TW201506128A - Organic electroluminescent device - Google Patents

Abstract

To provide an organic electroluminescent device including a capping layer composed of material having a high refractive index, excelling in stability and durability of a thin film and having no absorption in the respective wavelength regions of blue, green and red in order to improve device characteristics of the organic electroluminescent device, especially to greatly improve light extraction efficiency. In the organic electroluminescent device having at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and the capping layer in this order, the capping layer includes an arylamine compound represented by the following general formula (1): [Formula 1](1).

Description

Organic electroluminescent element

The present invention relates to an organic electroluminescence element (hereinafter simply referred to as an organic EL element) which is a self-luminous element suitable for various display devices, and more particularly to an organic EL element using a specific arylamine compound, particularly regarding light. An organic EL element having a greatly improved efficiency is taken out.

Since the organic EL element is a self-luminous element, it is brighter than the liquid crystal element and has excellent visibility, and can be clearly displayed, and has been actively studied.

In 1987, CWTang et al. of Eastman Kodak Company developed a laminated structural element in which various functions were distributed to various materials, and practical use of an organic EL element using an organic material capable of transporting electrons. When the phosphor is laminated with the organic material capable of transporting the hole, the charge of the two is injected into the phosphor layer to emit light, and the voltage of 10 V or less is obtained at a high luminance of 1000 cd/m ² or more (for example, Patent Document 1 and Patent Document 2).

Until now, there have been many improvements in the practical use of organic EL elements, and various functions have been further subdivided. On the substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer are sequentially disposed on the substrate. In the electric field light-emitting element of the cathode, high efficiency and durability can be achieved by a light-emitting element of a bottom-emission structure that emits light from the bottom (see, for example, Non-Patent Document 1).

In recent years, a light-emitting element having a high-work function metal as an anode and a top-emitting structure that emits light from the upper portion has been used. Unlike the light-emitting elements of the bottom-emitting structure whose area of the light-emitting portion is limited by the pixel circuit, the light-emitting element of the top light-emitting structure has an advantage that the light-emitting portion is wide. In the light-emitting element having a top emission structure, a cathode such as LiF/Al/Ag (see, for example, Non-Patent Document 2), Ca/Mg (for example, see Non-Patent Document 3), and a semi-transparent electrode such as LiF/MgAg are used.

In such a light-emitting element, when light emitted from the light-emitting layer is incident on another film, if it is incident at a certain angle or more, it is totally reflected at the interface between the light-emitting layer and the other film. Therefore, only part of the emitted light can be utilized. In recent years, in order to improve the light extraction efficiency, it has been proposed to provide a light-emitting element having a high refractive index "cover layer" on the outside of a semi-transparent electrode having a low refractive index (see, for example, Non-Patent Documents 2 and 3).

In the light-emitting element of the top light-emitting structure, the effect of the cover layer is as high as 38 cd/A in the case of a light-emitting element using Ir(ppy) ₃ as a light-emitting material, but ZnSe having a film thickness of 60 nm is used as a cover layer. The resulting light-emitting element was 64 cd/A, which was considered to have an efficiency improvement of about 1.7 times. Further, the maximum point of the transmittance of the translucent electrode and the cover layer and the maximum point of the efficiency do not necessarily coincide with each other, and the maximum point display of the light extraction efficiency is determined by the interference effect (see, for example, Non-Patent Document 3).

It has been proposed to use a high-definition metal mask in the formation of a cover layer, but the metal mask may have a problem that the accuracy of positional alignment is deteriorated due to deformation due to heat. In other words, the melting point of ZnSe is as high as 1,100 ° C or higher (see, for example, Non-Patent Document 3), and when a high-definition mask is used, vapor deposition cannot be performed at a correct position. Many inorganic materials have high vapor deposition temperatures, are not suitable for use with high-definition masks, and may cause damage to the light-emitting elements themselves. Further, when a film is formed by a sputtering method, the light-emitting element is damaged, and therefore, an inorganic material cannot be used as a coating layer of a constituent material.

As the cover layer for adjusting the refractive index, it is known to use ginseng (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq ₃ ) (for example, refer to Non-Patent Document 2), and Alq ₃ is used as a green light-emitting material or an electron transport material. An organic EL material generally used, but having a weak absorption in the vicinity of 450 nm used for the blue light-emitting element. Therefore, in the case of the blue light-emitting element, there is a problem that the color purity is lowered and the light extraction efficiency is lowered together.

In order to improve the element characteristics of the organic EL element, in particular, in order to greatly improve the light extraction efficiency, a material having a high refractive index, excellent film stability, or durability is sought for the material of the coating layer. [Prior Art Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. 3,194, 657.

[Non-Patent Document 1] Proceedings of the 9th Workshop of the Applied Physics Society, pp. 55-61 (2001) [Non-Patent Document 2] Appl. Phys. Lett., 78, 544 (2001) [Non-Patent Document 3] Appl. Phys .Lett., 82, 466 (2003) [Non-Patent Document 4] Aust. J. Chem., 45, 371 (1992) [Non-Patent Document 5] J. Org. Chem., 60, 7508 (1995) [Non-Patent Document 6] Synth. Commun., 11, 513 (1981) [Non-Patent Document 7] Appl. Phys. Let., 98, 083302 (2011)

[The subject to be solved by the invention]

An object of the present invention is to provide an organic EL device which is excellent in refractive index, excellent in film stability, and excellent in durability in order to improve the element characteristics of the organic EL element, in particular, in order to improve the light extraction efficiency. , green and red, each of the wavelength regions without a cover layer of absorbing material.

The physical properties in the material suitable for the coating layer of the present invention include (1) high refractive index, (2) vapor deposition and no thermal decomposition, (3) stable film state, and (4) high glass transition temperature. Further, as physical properties of the element suitable for the present invention, (1) high light extraction efficiency, (2) color purity is not lowered, (3) light transmission is not changed with time, and (4) long life is long. . [How to solve the problem]

In order to achieve the above object, the inventors of the present invention have focused on the stability and durability of the film of the arylamine-based material, and selected a specific arylamine compound having a high refractive index as a material constituting the coating layer, and produced an organic EL device, and worked hard to implement the device. The characteristics were evaluated, and the results were achieved.

That is, the following organic EL elements are provided in accordance with the present invention.

1) An organic electroluminescence device comprising, at least in order, an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode electrode, and a cover layer, the cover layer comprising an aromatic amine compound represented by the following formula (1);

【化1】 (1)

(wherein, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, substituted or The unsubstituted condensed polycyclic aromatic group, n represents an integer of 0 to 4; here, at least one of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ is a monovalent group represented by the following structural formula (B) Or having the monovalent group as a substituent)

[Chemical 2] (B)

(wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and may be a linking group, or a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group or a nitro group, and may have a substituent. a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear chain having 2 to 6 carbon atoms which may have a substituent Or a branched alkenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, substituted or Unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy group A single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ is bonded to each other to form a ring; X represents a carbon atom or a nitrogen atom, and Y represents a carbon atom, an oxygen atom, a sulfur atom. , or a nitrogen atom, Ar ₅ represents a substituted or non-substituted aromatic hydrocarbon group, substituted or non-substituted aromatic heterocyclic group, or substituted The unsubstituted condensed polycyclic aromatic group, or a linking group, Ar _6, Ar ₇ may be the same or different from each other, a substituted or non-substituted aromatic hydrocarbon group, substituted or non-substituted aromatic heterocyclic a group, or a substituted or unsubstituted condensed polycyclic aromatic group or a linking group, wherein Y is an oxygen atom or a sulfur atom, Y makes the number of Ar ₇ zero, and X and Y are nitrogen atoms, then Ar ₅ When any of Ar ₆ and Ar ₇ is a substituent or a linking group, X is a nitrogen atom and Y is a carbon atom, X makes the number of Ar ₆ 0. Ar ₈ represents a substituted or unsubstituted aromatic a hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group: R ₁ , R ₂ , R ₃ , R ₄ , Ar ₅ , Ar ₆ , Any one of Ar ₇ is a linking group, and X is a nitrogen atom and Y is an oxygen atom or a sulfur atom. Further, Ar ₆ , Ar ₆ , and Ar ₇ may be the same or different.

2) The organic EL device according to the above 1), wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-1);

[化3] (B-1)

(wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different and may be a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a carbon atom which may have a substituent. a linear or branched alkyl group of 1 to 6 or a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched alkene having 2 to 6 carbon atoms which may have a substituent a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, substituted or unsubstituted An aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and may also be a single bond, A substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ is bonded to each other to form a ring. Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic group. a heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

3) The organic EL device according to the above 1), wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-2);

【化4】 (B-2)

(wherein R ₁ , R ₃ and R ₄ may be the same or different from each other, and are a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, and may have a substituent having 1 to 6 carbon atoms. a linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent. a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group , substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy group, R ₃ and R ₄ may also be separated by a single A bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ is bonded to each other to form a ring. Ar ₆ and Ar ₈ may be the same or different, and represent a substituted or unsubstituted aroma. a hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

4) The organic EL device according to the above 1), wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-3);

【化5】 (B-3)

(wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different and may be a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a carbon atom which may have a substituent. a linear or branched alkyl group of 1 to 6 or a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched alkene having 2 to 6 carbon atoms which may have a substituent a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, substituted or unsubstituted An aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and may also be a single bond a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ bonded to each other to form a ring. Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic group. a heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

5) The organic EL device according to the above 1), wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-4);

【化6】 (B-4)

(wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different and may be a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a carbon atom which may have a substituent. a linear or branched alkyl group of 1 to 6 or a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched alkene having 2 to 6 carbon atoms which may have a substituent a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, substituted or unsubstituted An aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and may also be a single bond a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ bonded to each other to form a ring. Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic group. a heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

6) The organic EL device according to the above 1), wherein the structural formula (B) is a monovalent group represented by the following structural formula (B');

【化7】 (B')

(wherein R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may be the same or different and may be a linking group, or a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group or a nitro group; Further, it may have a linear or branched alkyl group having 1 to 6 carbon atoms as a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a carbon atom having 2 substituents. a linear or branched alkenyl group of 6 or a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, or a cycloalkane having 5 to 10 carbon atoms which may have a substituent An oxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aromatic group An oxy group, and may also be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ . X represents a carbon atom or a nitrogen atom, and Y is a carbon atom. , an oxygen atom, a sulfur atom, or a nitrogen atom, Ar ₅ represents a substituted or non-substituted aromatic hydrocarbon group, substituted or non-substituted aromatic heterocyclic group, The substituted or unsubstituted condensed polycyclic aromatic group, or a linking group, and Ar _6, Ar ₇ may be the same or different and each represents a substituted or non-substituted aromatic hydrocarbon group, substituted or non-substituted An aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group or a linking group, and Y is an oxygen atom or a sulfur atom, Y makes the number of Ar ₇ 0, and X and Y are nitrogen atoms. When any of Ar ₅ , Ar ₆ and Ar ₇ is a substituent or a linking group, and X is a nitrogen atom and Y is a carbon atom, X makes the number of Ar ₆ 0. Ar ₈ represents a substitution or Unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, or substituted or unsubstituted condensed polycyclic aromatic group. R ₃ , R ₄ , R ₅ , R ₆ , R _7. Any of R ₈ , Ar ₅ , Ar ₆ , and Ar ₇ is a linking group, and excluding X is a nitrogen atom and Y is an oxygen atom or a sulfur atom.)

7) The organic EL device according to the above 1), wherein, in the above formula (1), n is 0.

8) The organic EL device according to the above 1), wherein n is 1 in the above formula (1).

9) The organic EL device according to the above 1), wherein n is 2 in the above formula (1).

In the above-mentioned general formula (1), any one of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ is a monovalent group represented by the above structural formula (B). Or having the monovalent group as a substituent.

11) The organic EL device according to the above 1), wherein, in the above formula (1), Ar ₁ and Ar ₄ are a monovalent group represented by the above structural formula (B) or have a monovalent group as a substituent.

12) The organic EL device according to the above 1), wherein the thickness of the coating layer is in the range of 30 nm to 120 nm.

The organic EL device according to the above 1), wherein the refractive index of the coating layer is 1.85 or more in a range of a wavelength of light of 450 nm to 750 nm transmitted through the coating layer.

14) A method of using a compound represented by the formula (1) of 1) in a coating layer of an organic electroluminescence device.

As the "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the general formula (1), "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted" Specific examples of the "aromatic hydrocarbon group", the "aromatic heterocyclic group" or the "condensed polycyclic aromatic group" in the condensed polycyclic aromatic group include a phenyl group, a biphenyl group, and a biphenyl group. Naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl, fluorenyl, fluorenyl, alkadienyl fluorenyl, pyridyl, pyridyl, pyrrolyl, thiophenyl, Quinolinyl, isoquinolyl, benzofuranyl, benzothienyl, fluorenyl, oxazolyl, benzotriazolyl, benzo An azolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a porphyrin group, and the like. Further, Ar ₁ and Ar ₂ or Ar ₃ and Ar ₄ may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ to form a ring. Here, "N" of "N-Ar ₈ " represents a nitrogen atom, "Ar ₈ " represents "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or The "substituted or unsubstituted condensed polycyclic aromatic group" may be the same as those exemplified above, and the substituents which these groups may possess may also be exemplified by the substituents exemplified below.

The "substituent" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the formula (1), specifically A halogen atom such as a halogen atom, a trifluoromethyl group, a cyano group or a nitro group; a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group or a different group; a linear or branched alkyl group having 1 to 6 carbon atoms such as butyl, tert-butyl, n-pentyl, isopentyl, neopentyl or n-hexyl; methoxy, ethoxy, propoxy a linear or branched alkoxy group having 1 to 6 carbon atoms; an alkenyl group such as an allyl group; an aralkyl group such as a benzyl group, a naphthylmethyl group or a phenethyl group; and an aryl group such as a phenoxy group or a tolyloxy group; Alkoxy; alkoxy group such as benzyloxy or phenethyloxy; phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl, fluorenyl, fluorenyl An aromatic hydrocarbon group or a condensed polycyclic aromatic group such as a propadienyl fluorenyl group or a triphenylene phenyl group; a pyridyl group, a furyl group, a thienyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group or a benzofuranyl group; Benzo Thienyl, indolyl, carbazolyl, benzotriazolyl, benzo Aromatic heterocyclic group such as azolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, porphyrinyl; styryl, naphthyl An arylvinyl group such as a vinyl group; a mercapto group such as an ethyl fluorenyl group or a benzhydryl group; a dialkylamino group such as a dimethylamino group or a diethylamino group; an aromatic hydrocarbon group or a condensation group such as a diphenylamino group or a naphthylamino group; a polycyclic aromatic group-substituted disubstituted amine group; a diarylamino group such as a dibenzylamino group or a diphenylethylamino group; a dipyridylamino group or a dithienylamino group substituted with an aromatic heterocyclic group; a substituted aminyl group such as a diallylamine group; a substituent selected from an alkyl group, an aromatic hydrocarbon group, a condensed polycyclic aromatic group, an aralkyl group, an aromatic heterocyclic group or an alkenyl group; Substituents such as substituted amine groups may be further substituted with the substituents exemplified above. Further, the substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ to form a ring. Here, "N-Ar ₈ ", and "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), "substituted or unsubstituted aromatic""N-Ar ₈ " as defined in the "heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" has the same meaning.

As the R ₁ to R ₈ in the structural formulae (B), (B-1), (B-2), (B-3), (B-4), and (B'), "there may also have a substituent. a linear or branched alkyl group having 1 to 6 carbon atoms, "a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent" or "a carbon number of 2 to 6 which may have a substituent""Linear or branched alkyl group having 1 to 6 carbon atoms", "cycloalkyl group having 5 to 10 carbon atoms" or "carbon number 2 to 6" in a linear or branched alkenyl group" The linear or branched alkenyl group may specifically be a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group or an isopentyl group. , neopentyl, n-hexyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, vinyl, allyl, isopropenyl and 2-butenyl, etc. The ring may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ . Here, "N-Ar ₈ ", and "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), "substituted or unsubstituted aromatic""N-Ar ₈ " as defined in the "heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" has the same meaning.

As the substituted carbon, R ₁ to R ₈ in the structural formulae (B), (B-1), (B-2), (B-3), (B-4), and (B') a linear or branched alkyl group having 1 to 6 atoms, a "cycloalkyl group having 5 to 10 carbon atoms with a substituent" or a linear or branched carbon atom having 2 to 6 having a substituent The "substituent" in the alkenyl group may be a "substituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), a "substituted aromatic heterocyclic group" or a "substituted condensed group". The "substituent" in the cyclic aromatic group is disclosed by the same person, and the same can be cited.

As the R ₁ to R ₈ in the structural formulae (B), (B-1), (B-2), (B-3), (B-4), and (B'), "there may also have a substituent. a linear chain or branched alkoxy group having 1 to 6 carbon atoms or a linear alkyl group having 1 to 6 carbon atoms in a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent Alkoxy group or a "cycloalkyloxy group having 5 to 10 carbon atoms", specifically, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group or a n-butoxy group , a third butoxy group, a n-pentyloxy group, a n-hexyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a 1-adamantanyloxy group, a 2-adamantanyloxy group, etc. These groups may also be bonded to each other by a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ . Here, "N-Ar ₈ ", and "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), "substituted or unsubstituted aromatic""N-Ar ₈ " as defined in the "heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" has the same meaning.

As the substituted carbon, R ₁ to R ₈ in the structural formulae (B), (B-1), (B-2), (B-3), (B-4), and (B') The "substituent" in the linear or branched alkoxy group having 1 to 6 atoms or the "cycloalkyloxy group having 5 to 10 carbon atoms having a substituent" may be exemplified and related to the above formula (1). The "substituent" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the above is disclosed as the same. The same can be cited for the aspect.

As a structural formula (B), (B-1), (B-2), (B-3), (B-4), (B'), R ₁ to R ₈ represent "substituted or unsubstituted "Aromatic hydrocarbon group" or "aromatic heterocyclic ring" in the substituted aromatic hydrocarbon group, "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" The "condensed polycyclic aromatic group" and the "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), "substituted or unsubstituted""Aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the substituted aromatic heterocyclic group or "substituted or unsubstituted condensed polycyclic aromatic group" For the same person, the same can be cited.

"Substituted aromatic hydrocarbon group" represented by R ₁ to R ₈ in the structural formulae (B), (B-1), (B-2), (B-3), (B-4), and (B') The "substituent" in the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" may be exemplified by the "substituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1). The "substituent" in the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" is the same, and the same can be taken.

As a structural formula (B), (B-1), (B-2), (B-3), (B-4), (B'), R ₁ to R ₈ represent "substituted or unsubstituted Specific examples of the "aryloxy group" in the substituted aryloxy group include a phenoxy group, a tolyloxy group, a biphenyloxy group, a terphenyloxy group, a naphthyloxy group, a decyloxy group, and a phenanthryloxy group. a methoxy group, a decyloxy group, a decyloxy group, a decyloxy group or the like, which may also be a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ . Bonded to each other in a loop. Here, "N-Ar ₈ ", and "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), "substituted or unsubstituted aromatic""N-Ar ₈ " defined by a heterocyclic group or a "substituted or unsubstituted condensed polycyclic aromatic group" has the same meaning.

"Substituted aryloxy group" represented by R ₁ to R ₈ in the structural formulae (B), (B-1), (B-2), (B-3), (B-4), and (B') The "substituent group" in the above formula (1), "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the above formula (1) The "substitute" in the middle of the disclosure is the same, and the same can be taken.

As the "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₅ , Ar ₆ or Ar ₇ in the structural formulae (B), (B-2) and (B'), "substituted or unsubstituted""Aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" With respect to Ar ₁ to Ar ₄ in the above formula (1), "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted" The "aromatic hydrocarbon group", the "aromatic heterocyclic group" or the "condensed polycyclic aromatic group" in the substituted condensed polycyclic aromatic group are the same, and the same can be taken.

"Substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted aromatic heterocyclic group" represented by Ar ₅ , Ar ₆ or Ar ₇ in the structural formulae (B), (B-2) and (B') The "substituent" in the aromatic group may be a "substituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the above formula (1), a "substituted aromatic heterocyclic group" or a "substituted condensed group". The "substituent" in the cyclic aromatic group is disclosed by the same person, and the same can be cited.

In the formula (1), n represents an integer of 0 to 4, n is preferably 0, 1 or 2, more preferably 0 or 1. In the general formula (1), at least one of Ar ₁ , Ar ₂ , Ar ₃ and Ar _{4 is} in the form of the structural formula (B) or at least one of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ . The structure having the above structural formula (B) as a substituent thereof, or at least one of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ is the above structural formula (B) and Ar ₁ , Ar ₂ , Ar ₃ At least one of Ar ₄ has the above structural formula (B) as a substituent thereof, and any two of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are in the form of the above structural formula (B). Or any one of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ has the above structural formula (B) as a substituent thereof, or any one of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ It is preferable that any one of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ of the above structural formula (B) and not the above structural formula (B) has the above structural formula (B) as a substituent thereof. best of Ar ₁ and Ar ₄ is the aspect of the structural formula (B), the Ar ₁ and Ar ₄ having the foregoing structural formula (B) as an aspect of the substituent of, or Ar ₁ is the structural formula (B) and Ar ₄ having the aforementioned structural formula (B) as a kind of a substituent better state, and more preferably Ar ₁ to Ar ₄ having the aforementioned structure (B-1), (B-3) or (B-4) as a substituent group of aspects or aspects of the structural formula (B-2) of the. As Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ in the formula (1), an aromatic hydrocarbon group, a condensed polycyclic aromatic group, the above structural formula (B), a thienyl group, a benzothienyl group, and a diphenyl group are preferable. And furanyl, dibenzothiophenyl group is preferred, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, the above structural formula (B), thienyl, benzothienyl, diphenyl Further, a furyl group or a dibenzothiophene group is preferred, and a phenyl group, a biphenyl group, a fluorenyl group, and the above structural formula (B), a dibenzofuranyl group, and a dibenzothiophene group are particularly preferred. As the structural formula (B), (B-2), (B'), Ar ₅ , Ar ₆ , Ar ₇ , an aromatic hydrocarbon group, a condensed polycyclic aromatic group, a thienyl group, a benzothienyl group, a dibenzo Furanyl, dibenzothiophenyl is preferred, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothiophene The base is more ideal. In the formula (1), only one of R ₁ , R ₂ , R ₃ , R ₄ , Ar ₅ , Ar ₆ and Ar ₇ is a linking group. In the structural formulae (B) and (B'), X represents a carbon atom or a nitrogen atom, and Y represents a carbon atom, an oxygen atom, a sulfur atom, or a nitrogen atom. Here, when Y is an oxygen atom or a sulfur atom, Y has a linking group of Ar ₇ or a number of substituents of 0 (Ar _{7 is} not present), and when X and Y are nitrogen atoms, Ar ₅ and Ar _{6 are} Any one of Ar ₇ is a linking group or a substituent (any of Ar ₅ , Ar ₆ , and Ar ₇ are not present), and when X is a nitrogen atom and Y is a carbon atom, Ar ₅ and Ar ₆ are not included. One is a linking group or a substituent (any of Ar ₅ and Ar ₆ does not exist). In the structural formulae (B) and (B'), when X is a nitrogen atom, Y is preferably a nitrogen atom. In this case, a linking group of Ar ₅ , Ar ₆ or Ar ₇ and Ar ₁ , Ar ₂ , Ar ₃ , When the carbon atom of Ar ₄ is bonded (the structural formula (B) or (B') is a substituent of Ar ₁ , Ar ₂ , Ar ₃ or Ar ₄ ), it is preferable from the viewpoint of the stability of the compound. In the structural formulae (B) and (B'), when X is a carbon atom, Y is preferably a carbon atom, an oxygen atom or a sulfur atom, and more preferably an oxygen atom or a sulfur atom. In the structural formulae (B) and (B'), the case where X is a nitrogen atom and Y is an oxygen atom or a sulfur atom is not included in the present invention.

The arylamine compound represented by the above formula (1) which can be suitably used in the organic EL device of the present invention can be used as a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer or a cover layer of an organic EL device. Material use.

Further, in the organic EL device of the present invention, the thickness of the coating layer is preferably in the range of 30 nm to 120 nm, and more preferably in the range of 40 nm to 80 nm.

Further, in the organic EL device of the present invention, the wavelength of light transmitted through the coating layer is in the range of 450 nm to 750 nm, and the refractive index of the coating layer is preferably 1.85 or more, more preferably 1.90 or more.

Moreover, in the organic EL device of the present invention, the coating layer can be produced by laminating two or more different constituent materials. [Effects of the Invention]

Since the organic EL device of the present invention has a coating layer which is provided on the outer side of the transparent or semi-transparent electrode and has a higher refractive index than the translucent electrode, an organic EL device having greatly improved light extraction efficiency can be obtained. Further, by using the arylamine compound represented by the above formula (1) in the coating layer, the film can be formed at a temperature of 400 ° C or lower, so that the light extraction efficiency of each color can be made using a high-definition mask without damaging the light-emitting element. Optimized and suitable for use in full color displays, it can display vivid and bright images with good color purity.

In the organic EL device of the present invention, since a material for an organic EL device having a high refractive index, a film stability, and durability is used as a material of the coating layer, the light extraction efficiency can be made larger than that of the conventional organic EL device. improve. Further, an organic EL element having high efficiency and long life can be achieved.

The arylamine compound represented by the above formula (1) which can be suitably used in the organic EL device of the present invention is a novel compound which can be synthesized, for example, in the following manner. For example, a 2-aminoarylazobenzene derivative is synthesized from a 1,2-diaminobenzene derivative and a nitroaryl derivative by a known method, and a bis(acetate-O)phenyl group is used. A benzotriazole derivative having an aryl group can be synthesized by an oxidative cyclization reaction of bis(acetato-O)phenyliodine (see, for example, Non-Patent Document 4). Here, a bromine substituent of a benzotriazole derivative having an aryl group can be synthesized by using a 1,2-diaminobenzene derivative or a nitroaryl derivative having a halogen atom such as a bromine atom as a substituent. . Then, the aromatic amine compound represented by the formula (1) of the present invention can be synthesized by carrying out a condensation reaction of the Ullmann reaction, the Buchwald-Hartwig reaction or the like of the bromine substituent with the diarylamine. Further, the brominated benzotriazole derivative can also be synthesized by subjecting the above-described synthesized aryl-containing benzotriazole derivative to bromination using ruthenium N-bromosuccinate or the like. Here, by changing the bromination reagent and the conditions, a bromine substituent having a different substitution position can be obtained. Further, the aromatic amine compound represented by the formula (1) of the present invention can be synthesized by carrying out the same reaction. In addition, synthetic by boronic acid or ester of pinacol boronate (bis (pinacolato) diboron) for the reaction of this bromo substituent thereof, by the embodiment and various aryl halides and alkyl borane pinacol derivative or a double frequency The arylamine compound represented by the formula (1) of the present invention can also be synthesized by a cross-coupling reaction such as Suzuki coupling (see, for example, Non-Patent Document 6) by the object (for example, refer to Non-Patent Document 5). Further, a cross-coupling reaction such as Suzuki coupling with a aryl halide having a diarylamine group by synthesizing a boronic acid or a boric acid ester (for example, see Non-Patent Document 5) from the above-mentioned bromine substituent (For example, refer to Non-Patent Document 6), an aromatic amine compound represented by the formula (1) of the present invention can also be synthesized. Here, by a benzothiazole derivative having a corresponding substituent, benzo The azole derivative or the bromine substituent of the hydrazine derivative or the bromine substituent after bromination can be synthesized to synthesize a benzothiazolyl group and a benzo The arylamine compound represented by the formula (1) of the present invention which is an azolyl group or a fluorenyl group.

Among the arylamine compounds represented by the above formula (1) which can be preferably used in the organic EL device of the present invention, specific examples of the compounds which are particularly preferred are, but not limited to, the compounds.

【化8】 (1-1)

【化9】 (1-2)

【化10】 (1-3)

【化11】 (1-4)

【化12】 (1-5)

【化13】 (1-6)

【化14】 (1-7)

【化15】 (1-8)

【化16】 (1-9)

【化17】 (1-10)

【化18】 (1-11)

【化19】 (1-12)

【化20】 (1-13)

【化21】 (1-14)

【化22】 (1-15)

【化23】 (1-16)

【化24】 (1-17)

【化25】 (1-18)

【化26】 (1-19)

【化27】 (1-20)

【化28】 (1-21)

【化29】 (1-22)

【化30】 (1-23)

【化31】 (1-24)

【化32】 (1-25)

【化33】 (1-26)

【化34】 (1-27)

【化35】 (1-28)

【化36】 (1-29)

【化37】 (1-30)

【化38】 (1-31)

【化39】 (1-32)

【化40】 (1-33)

【化41】 (1-34)

【化42】 (1-35)

【化43】 (1-36)

【化44】 (1-37)

【化45】 (1-38)

【化46】 (1-39)

【化47】 (1-40)

【化48】 (1-41)

【化49】 (1-42)

【化50】 (1-43)

【化51】 (1-44)

【化52】 (1-45)

【化53】 (1-46)

【化54】 (1-47)

【化55】 (1-48)

【化56】 (1-49)

【化57】 (1-50)

【化58】 (1-51)

【化59】 (1-52)

【化60】 (1-53)

【化61】 (1-54)

【化62】 (1-55)

【化63】 (1-56)

The purification of these compounds is carried out by column chromatography, and is carried out by adsorption purification using a tannin extract, activated carbon, activated clay or the like, recrystallization by a solvent, or crystallization, and finally purification by sublimation purification or the like. In the case of physical properties, the measurement of the glass transition point (Tg) and the refractive index was carried out. The glass transition point (Tg) is an index for the stability of the film state, and the refractive index system is an index for improving the light extraction efficiency.

The glass transition point (Tg) was measured using a powder using a high-sensitivity differential scanning calorimeter (DSC3100S manufactured by BRUKER AXS).

The refractive index was measured by forming a film of 80 nm on a ruthenium substrate, and measuring using a spectrophotometer (F10-RT-UV, manufactured by Filmetrics Co., Ltd.).

The structure of the organic EL device of the present invention, for example, in the case of a light-emitting device having a top emission structure, has an anode, a hole transport layer, a light-emitting layer, an electron transport layer, a translucent cathode, and the like, which are composed of a metal on a glass substrate. If the cover layer is formed, and there is a hole injection layer between the anode and the hole transport layer, there is an electron blocking layer between the hole transport layer and the light-emitting layer, and there is electricity between the light-emitting layer and the electron transport layer. In the hole barrier layer, there is an electron injection layer between the electron transport layer and the cathode. In the multilayer structure, a plurality of organic layers may be omitted or several layers may be used in combination, and for example, it may be configured as a hole transport layer and an electron blocking layer, and also as an electron transport layer and a hole blocking layer. The thickness of each layer of the organic EL device is preferably from about 200 nm to 750 nm, more preferably from about 350 nm to 600 nm. Further, the film thickness of the coating layer is preferably 30 nm to 120 nm, and more preferably 40 nm to 80 nm. At this time, good light extraction efficiency can be obtained. In addition, the film thickness of the coating layer can be appropriately changed depending on the type of the light-emitting material used for the light-emitting element, the thickness of the organic EL element other than the coating layer, and the like.

As the anode of the organic EL device of the present invention, an electrode material having a large work function such as ITO or gold can be used.

As the hole injection layer of the organic EL device of the present invention, an arylamine compound having a structure in which three or more triphenylamine structures in a molecule are bonded by a single bond or a divalent group containing no hetero atom can be used, for example, a ray type. a material such as a triphenylamine derivative or a various triphenylamine tetramer, or a polyporphyrin compound represented by beryl phthalocyanine or a heterocyclic compound such as hexacyanoazide exemplified benzene, or a coating type Polymer materials, etc. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

The hole transporting layer of the organic EL device of the present invention is preferably, for example, N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (hereinafter abbreviated as TPD), N,N'- Diphenyl-N,N'-bis(α-naphthyl)benzidine (NPD), 1,1-bis[4-(di-4-toluamino)phenyl]cyclohexane (TAPC), especially The arylamine compound having a structure in which two triphenylamine structures are linked by a single bond or a divalent group containing no hetero atom, for example, N, N, N', N'-tetraphenylbenzidine or the like is preferable. . Further, it is preferred to use an arylamine compound having a structure in which three or more triphenylamine structures in the molecule are bonded by a single bond or a divalent group containing no hetero atom, and for example, various triphenylamine trimers and tetramers are preferable. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

Further, in the hole injection layer or the hole transport layer, a material which is usually used for the layer may be further doped with a P-type doped bromoxyaniline or a benzidine derivative such as TPD. Polymer compound.

As the electron blocking layer of the organic EL device of the present invention, 4,4',4''-tris(N-carbazolyl)triphenylamine (hereinafter referred to as TCTA), 9,9-bis[4-(carbazole) can be used. -9-yl)phenyl]anthracene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane ( Ad-Cz) and other carbazole derivatives, 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylindenyl)phenyl]-9H-indole are represented by three A compound having an electron blocking effect such as a compound of a phenylfluorenyl group and a triarylamine structure. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

As the light-emitting layer of the organic EL device of the present invention, a metal complex of a quinolinol derivative such as Alq ₃ , a complex of various metals, an anthracene derivative, a bisstyrylbenzene derivative, or an anthracene derivative can be used. , An azole derivative, a poly-p-phenylene vinyl derivative, and the like. Further, the light-emitting layer may be composed of a host material and a dopant material, and as the host material, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative or the like may be used in addition to the above-mentioned light-emitting material. As the dopant material, quinacridone, coumarin, erythritol, hydrazine and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, and the like can be used. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

Further, a phosphorescent material can also be used as the light-emitting material. As the phosphorescent material, a phosphorescent emitter of a metal complex such as ruthenium or platinum can be used. For example, a green phosphorescent emitter such as Ir(ppy) ₃ , a blue phosphorescent emitter such as FIrpic or FIr6, or a red phosphorescent emitter such as Btp ₂ Ir(acac). As the host material, 4,4'-bis(N-carbazolyl)biphenyl (CBP), a carbazole derivative such as TCTA or mCP, or the like can be used as the host material for hole injection and transport. As a host material for electron transport, p-bis(triphenylsulfonyl)benzene (UGH2), 2,2',2''-(1,3,5-phenylene)-para (1-benzene) can be used. A high-performance organic EL device can be produced by thiol-1H-benzimidazole (TPBI) or the like.

The doping of the host material by the phosphorescent luminescent material is preferably in the range of 1 to 30% by weight for the entire light-emitting layer in order to avoid concentration extinction, and is preferably doped by co-evaporation.

Further, as the luminescent material, a material which emits delayed fluorescence such as a CDCB derivative such as PIC-TRZ, CC2TA, PXZ-TRZ or 4CzIPN can be used (for example, refer to Non-Patent Document 7).

These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

Examples of the hole layer of the organic EL device of the present invention include a phenanthroline derivative such as Bathocuproin and bis(2-methyl-8-quinolinol)-4-phenylphenolate aluminum ( a metal complex of a quinoline phenol derivative such as III) (hereinafter abbreviated as BAlq), various rare earth complexes, triazole derivatives, triterpene derivatives, A compound having a hole blocking effect such as an oxadiazole derivative. These materials can also serve as materials for the electron transport layer. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

As the electron transport layer of the organic EL device of the present invention, a metal complex of a quinoline phenol derivative such as Alq ₃ or BAlq, various metal complexes, a triazole derivative, or a triterpene derivative can be used. An oxadiazole derivative, a thiadiazole derivative, a pyridoindole derivative, a carbodiimide derivative, a quinoxaline derivative, a phenanthroline derivative, a pyrene derivative, and the like. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

As the electron injecting layer of the organic EL device of the present invention, an alkali metal salt such as lithium fluoride or cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, or a metal oxide such as alumina can be used, but the electron transport layer and the cathode are used. Ideally, you can omit it.

Further, in the electron injecting layer or the electron transporting layer, a metal such as ruthenium may be further doped with an N-type material for a material generally used for the layer.

The translucent cathode of the organic EL device of the present invention may be an electrode material having a low work function such as aluminum, or an alloy having a lower work function such as a magnesium-silver alloy, a magnesium-calcium alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy, or an ITO. , IZO, etc. as electrode materials.

As the coating layer of the organic EL device of the present invention, an aromatic amine compound represented by the above formula (1) or the like is preferably used. These may be formed separately, or may be mixed with other materials to form a film into a single layer, or may be formed separately as layers, layers formed by mixing the layers, or layers formed separately and mixed into a film. The laminated structure of the layers. These materials may be formed into a film by a known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

Further, although the above description has been made on the organic EL device of the top emission structure, the present invention is not limited thereto, and the same applies to the organic EL device of the bottom emission structure or the organic EL device of the dual light emission structure that emits light from both the upper portion and the bottom portion. Can be applied. In these cases, the electrode positioned in the direction in which light is taken out from the light-emitting element to the outside must be transparent or translucent.

The refractive index of the material constituting the cover layer is preferably larger than the refractive index of the adjacent electrode. In other words, the use of the cover layer improves the light extraction efficiency in the organic EL element. However, when the reflectance of the interface between the cover layer and the material of the contact cover layer is large, the effect of light interference is large, so it is effective. . Therefore, the refractive index of the material constituting the coating layer is preferably larger than the refractive index of the adjacent electrode, and the refractive index is 1.70 or more, but it is preferably 1.80 or more, and more preferably 1.85 or more.

Hereinafter, embodiments of the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples. [Example 1]

<N,N'-bis{4-(2H-benzo[1,2,3]triazol-2-yl)phenyl}-N,N'-diphenyl-4,4'-diamino Synthesis of -1,1'-biphenyl (compound (1-1)) > 2-(4-bromophenyl)-2H-benzo[1,2,3]3 was added to a nitrogen-substituted reaction vessel 4.2 g of oxazole, 2.3 g of N,N'-diphenylbenzidine, and 2.0 g of sodium butoxide were added, and 50 ml of toluene was added thereto, and nitrogen gas was introduced while ultrasonic waves were irradiated for 30 minutes. 62.0 mg of palladium acetate and 0.2 ml of tri-tert-butylphosphine were added and heated, and the mixture was stirred at 91 ° C for 5 hours. After cooling to room temperature, 50 ml of toluene was added, and the organic layer was collected by an extraction operation. After concentrating the organic layer, it was purified by column chromatography (support: NH phthalate, eluent: toluene/n-hexane), and then washed with 100 ml of n-hexane to obtain N,N'-double {4-(2H). -Benzo[1,2,3]triazol-2-yl)phenyl}-N,N'-diphenyl-4,4'-diamino-1,1'-biphenyl (compound (1) -1)) Yellow powder 3.3 g (yield 66%).

The structure was identified using NMR for the obtained yellow powder. ¹ H-NMR (THF-d ₈ ) detected the following 34 hydrogen signals. δ (ppm) = 8.26 (4H), 7.89 (4H), 7.60 (4H), 7.39 (4H), 7.33 (4H), 7.24 (4H), 7.21 (8H), 7.10 (2H). [Example 2]

<N,N'-bis(2-phenyl-2H-benzo[1,2,3]triazol-5-yl)-N,N'-diphenyl-4,4'-diamino- Synthesis of 1,1'-biphenyl (compound (1-32)) > 5-bromo-2-phenyl-2H-benzo[1,2,3]triazole 4.1 was added to a nitrogen-substituted reaction vessel. g, N, N'-diphenylbenzidine 2.3 g, sodium terp-butoxide 2.0 g, toluene 50 ml, and nitrogen gas was supplied while being irradiated for 30 minutes. 62.0 mg of palladium acetate and 0.2 ml of tri-tert-butylphosphine were added and heated. Stir at 91 ° C for 3.5 hours. After cooling to room temperature, 50 ml of toluene was added, and the organic layer was collected by an extraction operation. After concentrating the organic layer, it was purified by column chromatography (support: silica gel, eluent: toluene/n-hexane). After further adding 25 ml of THF and dissolving, 100 ml of methanol was added dropwise to carry out crystallization purification to obtain N,N'-bis(2-phenyl-2H-benzo[1,2,3]triazol-5-yl)-N. , a yellow-brown powder of N'-diphenyl-4,4'-diamino-1,1'-biphenyl (compound (1-32)) 4.0 g (yield: 80%).

The structure was identified using NMR for the obtained yellow-brown powder. ¹ H-NMR (THF-d ₈ ) detected the following 34 hydrogen signals. δ (ppm) = 8.32 (4H), 7.81 (2H), 7.59 (4H), 7.54 (4H), 7.43 (2H), 7.40 (2H), 7.32 (4H), 7.28 (2H), 7.20 (4H), 7.18 (4H), 7.09 (2H). [Example 3]

<N,N'-bis{4-(2H-benzo[1,2,3]triazol-2-yl)phenyl}-N,N'-diphenyl-4,4''-diamine Synthesis of keto-1,1':4',1''-bitriphenyl (compound (1-2))> Add 4,4''-diiodo-1,1' to a nitrogen-substituted reaction vessel : 4', 1''-bitriphenyl 14.0g, {4-(2H-benzo[1,2,3]triazol-2-yl)phenyl}phenylamine 18.3g, potassium carbonate 13.2g, copper powder 0.3 g, 0.9 g of sodium hydrogen sulfite, 0.7 g of 3,5-di-t-butylsalicylic acid, and 30 ml of dodecylbenzene were heated and stirred at 210 ° C for 44 hours. After cooling to room temperature, 50 ml of toluene was added, and the precipitate was collected by filtration. To the precipitate, 230 ml of 1,2-dichlorobenzene was added, dissolved by heating, and insoluble matter was removed by filtration with hot air. The filtrate was concentrated, and subjected to crystallization purification using 1,2-dichlorobenzene, followed by dispersion washing using methanol to obtain N,N'-bis{4-(2H-benzo[1,2,3]triazole. -2-yl)phenyl}-N,N'-diphenyl-4,4''-diamino-1,1':4',1''-bitriphenyl (compound (1-2) The yellow powder was 22.2 g (yield 96%).

The structure was identified using NMR for the obtained yellow powder. ¹ H-NMR (CDCl ₃ ) detected the following 38 hydrogen signals. δ (ppm) = 8.24 (4H), 7.99 - 7.92 (4H), 7.72 - 7.58 (7H), 7.50 - 7.12 (23H). [Embodiment 4]

<N,N'-double {4-(benzo Zin-2-yl)phenyl}-N,N'-diphenyl-4,4''-diamino-1,1':4',1''-bitriphenyl (compound (1-22) Synthesis of)) Substituting {4-(2H-benzo[1,2,3]triazol-2-yl)phenyl}phenylamine in Example 3 for {4-(benzo Zyridin-2-yl)phenyl}aniline, reacted under the same conditions to obtain N,N'-double {4-(benzo Zin-2-yl)phenyl}-N,N'-diphenyl-4,4''-diamino-1,1':4',1''-bitriphenyl (compound (1-22) )) Yellow powder 12.4 g (yield 47%).

The structure was identified using NMR for the obtained yellow powder. ¹ H-NMR (CDCl ₃ ) detected the following 38 hydrogen signals. δ (ppm) = 8.13 (4H), 7.80 - 7.55 (11H), 7.50 - 7.16 (23H). [Embodiment 5]

<N,N'-double {4-(benzo Synthesis of oxazol-2-yl)phenyl}-N,N'-diphenyl-4,4'-diamino-1,1'-biphenyl (compound (1-23)) > Example 1 Replacement of 2-(4-bromophenyl)-2H-benzo[1,2,3]triazole with 2-(4-bromophenyl)-benzo The azole is reacted under the same conditions to obtain N,N'-double {4-(benzo Light yellow powder of oxazol-2-yl)phenyl}-N,N'-diphenyl-4,4'-diamino-1,1'-biphenyl (compound (1-23)) 8.8 g (Yield 54%).

The structure was identified using NMR for the obtained pale yellow powder. ¹ H-NMR (CDCl ₃ ) detected the following 34 hydrogen signals. δ (ppm) = 8.12 (4H), 7.80-7.72 (2H), 7.60-7.53 (5H), 7.41-7.14 (23H). [Embodiment 6]

<N,N'-bis{4-(benzothiazol-2-yl)phenyl}-N,N'-diphenyl-4,4'-diamino-1,1'-biphenyl (compound) Synthesis of (1-25)) > 2-(4-bromophenyl)-2H-benzo[1,2,3]triazole in Example 1 was replaced with 2-(4-bromophenyl)- Benzothiazole, reacted under the same conditions to obtain N,N'-bis{4-(benzothiazol-2-yl)phenyl}-N,N'-diphenyl-4,4'-diamine Light yellow powder of 1,3--1'-biphenyl (compound (1-25)) 9.3 g (yield 62%).

The structure was identified using NMR for the obtained pale yellow powder. ¹ H-NMR (CDCl ₃ ) detected the following 34 hydrogen signals. δ (ppm) = 8.10-7.88 (8H), 7.60-7.13 (26H). [Embodiment 7]

<N,N'-bis{4-(benzothiazol-2-yl)phenyl}-N,N'-diphenyl-4,4''-diamino-1,1':4', Synthesis of 1''-bitriphenyl (compound (1-27))> N-{4-(benzothiazol-2-yl)phenyl}aniline 9.3 g, 4 was added to a nitrogen-substituted reaction vessel. 4''-Diiodo-1,1':4',1''-bitriphenyl 7.1g, sodium butoxide sodium 4.6g, toluene 140ml, while passing through the ultrasonic wave for 30 minutes, nitrogen gas was introduced. After adding 0.20 g of palladium acetate and 0.5 g of a 50% (v/v) toluene solution of a third butylphosphine, the mixture was heated, and heated under reflux for 3 hours while stirring. After cooling to room temperature, the precipitate was collected by filtration, and then subjected to crystallization purification using a mixed solvent of 1,2-dichlorobenzene/methanol to obtain N,N'-bis{4-(benzothiazol-2-yl). Green powder of phenyl}-N,N'-diphenyl-4,4''-diamino-1,1':4',1''-bitriphenyl (compound (1-27)) 7.0 g (yield 58%). [Embodiment 8]

With respect to the compound of the present invention, a glass transition point was determined using a high-sensitivity differential scanning calorimeter (DSC3100S manufactured by BRUKER AXS). Glass transition point exemplified compound (1-1) 125 ° C exemplified compound (1-32) 110 ° C exemplified compound (1-2) 135 ° C exemplified compound (1-22) 137 ° C exemplified compound (1-23) 128 ° C exemplified compound (1-25) 127 ° C exemplified compound (1-27) 137 ° C

The compounds of the invention have a glass transition point above 100 °C. This shows that the compound of the present invention is stable in the state of the film. [Embodiment 9]

Using the compound of the present invention, a vapor deposited film having a thickness of 80 nm was formed on a ruthenium substrate, and a refractive index at 633 nm was measured using a spectrometer (F10-RT-UV, manufactured by Fillmetrics Co., Ltd.). For comparison, the comparative compounds (2-1), (2-2), and Alq _{3 of the} following structural formula were also measured (for example, refer to Patent Document 3). Refractive index exemplified compound (1-1) 1.90 exemplified compound (1-32) 1.90 exemplified compound (1-2) 1.90 exemplified compound (1-22) 1.89 exemplified compound (1-23) 1.93 exemplified compound (1-25) 1.93 Illustrative Compound (1-27) 1.91 Comparative Compound (2-1) 1.81 Comparative Compound (2-2) 1.80 Comparative Compound (Alq ₃ ) 1.70

【化64】 (2-1)

【化65】 (2-2)

As described above, the compound of the present invention has a larger enthalpy than the refractive indices of 1.70 to 1.81 of the comparative compounds (2-1), (2-2), and Alq ₃ , and it is expected that the light extraction efficiency in the organic EL device is improved. [Embodiment 10]

As shown in FIG. 7, the organic EL device is formed by depositing a hole injection layer 3, a hole transport layer 4, and a light-emitting layer 5 in this order on a glass substrate 1 as a reflective ITO electrode of the metal anode 2. The electron transport layer 6, the electron injection layer 7, the cathode 8, and the cover layer 9 are formed.

Specifically, the glass substrate 1 on which the ITO film having a film thickness of 150 nm was formed was ultrasonically washed in isopropyl alcohol for 20 minutes, heated to 250 ° C, and dried on a hot plate for 10 minutes. Thereafter, UV ozone treatment was carried out for 2 minutes, and then the glass substrate with ITO was attached to a vacuum vapor deposition machine, and the pressure was reduced to 0.001 Pa or less. Then, the compound of the following structural formula (HIM-1) was formed to have a film thickness of 5 nm as the hole injection layer 3 so as to cover the metal anode 2. On the hole injection layer 3, a film of the above comparative compound (2-1) was formed to have a film thickness of 70 nm as the hole transport layer 4. On the hole transport layer 4, the compound EMD-1 (NUBD370 manufactured by SFC Co., Ltd.) and the compound EMH-1 (ABH113 manufactured by SFC Co., Ltd.) were converted to EMD-1:EMH at a vapor deposition rate ratio. The vapor deposition rate of 1 = 5:95 was subjected to binary vapor deposition to have a film thickness of 25 nm, which was used as the light-emitting layer 5. On the light-emitting layer 5, the compound of the following structural formula (ETM-1) and the compound of the following structural formula (ETM-2) were made into (ETM-1) at a vapor deposition rate ratio: (ETM-2) = 50: The vapor deposition rate of 50 was subjected to binary vapor deposition to have a film thickness of 30 nm to serve as the electron transport layer 6. On the electron transport layer 6, a film of lithium fluoride was formed to have a film thickness of 0.5 nm as the electron injection layer 7. On the electron injecting layer 7, a film of a magnesium-silver alloy was formed to have a film thickness of 14 nm to serve as the cathode 8. Finally, a film of the compound (1-1) of Example 1 was formed to have a film thickness of 60 nm to serve as the cover layer 9. The organic EL device produced was subjected to characteristic measurement at room temperature in the atmosphere. The measurement results of the luminescence characteristics when a DC voltage was applied to the produced organic EL device were summarized in Table 1.

【化66】 (HIM-1)

【化67】 (ETM-1)

【化68】 (ETM-2) [Embodiment 11]

The organic EL was produced under the same conditions except that the compound (1-1) of Example 1 in Example 10 was formed by forming the compound (1-32) of Example 2 into a film thickness of 60 nm as the coating layer 9. element. The organic EL device produced was subjected to characteristic measurement at room temperature in the atmosphere. The measurement results of the luminescence characteristics when a DC voltage was applied to the produced organic EL device were summarized in Table 1. [Embodiment 12]

The compound (1-1) of Example 1 in Example 10 was replaced with the compound (1-2) of Example 3, and the film was formed to have a film thickness of 60 nm to serve as the cover layer 9, and other organic EL was produced under the same conditions. element. The organic EL device produced was subjected to characteristic measurement at room temperature in the atmosphere. The measurement results of the luminescence characteristics when a DC voltage was applied to the produced organic EL device were summarized in Table 1. [Example 13]

The compound (1-1) of Example 1 in Example 10 was replaced with the compound (1-22) of Example 4, and the film was formed to have a film thickness of 60 nm to serve as the cover layer 9, and other organic EL was produced under the same conditions. element. The organic EL device produced was subjected to characteristic measurement at room temperature in the atmosphere. The measurement results of the luminescence characteristics when a DC voltage was applied to the produced organic EL device were summarized in Table 1.

[Comparative Example 1] For comparison, the compound (1-1) of Example 1 in Example 10 was replaced with Alq ₃ , and the film was formed to have a film thickness of 60 nm to serve as the cover layer 9, and other organic materials were produced under the same conditions. EL component. The organic EL device produced was subjected to characteristic measurement at room temperature in the atmosphere. The measurement results of the light-emitting characteristics of the DC voltage applied to the produced organic EL device were summarized in Table 1.

【Table 1】

As shown in Table 1, with respect to the driving voltage at a current density of 10 mA/cm ² , the element (4.19 V) of Comparative Example 1 using Alq ₃ is substantially equivalent to the element (4.17 to 4.18 V) of Examples 10 to 13, and is relatively equivalent. Here, regarding the luminance, the luminous efficiency, and the power efficiency, the components of the examples 10 to 13 (the luminous efficiency: 5.13 cd/A, the electric power efficiency: 3.78 lm/W) were compared with the components of Comparative Example 1 using Alq ₃ ( Luminous efficiency: 5.31~5.36cd/A, power efficiency: 3.98~4.06lm/W) are improved. In particular, the external quantum efficiency was confirmed to be significantly higher than the components of Comparative Example 1 (10.72%), and the components of Examples 10 to 13 (11.41 to 11.93%) were greatly improved. This shows that the cover layer can greatly improve the light extraction efficiency by containing a material having a high refractive index and suitable for the organic EL element of the present invention. [Industry Utilization]

As described above, the arylamine compound represented by the formula (1) which is preferably used in the organic EL device of the present invention has a high refractive index, can greatly improve the light extraction efficiency, and has a stable film state, so that it is used for an organic EL device. Excellent compound. By using the compound to produce an organic EL device, high efficiency can be obtained and durability can be improved. Further, it is particularly preferable to use a compound which does not have absorption in respective wavelength regions of blue, green and red, and to display a bright and bright image with good color purity. For example, the use of household electrical products or lighting can be carried out.

【Symbol Description】
1‧‧‧ glass substrate
2‧‧‧Metal anode
3‧‧‧ hole injection layer
4‧‧‧ hole transport layer
5‧‧‧Lighting layer
6‧‧‧Electronic transport layer
7‧‧‧Electronic injection layer
8‧‧‧ cathode
9‧‧‧ Coverage

Fig. 1 shows a ¹ H-NMR chart of the compound (1-1) of Example 1 of the present invention. Fig. 2 shows a ¹ H-NMR chart of the compound (1-32) of Example 2 of the present invention. Fig. 3 shows a ¹ H-NMR chart of the compound (1-2) of Example 3 of the present invention. Fig. 4 shows a ¹ H-NMR chart of the compound (1-22) of Example 4 of the present invention. Fig. 5 shows a ¹ H-NMR chart of the compound (1-23) of Example 5 of the present invention. Fig. 6 shows a ¹ H-NMR chart of the compound (1-25) of Example 6 of the present invention. Fig. 7 shows the constitution of the organic EL elements of Examples 10 to 13 and Comparative Example 1.

Claims (14)

An organic electroluminescence device comprising, at least in order, an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode electrode and a cover layer, the cover layer comprising an arylamine compound represented by the following formula (1); 1】 (1) (wherein, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ may be the same or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, n represents an integer of 0 to 4; here, at least one of Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ is represented by the following structural formula (B) a monovalent group or a one having a valent group as a substituent) (B) (wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and may be a linking group, or a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group or a nitro group; a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, and 2 to 6 carbon atoms which may have a substituent a linear or branched alkenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, And may also be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ ; X represents a carbon atom or a nitrogen atom, and Y represents a carbon atom or an oxygen atom. a sulfur atom or a nitrogen atom, and Ar ₅ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a a substituted or unsubstituted condensed polycyclic aromatic group or a linking group, and Ar ₆ and Ar ₇ may be the same or different and may be a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic group. When a heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group or a linking group, and Y is an oxygen atom or a sulfur atom, Y makes the number of Ar ₇ 0, and X and Y are nitrogen atoms. When any of Ar ₅ , Ar ₆ and Ar ₇ is a substituent or a linking group, X is a nitrogen atom and Y is a carbon atom, X makes the number of Ar ₆ 0; Ar ₈ represents substituted or not a substituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; but R ₁ , R ₂ , R ₃ , R ₄ , Ar ₅ , Only one of Ar ₆ and Ar ₇ is a linking group, and the case where X is a nitrogen atom and Y is an oxygen atom or a sulfur atom is excluded. The organic electroluminescence device according to claim 1, wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-1); (B-1) (wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and may be a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group or a nitro group, and may be substituted. a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear chain having 2 to 6 carbon atoms which may have a substituent a linear or branched alkenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, and a substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and It may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ ; Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, substituted or Unsubstituted aromatic heterocyclic group, or substituted or unsubstituted condensed polycyclic aromatic group). The organic electroluminescence device according to claim 1, wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-2); (B-2) (wherein R ₁ , R ₃ and R ₄ may be the same or different, and are a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a carbon which may have a substituent a linear or branched alkyl group having 1 to 6 atoms, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched carbon number of 2 to 6 which may have a substituent. An alkenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, substituted or not a substituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and R ₃ and R ₄ may also be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ ; and Ar ₆ and Ar ₈ may be the same or different, indicating a substitution. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group). The organic electroluminescence device according to claim 1, wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-3); (B-3) (wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and may be a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group or a nitro group, and may be substituted. a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear chain having 2 to 6 carbon atoms which may have a substituent a linear or branched alkenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, and a substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and It may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ ; Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, substituted or Unsubstituted aromatic heterocyclic group, or substituted or unsubstituted condensed polycyclic aromatic group). The organic electroluminescence device according to claim 1, wherein the structural formula (B) is a monovalent group represented by the following structural formula (B-4); (B-4) (wherein R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and may be a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group or a nitro group, and may be substituted. a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear chain having 2 to 6 carbon atoms which may have a substituent a linear or branched alkenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkoxy group having 5 to 10 carbon atoms which may have a substituent, and a substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and It may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ ; Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, substituted or Unsubstituted aromatic heterocyclic group, or substituted or unsubstituted condensed polycyclic aromatic group). The organic electroluminescence device of claim 1, wherein the structural formula (B) is a monovalent group represented by the following structural formula (B'); (B') (wherein R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may be the same or different and may be a linking group, or a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom or a cyanogen. a base or a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent a linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 to a substituent a cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted a substituted aryloxy group, and may also be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or N-Ar ₈ ; X represents a carbon atom or a nitrogen atom, Y represents a carbon atom, an oxygen atom, a sulfur atom, or a nitrogen atom, and Ar ₅ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic hetero a cyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, or a linking group, and Ar ₆ and Ar ₇ may be the same or different and may be a substituted or unsubstituted aromatic hydrocarbon group, substituted or not a substituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group or a linking group, and when Y is an oxygen atom or a sulfur atom, Y makes the number of Ar ₇ 0, and X and Y are In the case of a nitrogen atom, any one of Ar ₅ , Ar ₆ and Ar ₇ is a substituent or a linking group, and when X is a nitrogen atom and Y is a carbon atom, X makes the number of Ar ₆ 0; Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; but R ₃ , R ₄ , R ₅ , R ₆ Any one of R ₇ , R ₈ , Ar ₅ , Ar ₆ and Ar ₇ is a linking group, and X is excluded from a nitrogen atom and Y is an oxygen atom or a sulfur atom). The organic electroluminescence device according to claim 1, wherein in the formula (1), n is 0. An organic electroluminescence device according to claim 1, wherein n is 1 in the formula (1). An organic electroluminescence device according to claim 1, wherein in the formula (1), n is 2. The organic electroluminescence device according to claim 1, wherein in the general formula (1), any one of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ is represented by the structural formula (B). A valence group or a one having a valent group as a substituent. The organic electroluminescence device according to the first aspect of the invention, wherein, in the formula (1), Ar ₁ and Ar _{4 are a} monovalent group represented by the structural formula (B) or have a monovalent group as a substitution. Base. The organic electroluminescence device according to claim 1, wherein the thickness of the coating layer is in the range of 30 nm to 120 nm. The organic electroluminescence device according to claim 1, wherein the refractive index of the coating layer is 1.85 or more in a range of a wavelength of light of 450 nm to 750 nm transmitted through the coating layer. One method is to use a compound represented by the formula (1) of the first aspect of the patent application as a coating layer of an organic electroluminescence device.