Organic electroluminescent element, electronic element, and electronic apparatus

Abstract

This organic electroluminescent element has at least an anode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and a cathode in this order, wherein the electron blocking layer includes an arylamine compound represented by general formula (I), and the light emitting layer includes a compound represented by general formula (III). This organic electroluminescent element demonstrates high efficiency and a low driving voltage, and has a long element lifespan. In the formulas, one or two among Ar1-Ar3 is or are each a substituted phenyl group represented by general formula (II), one or two among Ar6-Ar8 of general formula (III) is or are each a specific condensed polycyclic aromatic group, and L1-L6 are each a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

Description

Organic electroluminescent elements, electronic components, and electronic devices

[0001] This invention relates to organic electroluminescent elements (hereinafter abbreviated as organic EL elements), which are self-luminescent elements suitable for various display devices, and more specifically to organic electroluminescent elements (hereinafter abbreviated as organic EL elements) using specific arylamine compounds and specific heterocyclic compounds. The invention also relates to electronic elements and electronic devices using arylamine compounds and heterocyclic compounds.

[0002] Organic EL elements have been the subject of active research due to their brightness, superior visibility, and ability to display clearly compared to liquid crystal elements. In 1987, C. W. Tang et al. of Eastman Kodak made organic EL elements using organic materials practical by developing a multilayer structure element in which various roles are assigned to each material (see Patent Documents 1 and 2). Furthermore, many improvements have been made to the practical application of organic EL elements to date, and improvements in efficiency and durability have been achieved by further subdividing the roles of each layer in the multilayer structure and arranging the anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, and cathode in that order on the substrate (see, for example, Non-Patent Document 1).

[0003] Furthermore, attempts are being made to utilize triplet excitons to further improve luminescence efficiency, and the use of phosphorescent compounds and compounds exhibiting thermally activated delayed fluorescence (TADF) is being considered (see Non-Patent Literature 2 and Non-Patent Literature 3). For example, in 2011, Adachi et al. at Kyushu University achieved an external quantum efficiency of 5.3% with a device using TADF material.

[0004] To improve the efficiency, durability, and other properties of these organic EL elements, it is necessary to appropriately select the materials of each organic layer constituting the stacked structure to create an element with excellent carrier balance (see Non-Patent Literature 2). In other words, organic EL elements emit light when charges injected from both electrodes recombine in the light-emitting layer. Therefore, by selecting a material that efficiently transfers both holes and electrons to the light-emitting layer, the luminescence efficiency of the organic EL element can be improved. Furthermore, by selecting a material for the hole transport layer that not only has high hole injection properties but also high electron blocking properties that block electrons injected from the cathode, the probability of hole-electron recombination in the light-emitting layer is improved, and the generated excitons are confined within the light-emitting layer, thus achieving high luminescence efficiency. Thus, the role of hole transport materials is important, and there is a need for hole transport materials that have high hole injection properties, hole transport properties (i.e., hole mobility), and electron blocking properties, as well as high durability against electrons.

[0005] Furthermore, the heat resistance and amorphous properties of the material are also important for the lifespan of the device. The heat generated during the operation of the device can cause thermal decomposition in materials with low heat resistance and crystallization of the thin film in materials with low amorphous properties. Since thermal decomposition and crystallization of the thin film degrade the device, materials used in the organic layer are required to have high heat resistance and good amorphous properties.

[0006] U.S. Patent No. 5,792,557, U.S. Patent No. 5,639,914, U.S. Patent No. 7,759,030, International Publication No. 2016 / 006629

[0007] Proceedings of the 9th Workshop of the Japan Society of Applied Physics, 2001, pp. 55-61. Proceedings of the 9th Workshop of the Japan Society of Applied Physics, 2001, pp. 23-31. Appl. Phys. Lett., (USA), 2011, Vol. 98, No. 8, pp. 083302. Proceedings of the 3rd Meeting of the Symposium on Organic EL, 2006, pp. 13-14.

[0008] Conventionally, various aromatic amine derivatives such as N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) have been used as hole transport materials (see Patent Documents 1 and 2). However, although NPD has good hole transport properties, its glass transition temperature (Tg), which is an indicator of heat resistance, is low at 96°C, so it has the problem of crystallizing under high-temperature conditions, causing a decrease in device characteristics (see, for example, Non-Patent Document 4). Furthermore, Patent Document 3 reports an aromatic amine derivative with high durability, but this aromatic amine derivative was used as a charge transport material for electrophotographic photoreceptors, and not as a hole transport material for organic EL devices. In addition, some aromatic amine derivatives have a hole mobility of 10 －３ cm ２ Compounds with a Vs of 1 / Vs or higher and excellent hole transport properties are known (see Patent Documents 1 and 2). However, the aromatic amine derivatives used here have insufficient electron blocking properties, and when these compounds are used in the hole transport layer, some electrons pass through the light-emitting layer, resulting in insufficient luminescence efficiency.

[0009] Furthermore, aromatic amine compounds with improved properties such as heat resistance and hole injection capabilities have also been proposed (see, for example, Patent Document 4). However, even when these aromatic amine compounds are used in the hole injection layer or hole transport layer of an organic EL device, the heat resistance and luminous efficiency of the device cannot be sufficiently improved.

[0010] As described above, various hole-transporting materials have been proposed. However, improving hole-transporting materials alone has limitations in improving the efficiency, driving voltage, and lifespan of organic EL devices, and there is a need for new material designs that can effectively improve device characteristics.

[0011] The object of the present invention is to provide an organic EL element with low driving voltage, high efficiency, and long element life by finding an appropriate combination of materials to be used in a layered structure. Another object of the present invention is to provide electronic elements and electronic devices using such a combination of materials.

[0012] As a result of intensive studies conducted by the present inventors to achieve the above object, they have found that using an arylamine compound having a specific structure as a material for an electron blocking layer and a heterocyclic compound having a specific structure as a host material for a light emitting layer can realize an organic EL device with low driving voltage, high efficiency and long device lifetime. The present invention has been completed based on these findings and has the following constitution.

[0013] 1) An organic electroluminescence device comprising at least an anode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and a cathode in this order, wherein the electron blocking layer contains an arylamine compound represented by the following general formula (I), and the light emitting layer contains a compound represented by the following general formula (III).

[0014]

[0015] (wherein Ar １ to Ar ３ each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L １ to L ３ each independently represent a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking cyclic group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked via a single bond; provided that one or two of Ar １ to Ar ３ represent a substituted phenyl group represented by the following general formula (II), and at least one of L １ to L ３ is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.)

[0016]

[0017] (wherein the broken line represents the bonding site to L １ to L ３ in general formula (I). Ar ４ and Ar ５Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ n represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. １ This is the number of elements, representing an integer from 0 to 3. If n is 2 or 3, there are multiple elements R. １ They may be the same or different from each other, and when n is an integer from 1 to 3, R １ The benzene ring to which R is bonded １ , multiple adjacent R １ , R １ and Ar ４ , R １ and Ar ５ These elements may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring.

[0018]

[0019] (In the formula, Ar ６ ~Ar ８ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Ar ６ ~Ar ８ At least one of these represents a fused polycyclic aromatic group represented by any of the following general formulas (IV-1) to (IV-4). ４ ~L ６Each of these independently represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking ring group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked by a single bond. １ ~X ３ Each of these independently represents an unsubstituted methine group (-CH=) or a nitrogen atom. However, X １ ~X ３ At least one of them represents a nitrogen atom.

[0020]

[0021] (In the formula, the dashed line represents L in general formula (III) ４ ~L ６ This represents the connection point. Y and Z are independently -CR ４ R ５ -, -NR ６ -, -O-, or -S-, and at least one of Y and Z is -CR ４ R ５ Represents - or -O-. R ２ and R ３ Each independently represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ２ and R ３ Each of these may form a ring by bonding to the benzene ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. ４ ~R ６Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ４ and R ５ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. p is R ２ This is the number of elements, and represents an integer from 0 to 4. q is R ３ This is the number of elements, and represents an integer from 0 to 5. If p and q are each independent integers of 2 or greater, there are multiple R's. ２ or R ３ These may be identical or different from each other, and may be multiple adjacent Rs. ２ or R ３ These elements may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring.

[0022] 2) In the above general formula (I), Ar １ L is a substituted phenyl group represented by the general formula (II), １ The organic electroluminescent element according to 1), wherein the linking ring group is a combination of one or two groups selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted terphenylylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted thiophendiyl group, a substituted or unsubstituted pyridinediyl group, and a substituted or unsubstituted dibenzofuranyl group, and n in general formula (II) is 0.

[0023] 3) In the above general formula (I), Ar １ is a substituted phenyl group represented by the general formula (II), and in the general formula (II), Ar ４ and Ar ５ The organic electroluminescent element according to 1) or 2), wherein each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted thienyl group.

[0024] 4) In the above general formula (I), Ar １ is a substituted phenyl group represented by the general formula (II), and Ar ２ and Ar ３ At least one of the groups is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, or a substituted or unsubstituted triphenylenyl group, and is bonded to the substituted or unsubstituted aryl group. ２ and L ３ An organic electroluminescent element according to any one of claims 1) to 3), wherein at least one of the members is a linking ring group consisting of one or two groups selected from the group consisting of a single bond or a substituted or unsubstituted phenylene group and a substituted or unsubstituted naphthylene group.

[0025] 5) In the above general formula (I), L １ ~L ３ The organic electroluminescent element according to any one of items 1) to 4), wherein each is independently a linking ring group consisting of one or two groups selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted naphthylene group.

[0026] 6) In the above general formula (III), X １ ~X ３ At least two of them are nitrogen atoms, Ar ６However, it is a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-3) above, L ４ ~L ６ However, each is independently a single bond or a substituted or unsubstituted arylene group, as described in any one of items 1) to 5).

[0027] 7) In the above general formula (III), Ar ７ and Ar ８ The organic electroluminescent element according to any one of items 1) to 6), wherein each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

[0028] 8) In the above general formulas (IV-1) to (IV-4), Y is -CR ４ R ５ -, Z is -O- or -S-, p is an integer between 0 and 2, q is 0 or 1, R ２ and R ３ The organic electroluminescent element according to any one of items 1) to 7), wherein each is independently a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group.

[0029] 9) In the above general formulas (IV-1) to (IV-4), Y is -CR ４ R ５ - and Z is -O- or -S-, R ４ and R ５ The organic electroluminescent element according to any one of claims 1) to 8), wherein the alkyl group is a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group, and is identical to each other.

[0030] 10) In the above general formula (III), X １ ~X ３ is a nitrogen atom, Ar ６is a fused polycyclic aromatic group represented by general formula (IV-1) or (IV-2), and L ４ is a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group; in general formula (IV-1) or (IV-2), Y is -CR ４ R ５ -, Z is -O-, p is an integer of 0 to 2, q is 0, R ２ is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group, R ４ and R ５ are a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and are identical to each other. The organic electroluminescent device according to any one of 1) to 9).

[0031] 11) The organic electroluminescent device according to any one of 1) to 10), wherein the electron blocking layer has a two-layer structure consisting of a first electron blocking layer in contact with the hole transport layer and a second electron blocking layer in contact with the light-emitting layer, and the second electron blocking layer contains the arylamine compound represented by general formula (I).

[0032] 12) The organic electroluminescent device according to any one of 1) to 11), wherein when a direct current voltage is applied to the organic electroluminescent device in air at 25°C, the maximum emission wavelength of the light emission spectrum is 600 nm or more and 700 nm or less.

[0033] 13) An electronic device or electronic apparatus comprising a pair of electrodes and at least two organic layers sandwiched therebetween, wherein at least one of the organic layers contains the arylamine compound represented by general formula (I), and another organic layer in contact with the organic layer contains the compound represented by general formula (III).

[0034] The organic EL device of the present invention can achieve low driving voltage, high efficiency and long device lifetime because the electron blocking layer contains a specific arylamine compound and the light-emitting layer contains a specific heterocyclic compound.

[0035] This is a schematic cross-sectional view showing an example of the configuration of the organic EL element of the present invention.

[0036] The contents of the present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, numerical ranges expressed using "~" or "to" mean a range that includes the numbers written before and after "~" or "to" as the lower and upper limits, respectively. In this specification, the description "substituted or unsubstituted" means that the group to which the word is attached may be an unsubstituted group (a group in which hydrogen atoms are not substituted with substituents), or at least one hydrogen atom of the group may be substituted with substituents. All hydrogen atoms present in an unsubstituted group １ H is fine, or part or all of it ２ It may also be H (deuterium atom, deuterium D). Also, all hydrogen atoms present in the substituents. １ H is fine, or part or all of it ２ It may also be H (deuterium atom, deuterium D).

[0037] In this specification, "organic layer" means a layer containing 70% by weight or more of an organic compound, and "organic compound" means a compound containing one or more carbon atoms. For example, organic compounds can consist only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms, and halogen atoms. In this specification, "transparent" means a visible light transmittance of 50% or more, for example, 80% or more, for example, 90% or more, for example, 99% or more. Visible light transmittance can be measured using an ultraviolet-visible spectrophotometer.

[0038] <Organic Electroluminescent Element> The organic electroluminescent element (organic EL element) of the present invention has at least an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode in this order, the electron blocking layer contains the arylamine compound represented by general formula (I), and the light-emitting layer contains the compound represented by general formula (III). Hereinafter, the arylamine compound represented by general formula (I) and the compound represented by general formula (III) used in the present invention will be described.

[0039] [Arylamine Compound Represented by General Formula (I)] The organic EL element of the present invention contains the arylamine compound represented by the following general formula (I) in the light-emitting layer.

[0040]

[0041] In general formula (I), Ar １ to Ar ３ each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; provided that one or two of Ar １ to Ar ３ represent a substituted phenyl group represented by the following general formula (II), and at least one of L １ to L ３ is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

[0042] In general formula (I), Ar １ to Ar ３ and L １ to L ３ are specified according to the following rules. First, when a group corresponding to the substituted phenyl group represented by general formula (II) is present at the terminal of the portion corresponding to Ar １ -L １ -, Ar ２ -L ２ -, Ar ３ -L ３ - of the triarylamine compound, said group is Ar １ , Ar ２ or Ar ３ , and the linking group or single bond linking said group to the nitrogen atom (N) is L１ , L ２ or L ３ Let it be so. Next, the remaining Ar of the triarylamine compound １ -L １ -, Ar ２ -L ２ -, Ar ３ -L ３ Identify the aromatic ring or aromatic heterocycle closest to the end among the rings that make up the corresponding part, and if the closest to the end is an aromatic ring, define the range from that aromatic ring to the end as Ar １ Ar ２ or Ar ３ If the element closest to the end is an aromatic heterocycle, then the element from that aromatic heterocycle to the end is called Ar １ Ar ２ or Ar ３ Let's assume that Ar １ Ar ２ or Ar ３ The linking group or single bond connecting to the nitrogen atom (N) is L １ , L ２ or L ３ It shall be the case that... According to the above rules, compound 1-1 below is Ar １ The 2,5-diphenylphenyl group represented by general formula (II), L １ is a 1,4-phenylene group, Ar ２ and Ar ３ is a phenyl group, L ２ and L ３ This corresponds to a compound in which the group is 1,4-phenylene.

[0043]

[0044] In general formula (I), Ar １ ~Ar ３ One or two of these represent a substituted phenyl group represented by the following general formula (II).

[0045]

[0046] In general formula (II), the dashed line represents L in general formula (I). １ ~L ３ This represents the connection point.

[0047] In general formula (II), Ar ４ and Ar ５ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0048] Unless otherwise specified, the aromatic ring constituting the "aryl group" or the aromatic heterocycle constituting the "heteroaryl group" in this specification may be a monoring, a fused ring formed by the fusion of two or more rings, a linked ring formed by the single bond between two or more rings, or a spiroring formed by the spirobond between two or more rings. In the case of a fused ring, linked ring, or spiroring, the multiple rings may be identical or different, and may be a combination of identical or different aryl groups, a combination of identical or different heteroaryl groups, or a combination of aryl and heteroaryl groups. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example, 2 to 4. In the case of a linked ring, the number of linked rings is preferably 2 to 6, for example, 2 to 4. Examples of heteroatoms of the aromatic heterocycle constituting the heteroarylene group include nitrogen, oxygen, and sulfur atoms. The number of carbon atoms in aromatic rings and aromatic heterocycles is, for example, 6 to 42, 6 to 30, 6 to 22, 6 to 18, 6 to 14, 6 to 10, 2 to 40, 2 to 30, and 2 to 18.

[0049] Specific examples of "aryl groups" include aryl groups having 6 to 30 carbon atoms, such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthryl group, phenanthryl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perilenyl group, fluoranthenyl group, triphenylenyl group, and indenophenanthryl group. Specific examples of "heteroaryl groups" include heteroaryl groups consisting of 3 to 50 carbon atoms, such as pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthilidinyl group, phenanthrolinyl group, acridinyl group, carbolinyl group, indenodibenzofuranyl group, and indenodibenzothienyl group.

[0050] In general formula (II), Ar ４ and Ar ５ Each of these groups is preferably independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group; more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted thienyl group; and particularly preferably an unsubstituted phenyl group or an unsubstituted naphthyl group.

[0051] In general formula (II), R １R represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. １ The group is preferably a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryloxy group; more preferably a cyano group, a substituted or unsubstituted linear alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted phenyloxy group; and particularly preferably a cyano group, an unsubstituted phenyl group, an unsubstituted phenanthryl group, or an unsubstituted phenyloxy group.

[0052] In general formula (II), R １Examples of "linear or branched alkyl groups having 1 to 6 carbon atoms" in the expression "substituted or unsubstituted linear or branched alkyl groups having 1 to 6 carbon atoms" include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, and n-hexyl group. Examples of "cycloalkyl groups having 5 to 10 carbon atoms" in the expression "substituted or unsubstituted cycloalkyl groups having 5 to 10 carbon atoms" include cyclopentyl group, cyclohexyl group, 1-adamantyl group, and 2-adamantyl group. Examples of "linear or branched alkenyl groups having 2 to 6 carbon atoms" in the expression "substituted or unsubstituted linear or branched alkenyl groups having 2 to 6 carbon atoms" include alkenyl groups such as vinyl group, allyl group, isopropenyl group, and 2-butenyl group. Examples of "substituted or unsubstituted linear or branched alkyloxy groups having 1 to 6 carbon atoms" include alkyloxy groups such as methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, and n-hexyloxy group. Examples of "substituted or unsubstituted cycloalkyloxy groups having 5 to 10 carbon atoms" include cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, and 2-adamantyloxy group. Specific examples of "aryloxy groups" in "substituted or unsubstituted aryloxy groups" include phenyloxy group, biphenylyloxy group, terphenylyloxy group, naphthyloxy group, anthracenyloxy group, phenantrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, and perilennyloxy group. １ and R １A benzene ring to which R is bonded (a benzene ring as the base skeleton shown in general formula (II)), and multiple Rs bonded to the same benzene ring. １ Allies, R １ and Ar ４ , or R １ and Ar ５ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, substituted or unsubstituted amino groups, oxygen atoms, or sulfur atoms to form a ring. In one aspect of the present invention, R １ and R １ A benzene ring to which R is bonded, and multiple Rs bonded to the same benzene ring. １ Allies, R １ and Ar ４ , or R １ and Ar ５ These atoms are not bonded to each other via single bonds, substituted or unsubstituted methylene groups, substituted or unsubstituted amino groups, oxygen atoms, or sulfur atoms to form a ring.

[0053] n is R １ This is the number of elements, representing an integer from 0 to 3. If n is 2 or 3, there are multiple elements R. １ They may be the same or different from each other, and when n is an integer from 1 to 3, R １ and R １ A benzene ring to which is bonded, and multiple adjacent R １ Allies, R １ and Ar ４ , R １ and Ar ５ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. In general formula (II), n is preferably an integer from 0 to 2, more preferably 0 or 1, and particularly preferably 0.

[0054] In general formula (I), Ar １ ~Ar ３ One or two of them are substituted phenyl groups represented by general formula (II), and the remaining Ar １ ~Ar ３These are, independently, substituted or unsubstituted aryl groups not represented by general formula (II), or substituted or unsubstituted heteroaryl groups. １ ~Ar ３ and L １ ~L ３ According to the above rules for identifying aryl groups, unlike the definition of an aryl group above, linked rings in which two or more rings are connected by a single bond are not included in the definition of an "aryl group" as used here. １ ~Ar ３ This includes substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted spirobifluorenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted pyrimidinyl groups, substituted or unsubstituted triazinyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted benzoxazolyl groups, substituted or unsubstituted benzothiazolyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothienyl groups, or substituted or It is preferably an unsubstituted phenanthrolinyl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted dibenzofuranyl group, and particularly preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0055] In general formula (I), Ar １ ~Ar ３In the "substituted or unsubstituted naphthyl group" as a substituted or unsubstituted aryl group, the "naphthyl group" is preferably a 1-naphthyl group or a 2-naphthyl group. In the "substituted or unsubstituted phenanthryl group", the "phenanthryl group" is preferably a 2-phenanthryl group or a 9-phenanthryl group, and more preferably a 9-phenanthryl group. In the "substituted or unsubstituted fluorenyl group", the "fluorenyl group" is preferably a 2-fluorenyl group, a 3-fluorenyl group, or a 4-fluorenyl group, and more preferably a 2-fluorenyl group. In the "substituted or unsubstituted spirobifluorenyl group", the "spirobiofluorenyl group" is preferably a 2-spirobiofluorenyl group, a 3-spirobiofluorenyl group, or a 4-spirobiofluorenyl group, and more preferably a 2-spirobiofluorenyl group. The "triphenylenyl group" in "substituted or unsubstituted triphenylenyl group" is preferably a 2-triphenylenyl group. １ ~Ar ３ In the "substituted or unsubstituted pyridyl group" in the "substituted or unsubstituted pyridyl group", the "pyridyl group" is preferably a 2-pyridyl group or a 3-pyridyl group, with the 3-pyridyl group being more preferred. In the "substituted or unsubstituted benzoxazolyl group", the "benzoxazolyl group" is preferably a 2-benzoxazolyl group. In the "substituted or unsubstituted dibenzofuranyl group", the "dibenzofuranyl group" is preferably a 1-dibenzofuranyl group, a 2-dibenzofuranyl group or a 3-dibenzofuranyl group, with the 1-dibenzofuranyl group or a 2-dibenzofuranyl group being more preferred.

[0056] In general formula (I), L １ ~L ３ Each of these independently represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking ring group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked by a single bond. In general formula (I), L １ ~L ３The "arylene group" in the "substituted or unsubstituted arylene group" or the "heteroarylene group" in the "substituted or unsubstituted heteroarylene group" can be a group obtained by removing one hydrogen atom from the group shown above as the "aryl group" or "heteroaryl group". １ ~L ３ The "arylene group" in this context may have a ring skeleton consisting of two or more rings linked by single bonds, or L １ ~L ３ In this context, the "heteroarylene group" may have a ring skeleton of a linked ring in which two or more rings are connected by single bonds. That is, the aromatic ring constituting the "arylene group" or the aromatic heterocycle constituting the "heteroarylene group" may be a single ring, a fused ring in which two or more rings are fused, a linked ring in which two or more rings are connected by single bonds, or a spiro-ring in which two or more rings are connected by spiro bonds. In the case of a fused ring, linked ring, or spiro-ring, the multiple rings may be the same or different, and may be a combination of the same or different arylene groups, a combination of the same or different heteroarylene groups, or a combination of arylene groups and heteroarylene groups. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example 2 to 4. In the case of a linked ring, the number of linked rings is preferably 2 to 6, for example 2 to 4. Examples of heteroatoms of the aromatic heterocycle constituting the heteroarylene group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of carbon atoms in aromatic rings and aromatic heterocycles is, for example, 6 to 30, 6 to 22, 6 to 18, 6 to 14, 6 to 10, 2 to 40, 2 to 30, and 2 to 18.

[0057] In general formula (I), L １ ~L ３Specific examples of the "arylene group" in the "substituted or unsubstituted arylene group" represented by include phenylene group, biphenylylene group, terphenylylene group, naphthylene group, anthrylene group, phenanthrylene group, indenylene group, pyrenylene group, peryleneylene group, fluorantheylene group, triphenylenylene group, fluorenylene group, spirobifluorenylene group, and other arylene groups having 6 to 30 carbon atoms. １ ~L ３ Specific examples of "heteroarylene groups" in the "substituted or unsubstituted heteroarylene groups" represented by include heteroarylene groups having 2 to 20 carbon atoms, such as pyridinediyl group, pyrimidinediyl group, triazinediyl group, franziyl group, pyrrolediyl group, thiophenediyl group, quinolinediyl group, isoquinolinediyl group, benzofranziyl group, benzothiophenediyl group, indolediyl group, carbazolediyl group, benzoxazolediyl group, benzothiazolediyl group, imidazopyridinediyl group, oxazolopyridinediyl group, oxazolopyridinediyl group, quinoxalinediyl group, quinazolindiyl group, benzimidaldiyl group, pyrazolediyl group, dibenzofranziyl group, dibenzothiophenediyl group, naphthyridinediyl group, phenanthrolinediyl group, acridinediyl group, and carbolinediyl group.

[0058] In general formula (I), L １ ~L ３Preferably, each of these is a linking ring group consisting of one, two, or three groups independently selected from the group comprising: a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted terphenylylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted pyridinediyl group, a substituted or unsubstituted pyrimidinediyl group, a substituted or unsubstituted triazinediyl group, a substituted or unsubstituted franziyl group, a substituted or unsubstituted pyrrolediyl group, a substituted or unsubstituted thiophenediyl group, a substituted or unsubstituted dibenzofranziyl group, a substituted or unsubstituted dibenzothiophenediyl group, and a substituted or unsubstituted phenanthrolinediyl group. The combination of linking ring groups may be a combination of two or three identical or different arylene groups, or a combination of two or three identical or different heteroarylene groups, or a combination of one arylene group and one or two heteroarylene groups, or a combination of one or two arylene groups and one heteroarylene group. １ ~L ３ It is more preferably a linking ring group consisting of one or two groups selected from the group consisting of substituted or unsubstituted phenylene groups, substituted or unsubstituted biphenylylene groups, substituted or unsubstituted naphthylene groups, substituted or unsubstituted pyridinediyl groups, and substituted or unsubstituted thiophenediyl groups, and is particularly preferably a linking ring group consisting of one or two groups selected from the group consisting of unsubstituted phenylene groups, unsubstituted biphenylylene groups, and unsubstituted naphthylene groups. １ ~L ３It is also preferable that each of these groups independently be a linking ring group consisting of one or two groups selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted terphenylylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted an anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted thiophenediyl group, a substituted or unsubstituted pyridinediyl group, and a substituted or unsubstituted dibenzofuranyl group.

[0059] In general formula (I), L １ ~L ３ In the "substituted or unsubstituted phenylene group" in L, the "phenylene group" is preferably a 1,3-phenylene group or a 1,4-phenylene group, and more preferably a 1,4-phenylene group. In the "substituted or unsubstituted biphenylylene group", the "biphenylylene group" is preferably a 1,1'-biphenyl-4,3'-diyl group or a 1,1'-biphenyl-4,4'-diyl group, and more preferably a 1,1'-biphenyl-4,4'-diyl group. In the "substituted or unsubstituted naphthylene group", the "naphthylene group" is preferably a 1,3-naphthylene group or a 2,6-naphthylene group, and more preferably a 1,3-naphthylene group. １ ~L ３ In the "substituted or unsubstituted pyridinediyl group" as a substituted or unsubstituted heteroarylene group, the "pyridinediyl group" is preferably a 3,5-pyridinediyl group or a 2,5-pyridinediyl group, and more preferably a 3,5-pyridinediyl group. In the "substituted or unsubstituted thiophenediyl group", the "thiophenediyl group" is preferably a 2,5-thiophenediyl group or a 3,5-thiophenediyl group, and more preferably a 2,5-thiophenediyl group.

[0060] L bonded to a substituted phenyl group represented by general formula (II) １ ~L ３ These are, independently, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted terphenylylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted pyridinediyl group, a substituted or unsubstituted pyrimidinediyl group, a substituted or unsubstituted triazinediyl group, a substituted or unsubstituted thiophendiyl group, and a substituted or unsubstituted dibenzofrandiyl group. It is preferable that the linking ring group is a combination of one, two, or three groups selected from the group consisting of a phenyl group, a substituted or unsubstituted dibenzothiophenediyl group, and a substituted or unsubstituted phenanthrolinediyl group; more preferably that the linking ring group is a combination of one or two groups selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted pyridinediyl group, and a substituted or unsubstituted thiophenediyl group; and particularly preferably that the linking ring group is an unsubstituted phenylene group or an unsubstituted biphenylylene group.

[0061] L bonded to a substituted phenyl group represented by general formula (II) １ ~L ３ In this, the "phenylene group" in the "substituted or unsubstituted phenylene group" as a substituted or unsubstituted arylene group is preferably a 1,3-phenylene group or a 1,4-phenylene group, and more preferably a 1,4-phenylene group. The "biphenylene group" in the "substituted or unsubstituted biphenylylene group" is preferably a 1,1'-biphenyl-4,3'-diyl group or a 1,1'-biphenyl-4,4'-diyl group, and more preferably a 1,1'-biphenyl-4,4'-diyl group. L bonded to the substituted phenyl group represented by general formula (II) １ ~L ３In this, the "pyridinediyl group" of the "substituted or unsubstituted pyridinediyl group" as a substituted or unsubstituted heteroarylene group is preferably a 3,5-pyridinediyl group or a 2,5-pyridinediyl group, and more preferably a 3,5-pyridinediyl group. The "thiophenediyl group" of the "substituted or unsubstituted thiophenediyl group" is preferably a 2,5-thiophenediyl group or a 3,5-thiophenediyl group, and more preferably a 2,5-thiophenediyl group.

[0062] Ar １ ~Ar ３ Of these, those that are substituted phenyl groups represented by general formula (II) are Ar １ ~Ar ３ It is preferable that it be one of the following. For example, in general formula (I), Ar １ If is a substituted phenyl group represented by general formula (II), then Ar ２ and Ar ３ At least one of the groups is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, or a substituted or unsubstituted triphenylenyl group, and more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group. However, the substituted or unsubstituted aryl group here is not included in the substituted phenyl group represented by general formula (II). Also, L ２ and L ３ Each of these groups is preferably a linking ring group consisting of one or two groups selected independently from the group consisting of single-bonded, substituted or unsubstituted phenylene groups and substituted or unsubstituted naphthylene groups, and more preferably a single-bonded, substituted or unsubstituted phenylene group.

[0063] In general formulas (I) and (II), Ar １ ~Ar ５ , L １ ~L ３、R １The term "substituted or unsubstituted" for each group represented by means that at least one hydrogen atom of each group may or may not be substituted with a substituent, and if substituents are present, the number of substituents may be one or two or more. Specifically, "substituents" include: deuterium atoms; cyano groups, nitro groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; silyl groups such as trimethylsilyl and triphenylsilyl groups; linear or branched alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, and propyl groups; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy, ethyloxy, and propyloxy groups; alkenyl groups such as vinyl and allyl groups; aryloxy groups such as phenyloxy and tolyloxy groups; arylalkyloxy groups such as benzyloxy and phenethyloxy groups; phenyl, biphenylyl, and terphenylyl groups. Examples of aryl groups include naphthyl, anthracenyl, phenantrenyl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, perilenyl, fluoranthenyl, and triphenylenyl groups; and heteroaryl groups such as pyridyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carboninyl groups. These substituents may further have one or more of the exemplified substituents.The "substituent" is preferably a deuterium atom, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heteroaryl group; more preferably a deuterium atom, a cyano group, a substituted or unsubstituted linear alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenyloxy group, or a substituted or unsubstituted carbazolyl group; and particularly preferably a deuterium atom, a cyano group, an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, or an unsubstituted phenyloxy group. These substituents and the groups to which they substitute, or multiple substituents adjacent to each other, may be bonded via single bonds, substituted or unsubstituted methylene groups, N (nitrogen atom), O (oxygen atom), or S (sulfur atom) to form a ring. The resulting ring may be a monoring or a fused ring.

[0064] The arylamine compound represented by general formula (I) is preferably the arylamine compound represented by the following general formula (Ia).

[0065]

[0066] Ar ２ Ar ３ , L １ ~L ３ For an explanation of the general formula (I), see Ar ２ Ar ３ , L １ ~L ３ You can refer to the description regarding Ar ４ Ar ５ , R １ For the explanation of n, see Ar in general formula (II). ４ Ar ５ , R １ You can refer to the description of n. ２ and Ar３ It is preferably a substituted or unsubstituted aryl group, and more preferably a substituted or unsubstituted phenyl group (excluding substituted phenyl groups represented by general formula (II)), Ar ２ and Ar ３ It is also preferable that one of the groups is an aryl group which may be substituted with an alkyl group, and the other is an aryl group which is substituted with an aryl group (for example, a phenyl group which is substituted with a substituted or unsubstituted naphthyl group). ２ and L ３ It is preferably a single-bonded, substituted, or unsubstituted arylene group, and more preferably a single-bonded, substituted, or unsubstituted phenylene group, or a substituted or unsubstituted biphenylylene group. ４ and Ar ５ n is preferably a substituted or unsubstituted aryl group, and more preferably a substituted or unsubstituted phenyl group. n is preferably 0 or 1. １ It is preferably a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylylene group.

[0067] Specific examples of compounds represented by general formula (I) are given below. However, compounds represented by general formula (I) that can be used in the present invention should not be interpreted as being limited by these specific examples. Also, in the chemical structural formulas below, hydrogen atoms ( １ The notation H) is omitted, and the deuterium atom ( ２ H) is written as "D".

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] Compounds represented by general formula (I) can be synthesized by applying known coupling reactions and appropriately selecting known reaction conditions. For details of the reaction, please refer to the synthesis examples described later. The arylamine compounds represented by general formula (I) can be purified by known methods such as column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization with solvents, and sublimation purification. Compound identification can be performed, for example, by NMR analysis or mass spectrometry (MS).

[0075] Examples of physical properties of compounds represented by general formula (I) include the melting point, glass transition temperature (Tg), and HOMO (Highest Occupied Molecular Orbital) energy level. It is preferable to measure the glass transition temperature and HOMO energy level. The melting point is an indicator of vapor deposition properties, the glass transition temperature (Tg) is an indicator of the stability of the thin film state, and the HOMO energy level is an indicator of hole injection properties, hole transport properties, or electron blocking properties.

[0076] The melting point and glass transition point of the powder can be measured using a high-sensitivity differential scanning calorimeter (e.g., Bruker AXS, model: DSC3100SA). The HOMO energy level can be measured for a 100 nm thin film fabricated on a silicon substrate using an ionization potential analyzer (e.g., Sumitomo Heavy Industries, Ltd., model: PYS-202).

[0077] [Compound represented by general formula (III)] The organic electroluminescent element of the present invention contains a compound represented by the following general formula (III) in the light-emitting layer.

[0078]

[0079] In general formula (III), Ar ６ ~Ar ８ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Ar ６ ~Ar ８At least one of these represents a condensed polycyclic aromatic group represented by any of the following general formulas (IV-1) to (IV-4).

[0080] In general formula (III), Ar ６ ~Ar ８ and L ４ ~L ６ The following rules are used to identify the compound represented by general formula (III). ６ -L ４ -, Ar ７ -L ５ -, Ar ８ -L ６ If the terminal of the part corresponding to - has a group that corresponds to a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-4), then that group is Ar ６ Ar ７ or Ar ８ The linking group or single bond connecting that group to the nitrogen atom (N) is L ４ , L ５ or L ６ Let it be so. Next, the remaining Ar of the compound represented by general formula (III) ６ -L ４ -, Ar ７ -L ５ -, Ar ８ -L ６ Identify the aromatic ring or aromatic heterocycle closest to the end among the rings that make up the corresponding part, and if the closest to the end is an aromatic ring, define the range from that aromatic ring to the end as Ar ６ Ar ７ or Ar ８ If the element closest to the end is an aromatic heterocycle, then the element from that aromatic heterocycle to the end is called Ar ６ Ar ７ or Ar ８ Let's assume that Ar ６ Ar ７ or Ar ８ The linking group or single bond connecting to the nitrogen atom (N) is L ４ , L ５ or L ６ It shall be the case that... According to the above rules, compound 3-1 below is Ar ６L is a group represented by the general formula (IV-1). ４ is a single bond, Ar ７ and Ar ８ is a phenyl group, L ５ and L ６ This corresponds to a compound with a single bond.

[0081]

[0082] In general formula (III), Ar ６ ~Ar ８ For an explanation of the "aryl group" in "substituted or unsubstituted aryl group" or the "heteroaryl group" in "substituted or unsubstituted heteroaryl group" represented by Ar in general formula (I), please refer to the following: １ ~Ar ３ You can refer to the explanation of the "aryl group" or "heteroaryl group" represented by this symbol.

[0083] In general formula (III), Ar ６ ~Ar ８These are, independently, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted indenophenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, and a substituted... or unsubstituted benzothienyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted benzoxazolyl group, substituted or unsubstituted benzothiazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothienyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted indenodibenzofuranyl group Preferably, it is a substituted or unsubstituted indenodibenzothienyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted indenophenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted It is more preferably an unsubstituted indenodibenzofuranyl group or a substituted or unsubstituted indenodibenzothienyl group, and particularly preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted indenophenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indenodibenzofuranyl group, or a substituted or unsubstituted indenodibenzothienyl group.

[0084] In general formula (III), Ar ６ ~Ar ８In the substituted or unsubstituted aryl group, the "substituted or unsubstituted phenyl group" is preferably an unsubstituted phenyl group or a 4-substituted phenyl group. As substituents on the 4-substituted phenyl group, linear or branched alkyl groups having 1 to 4 carbon atoms are preferred. In the "substituted or unsubstituted naphthyl group", the "naphthyl group" is preferably a 1-naphthyl group or a 2-naphthyl group, and more preferably a 1-naphthyl group. In the "substituted or unsubstituted phenanthryl group", the "phenanthryl group" is preferably a 9-phenanthryl group. In the "substituted or unsubstituted fluorenyl group", the "fluorenyl group" is preferably a 1-fluorenyl group or a 2-fluorenyl group, and more preferably a 2-fluorenyl group. The "spirobifluorenyl group" in "substituted or unsubstituted spirobifluorenyl group" is preferably a 1-spirobifluorenyl group or a 2-spirobifluorenyl group, and more preferably a 2-spirobifluorenyl group. The "indenyl group" in "substituted or unsubstituted indenyl group" is preferably a 6-indenyl group. The "indenophenanthryl group" in "substituted or unsubstituted indenophenanthryl group" is preferably an 11H-indeno[2,1-a]phenanthryl group, more preferably an 11H-indeno[2,1-a]phenanthren-5-yl group, or more preferably an 11H-indeno[2,1-a]phenanthren-6-yl group. Ar ６ ~Ar ８In the "substituted or unsubstituted dibenzofuranyl group" as a substituted or unsubstituted heteroaryl group, the "dibenzofuranyl group" is preferably a 1-dibenzofuranyl group or a 2-dibenzofuranyl group. In the "substituted or unsubstituted dibenzothienyl group", the "dibenzothienyl group" is preferably a 1-dibenzothienyl group or a 2-dibenzothienyl group. In the "substituted or unsubstituted carbazolyl group", the "carbazolyl group" is preferably a 1-carbazolyl group, a 2-carbazolyl group, or a 9-carbazolyl group, and more preferably a 9-carbazolyl group. The "substituted or unsubstituted indenodibenzofuranyl group" or "substituted or unsubstituted indenodibenzothienyl group" is preferably an indenodibenzofuranyl group or indenodibenzothienyl group represented by any of the following general formulas (IV-1) to (IV-4), and more preferably an indenodibenzofuranyl group or indenodibenzothienyl group represented by the following general formulas (IV-1) or (IV-2).

[0085] In general formula (III), Ar ６ ~Ar ８ At least one of these represents a condensed polycyclic aromatic group represented by any of the following general formulas (IV-1) to (IV-4).

[0086]

[0087] In general formulas (IV-1) to (IV-4), the dashed line represents L in general formula (III). ４ ~L ６ This represents the connection point.

[0088] In general formulas (IV-1) to (IV-4), Y and Z are each independently -CR ４ R ５ -, -NR ６ -, -O-, or -S-, and at least one of Y and Z is -CR ４ R ５ Represents - or -O-. Here, -CR is represented by Y and Z. ４ R ５ - is R ４ and R５ Represents a methylene group substituted with -NR ６ - is R ６ The substituted nitrogen atom (imino group) is represented by -O-, the oxygen atom (ether bond) is represented by -S-, and the sulfur atom (sulfide bond) is represented by -CR. ４ R ５ - or -O- is preferred, and -CR ４ R ５ - is more preferable. Z is -CR ４ R ５ It is preferable that it be -, -O-, or -S-, more preferably -O-, or -S-, and particularly preferably -O-. As for the combination of Y and Z, Y is -CR ４ R ５ It is preferable that Z is -O- or -S-. For example, Y is -CR ４ R ５ When - and Z is -O-, the general formulas (IV-1) to (IV-4) represent an indenodibenzofuranyl group, and Y is -CR ４ R ５ When Z is -S-, general formulas (IV-1) to (IV-4) represent an indenodibenzothienyl group. In general formula (III), the indenodibenzofuranyl group or indenodibenzothienyl group represented by general formulas (IV-1) to (IV-4) is preferably an indenodibenzofuranyl group or indenodibenzothienyl group represented by general formula (IV-1) or (IV-2).

[0089] In general formulas (IV-1) to (IV-4), R ４ ~R ６Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ４ and R ５ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. ４ ~R ６ It is preferably a hydrogen atom, a deuterium atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryloxy group; more preferably a substituted or unsubstituted linear alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted phenyloxy group; and particularly preferably a hydrogen atom, a methyl group, or an unsubstituted phenyl group. ４ and R ５ If the group is a phenyl group, it may be bonded to each other by a single bond to form a ring.

[0090] In general formulas (IV-1) to (IV-4), R ２ and R ３Each independently represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ２ and R ３ Each of these may form a ring by bonding to the benzene ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. ２ and R ３ Each of these groups is preferably independently a deuterium atom, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group; more preferably a deuterium atom, a cyano group, a substituted or unsubstituted linear alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted phenyloxy group; and particularly preferably an unsubstituted phenyl group, a substituted triazinyl group, or an unsubstituted phenyloxy group.

[0091] In general formulas (IV-1) to (IV-4), R ２ ~R ６For an explanation and specific examples of the "substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms", "substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms", "substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms", "substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms", "substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms", "substituted or unsubstituted aryl group", "substituted or unsubstituted heteroaryl group", or "substituted or unsubstituted aryloxy group" represented by general formula (II), see R １ You can refer to the descriptions of "substituted or unsubstituted linear or branched alkyl groups having 1 to 6 carbon atoms," "substituted or unsubstituted cycloalkyl groups having 5 to 10 carbon atoms," "substituted or unsubstituted linear or branched alkenyl groups having 2 to 6 carbon atoms," "substituted or unsubstituted linear or branched alkyloxy groups having 1 to 6 carbon atoms," "substituted or unsubstituted cycloalkyloxy groups having 5 to 10 carbon atoms," "substituted or unsubstituted aryl groups," "substituted or unsubstituted heteroaryl groups," or "substituted or unsubstituted aryloxy groups."

[0092] In general formulas (IV-1) to (IV-4), p is R ２ This is the number of elements, and represents an integer from 0 to 4. q is R ３ This is the number of elements, and represents an integer from 0 to 5. If p and q are each independent integers of 2 or greater, there are multiple R's. ２ or R ３ These may be identical or different from each other, and may be multiple adjacent Rs. ２ or R ３ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring.) p is preferably an integer from 0 to 3, more preferably an integer from 0 to 2, and particularly preferably 0 or 2. q is preferably an integer from 0 to 2, more preferably 0 or 1, and particularly preferably 0.

[0093] In general formula (III), L ４ ~L ６ Each of these independently represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking ring group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked by a single bond. ４ ~L ６ For an explanation of the "arylene group" in "substituted or unsubstituted arylene group" or the "heteroarylene group" in "substituted or unsubstituted heteroarylene group" represented by L in general formula (I), see the following: １ ~L ３ You can refer to the explanation of the "arylene group" or "heteroarylene group" represented by this symbol.

[0094] In general formula (III), L ４ ~L ６ Preferably, each of these is a linking ring group consisting of one, two, or three groups independently selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridinediyl group, a substituted or unsubstituted pyrimidinediyl group, a substituted or unsubstituted triazinediyl group, and a substituted or unsubstituted quinolinediyl group. The combination of linking ring groups may be a combination of two or three identical or different arylene groups, a combination of two or three identical or different heteroarylene groups, a combination of one arylene group and one or two heteroarylene groups, or a combination of one or two arylene groups and one heteroarylene group. ４ ~L ６ It is more preferably a linking ring group consisting of one or two groups selected from the group consisting of substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, and substituted or unsubstituted pyridinediyl groups, and is particularly preferably a substituted or unsubstituted phenylene group. ４ ~L ６It is also preferable that each of these be a linking ring group consisting of one or two groups selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted pyridinediyl group, and more preferably a linking ring group consisting of one or two groups selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group.

[0095] In general formula (III), L ４ ~L ６ In the "substituted or unsubstituted phenylene group" in L, the "phenylene group" is preferably a 1,3-phenylene group or a 1,4-phenylene group, and more preferably a 1,4-phenylene group. In the "substituted or unsubstituted naphthylene group", the "naphthylene group" is preferably a 2,6-naphthylene group. ４ ~L ６ In the "substituted or unsubstituted pyridinediyl group" as a substituted or unsubstituted heteroarylene group in the above, the "pyridinediyl group" is preferably a 2,3-pyridinediyl group or a 2,5-pyridinediyl group.

[0096] In general formula (III), Ar ６ ~Ar ８ One or two of them are condensed polycyclic aromatic groups represented by any of the general formulas (IV-1) to (IV-4), and Ar ６ ~Ar ８ The remaining groups are substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups (excluding condensed polycyclic aromatic groups represented by any of the general formulas (IV-1) to (IV-4)).

[0097] In general formula (III), L is bonded to a condensed polycyclic aromatic group represented by any of general formulas (IV-1) to (IV-4). ４ ~L ６ It is preferable that the L bonded to the condensed polycyclic aromatic group represented by general formulas (IV-1) to (IV-4)４ ~L ６ In this, the "substituted or unsubstituted arylene group" is preferably a linking ring group consisting of one, two or three groups independently selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, and a substituted or unsubstituted naphthylene group; more preferably a linking ring group consisting of one or two groups independently selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted naphthylene group; and particularly preferably an unsubstituted phenylene group or an unsubstituted naphthylene group.

[0098] L to which a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-4) is bonded. ４ ~L ６ In this, the "phenylene group" in the "substituted or unsubstituted phenylene group" as a substituted or unsubstituted arylene group is preferably a 1,3-phenylene group or a 1,4-phenylene group, and more preferably a 1,4-phenylene group. The "biphenylene group" in the "substituted or unsubstituted biphenylylene group" is preferably a 1,1'-biphenyl-4,3'-diyl group or a 1,1'-biphenyl-4,4'-diyl group, and more preferably a 1,1'-biphenyl-4,4'-diyl group. The "naphthylene group" in the "substituted or unsubstituted naphthylene group" is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.

[0099] Ar ６ ~Ar ８ Of these, those that are condensed polycyclic aromatic groups represented by any of the general formulas (IV-1) to (IV-4) are Ar ６ ~Ar ８ It is preferable that it be one of the following. For example, in general formula (III), Ar ６ If is a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-4), then Ar ６It is preferably a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-3), and more preferably a condensed polycyclic aromatic group represented by the general formula (IV-1) or (IV-2). Also, Ar ７ and Ar ８ At least one of the groups is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group, and more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group. However, the substituted or unsubstituted aryl group and the substituted or unsubstituted heteroaryl group here are not included in the condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-4). Also, L ５ and L ６ Each of these groups is preferably a linking ring group consisting of one or two groups selected independently from the group consisting of single-bonded, substituted or unsubstituted phenylene groups and substituted or unsubstituted naphthylene groups, and more preferably a single-bonded, substituted or unsubstituted phenylene group.

[0100] In general formula (III), X １ ~X ３ Each of these independently represents an unsubstituted methine group (-CH=) or a nitrogen atom. However, X １ ~X ３ At least one of them represents a nitrogen atom. １ ~X ３ Preferably, at least two of them are nitrogen atoms, X １ ~X ３ It is more preferable that it is a nitrogen atom. １ ~X ３If any two of them are nitrogen atoms, then X adjacent to the carbon atom bonded to the condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-4) １ ~X ３ It is preferable that any two of them are nitrogen atoms. For example, Ar ６ If is a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-4), then X １ and X ２ It is preferable that it is a nitrogen atom.

[0101] In general formulas (III) and (IV-1) to (IV-4), Ar ６ ~Ar ８ , L ４ ~L ６ , R ２ ~R ６ For explanations of "substituted or unsubstituted" for each group represented by and specific examples of substituents, refer to the descriptions of "substituted or unsubstituted" for each group in general formulas (I) and (II).

[0102] In general formula (III) and (IV-1) to (IV-4), Ar ６ ~Ar ８ , L ４ ~L ６ , or R ２ ~R ６ When each of the substituted or unsubstituted groups represented by has a substituent, the substituent is preferably a deuterium atom, a cyano group, a fluorine atom, a silyl group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heteroaryl group; more preferably a deuterium atom, a substituted or unsubstituted linear alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted phenyloxy group, or a substituted or unsubstituted carbazolyl group; and particularly preferably a deuterium atom, a cyano group, an unsubstituted phenyl group, an unsubstituted biphenylyl group, or an unsubstituted phenyloxy group.

[0103] Specific examples of compounds represented by general formula (III) are shown in chemical formula 11. However, the compounds represented by general formula (III) that can be used in the present invention should not be interpreted as being limited by these specific examples. In addition, in the following chemical structural formulas, the notation for hydrogen atoms (1H) is omitted, and deuterium atoms (2H) are represented as "D".

[0104]

[0105] The heterocyclic compound of general formula (III) used in the present invention may be selected from chemical formulas 1 to 101 described in Korean Published Patent No. 10-2017-0056431. The descriptions of the Korean Published Patent as described in this paragraph are incorporated herein by reference as part of this specification. Furthermore, the heterocyclic compound represented by general formula (III) can be synthesized by referring to the synthesis procedures described in these publications.

[0106] [Electrodes and Organic Layers Constituting an Organic Electroluminescent Element] The organic EL element of the present invention has an anode, a cathode, a hole transport layer sandwiched between the anode and cathode, an electron blocking layer, an emissive layer, and an electron transport layer. At least one layer of the electron blocking layer contains a compound represented by general formula (I), and at least one layer of the emissive layer contains a compound represented by general formula (III). Examples of organic EL element structures include, as shown in Figure 1, a structure in which an anode 2, a hole transport layer 4, an electron blocking layer, an emissive layer 7, an electron transport layer 8, a cathode 10, and a capping layer 11 are sequentially stacked on a glass substrate 1. Other examples include a structure having a hole injection layer 3 between the anode 2 and the hole transport layer 4, a structure having a hole blocking layer (not shown) between the emissive layer 7 and the electron transport layer 8, and a structure having an electron injection layer 9 between the electron transport layer 8 and the cathode 10. In other words, the organic EL element of the present invention does not exclude configurations in which other layers are present between each layer, as long as it has at least an anode, a hole transport layer, an electron blocking layer, an emissive layer, an electron transport layer, and a cathode in that order. In these multilayer structures, one organic layer can perform multiple roles. For example, a configuration in which a hole injection layer and a hole transport layer are combined, and / or a configuration in which an electron transport layer and an electron injection layer are combined, is also possible. Furthermore, a configuration in which two or more organic layers having the same function are stacked is also possible. Specifically, examples include a configuration in which two hole transport layers are stacked, a configuration in which two electron blocking layers are stacked, a configuration in which two emissive layers are stacked, a configuration in which two electron transport layers are stacked, and / or a configuration in which two capping layers are stacked. The electron blocking layer can also be configured in which two or more layers are stacked, such as a first electron blocking layer 5 in contact with the hole transport layer and a second electron blocking layer 6 in contact with the emissive layer.

[0107] In one embodiment of the present invention, each organic layer constituting the organic EL element may be formed as a single film made of one type of material, or as a mixed film made by mixing multiple types of materials. Furthermore, it may be a single-layer structure of a single film or a mixed film, a laminated structure of multiple single films stacked together, a laminated structure of multiple mixed films stacked together, or a laminated structure of one or more single films and one or more mixed films stacked together. Film formation can be carried out by known methods such as vapor deposition, spin coating, and inkjet. In the following, each component and each layer of the organic EL element will be described in detail.

[0108] [Anode] For the anode of the organic EL element of the present invention, electrode materials with a large work function, such as ITO (indium tin oxide) or gold, are used.

[0109] [Hole Injection Layer, Hole Transport Layer] The hole injection layer is provided between the anode and the light-emitting layer, or between the anode and the hole transport layer, etc., and is provided to lower the injection barrier of holes supplied from the anode, thereby reducing the driving voltage and improving the luminescence brightness. The hole transport layer is a layer that has the function of transporting holes. The hole transport layer may also be a hole injection transport layer that also functions as a hole injection layer. Compounds represented by general formula (I) can be used as materials for the hole injection layer, hole transport layer, and hole injection transport layer. The compound represented by general formula (I) used in these layers may be one or more types from the group of compounds represented by general formula (I). In addition, compounds represented by general formula (I) may be used in combination with other hole injection materials and hole transport materials. Materials that can be used other than compounds represented by general formula (I) are described below.

[0110] As materials for the hole injection layer of the organic EL device of the present invention, the following can be used: porphyrin compounds represented by copper phthalocyanine, starburst-type triphenylamine derivatives, arylamine compounds having two or more triphenylamine structures or carbazolyl structures in the molecule, each linked by a single bond or a divalent group that does not contain a heteroatom, acceptor-type heterocyclic compounds such as hexacyanoazatriphenylene, and coated polymer materials.

[0111] As hole-transporting materials that can be used as the hole injection layer, hole transport layer, and hole injection transport layer of the organic EL device of the present invention, benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)-benzidine (TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (NPD), and N,N,N',N'-tetrabiphenylbenzidine, 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), and arylamine compounds having two or more triphenylamine structures or carbazolyl structures in the molecule, each linked by a single bond or a divalent group that does not contain a heteroatom, can be used. In addition, as the material for the hole injection layer, hole transport layer, and hole injection transport layer, a coating-type polymer material such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrene sulfonate) (PSS) can be used.

[0112] Furthermore, hole injection layers, hole transport layers, and hole injection transport layers may be constructed by adding P-type dopants such as trisbromophenylamine hexachloroantimony or radialene derivatives described in European Patent No. 2684932 to these hole injection materials or hole transport materials, or by adding polymer compounds having the structure of benzidine derivatives such as TPD as a substructure.

[0113] The absolute value of the HOMO energy level of a hole transport material is preferably greater than the absolute value of the HOMO energy level of a general hole transport material such as NPDs and TPDs (5.4 eV) (i.e., it has a deeper HOMO energy level), and preferably less than the absolute value of the HOMO energy level of an electron blocking material described later. Specifically, the absolute value of the HOMO energy level of a hole transport material is preferably between 5.45 eV and 5.80 eV, and more preferably between 5.60 eV and 5.75 eV.

[0114] [Electron Blocking Layer] An electron blocking layer is a layer that is placed, for example, between an emissive layer and a hole transport layer, and has the function of suppressing the diffusion of electrons present in the emissive layer to the outside of the emissive layer (towards the hole transport layer). This can improve the probability of electron-hole recombination in the emissive layer. Electron blocking layers usually also have the function of transporting holes. Furthermore, an electron blocking layer may also function as an exciton blocking layer, suppressing the diffusion of excitons from the emissive layer.

[0115] The material used for the electron blocking layer is a compound represented by general formula (I). Note that the compound represented by general formula (I) may also be included in organic layers other than the electron blocking layer. In a configuration with two stacked electron blocking layers, the compound represented by general formula (I) may be included in either the first electron blocking layer (the electron blocking layer in contact with the hole transport layer) or the second electron blocking layer (the electron blocking layer in contact with the light-emitting layer), or it may be included in both the first and second electron blocking layers, but it is preferable that it be included in the second electron blocking layer. The compound represented by general formula (I) may be included only in the electron blocking layer among the organic layers placed between the anode and the light-emitting layer, or it may also be included in the hole transport layer, for example. The compound represented by general formula (I) exhibits excellent hole injection, hole transport, and electron blocking properties, high electron resistance, stability even in a thin film state, and also has the characteristic of confining excitons generated in the light-emitting layer. As a result, organic EL devices using the compound represented by general formula (I) as an electron-blocking material have a higher probability of hole-electron recombination and suppress thermal deactivation, thus exhibiting high luminous efficiency, improved current tolerance due to a lower driving voltage, and enhanced maximum luminous brightness and device lifespan. The compound represented by general formula (I) used in the electron-blocking layer may be one or more compounds from the group of compounds represented by general formula (I). In addition, the compound represented by general formula (I) may be used in combination with other electron-blocking materials. The following describes materials that can be used other than the compound represented by general formula (I).

[0116] As the material for the electron blocking layer of the organic EL device of the present invention, in addition to the arylamine compound represented by the general formula (I) above, other electron-blocking compounds can be used, such as carbazole derivatives like 4,4′,4′′-tri(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazole-9-yl)phenyl]fluorene, 1,3-bis(carbazole-9-yl)benzene (mCP), and 2,2-bis(4-carbazole-9-ylphenyl)adamantane (Ad-Cz), and compounds having a triphenylsilyl group and a triarylamine structure, such as 9-[4-(carbazole-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene.

[0117] The glass transition temperature of the electron-blocking material is preferably 100.0°C or higher, more preferably 104.6°C or higher, and even more preferably 110.0°C or higher.

[0118] It is preferable that the absolute value of the HOMO energy level of the electron blocking material is greater than the absolute value of the HOMO energy level of the hole transport material (i.e., it has a deeper HOMO level). Specifically, it is preferable that the absolute value of the HOMO energy level of the electron blocking material is 5.55 eV or more and 5.90 eV or less, and more preferably 5.65 eV or more and 5.80 eV. Furthermore, it is preferable that the absolute value of the HOMO energy level of the electron blocking material is approximately 0.05 eV or more and 0.45 eV or less greater than the absolute value of the HOMO energy level of the hole transport material, more preferably 0.05 eV or more and 0.35 eV or less greater, and even more preferably 0.10 eV or more and 0.35 eV or less greater.

[0119] [Emitting Layer] The emitting layer is a layer that emits light after generating excitons by the recombination of holes and electrons injected from the anode and cathode, respectively. The emitting layer may be used alone, but it preferably includes an emitting material and a host material.

[0120] The light-emitting layer of the organic EL element of the present invention uses a compound represented by general formula (III). The compound represented by general formula (III) may be contained only in the light-emitting layer of the organic EL element, or it may be contained in organic layers other than the light-emitting layer (for example, the electron transport layer), but it is preferable that it is contained in the light-emitting layer.

[0121] The compound represented by general formula (I) can exhibit even better effects when used in combination with the compound represented by general formula (III) in an organic EL element. Specifically, by using the compound represented by general formula (I) and the compound represented by general formula (III) in combination in an organic EL element, the luminous efficiency is further improved, and the durability of the element can be further improved by lowering the driving voltage, making it easier to obtain characteristics of higher efficiency, lower driving voltage, and longer lifespan. For this reason, an electron-blocking material consisting of the compound represented by general formula (I) for use in combination with the compound represented by general formula (III) can be provided; and an organic EL element having an electron-blocking layer containing the compound represented by general formula (I) and an emissive layer containing the compound represented by general formula (III) (it is preferable that these two layers are adjacent to each other).

[0122] In addition to the compound represented by general formula (III), known light-emitting materials and host materials may be used for the light-emitting layer of the organic EL element of the present invention. The light-emitting material may be a fluorescent light-emitting material, a phosphorescent light-emitting material, or a delayed-fluorescence material, but a phosphorescent light-emitting material is preferred. The host material preferably contains the compound represented by general formula (III).

[0123] As a fluorescent material, tris(8-quinolinolato)aluminum (Alq ３ In addition to metal complexes of quinolinol derivatives, including ), various metal complexes, anthracene derivatives, bis-styrylbenzene derivatives, pyrene derivatives, oxazole derivatives, poly(p-phenylenevinylene) derivatives, etc., can be used. Furthermore, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, indenophenanthrene derivatives, rhodamine derivatives, aminostyryl derivatives, etc., can be used.

[0124] As the phosphorescent material, metal complexes with iridium or platinum as the central metal can be used. For example, green phosphorescent materials such as Ir(ppy)3, blue phosphorescent materials such as Firpic and Fir6, and red phosphorescent materials such as Btp2Ir(acac) can be used. To avoid concentration quenching, the amount of phosphorescent material doped into the host material is preferably in the range of 1 to 30% by weight of the total amount of the luminescent layer, and is preferably doped by co-deposition.

[0125] As delayed fluorescence materials, carbazolyl dicyanobenzene (CDCB) derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN can be used. For specific examples of these and other delayed fluorescence materials, please refer to Non-Patent Document 3.

[0126] Examples of host materials used in the light-emitting layer include anthracene derivatives, heterocyclic compounds having an indole ring as a substructure of the fused ring, heterocyclic compounds having a carbazole ring as a substructure of the fused ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives. Examples of host materials having hole injection and hole transport properties include carbazole derivatives such as 4,4′-di(N-carbazolyl)biphenyl (CBP), TCTA, and mCP, while examples of host materials having electron transport properties include p-bis(triphenylsilyl)benzene (UGH2) and 2,2′,2′′-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI).

[0127] [Hole Blocking Layer] The hole blocking layer is a layer that is placed, for example, between the light-emitting layer and the electron transport layer, and has the function of suppressing the diffusion of holes present in the light-emitting layer to the outside of the light-emitting layer (towards the electron transport layer), thereby improving the probability of electron-hole recombination in the light-emitting layer. The hole blocking layer usually also has the function of transporting electrons. Furthermore, the hole blocking layer may also function as an exciton blocking layer to suppress the diffusion of excitons from the light-emitting layer. As the material for the hole blocking layer of the organic EL device of the present invention, metal complexes of phenanthroline derivatives such as bathocuproine (BCP) and quinolinol derivatives such as bis(2-methyl-8-quinolinate)-4-(phenylphenolate)aluminum (BAlq), as well as various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and other compounds having hole-blocking properties can be used. These materials may also serve as the material for the electron transport layer.

[0128] [Electron injection layer, electron transport layer] The electron injection layer is provided between the cathode and the light-emitting layer, or between the cathode and the electron transport layer, etc., and is provided to lower the electron injection barrier of electrons supplied from the cathode, thereby reducing the driving voltage and improving the luminescence brightness. The electron transport layer is a layer that has the function of transporting electrons. The electron transport layer may also be an electron injection transport layer that also functions as an electron injection layer.

[0129] As a material for the electron transport layer of the organic EL element of the present invention, Alq ３ Metal complexes of quinolinol derivatives including BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, silole derivatives, etc. can be used.

[0130] As the material 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 aluminum oxide, or metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. By constructing the electron transport layer and cathode from preferred materials, the electron injection layer can be omitted.

[0131] Furthermore, in the electron injection layer or electron transport layer, metals such as cesium (N-type dopants) may be added to the electron injection material or electron transport material.

[0132] [Cathode] As the cathode of the organic EL element of the present invention, metals with a low work function such as aluminum, or alloys with an even lower work function such as magnesium-silver alloy, magnesium-indium alloy, or aluminum-magnesium alloy can be used.

[0133] <Electronic Elements or Electronic Devices> The electronic elements or electronic devices of the present invention have a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein at least one layer of the organic layer contains an arylamine compound represented by general formula (I), and at least one layer of the organic layer contains a heterocyclic compound represented by general formula (III). The organic layer preferably has a hole transport layer, an electron blocking layer, an emissive layer and an electron transport layer, and it is more preferable that the electron blocking layer contains the compound represented by general formula (I), and the emissive layer contains the compound represented by general formula (III). Examples of electronic devices include display devices and light-emitting devices equipped with organic EL elements, as well as electrophotographic photoreceptors, image sensors, photoelectric conversion elements, solar cells, etc. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablets, or personal computers. Examples of light-emitting devices include lighting or vehicle lights.

[0134] The embodiments of the present invention will be specifically described below with reference to examples. The materials, processing content, processing procedures, etc., shown below can be modified as appropriate, as long as they do not exceed the spirit of the present invention. Therefore, the scope of the present invention is not limited to the following examples. The reagents used in the synthesis examples were those manufactured by Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich, Alfa Aesar, etc. Furthermore, all reactions in the synthesis examples were carried out using a reaction vessel equipped with a condenser, a stirrer, and a thermometer. The identification of the compounds in the synthesis examples was as follows: １ 1H-NMR analysis (Bruker nuclear magnetic resonance spectrometer, model: Ascend) ＴＭ The analysis was performed using a 400 MHz (AVICY Excoria) or MS (AVICY Excoria Mass Spectrometer, Model: API3200).

[0135] [Synthesis Examples] <Synthesis Example 1: Synthesis of Compound (1-4)> In a reaction vessel, 10.0 g of bis(4-naphthalene-2-yl-phenyl)amine, 11.0 g of 4-bromo-2',5'-diphenyl-biphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri(t-butyl)phosphine, and 2.7 g of t-butoxysodium were charged and stirred under reflux in toluene for 3 hours. After cooling, the filtrate obtained by filtration was concentrated to obtain the crude product. The obtained crude product was purified by crystallization in a toluene / acetone mixed solvent to obtain 9.0 g of white powder of bis(4-naphthalene-2-yl-phenyl)-(2',5'-diphenyl-biphenyl-4-yl)amine (compound (1-4)): (yield: 52.3%).

[0136] Regarding the obtained white powder, １ H-NMR (CDCl ３ The following 39 hydrogen signals were detected and the structure was identified: δ (ppm) = 8.06 (2H), 7.92 (6H), 7.78 (4H), 7.73 (1H), 7.68 (5H), 7.53 (7H), 7.42 (1H), 7.39-7.23 (9H), 7.14 (4H). Melting point: 221°C

[0137] <Synthesis Example 2: Synthesis of Compound (1-58)> In a reaction vessel, 8.5 g of (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-1-ylphenyl)-amine, 4.8 g of 9-bromophenancelene, 0.1 g of palladium(II) acetate, 0.3 g of tri(t-butyl)phosphine, and 2.3 g of t-butoxysodium were charged and stirred under reflux in toluene for 3 hours. After cooling, the filtrate obtained by filtration was concentrated to obtain the crude product. The obtained crude product was purified by crystallization in a toluene / acetone mixed solvent to obtain 8.3 g of white powder (yield: 73.1%) of (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-1-ylphenyl)-phenancelene-9-ylamine (compound (1-58)).

[0138] Regarding the obtained white powder, １ H-NMR (CDCl ３ The following 37 hydrogen signals were detected and the structure was identified: δ (ppm) = 8.79 (1H), 8.75 (1H), 8.14 (1H), 8.03 (1H), 7.92 (1H), 7.85 (2H), 7.72 (6H), 7.65 (2H), 7.60 (1H), 7.50 (7H), 7.42 (1H), 7.36 (3H), 7.27-7.18 (6H), 7.09 (4H). Melting point: None

[0139] <Synthesis Example 3: Synthesis of Compound (1-59)> In a reaction vessel, 8.0 g of (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-2-ylphenyl)-amine, 4.5 g of 9-bromophenancelene, 0.1 g of palladium(II) acetate, 0.2 g of tri(t-butyl)phosphine, and 2.2 g of t-butoxysodium were charged and stirred under reflux in toluene for 3 hours. After cooling, the filtrate obtained by filtration was concentrated to obtain the crude product. The obtained crude product was purified by crystallization in a toluene / acetone mixed solvent to obtain 6.6 g (yield: 61.7%) of pale yellow powder (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-2-ylphenyl)-phenancelene-9-ylamine (compound (1-59)).

[0140] Regarding the pale yellow powder obtained,１ H-NMR (CDCl ３ The following 37 hydrogen signals were detected and the structure was identified: δ (ppm) = 8.79 (1H), 8.74 (1H), 8.09 (1H), 8.01 (1H), 7.86 (4H), 7.75 (1H), 7.71 (5H), 7.66 (2H), 7.60 (3H), 7.50 (5H), 7.39 (1H), 7.34-7.23 (6H), 7.20 (2H), 7.07 (4H). Melting point: None

[0141] <Synthesis Example 4: Synthesis of Compound (1-69)> In a reaction vessel, 6.0 g of (4-naphthalene-2-yl-phenyl)-phenylamine, 10.3 g of 4-bromo-2″,5″-diphenyl-[1,1′;4′,1″]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri(t-butyl)phosphine, and 2.3 g of t-butoxysodium were charged and stirred under reflux overnight in toluene. After cooling, the filtrate obtained by filtration was concentrated to obtain the crude product. The crude product was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain 7.1 g of white powder (yield: 51.7%) of (2″,5″-diphenyl-[1,1′;4′,1″]terphenyl-4-yl)-(4-naphthalene-2-yl-phenyl)-phenylamine (compound (1-69)).

[0142] Regarding the obtained white powder, １ H-NMR (CDCl ３ The following 37 hydrogen signals were detected and the structure was identified: δ (ppm) = 8.04 (1H), 7.91 (3H), 7.73 (5H), 7.66 (2H), 7.56 (2H), 7.51 (7H), 7.42 (1H), 7.39–7.18 (15H), 7.10 (1H). Melting point: None

[0143] <Synthesis Example 5: Synthesis of Compound (1-83)> In a reaction vessel, 11.0 g of (4-phenanthrene-9-yl-phenyl)-phenylamine, 16.2 g of 4-bromo-2″,5″-[1,1′;4′,1″]terphenyl, 0.1 g of palladium(II) acetate, 0.3 g of tri(t-butyl)phosphine, and 3.7 g of t-butoxysodium were charged and stirred under reflux overnight in toluene solvent. After cooling, the filtrate obtained by filtration was concentrated to obtain the crude product. The obtained crude product was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain 11.2 g of white powder (yield: 48.5%) of (2″,5″-diphenyl-[1,1′;4′,1″]terphenyl-4-yl)-(4-phenanthrene-9-yl-phenyl)-phenylamine (compound (1-83)).

[0144] Regarding the obtained white powder, １ H-NMR (CDCl ３ The following 39 hydrogen signals were detected and their structure was identified: δ (ppm) = 8.81 (1H), 8.75 (1H), 8.09 (1H), 7.93 (1H), 7.71 (7H), 7.65–7.44 (10H), 7.44–7.22 (17H), 7.11 (1H). Melting point: None

[0145] <Synthesis Example 6: Synthesis of Compound (1-96)> In a reaction vessel, 50.0 g of 4-bromoaniline, 113.9 g of 4,4,5,5-tetramethyl-2-[1,1′:4′,1′′-terphenyl]-2′-yl-1,3,2-dioxaborolane, 350 mL of toluene, 88 mL of ethanol, 80.4 g of potassium carbonate, and 290 mL of water were charged. 6.7 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred under reflux for 14 hours. After cooling, the mixture was separated, and the organic layer was washed sequentially with water and saturated brine, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the filtrate was concentrated. 450 mL of heptane was added to the residue and stirred overnight at room temperature. The solid was collected by filtration to obtain 77.8 g of yellowish-white powder of [1,1′:2′,1′′:4′′,1′′′-quarterphenyl]-4-amine (yield: 83.3%).

[0146] In a reaction vessel, 55.0 g of [1,1′:2′,1′′:4′′,1′′′-Quarterphenyl]-4-amine, 74.9 g of 2-(4-bromophenyl)naphthalene, 28.0 g of t-butoxysodium, 420 mL of toluene, 0.9 g of tris(dibenzylideneacetone)dipalladium, and 2.4 g of 2,2′-bis(diphenylphosphin)-1,1′-binaphthyl were charged and stirred under reflux for 15 hours. The mixture was cooled to 80°C, and the solid was removed by thermal filtration using a funnel lined with Celite. The filtrate was heated and stirred, 50 g of silica gel was added at 80°C, and the mixture was stirred for 1 hour. The solid was then removed by thermal filtration. The filtrate was concentrated, and the residue was recrystallized in a toluene / acetone mixed solvent to obtain 69.5 g (yield: 68.3%) of N-(4-(2-naphthyl)phenyl)-[1,1′:2′,1′′:4′′,1′′′-quarterphenyl]-4-amine as a yellowish-white powder.

[0147] In a reaction vessel, 69.5 g of N-(4-(2-naphthyl)phenyl)-[1,1′:2′,1′′:4′′,1′′′-quarterphenyl]-4-amine, 45.1 g of 1-bromo-4-iodobenzene, 25.7 g of t-butoxysodium, 700 mL of toluene, 2.5 g of copper iodide, and 2.3 g of N,N′-dimethylethylenediamine were charged and stirred under reflux for 16 hours. After cooling to 80°C, the solid was removed by thermal filtration using a funnel lined with Celite. The filtrate was concentrated, and the residue was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain 59.4 g (yield: 65.5%) of a yellowish-white powder of N-(4-bromophenyl)-N-(4-(2-naphthyl)phenyl)-[1,1′:2′,1′′:4′′,1′′′-quarterphenyl]-4-amine.

[0148] In a reaction vessel, 12.0 g of N-(4-bromophenyl)-N-(4-(2-naphthyl)phenyl)-[1,1′:2′,1′′:4′′,1′′′-quarterphenyl]-4-amine, 5.3 g of 3-(2-naphthyl)phenylboronic acid, 84 mL of toluene, 21 mL of ethanol, 4.9 g of potassium carbonate, and 18 mL of water were charged. 0.4 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred under reflux for 14 hours. After cooling, 84 mL of methanol was added, and the precipitated solid was collected by filtration. 70 mL of water and 70 mL of methanol were added to the solid, and it was dispersed and washed under reflux for 1 hour. The solid was collected by filtration, 140 mL of toluene was added, and the mixture was heated to 100°C to remove the water and methanol. After cooling to 80°C, 7 g of silica gel and 7 g of activated clay were added, and the mixture was stirred for 1 hour. The solid was removed by filtration, and the filtrate was concentrated. 140 mL of acetone was added to the residue, and the mixture was stirred overnight at room temperature. The solid was collected by filtration. The solid was recrystallized in a toluene / acetone mixed solvent to obtain 11.3 g (yield: 79.6%) of N-(3′-(naphthalene-2-yl)-[1,1′-biphenyl]-4-yl)-N-(4-(naphthalene)-2-yl)phenyl)-5′-phenyl-[1,1′:2′,1′′-terphenyl]-4-amine (compound (1-96)) as a yellowish-white powder.

[0149] Regarding the yellowish-white powder obtained, １ H-NMR (CDCl ３ The following 43 hydrogen signals were detected and their structure was identified: δ (ppm) = 8.09 (1H), 8.01 (1H), 7.77–7.92 (8H), 7.43–7.73 (19H), 7.21–7.38 (10H), 7.04–7.13 (4H). Melting point: None

[0150] <Synthesis Example 7: Synthesis of Compound (1-97)> In a reaction vessel, 20.0 g of 2'-chloro-[1,1':4',1''-terphenyl], 29.5 g of N-phenyl-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-amine, 200 mL of 1,4-dioxane, 32.1 g of potassium phosphate, and 60 mL of water were charged. 2.1 g of tris(dibenzylideneacetone)dipalladium and 2.1 g of tricyclohexylphosphine were added, and the mixture was stirred under reflux for 14 hours. After cooling, 200 mL of methanol was added, and the precipitated solid was collected by filtration. 360 mL of chlorobenzene was added to the solid, the mixture was heated to 100°C, cooled to 80°C, 9 g of silica gel and 9 g of activated clay were added, and the mixture was stirred for 1 hour. The solid was removed by filtration, and the filtrate was concentrated. 360 mL of acetone was added to the residue, and the mixture was stirred overnight at room temperature. The solid was collected by filtration to obtain 30.6 g of yellowish-white powder of N,4′-diphenyl-[1,1′:2′,1′′:4′′,1′′′-terphenyl]-4′′′-amine (yield: 85.5%).

[0151] In a reaction vessel, 20.0 g of N,4′-diphenyl-[1,1′:2′,1′′:4′′,1′′′-terphenyl]-4′′′-amine, 18.5 g of 2-bromo-9,9-diphenyl-9H-fluorene, 200 mL of toluene, and 6.1 g of t-butoxysodium were charged. 0.1 g of tris(dibenzylideneacetone)dipalladium and 0.2 g of a 50% toluene solution of tri(t-butyl)phosphine were added, and the mixture was stirred under reflux for 14 hours. After cooling to 80°C, the mixture was thermally filtered using a funnel lined with Celite to remove the solid. The filtrate was heated and stirred, and at 80°C, 12 g of silica gel and 12 g of activated clay were added and stirred for 1 hour. The solid was removed by filtration, and the filtrate was concentrated. The residue was recrystallized using a toluene / acetone mixed solvent to obtain 21.4 g (yield: 64.1%) of a yellowish-white powder of N,9,9-triphenyl-N-(4′-phenyl-[1,1′:2′,1′′:4′′,1′′′-quarterphenyl]-4′′′-yl)-9H-fluoren-2-amine (compound (1-97)).

[0152] Regarding the yellowish-white powder obtained,１ H-NMR (CDCl ３ The following 43 hydrogen signals were detected and their structure identified: δ (ppm) = 7.64–7.71 (5H), 7.58–7.60 (1H), 7.51–7.53 (1H), 7.41–7.48 (6H), 7.30–7.38 (3H), 7.14–7.24 (21H), 6.98–7.09 (6H). Melting point: None

[0153] <Synthesis Example 8: Synthesis of Compound (1-102)> In a reaction vessel, 31.0 g of 4-bromo-2-chloro-1,1'-biphenyl, 22.0 g of 2-naphthaleneboronic acid, 240 mL of toluene, 60 mL of ethanol, 24.1 g of potassium carbonate, and 80 mL of water were charged. 1.3 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred under reflux for 15 hours. After cooling, the mixture was separated, and the organic layer was washed with water. The organic layer was stirred, heated to 100°C to confirm the absence of water, cooled to 80°C, 20 g of silica gel was added, and the mixture was stirred for 1 hour. The solid was removed by thermal filtration, and the filtrate was concentrated. The residue was recrystallized in a toluene / heptane mixed solvent to obtain 25.6 g of gray powder of 2-(2-chloro-[1,1'-biphenyl]-4-yl)naphthalene (yield: 63.5%).

[0154] In a reaction vessel, 20.0 g of 2-(2-chloro-[1,1'-biphenyl]-4-yl)naphthalene, 24.8 g of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine, 160 mL of 1,4-dioxane, 27.0 g of potassium phosphate, and 60 mL of water were charged. 1.8 g of tris(dibenzylideneacetone)dipalladium and 1.8 g of tricyclohexylphosphine were added, and the mixture was stirred under reflux for 12 hours. After cooling, the mixture was concentrated. The residue, with water remaining, was extracted with toluene. The organic layer was sequentially washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, the filtrate was stirred and heated, and 20 g of silica gel was added at 80°C. The mixture was stirred for 1 hour, the solid was removed by thermal filtration, and the filtrate was concentrated. The residue was recrystallized in toluene to obtain 26.0 g (yield: 78.0%) of a yellowish-white powder of N-([1,1'-biphenyl]-4-yl)-5'-(naphthalene-2-yl)-[1,1':2',1''-terphenyl]-4-amine.

[0155] In a reaction vessel, 24.6 g of N-([1,1'-biphenyl]-4-yl)-5'-(naphthalene-2-yl)-[1,1':2',1''-terphenyl]-4-amine, 14.7 g of 2-(4-bromophenyl)naphthalene, 250 mL of toluene, and 6.8 g of t-butoxysodium were charged. 0.4 g of tris(dibenzylideneacetone)dipalladium and 0.4 g of a 50% toluene solution of tri(t-butyl)phosphine were added, and the mixture was stirred under reflux for 4 hours. After cooling to 80°C, the mixture was thermally filtered using a funnel lined with Celite to remove the solid. The filtrate was heated and stirred, and at 80°C, 17 g of silica gel and 17 g of activated clay were added and the mixture was stirred for 1 hour. The solid was removed by filtration, and the filtrate was concentrated. The residue was purified by crystallization using a toluene / acetone mixed solvent to obtain 21.0 g (yield: 61.5%) of a yellowish-white powder of N-([1,1'-biphenyl]-4-yl)-5'-(naphthalene-2-yl)-N-(4-(naphthalene-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-amine (compound (1-102)).

[0156] Regarding the yellowish-white powder obtained,１ H-NMR (CDCl ３ The following 39 hydrogen signals were detected and the structure was identified: δ (ppm) = 8.14 (1H), 8.01 (1H), 7.82–7.93 (8H), 7.71–7.77 (2H), 7.39–7.63 (13H), 7.05–7.32 (14H). Melting point: None

[0157] <Synthesis Example 9: Synthesis of Compound (1-103)> In a reaction vessel, 32.7 g of 2'-bromo-[1,1':4',1''-terphenyl], 24.8 g of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine, 320 mL of toluene, 90 mL of ethanol, 21.9 g of potassium carbonate, and 80 mL of water were charged. 1.2 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred under reflux for 13 hours. After cooling, the precipitated solid was collected by filtration, 250 mL of methanol and 250 mL of water were added, and the mixture was dispersed and washed under reflux for 1 hour, after which the solid was collected by filtration. 750 mL of toluene was added to the solid, and the mixture was stirred. The mixture was heated to 100°C to confirm the removal of methanol and water, and then cooled to 80°C. 10 g of silica gel was added and stirred for 1 hour, and the solid was removed by thermal filtration. The filtrate was concentrated, and the residue was crystallized with acetone solvent to obtain 33.0 g (yield: 65.9%) of a yellowish-white powder of N-([1,1'-biphenyl]-4-yl)-5'-phenyl-[1,1':2',1''-terphenyl]-4-amine.

[0158] In a reaction vessel, 10.2 g of N-([1,1'-biphenyl]-4-yl)-5'-phenyl-[1,1':2',1''-terphenyl]-4-amine, 7.0 g of 1-(4-bromophenyl)-3-phenylnaphthalene, 70 mL of toluene, and 2.8 g of t-butoxysodium were charged. 0.1 g of palladium acetate and 0.4 g of a 50% toluene solution of tri(t-butyl)phosphine were added, and the mixture was stirred under reflux for 4 hours. After cooling to room temperature, methanol was added, and the precipitated solid was collected by filtration. 300 mL of toluene was added to the solid, and the mixture was stirred and heated. At 80°C, 7 g of silica gel and 7 g of activated clay were added, and the mixture was stirred for 1 hour. The solid was removed by thermal filtration, and the filtrate was concentrated. The residue was recrystallized using a dichloromethane / acetone mixed solvent to obtain 10.9 g (yield: 74.2%) of a white powder N-([1,1'-biphenyl]-4-yl)-5'-phenyl-N-(4-(3-phenylnaphthalene-1-yl)phenyl)-[1,1':2',1''-terphenyl]-4-amine (compound (1-103)).

[0159] Regarding the obtained white powder, １ H-NMR (CDCl ３ The following 41 hydrogen signals were detected and their structure was identified: δ (ppm) = 8.01–8.03 (2H), 7.94–7.96 (1H), 7.58–7.77 (9H), 7.22–7.53 (25H), 7.08–7.15 (4H). Melting point: None

[0160] Compounds represented by general formula (I), other than those synthesized in Synthesis Examples 1 to 9, can also be synthesized in the same manner as in Synthesis Examples 1 to 9.

[0161]

[0162] <Measurement 1: Measurement of Glass Transition Temperature> For each arylamine compound represented by general formula (I) synthesized in Synthesis Examples 1 to 9, the glass transition temperature was measured using a high-sensitivity differential scanning calorimeter (Bruker AXS, model: DSC3100SA). The results are shown in Table 1.

[0163] <Measurement 2: Measurement of HOMO level> An arylamine compound represented by general formula (I) was used to create a 100 nm thick vapor-deposited film on an ITO substrate, and the HOMO energy level (HOMO level, ionization potential) was measured using an ionization potential analyzer (Sumitomo Heavy Industries, Ltd., model: PYS-202). The results are shown in Table 1.

[0164]

[0165] The arylamine compounds represented by general formula (I) synthesized in Synthesis Examples 1 to 9 have glass transition temperatures above 100°C, confirming that the thin film state is stable. Compared to the HOMO level (5.4 eV) of common hole transport materials such as NPDs and TPDs, the arylamine compounds represented by general formula (I) exhibit suitable energy levels, indicating good hole transport capability. Therefore, the arylamine compounds represented by general formula (I) are useful as materials for hole injection layers, hole transport layers, electron blocking layers, or light-emitting layers in organic EL devices, and can improve the luminous efficiency, driving voltage, and durability of conventional organic EL devices.

[0166] [Example 1] As shown in Figure 1, the organic EL element was fabricated by depositing a hole injection layer 3, a hole transport layer 4, a first electron blocking layer 5, a second electron blocking layer 6, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 9, a cathode 10, and a capping layer 11 in that order on a glass substrate 1 on which a reflective ITO electrode was pre-formed as a transparent anode 2.

[0167] Specifically, a glass substrate 1, on which a 50 nm thick ITO (Indium Tin Oxide) film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were sequentially deposited, was ultrasonically cleaned in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250°C for 10 minutes. After that, UV ozone treatment was performed for 15 minutes, and then this ITO-coated glass substrate was placed in a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, a hole injection layer 3 was formed covering the transparent anode 2 by binary deposition of an electron acceptor (Acceptor-1) with the following structural formula and the compound (HTM-1) with the following formula, at a deposition rate ratio of Acceptor-1:HTM-1 = 3:97, to a thickness of 10 nm. On this hole injection layer 3, a hole transport layer 4 of the compound (HTM-1) with a thickness of 140 nm was formed. On this hole transport layer 4, the following compound (HTM-2) was formed as a first electron blocking layer 5 to a thickness of 25 nm. On this first electron blocking layer 5, the compound (1-4) from synthesis example 1 was formed as a second electron blocking layer 6 to a thickness of 5 nm. On this second electron blocking layer 6, the following compounds (EMD-1) and (3-1) were deposited as an emissive layer 7 by binary deposition at a deposition rate where the deposition rate ratio of compounds (EMD-1):(3-1) = 5:95, to a thickness of 30 nm. On this emissive layer 7, the following compounds (ETM-1) and (ETM-2) were deposited as an electron transport layer 8 by binary deposition at a deposition rate where the deposition rate ratio of compounds (ETM-1):(ETM-2) = 50:50, to a thickness of 30 nm. On this electron transport layer 8, the compound (ETM-2) was formed as an electron injection layer 9 to a thickness of 1 nm. A magnesium-silver alloy was formed on this electron injection layer 9 as the cathode 10 to a thickness of 12 nm. Finally, a compound with the following structural formula (CPL-1) was formed as the capping layer 11 to a thickness of 60 nm.

[0168]

[0169] [Examples 2-90] Organic EL elements were fabricated in the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of the compounds (1-4) used as the material for the second electron blocking layer 6 and the compound (3-1) used as the material for the light-emitting layer 7. The light-emitting characteristics of the fabricated organic EL elements were measured when a DC voltage was applied in air at room temperature. The results are summarized in Table 2.

[0170] [Comparative Example 1] For comparison, an organic EL device was fabricated under the same conditions as in Example 1, except that compound (HTM-3) with the following structural formula was used instead of compound (1-4) as the material for the second electron blocking layer 6.

[0171] [Comparative Example 2] For comparison, an organic EL element was fabricated under the same conditions as in Example 1, except that compound (HTM-4) with the following structural formula was used instead of compound (1-4) as the material for the second electron blocking layer 6.

[0172] [Comparative Example 3] For comparison, an organic EL element was fabricated under the same conditions as in Example 1, except that the compound (EMH-1) with the following structural formula was used instead of compound (3-1) as the material for the light-emitting layer 7.

[0173] [Comparative Example 4] For comparison, an organic EL element was fabricated under the same conditions as in Example 1, except that compound (EMH-2) with the following structural formula was used instead of compound (3-1) as the material for the light-emitting layer 7.

[0174]

[0175] The luminescence characteristics of the organic EL elements fabricated in Examples 1 to 90 and Comparative Examples 1 to 4 were measured by applying a DC voltage in air at room temperature (current density: 10 mA / cm²). ２ ). Furthermore, the device lifetime was measured using the fabricated organic EL element. In this invention, the device lifetime is defined as the luminescence brightness at the start of light emission (initial brightness) of 2000 cd / m². ２ When driven with a constant current, the luminous intensity is 1900 cd / m². ２ The time it took for the brightness to decay to 95% (corresponding to 95% of the initial brightness, which is set to 100%: 95% decay) was measured. The measurement results are summarized in Table 2.

[0176]

[0177] As shown in Table 2, the current density is 10 mA / cm². ２ The drive voltage for the elements in Examples 1 to 90 was 3.55 to 3.71 V, compared to 3.83 to 3.98 V for the elements in Comparative Examples 1 to 4. The luminous efficiency was 53.08 to 57.81 cd / A for the elements in Examples 1 to 90, compared to 46.10 to 52.07 cd / A for the elements in Comparative Examples 1 to 4. In terms of power efficiency, the elements in Examples 1 to 90 were 45.48 to 49.19 lm / W, compared to 36.36 to 42.75 lm / W for the elements in Comparative Examples 1 to 4. Furthermore, the element lifespan (95% decay) was significantly longer for the elements in Examples 1 to 90, at 383 to 457 hours, compared to 303 to 366 hours for the elements in Comparative Examples 1 to 4.

[0178] As is clear from the above results, the arylamine compound having a specific structure represented by general formula (I) has a higher hole mobility and superior electron blocking ability compared to conventional arylamine compounds used as hole transport materials. It was found that by combining it with a heterocyclic compound represented by general formula (III), it is possible to realize an organic EL device with higher luminous efficiency and a longer lifespan compared to conventional organic EL devices.

[0179] The organic EL elements using arylamine compounds and heterocyclic compounds having specific structures according to the present invention offer improved luminous efficiency and enhanced durability, enabling applications such as home appliances and lighting. Furthermore, the arylamine compounds and heterocyclic compounds of the present invention can be used not only in organic EL elements but also in electronic devices such as electrophotographic photoreceptors, image sensors, photoelectric conversion elements, and solar cells.

[0180] 1. Glass substrate 2. Transparent anode 3. Hole injection layer 4. Hole transport layer 5. First electron blocking layer 6. Second electron blocking layer 7. Emitting layer 8. Electron transport layer 9. Electron injection layer 10. Cathode 11. Capping layer

Claims

1. An organic electroluminescent device having at least an anode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and a cathode in this order, wherein the electron blocking layer contains an arylamine compound represented by the following general formula (I), and the light emitting layer contains a compound represented by the following general formula (III). (In the formula, Ar １ to Ar ３ each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L １ to L ３ each independently represent a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking cyclic group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked via a single bond. Provided that one or two of Ar １ to Ar ３ represent a substituted phenyl group represented by the following general formula (II), and at least one of L １ to L ３ is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.) (In the formula, the broken line represents the bonding site to L １ to L ３ in general formula (I). Ar ４ and Ar ５ each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R １ n represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. １ This is the number of elements, representing an integer from 0 to 3. If n is 2 or 3, there are multiple elements R. １ They may be the same or different from each other, and when n is an integer from 1 to 3, R １ The benzene ring to which R is bonded １ , multiple adjacent R １ , R １ and Ar ４ , R １ and Ar ５ These elements may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. (In the formula, Ar ６ ~Ar ８ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Ar ６ ~Ar ８ At least one of these represents a fused polycyclic aromatic group represented by any of the following general formulas (IV-1) to (IV-4). ４ ~L ６ Each of these independently represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking ring group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked by a single bond. １ ~X ３ Each of these independently represents an unsubstituted methine group (-CH=) or a nitrogen atom. However, X １ ~X ３ At least one of them represents a nitrogen atom. (In the formula, the dashed line represents L in general formula (III) ４ ~L ６ This represents the connection point. Y and Z are independently -CR ４ R ５ -, -NR ６ -, -O-, or -S-, and at least one of Y and Z is -CR ４ R ５ Represents - or -O-. R ２ and R ３ Each independently represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ２ and R ３ Each of these may form a ring by being bonded to a benzene ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. ４ ~R ６ Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ４ and R ５ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. p is R ２ This is the number of elements, and represents an integer from 0 to 4. q is R ３ This is the number of elements, and represents an integer from 0 to 5. If p and q are each independent integers of 2 or greater, there are multiple R's. ２ or R ３ These may be identical or different from each other, and may be multiple adjacent Rs. ２ or R ３ These elements may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring.

2. In the above general formula (I), Ar １ L is a substituted phenyl group represented by the general formula (II), １ The organic electroluminescent element according to claim 1, wherein the linking ring group is a combination of one or two groups selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted terphenylylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted thiophendiyl group, a substituted or unsubstituted pyridinediyl group, and a substituted or unsubstituted dibenzofuranyl group, and n in general formula (II) is 0.

3. In the above general formula (I), Ar １ is a substituted phenyl group represented by the general formula (II), and in the general formula (II), Ar ４ and Ar ５ The organic electroluminescent element according to claim 1, wherein each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted thienyl group.

4. In the above general formula (I), Ar １ is a substituted phenyl group represented by the general formula (II), and Ar ２ and Ar ３ At least one of the groups is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, or a substituted or unsubstituted triphenylenyl group, and is bonded to the substituted or unsubstituted aryl group. ２ and L ３ The organic electroluminescent element according to claim 1, wherein at least one of the members is a linking ring group consisting of one or two groups selected from the group consisting of a single bond or a substituted or unsubstituted phenylene group and a substituted or unsubstituted naphthylene group.

5. In the above general formula (I), L １ ~L ３ The organic electroluminescent element according to claim 1, wherein each of the linking ring groups is independently one or more groups selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, and a substituted or unsubstituted naphthylene group.

6. In the above general formula (III), X １ ~X ３ At least two of them are nitrogen atoms, Ar ６ However, it is a condensed polycyclic aromatic group represented by any of the general formulas (IV-1) to (IV-3) above, L ４ ~L ６ The organic electroluminescent element according to claim 1, wherein each is independently a single bond, or a substituted or unsubstituted arylene group.

7. In the above general formula (III), Ar ７ and Ar ８ The organic electroluminescent element according to claim 1, wherein each of the groups is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

8. In the above general formulas (IV-1) to (IV-4), Y is -CR ４ R ５ -, Z is -O- or -S-, p is an integer between 0 and 2, q is 0 or 1, R ２ and R ３ The organic electroluminescent element according to claim 1, wherein each is independently a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group.

9. In the above general formulas (IV-1) to (IV-4), Y is -CR ４ R ５ - and Z is -O- or -S-, R ４ and R ５ The organic electroluminescent element according to claim 1, wherein the alkyl group is a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group, and is identical to each other.

10. In the above general formula (III), X １ ~X ３ is a nitrogen atom, Ar ６ However, it is a condensed polycyclic aromatic group represented by the general formula (IV-1) or (IV-2), L ４ However, Y is a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group, and in the general formula (IV-1) or (IV-2), Y is -CR ４ R ５ -, Z is -O-, p is an integer between 0 and 2, q is 0, R ２ R is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ４ and R ５ The organic electroluminescent element according to claim 1, wherein the alkyl group is a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group, and is identical to each other.

11. The organic electroluminescent element according to any one of claims 1 to 10, wherein the electron blocking layer has a two-layer structure comprising a first electron blocking layer in contact with the hole transport layer and a second electron blocking layer in contact with the light-emitting layer, and the second electron blocking layer contains an arylamine compound represented by the general formula (I).

12. The organic electroluminescent element according to claim 1, wherein the maximum wavelength of the emission spectrum when a DC voltage is applied to the organic electroluminescent element in air at 25°C is 600 nm or more and 700 nm or less.

13. An electronic element or electronic device comprising a pair of electrodes and at least two organic layers sandwiched therebetween, wherein at least one of the organic layers contains an arylamine compound represented by the following general formula (I), and another organic layer in contact with said organic layer contains a compound represented by the following general formula (III). (wherein Ar １ to Ar ３ each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L １ to L ３ each independently represent a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking cyclic group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked via a single bond; provided that one or two of Ar １ to Ar ３ represent a substituted phenyl group represented by the following general formula (II), and at least one of L １ to L ３ is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.) (wherein the broken line represents a bonding site to L １ to L ３ in general formula (I). Ar ４ and Ar ５ each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R １ n represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. １ This is the number of elements, representing an integer from 0 to 3. If n is 2 or 3, there are multiple elements R. １ They may be the same or different from each other, and when n is an integer from 1 to 3, R １ The benzene ring to which R is bonded １ , multiple adjacent R １ , R １ and Ar ４ , R １ and Ar ５ These elements may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. (In the formula, Ar ６ ~Ar ８ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Ar ６ ~Ar ８ At least one of these represents a fused polycyclic aromatic group represented by any of the following general formulas (IV-1) to (IV-4). ４ ~L ６ Each of these independently represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking ring group having a structure in which a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group are linked by a single bond. １ ~X ３ Each of these independently represents an unsubstituted methine group (-CH=) or a nitrogen atom. However, X １ ~X ３ At least one of them represents a nitrogen atom. (In the formula, the dashed line represents L in general formula (III) ４ ~L ６ This represents the connection point. Y and Z are independently -CR ４ R ５ -, -NR ６ -, -O-, or -S-, and at least one of Y and Z is -CR ４ R ５ Represents - or -O-. R ２ and R ３ Each independently represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ２ and R ３ Each of these may form a ring by being bonded to a benzene ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. ４ ~R ６ Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryloxy group. ４ and R ５ These may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring. p is R ２ This is the number of elements, and represents an integer from 0 to 4. q is R ３ This is the number of elements, and represents an integer from 0 to 5. If p and q are each independent integers of 2 or greater, there are multiple R's. ２ or R ３ These may be identical or different from each other, and may be multiple adjacent Rs. ２ or R ３ These elements may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring.

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