Arylamine Compound and Organic Electroluminescence Element

Abstract

The purpose of the present invention is to provide a material for an organic EL element which is excellent in terms of positive hole injection and transport performance and has electronic stopping power and which, in a thin-film state, has high stability and is excellent in terms of durability as a material for a highly-efficient and highly-durable organic EL element, and to also use this compound to provide a highly-efficient and highly-durable organic EL element.　The present invention is an arylamine compound represented by general formula (1) below. (In the formula, Ar1, Ar2, Ar3, and Ar4 represent substitutional or non-substitutional aromatic hydrocarbon groups, etc., L1 and L2 represent divalent substitutional or non-substitutional aromatic hydrocarbon groups, etc., R1 to R7 represent hydrogen atoms or heavy hydrogen atoms, etc., m and n represent integers from 0 to 2 which may be the same as or different from each other, L1 represents a single bond when m is 0, and L2 represents a single bond when n is 0.)

Description

Technical Field

[0001] The present invention relates to a compound and an element suitable for an organic electroluminescence element (hereinafter abbreviated as an organic EL element), which is a self-luminous element suitable for various display devices. Specifically, the present invention relates to an arylamine compound and an organic EL element using the compound.

Background Art

[0002] Since the organic EL element is a self-luminous element, it has been actively studied because it is brighter and has better visibility than a liquid crystal element, and can provide a clear display.

[0003] In 1987, C.W. Tang et al. of Eastman Kodak developed a laminated structure element in which various roles were assigned to each material, making the organic EL element using an organic material practical. They laminated a phosphor capable of transporting electrons and an organic substance capable of transporting holes, and injected both charges into the phosphor layer to emit light, thereby obtaining a high brightness of 1000 cd / m 2 or more at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).

[0004] To date, many improvements have been made for the practical application of organic EL elements. The various roles of the laminated structure have been further subdivided, and a field emission element having 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 sequentially provided on a substrate has been developed to achieve high efficiency and durability (see, for example, Non-Patent Document 1).

[0005] In addition, the use of triplet excitons has been attempted for further improvement of luminous efficiency, and the use of phosphorescent compounds has been studied (see, for example, Non-Patent Document 2). Furthermore, an element using light emission by thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Adachi et al. of Kyushu University achieved an external quantum efficiency of 5.3% with an element using a thermally activated delayed fluorescence material (see, for example, Non-Patent Document 3).

[0006] The light-emitting layer can generally be fabricated by doping a charge-transporting compound called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence. As described in the non-patent literature, the selection of organic materials in an organic EL device has a significant impact on various characteristics of the device, such as its efficiency and durability (see, for example, Non-Patent Document 2).

[0007] In an organic EL device, light is obtained when charges injected from both electrodes recombine in the light-emitting layer. However, it is important how efficiently both charges, holes and electrons, are transferred to the light-emitting layer, and it is necessary to make the device have excellent carrier balance. Therefore, by using a material having the characteristics of enhancing the hole injection property for supplying holes injected from the anode to the light-emitting layer and further enhancing the electron blocking property for blocking electrons injected from the cathode, the probability of recombination of holes and electrons in the light-emitting layer can be improved, and furthermore, by confining excitons generated in the light-emitting layer, high luminous efficiency can be obtained. For this purpose, the role played by the hole transport material is important, and a hole transport material with high hole injection property, high hole mobility, high electron blocking property, and furthermore high durability against electrons is required.

[0008] Regarding the lifetime of the device, the heat resistance and amorphousness of the material are also important. In a material with low heat resistance, thermal decomposition occurs even at a low temperature due to the heat generated during device driving, and the material deteriorates. In a material with low amorphousness, crystallization of the thin film occurs even in a short time, and the device deteriorates. Therefore, the materials to be used are required to have high heat resistance and good amorphousness.

[0009] Hitherto, hole transport materials used in organic EL devices include N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) and various aromatic amine derivatives (see, for example, Patent Document 1 and Patent Document 2). However, although NPD has good hole transport ability, its glass transition point (Tg), which is an index of heat resistance, is as low as 96°C, and the device characteristics deteriorate due to crystallization under high-temperature conditions (see, for example, Non-Patent Document 4).

[0010] In addition, among the aromatic amine derivatives described in the above patent documents, there are compounds having an excellent hole mobility of 10 -3 cm 2 / Vs or more (see, for example, Patent Document 1 and Patent Document 2). However, since the electron blocking property is insufficient, some electrons pass through the light-emitting layer, and there are problems such as the inability to expect an improvement in the light-emitting efficiency. For further high efficiency, materials with higher electron blocking properties, more stable thin films, and higher heat resistance have been demanded. In addition, there are reports of aromatic amine derivatives with high durability (see, for example, Patent Document 3), but they are used as charge transport materials for electrophotographic photoreceptors and there are no examples of use as organic EL elements.

[0011] To solve this problem, arylamine compounds having a substituted carbazole structure or a triarylbenezene structure have been proposed as compounds with improved properties such as heat resistance and hole injection properties (see, for example, Patent Document 4 and Patent Document 5). In the elements using these compounds for the hole injection layer or the hole transport layer, although improvements have been made in the element lifetime, light-emitting efficiency, etc., they are not yet sufficient, and further reduction of the driving voltage, higher light-emitting efficiency, and longer element lifetime are demanded.

Prior Art Documents

Patent Documents

[0012]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Patent Document 6

Non-Patent Documents

[0013]

Non-Patent Document 1

Non-Patent Document 2

Non-Patent Document 3

Non-Patent Document 4

Summary of the Invention

Problems to be Solved by the Invention

[0014] An object of the present invention is to provide a material for an organic EL element having high efficiency and high durability, which has (1) excellent hole injection and transport performance, (2) electron blocking ability, (3) high stability in a thin film state, and (4) excellent durability.

[0015] Another object of the present invention is to provide an organic EL element having (1) high luminous efficiency and power efficiency, (2) low emission start voltage and practical driving voltage, and (3) long life by using the material of the present invention.

Means for Solving the Problems

[0016] In order to achieve the above object, the present inventors have intensively studied, focusing on the fact that an arylamine compound having a triarylbenezene structure is excellent in hole injection and transport ability, thin film stability and durability, and by pursuing improvement and optimization of the substitution position, a material with dramatically improved characteristics was obtained. And by using this material in an organic EL element, it was found that the performance of luminous efficiency and power efficiency can be improved, the emission start voltage and practical driving voltage can be suppressed, and a long life exceeding the conventional life can be realized, thus completing the present invention.

[0017] 1) That is, the present invention is an arylamine compound represented by the following general formula (1).

[0018] [Chemical formula] (In the formula, Ar1, Ar2, Ar3, and Ar4 each independently represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, which may be the same or different. L1 and L2 each independently represent a divalent substituted or unsubstituted aromatic hydrocarbon group, a divalent substituted or unsubstituted aromatic heterocyclic group, or a divalent substituted or unsubstituted condensed polycyclic aromatic group, which may be the same or different. R1 to R7 each independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. m and n each independently represent an integer from 0 to 2, and when m is 0, L1 represents a single bond, and when n is 0, L2 represents a single bond.)

[0019] 2) Further, the present invention provides the arylamine compound according to 1) above, wherein in the general formula (1), R1 and R3 are each independently a hydrogen atom or a deuterium atom, which may be the same or different.

[0020] 3) Further, in the present invention, in the general formula (1), the arylamine compound according to 1) or 2) above, wherein Ar3 and Ar4 may each be the same or different and are a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

[0021] 4) Further, in the present invention, in the general formula (1), the arylamine compound according to any one of 1) to 3) above, wherein R2 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

[0022] 5) Further, in the present invention, in the general formula (1), the arylamine compound according to any one of 1) to 4) above, wherein Ar3 and Ar4 are the same.

[0023] 6) Further, in the present invention, in the general formula (1), the arylamine compound according to any one of 1) to 5) above, wherein Ar3, Ar4 and R2 are the same.

[0024] 7) Further, in the present invention, in the general formula (1), the arylamine compound according to any one of 1) to 6) above, wherein L1 or L2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted biphenylene group.

[0025] 8) Further, in the present invention, in the general formula (1), the arylamine compound according to any one of 1) to 7) above, wherein the sum of the integers m and n is 0 or 1.

[0026] 9) In an organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween, the organic EL device, wherein the organic layer contains the arylamine compound according to any one of 1) to 8) above.

[0027] 10) The present invention also provides the organic EL device according to 9) above, wherein the organic layer is a hole transport layer.

[0028] 11) The present invention also provides the organic EL device according to 9) above, wherein the organic layer is an electron blocking layer.

[0029] 12) The present invention also provides the organic EL device according to 9) above, wherein the organic layer is a hole injection layer.

[0030] 13) The present invention also provides the organic EL device according to 9) above, wherein the organic layer is a light emitting layer.

[0031] 14) The present invention also provides an electronic device using an electronic component having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains an arylamine compound according to any one of 1) to 8) above.

[0032] In the “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by Ar1 to Ar4 in the general formula (1), examples of the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” include, specifically, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, azafluorenyl group, diazafluorenyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carbolinyl group, etc., aryl groups having 6 to 30 carbon atoms, and heteroaryl groups having 2 to 20 carbon atoms, etc.

[0033] Examples of the "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1) specifically include deuterium atom, cyano group, nitro group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; silyl groups such as trimethylsilyl group, triphenylsilyl group; linear or branched alkyl groups having 1 to 6 carbon atoms such as methyl group, ethyl group, propyl group; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group, propyloxy group; alkenyl groups such as vinyl group, allyl group; aryloxy groups such as phenyloxy group, tolyloxy group; arylalkyloxy groups such as benzyloxy group, phenethyloxy group; aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; aromatic heterocyclic groups such as pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group. These substituents may further be substituted with the substituents exemplified above. Further, these substituents and the substituted benzene ring, or substituents substituted on the same benzene ring in plural may 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.

[0034] The "divalent aromatic hydrocarbon group", "divalent aromatic heterocyclic group", or "divalent condensed polycyclic aromatic group" in the "divalent substituted or unsubstituted aromatic hydrocarbon group", "divalent substituted or unsubstituted aromatic heterocyclic group", or "divalent substituted or unsubstituted condensed polycyclic aromatic group" represented by L1 and L2 in the general formula (1) includes those similar to the divalent groups obtained by removing one hydrogen atom from the "aromatic hydrocarbon group", "aromatic heterocyclic group", or "condensed polycyclic aromatic group" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1).

[0035] The "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed polycyclic aromatic group" represented by L1 and L2 in the general formula (1) includes those similar to the "substituent" shown in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group", or "substituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1), and the possible embodiments also include those similar to them.

[0036] The "linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent", "cycloalkyl group having 5 to 10 carbon atoms which may have a substituent", or "linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent" represented by R1 to R7 in the general formula (1), the "linear or branched alkyl group having 1 to 6 carbon atoms", "cycloalkyl group having 5 to 10 carbon atoms", or "linear or branched alkenyl group having 2 to 6 carbon atoms" specifically includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a vinyl group, an allyl group, an isopropenyl group, and a 2-butenyl group, etc. These groups and the substituted benzene ring, or these groups substituted in plurality on the same benzene ring, may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom or a sulfur atom to form a ring.

[0037] The "substituent" in the "linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent", "cycloalkyl group having 5 to 10 carbon atoms which may have a substituent", or "linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent" represented by R1 to R7 in the general formula (1) may include the same as those shown as the "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group", or "substituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1), and the possible embodiments may also include the same.

[0038] The "carbon atom having a linear or branched alkyloxy group with 1 to 6 carbon atoms which may have a substituent" or "carbon atom having a cycloalkyloxy group with 5 to 10 carbon atoms which may have a substituent" represented by R1 to R7 in the general formula (1), specifically, includes a methyloxy group, an ethyloxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a 1-adamantyloxy group, a 2-adamantyloxy group, and the like. These groups and the substituted benzene ring, or these groups substituted in plurality on the same benzene ring, may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom or a sulfur atom to form a ring.

[0039] Examples of the "substituent" in the "linear or branched alkyloxy group with 1 to 6 carbon atoms which may have a substituent" or "cycloalkyloxy group with 5 to 10 carbon atoms which may have a substituent" represented by R1 to R7 in the general formula (1) include the same ones as those shown as the "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1), and the possible embodiments also include the same ones.

[0040] The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R1 to R7 in the general formula (1) includes the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1), and examples thereof are the same as those shown as the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group".

[0041] The "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R1 to R7 in the general formula (1) includes the same substituents as those shown as the "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar1 to Ar4 in the general formula (1), and the possible embodiments are also the same.

[0042] As Ar1 to Ar4 in the general formula (1), a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, phenanthrenyl group, fluorenyl group, or spirobifluorenyl group is preferable, and a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group or phenanthrenyl group is more preferable. As Ar3 and Ar4, a substituted or unsubstituted phenyl group or naphthyl group is preferable, and it is more preferable that Ar3 and Ar4 are the same. In particular, Ar1 and Ar2 are a phenyl group, biphenyl group, naphthyl group or phenanthrenyl group, or a group having a structure in which two groups selected from these groups are bonded, and it is preferable that Ar3 and Ar4 are phenyl groups.

[0043] It is preferable that the sum of the integers m and n in the general formula (1) is 0 or 1, more preferably m is 0 or 1 and n is 0. When m and n are not 0, L1 and L2 in the general formula (1) are preferably a substituted or unsubstituted phenylene group, biphenylene group, or naphthalene group, and more preferably an unsubstituted phenylene group or naphthalene group.

[0044] As R1 to R7 in the general formula (1), a hydrogen atom, deuterium atom, or a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, or spirobifluorenyl group is preferable, and a hydrogen atom, deuterium atom, unsubstituted phenyl group, biphenyl group, or naphthyl group is more preferable. As R1 and R3, a hydrogen atom or deuterium atom is preferable, and as R2, a hydrogen atom, deuterium atom, or a substituted or unsubstituted phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group is preferable. Also, it is preferable that Ar3, Ar4, and R2 are the same. In particular, it is preferable that R1, R3, R4, R5, R6, and R7 are hydrogen atoms or deuterium atoms, and R2 is a phenyl group.

[0045] The arylamine compound represented by the general formula (1), which is suitably used in the organic EL element of the present invention, is preferably used as a constituent material of a hole injection layer, hole transport layer, electron blocking layer, or light emitting layer of the organic EL element, and more preferably used as a constituent material of a hole transport layer or electron blocking layer.

Advantages of the Invention

[0046] The arylamine compound of the present invention has the following characteristics compared with conventional hole transport materials: (1) good hole injection characteristics, (2) high hole mobility, (3) excellent electron blocking ability, (4) high electron resistance, (5) stable existence in a thin film state, (6) excellent heat resistance, etc. By using the arylamine compound of the present invention in an organic EL element, characteristics such as (7) high luminous efficiency, (8) low light emission start voltage, (9) low practical driving voltage, and (10) long life can be obtained.

[0047] The arylamine compound of the present invention is excellent in hole injection / transport performance, thin film stability, and durability. Therefore, an organic EL device having a hole injection layer and / or a hole transport layer formed by using the compound as a hole injection material and / or a hole transport material has improved hole transport efficiency to the light-emitting layer, improved light-emitting efficiency, and a reduced driving voltage, thereby improving the durability of the device, and it is possible to obtain characteristics of high efficiency, low driving voltage, and long life.

[0048] The arylamine compound of the present invention is excellent in electron blocking ability, has high electron resistance, and is stable even in a thin film state, and has the characteristic of confining excitons generated in the light-emitting layer. Therefore, an organic EL device having an electron blocking layer formed by using the compound as an electron blocking material has a high light-emitting efficiency because the probability of recombination of holes and electrons is improved and thermal deactivation is suppressed, and the maximum light-emitting luminance is improved because the driving voltage is reduced and the current resistance is improved.

[0049] The arylamine compound of the present invention is excellent in hole transportability and has a wide band gap. Therefore, an organic EL device having a light-emitting layer formed by using the compound as a host material forms a light-emitting layer by carrying a fluorescent phosphor, a phosphorescent phosphor, or a delayed fluorescent phosphor called a dopant, thereby reducing the driving voltage and improving the light-emitting efficiency.

[0050] Therefore, the arylamine compound of the present invention is useful as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or a light-emitting layer of an organic EL device, and can improve the light-emitting efficiency, driving voltage, and durability of a conventional organic EL device.

[0051] In addition, the arylamine compound of the present invention can be used not only for organic EL devices but also in the fields of electronic devices such as electrophotographic photoreceptors, image sensors, photoelectric conversion elements, and solar cells.

Brief Description of the Drawings

[0052]

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DETAILED DESCRIPTION OF THE INVENTION

[0053] Although the arylamine compounds of the present invention are novel compounds, these compounds can be synthesized according to methods known per se (see, for example, Patent Document 5).

[0054] Among the arylamine compounds represented by the general formula (1) that are preferably used in the organic EL elements of the present invention, specific examples of preferred compounds are shown in FIGS. 1 to 12, but the invention is not limited to these compounds.

[0055] Purification of the arylamine compound represented by the general formula (1) can be carried out by known methods such as purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, and sublimation purification. Identification of the compound can be carried out by NMR analysis. Examples of physical property values include measurement of melting point, glass transition temperature (Tg), and work function. The melting point is an index of vapor deposition property, the glass transition temperature (Tg) is an index of the stability in the thin film state, and the work function is an index of hole injection property, hole transport property, or electron blocking property.

[0056] The melting point and the glass transition temperature (Tg) can be measured, for example, using a powder with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100SA).

[0057] The work function can be determined, for example, by forming a 100-nm thin film on an ITO substrate and using an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS-202).

[0058] As the structure of the organic EL element of the present invention, those composed of 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 sequentially on a substrate, those having an electron blocking layer between the hole transport layer and the light-emitting layer, and those having a hole blocking layer between the light-emitting layer and the electron transport layer can be mentioned. In these multilayer structures, one organic layer can serve multiple roles. For example, one organic layer can be configured to serve as both a hole injection layer and a hole transport layer, or as both an electron injection layer and an electron transport layer. Also, it is possible to form a structure in which two or more organic layers having the same function are stacked, such as a structure in which two hole transport layers are stacked, a structure in which two light-emitting layers are stacked, or a structure in which two electron transport layers are stacked.

[0059] As the anode of the organic EL element of the present invention, electrode materials with a large work function such as ITO and gold are used. As the material for the hole injection layer of the organic EL element of the present invention, porphyrin compounds typified by copper phthalocyanine, starburst-type triphenylamine derivatives, arylamine compounds having two or more triphenylamine structures or carbazolyl structures in the molecule and each connected by a single bond or a divalent group not containing a heteroatom, acceptor-type heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials can be used. These materials can form thin films by known methods such as vapor deposition, spin coating, and inkjet methods.

[0060] As materials for the hole injection layer and the hole transport layer of the organic EL element of the present invention, in addition to the arylamine compound of the present invention, N,N'-diphenyl-N,N'-di(m-tolyl)-benzidine (hereinafter abbreviated as TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (hereinafter abbreviated as NPD), benzidine derivatives such as N,N,N',N'-tetrabiphenylylbenzidine, 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC), and arylamine compounds having two or more triphenylamine structures or carbazolyl structures in the molecule, each linked by a single bond or a divalent group containing no hetero atom can be used. These materials may be formed into a film alone, but a plurality of types can also be mixed to form a film, and each can be used as a single layer. Further, a laminated structure of layers formed from these materials alone, a laminated structure of layers formed by mixing, or a laminated structure of a layer formed from these materials alone and a layer formed by mixing a plurality of types can also be used. In addition, as materials for the hole injection / transport layer, coating-type polymer materials such as poly(3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly(styrenesulfonate) (hereinafter abbreviated as PSS) can be used. These materials can be formed into a thin film by known methods such as vapor deposition, spin coating, and inkjet methods.

[0061] In addition, for the hole injection layer or the hole transport layer, materials obtained by P-doping trisbromophenylamine hexachloroantimonate, a radialene derivative (for example, see Patent Document 6), etc. with respect to materials usually used in these layers, or polymer compounds having the structure of a benzidine derivative such as TPD in its partial structure can be used.

[0062] As a material for the electron blocking layer of the organic EL element of the present invention, in addition to using the arylamine compound of the present invention, 4,4’,4’’-tri(N-carbazolyl)triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter abbreviated as Ad-Cz), and other carbazole derivatives, compounds having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene can be used. These materials may also serve as the material for the hole transport layer. These materials may be formed into a film alone, but a plurality of types may be mixed and formed into a film, and each can be used as a single layer. Further, a laminated structure of layers formed from these materials alone, a laminated structure of layers formed by mixing, or a laminated structure of a layer formed from these materials alone and a layer formed by mixing a plurality of types may be used. These materials can form a thin film by known methods such as vapor deposition, spin coating, and inkjet methods.

[0063] As a material for the light-emitting layer of the organic EL element of the present invention, in addition to using the arylamine compound of the present invention, metal complexes of quinolinol derivatives such as Alq3, various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylenevinylene derivatives, etc. can be used. Further, the light-emitting layer may be composed of a host material and a dopant material. As the host material, an anthracene derivative is preferably used. In addition to the light-emitting materials including the arylamine compound of the present invention, heterocyclic compounds having an indole ring as a partial structure of a condensed ring, heterocyclic compounds having a carbazole ring as a partial structure of a condensed ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, etc. can be used. As the dopant material, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, etc. can be used. These materials may be formed into a film alone, but can also be mixed and formed into a film, and each can be used as a single layer. Further, a laminated structure of layers formed from these materials alone, a laminated structure of layers formed by mixing, or a laminated structure of a layer formed from these materials alone and a layer formed by mixing a plurality of types may be used. These materials can form a thin film by known methods such as vapor deposition, spin coating, and inkjet methods.

[0064] In addition, it is also possible to use a phosphorescent emitter as the light-emitting material. As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used. For example, green phosphorescent emitters such as Ir(ppy)3, blue phosphorescent emitters such as FIrpic and FIr6, red phosphorescent emitters such as Btp2Ir(acac), etc. can be mentioned. At this time, as the host material, as a hole injection / transporting host material, in addition to carbazole derivatives such as 4,4'-bis(N-carbazolyl)biphenyl (hereinafter abbreviated as CBP), TCTA, mCP, etc., the arylamine compound of the present invention can be mentioned. As an electron transporting host material, p-bis(triphenylsilyl)benzene (hereinafter abbreviated as UGH2), 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (hereinafter abbreviated as TPBI), etc. can be mentioned. By using such materials, a high-performance organic EL device can be fabricated.

[0065] Doping of the phosphorescent emitter into the host material is preferably carried out by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer in order to avoid concentration quenching.

[0066] In addition, as the light-emitting material, it is also possible to use a material that emits delayed fluorescence, such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN, etc. (see, for example, Non-Patent Document 3). These materials can form a thin film by known methods such as evaporation method, spin coating method, and inkjet method.

[0067] As materials for the hole-blocking layer of the organic EL element of the present invention, compounds having a hole-blocking action, such as phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), metal complexes of quinolinol derivatives such as BAlq, various rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives, can be used. These materials may also serve as materials for the electron transport layer. These materials may be formed into a film alone, but can also be formed into a film by mixing multiple types, and each can be used as a single layer. Further, a laminated structure of layers formed from these materials alone, a laminated structure of layers formed by mixing, or a laminated structure of a layer formed from these materials alone and a layer formed by mixing multiple types may be used. These materials can form a thin film by known methods such as vapor deposition, spin coating, and inkjet methods.

[0068] As materials for the electron transport layer of the organic EL element of the present invention, metal complexes of quinolinol derivatives such as Alq3 and 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 silole derivatives can be used. These materials may be formed into a film alone, but can also be formed into a film by mixing multiple types, and each can be used as a single layer. Further, a laminated structure of layers formed from these materials alone, a laminated structure of layers formed by mixing, or a laminated structure of a layer formed from these materials alone and a layer formed by mixing multiple types may be used. These materials can form a thin film by known methods such as vapor deposition, spin coating, and inkjet methods.

[0069] As materials for the electron injection layer of the organic EL element of the present invention, lithium fluoride, alkali metal salts such as cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinoline 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 a preferable selection of the electron transport layer and the cathode.

[0070] Furthermore, for the electron injection layer and the electron transport layer, those obtained by N-doping a metal such as cesium into the materials usually used for these layers can be used.

[0071] As the cathode of the organic EL element of the present invention, a metal having a low work function such as aluminum, and alloys having a lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, and an aluminum-magnesium alloy are used as electrode materials.

Example

[0072] Hereinafter, embodiments of the present invention will be specifically described by examples, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded.

[0073] 〔Example 1〕 <Synthesis of bis(biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2,’1”-terphenyl-3”-yl)-amine (Compound (58))> Into a reaction vessel, 7.0 g of 2,4,6-triphenyl-bromobenzene, 12.4 g of bis(biphenyl-4-yl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.3 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride·dichloromethane adduct, and 3.6 g of sodium hydrogen carbonate were charged, and the mixture was refluxed and stirred overnight under a THF / H2O mixed solvent. After cooling, ethyl acetate / H2O was added to the system, and the organic layer was taken out by extraction and liquid separation operations, and concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 9.5 g (yield: 74.5%) of a white powder of bis(biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1”-terphenyl-3”-yl)-amine (Compound (58)).

[0074]

Chemical Structure

[0075] The structure of the obtained white powder was identified using NMR. 1 The following 39 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 7.70 (2H), 7.67 (2H), 7.59 (4H), 7.51 - 7.29 (19H), 7.24 (4H), 7.00 (1H), 6.87 (6H), 6.67 (1H)

[0076] 〔Example 2〕 <Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (59))> Into a reaction vessel, 10.0 g of 2,4,6-triphenyl-bromobenzene, 22.3 g of (biphenyl-4-yl)-(4-naphthalen-1-yl-phenyl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.4 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride·dichloromethane adduct, and 5.1 g of sodium hydrogen carbonate were charged, and the mixture was refluxed and stirred overnight under a THF / H2O mixed solvent. After cooling, ethyl acetate / H2O was added to the system, and the organic layer was taken out by extraction and liquid separation operations, and concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 16.0 g (yield: 82.0%) of a white powder of (biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1''-terphenyl-3''-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (59)).

[0077]

Chemical formula

[0078] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.00 (2H), 7.87 (1H), 7.71 (2H), 7.69 (2H), 7.61 (2H), 7.59 - 7.43 (10H), 7.42 - 7.22 (14H), 7.03 (1H), 6.98 - 6.86 (6H), 6.69 (1H)

[0079] 〔Example 3〕 <Synthesis of (biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1''-terphenyl-3''-yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (60))> Into a reaction vessel, 11.0 g of 2,4,6-triphenyl-bromobenzene, 24.6 g of (biphenyl-4-yl)-(4-naphthalen-2-yl-phenyl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.5 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride·dichloromethane adduct, and 5.6 g of sodium hydrogen carbonate were charged, and the mixture was refluxed and stirred overnight under a THF / H2O mixed solvent. After cooling, ethyl acetate / H2O was added to the system, and the organic layer was taken out by extraction and liquid separation operations, and concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 15.5 g (yield: 72.0%) of a white powder of (biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1”-terphenyl-3”-yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (60)).

[0080]

Chemical Structure

[0081] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ(ppm)=8.00(1H), 7.91(1H), 7.89(2H), 7.73(1H), 7.67(4H), 7.60 - 7.37(12H), 7.37 - 7.27(8H), 7.25 - 7.19(4H), 6.99(1H), 6.89(2H), 6.85(4H), 6.65(1H)

[0082] 〔Example 4〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (15))> Into a reaction vessel, 13.7 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-phenanthren-9-yl-phenyl)-amine, 4.0 g of bromobenzene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.1 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred for 6 hours under a toluene solvent. After allowing it to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a dichloromethane / acetone mixed solvent to obtain 6.7 g (yield: 43.8%) of a pale yellow powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (15)).

[0083] [Chemical formula]

[0084] The structure of the obtained pale yellow powder was identified using NMR. 1 Thirty-nine hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.79 (1H), 8.72 (1H), 8.02 (1H), 7.89 (1H), 7.72 - 7.56 (9H), 7.45 (2H), 7.37 (1H), 7.33 - 7.17 (14H), 6.98 (2H), 6.89 (3H), 6.83 (3H), 6.64 (1H)

[0085] [Example 5] <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (31))>[[]] ​Into a reaction vessel, 10.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-amine, 7.8 g of 4-bromo-[1,1’:4’,1”]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 3.0 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 8.0 g (yield: 54.0%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (31)).

[0086]

Chemical formula

[0087] The structure of the obtained white powder was identified using NMR. 1 Thirty-nine hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ (ppm) = 7.69 - 7.60 (10H), 7.45 (4H), 7.40 (2H), 7.36 (2H), 7.29 (6H), 7.17 (2H), 7.20 (4H), 6.95 (2H), 6.80 (5H), 6.77 (1H), 6.62 (1H)

[0088] 〔Example 6〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4’-naphthalen-1-yl-biphenyl-4-yl)-phenyl-amine (Compound (32))> Into a reaction vessel, 12.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-amine, 10.0 g of 1-(4’-bromo-biphenyl-4-yl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.9 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 16.4 g (yield: 86.0%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-(4’-naphthalen-1-yl-biphenyl-4-yl)-amine (Compound (32)).

[0089] [Chemical formula]

[0090] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.00 (1H), 7.92 (1H), 7.87 (1H), 7.68 (4H), 7.65 (2H), 7.59 - 7.41 (10H), 7.36 (1H), 7.30 (2H), 7.29 (4H), 7.21 (4H), 7.18 (2H), 6.96 (2H), 6.82 (5H), 6.79 (1H), 6.63 (1H)

[0091] [Example 7] [Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4’-naphthalen-2-yl-biphenyl-4-yl)-phenyl-amine (Compound (33))] Into a reaction vessel, 12.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-amine, 10.0 g of 2-(4’-bromo-biphenyl-4-yl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.9 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a mixed solvent of chlorobenzene / acetone to obtain 14.9 g (yield: 78.4%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-(4’-naphthalen-2-yl-biphenyl-4-yl)-amine (Compound (33)).

[0092]

Chemical formula

[0093] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.09 (1H), 7.92 (2H), 7.87 (1H), 7.80 (3H), 7.68 (4H), 7.67 (2H), 7.50 (2H), 7.45 (1H), 7.43 (3H), 7.36 (1H), 7.32 - 7.26 (6H), 7.21 (4H), 7.18 (2H), 6.97 (1H), 6.96 (1H), 6.85 - 6.75 (6H), 6.62 (1H)

[0094] 〔Example 8〕 <Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(phenanthren-9-yl)-amine (Compound (61))> Into a reaction vessel, 10.0 g of 2,4,6-triphenyl-bromobenzene, 18.5 g of (biphenyl-4-yl)-(phenanthren-9-yl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.4 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride·dichloromethane adduct, and 5.1 g of sodium hydrogen carbonate were charged, and the mixture was refluxed and stirred overnight under a THF / H2O mixed solvent. After cooling, ethyl acetate / H2O was added to the system, and the organic layer was taken out by extraction and liquid separation operations, and concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 7.0 g (yield: 37.0%) of a pale yellow powder of (biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1''-terphenyl-3''-yl)-(phenanthren-9-yl)-amine (Compound (61)).

[0095]

Chemical formula

[0096] The structure of the obtained pale yellow powder was identified using NMR. 1 Thirty-nine hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ (ppm) = 8.72 (1H), 8.69 (1H), 7.90 (1H), 7.74 (1H), 7.65 (4H), 7.64 (2H), 7.58 (1H), 7.51 (3H), 7.48 - 7.32 (6H), 7.31 - 7.22 (9H), 7.19 (4H), 6.99 (1H), 6.82 (1H), 6.62 (3H), 6.52 (1H)

[0097] 〔Example 9〕 <Synthesis of (3',5'-diphenyl-1,1':2',1''-terphenyl-3''-yl)-(4-naphthalen-1-yl-phenyl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (76))> Into a reaction vessel, 13.4 g of (4-naphthalen-2-yl-phenyl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine, 7.6 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.3 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred for 6 hours under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a dichloromethane / acetone mixed solvent to obtain 10.6 g (yield: 59.2%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-1-yl-phenyl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (76)).

[0098] [Chemical formula]

[0099] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.02 (2H), 7.91 (3H), 7.86 (2H), 7.75 (1H), 7.69 (2H), 7.67 (2H), 7.57 (2H), 7.54 - 7.41 (8H), 7.37 (1H), 7.33 - 7.22 (12H), 7.02 (1H), 6.97 (2H), 6.94 (1H), 6.90 (1H), 6.88 (2H), 6.67 (1H)

[0100] [Example 10] [Synthesis of bis(4-naphthalen-2-yl-phenyl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine (Compound (77))] Into a reaction vessel, 7.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine, 11.0 g of 2-(4-bromo-phenyl)-naphthalene, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 4.4 g of 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl, and 6.8 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 4.1 g (yield: 29.1%) of white powder of bis(4-naphthalen-2-yl-phenyl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine (Compound (77)).

[0101]

Chemical formula

[0102] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ(ppm)=8.01(2H), 7.90(4H), 7.86(2H), 7.74(2H), 7.68(2H), 7.66(2H), 7.54(4H), 7.49(4H), 7.43(2H), 7.36(2H), 7.32(5H), 7.23(4H), 7.00(1H), 6.91(3H), 6.88(3H), 6.67(1H)

[0103] 〔Example 11〕 <Synthesis of bis(4-naphthalen-1-yl-phenyl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine (Compound (78))> Into a reaction vessel, 7.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine, 11.0 g of 1-(4-bromophenyl)-naphthalene, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 4.4 g of 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl, and 6.8 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After allowing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a dichloromethane / acetone mixed solvent to obtain 7.7 g (yield: 54.6%) of a white powder of bis(4-naphthalen-1-yl-phenyl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine (Compound (78)).

[0104]

Chemical formula

[0105] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.06 (1H), 7.94 (1H), 7.88 (1H), 7.79 (2H), 7.73 (4H), 7.62 (2H), 7.58 - 7.47 (5H), 7.44 (2H), 7.37 (2H), 7.32 - 7.19 (22H), 7.12 (1H)

[0106] 〔Example 12〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-2-yl-phenyl)-(phenanthren-9-yl)-amine (Compound (79))> Into a reaction vessel, 13.4 g of (4-naphthalen-2-yl-phenyl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-amine, 6.9 g of 9-bromo-phenanthrene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.3 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred for 6 hours under a toluene solvent. After allowing it to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 10.8 g (yield: 62.4%) of a pale yellow powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-2-yl-phenyl)-(phenanthren-9-yl)-amine (Compound (79)).

[0107]

Chemical formula

[0108] The structure of the obtained pale yellow powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.74 (1H), 8.70 (1H), 7.95 (1H), 7.92 (1H), 7.88 (1H), 7.86 (1H), 7.84 (1H), 7.75 (1H), 7.69 (1H), 7.66 (6H), 7.59 (1H), 7.49 (2H), 7.46 (1H), 7.43 (4H), 7.40 (1H), 7.35 (1H), 7.27 (6H), 7.20 (4H), 7.01 (1H), 6.84 (1H), 6.67 (2H), 6.65 (1H), 6.54 (1H)

[0109] 〔Example 13〕 <Synthesis of <(biphenyl-4-yl)-phenyl-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine (Compound (96))> Into a reaction vessel, 7.5 g of 2,4,6-triphenyl-bromobenzene, 12.2 g of (biphenyl-4-yl)-phenyl-[3'-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-biphenyl-4-yl]-amine, 0.5 g of tetrakis(triphenylphosphine)palladium(0), and 4.0 g of potassium carbonate were charged, and the mixture was refluxed and stirred overnight under a toluene / EtOH / H2O mixed solvent. After cooling, ethyl acetate / H2O was added to the system, and the organic layer was taken out by extraction and liquid separation operations, and concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / n-heptane) to obtain 12.9 g (yield: 94.4%) of a white powder of (biphenyl-4-yl)-phenyl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quarterphenyl-4"'-yl)-amine (Compound (96)).

[0110] [Chemical formula]

[0111] The structure of the obtained white powder was identified using NMR. 1 Thirty-nine hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ(ppm)=7.72(2H), 7.71(2H), 7.58(2H), 7.47(4H), 7.42(2H), 7.37(1H), 7.30(2H), 7.27(1H), 7.24 - 7.16(11H), 7.14(4H), 7.10 - 6.98(7H), 6.80(1H)

[0112] [Example 14] Synthesis of (3',5'-diphenyl-1,1':2',1":3"-1"'-quarterphenyl-4"'-yl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine (Compound (100)) Into a reaction vessel, 10.0 g of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-phenyl-amine, 5.7 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After allowing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 8.3 g (yield: 60.7%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine (Compound (100)).

[0113]

Chemical formula

[0114] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.02 (1H), 7.90 (1H), 7.84 (1H), 7.72 (2H), 7.71 (2H), 7.51 (2H), 7.46 (4H), 7.38 (3H), 7.31 (2H), 7.24 - 7.01 (22H), 6.80 (1H)

[0115] 〔Example 15〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (Compound (101))> Into a reaction vessel, 10.0 g of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-phenyl-amine, 6.2 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 7.7 g (yield: 56.3%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (Compound (101)).

[0116] [Chemical formula]

[0117] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.02 (1H), 7.89 (2H), 7.85 (1H), 7.73 (2H), 7.71 (3H), 7.61 (2H), 7.47 (4H), 7.37 (1H), 7.29 (2H), 7.25 - 7.13 (15H), 7.12 - 6.99 (7H), 6.80 (1H)

[0118] [Example 16] Synthesis of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (102)) Into a reaction vessel, 11.0 g of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-phenyl-amine, 8.0 g of 9-(4-bromo-phenyl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After allowing it to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 12.6 g (yield: 78.5%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (102)).

[0119] [Chemical formula]

[0120] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.78 (1H), 8.72 (1H), 8.06 (1H), 7.90 (1H), 7.73 (2H), 7.71 (3H), 7.67 (2H), 7.62 (1H), 7.58 (1H), 7.46 (2H), 7.43 (2H), 7.37 (1H), 7.32 (2H), 7.24 - 7.17 (15H), 7.17 - 7.02 (7H), 6.81 (1H)

[0121] [Example 17] [Synthesis of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-phenyl-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (107))] Into a reaction vessel, 10.0 g of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-phenyl-amine, 6.7 g of 4-bromo-[1,1’:4’,1”]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide were charged, and the mixture was refluxed with stirring overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 9.4 g (yield: 66.4%) of a pale yellow powder of (3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-phenyl-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (107)).

[0122]

Chemical Structure

[0123] The structure of the obtained pale yellow powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 7.72 (2H), 7.71 (2H), 7.66 (4H), 7.64 (2H), 7.53 (2H), 7.46 (4H), 7.36 (2H), 7.28 (2H), 7.24 - 7.12 (15H), 7.11 - 6.99 (7H), 6.80 (1H)

[0124] 〔Example 18〕 <Synthesis of bis(biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine (Compound (115))> Into a reaction vessel, 10.0 g of biphenyl-4-yl-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine, 4.5 g of 4-bromobiphenyl, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 10.5 g (yield: 84.5%) of a white powder of bis(biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine (Compound (115)).

[0125] [Chemical formula]

[0126] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 7.73 (2H), 7.72 (2H), 7.59 (4H), 7.51 (4H), 7.47 (2H), 7.43 (4H), 7.38 (1H), 7.32 (2H), 7.24 - 7.15 (15H), 7.14 - 7.01 (6H), 6.81 (1H)

[0127] [Example 19] <Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (116))>[[]] ​Into a reaction vessel, 10.0 g of biphenyl-4-yl-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine, 5.4 g of 2-(4-bromo-phenyl)-naphthalene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide were charged, and the mixture was refluxed with stirring overnight in a toluene solvent. After allowing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 9.1 g (yield: 68.8%) of a pale yellow powder of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (116)).

[0128]

Chemical formula

[0129] The structure of the obtained pale yellow powder was identified using NMR. 1 45 hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ(ppm)=8.03(1H), 7.90(2H), 7.86(1H), 7.75(2H), 7.72(3H), 7.64(2H), 7.60(2H), 7.54 - 7.41(8H), 7.38(1H), 7.33(1H), 7.25 - 7.17(15H), 7.16 - 7.02(6H), 6.81(1H)

[0130] 〔Example 20〕 <Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (117))> Into a reaction vessel, 10.0 g of biphenyl-4-yl-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine, 5.4 g of 1-(4-bromo-phenyl)-naphthalene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight in a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 12.5 g (yield: 94.5%) of a pale yellow powder of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (117)).

[0131] [Chemical formula]

[0132] The structure of the obtained pale yellow powder was identified using NMR. 1 45 hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ(ppm)=8.04(1H), 7.91(1H), 7.85(1H), 7.73(2H), 7.72(2H), 7.61(2H), 7.56 - 7.35(13H), 7.32(1H), 7.28 - 7.15(17H), 7.11(1H), 7.08(1H), 7.07(2H), 6.81(1H)

[0133] [Example 21] [Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(phenanthren-2-yl)-amine (Compound (118))] Into a reaction vessel, 10.0 g of biphenyl-4-yl-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine, 4.9 g of 2-bromo-phenanthrene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 8.7 g (yield: 67.9%) of a pale yellow powder of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(phenanthren-2-yl)-amine (Compound (118)).

[0134]

Chemical formula

[0135] The structure of the obtained pale yellow powder was identified using NMR. 1 43 hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ(ppm)=8.59(1H), 8.56(1H), 7.85(1H), 7.72(2H), 7.71(2H), 7.68(1H), 7.63(1H), 7.60(2H), 7.54(5H), 7.45(5H), 7.38(1H), 7.32(1H), 7.25 - 7.12(15H), 7.11(1H), 7.05(1H), 7.04(2H), 6.81(1H)

[0136] 〔Example 22〕 <Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(phenanthren-9-yl)-amine (Compound (119))> Into a reaction vessel, 10.0 g of biphenyl-4-yl-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-amine, 4.9 g of 9-bromophenanthrene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide were charged, and the mixture was refluxed with stirring overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 7.9 g (yield: 61.6%) of a pale yellow powder of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”:3”-1”’-quarterphenyl-4”’-yl)-(phenanthren-9-yl)-amine (Compound (119)).

[0137]

Chemical Structure

[0138] The structure of the obtained pale yellow powder was identified using NMR. 1 The following 43 hydrogen signals were detected by 1H-NMR (CDCl3). δ(ppm)=8.76(1H), 8.72(1H), 8.06(1H), 7.78(1H), 7.71(2H), 7.69(2H), 7.66(2H), 7.64(1H), 7.59(1H), 7.55(2H), 7.51(1H), 7.46(1H), 7.44(3H), 7.39(2H), 7.36(1H), 7.28(1H), 7.22 - 7.12(13H), 7.07(3H), 7.01(1H), 6.97(2H), 6.77(1H)

[0139] 〔Example 23〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4’-phenanthren-9-yl-biphenyl-4-yl)-phenyl-amine (Compound (127))> Into a reaction vessel, 10.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-amine, 9.5 g of 9-(4’-bromo-biphenyl-4-yl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.4 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 14.6 g (yield: 86.3%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-phenyl-(4’-phenanthren-9-yl-biphenyl-4-yl)-amine (Compound (127)).

[0140] [Chemical formula]

[0141] The structure of the obtained white powder was identified using NMR. 1 43 hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ (ppm) = 8.79 (1H), 8.74 (1H), 8.01 (1H), 7.91 (1H), 7.73 (1H), 7.69 (3H), 7.67 (3H), 7.65 (2H), 7.62 (3H), 7.56 (1H), 7.47 (2H), 7.44 (2H), 7.36 (1H), 7.29 (6H), 7.20 (6H), 6.97 (2H), 6.83 (5H), 6.79 (1H), 6.63 (1H)

[0142] [Example 24] <Synthesis of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-phenanthren-9-yl-phenyl)-amine (Compound (130))>[[]] ​Into a reaction vessel, 12.5 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-phenanthren-9-yl-phenyl)-amine, 5.4 g of 4-bromo-biphenyl, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 3.7 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred for 6 hours under a toluene solvent. After cooling to room temperature, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification using a dichloromethane / acetone mixed solvent to obtain 9.3 g (yield: 60.1%) of a white powder of (biphenyl-4-yl)-(3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-phenanthren-9-yl-phenyl)-amine (Compound (130)).

[0143]

Chemical Structure

[0144] The structure of the obtained white powder was identified using NMR. 1 43 hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ (ppm) = 8.79 (1H), 8.73 (1H), 8.03 (1H), 7.90 (1H), 7.70 (2H), 7.68 (2H), 7.67 (2H), 7.63 (1H), 7.61 (1H), 7.58 (2H), 7.44 (6H), 7.37 (1H), 7.33 (3H), 7.31 - 7.21 (11H), 7.01 (1H), 6.94 (3H), 6.89 (3H), 6.67 (1H)

[0145] 〔Example 25〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-1-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (132))> Into a reaction vessel, 8.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(1,1’:4’,1”-terphenyl-4-yl)-amine, 4.3 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 7.9 g (yield: 74.5%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-1-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (132)).

[0146]

Chemical Structure

[0147] The structure of the obtained white powder was identified using NMR. 1 The following 45 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 8.01 (1H), 7.91 (1H), 7.85 (1H), 7.71 - 7.62 (10H), 7.56 - 7.41 (10H), 7.36 (2H), 7.32 - 7.21 (12H), 7.01 (1H), 6.94 (3H), 6.88 (3H), 6.67 (1H)

[0148] 〔Example 26〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-2-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (133))> Into a reaction vessel, 8.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(1,1’:4’,1”-terphenyl-4-yl)-amine, 4.0 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-t-butylphosphine, and 1.5 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred for 3 hours under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 8.5 g (yield: 80.3%) of a light red powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(4-naphthalen-2-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (133)).

[0149]

Chemical Structure

[0150] The structure of the obtained light red powder was identified using NMR. 1 45 hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ(ppm)=8.00(1H), 7.91(1H), 7.89(1H), 7.86(1H), 7.73(1H), 7.70 - 7.62(10H), 7.53(2H), 7.51 - 7.40(8H), 7.35(2H), 7.30(6H), 7.22(4H), 6.99(1H), 6.91(2H), 6.86(4H), 6.66(1H)

[0151] 〔Example 27〕 <Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(3-naphthalen-1-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (134))> Into a reaction vessel, 8.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(1,1’:4’,1”-terphenyl-4-yl)-amine, 4.3 g of 1-(3-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a mixed solvent of toluene / acetone / n-heptane to obtain 6.0 g (yield: 56.6%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(3-naphthalen-1-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (134)).

[0152] [Chemical formula]

[0153] The structure of the obtained white powder was identified using NMR. 1 The following 45 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 7.87 (3H), 7.68 - 7.59 (10H), 7.50 (1H), 7.48 - 7.32 (11H), 7.29 (1H), 7.14 (4H), 7.09 (7H), 6.99 (2H), 6.91 (1H), 6.88 (1H), 6.87 (1H), 6.84 (2H), 6.63 (1H)

[0154] [Example 28] [Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(3-naphthalen-2-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (135))] Into a reaction vessel, 8.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(1,1’:4’,1”-terphenyl-4-yl)-amine, 4.3 g of 2-(3-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After allowing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 6.5 g (yield: 61.4%) of a white powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(3-naphthalen-2-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (135)).

[0155] [Chemical formula]

[0156] The structure of the obtained white powder was identified using NMR. 1 The following 45 hydrogen signals were detected by 1H-NMR (CDCl3). δ (ppm) = 7.93 (1H), 7.87 (2H), 7.85 (1H), 7.70 - 7.61 (11H), 7.53 - 7.39 (8H), 7.35 (2H), 7.31 (2H), 7.28 (1H), 7.25 - 7.15 (10H), 6.99 (1H), 6.87 (2H), 6.83 (2H), 6.81 (1H), 6.65 (1H)

[0157] [Example 29] [Synthesis of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(2-naphthalen-1-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (136))] Into a reaction vessel, 8.0 g of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(1,1’:4’,1”-terphenyl-4-yl)-amine, 4.3 g of 1-(2-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.5 g of sodium t-butoxide were charged, and the mixture was refluxed and stirred overnight under a toluene solvent. After allowing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was subjected to crystallization purification with a toluene / acetone mixed solvent to obtain 5.2 g (yield: 48.7%) of a pale yellow powder of (3’,5’-diphenyl-1,1’:2’,1”-terphenyl-3”-yl)-(2-naphthalen-1-yl-phenyl)-(1,1’:4’,1”-terphenyl-4-yl)-amine (Compound (136)).

[0158] [Chemical formula]

[0159] The structure of the obtained pale yellow powder was identified using NMR. 1 Forty-five hydrogen signals were detected by 1H-NMR (CDCl3) as follows. δ (ppm) = 7.66 (3H), 7.63 (2H), 7.59 (5H), 7.45 (5H), 7.38 - 7.23 (14H), 7.22 - 7.11 (6H), 7.01 (1H), 6.89 (1H), 6.78 (3H), 6.66 (1H), 6.56 (1H), 6.43 (1H), 6.09 (2H)

[0160] [Example 30] For the arylamine compounds obtained in Examples 1 to 29, the melting point and glass transition point were measured using a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100SA). The results are shown in Table 1.

[0161] [Table 1]

[0162] The arylamine compounds obtained in Examples 1 to 29 had a glass transition point of 100 °C or higher. This indicates that the thin film state is stable.

[0163] [Example 31] Using the arylamine compounds obtained in Examples 1 to 27, a vapor deposition film with a thickness of 100 nm was formed on an ITO substrate, and the work function was measured with an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.). The results are shown in Table 2.

[0164] [Table 2]

[0165] The arylamine compounds obtained in Examples 1 to 27 showed suitable energy levels compared to the work function of about 5.4 eV of general hole transport materials such as NPD and TPD, and it was found that they had good hole transport ability.

[0166] [Example 32] As shown in FIG. 13, the organic EL element was fabricated by sequentially depositing 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 capping layer 10 on a glass substrate 1 on which a reflective ITO electrode was previously formed as a transparent anode.

[0167] Specifically, a glass substrate 1 on which an ITO with a thickness of 50 nm, a reflective film of a silver alloy with a thickness of 100 nm, and an ITO with a thickness of 5 nm were sequentially formed was ultrasonically cleaned in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250 °C for 10 minutes. Thereafter, after performing UV ozone treatment for 2 minutes, this ITO-coated glass substrate was installed in a vacuum evaporator and depressurized to 0.001 Pa or less.

[0168] Subsequently, as the hole injection layer 3 covering the transparent anode 2, an electron acceptor (Acceptor-1) of the following structural formula and a compound (HTM-1) of the following structural formula were subjected to co-evaporation at an evaporation rate ratio of Acceptor-1:HTM-1 = 3:97 to form a film with a thickness of 10 nm.

[0169] On top of this hole injection layer 3, a compound (HTM-1) of the following structural formula was formed as the hole transport layer 4 with a thickness of 140 nm.

[0170] On top of this hole transport layer 4, the compound (58) of Example 1 was formed as the electron blocking layer 5 with a thickness of 5 nm.

[0171] On top of this electron blocking layer 5, a compound (EMD-1) of the following structural formula and a compound (EMH-1) of the following structural formula were subjected to co-evaporation at an evaporation rate ratio of EMD-1:EMH-1 = 5:95 to form the light-emitting layer 6 with a thickness of 20 nm.

[0172] On top of this light-emitting layer 6, a compound (ETM-1) of the following structural formula and a compound (ETM-2) of the following structural formula were subjected to co-evaporation at an evaporation rate ratio of ETM-1:ETM-2 = 50:50 to form the electron transport layer 7 with a thickness of 30 nm.

[0173] On top of this electron transport layer 7, lithium fluoride was formed as the electron injection layer 8 with a thickness of 1 nm.

[0174] On top of this electron injection layer 8, a magnesium-silver alloy was formed as the cathode 9 with a thickness of 12 nm.

[0175] Finally, a compound (CPL-1) of the following structure was formed as the capping layer 10 with a thickness of 60 nm.

[0176] Regarding the fabricated organic EL device, its characteristics were measured at room temperature in the air. The measurement results of the light-emitting characteristics obtained by applying a DC voltage to the fabricated organic EL device are summarized in Table 3.

[0177] [Chemical]

[0178] [Chemical]

[0179] [Chemical]

[0180] [Example 33] In Example 32, an organic EL device was fabricated under the same conditions except that Compound (59) of Example 2 was used instead of Compound (58) of Example 1 as the material of the electron blocking layer 5. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0181] [Example 34] In Example 32, an organic EL device was fabricated under the same conditions except that Compound (60) of Example 3 was used instead of Compound (58) of Example 1 as the material of the electron blocking layer 5. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0182] [Example 35] In Example 32, an organic EL device was fabricated under the same conditions except that Compound (15) of Example 4 was used instead of Compound (58) of Example 1 as the material of the electron blocking layer 5. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0183] [Example 36] In Example 32, an organic EL device was fabricated under the same conditions except that compound (31) of Example 5 was used as the material of the electron blocking layer 5 instead of compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0184] [Example 37] In Example 32, an organic EL device was fabricated under the same conditions except that compound (32) of Example 6 was used as the material of the electron blocking layer 5 instead of compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0185] [Example 38] In Example 32, an organic EL device was fabricated under the same conditions except that compound (33) of Example 7 was used as the material of the electron blocking layer 5 instead of compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0186] [Example 39] In Example 32, an organic EL device was fabricated under the same conditions except that compound (61) of Example 8 was used as the material of the electron blocking layer 5 instead of compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0187] [Example 40] In Example 32, an organic EL device was fabricated under the same conditions except that compound (76) of Example 9 was used as the material of the electron blocking layer 5 instead of compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0188] [Example 41] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (77) of Example 10 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0189] [Example 42] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (78) of Example 11 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0190] [Example 43] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (79) of Example 12 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0191] [Example 44] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (96) of Example 13 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0192] [Example 45] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (100) of Example 14 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0193] [Example 46] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (101) of Example 15 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0194] [Example 47] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (102) of Example 16 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0195] [Example 48] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (107) of Example 17 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0196] [Example 49] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (115) of Example 18 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light-emitting characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0197] [Example 50] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (116) of Example 19 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light-emitting characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0198] [Example 51] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (117) of Example 20 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light-emitting characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0199] [Example 52] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (118) of Example 21 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in air. The measurement results of the light-emitting characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0200] [Example 53] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (119) of Example 22 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0201] [Example 54] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (127) of Example 23 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0202] [Example 55] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (130) of Example 24 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0203] [Example 56] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (132) of Example 25 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0204] [Example 57] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (133) of Example 26 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0205] [Example 58] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (134) of Example 27 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0206] [Example 59] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (135) of Example 28 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0207] [Example 60] In Example 32, an organic EL device was fabricated under the same conditions except that the compound (136) of Example 29 was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0208] [Comparative Example 1] For comparison, in Example 32, an organic EL device was fabricated under the same conditions except that the compound (HTM-2) of the following structural formula (see, for example, Patent Document 5) was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0209]

Chemical formula

[0210] [Comparative Example 2] For comparison, in Example 32, an organic EL device was fabricated under the same conditions except that the compound (HTM-3) of the following structural formula was used as the material of the electron blocking layer 5 instead of the compound (58) of Example 1. For the fabricated organic EL device, characteristic measurements were performed at room temperature in the air. The measurement results of the light emission characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0211]

Chemical formula

[0212] Using the organic EL devices fabricated in Examples 32 to 60 and Comparative Examples 1 and 2, the measurement results of the device lifetime are summarized in Table 3. The device lifetime was measured as the time until the light emission luminance decayed to 950 cd / m 2 when constant current driving was performed with the light emission luminance at the start of light emission (initial luminance) set to 1000 cd / m 2 (corresponding to 95% when the initial luminance is set to 100%: 95% decay).

[0213]

Table 3

[0214] As shown in Table 3, the organic EL device using the arylamine compound of the present invention has a low driving voltage, and when a current of 10 mA / cm 2 flows, the luminous efficiency is 9.37 to 11.05 cd / A for the organic EL devices of Examples 32 to 60, which is higher than 8.97 to 9.15 cd / A for the organic EL devices of Comparative Examples 1 and 2. Also, in terms of power efficiency, it is 8.51 to 9.95 lm / W for the organic EL devices of Examples 32 to 60, which is higher than 8.19 to 8.23 lm / W for the organic EL devices of Comparative Examples 1 and 2. Furthermore, in terms of device lifetime (95% decay), it can be seen that the organic EL devices of Examples 32 to 60 have a lifetime equal to or longer than 267 to 632 hours compared to 245 to 269 hours for the organic EL devices of Comparative Examples 1 and 2.

[0215] As is clear from the above results, since the organic EL device of the present invention uses an arylamine compound having a large hole mobility and excellent electron blocking ability, it has been found that an organic EL device with a higher luminous efficiency and a longer lifetime can be realized while maintaining a low driving voltage as compared with conventional organic EL devices.

Industrial Applicability

[0216] The organic EL device using the arylamine compound having a specific structure of the present invention can improve the luminous efficiency and the durability of the organic EL device, and for example, it can be applied to household electrical appliances and lighting applications. In addition, the arylamine compound of the present invention can be used not only in organic EL devices but also in electronic device fields such as electrophotographic photoreceptors, image sensors, photoelectric conversion elements, and solar cells.

[0217] 1 Glass substrate 2 Transparent anode 3 Hole injection layer 4 Hole transport layer 5 Electron blocking layer 6 Light-emitting layer 7 Electron transport layer 8 Electron injection layer 9 Cathode 10 Capping layer

Claims

1. An arylamine compound represented by any of the following structures. 【Chemical 1】

2. An organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the arylamine compound according to Claim 1.

3. The organic electroluminescence device according to Claim 2, wherein the organic layer is a hole transport layer.

4. The organic electroluminescence device according to Claim 2, wherein the organic layer is an electron blocking layer.

5. The organic electroluminescence device according to Claim 2, wherein the organic layer is a hole injection layer.

6. The organic electroluminescence device according to Claim 2, wherein the organic layer is a light emitting layer.

7. An electronic device using an electronic component having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the arylamine compound according to Claim 1.

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