Arylamine compound, organic electroluminescent element, and electronic device

Abstract

Provided are an arylamine compound, an organic electroluminescent element, and an electronic device. The purpose of the present invention is to provide a material for organic EL elements, which has excellent hole transport ability and electron blocking ability, and has high thermal stability in a thin film state. Also provided is an organic EL element which is low in driving voltage, high in luminous efficiency and power efficiency, and long in element life. An arylamine compound represented by general formula (1). In the formula, Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, Ar2 to Ar5 may be the same or different from each other and represent a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, R1-R14 represent a hydrogen atom or a deuterium atom, and m and n each independently represent an integer of 1-2.

Description

TECHNICAL FIELD

[0001] The present application relates to a compound and an element suitable for an organic electroluminescent element (hereinafter referred to as an organic EL element) which is a self-emitting element suitable for various display devices, and in detail, to an arylamine compound and an organic EL element using the same. BACKGROUND

[0002] The organic EL element is a self-emitting element, and thus is brighter and has more excellent visibility than a liquid crystal element, and enables clear display, and thus is actively researched.

[0003] In 1987, C. W. Tang et al. of Eastman Kodak Company developed a stacked structure element in which each material assumes various functions, and thus put into practical use an organic EL element using an organic material. They stacked a fluorescent body capable of transporting electrons and an organic layer capable of transporting holes, and injected charges of both into the layer of the fluorescent body to make it emit light, and thus obtained 1000 cd / m2or more at a voltage of 10 V or less (Patent Document 1). 2 The above high brightness (for example, refer to Patent Documents 1 and 2).

[0004] Up to now, many improvements have been made for the practical use of the organic EL element, and an electric field light-emitting element in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate by further subdividing the various roles of the stacked structure has been realized, and high efficiency and durability have been achieved (for example, refer to Non-Patent Document 1).

[0005] In addition, for the purpose of further improving the light-emitting efficiency, application of triplet excitons has been attempted, and application of a phosphorescent light-emitting compound has been researched (for example, refer to Non-Patent Document 2). Furthermore, an element utilizing light emission based on thermally activated delayed fluorescence (TADF) has been developed, and in 2011, Ando et al. of Kyushu University achieved an external quantum efficiency of 5.3% using an element using a thermally activated delayed fluorescence material (for example, refer to Non-Patent Document 3).

[0006] The light-emitting layer can also be produced by doping a fluorescent compound, a phosphorescent light-emitting compound, or a material emitting delayed fluorescence in a charge-transporting compound generally called a host material. As described in the above Non-Patent Documents, the selection of the organic material in the organic EL element greatly influences many characteristics such as the efficiency and durability of the element (for example, refer to Non-Patent Documents 1 to 3).

[0007] In an organic EL element, charges injected from both electrodes recombine in a light-emitting layer to obtain light emission, but how to efficiently cause both holes and electrons to transition to the light-emitting layer is essential, and an element having excellent carrier balance is required. Therefore, by using a material having a property of improving the hole-injection property of holes injected from the anode to the light-emitting layer and improving the electron-blocking property of blocking electrons injected from the cathode, the probability of recombination of holes and electrons in the light-emitting layer is increased, and further, by limiting the generation of excitons in the light-emitting layer, a high light-emitting efficiency can be obtained. Therefore, the role of a hole-transporting material is essential, and a hole-transporting material having a high hole-injection property, a large hole mobility, a high electron-blocking property, and a high durability to electrons is required.

[0008] In addition, with respect to the lifetime of the element, the heat resistance and amorphousness of the material are also important. A material having low heat resistance is thermally decomposed even at low temperatures due to heat generated during driving of the element, and the material deteriorates. A material having low amorphousness is crystallized even in a short time, and the element deteriorates. Therefore, a material having high heat resistance and excellent amorphousness is required.

[0009] As a hole-transporting material for an organic EL element so far, there are N,N'-diphenyl-N,N'-di(a-naphthyl)benzidine (NPD) and various aromatic amine derivatives (for example, refer to Patent Document 1 and Patent Document 2). However, NPD has a good hole-transporting ability, but the glass transition temperature (Tg) as an index of heat resistance is as low as 96°C, and the characteristics of the element are reduced due to crystallization under high temperature conditions (for example, refer to Non-Patent Document 4).

[0010] In addition, among the aromatic amine derivatives described in the above patent documents, there are compounds having an excellent mobility of 10 -3 cm 2 / Vs or more (for example, refer to Patent Document 1 and Patent Document 2), but since the electron-blocking property is insufficient, a part of the electrons penetrates the light-emitting layer, and an improvement in light-emitting efficiency or the like cannot be expected, and for further high efficiency, a material having a higher electron-blocking property, a more stable thin film, and a higher heat resistance is required. In addition, there is a report of an aromatic amine derivative having a high durability (for example, refer to Patent Document 3), but it is used as a charge-transporting material for an electrophotographic photoreceptor, and there is no example of use as an organic EL element.

[0011] As a compound in which heat resistance, hole-injection property, and the like are improved in order to solve the problem, an arylamine compound having a substituted carbazole structure, a heterocyclic structure containing a fluorene skeleton (for example, refer to Patent Document 4 and Patent Document 5) has been proposed, but elements in which these compounds are used for a hole-injection layer or a hole-transport layer are not yet sufficient in improvement of element lifetime, luminous efficiency, and the like, and further reduction in driving voltage, higher luminous efficiency, and longer element lifetime are required.

[0012] Patent Document 1: U.S. Patent No. 5792557

[0013] Patent Document 2: U.S. Patent No. 5639914

[0014] Patent Document 3: U.S. Patent No. 7759030

[0015] Patent Document 4: Japanese Patent Application Laid-Open No. 2009-076817

[0016] Patent Document 5: Japanese Patent No. 7177966

[0017] Patent Document 6: European Patent No. 2684932

[0018] Non-Patent Document 1: Abstracts of the 9th Symposium of the Society of Applied Physics, pp. 55-61 (2001)

[0019] Non-Patent Document 2: Abstracts of the 9th Symposium of the Society of Applied Physics, pp. 23-31 (2001)

[0020] Non-Patent Document 3: Appl. Phys. Lett., 98, 083302 (2011)

[0021] Non-Patent Document 4: Abstracts of the 3rd Symposium of Organic EL Devices, pp. 13-14 (2006) SUMMARY

[0022] An object of the present application is to provide a material for an organic EL element, which has excellent hole-transporting ability and electron-blocking ability, and high thermal stability in a thin film state. Another object is to provide an organic EL element, which has low driving voltage, high luminous efficiency and power efficiency, and long element lifetime.

[0023] In order to achieve the above object, the present inventors have found that by introducing substituents at specific positions to pursue optimization of the structure, it is possible to dramatically improve the properties of the material, while focusing on the fact that specific triarylamine compounds have excellent hole injection / transport ability, electron blocking ability, stability of thin films, and durability. Furthermore, in an organic EL element, it is possible to improve the performance of luminous efficiency and power efficiency, to suppress the light emission start voltage and practical driving voltage, to achieve long life exceeding the life of the past, and thus the present application has been completed.

[0024] That is, according to the present application, it is possible to provide the following arylamine compound and an organic EL element and electronic device using the same.

[0025] 1) An arylamine compound represented by the following general formula (1).

[0026] [Chemical Formula 1]

[0027]

[0028] (In the formula, Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, Ar2 to Ar5 can be the same as or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, R1 to R 14 represent a hydrogen atom or a deuterium atom, and m and n each independently represent an integer of 1 to 2.)

[0029] 2) The arylamine compound according to the above 1), wherein in the general formula (1), Ar2 to Ar5 are arbitrarily the same as or different from each other, and are a group represented by the following general formula (2).

[0030] [Chemical Formula 2]

[0031]

[0032] (In the formula, R 15 to R 19 are arbitrarily the same as or different from each other, and represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, R 15 to R 19 are arbitrarily bonded to each other to form a ring.)

[0033] 3) The arylamine compound according to the above 2), wherein in the general formula (2), R 15 to R 19 are hydrogen atoms.

[0034] 4) The arylamine compound according to the above 1), wherein in the general formula (1), m or n is 1.

[0035] 5) An organic EL element having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein the organic layer contains any one of the arylamine compounds described in 1) to 4).

[0036] 6) The organic EL element according to 5) above, wherein the organic layer is a hole transport layer.

[0037] 7) The organic EL element according to 5) above, wherein the organic layer is an electron blocking layer.

[0038] 8) The organic EL element according to 5) above, wherein the organic layer is a hole injection layer.

[0039] 9) An electronic device comprising an electronic element having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein the organic layer comprises any one of the above-described arylamine compounds (1) to (4).

[0040] The compounds of this invention possess excellent hole transport and electron blocking capabilities, and exhibit high thermal stability in the thin-film state, thus making them useful as electron blocking and hole transport materials. Organic electroluminescent devices using the compounds of this invention as the organic layer material can achieve low driving voltage, high luminous efficiency, and long device lifetime. Attached Figure Description

[0041] Figure 1 The diagram shows compounds (1) to (12) as preferred examples of arylamine compounds represented by general formula (1).

[0042] Figure 2 The diagram shows compounds (13) to (24) as preferred examples of arylamine compounds represented by general formula (1).

[0043] Figure 3 The diagram shows compounds (25) to (36) as preferred examples of arylamine compounds represented by general formula (1).

[0044] Figure 4 The diagram shows compounds (37) to (48) as preferred examples of arylamine compounds represented by general formula (1).

[0045] Figure 5 The diagram shows compounds (49) to (60) as preferred examples of arylamine compounds represented by general formula (1).

[0046] Figure 6is a view showing compounds (61) to (72) as preferable specific examples of the arylamine compound represented by General Formula (1).

[0047] Figure 7 is a view showing compounds (73) to (84) as preferable specific examples of the arylamine compound represented by General Formula (1).

[0048] Figure 8 is a view showing compounds (85) to (96) as preferable specific examples of the arylamine compound represented by General Formula (1).

[0049] Figure 9 is a view showing compounds (97) to (108) as preferable specific examples of the arylamine compound represented by General Formula (1).

[0050] Figure 10 is a view showing compounds (109) to (118) as preferable specific examples of the arylamine compound represented by General Formula (1).

[0051] Figure 11 is a view showing the structure of the organic EL element of Examples 8 to 12 and Comparative Example 1.

[0052] (Explanation of Reference Numerals)

[0053] 1...glass substrate

[0054] 2...transparent anode

[0055] 3...hole injection layer

[0056] 4...hole transport layer

[0057] 5...electron blocking layer

[0058] 6...light emitting layer

[0059] 7...electron transport layer

[0060] 8...electron injection layer

[0061] 9...cathode

[0062] 10...cover layer DETAILED DESCRIPTION

[0063] Hereinafter, the content of the present application will be explained in detail. The explanation of the constituent elements described below is sometimes made based on representative embodiments, specific examples of the present application, but the present application is not limited to such embodiments, specific examples. Note that the numerical range indicated by "~" in the present specification means a range including the numerical values recited before and after the "~" as lower limit values and upper limit values.

[0064] The aromatic ring constituting the "aromatic hydrocarbon group" (aryl group) in the "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar1to Ar5in General Formula (1) can be a monocyclic ring, a condensed ring (condensed polycyclic aromatic group) in which 2 or more rings are condensed, a linked ring in which 2 or more rings are linked by a single bond, or a spiro ring in which 2 or more rings are linked by a spiro bond. The number of carbon atoms in the aromatic ring is, for example, selected from the range of 6 to 30. As the "aromatic hydrocarbon group", specifically, mention can be made of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenyl, fluorenyl, spirobifluorenyl, and the like.

[0065] The "aromatic heterocyclic group" (heteroaryl group) in the "substituted or unsubstituted aromatic heterocyclic group" represented by Ar1to Ar5in General Formula (1) can be a monocyclic ring, or a condensed ring in which 2 or more rings are condensed. The number of carbon atoms in the aromatic heterocyclic group is, for example, selected from the range of 2 to 40, or from the range of 2 to 20. As the "aromatic heterocyclic group", specifically, mention can be made of pyridyl, pyrimidinyl, triazinyl, furanyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, azaf luorenyl, diazaf luorenyl, azaspirofluorenyl, diazaspirofluorenyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthrydinyl, phenanthrolinyl, acridinyl, and carbolinyl groups, and the like.

[0066] As the "substituent" in the "substituted aromatic hydrocarbon group" and "substituted aromatic heterocyclic group" represented by Ar1to Ar5in General Formula (1), for example, there can be mentioned a deuterium atom, a cyano group, a nitro group; a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like halogen atom; a trimethylsilyl group, a triphenylsilyl group and the like silyl group; a methyl group, an ethyl group, a propyl group and the like straight-chain or branched alkyl group having 1 to 6 carbon atoms; a methyloxy group, an ethyloxy group, a propyloxy group and the like straight-chain or branched alkyloxy group having 1 to 6 carbon atoms; a vinyl group, an allyl group and the like alkenyl group; a phenyloxy group, a tolyloxy group and the like aryloxy group; a benzyl oxy group, a phenethyloxy group and the like aralkyloxy group; a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a spirobifluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenyl group and the like aromatic hydrocarbon group or fused polycyclic aromatic group; a pyridyl group, a thienyl group, a furanyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbolinyl group and the like aromatic heterocyclic group, and these substituents can be further substituted with the above-mentioned substituents. In addition, the benzene ring substituted with these substituents, or a plurality of substituents substituted on the same benzene ring can be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

[0067] As Ar1of General Formula (1), a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzofuranyl group is preferred, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzofuranyl group is more preferred, and an unsubstituted biphenyl group, an unsubstituted terphenyl group, a 9,9-dialkylfluorenyl group having 1 to 6, preferably 1 to 3 carbon atoms in the alkyl group, or an unsubstituted dibenzofuranyl group is most preferred.

[0068] In the aforementioned General Formula (1), Ar2to Ar5may be the same as or different from each other, and a substituted or unsubstituted aromatic hydrocarbon group is preferred, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group is more preferred, and a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group is further preferred.

[0069] Ar2and Ar4may be the same, Ar3and Ar5may be the same, or Ar2to Ar5may all be the same.

[0070] R1to R4of General Formula (1) 14 represents a hydrogen atom or a deuterium atom, and can be partially or entirely deuterium atoms.

[0071] In General Formula (1), m and n represent an integer of 1 to 2, and m can be 1 and n can be 1, or m can be 2 and n can be 2, or m can be 1 and n can be 2, or m can be 2 and n can be 1. In the present application, it is preferable that m or n be 1.

[0072] In addition, Ar2to Ar5may be the same as or different from each other, and are preferably a group represented by the above General Formula (2).

[0073] In the above General Formula (1), in the case where Ar2to Ar5are represented by the above General Formula (2), the "substituted or unsubstituted aromatic hydrocarbon group" represented by R 15 to R 19 in General Formula (2) can be a single ring, or a fused ring (fused polycyclic aromatic group) in which 2 or more rings are fused, can be a linked ring in which 2 or more rings are linked by a single bond, or can be a linked ring in which 2 or more rings are linked by a single bond or a spiro ring in which 2 or more rings are linked by a spiro bond. The same groups as those exemplified in the "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar1to Ar5in General Formula (1) can be given.

[0074] In addition, the "aromatic heterocyclic group" (heteroaryl group) in the "substituted or unsubstituted aromatic heterocyclic group" represented by R 15 to R 19 in General Formula (2) can be a single ring, or a fused ring in which 2 or more rings are fused. The number of carbon atoms in the aromatic heterocyclic group is, for example, selected from the range of 2 to 40, or can be selected from the range of 2 to 20. The same groups as those exemplified in the "substituted or unsubstituted aromatic heterocyclic group" represented by Ar1to Ar5in General Formula (1) can be given.

[0075] As the "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group" and the "substituted or unsubstituted aromatic heterocyclic group" represented by R 15 to R 19 in General Formula (2), the same groups as those exemplified in the "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" represented by Ar1to Ar5in General Formula (1) can be given.

[0076] In General Formula (2), adjacent groups in R 15 to R 19 may be bonded to each other by a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.

[0077] In General Formula (2), R 15 to R 19They can be the same or different from each other, preferably hydrogen atoms or deuterium atoms, and more preferably all hydrogen atoms.

[0078] From the perspective of excelling hole injection / transport capability, film stability and durability, the arylamine compound represented by the above general formula (1) is preferably used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer or light emission layer of the organic EL element, and more preferably as a constituent material of the hole transport layer or electron blocking layer.

[0079] The arylamine compound represented by the above general formula (1) suitable for use in the organic EL element of the present invention is preferably used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer or light emission layer of the organic EL element, and more preferably as a constituent material of the hole transport layer or electron blocking layer.

[0080] The arylamine compounds of the present invention are novel compounds, but these compounds can be synthesized by methods known in themselves (e.g., see Patent Document 5).

[0081] The purification of arylamine compounds represented by general formula (1) can be carried out using known methods such as column chromatography, adsorption purification based on silica gel, activated carbon, activated clay, etc., solvent-based recrystallization, crystallization, and sublimation purification. The compounds can be identified by NMR analysis.

[0082] Among the arylamine compounds represented by the above general formula (1) suitable for use in the organic EL element of the present invention, preferred compounds include, for example... Figures 1-10 As shown, but not limited to these compounds. Hydrogen atoms are omitted from the chemical structural formula. 1 The representation of H). Additionally, D represents a deuterium atom (H). 2 H). Aromatic amine compounds represented by general formula (1) can have all hydrogen atoms in the illustrated structure replaced by deuterium atoms.

[0083] The compounds of the present invention, represented by general formula (1), possess excellent hole transport and electron blocking capabilities and high thermal stability in the thin film state, thus making them useful as materials for the organic layers of organic electroluminescent devices. The compounds represented by general formula (1) can be used, for example, as constituent materials for hole injection layers, electron blocking layers, hole transport layers, and light-emitting layers of organic electroluminescent devices, and are particularly useful as constituent materials for electron blocking layers and hole transport layers.

[0084] The present application aims to provide a material for an organic EL element which is high in efficiency and durability, and which is excellent in (1) hole injection / transport properties, (2) electron blocking ability, (3) stability in a thin film state, and (4) durability.

[0085] In addition, the present application aims to provide an organic EL element which is high in (1) luminous efficiency and power efficiency, (2) low in luminous onset voltage and practical driving voltage, and (3) long in lifetime, by using the material of the present application.

[0086] As the physical property values as the indices of usefulness of the compound represented by General Formula (1), there can be mentioned, for example, measurement of melting point, glass transition temperature (Tg), and work function (energy level of HOMO). The melting point is a physical property value as an index of evaporation property, the glass transition temperature (Tg) is a physical property value as an index of stability in a thin film state, and the work function is a physical property value as an index of hole injection property, hole transport property, or electron blocking property.

[0087] The melting point and the glass transition temperature (Tg) can be measured, for example, by using a powder and using a high-sensitivity differential scanning calorimeter (Rigaku, DSCvesta Thermοplus EV02 series).

[0088] The work function (energy level of HOMO) can be calculated, for example, by forming a thin film of 100 nm on an ITO substrate and using an ionization potential measuring device (Sumitomo Heavy Industries, Ltd., PYS-202).

[0089] <Organic electroluminescent element>

[0090] The organic electroluminescent element (organic EL element) of the present application has a pair of electrodes and an organic layer containing at least a light-emitting layer between the pair of electrodes, and can contain one or more organic layers in addition to the light-emitting layer. Here, the pair of electrodes is an anode and a cathode.

[0091] The organic EL element of the present application has an organic layer containing at least a light-emitting layer, and can have one or more organic layers in addition to the light-emitting layer. Here, the compound represented by General Formula (1) can be contained in the light-emitting layer or in an organic layer other than the light-emitting layer, but is preferably contained in an organic layer disposed between the light-emitting layer and the anode. As a specific example of the organic layer disposed between the light-emitting layer and the anode, there can be mentioned a hole injection layer, a hole transport layer, an electron blocking layer, and the like, and the compound represented by General Formula (1) is preferably contained in the hole transport layer, the electron blocking layer, and more preferably in the electron blocking layer. The materials of these organic layers can be appropriately selected from publicly known materials.

[0092] As the structure of the organic EL element of the present application, there are a structure in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate, a structure in which an electron blocking layer is provided between the hole transport layer and the light-emitting layer, and a structure in which a hole blocking layer is provided between the light-emitting layer and the electron transport layer. In these multilayer structures, one organic layer can have the functions of several layers, for example, one organic layer can function as both the hole injection layer and the hole transport layer, one organic layer can function as both the electron injection layer and the electron transport layer, and the like. In addition, the organic layer having the same function can be stacked in two or more layers, the hole transport layer can be stacked in two layers, the light-emitting layer can be stacked in two layers, the electron transport layer can be stacked in two layers, and the like. The organic EL element of the present application does not exclude other layers between the layers as long as it has at least an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode in the above order.

[0093] [Anode]

[0094] As the anode of the organic EL element of the present application, an electrode material having a large work function such as ITO, gold, and the like can be used. As the material of the hole injection layer of the organic EL element of the present application, a porphyrin compound typified by copper phthalocyanine, a Star Burst type triphenylamine derivative, an arylamine compound having two or more triphenylamine structures or carbazole structures in a molecule and each having a structure linked by a single bond or a 2-valent group not containing a hetero atom, an acceptor heterocyclic compound such as hexacyanobenzophenanthroline, and a coating type high molecular material, and the like can be used. These materials can be formed into a thin film by a publicly known method such as an evaporation method, a spin coating method, an inkjet method, and the like.

[0095] [Hole injection layer, hole transport layer]

[0096] The hole injection layer is a layer provided between the anode and the light-emitting layer, between the anode and the hole transport layer, and the like, for reducing the driving voltage by lowering the injection barrier of the holes supplied from the anode, and for increasing the light-emitting luminance.

[0097] The hole transport layer is a layer having a function of transporting holes. The hole transport layer can be a hole injection transport layer having a function of the hole injection layer.

[0098] As the material of the hole injection layer of the organic EL element of the present application, a phthalocyanine compound represented by copper phthalocyanine, a Star Burst type triphenylamine derivative, an arylamine compound having two or more triphenylamine structures or carbazole structures in the molecule and each having a structure linked by a single bond or a divalent group not containing a hetero atom, an acceptor heterocyclic compound such as hexacyanobenzophenanthroline, and a coating type high molecular material, etc. can be used. These materials can be formed into a thin film by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0099] As the material of the hole injection layer and the hole transport layer of the organic EL element of the present application, in addition to the arylamine compound of the present application, a diphenylamine derivative such as N,N'-diphenyl-N,N'-di(m-tolyl)-phenylamine (TPD), N,N'-diphenyl-N,N'-di(a-naphthyl)-phenylamine (NPD), N,N,N',N'-tetraphenylphenylamine, and an arylamine compound having two or more triphenylamine structures or carbazole structures in the molecule and each having a structure linked by a single bond or a divalent group not containing a hetero atom, etc. can be used. These materials can be formed into a thin film individually or in a mixture of a plurality of kinds, and each can be used as a single layer. In addition, it can be a stacked structure between layers formed of these materials individually, a stacked structure between layers formed of a mixture, or a stacked structure between a layer formed of these materials individually and a layer formed of a mixture of a plurality of kinds. In addition, as the material of the hole injection / transport layer, a coating type high molecular material such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrenesulfonate) (PSS) can be used. These materials can be formed into a thin film by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0100] In addition, in the hole injection layer or the hole transport layer, a substance formed by further P-type doping of a material generally used for these layers with tribromoaniline antimony hexachloride, an axeridine derivative (see, for example, Patent Document 6), etc., a high molecular compound having a structure of a diphenylamine derivative such as TPD in a partial structure thereof, etc. can be used.

[0101] The arylamine compound represented by General Formula (1) of the present application has excellent hole injection / transport properties, stability, and durability of a thin film. Therefore, the organic EL element having a hole injection layer and / or a hole transport layer produced using this compound as a hole injection material and / or a hole transport material can improve the durability of the element by improving the hole transport efficiency in the light emitting layer and reducing the driving voltage, and can achieve high efficiency, low driving voltage, and long life characteristics.

[0102] [Electron blocking layer]

[0103] The electron-blocking layer is, for example, provided between the light-emitting layer and the hole-transporting layer, and has a function of inhibiting diffusion of electrons present in the light-emitting layer to the outside (hole-transporting layer side) of the light-emitting layer. Thereby, the probability of recombination of electrons and holes in the light-emitting layer can be increased. The electron-blocking layer generally also has a function of transporting holes. In addition, the electron-blocking layer can have a function of an exciton-blocking layer that inhibits diffusion of excitons from the light-emitting layer.

[0104] As the material of the electron-blocking layer of the organic EL element of the present application, in addition to the arylamine compound of the present application, a compound having an electron-blocking action such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (Ad-Cz), and the like, carbazole derivatives, a compound having a triphenylsilyl group and a triarylamine structure represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, and the like can also be used. These materials can also serve as the material of the hole-transporting layer. These materials can be formed into a film alone or in a mixture of a plurality of kinds, and each can be used as a single layer. In addition, it can be a stacked structure between layers formed of these materials alone, a stacked structure between layers formed of a mixture, or a stacked structure of a layer formed of these materials alone and a layer formed of a mixture of a plurality of kinds. These materials can be formed into a film by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0105] The arylamine compound of the present application has the following characteristics: the electron-blocking ability is excellent, the electron resistance is high, and even in a thin film state, the compound is stable and limits excitons generated in the light-emitting layer. Thereby, for an organic EL element having an electron-blocking layer made using this compound as an electron-blocking material, the probability of recombination of holes and electrons is increased and thermal deactivation is inhibited, and thus the light-emitting efficiency is high, the driving voltage is low, and the current resistance is improved, and thereby the maximum light-emitting luminance is increased.

[0106] [Light-emitting layer]

[0107] The light-emitting layer is a layer that generates excitons by recombination of holes and electrons injected from the anode and the cathode, respectively, and then emits light, and the light-emitting layer can be used alone as the light-emitting layer, but preferably contains a light-emitting material and a host material.

[0108] As a material of the light-emitting layer of the organic EL element of the present application, in addition to the arylamine compound of the present application, a metal complex of a quinolinol derivative such as tris(8-hydroxyquinoline)aluminum (Alq3), various metal complexes, an anthracene derivative, a distyrylbenzene derivative, a pyrene derivative, an oxazole derivative, a poly-p-phenylenevinylene derivative, and the like can be used. In addition, the light-emitting layer can be composed of a host material and a dopant material, and as the host material, an anthracene derivative can be preferably used, but in addition to the above light-emitting materials including the arylamine compound of the present application, a heterocyclic compound having an indole ring as a partial structure of a condensed ring, a heterocyclic compound having a carbazole ring as a partial structure of a condensed ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, and the like can be used. In addition, as the dopant material, quinacridone, coumarin, rubrene, perylene and derivatives thereof, a benzopyran derivative, a rhodamine derivative, an aminostyryl derivative, and the like can be used. These materials can be deposited alone or in a mixture of a plurality of kinds, and each can be used as a single layer. In addition, it can be a stacked structure between layers each of which is deposited from these materials alone, a stacked structure between layers each of which is deposited from a mixture of a plurality of kinds, or a stacked structure between a layer deposited from these materials alone and a layer deposited from a mixture of a plurality of kinds. These materials can be formed into thin films by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0109] In addition, as the light-emitting material, a phosphorescent emitter can be used. As the phosphorescent emitter, a phosphorescent emitter of a metal complex of iridium, platinum, or the like can be used. For example, a green phosphorescent emitter such as Ir(ppy)3, a blue phosphorescent emitter such as FIrpic, FIr6, a red phosphorescent emitter such as Btp2Ir(acac), and the like can be exemplified, and as the host material at this time, as a hole-injection / transporting host material, in addition to a carbazole derivative such as 4,4'-di(N-carbazolyl)diphenyl (CBP), TCTA, mCP, and the like, the arylamine compound of the present application can be exemplified, and as an electron-transporting host material, p-bis(triphenylsilyl)benzene (UGH2), 2,2',2"-(l,3,5-phenylene)-tris(l-phenyl-lH-benzimidazole) (TPBI), and the like can be exemplified. By using such a material, an organic EL element of high performance can be produced.

[0110] As for doping of a phosphorescent light-emitting material into a host material, in order to avoid concentration quenching, doping in a range of 1 to 30 weight percent to the entire light-emitting layer by co-evaporation is preferable.

[0111] In addition, as the light-emitting material, a material that emits delayed fluorescence, such as a triazine derivative such as PIC-TRZ, CC2TA, a phenoxazine derivative such as PXZ-TRZ, a carbazole dicyanobenzene derivative (CDCB derivative) such as 4CzIPN, and the like (see Non-Patent Document 3) can also be used. These materials can be formed into a thin film by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0112] The arylamine compound represented by General Formula (1) of the present application has excellent hole-transporting properties and a wide band gap. Thus, an organic EL element having a light-emitting layer produced using this compound as a host material carries a fluorescent emitter, a phosphorescent emitter, or a delayed fluorescent emitter, which is called a dopant, to form a light-emitting layer, thereby reducing the driving voltage and improving the emission efficiency.

[0113] [Hole-blocking layer]

[0114] The hole-blocking layer is, for example, a layer provided between the light-emitting layer and the electron-transporting layer, which has a function of inhibiting the diffusion of holes present in the light-emitting layer to the outside (electron-transporting layer side) of the light-emitting layer.

[0115] As the material of the hole-blocking layer of the organic EL element of the present application, a compound having a hole-blocking function, such as a phenanthroline derivative such as bathocuproin (BCP), a metal complex of a quinol alcohol derivative such as bis(2-methyl-8-quinolinolato)-4-phenylphenoxy)aluminum (BAlq), various rare earth complexes, an oxazole derivative, a triazole derivative, and a triazine derivative, can be used. These materials can function as the material of the electron-transporting layer. These materials can be formed into a film individually or in a mixture of a plurality of kinds, and each can be used as a single layer. Alternatively, the hole-blocking layer can be a stacked structure of layers formed by individually forming films of these materials, a stacked structure of layers formed by mixing and forming films of these materials, or a stacked structure of layers formed by individually forming films of these materials and layers formed by mixing and forming films of a plurality of kinds. These materials can be formed into a thin film by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0116] [Electron-transporting layer, electron-injecting layer]

[0117] The electron-injecting layer is a layer provided between the cathode and the light-emitting layer, or between the cathode and the electron-transporting layer, or the like, for reducing the injection barrier of the electrons supplied from the cathode, thereby reducing the driving voltage and improving the emission brightness.

[0118] The electron-transporting layer is a layer having a function of transporting electrons. The electron-transporting layer can be an electron-injecting and transporting layer having a function of an electron-injecting layer.

[0119] As the material of the electron transport layer of the organic EL element of the present application, metal complexes of quinolinol derivatives such as Alq3, BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, and silol derivatives, etc. can be used. These materials can be deposited as a single layer or as a plurality of layers, and each of them can be used as a single layer. Alternatively, a stacked structure of layers each of which is deposited from a single material, a stacked structure of layers each of which is deposited from a plurality of materials, or a stacked structure of layers each of which is deposited from a single material and layers each of which is deposited from a plurality of materials can be used. These materials can be deposited by a publicly known method such as an evaporation method, a spin coating method, and an inkjet method.

[0120] As the material of the electron injection layer of the organic EL element of the present application, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. The electron injection layer can be omitted by the preferred selection of the electron transport layer and the cathode.

[0121] Further, in the electron injection layer and the electron transport layer, a substance in which a metal such as cesium is added to a material normally used for these layers (N-type doping) can be used.

[0122] [Cathode]

[0123] As the cathode of the organic EL element of the present application, a metal having a low work function such as aluminum, and an alloy having a lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, and an aluminum-magnesium alloy can be used as an electrode material.

[0124] The arylamine compound represented by the above general formula (1) that is suitable for the organic EL element of the present application is preferably used as a material of a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer of the organic EL element, and more preferably used as a material of a hole transport layer or an electron blocking layer.

[0125] Therefore, the arylamine compound represented by general formula (1) of the present application is useful as a material of a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer of an organic EL element, and can improve the luminous efficiency, the driving voltage, and the durability of a conventional organic EL element.

[0126] <Electronic device>

[0127] The electronic device of the present application has a pair of electrodes and at least one organic layer disposed between the pair of electrodes, and contains a compound represented by General Formula (I) in at least one of the aforementioned organic layers. As for the compound represented by General Formula (I), refer to the description in the above-mentioned column of "Compound represented by General Formula (I)".

[0128] As the electronic device, a display device equipped with an organic EL element, a light emitting device, etc. can be given, but as the display device, for example, a display component such as an organic EL panel module, a television, a mobile phone, a tablet, a personal computer, etc. can be given. As the light emitting device, for example, a lighting or a vehicle lamp, etc. can be given.

[0129] Examples

[0130] Hereinafter, the embodiments of the present application will be described more specifically using examples, but the present application is not limited to the following examples as long as the gist thereof is not exceeded.

[0131] [Example 1] Synthesis of Compound (1-4)

[0132] Into a reaction vessel, bis[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-diphenyl-4-ylamine: 5.0 g, 4'-iodo-l,l':2',l"-terphenyl: 6.4 g, potassium carbonate: 3.6 g, tetrakis(triphenylphosphine)palladium(0): 202 mg were charged, and stirred under reflux in a mixed solvent of 1,4-dioxane (40 mL) / purified water (12 mL) for 8 hours. After natural cooling, methanol was added, and filtered to obtain a crude product. The obtained crude product was subjected to adsorption purification using silica gel, and subjected to crystallization purification in toluene, whereby white powder of bis[4-(l,l':2',l"-terphenyl-4-yl)phenyl]-diphenyl-4-ylamine (compound (1-4)) was obtained: 4.3 g (yield: 63.1%).

[0133] The structure of the obtained compound (1-4) was identified using NMR.

[0134] Using 1 The following 43 hydrogen signals were detected by H-NMR (CDCI3).

[0135] δ (ppm) = 7.60-7.66 (11H), 7.49-7.55 (4H), 7.42-7.44 (2H), 7.31-7.33 (1H), 7.17-7.27 (25H).

[0136] [Chemical Formula 3]

[0137]

[0138] [Example 2] <Synthesis of Compound (1-7)>

[0139] In a reaction vessel, bis(4-bromophenyl)amine: 10.0 g, 4,4,5,5-tetramethyl-2-(o-terphenyl-4'-yl)-1,3,2-dioxaborinane: 22.9 g, potassium carbonate: 12.7 g, tetrakis(triphenylphosphine)palladium(0): 707 mg were stirred under reflux for 15 hours in a mixed solvent of toluene (100 mL) / ethanol (25 mL) / purified water (12 mL). After natural cooling, toluene / saturated brine was added to the system, and the organic layer was separated by extraction and liquid separation, and then concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (support: silica gel, eluent: toluene / hexane) to obtain white powder of bis[p-(o-terphenyl-4'-yl)phenyl]amine (intermediate 1): 12.3 g (yield: 64.5%).

[0140] [Chemical Formula 4]

[0141]

[0142] Next, in a reaction vessel, bis[p-(o-terphenyl-4'-yl)phenyl]amine: 4.0 g, 4-bromoterphenyl: 2.2 g, sodium tert-butoxide: 0.9 g, tris(dibenzylideneacetone)dipalladium(0): 59 mg, tris(tert-butyl)phosphine: 51 mg were stirred under reflux for 2 hours in a toluene (40 mL) solvent. After natural cooling, methanol was added, and the mixture was filtered to obtain a crude product. The obtained crude product was purified by crystallization using a mixed solvent of toluene / acetone to obtain white powder of bis[4-(1,1':2',1"-terphenyl-4'-yl)phenyl]-1,1':4',1"-terphen-4-ylamine (compound (1-7)): 2.5 g (yield: 46.5%).

[0143] The structure of the obtained compound (1-7) was identified using NMR.

[0144] The structure of the obtained compound (1-7) was identified using NMR. 1 The following 47 hydrogen signals were detected by1H-NMR (CDCI3).

[0145] δ (ppm) = 7.66 (4H), 7.63-7.64 (2H), 7.40-7.55 (20H), 7.33-7.36 (1H), 7.18-7.24 (20H).

[0146] [Chemical Formula 5]

[0147]

[0148] [Example 3] <Synthesis of Compound (1-16)>

[0149] In a reaction vessel, (bis[p-(o-terphenyl-4'-yl)phenyl]amine: 4.0 g, 3-bromodibenzofuran: 1.7 g, sodium tert-butoxide: 0.9 g, tris(dibenzylideneacetone)dipalladium(0): 59 mg, tri-tert-butylphosphine: 51 mg) were stirred under reflux for 2 hours in toluene (40 mL) solvent. After natural cooling, filtration was performed to obtain a crude product. The obtained crude product was subjected to adsorption purification using silica gel, and the obtained crude product was subjected to crystallization purification using a toluene / acetone mixed solvent, whereby white powder of bis(4-[1,1':2',1"-terphenyl-4'-yl]phenyl)-dibenzofuran-3-yl-amine (compound (1-16)) was obtained: 2.1 g (yield: 40.9%).

[0150] The structure of the obtained compound (1-16) was identified using NMR.

[0151] The structure of the obtained compound (1-16) was identified using NMR. 1 The following 41 hydrogen signals were detected by1H-NMR (CDCI3).

[0152] δ (ppm) = 7.85-7.86 (1H), 7.78-7.79 (1H), 7.40-7.51 (17H), 7.36-7.39 (1H), 7.29-7.32 (2H), 7.17-7.24 (18H), 7.13-7.15 (1H).

[0153] [Chemical Formula 6]

[0154]

[0155] [Example 4] Synthesis of Compound (1-26)

[0156] In a reaction vessel, (bis[p-(o-terphenyl-4'-yl)phenyl]amine: 4.0 g, 3-bromodibenzofuran: 1.7 g, sodium tert-butoxide: 0.9 g, tris(dibenzylideneacetone)dipalladium(0): 59 mg, tri-tert-butylphosphine: 51 mg) were stirred under reflux for 2 hours in toluene (40 mL) solvent. After natural cooling, filtration was performed to obtain a crude product. The obtained crude product was subjected to adsorption purification using silica gel, and the obtained crude product was subjected to crystallization purification using a toluene / acetone mixed solvent, whereby white powder of bis(4-[1,1':2',1"-terphenyl-4'-yl]phenyl)-dibenzofuran-3-yl-amine (compound (1-16)) was obtained: 2.1 g (yield: 40.9%).

[0157] The structure of the obtained compound (1-26) was identified using NMR.

[0158] Using 1 The following 47 hydrogen signals were detected by H-NMR (CDC13).

[0159] δ (ppm) = 7.66 (4H), 7.60 (2H), 7.56 (2H), 7.54-7.42 (18H), 7.33 (1H), 7.27-7.18 (20H).

[0160] [Chemical Formula 7]

[0161]

[0162] [Example 5] Synthesis of Compound (1-117)

[0163] In a reaction vessel, (diphenyl-4-yl)-(4'-phenyl-[1,1':3',1"]terphenyl-4-yl)-amine: 3.3 g, 4-bromo-4"-phenyl-[1,1':4',1":3",1"']quaterphenyl: 3.2 g, sodium tert-butoxide: 0.9 g, tris(dibenzylideneacetone)dipalladium(0): 160 mg, tri-tert-butylphosphine: 140 mg were stirred at reflux for 5 hours in toluene (40 mL) solvent. After natural cooling, filtration was performed to obtain a crude product. The obtained crude product was subjected to adsorption purification using silica gel, and the obtained crude product was subjected to recrystallization purification using ethyl acetate solvent, thereby obtaining white powder of (diphenyl-4-yl)-(4'-phenyl-[1,1':3',1"]terphenyl-4-yl)-(4"-phenyl-[1,1':4',1":3",1"']quaterphenyl-4-yl)-amine (Compound (1-117)): 4.8 g (yield: 81.7%).

[0164] The structure of the obtained compound (1-117) was identified using NMR.

[0165] Using 1 The following 47 hydrogen signals were detected by H-NMR (CDC13).

[0166] δ (ppm) = 7.66 (4H), 7.60 (2H), 7.56 (2H), 7.54-7.42 (18H), 7.33 (1H), 7.27-7.18 (20H).

[0167] [Chemical Formula 8]

[0168]

[0169] [Example 6]

[0170] The glass transition temperature of the arylamine compound represented by the general formula (1) and EBM-1 of the following structure disclosed in Patent Document 5 as a comparative example compound was measured using a high-sensitivity differential scanning calorimeter (Rigaku, DSCvesta Thermoplus EV02 series). The results are summarized in Table 1.

[0171] [Chemical Formula 9]

[0172]

[0173] [Table 1]

[0174] Compound Glass transition temperature (°C) Compound (1-4) 122 Compound (1-7) 126 Compound (1-16) 122 Compound (1-26) 128 Compound (1-117) 126 EBM-1 103

[0175] The glass transition temperature of the comparative compound (EBM-1) was 103°C, and in contrast, the arylamine compound represented by the general formula (1) had a glass transition temperature of 120°C or more, indicating stability in a thin film state. Therefore, by using the arylamine compound represented by the general formula (1) for an organic EL element, an element having excellent thermal stability can be produced.

[0176] [Example 7]

[0177] <Measurement of HOMO Energy Level>

[0178] The arylamine compound represented by the general formula (1) and EBM-1 of the above structure were produced into an evaporation film having a film thickness of 100 nm on an ITO substrate. The work function (corresponding to the absolute value of the HOMO energy level) was measured using an ionization potential measuring device (Sumitomo Heavy Industries, Ltd., PYS-202), and the results are summarized in Table 2.

[0179] [Table 2]

[0180] Compound Work function (eV) Compound (1-4) 5.64 Compound (1-7) 5.64 Compound (1-16) 5.65 Compound (1-26) 5.57 Compound (1-117) 5.64 EBM-1 5.64

[0181] In comparison with the work function of 5.4 eV possessed by a general hole transport material such as NPD, TPD, etc., the arylamine compound represented by the general formula (1) showed a more suitable energy level and had a good hole transport ability.

[0182] [Example 8]

[0183] <Evaluation of Organic EL>

[0184] As shown in Figure 11 , an organic EL element was produced by previously forming a reflective ITO electrode as a transparent anode 2 on a glass substrate 1, and sequentially evaporating a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a cover layer 10 thereon.

[0185] Specifically, a glass substrate 1 on which ITO of 50 nm in thickness, a reflective film of silver alloy of 100 nm in thickness, and ITO of 5 nm in thickness were sequentially formed was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250°C for 10 minutes. After that, the glass substrate with ITO was installed in a vacuum deposition machine, and reduced to a pressure of 0.001 Pa or less.

[0186] Next, an electron acceptor (Acceptor-1) of the following structural formula and a compound (BCFN) of the following structural formula were two-dimensionally deposited at a deposition rate ratio of Acceptor-1 : BCFN = 3 : 97 to form a hole injection layer 3 of 10 nm in thickness so as to cover the transparent anode 2.

[0187] On the hole injection layer 3, a compound (BCFN) of the following structural formula was formed so as to have a thickness of 140 nm to form a hole transport layer 4.

[0188] On the hole transport layer 4, the compound (1-4) of Example 1 was formed so as to have a thickness of 5 nm to form an electron blocking layer 5.

[0189] On the electron blocking layer 5, a compound (Dopant-1) of the following structural formula and a compound (ADN) of the following structural formula were two-dimensionally deposited at a deposition rate ratio of Dopant-1 : ADN = 2 : 98 to form a light emitting layer 6 of 20 nm in thickness.

[0190] On the light emitting layer 6, a compound (ETM-1) of the following structural formula and a compound (ETM-2) of the following structural formula were two-dimensionally deposited at a deposition rate ratio of ETM-1 : ETM-2 = 50 : 50 to form an electron transport layer 7 of 30 nm in thickness.

[0191] On the electron transport layer 7, lithium fluoride was formed so as to have a thickness of 1 nm to form an electron injection layer 8.

[0192] On the electron injection layer 8, a magnesium-silver alloy was formed so as to have a thickness of 12 nm to form a cathode 9.

[0193] Finally, a compound (CPL-1) of the following structural formula was formed so as to have a thickness of 60 nm to form a cover layer 10.

[0194] [Chemical Formula 10]

[0195]

[0196] [Chemical Formula 11]

[0197]

[0198] [Chemical Formula 12]

[0199]

[0200] [Chemical Formula 13]

[0201]

[0202] [Example 9]

[0203] In Example 8, instead of the compound (1-4) of Example 1, the compound (1-7) of Example 2 was used as the material of the electron-blocking layer 5, and an organic EL element was produced under the same conditions except for this. The produced organic EL element was subjected to a property measurement in the atmosphere and at normal temperature. The measurement results of the light emission property when a direct current voltage was applied to the produced organic EL element are shown in Table 3.

[0204] [Example 10]

[0205] In Example 8, instead of the compound (1-4) of Example 1, the compound (1-16) of Example 3 was used as the material of the electron-blocking layer 5, and an organic EL element was produced under the same conditions except for this. The produced organic EL element was subjected to a property measurement in the atmosphere and at normal temperature. The measurement results of the light emission property when a direct current voltage was applied to the produced organic EL element are shown in Table 3.

[0206] [Example 11]

[0207] In Example 8, instead of the compound (1-4) of Example 1, the compound (1-26) of Example 4 was used as the material of the electron-blocking layer 5, and an organic EL element was produced under the same conditions except for this. The produced organic EL element was subjected to a property measurement in the atmosphere and at normal temperature. The measurement results of the light emission property when a direct current voltage was applied to the produced organic EL element are shown in Table 3.

[0208] [Example 12]

[0209] In Example 8, instead of the compound (1-4) of Example 1, the compound (1-117) of Example 5 was used as the material of the electron-blocking layer 5, and an organic EL element was produced under the same conditions except for this. The produced organic EL element was subjected to a property measurement in the atmosphere and at normal temperature. The measurement results of the light emission property when a direct current voltage was applied to the produced organic EL element are shown in Table 3.

[0210] [Comparative Example 1]

[0211] For comparison, in Example 8, instead of the compound (1-4) of Example 1, EBM-1 of the above structural formula was used as the material of the electron-blocking layer 5, and otherwise, an organic EL element was produced under the same conditions. The produced organic EL element was subjected to property measurement in the atmosphere at normal temperature. The results of measurement of the light emission property when a direct current voltage was applied to the produced organic EL element are summarized in Table 3.

[0212] The element life of the organic EL elements produced in Examples 8 to 12 and Comparative Example 1 was measured, and the results are summarized in Table 3. The light emission brightness at the start of light emission (initial brightness) was set to 1000 cd / m 2 On the other hand, when constant current drive was performed, the time until the light emission brightness decreased to 950 cd / m 2 (corresponding to 95% when the initial brightness is set to 100%: 95% of decrease) was measured as the element life.

[0213] [Table 3]

[0214]

[0215] As shown in Table 3, it was found that, with respect to the light emission efficiency at a current of 10 mA / cm 2 of the flowing current density, the organic EL element of Comparative Example 1 was 10.63 cd / A, and, in contrast to this, the organic EL elements of Examples 8 to 12 were 10.72 to 11.19 cd / A, showing high efficiency. In addition, with respect to the power efficiency, the organic EL element of Comparative Example 1 was 9.12 lm / W, and, in contrast to this, the organic EL elements of Examples 8 to 12 were 9.27 to 9.56 lm / W, showing high efficiency. Furthermore, with respect to the element life (95% of decrease), the organic EL element of Comparative Example 1 was 363 hours, and, in contrast to this, the organic EL elements of Examples 8 to 12 were 405 to 476 hours, showing long life.

[0216] From the above results, it is clear that the organic EL element of the present application uses an arylamine compound having high thermal stability and excellent electron-blocking ability, and thus, compared to conventional organic EL elements, is a high light emission efficiency organic EL element, and can achieve a long life organic EL element.

[0217] The organic EL element of the present application using an arylamine compound having a specific structure can improve light emission efficiency, and can improve the durability of the organic EL element, for example, can expand the use to home electric appliances or lighting.

Claims

1. An arylamine compound represented by the following general formula (1), [Chemical Formula 1] wherein Ar1represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, Ar2to Ar5arbitrarily represent the same or different groups, and represent a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, R1to R 14 represents a hydrogen atom or a deuterium atom, and m and n each independently represent an integer of 1 to 2.

2. The arylamine compound according to claim 1, wherein, in the general formula (1), Ar2 to Ar5 are arbitrarily the same as or different from each other, and are a group represented by the following general formula (2), [Chemical Formula 2] wherein R 15 ~R 19 are optionally the same as or different from each other, and represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, R 15 ~R 19 are optionally bonded to each other to form a ring.

3. The arylamine compound according to claim 2, wherein, In the general formula (2), R 15 ~R 19 is a hydrogen atom.

4. The arylamine compound according to claim 1, wherein, in the general formula (1), m or n is 1.

5. An organic EL element having a pair of electrodes and at least one organic layer interposed between the pair of electrodes, wherein, The arylamine compound according to any one of claims 1 to 4 is contained in the organic layer.

6. The organic EL element according to claim 5, wherein, the organic layer is a hole transport layer.

7. The organic EL element according to claim 5, wherein, the organic layer is an electron blocking layer.

8. The organic EL element according to claim 5, wherein, the organic layer is a hole injection layer.

9. An electronic device comprising an electronic element having a pair of electrodes and at least one organic layer interposed between the pair of electrodes, wherein The arylamine compound according to any one of claims 1 to 4 is contained in the organic layer.

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