JP2005113071A - Organic electroluminescent element material, and organic electroluminescent element using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element of longevity which emits red color light of high color purity and high luminous intensity by a low driving voltage. <P>SOLUTION: The organic electroluminescent element material comprises an amine compound represented by general formula [1], wherein Ar<SP>1</SP>is a substituted or unsubstituted perylenyl group and R<SP>1</SP>and R<SP>2</SP>are each a substituted or unsubstituted monovalent aromatic hydrocarbon group or the like, and a compound having a naphthofluoranthene structure represented by general formula [2], wherein X<SP>1</SP>-X<SP>20</SP>are each independently a hydrogen atom etc. <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 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, 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 element using a compound having a naphthofluoranthene structure as a dopant, for example, JP-A-2003-272866 is 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 JP 2003-272866 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, although an organic EL device using a compound having a naphthofluoranthene structure can produce a device with high color purity, it has a drawback of high driving voltage and short life. 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 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 ^{21 to} X ³⁸ each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In addition, adjacent groups among X ^{33 to} X ³⁸ may be combined to form a monocyclic or polycyclic aromatic 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 is an organic electroluminescent device material containing an amine compound represented by the general formula [1] and a compound having a naphthofluoranthene structure represented by the general formula [2]. The amine compound represented by the general formula [1] will be described.

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 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 unsubstituted 1 described with respect to the substituent for 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 [4].

General formula [4]

[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 [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 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 a direct bond, O, S, = C (R ¹¹ ) R ¹² , = Si (R ¹³ ) R ¹⁴ (where 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 [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 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 a substituted or unsubstituted divalent aromatic heterocyclic group, R ¹⁶ is a direct bond, O, S, = Any one of C (R ¹⁷ ) R ¹⁸ and ═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 an 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]

[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 hydrogen atoms, 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 [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 naphthofluoranthene structure represented by the general formula [2] used in the present invention will be described.

General formula [2]

[Wherein, X ^{21 to} X ³⁸ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted Alternatively, it represents an unsubstituted alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In addition, adjacent groups among X ^{33 to} X ³⁸ may form a monocyclic or polycyclic aromatic ring, and the formed aromatic rings are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted group. Substituted alkyl group having 1 to 18 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, dialkylamino group having 2 to 18 carbon atoms, substituted Alternatively, an unsubstituted diphenylamino group or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms may be bonded. ]

In the general formula [2], X ^{21 to} X ³⁸ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 20 carbon atoms. An alkenyl group, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms Represents.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine, and fluorine and chlorine are preferable.
Examples of the substituted or unsubstituted alkyl group having 1 to 18 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, and n-pentyl group. N-hexyl group, n-heptyl group, n-octyl group, dodecyl group, hexadecyl group, octadecyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2 -Dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2 -Chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl Group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2, 3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3- Diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1 , 2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3- Tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group 1,2,3-trinitropropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, phenethyl group, α-methylbenzyl group, phenylpropyl group, benzyl group, diphenylmethyl group, 4-biphenylmethyl Group, cyclohexylmethyl group and the like. Among these, a methyl group, a t-butyl group, and an isopropyl group are preferable.

  Examples of the substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms include ethenyl group, 1-propenyl group, 2-propenyl group, 1-methylpropenyl group, 2-methylpropenyl group, 1-butenyl group and 2-methylallyl group. , A styryl group, a 2-phenylstyryl group, and the like. Among these, a styryl group and a 2-phenylstyryl group are preferable.

  The substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms is a group represented by -OY, and examples of Y include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s -Butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2- Hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl Group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2, 3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3- Diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1 , 2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3- Tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group 1,2,3-trinitropropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, phenyl group, biphenyl group, benzyl group, phenylethyl group, phenylpropyl group and the like. Among these, Y is preferably a methyl group, a t-butyl group, or a phenyl group.

  Examples of the dialkylamino group having 2 to 18 carbon atoms include dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, methylethylamino group, dibenzylamino group, dicyclohexylamino group, and the like. Among these, a dimethylamino group and a diethylamino group are preferable. Examples of the substituted or unsubstituted aryl group having 6 to 20 carbon atoms include phenyl, naphthyl, anthryl, phenanthryl, naphthacenyl, pyrenyl, fluorenyl, fluoranthenyl, biphenyl, terphenyl, and stilbene. Groups and the like. Among these, a phenyl group, a biphenyl group, a naphthyl group, and a stilbene group are preferable.

In the general formula [2], adjacent groups among X ^{33 to} X ³⁸ may form a monocyclic or polycyclic aromatic ring. For example, a benzene ring, a naphthalene ring, an anthracene ring, an acenaphthyl ring, a phenalene ring Phenanthrene ring, fluoranthene ring and the like, and a benzene ring, naphthalene ring and anthracene ring are preferable. The formed aromatic rings are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms. A linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms May be combined. Specific examples of these linking groups include the same ones as described above.

  In the general formula [2], as each substituent, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or Unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted An aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, a carboxyl group, etc. are mentioned.

  An example of the general formula [2] is a compound represented by the following general formula [3].

General formula [3]

[Wherein, X ^{1 to} X ²⁰ each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted Alternatively, it represents an unsubstituted alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. Further, adjacent groups among X ^{15 to} X ¹⁸ may each form a monocyclic or polycyclic aromatic ring, and the formed aromatic rings are each independently a hydrogen atom, a halogen atom, a substituted or An unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, A substituted or unsubstituted diphenylamino group or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms may be bonded. ]

In the general formula [3], X ^{1 to} X ²⁰ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic carbon number. An alkenyl group having 2 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted carbon number Represents 6 to 20 aryl groups; In the general formula [3], adjacent groups among X ^{15 to} X ¹⁸ may each form a monocyclic or polycyclic aromatic ring. Specific examples thereof are the same as those in the general formula [2]. Things. The formed aromatic rings are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms. A linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms May be combined. Specific examples thereof include those similar to the above general formula [2].

  In the general formula [3], each substituent includes a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, and a substituted group. Or an unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted Aryloxy group, substituted or unsubstituted alkoxycarbonyl group, carboxyl group and the like.

  The compound represented by the general formula [2] that can be used in the present invention has been described above. The molecular weight of the compound having a naphthofluoranthene structure is preferably 2000 or less, more preferably 1500 or less, and 1000 or less. Is particularly preferred. 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 compounds having a naphthofluoranthene structure represented by the general formula [2] that can be used in the organic EL device of the present invention (Exemplary Compounds 81 to 105). However, it is not limited to these.

  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 is characterized by an amine compound represented by the general formula [1] and a compound having a naphthofluoranthene structure represented by the general formula [2]. These host materials and dopants may be contained. 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, the compound 3 of Table 1 as an amine compound and the compound 87 of Table 2 as a compound having a naphthofluoranthene structure were formed from different evaporation sources at a deposition rate of 0.2 nm / sec and a thickness of 50 nm. Then, co-evaporation (weight ratio 100: 0.5) was used to form a light emitting layer, and then tris (8-quinolinolato) aluminum was deposited to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to transport electrons. Further, magnesium and silver were co-deposited to a thickness of 200 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1) to form a cathode, thereby producing an organic electroluminescence device. And. Incidentally, deposition, in. Fabricated organic electroluminescent device were conducted while maintaining the vacuum of the deposition chamber, where the beat mark a DC voltage, red light emission brightest 40000 cd / m ² was observed. This device had a luminance of 400 cd / m ² at a driving voltage of 5 V. Further, the half life when driven at a constant current at an emission luminance of 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 .

Table 3

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.

Table 4

Examples 19 to 36
An organic EL device was produced in the same manner as in Example 1 except that a compound having a naphthofluoranthene structure shown in Table 5 was used instead of the compound 87. 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 ^{21 to} X ³⁸ each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to 18 carbon atoms, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In addition, adjacent groups among X ^{33 to} X ³⁸ may be combined to form a monocyclic or polycyclic aromatic 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.