Arylamine compound, organic electroluminescent element, and electronic device

Abstract

The present application aims to provide an organic compound having excellent properties of hole-injection / transporting performance, electron-blocking ability, and stability in a thin film state, as a material for an organic EL element with high efficiency and durability, and to provide an organic EL element with high efficiency and durability using the compound. The present application is an arylamine compound represented by the following general formula (1). In the formula, Ar1 and Ar2 represent a substituted or unsubstituted aromatic hydrocarbon group or the like, Ar3 and Ar4 represent a substituted or unsubstituted phenyl group or the like, L represents a substituted or unsubstituted divalent aromatic hydrocarbon group or the like, R1 to R3 represent a hydrogen atom or the like, and n represents an integer of 1 to 2.

Description

Technical Field

[0001] This invention relates to compounds and elements suitable for use as self-emissive elements in various display devices, specifically to an arylamine compound and an organic EL element using the compound. Background Technology

[0002] Organic EL elements are self-emissive elements, therefore they are brighter and have better visibility than liquid crystal elements, enabling clear displays, and thus have received active research.

[0003] In 1987, CWTang et al. from Eastman / Kodak developed a layered structure element in which various materials performed different functions, thus making organic EL elements using organic materials practical. They layered an electron-transferring phosphor with an organic material that could transport holes, and injected the charges of both into the phosphor layer to make it emit light, thereby achieving 1000 cd / m² at a voltage below 10V. 2 The above high brightness (for example, see Patent Document 1 and Patent Document 2).

[0004] To date, numerous improvements have been made to make organic EL devices practical, further subdividing the various functions of the stacked structure. By sequentially arranging an anode, hole injection layer, hole transport layer, light emission layer, electron transport layer, electron injection layer and cathode on a substrate, high efficiency and durability can be achieved (for example, see Non-Patent Literature 1).

[0005] In addition, with the aim of further improving luminescence efficiency, attempts have been made to apply triplet excitons to study the application of phosphorescent compounds (for example, see Non-Patent Literature 2). Moreover, devices that emit light using thermally activated delayed fluorescence (TADF) have also been developed. In 2011, Adachi et al. from Kyushu University in Japan achieved an external quantum efficiency of 5.3% using a device using thermally activated delayed fluorescence materials (for example, see Non-Patent Literature 3).

[0006] The luminescent layer can also be fabricated by doping a charge-transporting compound, generally referred to as the host material, with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence. As described in the aforementioned non-patent literature, the choice of organic material in an organic EL element has a significant impact on multiple characteristics of the element, such as its efficiency and durability. (See, for example, non-patent literature 2).

[0007] In organic electron microscope (EL) devices, light emission is achieved by the recombination of charges injected from the two electrodes in the light-emitting layer. Efficiently transferring both holes and electrons to the light-emitting layer is crucial, requiring devices exhibiting excellent carrier balance. Therefore, by using materials that enhance hole injection capability (supplying holes from the anode to the light-emitting layer) and improve electron blocking capability (blocking electrons injected from the cathode), the probability of hole-electron recombination within the light-emitting layer is increased, and the generation of excitons within the light-emitting layer is confined, thereby achieving high luminous efficiency. Thus, hole transport materials play a vital role, requiring materials with high hole injection capability, high hole mobility, high electron blocking capability, and high electron durability.

[0008] In addition, the heat resistance and amorphous properties of the material are also important factors regarding the lifespan of components. Materials with low heat resistance will undergo thermal decomposition even at low temperatures due to the heat generated during component operation, leading to material degradation. Materials with low amorphous properties will crystallize into thin films even in a short period of time, resulting in component degradation. Therefore, the materials used must possess high heat resistance and good amorphous properties.

[0009] To date, N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) and various aromatic amine derivatives (see, for example, Patent Documents 1 and 2) are known as hole transport materials for organic EL devices. However, although NPD has good hole transport capabilities, its glass transition point (Tg), an indicator of heat resistance, is as low as 96°C, and its device properties deteriorate due to crystallization at high temperatures (see, for example, Non-Patent Document 4).

[0010] Furthermore, among the aromatic amine derivatives described in the aforementioned patent documents, those with holes have a mobility of 10. - 3 cm 2 Compounds with excellent mobility of / Vs or higher (e.g., see Patent Documents 1 and 2) exhibit insufficient electron blocking properties, resulting in some electrons penetrating the luminescent layer and thus preventing the expectation of improved luminous efficiency. For further increases in efficiency, materials with higher electron blocking properties, more stable films, and higher heat resistance are required. Additionally, aromatic amine derivatives with high durability have been reported (e.g., see Patent Document 3), but they are used as charge transport materials in electrophotographic photosensitive elements, and therefore there are no examples of their use in organic EL elements.

[0011] As compounds that improve heat resistance, hole injection properties, etc. in order to solve this problem, arylamine compounds with substituted carbazole structure and triarylbenzene structure have been proposed (for example, see Patent Document 4 and Patent Document 5). However, although using these compounds in hole injection layer or hole transport layer devices improves device lifetime, luminous efficiency, etc., it is not enough. Further reductions in driving voltage, luminous efficiency, and device lifetime are needed.

[0012] Patent Document 1: US Patent No. 5,792,557

[0013] Patent Document 2: US Patent No. 5639914

[0014] Patent Document 3: US Patent No. 7759030 Specification

[0015] Patent Document 4: US Patent No. 8021764

[0016] Patent Document 5: US Patent No. 10,818,844

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

[0018] Non-patent literature 1: Proceedings of the 9th Workshop of the Chinese Society of Applied Physics, pp. 55-61 (2001)

[0019] Non-patent document 2: Proceedings of the 9th Workshop of the Chinese Society of Applied Physics, pp. 23-31 (2001)

[0020] Non-patent literature 3: Appl. Phys. Let., 98, 083302 (2011)

[0021] Non-patent literature 4: Proceedings of the Third Regular Meeting of the Organic EL Symposium, pp. 13-14 (2006) Summary of the Invention

[0022] The purpose of this invention is to provide an organic EL element material with the following characteristics as a high-efficiency and high-durability organic EL element material, namely, (1) excellent hole injection / transmission performance; (2) electron blocking capability; (3) high stability in thin film state; and (4) excellent durability.

[0023] In addition, by using the above materials, an organic EL element with the following characteristics is provided: (1) high luminous efficiency and power efficiency; (2) low luminous initiation voltage and practical driving voltage; and (3) long lifespan.

[0024] To achieve the aforementioned objectives, the inventors focused on the excellent hole injection / transport capabilities, electron blocking capabilities, film stability, and durability of arylamine compounds with a triarylphenyl structure. They discovered that by introducing substituents at specific positions to optimize the structure, the material properties could be dramatically improved. Furthermore, by using this material in organic EL devices, the luminous efficiency and electroefficiency were improved, the emission initiation voltage and practical driving voltage were suppressed, and a longer lifetime than before was achieved, thus completing this invention.

[0025] 1) That is, the present invention is: an arylamine compound represented by the following general formula (1).

[0026] [Chemical Formula 1]

[0027]

[0028] In the formula, Ar1 and Ar2 can be the same or different, and represent substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted fused polycyclic aromatic groups.

[0029] Ar3 and Ar4 can be the same or different, and represent substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted carbazole, or substituted or unsubstituted phenanthryl.

[0030] L represents a substituted or unsubstituted divalent aromatic hydrocarbon group, a substituted or unsubstituted divalent aromatic heterocyclic group, or a substituted or unsubstituted divalent fused polycyclic aromatic group.

[0031] R1 to R3 can be the same or different, and represent hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano, nitro, alkyl group with 1 to 6 carbon atoms that can have substituents (linear or branched), cycloalkyl group with 5 to 10 carbon atoms that can have substituents, alkenyl group with 2 to 6 carbon atoms that can have substituents, alkoxy group with 1 to 6 carbon atoms that can have substituents, cycloalkoxy group with 5 to 10 carbon atoms that can have substituents, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy group.

[0032] n represents an integer from 1 to 2. When n is 2, L can be the same or different from each other.

[0033] 2) In addition, the present invention is an arylamine compound according to 1), wherein R1 to R3 in the general formula (1) can be the same or different, and are hydrogen atoms or deuterium atoms.

[0034] 3) In addition, the present invention is: an arylamine compound according to 1) or 2), wherein at least one of Ar3 and Ar4 in the general formula (1) is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted carbazolyl.

[0035] 4) In addition, the present invention is: an arylamine compound according to any one of 1) to 3), wherein Ar4 in the general formula (1) is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted carbazolyl.

[0036] 5) In addition, the present invention is: an arylamine compound according to any one of 1) to 4), wherein L in the general formula (1) is an unsubstituted phenylene, an unsubstituted biphenylene, or an unsubstituted naphthylene.

[0037] 6) In addition, the present invention is: an arylamine compound according to any one of 1) to 5), wherein Ar1 and Ar2 in the general formula (1) can be the same or different, and are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0038] 7) In addition, the present invention is: an arylamine compound according to any one of 1) to 6), wherein n in the general formula (1) is 1.

[0039] 8) In addition, the present invention is: an organic EL element having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein the organic layer contains any one of the arylamine compounds described in 1) to 7) above.

[0040] 9) In addition, the present invention is: an organic EL element according to 8), wherein the organic layer is a hole transport layer.

[0041] 10) In addition, the present invention is: an organic EL element according to 8), wherein the organic layer is an electron blocking layer.

[0042] 11) In addition, the present invention is: an organic EL element according to 8), wherein the organic layer is a hole injection layer.

[0043] 12) In addition, the present invention is: an organic EL element according to 8), wherein the organic layer is a light-emitting layer.

[0044] 13) In addition, the present invention is: an electronic device comprising an element having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein the organic layer comprises any one of the arylamine compounds described in 1) to 6).

[0045] As in general formula (1), the "aromatic hydrocarbon group", "aromatic heterocyclic group", or "fused polycyclic aromatic group" represented by Ar1 to Ar4, for example, besides phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthryl, fluorenyl, spirodifluorenyl, indene, pyrene, perylene, fluoranyl, benzophenanthryl, pyridyl, pyrimidinyl, triphenylene, etc. In addition to azinoyl, furanyl, pyrroleyl, thiopheneyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiopheneyl, indolyl, carbazoyl, benzoxazolyl, benzothiazoyl, azafluorenyl, diazafluorenyl, azaspirodifluorenyl, diazaspirodifluorenyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, naphridinyl, phenanthrololinyl, acridineyl, and carolinyl, aryl groups with 6 to 30 carbon atoms or heteroaryl groups with 2 to 20 carbon atoms can also be listed.

[0046] As the "substituent" in general formula (1) represented by Ar1 to Ar4, which is "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted fused polycyclic aromatic group", examples include: deuterium atom, cyano, nitro; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; silyl groups such as trimethylsilyl, triphenylsilyl; straight-chain or branched alkyl groups with 1 to 6 carbon atoms such as methyl, ethyl, propyl; straight-chain or branched alkoxy groups with 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy; and alkenyl groups such as vinyl, allyl. ; aryloxy groups such as phenoxy and tolyoxy; arylalkyloxy groups such as benzyloxy and phenethoxy; aromatic hydrocarbon groups or fused polycyclic aromatic groups such as phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluorenyl, spirodifluorenyl, indyl, pyrene, perylene, fluoranyl, and benzo[a]phenanthryl; and aromatic heterocyclic groups such as pyridyl, thiophene, furanyl, pyrroleyl, quinolinyl, isoquinolinyl, benzo[a]furanyl, benzo[a]thiopheneyl, indolyl, carbazoyl, benzo[a]oxazolyl, benzo[a]thiazoyl, quinoxalyl, benzimidazolyl, pyrazolyl, dibenzo[a]furanyl, dibenzo[a]thiopheneyl, and carbazoyl. These substituents can be further substituted by the substituents exemplified above. In addition, these substituents and the substituted benzene ring, or multiple substituents substituted on the same benzene ring, can form rings by bonding with each other via single bonds, substituted or unsubstituted methylene, oxygen, or sulfur atoms.

[0047] As in general formula (1), the "divalent aromatic hydrocarbon group", "divalent aromatic heterocyclic group" or "divalent fused polycyclic aromatic group" represented by L, which are "substituted or unsubstituted divalent aromatic hydrocarbon group", "substituted or unsubstituted divalent aromatic heterocyclic group" or "substituted or unsubstituted divalent fused polycyclic aromatic group", can be listed as a group after removing one hydrogen atom from the group represented by Ar1 to Ar4 in general formula (1), which are "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted fused polycyclic aromatic group".

[0048] As for the "substituent" in general formula (1) represented by L, which is "substituted or unsubstituted divalent aromatic hydrocarbon group", "substituted or unsubstituted divalent aromatic heterocyclic group" or "substituted or unsubstituted divalent fused polycyclic aromatic group", the same group as the group represented by Ar1 to Ar4 in general formula (1) representing "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted fused polycyclic aromatic group" can be listed, and the same form can also be listed.

[0049] Examples of "linear or branched alkyl groups having 1 to 6 carbon atoms that can have substituents", "cycloalkyl groups having 5 to 10 carbon atoms that can have substituents", or "linear or branched alkenyl groups having 2 to 6 carbon atoms that can have substituents" represented by R1 to R3 in general formula (1) include "linear or branched alkyl groups having 1 to 6 carbon atoms", "cycloalkyl groups having 5 to 10 carbon atoms", or "linear or branched alkenyl groups having 2 to 6 carbon atoms". For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, vinyl, allyl, isopropenyl, and 2-butenyl, etc. These substituents and the substituted benzene ring, or multiple substituents substituted on the same benzene ring, can form a ring through single bonds, substituted or unsubstituted methylene groups, substituted or unsubstituted amino groups, oxygen atoms, or sulfur atoms.

[0050] As for the "substituents" in general formula (1) represented by R1 to R3, which are "linear or branched alkyl groups having 1 to 6 carbon atoms that can have substituents", "cycloalkyl groups having 5 to 10 carbon atoms that can have substituents", or "linear or branched alkenyl groups having 2 to 6 carbon atoms that can have substituents", the same groups that can take the same forms as the groups represented by "substituents" in general formula (1) represented by Ar1 to Ar4, which are "substituted aromatic hydrocarbon groups", "substituted aromatic heterocyclic groups" or "substituted fused polycyclic aromatic groups".

[0051] The terms "linear or branched alkoxy group with 1 to 6 carbon atoms capable of having a substituent" or "cycloalkoxy group with 5 to 10 carbon atoms capable of having a substituent" represented by R1 to R3 in general formula (1) can be exemplified by, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-pentoxy, n-hexoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, 1-adamantoxy, 2-adamantoxy, etc. These substituents and the substituted benzene ring, or multiple substituents substituted on the same benzene ring, can form a ring by mutual bonding via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom.

[0052] As for the "substituent" in general formula (1), which is represented by R1 to R3 as "a straight-chain or branched alkoxy group with 1 to 6 carbon atoms capable of having a substituent" or "a cycloalkoxy group with 5 to 10 carbon atoms capable of having a substituent", the same group as the group represented by Ar1 to Ar4 in general formula (1) as "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted fused polycyclic aromatic group", can also take the same form.

[0053] As for the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" represented by R1 to R3 in general formula (1), the same groups as those represented by Ar1 to Ar4 in general formula (1) can be listed.

[0054] As for the "substituent" in general formula (1) represented by R1 to R3, which is "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted fused polycyclic aromatic group", the same group as the group represented by Ar1 to Ar4 in general formula (1) is listed. The same forms can also be listed.

[0055] As for the "substituted or unsubstituted aryloxy group" represented by R1 to R3 in general formula (1), for example, in addition to phenoxy, biphenoxy, terphenyloxy, naphthoxy, anthrathoxy, phenanthroxy, fluorenoxy, spirodifluorenoxy, indoxy, pyreneoxy, peryloxy, fluoranthoxy, benzophenanthroxy, benzofuranoxy, benzothiophenoxy, indoloxy, carbazoleoxy, dibenzofuranoxy and dibenzothiophenoxy, aryl groups with 6 to 30 carbon atoms or heteroaryl groups with 2 to 20 carbon atoms can also be listed. These substituents and the substituted benzene ring, or multiple substituents substituted on the same benzene ring, can form a ring by mutual bonding through single bonds, substituted or unsubstituted methylene groups, substituted or unsubstituted amino groups, oxygen atoms, or sulfur atoms.

[0056] As for the "substituent" in "substituted or unsubstituted aryloxy group" represented by R1 to R3 in general formula (1), the same group as the group represented by "substituent" in "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted fused polycyclic aromatic group" represented by Ar1 to Ar4 in general formula (1) can be listed, and the same form can also be listed.

[0057] At least one of Ar3 and Ar4 in general formula (1) is preferably a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted carbazolyl, more preferably an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted carbazolyl.

[0058] Ar3 and Ar4 in general formula (1) can be the same or different. When they are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the electron blocking ability is excellent. Therefore, it is preferred, more preferably, to be unsubstituted phenyl, unsubstituted biphenyl or unsubstituted naphthyl, and particularly preferably unsubstituted phenyl or unsubstituted naphthyl.

[0059] When L in general formula (1) is an unsubstituted phenylene, an unsubstituted biphenylene, or an unsubstituted naphthylene, it has excellent electron blocking ability, and is therefore preferred, and more preferably, an unsubstituted phenylene or an unsubstituted biphenylene.

[0060] In addition, n in general formula (1) is preferably 1.

[0061] Ar1 and Ar2 in general formula (1) can be the same or different. When Ar1 and Ar2 are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, or substituted or unsubstituted terphenyl, the electron blocking ability is excellent. Therefore, Ar1 and Ar2 are preferred, and more preferably substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl.

[0062] In general formula (1), R1 to R3 can be the same or different, preferably hydrogen atoms or deuterium atoms, and more preferably hydrogen atoms for easy synthesis.

[0063] The arylamine compound represented by the above general formula (1) is preferably used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer or light emission layer of the organic EL element, and more preferably as a constituent material of the hole transport layer or electron blocking layer.

[0064] Compared with conventional materials, the arylamine compounds of the present invention have the following characteristics: (1) good hole injection characteristics; (2) high hole mobility; (3) excellent electron blocking ability; (4) high electron resistance; (5) stable existence in thin film state; (6) excellent heat resistance, etc. By using the arylamine compounds of the present invention in organic EL devices, the following characteristics are obtained: (7) high luminous efficiency; (8) low luminous initiation voltage; (9) low practical driving voltage; (10) long lifetime, etc.

[0065] The arylamine compounds of the present invention exhibit excellent hole injection / transport performance, thin film stability, and durability. Therefore, organic EL devices having hole injection layers and / or hole transport layers prepared by using this compound as a hole injection material and / or hole transport material can improve hole transport efficiency to the light-emitting layer, improve luminous efficiency, and enhance device durability by reducing the driving voltage, resulting in high efficiency, low driving voltage, and long lifespan.

[0066] The arylamine compound of the present invention has the following characteristics: excellent electron blocking ability, high electron tolerance, and stability in the thin film state, thereby restricting the excitons generated within the light-emitting layer. Therefore, organic EL devices having an electron blocking layer fabricated using this compound as an electron blocking material can increase the probability of hole-electron recombination and suppress thermal deactivation, thus exhibiting high luminous efficiency, improving current tolerance by reducing the driving voltage, and thereby increasing maximum luminous brightness.

[0067] The arylamine compounds of the present invention exhibit excellent hole transport properties and a wide band gap. Therefore, an organic EL element having a light-emitting layer fabricated using this compound as the host material can form a light-emitting layer by supporting phosphors, phosphors, or delayed phosphors, which are called dopants, thereby reducing the driving voltage and improving luminous efficiency.

[0068] Therefore, the arylamine compounds of the present invention can be effectively used as materials for hole injection layers, hole transport layers, electron blocking layers or light-emitting layers of organic EL devices, and can improve the luminous efficiency, driving voltage and durability of conventional organic EL devices.

[0069] Furthermore, the arylamine compounds of the present invention can be used not only for organic EL elements, but also for electronic devices such as electrophotographic photosensitive elements, image sensors, photoelectric conversion elements, and solar cells. Attached Figure Description

[0070] Figure 1 The figure shows preferred examples of compounds (1) to (12) as arylamine compounds represented by general formula (1).

[0071] Figure 2 The figure shows preferred examples of compounds (13) to (24) as arylamine compounds represented by general formula (1).

[0072] Figure 3 The figure shows preferred examples of compounds (25) to (36) as arylamine compounds represented by general formula (1).

[0073] Figure 4 The figure shows preferred examples of compounds (37) to (48) as arylamine compounds represented by general formula (1).

[0074] Figure 5 The figure shows preferred examples of compounds (49) to (60) as arylamine compounds represented by general formula (1).

[0075] Figure 6 The figure shows preferred examples of compounds (61) to (75) as arylamine compounds represented by general formula (1).

[0076] Figure 7 The figure shows preferred examples of compounds (76) to (87) as arylamine compounds represented by general formula (1).

[0077] Figure 8 The figure shows preferred examples of compounds (88) to (99) as arylamine compounds represented by general formula (1).

[0078] Figure 9 The figure shows preferred examples of compounds (100) to (111) as arylamine compounds represented by general formula (1).

[0079] Figure 10 The figure shows preferred examples of compounds (112) to (123) as arylamine compounds represented by general formula (1).

[0080] Figure 11The figure shows preferred examples of compounds (124) to (135) as arylamine compounds represented by general formula (1).

[0081] Figure 12 The figure shows preferred examples of compounds (136) to (146) as arylamine compounds represented by general formula (1).

[0082] Figure 13 The figure shows preferred examples of compounds (147) to (158) as arylamine compounds represented by general formula (1).

[0083] Figure 14 The figure shows preferred examples of compounds (159) to (170) as arylamine compounds represented by general formula (1).

[0084] Figure 15 The figure shows preferred examples of compounds (171) to (182) as arylamine compounds represented by general formula (1).

[0085] Figure 16 The figure shows preferred examples of compounds (183) to (185) as arylamine compounds represented by general formula (1).

[0086] Figure 17 This is a diagram showing the configuration of the organic EL elements in Examples 17-21 and Comparative Examples 1-2. Detailed Implementation

[0087] The arylamine compounds of the present invention are novel compounds, but these compounds can be synthesized by methods known in themselves (e.g., see Patent Document 5).

[0088] Specific examples of preferred compounds among the arylamine compounds represented by the above general formula (1) suitable for organic EL elements of the present invention are shown in Figures 1 to 16 However, it is not limited to these compounds.

[0089] The purification of arylamine compounds represented by general formula (1) can be carried out using known methods such as column chromatography, adsorption purification based on silica gel, activated carbon, activated clay, etc., solvent-based recrystallization, crystallization, and sublimation purification. The compounds can be identified by NMR analysis. Physical properties include melting point, glass transition temperature (Tg), and work function. Melting point is an indicator of vapor deposition properties, glass transition temperature (Tg) is an indicator of film stability, and work function is an indicator of hole injection, hole transport, or electron blocking properties.

[0090] Melting point and glass transition temperature (Tg) can be determined, for example, by using powder and utilizing a high-sensitivity differential scanning calorimeter (Bruker AXS, DSC3100SA).

[0091] The work function can be determined, for example, by fabricating a 100 nm thin film on an ITO substrate and using an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS-202).

[0092] Examples of the organic EL element structure of the present invention include: a structure comprising, in sequence on a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode; a structure having an electron blocking layer between the hole transport layer and the light-emitting layer; and a structure having a hole blocking layer between the light-emitting layer and the electron transport layer. In these multilayer structures, a single organic layer can perform multiple functions; for example, a single organic layer can function as both a hole injection layer and a hole transport layer, or as both an electron injection layer and an electron transport layer. Furthermore, it is possible to construct a structure in which two or more organic layers with the same function are stacked, and it is also possible to construct a structure in which two hole transport layers are stacked, two light-emitting layers are stacked, or two electron transport layers are stacked, etc.

[0093] As the anode of the organic EL element of the present invention, electrode materials with high work functions such as ITO and gold can be used.

[0094] As materials for the hole injection layer of the organic EL element of the present invention, porphyrin compounds represented by copper phthalocyanine, starburst-type triphenylamine derivatives, arylamine compounds having two or more triphenylamine or carbazole structures in the molecule, each having a structure linked by a single bond or a divalent group without heteroatoms, acceptor heterocyclic compounds such as hexacyanoazabenzophenanthrene, and coating-type polymeric materials can be used. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0095] In addition to the arylamine compounds of the present invention, materials for the hole injection layer and hole transport layer of the organic EL element of the present invention can also be used, such as benzidine derivatives such as N,N'-diphenyl-N,N'-bis(m-tolyl)benzidine (TPD), N,N'-diphenyl-N,N'-bis(α-naphthyl)benzidine (NPD), and N,N,N',N'-tetraphenylbenzidine, 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), and arylamine compounds having two or more triphenylamine or carbazole structures in their molecules and each having a structure formed by single bonds or divalent groups without heteroatoms. These materials can be formed into films individually or mixed together, and each can be used as a monolayer. Furthermore, the film can be a stacked structure of layers formed by forming films of these materials individually, a stacked structure of layers formed by mixing these materials, or a stacked structure of layers formed by forming films of these materials individually and layers formed by mixing these materials. In addition, coating-type polymers such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrene sulfonate) (PSS) can be used as materials for the hole injection / transport layer. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0096] In addition, in the hole injection layer or hole transport layer, substances that are further p-doped with antimony hexachloride tribromoaniline, axial alkene derivatives (for example, see Patent Document 6), etc., which are commonly used in these layers, or polymeric compounds whose partial structures have the structure of benzidine derivatives such as TPD, can be used.

[0097] In addition to the arylamine compounds of the present invention, the electron blocking layer of the organic EL element of the present invention can also be made of carbazole derivatives such as 4,4',4”-tris(N-carbazole-9-yl)triphenylamine (TCTA), 9,9-bis[4-(carbazole-9-yl)phenyl]fluorene, 1,3-bis(carbazole-9-yl)phenyl (mCP), and 2,2-bis(4-carbazole-9-ylphenyl)adamantane (Ad-Cz), as well as 9-[4-(carbazole-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H Compounds with electron-blocking properties, such as fluorene and compounds with triphenylsilyl and triarylamine structures, can be formed into films individually or in mixtures, each usable as a monolayer. Alternatively, films can be formed as stacks of layers formed individually, layers formed by mixing these materials, or layers formed by combining individual materials with layers formed by mixing various materials. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0098] In addition to the arylamine compounds of the present invention, materials for the light-emitting layer of the organic EL element of the present invention can also be used, such as metal complexes of quinolinol derivatives, primarily tris(8-hydroxyquinoline)aluminum (Alq3), various metal complexes, anthracene derivatives, bis(styrene)benzene derivatives, pyrene derivatives, oxazole derivatives, poly(p-phenylene)ethylene derivatives, etc. Furthermore, the light-emitting layer can be composed of a host material and a dopant material. Anthracene derivatives are preferably used as the host material; however, in addition to the aforementioned light-emitting materials, primarily the arylamine compounds of the present invention, heterocyclic compounds with a partial structure having an indole ring as a fused ring, heterocyclic compounds with a partial structure having a carbazole ring as a fused ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives, etc., can also be used. Furthermore, dopant materials can include quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, and aminostyrene derivatives, etc. These materials can be formed into films individually or in mixtures, and each can be used as a monolayer. Alternatively, it can be a stacked structure of layers formed by individually depositing these materials, a stacked structure of layers formed by mixing these materials, or a stacked structure of layers formed by individually depositing these materials and layers formed by mixing these materials. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0099] Furthermore, phosphorescent materials can also be used as luminescent materials. Phosphorescent materials can be metal complexes of iridium, platinum, etc. Examples include green phosphorescent materials such as Ir(ppy)3, blue phosphorescent materials such as Firpic and Fir6, and red phosphorescent materials such as Btp2Ir(acac). Regarding the host material, in addition to carbazole derivatives such as 4,4'-bis(N-carbazolyl)biphenyl (CBP), TCTA, and mCP, arylamine compounds of the present invention can be used as host materials for hole injection / transport. Examples of host materials for electron transport include p-bis(triphenylsilyl)benzene (UGH2) and 2,2',2”-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI). By using such materials, high-performance organic EL devices can be fabricated.

[0100] Regarding the doping of phosphorescent luminescent materials into the host material, in order to avoid concentration quenching, it is preferable to dope the entire luminescent layer in the range of 1 to 30% by weight through co-evaporation.

[0101] In addition, materials with delayed fluorescence, such as CDCB derivatives of PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, can also be used as luminescent materials (see, for example, Non-Patent Document 3). These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0102] As materials for the hole-blocking layer of the organic EL element of the present invention, compounds with hole-blocking properties such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of quinolinol derivatives like bis(2-methyl-8-hydroxyquinoline)-4-(phenylphenol)aluminum (BAAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives can be used. These materials can also serve as electron transport layer materials. These materials can be formed into films individually or in combination, and each can be used as a monolayer. Furthermore, the structures can be stacked between layers formed by individually forming these materials, stacked between layers formed by mixing these materials, or stacked between layers formed by individually forming these materials and layers formed by mixing these materials. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0103] Materials used as the electron transport layer of the organic EL element of this invention include metal complexes of quinolinol derivatives, primarily 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, pyridinodole derivatives, phenanthroline derivatives, and silicone derivatives. These materials can be formed individually or in combination, and each can be used as a monolayer. Furthermore, the layers can be stacked as individual films, as well as as mixed films, or as a combination of individual and mixed films. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0104] As materials for the electron injection layer of the organic EL element of the present invention, 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 alumina, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. The electron injection layer can be omitted depending on the preferred selection of the electron transport layer and the cathode.

[0105] Furthermore, in the electron injection layer and the electron transport layer, a material that is further N-doped with metals such as cesium can be used to further N-dope the material commonly used in this layer.

[0106] As the cathode of the organic EL element of the present invention, metals with low work function such as aluminum, and alloys with even lower work function such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-magnesium alloys can be used as electrode materials.

[0107] Example

[0108] The embodiments of the present invention will be described in more detail below. However, the present invention is not limited to the following embodiments as long as it does not depart from the spirit of the present invention.

[0109] [Example 1]

[0110] <Synthesis of biphenyl-4-yl-phenyl-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (2))>

[0111] 49.0 g of 4'-iodo-[1,1':2',1”]terphenyl, 55.3 g of biphenyl-4-yl-phenyl-amino-4-phenylboronic acid, 4.0 g of tetra(triphenylphosphine)palladium(0), and 28.5 g of potassium carbonate were added to the reaction vessel and stirred under reflux overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation, and the crude product was concentrated to obtain the crude product. The crude product was purified by column chromatography (support: silica gel, eluent: toluene / n-heptane) to obtain 65.7 g of pale yellow powder of biphenyl-4-yl-phenyl-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (2)) (yield: 86.9%).

[0112] [Chemical Formula 2]

[0113]

[0114] [Example 2]

[0115] <Synthesis of biphenyl-4-yl-{4-(naphth-2-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (33))>

[0116] 14.7 g of biphenyl-4-yl-{4-(naphthyl-2-yl)-phenyl}-phenylamine was added to a reaction vessel and stirred under ice-cold conditions in dichloromethane solvent. Then, 5.9 g of N-bromosuccinic imide was added, and the mixture was stirred overnight at room temperature. After the reaction was complete, H₂O was added to the system, and the organic layer was extracted by extraction and separation. The crude product was then concentrated to obtain the crude product. The crude product was purified by recrystallization using acetone solvent to obtain 16.7 g of a white powder of biphenyl-4-yl-(4-bromophenyl)-{4-(naphthyl-2-yl)phenyl}-amine (yield: 96.6%).

[0117] [Chemical Formula 3]

[0118]

[0119] Next, 9.0 g of biphenyl-4-yl-(4-bromophenyl)-{4-(naphth-2-yl)phenyl}-amine, 6.7 g of 4,4,5,5-tetramethyl-2-[1,1':2',1]terphenyl-4'-yl-[1,3,2]dioxaborane, 0.5 g of tetra(triphenylphosphine)palladium(0), and 3.1 g of potassium carbonate were added to the reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation, followed by concentration to obtain the crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain a white powder of biphenyl-4-yl-{4-(naphth-2-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (33)): 7.2 g (yield: 62.3%).

[0120] [Chemical Formula 4]

[0121]

[0122] The structure of the obtained white powder was identified using NMR.

[0123] use 1 The following 37 hydrogen signals were detected by H-NMR (CDCl3).

[0124] δ(ppm)=8.07(1H), 7.93(2H), 7.89(1H), 7.79(1H), 7.70(3H), 7.69(1H) , 7.65(2H), 7.63(2H), 7.58(2H), 7.52(3H), 7.47(2H), 7.39-7.18(17H).

[0125] [Example 3]

[0126] <Synthesis of biphenyl-4-yl-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-([1,1':4',1”]terphenyl-4”-yl)-amine (compound (34))>

[0127] 9.0 g of biphenyl-4-yl-phenyl-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (2)) was added to a reaction vessel and stirred under ice-cold conditions in dichloromethane solvent. Then, 21.0 g of N-bromosuccinic imide was added and stirred overnight at room temperature. After the reaction was completed, H2O was added to the system, and the organic layer was extracted by extraction and separation. The crude product was then concentrated to obtain the crude product. The crude product was purified by crystallization using a mixed solvent of acetone / n-heptane to obtain 64.0 g of white powder of biphenyl-4-yl-(4-bromophenyl)-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (yield: 85.4%).

[0128] [Chemical Formula 5]

[0129]

[0130] Next, 9.0 g of biphenyl-4-yl-(4-bromophenyl)-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine, 3.1 g of 4-biphenylboronic acid, 0.4 g of tetrakis(triphenylphosphine)palladium(0), and 2.6 g of potassium carbonate were added to the reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation, and concentrated to obtain the crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 9.5 g of white powder of biphenyl-4-yl-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-([1,1':4',1”]terphenyl-4”-yl)-amine (compound (34)) (yield: 94.5%).

[0131] [Chemical Formula 6]

[0132]

[0133] The structure of the obtained white powder was identified using NMR.

[0134] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0135] δ(ppm)=7.71(2H), 7.70(4H), 7.66(3H), 7.62(3H), 7.59(2H), 7.56(1H), 7.5 3(1H), 7.48(4H), 7.39(1H), 7.35(1H), 7.30(3H), 7.28(5H), 7.27-7.19(9H).

[0136] [Example 4]

[0137] <Synthesis of biphenyl-4-yl-{4-(phenanthrene-9-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (40))>

[0138] 9.0 g of biphenyl-4-yl-(4-bromophenyl)-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine, 3.5 g of 9-phenanthreneboronic acid, 0.4 g of tetra(triphenylphosphine)palladium(0), and 2.6 g of potassium carbonate were added to a reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation, and the crude product was concentrated to obtain the crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 8.4 g of white powder of biphenyl-4-yl-{4-(phenanthrene-9-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (40)) (yield: 80.8%).

[0139] [Chemical Formula 7]

[0140]

[0141] The structure of the obtained white powder was identified using NMR.

[0142] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0143] δ(ppm)=8.79(1H), 8.73(1H), 8.08(1H), 7.91(1H), 7.74(1H), 7.73-7.54(12H), 7.51(1H), 7.48(2H), 7.44(2H), 7.33(7H), 7.25-7.16(10H).

[0144] [Example 5]

[0145] <Synthesis of {4-(naphth-1-yl)-phenyl}-{4-(naphth-2-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (43))>

[0146] (4-Bromophenyl)-{4-(naphth-1-yl)-phenyl}-{4-(naphth-2-yl)-phenyl}-amine: 9.0 g, 4,4,5,5-tetramethyl-2-[1,1':2',1]terphenyl-4'-yl-[1,3,2]dioxaborane: 6.1 g, tetra(triphenylphosphine)palladium(0): 0.5 g, potassium carbonate: 2.8 g were added to a reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation, followed by concentration to obtain the crude product. The crude product was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain a white powder of {4-(naphth-1-yl)-phenyl}-{4-(naphth-2-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (43)): 9.3 g (yield: 82.1%).

[0147] [Chemical Formula 8]

[0148]

[0149] The structure of the obtained white powder was identified using NMR.

[0150] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0151] δ(ppm)=8.05(2H), 7.91(3H), 7.86(2H), 7.78(1H), 7.70(2H), 7.68(2H), 7.65(2H), 7.57-7.42(9H), 7.36(3H), 7.33(3H), 7.25-7.16(10H).

[0152] [Example 6]

[0153] <Synthesis of bis{4-(naphthyl-1-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (45))>

[0154] 9.0 g of bis{4-(naphthyl-2-yl)phenyl}-(4-bromophenyl)-amine, 6.1 g of 4,4,5,5-tetramethyl-2-[1,1':2',1]terphenyl-4'-yl-[1,3,2]dioxaborane, 0.5 g of tetra(triphenylphosphine)palladium(0), and 2.8 g of potassium carbonate were added to a reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation. The crude product was then concentrated. The crude product was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain a white powder of bis{4-(naphthyl-1-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (45)): 7.6 g (yield: 67.1%).

[0155] [Chemical Formula 9]

[0156]

[0157] The structure of the obtained white powder was identified using NMR.

[0158] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0159] δ (ppm)=8.07(2H), 7.92(2H), 7.86(2H), 7.68(2H), 7.66(1H), 7.65(1H), 7.57-7.44(13H), 7.40-7.34(6H), 7.25-7.17(10H).

[0160] [Example 7]

[0161] <Synthesis of biphenyl-4-yl-{4'-(naphth-1-yl)-biphenyl-4-yl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (55))>

[0162] Add 9.0 g of biphenyl-4-yl-(4-bromophenyl)-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine, 3.9 g of 4-(naphthyl-1-yl)phenylboronic acid, 0.4 g of tetrakis(triphenylphosphine)palladium(0), and 2.6 g of potassium carbonate to a reaction vessel, and reflux and stir overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, add toluene / H2O to the system, extract the organic layer by extraction and separation, and concentrate to obtain the crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain a white powder of biphenyl-4-yl-{4'-(naphth-1-yl)-biphenyl-4-yl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (55)): 9.6 g (yield: 89.1%).

[0163] [Chemical Formula 10]

[0164]

[0165] The structure of the obtained white powder was identified using NMR.

[0166] use 1 H-NMR (CDCl3) detected the following 41 hydrogen signals.

[0167] δ(ppm)=7.99(1H), 7.92(1H), 7.88(1H), 7.73(2H), 7.67(1H), 7.66-7.59(7H), 7.56(5H), 7 .53(1H), 7.51(1H), 7.49(1H), 7.47(2H), 7.43(2H), 7.34(1H), 7.29(6H), 7.25-7.16(9H).

[0168] [Example 8]

[0169] <Synthesis of biphenyl-4-yl-{3'-(naphthyl-1-yl)-biphenyl-4-yl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (58))>

[0170] Add 9.0 g of biphenyl-4-yl-(4-bromophenyl)-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine, 3.9 g of 3-(naphthyl-1-yl)phenylboronic acid, 0.4 g of tetra(triphenylphosphine)palladium(0), and 2.6 g of potassium carbonate to a reaction vessel and reflux and stir overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, add toluene / H2O to the system, extract the organic layer by extraction and separation, and concentrate to obtain the crude product. The crude product was purified by crystallization using a mixed solvent of acetone and methanol to obtain a white powder of biphenyl-4-yl-{3'-(naphth-1-yl)-biphenyl-4-yl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (58)): 10.4 g (yield: 96.6%).

[0171] [Chemical Formula 11]

[0172]

[0173] The structure of the obtained white powder was identified using NMR.

[0174] use 1 H-NMR (CDCl3) detected the following 41 hydrogen signals.

[0175] δ(ppm)=7.97(1H), 7.92(1H), 7.88(1H), 7.74(1H), 7.67(1H), 7.65(1H), 7.64 (1H), 7.60(6H), 7.57-7.49(6H), 7.49-7.40(6H), 7.32(1H), 7.28-7.14(15H).

[0176] [Example 9]

[0177] <Synthesis of biphenyl-4-yl-{1'-(naphthyl-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-{4-(naphthyl-2-yl)-phenyl}-amine (compound (93))>

[0178] 25.0 g of 1-(5-chloro-biphenyl-2-yl)-naphthalene, 32.4 g of biphenyl-4-yl-{4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborane-2-yl)-phenyl}-amine, 3.6 g of tris(dibenzylacetone)dipalladium(O), 4.5 g of tri-cyclohexylphosphine, and 50.6 g of tripotassium phosphate were added to a reaction vessel and refluxed and stirred overnight in a 1,4-dioxane / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation. The crude product was then concentrated. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 33.8 g of yellowish-brown powder of biphenyl-4-yl-{1'-(naphth-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-amine (yield: 81.3%).

[0179] [Chemical Formula 12]

[0180]

[0181] Next, 8.0 g of biphenyl-4-yl-{1'-(naphthyl-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-amine, 4.8 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of tris(dibenzylacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 1.8 g of sodium tert-butoxyl were added to the reaction vessel and stirred under reflux in toluene for 5 hours. After natural cooling, the mixture was filtered, and the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 8.8 g of pale yellow powder (yield: 79.4%) of biphenyl-4-yl-{1'-(naphth-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-{4-(naphth-2-yl)-phenyl}-amine (compound (93)).

[0182] [Chemical Formula 13]

[0183]

[0184] The structure of the obtained pale yellow powder was identified using NMR.

[0185] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0186] δ(ppm)=8.08(1H), 7.94(2H), 7.90(1H), 7.85(1H), 7.80(3H), 7.77(1H), 7.71(5H) , 7.65(2H), 7.59(2H), 7.53(2H), 7.47(4H), 7.42-7.23(10H), 7.16(2H), 7.08(3H).

[0187] [Example 10]

[0188] <Synthesis of biphenyl-4-yl-{1'-(naphth-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-([1,1':4',1”]terphenyl-4”-yl)-amine (compound (94))>

[0189] Add 8.0 g of biphenyl-4-yl-{1'-(naphthyl-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-amine, 5.2 g of 4-bromo-[1,1':4',1”]terphenyl, 0.1 g of tris(dibenzylacetone)dipalladium(O), 0.2 g of tri-tert-butylphosphine, and 1.8 g of sodium tert-butoxyl to a reaction vessel, and reflux and stir in toluene for 4 hours. After natural cooling, The solution was filtered, and the filtrate was concentrated to obtain a crude product. The crude product was purified by recrystallization using acetone solvent to obtain a pale yellow powder of biphenyl-4-yl-{1'-(naphth-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-([1,1':4',1”]terphenyl-4”-yl)-amine (compound (94)): 10.4 g (yield: 90.5%).

[0190] [Chemical Formula 14]

[0191]

[0192] The structure of the obtained pale yellow powder was identified using NMR.

[0193] use 1 H-NMR (CDCl3) detected the following 41 hydrogen signals.

[0194] δ(ppm)=7.82(1H), 7.78(1H), 7.75(2H), 7.71-7.63(9H), 7.61(4H), 7.55(2H), 7.50(1H) ), 7.46(2H), 7.42(3H), 7.36(4H), 7.29(6H), 7.22(1H), 7.13(1H), 7.11(1H), 7.04(3H).

[0195] [Example 11]

[0196] <Synthesis of biphenyl-4-yl-{1'-(naphthyl-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-{4-(phenanthrene-9-yl)-phenyl}-amine (compound (96))>

[0197] The following ingredients were added to a reaction vessel: 8.0 g of biphenyl-4-yl-{1'-(naphthyl-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-amine, 5.6 g of 9-(4-bromo-phenyl)-phenanthrene, 0.1 g of tris(dibenzylacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 1.8 g of sodium tert-butoxyl. The mixture was refluxed and stirred in toluene for 4 hours. After natural cooling, the mixture was filtered, and the filtrate was concentrated to obtain the crude product. The crude product was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain a white powder of biphenyl-4-yl-{1'-(naphth-1-yl)-[1,2':4',1”]terphenyl-4”-yl}-{4-(phenanthrene-9-yl)-phenyl}-amine (compound (96)): 8.1 g (yield: 68.4%).

[0198] [Chemical Formula 15]

[0199]

[0200] The structure of the obtained white powder was identified using NMR.

[0201] use 1 H-NMR (CDCl3) detected the following 41 hydrogen signals.

[0202] δ(ppm)=8.79(1H), 8.73(1H), 8.08(1H), 7.91(1H), 7.82(1H), 7.79(1H), 7.75(3H), 7.70(3H) , 7.67(2H), 7.62(3H), 7.58(3H), 7.50(3H), 7.47-7.30(12H), 7.22(1H), 7.13(2H), 7.04(3H).

[0203] [Example 12]

[0204] <Synthesis of {4-(naphthyl-1-yl)-phenyl}-phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (compound (148))>

[0205] 20.0 g of 4'-iodo-[1,1':2',1”]terphenyl, 21.9 g of phenyl-{4'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborane-2-yl)-biphenyl-4-yl}-amine, 0.7 g of tetra(triphenylphosphine)palladium(0), and 11.6 g of potassium carbonate were added to a reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, methanol / H2O was added to the system, and the solid was extracted by filtration to obtain the crude product. The crude product was purified by crystallization using a monochlorobenzene / acetone mixed solvent to obtain 23.3 g of light red powder of phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (yield: 87.6%).

[0206] [Chemical Formula 16]

[0207]

[0208] Next, 8.0 g of phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine, 5.3 g of 1-(4-bromo-phenyl)-naphthalene, 0.2 g of tris(dibenzylacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 2.0 g of sodium tert-butoxyl were added to the reaction vessel and stirred under reflux in toluene for 4 hours. After natural cooling, the mixture was filtered, and the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 10.9 g of a light red powder of {4-(naphthyl-1-yl)-phenyl}-phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (compound (148)) (yield: 95.4%).

[0209] [Chemical Formula 17]

[0210]

[0211] The structure of the obtained pale red powder was identified using NMR.

[0212] use 1 The following 37 hydrogen signals were detected by H-NMR (CDCl3).

[0213] δ(ppm)=8.06(1H), 7.94(1H), 7.87(1H), 7.76(3H), 7.73(2H), 7.62(2H) , 7.55(2H), 7.50(2H), 7.44(2H), 7.37(2H), 7.32-7.19(18H), 7.12(1H).

[0214] [Example 13]

[0215] <Synthesis of {4-(naphthyl-2-yl)-phenyl}-phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (compound (149))>

[0216] 7.5 g of phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine, 4.9 g of 2-(4-bromo-phenyl)-naphthalene, 0.2 g of tris(dibenzylacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 1.8 g of sodium tert-butoxyl were added to a reaction vessel and stirred under reflux in toluene for 4 hours. After natural 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 10.4 g of white powder of {4-(naphthyl-2-yl)-phenyl}-phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (compound (149)) (yield: 97.2%).

[0217] [Chemical Formula 18]

[0218]

[0219] The structure of the obtained white powder was identified using NMR.

[0220] use 1 The following 37 hydrogen signals were detected by H-NMR (CDCl3).

[0221] δ(ppm)=8.03(1H), 7.90(2H), 7.86(1H), 7.76(3H), 7.71(3H), 7.69(1H), 7.65(2H) , 7.58(2H), 7.53(1H), 7.49(1H), 7.47(1H), 7.32(2H), 7.25-7.16(16H), 7.09(1H).

[0222] [Example 14]

[0223] <Synthesis of {4-(phenanthrene-9-yl)-phenyl}-phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (compound (150))>

[0224] 7.5 g of phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine, 5.8 g of 9-(4-bromo-phenyl)-phenanthrene, 0.2 g of tris(dibenzylacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 1.8 g of sodium tert-butoxyl were added to a reaction vessel and stirred under reflux in toluene for 5 hours. After natural 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 11.0 g of a white powder of {4-(phenanthrene-9-yl)-phenyl}-phenyl-(2'-phenyl-[1,1':4',1”:4”,1”']tetraphenyl-4”'-yl)-amine (compound (150)) (yield: 95.7%).

[0225] [Chemical Formula 19]

[0226]

[0227] The structure of the obtained white powder was identified using NMR.

[0228] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0229] δ(ppm)=8.79(1H), 8.73(1H), 8.07(1H), 7.90(1H), 7.78-7.56(13H), 7.53(1H), 7.47(2H), 7.25-7.16(9H), 7.38-7.26(9H), 7.10(1H).

[0230] [Example 15]

[0231] <Synthesis of bis{4-(naphth-2-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (44))>

[0232] 12.0 g of bis{4-(naphthyl-2-yl)-phenyl}-(3,4-dichloro-biphenyl-4'-yl)-amine, 6.8 g of phenylboronic acid, 0.9 g of tris(dibenzylacetone)dipalladium(0), 1.1 g of tri-cyclohexylphosphine, and 19.8 g of tripotassium phosphate were added to a reaction vessel and refluxed and stirred overnight in a 1,4-dioxane / H2O mixed solvent. After natural cooling, the mixture was filtered, and the filtrate was concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: toluene / n-heptane) to obtain 11.6 g of white powder of bis{4-(naphthyl-2-yl)-phenyl}-(2'-phenyl-[1,1':4',1”]terphenyl-4”-yl)-amine (compound (44)) (yield: 85.5%).

[0233] [Chemical Formula 20]

[0234]

[0235] The structure of the obtained white powder was identified using NMR.

[0236] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl3).

[0237] δ(ppm)=8.05(2H), 7.90(4H), 7.86(2H), 7.77(2H), 7.68(4H), 7.67(2H), 7.63(2H), 7.49(5H), 7.31(6H), 7.25-7.14(10H).

[0238] [Example 16]

[0239] <Synthesis of biphenyl-4-yl-{1'-(naphthyl-2-yl)-[1,2':4',1”]terphenyl-4”-yl}-phenyl-amine (compound (103))>

[0240] 25.0 g of 2-chloro-4-bromo-iodobenzene, 14.2 g of 2-naphthylboronic acid, 1.8 g of tetrakis(triphenylphosphine)palladium(O), and 21.8 g of potassium carbonate were added to a reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, toluene / H2O was added to the system, and the organic layer was extracted by extraction and separation. The crude product was then concentrated to obtain the crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-heptane) to obtain 18.1 g of 3-chloro-4-(naphthyl-2-yl)-bromobenzene white powder (yield: 72.5%).

[0241] [Chemical Formula 21]

[0242]

[0243] Next, 9.4 g of 3-chloro-4-(naphth-2-yl)-bromobenzene, 9.0 g of 4-(biphenyl-4-yl-phenyl-amino)-phenylboronic acid, 0.6 g of tetra(triphenylphosphine)palladium(O), and 7.1 g of potassium carbonate were added to the reaction vessel and refluxed and stirred overnight in a toluene / EtOH / H2O mixed solvent. After natural cooling, methanol was added to the system, and the solid was extracted by filtration to obtain the crude product. The crude product was purified by crystallization using an MCB / methanol mixed solvent to obtain 13.4 g of a white powder of biphenyl-4-yl-{3-chloro-4-(naphth-2-yl)-biphenyl-4'-yl}-phenyl-amine (yield: 93.0%).

[0244] [Chemical Formula 22]

[0245]

[0246] Next, 13.5 g of biphenyl-4-yl-{3-chloro-4-(naphthyl-2-yl)-biphenyl-4'-yl}-phenyl-amine, 3.1 g of phenylboronic acid, 0.7 g of tris(dibenzylacetone)dipalladium(0), 0.7 g of tri-cyclohexylphosphine, and 10.3 g of tripotassium phosphate were added to the reaction vessel and refluxed and stirred overnight in a 1,4-dioxane / H2O mixed solvent. After natural cooling, methanol was added to the system, and the solid was extracted by filtration to obtain the crude product. The crude product was purified by recrystallization using toluene solvent to obtain 10.0 g of white powder of biphenyl-4-yl-{1'-(naphthyl-2-yl)-[1,2':4',1”]terphenyl-4”-yl}-phenyl-amine (compound (103)) (yield: 68.9%).

[0247] [Chemical Formula 23]

[0248]

[0249] The structure of the obtained white powder was identified using NMR.

[0250] use 1 The following 33 hydrogen signals were detected by H-NMR (DMSO-d6).

[0251] δ(ppm)=7.85(3H), 7.78(3H), 7.70(2H), 7.64(5H), 7.48(4H), 7.37(3H), 7.23(5H), 7.20-7.06(8H).

[0252] For the compounds synthesized in Examples 2-16, the melting point and glass transition temperature were determined using a high-sensitivity differential scanning calorimeter (Bruker AXS, DSC3100SA). Furthermore, using these compounds, 100 nm thick vapor-deposited films were fabricated on ITO substrates, and the work function was measured using an ionization potential measuring device (Sumitomo Heavy Industries, Ltd., PYS-202). The results are summarized in Table 1.

[0253] [Table 1]

[0254]

[0255] The compounds synthesized in Examples 2-16 have glass transition temperatures above 100°C and exhibit stable thin film states.

[0256] Compared to the work function of 5.4 eV of common hole transport materials such as NPD and TPD, the compounds synthesized in Examples 2-16 show more suitable energy levels and have good hole transport capabilities.

[0257] [Example 17]

[0258] <Fabrication and Evaluation of Organic EL Components>

[0259] like Figure 17 As shown, a reflective ITO electrode is pre-formed on a glass substrate 1 as a transparent anode 2, and a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a capping layer 10 are sequentially deposited on it, thereby fabricating an organic EL device.

[0260] Specifically, a glass substrate 1, consisting of a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film, is ultrasonically cleaned in isopropanol for 20 minutes and then dried on a hot plate heated to 250°C for 10 minutes. Afterward, it undergoes a 2-minute UV ozone treatment. Finally, the ITO-coated glass substrate is mounted in a vacuum evaporation machine, and the pressure is reduced to below 0.001 Pa.

[0261] Next, the electron acceptor (Acceptor-1) and the compound (HTM-1) with the following structure are subjected to binary vapor deposition at a vapor deposition rate of Acceptor-1:HTM-1 = 3:97, so as to form a hole injection layer 3 covering the transparent anode 2 with a film thickness of 10 nm.

[0262] On the hole injection layer 3, a hole transport layer 4 is formed by using a compound (HTM-1) with the following structural formula to make the film thickness 140 nm.

[0263] On the hole transport layer 4, the compound (33) of Example 2 is used to form an electron blocking layer 5 such that the film thickness is 5 nm.

[0264] On the electron blocking layer 5, a light-emitting layer 6 is formed by binary vapor deposition of a compound (EMD-1) with the following structural formula and a compound (EMH-1) with the following structural formula at a vapor deposition rate ratio of EMD-1:EMH-1 = 5:95, so that the film thickness is 20 nm.

[0265] On the light-emitting layer 6, the following compounds (ETM-1) and (ETM-2) are subjected to binary evaporation at a evaporation rate ratio of ETM-1:ETM-2 = 50:50 to form an electron transport layer 7 with a film thickness of 30 nm.

[0266] On the electron transport layer 7, lithium fluoride is used to form an electron injection layer 8 in such a way that the film thickness is 1 nm.

[0267] On the electron injection layer 8, a magnesium-silver alloy is formed to create a cathode 9 such that the film thickness is 12 nm.

[0268] Finally, the following compound (CPL-1) is used to form a capping layer 10 with a film thickness of 60 nm.

[0269] The characteristics of the fabricated organic EL element were measured in the atmosphere at room temperature.

[0270] The results of measuring the light emission characteristics of the fabricated organic EL element after applying a DC voltage are summarized in Table 2.

[0271] [Chemical Formula 24]

[0272]

[0273] [Chemical Formula 25]

[0274]

[0275] [Chemical Formula 26]

[0276]

[0277] [Example 18]

[0278] In Example 17, compound (93) of Example 9 was used instead of compound (33) of Example 2 as the material for the electron blocking layer 5. Otherwise, an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescence characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0279] [Example 19]

[0280] In Example 17, compound (148) of Example 12 was used instead of compound (33) of Example 2 as the material for the electron blocking layer 5. Otherwise, an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescence characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0281] [Example 20]

[0282] In Example 17, compound (44) of Example 15 was used instead of compound (33) of Example 2 as the material for the electron blocking layer 5. Otherwise, an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the light emission characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0283] [Example 21]

[0284] In Example 17, compound (103) of Example 16 was used instead of compound (33) of Example 2 as the material for the electron blocking layer 5. Otherwise, an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the light emission characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0285] [Comparative Example 1]

[0286] For comparison, in Example 17, instead of compound (33) of Example 2, compound (HTM-2) with the following structural formula was used as the material for the electron blocking layer 5 (see, for example, Patent Document 5). Otherwise, an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in air and at room temperature. The results of the measurement of the luminescence characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0287] [Chemical Formula 27]

[0288]

[0289] [Comparative Example 2]

[0290] For comparison, in Example 17, instead of compound (33) of Example 2, compound (HTM-3) with the following structural formula was used as the material for the electron blocking layer 5 (see, for example, Patent Document 5). Otherwise, an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in air and at room temperature. The results of the measurement of the luminescence characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0291] [Chemical Formula 28]

[0292]

[0293] The current density of 10 mA / cm² was measured using the organic EL elements prepared in Examples 17-21 and Comparative Examples 1 and 2. 2 The results obtained for voltage, luminous efficiency, power efficiency, and component lifespan at the given current are summarized in Table 2. Regarding component lifespan, the initial luminous brightness (luminance at the start of luminescence) is set to 1000 cd / m². 2 When driven by a constant current, the luminous intensity was measured until it decreased to 950 cd / m². 2 (Equivalent to 95% of the initial brightness set to 100%: decay to 95%).

[0294] [Table 2]

[0295]

[0296] As shown in Table 2, for a current density of 10 mA / cm² 2 Regarding the luminous efficiency at a given current, the organic EL elements of Comparative Examples 1 and 2 have a luminous efficiency of 9.34–9.85 cd / A, while the organic EL elements of Examples 17–21 have a luminous efficiency of 10.04–10.26 cd / A, exhibiting high efficiency. Furthermore, regarding power efficiency, the organic EL elements of Comparative Examples 1 and 2 have a power efficiency of 8.61–9.15 lm / W, while the organic EL elements of Examples 17–21 have a power efficiency of 9.56–9.66 lm / W, also exhibiting high efficiency. Moreover, regarding device lifetime (95% degradation), the organic EL elements of Comparative Examples 1 and 2 have a lifetime of 223–306 hours, while the organic EL elements of Examples 17–21 have a lifetime of 425–512 hours, representing long lifetime.

[0297] The results above clearly show that the organic EL element of the present invention, due to the use of arylamine compounds with high hole mobility and excellent electron blocking ability, can achieve high luminous efficiency and long lifetime compared with conventional organic EL elements.

[0298] The organic EL element of the present invention, which uses an arylamine compound with a specific structure, can improve luminous efficiency and durability, and can be extended to applications such as home appliances and lighting.

[0299] (Explanation of reference numerals in the attached diagram)

[0300] 1: Glass substrate

[0301] 2: Transparent anode

[0302] 3: Hole injection layer

[0303] 4: Hole transport layer

[0304] 5: Electron blocking layer

[0305] 6: Emissive layer

[0306] 7: Electron transport layer

[0307] 8: Electron injection layer

[0308] 9: Cathode

[0309] 10: Capping layer

Claims

1. An arylamine compound, represented by the following general formula (1), [Chemical Formula 1] In the formula, Ar1 represents a substituted phenyl, biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl. The substituents are naphthyl or phenanthrene. Ar2 represents substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene, wherein the substituent is naphthyl or phenanthryl. Furthermore, when Ar2 is phenyl, Ar1 is not phenanthrene. When Ar1 is biphenyl, Ar2 is phenyl or a biphenyl substituted with naphthyl group. Ar3 and Ar4 may be the same or different, and represent substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted carbazole, or substituted or unsubstituted phenanthryl, wherein at least one of Ar3 and Ar4 is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted carbazole. Furthermore, when Ar1 and Ar2 are both naphthyl-substituted phenyl groups, Ar4 is not naphthyl. L represents an unsubstituted phenylene or an unsubstituted biphenylene, wherein when L is an unsubstituted phenylene, and Located at positions 1 and 4 of L, respectively, when L is an unsubstituted biphenylene oxide. and They are located at the 4' and 4' bits of L, respectively. R1 to R3 can be the same or different, and represent either hydrogen or deuterium atoms. n represents an integer from 1 to 2. When n is 2, L can be the same or different from each other. Wherein, the general formula (1) indicates that the arylamine compound is not... .

2. The arylamine compound according to claim 1, wherein, Ar4 in the general formula (1) is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted carbazolyl.

3. The arylamine compound according to claim 1 or 2, wherein, In the general formula (1), n ​​is 1.

4. An organic electroluminescent element having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein, The organic layer contains an arylamine compound as described in any one of claims 1 to 3.

5. The organic electroluminescent element according to claim 4, wherein, The organic layer is a hole transport layer.

6. The organic electroluminescent element according to claim 4, wherein, The organic layer is an electron blocking layer.

7. The organic electroluminescent element according to claim 4, wherein, The organic layer is a hole injection layer.

8. The organic electroluminescent element according to claim 4, wherein, The organic layer is a light-emitting layer.

9. An electronic device comprising an element having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein, The organic layer contains an arylamine compound as described in any one of claims 1 to 3.

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