Organic compound and application thereof

Abstract

The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic compound and application thereof. According to the organic compound provided by the invention, the parent nucleus in the structure of the formula (1) is taken as a basis and is matched with different substituent groups, so that the whole compound shows relatively high electron transmission performance; the carrier mobility of the organic compound with the specific structure is relatively balanced, so that the organic electroluminescent device containing the organic compound has relatively low driving voltage, relatively high luminous efficiency and relatively long service life.

Description

An organic compound and its application Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, specifically relating to an organic compound and its applications. Background Technology

[0002] OLED (Organic Light Emitting Diode) is a highly integrated optical device, its core being a complex organic multilayer structure built between the cathode and anode. This system includes multiple functional layers such as a hole injection layer, a hole transport layer, an auxiliary layer, a light-emitting layer (a precise combination of host material and dopants), a hole blocking layer, an electron transport layer, and an electron injection layer. Under appropriate voltage driving, OLEDs can effectively inject and recombine holes and electrons within the light-emitting layer, forming high-energy excited-state molecules. Subsequently, these excited-state molecules release energy in the form of light radiation during de-excitation, achieving efficient light emission.

[0003] However, current OLED technology still faces several key challenges, mainly including high driving voltage requirements, insufficient luminous efficiency, and limited device lifespan. These issues severely restrict the widespread application and commercialization of OLED technology. Therefore, academia and industry are actively engaged in the research and development of new OLED materials, aiming to achieve low-voltage driving, high luminous efficiency output, and long-lifespan operation through material innovation. This will drive OLED technology to a higher level and expand its application potential in display, lighting, and other fields. Summary of the Invention

[0004] The purpose of this invention is to overcome the problems of high driving voltage, low luminous efficiency and short luminous lifetime of organic electroluminescent materials in organic electroluminescent devices in related technologies, and to provide an organic compound and its application.

[0005] In the definition of substituent terms in this invention:

[0006] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0007] The term "multiple organic electroluminescent materials" in this disclosure refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials being contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials can be a combination of at least two compounds, said materials being contained in at least one of: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be contained in the same layer or different layers, and can be mixed-evaporated or co-evaporated, or can be evaporated individually.

[0008] In this application, the term "substituent" has its common meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0009] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0010] In this application, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0011] In this application, the term "C3-C60 cycloalkyl" refers to a cycloalkyl group consisting of at least 3 atoms. More specifically, it refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0012] In this application, the terms "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups, wherein the rings may be interrupted by short non-aromatic units and may contain a spirostructure. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene, etc., and arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracene, fluorene, and spirodifluorene, etc.

[0013] In this application, the term "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups in this application include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridinyl, pyrazinyl, and pyrimidineyl. Pyridyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridyl And their derivatives, etc.; heteroaryl groups include, but are not limited to, pyrifos, pyrrolizyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl Furanyl, dibenzothiophene, benzimidazolyl, benzithiazolyl, benzisisothiazolyl, benzisisooxazolyl, benzisoxazolyl, isoindolyl, indolyl, ininzolyl, benzisazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenoxazinyl, phenanthridineyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc. As used herein, the term "substituted" means that a hydrogen atom in the compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0014] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0015] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0016] In this application, the definition of a group specifies the range of carbon atoms, and the number of carbon atoms is any integer within the defined range, such as C6-C60 aryl. The number of carbon atoms representing an aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.

[0017] In this application, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0018] This invention provides an organic compound having the structure shown in formula (1):

[0019]

[0020] In the formula,

[0021] Ar is selected from substituted or unsubstituted C6-C60 aryl groups;

[0022] Ar 1 Ar 2 Each is independently selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, or substituted or unsubstituted C6-C60 aryloxy groups;

[0023] n1 and n2 are each independently selected from any integer from 0 to 6;

[0024] The substituents of the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, and substituted C6-C60 aryloxy groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

[0025] Preferably, the organic compound has a structure shown in any one of Formulas 1-1 to 1-14:

[0026]

[0027] Preferably, Ar is selected from substituted or unsubstituted C6-C30 aryl groups;

[0028] Ar 1 Ar 2 Each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or substituted or unsubstituted C6-C30 aryloxy groups;

[0029] The substituents in the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, and substituted C6-C30 aryloxy groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

[0030] Preferably, Ar is selected from substituted or unsubstituted A groups, wherein the A group is selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluoranyl, triphenylene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl;

[0031] Ar 1 Ar 2 Each of the B groups is independently selected from substituted or unsubstituted groups, wherein the B groups are selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, phenylcarbazo-benzofuranyl;

[0032] Wherein, the substituents in the substituted A group and the substituted B group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0033] Preferably, Ar is selected from substituted or unsubstituted phenyl groups or substituted or unsubstituted naphthyl groups;

[0034] Ar 1 Ar 2 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthryl;

[0035] The substituents of the substituted phenyl, substituted naphthyl, substituted biphenyl, substituted dibenzofuranyl, and substituted phenanthrene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0036] Preferably, the substituents of the substituted phenyl, substituted naphthyl, substituted biphenyl, substituted dibenzofuranyl, and substituted phenanthryl are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

[0037] Preferably, the compound is selected from any one of the structures N-1 to N-445:

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] The present invention provides an organic electroluminescent material comprising an organic compound as described in any of the preceding claims.

[0053] Preferably, the organic electroluminescent material further comprises an organic compound represented by formula (2).

[0054]

[0055] In equation (2), Ar 3 Ar 4 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0056] The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl are each independently selected from deuterium, unsubstituted or C1-C6 alkyl or C6-C30 aryl substituted C6-C30 aryl; unsubstituted or C1-C6 alkyl or C6-C30 aryl substituted C3-C30 heteroaryl, C1-C6 alkyl;

[0057] Preferably, Ar 3 Ar 4 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl;

[0058] Preferably, Ar 3 Selected from dibenzofuranyl, phenyldibenzofuranyl, dibenzothiophenyl, phenyldibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl; Ar 4 Selected from phenyl, biphenyl, terphenyl, phenanthrene, naphthyl, phenylnaphthyl, and naphthylphenyl.

[0059] Preferably, the organic compound represented by formula (2) is selected from any compound from P-1 to P-15:

[0060]

[0061]

[0062] The preparation method of the organic compound represented by formula (2) of this invention is based on Chinese Patent CN116144347A (application number CN202111367059.0).

[0063] Preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 1:9-9:1;

[0064] Preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 2:8-8:2;

[0065] More preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 3:7-7:3;

[0066] More preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 4:6-6:4.

[0067] The present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic layer located between the anode and the cathode, the organic layer comprising an organic compound as described above or an organic electroluminescent material as described above.

[0068] Preferably, the organic layer includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0069] Preferably, the organic layer includes a light-emitting layer, which comprises an organic compound as described above;

[0070] Preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic compound as described above or an organic electroluminescent material as described above.

[0071] The present invention provides an electronic device, the electronic device comprising an organic electroluminescent device as described above, an organic compound as described above, or an organic electroluminescent material as described above.

[0072] The beneficial effects of this invention are:

[0073] The organic compound provided by the present invention, based on the core in the structure of formula (1), can exhibit high electron transport performance as a whole by combining different substituents; the carrier mobility of the organic compound with this specific structure is relatively balanced, thereby enabling the organic electroluminescent device containing the organic compound to have a lower driving voltage, higher luminous efficiency and longer lifetime. Attached Figure Description

[0074] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0075] Figure 1 is a structural diagram of the organic electroluminescent device in the embodiment of the present invention;

[0076] 1-Substrate; 2-Anode; 3-Hole injection layer; 4-Hole transport layer; 5-Light emission layer; 6-Electron transport layer; 7-Electron injection layer; 8-Cathode. Detailed Implementation

[0077] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0078] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0079] In this invention, the compound shown in Formula 1 is prepared via the following synthetic route:

[0080]

[0081] The starting materials Sx, Ax, and Bx can all be purchased directly or synthesized by referring to existing literature reports through conventional reaction routes and conditions.

[0082] The specific structures of the raw materials Sx, Ax, and Bx used in the embodiments of this invention are as follows:

[0083] The specific structure of raw material Sx is as follows:

[0084]

[0085] The specific structure of raw material Ax is as follows:

[0086]

[0087] The specific structure of raw material Bx is as follows:

[0088]

[0089] Example 1:

[0090] This invention provides a method for preparing compound N-4, comprising the following steps:

[0091]

[0092] Synthesis of intermediate N-4-1: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, the following starting materials were added sequentially: S-1 (1 mmol), A-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and quenched with saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate N-4-1 (yield 87%).

[0093] Synthesis of intermediate N-4-2: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate N-4-1 (1 mmol), pinacol diboronate (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were added sequentially. The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and quenched with saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate N-4-2 (yield 84%).

[0094] Synthesis of compound N-4: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, starting material B-2 (1 mmol), intermediate N-4-2 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were added sequentially. The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was washed twice with deionized water and twice with ethanol. The crude product was then purified twice by recrystallization from o-dichlorobenzene to obtain compound N-4 (yield 65%).

[0095] Elemental analysis: C 47 H 31 Theoretical N3 values: C, 88.51; H, 4.90; N, 6.59; Measured values: C, 88.54; H, 4.89; N, 6.57; HRMS(ESI) m / z [M+H] + Theoretical value: 637.79; Measured value: 638.72.

[0096] Example 2:

[0097] This invention provides a method for preparing compound N-32, comprising the following steps:

[0098]

[0099] Synthesis of intermediate N-32-1: The synthesis steps of intermediate N-32-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-2 and raw material A-1 is replaced with raw material A-2, thus obtaining intermediate N-32-1 (yield 88%).

[0100] Synthesis of intermediate N-32-2: The synthesis steps of intermediate N-32-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-32-1, thus obtaining intermediate N-32-2 (yield 83%).

[0101] Synthesis of compound N-32: The synthesis steps of compound N-32 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-32-2, and starting material B-2 is replaced with starting material B-3, thus obtaining compound N-32 (yield 63%).

[0102] Elemental analysis: C 47 H 29 Theoretical N₃O values: C, 86.61; H, 4.49; N, 6.45; O, 2.45 Measured values: C, 86.63; H, 4.47; N, 6.45; HRMS(ESI) m / z [M+H] +Theoretical value: 651.77; Measured value: 652.25.

[0103] Example 3:

[0104] This invention provides a method for preparing compound N-34, comprising the following steps:

[0105]

[0106] Synthesis of intermediate N-34-1: The synthesis steps of intermediate N-34-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-3 and raw material A-1 is replaced with raw material A-3, thus obtaining intermediate N-34-1 (yield 87%).

[0107] Synthesis of intermediate N-34-2: The synthesis steps of intermediate N-34-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-34-1, thus obtaining intermediate N-34-2 (yield 84%).

[0108] Synthesis of compound N-34: The synthesis steps of compound N-34 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-34-2, and starting material B-2 is replaced with starting material B-3, thus obtaining compound N-34 (yield 64%).

[0109] Elemental analysis: C 47 H 29 N₃O. Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.63; H, 4.49; N, 6.43; HRMS(ESI) m / z [M+H] + Theoretical value: 651.77; Measured value: 652.71.

[0110] Example 4:

[0111] This invention provides a method for preparing compound N-47, comprising the following steps:

[0112]

[0113] Synthesis of intermediate N-47-1: The synthesis steps of intermediate N-47-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-4 and raw material A-1 is replaced with raw material A-2, thus obtaining intermediate N-47-1 (yield 84%).

[0114] Synthesis of intermediate N-47-2: The synthesis steps of intermediate N-47-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-47-1, thus obtaining intermediate N-47-2 (yield 82%).

[0115] Synthesis of compound N-47: The synthesis steps of compound N-47 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-47-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-47 (yield 63%).

[0116] Elemental analysis: C 45 H 29 N3. Theoretical values: C, 88.35; H, 4.78; N, 6.87; Measured values: C, 88.37; H, 4.77; N, 6.86; HRMS(ESI) m / z [M+H] + Theoretical value: 611.75; Measured value: 612.73.

[0117] Example 5:

[0118] This invention provides a method for preparing compound N-56, comprising the following steps:

[0119]

[0120] Synthesis of intermediate N-56-1: The synthesis steps of intermediate N-56-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-5 and raw material A-1 is replaced with raw material A-2, thus obtaining intermediate N-56-1 (yield 83%).

[0121] Synthesis of intermediate N-56-2: The synthesis steps of intermediate N-56-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-56-1, thus obtaining intermediate N-56-2 (yield 83%).

[0122] Synthesis of compound N-56: The synthesis steps of compound N-56 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-56-2, and starting material B-2 is replaced with starting material B-4, thus obtaining compound N-56 (yield 63%).

[0123] Elemental analysis: C 47 H 31N3. Theoretical values: C, 88.51; H, 4.90; N, 6.59; Measured values: C, 88.52; H, 4.90; N, 6.58; HRMS(ESI) m / z [M+H] + Theoretical value: 637.79; Measured value: 638.72.

[0124] Example 6:

[0125] Synthesis of compound N-85:

[0126]

[0127] Synthesis of intermediate N-85-1: The synthesis steps of intermediate N-85-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-12 and raw material A-1 is replaced with raw material A-11, thus obtaining intermediate N-85-1 (yield 82%).

[0128] Synthesis of intermediate N-85-2: The synthesis steps of intermediate N-85-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-85-1, thus obtaining intermediate N-85-2 (yield 84%).

[0129] Synthesis of compound N-85: The synthesis steps of compound N-85 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-85-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-85 (yield 63%).

[0130] Elemental analysis: C 41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.69; H, 4.85; N, 7.46; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.93.

[0131] Example 7:

[0132] This invention provides a method for preparing compound N-93, comprising the following steps:

[0133]

[0134] Synthesis of intermediate N-93-1: The synthesis steps of intermediate N-93-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-6 and raw material A-1 is replaced with raw material A-4, thus obtaining intermediate N-93-1 (yield 83%).

[0135] Synthesis of intermediate N-93-2: The synthesis steps of intermediate N-93-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-93-1, thus obtaining intermediate N-93-2 (yield 83%).

[0136] Synthesis of compound N-93: The synthesis steps of compound N-93 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-93-2, and starting material B-2 is replaced with starting material B-4, thus obtaining compound N-93 (yield 63%).

[0137] Elemental analysis: C 47 H 31 N3. Theoretical values: C, 88.51; H, 4.90; N, 6.59; Measured values: C, 88.54; H, 4.89; N, 6.57; HRMS(ESI) m / z [M+H] + Theoretical value: 637.79; Measured value: 638.72.

[0138] Example 8:

[0139] Synthesis of compound N-125:

[0140]

[0141] Synthesis of intermediate N-125-1: The synthesis steps of intermediate N-125-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-8 and raw material A-1 is replaced with raw material A-10, thus obtaining intermediate N-125-1 (yield 82%).

[0142] Synthesis of intermediate N-125-2: The synthesis steps of intermediate N-125-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-125-1, thus obtaining intermediate N-125-2 (yield 84%).

[0143] Synthesis of compound N-125: The synthesis steps of compound N-125 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-125-2, and starting material B-2 is replaced with starting material B-1, thus yielding compound N-125 (yield 63%). Elemental analysis: C41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.68; H, 4.85; N, 7.47; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.87.

[0144] Example 9:

[0145] This invention provides a method for preparing compound N-129, comprising the following steps:

[0146]

[0147] Synthesis of intermediate N-129-1: The synthesis steps of intermediate N-129-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-3 and raw material A-1 is replaced with raw material A-4, thus obtaining intermediate N-129-1 (yield 83%).

[0148] Synthesis of intermediate N-129-2: The synthesis steps of intermediate N-129-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-129-1, thus obtaining intermediate N-129-2 (yield 83%).

[0149] Synthesis of compound N-129: The synthesis steps of compound N-129 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-129-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-129 (yield 63%).

[0150] Elemental analysis: C 41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.65; H, 4.86; N, 7.49; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.67.

[0151] Example 10:

[0152] This invention provides a method for preparing compound N-152, comprising the following steps:

[0153]

[0154] Synthesis of intermediate N-152-1: The synthesis steps of intermediate N-152-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-3 and raw material A-1 is replaced with raw material A-2, thus obtaining intermediate N-152-1 (yield 84%).

[0155] Synthesis of intermediate N-152-2: The synthesis steps of intermediate N-152-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-152-1, thus obtaining intermediate N-152-2 (yield 85%).

[0156] Synthesis of compound N-152: The synthesis steps of compound N-152 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-152-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-152 (yield 65%).

[0157] Elemental analysis: C 41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.62; H, 4.88; N, 7.52; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.67.

[0158] Example 11:

[0159] This invention provides a method for preparing compound N-159, comprising the following steps:

[0160]

[0161] Synthesis of intermediate N-159-1: The synthesis steps of intermediate N-159-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-7, thus obtaining intermediate N-159-1 (yield 82%).

[0162] Synthesis of intermediate N-159-2: The synthesis steps of intermediate N-159-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-159-1, thus obtaining intermediate N-159-2 (yield 81%).

[0163] Synthesis of compound N-159: The synthesis steps of compound N-159 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-159-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-159 (yield 66%).

[0164] Elemental analysis: C 41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.66; H, 4.86; N, 7.50; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.67.

[0165] Example 12:

[0166] Synthesis of compound N-205:

[0167]

[0168] Synthesis of intermediate N-205-1: The synthesis steps of intermediate N-205-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-14 and raw material A-1 is replaced with raw material A-9, thus obtaining intermediate N-205-1 (yield 82%).

[0169] Synthesis of intermediate N-205-2: The synthesis steps of intermediate N-205-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-205-1, thus obtaining intermediate N-205-2 (yield 82%).

[0170] Synthesis of compound N-205: The synthesis steps of compound N-205 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-205-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-205 (yield 64%).

[0171] Elemental analysis: C 45 H 29 N3. Theoretical values: C, 88.35; H, 4.78; N, 6.87; Measured values: C, 88.38; H, 4.76; N, 6.86; HRMS(ESI) m / z [M+H] + Theoretical value: 611.75; Measured value: 612.97.

[0172] Example 13:

[0173] This invention provides a method for preparing compound N-211, comprising the following steps:

[0174]

[0175] Synthesis of intermediate N-211-1: The synthesis steps of intermediate N-211-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-8 and raw material A-1 is replaced with raw material A-5, thus obtaining intermediate N-211-1 (yield 82%).

[0176] Synthesis of intermediate N-211-2: The synthesis steps of intermediate N-211-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-211-1, thus obtaining intermediate N-211-2 (yield 81%).

[0177] Synthesis of compound N-211: The synthesis steps of compound N-211 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-211-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-211 (yield 66%).

[0178] Elemental analysis: C 41 H 21 D6N3. Theoretical values: C, 86.74; H, 5.86; N, 7.40; Measured values: C, 86.77; H, 5.84; N, 7.39; HRMS(ESI) m / z [M+H] + Theoretical value: 567.72; Measured value: 568.67.

[0179] Example 14:

[0180] This invention provides a method for preparing compound N-214, comprising the following steps:

[0181]

[0182] Synthesis of intermediate N-214-1: The synthesis steps of intermediate N-214-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-9 and raw material A-1 is replaced with raw material A-6, thus obtaining intermediate N-214-1 (yield 83%).

[0183] Synthesis of intermediate N-214-2: The synthesis steps of intermediate N-214-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-214-1, thus obtaining intermediate N-214-2 (yield 81%).

[0184] Synthesis of compound N-214: The synthesis steps of compound N-214 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-214-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-214 (yield 64%).

[0185] Elemental analysis: C 41 H 16 D 11 N3. Theoretical values: C, 85.98; H, 6.68; N, 7.34; Measured values: C, 85.95; H, 6.69; N, 7.36; HRMS(ESI) m / z [M+H] + Theoretical value: 572.76; Measured value: 573.79.

[0186] Example 15:

[0187] This invention provides a method for preparing compound N-219, comprising the following steps:

[0188]

[0189] Synthesis of intermediate N-219-1: The synthesis steps of intermediate N-219-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-10 and raw material A-1 is replaced with raw material A-2, thus obtaining intermediate N-219-1 (yield 82%).

[0190] Synthesis of intermediate N-219-2: The synthesis steps of intermediate N-219-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-219-1, thus obtaining intermediate N-219-2 (yield 80%).

[0191] Synthesis of compound N-219: The synthesis steps of compound N-219 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-219-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-219 (yield 64%).

[0192] Elemental analysis: C 41 H 21 D6N3. Theoretical values: C, 86.74; H, 5.86; N, 7.40; Measured values: C, 86.76; H, 5.85; N, 7.39; HRMS(ESI) m / z [M+H] + Theoretical value: 567.72; Measured value: 568.75.

[0193] Example 16:

[0194] This invention provides a method for preparing compound N-257, comprising the following steps:

[0195]

[0196] Synthesis of intermediate N-257-1: The synthesis steps of intermediate N-257-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-6, thus obtaining intermediate N-257-1 (yield 81%).

[0197] Synthesis of intermediate N-257-2: The synthesis steps of intermediate N-257-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-257-1, thus obtaining intermediate N-257-2 (yield 81%).

[0198] Synthesis of compound N-257: The synthesis steps of compound N-257 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-257-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-257 (yield 65%).

[0199] Elemental analysis: C 41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.66; H, 4.86; N, 7.50; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.67.

[0200] Example 17:

[0201] This invention provides a method for preparing compound N-294, comprising the following steps:

[0202]

[0203] Synthesis of intermediate N-294-1: The synthesis steps of intermediate N-294-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-3 and raw material A-1 is replaced with raw material A-3, thus obtaining intermediate N-294-1 (yield 82%).

[0204] Synthesis of intermediate N-294-2: The synthesis steps of intermediate N-294-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-294-1, thus obtaining intermediate N-294-2 (yield 80%).

[0205] Synthesis of compound N-294: The synthesis steps of compound N-294 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-294-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-294 (yield 64%).

[0206] Elemental analysis: C 41 H 27 N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.66; H, 4.87; N, 7.47; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.67.

[0207] Example 18:

[0208] This invention provides a method for preparing compound N-311, comprising the following steps:

[0209]

[0210] Synthesis of intermediate N-311-1: The synthesis steps of intermediate N-311-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-3, thus obtaining intermediate N-311-1 (yield 83%).

[0211] Synthesis of intermediate N-311-2: The synthesis steps of intermediate N-311-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-311-1, thus obtaining intermediate N-311-2 (yield 82%).

[0212] Synthesis of compound N-311: The synthesis steps of compound N-311 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-311-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-311 (yield 63%).

[0213] Elemental analysis: C 41 H 27N3. Theoretical values: C, 87.67; H, 4.85; N, 7.48; Measured values: C, 87.66; H, 4.84; N, 7.50; HRMS(ESI) m / z [M+H] + Theoretical value: 561.69; Measured value: 562.67.

[0214] Example 19:

[0215] This invention provides a method for preparing compound N-342, comprising the following steps:

[0216]

[0217] Synthesis of intermediate N-342-1: The synthesis steps of intermediate N-342-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-11 and raw material A-1 is replaced with raw material A-7, thus obtaining intermediate N-342-1 (yield 80%).

[0218] Synthesis of intermediate N-342-2: The synthesis steps of intermediate N-342-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-342-1, thus obtaining intermediate N-342-2 (yield 83%).

[0219] Synthesis of compound N-342: The synthesis steps of compound N-342 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-342-2, and starting material B-2 is replaced with starting material B-3, thus obtaining compound N-342 (yield 65%).

[0220] Elemental analysis: C 47 H 29 N₃O. Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.64; H, 4.48; N, 6.43; HRMS(ESI) m / z [M+H] + Theoretical value: 611.75; Measured value: 612.73.

[0221] Example 20:

[0222] This invention provides a method for preparing compound N-383, comprising the following steps:

[0223]

[0224] Synthesis of intermediate N-383-1: The synthesis steps of intermediate N-383-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-12 and raw material A-1 is replaced with raw material A-8, thus obtaining intermediate N-383-1 (yield 82%).

[0225] Synthesis of intermediate N-383-2: The synthesis steps of intermediate N-383-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-383-1, thus obtaining intermediate N-383-2 (yield 80%).

[0226] Synthesis of compound N-383: The synthesis steps of compound N-383 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-383-2, and starting material B-2 is replaced with starting material B-4, thus obtaining compound N-383 (yield 63%).

[0227] Elemental analysis: C 47 H 31 N3. Theoretical values: C, 88.51; H, 4.90; N, 6.59; Measured values: C, 88.52; H, 4.90; N, 6.58; HRMS(ESI) m / z [M+H] + Theoretical value: 637.79; Measured value: 638.72.

[0228] Example 21:

[0229] This invention provides a method for preparing compound N-439, comprising the following steps:

[0230]

[0231] Synthesis of intermediate N-439-1: The synthesis steps of intermediate N-439-1 are the same as those of intermediate N-4-1, except that raw material S-1 is replaced with raw material S-13, thus obtaining intermediate N-439-1 (yield 81%).

[0232] Synthesis of intermediate N-439-2: The synthesis steps of intermediate N-439-2 are the same as those of intermediate N-4-2, except that intermediate N-4-1 is replaced with intermediate N-439-1, thus obtaining intermediate N-439-2 (yield 84%).

[0233] Synthesis of compound N-439: The synthesis steps of compound N-439 are the same as those of compound N-4, except that intermediate N-4-2 is replaced with intermediate N-439-2, and starting material B-2 is replaced with starting material B-1, thus obtaining compound N-439 (yield 65%).

[0234] Elemental analysis: C 41 H 21 D6N3. Theoretical values: C, 86.74; H, 5.86; N, 7.40; Measured values: C, 86.77; H, 5.84; N, 7.39; HRMS(ESI) m / z [M+H] + Theoretical value: 567.72; Measured value: 568.76.

[0235] Device Examples:

[0236] The present invention provides an OLED device composed of different organic electroluminescent materials, the specific structural distribution of which is shown in Figure 1. The OLED device has the following layer structure: substrate 1 (a glass substrate coated with indium tin oxide (ITO) as anode 2) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light emission layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer (EIL) 7 / cathode 8.

[0237] The materials used in the OLED device are as follows:

[0238]

[0239] The fabrication of devices in Examples 1-25 and Comparative Examples 1-10 includes the following steps:

[0240] (1) Substrate cleaning:

[0241] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0242] (2) Evaporation of organic light-emitting functional layer:

[0243] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4Pa, a mixture of HATCN and HT is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of HATCN to HT is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0244] A hole transport layer (material HT) is deposited on the hole injection layer, with a film thickness of 80 nm.

[0245] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: the light-emitting host material (the materials are shown in Table 1) and the guest material (piq)2Ir(acac) are vacuum deposited by co-evaporation, and the total film thickness is 35nm.

[0246] An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: ET and LiQ (or the compound and LiQ provided by this invention) are vacuum deposited by co-evaporation. The specific materials are detailed in Table 1. The total film thickness is 30 nm.

[0247] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0248] Al was deposited on the electron injection layer, with a total film thickness of 90 nm.

[0249] Table 1 below shows the parameters of each layer, its material, and thickness in the device embodiments and comparative examples:

[0250] Table 1

[0251]

[0252]

[0253]

[0254]

[0255] The organic electroluminescent devices obtained in the above-mentioned device examples 1-25 and device comparative examples 1-10 were tested.

[0256] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0257] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0258] Lifetime test: Current density 50mA / cm2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0259] The device performance test results are shown in Table 2:

[0260] Table 2

[0261]

[0262]

[0263] The combination of a naphthyl group and a triazine group can endow the molecule with strong electron transport capabilities. However, since the two naphthalene groups are connected only by a single bond, the molecule's rigidity is poor, directly resulting in a low charge transfer rate (Tg) and consequently, poor material stability. Furthermore, for molecules with high degrees of freedom, the poor orderliness during vapor deposition leads to uneven charge transport. Therefore, it is necessary to introduce substituent groups onto the naphthyl group to improve molecular rigidity, help improve molecular packing, thereby increasing charge mobility, improving device current efficiency, and extending device lifespan.

[0264] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound, characterized in that, It has the structure shown in equation (1): In the formula, Ar is selected from substituted or unsubstituted C6-C60 aryl groups; 1 Ar 2 Each of the following is independently selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C6-C60 aryloxy; n1 and n2 are each independently selected from any integer from 0 to 6; wherein the substituents of the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, and substituted C6-C60 aryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

2. The organic compound according to claim 1, characterized in that, The organic compound has the structure shown in any of Formulas 1-1 to 1-14, wherein Ar, Ar 1 Ar 2 The definitions of n1 and n2 are the same as in claim 1:

3. The organic compound according to claim 1 or 2, characterized in that, Ar is selected from substituted or unsubstituted C6-C30 aryl groups; Ar 1 Ar 2 Each of the substituents is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryloxy groups; wherein the substituents in the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, and substituted C6-C30 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

4. The organic compound according to any one of claims 1-3, characterized in that, Ar is selected from substituted or unsubstituted A groups, wherein the A group is selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluoranyl, triphenylene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl; Ar 1 Ar 2 Each of the B groups is independently selected from substituted or unsubstituted groups, wherein the B group is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranyl, triphenylene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazole, phenylcarbazole The group comprises benzo[a]carbazole, benzo[a]phenylcarbazole, dibenzo[a]carbazole, biphenylcarbazole, phenanthrenebenzofuran, benzofuran-benzofuran, and phenylcarbazole-benzofuran; wherein the substituents in the substituted A group and the substituted B group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

5. The organic compound according to any one of claims 1-4, characterized in that, Ar is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups; Ar 1 Ar 2 Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted phenanthryl; wherein the substituents of the substituted phenyl, substituted naphthyl, substituted biphenyl, substituted dibenzofuranyl, and substituted phenanthryl are selected from one or at least two of the following groups: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromaticamine, and C3-C60 heteroarylamine. Preferably, the substituents of the substituted phenyl, substituted naphthyl, substituted biphenyl, substituted dibenzofuranyl, and substituted phenanthrene are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

6. The organic compound according to any one of claims 1-5, characterized in that, The compound is selected from any one of the structures from N-1 to N-445:

7. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises an organic compound as described in any one of claims 1-6.

8. The organic electroluminescent material according to claim 7, characterized in that, The organic electroluminescent material also includes an organic compound as shown in formula (2). In equation (2), Ar 3 Ar 4 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; the substituents in the substituted C6-C30 aryl groups and substituted C3-C30 heteroaryl groups are each independently selected from deuterium, unsubstituted or C1-C6 alkyl or C6-C30 aryl groups substituted with C6-C30 aryl groups; unsubstituted or C1-C6 alkyl or C6-C30 aryl groups substituted with C3-C30 heteroaryl groups and C1-C6 alkyl groups; preferably, Ar 3 Ar 4 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl; preferably, Ar 3 Selected from dibenzofuranyl, phenyldibenzofuranyl, dibenzothiophenyl, phenyldibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl; Ar 4 Selected from phenyl, biphenyl, terphenyl, phenanthrene, naphthyl, phenylnaphthyl, and naphthylphenyl.

9. The organic electroluminescent material according to claim 8, characterized in that, The organic compound shown in formula (2) is selected from any compound from P-1 to P-15:

10. The organic electroluminescent material according to claim 8 or 9, characterized in that, In the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 1:9-9:1; preferably, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 2:8-8:2; more preferably, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 3:7-7:3; even more preferably, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 4:6-6:

4.

11. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an organic compound as described in any one of claims 1-6 or an organic electroluminescent material as described in any one of claims 7-10.

12. The organic electroluminescent device according to claim 11, characterized in that, The organic layer comprises any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer; preferably, the organic layer comprises a light-emitting layer, which comprises an organic compound as described in any one of claims 1-6; preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic compound as described in any one of claims 1-6 or an organic electroluminescent material as described in any one of claims 7-10.

13. An electronic device, characterized in that, The electronic device includes an organic electroluminescent device as described in claim 11 or 12, an organic compound as described in any one of claims 1-6, or an organic electroluminescent material as described in any one of claims 7-10.

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