JP2005068366A - Material for organic electroluminescent element and organic electroluminescent element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element capable of obtaining a high color purity and luminance by a low driving electric voltage, showing a red color and having a long life. <P>SOLUTION: This electroluminescent element has a light-emitting layer containing an amine compound expressed by general formula [1] [wherein, Ar<SP>1</SP>is a substituted or un-substituted perylenyl group; and R<SP>1</SP>, R<SP>2</SP>are each a monovalent aromatic hydrocarbon group or the like] and dibenzo[f,f']diindeno[1,2,3-cd:1',2',3'-lm]perylene derivative expressed by general formula [2] [wherein, X<SP>1</SP>to X<SP>20</SP>are each H or the like]. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to an organic electroluminescence element used for a planar light source and display. More specifically, the present invention relates to a long-life organic electroluminescence device for obtaining red light emission exhibiting high color purity and luminance at a low driving voltage.

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

This study was conducted by Eastman Kodak's C.I. W. Tang et al., Appl. Phys. Lett. 51, 913, published in 1987, which originated from an EL element with an organic thin film laminated. In this report, a metal chelate complex is used for the light emitting layer and an amine compound is used for the hole injection layer. Thus, green light emission having a luminance of several thousand (cd / m ² ) at a direct voltage of 6 to 10 V and a maximum light emission efficiency of 1.5 (lm / W) is obtained. It can be said that the organic EL elements currently being developed by various research institutes basically follow the configuration of Eastman Kodak Company.

  Among organic EL elements, organic EL elements that emit red light have been researched for elements using various materials because of their usefulness, but a method such as co-evaporation of a small amount of dopant in the host material. A method of forming a light-emitting layer by mixing them to obtain light emission from a dopant has been studied as an effective method. As such an example, C.I. H. Chen et al., Macromol. Symp. 125, 34-36 and 49-58, published in 1997, tris (8-hydroxyquinolinate) aluminum as a host material and 4H such as DCM, DCJ, DCJT, DCJTB -An organic EL device capable of emitting orange to red light using a pyran derivative as a dopant has been reported.

  As for organic EL elements having a perylene structure, for example, JP-A-10-251633, JP-A-11-144869, JP-A-2001-11031, JP-A-2001-176664, 2002-2002. No. 129043 and JP-A-2003-201472 are known.

Furthermore, as an organic EL device using a compound having a dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative as a dopant, for example, Japanese Patent Application Laid-Open No. 10-125 No. -329595, JP-A-11-233261, JP-A 2000-48958, and JP-A-2000-86549 are known.
Appl. Phys. Lett. 51, 913, 1987 Macromol. Symp. 125, 34-36 and 49-58, 1997 JP-A-10-251633 Japanese Patent Laid-Open No. 11-144869 JP 2001-11031 A JP 2001-176664 A JP 2002-129043 A JP 2003-201472 A Japanese Patent Laid-Open No. 10-330295 JP-A-11-233261 JP 2000-48958 A JP 2000-86549 A

  The organic EL device for obtaining red high-intensity light emission described in the prior art has the disadvantages of poor color purity and short lifetime. An organic EL device using a 4H-pyran derivative as a dopant has a problem that the emission color is insufficient, the driving voltage is high, and the emission luminance is low. Further, in the case of an organic EL element having a perylene structure, the emission peak width is wide, so that the color purity is insufficient. Furthermore, an organic EL element using a dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative can produce an element with high color purity. Although it was possible, there was a drawback that the driving voltage was high and the life was short. For this reason, there has been a demand for a long-life organic EL element capable of obtaining red light emission with high color purity and brightness at a much lower driving voltage.

As a result of intensive studies to solve the above problems, the present inventors have arrived at the present invention. That is, this invention relates to the material for organic electroluminescent elements containing the compound represented by the following general formula [1], and the compound represented by the following general formula [2].
General formula [1]

[Wherein Ar1 represents a substituted or unsubstituted perylenyl group;
R ¹ and R ² are each independently a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group.
Ar ¹ and R ¹ , Ar ¹ and R ² , R ¹ and R ² may be bonded to each other to form a ring. ]
General formula [2]

Wherein X ^{1 to} X ²⁰ are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenyl group, a substituted Or an unsubstituted alkenyloxy group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted aryl group , Substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted amino group, cyano group, hydroxyl group, —COOR ³¹ group (where R ³¹ is a hydrogen atom, substituted or unsubstituted alkyl group) A group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, Rui represents a substituted or unsubstituted aryl group), - COR ³² group (wherein, R ³² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, A substituted or unsubstituted aryl group, or a substituted or unsubstituted amino group, or —OCOR ³³ (wherein R ³³ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted group) Represents a substituted aralkyl group or a substituted or unsubstituted aryl group), and X ^{1 to} X ²⁰ may be combined with each other to form a ring. ]

  In addition, the present invention provides an organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode. The present invention relates to an organic electroluminescence element including an element material.

  In addition, the present invention provides an organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode, wherein the light emitting layer is the above organic electroluminescence. The present invention relates to an organic electroluminescence element including an element material.

  The organic EL element produced by using the material for the organic EL element of the present invention emits light at a lower driving voltage and has a longer life than conventional ones, and thus is suitably used as a flat panel display such as a wall-mounted TV or a flat light emitter. It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights.

  Hereinafter, the present invention will be described in detail. The present invention relates to an amine compound represented by the general formula [1] and a dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3 represented by the general formula [2]. An amine compound represented by the general formula [1] will be described first, although it is a material for an organic electroluminescence device containing a '-lm] perylene derivative.

First, Ar ¹ in the general formula [1] represents a substituted or unsubstituted perylenyl group, and examples of the unsubstituted perylenyl group include a 1-perylenyl group, a 2-perylenyl group, and a 3-perylenyl group. These perylenyl groups may be further substituted with other substituents.
In the present invention, the substituent includes a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aliphatic heterocyclic group, a monovalent aromatic heterocyclic group, a halogen atom, and a cyano group. , Alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, and the like.

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

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

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

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

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

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

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

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

  In addition, as the monovalent aliphatic heterocyclic group, a monovalent fatty acid having 3 to 18 carbon atoms such as a 3-isochromanyl group, a 7-chromanyl group, a 3-coumarinyl group, a piperidino group, a morpholino group, and a 2-morpholino group. Group heterocyclic group.

  Examples of the monovalent aromatic heterocyclic group include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-benzofuryl group, 2-benzothienyl group, 2-pyridyl group, 3 Examples thereof include monovalent aromatic heterocyclic groups having 3 to 30 carbon atoms such as -pyridyl group, 4-pyridyl group, 2-quinolyl group, and 5-isoquinolyl group.

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

  As the alkoxy group, methoxy group, ethoxy group, propoxy group, butoxy group, tert-butoxy group, octyloxy group, tert-octyloxy group, 2-bornyloxy group, 2-isobornyloxy group, 1-adamantyl group C1-C18 alkoxy groups, such as an oxy group, are mention | raise | lifted.

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

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

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

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

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

  Examples of the aryloxycarbonyl group include aryloxycarbonyl groups having 7 to 30 carbon atoms such as a phenoxycarbonyl group and a naphthyloxycarbonyl group.

  Moreover, as an alkylsulfonyl group, C1-C18 alkylsulfonyl groups, such as a mesyl group, an ethylsulfonyl group, a propylsulfonyl group, are mention | raise | lifted.

  Examples of the arylsulfonyl group include arylsulfonyl groups having 6 to 30 carbon atoms such as a benzenesulfonyl group and a p-toluenesulfonyl group.

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

Ar ¹ in the general formula [1] described above includes a substituted or unsubstituted 1-perylenyl group, a substituted or unsubstituted 2-perylenyl group, and a substituted or unsubstituted 3-perylenyl group. Of these, a substituted or unsubstituted 3-perylenyl group is preferable, and an unsubstituted 3-perylenyl group is particularly preferable. Among the substituted 3-perylenyl groups, preferred substituents include the aforementioned alkyl groups, monovalent aromatic hydrocarbon groups, and monovalent aromatic heterocyclic groups. Particularly preferred substituents are 1 Valent aromatic hydrocarbon group.

  Moreover, as carbon number in the substituent described above, 1-18 are preferable and 1-12 are more preferable. The reason for this is that if the carbon number of these substituents increases, there is a concern that the vapor deposition property when an element is formed by vapor deposition is deteriorated.

Next, R ¹ and R ² in the general formula [1] will be described. R ¹ and R ² are monovalent organic residues selected from a substituted or unsubstituted monovalent aromatic hydrocarbon group or a substituted or unsubstituted monovalent aromatic heterocyclic group. The substituent here has the same meaning as the substituent described for the substituent of Ar ¹ . In addition, the unsubstituted monovalent aromatic hydrocarbon group and the unsubstituted monovalent aromatic heterocyclic group are the monovalent aromatic hydrocarbon group and the unsubstituted 1 described above for the substituent of Ar ¹ , respectively. Synonymous with a valent aromatic heterocyclic group.

Among the amine compounds represented by the general formula [1], a preferable one is an amine compound represented by the following general formula [3].
General formula [3]

[Wherein Ar ² represents a substituted or unsubstituted perylenyl group, R ³ and Ar ⁴ represent a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic ring. Group, Ar ³ is a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group, R ⁴ is a direct bond, O, S, ═C (R ⁵ ) any one of R ⁶ and = Si (R ⁷ ) R ⁸ (where R ^{5 to} R ⁸ are a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted group) Or a monovalent aromatic hydrocarbon group). Ar ² and R ³ , R ³ and Ar ³ , Ar ³ and Ar ² may be bonded to each other to form a ring. ]

  Substituent, substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent The aliphatic hydrocarbon group is a substituent described in the general formula [1], a substituted or unsubstituted perylenyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent group, respectively. Are the same as the aromatic heterocyclic group and the substituted or unsubstituted monovalent aliphatic hydrocarbon group.

  The divalent aromatic hydrocarbon group in the general formula [3] means a divalent monocyclic ring, condensed ring, or ring-aggregated aromatic hydrocarbon group. For example, phenylene group, naphthylene group, anthrylene group, biphenylene Group, p-terphenyl-4,4 ″ -diyl group, m-terphenyl-3,3 ″ -diyl group, m-terphenyl-4,4′-diyl group, [1,2′-binaphthalene ] A divalent aromatic hydrocarbon group having 6 to 30 carbon atoms such as -4,5'-diyl. In addition, the divalent aromatic heterocyclic group in the general formula [3] means a divalent monocyclic ring, a condensed ring, or a ring assembly aromatic heterocyclic group, for example, 2,5-furylene group, 2, A divalent group having 4 to 30 carbon atoms such as 5-thienylene group, 2,5-pyridylene group, 2,5-pyrazylene group, 2,6-quinylene group, 1,4-isoquinolylene group, 2,3-quinoxalylene group, etc. An aromatic heterocyclic group is mentioned.

  Among the divalent aromatic hydrocarbon groups or aromatic heterocyclic groups described above, preferred are divalent aromatic hydrocarbon groups having 6 to 12 carbon atoms such as a phenylene group, a naphthylene group, and a biphenylene group. can give.

Furthermore, among the amine compounds represented by the above general formula [3], more preferred are amine compounds represented by the following general formula [4].
General formula [4]

[Wherein Ar ⁵ represents a substituted or unsubstituted perylenyl group, Ar ⁶ and Ar ⁸ represent a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic ring. Groups Ar ⁷ and Ar ⁹ are substituted or unsubstituted monovalent aromatic hydrocarbon groups, or substituted or unsubstituted monovalent aromatic heterocyclic groups, R ⁹ and R ¹⁰ are direct bonds, O, S, = C (R ¹¹ ) R ¹² , = Si (R ¹³ ) R ¹⁴ (wherein R ^{11 to} R ¹⁴ are a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon, A group, either a substituted or unsubstituted monovalent aromatic hydrocarbon group). Ar ⁵ and Ar ⁶ , Ar ⁶ and Ar ⁸ , Ar ⁸ and Ar ⁵ may be bonded to each other to form a ring. ]

  Substituent, substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent The aliphatic hydrocarbon group, the substituted or unsubstituted divalent aromatic hydrocarbon group, or the substituted or unsubstituted divalent aromatic heterocyclic group is represented by the general formula [1] and the general formula [3], respectively. Substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent It is synonymous with an aliphatic hydrocarbon group, a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group.

Further, among the amine compounds represented by the general formula [1], other preferable compounds include amine compounds represented by the following general formula [5].
General formula [5]

[Wherein Ar ¹⁰ represents a substituted or unsubstituted perylenyl group, R ¹⁵ , Ar ¹² and Ar ¹³ represent a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic group. Group heterocyclic group, Ar ¹¹ is a substituted or unsubstituted divalent aromatic hydrocarbon group, or substituted or unsubstituted divalent aromatic heterocyclic group, R 16 is a direct bond, O, S, ═C (R ¹⁷ ) R ¹⁸ or any one of ═Si (R ¹⁹ ) R ²⁰ (where R ^{17 to} R ²⁰ are a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or Any of unsubstituted monovalent aromatic hydrocarbon groups). Ar10 and R ¹⁵ , R ¹⁵ and Ar ¹¹ , Ar ¹¹ and Ar ¹⁰ , Ar ¹² and Ar ¹³ , Ar ¹³ and R ¹⁶ , and R ¹⁶ and Ar ¹² may be bonded to each other to form a ring. ]

  Substituent, substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent The aliphatic hydrocarbon group, the substituted or unsubstituted divalent aromatic hydrocarbon group, or the substituted or unsubstituted divalent aromatic heterocyclic group is represented by the general formula [1] and the general formula [3], respectively. Substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent It is synonymous with an aliphatic hydrocarbon group, a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group.

Furthermore, among the amine compounds represented by the general formula [5], particularly preferred are amine compounds represented by the following general formula [6].
General formula [6]

[Wherein Ar ¹⁴ represents a substituted or unsubstituted perylenyl group, Ar ¹⁵ and Ar ¹⁸ represent a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic ring. The groups Ar ¹⁶ , Ar ¹⁷ , Ar ¹⁹ and Ar ²⁰ are a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group, R ²¹ and R ²² are , Direct bond, O, S, ═C (R ²³ ) R ²⁴ , ═Si (R ²⁵ ) R ²⁶ (wherein R ^{23 to} R ²⁶ are each a hydrogen atom, substituted or unsubstituted 1 A divalent aliphatic hydrocarbon group or a substituted or unsubstituted monovalent aromatic hydrocarbon group). Ar ¹⁶ and Ar ¹⁷ , Ar ¹⁷ and R ²¹ , R ²¹ and Ar ¹⁶ , Ar ¹⁹ and Ar ²⁰ , Ar ²⁰ and R ²² , R ²² and R ¹⁹ , Ar ¹⁴ and Ar ¹⁵ , Ar ¹⁵ and Ar ¹⁸ , Ar ¹⁸ And Ar ¹⁴ may be bonded to each other to form a ring. ]

  Substituent, substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent The aliphatic hydrocarbon group, the substituted or unsubstituted divalent aromatic hydrocarbon group, or the substituted or unsubstituted divalent aromatic heterocyclic group is represented by the general formula [1] and the general formula [3], respectively. Substituted or unsubstituted perylenyl group, substituted or unsubstituted monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent aromatic heterocyclic group, substituted or unsubstituted monovalent It is synonymous with an aliphatic hydrocarbon group, a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group.

  The amine compound represented by the general formula [1] used in the present invention has been described above. The molecular weight of these amine compounds is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. This is because, when the molecular weight is large, there is a concern that the vapor deposition property in the case of producing an element by vapor deposition is deteriorated.

  Table 1 below shows typical examples of the amine compound represented by the general formula [1] that can be used as the material for the organic EL device of the present invention (Exemplary Compounds 1 to 80). However, it is not limited (in Table 1, t-Bu represents a tert-butyl group, Ph represents a phenyl group, and tol represents a p-tolyl group).

  Next, the dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative represented by the general formula [2] used in the present invention will be described. The name dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative is bisbenzo [5,6] indeno [1,2,3- cd: 1 ′, 2 ′, 3′-lm] perylene derivatives, the names used herein follow the method described in J. Amer. Chem. Soc., 118, 2374 (1996). .

X ^{1 to} X ²⁰ in the general formula [2] are a hydrogen atom, a halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted linear, branched or cyclic alkoxy group, Substituted or unsubstituted linear, branched or cyclic alkylthio group, substituted or unsubstituted linear, branched or cyclic alkenyl group, substituted or unsubstituted linear, branched or cyclic alkenyloxy group, substituted or unsubstituted Linear, branched or cyclic alkenylthio group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aralkyloxy group, substituted or unsubstituted aralkylthio group, substituted or unsubstituted aryl group, substituted or unsubstituted Aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted amino group, cyano group, hydroxyl group,- OOR ³¹ group (wherein, R ³¹ is a hydrogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group, straight chain substituted or unsubstituted, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group Or a substituted or unsubstituted aryl group), a —COR ³² group (wherein R ³² is a hydrogen atom, a substituted or unsubstituted straight chain, a branched or cyclic alkyl group, a substituted or unsubstituted straight chain, Represents a branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or an amino group), or —OCOR ³³ (wherein R ³³ represents a substituted or unsubstituted linear or branched group) Or a cyclic alkyl group, a substituted or unsubstituted linear, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted Represents represents) the conversion of the aryl group, further, X ¹ to X ²⁰ are taken together with adjacent groups may form a ring.

-COOR ³¹ group (wherein R ³¹ is a hydrogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted linear, branched or cyclic alkenyl group, substituted or unsubstituted aralkyl. Group or a substituted or unsubstituted aryl group) includes an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aralkyloxycarbonyl group, and an aryloxycarbonyl group having 4 to 20 carbon atoms.

-COR ³² group (in which R ³² is a hydrogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted linear, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl Group, a substituted or unsubstituted aryl group or an amino group) includes an alkylcarbonyl group, an alkenylcarbonyl group, an aralkylcarbonyl group, and an arylcarbonyl group.

—OCOR ³³ (wherein R ³³ represents a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted linear, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted group) Examples of an unsubstituted aryl group include an alkylcarbonyloxy group, an alkenylcarbonyloxy group, an aralkylcarbonyloxy group, and an arylcarbonyloxy group.

In the general formula [2], a linear, branched or cyclic alkyl group of X ^{1 to} X ^20, a linear, branched or cyclic alkoxy group, a linear, branched or cyclic alkylthio group, a linear, branched or The cyclic alkenyl group, the linear, branched or cyclic alkenyloxy group, and the linear, branched or cyclic alkenylthio group may have a substituent, for example, a halogen atom having 4 to 20 carbon atoms. Aryl group, alkoxy group having 1 to 20 carbon atoms, alkenyloxy group having 2 to 20 carbon atoms, aralkyloxy group having 4 to 20 carbon atoms, aryloxy group having 3 to 20 carbon atoms, aryl alkenyl having 5 to 20 carbon atoms Group, an alkylthio group having 1 to 20 carbon atoms, an alkenylthio group having 2 to 20 carbon atoms, an aralkylthio group having 4 to 20 carbon atoms, and an arylthio group having 3 to 20 carbon atoms Alternatively, it may be monosubstituted or polysubstituted with a halogen atom or the like. Furthermore, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 3 to 10 carbon atoms, and an aryl group having 4 to 10 carbon atoms. It may be substituted with an aralkyl group.

In general formula [2], the aryl group in X ^{1 to} X ²⁰ aralkyl group, aralkyloxy group, aralkylthio group, aryl group, aryloxy group, and arylthio group may have a substituent, For example, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aralkyl group having 4 to 20 carbon atoms, an aryl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and 2 carbon atoms -20 alkenyloxy group, C4-20 aralkyloxy group, C3-20 aryloxy group, C2-20 alkylcarbonyl group, C3-20 alkenylcarbonyl group, C5 -20 aralkylcarbonyl group, C4-20 arylcarbonyl group, C2-20 alkoxycarbonyl group, C3-20 alkenyloxy. A sicarbonyl group, an aralkyloxycarbonyl group having 5 to 20 carbon atoms, an aryloxycarbonyl group having 4 to 20 carbon atoms, an alkylcarbonyloxy group having 2 to 20 carbon atoms, an alkenylcarbonyloxy group having 3 to 20 carbon atoms, An aralkylcarbonyloxy group having 5 to 20 carbon atoms, an arylcarbonyloxy group having 4 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an aralkylthio group having 4 to 20 carbon atoms, an arylthio group having 3 to 20 carbon atoms, Nitro group, cyano group, formyl group, halogen atom, halogenated alkyl group, hydroxyl group, amino group, N-monosubstituted amino group having 1 to 20 carbon atoms, N, N-disubstituted amino group having 2 to 40 carbon atoms, etc. These substituents may be mono- or polysubstituted.

  Furthermore, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryl group having 7 to 10 carbon atoms. It may be substituted with an aralkyl group.

In the general formula [2], the amino group of X ^{1 to} X ²⁰ may have a substituent, for example, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 4 to 20 carbon atoms, or 3 carbon atoms. It may be monosubstituted or disubstituted with ˜20 aryl groups.

In the general formula [2], the alkyl group, alkenyl group, aralkyl group and aryl group of R ³¹ , R ³² and R ³³ may have a substituent, for example, the substituents mentioned for X ^{1 to} X ²⁰ May be mono- or polysubstituted.

R ³¹ is more preferably a hydrogen atom, a substituted or unsubstituted straight chain having 1 to 24 carbon atoms, a branched or cyclic alkyl group, a substituted or unsubstituted straight chain having 2 to 24 carbon atoms, branched or A cyclic alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted atom. A linear, branched or cyclic alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 24 carbon atoms.

R ³² is more preferably a hydrogen atom, a substituted or unsubstituted straight chain having 1 to 24 carbon atoms, a branched or cyclic alkyl group, a substituted or unsubstituted straight chain having 2 to 24 carbon atoms, branched or A cyclic alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, or an amino group, more preferably a hydrogen atom, An unsubstituted straight chain, branched or cyclic alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, Or it is an amino group.

R ³³ is more preferably a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted linear, branched or cyclic group having 2 to 24 carbon atoms. An alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms in total, or a substituted or unsubstituted aryl group having 6 to 24 carbon atoms in total, more preferably a substituted or unsubstituted 1 to 1 carbon atom in total. 24 linear, branched or cyclic alkyl groups, substituted or unsubstituted aralkyl groups having 7 to 24 carbon atoms in total, or substituted or unsubstituted aryl groups having 6 to 24 carbon atoms in total.

X ^{1 to} X ²⁰ are more preferably a hydrogen atom, a halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted total carbon number of 1 to 24. A linear, branched or cyclic alkoxy group, a substituted or unsubstituted linear chain having 1 to 24 carbon atoms, a branched or cyclic alkylthio group, a substituted or unsubstituted linear chain having 2 to 24 carbon atoms, branched or Cyclic alkenyl group, substituted or unsubstituted straight chain, branched or cyclic alkenyloxy group having 2 to 24 carbon atoms, substituted or unsubstituted straight chain, branched or cyclic alkenylthio group having 2 to 24 carbon atoms A substituted or unsubstituted aralkyl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 24 carbon atoms, a substituted or unsubstituted araalkyloxy group having 7 to 24 carbon atoms. Kirthio group, substituted or unsubstituted aryl group having 4 to 24 carbon atoms, substituted or unsubstituted aryloxy group having 4 to 24 carbon atoms, substituted or unsubstituted arylthio group having 6 to 24 carbon atoms, substituted amino group, a total substituted amino group having a carbon number of 1 to 24, a cyano group, a hydroxyl group, -COOR ^31, -C oR ^32, or -OCOR ³³ (where in the radical, R ³¹ to R ³³ are as defined in the Represents).

More preferably, X ¹³ to X ²⁰ is a hydrogen atom, and X ¹ to X ¹² is a hydrogen atom, a halogen atom, a straight-chain having a total carbon number of 1 to 24 substituted or unsubstituted, branched or cyclic alkyl group, A substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 24 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkenyl group having 2 to 24 carbon atoms, a substituted or unsubstituted total Aralkyl group having 7 to 24 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 carbon atoms in total, cyano group, hydroxyl group, —COOR ³¹ , —C OR ³² , or —OCOR ³³ (provided that R ³¹ to R ³³ is represented) as defined above.

Particularly preferably, X ^{13 to} X ²⁰ are a hydrogen atom, and X ^{1 to} X ¹² are a hydrogen atom, a halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 24 carbon atoms in total, A substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 24 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkenyl group having 2 to 24 carbon atoms, a substituted or unsubstituted total Aralkyl group having 7 to 24 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 carbon atoms in total, cyano group, hydroxyl group, —COOR ³¹ , —C OR ³² , or —OCOR ³³ (provided that R ³¹ to R ³³ is a compound which is substituted with representative) as defined above.

Further, the adjacent group selected from X ^{1 to} X ²⁰ , or the group selected from X ¹ and X ⁶ , X ⁷ and X ¹² are bonded to each other, and are substituted or unsubstituted together with a substituted carbon atom. A carbocyclic aliphatic ring may be formed, and preferably a substituted or unsubstituted carbocyclic aliphatic ring having 4 to 20 carbon atoms in total is formed.

Specific examples of X ^{1 to} X ²⁰ include a hydrogen atom, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2 -Ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group, n-undecyl group, 1 Methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group N-octadecyl group, 1-nonyldecyl group, 1-decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2-cyclohexylethyl group, Bornel group, isobornel group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, Cyclopentyl group, 1-methylcyclopentyl group, cyclo Xyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethyl group Cyclohexyl group, 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3-tert -Butylcyclohexyl group, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, cyclododecyl group, cyclotetradecyl group,

Methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2- (2′-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2′-ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group, 2-n-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypro Group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3- (n-butoxy) propyl group, 3- (n-pentyloxy) propyl group , 3- (n-hexyloxy) propyl group, 3- (2′-ethylbutoxy) propyl group, 3- (n-octyloxy) propyl group, 3- (2′-ethylhexyloxy) propyl group, 3- ( n-decyloxy) propyl group, 3- (n-dodecyloxy) propyl group, 3- (n-tetradecyloxy) propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4 -N-propoxybutyl group, 4-isopropoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4-n-o Cutyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl group, 6-ethoxyhexyl group, 6 -Isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group 8-methoxyoctyl group, 10-methoxydecyl group, 10-n-butoxydecyl group, 12-ethoxydodecyl group, 12-isopropoxide decyl group, tetrahydrofurfuryl group,

2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butoxyethoxy) ethyl group, 3- (2′-ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4′-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2′-hexenyloxy) propyl group, 3- (2′-heptenyloxy) propyl group, 3 -(1'-cyclohexenyloxy) propyl group, 4-allyloxybutyl group, benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4'-methylbenzyloxy) ethyl group 2- (2′-methylbenzyloxy) ethyl group, 2- (4′-fluorobenzyloxy) ethyl group, 2- (4′-chlorobenzyloxy) Ethyl group, 3-benzyloxypropyl group, 3- (4′-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) ethyl group, 2- (4′-methylbenzyloxymethoxy) ) Ethyl group,

Phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4-chlorophenyloxymethyl group Group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl group, 2- (4′-methoxyphenyl) Oxy) ethyl group, 2- (4′-chlorophenyloxy) ethyl group, 2- (4′-bromophenyloxy) ethyl group, 2- (1′-naphthyloxy) ethyl group, 2- (2′-naphthyloxy) ) Ethyl group, 3-phenyloxypropyl group, 3- (2′-naphthyloxy) propyl group, 4- Enyloxybutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl Group, 10-phenyloxydecyl group, 10- (3′-chlorophenyloxy) decyl group, 2- (2′-phenyloxyethoxy) ethyl group, 3- (2′-phenyloxyethoxy) propyl group, 4- ( 2′-phenyloxyethoxy) butyl group, cinnamyl group, cinnamylmethyl group, 2-cinnamylethyl group,

n-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2-n-octyl Thioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2 ′ -Methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl group, 2-allylthioethyl group, 2-benzylthioethyl group, 3- (4′-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2′-benzyloxyethylthio) ethyl group, 3- (3′-benzylthiopropyl) Thio) propyl group, 2-phenylthioethyl group, 2- (4′-methoxyphenylthio) ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) Propyl group,

Fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8-fluorooctyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro-n-propyl 1,1,3-trihydro-perfluoro-n-propyl group, 1,1-dihydro-perfluoro-n-butyl group, 1,1-dihydro-perfluoro-n-pentyl group, 1,1- Dihydro-perfluoro-n-hexyl group, 6-fluorohexyl group, 4-fluorocyclohexyl group, 1,1-dihydro-perfluoro-n-octyl group, 1,1-dihydro-perfluoro-n-decyl group, 1,1-dihydro-perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro-n-tetradecyl group, 1,1-dihydro-per Fluoro-n-hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chlorooctyl group, 2, 2,2-trichloroethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, A linear, branched or cyclic alkyl group which may have a substituent such as an 8-hydroxyoctyl group, a 10-hydroxydecyl group, a 12-hydroxydodecyl group, a 2-hydroxycyclohexyl group,

For example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 2-ethylbutoxy group, 3,3-dimethylbutoxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy Group, n-dodecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, n-octadecyloxy group, n-eicosyloxy group, n-docosyloxy group, n-tetracosyloxy group,

Fluoromethoxy group, trifluoromethoxy group, 1,1-dihydroperfluoroethoxy group, perfluoroethoxy group, 1,1-dihydroperfluoro-n-propoxy group, 1,1,3-trihydroperfluoro-n- Propoxy group, 1,1-dihydroperfluoro-n-butoxy group, 1,1-dihydroperfluoro-n-pentyloxy group, 1,1-dihydroperfluoro-n-hexyloxy group, 4-chlorocyclohexyloxy group 1,1-dihydroperfluoro-n-octyloxy group, 1,1-dihydroperfluoro-n-decyloxy group, 1,1-dihydroperfluoro-n-dodecyloxy group, 1,1-dihydroperfluoro- n-hexadecyloxy group,

Ethoxymethoxy group, 1-methoxyethoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propoxyethoxy group, 2-isopropoxyethoxy group, 2-n-butoxyethoxy group, 2-n-hexyl Oxyethoxy group, 2-n-octyloxyethoxy group, 2- (2′-ethylhexyloxy) ethoxy group, 2-n-decyloxyethoxy group, 2-methoxypropoxy group, 3-methoxypropoxy group, 3-ethoxypropoxy group Group, 3-isopropoxypropoxy group, 3-n-butoxypropoxy group, 3-n-hexyloxypropoxy group, 3-n-octyloxypropoxy group, 2-methoxybutoxy group, 3-methoxybutoxy group, 4-methoxy Butoxy group, 4-ethoxybutoxy group, 4-isopropoxybutoxy group, -N-butoxybutoxy group, 4-n-hexyloxybutoxy group, 4-n-decyloxybutoxy group, 4-n-dodecyloxybutoxy group, 5-ethoxypentyloxy group, 6-methoxyhexyloxy group, 6- Ethoxyhexyloxy group, 6-isopropoxyhexyloxy group, 4-methoxycyclohexyloxy group, 7-methoxyheptyloxy group, 8-ethoxyoctyloxy group, 10-methoxydecyloxy group, 12-ethoxydodecyloxy group, 2- [(2′-methoxyethyl) oxy] ethoxy group, 3-[(2′-ethoxyethyl) oxy] propoxy group,

2-benzyloxyethoxy group, 2- (4-methylbenzyloxy) ethoxy group, 2- (4-methoxybenzyloxy) ethoxy group, 3- (4-ethylbenzyloxy) propoxy group, 4- (3-fluorobenzyl) Oxy) butoxy group, 4- (4-chlorobenzyloxy) butoxy group, 6- (3-methylbenzyloxy) hexyloxy group, phenyloxymethoxy group, 2-phenyloxyethoxy group, 2- (1′-naphthyloxy) ) Ethoxy group, 2- (2′-naphthyloxy) ethoxy group, 2- (4′-methylphenyloxy) ethoxy group, 2- (4′-methoxyphenyloxy) ethoxy group, 2- (3′-ethoxyphenyl) Oxy) ethoxy group, 2- (4′-chlorophenyloxy) ethoxy group, 3-phenyloxypropoxy group, 3- (4′-ethylphenyloxy) propoxy group, 3- (4′-chlorophenyloxy) propoxy group, 3- (2′-naphthyloxy) propoxy group, 4-phenyloxybutoxy group, 6-phenyloxyhexyloxy group, A linear, branched or cyclic alkoxy group which may have a substituent such as an 8-phenyloxyoctyloxy group, a 10-phenyloxydecyloxy group,

For example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, n-pentylthio group, neopentylthio group, isopentylthio group, cyclopentylthio group, n-hexylthio group, 2-ethylbutylthio group, 3,3-dimethylbutylthio group, cyclohexylthio group, n-heptylthio group, n-octylthio group, 2-ethylhexylthio group, n-nonylthio group, n-decylthio group N-dodecylthio group, n-tetradecylthio group, n-hexadecylthio group, n-octadecylthio group, n-eicosylthio group, n-docosylthio group, n-tetracosylthio group,

Fluoromethylthio group, trifluoromethylthio group, 1,1-dihydroperfluoroethylthio group, perfluoroethylthio group, 1,1-dihydroperfluoro-n-propylthio group, 1,1,3-trihydroperfluoro- n-propylthio group, 1,1-dihydroperfluoro-n-butylthio group, 1,1-dihydroperfluoro-n-pentylthio group, 1,1-dihydroperfluoro-n-hexylthio group, 4-chlorocyclohexylthio group 1,1-dihydroperfluoro-n-octylthio group, 1,1-dihydroperfluoro-n-decylthio group, 1,1-dihydroperfluoro-n-dodecylthio group, 1,1-dihydroperfluoro-n- Hexadecylthio group,

Ethoxymethylthio group, 1-methoxyethylthio group, 2-methoxyethylthio group, 2-ethoxyethylthio group, 2-n-propoxyethylthio group, 2-isopropoxyethylthio group, 2-n-butoxyethylthio group 2-n-hexyloxyethylthio group, 2-n-octyloxyethylthio group, 2- (2′-ethylhexyloxy) ethylthio group, 2-n-decyloxyethylthio group, 2-methoxypropylthio group, 3-methoxypropylthio group, 3-ethoxypropylthio group, 3-isopropoxypropylthio group, 3-n-butoxypropylthio group, 3-n-hexyloxypropylthio group, 3-n-octyloxypropylthio group 2-methoxybutylthio group, 3-methoxybutylthio group, 4-methoxybutylthio group, 4-ethoxybutyl Tilthio group, 4-isopropoxybutylthio group, 4-n-butoxybutylthio group, 4-n-hexyloxybutylthio group, 4-n-decyloxybutylthio group, 4-n-dodecyloxybutylthio group, 5-ethoxypentylthio group, 6-methoxyhexylthio group, 6-ethoxyhexylthio group, 6-isopropoxyhexylthio group, 4-methoxycyclohexylthio group, 7-methoxyheptylthio group, 8-ethoxyoctylthio group, 10-methoxydecylthio group, 12-ethoxydodecylthio group, 2-[(2′-methoxyethyl) oxy] ethylthio group, 3-[(2′-ethoxyethyl) oxy] propylthio group,

2-benzyloxyethylthio group, 2- (4-methylbenzyloxy) ethylthio group, 2- (4-methoxybenzyloxy) ethylthio group, 3- (4-ethylbenzyloxy) propylthio group, 4- (3-fluoro Benzyloxy) butylthio group, 4- (4-chlorobenzyloxy) butylthio group, 6- (3-methylbenzyloxy) hexylthio group, phenyloxymethylthio group, 2-phenyloxyethylthio group, 2- (1′-naphthyl) Oxy) ethylthio group, 2- (2′-naphthyloxy) ethylthio group, 2- (4′-methylphenyloxy) ethylthio group, 2- (4′-methoxyphenyloxy) ethylthio group, 2- (3′-ethoxy) Phenyloxy) ethylthio group, 2- (4′-chlorophenyloxy) ethylthio group, 3-pheni Ruoxypropylthio group, 3- (4′-ethylphenyloxy) propylthio group, 3- (4′-chlorophenyloxy) propylthio group, 3- (2′-naphthyloxy) propylthio group, 4-phenyloxybutylthio group A linear, branched or cyclic alkylthio group which may have a substituent such as 6-phenyloxyhexylthio group, 8-phenyloxyoctylthio group, 10-phenyloxydecylthio group,

For example, vinyl group, allyl group, 2-butenyl group, 3-butenyl group, 1-methyl-4-pentenyl group, 2-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-hexenyl group 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 2-heptenyl group, 1-vinylhexyl group, 3-nonenyl group, 6-nonenyl group, 9-decenyl group, 10-undecenyl group, 13-tetradecenyl group Group, 15-hexadecenyl group, 17-octadecenyl group, 23-tetracocenyl group, 1-cyclopentenyl group, 1-cyclohexenyl group, ethoxyvinyl group, n-butoxyvinyl group, benzylvinyl group, cinnamyl group, 2,2 -Diphenylvinyl group, 2- (4'-methylphenyl) vinyl group, 2- (3'-methylphenyl) vinyl group, 2- (4 ' A linear, branched or cyclic alkenyl group which may have a substituent such as -methoxyphenyl) vinyl group, 2- (4'-chlorophenyl) vinyl group, phenyloxyvinyl group,

For example, vinyloxy group, allyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl-4-pentenyloxy group, 2-pentenyloxy group, 4-pentenyloxy group, 1-methyl-2-butenyloxy group, 2 -Hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 2-heptenyloxy group, 1-vinylhexyloxy group, 3-nonenyloxy group, 6-nonenyloxy group, 9-decenyloxy group, 10-undecenyloxy group, 13-tetradecenyloxy group, 15-hexadecenyloxy group, 17-octadecenyloxy group, 23-tetracocenyloxy group, 1-cyclopentenyloxy group 1-cyclohexenyloxy group, ethoxyvinyloxy group, n-butoxybini Oxy group, a benzyl vinyl group, cinnamyloxy group, may straight chain optionally having a substituent, such as phenyloxy vinyl group, branched or cyclic alkenyloxy group,

For example, vinylthio group, allylthio group, 2-butenylthio group, 3-butenylthio group, 4-pentenylthio group, 5-hexenylthio group, 9-decenylthio group, 13-tetradecenylthio group, 15-hexadecenylthio group , 17-octadecenylthio group, 23-tetracocenylthio group, 1-cyclohexenylthio group, n-butoxyvinylthio group and the like, which may have a substituent, linear, branched or cyclic alkenylthio Group,

For example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4- Methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2- tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4- Phenethylbenzyl group, 4-phenylbenzyl group, 4- (4′-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n-tetradecyl Oxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl Group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group, 4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4- Hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2- Fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group A substituted or unsubstituted aralkyl group having 4 to 20 carbon atoms, such as

For example, benzyloxy group, phenethyloxy group, β-methylphenethyloxy group, 4-methylphenethyloxy group, 4-methylbenzyloxy group, 3-methylbenzyloxy group, 2-methylbenzyloxy group, 4-ethylbenzyloxy group Group, 4-isopropylbenzyloxy group, 4-tert-butylbenzyloxy group, 4-cyclohexylbenzyloxy group, 4-n-octylbenzyloxy group, 4-allylbenzyloxy group, 4-benzylbenzyloxy group, 4- Phenylbenzyloxy group, 4- (4′-methylphenyl) benzyloxy group, 4-methoxybenzyloxy group, 2-methoxybenzyloxy group, 2-ethoxybenzyloxy group, 4-n-butoxybenzyloxy group, 4- n-heptyloxybenzyloxy group, 4-n-decyl Oxybenzyloxy group, 4-n-tetradecyloxybenzyloxy group, 4-n-heptadecyloxybenzyloxy group, 3,4-dimethoxybenzyloxy group, 4-methoxymethylbenzyloxy group, 4-isobutoxymethylbenzyl Oxy group, 4-allyloxybenzyloxy group, 4-vinyloxymethylbenzyloxy group, 4-benzyloxybenzyloxy group, 4-phenethyloxybenzyloxy group, 4-phenyloxybenzyloxy group, 3-phenyloxybenzyloxy group Group, 4-hydroxybenzyloxy group, 4-fluorobenzyloxy group, 4-chlorobenzyloxy group, 3-chlorobenzyloxy group, 3,4-dichlorobenzyloxy group, 1-naphthylmethyloxy group, 2-naphthylmethyl 4 carbon atoms such as oxy group 20 substituted or unsubstituted aralkyl group,

For example, benzylthio group, phenethylthio group, β-methylphenethyloxy group, 4-methylphenethylthio group, 4-methylbenzylthio group, 3-methylbenzylthio group, 4-ethylbenzylthio group, 4-isopropylbenzylthio group 4-tert-butylbenzylthio group, 4-cyclohexylbenzylthio group, 4-n-octylbenzylthio group, 4-allylbenzylthio group, 4-benzylbenzylthio group, 4-phenylbenzylthio group, 4- ( 4'-methylphenyl) benzylthio group, 4-methoxybenzylthio group, 2-methoxybenzylthio group, 2-ethoxybenzylthio group, 4-n-butoxybenzylthio group, 4-n-heptyloxybenzylthio group, 4 -N-decyloxybenzylthio group, 4-n-tetradecyloxybenzylthio group, 4 -N-heptadecyloxybenzylthio group, 3,4-dimethoxybenzylthio group, 4-methoxymethylbenzylthio group, 4-allyloxybenzylthio group, 4-benzyloxybenzylthio group, 4-phenethyloxybenzylthio group 4-phenyloxybenzylthio group, 3-phenyloxybenzylthio group, 4-hydroxybenzylthio group, 4-fluorobenzylthio group, 4-chlorobenzylthio group, 1-naphthylmethylthio group, 2-naphthylmethylthio group, etc. A substituted or unsubstituted aralkylthio group having 4 to 20 carbon atoms,

For example, phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 9-anthracenyl group, fluorenyl group, 4-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 3- Furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, 4-methylphenyl Group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl Group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butyl Phenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-nonylphenyl group 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-n-hexadecylphenyl group, 4-n-octadecylphenyl group, 4-cyclopentylphenyl group, 4 -Cyclohexylphenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 4- (4'-methyl) Kurohekishiru) phenyl group, 3-phenyl group, 2-cyclohexyl-phenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group,

2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2, 3,5-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6- Diethylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5-di- tert-butylphenyl group, 2,4-dineopentylphenyl group, 2,5-di-tert-pentylphenyl group, 4,6-di-tert-butyl-2-methylphenol Nyl group, 5-tert-butyl-2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-indanyl group, 1,2 , 3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group,

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl Group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2 -Isopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2'-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyl Oxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphene Group, 4-n-hexadecyloxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-1-naphthyl group, 4-methoxy-1 -Naphtyl group, 4-n-butoxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n-hexyloxy -2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy-2-naphthyl group,

2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3, 5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3 -Methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3 , 4,5-trimethoxyphenyl group,

4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-chloro-1 -Naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6- Difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3, 4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichloroph An phenyl group, a 2,3,6-tribromophenyl group, a 3,4,5-trifluorophenyl group, a 2,4-dichloro-1-naphthyl group, a 1,6-dichloro-2-naphthyl group,

2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 3-fluoro-2-methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4-chloro-3-methylphenyl group, 2-chloro-4,6-dimethylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl Group, 3-fluoro-4-ethoxyphenyl group, 5-chloro-2-methoxyphenyl group, 6-chloro-3-methoxyphenyl group, 5-chloro-2, -Dimethoxyphenyl group, 2-chloro-4-nitrophenyl group, 4-chloro-2-nitrophenyl group, 4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3 , 5-bis (trifluoromethyl) phenyl group, 4-trifluoromethyloxyphenyl group,

4-allylphenyl group, 2-allylphenyl group, 2-isopropenylphenyl group, 4-benzylphenyl group, 2-benzylphenyl group, 4- (4′-methylbenzyl) phenyl group, 4-cumylphenyl group, 4- (4′-methoxycumyl) phenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-ethylphenyl) phenyl group 4- (4′-isopropylphenyl) phenyl group, 4- (4′-tert-butylphenyl) phenyl group, 4- (4′-n-hexylphenyl) phenyl group, 4- (4′-n-octyl) Phenyl) phenyl group, 4- (4′-methoxyphenyl) phenyl group, 4- (4′-ethoxyphenyl) phenyl group, 4- (4′-n-butyl) Toxiphenyl) phenyl group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-fluorophenyl) phenyl group, 4- (4′-chlorophenyl) phenyl group, 3-methyl-4-phenyl group, 2-methoxy-5-phenylphenyl group, 3-methoxy-4-phenylphenyl group,

4-methoxymethylphenyl group, 4-ethoxymethylphenyl group, 4-n-butoxymethylphenyl group, 3-methoxymethylphenyl group, 4- (2′-methoxyethyl) phenyl group, 4- (2′-ethoxyethyl) Oxy) phenyl group, 4- (2′-n-butoxyethyloxy) phenyl group, 4- (3′-ethoxypropyloxy) phenyl group, 4-vinyloxyphenyl group, 4-allyloxyphenyl group, 3-allyl Oxyphenyl group, 4- (4′-pentenyloxy) phenyl group, 4-allyloxy-1-naphthyl group, 4-allyloxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group,

4-benzyloxyphenyl group, 2-benzyloxyphenyl group, 4-phenethyloxyphenyl group, 4- (4′-chlorobenzyloxy) phenyl group, 4- (4′-methylbenzyloxy) phenyl group, 4- ( 4′-methoxybenzyloxy) phenyl group, 4- (3′-ethoxybenzyloxy) phenyl group, 4-benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, 6 -Benzyloxy-2-naphthyl group, 6- (4'-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4- (2 ' -Benzyloxyethyloxy) phenyl group,

4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-phenoxyphenyl group, 4- (4′-methylphenoxy) phenyl group, 4- (4′-methoxyphenoxy) phenyl group, 4- (4′-chlorophenoxy) ) Phenyl group, 4-phenoxy 1-naphthyl group, 6-phenoxy 2-naphthyl group, 7-phenoxy 2-naphthyl group, 4-phenoxymethylphenyl group, 4- (2′-phenoxyethyloxy) phenyl group, 4- [2 ′-(4′-methylphenoxy) ethyloxy] phenyl group, 4- [2 ′-(4′-methoxyphenoxy) ethyloxy] phenyl group, 4- [2 ′-(4′-chlorophenoxy) ethyloxy] phenyl Group, 4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4-ethylcarbonylphenol Nyl group, 2-ethylcarbonylphenyl group, 4-n-butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1- Naphtyl group, 6-acetyl-2-naphthyl group, 6-n-butylcarbonyl-2-naphthyl group, 4-allylcarbonylphenyl group, 4-benzylcarbonylphenyl group, 4- (4′-methylbenzyl) carbonylphenyl group 4-phenylcarbonylphenyl group, 4- (4′-methylphenyl) carbonylphenyl group, 4- (4′-chlorophenyl) carbonylphenyl group, 4-phenylcarbonyl-1-naphthyl group,

4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propoxycarbonylphenyl group, 4-n-butoxycarbonylphenyl group, 4-n- Hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6-methoxycarbonyl-2-naphthyl group, 6-n-butoxycarbonyl 2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4′-chlorobenzyl) oxycarbonylphenyl group, 4-phenethyloxycarbonylphenyl group, 6-benzyloxy Rubonyl-2-naphthyl group, 4-phenoxycarbonylphenyl group, 4- (4′-ethylphenyl) oxycarbonylphenyl group, 4- (4′-chlorophenyl) oxycarbonylphenyl group, 4- (4′-ethoxyphenyl) An oxycarbonylphenyl group, a 6-phenoxycarbonyl-2-naphthyl group,

4-acetyloxyphenyl group, 3-acetyloxyphenyl group, 2-acetyloxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2-ethylcarbonyloxyphenyl group, 4-n-propylcarbonyloxyphenyl group, 4-n -Pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 4-n-butylcarbonyloxy -1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyloxy Phenyl group 4-phenethylcarbonyloxyphenyl group, 6-benzylcarbonyloxy-2-naphthyl group, 4-phenylcarbonyloxyphenyl group, 4- (4′-methylphenyl) carbonyloxyphenyl group, 4- (2′-methylphenyl) Carbonyloxyphenyl group, 4- (4′-chlorophenyl) carbonyloxyphenyl group, 4- (2′-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2- A naphthyl group, a 7-phenylcarbonyloxy-2-naphthyl group,

4-methylthiophenyl group, 2-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2-isopropylthiophenyl group, 4-n-butylthiophenyl group 2-isobutylthiophenyl group, 2-neopentylphenyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group, 3-benzyl Thiophenyl group, 2-benzylthiophenyl group, 4- (4′-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2-phenylthiophenyl group, 4- (4 ′ -Methylphenylthio) phenyl group, 4- (3'-methylphenylthio) phenyl group, 4- (4'- Methoxyphenylthio) phenyl group, 4- (4′-chlorophenylthio) phenyl group, 2-ethylthio-1-naphthyl group, 4-methylthio-1-naphthyl group, 6-ethylthio-2-naphthyl group, 6-phenylthio- 2-naphthyl group,

4-nitrophenyl group, 3-nitrophenyl group, 2-nitrophenyl group, 3,5-dinitrophenyl group, 4-nitro-1-naphthyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formyl Phenyl group, 4-formyl-1-naphthyl group, 1-formyl-2-naphthyl group,

4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N-ethylpiperazino) phenyl group, 4-pyrrolidino-1-naphthyl group,

4-aminophenyl group, 3-aminophenyl group, 2-aminophenyl group, 4- (N-methylamino) phenyl group, 3- (N-methylamino) phenyl group, 4- (N-ethylamino) phenyl group 2- (N-isopropylamino) phenyl group, 4- (Nn-butylamino) phenyl group, 2- (Nn-butylamino) phenyl group, 4- (Nn-octylamino) phenyl group 4- (Nn-dodecylamino) phenyl group, 4- (N-benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group,

4- (N, N-dimethylamino) phenyl group, 3- (N, N-dimethylamino) phenyl group, 4- (N, N-diethylamino) phenyl group, 2- (N, N-dimethylamino) phenyl group 2- (N, N-diethylamino) phenyl group, 4- (N, N-di-n-butylamino) phenyl group, 4- (N, N-di-n-hexylamino) phenyl group, 4- (N N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group, 4- (N, N-diphenyl) Amino) phenyl group, 4- [N-phenyl-N- (4-methylphenyl) amino] phenyl group, 4- [N, N-di (3′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methyl) Phenyl) amino] phenyl group, 4- [N, N-di (4'-methoxyphenyl) amino] phenyl group, 2- (N, N-diphenylamino) phenyl group,

4-hydroxyphenyl group, 3-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methyl-3-hydroxyphenyl group, 6-methyl-3-hydroxyphenyl group, 2-hydroxy-1-naphthyl group, 8-hydroxy -1-naphthyl group, 4-hydroxy-1-naphthyl group, 1-hydroxy-2-naphthyl group, 6-hydroxy-2-naphthyl group, 4-cyanophenyl group, 2-cyanophenyl group, 4-cyano-1 A substituted or unsubstituted aryl group having 3 to 20 carbon atoms, such as -naphthyl group and 6-cyano-2-naphthyl group;

For example, phenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 4-ethylphenoxy group, 4-n-propylphenoxy group, 4-isopropylphenoxy group, 4-n-butylphenoxy group 4-tert-butylphenoxy group, 4-isopentylphenoxy group, 4-tert-pentylphenoxy group, 4-n-hexylphenoxy group, 4-cyclohexylphenoxy group, 4-n-octylphenoxy group, 4-n- Decylphenoxy group, 4-n-octadecylphenoxy group,

2,3-dimethylphenoxy group, 2,4-dimethylphenoxy group, 2,5-dimethylphenoxy group, 3,4-dimethylphenoxy group, 5-indanyloxy group, 1,2,3,4-tetrahydro-5 -Naphtyloxy group, 1,2,3,4-tetrahydro-6-naphthyloxy group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 3-ethoxyphenoxy group, 4-ethoxyphenoxy group 4-n-propoxyphenoxy group, 4-isopropoxyphenoxy group, 4-n-butoxyphenoxy group, 4-n-pentyloxyphenoxy group, 4-n-hexyloxyphenoxy group, 4-cyclohexyloxyphenoxy group, 4 -N-heptyloxyphenoxy group, 4-n-octyloxyphenoxy group, 4-n-de Ruoxyphenoxy group, 2,3-dimethoxyphenoxy group, 2,5-dimethoxyphenoxy group, 3,4-dimethoxyphenoxy group, 2-methoxy-5-methylphenoxy group, 3-methyl-4-methoxyphenoxy group, 2 -Fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group, 3-chlorophenoxy group, 4-chlorophenoxy group, 4-bromophenoxy group, 4-trifluoromethylphenoxy group, 3 , 4-dichlorophenoxy group, 2-methyl-4-chlorophenoxy group, 2-chloro-4-methylphenoxy group, 3-chloro-4-methylphenoxy group, 2-chloro-4-methoxyphenoxy group, 4-phenyl Phenoxy group, 3-phenylphenoxy group, 4- (4′-methylphenyl) phen Xyl group, 4- (4′-methoxyphenyl) phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-ethoxy-1-naphthyloxy group, 6-methoxy-2-naphthyloxy group, 7-ethoxy C2-C20 such as 2-naphthyloxy group, 2-furyloxy group, 2-thienyloxy group, 3-thienyloxy group, 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group A substituted or unsubstituted aryloxy group,

For example, phenylthio group, 3-methylphenylthio group, 4-methylphenylthio group, 4-ethylphenylthio group, 4-n-propylphenylthio group, 4-n-butylphenylthio group, 4-tert-butylphenyl Thio group, 4-n-hexylphenylthio group, 4-cyclohexylphenylthio group, 4-n-octylphenylthio group, 4-n-dodecylphenylthio group, 4-n-octadecylphenylthio group, 2,3- Dimethylphenylthio group, 3,4-dimethylphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 3-ethoxyphenylthio group, 4-ethoxyphenylthio group, 4-n-propoxyphenylthio group 4-n-butoxyphenylthio group, 4-n-hexyloxyphenylthio group, 4-n-octyloxy Phenylthio group, 4-n-decyloxyphenylthio group, 3,4-dimethoxyphenylthio group, 3-methyl-4-methoxyphenylthio group, 3-fluorophenylthio group, 4-fluorophenylthio group, 4-chlorophenyl Thio group, 2-methyl-4-chlorophenylthio group, 2-chloro-4-methoxyphenylthio group, 4-phenylphenylthio group, 4- (4′-methylphenyl) phenylthio group, 4- (4′-methoxy) Phenyl) phenylthio group, 1-naphthylthio group, 2-naphthylthio group and the like, a substituted or unsubstituted arylthio group having 3 to 20 carbon atoms,

For example, N-methylamino group, N-ethylamino group, N-isopropylamino group, Nn-butylamino group, Nn-hexylamino group, Nn-decylamino group, Nn-tetradecylamino group Group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-butylamino group, N, N-di-n-hexylamino group, N, N-di-n-octyl Amino group, N, N-di-n-decylamino group, N, N-di-n-dodecylamino group, N-phenylamino group, N- (4-methylphenyl) amino group, N-phenyl-N-methyl Amino group, N-phenyl-N-ethylamino group, N, N-diphenylamino group, N, N-di (4-methylphenyl) amino group, N, N-di (4-ethylphenyl) amino group, N , N-di (4-methoxyphenyl) Amino group, N- phenyl--N- naphthylamino number 1 to 40 substituted amino group carbons such group, an amino group, a cyano group, a hydroxyl group,

For example, carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-octyloxycarbonyl group 2-ethylhexyloxycarbonyl group, n-decyloxycarbonyl group, n-dodecyloxycarbonyl group, n-tetradecyloxycarbonyl group, n-hexadecyloxycarbonyl group, n-octadecyloxycarbonyl group, cyclohexyloxycarbonyl group, Benzyloxycarbonyl group, phenethyloxycarbonyl group, (4-methylbenzyloxy) carbonyl group, (3-methylbenzyloxy) carbonyl group, (4-tert-butylbenzyloxy) Rubonyl group, (4-methoxybenzyloxy) carbonyl group, (4-chlorobenzyloxy) carbonyl group, phenoxycarbonyl group, (4-methylphenoxy) carbonyl group, (3-methylphenoxy) carbonyl group, (4-ethylphenoxy) ) Carbonyl group, (4-tert-butylphenoxy) carbonyl group, (4-methoxyphenoxy) carbonyl group, (2-methoxyphenoxy) carbonyl group, (4-ethoxyphenoxy) carbonyl group, (4-fluorophenoxy) carbonyl group -COOR ³¹ group such as (in the group, R ³¹ represents the same meaning as above),

For example, formyl group, methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, n-butylcarbonyl group, n-hexylcarbonyl group, n-octylcarbonyl group, 2-ethylhexylcarbonyl group, n-decylcarbonyl group, n -Dodecylcarbonyl group, n-tetradecylcarbonyl group, n-hexadecylcarbonyl group, n-octadecylcarbonyl group, cyclohexylcarbonyl group, benzylcarbonyl group, phenethylcarbonyl group, (4-methylbenzyl) carbonyl group, (4-tert -Butylbenzyl) carbonyl group, (4-methoxybenzyl) carbonyl group, (4-chlorobenzyl) carbonyl group, phenylcarbonyl group, (4-methylphenyl) carbonyl group, (3-methylphenyl) carbonyl group, (4- D Tilphenyl) carbonyl group, (4-tert-butylphenyl) carbonyl group, (4-methoxyphenyl) carbonyl group, (2-methoxyphenyl) carbonyl group, (4-ethoxyphenyl) carbonyl group, (4-fluorophenyl) carbonyl -COR ³² group such as group, amide (in the group, R ³² has the same meaning as above),

For example, methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, n-butylcarbonyloxy group, n-pentylcarbonyloxy group, n-hexylcarbonyloxy group, n-octylcarbonyloxy group, 2-ethylhexyl Carbonyloxy group, n-decylcarbonyloxy group, n-dodecylcarbonyloxy group, n-tetradecylcarbonyloxy group, n-hexadecylcarbonyloxy group, n-octadecylcarbonyloxy group, cyclohexylcarbonyloxy group, benzylcarbonyloxy group , Phenethylcarbonyloxy group, (4′-methylbenzylcarbonyl) oxy group, (4′-tert-butylbenzylcarbonyl) oxy group, (4′-methoxybenzylcarbonyl) oxy group, (4′- (Rorobenzylcarbonyl) oxy group, phenylcarbonyloxy group, (4′-methylphenylcarbonyl) oxy group, (3′-methylphenylcarbonyl) oxy group, (4′-ethylphenylcarbonyl) oxy group, (4′-tert) -Butylphenylcarbonyl) oxy group, (4'-methoxyphenylcarbonyl) oxy group, (2'-methoxyphenylcarbonyl) oxy group, (4'-ethoxyphenylcarbonyl) oxy group, (4'-fluorophenylcarbonyl) oxy And —OCOR ³³ group (in the group, R ³³ represents the same meaning as described above).

  Although the compound represented by the general formula [2] that can be used in the present invention has been described above, these dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3 ′ The molecular weight of the -lm] perylene derivative is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. This is because there is a concern that if the molecular weight is large, the vapor deposition property may be deteriorated when an element is formed by vapor deposition.

  Table 2 below shows typical examples of dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivatives that can be used in the organic EL device of the present invention ( Exemplified compounds 81 to 200) are shown, but the present invention is not limited to these compounds (however, in Table 2, t-Bu is a tert-butyl group, Ph is a phenyl group, and tol is p-tolyl). Group, Bz represents a benzyl group).

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

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

  Among the above materials, examples of the hole injection material or the hole transport material that can be particularly preferably used include aromatic tertiary amine derivatives and phthalocyanine derivatives. Examples of the aromatic tertiary amine derivative include N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N, N ′. , N ′-(4-methylphenyl) -1,1′-phenyl-4,4′-diamine, N, N, N ′, N ′-(4-methylphenyl) -1,1′-biphenyl-4 , 4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-(methylphenyl) -N, N ′-( 4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, and oligomers having these aromatic tertiary amine skeletons Or polymers, these are holes Input materials, can be suitably used for any hole transport material. Examples of the phthalocyanine (Pc) derivative include H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, Examples thereof include phthalocyanine derivatives such as TiOPc, MoOPc, and GaPc—O—GaPc, and these can be suitably used particularly for hole injection materials.

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

  Among the electron injection materials, particularly effective electron injection materials include metal complex compounds and nitrogen-containing five-membered ring derivatives. Among the electron injection materials that can be used in the present invention, preferable metal complex compounds include tris (8-hydroxyquinolinate) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, and tris (5-phenyl). -8-hydroxyquinolinato) aluminum, bis (8-hydroxyquinolinato) (1-naphtholato) aluminum, bis (8-hydroxyquinolinato) (2-naphtholato) aluminum, bis (8-hydroxyquinolinate) ) (Phenolate) aluminum, bis (8-hydroxyquinolinato) (4-cyano-1-naphtholato) aluminum, bis (4-methyl-8-hydroxyquinolinato) (1-naphtholato) aluminum, bis (5- Methyl-8-hydroxyquinolinate) (2-naphthler) ) Aluminum, bis (5-phenyl-8-hydroxyquinolinato) (phenolate) aluminum, bis (5-cyano-8-hydroxyquinolinato) (4-cyano-1-naphtholato) aluminum, bis (8-hydroxy) Quinolinate) chloroaluminum, aluminum complex compounds such as bis (8-hydroxyquinolinate) (o-cresolate) aluminum, tris (8-hydroxyquinolinato) gallium, tris (2-methyl-8-hydroxyquinoli) Nato) gallium, tris (2-methyl-5-phenyl-8-hydroxyquinolinato) gallium, bis (2-methyl-8-hydroxyquinolinato) (1-naphtholato) gallium, bis (2-methyl-8) -Hydroxyquinolinate) (2-naphtholate) gallium, bi (2-Methyl-8-hydroxyquinolinate) (phenolate) gallium, bis (2-methyl-8-hydroxyquinolinato) (4-cyano-1-naphtholato) gallium, bis (2,4-dimethyl-8) -Hydroxyquinolinate) (1-naphtholato) gallium, bis (2,5-dimethyl-8-hydroxyquinolinato) (2-naphtholato) gallium, bis (2-methyl-5-phenyl-8-hydroxyquinolinate) Nato) (phenolate) gallium, bis (2-methyl-5-cyano-8-hydroxyquinolinato) (4-cyano-1-naphtholato) gallium, bis (2-methyl-8-hydroxyquinolinato) chlorogallium Gallium complex compounds such as bis (2-methyl-8-hydroxyquinolinate) (o-cresolate) gallium In addition, 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinate) copper, bis (8-hydroxyquinolinate) manganese, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (8-hydroxyquinone) Nolinato) zinc and metal complex compounds such as bis (10-hydroxybenzo [h] quinolinato) zinc.

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

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

  The light emitting layer of the organic EL device of the present invention comprises an amine compound represented by the general formula [1] and a dibenzo [f, f ′] diindeno [1,2,3- cd: 1 ′, 2 ′, 3′-lm] perylene derivatives are featured, but may contain other host materials or dopants. In this case, the dopant concentration is preferably contained in the range of 0.001 to 30% by weight with respect to the host material, more preferably in the range of 0.01 to 10% by weight, More preferably, it is contained in the range of ˜5% by weight.

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

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

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

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

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

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

  As described above, this organic EL element can obtain red light emission exhibiting high color purity and luminance at a low driving voltage. Therefore, this organic EL device can be applied to flat panel displays such as wall-mounted televisions and flat light emitters, as well as light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. Can be considered.

  EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example at all. In this example, all mixing ratios indicate weight ratios unless otherwise specified.

Example 1
A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and then the vapor deposition tank was depressurized to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, a compound 3 in Table 1 as an amine compound and a dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative as an amine compound were used. Compound 87 of No. 2 was co-deposited from a different vapor deposition source to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec (weight ratio 100: 0.5) to obtain a light emitting layer, and then tris (8-quinolinolate). ) Aluminum was vapor deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron transport layer, and magnesium and silver were further deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm. Vapor deposition (weight ratio 10: 1) is used as the cathode, and organic To prepare a click Toro EL device. Incidentally, the deposition was performed while maintaining the vacuum of the deposition chamber. The organic electroluminescent element produced, was defeated indicia DC voltage, red brightest 31000cd / m ² of the light-emitting there was confirmed. this element is brightness at the driving voltage of 5V was 450 cd / m ^2. half life when further driven with a constant current in emission luminance 500 cd / m ² was 5000 hours.

Examples 2 to 18
An organic EL device was produced in the same manner as in Example 1 except that the amine compound shown in Table 3 was used instead of Compound 3. When a direct current voltage was applied to each element in a dry atmosphere, light emission of orange red to red was confirmed. Table 3 shows the half-life when these elements are driven at a constant current at the maximum luminance, the luminance at a driving voltage of 5 V, and the emission luminance of 500 cd / m ² . All of these elements had a luminance of 250 cd / m ² or more at a driving voltage of 5 V, and a half life of 2500 hours or more when driven at a constant current at an emission luminance of 500 cd / m ² .

Comparative Examples 1 to 3
Tris (8-quinolinolato) aluminum (Alq3) (Comparative Example 1), bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum (BAlq) (Comparative Example) 2) The same as Example 1 except that 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl (α-NPD) (Comparative Example 3) was used. An organic EL device was produced by the method described above, and when direct current voltage was applied to each device, emission of orange red to red was confirmed. The half life when driven at a constant current at a luminance and emission luminance of 500 cd / m ² is shown in Table 4. All of these elements have a luminance of less than 100 cd / m ² at a driving voltage of 5 V, and emit light emission. The half-life when driven at a constant current at a degree of 500 cd / m ² was less than 600 hours.

Examples 19 to 36
The same procedure as in Example 1 except that dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivatives shown in Table 5 are used instead of compound 87. The organic EL element was produced by the method. When direct current voltage was applied to each device, light emission of orange red to red was confirmed. Table 5 shows the half-life when these elements are driven at a constant current at the maximum luminance, the luminance at a driving voltage of 5 V, and the emission luminance of 500 cd / m ² . All of these elements had a luminance of 350 cd / m ² or more at a driving voltage of 5 V, and a half life of 2500 hours or more when driven at a constant current at an emission luminance of 500 cd / m ² .

Comparative Example 4
An organic EL device was produced in the same manner as in Example 1 except that DCJTB shown below was used instead of Compound 87. Luminance at a drive voltage of 5V in this device was 2.3 cd / m ^2, the half-life when the constant current driving with emission luminance 500 cd / m ² was 210 hours.

  As is clear from the embodiments described above, the organic EL device of the present invention can achieve an improvement in light emission luminance and a longer life when driven at a low voltage.

Claims (3)

An organic electroluminescent element material comprising a compound represented by the following general formula [1] and a compound represented by the following general formula [2].
General formula [1]

[Wherein Ar ¹ represents a substituted or unsubstituted perylenyl group;
R ¹ and R ² are each independently a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group.
Ar ¹ and R ¹ , Ar ¹ and R ² , R ¹ and R ² may be bonded to each other to form a ring. ]
General formula [2]

Wherein X ^{1 to} X ²⁰ are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenyl group, a substituted Or an unsubstituted alkenyloxy group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted aryl group , Substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted amino group, cyano group, hydroxyl group, —COOR ³¹ group (where R ³¹ is a hydrogen atom, substituted or unsubstituted alkyl group) A group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, Rui represents a substituted or unsubstituted aryl group), - COR ³² group (wherein, R ³² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, A substituted or unsubstituted aryl group, or a substituted or unsubstituted amino group, or —OCOR ³³ (wherein R ³³ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted group) Represents a substituted aralkyl group or a substituted or unsubstituted aryl group), and X ^{1 to} X ²⁰ may be combined with each other to form a ring. ] 2. The organic electroluminescent device according to claim 1, wherein at least one layer is formed by forming a light emitting layer or a plurality of layers of organic compound thin films including a light emitting layer between a pair of electrodes composed of an anode and a cathode. An organic electroluminescence device including a material. 2. The organic electroluminescence device according to claim 1, wherein a light emitting layer or a plurality of organic compound thin film including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode. An organic electroluminescence device including a material.