, the worse the vapor deposition property when an element is created by vapor deposition.

  Table 1 shows typical examples of the anthracene compound represented by the general formula [1] that can be used as the organic EL device material of the present invention. However, the present invention is not limited to these.

Table 1

  The anthracene derivative of the general formula [1] used in the organic EL device of the present invention can be synthesized by amination reaction using a commercially available amine or an amine synthesized by a known method or a derivative thereof and a halogenated anthracene derivative as starting materials. (J. Am. Chem. Soc. 1994. 116, 7901., etc.). Examples of the synthesis scheme are shown below.

Formula 1

  The anthracene derivative of the general formula [1] used in the organic EL device of the present invention is synthesized by a Suzuki coupling reaction using a commercially available boronic acid or a boronic acid synthesized by a known method or a derivative thereof and a halogenated anthracene derivative as starting materials. (Synth. Commun., 1981.11, 513. etc.). Examples of the synthesis scheme are shown below.

Formula 2

  A halogenated anthracene derivative can be synthesized from an anthraquinone derivative, a halogenated Grignard reagent and a halogenated aryllithium derivative by a known method (Molecules, 2000, 5, 620-628, etc.). Examples of the synthesis scheme are shown below.

Formula 3

Next, the anthracene compound represented by the general formula [3] will be described. In the general formula [3], R ^{22 to} R ³¹ each independently represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group. Substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted arylthio group, substituted or unsubstituted It represents an alkylthio group or a substituted or unsubstituted acyl group, and adjacent substituents may form a cyclic structure.

Here, in R ^{22 to} R ³¹ , a substituted or unsubstituted amino group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted An aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, and a substituted or unsubstituted acyl group, The substituted or unsubstituted amino group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl described in the general formula [1] Oxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted Or it is synonymous with an unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, and a substituted or unsubstituted acyl group.

  The anthracene compound represented by the general formula [3] used in the present invention has been described above, but the molecular weight of these anthracene compounds is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. This is because, when the molecular weight is large, there is a concern that the vapor deposition property in the case of producing an element by vapor deposition is deteriorated.

  Hereinafter, typical examples of the anthracene compound represented by the general formula [3] that can be used as the material for the organic EL device of the present invention are shown in Table 2, but the present invention is not limited to these.

Table 2

  By the way, the organic EL element is composed of an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode. Here, the single layer type organic EL element is composed only of a light emitting layer between an anode and a cathode. The element which becomes. On the other hand, the multilayer organic EL element facilitates injection of holes and electrons into the light emitting layer in addition to the light emitting layer, and facilitates recombination of holes and electrons in the light emitting layer. For the purpose of this, it refers to a layer in which a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and the like are laminated. Therefore, typical element configurations of the multilayer organic EL element include (1) anode / hole injection layer / light emitting layer / cathode, and (2) anode / hole injection layer / hole transport layer / light emitting layer / cathode. (3) Anode / hole injection layer / light emitting layer / electron injection layer / cathode, (4) Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode, (5) Anode / positive Hole injection layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (6) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (7) An element structure in which a multilayer structure of anode / light emitting layer / hole blocking layer / electron injection layer / cathode, (8) anode / light emitting layer / electron injection layer / cathode, etc., is considered.

  The anthracene compound of the present invention may be used in any of the above-described layers, but can be suitably used particularly for the light emitting layer. The organic EL device material of the present invention can be used not only as a single compound but also as a combination of two or more compounds, that is, mixed, co-evaporated, laminated, etc. is there. Furthermore, in the above-mentioned hole injection layer, hole transport layer, light emitting layer, and electron injection layer, they may be used together with other materials.

  Here, the hole injection layer has a hole injection material that exhibits an excellent hole injection effect for the light emitting layer and can form a hole injection layer having excellent adhesion to the anode interface and thin film formation. Used. In addition, when such materials are laminated in multiple layers and a material having a high hole injection effect and a material having a high hole transport effect are laminated, the materials used for each are called a hole injection material and a hole transport material. Sometimes. Examples of such hole injection materials or hole transport materials include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives, imidazolethione derivatives, pyrazoline derivatives, pyrazolone derivatives. , Tetrahydroimidazole derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, acyl hydrazone derivatives, stilbene derivatives, aromatic tertiary amine derivatives, polyvinyl carbazole derivatives, polysilane derivatives, etc. However, the material is not particularly limited as long as the material can inject holes from the anode and transport holes.

Among the above materials, examples of the hole injection material or the hole transport material that can be particularly preferably used include aromatic tertiary amine derivatives and phthalocyanine derivatives. Examples of the aromatic tertiary amine derivative include 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, and oligomers having these aromatic tertiary amine skeletons Or a polymer, which is a hole injection material or a hole transport material. In Le it can be suitably used. 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) Examples include phthalocyanine derivatives such as GaPc, VOPc, TiOPc, MoOPc, and GaPc-O-GaPc, and these can be suitably used for hole injection materials.

  On the other hand, for the electron injection layer, an electron injection material that exhibits an excellent electron injection effect with respect to the light emitting layer and that can form an electron injection layer excellent in adhesion to the cathode interface and thin film formability is used. Examples of such electron injection materials include metal complex compounds, nitrogen-containing five-membered ring derivatives, fluorenone derivatives, anthraquinodimethane derivatives, diphenoquinone derivatives, thiopyrandioxide derivatives, perylenetetracarboxylic acid derivatives, fluorenylidenemethane. Derivatives, anthrone derivatives, silole derivatives, calcium acetylacetonate, sodium acetate and the like. In addition, inorganic / organic composite materials doped with metal such as cesium in bathophenanthroline (Proceedings of the Society of Polymer Science, Vol. 50, No. 4, 660, published in 2001) and the 50th Applied Physics Related Lecture Conference Proceedings, No. Examples of electron injection materials include BCP, TPP, T5MPyTZ, etc. published on page 3, 1402, 2003. Electrons can be transported by forming a thin film necessary for device fabrication and injecting electrons from the cathode. If it is material, it will not specifically limit to these.

  Among the electron injection materials, particularly effective electron injection materials include metal complex compounds and nitrogen-containing five-membered ring derivatives. Among the electron injection materials that can be used in the present invention, preferred metal complex compounds include tris (8-quinolinolato) aluminum, tris (2-methyl-8-quinolinolato) aluminum, and tris (5-phenyl-8-quinolinolato) aluminum. Bis (8-quinolinolato) (1-naphtholato) aluminum, bis (8-quinolinolato) (2-naphtholato) aluminum, bis (8-quinolinolato) (phenolate) aluminum, bis (8-quinolinolato) (4-cyano-1) -Naphtholate) aluminum, bis (4-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (5-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (5-phenyl-8-quinolinolato) ( Phenolate) aluminum, bis Aluminum complex compounds such as 5-cyano-8-quinolinolato) (4-cyano-1-naphtholato) aluminum, bis (8-quinolinolato) chloroaluminum, bis (8-quinolinolato) (o-cresolato) aluminum, tris (8- Quinolinolato) gallium, tris (2-methyl-8-quinolinolato) gallium, tris (2-methyl-5-phenyl-8-quinolinolato) gallium, bis (2-methyl-8-quinolinolato) (1-naphtholato) gallium, bis (2-Methyl-8-quinolinolato) (2-naphtholato) gallium, bis (2-methyl-8-quinolinolato) (phenolate) gallium, bis (2-methyl-8-quinolinolato) (4-cyano-1-naphtholate) Gallium, bis (2,4-dimethyl-8-quinolinolato) 1-naphtholato) gallium, bis (2,5-dimethyl-8-quinolinolato) (2-naphtholato) gallium, bis (2-methyl-5-phenyl-8-quinolinolato) (phenolate) gallium, bis (2-methyl- 5-cyano-8-quinolinolato) (4-cyano-1-naphtholato) gallium, bis (2-methyl-8-quinolinolato) chlorogallium, bis (2-methyl-8-quinolinolato) (o-cresolato) gallium, etc. Besides gallium complex compounds, 8-quinolinolatolithium, bis (8-quinolinolato) copper, bis (8-quinolinolato) manganese, bis (10-benzo [h] quinolinolato) beryllium, bis (8-quinolinolato) zinc, bis And metal complex compounds such as (10-benzo [h] quinolinolato) zinc.

  Among the electron injection materials that can be used in the present invention, preferable nitrogen-containing five-membered ring derivatives include oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and triazole derivatives. , 5-bis (1-phenyl) -1,3,4-oxazole, 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-butyl benzene], 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- Examples thereof include bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene and the like.

  Furthermore, a hole blocking material that can prevent holes from passing through the light emitting layer from reaching the electron injection layer and form a layer having excellent thin film formability is used for the hole blocking layer. Examples of such hole blocking materials include aluminum complex compounds such as bis (8-quinolinolato) (4-phenylphenolate) aluminum, and bis (2-methyl-8-quinolinolato) (4-phenylphenolate). Examples thereof include gallium complex compounds such as gallium and nitrogen-containing condensed aromatic compounds such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP).

  The material for an organic EL device of the present invention is a compound having strong fluorescence in a solid state, and is suitable as a light emitting material in a light emitting layer. Furthermore, when it is used as a doping material combined with other host materials, it is possible to select a high light emission efficiency and light emission wavelength by doping at an optimum ratio in the light emitting layer. Further, by using another doping material as the doping material together with the material for the organic EL device of the present invention, light emission from blue to red and further to white can be obtained.

  When the light emitting layer is composed of a host material and a doping material, the ratio is 50.0 to 99.999% by weight of the host material and 0.001 to 50.0% by weight of the dopant material. It is the range of 0.001-30 weight% with respect to host material, More preferably, it is the range of 0.01-10 weight%, More preferably, it is the range of 0.1-5 weight%.

  Although there is no limitation in particular as another host material, It is preferable to contain an anthracene derivative, a naphthalene derivative, or a biphenyl derivative.

  Although there is no limitation in particular as another dopant material, It is preferable to contain a perylene derivative, a coumarin derivative, or a quinacridone derivative.

  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. In addition, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers.

  Furthermore, the materials used for the anode of the organic EL device of the present invention are metals such as carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and alloys thereof, zinc oxide, oxidation Examples thereof include conductive metal oxides such as tin, indium oxide and indium tin oxide (ITO), and conductive polymers such as polythiophene, polypyrrole and polyaniline. In particular, as a conductive material used for the anode of the organic EL device of the present invention, a material having a resistance value as low as possible is preferable, and ITO glass and NESA glass are preferably used.

  The material used for the cathode of the organic EL device of the present invention is not particularly limited as long as it can efficiently inject electrons into the organic EL device, but in general, platinum, gold, silver, copper, iron, tin, Examples thereof include zinc, aluminum, indium, chromium, lithium, sodium, potassium, calcium, magnesium, and alloys thereof. Here, examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but alloys containing a low work function metal such as lithium, sodium, potassium, calcium, and magnesium are preferable. In addition, an inorganic salt such as lithium fluoride can be used in place of the low work function metal. Moreover, as a preparation method of these cathodes, they can be prepared by methods known in the industry such as resistance heating, electron beam beam irradiation, sputtering, ion plating, and coating. The anode and cathode described above may be formed with a layer structure of two or more layers as necessary.

  In order to efficiently extract light emitted from the organic EL device of the present invention, it is desirable that the substrate material on the surface from which light is extracted is sufficiently transparent. Specifically, the transmittance of light emitted from the device in the emission wavelength region is high. It is desirable that it is 50% or more, preferably 90% or more. These substrates have mechanical and thermal strength and are not particularly limited as long as they are transparent. For example, in addition to glass, transparent polymers such as polyethylene, polyethersulfone, and polypropylene are recommended.

  In addition, as a method for forming each layer of the organic EL element of the present invention, a dry film forming method such as vacuum deposition, electron beam beam irradiation, sputtering, plasma, ion plating, or a wet process such as spin coating, dipping, or flow coating is used. Any of the membrane methods can be applied. The film thickness of each layer is not particularly limited, but if the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. Conversely, if the film thickness is too thin, pinholes, etc. And it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied. Accordingly, the thickness of each layer is suitably in the range of 1 nm to 1 μm, but more preferably in the range of 10 nm to 0.2 μm.

  Further, in order to improve the stability of the organic EL element with respect to temperature, humidity, atmosphere and the like, a protective layer may be provided on the surface of the element, or the entire element may be covered or sealed with a resin or the like. In particular, when the entire element is covered or sealed, a photocurable resin that is cured by light is preferably used.

  As described above, this organic EL element can obtain blue light emission exhibiting high color purity and luminance at a low driving voltage. 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.

Synthesis Example 1 Synthesis Method of Compound (C) The synthesis scheme is as shown in Formula 4.

Formula 4

  Add 60.2 g of 5-bromo-2-iodotoluene in 90 g of THF, and cool to −10 ° C. with stirring under a nitrogen atmosphere. Thereafter, 2.6 ml of a 2.6 mol / l n-butyllithium-hexane solution was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was stirred for 1 hour while maintaining at 0 ° C. or lower to prepare a THF solution. Next, 20.8 g of anthraquinone was added to 90 g of toluene in another container, and the mixture was cooled to −15 ° C. while stirring in a nitrogen atmosphere. And the THF solution prepared previously was dripped over 25 minutes, and it stirred at room temperature after completion | finish of dripping for 6 hours. 1000 g of water was added to the reaction solution, and only the organic layer was extracted. This was concentrated under reduced pressure to obtain 44.2 g of compound (C) (yield 85%). When the TOF-MS (manufactured by Bruker Daltonics, Autoflex II) of this compound was measured, the structure was confirmed from the fact that m / z = 550 was obtained with respect to the molecular weight of the compound (C) = 550 1.

Synthesis Example 2 Synthesis Method of Compound (D) The synthesis scheme is as shown in Formula 5.

Formula 5

  To 300 g of acetic acid, 5.5 g of compound (C), 14.6 g of sodium iodide and 14.4 g of sodium phosphinate monohydrate were added, and the mixture was stirred at 120 ° C. for 1 hour under a nitrogen atmosphere. Thereafter, it was allowed to cool to room temperature. Next, this reaction solution was added to 450 g of water and stirred, and a pale yellow precipitate was collected by filtration to obtain 4.0 g of Compound (D) (yield 77%). When the TOF-MS of this compound was measured, the structure was confirmed from the fact that m / z = 516 was obtained with respect to the molecular weight of the compound (D) = 516.

Synthesis Example 3 Synthesis Method of Compound (A1) In 150 g of toluene, 2.6 g of compound (D), 2.8 g of diphenylamine, 0.15 g of palladium acetate, 0.34 g of bis- [2- (diphenylphosphino) phenyl] ether , 4.5 g of t-butoxy sodium was added, and the mixture was heated to reflux for 3 hours with stirring under a nitrogen atmosphere. After allowing to cool, this toluene solution was then added to 200 g of methanol and stirred at room temperature for 1 hour. The precipitate was collected by filtration. This was dissolved in a mixed solvent of chloroform: hexane = 1: 3 and purified by column chromatography to obtain 3.1 g of Compound (A1) (yield 91%). When TOF-MS of this compound was measured, m / z = 693 was obtained with respect to the molecular weight of compound (A1) = 693, and the structure was confirmed.

Synthetic Example 4 Synthetic Method of Compound (A2) In Synthetic Example 3, except that 3.0 g of ditolylamine was used instead of 2.8 g of diphenylamine, a reaction was carried out in the same manner to find 3.2 g of Compound (A2) (yield 85). %). When the TOF-MS of this compound was measured, m / z = 749 was obtained with respect to the molecular weight of the compound (A2) = 749, and the structure was confirmed.

Synthesis Example 5 Synthesis Method of Compound (A41) In 130 g of THF, 2.6 g of Compound (D), 1.5 g of benzo [b] thiophen-2-ylboronic acid, 1.3 g of tetrakis (triphenylphosphine) palladium, 38 potassium carbonate 0.5 g and 128 g of water were added, and the mixture was stirred at 60 ° C. for 3 hours under a nitrogen atmosphere. After allowing to cool, the precipitate was collected by filtration. This was added to 400 g of methanol and stirred at room temperature for 1 hour, and the crystals were collected by filtration. The obtained crystals were recrystallized from toluene to obtain 2.4 g (yield 77%) of Compound (A41). When the TOF-MS of this compound was measured, m / z = 623 was obtained with respect to the molecular weight of the compound (A41) = 623, and thus the structure was confirmed.

Synthesis Example 6 Synthesis Method of Compound (A52) The same procedure as in Synthesis Example 5 except that 1.3 g of benzo [b] furan-2-ylboronic acid was used instead of 1.5 g of benzo [b] thiophen-2-ylboronic acid. Then, 2.2 g (yield 75%) of compound (A52) was obtained. When TOF-MS of this compound was measured, m / z = 591 was obtained with respect to the molecular weight of compound (52) = 591, and the structure was confirmed.

  EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example at all. In this example, all mixing ratios are weight ratios unless otherwise specified. Moreover, the characteristic of the organic EL element with an electrode area of 2 mm × 2 mm was measured.

Example 1
A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and then the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, the compound (A1) in Table 1 was vacuum-deposited to obtain a light-emitting layer having a thickness of 20 nm, and then tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec. An electron transport layer was deposited to a thickness of 50 nm, and further, lithium fluoride was deposited to a thickness of 1 nm, and then aluminum was deposited to a thickness of 150 nm. work. in this way, an organic EL element was manufactured. the organic EL devices fabricated, was defeated indicia DC voltage, voltage 6.5V, at a current density of 10 mA / cm ^2, blue light emission of 200 cd / m ² Emission maximum wavelength:. 450 nm) where the sample was continuously burn-DC obtained current density 10 mA / cm ^2, the half-life was 110 hours.

Example 2 to Example 10
An organic EL device was produced in the same manner as in Example 1 except that the anthracene compound shown in Table 3 was used instead of the compound (A1). Table 3 shows the brightness and half-life at a current density of 10 mA / cm ² in these devices.

Table 3

Comparative Example 1
An organic EL device was produced in the same manner as in Example 1 except that the following 6,12-bis (diphenylamino) chrysene was used instead of the compound (A1). Blue light emission (emission maximum wavelength: 451 nm) of 90 cd / m ² was obtained at a driving voltage of 6.8 V and a current density of 10 mA / cm ² in this device. When a DC continuous energization test was performed at a current density of 10 mA / cm ² , the half-life was 30 hours.

Example 11
The structure of the light-emitting layer was the same as in Example except that the compound (A1) in Table 1 and the compound (B36) in Table 2 were co-deposited at a composition ratio of 1:99 (weight ratio) to form a light-emitting layer with a thickness of 20 nm. 1 was used to produce an organic EL device. When a direct current voltage was applied to the produced organic EL device, this device emitted blue light (emission maximum wavelength: 445 nm) with an emission luminance of 800 cd / m ² at a voltage of 6.5 V and a current density of 10 mA / cm ² . Obtained. When a continuous energization test was performed at a current density of 10 mA / cm ² , the half-life was 2000 hours.

Example 12 to Example 21
An organic EL device was produced in the same manner as in Example 11 except that the compound shown in Table 4 was used instead of the compound (A1) in Example 11. Table 4 shows the brightness and half-life of these devices at a current density of 10 mA / cm ² .

Table 4

Examples 22-45
An organic EL device was produced in the same manner as in Example 11 except that the compound shown in Table 5 was used instead of the compound in Example 11 (B36). Table 5 shows the luminance and half-life at a current density of 10 mA / cm ² in these devices.

Table 5

Examples 46 and 47
An organic EL device was prepared in the same manner as in Example 11 except that the compound (E) and compound (F) shown in Table 6 were used instead of the compound (B36) in Example 11 as a film. did. Table 7 shows the luminance and half-life at a current density of 10 mA / cm ² in these devices.

Table 6

Table 7

Comparative Example 2
An organic EL device was produced in the same manner as in Example 11 except that 6,12-bis (diphenylamino) chrysene shown below was used instead of the compound (A1) in Example 11. Blue light emission (emission maximum wavelength: 455 nm) of 270 cd / m ² was obtained at a drive voltage of 7.2 V and a current density of 10 mA / cm ² in this device. When a DC continuous energization test was performed at a current density of 10 mA / cm ² , the half-life was 270 hours.

Comparative Example 3 and Comparative Example 4
An organic EL device was produced in the same manner as in Example 11 except that the compound (G) and compound (H), which are known compounds shown in Table 8, were used instead of the compound (B36) in Example 11 as a film. Produced. Table 9 shows the luminance and half-life at a current density of 10 mA / cm ² in these devices.

Table 8

Table 9

Example 48
The structure of the light-emitting layer was as follows: DCJTB shown below, compound (A1) in Table 1 and compound (B36) in Table 2 were co-evaporated at a composition ratio of 1:29:70 (weight ratio), and a light-emitting layer having a thickness of 15 nm An organic EL element was produced in the same manner as in Example 1 except that. When a direct current voltage was applied to the produced organic EL element, white light emission with a light emission luminance of 600 cd / m ² was obtained at a driving voltage of 7.2 V and a current density of 10 mA / cm ² . When a continuous energization test was performed at a current density of 10 mA / cm ² , the half-life was 1800 hours.

Examples 49-57
An organic EL device was produced in the same manner as in Example 36 except that the compound shown in Table 10 was used instead of the compound (A1) in Example 45. Table 10 shows the luminance and half-life at a current density of 10 mA / cm ² for these devices.

Table 10

Examples 58-66
An organic EL device was produced in the same manner as in Example 48 except that the compound shown in Table 11 was used instead of the compound in Example 48 (B36). Table 11 shows the luminance and half-life at a current density of 10 mA / cm ² for these devices.

Table 11

Example 67
On the cleaned glass plate with ITO electrode, PEDOT was formed into a film thickness of 50 nm by spin coating, and then Compound 2 and Compound 61 were mixed at a ratio of 1:99, and toluene was added at a concentration of 2 mmol / l. A light emitting layer having a thickness of 100 nm was obtained by spin coating. On top of that, an electrode having a thickness of 40 nm for calcium and 80 nm for aluminum was formed to produce an organic EL element. When direct current voltage was applied to the produced organic EL element, blue light emission with a maximum luminance of 500 cd / m ² was obtained.

Example 68
On the washed glass plate with an ITO electrode, the compound (A6) was deposited to a thickness of 75 nm at a deposition rate of 0.2 nm / sec to form a hole transport layer. Subsequently, the compound (G) was vacuum-deposited to obtain a light emitting layer having a thickness of 20 nm. Next, tris (8-quinolinolato) aluminum was deposited to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron transport layer. On top of this, an electrode having a thickness of 1 nm of lithium fluoride and 150 nm of aluminum was formed to produce an organic EL device. When a direct current voltage was applied to the produced organic EL element, blue light emission (emission maximum wavelength: 450 nm) of 200 cd / m ² was obtained at a voltage of 6.0 V and a current density of 10 mA / cm ² . When a DC continuous energization test was performed at a current density of 10 mA / cm ² , the half-life was 100 hours.

  As is clear from the above-described embodiments, the use of the organic EL element material of the present invention makes it possible to improve the light emission luminance and extend the lifetime when the organic EL element is driven at a low voltage. .

Claims (8)

A material for an organic electroluminescence element represented by the following general formula [1].
General formula [1]

[Wherein, X ¹ and X ² are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
R ^{1 to} R ¹⁶ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy Group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted It represents a substituted acyl group, and adjacent substituents may form a cyclic structure. However, at least one of R ^{9 to} R ¹⁶ is a substituted or unsubstituted amino group, or a group represented by the following general formula [2]. ]
General formula [2]

[Wherein, R ^{17 to} R ²¹ are each independently a fluorine atom, a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, substituted or Unsubstituted aryloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted acyl group And adjacent substituents may form a cyclic structure.
Y represents a sulfur atom or an oxygen atom. ] ^{2. The} material for an organic electroluminescence device according to claim 1, wherein X ¹ and X ² are each independently a substituted or unsubstituted alkyl group. The light emitting layer material for organic electroluminescent elements which comprises the material for organic electroluminescent elements of Claim 1 or 2. The light emitting layer material for an organic electroluminescence device according to claim 3, which is a light emitting layer dopant material for an organic electroluminescence device. 3. The organic electroluminescence device 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 including an anode and a cathode, and at least one organic compound thin film is formed on at least one organic compound thin film. An organic electroluminescence device comprising the material for organic electroluminescence device. The organic electroluminescent device according to claim 3, wherein a light emitting layer or a plurality of organic compound thin film including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode. An organic electroluminescence device comprising a light emitting layer material. 5. The organic electroluminescence device according to claim 4, wherein a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode. An organic electroluminescence device comprising a light emitting layer material. The organic electroluminescent element according to claim 5, wherein the light emitting layer comprises a compound represented by the following general formula [3] as a host material.
General formula [3]

[Wherein, R ^{22 to} R ³¹ each independently represents a hydrogen atom, a fluorine atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or An unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, Alternatively, it represents a substituted or unsubstituted acyl group, and adjacent substituents may form a cyclic structure. ]