Organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element using a compound represented by general formula and an organoboron compound has high efficiency, low driving voltage, and long life. A3, R1, and R2 each represents a monovalent aromatic hydrocarbon group or the like, A1 and A2 each represents a naphthylene group, and L1 to L3 each represents a single bond or a divalent aromatic hydrocarbon group or the like.

Description

Technical Field

[0001] This invention relates to a self-emissive element, namely an organic electroluminescent element, suitable for various display devices and electronic devices. More specifically, it relates to an organic electroluminescent element (hereinafter referred to as an organic EL element) and electronic devices using specific aromatic amine compounds and specific organoboron compounds. Background Technology

[0002] Because organic EL elements are self-emissive, they are brighter and have better visual clarity than liquid crystal elements, enabling clear displays, and therefore are under active research.

[0003] In 1987, CWTang et al. from Eastman Kodak developed a layered structure element that distributed various functions among different materials as a practical organic EL element. Specifically, they layered a phosphor capable of transporting electrons and an organic material capable of transporting holes, injected both charges into the phosphor layer to cause it to emit light, thereby achieving a voltage of 1000 cd / m² at voltages below 10 V. 2 The above high brightness (for example, see Patent Document 1 and Patent Document 2).

[0004] To date, many improvements have been made to make organic EL devices practical, and the various functions of the stacked structure have been further subdivided. High efficiency and durability have been achieved by stacking 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 in sequence on a substrate (for example, see Non-Patent Literature 1).

[0005] Furthermore, with the aim of further improving luminescence efficiency, the use of phosphorescent compounds is being investigated by utilizing triplet excitons (for example, see Non-Patent Literature 2).

[0006] Furthermore, a device utilizing light emission based on thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Adachi et al. from Kyushu University achieved an external quantum efficiency of 5.3% using a device made of thermally activated delayed fluorescence material (see, for example, non-patent literature 3).

[0007] The light-emitting layer of these organic EL elements is typically made by doping a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence into a charge-transporting compound known as the host material. Furthermore, as described in the aforementioned non-patent documents, various organic layers are provided in the organic EL elements, and the choice of organic material has a significant impact on the efficiency or durability of the element (see, for example, non-patent document 2).

[0008] In organic electroluminescent (EL) devices, light emission is achieved by the rebonding of charges injected from the two electrodes in the light-emitting layer. Therefore, efficiently transferring the charges of holes and electrons to the light-emitting layer is crucial, requiring the fabrication of devices with excellent carrier balance. Furthermore, by improving hole injection capability and electron blocking capability, the probability of hole-electron rebonding is increased, further restricting the excitons generated within the light-emitting layer, thereby achieving high luminous efficiency. Thus, the role of hole transport materials is critical, requiring materials with high hole injection capability, high hole mobility, high electron blocking capability, and consequently, high electron durability.

[0009] Furthermore, the heat resistance and amorphous properties of the material are also important factors regarding the lifespan of the device. In materials with low heat resistance, the heat generated during device operation can cause thermal decomposition even at relatively low temperatures, leading to material degradation. In materials with low amorphous properties, thin film crystallization can occur even within a short period, resulting in device degradation. Therefore, the materials used must possess both high heat resistance and good amorphous properties.

[0010] To date, N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) or various aromatic amine derivatives have been known as hole transport materials for organic electroluminescent (EL) devices (e.g., see Patent Documents 1 and 2). While NPD exhibits good hole transport capabilities, its glass transition point (Tg), an indicator of heat resistance, is as low as 96°C, leading to a decrease in device characteristics due to crystallization at high temperatures (e.g., see Non-Patent Document 4). Furthermore, among the aromatic amine derivatives described in the aforementioned patent documents, those with a hole mobility of 10-1 are known. -3 cm 2 Compounds with excellent mobility of / Vs or higher (e.g., see Patent Documents 1 and 2) have insufficient electron blocking properties, causing some electrons to pass through the light-emitting layer, thus preventing the expectation of improved luminous efficiency. Therefore, for further high efficiency, materials with higher electron blocking properties, more stable films, and higher heat resistance are required. Furthermore, although there are reports of highly durable aromatic amine derivatives (e.g., see Patent Document 3), these aromatic amine derivatives are used as charge transport materials for electrophotographic photosensitive devices, but there are no examples of their use in organic EL elements.

[0011] As compounds that improve properties such as heat resistance or hole injection capability, aromatic amine compounds with substituted carbazole structures have been proposed (for example, see Patent Documents 4 and 5). However, when these compounds are used in devices with hole injection layers or hole transport layers, although improvements in heat resistance or luminous efficiency are achieved, they are not sufficient, and further reductions in driving voltage or further increases in luminous efficiency are required.

[0012] Furthermore, in order to improve the device characteristics of organic EL devices, by combining materials with excellent hole and electron injection / transport performance and thin film stability or durability, devices with high efficiency, low driving voltage and long lifespan with carrier balance are required.

[0013] Previous technical documents

[0014] Patent documents

[0015] Patent Document 1: US Patent No. 5,792,557

[0016] Patent Document 2: US Patent No. 5639914

[0017] Patent Document 3: US Patent No. 7759030

[0018] Patent Document 4: JP2009076817A1

[0019] Patent Document 5: JP6674892B2

[0020] Patent Document 6: Description of European Patent No. 2684932

[0021] Patent Document 7: Korean Patent No. 10-2020-0131929

[0022] Patent Document 8: WO2017 / 073594A1

[0023] Non-patent literature

[0024] Non-patent literature 1: Proceedings of the 9th Symposium of the Chinese Society of Applied Physics, pp. 55-61 (2001)

[0025] Non-patent literature 2: Proceedings of the 9th Symposium of the Chinese Society of Applied Physics, pp. 23-31 (2001)

[0026] Non-patent literature 3: Appl. Phys. Let., 98, 083302 (2011)

[0027] Non-patent literature 4: Proceedings of the Third Regular Meeting of the Organic EL Symposium, pp. 13-14 (2006) Summary of the Invention

[0028] The technical problem to be solved by the invention

[0029] The object of this invention is to provide an organic EL element with high efficiency, low drive voltage, and long lifespan by appropriately combining the materials used. Furthermore, the object of this invention is also to provide an electronic device using this organic EL element.

[0030] means for solving technical problems

[0031] Therefore, in order to achieve the above objectives, the inventors, focusing on the excellent hole injection / transport capabilities, film stability, and durability of aromatic amine compounds, conducted in-depth research on various aromatic amine compounds and evaluated the characteristics of organic EL devices fabricated using them. As a result, the inventors obtained the following insight: if an aromatic amine compound with a specific structure is used as a material for the hole transport layer, holes injected from the anode side can be transported efficiently. Furthermore, they obtained the following insight: by combining organoboron compounds with specific structures, various organic EL devices with low driving voltage, high efficiency, and long lifetime can be fabricated. As a result, the present invention was completed.

[0032] That is, according to the present invention, the following organic EL element is provided.

[0033] 1) An organic EL element having an anode, a cathode and an organic layer sandwiched between the anode and the cathode, wherein the organic layer contains an aromatic amine compound represented by the following general formula (1) and an organoboron compound represented by the following general formula (2-1) or the following general formula (2-2).

[0034] [Chemical Formula 1]

[0035]

[0036] (In the formula, L1 to L3 can be the same or different from each other, and represent single bonds, divalent aromatic hydrocarbon groups with 6 to 30 deuterated or unsubstituted carbon atoms, divalent fused polycyclic aromatic hydrocarbon groups with 10 to 30 deuterated or unsubstituted carbon atoms, divalent aromatic heterocyclic groups with 2 to 20 deuterated or unsubstituted carbon atoms, or divalent fused polycyclic aromatic heterocyclic groups with 2 to 30 deuterated or unsubstituted carbon atoms.)

[0037] A1 and A2 can be the same or different from each other, and represent deuterated or unsubstituted naphthyl groups.

[0038] A3 represents an aromatic hydrocarbon group with 6 to 30 substituted or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon group with 10 to 30 substituted or unsubstituted carbon atoms, an aromatic heterocyclic group with 2 to 20 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0039] R1 and R2 can be the same or different from each other, and represent an aromatic hydrocarbon group with 6 to 30 deuterated or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon group with 10 to 30 deuterated or unsubstituted carbon atoms, an aromatic heterocyclic group with 2 to 20 deuterated or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocyclic group with 2 to 30 deuterated or unsubstituted carbon atoms.

[0040] The term "substituted or unsubstituted" means having one or two or more substituents, or having no substituents.

[0041] The "substituents" may be the same or different from each other, and may represent deuterium, halogen, cyano, alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 30 carbon atoms, alkenyl with 2 to 30 carbon atoms, aromatic hydrocarbon with 6 to 50 carbon atoms, fused polycyclic aromatic hydrocarbon with 10 to 30 carbon atoms, aromatic heterocyclic group with 2 to 50 carbon atoms, fused polycyclic aromatic heterocyclic group with 2 to 30 carbon atoms, amino with 0 to 30 carbon atoms, or silyl group with 0 to 30 carbon atoms.

[0042] Furthermore, these "substituents" may have one or more substituents.

[0043] Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the categories of "6-30 carbon atoms", "10-30 carbon atoms", "2-20 carbon atoms", and "2-30 carbon atoms" in A3, R1, and R2.

[0044] [Chemical Formula 2]

[0045]

[0046] (In the formula, Q1 to Q3 can be the same or different from each other, and represent an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon ring with 10 to 50 substituted or unsubstituted carbon atoms, an aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms.)

[0047] Y1 to Y3 can be the same or different from each other, and can represent N-R3, CR4R5, O, S, Se, or SiR6R7.

[0048] R3 to R7 can be the same or different from each other, and represent hydrogen atoms, deuterium atoms, halogen atoms, nitro groups, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 30 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 30 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, and fused groups with 10 to 50 substituted or unsubstituted carbon atoms. Polycyclic aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups with 2 to 50 carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 50 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, substituted or unsubstituted arylthio groups with 5 to 30 carbon atoms, substituted or unsubstituted amino groups with 0 to 30 carbon atoms, or substituted or unsubstituted silyl groups with 3 to 30 carbon atoms.

[0049] R3 to R7 can form a ring by bonding or fusion with any one of Q1 to Q3 via single bonds, N, O, P or S. R4 and R5, and R6 and R7 can bond with each other to further form a ring.

[0050] The meaning of “substituted or unsubstituted” is the same as that of the general formula (1), and “substituent” refers to the same group as “substituent” in the general formula (1).

[0051] Furthermore, these "substituents" may have one or more substituents.

[0052] In addition, when the "substituent" has a carbon atom, the carbon atom is included in the "number of carbon atoms 6-50", "number of carbon atoms 10-50", "number of carbon atoms 2-50", "number of carbon atoms 1-30", "number of carbon atoms 3-30", "number of carbon atoms 2-30", "number of carbon atoms 6-30" and "number of carbon atoms 5-30" in Q1-Q3, Y1-Y3 and R3-R7.

[0053] When Y2 or Y3 is N-R3, at least one of R3 represents a fused polycyclic aromatic heterocyclic group represented by the following general formula (2-A) or an aromatic hydrocarbon group, fused polycyclic aromatic hydrocarbon group, or fused polycyclic aromatic heterocyclic group represented by the following general formula (2-B).

[0054] [Chemical Formula 3]

[0055]

[0056] (In the formula, X represents O or S,)

[0057] R8~R 15 These can be the same as or different from each other, and represent single bonds, hydrogen atoms, deuterium atoms, halogen atoms, hydroxyl groups, nitro groups, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 30 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkynyl groups with 2 to 30 substituted or unsubstituted carbon atoms, heterocyclic alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, and fused polycyclic aromatic hydrocarbon groups with 2 to 30 substituted or unsubstituted carbon atoms. Polycyclic aromatic heterocyclic groups, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, substituted or unsubstituted arylthio groups with 5 to 30 carbon atoms, substituted or unsubstituted amino groups with 0 to 30 carbon atoms, substituted or unsubstituted silyl groups with 3 to 30 carbon atoms, substituted or unsubstituted germanyl groups with 0 to 30 carbon atoms, substituted or unsubstituted boronyl groups with 0 to 30 carbon atoms, substituted or unsubstituted aluminumyl groups with 0 to 30 carbon atoms, substituted phosphoryl groups with 0 to 30 carbon atoms, substituted or unsubstituted selenyl groups with 0 to 30 carbon atoms, or substituted or unsubstituted telluryl groups with 0 to 30 carbon atoms.

[0058] R8~R 15 Any one of them is N-bonded to N-R3 represented by Y2 or Y3.

[0059] R8~R 15 It can form a ring by bonding or fusion with adjacent groups via single bonds, N, O or S.

[0060] The meaning of “substituted or unsubstituted” is the same as that of the general formula (1), and “substituent” refers to the same group as “substituent” in the general formula (1).

[0061] Furthermore, these "substituents" may have one or more substituents.

[0062] Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R8 to R9 groups. 15 The terms "carbon number 1-30", "carbon number 3-30", "carbon number 2-30", "carbon number 10-30", "carbon number 6-50", "carbon number 2-50", "carbon number 6-30", "carbon number 5-30", and "carbon number 0-30" are used.

[0063] [Chemical Formula 4]

[0064]

[0065] (where R) 16 The following groups represent hydrogen atoms, deuterium atoms, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms.

[0066] R 17 The following groups represent hydrogen atoms, deuterium atoms, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 30 substituted or unsubstituted carbon atoms.

[0067] R 18 ~R 20 They can be the same as or different from each other, and can represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 30 substituted or unsubstituted carbon atoms, alkylthio groups with 1 to 30 substituted or unsubstituted carbon atoms, amino groups with 0 to 30 substituted or unsubstituted carbon atoms, or silyl groups with 3 to 30 substituted or unsubstituted carbon atoms.

[0068] The wavy line represents the N-bonding portion of N-R3 represented by Y2 or Y3.

[0069] R 16 ~R 20 It can form a ring by bonding or fusion with adjacent groups via single bonds, N, O or S.

[0070] The meaning of “substituted or unsubstituted” is the same as that of the general formula (1), and “substituent” refers to the same group as “substituent” in the general formula (1).

[0071] Furthermore, these "substituents" may have one or more substituents.

[0072] Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R. 16 ~R 20The terms "carbon number 1-30", "carbon number 6-50", "carbon number 2-50", "carbon number 3-30", "carbon number 10-30", "carbon number 2-30", and "carbon number 0-30" are included.

[0073] 2) The organic EL element according to 1) above comprises an aromatic amine compound, wherein A1 and A2 in the general formula (1) may be the same or different from each other, and are deuterated or unsubstituted 1,2-naphthylene, deuterated or unsubstituted 1,3-naphthylene, deuterated or unsubstituted 1,4-naphthylene, deuterated or unsubstituted 2,6-naphthylene, deuterated or unsubstituted 2,7-naphthylene, or deuterated or unsubstituted 2,8-naphthylene.

[0074] 3) The organic EL element according to 1) or 2) above contains an aromatic amine compound, wherein L1 and L2 in the general formula (1) are deuterated or unsubstituted phenylene or deuterated or unsubstituted biphenylene.

[0075] 4) An organic EL element according to any one of 1) to 3) above, comprising an aromatic amine compound, wherein R1 and R2 in the general formula (1) may be the same as or different from each other, and are deuterated or unsubstituted phenyl, deuterated or unsubstituted naphthyl, deuterated or unsubstituted dibenzofuranyl, deuterated or unsubstituted phenanthryl, or deuterated or unsubstituted biphenyl (C6H5-C6H4-).

[0076] 5) An organic EL element according to any one of 1) to 4) above, comprising an aromatic amine compound, wherein A3 in the general formula (1) is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted biphenyl.

[0077] 6) An organic EL element according to any one of 1) to 5) above, comprising an aromatic amine compound in which A1 and A2 in the general formula (1) are the same groups.

[0078] 7) The organic EL element according to 6) above comprises an aromatic amine compound in which R1 and R2 in the general formula (1) are the same groups.

[0079] 8) The organic EL element according to 6) above comprises an aromatic amine compound in which R1 and R2 in the general formula (1) are different groups.

[0080] 9) An organic EL element according to any one of 1) to 5) above, comprising an aromatic amine compound in which A1 and A2 in the general formula (1) are different groups.

[0081] 10) The organic EL element according to 9) above comprises an aromatic amine compound in which R1 and R2 in the general formula (1) are the same groups.

[0082] 11) The organic EL element according to 9) above comprises an aromatic amine compound in which R1 and R2 in the general formula (1) are different groups.

[0083] 12) The organic EL element according to any one of 1) to 11) above, wherein,

[0084] The general formulas (2-1) and (2-2) comprise organoboron compounds represented by the following general formulas (2-3), (2-4), (2-5), or (2-6).

[0085] [Chemical Formula 5]

[0086]

[0087] (where Y) 1、 Y 2、 Y3 has the same meaning as the general formulas (2-1) and (2-2).

[0088] Y4 represents N-R3, C-R4R5, O, S, Se, or Si-R6R7.

[0089] R3 to R7 have the same meaning as general formulas (2-1) and (2-2).

[0090] Z can be the same as or different from each other, and represents N or CR. 21 ,

[0091] R 21This refers to hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 30 substituted or unsubstituted carbon atoms, and substituted or unsubstituted... Alkoxy with 1 to 30 carbon atoms, aryloxy with 6 to 30 carbon atoms (substituted or unsubstituted), alkylthio with 1 to 30 carbon atoms (substituted or unsubstituted), arylthio with 5 to 30 carbon atoms (substituted or unsubstituted), alkylamino with 1 to 30 carbon atoms (substituted or unsubstituted), arylamino with 5 to 30 carbon atoms (substituted or unsubstituted), alkylsilyl with 1 to 30 carbon atoms (substituted or unsubstituted), or arylsilyl with 5 to 30 carbon atoms (substituted or unsubstituted).

[0092] R 21 They can form rings by bonding or fusion with adjacent groups via single bonds, N, O, or S.

[0093] The meaning of “substituted or unsubstituted” is the same as that of the general formula (1), and “substituent” refers to the same group as “substituent” in the general formula (1).

[0094] Furthermore, these "substituents" may have one or more substituents.

[0095] Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R. 21 (The categories are: "carbon number 1-30", "carbon number 3-30", "carbon number 6-50", "carbon number 2-50", "carbon number 6-30", and "carbon number 5-30".)

[0096] 13) The organic EL element according to any one of 1) to 12) above, wherein,

[0097] The organic layer comprises at least a hole transport layer and a light-emitting layer, wherein the hole transport layer contains a compound represented by the general formula (1), and the light-emitting layer contains an organoboron compound represented by the general formula (2-1) or the general formula (2-2).

[0098] 14) The organic EL element according to any one of 1) to 12) above, wherein,

[0099] The organic layer comprises at least an electron blocking layer and a light-emitting layer, wherein the electron blocking layer contains a compound represented by the general formula (1), and the light-emitting layer contains an organoboron compound represented by the general formula (2-1) or the general formula (2-2).

[0100] 15) The organic EL element according to any one of 1) to 12) above, wherein,

[0101] The organic layer comprises at least a hole injection layer and a light-emitting layer, wherein the hole injection layer contains a compound represented by the general formula (1), and the light-emitting layer contains an organoboron compound represented by the general formula (2-1) or the general formula (2-2).

[0102] 16) An electronic device having a pair of electrodes and an organic layer sandwiched between the pair of electrodes, wherein the organic layer contains an aromatic amine compound represented by general formula (1) and an organoboron compound represented by general formula (2-1) or general formula (2-2).

[0103] Invention Effects

[0104] According to the present invention, by combining the aromatic amine compound represented by the general formula (1) and the organoboron compound represented by the general formula (2-1) or the general formula (2-2), it is possible to realize an organic EL device with high efficiency, low driving voltage and long life. Attached Figure Description

[0105] Figure 1 This is a diagram showing the structure of the organic EL element of Examples 1 to 189 and Comparative Examples 1 to 3. Detailed Implementation

[0106] <Compounds represented by general formula (1)>

[0107] The organic electroluminescent element of the present invention comprises the compound represented by the above general formula (1).

[0108] The terms A3, R1, and R2 in general formula (1) represent "aromatic hydrocarbon groups with 6 to 30 carbon atoms", "fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms", "aromatic heterocyclic groups with 2 to 20 carbon atoms", or "fused polycyclic aromatic heterocyclic groups with 2 to 30 carbon atoms". Specifically, examples include aromatic hydrocarbon groups such as phenyl, biphenyl, and triphenyl; and fused polycyclic aromatic hydrocarbon groups such as naphthyl, anthracene, phenanthryl, indene, pyrene, perylene, fluoranyl, triphenylene, fluorene, and spirodifluorene. Polycyclic aromatic hydrocarbon groups; aromatic heterocyclic groups such as pyridyl, pyrimidinyl, triazine, furanyl, pyrroloyl, and thiophene; fused polycyclic aromatic heterocyclic groups such as quinolinyl, isoquinolinyl, benzofuranyl, benzothiophene, indolyl, carbazole, benzoxazolyl, benzothiazolyl, azafluorenyl, diazafluorenyl, azaspirodifluorenyl, diazaspirodifluorenyl, quinoxolinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiophene, naphthinyl, phenanthrololinyl, acridineyl, and carbolinyl. "Aromatic hydrocarbon groups" include groups where benzene rings are linked by single bonds. In "fused polycyclic aromatic hydrocarbon groups," the ring skeleton of the fused ring consists only of carbon atoms. "Aromatic hydrocarbon groups" do not include fused polycyclic aromatic hydrocarbon groups. In the term "fused polycyclic aromatic heterocyclic group," the ring skeleton of the fused ring includes heteroatoms. The term "aromatic heterocyclic group" does not include fused polycyclic aromatic heterocyclic groups. Furthermore, the terms "aromatic hydrocarbon group," "fused polycyclic aromatic hydrocarbon group," "fused polycyclic aromatic heterocyclic group," and "aromatic heterocyclic group" omit the "monovalent" designation when referring to a monovalent group. When referring to a divalent group, it is indicated as "divalent."

[0109] In the general formula (1), A3, R1, and R2 represent "substituted aromatic hydrocarbon group", "substituted fused polycyclic aromatic hydrocarbon group", "substituted aromatic heterocyclic group", or "substituted fused polycyclic aromatic heterocyclic group". These groups may have one or more substituents as "substituents". Specifically, examples include deuterium atom, cyano, nitro; halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; straight-chain or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 1-adamantyl. 2-Adamantyl and other cycloalkyl groups; vinyl, allyl, isopropenyl, 2-butenyl and other alkenyl groups; phenyl, biphenyl, triphenyl and other aromatic hydrocarbon groups; naphthyl, anthracene, phenanthryl, fluorenyl, spirodifluorenyl, indyl, pyrene, perylene, fluoranyl, triphenylene and other fused polycyclic aromatic hydrocarbon groups; pyridyl, pyrimidinyl, triazinyl, pyrroleyl, thiopheneyl, furanyl and other aromatic heterocyclic groups; quinolinyl, isoquinolinyl, benzofuranyl, benzothiopheneyl, indolyl, carbazoleyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl Fused polycyclic aromatic heterocyclic groups such as carbolinel; unsubstituted amino groups; monoalkyl amino groups such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, tert-butylamino, n-pentylamino, isopentylamino, neopentylamino, and n-hexylamino; dialkyl amino groups such as dimethylamino, diethylamino, di-n-propylamino, and diisopropylamino; monoaryl amino groups such as phenylamino, biphenylamino, triphenylamino, naphthylamino, anthraceneylamino, pyreneylamino, and perylamino; and diphenylamino, bis(biphenyl)amino, bis(triphenyl)amino, and dinaphthylamino. Diarylamino groups such as amino, dianthrylamino, difluorenylamino, diindylamino, and N-phenyl-N-naphthylamino; alkylarylamino groups such as N-methyl-N-phenylamino; alkylsilyl groups such as trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, and tert-butyldimethylsilyl; arylsilyl groups such as triphenylsilyl, trinaphthylsilyl, biphenylsilyl, and tri(biphenyl)silyl; and alkylarylsilyl groups such as tert-butyldiphenylsilyl. For example, as a "substituent," one or more groups may be selected from the group consisting of a deuterium atom, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a fused polycyclic aromatic hydrocarbon group having 10 to 40 carbon atoms, and groups formed by combining these groups.

[0110] These substituents may further have one or more of the exemplified substituents. Furthermore, these substituents may form a ring via a single bond, a substituted or unsubstituted methylene group, N, O, or S bonded to or fused with adjacent groups. Additionally, N represents a nitrogen atom, O represents an oxygen atom, and S represents a sulfur atom. Furthermore, when a "substituent" has a carbon atom, that carbon atom is included in the categories of "6-30 carbon atoms," "10-30 carbon atoms," "2-20 carbon atoms," and "2-30 carbon atoms" in A3, R1, and R2.

[0111] As L1, L2 and L3 in general formula (1) represent “divalent aromatic hydrocarbon group”, “divalent aromatic heterocyclic group”, “divalent fused polycyclic aromatic hydrocarbon group” or “divalent fused polycyclic aromatic heterocyclic group”, examples can be given of groups obtained by removing one hydrogen atom from the groups represented by “aromatic hydrocarbon group”, “fused polycyclic aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic heterocyclic group” as A3, R1 and R2 in general formula (1).

[0112] There is no particular limitation on the position of the linking bond of "naphthyl" in "deuterated or unsubstituted naphthyl" shown in A1 and A2. Examples of naphthyl include 1,2-naphthyl, 1,3-naphthyl, 1,4-naphthyl, 2,4-naphthyl, 1,6-naphthyl, 1,7-naphthyl (2,8-naphthyl), 2,5-naphthyl, 2,6-naphthyl, and 2,7-naphthyl.

[0113] L1 and L2 in general formula (1) are preferably phenylene, more preferably 1,4-phenylene. A3 in general formula (1) is preferably phenyl or 9-phenanthyl. A1 and A2 in general formula (1) are preferably 1,2-naphthylene or 1,3-naphthylene. R1 and R2 in general formula (1) are preferably phenyl or naphthyl.

[0114] The compounds represented by the general formula (1) used in this invention can be selected from the groups shown below. For example, they can be selected from group 1 of compounds where R1-A1-L1 and R2-A2-L2 are different groups. Furthermore, in group 1 of compounds, they can be further selected from groups 2 to 10 of compounds that satisfy the following conditions A to I. That is, they can be selected from any one of the following groups of compounds: group 2 of compounds that satisfy condition A, group 3 of compounds that satisfy condition B, group 4 of compounds that satisfy condition C, group 5 of compounds that satisfy condition D, group 6 of compounds that satisfy condition E, group 7 of compounds that satisfy condition F, group 8 of compounds that satisfy condition G, group 9 of compounds that satisfy condition H, and group 10 of compounds that satisfy condition I. In group 2 of compounds that satisfy condition A, L3 is a single bond, and A3 is an aromatic hydrocarbon group with 6 to 30 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic hydrocarbon group with 10 to 30 substituted or unsubstituted carbon atoms. In compound group 3 of B, L3 is a divalent aromatic hydrocarbon group with 6 to 30 carbon atoms that is deuterated or unsubstituted, or a divalent fused polycyclic aromatic hydrocarbon group with 10 to 30 carbon atoms that is deuterated or unsubstituted (e.g., a deuterated or unsubstituted biphenylene, preferably a deuterated or unsubstituted phenylene), and A3 is an aromatic hydrocarbon group with 6 to 30 carbon atoms that is substituted or unsubstituted, or a fused polycyclic aromatic hydrocarbon group with 10 to 30 carbon atoms that is substituted or unsubstituted (e.g., a deuterated or phenyl-substituted or unsubstituted phenyl, naphthyl, or phenanthrene). In compound group 4 that satisfies condition C, L3 is deuterated. The compounds in group 5 that satisfy condition D are either an unsubstituted aromatic hydrocarbon group with 6 to 30 carbon atoms in a divalent state, or a fused polycyclic aromatic hydrocarbon group with 10 to 30 carbon atoms in a divalent state (e.g., a deuterated or unsubstituted biphenylene, preferably a deuterated or unsubstituted phenylene), and A3 is an substituted or unsubstituted aromatic heterocyclic group with 2 to 20 carbon atoms in a divalent aromatic heterocyclic group, or a fused polycyclic aromatic heterocyclic group with 2 to 30 carbon atoms in a divalent polycyclic aromatic heterocyclic group (e.g., a deuterated or unsubstituted dibenzofuranyl, a deuterated or unsubstituted dibenzothiopheneyl). In group 5, L1 and L2 are single bonds, satisfying condition D. In compound group 6 of category E, L1 and L2 are deuterated or unsubstituted divalent aromatic hydrocarbon groups with 6 to 30 carbon atoms (e.g., deuterated or unsubstituted biphenylene, preferably deuterated or unsubstituted phenylene). In compound group 7 satisfying condition F, A1 and A2 are deuterated or unsubstituted 1,2-naphthylene, deuterated or unsubstituted 1,3-naphthylene, or deuterated or unsubstituted 1,4-naphthylene. In compound group 8 satisfying condition G, A1 and A2 are deuterated or unsubstituted 2,6-naphthylene, deuterated or unsubstituted 2,7-naphthylene, or deuterated or unsubstituted 2,6-naphthylene.8-Naphthylene, in group 9 of compounds satisfying condition H, R1 and R2 are deuterated or unsubstituted aromatic hydrocarbon groups with 6 to 30 carbon atoms, or fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms (e.g., phenyl, naphthyl, phenanthrene). In group 10 of compounds satisfying condition I, R1 and R2 are deuterated or phenyl-substituted or unsubstituted aromatic heterocyclic groups with 2 to 20 carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 30 carbon atoms (e.g., dibenzofuranyl).

[0115] Furthermore, when the repetition range of each of groups 2 and groups 5 to 10 is sequentially set to groups 11 to 16, the repetition range of each of groups 3 and groups 5 to 10 is sequentially set to groups 17 to 22, and the repetition range of each of groups 4 and groups 5 to 10 is sequentially set to groups 23 to 28, the compound represented by the general formula (1) used in this invention can be selected from any one of groups 11 to 28. Moreover, the compound represented by the general formula (1) used in this invention can be selected from any one of the following groups: compound group 29 with R1 and R2 being the same and L1 and L2 being the same and A1 and A2 being different; compound group 30 with A1 and A2 being the same and L1 and L2 being the same and R1 and R2 being different; and compound group 31 with L1 and L2 being the same and R1 and R2 being different and A1 and A2 being different.

[0116] The compounds represented by general formula (1) used in this invention can be selected from compound group 32, which contains compounds with the same groups R1-A1-L1 and R2-A2-L2. Furthermore, within compound group 32, when compounds that further satisfy the above conditions A to I are sequentially designated as compound groups 33 to 41, they can be selected from any one of these compound groups. Moreover, the compounds represented by general formula (1) used in this invention can be selected from compound group 42, which contains compounds with the same groups R1-A1-L1 and R2-A2-L2 but different groups from A3-L3.

[0117] Hereinafter, specific examples of compounds represented by general formula (1) are given. However, the compounds represented by general formula (1) that can be used in this invention should not be interpreted as limiting by these specific examples. Furthermore, in the following chemical structural formulas, hydrogen atoms are omitted. 1 The display of H) shows that deuterium atoms ( 2 H) is displayed as "D".

[0118] [Chemical Formula 6]

[0119]

[0120] [Chemical Formula 7]

[0121]

[0122] [Chemical Formula 8]

[0123]

[0124] [Chemical Formula 9]

[0125]

[0126] [Chemical Formula 10]

[0127]

[0128] [Chemical Formula 11]

[0129]

[0130] [Chemical Formula 12]

[0131]

[0132] [Chemical Formula 13]

[0133]

[0134] [Chemical Formula 14]

[0135]

[0136] [Chemical Formula 15]

[0137]

[0138] [Chemical Formula 16]

[0139]

[0140] [Chemical Formula 17]

[0141]

[0142] [Chemical Formula 18]

[0143]

[0144] The compounds represented by general formula (1) can be synthesized using known coupling reactions and by appropriately selecting known reaction conditions. For details of the reaction, please refer to the synthesis examples described later.

[0145] The purification of aromatic amine compounds represented by general formula (1) can be carried out by known methods such as column chromatography, adsorption purification based on silica gel, activated carbon, activated clay, etc., solvent-based recrystallization or crystallization, and sublimation purification. The identification of the compounds can be carried out by NMR analysis and mass spectrometry (MS). As physical properties, the melting point, glass transition point (Tg), and HOMO energy level can be measured. The melting point is used as an indicator of vapor deposition properties, the glass transition point (Tg) is used as an indicator of the stability of the thin film state, and the HOMO energy level is used as an indicator of hole injection or hole transport properties, or electron blocking properties.

[0146] <Organoboron compounds>

[0147] The organic electroluminescent element of the present invention comprises an organoboron compound represented by the above general formula (2-1) or the above general formula (2-2).

[0148] The terms "aromatic hydrocarbon ring", "fused polycyclic aromatic hydrocarbon ring", "aromatic heterocycle" or "fused polycyclic aromatic heterocycle" as represented by Q1 to Q3 in general formulas (2-1) and (2-2) refer to "aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms", "fused polycyclic aromatic hydrocarbon ring with 10 to 50 substituted or unsubstituted carbon atoms", "aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms", or "fused polycyclic aromatic heterocycle". Specifically, examples include benzene rings; fused polycyclic aromatic hydrocarbon rings such as indene rings, naphthalene rings, anthracene rings, pyrene rings, perylene rings, fluorene rings, and phenanthrene rings; aromatic heterocycles such as pyridine rings, pyrimidine rings, triazine rings, pyrrole rings, furan rings, and thiophene rings; and fused polycyclic aromatic heterocycles such as quinoline rings, isoquinoline rings, benzofuran rings, benzothiophene rings, indole rings, indoline rings, carbazole rings, carbline rings, benzoxazole rings, benzothiazole rings, quinoxaline rings, benzimidazole rings, pyrazole rings, dibenzofuran rings, dibenzothiophene rings, naphthidine rings, phenanthrene-rhein rings, and acridine rings.

[0149] These "rings" may have one or more substituents, which can be groups that are the same as the groups represented by "substituent" in "substituted aromatic hydrocarbon group", "substituted fused polycyclic aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted fused polycyclic aromatic heterocyclic group" as A3, R1 and R2 in the general formula (1), and these substituents may further have one or more substituents.

[0150] Furthermore, these "rings" can be bonded or fused with substituents, or with each other, via single bonds, substituted or unsubstituted methylene groups, N, O, P, or S to form rings. Specifically, the following structures can be cited as examples of structures where "rings" are bonded or fused with substituents to form rings.

[0151] [Chemical Formula 19]

[0152]

[0153] In addition, when the "substituent" has a carbon atom, the carbon atom is included in "6 to 50 carbon atoms", "10 to 50 carbon atoms" and "2 to 50 carbon atoms" in Q1 to Q3.

[0154] In the general formulas (2-1) and (2-2), Y1 to Y3 can be the same or different from each other, and represent N-R3, C-R4R5, O, S, Se, or Si-R6R7.

[0155] N-R3 indicates a nitrogen atom with R3 as a substituent.

[0156] C-R4R5 indicates a carbon atom with R4 and R5 as substituents.

[0157] O represents oxygen atom, S represents sulfur atom, and Se represents selenium atom.

[0158] Si-R6R7 indicates silicon atoms having R6 and R7 as substituents.

[0159] Furthermore, the definitions of R3 to R7 are explained in more detail in the following description.

[0160] R3 to R in the general formulas (2-1), (2-2), (2-A), and (2-B) 15 R 18 ~R 20 The halogen atoms referred to can specifically include fluorine, chlorine, bromine, and iodine atoms.

[0161] R3 to R in the general formulas (2-1), (2-2), (2-A), and (2-B) 20 The terms "substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms", R3 to R4, are used to indicate the presence of alkyl groups with 1 to 30 carbon atoms. 15 and R 17 ~R 20 The term "substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms" or R3 to R 15The terms "substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms," "substituted or unsubstituted cycloalkenyl group with 3 to 30 carbon atoms," or "substituted or unsubstituted heterocyclic alkyl group with 1 to 30 carbon atoms" specifically refer to "alkyl group with 1 to 30 carbon atoms," "cycloalkyl group with 3 to 30 carbon atoms," "alkenyl group with 2 to 30 carbon atoms," "cycloalkenyl group with 3 to 30 carbon atoms," or "heterocyclic alkyl group with 1 to 30 carbon atoms." Examples of alkyl groups include straight-chain or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl; cycloalkyl groups such as cyclopentyl, cyclohexyl, 1-adamantyl, and 2-adamantyl; alkenyl groups such as vinyl, allyl, isopropenyl, and 2-butenyl; cycloalkenyl groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl; and heterocyclic alkyl groups such as tetrahydrofuranyl and tetrahydrothiophenyl.

[0162] R3 to R in general formulas (2-1), (2-2), (2-A), and (2-B) 20 The term "aromatic hydrocarbon group with 6 to 50 carbon atoms, substituted or unsubstituted" and R3 to R 15 and R 17 The term "fused polycyclic aromatic hydrocarbon group with 10 to 50 carbon atoms, substituted or unsubstituted" and R3 to R4 are used to indicate this. 20 The term "aromatic heterocyclic group with 2 to 50 carbon atoms, substituted or unsubstituted" or R3 to R 17 The groups represented as “fused polycyclic aromatic heterocyclic groups with 2 to 50 carbon atoms”, “aromatic hydrocarbon groups with 6 to 50 carbon atoms”, “fused polycyclic aromatic hydrocarbon groups with 10 to 50 carbon atoms”, “aromatic heterocyclic groups with 2 to 50 carbon atoms” or “fused polycyclic aromatic heterocyclic groups with 2 to 50 carbon atoms” can be the same groups as the groups represented by “aromatic hydrocarbon groups”, “fused polycyclic aromatic hydrocarbon groups”, “aromatic heterocyclic groups” or “fused polycyclic aromatic heterocyclic groups” as A3, R1 and R2 in the general formula (1).

[0163] R3 to R in general formulas (2-1), (2-2), (2-A), and (2-B) 15 and R 18 ~R 20 The term "alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted", R3 to R 15 The term "aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted", R3 to R 15 and R 18 ~R 20 The term "substituted or unsubstituted alkylthio group with 1 to 30 carbon atoms" or R3 to R4 indicates a substituted or unsubstituted alkylthio group. 15The "substituted or unsubstituted arylthio group with 5 to 30 carbon atoms" refers to "alkoxy group with 1 to 30 carbon atoms," "aryloxy group with 6 to 30 carbon atoms," "alkoxy group with 1 to 30 carbon atoms," or "arylthio group with 5 to 30 carbon atoms." Specifically, examples include alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-pentoxy, and n-hexoxy; phenoxy, biphenyl, etc. Aromatic oxy groups include hydroxyl, triphenyloxyl, naphthoxy, anthraquinone, phenanthrene, fluorenyloxy, indoxy, pyrene, and perylene oxy; alkyl thio groups include methylthiol, ethylthiol, n-propylthiol, isopropylthiol, n-butylthiol, isobutylthiol, tert-butylthiol, n-pentylthiol, isopentylthiol, neopentylthiol, and n-hexylthio; and aryl thio groups include phenylthiol, biphenylthiol, triphenylthiol, naphthiol, anthraquinone, phenanthrene, fluorenylthiol, indoxyl, pyrene, and perylene thiol.

[0164] R3 to R in general formulas (2-1), (2-2), (2-A), and (2-B) 15 and R 18 ~R 20 The "amino group with 0-30 carbon atoms" or "silyl group with 3-30 carbon atoms" referred to in the phrase "substituted or unsubstituted amino group with 0-30 carbon atoms" specifically includes unsubstituted amino groups; monoalkyl amino groups such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, tert-butylamino, n-pentylamino, isopentylamino, neopentylamino, and n-hexylamino; dialkyl amino groups such as dimethylamino, diethylamino, di-n-propylamino, and diisopropylamino; and phenylamino, biphenylamino, triphenylamino, naphthylamino, anthraceneamino, phenanthreneamino, fluorenylamino, and indeneamino. Monoaryl amino groups such as pyrene-amino and perylamino; diaryl amino groups such as diphenylamino, bis(biphenyl)amino, bis(triphenyl)amino, dinaphthylamino, dianthrylamino, difluorenylamino, diindylamino, N-phenyl-N-naphthylamino; alkylaryl amino groups such as N-methyl-N-phenylamino; alkylsilyl groups such as trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, tert-butyldimethylsilyl; arylsilyl groups such as triphenylsilyl, trinaphthylsilyl, biphenylsilyl, tri(biphenyl)silyl; and alkylarylsilyl groups such as tert-butyldiphenylsilyl.

[0165] As R8~R in general formula (2-A) 15 The "alkynyl group with 2 to 30 carbon atoms" mentioned in the phrase "substituted or unsubstituted alkynyl group" can specifically include ethynyl, 2-propynyl, 2-butynyl, etc.

[0166] As R8~R in general formula (2-A) 15 The terms "germanium group with 0-30 carbon atoms (substituted or unsubstituted)," "boron group with 0-30 carbon atoms (substituted or unsubstituted)," "aluminum group with 0-30 carbon atoms (substituted or unsubstituted)," "substituted phosphoryl group with 0-30 carbon atoms (substituted)," "selenoyl group with 0-30 carbon atoms (substituted or unsubstituted)," or "tellurium group with 0-30 carbon atoms (substituted or unsubstituted)" specifically include germanium groups such as triphenylgermanium; boron groups such as pinacolboryl and diphenylboryl; aluminum groups such as diphenylaluminyl; substituted phosphoryl groups such as diphenylphosphyl; selenoyl groups such as phenylselenoyl; and tellurium groups such as phenyltellurium.

[0167] In the general formulas (2-1), (2-2), (2-A), and (2-B), R3 to R... 20 The groups represented by "substituted alkyl", "substituted cycloalkyl", "substituted alkenyl", "substituted cycloalkenyl", "substituted heterocyclic alkyl", "substituted aromatic hydrocarbon", "substituted fused polycyclic aromatic hydrocarbon", "substituted aromatic heterocyclic", "substituted fused polycyclic aromatic heterocyclic", "substituted alkoxy", "substituted aryloxy", "substituted alkylthio", "substituted arylthio", "substituted amino", "substituted silyl", "substituted alkynyl", "substituted germanyl", "substituted boron", "substituted aluminum", "substituted phosphoryl", "selenoyl", or "substituted telluryl" may have one or more substituents. As a "substituent", examples can be the same groups as those represented by "substituent" in "substituted aromatic hydrocarbon", "substituted fused polycyclic aromatic hydrocarbon", "substituted aromatic heterocyclic", or "substituted fused polycyclic aromatic heterocyclic" as A3, R1, and R2 in the general formula (1). These substituents may further have one or more substituents. Furthermore, these substituents can form rings by bonding or fusion with adjacent groups via single bonds, substituted or unsubstituted methylene, N, S or O.

[0168] Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R3 to R4 groups. 20 The terms "carbon number 1-30", "carbon number 3-30", "carbon number 2-30", "carbon number 6-50", "carbon number 10-50", "carbon number 2-50", "carbon number 6-30", "carbon number 5-30", and "carbon number 0-30" are used.

[0169] In the general formulas (2-1) and (2-2), R3 to R7 of Y1 to Y3 form rings by bonding or fusion with any one of Q1 to Q3 via single bonds, N, O, or S. R4 and R5, and R6 and R7 can bond with each other to further form rings. The formed "ring" can be an alicyclic ring, an aromatic ring, or a ring formed by the fusion of alicyclic rings, aromatic rings, or alicyclic and aromatic rings. Specifically, as "alicyclic rings", examples include cycloalkanes such as cyclopentane, cyclohexane, and adamantane; cycloalkenes such as cyclopentene and cyclohexene; and heterocyclic alkanes such as tetrahydrofuran and tetrahydrothiophene. As "aromatic rings", examples include rings that are the same as those represented by Q1 to Q3 in general formulas (2-1) and (2-2) as "aromatic hydrocarbon rings", "fused polycyclic aromatic hydrocarbon rings", "aromatic heterocycles", or "fused polycyclic aromatic heterocycles".

[0170] R3 to R in the general formulas (2-1) and (2-2) 15 and R 17 The "aromatic hydrocarbon group", "fused polycyclic aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic heterocyclic group" represented are preferably phenyl, biphenyl, triphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, triazine, furanyl, pyrroleyl or thiophene.

[0171] R in the general formulas (2-3) to (2-6) 21 The "halogen atom" referred to can be any of the R3 to R4 atoms in the general formulas (2-1), (2-2), (2-A), and (2-B). 15 and R 18 ~R 20 The "halogen atom" indicated is the same group as the group shown.

[0172] R in the general formulas (2-3) to (2-6) 21 The "alkyl group with 1 to 30 carbon atoms" or "cycloalkyl group with 3 to 30 carbon atoms" referred to as "substituted or unsubstituted alkyl group with 3 to 30 carbon atoms" can be exemplified by R3 to R4 in the general formulas (2-1), (2-2), (2-A), and (2-B). 20 The terms "alkyl groups having 1 to 30 carbon atoms" and R3 to R4 are used to indicate this. 15 and R 17 ~R 20 The group represented by "cycloalkyl group with 3 to 30 carbon atoms" is the same as the group shown.

[0173] R in the general formulas (2-3) to (2-6) 21 The terms “aromatic hydrocarbon group with 6 to 50 carbon atoms that are substituted or unsubstituted,” “fused polycyclic aromatic hydrocarbon group with 10 to 30 carbon atoms that are substituted or unsubstituted,” “aromatic heterocyclic group with 2 to 50 carbon atoms that are substituted or unsubstituted,” or “fused polycyclic aromatic heterocyclic group with 2 to 30 carbon atoms that are substituted or unsubstituted,” can be exemplified as the same groups represented by “aromatic hydrocarbon group,” “fused polycyclic aromatic hydrocarbon group,” “aromatic heterocyclic group,” or “fused polycyclic aromatic heterocyclic group” as A3, R1, and R2 in the general formula (1).

[0174] R in the general formulas (2-3) to (2-6) 21 The terms "substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms", "substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms", "substituted or unsubstituted alkylthio group with 1 to 30 carbon atoms", or "substituted or unsubstituted arylthio group with 5 to 30 carbon atoms" can be associated with R3 to R4 in the general formulas (2-1), (2-2), (2-A), and (2-B). 15 and R 18 ~R 20 The term "alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted", R3 to R 15 The "aryloxy group" and R3~R3 are represented by these terms. 15 and R 18 ~R 20 The term "substituted or unsubstituted alkylthio group with 1 to 30 carbon atoms" or R3 to R4 indicates a substituted or unsubstituted alkylthio group. 15 The group represented by "arylthio group with 5 to 30 carbon atoms" is the same group as the group shown.

[0175] R in the general formulas (2-3) to (2-6) 21The terms "substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms", "substituted or unsubstituted arylamino group with 5 to 30 carbon atoms", "substituted or unsubstituted alkylsilyl group with 1 to 30 carbon atoms", or "substituted or unsubstituted arylsilyl group with 5 to 30 carbon atoms" can be associated with R3 to R4 in the general formulas (2-1), (2-2), (2-A), and (2-B). 15 R 18 ~R 20 The same group as the group indicated by "amino with 0 to 30 carbon atoms" or "silyl with 3 to 30 carbon atoms".

[0176] In the general formulas (2-3) to (2-6), R 21 The groups represented by “substituted alkyl,” “substituted cycloalkyl,” “substituted aromatic hydrocarbon,” “substituted fused polycyclic aromatic hydrocarbon,” “substituted aromatic heterocyclic,” “substituted fused polycyclic aromatic heterocyclic,” “substituted alkoxy,” “substituted aryloxy,” “substituted alkylthio,” “substituted arylthio,” “substituted amino,” or “substituted silyl” may have one or more substituents. As a “substituent,” examples can be the same groups represented by the substituents in “substituted aromatic hydrocarbon,” “substituted fused polycyclic aromatic hydrocarbon,” “substituted aromatic heterocyclic,” or “substituted fused polycyclic aromatic heterocyclic” as represented by A3, R1, and R2 in the general formula (1). These substituents may further have one or more substituents. Furthermore, these substituents may form a ring by bonding or fusion with adjacent groups via a single bond, substituted or unsubstituted methylene, N, S, or O.

[0177] Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R. 21 The terms "carbon number 1-30", "carbon number 3-30", "carbon number 6-50", "carbon number 10-30", "carbon number 2-50", "carbon number 2-30", "carbon number 6-30", and "carbon number 5-30" are used.

[0178] The organoboron compounds used in this invention can be selected from the groups shown below. For example, they can be selected from group 101 represented by general formula (2-3), group 102 represented by general formula (2-4), group 103 represented by general formula (2-5), and group 104 represented by general formula (2-6). Furthermore, in general formulas (2-1) to (2-6), they can be selected from group 105 where Y1 is O, group 106 where Y1 is S, group 107 where Y2 and Y3 are the same, group 108 where Y2 and Y3 are different, group 109 where one of Y2 and Y3 is N-R3 and the other is CR4R5, O, S, Se, or SiR6R7, group 110 where Y2 and Y3 are independently N-R3, and so on. Compounds selected from group 111, where at least one of Y2 and Y3 is N-R3 and the R3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms (e.g., a phenyl group substituted with an alkyl group having 3 to 20 carbon atoms, or a phenyl group substituted with an aromatic hydrocarbon group having 6 to 14 carbon atoms), or compounds selected from group 112, where at least one of Y2 and Y3 is N-R3 and the R3 is a fused polycyclic aromatic heterocyclic group having 2 to 50 carbon atoms (e.g., a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiopheneyl group). Furthermore, in general formulas (2-3) to (2-6), compounds selected from group 113, where Z is CH or CD, or compounds selected from group 113, where at least one Z is CR, are also acceptable. 21 And the R 21 Compounds selected from group 114 are alkyl groups having 1 to 20 carbon atoms (e.g., 3 to 20), or may be selected from compounds with at least one Z being CR. 21 And the R 21 Compounds selected from group 115 containing substituted or unsubstituted aromatic hydrocarbon groups with 6 to 50 carbon atoms, or from compounds with at least one Z being CR 21 And the R 21 The compounds selected are from group 116 of compounds having fused polycyclic aromatic heterocyclic groups (e.g., substituted or unsubstituted dibenzofuranyl, e.g., substituted or unsubstituted dibenzothiopheneyl) with 2 to 30 carbon atoms, or may be selected from compounds with at least one Z being CR. 21 And the R 21 The compounds selected from group 117 are substituted or unsubstituted arylamino groups having 5 to 30 carbon atoms (e.g., diphenylamino groups that can be substituted by alkyl groups having 1 to 20 carbon atoms or aromatic hydrocarbon groups having 6 to 20 carbon atoms), or may be selected from compounds in which at least one Z constituting each ring is CR. 21 And the R 21The compounds are selected from the group 118, which consists of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 50 carbon atoms, substituted or unsubstituted fused polycyclic aromatic heterocyclic groups having 2 to 30 carbon atoms, or substituted or unsubstituted arylamino groups having 5 to 30 carbon atoms. Furthermore, when the repetition range of each of groups 107 and groups 113 to 118 is sequentially set to groups 119 to 124, the repetition range of each of groups 108 and groups 113 to 118 is sequentially set to groups 125 to 130, the repetition range of each of groups 109 and groups 113 to 118 is sequentially set to groups 131 to 136, the repetition range of each of groups 110 and groups 113 to 118 is sequentially set to groups 137 to 142, the repetition range of each of groups 111 and groups 113 to 118 is sequentially set to groups 143 to 148, and the repetition range of each of groups 112 and groups 113 to 118 is sequentially set to groups 149 to 154, the organoboron compounds used in this invention can be selected from any one of groups 119 to 154.

[0179] The following are examples of selection conditions for choosing the organoboron compound used in this invention from the group of compounds represented by general formula (2-1). As examples of selection conditions, compounds in which Y1 is N-R3, CR4R5, O, Se, or SiR6R7 can be selected; for example, compounds in which Y1 is O can be selected (condition 1). Furthermore, compounds in which at least one of Y2 and Y3 is CR4R5, O, S, Se, or SiR6R7 can also be selected; for example, compounds in which at least one of Y2 and Y3 is O can be selected (condition 2). Furthermore, compounds in which Y2 and Y3 are the same N-R3 group can also be selected; for example, compounds in which both R3 groups are substituted or unsubstituted aromatic hydrocarbon groups with 6 to 50 carbon atoms, substituted or unsubstituted fused polycyclic aromatic hydrocarbon groups with 10 to 50 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups with 2 to 50 carbon atoms, or substituted or unsubstituted fused polycyclic aromatic heterocyclic groups with 2 to 50 carbon atoms can be selected (condition 3). Furthermore, one or both of Y2 and Y3 may be selected as N-R3 and at least one R3 may be a fused polycyclic aromatic hydrocarbon group represented by general formula (2-A). For example, a compound may be selected where only one R3 is a fused polycyclic aromatic hydrocarbon group represented by general formula (2-A), or a compound may be selected where both Y2 and Y3 are N-R3 and both R3 are fused polycyclic aromatic hydrocarbon groups represented by general formula (2-A) (condition 4). Furthermore, the following compounds may also be selected: Y2 and Y3 are distinct N-R3, and R3 is an aromatic hydrocarbon group with 6 to 50 carbon atoms substituted or unsubstituted with a substituent other than a deuterium atom; a fused polycyclic aromatic hydrocarbon group with 10 to 50 carbon atoms substituted or unsubstituted with a substituent other than a deuterium atom; an aromatic heterocyclic group with 2 to 50 carbon atoms substituted or unsubstituted with a substituent other than a deuterium atom; or a fused polycyclic aromatic heterocyclic group with 2 to 50 carbon atoms substituted or unsubstituted with a substituent other than a deuterium atom (Condition 5). Additionally, compounds may be selected from the group of compounds in which at least one ring from Q1 to Q3 is unsubstituted, for example, compounds in which all rings from Q1 to Q3 are unsubstituted, compounds in which two rings from Q1 to Q3 are unsubstituted, or compounds in which one ring from Q1 to Q3 is unsubstituted (Condition 6). Furthermore, it is possible to select from two or more groups of compounds that simultaneously satisfy conditions 1 to 6.

[0180] The following examples illustrate specific examples of organoboron compounds represented by general formula (2-1) or general formula (2-2). However, the organoboron compounds that can be used in this invention should not be interpreted as limiting by these specific examples. Furthermore, in the following chemical structural formulas, hydrogen atoms are omitted (…). 1 The display of H) shows that deuterium atoms ( 2 H) is displayed as "D".

[0181] [Chemical Formula 20]

[0182]

[0183] [Chemical Formula 21]

[0184]

[0185] As the organoboron compound used in this invention, it may be a compound represented by general formula (2-1) or general formula (2-2) and having a structure other than compound (2-18). For example, it may be selected from the group consisting of compounds (2-1) to (2-17) and compounds (2-19) to (2-27) described above.

[0186] The organoboron compounds used in this invention can be selected from the group consisting of compounds 1 to 87 described in Korean Patent Publication No. 10-2453929

[0059] to

[0067] . Furthermore, the organoboron compounds used in this invention can be selected from the group consisting of compounds 1 to 176 described in Korean Patent Publication No. 10-2094830

[0054] to

[0141] . Alternatively, the organoboron compounds used in this invention can be selected from the group consisting of compounds 1 to 149 and 151 to 176 described in Korean Patent Publication No. 10-2094830

[0054] to

[0141] . The organoboron compounds used in this invention can be selected from the group consisting of compounds 1 to 156 described in Korean Patent Publication No. 10-2022-0051822

[0065] to

[0077] . The descriptions in the Korean Patent Publication published in this paragraph are incorporated herein as part of this specification. Furthermore, organoboron compounds represented by general formula (2-1) or general formula (2-2) can be synthesized with reference to the synthetic steps described in those publications.

[0187] Organic electroluminescent devices

[0188] [Electrodes and organic layers constituting the component]

[0189] The organic electroluminescent element (organic EL element) of the present invention has an anode, a cathode and an organic layer sandwiched between the anode and the cathode, wherein at least one layer of the organic layer contains a compound represented by general formula (1), and at least one layer of the organic layer contains a compound represented by general formula (2-1) or general formula (2-2).

[0190] The organic EL element of the present invention has an organic layer that includes at least a light-emitting layer. It may consist of only a light-emitting layer or may have one or more organic layers in addition to the light-emitting layer. Preferably, one or more organic layers are further provided between the anode and the light-emitting layer, and one or more organic layers are further provided between the cathode and the light-emitting layer. Specific examples of organic layers disposed between the light-emitting layer and the anode include hole injection layers, hole transport layers, and electron blocking layers. Specific examples of organic layers disposed between the light-emitting layer and the cathode include hole blocking layers, electron transport layers, and electron injection layers. The compound represented by general formula (1) may be included in the light-emitting layer or in organic layers other than the light-emitting layer, but is preferably included in the organic layer disposed between the light-emitting layer and the anode. The compound represented by general formula (1) is preferably included in one or more of the hole injection layer, hole transport layer, and electron blocking layer, more preferably in one or more of the hole transport layer and electron blocking layer, and even more preferably in the electron blocking layer. For example, the compound represented by general formula (1) may be contained only in one layer of the organic layer disposed between the anode and the light-emitting layer, for example, it may be contained only in the electron blocking layer, for example, it may be contained only in the hole transport layer. The compound represented by general formula (1) has excellent hole injection / transport performance, electron blocking performance, film stability and durability. As a result, in organic EL devices having hole injection layers, hole transport layers and / or electron blocking layers made by using the compound represented by general formula (1) as hole injection materials, hole transport materials and / or electron blocking materials, the hole transport efficiency to the light-emitting layer is improved, the luminous efficiency is improved, and the driving voltage is reduced, thereby improving the durability of the device and tending to easily obtain the characteristics of high efficiency, low driving voltage and long life.

[0191] In one aspect of the present invention, examples of organic EL elements include: an organic EL element comprising, sequentially on a substrate, an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode; an organic EL element having a hole injection layer between the anode and the hole transport layer; an organic EL element having a hole blocking layer between the light-emitting layer and the electron transport layer; and an organic EL element having an electron injection layer between the electron transport layer and the cathode. In these multilayer structures, several organic layers can be omitted, or a single organic layer performing two or more functions can be constructed. For example, it can be constructed as a single organic layer performing both a hole injection layer and a hole transport layer, or as a single organic layer performing both an electron injection layer and an electron transport layer. Furthermore, the structure can be formed by stacking two or more organic layers with the same function, and can also be formed as a structure consisting of stacked two hole transport layers, stacked two electron blocking layers, stacked two light-emitting layers, or stacked two electron transport layers, etc. Furthermore, each organic layer constituting the organic EL element can be formed as a single film composed of a single material, or as a hybrid film composed of multiple materials. It can also be a single-layer structure of a single film or a hybrid film, or a laminated structure of multiple single films, multiple hybrid films, or one or more single films and one or more hybrid films. Film fabrication can be performed using known methods such as vapor deposition, spin coating, and inkjet printing.

[0192] The following is a detailed description of each component and layer of the organic EL element.

[0193] [anode]

[0194] As the anode of the organic EL element of the present invention, an electrode material with a high work function, such as ITO (indium tin oxide) or gold, is used.

[0195] [Hole injection layer, hole transport layer]

[0196] A hole injection layer is positioned between the anode and the light-emitting layer, or between the anode and the hole transport layer, etc., to reduce the injection barrier of holes supplied from the anode, thereby lowering the driving voltage and increasing the luminous brightness. A hole transport layer is a layer that functions to transport holes. A hole transport layer can also be a hole injection transport layer that also functions as a hole injection layer.

[0197] As materials for hole injection layers, hole transport layers, or hole injection transport layers, compounds represented by general formula (1) can be used. The compound represented by general formula (1) used for these layers can be one or more of the compounds represented by general formula (1). Furthermore, compounds represented by general formula (1) and other hole transport or hole injection materials can also be used in combination. Hereinafter, materials that can be used other than compounds represented by general formula (1) will be described.

[0198] As materials for the hole injection layer of the organic EL element of the present invention, porphyrin compounds represented by copper phthalocyanine, starburst-type triphenylamine derivatives, aromatic amine compounds having two or more triphenylamine or carbazole groups in the molecule and having structures linked by single bonds or divalent groups without heteroatoms, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials can be used. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0199] As hole-transporting materials for the hole injection layer, hole transport layer, and hole injection transport layer of the organic EL element of the present invention, N,N'-diphenyl-N,N'-bis(m-tolyl)-benzidine (TPD) or N,N'-diphenyl-N,N'-bis(α-naphthyl)-benzidine (NPD), benzidine derivatives such as N,N,N',N'-tetraphenylbenzidine, 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), and aromatic amine compounds having two or more triphenylamine or carbazole groups in the molecule and having structures formed by single bonds or divalent groups without heteroatoms linked together are all possible. Furthermore, coating-type polymers such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrene sulfonate) (PSS) can be used as materials for the hole injection layer, hole transport layer, and hole injection transport layer. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet printing.

[0200] Furthermore, the hole injection layer, hole transport layer, or hole injection transport layer can also be formed from materials in which p-type dopants such as tribromoaniline hexachloroantimony or radialene derivatives as described in European Patent No. 2684932 are further added, or from materials containing polymeric compounds having benzidine derivatives such as TPD in part of their structure.

[0201] The absolute value of the HOMO energy level of the hole transport material is preferably larger than the absolute value of the HOMO energy level (5.4 eV) of general hole transport materials such as NPD and TPD (i.e., having a deeper HOMO energy level), and preferably smaller than the absolute value of the HOMO energy level of the electron blocking material described later. Specifically, the absolute value of the HOMO energy level of the hole transport material is preferably 5.45 eV or more and 5.80 eV or less, more preferably 5.60 eV or more and 5.75 eV or less.

[0202] [Electron blocking layer]

[0203] An electron blocking layer, for example, is disposed between a light-emitting layer and a hole transport layer, and has the function of suppressing the diffusion of electrons present in the light-emitting layer to the outside of the light-emitting layer (the hole transport layer side). This increases the rebonding probability of electrons and holes in the light-emitting layer. The electron blocking layer typically also has the function of transporting holes. Furthermore, the electron blocking layer can also function as an exciton blocking layer, suppressing the diffusion of excitons from the light-emitting layer.

[0204] The compounds represented by general formula (1) can be used in the electron blocking layer. The compounds represented by general formula (1) have excellent electron blocking ability, high electron resistance, and are stable in the thin film state. They also have the characteristic of restricting the excitons generated in the light-emitting layer. Therefore, when the compounds represented by general formula (1) are used as electron blocking materials in organic EL elements, the probability of hole and electron rebonding is increased, thermal deactivation is suppressed, and thus high luminous efficiency is achieved. Furthermore, the driving voltage is reduced, the current resistance is improved, and the maximum luminous brightness is increased. The compounds represented by general formula (1) used in the electron blocking layer can be one or more of the compounds represented by general formula (1). In addition, compounds represented by general formula (1) and other electron blocking materials can also be used in combination.

[0205] In addition to the aromatic amine compounds represented by the general formula (1), compounds with electron blocking effects, such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazo-9-yl)phenyl]fluorene, 1,3-bis(carbazo-9-yl)phenyl (mCP), 2,2-bis(4-carbazo-9-yl-phenyl)adamantane (Ad-Cz), and compounds with triphenylsilyl and triarylamine structures, represented by 9-[4-(carbazo-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, can also be used as the electron blocking layer material for the organic EL element of the present invention.

[0206] The absolute value of the HOMO energy level of the electron blocking material is preferably larger than the absolute value of the HOMO energy level of the hole transport material (i.e., having a deeper HOMO energy level). Specifically, the absolute value of the HOMO energy level 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 HOMO energy level of the electron blocking material is preferably larger than 0.05 eV or more and 0.45 eV or less, more preferably larger than 0.05 eV or more and 0.35 eV or less, and even more preferably larger than 0.10 eV or more and 0.35 eV or less.

[0207] [Emitting Layer]

[0208] The light-emitting layer is a layer that emits light after generating excitons by rebonding holes and electrons injected from the anode and cathode respectively. The light-emitting material can be used alone in the light-emitting layer, but it is preferable to include both the light-emitting material and the host material.

[0209] In the light-emitting layer of the organic EL element of the present invention, an organoboron compound represented by general formula (2-1) or general formula (2-2) can preferably be used. The organoboron compound represented by general formula (2-1) or general formula (2-2) may be included only in the light-emitting layer of the organic EL element.

[0210] The compound represented by general formula (1) can achieve better results when used in organic EL devices in combination with the compound represented by general formula (2-1) or (2-2). That is, by combining the compound represented by general formula (1) with the compound represented by general formula (2-1) or (2-2) in organic EL devices, the luminous efficiency is further improved and the driving voltage is reduced, thereby further improving the durability of the device. It tends to easily obtain the characteristics of higher efficiency, lower driving voltage and longer life.

[0211] Therefore, it is possible to provide: an electron blocking material composed of a compound represented by general formula (1) for use in combination with a compound represented by general formula (2-1) or (2-2); a laminate (preferably a light-emitting laminate) comprising a layer of a compound represented by general formula (2-1) or (2-2) and a layer comprising a compound represented by general formula (1); an organic EL element comprising a compound represented by general formula (2-1) or (2-2) and a compound represented by general formula (1); an organic EL element having a layer comprising a compound represented by general formula (1) and a layer comprising a compound represented by general formula (2-1) or (2-2) (these two layers are preferably adjacent); and an organic EL element having an electron blocking layer comprising a compound represented by general formula (1) and a light-emitting layer comprising a compound represented by general formula (2-1) or (2-2) (these two layers are preferably adjacent).

[0212] In the organic EL element of the present invention, compounds represented by general formula (1) and compounds represented by general formula (2-1) or general formula (2-2) can be used in any combination. As an example of combination, the combinations obtained by sequentially combining compound group 1 and compound groups 101 to 154 are designated as pairs 1 (101) to 1 (154). Furthermore, the combinations obtained by sequentially combining compound group 2 and compound groups 101 to 154 are designated as pairs 2 (101) to 2 (154), and the combinations obtained by sequentially combining compound group 3 and compound groups 101 to 154 are designated as pairs 3 (101) to 3 (154). It is also possible to determine the combinations obtained by sequentially combining each of compound groups 3 to 42 and compound groups 101 to 154 according to the same principle. In the organic EL element of the present invention, one of the pairs 1 (1) to 42 (154) determined in this way can be selected and used.

[0213] In the light-emitting layer of the organic EL element of the present invention, known light-emitting materials or host materials may also be used as materials other than those represented by general formulas (2-1) or (2-2). The light-emitting material may be any one of fluorescent light-emitting materials, phosphorescent light-emitting materials, and delayed fluorescence materials.

[0214] As fluorescent luminescent materials, in addition to metal complexes of quinolinol derivatives represented by tris(8-hydroxyquinoline)aluminum (Alq3), various metal complexes, anthracene derivatives, bis(5-phenylene)benzene derivatives, pyrene derivatives, oxazole derivatives, poly(p-phenylene)ethylene derivatives, etc. can also be used. Furthermore, quinacrine, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, indophenanthrene derivatives, rhodamine derivatives, aminostyrene derivatives, etc., can also be used.

[0215] As phosphorescent materials, metal complexes with iridium or platinum as the core metal can be used. For example, green phosphorescent materials such as Ir(ppy)3, blue phosphorescent materials such as Firpic and Fir6, and red phosphorescent materials such as Btp2Ir(acac) can be used. Regarding the doping amount of the phosphorescent material in the host material, to avoid concentration quenching, it is preferable to dope by co-evaporation in the range of 1 to 30% by weight relative to the total amount of the luminescent layer.

[0216] Furthermore, carbazole dicyanophenylene (CDCB) derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN can be used as delayed fluorescence materials. For specific examples of delayed fluorescence materials represented by these, please refer to Appl. Phys. Let., 98, 083302 (2011).

[0217] Examples of host materials for the light-emitting layer include anthracene derivatives, heterocyclic compounds with a partial structure containing an indole ring as a fused ring, heterocyclic compounds with a partial structure containing a carbazole ring as a fused ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives. Furthermore, examples of carbazole derivatives with hole injection / transport capabilities include 4,4'-bis(N-carbazolyl)biphenyl (CBP), TCTA, and mCP; examples of carbazole derivatives with electron transport capabilities include p-bis(triphenylsilyl)benzene (UGH2) or 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI).

[0218] [Cavity barrier]

[0219] A hole-blocking layer, for example, is disposed between the light-emitting layer and the electron transport layer. It functions to suppress the diffusion of holes present in the light-emitting layer to the outside of the light-emitting layer (the electron transport layer side), thereby increasing the probability of rebonding between electrons and holes in the light-emitting layer. The hole-blocking layer typically also functions as an electron transport layer. Furthermore, the hole-blocking layer can also function as an exciton-blocking layer, suppressing the diffusion of excitons from the light-emitting layer.

[0220] In addition to metal complexes of phenanthrene-coral derivatives such as copper hydroxide (BCP) and quinolinol derivatives such as bis(2-methyl-8-quinolinol)-4-(phenylphenol)aluminum (BAlq), various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and other compounds with hole-blocking properties can be used as the hole-blocking layer materials for the organic EL element of the present invention. These materials can also function as electron transport layer materials.

[0221] [Electron transport layer, electron injection layer]

[0222] An electron injection layer is disposed between the cathode and the light-emitting layer, or between the cathode and the electron transport layer, etc., in order to reduce the injection barrier of electrons supplied from the cathode, thereby reducing the driving voltage and increasing the luminous brightness.

[0223] An electron transport layer is a layer that functions to transport electrons. An electron transport layer can also function as an electron injection layer.

[0224] As materials for the electron transport layer of the organic EL element of the present invention, metal complexes of quinolinol derivatives represented 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, pyridine indole derivatives, phenanthroline derivatives, thiarroline derivatives, etc., can be used.

[0225] As the material for the electron injection layer of the organic EL element of the present invention, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, metal oxides such as alumina, or metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. By using preferred materials to construct the electron transport layer and the cathode, the electron injection layer can be omitted.

[0226] Furthermore, metals such as cesium (N-type dopants) can be added to the electron injection layer or electron transport layer.

[0227] [cathode]

[0228] As the cathode of the organic EL element of the present invention, metals with low work functions such as aluminum, magnesium-silver alloys, magnesium-indium alloys, and aluminum-magnesium alloys can be used.

[0229] <Electronic Devices>

[0230] The electronic device of the present invention is characterized in that it has a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes, wherein the at least one organic layer contains an aromatic amine compound represented by general formula (1), and wherein the at least one organic layer contains an organoboron compound represented by general formula (2-1) or general formula (2-2).

[0231] As electronic devices, examples include display devices or light-emitting devices incorporating organic EL elements, as well as electrophotographic sensors, image sensors, photoelectric conversion elements, and solar cells. 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 lights.

[0232] Example

[0233] The embodiments of the present invention will be specifically described below through examples. Regarding the materials, processing contents, processing steps, etc., shown below, appropriate modifications can be made without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the following examples. The reagents described in the synthesis examples used are products manufactured by Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Co. LLC, Alfa Aesar, etc. Furthermore, the reactions in the synthesis examples were all carried out using reaction vessels equipped with cooling pipes, stirring devices, and thermometers. In addition, the identification of the compounds in the synthesis examples was performed using… 1H-NMR analysis (NMR device manufactured by Bruker Corporation, model: Ascend) TM The analysis was performed using either a 400MHz mass spectrometer or an MS (mass spectrometer manufactured by AB Sciex Korea Limited Company, model: API3200).

[0234] <Synthetic Example 1: Synthesis of Compounds (1-89)>

[0235] In a nitrogen-purged reaction vessel, 10.0 g of N-phenyl-4-(phenylnaphth-3-yl)aniline, 9.3 g of 3-(4-chlorophenyl)-1-phenylnaphthyl, 5.2 g of sodium tert-butoxy, 0.3 g of bis[tris(tert-butylphosphine)]palladium(0), and 100 mL of toluene were added, and the mixture was stirred under reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain compound (1-89): 14.4 g (yield: 82.3%).

[0236] [Chemical Formula 22]

[0237]

[0238] The obtained white powder was subjected to NMR analysis, and the signals of the following 35 hydrogen atoms were detected, which identified the structure of the compound represented by compound (1-89).

[0239] 1 H-NMR (CDCl3): δ (ppm) = 8.05 (2H), 7.95 (2H), 7.90 (2H), 7.71 (2H), 7.67 (4H) ), 7.65-7.49 (10H), 7.47-7.40 (4H), 7.31 (2H), 7.26-7.21 (6H), 7.08 (1H).

[0240] Melting point: 216℃

[0241] <Synthetic Example 2: Synthesis of Compound (1-181)>

[0242] In a nitrogen-purged reaction vessel, 10.0 g of N-phenyl-4-([1,1'-binaphthyl]-3-yl)aniline, 7.8 g of 3-(4-chlorophenyl)-1-phenylnaphthalene, 3.4 g of sodium tert-butoxy, 0.2 g of tri-tert-butylphosphine, 0.4 g of tris(dibenzylacetone)dipalladium(0), and 100 mL of xylene were added. The mixture was stirred under reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain the crude product. The crude product was purified by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) to obtain compound (1-181): 12.6 g (yield: 75.9%).

[0243] [Chemical Formula 23]

[0244]

[0245] The obtained white powder was subjected to NMR analysis, and the signals of the following 37 hydrogen atoms were detected, which identified the structure of the compound represented by compound (1-181).

[0246] 1 H-NMR (CDCl3): δ (ppm) = 8.18 (1H), 8.07 (1H), 8.00 (4H), 7.93 (1H), 7.83 (1H), 7.72 (4H), 7.68 (1H), 7.64 (1H), 7.61-7.41 (12H), 7.33 (4H) 7.28-7.22 (6H), 7.10 (1H).

[0247] <Synthetic Example 3: Synthesis of Compound (1-182)>

[0248] In a nitrogen-purged reaction vessel, 15.6 g of N-phenyl-4-([1,2'-binaphthyl]-3-yl)aniline, 11.7 g of 3-(4-chlorophenyl)-1-phenylnaphthalene, 7.1 g of sodium tert-butoxy, 0.3 g of tri-tert-butylphosphine, 0.7 g of tris(dibenzylacetone)dipalladium(0), and 160 mL of xylene were added, and the mixture was stirred under reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using an ethyl acetate / toluene mixture to obtain compound (1-182): 20.0 g (yield: 74.1%).

[0249] [Chemical Formula 24]

[0250]

[0251] The obtained white powder was subjected to NMR analysis, and the signals of the following 37 hydrogen atoms were detected, which identified the structure of the compound represented by compound (1-182).

[0252] 1 H-NMR (CDCl3): δ (ppm) = 8.12 (1H), 8.07 (2H), 8.01 (2H), 7.99-7.91 (5H), 7.84 (1H), 7.76 -7.67 (6H), 7.62-7.51 (8H), 7.49 (1H), 7.45 (2H), 7.34 (2H), 7.31-6.91 (6H), 7.11 (1H).

[0253] <Synthetic Example 4: Synthesis of Compounds (1-23)>

[0254] After nitrogen purging, 1.8 g of aniline, 12.2 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 0.7 g of tris(dibenzylideneacetone)palladium(0), 0.3 g of tri-tert-butylphosphine, 7.4 g of sodium tert-butoxyl, and 180 ml of xylene were added to the reaction vessel and stirred overnight under reflux.

[0255] After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain the crude product. The crude product was separated by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) and purified by recrystallization using ethanol solvent, thereby obtaining compound (1-23): 4.0 g (yield: 31.8%).

[0256] [Chemical Formula 25]

[0257]

[0258] The obtained pale yellow powder was subjected to NMR analysis, and the signals of the following 35 hydrogen atoms were detected, which identified the structure of the compound represented by compounds (1-23).

[0259] 1 H-NMR (CDCl3): δ (ppm) = 8.12 (2H), 7.99 (2H), 7.90 (2H), 7.78 (2H), 7.59-7.51 (14H), 7.48-7.44 (4H), 7.30 (2H), 7.20-7.16 (6H), 7.08 (1H).

[0260] <Synthetic Example 5: Synthesis of Compound (1-190)>

[0261] In a nitrogen-purged reaction vessel, 8.0 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 7.5 g of N-(phenyl)-4-(phenylnaphth-3-yl)aniline, 3.1 g of sodium tert-butoxy, 0.2 g of bis[tris(tert-butylphosphine)]palladium(0), and 96 mL of toluene were added, and the mixture was stirred under reflux for 3 hours. After confirming the completion of the reaction, the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain compound (1-190): 10.3 g (yield: 73.6%).

[0262] [Chemical Formula 26]

[0263]

[0264] The obtained white powder was subjected to NMR analysis, and the signals of the following 35 hydrogen atoms were detected, which identified the structure of the compound represented by compound (1-190).

[0265] 1 H-NMR (CDCl3): δ (ppm) = 8.13 (1H), 8.07 (1H), 7.99 (2H), 7.91 (2H), 7.79 (1H), 7.73 (1H), 7.68 (2H), 7.59-7.42 (16H), 7.33 (2H), 7.26-7.20 (6H), 7.10 (1H).

[0266] <Synthetic Example 6: Synthesis of Compound (1-214)>

[0267] In a nitrogen-purged reaction vessel, 8.2 g of 7-(4-bromophenyl-d4)-1-phenylnaphthalene, 9.0 g of N-(phenyl-d4)-4-(phenylnaphth-3-yl)aniline-d5, 4.3 g of sodium tert-butoxy, 0.2 g of bis[tris(tert-butylphosphine)]palladium(0), and 90 mL of toluene were added, and the mixture was stirred under reflux for 2 hours. After confirming the completion of the reaction, the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain compound (1-214): 13.5 g (yield: 90.2%).

[0268] [Chemical Formula 27]

[0269]

[0270] The obtained white powder was subjected to NMR analysis, and the signals of the following 22 hydrogen atoms were detected, which identified the structure of the compound represented by compound (1-214).

[0271] 1 H-NMR (CDCl3): δ (ppm) = 8.13 (1H), 8.06 (1H), 7.99 (2H), 7.91 (2H), 7.79 (1H), 7.73 (1H), 7.59-7.52 (10H), 7.50-7.42 (4H).

[0272] <Synthetic Example 7: Synthesis of Compound (1-215)>

[0273] In a nitrogen-purged reaction vessel, 14.0 g of 3-(4-bromophenyl-d4)-1-phenylnaphthalene, 15.4 g of N-(phenyl-d4)-4-(phenylnaphth-3-yl)aniline-d5, 7.4 g of sodium tert-butoxy, 0.4 g of bis[tris(tert-butylphosphine)]palladium(0), and 140 mL of toluene were added, and the mixture was stirred under reflux for 1 hour. After confirming the completion of the reaction, the filtrate was concentrated to obtain the crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain compound (1-215): 24.0 g (yield: 94.1%).

[0274] [Chemical Formula 28]

[0275]

[0276] The obtained white powder was subjected to NMR analysis, and the signals of the following 22 hydrogen atoms were detected, which identified the structure of the compound represented by compound (1-215).

[0277] 1 H-NMR (CDCl3): δ (ppm) = 8.08 (2H), 7.98 (2H), 7.92 (2H), 7.74 (2H), 7.59-7.52 (10H), 7.49-7.43 (4H).

[0278] Compounds represented by general formula (1) other than those synthesized in Synthesis Examples 1 to 7 can also be synthesized in the same manner as in Synthesis Examples 1 to 7.

[0279] <Determination 1: Determination of Glass Transition Point>

[0280] The glass transition points of the aromatic amine compounds represented by general formula (1) synthesized in Synthesis Examples 1 to 7 were determined by a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, model: DSC3100SA). The results are shown in Table 1.

[0281] It was confirmed that the aromatic amine compounds represented by general formula (1) have a glass transition point of over 100°C and the thin film is stable.

[0282] <Determination 2: Determination of HOMO Levels>

[0283] A vapor-deposited film with a thickness of 100 nm was fabricated on an ITO substrate using an aromatic amine compound represented by general formula (1), and the HOMO energy levels (HOMO energy level, ionization potential) were measured using an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., model: PYS-202). The results are shown in Table 1.

[0284] [Table 1]

[0285]

[0286] It can be seen that the aromatic amine compounds represented by general formula (1) synthesized in Synthesis Examples 1 to 7 show a preferred energy level (5.4 eV) compared with the HOMO energy level of general hole transport materials such as NPD and TPD, and have good hole transport capability.

[0287] Therefore, the aromatic amine compounds represented by general formula (1) are useful as materials for hole injection layer, hole transport layer, electron blocking layer or light emission layer of organic EL devices, which can improve the luminous efficiency, driving voltage and durability of conventional organic EL devices.

[0288] [Example 1]

[0289] In Example 1, as Figure 1 As shown, after 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 sequentially deposited on it, thereby fabricating an organic EL element.

[0290] Specifically, a glass substrate 1, formed by sequentially depositing a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film in isopropanol, was ultrasonically cleaned for 20 minutes and then dried on a heating plate heated to 250°C for 10 minutes. After a 2-minute UV ozone treatment, the ITO-coated glass substrate was placed in a vacuum evaporation machine, and the pressure was reduced to below 0.001 Pa. Next, using a transparent anode 2 as a hole injection layer 3, the following compounds (Acceptor-1) and (HTM-1) as electron acceptors were co-deposited at a deposition rate ratio of (Acceptor-1):compound (HTM-1) = 3:97, forming a film with a thickness of 10 nm. On this hole injection layer 3, the following compound (HTM-1) was formed as a hole transport layer 4 with a thickness of 140 nm. On the hole transport layer 4, an electron blocking layer 5 is formed of compound (1-89) synthesized in Synthesis Example 1, with a film thickness of 5 nm. On the electron blocking layer 5, as the light-emitting layer 6, compound (2-1) and compound (EMH-1) are co-deposited at a deposition rate ratio of (2-1):(EMH-1) = 5:95, forming a film thickness of 20 nm. On the light-emitting layer 6, as the electron transport layer 7, compound (ETM-1) and compound (ETM-2) are co-deposited at a deposition rate ratio of (ETM-1):(ETM-2) = 50:50, forming a film thickness of 30 nm. On the electron transport layer 7, as the electron injection layer 8, lithium fluoride is formed with a film thickness of 1 nm. On the electron injection layer 8, as the cathode 9, a magnesium-silver alloy is formed with a film thickness of 12 nm. Finally, as the capping layer 10, the following compound (CPL-1) was formed into a film with a thickness of 60 nm. The characteristics of the fabricated organic EL element were measured in atmospheric conditions at room temperature (manufactured by ENC Technology, Inc., model: IVL-12M). The results of the measurement of the luminescence characteristics of the fabricated organic EL element under a DC voltage are summarized in Table 2.

[0291] [Chemical Formula 29]

[0292]

[0293] [Examples 2 to 189]

[0294] In Example 1, the compounds shown in Table 2 were used instead of compounds (1-89) used as the material for electron blocking layer 5 and compounds (2-1) used as the material for luminescent layer 6. Otherwise, an organic EL element was fabricated using the same method. The luminescence characteristics of the fabricated organic EL element were measured under atmospheric conditions and at room temperature with an applied DC voltage. The results are summarized in Table 2.

[0295] [Comparative Example 1]

[0296] For comparison, in Example 1, the compound with the following structural formula (HTM-2) was used instead of compound (1-89) as the material for the electron blocking layer 5. Otherwise, an organic EL element was fabricated under the same conditions (see Patent Document 8). The characteristics of the fabricated organic EL element were measured in air at room temperature. The results of the measurement of the light emission characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0297] [Comparative Example 2]

[0298] For comparison, in Example 1, the electron blocking layer 5 was made of a compound with the following structural formula (HTM-3) instead of compound (1-89), and an organic EL element was fabricated under the same conditions (see Patent Document 7). The characteristics of the fabricated organic EL element were measured in air at room temperature. The results of the measurement of the luminescence characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0299] [Comparative Example 3]

[0300] For comparison, in Example 1, the material for the light-emitting layer 6 was replaced by compound (2-1) with compound (EMD-1) of the following structural formula, and an organic EL element was fabricated under the same conditions. The characteristics of the fabricated organic EL element were measured in air at room temperature. The results of the measurement of the light-emitting characteristics of the fabricated organic EL element when a DC voltage was applied are summarized in Table 2.

[0301] [Chemical Formula 30]

[0302]

[0303] The results of measuring the lifetime of organic EL devices prepared in Examples 1 to 189 and Comparative Examples 1 to 3 are summarized in Table 2. The luminous intensity at the start of emission (initial intensity) was set to 2000 cd / m². 2 When driven by constant current, the luminous intensity decreases to 1900 cd / m². 2The time it takes for the component's lifespan to be measured is equivalent to 95% of the initial brightness when it is set to 100% and then decays to 95%.

[0304] [Table 2-1]

[0305]

[0306] [Table 2-2]

[0307]

[0308] [Table 2-3]

[0309]

[0310] [Table 2-4]

[0311]

[0312] [Table 2-5]

[0313]

[0314] As shown in Table 2, regarding the flow current density of 10 mA / cm² 2 The luminous efficiency at the specified current is 9.40 to 10.26 cd / A, which is higher than that of the organic EL elements in Examples 1 to 189, which is 8.01 to 8.87 cd / A. Furthermore, in terms of power efficiency, it is 8.84 to 9.69 lm / W, which is higher than that of the organic EL elements in Examples 1 to 189, which is 7.34 to 7.94 lm / W. Moreover, in terms of device lifetime (attenuation to 95%), it is 196 to 304 hours, which is longer than that of the organic EL elements in Examples 1 to 189, which is 156 to 183 hours.

[0315] The results above clearly show that, compared with the aromatic amine compounds that are conventional hole transport materials, the aromatic amine compounds with the specific structure represented by general formula (1) have a large hole mobility and excellent electron blocking ability. Furthermore, by combining them with organoboron compounds represented by general formula (2-1) or general formula (2-2), it is possible to achieve organic EL elements with higher luminous efficiency and longer lifetime compared with conventional organic EL elements.

[0316] Industrial availability

[0317] The organic EL element using aromatic amine compounds and organoboron compounds with specific structures in this invention improves luminous efficiency and durability, thus enabling its application in household appliances or lighting. Furthermore, the aromatic amine compounds of this invention can be used not only in organic EL elements but also in electronic devices such as electrophotographic sensors, image sensors, photoelectric conversion elements, and solar cells.

[0318] Symbol Explanation

[0319] 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. An organic electroluminescent element having an anode, a cathode, and an organic layer sandwiched between the anode and the cathode, said organic layer comprising an aromatic amine compound represented by general formula (1) and an organoboron compound represented by general formula (2-1) or general formula (2-2). [Chemical Formula 1] In the formula, L1 to L3 can be the same or different from each other, and represent a single bond, a divalent aromatic hydrocarbon group with 6 to 30 deuterated or unsubstituted carbon atoms, a divalent fused polycyclic aromatic hydrocarbon group with 10 to 30 deuterated or unsubstituted carbon atoms, a divalent aromatic heterocyclic group with 2 to 20 deuterated or unsubstituted carbon atoms, or a divalent fused polycyclic aromatic heterocyclic group with 2 to 30 deuterated or unsubstituted carbon atoms. A1 and A2 can be the same or different from each other, and represent deuterated or unsubstituted naphthyl groups. A3 represents an aromatic hydrocarbon group with 6 to 30 substituted or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon group with 10 to 30 substituted or unsubstituted carbon atoms, an aromatic heterocyclic group with 2 to 20 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms. R1 and R2 can be the same or different from each other, and represent an aromatic hydrocarbon group with 6 to 30 deuterated or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon group with 10 to 30 deuterated or unsubstituted carbon atoms, an aromatic heterocyclic group with 2 to 20 deuterated or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocyclic group with 2 to 30 deuterated or unsubstituted carbon atoms. The term "substituted or unsubstituted" indicates having one or two or more substituents, or having no substituents. The "substituents" can be the same or different from each other, and can represent deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 carbon atoms, cycloalkyl groups with 3 to 30 carbon atoms, alkenyl groups with 2 to 30 carbon atoms, aromatic hydrocarbon groups with 6 to 50 carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms, aromatic heterocyclic groups with 2 to 50 carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 30 carbon atoms, amino groups with 0 to 30 carbon atoms, or silyl groups with 3 to 30 carbon atoms. Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the categories of "6-30 carbon atoms", "10-30 carbon atoms", "2-20 carbon atoms", and "2-30 carbon atoms" in A3, R1, and R2. [Chemical Formula 2] In the formula, Q1 to Q3 can be the same or different from each other, and represent an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon ring with 10 to 50 substituted or unsubstituted carbon atoms, an aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms. Y1 to Y3 can be the same or different from each other, and can represent N-R3, CR4R5, O, S, Se, or SiR6R7. R3 to R7 can be the same or different from each other, and represent hydrogen atoms, deuterium atoms, halogen atoms, nitro groups, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 30 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 30 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, and fused groups with 10 to 50 substituted or unsubstituted carbon atoms. Polycyclic aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups with 2 to 50 carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 50 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, substituted or unsubstituted arylthio groups with 5 to 30 carbon atoms, substituted or unsubstituted amino groups with 0 to 30 carbon atoms, or substituted or unsubstituted silyl groups with 3 to 30 carbon atoms. R3 to R7 can form rings by bonding or fusion with any one of Q1 to Q3 via single bonds, N, O, P, or S. R4 and R5, and R6 and R7 can bond with each other to further form rings. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the categories of "6-50 carbon atoms", "10-50 carbon atoms", "2-50 carbon atoms", "1-30 carbon atoms", "3-30 carbon atoms", "2-30 carbon atoms", "6-30 carbon atoms", "5-30 carbon atoms", and "0-30 carbon atoms" in Q1-Q3, Y1-Y3, and R3-R7. When Y2 or Y3 is N-R3, at least one of R3 represents a fused polycyclic aromatic heterocyclic group represented by the following general formula (2-A) or an aromatic hydrocarbon group, fused polycyclic aromatic hydrocarbon group, or fused polycyclic aromatic heterocyclic group represented by the following general formula (2-B). [Chemical Formula 3] In the formula, X represents O or S. R8~R 15 These can be the same as or different from each other, and represent single bonds, hydrogen atoms, deuterium atoms, halogen atoms, hydroxyl groups, nitro groups, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 30 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkynyl groups with 2 to 30 substituted or unsubstituted carbon atoms, heterocyclic alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, and fused polycyclic aromatic hydrocarbon groups with 2 to 30 substituted or unsubstituted carbon atoms. Polycyclic aromatic heterocyclic groups, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, substituted or unsubstituted arylthio groups with 5 to 30 carbon atoms, substituted or unsubstituted amino groups with 0 to 30 carbon atoms, substituted or unsubstituted silyl groups with 3 to 30 carbon atoms, substituted or unsubstituted germanyl groups with 0 to 30 carbon atoms, substituted or unsubstituted boronyl groups with 0 to 30 carbon atoms, substituted or unsubstituted aluminumyl groups with 0 to 30 carbon atoms, substituted phosphoryl groups with 0 to 30 carbon atoms, substituted or unsubstituted selenyl groups with 0 to 30 carbon atoms, or substituted or unsubstituted telluryl groups with 0 to 30 carbon atoms. R8~R 15 Any one of them is bonded to the N-R3 represented by Y2 or Y3. R8~R 15 It can form rings by bonding or fusion with adjacent groups via single bonds, N, O, or S. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R8 to R9 groups. 15 Among the terms "carbon number 1-30", "carbon number 3-30", "carbon number 2-30", "carbon number 10-30", "carbon number 6-50", "carbon number 2-50", "carbon number 6-30", "carbon number 5-30", "carbon number 0-30", and "carbon number 3-30", [Chemical Formula 4] In the formula, R 16 The following groups represent hydrogen atoms, deuterium atoms, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms. R 17 The following groups represent hydrogen atoms, deuterium atoms, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 30 substituted or unsubstituted carbon atoms. R 18 ~R 20 They can be the same as or different from each other, and can represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 30 substituted or unsubstituted carbon atoms, alkylthio groups with 1 to 30 substituted or unsubstituted carbon atoms, amino groups with 0 to 30 substituted or unsubstituted carbon atoms, or silyl groups with 3 to 30 substituted or unsubstituted carbon atoms. The wavy line represents the bonding portion with N in N-R3 represented by Y2 or Y3. R 16 ~R 20 It can form rings by bonding or fusion with adjacent groups via single bonds, N, O, or S. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R. 16 ~R 20 Among them are "carbon number 1-30", "carbon number 6-50", "carbon number 2-50", "carbon number 3-30", "carbon number 10-30", "carbon number 2-30" and "carbon number 0-30".

2. The organic electroluminescent element according to claim 1, comprising an aromatic amine compound, wherein A1 and A2 in the general formula (1) may be the same as or different from each other, and are deuterated or unsubstituted 1,2-naphthylene, deuterated or unsubstituted 1,3-naphthylene, deuterated or unsubstituted 1,4-naphthylene, deuterated or unsubstituted 2,6-naphthylene, deuterated or unsubstituted 2,7-naphthylene, or deuterated or unsubstituted 2,8-naphthylene.

3. The organic electroluminescent element according to claim 1, comprising an aromatic amine compound, wherein L1 and L2 in the general formula (1) are deuterated or unsubstituted phenylene or deuterated or unsubstituted biphenylene.

4. The organic electroluminescent element according to claim 1, comprising an aromatic amine compound, wherein R1 and R2 in the general formula (1) may be the same or different from each other, and are deuterated or unsubstituted phenyl, deuterated or unsubstituted naphthyl, deuterated or unsubstituted dibenzofuranyl, deuterated or unsubstituted phenanthryl, or deuterated or unsubstituted biphenyl.

5. The organic electroluminescent element according to claim 1, comprising an aromatic amine compound, wherein A3 in the general formula (1) is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted biphenyl.

6. The organic electroluminescent element according to any one of claims 1 to 5, comprising an aromatic amine compound in which A1 and A2 in the general formula (1) are the same group.

7. The organic electroluminescent element according to claim 6, comprising an aromatic amine compound in which R1 and R2 in the general formula (1) are the same group.

8. The organic electroluminescent element according to claim 6, comprising an aromatic amine compound in which R1 and R2 in the general formula (1) are different groups.

9. The organic electroluminescent element according to any one of claims 1 to 5, comprising an aromatic amine compound in which A1 and A2 in the general formula (1) are different groups.

10. The organic electroluminescent element according to claim 9, comprising an aromatic amine compound in which R1 and R2 in the general formula (1) are the same groups.

11. The organic electroluminescent element according to claim 9, comprising an aromatic amine compound in which R1 and R2 in the general formula (1) are different groups.

12. The organic electroluminescent element according to claim 1, wherein, The general formula (2-1) or general formula (2-2) includes organoboron compounds represented by the following general formulas (2-3), (2-4), (2-5), or (2-6). [Chemical Formula 5] In the formula, Y 1、 Y 2、 Y3 has the same meaning as the general formulas (2-1) and (2-2). Y4 represents N-R3, C-R4R5, O, S, Se, or Si-R6R7. R3 to R7 have the same meaning as general formulas (2-1) and (2-2). Z can be the same as or different from each other, and represents N or CR. 21 , R 21 The following groups represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 30 substituted or unsubstituted carbon atoms, and substituted or unsubstituted carbon atoms. The following are compounds: alkoxy groups with 1 to 30 atoms; aryloxy groups with 6 to 30 substituted or unsubstituted carbon atoms; alkathio groups with 1 to 30 substituted or unsubstituted carbon atoms; arylthio groups with 5 to 30 substituted or unsubstituted carbon atoms; alkylamino groups with 1 to 30 substituted or unsubstituted carbon atoms; arylamino groups with 5 to 30 substituted or unsubstituted carbon atoms; alkylsilyl groups with 1 to 30 substituted or unsubstituted carbon atoms; or arylsilyl groups with 5 to 30 substituted or unsubstituted carbon atoms; R 21 They can form rings by bonding or fusion with adjacent groups via single bonds, N, O, or S. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R. 21 Among the terms "carbon number 1-30", "carbon number 3-30", "carbon number 6-50", "carbon number 2-50", "carbon number 6-30" and "carbon number 5-30".

13. The organic electroluminescent element according to claim 1, wherein, The organic layer comprises at least a hole transport layer and a light-emitting layer, wherein the hole transport layer contains a compound represented by the general formula (1), and the light-emitting layer contains an organoboron compound represented by the general formula (2-1) or the general formula (2-2).

14. The organic electroluminescent element according to claim 1, wherein, The organic layer comprises at least an electron blocking layer and a light-emitting layer, wherein the electron blocking layer contains a compound represented by the general formula (1), and the light-emitting layer contains an organoboron compound represented by the general formula (2-1) or the general formula (2-2).

15. The organic electroluminescent element according to claim 1, wherein, The organic layer comprises at least a hole injection layer and a light-emitting layer, wherein the hole injection layer contains a compound represented by the general formula (1), and the light-emitting layer contains an organoboron compound represented by the general formula (2-1) or the general formula (2-2).

16. An electronic device having a pair of electrodes and an organic layer sandwiched between the pair of electrodes, said organic layer comprising an aromatic amine compound represented by general formula (1) and an organoboron compound represented by general formula (2-1) or general formula (2-2). [Chemical Formula 6] In the formula, L1 to L3 can be the same or different from each other, and represent single bonds, divalent aromatic hydrocarbon groups with 6 to 30 deuterated or unsubstituted carbon atoms, divalent fused polycyclic aromatic hydrocarbon groups with 10 to 30 deuterated or unsubstituted carbon atoms, divalent aromatic heterocyclic groups with 2 to 20 deuterated or unsubstituted carbon atoms, or divalent fused polycyclic aromatic heterocyclic groups with 2 to 30 deuterated or unsubstituted carbon atoms. A1 and A2 can be the same or different from each other, and represent deuterated or unsubstituted naphthyl groups. A3 represents an aromatic hydrocarbon group with 6 to 30 substituted or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon group with 10 to 30 substituted or unsubstituted carbon atoms, an aromatic heterocyclic group with 2 to 20 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms. R1 and R2 can be the same or different from each other, and represent an aromatic hydrocarbon group with 6 to 30 deuterated or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon group with 10 to 30 deuterated or unsubstituted carbon atoms, an aromatic heterocyclic group with 2 to 20 deuterated or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocyclic group with 2 to 30 deuterated or unsubstituted carbon atoms. The term "substituted or unsubstituted" indicates having one or two or more substituents, or having no substituents. The "substituents" can be the same or different from each other, and can represent deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 carbon atoms, cycloalkyl groups with 3 to 30 carbon atoms, alkenyl groups with 2 to 30 carbon atoms, aromatic hydrocarbon groups with 6 to 50 carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms, aromatic heterocyclic groups with 2 to 50 carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 30 carbon atoms, amino groups with 0 to 30 carbon atoms, or silyl groups with 3 to 30 carbon atoms. Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the categories of "6-30 carbon atoms", "10-30 carbon atoms", "2-20 carbon atoms", and "2-30 carbon atoms" in A3, R1, and R2. [Chemical Formula 7] In the formula, Q1 to Q3 can be the same or different from each other, and represent an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, a fused polycyclic aromatic hydrocarbon ring with 10 to 50 substituted or unsubstituted carbon atoms, an aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms, or a fused polycyclic aromatic heterocycle with 2 to 50 substituted or unsubstituted carbon atoms. Y1 to Y3 can be the same or different from each other, and can represent N-R3, CR4R5, O, S, Se, or SiR6R7. R3 to R7 can be the same or different from each other, and represent hydrogen atoms, deuterium atoms, halogen atoms, nitro groups, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 30 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 30 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, and fused groups with 10 to 50 substituted or unsubstituted carbon atoms. Polycyclic aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups with 2 to 50 carbon atoms, fused polycyclic aromatic heterocyclic groups with 2 to 50 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, substituted or unsubstituted arylthio groups with 5 to 30 carbon atoms, substituted or unsubstituted amino groups with 0 to 30 carbon atoms, or substituted or unsubstituted silyl groups with 3 to 30 carbon atoms. R3 to R7 can form rings by bonding or fusion with any one of Q1 to Q3 via single bonds, N, O, P, or S. R4 and R5, and R6 and R7 can bond with each other to further form rings. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the categories of "6-50 carbon atoms", "10-50 carbon atoms", "2-50 carbon atoms", "1-30 carbon atoms", "3-30 carbon atoms", "2-30 carbon atoms", "6-30 carbon atoms", "5-30 carbon atoms", and "0-30 carbon atoms" in Q1-Q3, Y1-Y3, and R3-R7. When Y2 or Y3 is N-R3, at least one of R3 represents a fused polycyclic aromatic heterocyclic group represented by the following general formula (2-A) or an aromatic hydrocarbon group, fused polycyclic aromatic hydrocarbon group, or fused polycyclic aromatic heterocyclic group represented by the following general formula (2-B). [Chemical Formula 8] In the formula, X represents O or S. R8~R 15 These can be the same as or different from each other, and represent single bonds, hydrogen atoms, deuterium atoms, halogen atoms, hydroxyl groups, nitro groups, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 30 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 30 substituted or unsubstituted carbon atoms, alkynyl groups with 2 to 30 substituted or unsubstituted carbon atoms, heterocyclic alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, and fused polycyclic aromatic hydrocarbon groups with 2 to 30 substituted or unsubstituted carbon atoms. Polycyclic aromatic heterocyclic groups, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, substituted or unsubstituted arylthio groups with 5 to 30 carbon atoms, substituted or unsubstituted amino groups with 0 to 30 carbon atoms, substituted or unsubstituted silyl groups with 3 to 30 carbon atoms, substituted or unsubstituted germanyl groups with 0 to 30 carbon atoms, substituted or unsubstituted boronyl groups with 0 to 30 carbon atoms, substituted or unsubstituted aluminumyl groups with 0 to 30 carbon atoms, substituted phosphoryl groups with 0 to 30 carbon atoms, substituted or unsubstituted selenyl groups with 0 to 30 carbon atoms, or substituted or unsubstituted telluryl groups with 0 to 30 carbon atoms. R8~R 15 Any one of them is bonded to the N-R3 represented by Y2 or Y3. R8~R 15 It can form rings by bonding or fusion with adjacent groups via single bonds, N, O, or S. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R8 to R9 groups. 15 Among the terms "carbon number 1-30", "carbon number 3-30", "carbon number 2-30", "carbon number 10-30", "carbon number 6-50", "carbon number 2-50", "carbon number 6-30", "carbon number 5-30", "carbon number 0-30", and "carbon number 3-30", [Chemical Formula 9] In the formula, R 16 The following groups represent hydrogen atoms, deuterium atoms, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms. R 17 The following groups represent hydrogen atoms, deuterium atoms, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, fused polycyclic aromatic hydrocarbon groups with 10 to 30 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, or fused polycyclic aromatic heterocyclic groups with 2 to 30 substituted or unsubstituted carbon atoms. R 18 ~R 20 They can be the same as or different from each other, and can represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 30 substituted or unsubstituted carbon atoms, aromatic hydrocarbon groups with 6 to 50 substituted or unsubstituted carbon atoms, aromatic heterocyclic groups with 2 to 50 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 30 substituted or unsubstituted carbon atoms, alkylthio groups with 1 to 30 substituted or unsubstituted carbon atoms, amino groups with 0 to 30 substituted or unsubstituted carbon atoms, or silyl groups with 3 to 30 substituted or unsubstituted carbon atoms. The wavy line represents the bonding portion of N with N-R3 represented by Y2 or Y3. R 16 ~R 20 It can form rings by bonding or fusion with adjacent groups via single bonds, N, O, or S. The terms "substituted or unsubstituted" have the same meaning as those in general formula (1), and "substituent" refers to the same group as the "substituent" in general formula (1). Furthermore, these "substituents" may have one or more substituents. Furthermore, when the "substituent" has a carbon atom, that carbon atom is included in the R. 16 ~R 20 Among them are "carbon number 1-30", "carbon number 6-50", "carbon number 2-50", "carbon number 3-30", "carbon number 10-30", "carbon number 2-30" and "carbon number 0-30".

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