Arylamine compound, organic electroluminescent element, and electronic device

Abstract

The present application provides an arylamine compound as a material for an organic EL element having high efficiency and durability, which has excellent hole injection and transport properties, excellent electron blocking ability, high stability in a thin film state, and excellent durability. The arylamine compound of the present application is represented by the following general formula (I), wherein Ar 1 and Ar 2 represent an aryl group or a heteroaryl group, L 1 to L 3 represent a single bond, an arylene group, or a heteroarylene group, and A represents a di- or tri-substituted naphthyl group.

Description

Technical Field

[0001] This invention relates to arylamine compounds suitable for organic electroluminescent elements (hereinafter referred to as "organic EL elements") in various display devices, and organic EL elements and electronic devices using the compounds. Background Technology

[0002] Organic EL elements are self-emissive, thus offering superior brightness and visibility compared to liquid crystal elements, enabling clear displays and thus attracting significant research attention. In 1987, CWTang et al. from Eastman Kodak developed a multilayer structure element where various materials performed different functions, making organic EL elements using organic materials practical applications. To date, numerous improvements have been made to facilitate the practical application of organic EL elements, further refining the various functions of the multilayer structure. High efficiency and durability have been achieved by sequentially arranging an anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, and cathode on a substrate.

[0003] In organic electron luminescent devices (ELs), light emission is achieved by the recombination of charges injected from the two electrodes within the light-emitting layer. However, effectively transporting both holes and electrons to the light-emitting layer becomes crucial, requiring a device with excellent carrier balance. Specifically, by using materials with high hole injection capability (supplying holes injected from the anode) and high electron blocking capability (blocking electrons injected from the cathode), the probability of hole-electron recombination within the light-emitting layer can be increased. Furthermore, by confining the excitons generated within the light-emitting layer, high luminous efficiency can be obtained. Therefore, the role of hole transport materials is critical, requiring materials with high hole injection capability, high hole mobility, high electron blocking capability, and high electron durability.

[0004] Furthermore, the heat resistance and amorphous properties of the material are also crucial to the lifespan of components. Specifically, materials with low heat resistance can undergo thermal decomposition even at low temperatures due to the heat generated during component operation, easily leading to material degradation. Materials with low amorphous properties can experience thin-film crystallization even in a short time, resulting in component degradation. Therefore, in addition to high heat resistance, excellent amorphous properties are also required for the materials used.

[0005] To date, N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) and various aromatic amine derivatives have been known as hole transport materials for use in organic EL devices. However, while NPD exhibits good hole transport capabilities, its glass transition temperature (Tg), an indicator of heat resistance, is low at 96°C. Under high-temperature conditions, crystallization can lead to a decrease in device performance (see Non-Patent Literature 1). Furthermore, while some aromatic amine derivatives possess excellent hole mobility, their electron blocking properties are insufficient, allowing some electrons to pass through the emissive layer, thus failing to improve luminous efficiency.

[0006] Therefore, substituted carbazole compounds and arylamine compounds have been proposed as compounds that improve properties such as heat resistance and hole injection capability (see Patent Document 1 and Patent Document 2). However, although the device lifetime and luminous efficiency are improved when these compounds are used in devices with hole injection layers or hole transport layers, it is not sufficient, and further reductions in driving voltage, higher luminous efficiency, and longer device lifetime are required.

[0007] Existing technical documents Patent documents Patent Document 1: Japanese Patent Application Publication No. 2009-076817 Patent Document 2: International Publication No. 2016 / 006629 Patent Document 3: European Patent Application Publication No. 2684932 Patent Document 4: Korean Patent Publication No. 10-2020-0131929 Non-patent literature Non-patent literature 1: Proceedings of the Third Regular Meeting of the Organic EL Symposium, 2006, pp. 13-14 Non-patent literature 2: Chem. Rev., 2016, Vol. 116, pp. 12564-12649 Non-patent literature 3: Appl. Phys. Let., 2011, Vol. 98, No. 8, 083302 Summary of the Invention The present invention aims to provide an arylamine compound as a material for organic EL devices with high efficiency and durability. This arylamine compound exhibits excellent hole injection and transport properties, excellent electron blocking ability, high stability in the thin-film state, and excellent durability. Furthermore, the present invention aims to provide, through the use of this arylamine compound, an organic EL device and electronic device with high luminous efficiency and power efficiency, low emission start voltage and practical driving voltage, and long lifetime.

[0008] To achieve the aforementioned objectives, the inventors focused on the superior hole injection and transport capabilities of aryl amine compounds, as well as the excellent stability and durability of the thin films. Furthermore, they discovered that by introducing a substituted naphthyl group into the aryl amine compound and optimizing the substitution position and number of substituents in this substituted naphthyl group, the material properties can be significantly improved. Additionally, they found that organic EL devices using this aryl amine compound exhibit improved luminous efficiency and electroluminescence efficiency, suppressed luminescence onset voltage and practical driving voltage, and achieved a lifespan exceeding that of existing devices, thus completing the present invention. In short, the present invention has the following main points.

[0009] 1) An arylamine compound, represented by the following general formula (I), wherein, [Chemical Formula 1]

[0010] In general formula (I), Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, L 1 ~L 3 Each of these independently represents a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, where A represents a naphthyl group optionally substituted with a deuterium atom, represented by the following general formula (II). [Chemical Formula 2]

[0011] In general formula (II), R represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, n represents an integer of 2 or 3, and there are multiple Rs that are optionally the same or different, L 3 Same as the definition in general formula (I).

[0012] 2) The arylamine compound according to 1), wherein, In the general formula (II), n is 2.

[0013] 3) The arylamine compound according to 1) or 2), wherein, In the general formula (I), L 1 For a single bond, Ar 1 It is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group, where A is a naphthyl group selected from the group consisting of general formulas (II-A-8) to (II-A-14) that is optionally substituted with a deuterium atom. [Chemical Formula 3]

[0014] L in general formulas (II-A-8) to (II-A-14) 3 And R is the same as the definition in general formula (I) and general formula (II).

[0015] 4) The arylamine compound according to 3), wherein, In the general formula (I), L 3 It is a deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenyl dimethyl, or a deuterated or unsubstituted naphthylene.

[0016] 5) The arylamine compound according to 3) or 4), wherein, In the general formula (I), Ar 1 It is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

[0017] 6) An arylamine compound according to any one of 3) to 5), wherein, In the general formula (II), R is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

[0018] 7) An arylamine compound according to any one of 3) to 6), wherein, In the general formula (II), R is a deuterated or unsubstituted phenyl group.

[0019] 8) The arylamine compound according to 1), wherein, In the general formula (I), A is a naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-7), which is optionally substituted with a deuterium atom. [Chemical Formula 4]

[0020] L in general formulas (II-A-1) to (II-A-7) 3 And R is the same as the definition in general formula (I) and general formula (II).

[0021] 9) The arylamine compound according to 8), wherein, In the general formulas (II-A-1) to (II-A-7), R is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

[0022] 10) The arylamine compound according to 8) or 9), wherein, In general formula (I), L 3 It is a single bond, a deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenyl dimethyl, or a deuterated or unsubstituted naphthylene.

[0023] 11) An arylamine compound according to any one of 8) to 10), wherein, In the general formula (I), Ar 1 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted dibenzofuranyl.

[0024] 12) An arylamine compound according to any one of 8) to 11), wherein, In the general formula (I), A is a naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-3).

[0025] 13) An arylamine compound according to any one of 8) to 12), wherein, In the general formula (I), Ar 1 It is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

[0026] 14) An arylamine compound according to any one of 8) to 13), wherein, In the general formulas (II-A-1) to (II-A-3), R is a deuterated or unsubstituted phenyl group.

[0027] 15) 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 comprises any one of arylamine compounds from 1 to 14).

[0028] 16) The organic electroluminescent element according to 15), wherein, The organic layer containing the arylamine compound is at least one layer selected from the hole injection layer, hole transport layer, electron blocking layer and light-emitting layer.

[0029] 17) An electronic device 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 arylamine compounds from 1 to 14).

[0030] According to the present invention, arylamine compounds with excellent hole injection and transport properties, excellent electron blocking ability, high stability in the thin film state, and excellent durability can be obtained as materials for organic EL devices with high efficiency and durability. Furthermore, according to the present invention, by using this arylamine compound, organic EL devices and electronic devices with high luminous efficiency and power efficiency, low emission start voltage and practical driving voltage, and long lifetime can be obtained.

[0031] The arylamine compounds of this invention exhibit excellent hole injection and transport properties, as well as the stability and durability of the thin films. Therefore, in organic EL devices using these compounds as hole injection and / or hole transport materials, the hole transport efficiency to the light-emitting layer is improved, the luminous efficiency is increased, and the driving voltage is reduced, thereby improving the durability of the device and achieving characteristics of high efficiency, low driving voltage, and long lifespan.

[0032] The arylamine compound of this invention exhibits excellent electron blocking ability, high electron tolerance, and stability even in the thin-film state, demonstrating excellent ability to contain excitons generated within the luminescent layer. Therefore, in organic EL devices using this compound as an electron blocking material, the probability of hole-electron recombination is increased, and thermal deactivation is suppressed. As a result, luminous efficiency is increased, driving voltage is reduced, current tolerance is improved, and thus maximum luminous brightness is increased.

[0033] The arylamine compounds of this invention exhibit excellent hole transport properties and a wide band gap. Therefore, organic EL elements using these compounds as the host material in the luminescent layer achieve improved luminous efficiency by reducing the driving voltage through the loading of dopants (phosphorescent emitters, phosphorescent emitters, delayed phosphors).

[0034] As described above, the arylamine compounds of the present invention are useful as materials for constituting layers selected from the hole injection layer, hole transport layer, electron blocking layer, and light-emitting layer of an organic EL device. Furthermore, organic EL devices using these arylamine compounds can improve the luminous efficiency, driving voltage, and durability of existing organic EL devices. In addition, the arylamine compounds of the present invention can also be used in the field of electronic devices such as electrophotographic photosensors, image sensors, photoelectric conversion elements, and solar cells. Attached Figure Description

[0035] Figure 1 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0036] Figure 2 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0037] Figure 3 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0038] Figure 4 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0039] Figure 5 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0040] Figure 6 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0041] Figure 7 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0042] Figure 8 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0043] Figure 9 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0044] Figure 10 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0045] Figure 11 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0046] Figure 12 This is a diagram showing specific examples of arylamine compounds represented by general formula (I).

[0047] Figure 13 This is a schematic diagram illustrating the structure of an organic EL element according to an embodiment of the present invention. Detailed Implementation

[0048] The embodiments of the present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. It should be noted that, in this specification, the numerical range represented by “~” means the range encompassed by the values ​​recorded before and after “~” as the lower and upper limits. Furthermore, when the numerical range is recorded in stages, the upper and lower limits of each numerical range, as well as the values ​​recorded in the embodiments, can be arbitrarily combined to form new numerical ranges.

[0049] The types of hydrogen isotopes present in the molecules of the compounds used in this invention are not particularly limited; for example, all hydrogen atoms in the molecule may be... 1 H can be partially or entirely... 2H (deuterium). In this specification, the term "substituted or unsubstituted" means that the group labeled with this term can be an unsubstituted group (a group in which the hydrogen atom is not substituted by a substituent), and at least one hydrogen atom of the group labeled with this term can also be substituted by a substituent. The term "deuterium substituted or unsubstituted" means that the group labeled with this term can be an unsubstituted group (a group in which the hydrogen atom is not substituted by a substituent), and at least one hydrogen atom of the group labeled with this term can be a deuterium atom (deuterium). 2 H). Wherein, as described above, the hydrogen atoms present within the molecules of the compounds used in this invention can be... 1 H can also be 2 H (deuterium). Therefore, the description of "deuterium substitution" in "deuterium-substituted or unsubstituted" is specifically recorded to indicate that the description of "unsubstituted" does not exclude the possibility that the hydrogen atom is a "deuterium atom".

[0050] In this specification, "organic compound" means a compound containing one or more carbon atoms, and "organic layer" means a layer containing 70% or more organic compound by mass. As an organic compound, for example, an organic compound composed solely of atoms selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, sulfur, boron, and halogen atoms can be used. In this specification, "transparent" means that the transmittance of visible light is 50% or more, and the transmittance of visible light is, for example, 80% or more, 90% or more, or 99% or more. The transmittance of visible light can be measured using a UV-Vis spectrophotometer.

[0051] <Aromatic Amine Compounds> The arylamine compounds of the present invention are compounds represented by the above general formula (I). In general formula (I), Ar 1 and Ar 2 Each can independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L 1 ~L 3 Each independently represents a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. A represents a naphthyl group represented by the above general formula (II) that is optionally substituted with a deuterium atom. In general formula (II), R represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. n represents an integer of 2 or 3, and there may be multiple Rs that are optionally the same or different. It should be noted that L in general formula (II) 3 L in general formula (I) 3 , refers to the group attached to A (the naphthyl group represented by general formula (II)) in general formula (I). Additionally, L 1 L 2 and L 3 For a single bond, Ar refers to 1 Ar 2A and A are directly bonded to nitrogen atoms (N) represented by general formula (I).

[0052] Ar constitutes the general formula (I) 1 and Ar 2 The aromatic ring of "aryl" in general formula (II), represented by R as "substituted or unsubstituted aryl", can be a monocyclic ring, a fused ring composed of two or more rings, a linking ring composed of two or more rings connected by a single bond, or a spirocyclic ring composed of two or more rings connected by a helical bond. When the aromatic ring is a fused ring, the number of fused rings is, for example, 2 to 6, preferably 2 to 4. When the aromatic ring is a linking ring, the number of linked rings is, for example, 2 to 6, preferably 2 to 4. The number of carbon atoms constituting the aromatic ring (hereinafter also simply referred to as "number of carbon atoms") is, for example, 6 to 30, for example, 6 to 22, for example, 6 to 20, for example, 6 to 18, for example, 6 to 14, for example, 6 to 12, for example, 6 to 10. Specific examples of "aryl" include aryl groups with 6 to 30 carbon atoms, such as phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indole, pyrene, peryl, fluoranyl, triphenylene, fluorenyl, and spirobisfluorenyl.

[0053] Ar constituted in general formula (I) 1 and Ar 2 The aromatic heterocycle of "heteroaryl" in general formula (II), represented by R as "substituted or unsubstituted heteroaryl", can be a monocyclic ring or a fused ring composed of two or more rings. When the aromatic heterocycle is a fused ring, the number of fused rings is, for example, 2 to 6, preferably 2 to 4. Examples of heteroatoms constituting the aromatic heterocycle include nitrogen, oxygen, and sulfur atoms. The number of carbon atoms constituting the aromatic heterocycle (hereinafter also simply referred to as "number of carbon atoms") is, for example, 2 to 30, for example, 2 to 18, for example, 2 to 12. Specific examples of "heteroaryl" groups include pyridyl, pyrimidinyl, triazinyl, furanyl, pyrrolithyl, thiopheneyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiopheneyl, indolyl, carbazolyl, benzooxazolyl, benzothiazolyl, imidazopyridyl, oxazolylpyridyl, oxazolylpyrazinyl, quinoxolinyl, quinazolyl, benzoimidazolyl, pyrazolyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiopheneyl, naphridyl, phenanthrololinyl, acridineyl, and carbazolyl, which have 2 to 30 carbon atoms.

[0054] In general formula (I), L 1 ~L 3The "arylene" or "heteroarylene" in "substituted or unsubstituted arylene" has the same meaning as "divalent aromatic hydrocarbon" or "divalent aromatic heterocyclic group," respectively. That is, as "arylene" or "heteroarylene," examples can be derived from the Ar... 1 Ar 2 And R represents a divalent aromatic hydrocarbon group or aromatic heterocyclic group obtained by removing one hydrogen atom from the specific group exemplified by "aryl" or "heteroaryl". It should be noted that the number of carbon atoms in the aromatic ring constituting the "arylene" is, for example, 6–30, 6–22, 6–20, 6–18, 6–14, 6–12, or 6–10. Furthermore, the number of carbon atoms in the aromatic heterocycle constituting the "heteroarylene" is, for example, 2–30, 2–18, or 2–12.

[0055] As Ar in general formula (I) 1 and Ar 2 And the "substituent" in formula (II) represented by R, which is either "substituted aryl" or "substituted heteroaryl", can be exemplified as follows: Deuterium atom, cyano group, nitro group; Halogen atoms such as fluorine, chlorine, bromine, and iodine; Trimethylsilyl, triphenylsilyl, and other silyl groups; Alkyl groups such as methyl, ethyl, and propyl, which are straight-chain or branched chains with 1 to 6 carbon atoms; Alkoxy groups, such as methoxy, ethoxy, and propoxy, which are straight-chain or branched chains with 1 to 6 carbon atoms; vinyl, allyl, and other alkenyl groups; Aryl groups with 6 to 30 carbon atoms, including phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indole, pyrene, peryl, fluoranyl, triphenylene, fluorenyl, and spirobisfluorenyl. Pyridyl, pyrimidinyl, triazinyl, furanyl, pyrroleyl, thiopheneyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiopheneyl, indolyl, carbazoyl, benzooxazolyl, benzothiazoyl, imidazopyridyl, oxazolylpyridyl, oxazolylpyrazinyl, quinoxolinyl, quinazolyl, benzoimidazoyl, pyrazolyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiopheneyl, naphridyl, phenanthrololinyl, acridineyl, and carbazoyl, etc., heteroaryl groups with 2 to 30 carbon atoms; Aryloxy groups such as phenyloxy, tolyloxy, biphenyloxy, and naphthoxy; Arylalkyloxy groups such as benzyloxy and phenethyloxy.

[0056] The hydrogen atoms in these substituents can be further replaced by substituents exemplified here. It should be noted that, for substituents that further replace the substituents, the substituent that directly replaces the parent skeleton (aromatic hydrocarbon group or aromatic heterocyclic group) is sometimes called the "first substituent," and the substituent replacing the first substituent is called the "second substituent." Where the first substituent contains a benzene ring, the benzene ring can bond to the parent skeleton to form a cyclic structure. Furthermore, where the benzene ring of the first substituent is replaced by two or more second substituents, adjacent second substituents can bond to each other to form a cyclic structure. It should be noted that the bonding of the benzene ring in the first substituent to the parent skeleton and the bonding of the second substituents to each other can be a single bond or a bond via a linker. Examples of linkers include substituted or unsubstituted methylene groups, as well as oxygen and sulfur atoms. Preferred substituents as the first and second substituents include deuterium atoms, straight-chain or branched alkyl groups having 1 to 6 carbon atoms, and aryl groups having 6 to 20 carbon atoms constituting an aromatic ring.

[0057] As in general formula (I) by L 1 ~L 3 The "substituent" in "substituted aryl" or "substituted heteroaryl" can be exemplified by the group that is formed by the Ar 1 Ar 2 And the same group as the substituent exemplified in "substituted aryl" or "substituted heteroaryl" where R represents "substituted aryl". Furthermore, the substituent can be in the same manner.

[0058] In general formula (I), Ar 1 and Ar 2 Preferably, it is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted, or a heteroaryl group with 2 to 30 carbon atoms that is substituted or unsubstituted; more preferably, it is an aryl group with 6 to 12 carbon atoms that is substituted or unsubstituted, or a heteroaryl group with 2 to 12 carbon atoms that is substituted or unsubstituted. As "aryl group with 6 to 30 carbon atoms" or "heteroaryl group with 2 to 30 carbon atoms" in "aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted" or "heteroaryl group with 2 to 30 carbon atoms", it is preferably phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, spirobisfluorenyl, carbazolyl, dibenzofuranyl or naphthobenzofuranyl, more preferably phenyl, biphenyl, terphenyl, naphthyl, phenanthrene or dibenzofuranyl, and even more preferably phenyl, biphenyl, naphthyl or dibenzofuranyl. It should be noted that "aryl groups with 6 to 30 carbon atoms, whether substituted or unsubstituted" or "heteroaryl groups with 2 to 30 carbon atoms, whether substituted or unsubstituted" are preferably deuterated or unsubstituted. That is, Ar 1 and Ar 2Preferably, the aryl or heteroaryl groups are substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, spirobisfluorenyl, carbazole, dibenzofuranyl, or naphthobenzofuranyl; more preferably, they are substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, or dibenzofuranyl; and even more preferably, they are substituted or unsubstituted phenyl, biphenyl, naphthyl, or dibenzofuranyl. Furthermore, these aryl or heteroaryl groups are preferably deuterated or unsubstituted. Additionally, Ar... 1 and Ar 2 At least one of them is preferably a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, even more preferably a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, and particularly preferably a deuterated or unsubstituted aryl group with 6 to 12 carbon atoms.

[0059] In general formula (I), as L 1 and L 2 Preferably, it is an arylene group with 6 to 20 carbon atoms, either with a single bond or with substituted or unsubstituted carbon atoms; more preferably, it is an arylene group with 6 to 20 carbon atoms, either with a single bond or with deuterium-substituted or unsubstituted carbon atoms; and even more preferably, it is an arylene group with 6 to 12 carbon atoms, either with a single bond or with deuterium-substituted or unsubstituted carbon atoms. As for the "arylene group with 6 to 20 carbon atoms (deuterium-substituted or unsubstituted carbon atoms)," the "arylene group with 6 to 20 carbon atoms" is preferably phenylene or biphenyldiyl, more preferably phenylene, and particularly preferably 1,4-phenylene. 1 and L 2 At least one of them is preferably a single bond. Additionally, in L... 1 In the case of a single bond, Ar 1 Preferably, it is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group, in L 2 In the case of a single bond, Ar 2 Preferably, it is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group.

[0060] In general formula (I), L 3 Preferably, it is an arylene group with 6 to 30 carbon atoms, either with a single bond or with substituted or unsubstituted carbon atoms; more preferably, it is an arylene group with 6 to 30 carbon atoms, either with a single bond or with deuterium-substituted or unsubstituted carbon atoms; even more preferably, it is an arylene group with 6 to 12 carbon atoms, either with a single bond or with deuterium-substituted or unsubstituted carbon atoms; and particularly preferably, it is an arylene group with 6 to 12 carbon atoms, either with deuterium-substituted or unsubstituted carbon atoms. The "arylene group with 6 to 30 carbon atoms" in "arylene group with 6 to 30 carbon atoms" is preferably phenylene, biphenyldiyl, or naphthylene; more preferably, it is phenylene or biphenyldiyl; even more preferably, it is phenylene; and particularly preferably, it is 1,4-phenylene.

[0061] In general formula (I), A is preferably L. 3A 2-naphthyl group bonded to the 2-position of the naphthalene ring. Furthermore, in general formula (II), n is 2 or 3, preferably 2. The naphthyl group represented by A is preferably a disubstituted or trisubstituted 2-naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-7), the group consisting of general formulas (II-A-8) to (II-A-14), or the group consisting of general formulas (II-A-1) to (II-A-14). More preferably, it is a disubstituted 2-naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-3) and general formulas (II-A-8) to (II-A-14). Even more preferably, it is a disubstituted 2-naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-3), (II-A-8), and (II-A-11).

[0062] Especially when A is a naphthyl group selected from the group consisting of general formulas (II-A-8) to (II-A-14), L is preferred. 1 and L 2 At least one of them is preferably a single bond, more preferably an L bond. 1 and L 2 One is a single bond, and the other is a group other than a single bond. Furthermore, in L... 1 and L 2 When one group is a single bond and the other is a group other than a single bond, it interacts with L, which is a single bond. 1 Or L 2 bonded Ar 1 Or Ar 2 Preferably, it is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group. That is, preferably L... 1 It is a single bond, and Ar 1 It is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group, or L 2 It is a single bond, and Ar 2 It is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group; in the case of the former, L is preferred. 2 It is not a single bond; in the latter case, L is preferred. 1 It's not a single key.

[0063] In general formula (II), R is preferably an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted, more preferably an aryl group with 6 to 12 carbon atoms, and even more preferably a deuterated or unsubstituted aryl group with 6 to 12 carbon atoms. The "aryl group with 6 to 30 carbon atoms" in "substituted or unsubstituted aryl group with 6 to 30 carbon atoms" is preferably phenyl, biphenyl, naphthyl, phenanthryl, or dibenzofuranyl, more preferably phenyl, biphenyl, naphthyl, or phenanthryl, and even more preferably phenyl. That is, R is particularly preferably a deuterated or unsubstituted phenyl group.

[0064] The arylamine compounds of the present invention represented by general formula (I) are novel compounds, but these compounds can be synthesized by methods known in themselves (see, for example, non-patent literature 2).

[0065] exist Figures 1-12 Specific examples of preferred compounds in the arylamine compounds represented by general formula (I) are shown, but the invention is not limited to these compounds. As described above, in the arylamine compounds represented by general formula (I), all hydrogen atoms in the molecule can be […]. 1 H, some or all of the hydrogen atoms can be 2 H(D). Therefore, in Figures 1-12 The text also shows that some or all of the hydrogen atoms within the molecule are... 2 Compounds of H(D), they represent 2 An example of the substitution method for H(D), 2 The substitution method for H(D) is not limited to the method shown in the figure.

[0066] The purification method for arylamine compounds represented by general formula (I) is not particularly limited, and well-known methods for purifying organic compounds, such as purification by column chromatography, adsorption purification by silica gel, activated carbon, or activated clay, recrystallization purification by solvent, crystallization purification, and sublimation purification, can be used. The compounds can be identified by NMR analysis.

[0067] For the physical properties of arylamine compounds represented by general formula (I), the melting point, glass transition temperature (Tg), and work function are preferably measured. The melting point serves as an indicator of vapor deposition performance, while the glass transition temperature serves as an indicator of the stability of the thin film. The melting point and glass transition temperature can be measured on powders of the compound using a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, trade name: DSC3100SA). Furthermore, the work function serves as an indicator of hole injection performance, hole transport performance, and electron blocking performance. The work function can be measured on thin films (100 nm) of the compound fabricated on ITO substrates using an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., trade name: PYS-202).

[0068] <Organic EL Components and Electronic Devices> The arylamine compounds of the present invention, represented by general formula (I), can be suitably used in organic EL devices. Specifically, the arylamine compounds of the present invention are preferably used as materials constituting layers selected from hole injection layers, hole transport layers, electron blocking layers, and light-emitting layers in organic EL devices, and more preferably as materials constituting layers selected from hole transport layers and electron blocking layers. In addition, the arylamine compounds of the present invention are preferably used as constituent materials of organic layers in electronic devices having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes.

[0069] [Organic EL Components] Figure 13 This is a schematic diagram illustrating the structure of an organic EL element according to an embodiment of the present invention. As an example of the structure of an organic EL element, in the case of a top-emitting structure, a structure in which an anode 2, a hole transport layer 4, a light-emitting layer 6, an electron transport layer 7, a cathode 9, and a capping layer 10 are sequentially stacked on a glass substrate 1. Other examples include structures with a hole injection layer 3 between the anode and the hole transport layer, structures with an electron blocking layer 5 between the hole transport layer and the light-emitting layer, structures with a hole blocking layer (not shown) between the light-emitting layer and the electron transport layer, and structures with an electron injection layer 8 between the electron transport layer and the cathode. In these multilayer structures, a single organic layer can perform multiple functions. For example, it can be configured as both a hole injection layer and a hole transport layer, both a hole transport layer and an electron blocking layer, both a hole blocking layer and an electron transport layer, or both an electron transport layer and an electron injection layer. Alternatively, it can be a structure consisting of two or more organic layers with the same function, such as a structure consisting of two hole transport layers, a structure consisting of two light-emitting layers, a structure consisting of two electron transport layers, and a structure consisting of two capping layers.

[0070] The total thickness of all layers constituting the organic EL element is preferably 200 nm to 750 nm, more preferably 350 nm to 600 nm. Furthermore, the thickness of the capping layer is preferably 30 nm to 120 nm, more preferably 40 nm to 80 nm. With such film thicknesses in the organic EL element, good light extraction efficiency can be obtained. It should be noted that the thickness of the capping layer can be appropriately varied depending on the type of light-emitting material used in the light-emitting element and the film thicknesses of the layers other than the capping layer.

[0071] (Substrate) The substrate is not particularly limited and can include glass substrates, plastic substrates, etc. The substrate can be transparent or opaque. Examples of substrates include: polyethylene terephthalate, polyethylene naphthalate, polyethylene, polypropylene, celluloid, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate, cellulose acetate phthalate, cellulose nitrocellulose, polyvinylidene chloride, polyvinyl alcohol, polyvinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyetherketone, polyimide, polyethersulfone, polyphenylene sulfide, polysulfones, polyetherimide, polyetherketoneimide, polyamide, fluoropolymers, nylon, polymethyl methacrylate, acrylic or polyarylates, organic-inorganic hybrid resins, etc.; inorganic substrates such as glass, quartz, alumina, silicon, silica, tantalum dioxide, tantalum pentoxide, indium tin oxide, etc.; and metal substrates such as gold, copper, chromium, titanium, aluminum, etc. From the viewpoint of forming transistors, glass substrates and polyimide substrates with excellent heat resistance are preferred.

[0072] (anode) As an anode, electrode materials with high work functions, such as ITO and gold, can be used.

[0073] (Hole injection layer and hole transport layer) The arylamine compounds of the present invention, represented by general formula (I), can be used as materials for hole injection layers and hole transport layers. Furthermore, arylamine compounds having only one triphenylamine structure in the molecule can be cited as materials for hole injection layers. Other materials that can be used include porphyrin compounds represented by copper phthalocyanine, starburst-type triphenylamine derivatives, arylamine compounds having two or more triphenylamine structures or carbazole structures in the molecule, each having a structure formed by single bonds or divalent groups without heteroatoms, acceptor heterocyclic compounds such as hexacyanoazitrimethylene, and coating-type polymeric materials. Thin film formation using these materials can be performed by known methods such as vapor deposition, spin coating, and inkjet printing.

[0074] As materials for the hole injection layer and hole transport layer, in addition to the arylamine compounds represented by general formula (I) of the present invention, arylamine compounds having only one triphenylamine structure in the molecule are preferably used. Furthermore, 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 structures or carbazole structures in the molecule, each having a structure formed by single bonds or divalent groups without heteroatoms, can be used. These materials can be formed into films individually or in mixtures, and each can be used as a monolayer. Alternatively, the structure can be a stack of layers formed by forming a film from a single material, a stack of layers formed by mixing multiple materials, or a stack of a single layer and a mixture of multiple layers. Furthermore, coating-type polymers such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrene sulfonate) (PSS) can be used as materials for both the hole injection layer and the hole transport layer. Thin films using these materials can be formed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0075] Alternatively, in the hole injection layer or hole transport layer, materials obtained by further p-doping the materials commonly used in these layers with tribromoaniline hexachloroantimony, axialene derivatives (for example, see Patent Document 3), etc., can also be used. Furthermore, polymeric compounds having a benzidine derivative structure such as TPD as a partial structure can be used.

[0076] (Electron blocking layer) As the electron blocking layer material, the arylamine compound of the present invention represented by general formula (I) is preferably used. Furthermore, as the electron blocking layer material, 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), and compounds with electron blocking properties such as compounds having triphenylsilyl and triarylamine structures, represented by 9-[4-(carbazole-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, can also be used. These materials can also serve as hole transport layer materials. These materials can be formed into films individually or in mixtures, and each can be used as a monolayer. Alternatively, the structure can be a stack of layers formed by forming a film from one of these materials alone, a stack of layers formed by mixing multiple materials, or a stack of a single layer formed by forming a film from a mixture of multiple materials. Thin film formation using these materials can be carried out by known methods such as vapor deposition, spin coating, and inkjet printing.

[0077] (Emitting layer) As the material for the light-emitting layer, the arylamine compound of the present invention represented by general formula (I) is preferably used. Furthermore, as the material for the light-emitting layer, metal complexes of hydroxyquinoline derivatives represented by tris(8-hydroxyquinoline)aluminum (Alq3), various metal complexes, anthracene derivatives, bis(5-phenylene)benzene derivatives, pyrene derivatives, oxazole derivatives, and poly(p-phenylene)acetylene derivatives, etc., can be used. Additionally, the light-emitting layer can be composed of a host material and a dopant material. In this case, as the host material, the arylamine compound of the present invention represented by general formula (1) and anthracene derivatives are preferably used. Furthermore, in addition to the light-emitting layer materials illustrated above, heterocyclic compounds having a partial structure with an indole ring as a fused ring, heterocyclic compounds having a partial structure with a carbazole ring as a fused ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives, etc., can also be used. Furthermore, as the dopant material, heterocyclic compounds having S, B, and N as ring constituent elements are preferably used. In addition, quinacridones, coumarins, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, and aminostyrene derivatives can be used. These materials can be used individually or in combination to form films, each as a monolayer. Furthermore, the film can be a stack of layers formed by individually forming films from these materials, a stack of layers formed by combining multiple materials, or a stack of a single layer and a mixture of multiple layers. Thin film formation using these materials can be performed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0078] Alternatively, phosphorescent materials can be used as luminescent materials. Phosphorescent materials composed of metal complexes such as iridium and platinum can be used. Examples of phosphorescent materials 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). In this case, as the host material, as a host material possessing hole injection and hole transport properties, in addition to carbazole derivatives such as 4,4'-bis(N-carbazolyl)biphenyl (CBP), TCTA, and mCP, the arylamine compounds of this invention can also be used. Furthermore, as a host material possessing electron transport properties, p-bis(triphenylsilyl)benzene (UGH2) and 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI) can be used. By using such materials, high-performance organic EL devices can be fabricated. It should be noted that, in order to avoid concentration quenching, the doping of the phosphorescent material into the host material is preferably carried out by co-evaporation in the range of 1% to 30% by mass relative to the overall luminescent layer.

[0079] Alternatively, materials with delayed fluorescence, such as CDCB derivatives like PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, can also be used as luminescent materials (see, for example, Non-Patent Literature 3). Thin films using these materials can be formed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0080] (Cavity barrier layer) Materials used as hole-blocking layers include phenanthroline derivatives such as copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives such as bis(2-methyl-8-quinoline)-4-(phenylphenol)aluminum (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives, all of which possess hole-blocking properties. These materials can also serve as electron transport layer materials. These materials can be formed individually or in combination, each acting as a monolayer. Alternatively, the film can be a stack of layers formed by individually forming one of these materials, a stack of layers formed by combining multiple materials, or a stack of a single layer and a mixture of multiple layers. Thin films using these materials can be formed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0081] (Electron transport layer) As materials for the electron transport layer, benzimidazole derivatives, anthracene derivatives, pyrimidine derivatives, and triazine derivatives are preferred. In addition, metal complexes of hydroxyquinoline derivatives represented by Alq3 and BAlq, various metal complexes, triazole derivatives, oxadiazole derivatives, pyridine derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridinodole derivatives, phenanthroline derivatives, and thiophene derivatives can be used. These materials can be formed into films individually or in mixtures, each serving as a monolayer. Furthermore, the film can be a stack of layers formed by individually forming films from these materials, a stack of layers formed by mixing multiple materials, or a stack of a single layer and a mixture of multiple layers. Thin films using these materials can be formed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0082] (Electron injection layer) Materials used for the electron injection layer include alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of hydroxyquinoline derivatives such as lithium hydroxyquinoline, metal oxides such as alumina, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs). By optimizing the electron transport layer and the cathode, the electron injection layer can be omitted.

[0083] Furthermore, in the electron injection layer and the electron transport layer, a material that is further doped with N metals such as cesium can be used to make the material commonly used in this layer.

[0084] (cathode) As a cathode, metals with low work functions such as aluminum, as well as alloys with even lower work functions such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-magnesium alloys, can be used.

[0085] (Covering layer) The preferred materials for the capping layer are monoamine derivatives, diamine derivatives, or carbazole derivatives having a benzoxazole structure, such as benzoxazole-based or benzothiazol-based materials. These materials can be formed individually or in combination, each serving as a single layer. Alternatively, the film can be a stack of layers selected from these materials, a stack of layers formed by mixing multiple materials, or a stack of a single layer and multiple layers formed by mixing. Thin films using these materials can be formed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0086] The above describes an organic EL element with a top-emitting structure, but the present invention is not limited thereto. It can also be applied to organic EL elements with a bottom-emitting structure, and to organic EL elements with a dual-emitting structure that emits light from both the top and bottom. In organic EL elements with any structure, the electrode located in the direction in which light is emitted from the emitting element is preferably transparent or semi-transparent.

[0087] Example The embodiments of the present invention will be described in more detail below using examples; however, the present invention is not limited to the following examples as long as it does not depart from its spirit. The reagents used in the examples are those manufactured by Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich, and Alfa Aesar, among others. Furthermore, all reactions used to synthesize the compounds of the present invention were carried out in reaction vessels equipped with cooling tubes, stirring devices, and thermometers under a nitrogen gas flow. It should be noted that the identification of the compounds in the examples was achieved through… 1 H-NMR analysis (Bruker Ascend nuclear magnetic resonance device, model: 1H-NMR) TM (400MHz)

[0088] [Example 1: Synthesis of compound (A-28)] In a reaction vessel, 8.0 g of N-phenyl-4-(7,8-diphenyl-2-naphthylaniline), 5.6 g of 4-bromo-(2-naphthyl)benzene, 2.6 g of sodium tert-butoxy, 0.3 g of tris(dibenzylacetone)palladium(O), 0.2 g of Sphos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl), and 80 mL of toluene were added, and the mixture was stirred under reflux overnight. After confirming the reaction was complete, 80 mL of toluene was added to the mixture, followed by 4.5 g of silica gel, and the mixture was stirred at 90 °C for 30 minutes. The resulting reaction mixture was then filtered through diatomaceous earth at this temperature. The filtrate was concentrated and purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain the crude product. The crude product was purified by crystallization using a tetrahydrofuran / ethyl acetate mixed solvent to obtain compound (A-28): 5.7 g (yield: 49.1%, white powder).

[0089] [Chemical Formula 5]

[0090] Compound (A-28) was subjected to 1 H-NMR analysis (DMSO-d6) detected the following 35 hydrogen signals.

[0091] δ(ppm)=8.19(1H), 8.12(1H), 8.07(1H), 8.00-7.93(3H), 7.87(2H), 7.78(2H), 7.69(1H), 7.58-7.49(5H), 7.38-7.31(5H), 7.26-7.12(14H).

[0092] [Example 2: Synthesis of compound (A-34)] 6-(4-chlorophenyl)-1,4-diphenylnaphthalene: 6.1 g, 4-(2-naphthyl)-N-phenylaniline: 8.0 g, sodium tert-butoxy: 3.9 g, tris(dibenzylacetone)palladium(O): 0.4 g, tri-tert-butylphosphine: 0.2 g, and xylene: 80 mL were added to a reaction vessel and stirred under reflux overnight. After confirming the reaction was complete, the reaction mixture was cooled to room temperature. Then, 80 mL of methanol was added to the reaction mixture, and the resulting precipitate was filtered off to obtain the crude product. The crude product was purified by crystallization using a tetrahydrofuran / ethyl acetate mixed solvent to obtain compound (A-34): 7.2 g (yield: 54.1%, white powder).

[0093] [Chemical Formula 6]

[0094] Compound (A-34) was subjected to 1 H-NMR analysis (DMSO-d6) detected the following 35 hydrogen signals.

[0095] δ(ppm)=8.19(1H), 8.08(1H), 8.00-7.93(4H), 7.85(2H), 7.78(2H), 7.60-7.49(16H), 7.37(2H), 7.17-7.10(7H).

[0096] [Example 3: Synthesis of compound (A-130)] In a reaction vessel, 9.0 g of N-phenyl-4-(4,8-diphenyl-2-naphthylaniline), 5.0 g of 3-bromodibenzofuran, 3.9 g of sodium tert-butoxy, 0.4 g of tris(dibenzylacetone)palladium(O), 0.2 g of tri-tert-butylphosphine, and 90 mL of toluene were added, and the mixture was stirred under reflux overnight. After confirming the reaction was complete, the reaction mixture was cooled to room temperature. Then, 90 mL of methanol was added to the reaction mixture, and the resulting precipitate was filtered off to obtain the crude product. The crude product was purified by crystallization using a tetrahydrofuran / ethyl acetate mixture to obtain compound (A-130): 10.0 g (yield: 81.0%, white powder).

[0097] [Chemical Formula 7]

[0098] Compound (A-130) was subjected to 1 ¹H-NMR analysis (DMSO-d6) detected the following 31 hydrogen signals.

[0099] δ(ppm)=8.25(1H), 8.11(3H), 7.93(1H), 7.76(1H), 7.72-7.57(10H), 7.54-7.38(8H), 7.33(1H), 7.26(4H), 7.22-7.16(2H).

[0100] [Example 4: Synthesis of compound (A-152)] 10.9 g of 6-(4-chlorophenyl)-1,2-bis(phenyl-d5-)naphthalene, 8.0 g of 4-(2-naphthyl)-N-phenylaniline, 3.1 g of sodium tert-butoxy, 0.5 g of tris(dibenzylacetone)palladium(O), 0.2 g of tri-tert-butylphosphine, and 80 mL of xylene were added to a reaction vessel and stirred under reflux overnight. After confirming the reaction was complete, 80 mL of toluene was added to the reaction mixture, followed by 4.5 g of silica gel, and the mixture was stirred at 90 °C for 30 minutes. The resulting reaction mixture was then filtered through diatomaceous earth at this temperature. The filtrate was concentrated to obtain a crude product. The crude product was purified by crystallization using a tetrahydrofuran / acetone mixed solvent to obtain compound (A-152): 13.9 g (yield: 77.8%, white powder).

[0101] [Chemical Formula 8]

[0102] Compound (A-152) was subjected to 1 H-NMR analysis (DMSO-d6) detected the following 25 hydrogen signals.

[0103] δ(ppm)=8.32(1H), 8.21(1H), 8.10(1H), 8.01-7.97(2H), 7.94(1H), 7.86(1 H), 7.83-7.80(5H), 7.59(1H), 7.56-7.49(3H), 7.39(2H), 7.20-7.12(7H).

[0104] [Characteristic Evaluation of Compounds] (Determination of melting point and glass transition temperature) The melting point and glass transition temperature (Tg) of each compound obtained in Examples 1 to 4 were determined. The measurements were performed using a high-sensitivity differential scanning calorimeter (Brook AXS, trade name: DSC3100SA). The results are shown in Table 1.

[0105] [Table 1]

[0106] As shown in Table 1, the compounds of the present invention obtained in Examples 1 to 4 have high melting points and glass transition temperatures of 100°C or higher. This result indicates that the thin films of the compounds in Examples 1 to 4 exhibit stable properties and excellent durability.

[0107] (Determination of work function) Using the compounds obtained in Examples 1 to 4, 100 nm thick vapor-deposited films were fabricated on ITO substrates, and their work functions (in eV) were measured. The measurements were performed using an ionization potential measuring apparatus (manufactured by Sumitomo Heavy Industries, Ltd., trade name: PYS-202). The results are shown in Table 2.

[0108] [Table 2]

[0109] As shown in Table 2, the compounds of the present invention obtained in Examples 1 to 4 exhibit suitable energy levels compared to the work function (5.4 eV) of general hole transport materials such as NPD and TPD. This result demonstrates that the compounds of Examples 1 to 4 possess good hole transport capabilities and excellent electron blocking capabilities.

[0110] [Characteristic Evaluation of Organic EL Devices] (Fabrication of organic EL components) The compounds of the present invention obtained in Examples 1 to 4, as well as comparative compounds (EBL-1), (EBL-2), and (EBL-3) having the following structures (see, for example, Patent Document 4), were used as electron blocking layers to fabricate organic EL devices. It should be noted that, as Figure 13 As shown, a reflective ITO electrode is pre-formed on a glass substrate 1 as a transparent anode 2. 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 then sequentially deposited on the substrate to fabricate an organic EL device. The specific fabrication steps are described below.

[0111] [Chemical Formula 9]

[0112] A 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film as a transparent anode 2 are sequentially formed on a glass substrate 1. The resulting substrate is ultrasonically cleaned in isopropanol for 20 minutes and then dried on a hot plate heated to 250°C for 10 minutes. After a 2-minute UV ozone treatment, the ITO-coated glass substrate is mounted in a vacuum evaporation machine, and the pressure is reduced to below 0.001 Pa. Next, an electron acceptor (acceptor-1) and a compound (HTM-1) with the following structure are binary deposited at a deposition rate ratio of acceptor-1:compound (HTM-1) = 3:97, covering the transparent anode 2, to form a 10 nm thick hole injection layer 3. The compound (HTM-1) with the following structure is then deposited on the hole injection layer 3 to form a 140 nm thick hole transport layer 4. The compound of the example or a comparative compound is then deposited on the hole transport layer 4 to form a 5 nm thick electron blocking layer 5. On the electron blocking layer 5, compound (EMD-1) and compound (EMH-1) with the following structures are binary deposited at a deposition rate of compound (EMD-1): compound (EMH-1) = 5:95 to form a light-emitting layer 6 with a film thickness of 20 nm. On the light-emitting layer 6, compound (ETM-1) and compound (ETM-2) with the following structures are binary deposited at a deposition rate of compound (ETM-1): compound (ETM-2) = 50:50 to form an electron transport layer 7 with a film thickness of 30 nm. Lithium fluoride is deposited on the electron transport layer 7 to form an electron injection layer 8 with a film thickness of 1 nm. A magnesium-silver alloy is deposited on the electron injection layer 8 to form a cathode 9 with a film thickness of 12 nm. Finally, compound (CPL-1) with the following structure is deposited on the cathode 9 to form a capping layer 10 with a film thickness of 60 nm. As described above, organic EL elements were prepared using the compounds of Examples 1 to 4 and the comparative compounds 1 to 3 of Examples 1 to 4 and the comparative examples 1 to 3 of Comparative Examples 1 to 3.

[0113] [Chemical Formula 10]

[0114] [Chemical Formula 11]

[0115] [Chemical Formula 12]

[0116] (Determination of the luminescence properties of organic EL elements) For each organic EL element fabricated, a current density of 10 mA / cm² was applied at room temperature and in atmospheric conditions. 2 The luminescence characteristics at a given current were determined. The results are shown in Table 3.

[0117] (Determination of the lifespan of organic EL elements) The results of measuring the lifetime of each organic EL element fabricated are shown in Table 3. It should be noted that, in this invention, the lifetime is measured at a current density of 10 mA / cm². 2 The initial brightness was set to 100% when driven by constant current, and the time it took for the brightness to decay to 95% was measured.

[0118] [Table 3]

[0119] As shown in Table 3, the current density is 10 mA / cm². 2 Regarding the luminous efficiency at a given current, the organic EL elements of Examples 1 to 4 exhibit a high efficiency of 8.96 cd / A to 9.12 cd / A, compared to the organic EL elements of Comparative Examples 1 to 3 (8.25 cd / A to 8.26 cd / A). Furthermore, regarding power efficiency, the organic EL elements of Examples 1 to 4 also exhibit a high efficiency of 8.29 lm / W to 8.39 lm / W, compared to the organic EL elements of Comparative Examples 1 to 3 (8.21 lm / W to 8.22 lm / W). Moreover, in terms of element lifespan, the organic EL elements of Examples 1 to 4 achieve a long lifespan of 425 hours to 467 hours, compared to the organic EL elements of Comparative Examples 1 to 3 (351 hours to 360 hours).

[0120] The results above show that, compared with existing organic EL devices, the organic EL device of the present invention, which uses arylamine compounds with high hole mobility, excellent electron blocking ability, and excellent stability and durability in the thin film state, has high luminous efficiency and power efficiency, low luminous start voltage and practical driving voltage, and long lifetime.

[0121] The above describes several preferred embodiments of the present invention in detail. However, the present invention is not limited to the above embodiments and should be understood to allow for various changes and modifications without departing from the spirit or scope of the appended technical solutions.

[0122] This application claims priority based on Japanese Patent Application No. 2024-048794, filed on March 25, 2024, the entire contents of which are incorporated herein by reference.

[0123] Industrial availability In organic EL elements using the arylamine compounds of the present invention with specific structures, luminous efficiency is improved and element durability is enhanced, thus enabling applications such as in home appliances and lighting.

[0124] (Explanation of reference numerals in the attached image) 1: Glass substrate 2: Anode 3: Hole injection layer 4: Hole transport layer 5: Electron blocking layer 6: Emissive layer 7: Electron transport layer 8: Electron injection layer 9: Cathode 10: Overlay

Claims

1. An arylamine compound, represented by the following general formula (I), wherein, [Chemical Formula 1] In general formula (I), Ar 1 and Ar 2 Each can independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L 1 ~L 3 Each can independently represent a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. A represents a naphthyl group, optionally substituted with a deuterium atom, represented by the following general formula (II). [Chemical Formula 2] In general formula (II), R represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. n represents an integer of 2 or 3, and there exist multiple R values ​​that are either the same or different. L 3 Same as the definition in general formula (I).

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

3. The arylamine compound according to claim 2, wherein, In the general formula (I), L 1 It is a single key. Ar 1 It is a deuterated or unsubstituted aryl group or a deuterated or unsubstituted heteroaryl group. A is a naphthyl group selected from the group consisting of general formulas (II-A-8) to (II-A-14) that is optionally substituted with a deuterium atom. [Chemical Formula 3] L in general formulas (II-A-8) to (II-A-14) 3 And R is the same as the definition in general formula (I) and general formula (II).

4. The arylamine compound according to claim 3, wherein, In the general formula (I), L 3 It is a deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenyl dimethyl, or a deuterated or unsubstituted naphthylene.

5. The arylamine compound according to claim 4, wherein, In the general formula (I), Ar 1 It is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

6. The arylamine compound according to claim 5, wherein, In the general formula (II), R is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

7. The arylamine compound according to claim 6, wherein, In the general formula (II), R is a deuterated or unsubstituted phenyl group.

8. The arylamine compound according to claim 1, wherein, In the general formula (I), A is a naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-7), which is optionally substituted with a deuterium atom. [Chemical Formula 4] L in general formulas (II-A-1) to (II-A-7) 3 And R is the same as the definition in general formula (I) and general formula (II).

9. The arylamine compound according to claim 8, wherein, In the general formulas (II-A-1) to (II-A-7), R is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

10. The arylamine compound according to claim 9, wherein, In the general formula (I), L 3 It is a single bond, a deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenyl dimethyl, or a deuterated or unsubstituted naphthylene.

11. The arylamine compound according to claim 10, wherein, In the general formula (I), Ar 1 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted dibenzofuranyl.

12. The arylamine compound according to claim 11, wherein, In the general formula (I), A is a naphthyl group selected from the group consisting of general formulas (II-A-1) to (II-A-3).

13. The arylamine compound according to claim 12, wherein, In the general formula (I), Ar 1 It is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted dibenzofuranyl.

14. The arylamine compound according to claim 13, wherein, In the general formulas (II-A-1) to (II-A-3), R is a deuterated or unsubstituted phenyl group.

15. 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 comprises the arylamine compound of claim 1.

16. The organic electroluminescent element according to claim 15, wherein, The organic layer containing the arylamine compound is at least one layer selected from the hole injection layer, hole transport layer, electron blocking layer and light-emitting layer.

17. An electronic device having a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein, The organic layer comprises the arylamine compound of claim 1.

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