TW200911731A - Chrysene derivative, material for organic electroluminescence device, emitting material for organic electroluminescence device and organic electroluminescence device - Google Patents

Abstract

A compound obtained by bonding a different aryl group to chrysene having a large energy gap is used as a host for constituting a light-emitting layer of an organic EL device. Consequently, association of molecules is suppressed, thereby making crystallization less likely. An organic EL device having a longer life can be therefore produced easily.

Description

[Technical Field] The present invention relates to a cave derivative, a material for an organic EL device, a light-emitting material for an organic EL device, and an organic EL device. [Prior Art] Conventionally, the light-emitting layer is not composed of a single organic compound, and an organic EL (EleCtr luminescence) device comprising a dopant added to a host material is known. In the organic EL device, as the main material of the light-emitting layer, it is known that the structure of the hole is applied (for example, Document 1: Reference JP-A-2004-75 567), and Document 1 describes the use of the cave as the center and the same Examples of the aryl substituent-bonded compound as a host material. However, when such a compound is used as a host material, there is a possibility that a practical element life cannot be obtained. In order to solve this problem, an object of the present invention is to provide an anthracene derivative, an organic EL material for a material, a light-emitting material for an organic element, and an organic EL element which can be easily extended in life. In order to solve this problem, the inventors of the present invention have found that it is possible to prevent the host material from meeting and extending the life of the host material by using a hetero-aryl substituent as a center. -5- 200911731 The present invention has been completed in accordance with this knowledge. Namely, the characteristics of the cave derivatives of the present invention are expressed by the following general formula (丨).

In the general formula (1), Ar1 and Ar2 are each independently, and represent a substituent in which a substituted or unsubstituted aryl group having 6 to 14 carbon atoms is composed of a single or a combination of plural. However, 'ArkAr2' Ar1 and Ar2 do not contain cockroaches. Ri~Rio represents a hydrogen atom or a substituent. However, when 'A r 1 is not substituted β-naphthyl, ar 2 is unsubstituted phenyl, unsubstituted biphenyl, 4-methyl substituted phenyl, 4-(1-naphthyl)phenyl-1-yl And the case of α-naphthyl. The cave derivative of the present invention is characterized by the following general formula (2). 200911731

In the general formula (2), the Ar 3 substituted or unsubstituted phenanthrene 'Ar4 represents a core-like or unsubstituted aryl group having a core carbon number of 6 to 4, either alone or A substituent consisting of a combination of plural numbers. R1 to R11 represent a hydrogen atom or a substituent. k is an integer of 1 to 4. Further, when k is 2 or more, R11 may be the same or different from each other. Further, in the case where Ar3 is an unsubstituted β-naphthyl group, Ar4 is not a substituted phenyl group or an α-naphthyl group. The phenanthrene derivative of the present invention is characterized by the following general formula (3)

(3) In the general formula (3), Ar4 and Ar5 are each independently, and represent a substituent in which a substituted or unsubstituted aryl group having 6 to 14 carbon atoms is composed of a single or a combination of plural. However, 'Ar4#Ar5' Ar4 and Ar5 do not contain bismuth. R1 to R12 represent a hydrogen atom or a substituent. k is an integer of 1 to 4. Further, when k is 2 or more, R11 may be the same or different from each other. 1 is an integer of 1 to 4. Further, when 1 is 2 or more, R12 may be the same or different from each other. The feature of the cave derivative of the present invention is represented by the following general formula (4)

In the general formula (4), Ar6 and Ar7 are each independently a substituent represented by a single or plural combination of a substituted or unsubstituted aryl group having 5 to 14 carbon atoms. However, Ar6#Ar7, Ar6, and Ar7 do not contain strontium. R2i to R3〇 represent a hydrogen atom or a substituent. Next, in the cave derivative of the present invention, it is preferred that R1 to R1Q be composed of at least one substituted or unsubstituted aryl group having 6 to 14 carbon atoms. Further, the cave derivative of the present invention preferably comprises at least one substituted or unsubstituted aryl group having 6 to 14 carbon atoms in the r21 to r3. Further, in the deer derivative of the present invention, R22 and R27 are each independently, and a substituted or unsubstituted aryl group having a carbon number of 6 to 14 is preferably formed by a substituent of 0.111731. Further, the ylide substituent of the present invention preferably comprises at least one phenylene group between the structures of the following general formula (5).

In the general formula (5), 'Ar8 is a substituent in which the substituted or unsubstituted aryl group having a carbon number of 6 to 14 is used singly or in combination. R 13 represents a hydrogen atom or a substituent, and m is an integer of 1 to 4. When m is 2 or more, R13 may be the same or different from each other. The material for an organic EL device of the present invention is characterized by the above-mentioned cave derivatives. The luminescent material for an organic EL device of the present invention is characterized by containing the above-mentioned cave derivatives. The organic EL device of the present invention is an organic EL device in which an organic thin film layer comprising at least one layer or a plurality of layers of a light-emitting layer is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer contains the above-mentioned cave derivative as A separate or a mixture of ingredients. In the organic EL device of the present invention, it is preferable that the light-emitting layer has a structure containing the above-mentioned cave derivative as a light-emitting material. Further, in the organic EL device of the present invention, the light-emitting layer is preferably composed of the above-mentioned -9-200911731 cave derivative as a host material. According to the present invention, since the aryl group constituting the light-emitting layer is used in the aryl group in which the holes are bonded, the molecules are prevented from coming into contact with each other, and the crystallization of the light-emitting layer is less likely to occur, and a homogeneous film can be formed. Further, an organic EL device which is easy to extend its life can be obtained. Further, in the organic EL device of the present invention, the light-emitting layer is preferably a composition containing a fluorescent or phosphorescent dopant. Further, in the organic EL device of the present invention, the light-emitting layer is preferably a composition containing an arylamine compound. In the organic EL device of the present invention, it is preferred that the light-emitting layer has a phenylvinylamine-containing compound. Further, in the organic EL device of the present invention, the light-emitting layer is preferably composed of an aromatic amine-containing compound. Further, in the present invention, the energy gap of the light-emitting layer host material is increased, and the ionization potential Ip is also increased. As a result, the difference in Ip between the host material and the hole injection/transport layer becomes large, and it is difficult to inject the hole into the light-emitting layer, and the drive voltage for obtaining sufficient brightness is increased. At this time, it is preferable to add a charge injection auxiliary agent to the light-emitting layer to alleviate the hole injection barrier. Such a charge injecting agent can be injected and transported by a known hole. In the present specification, "hole injection. Transport layer" means "at least one of a hole injection layer and a hole transport layer", and "electron injection/transmission-10-200911731 delivery layer" means "electronic EMBODIMENT OF THE INVENTION In the following, an embodiment of the present invention will be described. [Configuration of Organic EL Element] First, the element configuration of the organic EL element will be described. The composition of the components can be exemplified as follows: (1) anode/light-emitting layer/cathode (2) anode/hole injection layer/light-emitting layer/cathode (3) anode/light-emitting layer/electron injection layer/cathode (4) anode/hole injection Layer / luminescent layer / electron injection layer / cathode (5) anode / organic semiconductor layer / luminescent layer / cathode (6) anode / organic semiconductor layer / electron barrier layer / luminescent layer / cathode (7) anode / organic semiconductor layer / luminescence Layer/Adhesion Improvement Layer/Cathode (8) Anode/Curve Injection Layer/Polar Transport Layer/Light Emitting Layer/Electron Injection Layer/Cathode (9) Anode/Insulation/Light Emitting/Insulation/Cathode (10) Anode/ Inorganic semiconductor layer / insulating layer / luminescent layer / insulating layer / cathode (1 1) anode / Semiconductor layer / insulating layer / luminescent layer / insulating layer / cathode (12) anode / insulating layer / hole injection layer / hole transport layer / luminescent layer / insulating layer / cathode (13) anode / insulating layer / hole injection Layer/hole transport layer/light-emitting layer/electron injection layer/cathode-11-200911731. The organic EL device of the present embodiment injects at least a layer, a light-emitting layer, an electron transport layer, and a cathode in this order. It is preferable to use the configuration of (8). (Translucent substrate) The organic EL device is a substrate on which a light-transmitting substrate is a substrate supporting an organic EL element, and the transmittance of 400 to light is 50%. The above-mentioned smooth substrate is preferably a glass plate, a polymer plate, etc. Examples of the glass plate include soda lime glass, lead glass, aluminosilicate glass, borosilicate glass, and the like. Examples of the polymer sheet include polycarbonate, ethylene phthalate, polyether sulfide, polyfluorene, etc. (Anode) The anode of the organic EL element has a function of injecting a hole into the electric layer, and has a work of 4_5 eV or more. Indium tin oxide alloy (IT) can be used as a specific example of the function O), indium zinc oxide, gold, silver, platinum, copper, etc. For the purpose of entering the electron transport layer or the light-emitting layer, the work function anode can be used for vapor deposition or with anodes and holes. However, it is not limited to the so-called translucent 700 nm visible region, containing bismuth-germanium glass borosilicate glass, stone acrylate, poly-pair transport layer or luminescent fruit. Anode material tin (NESA) 'oxygen anode It is preferable to make the material of the electron injection small. The method of sputtering, etc., is formed by forming a film into a film -12-200911731. When the light emission from the light-emitting layer is taken out from the anode, the light-emitting transmittance to the anode is preferably greater than 10%. Further, the sheet resistance of the anode is preferably several hundred Ω / or less. The film thickness of the anode depends on the material, but is generally selected from the range of 10 nm to 1 μm, preferably 10 to 200 nm. (Light Emitting Layer) The light emitting layer of the organic EL element has the following functions. That is, it has (1) injection function; when an electric field is applied, a hole can be injected from the anode or the hole injection layer, an electron can be injected from the cathode or the electron injection layer, (2) a conveyor function; and the injected charge (electron and The function of the electric hole to move by the force of the electric field, (3) the illuminating function; the place where the electron and the hole are re-bonded, and the function of the illuminating is connected. However, the ease of injecting a hole may be different from the ease of injecting electrons, and the transfer energy expressed by the hole and the degree of electron mobility may be different in size, but it is preferable to move either one of the charges. As a method of forming the light-emitting layer, a known method such as a vapor deposition method, a spin coating method, or an LB method can be used. The light-emitting layer is preferably a molecular deposition film. The molecular deposition film is a film formed by deposition of a material compound in a gas phase state or a film formed by solidification of a material compound in a solution state or a liquid phase state, generally a film formed by the molecular deposition film and a film formed by the LB method ( Sub--13-200911731 sub-accumulation membranes can be distinguished by agglutination structure, high-order structure, or the resulting function. Further, as disclosed in Japanese Laid-Open Patent Publication No. Hei. No. Hei. Further, the thickness of the light-emitting layer is preferably 5 to 50 nm, more preferably 7 to 5 nm, and most preferably 10 to 50 nm. When it is less than 5 nm, it is difficult to form a light-emitting layer, and it is difficult to adjust the chromaticity. When the voltage exceeds 5 Onm, the driving voltage rises. In the organic EL device of the present embodiment, the light-emitting layer is composed of a host material and a dopant. Next, specific examples of the host material include compounds represented by any one of the following general formulas (1), (2), (3), and (4).

In the above general formula (1), A^ and Ar2 are each independently, and represent a substituent in which a substituted or unsubstituted aryl group having a carbon number of 6 to 14 is a combination of singly or plural. However, Ar^Ar2, Ar1, and Ar2 do not contain ruthenium. R1 to R10 represent a hydrogen atom or a substituent of -14-200911731. However, when Ar1 is not substituted with an unsubstituted β-naphthyl group, 'Ar2 is an unsubstituted phenyl group, an unsubstituted biphenyl group, a 4-methyl substituted phenyl group, a 4-(1-naphthyl)phenyl-1-yl group and α. The case of naphthyl. When ruthenium is contained, since the crystallinity is too high, there is a possibility that the performance of the element is adversely affected, which is not preferable. An aryl group having 6 to 14 carbon atoms, for example, a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a fluorenyl group, a binaphthyl group, a phenylnaphthyl group or the like. Preferred are phenyl, biphenyl, naphthyl and phenanthryl. The substituent may, for example, be an alkyl group (preferably having a carbon number of 1 to 2 Å), more preferably a carbon number of 1 to 12, particularly preferably an alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group or an isopropyl group. , t-butyl, η-octyl, η-fluorenyl, η-hexadecanyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl (preferably carbon number 2 to 20, more Preferably, it is a carbon number of 2 to 12, particularly preferably an alkenyl group having 2 to 8 carbon atoms, such as a vinyl group, an allyl group, a 2-butenyl group, a 3-pentenyl group or the like, an alkynyl group (preferably a carbon number of 2 to 20, more preferably a carbon number of 2 to 1, 2, particularly preferably an alkynyl group having a carbon number of 2 to 8, such as a propynyl group or a 3-pentynyl group, or an aryl group (preferably a carbon number) 6 to 20, particularly preferably an aryl group of 6 to 14, such as a phenyl group, a naphthyl group, a phenanthryl group or a fluorenyl group, or a heterocyclic group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 12) Heterocyclic group 'e.g. imidazolyl, succinyl, quinolinyl, fluorenyl, thienyl, aryl, morphinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl , carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, etc.), substituted or unsubstituted An amine group (preferably having a carbon number of 〇20 to 20, more preferably a carbon number of 0 to 1 2, particularly preferably an amine group having a carbon number of 〇6, such as an amine group, a methylamino group, a dimethylamino group, or a second group; Ethylamino group, diphenylamino group, dibenzylamino group, etc.) -15-200911731, alkoxy group (preferably having a carbon number of 1 to 20, more preferably a carbon number of 1 to 12, particularly preferably a carbon number) 1 to 8 alkoxy group, such as methoxy, ethoxy, butoxy, etc.), aryloxy group (preferably having a carbon number of 6 to 20, more preferably 6 to 16 carbon atoms, particularly preferably a carbon number) 6 to 12 aryloxy groups, such as phenyloxy group, 2-naphthyloxy group, etc.), fluorenyl group (preferably having a carbon number of 1 to 20, more preferably a carbon number of 1 to 16, and particularly preferably a carbon number of 1) a fluorenyl group of ～12, such as an ethyl fluorenyl group, a benzamidine group, a decyl group, a neopentyl group, etc., an alkoxycarbonyl group (preferably having a carbon number of 2 to 20, more preferably a carbon number of 2 to 16, Particularly preferred is an alkoxycarbonyl group having 2 to 12 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group, and an aryloxycarbonyl group (preferably having a carbon number of 7 to 20, more preferably a carbon number of 7 to 16). Particularly preferred is an aryloxycarbonyl group having a carbon number of 7 to 10, such as a phenyloxycarbonyl group, or a mercaptooxy group (preferably a carbon number of 2 to 2). 20, more preferably a carbon number of 2 to 16, particularly preferably a decyloxy group having a carbon number of 2 to 10, such as an ethoxycarbonyl group, a benzhydryloxy group, or the like, or a mercaptoamine group (preferably a carbon number of 2) More preferably, it is a carbon number of 2 to 16, more preferably a fluorenylamino group having a carbon number of 2 to 10, such as an acetamino group or a benzylamino group, or an alkoxycarbonylamino group. It is a carbon number of 2 to 20, more preferably a carbon number of 2 to 16, particularly preferably an alkoxycarbonylamino group having a carbon number of 2 to 12, such as a methoxycarbonylamino group, or an aryloxycarbonylamino group. Preferred is a carbon number of 7 to 20, more preferably a carbon number of 7 to 16, particularly preferably an aryloxycarbonylamino group having a carbon number of 7 to 12, such as a phenyloxycarbonylamino group, a substituted or unsubstituted sulfonate. a mercaptoamine group (preferably a carbon number of 1 to 20, more preferably a carbon number of 1 to 16, particularly preferably a sulfonylamino group having a carbon number of 1 to 12, such as methanesulfonylamino, phenylsulfonylamine a sulfonamide group which is substituted or unsubstituted (preferably having a carbon number of 0 to 20, more preferably a carbon number of 0 to 16, particularly preferably a sulfonylamino group having a carbon number of 0 to 12) such as a sulfonium sulfonate. Amine, methylsulfonylamino, dimethylsulfonylamino, phenylsulfonylamino, etc.), substituted or -16- 200911731 Substituted amine formazan base age (preferably fe number 1 to 2 Å, more preferably carbon number 1 to 16, particularly preferably carbon number 1 to methionyl group) Methylamine methyl alcohol, monoethyl ester ^^; ^ female formate, phenylamine carbenyl, etc., alkylthio (preferably carbon number 1~2 〇, m ^ Μ machine, more Preferably, the number is from 1 to 16, particularly preferably from 1 to 12 carbon atoms, by way of example, m-methylthio group, ethylthio group or the like, and arylthio group (preferably having a carbon number of from 6 to 20). More preferably, it is an arylthio group having a carbon number of 6 to 16, particularly preferably a carbon number of 6 to 12, such as > ^thio group, etc., a substituted or unsubstituted sulfonyl group (preferably having a carbon number of 1 to 2) 〇, more k is a carbon number of 1 to 16, particularly preferably a sulfonyl group having a carbon number of 1 to 12, such as a guagan #-, a thiol group, etc., a substituted or unsubstituted sulfinyl group (more Preferably, the carbon number is 1 to 2 Å, more preferably the carbon number is 1 to 16, and particularly preferably the carbon number is 1 to 12, and the sulfinium is very low. 'For example, methane sulfinyl group, phenyl sulfinyl group, etc.), substituted Or unsubstituted cellulite / & base (preferably carbon number! ~] 〇, more preferably carbon number, especially carbon number], + ureido group [such as urea group, methyl urea group, phenyl group, etc.), taking π or unsubstituted guanamine phosphate The base (preferably having a carbon number of 1 to 2 〇' is more preferably a carbon number!, r Μ1 to 16, particularly preferably a guanamine group having a carbon number of 1 to 12, such as a ethyl group, an amine group, a phenyl group. a guanidinium phosphate group, etc., a hydroxyl group, a sulfhydryl halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyanostone, a sulfhydryl group, a nitro group, a hydroxamic acid group, a suifino group, a fluorenyl group, An imido group or a heterocyclic group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 12, a hetero atom), for example, a nitrogen atom or an oxygen atom 'sulfur atom', for example, Imidazolyl, pyridyl, quinolyl, furyl, thienyl', sulphonyl, benzoxyl, benzimidazolyl, benzimidyl, oxazolyl, benzofuran基.一言,1 (10)Shishi, !.__廿phenyl, etc.), formylalkyl (preferably carbon number 3~40, more..., dibenzofuranyl, benzothiophenyl, two Benzosulfone-17- 200911731 0 3~3 carbon atoms, and particularly preferably an alkyl group having a carbon number of 3~24 A silicon of, for example, alkyl-dimethylformamide silicon, silicon triphenylsilyl group, etc.) and the like. These substituents can be substituted. When there are two or more substituents, they may be the same or different. Further, in the case of b, it is possible to form a ring by being connected to each other. In the above, 'alkyl group, alkenyl group and aryl group are preferred.

(2) In the above general formula (2), Ar3 is a substituted or unsubstituted naphthalene, a substituted or a substituted phenanthrene, and A〆 represents a substituted or unsubstituted aryl group having a core carbon number of 6 to 14 in a single or plural number. The substituents formed by the combination. R 1 to R 1 1 represent a hydrogen atom Ge substituent. k is an integer of 1 to 4. Further, when k is 2 or more, R11 may be the same or different from each other. Further, when Ar3 is not substituted with a β-naphthyl group, Ar4 is an unsubstituted phenyl group and an α-naphthyl group. When the organic thin film layer constituting the organic EL element contains the above-mentioned general formula (2), it is preferable from the viewpoint of improving quantum efficiency. -18- (3) (3) 200911731

In the above general formula (3), Ar4 and Ar5 each independently represent a substituent in which a substituted or unsubstituted aryl group having a carbon number of 6 to 14 is used alone or in combination. However, ArWAr5 ’ Α〆 and Ar5 do not contain 蒽. R1 to R12 represent a hydrogen atom or a substituent. k is an integer of 1 to 4. Further, when 'k is 2 or more', Rl1 may be the same or different from each other. 1 is an integer of 1 to 4. Further, when '1 is 2 or more', R 12 may be the same or different from each other. When the organic thin film layer constituting the organic EL element contains the above-mentioned general formula (3), it is preferable from the viewpoint of improving quantum efficiency.

In the above formula (4), Ar6 and Ar7 are each independently a substituent represented by a combination of a single or plural number of substituted or unsubstituted aryl groups having a carbon number of 6 to 14 . However, Ar6#Ar7, Ar6, and Ar7 do not contain strontium. R21 to R3G represent hydrogen -19-200911731 atom or substituent. Here, in the general formula (1), the constitution of the substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene is from the viewpoint of heat resistance. Further, in the general formulae (1) to (4), among Ri to Rl 〇' or 'r21 to r3 〇, it is preferred that at least one S-nuclear carbon number 6 to 丨4 substituted or unsubstituted aryl group is preferable. . 6~ Further 'In the general formula (4), in the case of a substituted or unsubstituted aryl group of R21 to 14 4, at least one of the nucleus carbon atoms in the R3Q, and the R22 and R27 systems are each independently substituted by a nuclear carbon number of 6 to 14 or Replace: > $ Gan,,. It is preferable that the composition of the substituent formed by the core or the rc e group in a single or complex array is preferable from the viewpoint of heat resistance. Further, in the general formulae (1) to (4), the aryl substituent is preferably constituted by a phenylene group at least in the structure of the general formula (5).

In the general formula (5), 八 is a substituent in which the aryl group having a carbon number of 6 to M is substituted or not, and the aryl group is a combination of singly or plural. Ri 3 shows the sub or substituent, m is! An integer of ~4. When m is 2 or more, the same or opposite, and the following compounds satisfying such requirements are as follows. -20- 200911731

-21 - 200911731

In the present invention, the fluorescent dopant is preferably an amine compound represented by the following formula (13). -22 - (13) (13)200911731

In the above formula (13), p is a substituted or unsubstituted aryl group having 6 to 4 Å of a core carbon number, a substituted or unsubstituted heterocyclic group having a core number of 3 to 4 Å, or a substituted or unsubstituted group. Styryl. k is an integer of 1 to 3.

Arl~ΑΓ each independently' is a substituted or unsubstituted aryl group having 6 to 4 Å of an aromatic carbon group or a substituted or unsubstituted heterocyclic group having a number of cores of 3 to 40 ’s is an integer of 〇~4. Any two adjacent substituents selected from Αγ1, Λι·2, and P may be bonded to each other to form a ring. When k is 2 or more, Ρ may be the same or different. Examples of the aromatic hydrocarbon group and the heterocyclic group of P include, for example, a substituted or unsubstituted aromatic hydrocarbon group having a core carbon number of from 6 to 40, and a substituted or unsubstituted heterocyclic group having a core number of from 3 to 40. For example, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, fluoranthene, anthracene, anthracene, anthracene, pyrene, cave, smith, dinaphthalene, trinaphthalene, phenyl hydrazine, diphenyl hydrazine, hydrazine, triphenylene , Yuhong Province, benzoquinone, diphenyl hydrazine, fluoranthene, fluorenyl, tribendivenyl, fluoranthene and fluoranthene, benzofluoranthene, benzofluoranthene, diindenoperylene The base is particularly preferably a residue of naphthalene, phenanthrene, fluoranthene, anthracene, fluorenyl, fluorenyl, sulfonium, phenylhydrazine, diphenylphosphonium and the like. In the above formula (13), Ar1 to Ar4 are each independently substituted or unsubstituted -23-200911731 having an aromatic hydrocarbon group having 6 to 40 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 40 nuclear atoms, s It is an integer from 0 to 4.

Examples of the aromatic hydrocarbon group of Ar1 to Ar4 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 9-fluorenyl group, a 1-phenanthryl group, and a 2-phenanthrene group. Base, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-butyl, 2-butyl, 9-butyl, diterpene, 2-mercapto, 4-indenyl, 2-linked Phenyl, 3-biphenylyl, 4-biphenylyl, p-bitriphenyl-4-yl, p-bitriphenyl-3-yl, p-bitriphenyl-2-yl, m- Biphenyl-4-yl, m-bitriphenyl-3-yl, m-bitriphenyl-2-yl, fluorenyl-tolyl, m-tolyl, p-tolyl, pt-butyl Phenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-indenyl, 4'-A A phenyl group, a 4"-t-butyl-P-biphenyl-4-yl group, and the like.

Examples of the heterocyclic group of Ar1 to Ar4, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-oxo noise Base, 2 - D, U, D, D, D, D, D, D, D, D, D, D, D, D, D, D, D, D, D, D Base, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isodecyl, 6-isodecyl, 7-isoindolyl, 2-furyl, 3 -furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isophenyl And furyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl, 3- Quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4- Isoquinolinyl, 5-isoquinolyl, 6-isoquinolinyl, 7-isoquinolyl, 8-isoquinoline-24- 200911731, 2 -quinoxalinyl, 5-quinoxalinyl , 6-quinoxalinyl, 1-oxazolyl, 2-hydrazine Azyl, 3-oxazolyl, 4-oxazolyl, 9-oxazolyl, 1-phenanthryl, 2-phenanthridine, 3-phenanthrene, 4-nonyl, 6-non Indenyl, 7-non-D-decyl, 8-phenanthryl, 9-phenanthryl, 10-phenanthryl, 1-anridinoyl, 2-anridinoyl, 3-anthridyl, 4- Acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7- Phenanthroline-5-yl, 1,7-phenolene-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenro Porphyrin-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenolene-4-yl, 1,8-phenanthrene- 5-Based, 1,8-Norveline-6-yl, 1,8-non-roroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-10_ 1,1, phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1, 10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2,9- Phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenro 4-yl, 2,9-phenolene-5-yl, 2,9-phenanthrene-6-yl, 2,9-non-vitamin-7-yl, 2,9-felolin 8-Based, 2,9-N-Verylin-10-yl, 2,8-N-Velin-1-yl, 2,8-Norrotolin-3-yl, 2,8-phenanthroline-4- , 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2, 7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7- Phenanthroline-10-yl, 1-phenazine, 2-phenazine, 1-phenothiazine, 2-phenothiazine, 3-phenothiazine, 4-phenothiphenyl, 10- Phenothiaphthyl, 1-Phenoxazinyl, 2-Phenoxazinyl-25-200911731, 3-Phenoxazinyl, 4-Phenoxazinyl, 10-Phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxo Diazolyl, 5-oxadiazolyl, 3-furenyl, 2-thienyl, 3-thiophenyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methyl Pyridyl-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methyl Pyrrol-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl'2-methyl-1 - mercapto, 4-methyl-1-indenyl, 2-methyl-3-indenyl, 4-methyl-3-D-indenyl, 2-t-butyl 1-D Base, 4-t-Dingmou 1-port 卩 卩, 2 -1 - butyl 3 - 卩 卩 卩, 4 -1 - butyl 3 - D 卩 卩 基 。 。. In the following, a condensed aromatic amine, a styrylamine, a benzidine or the like which is a specific example of the amine compound represented by the above formula (13) is shown, but is not limited thereto. Also, Me represents a methyl group. -26- 200911731

-27- 200911731

Z3-(V) 92-(v) s-(v) Integrity V) ω 28- 200911731 α

S-(v) 9ε-<) ζε-(ν) s-(v) -29- 200911731

ΘΙΛΙ 11ΛΙ llv) CN inch-(V)

9'(ν)

Cn9-(v)

11ΛΙ s-(v) 0 inch-<)

61V) -30- 200911731

09-(v) s-(v)

S9-(V)

S—(v)

Co9_(v) -31 - 200911731

§-(< 0ΙΛΙω1ΛΙ

A2 99-(ν)

9ιλι εζ—(ν) 92

3Z people V) 1ΙΛΙ

Ζζ into V) 1ΙΛΙ

U

d Ρ

Zz-(v) 9Z-(V) sz—(v) 91ΛΙ 91Λ1 9ΙΛΙ 11Λ!

Inch z-<) -32- 200911731

91ΛΙ

岑(V) 11Λ111ΛΙ 1ΙΛΙ

Inch 8-(<) 1 ΙΛΙωΙΛΙωΙΛ1

Εοοέ ^ΙΛΙΘΙΛΙ

Ν9-(ν) ωιΛιωιΛΙΟΙΛΙ

0000_(<) §-<) Bu 9-(< 99-( V) -33- 200911731

Co6_(v)

9ΙΛ1ωΙΛ! s-(v)

Bu 6-(v)

I—(v)

06-(v)

-34- 200911731

I 11ΛΙ

Εον(ν) mm

ΦΙΛΙ 1 |/\1人1 ΙΛί- ωΙΛΙ 1 ΙΛΙ 1! ΛΓΦ1ΛΙ

Οοοτ(ν) 301_(< 1 1ΛΙωΙΛΙ11ΛΙ 1ΙΛΙ _ωΙΛΙ yl02ΦΙΛΙ sok(v) αγγ Λ 1ΙΛΙ

11Λ1

9ΙΛ1 9ΙΛΙΛ 1 ΙΛΙ- 1 ΙΛΙωιΛΙ 1 1ΛΓ 1 1ΛΙ

ΩΙΛΙ θ1ΛΙωΙΛΙω1ΛΙ ,,ωΙΛΙ ^_ωι/\ιωΙΛΙ ST(V) 1ΙΛΙ-/ i

11ΛΙ11ΛΙ ΘΙΛΙωιΛΙ

ΘΙΛΙωιΛΙ ST(V) 90T(V) 35- 200911731

Ni(v) 9U, (V) su-(v) -36- 200911731

Δ-(ν) §-( V) 6U-(V) 9U-(V)

63T(V) s-(v) ζ9-(ν) 93ZV) -37- 200911731

Εετ(ν) οιλιθιλι

^τ(ν) οετ(ν)

ΦΙΛΙ 91ΛΙ 9ετ(ν)

ω!ΛΙ 6εζν)

3ετ(ν)

95 inches ετ(ν) ωΙΛΙιυΙΛΙ ω1ΛΙ ΦΙΛΙ ΦΙΛΙ

i 9εν(ν)

Ζετ(ν) 9|Λ1 -38- 200911731 ΖΗ-(ν)

9 inch k<) ΘΙΛΙωιΛΙ -I 9|Λ| Most αιΛΙ m-(v) ωιΛΙ

Inch' (<)

ZH-(V) as ώιΛΙ ΦΙΛΙ ωΙΛΙ 9|Λ1

ΗΗ_(ν) i >‘Φ1ΛΙ

Υυ5<υΙΛΙ 9H-(V) -39- 200911731

-40- 200911731

-41 - 200911731 EM32

EM34 EM35

(A)-168 (A)_169

-42 - 200911731 EM41

CH=CH

CH=CH

(A)-172 (A)-173

-43- 200911731

(A)-176 (A)-177 EM48

EM50

(A)-180 -44- 200911731 EM51

(A)-182 (A)-183 (A)-184

Me Me -45- 200911731 EM56 EM57

EM58

(A)-188 EM59 EM60 Or

CH=CH EM61 EM62 Or

CH=CH (AH 89 (A)-190 (A)-191 "Ο (A)-192 -46 - 200911731

(A)-194 CH=CH (A)-193

CH=CH (A)-195

Further, it may be a compound containing the following carbazolyl group. -47- 200911731

(A)-164 In the present invention, the fluorescent dopant may be a fluoranthene derivative represented by any one of the following formulas (21) to (24).

• · · (21) • (22) -48- (23) 200911731

In the formulae (21) to (24), Xi to X52 are each independently represented by a hydrogen atom, a halogen atom, a substituted or unsubstituted linear, branched or cyclic carbon atom, and are substituted or unsubstituted. a linear, branched or cyclic k-oxy group having 1 to 30 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted. a chain, a branched or a cyclic carbon atom having a number of 2 to 3 Å, a (4) or unsubstituted direct bond, a branched or cyclic chain having 2 to 1 ring of an alkenyloxy group, substituted or unsubstituted. a linear, branched or cyclic alkenylthio group having 2 to 3 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted carbon atom number of 7 to 30 Aralkyloxy, substituted or unsubstituted aralkylthio group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 2 carbon atoms, substituted or unsubstituted carbon atom number 6~ 20 aryloxy, substituted or unsubstituted arylthio group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 2 to 30 carbon atoms, cyano group, formyl group, , _c〇〇Rie group (alkyl group having a carbon atom number of 1 to 30 in the ring) substituted or unsubstituted direct bond branch or cyclic alkenyl group having 2 to 30 carbon atoms, substituted μ 琛Unsubstituted aralkyl group having 7 to 30 carbon atoms, or substituted or unsubstituted 7 ^ | <fine atom number 6 to -49- 1 aryl group), -c〇R2e group (based, R2e Hydrogen hydrazine; w 4 atom, substituted or unsubstituted 200911731 substituted straight chain, branched or cyclic, 1 to 30 carbon atom, substituted or unsubstituted linear, branched or cyclic carbon atom 2~ An alkenyl group of 30, a substituted or unsubstituted aralkyl group having 7 to 3 Å of a carbon atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or an amine group, and a 〇COR3e group. , 1136 is a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkene having 2 to 30 carbon atoms. a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and further, a radical of the adjacent group and each of X1 to X52 Groups bonded to each other, may form a substituted or unsubstituted ring of carbon. Such a fluoranthene derivative can be exemplified by the following. -50- 200911731

-51 - 200911731

-52- 200911731

-53- 200911731

-54- 200911731

-55 200911731

-56- 200911731

-57- 200911731

S CO

-58- 200911731

-59- 200911731

-60- 200911731

-61 200911731

sTl·CNJokl· 62 -62 - 200911731

-63- 200911731

7 τ ι CM

00 τ ι CNJ

•64- 200911731

-65 - 200911731

-66- 200911731

-67- 200911731

In the present invention, the fluorescent dopant may be represented by the following formula (3 1 ). -68- (31) (31)200911731

In the above formula (31), A and A' represent an independentazine ring system corresponding to a 6-member aromatic ring containing one or more nitrogens.

Xa&amp;Xb represents independently selected substituents, and the two bonds may form a condensed ring for A or A', and m and η each independently represent 0 to 4,

Za and Zb are independently selected substituents, and 2, 3, 4, 1', 2', 3' and 4' are each a carbon atom or a nitrogen atom, and are independently selected. The azine ring is represented by 1, 2, 3, 4, 1, 2, 3, and 4, all of which are carbon atoms, and m and η are 2 or more, and Xa and χ*&gt; indicate formation of an aromatic ring. Preferably, a quinoline ring or an isoquinoline ring having two or more carbon substituents bonded thereto is preferred. Preferably, za and Zb are fluorine atoms. In a preferred embodiment, the two fused ring systems are quinoline or isoquineline, the aryl or heteroaryl substituent is phenyl, and at least two Xa groups and two bonds forming a 6-6 condensed ring are present. Xb-based, condensed ring systems are each condensed in the 1-2 position, the 3-4 position, the I'-2' position or the 3,-4' position, and one or both of the condensation rings are substituted by a phenyl group, and can be exemplified A fluorescent dopant such as represented by the following formula (91), (92) or (93). -69- • · · (91) 200911731 xe

Xh xh xh • (92) (93) In the above formulae (91) to (93), each of Xc, Xd, and Xe is hydrogen or an independently selected substituent, but one of them is an aryl group. The azine ring is 2, 3, 4, 1, 2, 3, and 4, and η is 2 or more, and Xa and Xb are expressed in order to form a fragrance! More than one carbon substituent, and one is an aryl group or a substituted aryl group xf, xg and xh must be an aryl group or a heteroatom carbon atom, a m-quinone ring-bonded 2-base quinoline ring or -70-200911731 isoquine A porphyrin ring is preferred. Preferably, za and zb are fluorine atoms. Hereinafter, a boron compound which is decomposed by two ring nitrogens which are deprotonated bis(azinyl)amine ligands, wherein the two ring nitrogens are different 6,6 condensed ring systems, the at least one As a part of those containing an aryl or heteroaryl substituent, in the present invention, a useful boron compound is exemplified.

-71 - 200911731 Dopant, can be used for phosphorescence. Specific examples of the light-sensitive 35 dopants, for example, PQIr (iridium (III) bis (2-phenyl quinolyl-N, C2) acetylacetonate), and the like can be exemplified as the following compounds.

• N,

-72- 200911731

-73- 200911731

i"(ppy)3

-74 - 200911731

(The hole injection/transport layer (hole transport area)) The hole injection/transport layer is a layer that facilitates injection into the hole of the light-emitting layer and transports the light-emitting region. The hole mobility is large, and the ionization energy is usually small. 75- 200911731 to 5 · 5 e V or less. Such a hole injection/transport layer is preferably a material that transports holes to the light-emitting layer at a lower electric field strength, and further mobility of the hole is, for example, at least 10 to 4 cm 2 /Vs when an electric field of 104 to 106 V/cm is applied. It is better. Such a material for forming a hole injection layer or a hole transport layer, specifically, for example, a triazole derivative (refer to the specification of U.S. Patent No. 3,1,12,197, etc.), an oxadiazole derivative (US Patent No. 3,1,89,447) (For reference), an imidazole derivative (for reference), a polyarylalkane derivative (U.S. Patent No. 3,6,5,042, the same as No. 3,8 2, No. 9 8-9, the same as No. 3, 5 42, 5 44, Japanese Patent Publication No. 45-55 5, the same as 5 1 - 1 0 9 8 3, and JP-A-5-93224 Japanese Patent Publication No. 55-17105, Japanese Patent Publication No. 56-4148, No. 55-108667, the same as the Japanese Patent Publication No. 5-5-35656, and the like. And a pyrazolone derivative (U.S. Patent No. 3,180,729, the specification of which is the same as the specification of No. 4,278,746, the Japanese Patent Publication No. 5-5-8 8064, the same as No. 55-88065, the same as No. 49-105537, the same Japanese Patent Publication No. 55-51086, the same as 5-6-8 00 5 1 , the same as 5-6-8 141, the same as 57-45545, the same as 54-112637, the same 55 -74546, etc., as a reference), a phenylene diamine derivative (U.S. Patent No. 3,6,5,404, Japanese Patent Publication No. 51-10105, the same as No. 46-3 7 1 2, the same as 47-25336 An arylamine derivative (U.S. Patent No. 3,5 67,45 0), the disclosure of which is incorporated herein by reference. , with the 3rd, 180th, 7th and 3rd instructions, the same as the 3rd, 240th, 597th, the same as the 3rd, 658, 520, the 4th, 232, 103, the 4th, 175, 961, the same -76-200911731 4, 012, 376, the special public 49 -35702, Japanese Patent Publication No. 39-27577, Japanese Patent Application Laid-Open No. Hei 55-144250, No. 56-119132, No. 56-22437, No. 1,11, No. 518, etc. , amine-substituted chalcone derivatives (US Patent No. 3, 5 2, 5, 1 1 and the like), oxazole derivatives (disclosed in the specification of U.S. Patent No. 3, 25, 203, etc.), benzene Vinyl hydrazine derivative (Japanese Patent Laid-Open No. Hei 5-6-46234, etc.) (Japanese Patent Laid-Open No. Sho 54-110837, etc.) and anthracene derivatives (U.S. Patent No. 3,7,7,4,6, 2, and JP-A-54-59 1 43, the same as 5 5 - 5 Japanese Patent Publication No. 2-6, No. 5-5-5, No. 55-46760, Japanese Patent Publication No. 55-85495, Japanese Patent Publication No. 57-1135, and Japanese Patent Publication No. 5-7-148749 Japanese Laid-Open Patent Publication No. Hei No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. Nos. Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. 60-. - 1 74749, the same as the reference of 60- 1 75052, etc.), a decazane derivative (U.S. Patent No. 4,900,900), and a polydecane system (Japanese Patent Laid-Open No. 2-204996) Japanese Laid-Open Patent Publication No. Hei. The material of the hole injection layer or the hole transport layer may be a porphyrin compound (except as disclosed in JP-A-63-295 69 5), an aromatic tertiary amine compound, and the like. Styrylamine compound (U.S. Patent No. 4,127,412, Japanese Patent Application Laid-Open No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. -64299, the same as 55-79450, the same as 5 5 - 1 4425 0, the same as 5 6 - 1 1 9 1 3 2, the same as 6 1 - 2 9 5 5 5 8 1 - 9 8 3 5 No. 3, the same as the Japanese Patent Publication No. 63-29W95, etc.), an aromatic tertiary amine compound. Further, as described in U.S. Patent No. 5,06,5,69, there are two condensed aromatic rings in the molecule, such as 4,4'-bis(N-(l-naphthyl)-N-phenylamine). The triphenylamine unit described in the phenyl group and the special opening 4-3 0 8 6 8 8 is connected to 3 starburst type 4,4',4&quot;-tris(N-(3-methylbenzene) Base) -N-phenylamine) triphenylamine or the like. Further, the hexaazatriphenylene derivative described in Patent Publication No. 3614405, No. 3571977 or U.S. Patent No. 4,78 0,5 3 6 can also be suitably used as a material for hole injection. Further, in addition to the above-described aromatic secondary methyl compound as the material of the light-emitting layer, an inorganic compound such as p-type Si or p-type SiC may be used as the material of the hole injection layer or the hole transport layer. The hole injection layer or the hole transport layer may be formed of one or more of the above materials, and may also be a compound in which the hole injection layer or the hole transport layer is a different kind of compound. The layer is injected by the hole injection layer or the hole transport layer. The film thickness of the hole injection layer or the hole transport layer is not particularly limited, but is preferably 20 to 200 nm. (Organic semiconductor layer) The organic semiconductor layer is preferably a layer which contributes to hole injection or electron injection to the light-emitting layer, and has a conductivity of 10-1 GS/cm or more. As the material of the organic semiconductor layer, a conductive oligomer containing an arylamine oligomer or the like described in Japanese Laid-Open Patent Publication No. Hei 8-193191-78-200911731 can be used. Conductive dendrimers such as molecules. The film thickness of the organic semiconductor layer is not particularly limited, but is preferably 〜1, 〇〇〇nm. (Electron injection/transport layer (electron transporting region)) An electron injecting layer or an electron transporting layer or the like may be provided as the second organic layer between the cathode and the yellow to red light emitting layer. The electron injecting layer or the electron transporting layer is a layer that assists electron injection into the light emitting layer, and the electron mobility is large. The electron injection layer is provided to adjust the energy level in order to alleviate the rapid change of the energy level. The material used for the electron injecting layer or the electron transporting layer is preferably a metal complex of 8-hydroxyquinoline or a derivative thereof, an oxadiazole derivative or a nitrogen-containing heterocyclic derivative. As a specific example of the metal complex of the above 8-hydroxyquinoline or a derivative thereof, a metal chelate compound containing a chelating compound of 〇XINE (normally 8-quinolinol or 8-hydroxyquinoline) can be used. ο X i η 〇 id compound, for example, tris(8-salofolinium)aluminum. Next, the oxadiazole derivative may, for example, be an electron transporting compound represented by the following general formula.

Ar23 —〇— Ar24

-79- 200911731 Where, Ar17, Ar18,

Ar

Ar2 i aryl with or without a substituent, Ar1 2 5

Ar22 and Ar23 may be identical or different from each other. a 2| , Ar 〃 and represent each 螂 Ar 18 , Ar 19 and Ar 21 , from an extended aryl group with or without a substituent, or different.

Ar23 and Ar24 indicate each

Ar23 and Ar24 may be mutually the same as the aryl group in the above formula, and examples thereof include a phenyl group, a biphenyl group, a fluorenyl group, a fluorenyl group, a benzyl group, and the like. Further, the aryl group may, for example, be a benzoinyl group, a naphthalene group, a biphenylene group, an anthracene group, an anthracene group or an anthracene group. Next, the substituent '' may, for example, be an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a cyano group. The electron transporting compound is preferably one which is excellent in film formability. Next, specific examples of such electron-transporting compounds include the following.

200911731 &amp;Organization of general formula 〇 ΥGeneral formula of organic compound For example, including (1 0 1). The nitrogen-containing heterocyclic derivative may, for example, be a nitrogen-containing and nitrogen-containing heterocyclic derivative of a metal complex which is not a compound, and may be exemplified by a nitrogen-containing metal complex. Compound. The 5-member ring or the 6-member ring of the skeleton or the formula (1〇2)

* * * (101)

Guang, X-Ζ1 I,,, N

?2 · · · (102) where X is a carbon atom or a nitrogen atom. 21 and 22 are each independent, indicating that a group of atoms containing a nitrogen-containing hetero ring can be formed. N · · · (103) It is preferably a nitrogen-containing aromatic polycyclic group having a 5-membered ring or a 6-membered ring, and a plurality of nitrogen atoms are present in the case of having an organic compound having a skeleton at a non-adjacent bonding site. Further, the case of a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms is a bone-81*200911731 having a combination of the above (1()1) and (1〇2) or (101) and (103) A nitrogen-containing aromatic polycyclic organic compound. The nitrogen-containing group (HAr) of the nitrogen-containing organic compound is a nitrogen-containing heterocyclic derivative selected from the nitrogen-containing heterocyclic group represented by the following general formula.

-82- 200911731 In the above formula, R is an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 4 carbon atoms, an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms, n For an integer of 〇~5, when η is an integer of 2 or more, the plural numbers R may be the same or different from each other. Further, a preferred specific compound is a nitrogen-containing heterocyclic derivative represented by the following general formula. HAr—L1 Ar1-Ar2 In the above formula, HAr is a nitrogen-containing heterocyclic group having 3 to 40 carbon atoms which may have a substituent, and L is a single bond, and may have a substituent having a carbon number of 6 to 4 Å. a heterocyclic aryl group having a carbon number of 3 to 40 having a substituent, Ar1 being a divalent aromatic hydrocarbon group having 6 to 40 carbon atoms which may have a substituent, and Ar2 being a carboxyl group having 6 to 40 carbon atoms which may have a substituent Or a heteroaryl group having a carbon number of 3 to 40 which may have a substituent, and HA r is a nitrogen-containing heterocyclic derivative selected from the group formed by the following: -83- 200911731

L is a nitrogen-containing heterocyclic derivative selected from the group formed below.

Ar2 is a nitrogen-containing heterocyclic derivative selected from the group formed below. -84- 200911731

Ar1 is a nitrogen-containing heterocyclic derivative having an arylsulfonyl group represented by the following

In the above formula, R1 to R14 are each independently and represent a hydrogen atom, a halogen atom, a group having 1 to 20 carbon atoms, a oxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, and may have a substituent. The aryl group having 6 to 40 carbon atoms or the heteroaryl group having 3 to 40 carbon atoms, and Ar3 is an aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent.

In Ar1, all of R1 to R8 are nitrogen-containing heterocyclic derivatives of a hydrogen atom. The nitrogen-containing heterocyclic derivative represented by the following formula is also suitable as an electron injecting (transporting) material. -85- 200911731

• (1A)

(1B) In the above formula, A1 to A3 are a nitrogen atom or a carbon atom, R is an aryl group having 6 to 60 carbon atoms, a carbon number which may have a substituent, an aryl group, and an alkyl group having 1 to 20 carbon atoms. The base, the alkoxy group of the haloalkyl group having 1 to 20 carbon atoms, η is an integer of 〇~5', and R, which is an integer of 2 or more, may be the same or different from each other. Further, the adjacent plural R groups may be bonded to each other to form an unsubstituted carbocyclic aliphatic ring, or a substituted or unsubstituted aromatic ring.

Ar1 is an optionally substituted aryl group having 6 to 60 carbon atoms, a heteroaryl group having 3 to 60 carbon atoms, and a hydrogen atom, a carbon number of 1 group, and a haloalkyl group having 1 to 20 carbon atoms. An alkoxy group having 1 to 20 carbon atoms; an aryl group having 6 to 60 carbon atoms; and a carbon number which may have a substituent: an aryl group. However, any of Ar1 and Ar2 may be a condensed cyclic group of 60 which may have a substituent, and a carbon number of 3 to 60 which may have a substituent may have a heteropoly number of 1 to 60, and a plural number is substituted. Or a carbocyclic aromatic having a substituted ～0 0 alkane may have a heterocarbon number of from ～60 to 10 condensed cyclic group -86- 200911731 L, each of L2 is a single bond, and may have a substituent having a carbon number of 6 to 60. a condensed ring, a heterocondensed ring having a carbon number of 3 to 60 which may have a substituent or a fluorenyl group which may have a substituent. HAr——L1-Ar1-Ar2 In the above formula, H Ar is a nitrogen-containing anthracene ring having a carbon number of 3 to 40 which may have a substituent, and L1 is a single bond, and the carbon number which may have a substituent is 6 to 6 Å. a heterocyclic aryl group having 3 to 60 carbon atoms which may have a substituent or a substituent which may have a substituent 'Ar1 is a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, and Ar is a An aryl group having 6 to 6 carbon atoms having a substituent or a heteroaryl group having 3 to 60 carbon atoms which may have a substituent. Further, the following indole cyclopentadiene derivative is also suitable for electron injecting (transporting) materials.

a hydrocarbon group of the formula, X and Y,

, 乂 and ¥ are each independently, a saturated or unsaturated hydrocarbon group having a carbon number of 66-6, an alkoxy group, an alkenyloxy group, an alkynyloxy group or an unsubstituted aryl group, substituted or unsubstituted. The structure of a heterocyclic ring or a saturated or unsaturated ring. , hydroxy, substituted χ and Υ bond

Ri~R4 are each independently hydrogen, halogen, substituted or unsubstituted carbon number 1-87-200911731. Courtyl, alkoxy, aryloxy, perfluoroalkyl, perfluoroalkoxy, amine, hospital Preference group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, fluorenyl fluorenyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxylcyloxy group, sub Sulfonyl, sulfonyl, sulfanyl, formyl, amidyl, aryl, heterocyclic, alkenyl, alkynyl, nitro, formic, nitroso, methyloxy, An isocyano group, a cyanate group, an isocyanato group, a thiocyanate group, an isothiocyanate group or a cyano group or a structure in which a ring which is substituted or unsubstituted in the case of contiguous is condensed. However, when 1^1 and r4 are a phenyl group, X and Y are not an alkyl group, and when phenyl 'R and R4 are a thienyl group, X and γ are not simultaneously satisfying a monovalent hydrocarbon group, and R2 and R3 are an alkyl group. The structure of an aryl group, an alkenyl group or an aliphatic group in which 112 and r3 are bonded to form a ring, and when the rule 4 is a formyl group, R2, R3, X and Y are each independently, and are not a hydrocarbon group having 1 to 6 carbon atoms. Or a hydrogen atom 'in the structure of the condensation of the 1 and R 2 benzene rings, X and Y are not an alkyl group and a phenyl group. The borane derivative represented by the subtype is also suitable for electron injection (transport)

Wherein ' and Z2 are each independently and represent a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amine group, a substituted boron (-88-200911731 alkyl) group, an alkoxy group or an aryloxy group, \, 丫 and Z! are each independently, indicating a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, an alkoxy group or an aryloxy group, and 2, and the substituents of Z2 may be bonded to each other to form a condensation. In the ring, η is an integer of 1 to 3'. When η is 2 or more, Ζι Ζ 2 can be different from each other. However, the case where η is 1, Χ, γ, and R2 is a methyl group, and R8 is a hydrogen atom or a substituted boron (alkyl) group, and η is 3, and Z is a methyl group. The gallium complex represented by the sub-type is also suitable for electron injection (transport)

Ga—L Q2 y is independent of each other, and represents a group represented by the following formula: y Α Α Π丨 Π丨 虻 1H, L represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or uncycloalkyl group, a substitution Or not ribbed you + ^ ^ ^, _0Rl (Rl is a ruthenium of t, a substituted or unsubstituted heterocyclic group', a sulfonium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted naphthenic The base, the substituted gentleman replaces the 2 unsubstituted base), or the "substituted aryl group". (QS Q4 and Ql and (4) have the same meanings as the residue represented by the formula, although w 2-methyl-8-hydroxyquino is not a residue of 8-hydroxyl temple, but is not limited to such A '1 , \ ' N—

-89- 200911731 Rings A1 and A2 are mutually substituted or unsubstituted aryl ring or heterocyclic structures. The above metal complex has high properties as an n-type semiconductor and has a large electron injecting ability. Further, the energy generated by the formation of the complex compound is also low, and the bond between the metal of the formed metal complex and the ligand is also strengthened, and the fluorescence quantum efficiency as the light-emitting material also becomes large. Here, specific examples of the substituent of the ring Α1 and Α2 forming the ligand of the above formula include, for example, a halogen atom of a chlorine, a bromine, an iodine or a fluorine, a methyl group, an ethyl group, a propyl group, a butyl group, and a sec- Substituted or unsubstituted alkyl, phenyl, naphthyl, 3-methylphenyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, stearic acid, trichloromethyl, etc. a substituted or unsubstituted aryl group of 3-methoxyphenyl, 3-fluorophenyl '3-trichloromethylphenyl, 3-trifluoromethylphenyl, 3-nitrophenyl, etc. Oxy, η-butoxy, tert. butoxy, dichloromethoxy, trifluoroethoxy, pentafluoropropoxy, 2,2,3,3·tetrafluoropropoxy, 1,1 a substituted or unsubstituted alkoxy group, a phenoxy group, a nitrophenoxy group, a 1,3,3,3-hexafluoro-2-propoxy '6-(perfluoroethyl)hexyloxy group, etc. P_tert • substituted or unsubstituted aryloxy group, methylthio group, ethylthio group, such as butylphenoxy, 3-fluorophenoxy, pentafluorophenyl, 3-trifluoromethylphenoxy, etc. Substituted or unsubstituted alkylthio, phenylsulfide, tert-butylthio, hexylthio, octylthio, dimethylthio Substituted or unsubstituted, p-nitrophenylthio, p_tert_butylphenylthio, 3-fluorophenylthio, pentafluorophenylthio, 3-difluoromethylphenylthio, etc. Square thio, cyano, nitro, amine, methylamino, diethylamino, ethylamino, dimethylamino, dipropylamino, dibutylamino, diphenyl Mono- or monosubstituted amines of the amino group, etc. -90 - 200911731, bis(ethyloxymethyl)amino, bis(ethyloxyethyl)amino, bisethoxypropyl propyl) a mercaptoamine group, a hydroxy group, a decyloxy group, a decyl group, a methylamine carbaryl group, a dimethylamine carbhydryl group, an ethylamine carbhydryl group, a bis(acetoxybutyl)amino group, or the like. Aminomercapto, carboxylic acid, sulfonic acid, imido, cyclopentane, etc. of diethylamine, mercaptomethyl, propylamine, mercaptomethyl, phenylamine, mercapto or the like a cyclyl group such as a cycloalkyl group, a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a phenanthryl group, a fluorenyl group or a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or the like. Triazinyl, porphyrinyl, sialolinyl, acridinyl, pyrrolidinyl, Azyl, piperidinyl, morpholinyl, piperazinyl, oxazolyl, furyl, thiophenyl, oxazolinyl, oxadiazolyl, benzoxazolinyl, thiazolyl, thiadiazolyl a heterocyclic group such as a benzothiazolyl group, a triazolyl group, an imidazolyl group or a benzimidazolyl group. Further, the above substituents may be bonded to each other to form a 6-membered aryl ring or a heterocyclic ring. Further, in the following description of JP-A-9-3448, an organic compound which satisfies the above constitutional conditions can be exemplified. R! X2

Wherein X, R, R4 are each independently 'existing a hydrogen atom, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic cyclic group, a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted group The heterocyclic group, Χι, X: represents an oxygen atom, a sulfur atom or a dicyanomethylene group. The carbon-cyclic aromatic ring group is replaced by an organic compound which satisfies the above-described constitutional conditions, for example, as described in JP-A-2000-172-200911731.

However, in the above general formula, Ri, R2, R3 and R4 are the same or different groups, and are aryl groups represented by the following general formula.

However, in the above general formula, 'R5' R6, R7, uldent 8 and r9 are the same or different groups, and are a hydrogen atom, or at least one of them, a saturated or unsaturated alkoxy group, an alkyl group, an amine. Base or alkylamine group. Further, it may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative. The film thickness of the electron injecting layer or the electron transporting layer is not particularly limited, but is preferably 1 to 1 0 0 nm. The organic layer closest to the anode, i.e., the first luminescent layer or the first organic layer, preferably contains an oxidizing agent. The oxidizing agent suitable for the first luminescent layer or the first organic layer is an electron attracting or electron accepting body. Preferred are Lewis acid, various -92-200911731 anthracene derivatives, dicyandiimethane derivatives, salts of aromatic amines and Lewis acids. Particularly good Lewis acids are ferric chloride, barium chloride, aluminum chloride and the like. The organic layer closest to the cathode, i.e., the luminescent layer or the second organic layer, preferably contains a reducing agent. Preferred reducing agents are alkali metals, alkaline earth metals, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, alkali metals and aromatic compounds. The complex formed. Particularly preferred alkali metals are C s, L i, N a, K. A preferred form of the organic EL element is an element having a reducing dopant in the field of transporting electrons or the interface between the cathode and the organic layer. Here, the reducing dopant is defined as a substance which can reduce the electron transporting compound. And 'for a certain reduction, you can use various substances, such as alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth. a metal halide, a rare earth metal oxide or a rare earth metal halide, an alkali metal organic complex, an alkaline earth metal organic complex, and an organic complex of a rare earth metal Choose one of the lesser substances. Further, more specifically, preferred reductive dopants include, for example, L i (work function: 2-9 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), and Rb (work function: 2.16). At least one alkali metal selected from the group formed by eV) and Cs (work function: l_95eV), or Ca (work function · 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work) Function: 2.52 eV) At least one alkaline earth metal selected from the group formed, and the work function is particularly preferably 2.9 eV or less. Among these, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, R b -93- 200911731 and Cs, and more preferably Rb or Cs' is Cs. These alkali metals are particularly high in reducing ability, and a small amount of addition to the electron injecting region can achieve an increase in luminance or a long life of the organic EL element. Further, a reducing dopant having a work function of 2.9 eV or less may be a combination of two or more kinds of alkali metals, particularly a combination of Cs, for example, Cs and Na, Cs and K, Cs and Rb or Cs. It is better to combine with N a and K. By using a combination of C s , the reduction ability can be effectively achieved. By adding the electron injection region, the luminance of the organic EL element can be improved or the lifetime can be extended. An electron injecting layer composed of an insulator or a semiconductor may be further disposed between the cathode and the organic layer. At this time, current leakage can be effectively prevented and electron injectability can be improved. As the insulator, at least one metal compound selected from the group consisting of an alkali metal chalcogenide, an alkaline earth metal chalcogenide, an alkali metal halide, and an alkaline earth metal halide is preferably used. The electron injecting layer is preferably composed of an alkali metal chalcogenide or the like, and can further improve electron injectability. Specifically, preferred alkali metal chalcogenides are, for example, Li2, K20, Na2S, Na2Se and Na20, preferably soil-like metal chalcogenides such as CaO, BaO, SrO, BeO, BaS, and CaSe. Further, preferred halides of alkali metals are, for example, LiF, NaF, KF, LiCl, KC1 and NaCl. Further, a preferred halide of an alkaline earth metal, for example, a fluoride of C a F 2, B a F 2, S r F 2, M g F 2 and B e F 2 , or a halide other than a fluoride. Further, the semiconductor constituting the electron transport layer may include Ba, Ca, Sr, Yb, A1, Ga, Iη, Li, Na, Cd, Mg, S i, Ta, Sb, and -94-200911731.

One or a combination of two or more kinds of oxides, nitrides, or oxynitrides of at least one element of Zn. Further, the inorganic compound constituting the electron transport layer is preferably a microcrystalline or amorphous insulating film. When the electron transport layer is formed of such an insulating film, a more uniform film can be formed, and pixel defects such as dark spots (DARK SPOT) can be reduced. Further, examples of the inorganic compound include the above-mentioned alkali metal chalcogenide, alkaline earth metal chalcogenide, alkali metal halide, and alkaline earth metal halide. (Cathode) Cathode, in order to inject electrons into the electron injecting/transporting layer or the light-emitting layer, a metal having a small work function (4 e V or less), an alloy, an electrically conductive compound, or a mixture thereof may be used as the electrode material. Specific examples of the electrode material include sodium, sodium potassium alloy, magnesium, lithium, magnesium, silver alloy, aluminum oxide, aluminum lithium alloy, indium, and rare earth metal. This cathode can be produced by forming such a thin film by vapor deposition, sputtering or the like. Here, when the light emitted from the light-emitting layer is taken out from the cathode, the transmittance to the cathode is preferably greater than 10%. Further, the film resistance of the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually from 10 nm to Ι μηι, preferably from 50 to 200 nm. (Insulating Layer) Since the organic EL element has an electric field applied to the ultrathin film, it is liable to cause pixel defects due to leakage or short circuit. In order to prevent this, it is preferable to insert a rim-95-200911731 edge film layer between a pair of electrodes. Materials used for the insulating layer, such as alumina, lithium fluoride, lithium oxide, barium fluoride, barium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, barium oxide, barium oxide , tantalum nitride, boron nitride, molybdenum oxide, antimony oxide, vanadium oxide, and the like. Mixtures or laminates of these may also be used. [Manufacturing Method of Organic EL Element] Next, a method of manufacturing the organic EL element will be described. By the materials and the formation methods exemplified above, an anode, a light-emitting layer, a necessary hole injection layer, and an electron injection layer necessary for the formation of the cathode are used to form an organic EL element. Further, an organic EL element can be fabricated from the cathode to the anode or in the reverse order of the foregoing. In the following, an example of the production of an organic EL device having a structure in which an anode/hole injection layer/light-emitting layer/electron injection layer/cathode is sequentially disposed on a light-transmitting substrate is described. First, an anode is formed by vapor deposition or sputtering on a suitable light-transmissive substrate so that the film formed of the anode material has a film thickness of Ιμηη or less, preferably 10 to 200 nm. A hole injection layer is then provided on the anode. The formation of the electrodeposited layer can be carried out by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. A film thickness of 5 nm to 5 μM is preferably selected. Then, the formation of the light-emitting layer on the hole injection layer can be performed by a wet process such as a dry process or a spin coating method or a casting method represented by a vacuum evaporation method using an organic light-emitting material desired by -96-200911731. The organic light-emitting material is formed by thinning. Next, an electron injecting layer is provided on the light emitting layer. The formation by vacuum evaporation is taken as an example. Finally, the organic EL element can be obtained by laminating the cathode. The cathode is made of a metal, and a vapor deposition method or sputtering can be used. However, in order to protect the underlying organic layer from damage during film formation, vacuum evaporation is preferred. The method of forming each layer of the organic EL element is not particularly limited. A conventionally known method of forming a vacuum deposition method, a spin coating method, or the like, that is, the organic thin film layer can be impregnated by a vacuum deposition method, a molecular vapor deposition method (MB E method), or a solution dissolved in a solvent. A known method such as a coating method such as a method, a spin coating method, a casting method, a bar coating method, a roll coating method, or an inkjet method is used. The film thickness of each organic layer of the organic EL element is not particularly limited. Generally, when the film thickness is too small, defects such as pinholes are likely to occur, and if it is too thick, a high applied voltage is required, and efficiency is deteriorated. A range of several nm ~ Ι μιη is preferred. Further, when a DC voltage is applied to the organic EL element, light is observed by applying a voltage of 5 to 40 V with the anode being + and the cathode being -. Moreover, even if the voltage is applied in the opposite polarity, no current flows, and no light is emitted at all. When the AC voltage is further applied, uniform light emission is observed only when the anode is + and the cathode is -. The waveform of the external communication can be arbitrary. -97 - 200911731 [Embodiment] [Embodiment] The following describes an embodiment of the present invention. [Synthesis of Compound] First, the synthesis of the compound used in the preparation of the sample of the example was described. (1) Synthesis of Compound 1 The synthesis of Compound 1 was carried out in accordance with the following scheme.

NBS DMF

Toluene

(1-1) Synthesis of 6-bromine crater A solution of 17.8 g (100 mmol) of N-bromosuccinimide in DMF1L solution of 22.8 g (100 mmol) was stirred and stirred at room temperature for 20 hours. After completion of the reaction, the reaction solution was added to 2 L of water, and the crystals of -98 to 200911731 were collected by filtration. The obtained solid was washed with water, methanol and hexane, and dried under reduced pressure to give 6 - bromine 2 8.5 g (yield 93%). (1-2) 6-(2-naphthyl) crater in the argon environment, 6.14g (20.0mm〇l) at 6-bromine, 2.10g (24.0mmol) of 2-naphthaleneboronic acid, tetrakis(triphenyl) Palladium (0) 0.462 g (0.400 mmol) 40 mL of DME and 2 mL of a 2M aqueous sodium carbonate solution were added, and the mixture was heated under reflux for 16 hours. After completion of the reaction, precipitated crystals were collected by filtration, and the obtained crystals were washed with water, methanol and hexane. The obtained solid was recrystallized from toluene to give 4-(2-naphthyl)® 4.25 g (yield: 60%). (1-3) Synthesis of 6-bromo-12-(2-naphthyl) Grottoes In a solution of 4.25 g (12.0 mmol) of DMF 100 mL of 6-bromine broth, N-bromoammonium imine 2.56 g (14.4 mm 〇l) was added. The DMF 10 mL solution was stirred at room temperature for 20 hours. After completion of the reaction, the reaction solution was added to 200 ml of water, and the precipitated crystals were filtered. The obtained solid was washed with water, methanol and hexane, and dried under reduced pressure to give 6.68 g (yield: 90%) (1 - 4 ) compound of 6-bromo-12-(2-naphthyl). In a synthetic argon atmosphere, 4.33g (10_0mmol) at 6-bromo-12-(2-naphthyl), 2.06g (12_0mmol) of 1-naphthaleneboronic acid, tetrakis(triphenylphosphine)palladium(〇)〇.231g (0.200 mmol) DME 40 mL, 2M sodium carbonate aqueous solution 20 mL 'in-99-200911731 was added and heated under reflux for 16 hours. After the completion of the reaction, the precipitated crystals were collected by filtration, and the obtained crystals were washed with water, methanol and hexane. The obtained solid was recrystallized from toluene to obtain 2.8 g of white crystals. The result of mass spectrometry was found to be the target 'm/e = 480 for molecular weight 480.19. (2) Synthesis of Compound 2 The synthesis of Compound 2 was carried out in accordance with the following scheme.

NBS -- DMF

Toluene

(2-1) Synthesis of 2-(4-bromophenyl)naphthalene in argon atmosphere, 4-bromoiodobenzene (WOgUdlmol), 2-naphthaleneboronic acid 243g (1.41 mol), tetrakis(triphenylphosphine)palladium (〇) 32.7 g (28.2 mmol), 3.2 L of toluene and 3.2 L of a 2 M sodium carbonate aqueous solution were added, and the mixture was heated and refluxed for 17 hours. After completion of the reaction, the mixture was filtered and the aqueous layer was removed. The organic layer was washed with water and dried over magnesium sulfate. The residue was purified by column chromatography on silica gel - 100 - 200911731 to give 2-(4-bromophenyl)naphthalene 3 0 3 g (yield 76%). (2-2) Synthesis of 4-(2-naphthyl)phenylboronic acid in an argon atmosphere, adding 212 g (748 mol) of 2-(4-bromophenyl)naphthalene to anhydrous THF, stirring at -10 °C 600 mL (948 mmol) of a 1.6 M η-butyllithium hexane solution was added. The reaction solution was stirred while stirring to 〇 ° C for 2 hours. The reaction solution was further cooled to -78 ° C, and 450 g (2.39 mol) of triisopropyl borate was added dropwise. The reaction solution was stirred at room temperature for 17 hours. 500 mL of water and 3 L of toluene were added, and after stirring for 1 hour, the aqueous layer was removed. The organic layer was dried over magnesium sulfate, and the solvent was evaporated. The obtained solid was washed with hexane to obtain 4-(2-naphthyl)phenylboronic acid I26 g (yield: 67%). (2-3) Synthesis of Compound 2 In the synthesis of Compound 1, a substituted naphthalene boronic acid was synthesized in the same manner using 4-(2-naphthyl)phenylboronic acid. This product was analyzed by mass spectrometry and found to be the target, with a molecular weight of 556.22 and a target of 〇 1 / 6 = 556. (3) Synthesis of Compound 3 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry and found to be the target. For molecular weight 556·22, m/e = 556. -101 - 200911731

Toluene

(4) Synthesis of Compound 4 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry to give the object, m/e = 556 for molecular weight 5 5 6.22.

(5) Synthesis of Compound 5 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. -102-200911731. This product was analyzed by mass spectrometry and was the target. For molecular weight 5 5 6.22, m/e = 556 o

(6) Synthesis of Compound 6 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by the following scheme. The result of mass spectrometry analysis is the target product, m/e=506° for the molecular weight of 5 0 6.2 0

-103- 200911731 (7) Synthesis of Compound 7 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by the following scheme. This product is analyzed by mass spectrometry and is the target. For the molecular weight of 5 0 6.2 0, m/e = 506o

NBS DMF

(8) Synthesis of Compound 8 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by the following scheme. This product was analyzed by mass spectrometry and found to be the object. For molecular weight 5 0 6.2 0 , m/e = 506. -104- 200911731

NBS DMF

Toluene (9) Synthesis of Compound 9 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by the following scheme. This product was analyzed by mass spectrometry and was the target. For molecular weight 5 3 0.2 0 , 111/6 = 530 0

Toluene

b(〇h)2

Synthesis of toluene (1 〇) Compound 1 〇 -105- 200911731 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by following the following scheme. This product was analyzed by mass spectrometry as the target, m/e = 556 for a molecular weight of 5 5 6.2 2 .

b(oh)2

Toluene

(1 1) Synthesis of Compound 1 1 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry to give the object, m/e = 556 for molecular weight 5 5 6.22.

NBS DMF

b(〇h)2

Toluene

Toluene -106- 200911731 (1 2 ) Synthesis of Compound 1 2 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry and was the target. For molecular weight 5 5 6.2 2 , m/e = 556 〇

b(oh)2

Toluene

Toluene (13) Synthesis of Compound 13 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry to give the object, m/e = 556 for molecular weight 5 5 6.22. -107- 200911731

B(OH)2

Toluene

Toluene (1 4 ) Synthesis of Compound 1 4 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by the following scheme. This product was analyzed by mass spectrometry and found to be the object. For molecular weight 5 0 6.2 0 , m/e = 506.

b(〇h)2

Toluene

Toluene (1 5 ) Synthesis of Compound 1 5 -108 - 200911731 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by following the following scheme. This product was analyzed by mass spectrometry and found to be the target. For the molecular weight of 5 0 6.2 0 , m/e 2 5 06.

B(OH)2

Toluene

_2bhO^Q -3 Pd(PPh3)4 Na2C03aq toluene

(1 6 ) Synthesis of Compound 16 The synthesis was carried out in the same manner as in the synthesis of Compound 1 by the following scheme. This product was analyzed by mass spectrometry and found to be the object. For molecular weight 5 0 6.2 0 , m/e = 506. -109- 200911731

NBS DMF

(17) Synthesis of Compound 17 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry as the target, m/e = 632 for a molecular weight of 6 3 2.2 5 .

(1 8 ) Synthesis of Compound 18 The synthesis was carried out in the same manner as in the synthesis of Compound 2 by the following scheme. This product was analyzed by mass spectrometry as the target, m/e = 632 for molecular weight 63 2.2 5 .

NBS DMF

Toluene (1 9) Synthesis of Compound 19 The synthesis of Compound 1 9 was carried out following the following scheme. 111 - 200911731

(Issopd 〇J1 ε(ά;!〇ω

(19-1) 2-bromo-6-phenylnaphthalene in the presence of argon, adding 6-bromo-2-naphthyltrifluoromethanesulfonate 1195 g (3.37 mol), 1,3-bis(diphenyl) Palladium (propane) palladium (0) dichloride

99.3 g (168 mmol) and dehydrated diethyl ether 4L were placed in a beaker and cooled to 0 ° C -112 - 200911731. A solution of 1 Μ phenyl magnesium bromide in THF (4.1 L) was added dropwise and stirred at room temperature for 22 hours. After adding 2 L of toluene and 2 L of water, it was filtered. After the organic layer of the filtrate was dried over magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was washed with toluene (s 1 u r r y w a s h i n g), and the crystals were collected by filtration. The crystals were dried under reduced pressure to give 2-bromo-6-phenylnaphthalene (yield: 8%). (19-2) Synthesis of 6-phenylnaphthalene-2-boronic acid Under the argon atmosphere, add 2-bromo-6-phenylnaphthalene 3 60 g (1-27 mol), dehydrated diethyl ether 2 L, dehydrated toluene 2 L, and cooled to - 10 ° C. 1 L (1.58 mol) of 1.58 M n-butyllithium in hexane was added dropwise, and stirred at -1 ° C for 5 hours. The reaction solution was cooled to -60 ° C, and 718 g (3.81 mol) of triisopropyl borate was added dropwise, followed by stirring at room temperature for 17 hours. 1 L of water and 1 L of toluene were added to the reaction solution, and the mixture was stirred for 1 hour, and then the aqueous layer was removed. The organic layer was washed with water and dried over magnesium sulfate. After concentrating the organic layer, it was washed with toluene to obtain 276 g of 6-phenylnaphthalene-2-boronic acid (yield: 87%). (19-3) Synthesis of 3-methylhydrazine_4_hydroxybiphenyl in argon, adding 496 g (2.46 mol) of 5-bromo salicylaldehyde, 361 g (2.96 mol) of phenylboric acid, and tetrakis(triphenylphosphine) Palladium (0) 57 g (49. 〇mniol), DME 8.6 L, sodium carbonate 784 g / water 3.7 L, heated under reflux for 17 hours, and stirred. After cooling to room temperature, 3 L of toluene was added to remove the aqueous layer. The organic layer was washed with water and dried over magnesium sulfate. The crystals were purified by silica gel column chromatography to give 382 g (yield: 78%) of 3-carbazin-4-hydroxybiphenyl. 200911731 (19-4) Synthesis of 3-methylindole-4-biphenyltrifluoromethanesulfonate in the argon atmosphere, adding 3-methylindole-4-hydroxybiphenyl 3 82g (1.93mol), diisopropyl 390 g (3.85 mol) of alkylamine, 4 L of dehydrated dichloromethane, and 88 g (3.85 mol) of anhydrous trifluoromethanesulfonic acid were added dropwise, and the mixture was stirred at room temperature for 21 hours. After adding sodium hydrogencarbonate 1 〇 〇 g / water 3 L, the aqueous layer was removed. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography toield of crude product of 6-carbazol-4-diphenyltrifluoromethanesulfonate (65 g). (19-5) 2-(3-Methylbiphenyl-4-yl)-6-phenylnaphthalene was synthesized under the argon atmosphere, and 3-butyrene-4-biphenyltrifluoromethanesulfonate 444g was added. (l.llmol), phenylboronic acid 276g (1.33mol), tetrakis(triphenylphosphine)palladium(0)26g (22.2mmo〇, toluene 5L, sodium carbonate 3 54g/water 1.7L, heated for 17 hours under reflux After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure and washed with toluene-acetone to give 2-(3-methylbiphenyl)- 4-yl)-6-phenylnaphthalene 3 70 g (yield 8 6%) ° (19-6) 2-[3-[(2-methoxy)vinyl-1-yl]biphenyl-4 Synthesis of -6-phenylnaphthalene under argon, adding (methoxymethyl)triphenylphosphonium chloride 823 g (2.40 mol), dehydrated diethyl ether 4L in a beaker, adding 1 M potassium- T-butoxy THF solution 2.4 L (2.40 mol), stirred at room temperature for 2 hours. Drop -114- 200911731

A THF 6L dispersion of 2-(3-methylbiphenyl-4-yl)-6-phenylnaphthalene 370 g (961 mm) was stirred at room temperature for 17 hours. After the reaction, the insoluble matter was concentrated to concentrate the filtrate. The residue was purified by silica gel column chromatography to give 2-[3·[(2-methoxy)vinyl-1-yl]biphenyl-4-yl]-6-phenylnaphthalene 3 3 0 g (received Rate 83%). Synthesis of (19-7) 2,8-diphenyl crater by adding 2-[3-[(2-methoxy)vinyl-1-yl]biphenyl-4-yl]-6-phenylnaphthalene 330 g (800 mmol), methanesulfonic acid 60 g (624 mmol), and dehydrated dichloromethane 4·5 L were stirred at room temperature for 18 hours. 1 L of methanol was added, and the precipitated crystals were taken. The obtained crystal was washed with methanol to obtain 2,8-diphenyl broth (40%) (yield 78%). (19-8) Synthesis of Compound 19 In the synthesis of Compound 1, the synthesis was carried out in the same manner as in the case of using 2,8-diphenyl crater. The mass spectrometry result of this material was 'target'. For molecular weight 63 2.25, 1114 = 63 2 . (20) Synthesis of Compound 20 The synthesis was carried out in the same manner as in the synthesis of Compound 3 by the following scheme. This product was analyzed by mass spectrometry and found to be the target. For molecular weight 70 8 · 2 8 , m/e = 708. -115- 200911731

(21) Synthesis of Compound 21 The synthesis of Compound 2 1 was carried out in accordance with the following scheme. -116 - 200911731 cslxoa.

Nnffl-u ί =\ro("d!o)a

Jg6s i—

=\addp)zopd

(21-1) Synthesis of 2-naphthyl-12-phenyl sulphate Following the above-mentioned scheme, the synthesis was carried out in the same manner as in the synthesis of the compound -19-117-200911731. (21-2) Synthesis of 6,12-dibromo-2-naphthyl-12-phenyl porphyrin in 2-naphthyl-12-phenyl crater 43.〇g (l〇〇mmol) in DMF1L solution was added to N - bromide amber imine 53.4 g (300 mmol) in DMF3 00 mL solution' was stirred at 60 ° C for 2 hours. After completion of the reaction, a reaction solution was added to 2 L of water, and the precipitated crystals were collected by filtration. The obtained solid was washed with water, methanol and hexane, and dried under reduced pressure to obtain 50.2 g (yield: 85%) of 6-bromo. (21-3) Synthesis of Compound 21 in an argon atmosphere at 6,12-dibromo-2-naphthalenyl-12-phenyl crater 5.88 g (l〇_〇mm〇l), 2-naphthalene boronic acid 4.12 g ( 24.0 mmol), tetrakis(triphenyl)palladium (〇)〇_462g (0.400 mmol), 8 mL of toluene and 4O mL of 2M sodium carbonate aqueous solution were added, and the mixture was refluxed for 16 hours. After the completion of the reaction, the crystal obtained by the filtration of the precipitated crystals was washed with water, methanol and hexane. The obtained solid was recrystallized from toluene to give white crystals 2.8 g. This product is the target of the '曰' analysis result. For the molecular weight of 682.27, m/e = 682 [composition of the phrase] Next, the composition of the sample is explained. (Example 1) A glass substrate (manufactured by Geomatec Co., Ltd.) having an IT〇 transparent electrode (anode) -118-200911731, which was attached to a thickness of 25 mm x 75 mm x 1.0 mm, was washed in isopropyl alcohol for 5 minutes after the first wave was washed. Wash with UV ozone for 30 minutes. The glass substrate with the transparent electrode wire after the cleaning is attached to the substrate holder of the vacuum vapor deposition apparatus, and the film thickness of 75 nm is formed by coating the transparent electrode on the surface on the side where the transparent electrode line is formed. Compound A-1. Further, on the A-1 film, the compound 1 of the present invention and the following compound D-1 were formed into a film having a thickness of 40 nm at a film thickness ratio of 40:2 to form a blue light-emitting layer. Compound 1 was used as a host material and D-1 was used as a dopant. On the film, Alq was deposited as a film having a thickness of 20 nm as the electron transport layer. Thereafter, LiF was formed into a film at a film thickness of 1 nm. On the LiF film, the metal A1 was vapor-deposited to 150 nm to form a metal cathode to form an organic EL device.

-119 - 200911731 (Example 2) In Example 1, an organic EL device was produced in the same manner by using Compound 2 instead of Compound 1. (Example 3) In Example 1, an organic EL device was produced in the same manner by using Compound 3 instead of Compound 1. (Example 4) In the example 1, the compound 1 was substituted, and the organic EL device was produced in the same manner using the compound 4. (Example 5) In Example 1, an organic EL device was produced in the same manner by using Compound 5 instead of Compound 1. (Example 6) In the example 1, the compound 1 was substituted, and the organic EL device was produced in the same manner using the compound 6. (Example 7) In the example 1, the compound 1 was substituted, and the organic EL device was produced in the same manner using the compound 7. -120-200911731 (Example 8) In Example 1, an organic EL device was produced in the same manner by using Compound 8 instead of Compound 1. (Example 9) In the example 1, the compound 1 was substituted, and the organic EL device was produced in the same manner using the compound 9. (Example 10) In the example 1, the compound 1 was substituted, and the organic EL device was produced in the same manner using the compound 1 oxime. (Example 1 1) In Example 1, an organic EL device was produced in the same manner by using the compound 1 1 instead of the compound 1. (Example 12) In Example 1, an organic EL device was produced in the same manner by using the compound i 2 instead of the compound 1 '. (Example 13) An organic EL device was produced in the same manner as in Example 1 by substituting the compound 1 '. -121 - 200911731 (Example 1 4) In Example 1, an organic EL device was produced in the same manner by using the compound 1 4 instead of the compound 1. (Example 15) In Example 1, an organic EL device was produced in the same manner as in the compound 1 except that the compound 1 was used. (Example 16) In Example 1, an organic EL device was produced in the same manner as in the compound 1 except that the compound 1 was used. (Example 17) In Example 1, an organic EL device was produced in the same manner as in the case of the compound 1 by using the compound 1 (Example 18). In the example 1, the compound 1 was used, and the compound 1 was used in the same manner. Organic EL element. (Example 19) In Example 1, an organic EL device was produced in the same manner as in the compound 1 except that the compound 1 was used. -122-200911731 (Example 2) In Example 1, an organic EL device was produced in the same manner by using Compound 20 instead of Compound 1. (Example 2 1) In Example 1, an organic EL device was produced in the same manner by using the compound 2 1 instead of the compound 1. (Comparative Example 1) In Example 1, an organic EL device was produced in the same manner as in the case of Substituting Compound 1, using the following Compound A.

(Comparative Example 2) An organic EL device was produced in the same manner as in Example 1 except that Compound 1 was substituted. (Comparative Example 3) -123- 200911731 Compound C In the same manner as in Example 1, substituting Compound 1, an organic EL device was produced by the above-described method. [Evaluation Method] Next, the evaluation method will be described. 1 EL element ’ is the external half-life. In the above-mentioned Examples 1 to 21 and Comparative Examples 1 to 3, the results of measuring the element performance sub-product, the emission wavelength, and the initial luminance of 100 cd/m 2 at the time of driving the current density of 10 mA/cm 2 are shown in the table. 1 is shown. -124- 200911731 [Table i] Host material dopant material External quantum yield Luminescence wavelength (mm) Lifetime period) Example 1 1 D-1 3.9 424 10000 Example 2 2 D-1 3.9 424 10000 Example 3 3 D-1 3.9 424 10000 Example 4 4 D-1 3.9 424 13000 Example 5 5 D-1 3.9 424 12000 Example 6 6 D-1 3.9 424 12000 Example 7 7 D-1 3.9 424 10000 Example 8 8 D-1 3.9 424 10000 Example 9 9 D-1 3.9 424 10000 Example 10 10 D-1 3.9 424 10000 Example 11 11 D-1 3.9 424 10000 Example 12 12 D-1 3.9 424 13000 Example 13 13 D-1 3.9 424 13000 Example 14 14 D-1 3.9 424 12000 Example 15 15 D-1 3.9 424 10000 Example 16 16 D-1 3.9 424 10000 Example 17 17 D-1 3.9 424 11000 Example 18 18 D-1 3.9 424 13000 Example 19 19 D-1 3.9 424 12000 Example 20 20 D-1 3.9 424 12000 Example 21 21 D-1 3.9 424 12000 Comparative Example 1 A D-1 3.9 424 7000 Comparative Example 2 B D-1 3.9 424 7000 Comparative Example 3 C D-1 3.9 424 7000 [Evaluation Result] As shown in Table 1, examples 1 to 21 and Comparative Example 1 were confirmed regarding the external quantum yield. 3 no big difference. Further, regarding the emission wavelength, it was confirmed that there was no significant difference between Examples 1 to 2 1 and Comparative Examples 1 to 3. Further, regarding the lifespan, it was confirmed that Examples 1 to 2 1 were longer than Comparative Examples 1 to 3. Further, from Examples 4, 5, 6, 12, 13, 14, and 18, the inter-phenylene-based cave derivatives have a particularly long life compared with others. Further, the introduction of a substituent at the 2,8 position of ruthenium can also extend the life. By asymmetry of the compound, the amorphous property is increased, and the life is prolonged. Further, by introducing such a specific structure into the cave derivative, crystallization can be further suppressed and the life can be extended. In other words, it has been confirmed that an organic EL device which can easily achieve a long life can be obtained by using the light-emitting layer of the constitution of the present invention. (Example 22) A glass substrate (manufactured by Geomatec Co., Ltd.) having an ITO transparent electrode (anode) of 25 mm x 75 mm x 1 mm thick was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then subjected to UV ozone washing for 30 minutes. The glass substrate with the transparent electrode wire after the cleaning is attached to the substrate holder of the vacuum vapor deposition apparatus, and the film thickness of 75 nm is formed by coating the transparent electrode on the surface on the side where the transparent electrode line is formed. Compound A-1. Further, on the A·1 film, the compound 1 of the present invention and the following compound D-2 were formed into a film at a film thickness ratio of 40:2 at a film thickness of 40 nm to form a blue light-emitting layer. Compound 1 is a host material and D-2 is a dopant. On the film, E-1 of the following structure was deposited as an electron transport layer as a film thickness of 2 Onm. Thereafter, LiF was deposited at a film thickness of inm -126-200911731. On the LiF film, metal Al and 150 nm were vapor-deposited to form a metal cathode, thereby forming an organic EL device.

(Examples 23 to 42) In Example 1, an organic EL device was produced in the same manner as in the compound 2 to 23 by substituting the compound 1. (Comparative Examples 4 to 6) In Comparative Examples 1 to 3, an organic EL element was produced in the same manner by substituting the compound 1 and using the following compounds A to C. [Evaluation method] Example 2 2 to 4 2, Organic EL elements of Comparative Examples 4 to 6, measured -127-200911731 External quantum yield, luminescence wavelength, and elemental performance at a constant current density of 10 mA/cm 2 And the initial half-life of the brightness l〇〇cd/m2. The results of these are shown in Table 2. [Table 2] host material dopant material luminous efficiency cd/A emission wavelength (mm) lifetime (time) Example 22 1 D-2 5.1 450 6000 Example 23 2 D-2 5.1 450 6000 Example 24 3 D- 2 5.1 450 6000 Example 25 4 D-2 5.1 450 13000 Example 26 5 D-2 5.2 450 12000 Example 27 6 D-2 5.2 450 12000 Example 28 7 D-2 5.1 450 6000 Example 29 8 D- 2 5.1 450 6000 Example 30 9 D-2 5.2 450 6000 Example 31 10 D-2 5.2 450 6000 Example 32 11 D-2 5.1 450 6000 Example 33 12 D-2 5.1 450 13000 Example 34 13 D- 2 5.1 450 13000 Example 35 14 D-2 5.1 450 12000 Example 36 15 D-2 5.1 450 6000 Example 37 16 D-2 5.1 450 6000 Example 38 17 D-2 6.0 450 11000 Example 39 18 D- 2 6.0 450 13000 Example 40 19 D-2 5.2 450 12000 Example 41 20 D-2 5.1 450 1000 Example 42 21 D-2 5.1 450 1000 Comparative Example 4 A D-2 4.5 450 4000 Comparative Example 5 B D- 2 4.5 450 4000 Comparative Example 6 C D-2 4.5 450 4000 -128- 200911731 [Evaluation Results] From the above, it is clear that materials with a metaphenylene skeleton have a longer life than other systems.It is considered to enhance the amorphous state of the deposited film. Further, a material having a diphenyl cave skeleton is considered to particularly improve the luminous efficiency. -129-

Claims (1)

200911731 X. Patent application scope 1 ·—The species of caves, characterized by the following general formula (1), In the general formula (1), Ar1 and Ar2 are each independently, and the substituted or unsubstituted aryl group having a carbon number of 6 to 14 is a substituent composed of a single or a combination of plural 'ArVAr2, Ar1 and Ar2. Containing ruthenium, R1 to R1G represent a hydrogen atom or a substituent, but, when Arl is an unsubstituted fluorenylnaphthyl group, oxime is an unsubstituted phenyl group, an unsubstituted biphenyl group, a 4-methyl substituted phenyl group, 4_( The case of 1_naphthyl)phenyl-1·yl and α-naphthyl. 2. The cave derivative of claim 1, wherein the Ar is substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and Ar'iAr2. 3. ~ The species of bribes, characterized by the following general formula (2), -130- (2) 200911731 In the general formula (2), Ar3 is a substituted or unsubstituted naphthalene, a substituted or unsubstituted phenanthrene, and Ar4 represents a substituent of a substituted or unsubstituted aryl group having a core number of 6 to 14 in a single or plural combination. R1 to rm represent a hydrogen atom or a substituent 'k is an integer of 1 to 4, and when k is 2 or more, R11 may be the same or different from each other'. In addition to Ar3 being an unsubstituted β-naphthyl group, Ar4 is absent. The case of substituting phenyl and α-naphthyl. 4. A cave derivative' characterized by the following general formula (3), R2 R3 R8 In the general formula (3), Ar4 and Ar5 are each independently, and represent a substituent of a substituted or unsubstituted aryl group having a carbon number of 6 to 14 -131 to 200911731 in a single or plural combination. Ar5, Ar4' Ar5 does not contain ruthenium, R1 to R] 2 represents a hydrogen atom or a substituent, k is an integer of 1 to 4, and when k is 2 or more, 'R11 may be the same or different from each other, and 1 is 1 to 4 In an integer, when 1 is 2 or more, R12 may be the same or different from each other. 5 · ~ species of cave derivatives, the characteristics are expressed by the following general formula (4), In the general formula (4), 'Ar6 and Ar7 are each independently, and represent a substituent in which a substituted or unsubstituted aryl group having a carbon number of 6 to 14 is a combination of singly or plural, but ArVAr7, Ar6, and Ar7 are not contained.蒽, r21 to r3Q represent a hydrogen atom or a substituent. 6_. The cave derivative according to any one of claims 1, 3 and 4, wherein at least one of R1 to R1Q is a substituted or unsubstituted square having a carbon number of 6 to M. 7. The hydrazine derivative of claim 5, wherein at least one of R R is a substituted or unsubstituted aryl group having 6 to 14 carbon atoms. ^ 8 · Such as the s 靑 靑 patent scope of the seventh item of the cave derivatives, where -132- 200911731 R22 and R2 7 are independent of each other, the number of carbon atoms 6 to 14 substituted or unsubstituted aryl group alone or in plural The substituents formed by the combination. 9. The cave derivative according to any one of claims 1, 3, 4 and 5, wherein at least one of the aryl substituents is a phenylene group having the following formula (5) , In the general formula (5), Ar8 is a substituent in which a substituted or unsubstituted aryl group having 6 to 14 carbon atoms is formed singly or in combination, and R 13 represents a hydrogen atom or a substituent, and m is 1 to 4; An integer, when m is 2 or more, R13 may be the same or different from each other. A material for an organic EL device, which is characterized by containing a cave derivative according to any one of claims 1, 3, 4 and 5. A luminescent material for an organic EL device, which is characterized by containing a cave derivative according to any one of claims 1, 3, 4 and 5. 12. An organic EL device, wherein an organic thin film layer comprising at least one layer or a plurality of layers of a light-emitting layer is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer comprises a patent application scope number 1. The cave derivatives of any of items 3, 4 and 5 are used as separate or mixtures. -133- 200911731 13. Organic EL as claimed in claim 12 The above-mentioned light-emitting layer contains the derivative of the first, third, and third parties of the patent application as a light-emitting material. 14. The organic EL as claimed in item 12 of the patent application includes the cave derivative of the first and third paragraphs of the patent application as the main material. 15. The organic EL as claimed in claim 12, wherein the luminescent layer further contains fluorescing or phosphorescent. 16. The organic EL of claim 15 is an arylamine-containing compound. 17. The organic EL as claimed in claim 16 wherein the luminescent layer contains a styrylamine compound. 18. The organic EL as claimed in claim 1 of the invention, wherein the luminescent layer contains an aromatic amine compound. An element, wherein any one of the items 4 and 5, wherein, any of the items 4, 5, and 5, wherein, the dopant. Component, wherein, component, wherein, component, wherein, -134- 200911731 Ming said that there is no simple lgu: # is a map of the map element on behalf of the map • • refers to the table pattern represents the book without generation N ZN fixed one two t 曰X 8. If there is a chemical formula in this case, please reveal the chemical formula that best shows the characteristics of the invention.