JP2007027356A - Material for organic electroluminescence - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an element for long-life organic electroluminescence for emitting red-color light of higher color purity and luminance with a lower drive voltage. <P>SOLUTION: A material for organic electroluminescence comprises: a compound expressed by a general expression [1] wherein Ar<SP>1</SP>is substituted or non-substituted perilenyl group, R<SP>1</SP>and R<SP>2</SP>are independent substituted or non-substituted monohydric aromatic hydrocarbon groups or substituted or non-substituted monohydric aromatic heterocyclic groups; and a compound expressed by a general expression [2] wherein X<SP>1</SP>to X<SP>14</SP>are independent hydrogen atoms. <P>COPYRIGHT: (C)2007,JPO&INPIT

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 an organic electroluminescence device that emits orange or red light at a low driving voltage, and more particularly to an organic electroluminescence device for obtaining red light that exhibits a long lifetime and high color purity and luminance.

  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 the 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. As a result, green light emission with a luminance of several thousand (cd / m 2) at a DC voltage of 6 to 10 V and a maximum luminous 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, using tris (8-quinolinolato) aluminum as a host material and 4H-pyran derivatives such as DCM, DCJ, DCJT, DCJTB An organic EL device that emits orange to red light by using as a dopant is reported.

  As for organic EL elements using a material having a perylene structure, for example, JP-A-10-251633, JP-A-11-144869, JP-A-2001-11031, JP-A-2001-176664, JP-A-2002-129043 and JP-A-2003-201472 are known.

Furthermore, as an organic EL element using a compound having a rubicene structure as a dopant, for example, JP-A-10-340785 and WO98 / 51757 pamphlets can be mentioned.
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. 10-340785 WO98 / 51757 pamphlet

  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 device using a compound having a rubicene structure has a drawback of high driving voltage. 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 Ar ¹ represents a substituted or unsubstituted perylenyl group, R ¹ and R ² each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent group. An 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 ¹⁴ are each independently a hydrogen atom, a hydroxyl group, a carboxylic acid group, a halogen atom, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or an acylamino group. N-alkylcarbamoyl group, N-arylcarbamoyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aromatic group, substituted or unsubstituted alkyloxy group, substituted or unsubstituted aryloxy group, substituted or Represents an unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group (even if adjacent substituents are bonded to form a new ring) Good.) ]

  In addition, the present invention provides an organic electroluminescent 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 a material for a luminescence element.

  The present invention also relates to 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 a material for a luminescence element.

  The organic EL element produced using the organic EL element material of the present invention has heat resistance, emits light at a lower driving voltage than a conventional one, and has a long life, so that it is a flat panel display such as a wall-mounted TV or a flat light emitter. And 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 is an organic electroluminescent element material containing an amine compound represented by the general formula [1] and a compound having a rubicene structure represented by the general formula [2]. The amine compound represented by 1] will be described.

Ar ¹ in the general formula [1] represents a substituted or unsubstituted perylenyl group, and examples of the 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 explained for the substituent of Ar ¹ . The unsubstituted monovalent aromatic hydrocarbon group and the unsubstituted monovalent aromatic heterocyclic group are the monovalent aromatic hydrocarbon group and the unsubstituted monovalent group described for the Ar1 substituent, respectively. It is synonymous with the 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 [4].

General formula [4]

[Wherein Ar ² represents a substituted or unsubstituted perylenyl group, R ³ and Ar ⁴ each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent group. An aromatic heterocyclic 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} ) R 6 -, - Si (R 7) R 8 - is either (here, R ⁵ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted A monovalent aliphatic hydrocarbon group or a substituted or unsubstituted 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 [4] 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 [4] means a divalent monocyclic ring, a condensed ring, or a ring assembly aromatic heterocyclic group, and includes, for example, a 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 general formula [4], more preferred are amine compounds represented by the following general formula [5].

General formula [5]

[Wherein, Ar ⁵ represents a substituted or unsubstituted perylenyl group, Ar ⁶ and Ar ⁸ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent group. Aromatic heterocyclic group, Ar ⁷ and Ar ⁹ are substituted or unsubstituted monovalent aromatic hydrocarbon group, or substituted or unsubstituted monovalent aromatic heterocyclic group, R ⁹ and R ¹⁰ are respectively Independently, it is any one of a direct bond, —O—, —S—, —C (R ¹¹ ) R ¹² —, and —Si (R ¹³ ) R ¹⁴ — (wherein R ^{11 to} R ¹⁴ are respectively Independently, any of a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, and 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 [4], 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.

  In addition, among the amine compounds represented by the general formula [1], other preferable compounds include amine compounds represented by the following general formula [6].

General formula [6]

[Wherein Ar ¹⁰ represents a substituted or unsubstituted perylenyl group, R ¹⁵ , Ar ¹² and Ar ¹³ each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted group. A monovalent aromatic heterocyclic group, Ar ¹¹ is a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group, R ¹⁶ is a direct bond, O -, - S -, - C (R 17) R 18 -, - Si (R 19) R 20 - is either (here, R ¹⁷ to R ²⁰ each independently represent a hydrogen atom, a substituted Or an unsubstituted monovalent aliphatic hydrocarbon group or a substituted or unsubstituted monovalent aromatic hydrocarbon group). Ar ¹⁰ 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 [4], 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 [6], particularly preferred are amine compounds represented by the following general formula [7].

General formula [7]

[In the formula, Ar ¹⁴ represents a substituted or unsubstituted perylenyl group, Ar ¹⁵ and Ar ¹⁸ each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent group. The aromatic heterocyclic group, Ar ¹⁶ , Ar ¹⁷ , Ar ¹⁹ and Ar ²⁰ are each independently a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic ring. The groups R ²¹ and R ²² are any of a direct bond, —O—, —S—, —C (R ²³ ) R ²⁴ —, —Si (R ²⁵ ) R ²⁶ — (wherein R ²³ to R ²⁶ each independently represent a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, or a monovalent aromatic hydrocarbon group substituted or unsubstituted). 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 [4], 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 compound having a rubicene structure represented by the general formula [2] used in the present invention will be described.

General formula [2]

[Wherein X ^{1 to} X ¹⁴ are each independently a hydrogen atom, a hydroxyl group, a carboxylic acid group, a halogen atom, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or an acylamino group. N-alkylcarbamoyl group, N-arylcarbamoyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted alkyloxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted Represents a substituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heterocyclic group (may combine with adjacent substituents to form a new ring. .) ]

In the general formula [2], X ^{1 to} X ¹⁴ are each independently a hydrogen atom, a hydroxyl group, a carboxylic acid group, a halogen atom, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, or an aryloxycarbonyl. Group, acyloxy group, acylamino group, N-alkylcarbamoyl group, N-arylcarbamoyl group, alkyl group, aryl group, alkyloxy group, aryloxy group, alkylthio group, arylthio group, amino group, or heterocyclic group The adjacent groups may be bonded to each other to form a condensed 5-membered ring, a condensed 6-membered ring, a condensed hetero 5-membered ring, or a condensed hetero 6-membered ring. The acyl, alkyl, aryl, amino, and heterocycle may further have a substituent.

Examples of the halogen atom of the substituent represented by X ^{1 to} X ¹⁴ of the present invention include chlorine, bromine, iodine and fluorine. Of these, fluorine and chlorine are preferred.

  Examples of the acyl group include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, cyclohexylcarbonyl group, benzoyl group, and phenylacetyl group. Among these, an acetyl group, a propionyl group, and a phenylacetyl group are preferable.

  Examples of the alkyloxycarbonyl group include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a cyclohexyloxycarbonyl group, and a benzyloxycarbonyl group. Among these, a methyloxycarbonyl group, an ethyloxycarbonyl group, and a cyclohexyloxycarbonyl group are preferable.

  Examples of the aryloxycarbonyl group include a phenyloxycarbonyl group, a tolyloxycarbonyl group, a biphenylyloxycarbonyl group, a naphthyloxycarbonyl group, an anthryloxycarbonyl group, a pyrenyloxycarbonyl group, and a perylenyloxycarbonyl group. Etc. Among these, a phenyloxycarbonyl group, a tolyloxycarbonyl group, and a biphenylyloxycarbonyl group are preferable.

  Examples of the acyloxy group include formyloxy group, acetyloxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, cyclohexylcarbonyloxy group, benzoyloxy group, and phenylacetyloxy group. Among these, an acetyloxy group, a cyclohexylcarbonyloxy group, and a phenylacetyloxy group are preferable.

  Examples of the acylamino group include formylamino group, acetylamino group, propionylamino group, butyrylamino group, isobutyrylamino group, benzoylamino group, and the like. Among these, an acetylamino group, a propionylamino group, and a butylamino group are preferable.

  Examples of the N-alkylcarbamoyl group include a carbamoyl group, an N-methylcarbamoyl group, an N-ethylcarbamoyl group, an N-propylcarbamoyl group, an N-isopropylcarbamoyl group, an N-cyclohexylcarbamoyl group, and an N-benzylcarbamoyl group. Etc. Among these, an N-methylcarbamoyl group, an N-ethylcarbamoyl group, and an N-cyclohexylcarbamoyl group are preferable.

  Examples of the N-arylcarbamoyl group include N-phenylcarbamoyl group, N-tolylcarbamoyl group, N-biphenylylcarbamoyl group, N-naphthylcarbamoyl group, N-anthrylcarbamoyl group, and N-pyrenylcarbamoyl group. And N-perylenylcarbamoyl group. Among these, N-phenylcarbamoyl group, N-tolylcarbamoyl group, and N-biphenylylcarbamoyl group are preferable.

  Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, and a trichloromethyl group. Is mentioned. Among these, a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, and a tert-butyl group are preferable.

  Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a 3-methylphenyl group, a 3-methoxyphenyl group, a 3-fluorophenyl group, a 3- A trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitrophenyl group, etc. are mentioned. Of these, a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, and a fluorenyl group are preferable.

  Examples of the alkyloxy group include a methoxy group, n-butoxy group, tert-butoxy group, trichloromethoxy group, trifluoroethoxy group, pentafluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group, Examples include 1,1,1,3,3,3-hexafluoro-2-propoxy group, 6- (perfluoroethyl) hexyloxy group, and benzyloxy group. Among these, a methoxy group, n-butoxy group, and tert-butoxy group are preferable.

  Examples of the aryloxy group include a phenoxy group, a p-nitrophenoxy group, a p-tert-butylphenoxy group, a 3-fluorophenoxy group, a pentafluorophenyl group, a 3-trifluoromethylphenoxy group, a naphthyloxy group, And anthryloxy group. Among these, a phenoxy group, a naphthyloxy group, and an anthryloxy group are preferable.

  Examples of the alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and a trifluoromethylthio group. Among these, a methylthio group, an ethylthio group, and a tert-butylthio group are preferable.

  Examples of the arylthio group include a phenylthio group, a p-nitrophenylthio group, a p-tert-butylphenylthio group, a 3-fluorophenylthio group, a pentafluorophenylthio group, and a 3-trifluoromethylphenylthio group. Is mentioned. Among these, a phenylthio group and a p-tert-butylphenylthio group are preferable.

  Examples of the amino group include an amino group, a methylamino group, a diethylamino group, an ethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, and a diphenylamino group. Among these, a diethylamino group, a dipropylamino group, a dibutylamino group, and a diphenylamino group are preferable.

  Examples of the heterocyclic group include pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, indolinyl group, quinolinyl group, acridinyl group, pyrrolidinyl group, dioxanyl group, piperidinyl group, morpholinyl group, piperazinyl group, carbazolyl Group, furanyl group, thiophenyl group, oxazolyl group, oxadiazolyl group, benzoxazolyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group, imidazolyl group, benzoimidazolyl group, pranyl group and the like. Among these, a pyridinyl group, a quinolinyl group, a carbazolyl group, a furanyl group, a thiophenyl group, and an oxazolyl group are preferable.

  These substituents include condensed 5-membered rings formed by bonding adjacent groups to each other, condensed 6-membered rings formed by bonding adjacent groups, and condensed groups formed by bonding adjacent groups to each other. A telo 5-membered ring or a condensed hetero 6-membered ring formed by bonding with each other between adjacent groups may be formed.

  Examples of the 5-membered ring formed as a result of bonding between adjacent groups include a cyclopentane ring and a cyclopentene ring.

  Examples of the 6-membered ring formed as a result of bonding between adjacent groups include a cyclohexane ring, a cyclohexene ring, and a benzene ring.

  Hetero 5-membered rings formed as a result of bonding between adjacent groups include dihydrofuran ring, pyrrolidine ring, dihydrothiophene ring, furan ring, pyrrole ring, thiophene ring, imidazole ring, pyrazole ring, oxazole ring, thiazole A ring etc. are mentioned.

  Examples of the hetero 6-membered ring formed as a result of bonding of adjacent groups to each other include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and a pyranone ring.

In addition, the above acyl (acyl group, acyloxy group, acylamino group), alkyl (alkyloxycarbonyl group, N-alkylcarbamoyl group, alkyl group, alkyloxy group, alkylthio group), aryl (aryloxycarbonyl group, N-ary) The rucarbamoyl group, aryl group, aryloxy group, arylthio group), amino (amino group), and heterocyclic ring (heterocyclic group) may further have a substituent.
Examples of the substituent that the substituent may further have include a hydroxyl group, a carboxylic acid group, a halogen atom, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, N- Examples thereof include an alkylcarbamoyl group, an N-arylcarbamoyl group, an alkyl group, an aryl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, and a heterocyclic group, and examples thereof are the same as those described above. .

  The compound represented by the general formula [2] that can be used in the present invention has been described above, but the molecular weight of the compound having a rubicene structure is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. . The reason for this is that if the molecular weight is large, there is a concern that the vapor deposition property is deteriorated when an element is formed by vapor deposition.

  Table 2 below shows representative examples (exemplary compounds D1 to D75) of compounds having a rubicene structure represented by the general formula [2] that can be used in the organic EL device of the present invention. It is not limited to.

  In the present invention, it is preferable to use 0.01 to 100 parts by weight of the compound represented by the following general formula [2] with respect to 100 parts by weight of the compound represented by the general formula [1]. More preferably, it is 0.1-50 weight part. Moreover, as a preferable usage method, for example, a compound represented by the general formula [1] in the light emitting layer is used as a host material, and a compound represented by the general formula [2] is used as a guest material.

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

  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 injecting material or hole transporting material that can be particularly preferably used include aromatic tertiary amine derivatives and phthalocyanine derivatives. Examples of the aromatic tertiary amine derivative include N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N, N ′. , N ′-(4-methylphenyl) -1,1′-phenyl-4,4′-diamine, N, N, N ′, N ′-(4-methylphenyl) -1,1′-biphenyl-4 , 4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-(methylphenyl) -N, N ′-( 4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, and oligomers having these aromatic tertiary amine skeletons Or a polymer, which is a hole injection material or a hole transport material. In Le it can be suitably used. Examples of the phthalocyanine (Pc) derivative include 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 Meeting Proceedings, No. Examples of electron injection materials include BCP, TPP, T5MPyTZ, etc. published on page 3, 1402, 2003. Electrons can be transported by forming a thin film necessary for device fabrication and injecting electrons from the cathode. If it is material, it will not specifically limit to these.

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

  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-bis ( 1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene and the like.

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

  The light emitting layer of the organic EL device of the present invention preferably uses an amine compound represented by the general formula [1] and a compound having a rubicene structure represented by the general formula [2]. These host materials and dopants may be contained. In this case, the dopant concentration is preferably in the range of 0.01 to 100% by weight and more preferably in the range of 0.1 to 50% by weight with respect to the host material.

  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, examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but alloys containing a low work function metal such as lithium, sodium, potassium, calcium, and magnesium are preferable. In addition, an inorganic salt such as lithium fluoride can be used in place of the low work function metal. Moreover, as a preparation method of these cathodes, they can be prepared by methods known in the industry such as resistance heating, electron beam beam irradiation, sputtering, ion plating, and coating. The anode and cathode described above may be formed with a layer structure of two or more layers as necessary.

  In order to efficiently extract light emitted from the organic EL device of the present invention, it is desirable that the substrate material on the surface from which light is extracted is sufficiently transparent. Specifically, the transmittance of light emitted from the device in the 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.

  In addition, in order to improve the stability of the organic EL element with respect to temperature, humidity, atmosphere, etc., 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 the vapor deposition tank was depressurized to 4 × 10 ⁻⁶ Torr. First, N, N′-di (naphthalen-1-yl) -N, N′-diphenyl-benzidine having a molecular structure represented by the following formula (A) is deposited on an ITO transparent electrode at a deposition rate of 0.2 nm. The film was deposited at a thickness of 80 nm at / sec to form a hole transport layer. Next, the compound 3 of Table 1 as an amine compound and the compound D19 of Table 2 as a compound having a rubicene structure were co-deposited to a thickness of 45 nm at a deposition rate of 0.2 nm / sec from a different deposition source (weight ratio 100: 2) to obtain a light emitting layer. Next, tris (8-quinolinolato) aluminum having a molecular structure represented by the following formula (B) was deposited to a thickness of 60 nm at a deposition rate of 0.2 nm / sec to form an electron transport layer. Furthermore, magnesium and silver were co-evaporated to a thickness of 200 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. In addition, vapor deposition was implemented, maintaining the pressure reduction state of a vapor deposition tank. When direct current voltage was applied to the produced organic electroluminescence device, red light emission with a maximum luminance of 40000 cd / m ² was confirmed. This element is brightness at the driving voltage of 5V was 700 cd / m ^2. Further, the half-life when driven at a constant current at an emission luminance of 1000 cd / m ² was 2900 hours.

Examples 2 to 20
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, red light emission was confirmed. In these devices, it is shown in Table 3 together half life when driven with a constant current in luminance and emission luminance 1000 cd / m ² at the maximum brightness and the driving voltage 5V. All of these elements had a luminance of 500 cd / m ² or more at a driving voltage of 5 V, and a half life of 2000 hours or more when driven at a constant current at an emission luminance of 1000 cd / m ² .

Table 3

Comparative Examples 1 to 3
N, N′-di (naphthalen-1-yl) -N, N′-diphenyl-benzidine (formula (A)) (Comparative Example 1), tris (8-quinolinolato) which are known compounds instead of compound 3 ) Aluminum (Formula (B)) (Comparative Example 2), Bis (2-methyl-8-quinolinolato) (4-phenylphenolate) Aluminum (Formula (C) below) (Comparative Example 3) An organic EL device was produced in the same manner as in Example 1. When a direct current voltage was applied to each device under a dry atmosphere, light emission of orange to red-orange was confirmed. Table 4 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 1000 cd / m ² . All of these devices, the luminance of the drive voltage 5V is less than 200 cd / m ^2, the half-life when the constant current driving with emission luminance 1000 cd / m ² was less than 500 hours.

Table 4

Example 21 to Example 36
An organic EL device was produced in the same manner as in Example 1 except that a compound having a rubicene structure shown in Table 5 was used instead of the compound D19. When direct current voltage was applied to each element, red light emission was confirmed. Table 5 shows the half life when these elements were driven at a constant current at the maximum luminance, the luminance at a driving voltage of 5 V, and the emission luminance of 1000 cd / m ² . All of these elements had a luminance of 500 cd / m ² or more at a driving voltage of 5 V, and a half life of 2000 hours or more when driven at a constant current at an emission luminance of 1000 cd / m ² .

Comparative Example 4
An organic EL device was produced in the same manner as in Example 1 except that DCJTB represented by the following formula (D) was used instead of compound D19. The maximum brightness in the element at 2800 cd / m ^2, the luminance of the drive voltage 5V is 10 cd / m ^2, the half-life when the constant current driving with emission luminance 500 cd / m ² was 36 hours.

  As is clear from the above-described embodiments, 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 each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent group. An 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 ¹⁴ are each independently a hydrogen atom, a hydroxyl group, a carboxylic acid group, a halogen atom, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or an acylamino group. N-alkylcarbamoyl group, N-arylcarbamoyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aromatic group, substituted or unsubstituted alkyloxy group, substituted or unsubstituted aryloxy group, substituted or Represents an unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group (even if adjacent substituents are bonded to form a new ring) Good.) ] The organic electroluminescence device according to claim 1, wherein at least one layer is formed by forming a light emitting layer or a plurality of organic compound thin films including the light emitting layer between a pair of electrodes comprising an anode and a cathode. Organic electroluminescence device containing materials for use. 2. The organic electroluminescence device according to claim 1, wherein a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode. Organic electroluminescence device containing materials for use.