Compound, organic electroluminescent element, and electronic device

Abstract

The compound represented by general formula (1) has excellent hole transport ability and electron blocking ability. Ar1 and Ar2 each represents a monovalent aromatic hydrocarbon group or aromatic heterocyclic group; ar3 and Ar4 each represents a phenyl group, a biphenyl group or the like; l represents a divalent aromatic hydrocarbon group or aromatic heterocyclic group; r1-R3 each represents a hydrogen atom, an alkyl group or the like; and n represents 1 or 2.

Description

Technical Field

[0001] The present invention relates to a compound useful as an electron blocking material or a hole transporting material, and an organic electroluminescent device and an electronic device using the compound. Background Art

[0002] Organic electroluminescent elements (organic EL elements) are self-luminous elements and are therefore brighter and more visible than liquid crystal elements, and are capable of clear display. Therefore, active research is being conducted.

[0003] In 1987, CWTang of Eastman Kodak Company developed a layered structure element that assigned various functions to each material, making it a practical organic EL element. Specifically, they stacked a phosphor that can transport electrons and an organic substance that can transport holes, injected the two charges into the phosphor layer, and caused it to emit light. As a result, they achieved 1000 cd / m at a voltage of less than 10V. 2 The above high brightness (for example, refer to Patent Document 1 and Patent Document 2).

[0004] To date, many improvements have been made to the practical application of organic EL elements, and the various functions of the stacked structure have been further subdivided. High efficiency and durability have been achieved by sequentially arranging a stacked structure of an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode on a substrate (for example, refer to non-patent document 1).

[0005] Furthermore, attempts to utilize triplet excitons to further improve luminous efficiency are underway, with research into the use of phosphorescent compounds (e.g., see Non-Patent Document 2). Furthermore, devices utilizing luminescence based on thermally activated delayed fluorescence (TADF) have also been developed. In 2011, Adachi et al. at Kyushu University achieved an external quantum efficiency of 5.3% using a device using a thermally activated delayed fluorescence material (e.g., see Non-Patent Document 3).

[0006] The light-emitting layer of these organic EL devices is typically made by doping a charge-transporting compound, known as a host material, with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence. Furthermore, as described in the aforementioned non-patent documents, organic EL devices are provided with various organic layers, and the choice of these organic materials significantly influences various characteristics of the device, such as efficiency and durability (see, for example, Non-Patent Document 2).

[0007] That is, in an organic EL element, the charges injected from the two electrodes are re-bonded in the light-emitting layer to obtain light emission. Therefore, it is important to efficiently deliver the two charges of holes and electrons to the light-emitting layer, and it is necessary to make an element with excellent carrier balance. For example, by using a material with hole injection properties that supply holes injected from the anode to the light-emitting layer or electron blocking properties that block electrons injected from the cathode, the probability of holes and electrons re-bonding in the light-emitting layer is increased, thereby locking the excitons generated in the light-emitting layer, thereby obtaining high luminous efficiency. Therefore, it is required that the hole mobility of the hole transport material is large, the electron blocking property is high, and the durability to electrons is high.

[0008] Furthermore, the material's heat resistance and amorphicity are crucial for device lifespan. Materials with low heat resistance can decompose even at relatively low temperatures due to the heat generated during device operation, leading to material degradation. Materials with low amorphicity can crystallize thin films even in a short period of time, causing device degradation. Therefore, the materials used must possess both high heat resistance and good amorphicity.

[0009] Until now, hole-transporting materials used in organic EL devices have included N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) and various aromatic amine derivatives (see, for example, Patent Documents 1 and 2). However, while NPD has excellent hole-transporting properties, its glass transition point (Tg), an indicator of heat resistance, is relatively low at 96°C. Crystallization at high temperatures can degrade device performance (see, for example, Non-Patent Document 4).

[0010] Among the above aromatic amine derivatives, there are some with a hole mobility of 10 -3 cm 2 / Vs or more excellent mobility compound (for example, reference patent document 1 and patent document 2), but due to insufficient electron blocking property, a part of the electrons will pass through the luminous layer, thereby can not expect the improvement of luminous efficiency. Therefore, in order to achieve further high efficiency, it is required that the electron blocking property is higher, the film is more stable and the material with higher heat resistance is higher. In addition, although there is a report of aromatic amine derivatives with high durability (for example, reference patent document 3), it is used as a charge transport material for an electronic photographic photoreceptor, and there is no example used as an organic EL element.

[0011] In order to solve this problem, substituted carbazole structures or arylamine compounds have been proposed as compounds with improved properties such as heat resistance and hole injection properties (for example, refer to Patent Documents 4 and 5). However, in elements using these compounds in the hole injection layer or hole transport layer, although improvements have been made in the element life and luminous efficiency, these improvements are not sufficient, and further reduction in driving voltage or improvement in luminous efficiency and extension of the element life are required.

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

[0013] Patent Document 2: U.S. Patent No. 5,639,914

[0014] Patent Document 3: U.S. Patent No. 7,759,030

[0015] Patent Document 4: U.S. Patent No. 8,021,764

[0016] Patent Document 5: Japanese Patent No. 7177966

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

[0018] Patent Document 7: Japanese Patent No. 7144743

[0019] Non-patent document 1: Proceedings of the 9th Symposium of the Society of Applied Physics, pp. 55-61 (2001)

[0020] Non-patent document 2: Proceedings of the 9th Symposium of the Society of Applied Physics, pp. 23-31 (2001)

[0021] Non-patent document 3: Appl. Phys. Let., 98, 083302 (2011)

[0022] Non-Patent Document 4: Preliminary Proceedings of the Third Regular Meeting of the Organic EL Symposium, pp. 13-14 (2006) Summary of the Invention

[0023] As described above, various organic compounds have been proposed as materials for organic EL devices. However, in reality, a compound that has both excellent hole-transporting ability and electron-blocking ability and high thermal stability has not yet been realized.

[0024] The present invention aims to provide a material for an organic EL element having excellent hole-transporting and electron-blocking properties and high thermal stability in a thin film state. Furthermore, the present invention aims to provide an organic EL element having high luminous efficiency and power efficiency and a long device life.

[0025] As a result of in-depth research to achieve the above-mentioned purpose, the present inventors have discovered a compound having a structure in which an arylamino group or a heteroarylamino group is bonded to a connecting ring structure formed by connecting multiple aromatic rings. Among them, the specific compound having a meta-position relationship in the connecting ring structure has excellent hole transport ability and electron blocking ability, and is also highly stable in a thin film state. Then, it was found that by using this compound, an organic EL element with high luminous efficiency and power efficiency and a long life was achieved. The present invention was completed based on these insights and specifically has the following structure.

[0026] 1) A compound represented by the following general formula (1) and satisfying at least one of the following (Condition 1) to (Condition 5).

[0027] [Chemical Formula 1]

[0028]

[0029] [Ar1 and Ar2 in the general formula (1) represent a monovalent aromatic hydrocarbon group which may be the same or different, substituted or unsubstituted, or

[0030] a substituted or unsubstituted monovalent aromatic heterocyclic group,

[0031] X1 represents a group represented by the above-mentioned general formula (2).

[0032] In the following general formula (2), when n is 1, L is an unsubstituted phenylene group, Ar3 and Ar4 are unsubstituted phenyl groups, Ar1, Ar2 and X1 are different.]

[0033] [Chemical Formula 2]

[0034]

[0035] [Ar3 and Ar4 in the general formula (2) represent the same or different

[0036] Substituted or unsubstituted phenyl,

[0037] Substituted or unsubstituted biphenyl,

[0038] Substituted or unsubstituted naphthyl,

[0039] substituted or unsubstituted carbazolyl,

[0040] Substituted or unsubstituted dibenzofuranyl,

[0041] Substituted or unsubstituted dibenzothienyl, or

[0042] substituted or unsubstituted Fiki,

[0043] L means

[0044] a substituted or unsubstituted divalent aromatic hydrocarbon group, or

[0045] a substituted or unsubstituted divalent aromatic heterocyclic group,

[0046] R1 to R3 may be the same or different.

[0047] Hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group,

[0048] a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms,

[0049] a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms,

[0050] a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms,

[0051] a substituted or unsubstituted linear or branched alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms, or

[0052] a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,

[0053] n represents an integer of 1 or 2. When n is 2, L may be the same as or different from each other.

[0054] * represents the bonding position to N in the general formula (1).]

[0055] (Condition 1) L in the general formula (2) is a substituted or unsubstituted biphenylene group.

[0056] (Condition 2) Ar3 in the general formula (2) is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted phenanthrenyl group.

[0057] (Condition 3) At least one of Ar3 and Ar4 in the general formula (2) is a substituted or unsubstituted biphenyl group.

[0058] (Condition 4) At least one of Ar1 and Ar2 in the general formula (1) is a substituted or unsubstituted monovalent aromatic hydrocarbon group including a condensed polycyclic structure, or a substituted or unsubstituted monovalent aromatic heterocyclic group including a condensed polycyclic structure.

[0059] (Condition 5) At least one of Ar1 and Ar2 in the general formula (1) is a substituted or unsubstituted 3,4-diphenylphenyl group.

[0060] 2) Furthermore, the present invention includes the compound described in 1) above, wherein, in the general formula (2), R1 to R3 are hydrogen atoms or deuterium atoms, which may be the same or different.

[0061] 3) Furthermore, the present invention includes the compound described in 1) or 2) above, wherein, in the general formula (2), at least one of Ar3 and Ar4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0062] 4) Furthermore, the present invention includes the compound according to any one of 1) to 3) above, wherein, in the general formula (2), Ar3 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0063] 5) Furthermore, the present invention includes the compound described in any one of 1) to 4) above, wherein, in the general formula (2), Ar4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0064] 6) Furthermore, the present invention includes the compound described in any one of 1) to 5) above, wherein, in the general formula (2), L is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.

[0065] 7) Furthermore, the present invention includes the compound according to any one of 1) to 6) above, wherein, in the general formula (2), L is an unsubstituted or deuterium-substituted phenylene group.

[0066] 8) Furthermore, the present invention includes compounds described in any one of 1) to 7) above, wherein, in the general formula (1), Ar1 and Ar2 are each the same or different, and are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylsilylphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted fluorenyl.

[0067] 9) Furthermore, the present invention includes the compound according to any one of 1) to 8) above, wherein in the general formula (2), the integer of n is 1.

[0068] 10) Furthermore, the present invention includes an organic EL device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the compound described in any one of 1) to 9) above.

[0069] 11) Furthermore, the present invention includes the organic EL device described in 10) above, wherein the organic layer is a hole transport layer.

[0070] 12) Furthermore, the present invention includes the organic EL device described in 10) above, wherein the organic layer is an electron blocking layer.

[0071] 13) Furthermore, the present invention includes an electronic device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the arylamine compound described in any one of 1) to 9) above.

[0072] Effects of the Invention

[0073] The compounds of the present invention have excellent hole transport and electron blocking abilities and are highly thermally stable in thin film form, making them useful as electron blocking or hole transport materials. Organic electroluminescent devices using the compounds of the present invention as materials for organic layers can achieve high luminous efficiency, high power efficiency, and long device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0074] Figure 1 These are schematic cross-sectional views showing the layer structures of the organic EL devices produced in Examples 1 to 10 and Comparative Examples 1 and 2. DETAILED DESCRIPTION

[0075] Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below is sometimes made based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in this specification, the numerical range represented by "to" refers to a range that includes the numerical values ​​recorded before and after "to" as the lower limit and the upper limit. In addition, there is no particular limitation on the isotope types of hydrogen atoms present in the molecules of the compounds used in the present invention. For example, the hydrogen atoms in the molecules may all be 1 H, or part or all of it 2 H (deuterium D). In this specification, the term "substituted or unsubstituted" means that the group marked with the term may be an unsubstituted group (a group in which a hydrogen atom is not replaced by a substituent), or at least one hydrogen atom of the group may be substituted by a substituent.

[0076] <Compound represented by general formula (1)>

[0077] Hereinafter, the compound represented by the general formula (1) of the present invention will be described in detail.

[0078] The aromatic ring constituting the "monovalent aromatic hydrocarbon group" (aryl group) in the "substituted or unsubstituted monovalent aromatic hydrocarbon group" represented by Ar1 and Ar2 in the general formula (1) may be a monocyclic ring, a condensed ring formed by condensing two or more rings (condensed polycyclic aromatic hydrocarbon group), a connected ring formed by connecting two or more aromatic rings that can be condensed via a single bond, a connected ring formed by connecting two or more rings via a single bond, or a spiro ring formed by connecting two or more rings via a spiro bond. The number of carbon atoms in the aromatic ring is, for example, selected from the range of 6 to 30. Specific examples of the "monovalent aromatic hydrocarbon group" include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylene, fluorenyl, spirobifluorenyl, and the like. Examples of the "substituted or unsubstituted monovalent aromatic hydrocarbon group" including a group having a condensed polycyclic structure include naphthyl, naphthylphenyl, naphthylbiphenyl, anthracenyl, phenanthrenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylene, fluorenyl, and spirobifluorenyl.

[0079] The "monovalent aromatic heterocyclic group" (heteroaryl group) in the "substituted or unsubstituted monovalent aromatic heterocyclic group" represented by Ar1 and Ar2 in general formula (1) may be a monocyclic ring or a condensed ring formed by condensing a heterocyclic ring with one or more rings (condensed polycyclic aromatic heterocyclic group). The number of carbon atoms in the aromatic heterocyclic ring is, for example, 2 to 40, or may be selected from the range of 2 to 20. Specific examples of the “monovalent aromatic heterocyclic group” include a pyridyl group, a pyrimidyl group, a triazine group, a furyl group, a pyrrolyl group, a thienyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, an azafluorenyl group, a diazafluorenyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group. Examples of the “substituted or unsubstituted monovalent aromatic heterocyclic group” including a group having a condensed polycyclic structure include a naphthylpyridyl group, a naphthylpyrimidinyl group, a naphthylbiphenyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, an azafluorenyl group, a diazafluorenyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group.

[0080] When the "substituted or unsubstituted monovalent aromatic hydrocarbon group" or "substituted or unsubstituted monovalent aromatic heterocyclic group" represented by Ar1 and Ar2 in the general formula (1) has a substituent, the "substituent" may include, for example, a deuterium atom, a cyano group, a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom; a silyl group such as a trimethylsilyl group, a triphenylsilyl group; a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group; a linear or branched alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group; an alkenyl group such as a vinyl group, an allyl group; an aryloxy group having 6 to 30 carbon atoms such as a phenoxy group, a tolyloxy group; a carbon atom such as a benzyloxy group, a phenethoxy group an aromatic hydrocarbon group having 6 to 30 carbon atoms (including a condensed polycyclic aromatic hydrocarbon group), such as phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, and triphenylene; an aromatic heterocyclic group having 5 to 30 carbon atoms (including a condensed polycyclic aromatic heterocyclic group), such as pyridyl, thienyl, furanyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carbolyl; and the hydrogen atoms of these substituents may be substituted with the substituents exemplified herein. In one embodiment of the present invention, the substituent is selected from the group consisting of a deuterium atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, and an aromatic heterocyclic group having 5 to 30 carbon atoms. In one embodiment of the present invention, the substituent is a deuterium atom or a linear or branched alkyl group having 1 to 6 carbon atoms.

[0081] In addition, about the situation that the hydrogen atom of the substituent is further substituted by a substituent, the substituent directly substituted on the parent skeleton (aromatic hydrocarbon group, aromatic heterocyclic group) is sometimes referred to as the "first substituent", and the substituent substituted on the first substituent is referred to as the "second substituent". Here, when the first substituent includes a benzene ring, the benzene ring can be bonded to the parent skeleton to form a cyclic structure. And, when the benzene ring of the first substituent is substituted with more than two second substituents, adjacent second substituents can be bonded to each other to form a cyclic structure. Here, the bonding between the benzene ring and the parent skeleton in the first substituent and the bonding between the second substituents can be a single bond or a bonding via a linking group. As examples of linking groups, substituted or unsubstituted methylene, oxygen atom or sulfur atom can be cited.

[0082] Ar1 and Ar2 may be the same as or different from each other. In one embodiment of the present invention, the chemical structures of Ar1 and Ar2 are different from each other. In one embodiment of the present invention, Ar1 and Ar2 are both connected rings formed by two or more aromatic rings connected by a single bond. In one embodiment of the present invention, Ar1 and Ar2 are both connected rings formed by two or more aromatic rings connected by a single bond, but the chemical structures are different from each other. In one embodiment of the present invention, one of Ar1 and Ar2 is a substituted or unsubstituted monovalent aromatic hydrocarbon group, and the other is a substituted or unsubstituted monovalent aromatic heterocyclic group. In one embodiment of the present invention, at least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent aromatic hydrocarbon group and includes a condensed polycyclic structure. In one embodiment of the present invention, at least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent aromatic heterocyclic group and includes a condensed polycyclic structure. In one embodiment of the present invention, at least one of Ar1 and Ar2 is a substituted or unsubstituted 3,4-diphenylphenyl group, for example, an unsubstituted 3,4-diphenylphenyl group.

[0083] In the general formula (1), X1 is a group represented by the above-mentioned general formula (2).

[0084] Regarding the “substituent” when the “substituted or unsubstituted phenyl group,” “substituted or unsubstituted biphenyl group,” “substituted or unsubstituted naphthyl group,” “substituted or unsubstituted carbazolyl group,” “substituted or unsubstituted dibenzofuranyl group,” “substituted or unsubstituted dibenzothiophene group,” and “substituted or unsubstituted phenanthrenyl group” represented by Ar3 and Ar4 in the general formula (2) have a substituent, reference can be made to the description and specific examples of the “substituent” in the “substituted or unsubstituted monovalent aromatic hydrocarbon group” and “substituted or unsubstituted monovalent aromatic heterocyclic group” represented by Ar1 and Ar2 in the general formula (1).

[0085] Ar3 and Ar4 may be the same as or different from each other.

[0086] In one embodiment of the present invention, Ar3 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted phenanthrenyl group. For example, Ar3 is a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, at least one of Ar3 and Ar4 is a substituted or unsubstituted biphenyl group. For example, only Ar3 is a substituted or unsubstituted biphenyl group, for example, only Ar4 is a substituted or unsubstituted biphenyl group.

[0087] Regarding the description of the aromatic ring constituting the "divalent aromatic hydrocarbon group" of the "substituted or unsubstituted divalent aromatic hydrocarbon group" represented by L in general formula (2), reference can be made to the description of the aromatic ring constituting the "monovalent aromatic hydrocarbon group" in Ar1 and Ar2 in general formula (1). Specific examples of the "divalent aromatic hydrocarbon group" include divalent groups obtained by removing one hydrogen atom from the specific examples of the "monovalent aromatic hydrocarbon group" described above.

[0088] Regarding the description of the aromatic heterocycle constituting the "divalent aromatic heterocyclic group" of the "substituted or unsubstituted divalent aromatic heterocyclic group" represented by L in general formula (2), reference can be made to the description of the aromatic heterocycle constituting the "monovalent aromatic heterocyclic group" in Ar1 and Ar2 in general formula (1). Specific examples of the "divalent aromatic heterocyclic group" include divalent groups obtained by removing one hydrogen atom from the specific examples of the "monovalent aromatic heterocyclic group" described above.

[0089] Regarding the “substituent” when the “substituted or unsubstituted divalent aromatic hydrocarbon group” or “substituted or unsubstituted divalent aromatic heterocyclic group” represented by L in the general formula (2) has a substituent, reference can be made to the description and specific examples of the “substituent” in the “substituted or unsubstituted monovalent aromatic hydrocarbon group” or “substituted or unsubstituted monovalent aromatic heterocyclic group” represented by Ar1 and Ar2 in the general formula (1).

[0090] In the general formula (2), n represents an integer of 1 or 2, and is preferably 1. When n is 2, the two L's may be the same as or different from each other.

[0091] In the general formula (2), R1 to R3 represent a hydrogen atom, 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 alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms. R1 to R3 may be the same as or different from each other. In one embodiment of the present invention, R1 to R3 are selected from the group consisting of a hydrogen atom, a deuterium atom, and a linear or branched alkyl group having 1 to 6 carbon atoms. In one embodiment of the present invention, R1 to R3 are hydrogen atoms or deuterium atoms.

[0092] Specific examples of the "straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms" of the "substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms" represented by R1 to R3 in general formula (2) include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl. Specific examples of the "cycloalkyl group having 5 to 10 carbon atoms" of the "substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms" represented by R1 to R3 include cyclopentyl, cyclohexyl, 1-adamantyl, and 2-adamantyl. Specific examples of the "straight-chain or branched-chain alkenyl group" of the "substituted or unsubstituted straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms" represented by R1 to R3 include vinyl, allyl, isopropenyl, and 2-butenyl. R1 and R2 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom to form a ring. In one embodiment of the present invention, R1 and R2 are not bonded to each other to form a ring.

[0093] Regarding the “substituent” when the “substituted or unsubstituted straight-chain or branched alkyl group having 1 to 6 carbon atoms”, “substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms”, or “substituted or unsubstituted straight-chain or branched alkenyl group having 2 to 6 carbon atoms” represented by R1 to R3 in the general formula (2) has a substituent, reference can be made to the description and specific examples of the “substituent” in the “substituted or unsubstituted monovalent aromatic hydrocarbon group” and “substituted or unsubstituted monovalent aromatic heterocyclic group” represented by Ar1 and Ar2 in the general formula (1).

[0094] Specific examples of the "straight-chain or branched alkoxy group having 1 to 6 carbon atoms" of the "substituted or unsubstituted straight-chain or branched alkoxy group having 1 to 6 carbon atoms" represented by R1 to R3 in general formula (1) include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-pentoxy, and n-hexyloxy. Specific examples of the "cycloalkoxy group having 5 to 10 carbon atoms" of the "substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms" represented by R1 to R3 include cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, 1-adamantyloxy, and 2-adamantyloxy. R1 and R2 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted imino group, an oxygen atom, or a sulfur atom to form a ring.

[0095] Regarding the “substituent” in the “substituted or unsubstituted linear or branched alkoxy group having 1 to 6 carbon atoms” represented by R1 to R3 in the general formula (1), or the “substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms having a substituent”, reference can be made to the description and specific examples of the “substituent” in the “substituted or unsubstituted monovalent aromatic hydrocarbon group” and “substituted or unsubstituted monovalent aromatic heterocyclic group” represented by Ar1 and Ar2 in the general formula (1).

[0096] Examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R1 to R3 in the general formula (1) include aryloxy groups having 6 to 30 carbon atoms, such as phenoxy, biphenyloxy, terphenyloxy, naphthyloxy, anthryloxy, phenanthrenoxy, fluorenyloxy, spirobifluorenyloxy, indenyloxy, pyreneoxy, peryleneoxy, peryleneoxy, fluoranthenyloxy, and triphenyleneoxy. R1 and R2 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom to form a ring.

[0097] Regarding the “substituent” when the “substituted or unsubstituted aryloxy group” represented by R1 to R3 in the general formula (2) has a substituent, reference can be made to the description and specific examples of the “substituent” in the “substituted or unsubstituted monovalent aromatic hydrocarbon group” and “substituted or unsubstituted monovalent aromatic heterocyclic group” represented by Ar1 and Ar2 in the general formula (1).

[0098] In the general formula (2), either or both of Ar3 and Ar4 are preferably substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzofuranyl, and more preferably unsubstituted phenyl, unsubstituted biphenyl, or unsubstituted naphthyl. In one embodiment of the present invention, Ar3 in the general formula (2) is substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl. In one embodiment of the present invention, Ar4 in the general formula (2) is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0099] L in the general formula (2) is preferably an unsubstituted phenylene group, an unsubstituted biphenylene group, or an unsubstituted naphthylene group, and more preferably an unsubstituted phenylene group or an unsubstituted biphenylene group.

[0100] As Ar1 or Ar2 in the general formula (1), preferably, it is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylsilylphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted fluorenyl group, and more preferably, it is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0101] R1 to R3 in the general formula (2) are preferably a hydrogen atom or a deuterium atom, and more preferably a hydrogen atom.

[0102] Specific examples of preferred compounds among the compounds represented by the general formula (1) are shown below. However, the compounds represented by the general formula (1) 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 formula, hydrogen atoms ( 1 H) display, deuterium atoms ( 2 H) is represented by "D". In the compound represented by the general formula (1), some or all of the hydrogen atoms in the exemplified structure may be deuterium atoms.

[0103] [Chemical Formula 3]

[0104]

[0105] [Chemical Formula 4]

[0106]

[0107] [Chemical Formula 5]

[0108]

[0109] [Chemical Formula 6]

[0110]

[0111] [Chemical Formula 7]

[0112]

[0113] [Chemical Formula 8]

[0114]

[0115] [Chemical Formula 9]

[0116]

[0117] [Chemical Formula 10]

[0118]

[0119] [Chemical Formula 11]

[0120]

[0121] [Chemical Formula 12]

[0122]

[0123] [Chemical Formula 13]

[0124]

[0125] [Chemical Formula 14]

[0126]

[0127] [Chemical Formula 15]

[0128]

[0129] [Chemical Formula 16]

[0130]

[0131] [Chemical Formula 17]

[0132]

[0133] [Chemical Formula 18]

[0134]

[0135] [Chemical Formula 19]

[0136]

[0137] [Chemical Formula 20]

[0138]

[0139] [Chemical Formula 21]

[0140]

[0141] [Chemical Formula 22]

[0142]

[0143] [Chemical Formula 23]

[0144]

[0145] [Chemical Formula 24]

[0146]

[0147] [Chemical Formula 25]

[0148]

[0149] [Chemical Formula 26]

[0150]

[0151] [Chemical Formula 27]

[0152]

[0153] [Chemical Formula 28]

[0154]

[0155] [Synthesis Method and Property Evaluation Method of the Compound Represented by General Formula (1)]

[0156] The compound represented by the general formula (1) of the present invention is a novel compound.

[0157] The compound represented by the general formula (1) can be synthesized by a known method. For details of the synthesis method, reference can be made to the method described in Japanese Patent No. 7177966 (Patent Document 5) or the synthesis examples described below.

[0158] The compound represented by general formula (1) can be purified by known methods such as column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization from a solvent, and sublimation purification. The compound can be identified by NMR analysis.

[0159] [Usefulness of the compound represented by general formula (1)]

[0160] The compound represented by the general formula (1) of the present invention has excellent hole transport ability and electron blocking ability, and has high thermal stability in a thin film state, and is therefore useful as a material for the organic layer of an organic electroluminescent element. The compound represented by the general formula (1) can be used as a constituent material of, for example, a hole injection layer, an electron blocking layer, a hole transport layer, and a light-emitting layer of an organic electroluminescent element, and is particularly useful as a constituent material of an electron blocking layer and a hole transport layer. An organic EL element comprising a compound represented by the general formula (1) in an organic layer (such as at least one of an electron blocking layer, a hole transport layer, and a light-emitting layer) can achieve high luminous efficiency and high power efficiency, and long element life.

[0161] Examples of physical properties that serve as indicators of the usefulness of the compound represented by general formula (1) include the melting point, glass transition point (Tg), and work function (HOMO energy level). The melting point serves as an indicator of vapor deposition properties, the glass transition point (Tg) serves as an indicator of thin film stability, and the work function serves as an indicator of hole injection properties, hole transport properties, or electron blocking properties.

[0162] The melting point and the glass transition point (Tg) can be measured, for example, using a powder of the compound to be measured with a high-sensitivity differential scanning calorimeter (DSCvesta Thermo plus EV02 series, manufactured by Rigaku Corporation).

[0163] The work function (HOMO energy level) can be determined, for example, by forming a 100 nm thick thin film of the compound to be measured on an ITO-coated substrate and using an ionization potential measuring apparatus (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).

[0164] Organic electroluminescent devices

[0165] The organic electroluminescent element (organic EL element) of the present invention comprises: a pair of electrodes; and an organic layer disposed between the pair of electrodes and including at least a light-emitting layer, wherein at least one layer of the organic layer comprises a compound represented by the general formula (1). Here, the pair of electrodes is an anode and a cathode. For the description of the compound represented by the general formula (1), reference can be made to the description in the column "Compound represented by the general formula (1)". The compound represented by the general formula (1) has excellent hole transporting ability and electron blocking ability, and has high thermal stability in a thin film state. Therefore, by using it as a material for the organic layer, an organic EL element having high luminous efficiency and high power efficiency and a long element life can be realized.

[0166] The organic layer possessed by the organic EL element of the present invention includes at least a light-emitting layer, and may also have one or more organic layers other than the light-emitting layer. Here, the compound represented by the general formula (1) may be contained in the light-emitting layer, or in the organic layer other than the light-emitting layer, but is preferably contained in the organic layer disposed between the light-emitting layer and the anode. As a specific example of the organic layer disposed between the light-emitting layer and the anode, a hole injection layer, a hole transport layer, an electron blocking layer, etc. may be cited. The compound represented by the general formula (1) is preferably contained in the hole transport layer or the electron blocking layer, and is more preferably contained in the electron blocking layer. The materials of these organic layers can be appropriately selected and used from known materials in addition to the compounds represented by the general formula (1).

[0167] In one embodiment of the present invention, the organic EL element has a stacked structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode are stacked in sequence on a substrate, and at least a compound represented by the general formula (1) is contained in the electron blocking layer. Here, a hole blocking layer may be provided between the light-emitting layer and the electron transport layer. Furthermore, in the organic EL element of the present invention, one organic layer may have two or more functions. As such an organic layer, a hole injection transport layer having both a hole injection layer and a hole transport layer, or an electron injection transport layer having both an electron injection layer and an electron transport layer can be cited. Furthermore, in the organic EL element of the present invention, a structure in which two or more organic layers having the same function are stacked can also be provided. For example, a structure in which two layers of hole transport layers are stacked, a structure in which two layers of light-emitting layers are stacked, a structure in which two layers of electron transport layers are stacked, etc. can be cited. As long as the organic EL element of the present invention has at least an anode, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode in sequence, a mode in which other layers are provided between each layer is not excluded.

[0168] Hereinafter, each member and each layer of the organic EL element will be described in detail.

[0169] [anode]

[0170] As the anode of the organic EL element of the present invention, an electrode material having a large work function, such as ITO or gold, is used.

[0171] [Hole injection layer, hole transport layer]

[0172] 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 reduce the injection barrier of holes supplied from the anode, thereby reducing the driving voltage and increasing the luminance.

[0173] 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.

[0174] In the organic EL element of the present invention, a compound represented by the general formula (1) can be used as a material for a hole transport layer or a hole injection transport layer. Here, the hole transport layer or the hole injection transport layer may be composed of the compound represented by the general formula (1), or may be composed of a combination of the compound represented by the general formula (1) and other hole transport materials or hole injection materials.

[0175] The hole injection / transport performance, film stability and durability of the compound represented by the general formula (1) are excellent. Thus, the hole transport efficiency of the organic EL element using the compound represented by the general formula (1) as a hole injection material or a hole transport material to the light-emitting layer is improved, and the driving voltage is reduced, thereby improving the durability of the element, and obtaining high efficiency, low driving voltage and long life characteristics. The compound represented by the general formula (1) used in the hole injection layer, the hole transport layer and the hole injection and transport layer can be one of the compound group represented by the general formula (1), or two or more.

[0176] Furthermore, in the organic EL device of the present invention, the hole injection layer, the hole transport layer, or the hole injection transport layer may be composed of a material other than the compound represented by the general formula (1).

[0177] As materials for the hole injection layer, in addition to the compounds represented by the general formula (1), phthalocyanine compounds represented by copper phthalocyanine, porphyrin compounds, starburst-type triphenylamine derivatives, aromatic amine compounds having two or more triphenylamine structures or carbazole structures in the molecule and each having a structure formed by linking a single bond or a divalent group not containing a heteroatom, acceptor heterocyclic compounds such as hexacyanotriphenylene, and coating-type polymer materials can also be used.

[0178] As materials for the hole injection layer and the hole transport layer, in addition to the compound represented by the general formula (1), benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)-benzidine (TPD) or N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (NPD), N,N,N',N'-tetraphenylbenzidine, 1,1-bis[(di-4-methylphenylamino)phenyl]cyclohexane (TAPC), and arylamine compounds having two or more triphenylamine structures or carbazole structures in the molecule, each of which has a structure connected by a single bond or a divalent group not containing a hetero atom. Furthermore, coating-type polymer materials such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrenesulfonic acid) (PSS) and polymer compounds having the structure of a benzidine derivative such as TPD in part of their structure can also be used.

[0179] These materials can be formed as a single film composed of a single type or as a mixed film composed of multiple types. Furthermore, the hole injection layer, hole transport layer, and hole injection transport layer may have a single-layer structure of a single film or a mixed film, or may have a stacked structure composed of multiple single films, a stacked structure composed of multiple mixed films, or a stacked structure composed of one or more single films and one or more mixed films.

[0180] Furthermore, a hole injection layer or a hole transport layer may be formed by adding a p-type dopant such as tribromoaniline hexachloroantimony or a radialene derivative described in European Patent No. 2684932 to these hole injection materials or hole transport materials.

[0181] The absolute value of the energy level of the HOMO of the hole transport material is preferably a value greater than the absolute value (5.4 eV) of the HOMO level of the general hole transport materials such as NPD and TPD (that is, with a deeper HOMO level), preferably a value smaller than the absolute value of the energy level of the HOMO of the electron blocking material described later. By having a deeper HOMO level, there is a better hole transport ability. On the other hand, if the absolute value of the energy level of the HOMO of the hole transport material is smaller than the absolute value of the HOMO level of the electron blocking material, the transmission of holes to the light-emitting layer is hindered. Specifically, the absolute value of the energy level of the HOMO of the hole transport material is preferably more than 5.45 eV and less than 5.80 eV, more preferably more than 5.50 eV and less than 5.65 eV.

[0182] [Electron blocking layer]

[0183] The electron blocking layer is, for example, a layer disposed between the light-emitting layer and the hole transport layer, and has the function of inhibiting the diffusion of electrons present in the light-emitting layer to the outside of the light-emitting layer (the hole transport layer side). This can increase the probability of rebonding between electrons and holes in the light-emitting layer. The electron blocking layer generally also has the function of transporting holes. Furthermore, the electron blocking layer may also function as an exciton blocking layer, inhibiting the diffusion of excitons from the light-emitting layer.

[0184] As the material of the electron blocking layer, a compound represented by the general formula (1) can be used.

[0185] The compound represented by the general formula (1) has excellent electron blocking ability, high electron tolerance and is stable in a thin film state, and also has the characteristic of blocking excitons generated in the light-emitting layer. Thus, in an organic EL element using the compound represented by the general formula (1) as an electron blocking material, the probability of rebonding of holes and electrons is increased, thermal deactivation is suppressed, and therefore has high luminous efficiency, and by reducing the driving voltage, the current tolerance is improved, thereby increasing the maximum luminous brightness. The compound represented by the general formula (1) used for the electron blocking layer can be one of the compound group represented by the general formula (1), or two or more. Furthermore, the compound represented by the general formula (1) and other electron blocking materials can also be used in combination.

[0186] As materials for the electron blocking layer, in addition to the compound represented by the general formula (1), compounds having an electron blocking effect such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (Ad-Cz), and compounds having a triphenylsilyl and triarylamine structure, such as 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, can also be used. These materials can also function as hole transport materials.

[0187] These electron-blocking materials may be formed as a single film composed of a single type or as a mixed film composed of multiple types. Furthermore, the hole injection layer, hole transport layer, and hole injection transport layer may be single-layer structures composed of single films or mixed films, or may be stacked structures composed of multiple single films, stacked structures composed of multiple mixed films, or stacked structures composed of one or more single films and one or more mixed films.

[0188] The absolute value of the energy level of the HOMO of the electron blocking material is preferably a value greater than the absolute value of the energy level of the HOMO of the hole transport material (i.e., having a deeper HOMO level). Specifically, the absolute value of the energy level of the HOMO of the electron blocking material is preferably 5.55 eV or more and 5.90 eV or less, more preferably 5.60 eV or more and 5.80 eV or less. Furthermore, the absolute value of the energy level of the HOMO of the electron blocking material is preferably greater than 0.05 eV and less than 0.45 eV of the absolute value of the energy level of the HOMO of the hole transport material, more preferably greater than 0.05 eV and less than 0.35 eV, and further preferably greater than 0.10 eV and less than 0.35 eV.

[0189] [Luminous layer]

[0190] The light-emitting layer emits light by the rebonding of holes and electrons injected from the anode and cathode, respectively, to generate excitons. A light-emitting material alone may be used for the light-emitting layer, but preferably the light-emitting layer contains a light-emitting material and a host material.

[0191] As the host material, a compound represented by the general formula (1) can be used.

[0192] The compound represented by the general formula (1) has excellent hole transport properties and a wide energy band gap. Thus, when the compound represented by the general formula (1) is used as an organic EL element of a host material, the driving voltage is reduced and the luminous efficiency is improved. The compound represented by the general formula (1) used as the host material may be one of the compound group represented by the general formula (1), or may be two or more. Furthermore, the compound represented by the general formula (1) and other host materials may also be used in combination.

[0193] As a host material, in addition to the compound represented by the general formula (1), an anthracene derivative, a heterocyclic compound having an indole ring as a partial structure of a condensed ring, a heterocyclic compound having a carbazole ring as a partial structure of a condensed ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, and a polydialkylfluorene derivative can be used. In addition, as a host material having hole injection / transport properties, carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl (CBP), TCTA, and mCP can be cited. As a host material having electron transport properties, p-bis(triphenylsilyl)benzene (UGH2) or 2,2',2"-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI) can be cited.

[0194] The light-emitting material may be any one of a fluorescent light-emitting material, a phosphorescent light-emitting material, and a delayed fluorescent material.

[0195] Examples of light-emitting materials include metal complexes of quinolinol derivatives, including tris(8-hydroxyquinolinate)aluminum (Alq3), various metal complexes, anthracene derivatives, bis(phenylene)benzene derivatives, pyrene derivatives, oxazole derivatives, and poly(p-phenylene vinylene) derivatives. Examples include quinacridone, coumarin, rubrene, perylene, and their derivatives, benzopyran derivatives, rhodamine derivatives, and aminostyrene derivatives.

[0196] As the phosphorescent material, a phosphorescent light emitting body of a metal complex such as iridium or platinum can be used. For example, green phosphorescent light emitting bodies such as tris(2-phenylpyridyl)iridium(III) (Ir(ppy)3), bis[2-(4,6-difluorophenyl)pyridyl-C 2 , N](picolinate)iridium(III) (FIrpic), bis(2,4-difluorophenylpyridinyl)-tetrakis(1-pyrazolyl)borateiridium(III) (FIr6) and other blue phosphorescent light-emitting bodies, bis(2-benzo[b]thiophen-2-yl-pyridinyl)(acetylacetonato)iridium(III) (Btp2Ir(acac)) and other red phosphorescent light-emitting bodies, etc.

[0197] In order to avoid concentration quenching, the doping amount of the host material of the phosphorescent material is preferably set in the range of 1 to 30 wt % relative to the total weight of the light-emitting layer.

[0198] Examples of delayed fluorescent materials include triazine derivatives such as PIC-TRZ and CC2TA, phenoxazine derivatives such as PXZ-TRZ, and carbazolyl dicyanobenzene derivatives (CDCB derivatives) such as 4CzIPN. Specific examples of delayed fluorescent materials can be found in Appl. Phys. Let., 98, 083302 (2011).

[0199] [Chemical Formula 29]

[0200]

[0201] In the light-emitting layer, a compound represented by the following general formula (III-1) or (III-2) can be preferably used as a light-emitting material.

[0202] [Chemical formula 30]

[0203]

[0204] In the formula, Q1 to Q3 may be the same or different and represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms. Y1 to Y3 may be the same or different and represent N-R3, CR4R5, O, S, Se, or SiR6R7. R3 to R7 may be the same or different and represent a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monovalent alkyl group having 6 to 50 carbon atoms. An aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 30 carbon atoms. R3 to R7 may each be bonded to any one of Q1 to Q3 via a single bond, N, O, P, or S, or by condensation to form a ring. R4 and R5, and R6 and R7 may each be bonded to each other to further form a ring. When Y2 or Y3 is N-R3, at least one of R3 represents a group represented by the following general formula (IV-A) or a group represented by the following general formula (IV-B).

[0205] [Chemical Formula 31]

[0206]

[0207] In the general formula (IV-A), X represents O or S. R8 to R 15The alkyl radicals may be the same as or different from each other and represent a single bond, a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkyl radical having 1 to 30 carbon atoms R8~R 15 Any one of R8 to R 15 A ring may be formed by bonding to adjacent groups via a single bond, N, O, or S, or by ring condensation.

[0208] In the general formula (IV-B), R 16 R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms. 17 R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms. 18 ~R 20They may be the same as or different from each other and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 30 carbon atoms. The wavy portion represents the bond to N. R 16 ~R 20 A ring may be formed by bonding to adjacent groups via a single bond, N, O, or S, or by ring condensation.

[0209] Q1 to Q3 of the general formula (III-1) and (III-2) are preferably benzene rings. The benzene rings of Q1 and Q2 preferably adopt a benzofuran condensed ring structure or a benzothiophene condensed ring structure. As substituents for the benzene rings of Q1 to Q3, deuterium atoms, alkyl groups having 1 to 30 carbon atoms, aromatic hydrocarbon groups having 6 to 50 carbon atoms, diarylamino groups having 12 to 30 carbon atoms, and groups formed by combining two or more of these are preferred. Q2 of the general formula (III-1) and (III-2) is also preferably a furan ring formed by the condensation of a benzene ring (i.e., a benzofuran structure) or a thiol ring formed by the condensation of a benzene ring (i.e., a benzothiophene structure). Y1 of the general formula (III-1) and (III-2) is preferably O or S. Y2 and Y3 are preferably N-R3, respectively and independently. R3 is preferably a substituted or unsubstituted phenyl group (a ring may be condensed in the phenyl group). Preferred substituents include deuterium atoms, alkyl groups having 1 to 30 carbon atoms, aromatic hydrocarbon groups having 6 to 50 carbon atoms, dibenzofuranyl groups, dibenzothiophene groups, and combinations of two or more of these. The benzene ring constituting the phenyl group may have a benzofuran condensed ring structure or a benzothiophene condensed ring structure. Y3 is also preferably O.

[0210] Preferred compounds include compounds represented by the following general formula (III-1) and (III-2), compounds represented by the following general formula (III-3), compounds represented by the following general formula (III-4), compounds represented by the following general formula (III-5), and compounds represented by the following general formula (III-6).

[0211] [Chemical Formula 32]

[0212]

[0213] In general formulas (III-3) to (III-6), Y1 to Y3, R3 to R7 have the same meanings as in general formulas (III-1) and (III-2). Y4 represents N-R3, C-R4R5, O, S, Se, or Si-R6R7. Z may be the same or different and represents N or CR 21 . R 21 R represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms. 21 The groups may be bonded to adjacent groups via a single bond, N, O, or S, or may be condensed to form a ring.

[0214] In addition, the definitions and details of terms such as groups in the description of general formulae (III-1) to (III-5) are the same as the definitions and details of the corresponding terms of groups described in general formula (I).

[0215] The compound represented by the general formula (I) can exhibit more excellent effects by being used in combination with the compound represented by the general formula (III-1) or (III-2). Therefore, it is possible to provide: an electron-blocking material composed of a compound represented by the general formula (I) for use in combination with a compound represented by the general formula (III-1) or (III-2); a stack (preferably a light-emitting stack) comprising a layer of a compound represented by the general formula (III-1) or (III-2) and a layer comprising a compound represented by the general formula (I); an organic EL element comprising a compound represented by the general formula (III-1) or (III-2) and a compound represented by the general formula (I); an organic EL element having a layer comprising a compound represented by the general formula (I) and a layer comprising a compound represented by the general formula (III-1) or (III-2) (these two layers are preferably adjacent); and an organic EL element having an electron-blocking layer comprising a compound represented by the general formula (I) and a light-emitting layer comprising a compound represented by the general formula (III-1) or (III-2) (these two layers are preferably adjacent).

[0216] In addition, by using it in combination with a compound represented by the general formula (II) (WO2024 / 071332), an excellent effect can be exerted. Therefore, it is possible to provide: an electron blocking material composed of a compound represented by the general formula (I) for use in combination with a compound represented by the general formula (II) and a compound represented by the general formula (III-1) or (III-2); a laminate (preferably a light-emitting laminate) comprising a layer of a compound represented by the general formula (II), a layer of a compound represented by the general formula (III-1) or (III-2), and a layer of a compound represented by the general formula (I); a layer comprising a compound represented by the general formula (II), a compound represented by the general formula (III-1) or (III-2), a compound represented by the general formula (I); an organic EL element comprising a compound represented by the general formula (II), a layer comprising a compound represented by the general formula (I), and a layer comprising a compound represented by the general formula (III-1) or (III-2) (these three layers are preferably stacked in sequential contact); and an organic EL element comprising a hole transport layer comprising a compound represented by the general formula (II), an electron blocking layer comprising a compound represented by the general formula (I), and a light-emitting layer comprising a compound represented by the general formula (III-1) or (III-2) (these three layers are preferably stacked in sequential contact).

[0217] Specific examples of the compound represented by (III-1) or (III-2) are shown below. However, the compound represented by the general formula (III-1) or (III-2) that can be used in the present invention should not be construed as being limited by these specific examples.

[0218] [Chemical Formula 33]

[0219]

[0220] [Chemical Formula 34]

[0221]

[0222] [Chemical Formula 35]

[0223]

[0224] [Hole blocking layer]

[0225] The hole blocking layer is, for example, disposed between the light-emitting layer and the electron transporting 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 (toward the electron transporting layer).

[0226] As materials for the hole-blocking layer of the organic EL device of the present invention, compounds having hole-blocking properties, such as phenanthroline derivatives such as bathocuproine (BCP), metal complexes of quinolinol derivatives such as bis(2-methyl-8-quinolinate)-4-(phenylphenol)aluminum (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives, can be used. These materials can also function as electron-transporting materials.

[0227] These materials can be formed as a single film composed of a single type or as a mixed film composed of multiple types. Furthermore, the hole blocking layer can be a single-layer structure of a single film or a mixed film, or a stacked structure of multiple single films, a stacked structure of multiple mixed films, or a stacked structure of one or more single films and one or more mixed films.

[0228] [Electron transport layer, electron injection layer]

[0229] 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 reduce the injection barrier of electrons supplied from the cathode, thereby reducing the driving voltage and improving the luminance.

[0230] The electron transport layer is a layer that has the function of transporting electrons. The electron transport layer may also function as an electron injection transport layer.

[0231] As materials for the electron transport layer, metal complexes of quinolinol derivatives headed by Alq3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives and silole derivatives can be used.

[0232] These materials can be formed as a single film composed of a single type or as a mixed film composed of multiple types. Furthermore, the electron transport layer and the electron injection layer can have a single-layer structure of a single film or a mixed film, or a stacked structure of multiple single films, a stacked structure of multiple mixed films, or a stacked structure of one or more single films and one or more mixed films.

[0233] As materials for the electron injection layer, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. By preferably selecting the electron transport layer and the cathode, the electron injection layer can be omitted.

[0234] Furthermore, an electron injection layer or an electron transport layer may be formed by adding a metal (N-type dopant) such as cesium to these electron injection materials or electron transport materials.

[0235] [cathode]

[0236] As the cathode, a material using a metal having a low work function such as aluminum, or an alloy having an even lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy as an electrode material can be used.

[0237] Each layer constituting the above-described organic EL element can be formed by a known method such as vapor deposition, spin coating, and inkjet.

[0238] The compound represented by general formula (1) preferably used in the organic EL element of the present invention is preferably used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer or light emitting layer of the organic EL element, and more preferably used as a constituent material of the hole transport layer or electron blocking layer.

[0239] Therefore, the compound represented by general formula (1) of the present invention can be used as a material for the hole injection layer, hole transport layer, electron blocking layer or light emitting layer of an organic EL device to improve the luminous efficiency, driving voltage and durability of conventional organic EL devices.

[0240] Electronic equipment

[0241] The electronic device of the present invention comprises: a pair of electrodes; and at least one organic layer disposed between the pair of electrodes, wherein at least one of the organic layers comprises a compound represented by general formula (I). For a description of the compound represented by general formula (I), reference can be made to the description in the "Compound represented by general formula (I)" section above.

[0242] Examples of electronic devices include display devices or light-emitting devices equipped with organic EL elements. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting fixtures and vehicle lamps.

[0243] Example

[0244] Below, enumerate synthesis example and embodiment, feature of the present invention is further specifically described.About material shown below, processing content, processing sequence etc., as long as do not depart from the purport of the present invention, then can suitably change.Therefore, scope of the present invention is not limited to following embodiment.

[0245] [Synthesis Example 1] Synthesis of Compound (1-3)

[0246] 25 g of 1-chloro-2,4-dibromobenzene, 23 g of phenylboronic acid, 38.4 g of potassium carbonate, 2.1 g of tetrakistriphenylphosphine palladium (0), and a mixed solvent of toluene (100 ml) / EtOH (25 ml) / H₂O (115 ml) were added to a reaction vessel, followed by reflux stirring for 10 hours. The reaction solution was allowed to cool naturally, and then toluene and saturated brine were added. The organic layer was removed by extraction and separation, and then concentrated to obtain 24.2 g of 4'-chloro-1,1':3',1"-terphenyl in the form of butter (yield: 99.9%).

[0247] [Chemical Formula 36]

[0248]

[0249] Next, 8.3 g of (4,4,5,5-tetramethyl-1,3,2-dioxolan-2-yl)aniline, 9.8 g of 4'-chloro-1,1':3',1"-terphenyl, 16.1 g of tripotassium phosphate, 43 mg of palladium(II) acetate, 155 mg of Sphos, and a mixed solvent of 1,4-dioxane (40 ml) and purified water (12 ml) were added to the reaction vessel, and the mixture was stirred under reflux for 2 hours. After the reaction solution was naturally cooled, toluene and saturated brine were added, and the organic layer was removed by extraction and separation, and concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: toluene) to obtain 7.3 g of 4'-phenyl-[1,1':2',1"]terphenyl-4-amine as an off-white powder (yield: 61.6%).

[0250] [Chemical Formula 37]

[0251]

[0252] Next, 2.1 g of 4'-phenyl-[1,1':2',1"]terphenyl-4-amine, 2.0 g of 5'-bromo-[1,1':2',1"]terphenyl, 0.6 g of sodium tert-butoxide, 120 mg of tris(dibenzylideneacetone)dipalladium(0), 163 mg of 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl (BINAP), and 30 ml of toluene were added to the reaction vessel, followed by reflux stirring for 13 hours. The reaction solution was allowed to cool naturally, and the filtrate obtained by concentration and filtration was obtained to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / n-hexane) to obtain a pale yellow oil of (4'-phenyl-[1,1':2',1"]terphenyl-4-yl)-([1,1':2',1"]terphenyl-4'-yl)-amine: 3.0 g (yield: 84.1%).

[0253] [Chemical Formula 38]

[0254]

[0255] Next, (4'-phenyl-[1,1':2',1"]terphenyl-4-yl)-([1,1':2',1"]terphenyl-4'-yl)-amine: 2.8 g, 4"-bromo-[1,1':4',1"]terphenyl: 1.5 g, sodium tert-butoxide: 0.7 g, tris(dibenzylideneacetone)dipalladium(0): 117 mg, tri(tert-butyl)phosphine: 103 mg, and toluene (25 ml) were added to the reaction vessel, and the mixture was refluxed and stirred for 9 hours. After the reaction solution was naturally cooled, it was filtered to obtain a crude product. The obtained crude product was purified by adsorption on silica gel and purified by crystallization using a toluene / methanol mixed solvent, thereby obtaining the target compound (1-3) as an off-white powder: 3.2 g (yield: 84.6%).

[0256] The structure of the obtained compound (1-3) was identified using NMR.

[0257] use 1 The following 43 hydrogen signals were detected by H-NMR (CDCl 3 ).

[0258] δ(ppm)=7.63-7.68(10H), 7.33-7.54(13H), 7.18-7.29(10H), 7.10-7.12(2H), 7.01-7.05(4H), 6.95-6.97(4H)

[0259] [Chemical Formula 39]

[0260]

[0261] [Synthesis Example 2] Synthesis of Compound (1-22)

[0262] 4'-Chloro-1,1':3',1"-terphenyl: 24.4 g, bis(pinacol borate): 27.6 g, potassium acetate: 18.1 g, tris(dibenzylideneacetone)dipalladium(0): 0.8 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphоs): 1.5 g, and 1,4-dioxane: 125 ml were added to a reaction vessel, and the mixture was refluxed and stirred for 13 hours. After the reaction solution was naturally cooled, toluene and saturated brine were added, and the organic layer was collected by extraction and separation operations and concentrated to obtain 30.0 g (yield: 91.4%) of the yellow oil of 4,4,5,5-tetramethyl-(2-[1,1':3',1"-terphenyl]-4'-yl)-1,3,2-dioxolane.

[0263] [Chemical Formula 40]

[0264]

[0265] Next, 29.3 g of 4-bromo-4'-iodobiphenyl, 30.5 g of 4,4,5,5-tetramethyl-(2-[1,1':3',1"-terphenyl]-4'-yl)-1,3,2-dioxolane, 22.6 g of potassium carbonate, 0.9 g of tetrakistriphenylphosphine palladium (0), and a 1,4-dioxane (120 ml) / H2O (66 ml) mixed solvent were added to the reaction vessel, and the mixture was refluxed and stirred for 4 hours. After the reaction solution was naturally cooled, it was filtered to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: chloroform / n-hexane) to obtain 24.4 g of an off-white powder of 4"'-bromo-5'-phenyl-[1,1':2',1":4",1"'-tetraphenyl] (yield: 64.9%).

[0266] [Chemical Formula 41]

[0267]

[0268] Next, 2.6 g of bis(4-biphenylyl)amine, 3.7 g of 4'-bromo-5'-phenyl-[1,1':2',1':4',1'-tetraphenyl], 1.0 g of sodium tert-butoxide, 185 mg of tris(dibenzylideneacetone)dipalladium(0), 164 mg of tri(tert-butyl)phosphine, and 40 ml of toluene were added to the reaction vessel, and the mixture was refluxed and stirred for 6 hours. After the reaction solution was naturally cooled, the filtrate obtained by concentration and filtration was obtained to obtain a crude product. The obtained crude product was purified by adsorption on silica gel and crystallized from a toluene / methanol mixed solvent to obtain 3.9 g of the target compound (1-22) as a pale yellowish-white powder (yield: 68.3%).

[0269] The structure of the obtained compound (1-22) was identified using NMR.

[0270] use 1 The following 39 hydrogen signals were detected by H-NMR (CDCl 3 ).

[0271] δ(ppm)=7.66-7.69(4H), 7.55-7.60(5H), 7.51-7.53(6H), 7.41-7.48(8H), 7.36-7.38(1H), 7.30-7.33(2H), 7.21-7.25(13H)

[0272] [Chemical Formula 42]

[0273]

[0274] [Synthesis Example 3] Synthesis of Compound (1-7)

[0275] To the reaction vessel were added ([1,1'-biphenyl]-4-yl)-(4'-phenyl-[1,1':2',1"]terphenyl-4-yl)-amine: 3.0 g, 4-chloro-3'-(naphthalene-1-yl)-1,1'-biphenyl: 2.0 g, sodium tert-butoxide: 0.9 g, tris(dibenzylideneacetone)dipalladium(0): 58 mg, tri(tert-butyl)phosphine: 103 mg, and toluene (30 ml), and the mixture was refluxed and stirred for 10 hours. After the reaction solution was naturally cooled, it was filtered to obtain a crude product. The obtained crude product was purified by adsorption on silica gel and purified by crystallization using a toluene / methanol mixed solvent, thereby obtaining the target compound (1-7) as an off-white powder: 3.4 g (yield: 71%).

[0276] The structure of the obtained compound (1-7) was identified using NMR.

[0277] use 1 The following 41 hydrogen signals were detected by H-NMR (CDCl 3 ).

[0278] δ(ppm)=7.97(1H), 7.92(1H), 7.87(1H), 7.72(1H), 7.68-7.64(5H), 7.57 -7.40(17H), 7.36(1H), 7.32-7.23(6H), 7.17(4H), 7.07(2H), 7.02(2H).

[0279] [Chemical Formula 43]

[0280]

[0281] [Synthesis Example 4] Synthesis of Compound (1-337)

[0282] To a reaction vessel were added ([1,1'-biphenyl]-4-yl)-(4'-phenyl-[1,1':2',1"]terphenyl-4-yl)-amine: 3.0 g, 3-bromodibenzofuran: 1.9 g, sodium tert-butoxide: 0.8 g, tris(dibenzylideneacetone)dipalladium(0): 130 mg, tri(tert-butyl)phosphine: 170 mg, and toluene (40 ml), and the mixture was refluxed and stirred for 1 hour. After the reaction solution was naturally cooled, it was filtered to obtain a crude product. The obtained crude product was purified by adsorption on silica gel and purified by crystallization using a toluene / methanol mixed solvent, thereby obtaining the target compound (1-337) as an off-white powder: 5.0 g (yield: 90%).

[0283] The structure of the obtained compound (1-337) was identified using NMR.

[0284] use 1 The following 37 hydrogen signals were detected by H-NMR (CDCl 3 ).

[0285] δ(ppm)=7.87(1H), 7.82(1H), 7.68-7.64(10H), 7.57-7.52(4H), 7.47(4H), 7.41-7.27(10H), 7.20(2H), 7.15(1H), 7.09(2H), 7.09(2H).

[0286] [Chemical Formula 44]

[0287]

[0288] [Synthesis Example 5] Synthesis of Compound (1-93)

[0289] N-[4-([1,1':5',1":4",1"'-tetraphenyl]-2'-yl)phenyl-([1,1'-biphenyl]-4-yl)amine: 12.5 g, 4-bromo-1,1'-biphenyl: 5.8 g, trisdibenzylideneacetone dipalladium: 0.2 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.3 g, and toluene: 125 mL were added to a reaction vessel, and the mixture was stirred under heating and reflux for 3 hours. After confirming the completion of the reaction, the reaction residue was filtered and washed with methanol, and the obtained crude crystals were recrystallized with toluene and acetone solvents to obtain the target compound (1-93) as a white powder: 10.7 g (yield: 67%).

[0290] The structure of the obtained compound (1-93) was identified using NMR.

[0291] use 1 H-NMR (CDCl 3 ) detected the following 39 hydrogen signals.

[0292] δ(ppm)=7.77(2H), 7.73-7.70(4H), 7.67(2H), 7.61-7.57(5H), 7.52-7.42(10H), 7.39-7.26(8H), 7.19(4H), 7.10-7.03(4H).

[0293] [Chemical Formula 45]

[0294]

[0295] [Synthesis Example 6] Synthesis of Compound (1-306)

[0296] To a reaction vessel were added 13.3 g of N-[4-([1,1':5',1":3",1"'-tetraphenyl]-2'-yl)phenyl]-[1,1'-biphenyl]-4-yl)amine, 6.2 g of 4-bromo-1,1'-biphenyl, 0.2 g of trisdibenzylideneacetone dipalladium, 0.2 g of tri-tert-butylphosphine, 3.5 g of sodium tert-butoxide, and 133 mL of toluene, followed by stirring under heating and reflux overnight. After confirming completion of the reaction, the filtrate obtained by filtration was concentrated. The concentrate was washed with toluene and acetone solvents and recrystallized to obtain 13.1 g of the target compound (1-306) as a white powder (yield: 78%).

[0297] The structure of the obtained compound (1-306) was identified using NMR.

[0298] use 1 H-NMR (CDCl 3 ) detected the following 39 hydrogen signals.

[0299] δ(ppm)=7.89(1H), 7.73-7.70(2H), 7.67(3H), 7.60-7.26(25H), 7.18(4H), 7.10-7.03(4H).

[0300] [Chemical Formula 46]

[0301]

[0302] [Synthesis Example 7] Synthesis of Compound (1-335)

[0303] To a reaction vessel were added 12.8 g of N-[4-([1,1':5',1":2",1"'-quaterphenyl]-2'-yl)phenyl]-([1,1'-biphenyl]-4-yl)amine, 6.0 g of 4-bromo-1,1'-biphenyl, 0.2 g of trisdibenzylideneacetone dipalladium, 0.2 g of tri-tert-butylphosphine, 3.4 g of sodium tert-butoxide, and 128 mL of toluene, followed by stirring under heating and reflux overnight. After confirming the completion of the reaction, acetone was added to the reaction solution and the precipitated solid was filtered out. The obtained solid was washed with toluene and acetone solvents and recrystallized to obtain 7.5 g of the target compound (1-335) as a white powder (yield: 46%).

[0304] The structure of the obtained compound (1-335) was identified using NMR.

[0305] use 1 H-NMR (DMSO-d6) detected the following 39 hydrogen signals.

[0306] δ(ppm)=7.67-7.58(9H), 7.51-7.43(7H), 7.39-7.28(7H), 7.23(5H), 7.09(4H), 7.05-7.00(3H), 6.95-6.93(2H), 6.87-6.85(2H).

[0307] [Chemical Formula 47]

[0308]

[0309] [Synthesis Example 8] Synthesis of Compound (1-339)

[0310] To a reaction vessel were added 10.0 g of N-phenyl-(4'-(naphthalen-1-yl)-[1,1':2',1"-terphenyl]-4-yl)-amine, 7.0 g of 2-(4-bromophenyl)naphthalene, 0.2 g of trisdibenzylideneacetone dipalladium, 0.2 g of tri-tert-butylphosphine, 3.2 g of sodium tert-butoxide, and 100 mL of toluene, followed by stirring under heating and reflux for 3 hours. After confirming the completion of the reaction, the filtrate obtained by concentrating and filtering the reaction solution was purified by silica gel chromatography using dichloromethane and n-heptane to obtain 13.6 g of the target compound (1-339) as a white powder (yield: 94%).

[0311] The structure of the obtained compound (1-339) was identified using NMR.

[0312] use 1 The following 35 hydrogen signals were detected by H-NMR (CDCl 3 ).

[0313] δ(ppm)=8.09(1H), 8.02(1H), 7.94-7.85(5H), 7.75(1H), 7.64-7.45(11H), 7.32-7.24(7H), 7.20-7.12(6H), 7.07-7.02(3H).

[0314] [Chemical Formula 48]

[0315]

[0316] [Synthesis Example 9] Synthesis of Compound (1-341)

[0317] To a reaction vessel were added 7.5 g of N-([1,1'-biphenyl]-4-yl)-(4'-(naphthalene-1-yl)-[1,1':2',1"-terphenyl]-4-yl)-amine, 4.5 g of 1-(4-bromophenyl)naphthalene, 0.3 g of trisdibenzylideneacetone dipalladium, 0.1 g of tri-tert-butylphosphine, 2.8 g of sodium tert-butoxide, and 75 mL of toluene, followed by stirring under heating and reflux overnight. After confirming the completion of the reaction, the filtrate obtained by concentrating and filtering the reaction solution was purified by silica gel chromatography and recrystallized using dichloromethane and methanol solvents to obtain 8.9 g of the target compound (1-341) as a white powder (yield: 86%).

[0318] The structure of the obtained compound (1-341) was identified using NMR.

[0319] use 1 H-NMR (CDCl 3 ) detected the following 39 hydrogen signals.

[0320] δ(ppm)=8.10(1H), 8.04(1H), 7.94-7.85(4H), 7.63-7.41(20H), 7.35-7.24(9H), 7.18(2H), 7.13(2H).

[0321] [Chemical Formula 49]

[0322]

[0323] [Synthesis Example 10] Synthesis of Compound (1-342)

[0324] To the reaction vessel were added 13.0 g of N-([1,1'-biphenyl]-4-yl)-(4'-(naphthalene-1-yl)-[1,1':2',1"-terphenyl]-4-yl)-amine, 7.7 g of 2-(4-bromophenyl)naphthalene, 0.5 g of trisdibenzylideneacetone dipalladium, 0.2 g of tri-tert-butylphosphine, 4.7 g of sodium tert-butoxide, and 130 mL of toluene, and the mixture was stirred under heating and reflux overnight. After confirming the completion of the reaction, methanol was added to the reaction solution and the precipitated solid was filtered out. By recrystallizing the obtained solid with toluene and acetone solvents, 3.6 g of compound (1-342) as a white powder was obtained (yield: 20%).

[0325] The structure of the obtained compound (1-342) was identified using NMR.

[0326] use 1 H-NMR (CDCl 3 ) detected the following 39 hydrogen signals.

[0327] δ(ppm)=8.10(1H), 8.04(1H), 7.95-7.85(5H), 7.76(1H), 7.66-7.43(17H), 7.35-7.22(10H), 7.16(2H), 7.09(2H).

[0328] [Chemical Formula 50]

[0329]

[0330] [Synthesis Example 11] Synthesis of Compound (1-343)

[0331] To a reaction vessel were added 7.5 g of N-([1,1'-biphenyl]-4-yl)-(4'-(naphthalen-1-yl)-[1,1':2',1"-terphenyl]-4-yl)-amine, 5.3 g of 9-(4-bromophenyl)phenanthrene, 0.3 g of trisdibenzylideneacetone dipalladium, 0.1 g of tri-tert-butylphosphine, 2.8 g of sodium tert-butoxide, and 75 mL of toluene, followed by stirring under heating and reflux overnight. After confirming the completion of the reaction, the filtrate obtained by concentrating and filtering the reaction solution was purified by silica gel chromatography and recrystallized using dichloromethane and methanol solvents to obtain 9.2 g of the target compound (1-343) as a white powder (yield: 83%).

[0332] The structure of the obtained compound (1-343) was identified using NMR.

[0333] use 1 The following 41 hydrogen signals were detected by H-NMR (CDCl 3 ).

[0334] δ(ppm)=8.80(1H), 8.74(1H), 8.09(2H), 7.95-7.88(3H), 7.77-7.43(21H), 7.35-7.26(9H), 7.19(2H), 7.15(2H).

[0335] [Chemical Formula 51]

[0336]

[0337] [Synthesis Example 12] Synthesis of Compound (1-344)

[0338] N-phenyl-(4'-(phenanthrene-9-yl)[1,1':2',1"-terphenyl]-4-yl)-amine: 10.0 g, 1-(4-bromophenyl)naphthalene: 6.3 g, trisdibenzylideneacetone dipalladium: 0.2 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 2.9 g, and toluene: 100 mL were added to a reaction vessel, and the mixture was stirred under heating and reflux for 3 hours. After confirming the completion of the reaction, the filtrate obtained by concentration and filtration was purified by silica gel chromatography using dichloromethane and n-heptane to obtain the target compound (1-344) as a white powder: 10.0 g (yield: 67%).

[0339] The structure of the obtained compound (1-344) was identified using NMR.

[0340] use 1 H-NMR (CDCl 3 ) detected the following 37 hydrogen signals.

[0341] δ(ppm)=8.80(1H), 8.74(1H), 8.12(1H), 8.03(1H), 7.91(2H), 7.85(1H), 7.80(1H), 7.72-7.44(11H), 7.39(2H), 7.34-7.15(13H), 7.10-7.05(3H).

[0342] [Chemical Formula 52]

[0343]

[0344] [Synthesis Example 13] Synthesis of Compound (1-346)

[0345] To a reaction vessel were added 10.0 g of N-phenyl-(4'-(phenanthrene-9-yl)[1,1':2',1"-terphenyl]4-yl)-amine, 7.4 g of 9-(4-bromophenyl)phenanthrene, 0.2 g of trisdibenzylideneacetone dipalladium, 0.2 g of tri-tert-butylphosphine, 2.9 g of sodium tert-butoxide, and 75 mL of toluene, followed by stirring under heating and reflux overnight. After confirming completion of the reaction, the filtrate obtained by concentrating and filtering the reaction solution was purified by silica gel chromatography using dichloromethane and n-heptane to obtain 10.0 g of the target compound (1-346) as a white powder (yield: 66%).

[0346] The structure of the obtained compound (1-346) was identified using NMR.

[0347] use 1 H-NMR (CDCl 3 ) detected the following 39 hydrogen signals.

[0348] δ(ppm)=8.80(2H), 8.74(2H), 8.13(1H), 8.06(1H), 7.91(2H), 7.81(1H), 7.73-7.58(12H), 7.45(2H), 7.35-7.22(11H), 7.18(2H), 7.12-7.06(3H).

[0349] [Chemical Formula 53]

[0350]

[0351] <Evaluation of properties of the compound represented by general formula (1)>

[0352] Determination of glass transition temperature

[0353] The glass transition temperature of each compound synthesized in Synthesis Examples 1 to 13 and the comparative example compound (EBM-1) was measured using a high-sensitivity differential scanning calorimeter (DSCvesta Thermo plus EV02 series, manufactured by Rigaku Corporation).

[0354] [Chemical Formula 54]

[0355]

[0356] EBM-1 is a compound described in Patent Document 5.

[0357] [Table 1]

[0358] Compound Glass transition temperature (℃) Compound (1-3) 110 Compound (1-7) 112 Compound (1-22) 118 Compound (1-99) 107 Compound (1-335) 100 Compound (1-337) 115 Compound (1-339) 100 Compound (1-341) 114 Compound (1-342) 111 Compound (1-343) 127 Compound (1-344) 117 Compound (1-346) 134 EBM-1 103

[0359] As shown in Table 1, the glass transition temperatures of the compounds synthesized in Synthesis Examples 1 to 13 were all 97°C or higher, the same as those of the comparative compound (EBM-1). This confirms that the compounds represented by general formula (1) are stable in thin film form. Therefore, by using the compounds represented by general formula (1) as materials for organic EL devices, devices with excellent thermal stability can be produced.

[0360] Determination of HOMO energy levels

[0361] Thin films of compounds (1-3), (1-7), (1-22), (1-337), and EBM-1 were formed on an ITO substrate by vacuum deposition to a thickness of 100 nm. The absolute value of the HOMO energy level (equivalent to the work function) of each thin film was measured using an ionization potential measurement device (Sumitomo Heavy Industries, Ltd., PYS-202). The results are summarized in Table 2.

[0362] [Table 2]

[0363] Compound Absolute value of HOMO energy level (eV) Compound (1-3) 5.65 Compound (1-7) 5.64 Compound (1-22) 5.64 Compound (1-337) 5.63 EBM-1 5.64

[0364] As shown in Table 2, compounds (1-3), (1-7), (1-22), and (1-337) were confirmed to have a work function larger than 5.4 eV, which is a work function of common hole transport materials such as NPD and TPD, and to have good hole transport capabilities.

[0365] <Evaluation of Organic EL Devices>

[0366] [Example 1]

[0367] The layer structure of the organic EL element produced in this example is shown in FIG. Figure 1 In this embodiment, a reflective ITO electrode is pre-formed on a glass substrate 1 as a transparent anode 2. A hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a capping layer 10 are then sequentially deposited thereon to produce an organic EL element.

[0368] Specifically, a glass substrate 1, on which a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were sequentially formed, was ultrasonically cleaned in isopropyl alcohol for 20 minutes and then dried on a hot plate heated to 250°C for 10 minutes. After a 2 minute UV ozone treatment, the glass substrate with ITO (transparent anode) was placed in a vacuum deposition machine and the pressure was reduced to below 0.001 Pa.

[0369] Next, a compound (Acceptor-1) and a compound (BCFN) were deposited by dual deposition to form a 10 nm thick hole injection layer 3 so as to cover the transparent anode 2. The deposition rate ratio was set to Acceptor-1:BCFN = 3:97.

[0370] On the hole injection layer 3 , the hole transport layer 4 was formed by vapor deposition of a compound (BCFN) to a film thickness of 140 nm.

[0371] On the hole transport layer 4 , the electron blocking layer 5 was formed by vapor deposition of the compound (1-3) to a film thickness of 5 nm.

[0372] On the electron blocking layer 5, a compound (Dopant-1) and a compound (ADN) were binary deposited to form a 20 nm thick light emitting layer 6. At this time, the deposition rate ratio was set to Dopant-1:ADN=2:98.

[0373] Compound (ETM-1) and compound (ETM-2) were deposited binary to form a 30 nm thick electron transport layer 7 on the light emitting layer 6. The deposition rate ratio was set to ETM-1:ETM-2=50:50.

[0374] On the electron transport layer 7 , lithium fluoride was vapor-deposited to a film thickness of 1 nm to form the electron injection layer 8 .

[0375] On the electron injection layer 8 , a cathode 9 was formed by vapor deposition of a magnesium-silver alloy to a film thickness of 12 nm.

[0376] Finally, the compound (CPL-1) was vapor-deposited to a film thickness of 60 nm to form the cover layer 10 .

[0377] An organic EL device was manufactured through the above steps.

[0378] [Chemical Formula 55]

[0379]

[0380] [Chemical Formula 56]

[0381]

[0382] [Chemical Formula 57]

[0383]

[0384] [Chemical Formula 58]

[0385]

[0386] [Examples 2 to 10, Comparative Examples 1 and 2]

[0387] An organic EL device was produced under the same conditions as in Example 1, except that the compounds shown in Table 3 below were used instead of the compound (1-3) used as the material of the electron blocking layer 5 in Example 1.

[0388] [Chemical Formula 59]

[0389]

[0390] EBM-2 is a compound described in Patent Document 7.

[0391] The organic EL devices prepared in Examples 1 to 10 and Comparative Examples 1 and 2 were subjected to a DC voltage in the atmosphere at room temperature, and the device characteristics were measured. The results are summarized in Table 3. The luminance at the start of luminescence (initial luminance) was set to 1000 cd / m 2When the constant current is driven, the luminous brightness decays to 950cd / m 2 The device life was measured by the time (corresponding to 95%:95% decay when the initial luminance was 100%).

[0392] [Table 3]

[0393]

[0394] As shown in Table 3, the flowing current density is 10 mA / cm 2 The luminous efficiency at a current of 10.63 to 10.81 cd / A for the organic EL elements of Comparative Examples 1 to 2 was, on the other hand, 10.83 to 11.13 cd / A for the organic EL elements of Examples 1 to 10, which is equivalent to or better. Furthermore, the power efficiency was 9.12 to 9.15 lm / W for the organic EL elements of Comparative Examples 1 to 2, on the other hand, 9.15 to 9.54 lm / W for the organic EL elements of Examples 1 to 10, which is equivalent to or better. Furthermore, the device life (95% attenuation) was 363 to 365 hours for the organic EL elements of Comparative Examples 1 to 2, on the other hand, 365 to 466 hours for the organic EL elements of Examples 1 to 10, which is equivalent to or better.

[0395] The above results indicate that the use of a compound represented by the general formula (1) having high thermal stability and excellent electron-blocking ability can realize an organic EL element having high luminous efficiency and a long life compared to conventional organic EL elements.

[0396] Industrial applicability

[0397] The compound of the present invention has excellent electron blocking ability and hole transport ability, and has high thermal stability in a thin film state. Therefore, the organic EL device using the compound of the present invention can achieve high luminous efficiency and high power efficiency, long device life, for example, it can be expanded to the display device or lighting of household electrical appliances. Therefore, the industrial availability of the present invention is high.

[0398] Explanation of symbols

[0399] 1-glass substrate, 2-transparent anode, 3-hole injection layer, 4-hole transport layer, 5-electron blocking layer, 6-light-emitting layer, 7-electron transport layer, 8-electron injection layer, 9-cathode, 10-covering layer.

Claims

1. A compound represented by the following general formula (1) and satisfying at least one of the following (Condition 1) to (Condition 5), [Chemical Formula 1] Ar1 and Ar2 in the general formula (1) may be the same or different, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group, X1 represents a group represented by the following general formula (2), in, In the following general formula (2), when n is 1, L is an unsubstituted phenylene group, Ar3 and Ar4 are unsubstituted phenyl groups, Ar1, Ar2 and X1 are different, [Chemical Formula 2] Ar3 and Ar4 in the general formula (2) may be the same or different, Substituted or unsubstituted phenyl, Substituted or unsubstituted biphenyl, Substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, Substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted Fiki, L means a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group, R1 to R3 may be the same or different. Hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, 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 alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, n represents an integer of 1 or 2. When n is 2, L may be the same as or different from each other. * represents the bonding position to N in the general formula (1), (Condition 1) L in the general formula (2) is a substituted or unsubstituted biphenylene group, (Condition 2) Ar3 in the general formula (2) is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted phenanthrenyl group, (Condition 3) At least one of Ar3 and Ar4 in the general formula (2) is a substituted or unsubstituted biphenyl group, (Condition 4) At least one of Ar1 and Ar2 in the general formula (1) is a substituted or unsubstituted monovalent aromatic hydrocarbon group including a condensed polycyclic structure, or a substituted or unsubstituted monovalent aromatic heterocyclic group including a condensed polycyclic structure, (Condition 5) At least one of Ar1 and Ar2 in the general formula (1) is a substituted or unsubstituted 3,4-diphenylphenyl group.

2. The compound according to claim 1, wherein In the general formula (2), R1 to R3 are hydrogen atoms or deuterium atoms, which may be the same or different.

3. The compound according to claim 1, wherein In the general formula (2), at least one of Ar3 and Ar4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

4. The compound according to claim 3, wherein In the general formula (2), Ar3 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

5. The compound according to claim 3, wherein In the general formula (2), Ar4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

6. The compound according to claim 1, wherein In the general formula (2), L is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.

7. The compound according to claim 1, wherein In the general formula (1), Ar1 and Ar2 are respectively the same or different, and are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylsilylphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted fluorenyl.

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

9. The compound according to claim 1, which satisfies (Condition 1). The compound according to claim 1 , which satisfies (Condition 2). The compound according to claim 1 , which satisfies (Condition 3). The compound according to claim 1 , which satisfies (Condition 4). The compound according to claim 1 , which satisfies (Condition 5).

14. An organic electroluminescent element comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein: The organic layer contains the compound according to any one of claims 1 to 13.

15. The organic electroluminescent element according to claim 14, wherein The organic layer is a hole transport layer.

16. The organic electroluminescent element according to claim 14, wherein The organic layer is an electron blocking layer.

17. An electronic device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein: The organic layer contains the compound according to any one of claims 1 to 13.

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