TW201410663A - Compound having triphenylene ring structure, and organic electroluminescent device - Google Patents

Abstract

A host compound of a light emitting layer, which has a high excited triplet level and is capable of completely confining a triplet exciton of a phosphorescent emitter, is provided as a material for an organic electroluminescent device of high efficiency, and the organic electroluminescent device of high efficiency and high luminance is provided using this compound. The compound having a triphenylene ring structure is represented by a general formula (1), and the organic electroluminescent device having a pair of electrodes and at least one organic layer sandwitched therebetween is characterized in that the compound is used as a constitutive material of at least one organic layer in the organic electroluminescent device.

Description

Compound having a benzene ring structure and an organic electroluminescence device

The present invention relates to a compound of an organic electroluminescence element suitable for a self-luminous element which is suitable for various display devices, and in particular to a compound having a benzene ring structure, and the use thereof An organic electroluminescent device of a compound.

Since the organic electroluminescence element is a self-luminous element, it is brighter than the liquid crystal element and is more excellent in readability, and since it can be clearly displayed, it has become a hot research.

In recent years, as an attempt to improve the luminous efficiency of an element, an element which uses phosphorescent light to generate phosphorescence, that is, to emit light from a triplet excited state has been developed. According to the theory of the excited state, when phosphorescence is used, about four times the luminous efficiency of conventional fluorescent light emission is possible, and remarkable improvement in luminous efficiency is expected.

In 1993, M.A. Baldo et al. of Princeton University achieved an external quantum efficiency of 8% by using a phosphorescent light-emitting element of a ruthenium complex.

Further, an element using light emission by thermal activation delayed fluorescence (TADF) has also been developed. In 2011, Anda et al. of Kyushu University achieved an external quantum efficiency of 5.3% by using an element using a thermally activated delayed fluorescent material (for example, refer to Non-Patent Document 1).

Since the phosphorescent emitter causes concentration extinction, it is generally carried by doping it with a charge transporting compound called a host compound. Guest phosphors Things. The host compound is usually 4,4'-bis(N-carbazolyl)biphenyl (hereinafter abbreviated as CBP) represented by the following formula (for example, see Non-Patent Document 2).

However, since CBP has a low glass transition point (Tg) of 62 ° C and is highly crystalline, it has been pointed out that the stability of the film state is lacking. Therefore, in the case where heat resistance such as high-luminance luminescence is required, satisfactory element characteristics cannot be obtained.

With the progress of research on phosphorescent light-emitting elements, the energy transfer process between phosphorescent emitters and host compounds has been further improved. In order to improve the luminous efficiency, the excited triplet level of the host compound must be higher than that of phosphorescence. It is very clear that the excitation of the triplet energy level is very clear.

When FIrpic of the blue phosphorescent material represented by the following formula is doped to the above-mentioned CBP as a host compound of the light-emitting layer, the external quantum efficiency of the phosphorescent light-emitting element is arrested at about 6%. The reason can be considered as follows: the excitation triplet energy level relative to FIrpic is 2.67 eV, and the excitation triplet energy level of CBP is low value of 2.57 eV. Therefore, the triplet exciton generated by FIrpic cannot be sufficiently sealed by CBP system. . This argument has been confirmed by the fact that the photoluminescence intensity of the film obtained by doping FIrpic with CBP exhibits temperature dependence (for example, refer to Non-Patent Document 3).

A host compound having a higher triplet energy level than CBP is excited, and 1,3-bis(carbazol-9-yl)benzene (hereinafter, abbreviated as mCP) represented by the following formula is known, but mCP is also due to a glass transition point ( Tg) is a low value of 55 ° C and has high crystallinity, so the stability of the film state is lacking. Therefore, in the case where heat resistance is required such as high-luminance illuminance, satisfactory element characteristics cannot be obtained (for example, refer to Non-Patent Document 3).

Further, in order to investigate a host compound having a higher excited triplet energy level, it is known that a high light-emitting efficiency can be obtained when a host compound is doped with an electron transporting or bipolar transporting compound (for example, reference) Non-patent document 4).

As described above, in order to improve the luminous efficiency of the phosphorescent light-emitting device at the time of practical use, it has been considered necessary to excite a host compound of a light-emitting layer having a high triplet energy level and high film stability.

[Previous Technical Literature] [Non-patent literature]

Non-Patent Document 1: Appl. Phys. Let., 98, 083302 (2011)

Non-Patent Document 2: Appl. Phys. Let., 75, 4 (1999)

Non-Patent Document 3: Development and Evaluation Techniques for Materials for Organic EL Lighting, p102-106, Science & Technology (2010)

Non-Patent Document 4: Organic EL Display p90, Ohmsha Co., Ltd. (2005)

Non-Patent Document 5: J. Org. Chem., 60, 7508 (1995)

Non-Patent Document 6: Synth. Commun., 11, 513 (1981)

Non-Patent Document 7: The First Regular Meeting of the Organic EL Symposium, 19 (2005)

The object of the present invention is to provide a host compound of a light-emitting layer which is used as a material for a high-efficiency organic electroluminescence device, has a high excitation triplet energy level, and can completely seal the triplet state of the phosphorescent emitter. Further, the compound is used to provide a highly efficient, high-luminance organic electroluminescent device. The physical properties of the organic compound to be provided by the present invention can be exemplified by (1) excitation triplet energy level is high, (2) bipolar transportability, and (3) film state stability. Further, the physical properties of the organic electroluminescence device to be provided by the present invention can be exemplified by (1) high luminous efficiency and (2) low practical driving voltage.

Therefore, in order to achieve the above object, the inventors of the present invention have focused on the possibility that the triphenylene ring, the dibenzofuran ring and the dibenzothiophene ring have high excitation triplet energy levels, and are designed with the energy level as an index. The compound was chemically synthesized, and the work function was actually measured to confirm the energy level of the compound, and a novel compound having a biphenylene ring structure suitable for the characteristics of the phosphorescent element was found. Further, the use of this compound was carried out to test various organic electroluminescence elements, and the results of the evaluation of the characteristics of the elements were carried out to complete the present invention.

1) That is, the present invention is a compound having a benzene ring structure, which is represented by the formula (1).

(wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ A ₂ may be the same or different and represents a monovalent group represented by the following structural formula (B).

(wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom.)

2) Further, the present invention is a compound having a benzene ring structure as in 1), which is represented by the following formula (1').

(wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ A ₂ may be the same or different and represents a monovalent group represented by the above structural formula (B).

3) Further, the present invention is a compound having a benzene ring structure as in 1), which is represented by the following formula (1").

(wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ A ₂ may be the same or different and represents a monovalent group represented by the above structural formula (B).

4) The present invention is a compound having a benzene ring structure as in the above formula (1), wherein the above structural formula (B) in the formula (1) is a monovalent group represented by the following structural formula (B') Said.

(wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom.)

5) The present invention is a compound having a benzene ring structure as in the above formula (1), wherein the above structural formula (B) in the formula (1) is a monovalent group represented by the following structural formula (B") Said.

(wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom.)

6) Further, the present invention is an organic electroluminescence device having a pair of electrodes and an organic layer sandwiching at least one layer therebetween, wherein at least one layer of the organic layer comprises the formula (1) A compound of a benzene ring structure.

7) The organic electroluminescent device according to 6), wherein the organic layer is a hole blocking layer, and the compound represented by the formula (1) having a triazine structure is attached to the electricity The hole barrier layer is used as at least one constituent material.

8) The present invention is the organic electroluminescence device of (6), wherein the organic layer is a light-emitting layer, Further, the compound represented by the formula (1) having a biphenylene ring structure is used as at least one constituent material in the light-emitting layer.

Further, the present invention is the organic electroluminescence device of (8), wherein the organic layer is a light-emitting layer, and the compound having the structure of a tri-phenylene ring structure represented by the formula (1) is used as the light-emitting layer. The main material is used.

Further, the present invention is the organic electroluminescence device of (6), which has a pair of electrodes and a light-emitting layer containing a phosphorescent luminescent material interposed therebetween and at least one organic layer, wherein the formula (1) represents The compound having a benzene ring structure is used as at least one constituent material in the light-emitting layer.

Further, the invention is the organic electroluminescence device according to 10), wherein the phosphorescent luminescent material comprises a metal complex of ruthenium or platinum.

Further, the present invention is the organic electroluminescence device of (10), wherein the phosphorescent luminescent material is a red luminescent material.

R ₁ to R ₁₇ in the general formula (1), the general formula (1'), the general formula (1), and the structural formula (B), the structural formula (B'), and the structural formula (B") The "alkyl group" which may have a linear or branched alkyl group having 1 to 6 carbon atoms of a substituent, and specifically, may be, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group or a positive group. Butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl and the like.

R ₁ to R ₁₇ in the general formula (1), the general formula (1'), the general formula (1"), and the structural formula (B), the structural formula (B'), and the structural formula (B") The "substituent" of the linear or branched alkyl group having 1 to 6 carbon atoms of the substituent, specifically, the following are exemplified: a halogen atom, a fluorine atom, a chlorine atom, a cyano group, and a trifluoro group. a methyl group, a nitro group, a cyclopentyl group, a cyclohexyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and a linear or branched alkyl group having 1 to 6 carbon atoms; Dialkylamino, phenyl, biphenyl, terphenyl, anthracenyl, styryl, naphthyl, anthryl, phenanthryl, anthracenyl, fluorenyl, pyridyl, bipyridyl, three a group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a fluorenyl group, a pyridocarbonyl group, a carbazolyl group, a quinoxalyl group, a pyrazolyl group; these substituents may further be substituted with the substituents exemplified above Alternatively, the substituents may be bonded to each other to form a ring.

R ₁ to R ₁₇ in the general formula (1), the general formula (1'), the general formula (1"), and the structural formula (B), the structural formula (B'), and the structural formula (B") "Aromatic hydrocarbon group" or "aromatic substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" a heterocyclic group or a "condensed polycyclic aromatic group", specifically, the following are exemplified: phenyl, biphenyl, terphenyl, anthracenyl, styryl, naphthyl, anthracenyl , ethane naphthyl (acenaphthenyl), fluorenyl, phenanthryl, fluorenyl, fluorenyl, pyridyl, bipyridyl, three , pyrimidinyl, furyl, pyrrolyl, thienyl, quinolyl, isoquinolinyl, benzofuranyl, benzothienyl, fluorenyl, carbazolyl, benzo Azyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, pyridohydrazino, dibenzofuranyl, dibenzothiophenyl, Naphthyridinyl, morpholinyl, acridinyl.

R ₁ to R ₁₇ in the general formula (1), the general formula (1'), the general formula (1"), and the structural formula (B), the structural formula (B'), and the structural formula (B") The "substituent" of the substituted aromatic hydrocarbon group, the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" may, for example, be exemplified by a ruthenium atom or a fluorine atom. a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, a cyclopentyl group, a cyclohexyl group, a linear chain having 1 to 6 carbon atoms or a branched alkoxy group, a dialkylamino group substituted with a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, a biphenyl group, a triphenylene group, a fluorenylphenyl group, a styrene group Base, naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl, pyridyl, bipyridyl, three a group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a fluorenyl group, a pyridocarbonyl group, a carbazolyl group, a quinoxalyl group, a pyrazolyl group; these substituents may further be substituted with the substituents exemplified above Replace.

The compound of the formula (1), the formula (1'), and the formula (1") of the present invention having a triphenylene ring structure is a novel compound having a suitable energy level as a host compound of the light-emitting layer. Precise, and has the excellent ability to seal triplet excitons.

The general formula (1), the general formula (1'), and the general formula (1") of the present invention have a structure of a ternary benzene ring structure. The compound can be used as a constituent material of a light-emitting layer or a hole barrier layer of an organic electroluminescence device (hereinafter, simply referred to as an organic EL device). By using the compound of the present invention which is more excellent in bipolar transportability than conventional materials, there is an effect of improving power efficiency or lowering the practical driving voltage.

The compound having a benzene ring structure of the present invention is useful as a compound of a hole blocking layer of an organic EL device or a host compound of a light-emitting layer, and an organic EL device can be produced by using the compound to obtain high efficiency. Low EL voltage organic EL device.

1‧‧‧ glass substrate

2‧‧‧Transparent anode

3‧‧‧ hole transport layer

4‧‧‧Lighting layer

5‧‧‧ hole barrier

6‧‧‧Electronic transport layer

7‧‧‧Electronic injection layer

8‧‧‧ cathode

Fig. 1 is a ¹ H-NMR spectrum chart of a compound (Compound 2) of Example 1 of the present invention.

Fig. 2 is a ¹ H-NMR spectrum chart of the compound (Compound 3) of Example 2 of the present invention.

Fig. 3 is a ¹ H-NMR spectrum chart of the compound (Compound 4) of Example 3 of the present invention.

Figure 4 is a ¹ H-NMR spectrum chart of the compound (Compound 5) of Example 4 of the present invention.

Fig. 5 is a view showing the configuration of EL elements of Examples 7 to 10 and Comparative Examples 1 to 3.

The compound having a biphenylene ring structure of the present invention is a novel compound, and such compounds can be synthesized, for example, in the following manner. First, a corresponding borate body is synthesized by subjecting a dihalide of a comparable triazine compound to boration using bis(pinacolato) diboron or the like (for example, Referring to Non-Patent Document 5), a cross-coupling reaction of the equivalent boric acid ester with a halogenated dibenzofuran or a halogenated dibenzothiophene having various substituents by Suzuki coupling or the like (for example, Referring to Non-Patent Document 6), a compound having a biphenylene ring structure can be synthesized.

On the other hand, by dilating a halogenated dibenzofuran or a halogenated dibenzothiophene having various substituents with a bis (pinacol) diboron or the like, a diphenyl group having various substituents is synthesized. And a boric acid ester of furan or dibenzothiophene, and further, the boric acid ester of dibenzofuran or dibenzothiophene having various substituents and the dihalide of the equivalent triazine compound Suzuki couple The cross-coupling reaction is combined to thereby synthesize a compound having a benzene ring structure.

Specific examples of preferred compounds among the compounds having a tri-phenylene ring structure represented by the general formula (1), the general formula (1'), and the general formula (1") are shown below, but the present invention is not limited thereto. Compound.

(Compound 8)

(Compound 16)

The purification of these compounds is carried out by purification by column chromatography, adsorption purification using tannin extract, activated carbon, activated clay or the like, recrystallization by a solvent, or crystallization. Identification of the compounds was carried out by NMR analysis. For the physical property values, the melting point, the glass transition point (Tg), and the work function were measured. The melting point is an indicator of the vapor deposition property, and the glass transition point (Tg) is an indicator of the stability of the film state, and the work function is an indicator of the energy level of the light-emitting host material.

The melting point and the glass transition point (Tg) were measured using a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S).

Further, the work function was a film of 100 nm on an ITO substrate, and it was measured using an atmospheric photoelectron spectroscope (manufactured by Riken Keiki Co., Ltd., AC-3 type).

The structure of the organic EL device of the present invention can be exemplified by: an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode; Further, an electron injecting layer is further provided between the electron transporting layer and the cathode; and further, an exciton blocking layer is provided on the anode side and/or the cathode side of the light emitting layer. In the multilayer structure, some organic layers may be omitted. For example, the anode, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer, and the cathode may be sequentially formed on the substrate, or the anode and the hole may be formed. The composition of the transport layer, the light-emitting layer, the electron transport layer, and the cathode.

The light-emitting layer, the hole transport layer, and the electron transport layer may each be laminated in two layers. The structure on it.

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. In the hole injection layer of the organic EL device of the present invention, in addition to the porphyrin compound typified by copper phthalocyanine, a naphthalene diamine derivative or a starburst type triphenylamine derivative may be used, and the molecule may have 3 A triphenylamine 3 polymer such as an arylamine compound having a structure in which a triphenylamine structure is bonded by a single bond or a divalent group containing no hetero atom, and a tetramer such as hexacyanoazide An acceptor heterocyclic compound or a coated polymer material of hexacyanoazatriphenylene). These materials may be formed into a film by a conventionally known method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

In the hole transport layer of the organic EL device of the present invention, in addition to the compound containing a m-carbazolylphenyl group, N,N'-diphenyl-N,N'-di(m-tolyl)- can also be used. Benzidine (hereinafter, abbreviated as TPD) or N,N'-diphenyl-N,N'-bis(α-naphthyl)-benzidine (hereinafter, abbreviated as NPD), N, N, N', N '-Biphenylamine derivative such as tetraphenylbenzidine, 1,1-bis[(di-4-toluamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine terpolymers and 4-mer or carbazole derivatives and the like. These may be formed separately, but may be used in the form of a single layer which is mixed with other materials and formed into a film, or may be formed by laminating a layer of a separate film, and laminating the layers formed by mixing the film. A laminated structure of a structure, or a layer formed separately and a layer formed by mixing a film. Further, as the injection hole of the hole, the transport layer can be coated with poly(3,4-ethylenedioxythiophene) (hereinafter, abbreviated as PEDOT)/poly(styrenesulfonate) (hereinafter, abbreviated as PSS). Type of polymer material. These materials may be formed into a film by a conventional 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 further P-doped with tribromoaniline hexachloropyrene or a polymer compound having a TPD structure in a secondary structure may be used as a material which is usually used for the layer.

The electron blocking layer of the organic EL device of the present invention may be 4,4',4"-tris(N-carbazolyl)triphenylamine (hereinafter, abbreviated as TCTA), 9,9-bis[4-(carbazole). -9-yl)phenyl]anthracene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP), 2,2-bis(4-carbazol-9-ylphenyl) diamond Alkane (hereinafter, referred to as Ad-Cz) An oxazole derivative having triphenyl group represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylindenyl)phenyl]-9H-indole A compound having an electron blocking effect, such as a compound of a mercapto group and a triarylamine structure. These may be formed separately, but may be used in the form of a single layer which is mixed with other materials and formed into a film; or may be formed by laminating a layer of a separate film, and laminating the layers formed by mixing the film. A laminated structure of a structure, or a layer formed separately and a layer formed by mixing a film. These materials may be formed into a film by a conventional 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, various metal complexes such as a metal complex of a hydroxyquinoline derivative including quinone (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq ₃ ) can be used. Anthracene derivatives, bisstyrylbenzene derivatives, anthracene derivatives, An azole derivative, a polyparaphenylenevinylene derivative or the like. Further, the light-emitting layer may be composed of a host material and a dopant material. In this case, the host material may be a compound having a triphenylene ring structure represented by the general formula (1) of the present invention, mCP, a thiazole derivative, and a benzo compound. An imidazole derivative, a polydialkylguanidine derivative or the like. Further, as the dopant material, quinacridone, coumarin, erythritol, hydrazine, hydrazine, and the like, a benzopyran derivative, a rhodamine derivative, an amine benzene can be used. Vinyl derivatives and the like. These may be formed separately, but may be used in the form of a single layer which is mixed with other materials and formed into a film; or may be formed by laminating a layer of a separate film, and laminating the layers formed by mixing the film. A laminated structure of a structure, or a layer formed separately and a layer formed by mixing a film.

Further, as the luminescent material, a phosphorescent luminescent material can also be used. As the phosphorescent phosphor, a phosphorescent emitter of a metal complex such as ruthenium or platinum can be used. A green phosphorescent emitter such as Ir(ppy) ₃ , a blue phosphorescent emitter such as FIrpic or FIr6, a red phosphorescent emitter such as Btp ₂ Ir(acac) or Ir(piq) _{3 ,} or the like; For the injection of the hole and the carrier material for transport, a carbazole derivative such as CBP or TCTA or mCP can be used. As a host material for electron transportability, p-bis(triphenylsulfonyl)benzene (hereinafter, abbreviated as UGH2) or 2,2',2"-(1,3,5-phenylene)-para ( 1-phenyl-1H-benzimidazole (hereinafter, abbreviated as TPBI) or the like.

The doping of the host material by the phosphorescent luminescent material is preferably performed by co-evaporation in a range of 1 to 30% by weight with respect to the entire light-emitting layer in order to avoid concentration extinction.

Further, the material of the light-emitting layer may also use a thermally activated delayed fluorescent material. Thermally activated delayed phosphor For the material, PIC-TRZ (for example, refer to Non-Patent Document 1), a compound described in Japanese Patent Application No. 2012-088615, and the like can be used.

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

In addition, an element having a structure in which a light-emitting layer produced by using a compound having a different work function as a host material is adjacent to the light-emitting layer produced by using the compound of the present invention can be produced (for example, see Non-Patent Document 7). .

As the hole blocking layer of the organic EL device of the present invention, in addition to the compound having a ternary benzene ring structure represented by the general formula (1) of the present invention, bathocuproin (hereinafter, abbreviated as BCP) may be used. a metal complex of a hydroxyquinoline derivative such as a phenanthroline derivative or a bis(2-methyl-8-hydroxyquinoline)-4-phenylphenol aluminum (III) (hereinafter abbreviated as BAlq), , can also use a variety of rare earth complexes, Azole derivative, triazole derivative, three A compound having a hole blocking effect such as a derivative. These materials can also serve as materials for the electron transport layer. These may be formed separately, but may be used in the form of a single layer which is mixed with other materials and formed into a film; or may be formed by laminating a layer of a separate film, and laminating the layers formed by mixing the film. A laminated structure of a structure, or a layer formed separately and a layer formed by mixing a film. These materials may be formed into a film by a conventional 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 hydroxyquinoline derivative such as Alq ₃ or BAlq can be used, and various metal complexes, triazole derivatives, and trisole can also be used. derivative, An oxadiazole derivative, a thiadiazole derivative, a carbodiimide derivative, a quinoxaline derivative, a phenanthroline derivative, a silole derivative, or the like. These may be formed separately, but may be used in the form of a single layer which is mixed with other materials and formed into a film; or may be formed by laminating a layer of a separate film, and laminating the layers formed by mixing the film. A laminated structure of a structure, or a layer formed separately and a layer formed by mixing a film. These materials may be formed into a film by a conventional method such as a spin coating method or an inkjet method, in addition to the vapor deposition method.

In 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. In the preferred alternative, it can be omitted.

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

The 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 as an electrode material such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy.

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]

Synthesis of <2,7-bis(8-phenyldibenzo[b,d]furan-2-yl)-triazine (Compound 2)

In a reaction vessel substituted with nitrogen, 10 g of 2,8-dibromodibenzofuran, 4.1 g of phenylboronic acid, 20 ml of 2M aqueous potassium carbonate solution, 1.8 g of hydrazine (triphenylphosphine)palladium (0), 100 ml of toluene, and ethanol were added. 25 ml and heated, and stirred at 60 ° C for 15 hours. After cooling to room temperature, 100 ml of water and 100 ml of toluene were added and subjected to a liquid separation operation, whereby an organic layer was collected. The organic layer was washed twice with 50 ml of water, dried over anhydrous magnesium sulfate, and evaporated to give a crude material. The crude material was purified by column chromatography (support: silica gel, elution solvent: n-hexane) to give white powder of 2-bromo-8-phenyldibenzo[b,d]furan (yield 33%) ).

2-Bromo-8-phenyldibenzo[b,d]furan obtained 3.0 g, and 2,7-bis(4,4,5,5-tetramethyl-[1,3,2] 2-(7-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)triphenylene) 2.2 g, oxetane borane-2-yl) 7.0 ml of 2M potassium carbonate aqueous solution, 0.3 g of hydrazine (triphenylphosphine)palladium (0), 40 ml of toluene, and 10 ml of ethanol were added to a reaction vessel substituted with nitrogen, heated, and refluxed for 8 hours under stirring. The mixture was cooled to room temperature and the precipitate was collected by filtration. 300 ml of tetrahydrofuran was added to the precipitate, and the insoluble matter was removed by filtration, followed by recrystallization using 1,2-dichlorobenzene, thereby obtaining 2,7-bis(8-phenyldibenzo[b,d]furan. -2-yl)-triazine (compound 2) and the like Color powder 1.1 g (yield 34%).

For the white powder obtained, NMR was used to identify the structure. The results of ¹ H-NMR measurement are shown in Fig. 1 .

The following 32 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ). δ(ppm)=9.14(2H), 9.02-9.04(2H), 8.93-8.95(2H), 8.82(2H), 8.60(2H), 8.16-8.18(2H), 8.11-8.14(2H), 7.77- 7.86 (12H), 7.50-7.54 (4H), 7.37-7.42 (2H).

[Embodiment 2]

Synthesis of <2,7-bis(8-phenyldibenzo[b,d]thiophen-2-yl)-triazine (Compound 3) >

In a reaction vessel substituted with nitrogen, 10 g of 2,8-dibromodibenzothiophene, 4.6 g of phenylboronic acid, 22 ml of 2M potassium carbonate aqueous solution, 肆(triphenylphosphine)palladium(0)1.7 g, toluene 100 ml, ethanol were added. 25 ml and heated, and stirred at 60 ° C for 7 hours. After cooling to room temperature, a liquid separation operation was carried out, whereby the organic layer was collected. The organic layer was washed three times with 30 ml of water, dried over anhydrous sodium sulfate and concentrated to give a crude material. The crude product was purified by column chromatography (support: silica gel, elution solvent: n-hexane) to obtain white powder of 2-bromo-8-phenyldibenzo[b,d]thiophene 1.8 g (yield 18%) ).

The obtained 2-bromo-8-phenyldibenzo[b,d]thiophene 1.7g, and 2,7-bis(4,4,5,5-tetramethyl-[1,3,2] 1.2 g of oxaborolan-2-yl)triazine, 3.9 ml of 2M aqueous potassium carbonate solution, 0.2 g of hydrazine (triphenylphosphine)palladium (0), 20 ml of toluene, and 5 ml of ethanol were added under nitrogen substitution. The reaction vessel was heated and refluxed for 5 hours with stirring. The mixture was cooled to room temperature and the precipitate was collected by filtration. 350 ml of tetrahydrofuran was added to the precipitate, and the insoluble matter was removed by filtration, and then recrystallized using 1,2-dichlorobenzene, thereby obtaining 2,7-bis(8-phenyldibenzo[b,d]thiophene. -2-yl) 0.8 g (yield 41%) of a white powder such as benzene (Compound 3).

For the white powder obtained, NMR was used to identify the structure. The results of ¹ H-NMR measurement are shown in Fig. 2 .

The following 32 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ). δ(ppm)=9.19(2H), 9.04-9.07(4H), 8.94-8.96(2H), 8.88(2H), 8.23-8.26(2H), 8.09-8.18(6H), 7.83-7.89(6H), 7.78-7.81 (2H), 7.51-7.55 (4H), 7.39-7.43 (2H).

[Example 3]

Synthesis of <2,7-bis(dibenzofuran-2-yl)-triazine (Compound 4) >

To the reaction vessel, 10 g of dibenzofuran, 2.7 ml of bromine, and 60 ml of acetic acid were added, and the mixture was stirred at room temperature for 24 hours. The precipitated crude product was collected by filtration and washed with methanol, and purified to give white powder of 2-bromodibenzofuran (yield: 23%).

2-Bromodibenzofuran 2.8 g, 2,7-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) 2.5 g of benzene, 8.0 ml of 2M potassium carbonate solution, 0.3 g of ruthenium (triphenylphosphine) palladium (0), 60 ml of toluene, and 15 ml of ethanol were added to a reaction vessel substituted with nitrogen and heated to reflux under stirring. 7 hours. The mixture was cooled to room temperature and the precipitate was collected by filtration. 150 ml of tetrahydrofuran was added to the precipitate, and the insoluble matter was removed by filtration, and then recrystallized using 1,2-dichlorobenzene, thereby obtaining 2,7-bis(dibenzofuran-2-yl)-linked triphenylene. White powder (Compound 4) 1.7 g (yield 57%).

For the white powder obtained, NMR was used to identify the structure. The results of ¹ H-NMR measurement are shown in Fig. 3 .

The following 24 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ). δ(ppm)=9.20(2H), 9.12-9.14(2H), 8.99-9.01(2H), 8.84(2H), 8.34-8.36(2H), 8.16-8.20(4H), 7.88-7.90(2H), 7.81-7.83 (2H), 7.77-7.78 (2H), 7.58-7.61 (2H), 7.48-7.51 (2H).

[Example 4]

Synthesis of <2,7-bis(dibenzothiophen-2-yl)-triazine (Compound 5) >

2-bromodibenzothiophene synthesized by the same bromination as in Example 3, 3.0 g, 2,7-bis(4,4,5,5-tetramethyl-[1,3,2]dioxa 2.5 g of cyclopentaboran-2-yl)triazine, 8.0 ml of 2M aqueous potassium carbonate solution, 0.3 g of hydrazine (triphenylphosphine)palladium (0), 60 ml of toluene, and 15 ml of ethanol were added to a reaction vessel substituted with nitrogen. It was heated and refluxed for 8 hours with stirring. Cool to room temperature and collect by filtration Precipitates. 200 ml of tetrahydrofuran was added to the precipitate, and the insoluble matter was removed by filtration, and then recrystallized using 1,2-dichlorobenzene, thereby obtaining 2,7-bis(dibenzothiophen-2-yl)-linked triphenylene. 1.8 g (yield 58%) of a white powder (Compound 5).

For the white powder obtained, NMR was used to identify the structure. The results of ¹ H-NMR measurement are shown in Fig. 4 .

The following 24 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ). δ(ppm)=9.27(2H), 9.17-9.19(2H), 9.06(2H), 9.03-9.05(2H), 8.70-8.71(2H), 8.27-8.29(2H), 8.19-8.24(4H), 8.09-8.10 (2H), 7.83-7.85 (2H), 7.57-7.62 (4H).

[Comparative Synthesis Example 1]

Synthesis of <2,7-bis(9-phenyl-9H-carbazol-3yl)-triazine (Comparative Compound 1)

In a reaction vessel substituted with nitrogen, 3.0 g of 2-,7-bis(trifluoromethanesulfonyl)-triazine was added, 3-(4,4,5,5-tetramethyl-[1,3,2 4.4 g of dioxaborolan-2-yl)-N-phenylcarbazole, 8.9 ml of 2M aqueous potassium carbonate solution, 0.3 g of ruthenium (triphenylphosphine)palladium (0), 60 ml of toluene, 15 ml of ethanol and It was heated and refluxed for 10 hours with stirring. The mixture was cooled to room temperature and the precipitate was collected by filtration. 350 ml of tetrahydrofuran was added to the precipitate, and the insoluble matter was removed by filtration, and then refluxed with toluene to be purified to obtain 2,7-bis(9-phenyl-9H-carbazole-3yl)-linked three. 3.0 g (yield 74%) of a white powder of benzene (Comparative Compound 1).

For the obtained white powder, NMR was used to identify the structure.

The following 34 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ). δ(ppm)=9.11(2H), 8.99-9.02(2H), 8.86-8.88(2H), 8.81(2H), 8.41-8.43(2H), 8.13-8.15(2H), 7.99-8.02(2H), 7.77-7.79 (2H), 7.70-7.73 (4H), 7.64-7.66 (4H), 7.55-7.58 (2H), 7.45-7.51 (4H), 7.38-7.40 (2H), 7.32-7.36 (2H).

[Example 5]

For the compound of the present invention, a melting point and a glass transition point were determined using a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S).

The compound of the present invention does not have a glass transition point, or has a glass transition point of 100 ° C or higher, indicating that the film state of the compound of the present invention is stability.

[Embodiment 6]

Using the compound of the present invention, a vapor deposited film having a thickness of 50 nm was formed on an ITO substrate, and a work function was measured by an atmospheric photoelectron spectroscope (manufactured by Riken Keiki Co., Ltd., AC-3 type).

As such, the compound of the present invention has an equivalent energy level as compared to CBP which is generally used as a host compound of the light-emitting layer.

[Embodiment 7]

As shown in FIG. 5, the organic EL element is formed by preliminarily forming an ITO electrode as a transparent anode 2 on the glass substrate 1, and sequentially vapor-depositing the hole transport layer 3, the light-emitting layer 4, the hole barrier layer 5, and the electron transport layer. 6. An electron injecting layer 7 and a cathode (aluminum electrode) 8 are obtained.

Specifically, the glass substrate 1 on which the ITO film having a film thickness of 100 nm was formed was washed with an organic solvent, and then the surface was washed by UV ozone treatment. Then, the glass substrate with the ITO electrode was placed in a vacuum vapor deposition machine and depressurized to 0.001 Pa or less. Next, a compound of the following structural formula (Tris-PCz) was deposited as a hole transport layer 3 at a deposition rate of 2 Å/s to a film thickness of 50 nm so as to cover the transparent anode 2. On the hole transport layer 3, the compound (Compound 2) of the present invention and the red phosphorescent emitter Ir(piq) ₃ were compared at a vapor deposition rate to a compound 2: Ir(piq) ₃ = 94:6 The vapor deposition rate was subjected to binary vapor deposition, and a film thickness of 20 nm was formed to form a light-emitting layer 4. On the light-emitting layer 4, BCP was formed as a hole blocking layer 5 by forming a film thickness of 10 nm at a deposition rate of 2 Å/s. On the hole barrier layer 5, Alq ₃ was formed into a film thickness of 30 nm at a vapor deposition rate of ₂ Å/s as the electron transport layer 6. On the electron transport layer 6, lithium fluoride was deposited as an electron injection layer 7 at a deposition rate of 0.1 Å/s to a thickness of 1 nm. Finally, aluminum was vapor-deposited so that the film thickness became 70 nm to form the cathode 8. The characteristics of the organic EL device produced were measured in the air at room temperature.

The measurement results of the luminescence characteristics when a DC voltage was applied to the organic EL device produced by using the compound (Compound 2) of Example 1 of the present invention are shown in Table 1.

[Embodiment 8]

The material of the light-emitting layer 4 of Example 7 was replaced with the compound (Compound 2) of Example 1 as the compound (Compound 3) of Example 2 of the present invention, and an organic EL device was produced under the same conditions as in Example 7. The characteristics of the organic EL device produced were measured in the air at room temperature. The measurement results of the light-emitting characteristics when a DC voltage was applied to the produced organic EL device are shown in Table 1.

[Comparative Example 1]

For comparison, the material of the light-emitting layer 4 of Example 7 was replaced with the compound of Example 1 (Compound 2) to CBP, and an organic EL device was produced under the same conditions as in Example 7. The characteristics of the organic EL device produced were measured in the air at room temperature. The measurement results of the light-emitting characteristics when a DC voltage was applied to the produced organic EL device are shown in Table 1.

[Comparative Example 2]

For comparison, the material of the light-emitting layer 4 of Example 7 was replaced with the compound of Example 1 (Compound 2) to Comparative Compound 1, and an organic EL device was produced under the same conditions as in Example 7. The characteristics of the organic EL device produced were measured in the air at room temperature. The measurement results of the light-emitting characteristics when a DC voltage was applied to the produced organic EL device are shown in Table 1.

As shown in Table 1, the driving voltage at a current density of 10 mA/cm ² was 9.8 V for the organic EL device of Comparative Example 1 using CBP, and 9.6 V for the organic EL device of Comparative Example 2 using Comparative Compound 1. The organic EL device of Example 7 was 9.0 V, and the organic EL device of Example 8 was 8.2 V, which showed a decrease in voltage.

As shown in Table 1, the external quantum efficiency at a current density of 10 mA/cm ² was 6.7% with respect to the organic EL device of Comparative Example 1 using CBP, and 6.5% of the organic EL device of Comparative Example 2 using Comparative Compound 1. The organic EL device of Example 7 was 7.0%, and the organic EL device of Example 8 was 7.2%, which showed high efficiency.

[Embodiment 9]

The glass substrate 1 on which the ITO film having a film thickness of 100 nm was formed was washed with an organic solvent, and then the surface was washed by UV ozone treatment. Then, the glass substrate with the ITO electrode was placed in a vacuum vapor deposition machine and depressurized to 0.001 Pa or less. Next, the compound of the above formula (Tris-PCz) was formed into a hole transport layer 3 by a film thickness of 50 nm at a deposition rate of 2 Å/s so as to cover the transparent anode 2. On the hole transport layer 3, the compound (Compound 4) of the present invention and the red phosphorescent emitter Ir(piq) ₃ were compared at a vapor deposition rate to a compound 4: Ir(piq) ₃ = 94:6 The vapor deposition rate was subjected to binary vapor deposition, and a film thickness of 20 nm was formed to form a light-emitting layer 4. On the light-emitting layer 4, BCP was formed as a hole blocking layer 5 by forming a film thickness of 10 nm at a deposition rate of 2 Å/s. On the hole blocking layer 5, a compound of the following structural formula (Bpy-TP2) was formed into a film as an electron transporting layer 6 at a vapor deposition rate of 2 Å/s to a film thickness of 60 nm. On the electron transport layer 6, lithium fluoride was deposited as an electron injection layer 7 at a deposition rate of 0.1 Å/s to a thickness of 1 nm. Finally, aluminum was vapor-deposited so that the film thickness became 70 nm to form the cathode 8. The characteristics of the organic EL device produced were measured in the air at room temperature.

The measurement results of the luminescence characteristics when a DC voltage was applied to the organic EL device produced by using the compound (Compound 4) of Example 3 of the present invention are shown in Table 2.

[Embodiment 10]

The material of the light-emitting layer 4 of Example 9 was replaced with the compound of Example 3 (Compound 4) as the compound of Example 4 (Compound 5), and an organic EL device was produced under the same conditions as in Example 9. The characteristics of the organic EL device produced were measured in the air at room temperature. The measurement results of the light-emitting characteristics when a DC voltage was applied to the produced organic EL device are shown in Table 2.

[Comparative Example 3]

For comparison, the material of the light-emitting layer 4 of Example 9 was replaced with CBP by the compound of Example 3 (Compound 4), and an organic EL device was produced under the same conditions as in Example 9. The characteristics of the organic EL device produced were measured in the air at room temperature. The measurement results of the light-emitting characteristics when a DC voltage was applied to the produced organic EL device are shown in Table 2.

As shown in Table 2, the driving voltage at a current density of 10 mA/cm ² was 6.4 V with respect to the organic EL device of Comparative Example 3 using CBP, and the organic EL device of Example 9 was 6.4 V. The EL element is 7.2V, which shows a low voltage.

As shown in Table 2, the external quantum efficiency at a current density of 10 mA/cm ² was 9.1% with respect to the organic EL device of Comparative Example 3 using CBP, and the organic EL device of Example 9 was 9.1%. The organic EL element was 12.3%, which showed high efficiency.

From the results, it is clear that the organic EL device having the compound having a benzene ring structure of the present invention can achieve a reduction in driving voltage and an increase in external quantum efficiency as compared with CBP of a general luminescent host material.

As above, the compounds of the invention have a suitable energy level and have a suitable seal The ability of heavy energy.

[Industrial use]

The compound having a biphenylene ring structure of the present invention exhibits an excellent energy level and has an ability to block triplet energy, and is excellent as a host compound of a light-emitting layer and a hole blocking property. Moreover, by using the compound to produce an organic EL device, the luminance and luminous efficiency of the conventional organic EL device can be improved.

1‧‧‧ glass substrate

2‧‧‧Transparent anode

3‧‧‧ hole transport layer

4‧‧‧Lighting layer

5‧‧‧ hole barrier

6‧‧‧Electronic transport layer

7‧‧‧Electronic injection layer

8‧‧‧ cathode

Claims (12)

a compound having a benzene ring structure, represented by the following formula (1); (wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ , A ₂ may be the same or different, and represents a monovalent group represented by the following structural formula (B); (wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom). a compound having a benzene ring structure as disclosed in claim 1 of the patent, represented by the following formula (1'); (wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ A ₂ may be the same or different and represents a monovalent group represented by the structural formula (B). A compound having a biphenylene ring structure as claimed in claim 1 is represented by the following formula (1"); (wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ A ₂ may be the same or different and represents a monovalent group represented by the structural formula (B). A compound having a biphenylene ring structure according to the first aspect of the invention, wherein the structural formula (B) in the formula (1) is represented by a monovalent group represented by the following structural formula (B'); (wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom). A compound having a benzene ring structure according to the first aspect of the invention, wherein the structural formula (B) in the formula (1) is represented by a monovalent group represented by the following structural formula (B"); (wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom). An organic electroluminescence device having a pair of electrodes and an organic layer sandwiching at least one layer therebetween, wherein a compound having a benzene ring structure represented by the following formula (1) is used as at least one organic layer The constituent materials are used; (wherein R ₁ to R ₁₀ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; A ₁ , A ₂ may be the same or different, and represents a monovalent group represented by the following structural formula (B); (wherein R ₁₁ to R ₁₇ may be the same or different and each represents a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or a carbon atom having a substituent of from 1 to 6 a chain or branched alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; X represents An oxygen atom, a sulfur atom or a selenium atom). The organic electroluminescence device of claim 6, wherein the organic layer is a hole blocking layer, and the compound represented by the formula (1) is used as at least one constituent material in the hole blocking layer. The organic electroluminescence device according to claim 6, wherein the organic layer is a light-emitting layer, and the compound represented by the formula (1) is used as at least one constituent material in the light-emitting layer. The organic electroluminescence device according to claim 8, wherein the organic layer is a light-emitting layer, and the compound represented by the formula (1) is used as a host material of the light-emitting layer. An organic electroluminescent device according to claim 6 which has a pair of electrodes and clips In the luminescent layer containing the phosphorescent luminescent material and the organic layer of at least one layer, the compound represented by the formula (1) is used as at least one constituent material in the luminescent layer. The organic electroluminescence device according to claim 10, wherein the phosphorescent luminescent material comprises a metal complex of ruthenium or platinum. The organic electroluminescence device according to claim 10, wherein the phosphorescent luminescent material is a red luminescent material.