Arylamine compounds and organic electroluminescent devices

Abstract

To provide, as a material for highly efficient, highly durable organic EL devices, an organic EL device material having excellent hole injectability and transportability, electron blockability, high stability in a thin-film state, and excellent durability, and also to provide a highly efficient, highly durable organic EL device by using this compound.SOLUTION: The present invention concerns an arylamine compound represented by general formula (1). (In the formula, Ar1 to Ar4 are an aromatic hydrocarbon group, etc.; L1 and L2 are a divalent aromatic hydrocarbon group, etc.; R1 to R7 are a hydrogen atom, a deuterium atom, etc.; m and n are each independently an integer from 0 to 2; when m is 0, L1 represents a single bond, and when n is 0, L2 represents a single bond).SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Organic EL elements are self-luminous elements, and therefore are brighter and more visible than liquid crystal elements, enabling clearer displays, and therefore active research has been conducted on them.

[0003] In 1987, C.W. Tang and his colleagues at Eastman Kodak Company developed a layered structure element in which various roles were assigned to each material, making organic EL devices practical. They layered a phosphor capable of transporting electrons and an organic material capable of transporting holes, and injected both charges into the phosphor layer to emit light, achieving an luminance of 1000 cd / m at a voltage of 10 V or less. 2 Such high brightness has been achieved (see, for example, Patent Documents 1 and 2).

[0004] To date, many improvements have been made to the practical application of organic EL devices, and the various roles of the laminated structure have been further subdivided, resulting in high efficiency and durability being achieved by electroluminescent devices in which an anode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate (see, for example, Non-Patent Document 1).

[0005] Furthermore, attempts have been made to utilize triplet excitons with the aim of further improving luminous efficiency, and the use of phosphorescent compounds has been investigated (see, for example, Non-Patent Document 2). Furthermore, devices that utilize luminescence due to thermally activated delayed fluorescence (TADF) have also been developed, and in 2011, Adachi et al. of Kyushu University achieved an external quantum efficiency of 5.3% using a device that uses a thermally activated delayed fluorescence material (see, for example, Non-Patent Document 3).

[0006] The light-emitting layer can generally be prepared 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 aforementioned non-patent document, the selection of organic materials in an organic EL device significantly affects various properties of the device, such as efficiency and durability (see, for example, non-patent document 2).

[0007] In organic EL devices, charges injected from both electrodes recombine in the light-emitting layer to emit light. However, it is important to efficiently transfer both charges (holes and electrons) to the light-emitting layer, making it necessary to achieve an element with excellent carrier balance. Therefore, by using a material that has the properties of improving hole injection properties (supplying holes injected from the anode to the light-emitting layer) and improving electron blocking properties (blocking electrons injected from the cathode), the probability of holes and electrons recombining in the light-emitting layer can be increased, and by confining excitons generated in the light-emitting layer, high luminous efficiency can be achieved. To achieve this, the role played by hole transport materials is important, and hole transport materials with high hole injection properties, high hole mobility, high electron blocking properties, and high durability against electrons are required.

[0008] Furthermore, the heat resistance and amorphous nature of the material are also important factors in determining the lifespan of the element. Materials with low heat resistance will undergo thermal decomposition even at low temperatures due to the heat generated when the element is in operation, causing the material to deteriorate. Materials with low amorphous nature will undergo crystallization of the thin film even in a short period of time, causing the element to deteriorate. Therefore, the materials used must have high heat resistance and good amorphous nature.

[0009] Hole transport materials that have been used in organic EL devices to date 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 capabilities, its glass transition temperature (Tg), which is an indicator of heat resistance, is as low as 96°C, and crystallization occurs under high-temperature conditions, causing a deterioration in device characteristics (see, for example, Non-Patent Document 4).

[0010] In addition, among the aromatic amine derivatives described in the above patent documents, the hole mobility is 10 -3 cm 2 Although there are compounds with excellent mobility of 1000 times or more than 1000 times / Vs (see, for example, Patent Documents 1 and 2), there are problems such as insufficient electron blocking properties, which allow some electrons to pass through the light-emitting layer, making it impossible to expect an improvement in luminous efficiency, and therefore, in order to achieve even higher efficiency, materials with better electron blocking properties, more stable thin films, and higher heat resistance have been required. Also, although highly durable aromatic amine derivatives have been reported (see, for example, Patent Document 3), they were used as charge transport materials in electrophotographic photoreceptors, and there have been no examples of their use in organic EL devices.

[0011] In order to solve this problem, arylamine compounds having a substituted carbazole structure or a triarylbenzene structure have been proposed as compounds with improved properties such as heat resistance and hole injection properties (see, for example, Patent Documents 4 and 5). However, although the device life and luminous efficiency have been improved in devices using these compounds in the hole injection layer or hole transport layer, they are still not sufficient, and there is a demand for further reduction in driving voltage, improvement in luminous efficiency, and extension of the device life. [Prior art documents] [Patent documents]

[0012] [Patent Document 1] US5792557 [Patent Document 2] US5639914 [Patent Document 3] US7759030 [Patent Document 4] US8021764 [Patent Document 5] US20180175301 [Patent Document 6] EP2684932 [Non-patent literature]

[0013] [Non-Patent Document 1] Proceedings of the 9th Seminar of the Japan Society of Applied Physics, pp. 55-61 (2001) [Non-patent document 2] Proceedings of the 9th Seminar of the Japan Society of Applied Physics, pp. 23-31 (2001) [Non-patent document 3] Appl.Phys.Let.,98,083302(2011) [Non-patent document 4] Proceedings of the 3rd Regular Meeting of the Organic EL Symposium, pages 13-14 (2006) Summary of the Invention [Problem to be solved by the invention]

[0014] The object of the present invention is to provide a material for highly efficient and durable organic EL devices, which has (1) excellent hole injection and transport properties, (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 device that uses the material of the present invention and has (1) high luminous efficiency and power efficiency, (2) low luminous initiation voltage and practical driving voltage, and (3) long life. [Means for solving the problem]

[0016] In order to achieve the above object, the present inventors have conducted extensive research focusing on the excellent hole injection / transport capabilities, thin film stability, and durability of arylamine compounds having a triarylbenzene structure, and have obtained a material with dramatically improved properties by pursuing improvements and optimization of the substitution position. They have also found that the use of this material in organic EL devices improves luminous efficiency and power efficiency, enables reductions in light emission onset voltage and practical driving voltage, and realizes a longer lifespan than conventional devices, thereby completing the present invention.

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

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

[0019] 2) The present invention also relates to the arylamine compound according to the above 1), wherein in the general formula (1), R1 and R3, which may be the same or different, are hydrogen atoms or deuterium atoms.

[0020] 3) The present invention also relates to an arylamine compound according to 1) or 2) above, wherein, in general formula (1), Ar3 and Ar4, which may be the same or different, 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) The present invention also relates to an arylamine compound according to any one of 1) to 3) above, wherein, in general formula (1), 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) The present invention also relates to an arylamine compound according to any one of the above 1) to 4), wherein, in general formula (1), Ar3 and Ar4 are the same.

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

[0024] 7) The present invention also relates to the arylamine compound according to any one of 1) to 6) above, wherein, in general formula (1), 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) The present invention also relates to the arylamine compound according to any one of the above 1) to 7), wherein in general formula (1), the sum of the integers m and n is 0 or 1.

[0026] 9) An organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched between them, wherein the organic layer contains the arylamine compound described in any one of 1) to 8) above.

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

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

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

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

[0031] 14) The present invention also relates to an electronic device using an electronic component having a pair of electrodes and at least one organic layer sandwiched between them, wherein the organic layer contains the 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 fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1), the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" specifically includes a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, a spirobifluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a phenyl ... and heteroaryl groups having 2 to 20 carbon atoms, such as an aryl group, a pyrrolyl group, a thienyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, an azafluorenyl group, a diazafluorenyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group.

[0033] Specific examples of the "substituent" in the "substituted aromatic hydrocarbon group," "substituted aromatic heterocyclic group," or "substituted fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1) include a deuterium atom, a cyano group, a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a silyl group such as a trimethylsilyl group or a triphenylsilyl group; a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, or a propyloxy group; an alkenyl group such as a vinyl group or an allyl group; an aryloxy group such as a phenyloxy group or a tolyloxy group; a benzyloxy group or a 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, and triphenylenyl group; and 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, and carbolinyl group. These substituents may be further substituted with the substituents exemplified above. Furthermore, these substituents and the substituted benzene ring, or multiple substituents substituted on the same benzene ring, 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] Examples of the "divalent aromatic hydrocarbon group," "divalent aromatic heterocyclic group," or "divalent fused polycyclic aromatic group" in the "divalent substituted or unsubstituted aromatic hydrocarbon group," "divalent substituted or unsubstituted aromatic heterocyclic group," or "divalent substituted or unsubstituted fused polycyclic aromatic group" represented by L1 and L2 in general formula (1) include the same divalent groups obtained by removing one hydrogen atom from the "aromatic hydrocarbon group," "aromatic heterocyclic group," or "fused polycyclic aromatic group" in the "substituted or unsubstituted aromatic hydrocarbon group," "substituted or unsubstituted aromatic heterocyclic group," or "substituted or unsubstituted fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1).

[0035] Examples of the "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group," "substituted or unsubstituted aromatic heterocyclic group," or "substituted or unsubstituted fused polycyclic aromatic group" represented by L1 and L2 in general formula (1) include the same as those shown as the "substituent" in the "substituted aromatic hydrocarbon group," "substituted aromatic heterocyclic group," or "substituted fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1), and possible embodiments thereof are also similar.

[0036] In the "linear or branched alkyl group of 1 to 6 carbon atoms, which may have a substituent," "cycloalkyl group of 5 to 10 carbon atoms, which may have a substituent," or "linear or branched alkenyl group of 2 to 6 carbon atoms, which may have a substituent," represented by R1 to R7 in general formula (1), specific examples of the "linear or branched alkyl group of 1 to 6 carbon atoms," "cycloalkyl group of 5 to 10 carbon atoms," or "linear or branched alkenyl group of 2 to 6 carbon atoms" include 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. These groups and the substituted benzene ring, or a plurality of these groups substituted 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] Examples of the "substituent" in the "optionally substituted linear or branched alkyl group of 1 to 6 carbon atoms," "optionally substituted cycloalkyl group of 5 to 10 carbon atoms," or "optionally substituted linear or branched alkenyl group of 2 to 6 carbon atoms," represented by R1 to R7 in general formula (1) include the same as those shown as the "substituent" in the "substituted aromatic hydrocarbon group," "substituted aromatic heterocyclic group," or "substituted fused polycyclic aromatic group," represented by Ar1 to Ar4 in general formula (1), and possible embodiments thereof are also similar.

[0038] In the "carbon atom having a linear or branched alkyloxy group of 1 to 6 carbon atoms, which may have a substituent" or the "carbon atom having a cycloalkyloxy group of 5 to 10 carbon atoms, which may have a substituent", represented by R1 to R7 in general formula (1), specific examples of the "carbon atom having a linear or branched alkyloxy group of 1 to 6 carbon atoms" or the "carbon atom having a cycloalkyloxy group of 5 to 10 carbon atoms" include 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, and a 2-adamantyloxy group. These groups and the substituted benzene ring, or a plurality of these groups substituted 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 having 1 to 6 carbon atoms, which may have a substituent," or the "cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent," represented by R1 to R7 in general formula (1) include the same as those shown as the "substituent" in the "substituted aromatic hydrocarbon group," "substituted aromatic heterocyclic group," or "substituted fused polycyclic aromatic group," which are represented by Ar1 to Ar4 in general formula (1), and possible embodiments thereof are also similar.

[0040] Examples of the "aromatic hydrocarbon group," "aromatic heterocyclic group," or "fused polycyclic aromatic group" in the "substituted or unsubstituted aromatic hydrocarbon group," "substituted or unsubstituted aromatic heterocyclic group," or "substituted or unsubstituted fused polycyclic aromatic group" represented by R1 to R7 in general formula (1) include the same as those given as the "aromatic hydrocarbon group," "aromatic heterocyclic group," or "fused polycyclic aromatic group" in the "substituted or unsubstituted aromatic hydrocarbon group," "substituted or unsubstituted aromatic heterocyclic group," or "substituted or unsubstituted fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1).

[0041] Examples of the "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group," "substituted or unsubstituted aromatic heterocyclic group," or "substituted or unsubstituted fused polycyclic aromatic group" represented by R1 to R7 in general formula (1) include the same as those shown as the "substituent" in the "substituted aromatic hydrocarbon group," "substituted aromatic heterocyclic group," or "substituted fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1), and possible embodiments thereof are also similar.

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

[0043] The sum of the integers m and n in general formula (1) is preferably 0 or 1, and more preferably m is 0 or 1 and n is 0. When m and n are not 0, L1 and L2 in 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] In general formula (1), R1 to R7 are preferably a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, or spirobifluorenyl group, and more preferably a hydrogen atom, a deuterium atom, or an unsubstituted phenyl group, biphenyl group, or naphthyl group. R1 and R3 are preferably a hydrogen atom or a deuterium atom, and R2 is preferably a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group. It is also preferred that Ar3, Ar4, and R2 are the same. It is particularly preferred 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) and suitably used in the organic EL device of the present invention is preferably used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer, or light-emitting layer of the organic EL device, and more preferably as a constituent material of the hole transport layer or electron blocking layer. [Effects of the Invention]

[0046] The arylamine compounds of the present invention have properties such as (1) better hole injection characteristics, (2) higher hole mobility, (3) superior electron blocking ability, (4) high electron resistance, (5) stable existence in a thin film state, and (6) superior heat resistance, compared to conventional hole transport materials. By using the arylamine compounds of the present invention in organic EL devices, properties such as (7) high luminous efficiency, (8) low luminous initiation 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. As a result, an organic EL device having a hole injection layer and / or hole transport layer prepared using the compound as a hole injection material and / or hole transport material has improved hole transport efficiency to the light-emitting layer, thereby improving luminous efficiency, and can also improve durability of the device by reducing the driving voltage, thereby achieving high efficiency, low driving voltage, and long life.

[0048] The arylamine compound of the present invention has excellent electron blocking ability, high electron resistance, and is stable even in a thin film state, and is characterized by its ability to confine excitons generated in the light-emitting layer. As a result, organic EL devices having an electron-blocking layer prepared using the compound as an electron-blocking material have high luminous efficiency due to an improved probability of hole-electron recombination and suppression of thermal deactivation, and also have improved maximum luminance due to a reduced driving voltage and improved current resistance.

[0049] The arylamine compound of the present invention has excellent hole-transporting properties and a wide band gap. As a result, an organic EL device having an emitting layer fabricated using the compound as a host material can have a reduced driving voltage and improved luminous efficiency by forming the emitting layer with a fluorescent emitter, a phosphorescent emitter, or a delayed fluorescent emitter, which are called dopants.

[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 an emitting layer of an organic EL device, and can improve the luminous efficiency, driving voltage, and durability of conventional organic EL devices.

[0051] Additionally, the arylamine compound of the present invention can be used not only in organic EL devices but also in the field of electronic devices such as electrophotographic photoreceptors, image sensors, photoelectric conversion elements, and solar cells. [Brief explanation of the drawings]

[0052] [Figure 1]FIG. 1 shows compounds (1) to (12) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 2] FIG. 1 shows compounds (13) to (24) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 3] FIG. 1 shows compounds (25) to (36) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 4] FIG. 1 shows compounds (37) to (48) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 5] FIG. 1 shows compounds (49) to (60) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 6] FIG. 1 shows compounds (61) to (72) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 7] FIG. 1 shows compounds (73) to (84) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 8] FIG. 1 shows compounds (85) to (96) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 9] FIG. 1 shows compounds (97) to (108) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 10] FIG. 1 shows compounds (109) to (120) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 11] FIG. 1 shows compounds (121) to (132) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 12] FIG. 1 shows compounds (133) to (144) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 13]FIG. 1 shows compounds (145) to (153) as preferred specific examples of the arylamine compound represented by general formula (1). [Figure 14] FIG. 1 shows the configurations of the organic EL devices of Examples 32 to 60 and Comparative Examples 1 and 2. DETAILED DESCRIPTION OF THE INVENTION

[0053] The arylamine compounds of the present invention are novel compounds, but 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 suitably used in the organic EL device of the present invention, specific examples of preferred compounds are shown in Figures 1 to 12, but the present invention is not limited to these compounds.

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

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

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

[0058] The organic EL device of the present invention may have a structure comprising, in order on a substrate, an anode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, and a cathode; an electron blocking layer between the hole transport layer and the emitting layer; or a hole blocking layer between the emitting layer and the electron transport layer. In these multilayer structures, one organic layer may serve multiple functions. For example, one organic layer may serve both as a hole injection layer and a hole transport layer, or as an electron injection layer and an electron transport layer. Two or more organic layers having the same function may also be stacked, such as two stacked hole transport layers, two stacked emitting layers, or two stacked electron transport layers.

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

[0060] In addition to the arylamine compound of the present invention, materials for the hole injection layer and hole transport layer of the organic EL device of the present invention can include benzidine derivatives such as 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), and 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 of which is linked by a single bond or a divalent group containing no heteroatom. These materials can be used to form a film alone or in combination, and each can be used as a single layer. Alternatively, the layer structure may be a laminate structure of layers formed from these materials alone, a laminate structure of layers formed from a mixture of these materials, or a laminate structure of layers formed from a mixture of these materials alone and a mixture of these materials. Furthermore, a coating-type polymer material such as poly(3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly(styrene sulfonate) (hereinafter abbreviated as PSS) can be used as the material for the hole injection / transport layer. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet printing.

[0061] Furthermore, for the hole injection layer or the hole transport layer, materials that are normally used for these layers can be doped with P such as trisbromophenylaminehexachloroantimony or radialene derivatives (see, for example, Patent Document 6), or polymer compounds having a structure of a benzidine derivative such as TPD in their partial structure can be used.

[0062] In addition to the arylamine compound of the present invention, other materials that can be used for the electron-blocking layer of the organic EL device of the present invention include carbazole derivatives such as 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), and 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter abbreviated as Ad-Cz), as well as compounds having a triphenylsilyl group and a triarylamine structure, such as 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene. These materials may also serve as materials for the hole-transporting layer. These materials may be used alone or in combination to form a film, and each may be used as a single layer. Furthermore, the laminated structure may be a laminated structure of layers formed from these materials alone, a laminated structure of layers formed from a mixture of these materials, or a laminated structure of layers formed from a single material and a mixture of multiple materials. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet printing.

[0063] In addition to the arylamine compound of the present invention, other materials that can be used for the light-emitting layer of the organic EL device of the present invention include metal complexes of quinolinol derivatives such as Alq3, various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, and polyparaphenylenevinylene derivatives. The light-emitting layer may also be composed of a host material and a dopant material. Anthracene derivatives are preferably used as the host material. In addition to the light-emitting materials, such as the arylamine compound of the present invention, heterocyclic compounds having an indole ring as a fused ring substructure, heterocyclic compounds having a carbazole ring as a fused ring substructure, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives can also be used. Furthermore, dopant materials that can be used include quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, and aminostyryl derivatives. These materials can be used alone or in combination to form a film, and each can be used as a single layer. Furthermore, the laminated structure may be a laminated structure of layers formed from these materials alone, a laminated structure of layers formed from a mixture of these materials, or a laminated structure of layers formed from a single material and a mixture of multiple materials. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet printing.

[0064] Phosphorescent emitters can also be used as light-emitting materials. Examples of phosphorescent emitters include metal complexes of iridium, platinum, and the like. Examples include green phosphorescent emitters such as Ir(ppy)3, blue phosphorescent emitters such as FIrpic and FIr6, and red phosphorescent emitters such as Btp2Ir(acac). In this case, examples of host materials include hole-injecting / transporting host materials such as carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl (hereinafter abbreviated as CBP), TCTA, and mCP, as well as the arylamine compounds of the present invention. Examples of electron-transporting host materials include p-bis(triphenylsilyl)benzene (hereinafter abbreviated as UGH2) and 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (hereinafter abbreviated as TPBI). Using these materials allows for the fabrication of high-performance organic EL devices.

[0065] The phosphorescent material is preferably doped into the host material by co-evaporation in a range of 1 to 30 weight percent based on the total weight of the light-emitting layer to avoid concentration quenching.

[0066] Furthermore, materials that emit delayed fluorescence, such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, can also be used as light-emitting materials (see, for example, Non-Patent Document 3). These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and ink-jet printing.

[0067] Materials for the hole-blocking layer of the organic EL device of the present invention include compounds with hole-blocking properties, 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. These materials may also serve as materials for the electron-transporting layer. These materials may be formed into films alone or in combination, and each may be used as a single layer. Furthermore, these materials may be used in a laminated structure consisting of layers formed alone or in a mixture, or in a laminated structure consisting of layers formed alone and layers formed in a mixture. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet printing.

[0068] Materials that can be used for the electron transport layer of the organic EL device of the present invention include 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. These materials can be used to form films alone or in combination, and each can be used as a single layer. Furthermore, these materials can be used in a laminated structure consisting of layers formed alone, layers formed in a mixture, or layers formed in a mixture of these materials alone and layers formed in a mixture. These materials can be used to form thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0069] Materials that can be used for the electron injection layer of the organic EL device of the present invention include alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs). The electron injection layer can be omitted by selecting the electron transport layer and the cathode appropriately.

[0070] Furthermore, for the electron injection layer and the electron transport layer, materials that are normally used for these layers and are doped with N metal such as cesium can be used.

[0071] For the cathode of the organic EL device of the present invention, a metal having a low work function such as aluminum, or an alloy having an even lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy is used as the electrode material. [Example]

[0072] Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples as long as it does not depart from the gist of the invention.

[0073] Example 1 <Synthesis of bis(biphenyl-4-yl)-(3',5'-diphenyl-1,1':2,'1"-terphenyl-3"-yl)-amine (compound (58))> A reaction vessel was charged with 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 bicarbonate, and the mixture was refluxed overnight under a THF / HO mixture. After cooling, ethyl acetate / HO was added to the mixture, and the organic layer was extracted and separated. The crude product was then concentrated. 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 white powder of bis(biphenyl-4-yl)-(3',5'-diphenyl-1,1':2,'1"-terphenyl-3"-yl)-amine (compound (58)).

[0074] [ka]

[0075] The structure of the obtained white powder was identified using NMR. 1 The following 39 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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 bicarbonate, and the mixture was refluxed overnight under a THF / HO mixture. After cooling, ethyl acetate / HO was added to the mixture, and the organic layer was extracted and separated. The crude product was then concentrated. 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 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] [ka]

[0078] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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 bicarbonate, and the mixture was refluxed overnight under a THF / HO mixture. After cooling, ethyl acetate / HO was added to the mixture, and the organic layer was extracted and separated. The crude product was then concentrated. 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 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] [ka]

[0081] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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, and the mixture was refluxed under stirring in toluene for 6 hours. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using 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] [ka]

[0084] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 39 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight in a toluene solvent. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent, yielding 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] [ka]

[0087] The structure of the obtained white powder was identified using NMR. 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3). 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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight under stirring in toluene. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent, yielding 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] [ka]

[0090] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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(1 H), 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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight under stirring in toluene. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent 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] [ka]

[0093] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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 bicarbonate, and the mixture was refluxed overnight under a THF / HO mixture. After cooling, ethyl acetate / HO was added to the mixture, and the organic layer was extracted and separated. The crude product was then concentrated. 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 pale yellow powder of (biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(phenanthren-9-yl)-amine (compound (61)).

[0095] [ka]

[0096] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3). 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)) A reaction vessel was charged with 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, and the mixture was refluxed under stirring in a toluene solvent for 6 hours. After cooling, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using 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] [ka]

[0099] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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))> A reaction vessel was charged with 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, and the mixture was refluxed and stirred overnight in a toluene solvent. After allowing to cool, the mixture was filtered, and the filtrate 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 a white powder of bis(4-naphthalen-2-yl-phenyl)-(3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-amine (compound (77)).

[0101] [ka]

[0102] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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))> A reaction vessel was charged with 7.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)amine, 11.0 g of 1-(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, and the mixture was refluxed and stirred overnight in a toluene solvent. After cooling, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using 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] [ka]

[0105] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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, and the mixture was refluxed under stirring in a toluene solvent for 6 hours. After cooling, the mixture was filtered, and the filtrate 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 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] [ka]

[0108] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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"'-quaterphenyl-4"'-yl)-amine (compound (96)) A reaction vessel was charged with 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, and the mixture was refluxed overnight in a toluene / EtOH / HO mixed solvent. After cooling, ethyl acetate / HO was added to the mixture, and the organic layer was extracted and separated, followed by concentration to obtain a crude product. The resulting crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / n-heptane) to obtain 12.9 g (yield: 94.4%) of (biphenyl-4-yl)-phenyl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-amine (compound (96)) as a white powder.

[0110] [ka]

[0111] The structure of the obtained white powder was identified using NMR. 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3). 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"'-quaterphenyl-4"'-yl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine (compound (100)) A reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-phenylamine, 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, and the mixture was refluxed overnight in toluene. After cooling, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting 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"'-quaterphenyl-4"'-yl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine (compound (100)).

[0113] [ka]

[0114] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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"'-quaterphenyl-4"'-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (compound (101)) A reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-phenylamine, 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, and the mixture was refluxed under stirring in toluene overnight. After allowing to cool, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting 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"'-quaterphenyl-4"'-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (compound (101)).

[0116] [ka]

[0117] The structure of the obtained white powder was identified using NMR. 1 The following 41 hydrogen signals were detected by H-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"'-quaterphenyl-4"'-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (compound (102)) A reaction vessel was charged with 11.0 g of (3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-phenylamine, 8.0 g of 9-(4-bromophenyl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was refluxed overnight under toluene. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using 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"'-quaterphenyl-4"'-yl)-(4-phenanthren-9-yl-phenyl)-phenylamine (compound (102)).

[0119] [ka]

[0120] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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"'-quaterphenyl-4"'-yl)-phenyl-(1,1':4',1"-terphenyl-4-yl)-amine (compound (107)) A reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-phenylamine, 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, and the mixture was refluxed overnight in a toluene solvent with stirring. After cooling, the filtrate obtained by filtration was The mixture was concentrated to give a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to give 9.4 g (yield: 66.4%) of a pale yellow powder of (3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-phenyl-(1,1':4',1"-terphenyl-4-yl)-amine (compound (107)).

[0122] [ka]

[0123] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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"'-quaterphenyl-4"'-yl)-amine (compound (115))> A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-amine, 4.5 g of 4-bromo-biphenyl, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide, and the mixture was refluxed overnight under stirring in toluene. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent, yielding 10.5 g (yield: 84.5%) of bis(biphenyl-4-yl)-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-amine (compound (115)) as a white powder.

[0125] [ka]

[0126] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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"'-quaterphenyl-4"'-yl)-(4-naphthalen-2-yl-phenyl)-amine (compound (116)) A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-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, and the mixture was refluxed under toluene overnight with stirring. After allowing to cool, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting crude product was purified by crystallization using 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"'-quaterphenyl-4"'-yl)-(4-naphthalen-2-yl-phenyl)-amine (compound (116)).

[0128] [ka]

[0129] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-NMR (CDCl3). 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"'-quaterphenyl-4"'-yl)-(4-naphthalen-1-yl-phenyl)-amine (compound (117)) A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-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, and the mixture was refluxed overnight in toluene. After cooling, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting 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"'-quaterphenyl-4"'-yl)-(4-naphthalen-1-yl-phenyl)-amine (compound (117)).

[0131] [ka]

[0132] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-NMR (CDCl3). 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"'-quaterphenyl-4"'-yl)-(phenanthren-2-yl)-amine (compound (118)) A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-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, and the mixture was refluxed and stirred overnight in a toluene solvent. After allowing to cool, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using 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"'-quaterphenyl-4"'-yl)-(phenanthren-2-yl)-amine (compound (118)).

[0134] [ka]

[0135] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-NMR (CDCl3). 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), 7.5 4(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"'-quaterphenyl-4"'-yl)-(phenanthren-9-yl)-amine (compound (119)) A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1"'-quaterphenyl-4"'-yl)-amine, 4.9 g of 9-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, and the mixture was refluxed under stirring in toluene overnight. After allowing to cool, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting 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"'-quaterphenyl-4"'-yl)-(phenanthren-9-yl)-amine (compound (119)).

[0137] [ka]

[0138] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-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), 7.5 1(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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight under stirring in toluene. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent, yielding 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] [ka]

[0141] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-NMR (CDCl3). 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)) A reaction vessel was charged with 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, and the mixture was refluxed and stirred in toluene for 6 hours. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization 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] [ka]

[0144] The structure of the obtained white powder was identified using NMR. 1 The following 43 hydrogen signals were detected by H-NMR (CDCl3). 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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight in a toluene solvent with stirring. The mixture was then allowed to cool. The resulting mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting crude product was purified by crystallization using 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] [ka]

[0147] The structure of the obtained white powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-NMR (CDCl3). δ(ppm)=8.01(1H), 7.91(1H), 7.85(1H), 7.71-7.62(10H), 7.56-7.41(10 H), 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)) A reaction vessel was charged with 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, and the mixture was refluxed in a toluene solvent for 3 hours. The mixture was stirred. After cooling, the mixture was filtered and the filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 8.5 g (yield: 80.3%) of a pale 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] [ka]

[0150] The structure of the resulting pale red powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-NMR (CDCl3). 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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight in a toluene solvent with stirring. After allowing to cool, The filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using 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] [ka]

[0153] The structure of the obtained white powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-NMR (CDCl3). δ(ppm)=7.87(3H), 7.68-7.59(10H), 7.50(1H), 7.48-7.32(11H), 7.29(1H), 7.1 4(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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight in toluene with stirring. The mixture was then allowed to cool. The resulting mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting crude product was purified by crystallization using 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] [ka]

[0156] The structure of the obtained white powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-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)) A reaction vessel was charged with 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, and the mixture was refluxed overnight in a toluene solvent with stirring. After allowing to cool, The resulting mixture was filtered, and the filtrate was concentrated to obtain a crude product. The resulting crude product was purified by crystallization using 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] [ka]

[0159] The structure of the resulting pale yellow powder was identified using NMR. 1 The following 45 hydrogen signals were detected by H-NMR (CDCl3). 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 The melting points and glass transition points of the arylamine compounds obtained in Examples 1 to 29 were measured using a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). The results are shown in Table 1.

[0161] [Table 1]

[0162] The arylamine compounds obtained in Examples 1 to 29 had glass transition points of 100° C. or higher, which indicates that the thin film state was stable.

[0163] Example 31 Using the arylamine compounds obtained in Examples 1 to 27, vapor-deposited films with a thickness of 100 nm were formed on ITO substrates, and the work functions were measured using an ionization potential measurement 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 exhibit a preferable energy level compared to the work function of about 5.4 eV of common hole transport materials such as NPD and TPD, and are found to have good hole transport ability.

[0166] Example 32 As shown in Figure 13, the organic EL device was fabricated by depositing a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, an emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a capping layer 10 in this order on a glass substrate 1 on which a reflective ITO electrode had previously been formed as a transparent anode 2.

[0167] Specifically, a glass substrate 1 on which a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were formed in this order was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried for 10 minutes on a hot plate heated to 250° C. After that, it was subjected to UV ozone treatment for 2 minutes, and then the ITO-coated glass substrate was placed in a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less.

[0168] Subsequently, a hole injection layer 3 was formed to cover the transparent anode 2 by binary deposition of an electron acceptor (Acceptor-1) having the following structural formula and a compound (HTM-1) having the following structural formula at a deposition rate ratio of Acceptor-1:HTM-1=3:97, to a thickness of 10 nm.

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

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

[0171] On this electron blocking layer 5, a compound (EMD-1) having the following structural formula and a compound (EMH-1) having the following structural formula were deposited by binary deposition at a deposition rate ratio of EMD-1:EMH-1=5:95 to form an emitting layer 6 having a thickness of 20 nm.

[0172] On this light-emitting layer 6, an electron transport layer 7 was formed by binary deposition of a compound (ETM-1) with the following structural formula and a compound (ETM-2) with the following structural formula at a deposition rate ratio of ETM-1:ETM-2=50:50, to a thickness of 30 nm.

[0173] On this electron transport layer 7, an electron injection layer 8 was formed of lithium fluoride to a thickness of 1 nm.

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

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

[0176] The characteristics of the fabricated organic EL device were measured in air at room temperature. 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.

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[0180] Example 33 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (59) of Example 2 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0181] Example 34 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (60) of Example 3 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0182] Example 35 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (15) of Example 4 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0183] Example 36 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (31) of Example 5 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0184] Example 37 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (32) of Example 6 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. 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.

[0185] Example 38 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (33) of Example 7 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0186] Example 39 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (61) of Example 8 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0187] Example 40 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (76) of Example 9 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

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

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

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

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

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

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

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

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

[0196] Example 49 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (115) of Example 18 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0197] Example 50 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (116) of Example 19 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0198] Example 51 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (117) of Example 20 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0199] Example 52 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (118) of Example 21 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0200] Example 53 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (119) of Example 22 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0201] Example 54 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (127) of Example 23 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. 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.

[0202] Example 55 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (130) of Example 24 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0203] Example 56 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (132) of Example 25 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0204] Example 57 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (133) of Example 26 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0205] Example 58 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (134) of Example 27 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0206] Example 59 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (135) of Example 28 was used instead of compound (58) of Example 1 as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0207] Example 60 An organic EL device was fabricated under the same conditions as in Example 32, except that compound (136) of Example 29 was used as the material for the electron-blocking layer 5 instead of compound (58) of Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. The measurement results of the luminescence characteristics when a DC voltage was applied to the fabricated organic EL device are summarized in Table 3.

[0208] Comparative Example 1 For comparison, an organic EL device was fabricated under the same conditions as in Example 32, except that the compound (58) used in Example 1 was replaced with a compound (HTM-2) having the following structural formula (see, for example, Patent Document 5) as the material for the electron-blocking layer 5. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. 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.

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[0210] Comparative Example 2 For comparison, an organic EL device was fabricated under the same conditions as in Example 32, except that the compound (HTM-3) of the following structural formula was used as the material for the electron-blocking layer 5 instead of the compound (58) in Example 1. The characteristics of the fabricated organic EL device were measured in the atmosphere at room temperature. 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.

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[0212] The device life was measured using the organic EL devices fabricated in Examples 32 to 60 and Comparative Examples 1 and 2, and the results are summarized in Table 3. The device life was measured when the luminance at the start of light emission (initial luminance) was increased to 1000 cd / m 2 When driven at a constant current, the luminance was 950 cd / m 2 The time it took for the brightness to decay to 95% (corresponding to 95% of the initial brightness of 100%) was measured.

[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 a current density of 10 mA / cm. 2 The luminous efficiency when a current of 100 kJ / s was passed was 8.97 to 9.15 cd / A for the organic EL elements of Comparative Examples 1 and 2, while the organic EL elements of Examples 32 to 60 were highly efficient at 9.37 to 11.05 cd / A. The power efficiency was also high, at 8.51 to 9.95 lm / W for the organic EL elements of Examples 32 to 60, while the power efficiency was 8.19 to 8.23 ​​lm / W for the organic EL elements of Comparative Examples 1 and 2. Furthermore, the element lifetime (95% decay) was 267 to 632 hours for the organic EL elements of Examples 32 to 60, which was equivalent to or greater than the 245 to 269 hours for the organic EL elements of Comparative Examples 1 and 2.

[0215] As is clear from the above results, the organic EL element of the present invention uses an arylamine compound having high hole mobility and excellent electron blocking ability, and therefore, it has been found that it is possible to realize an organic EL element that has higher luminous efficiency and longer life while maintaining a low driving voltage compared to conventional organic EL elements. [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 durability of the organic EL device, making it possible to expand the use of the organic EL device to, for example, household electrical appliances and lighting. Furthermore, the arylamine compound of the present invention can be used not only in organic EL devices but also in the field of electronic devices 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: 【Chemistry 1】

2. 10. 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. 3. The organic electroluminescence device according to claim 2, wherein the organic layer is a hole transport layer.

4. 3. The organic electroluminescent 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. 10. An electronic device using an electronic component having a pair of electrodes and at least one organic layer sandwiched between them, wherein the organic layer contains the arylamine compound according to claim 1.

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