Organic compound and use thereof

Abstract

The present application relates to the technical field of displays, and specifically relates to an organic compound and the use thereof. The organic compound provided by the present application has a structure as represented by formula (I) below. An organic electroluminescent device containing the organic compound can be endowed with a relatively low driving voltage, relatively high luminous efficiency and relatively long service life.

Description

An organic compound and its application

[0001] Cross-reference to related applications

[0002] This application claims priority to Chinese Patent Application No. 202510350017.8, filed on March 24, 2025, entitled “An Organic Compound and Its Application”, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This application relates to the field of display technology, specifically to an organic compound and its applications. Background Technology

[0004] Organic light-emitting diodes (OLEDs) are devices that convert electrical energy into light by applying electricity to organic light-emitting materials. They generally have a structure comprising an anode, a cathode, and an organic layer between the anode and cathode. The organic layer of an organic OLED can consist of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host material and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The materials used in the organic layer are classified according to their function as hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. In these organic OLEDs, due to the application of voltage, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The recombination of holes and electrons forms high-energy excitons. With this energy, the organic light-emitting compound reaches an excited state, and light is emitted by the energy generated when the excited state of the organic light-emitting compound returns to its ground state.

[0005] The most important factor determining the luminescence efficiency of organic EL devices is the luminescent material. The luminescent material must possess high quantum efficiency and high electron and hole mobility, and the resulting luminescent material layer must be uniform and stable. Luminescent materials are classified according to the color of their emission into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials. Furthermore, luminescent materials can also be classified according to their function into host materials and dopant materials.

[0006] However, existing organic electroluminescent materials have poor hole transport capabilities, which leads to problems such as high driving voltage, low luminous efficiency, and short lifespan in organic electroluminescent devices containing these materials, severely limiting their application. Summary of the Invention

[0007] The purpose of this application is to overcome the problem that the poor hole transport capability of existing organic electroluminescent materials results in high driving voltage, low luminous efficiency, and short lifespan of organic electroluminescent devices containing such materials, and to provide an organic compound and its application.

[0008] The substituent terminology is defined in this application as follows:

[0009] 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.

[0010] 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 may be 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 may be a combination of at least two compounds, said materials may contain at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary 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 may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0011] In this application, the descriptive terms “each…independently selected”, “…independently constitute”, and “…independently constitute” are interchangeable and should be interpreted broadly. They can mean that the specific options expressed by the same symbols in different groups do not affect each other, or that the specific options expressed by the same symbols in the same group do not affect each other.

[0012] 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.

[0013] 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 two adjacent substituents Rc can exist independently or fused with the functional group to which they are attached to form a ring.

[0014] 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, optionally 1 to 40 carbon atoms, and alternatively 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.

[0015] 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.

[0016] 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 in this application, the term "substituted" means that a hydrogen atom in a 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.

[0017] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0018] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0019] In this application, the definition of a group specifies a 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, 30, 35, 40, 45, 50, 55 or 60, etc.

[0020] Unless otherwise specified in this application, the substituents do not fuse with the group to which they belong.

[0021] In this application, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0022] The solution adopted in this application is as follows:

[0023] In a first aspect, this application provides an organic compound having the structure shown in formula (1):

[0024] In equation (1), Y1 and Y2 are each independently selected from O or S;

[0025] Ring A may or may not exist, and if ring A is present, it is selected from the benzene ring;

[0026] Ar 1 Ar 2 They may be the same or different, and each is independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl;

[0027] L 1 L 2 Whether the same or different, each is independently selected from single-bonded, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;

[0028] R1 and R2 are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0029] n1 is selected from any integer from 1 to 9. When n1 equals 1, R1 is a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C3-C60 heteroaryl. When n1 is greater than 1, R1 is the same or different, and at least one of R1 is a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C3-C60 heteroaryl.

[0030] n2 is selected from any integer between 0 and 3. When n2 is greater than 1, R2 is the same or different.

[0031] The substituents of the substituted C6-C60 arylene, substituted C3-C60 heteroarylene, substituted C6-C60 aryl, and substituted C3-C60 heteroarylene 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 heteroarylene, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0032] Understandably, when ring A is present, ring A is fused and connected to the benzene ring in which it resides;

[0033] Optionally, when n1 is 1, R1 is a substituted or unsubstituted phenyl group; when n1 is greater than 1, at least one of R1 is a substituted or unsubstituted phenyl group.

[0034] The substituents in the substituted phenyl 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 heteroaryl.

[0035] Optionally, the organic compound of formula (1) is selected from any one of the structures of formulas 1-1 to 1-12, wherein Y1, Y2, and Ar 1 Ar 2 L 1 L 2 The definitions of R1, R2, n1, and n2 are the same as those described above:

[0036] Optionally, the organic compound of formula (1) is selected from any one of the structures of formula A-1 to A-84, wherein Y1, Y2, and Ar 1 Ar 2 L 1 L 2 The definitions of R1, R2, n1, and n2 are the same as those described above:

[0037] Optionally, when ring A is absent, Ar1 is selected from substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 heteroaryl with O as a heteroatom, or substituted or unsubstituted C3-C24 heteroaryl with S as a heteroatom.

[0038] The substituents of the substituted C6-C24 aryl, the substituted O-as heteroatom C3-C24 heteroaryl, and the substituted S-as heteroatom C3-C24 heteroaryl 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 amino.

[0039] Optionally, L1 is not a single bond when ring A does not exist.

[0040] Optionally, in equation (1) or equations 1-1 to 1-16, Ar 1Ar 2 They may be the same or different, and each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0041] Optional, L 1 L 2 Whether the groups are the same or different, they are each independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;

[0042] Optionally, R1 and R2 may be the same or different, and each may be independently selected from deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0043] The substituents of the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C30 aryl, and substituted C3-C30 heteroarylene 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 heteroarylene, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0044] Optionally, in equation (1) or equations 1-1 to 1-16, Ar 1 Ar 2 Whether identical or different, each is independently selected from substituted or unsubstituted A groups, wherein the A group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzospirodifluorenyl, benzo[] Furanyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, N-phenylcarbazoyl, benzocarbazoyl, N-phenylbenzocarbazoyl, dibenzocarbazoyl, biphenylcarbazoyl, benzooxazolyl, naphthooxazolyl, phenanthreneoxazolyl, phenanthrenebenzofuranyl, benzofuranobenzofuranyl, N-phenylbenzofuranocarbazoyl;

[0045] Wherein, the substituents in the substituted A 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 heteroaryl.

[0046] Alternatively, the substituent of the substituted A group is 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, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazoyl, and benzocarbazoyl.

[0047] Optional, L 1 L 2 Whether the groups are the same or different, each group is independently selected from single-bonded, substituted or unsubstituted B groups, wherein the B groups are selected from: phenylene, naphthylene, phenanthrene, binatrimethylene, dibenzofuranyl, dibenzothiophene, benzonaphthiophene, and benzonaphthiophene.

[0048] Wherein, the substituents in 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 heteroaryl.

[0049] Alternatively, the substituent of the substituted B group is 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, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazoyl, and benzocarbazoyl.

[0050] Optionally, R1 and R2 may be the same or different, each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C groups; wherein the C group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, Benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, N-phenylcarbazoyl, benzocarbazoyl, N-phenylbenzocarbazoyl, dibenzocarbazoyl, biphenylcarbazoyl, benzooxazolyl, naphthooxazolyl, phenanthreneoxazolyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, N-phenylbenzofuran-carbazoyl;

[0051] Wherein, the substituents in the substituted C 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 heteroaryl.

[0052] Alternatively, the substituent in the substituted C group is 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, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

[0053] Optionally, the organic compounds described in formula (1) or formulas 1-1 to 1-16 are selected from any of the following structures:

[0054] Secondly, this application provides a method for preparing the aforementioned organic compound, as follows:

[0055] Compound Nn can be obtained via the following synthetic route:

[0056] Synthesis Route 1:

[0057] Synthesis Route 2:

[0058] Synthesis Route 3:

[0059] Synthesis Route 4:

[0060] Synthesis Route 5:

[0061] Synthesis Route 6:

[0062] Synthesis Route 7:

[0063] Synthesis Route 8:

[0064] Synthesis Route 9:

[0065] Synthesis Route 10:

[0066] Synthesis Route 11:

[0067] Synthesis Route 12:

[0068] Synthesis Route 13:

[0069] Of X1 and X2, one is a borate group and the other is an iodine group.

[0070] The raw materials ax, bx, cx, dx, ex, and fx can all be purchased directly or synthesized by referring to existing literature reports through conventional reaction routes and conditions.

[0071] Thirdly, this application also provides an organic electroluminescent material comprising the organic compounds described above.

[0072] Fourthly, this application also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising the organic compound or the organic electroluminescent material described above.

[0073] Optionally, the organic layer located between the cathode and the anode includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0074] Optionally, the organic layer includes a hole injection layer to enhance the ability to inject holes into the hole transport layer. The hole injection layer may be selected from benzidine derivatives, arylamine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer includes, but is not limited to, the following compounds:

[0075] Optionally, the organic layer includes a hole transport layer, which may include one or more hole transport materials. The hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any special limitations on this. The material of the hole injection layer includes, but is not limited to, the following compounds:

[0076] Optionally, the organic layer includes a light-emitting auxiliary layer, which can be a single-layer or multi-layer structure.

[0077] Optionally, the organic layer includes a light-emitting layer comprising an organic compound as shown in formula (1).

[0078] Optionally, the organic layer includes a light-emitting layer, which includes a host material and a guest material. The host material includes multiple host materials or a single host material. The composition of the multiple host materials or the single host material includes, but is not limited to, aromatic amine compounds and their derivatives, triazine compounds and their derivatives, carbazole compounds and their derivatives, and organic compounds as shown in formula (1). This application does not impose any special restrictions on this. The host material is also called the matrix material.

[0079] The guest material can be a compound having a condensed aryl ring or its derivative, a compound having a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials, and this application does not impose any special limitations on this; the guest material is also referred to as a dopant or dopant. The guest material includes, but is not limited to, the following structures:

[0080] Optionally, the organic layer includes a hole-blocking layer, which can be a single-layer or multi-layer structure.

[0081] Optionally, the organic layer includes an electron transport layer, which can be a single-layer structure or a multi-layer structure. It may include one or more electron transport materials, selected from, but not limited to, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any special limitations on this. The materials of the electron transport layer include, but are not limited to, the following structures:

[0082] Optionally, an electron injection layer is provided between the cathode and the electron transport layer to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metal halides, or it may include complexes of alkali metals and organic materials.

[0083] Fifthly, this application also provides an electronic device comprising an organic electroluminescent device as described above, an organic electroluminescent material as described above, or an organic compound as shown in formula (1).

[0084] The electronic devices include, but are not limited to, mobile phones, wearable watches, fiber optic devices, lighting devices, electrophotographic photosensitive devices, photoelectric converters, organic solar cells, switching element devices, organic light-emitting field-effect transistors, image sensors, or dye lasers.

[0085] The beneficial effects of this application are:

[0086] The organic compound provided in this application, based on the structure of formula (1), introduces specific substituents on the structural fragments of dibenzofuran, dibenzothiophene, benzonaphthofuran, and benzonaphthothiophene, which can make the overall configuration of the molecule more three-dimensional, thereby effectively increasing the dipole moment of the molecule, thereby enhancing the hole transport capability of the overall molecular structure, and thus enabling the organic electroluminescent device containing the organic compound to have a lower driving voltage, higher luminous efficiency, and longer lifetime. Attached Figure Description

[0087] To more clearly illustrate the technical solutions in the specific embodiments of this application or 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 this application. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0088] Figure 1 is a structural diagram of the organic electroluminescent device in the device embodiment of this application; 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-light emitting layer; 6-electron transport layer; 7-electron injection layer; 8-cathode. Detailed Implementation

[0089] 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.

[0090] 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.

[0091] In the embodiments of this application, the raw material ax includes the following structure:

[0092] In the embodiments of this application, the raw material bx includes the following structure:

[0093] In the embodiments of this application, the raw material cx includes the following structure:

[0094] In the embodiments of this application, the raw material dx includes the following structure:

[0095] In the embodiments of this application, the raw material ex includes the following structure:

[0096] In the embodiments of this application, the raw material fx includes the following structure:

[0097] The synthesis of raw material e-10 can be referenced from the following method:

[0098] Preparation of intermediate sub-e-10-3: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, the following raw materials were added sequentially: sub-e-10-1 (1.0 mmol), sub-e-10-2 (1.1 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, dried over anhydrous magnesium sulfate, and 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 sub-e-10-3 (yield 82%).

[0099] Preparation of compound e-10: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate sub-e-10-3 (1.0 mmol), starting material sub-e-10-4 (1.1 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 e-10 (yield 78%).

[0100] 1. Synthesis of intermediate sub-n-4:

[0101] 1.1 Synthesis of intermediate sub-38-4:

[0102] Synthesis of intermediate sub-38-1: A 500 mL three-necked round-bottom flask was fitted with a stir bar and a reflux tube. Under nitrogen protection, starting material a-1 (275.5 mmol), starting material b-1 (574.7 mmol), Pd(PPh)₂Cl₂ (6 mmol), K₂CO₃ (596.4 mmol), toluene (700 mL), ethanol (100 mL), and water (100 mL) were added sequentially. The mixture was heated under nitrogen protection until the internal temperature reached 90 ± 2 °C, and the reaction was carried out for 24 h. After the reaction was completed, the mixture was extracted with ethyl acetate and water. The resulting organic layer was dried over magnesium sulfate (MgSO₄) and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallized to give intermediate sub-38-1 in 34% yield.

[0103] Synthesis of intermediate sub-38-2: A 500 mL three-necked round-bottom flask was fitted with a stir bar and a reflux tube. Under nitrogen protection, intermediate sub-38-1 (54.7 mmol), phenylboronic acid (60.2 mmol), Pd(PPh3)4 (1.1 mmol), Na2CO3 (109.4 mmol), dioxane (200 mL), and water (100 mL) were added sequentially. The mixture was heated under nitrogen protection until the internal temperature reached 90 ± 2 °C, and the reaction was carried out for 24 h. After the reaction was completed, the mixture was extracted with ethyl acetate and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. Subsequently, the compound was subjected to silica gel column chromatography and recrystallized to obtain intermediate sub-38-2 in 68% yield.

[0104] Synthesis of intermediate sub-38-3: A 500 mL three-necked round-bottom flask was fitted with a stir bar and a reflux flask. Under nitrogen protection, intermediate sub-38-2 (46.9 mmol) and dichloromethane (100 mL) were added sequentially. The mixture was stirred at low temperature (-10 °C) for 20 min, and then 71.2 mmol of BBr3 was slowly added dropwise while maintaining the internal temperature at -10 to 0 °C. After the addition was complete, the mixture was stirred continuously for 30 min. After the reaction was complete, the reaction solution was poured into ice water and extracted with dichloromethane and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The resulting compound was then crystallized with n-hexane to obtain intermediate sub-38-3 in 92% yield.

[0105] Synthesis of intermediate sub-38-4: A 500 mL three-necked round-bottom flask was fitted with a stir bar and a reflux duct. Under nitrogen protection, intermediate sub-38-3 (33.0 mmol), K₂CO₃ (65.9 mmol), and NMP (100 mL) were added sequentially. The mixture was heated to 140 °C and reacted for 6 h. After the reaction was complete, the mixture was quenched with water, sodium chloride was added, and the mixture was extracted with ethyl acetate and water. The resulting organic layer was dried over magnesium sulfate (MgSO₄) and concentrated to obtain intermediate sub-38-4, yield: 87%.

[0106] 1.2 Synthesis of intermediate sub-8-4:

[0107] Synthesis of intermediate sub-8-1: The synthesis steps of intermediate sub-8-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-2 to obtain intermediate sub-8-1 (yield 33%).

[0108] Synthesis of intermediate sub-8-2: The synthesis steps of intermediate sub-8-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-8-1, thus obtaining intermediate sub-8-2 (yield 65%).

[0109] Synthesis of intermediate sub-8-3: The synthesis steps of intermediate sub-8-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-8-2, thus obtaining intermediate sub-8-3 (yield 91%).

[0110] Synthesis of intermediate sub-8-4: The synthesis steps of intermediate sub-8-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-8-3, thus obtaining intermediate sub-8-4 (yield 83%).

[0111] 1.3 Synthesis of intermediate sub-12-4:

[0112] Synthesis of intermediate sub-12-1: The synthesis steps of intermediate sub-12-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-3 and raw material b-1 is replaced with raw material b-3, thus obtaining intermediate sub-12-1 (yield 34%).

[0113] Synthesis of intermediate sub-12-2: The synthesis steps of intermediate sub-12-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-12-1, thus obtaining intermediate sub-12-2 (yield 67%).

[0114] Synthesis of intermediate sub-12-3: The synthesis steps of intermediate sub-12-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-12-2, thus obtaining intermediate sub-12-3 (yield 92%).

[0115] Synthesis of intermediate sub-12-4: The synthesis steps of intermediate sub-12-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-12-3, thus obtaining intermediate sub-12-4 (yield 86%).

[0116] 1.4 Synthesis of intermediate sub-82-4:

[0117] Synthesis of intermediate sub-82-1: The synthesis steps of intermediate sub-82-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-4 and raw material b-1 is replaced with raw material b-7, thus obtaining intermediate sub-82-1 (yield 36%).

[0118] Synthesis of intermediate sub-82-2: The synthesis steps of intermediate sub-82-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-82-1, thus obtaining intermediate sub-82-2 (yield 64%).

[0119] Synthesis of intermediate sub-82-3: The synthesis steps of intermediate sub-82-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-82-2, thus obtaining intermediate sub-82-3 (yield 90%).

[0120] Synthesis of intermediate sub-82-4: The synthesis steps of intermediate sub-82-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-82-3, thus obtaining intermediate sub-82-4 (yield 85%).

[0121] Synthesis of intermediate sub-96-4 (1.5):

[0122] Synthesis of intermediate sub-96-1: The synthesis steps of intermediate sub-96-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-8 and raw material b-1 is replaced with raw material b-7, thus obtaining intermediate sub-96-1 (yield 37%).

[0123] Synthesis of intermediate sub-96-2: The synthesis steps of intermediate sub-96-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-96-1, thus obtaining intermediate sub-96-2 (yield 63%).

[0124] Synthesis of intermediate sub-96-3: The synthesis steps of intermediate sub-96-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-96-2, thus obtaining intermediate sub-96-3 (yield 91%).

[0125] Synthesis of intermediate sub-96-4: The synthesis steps of intermediate sub-96-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-96-3, thus obtaining intermediate sub-96-4 (yield 85%).

[0126] 1.6 Synthesis of intermediate sub-136-4:

[0127] Synthesis of intermediate sub-136-1: The synthesis steps of intermediate sub-136-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-4 and raw material b-1 is replaced with raw material b-4, thus obtaining intermediate sub-136-1 (yield 36%).

[0128] Synthesis of intermediate sub-136-2: The synthesis steps of intermediate sub-136-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-136-1, thus obtaining intermediate sub-136-2 (yield 67%).

[0129] Synthesis of intermediate sub-136-3: The synthesis steps of intermediate sub-136-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-136-2, thus obtaining intermediate sub-136-3 (yield 90%).

[0130] Synthesis of intermediate sub-136-4: The synthesis steps of intermediate sub-136-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-136-3, thus obtaining intermediate sub-136-4 (yield 83%).

[0131] 1.7 Synthesis of intermediate sub-247-4:

[0132] Synthesis of intermediate sub-247-1: The synthesis steps of intermediate sub-247-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-5 and raw material b-1 is replaced with raw material b-5, thus obtaining intermediate sub-247-1 (yield 34%).

[0133] Synthesis of intermediate sub-247-2: The synthesis steps of intermediate sub-247-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-247-1, thus obtaining intermediate sub-247-2 (yield 65%).

[0134] Synthesis of intermediate sub-247-3: The synthesis steps of intermediate sub-247-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-247-2, thus obtaining intermediate sub-247-3 (yield 91%).

[0135] Synthesis of intermediate sub-247-4: The synthesis steps of intermediate sub-247-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-247-3, thus obtaining intermediate sub-247-4 (yield 81%).

[0136] 1.8 Synthesis of intermediate sub-271-4:

[0137] Synthesis of intermediate sub-271-1: The synthesis steps of intermediate sub-271-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-6 and raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-271-1 (yield 31%).

[0138] Synthesis of intermediate sub-271-2: The synthesis steps of intermediate sub-271-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-271-1, thus obtaining intermediate sub-271-2 (yield 66%).

[0139] Synthesis of intermediate sub-271-3: The synthesis steps of intermediate sub-271-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-271-2, thus obtaining intermediate sub-271-3 (yield 90%).

[0140] Synthesis of intermediate sub-271-4: The synthesis steps of intermediate sub-271-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-271-3, thus obtaining intermediate sub-271-4 (yield 82%).

[0141] 1.9 Synthesis of intermediate sub-299-4:

[0142] Synthesis of intermediate sub-299-1: The synthesis steps of intermediate sub-299-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-7 and raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-299-1 (yield 33%).

[0143] Synthesis of intermediate sub-299-2: The synthesis steps of intermediate sub-299-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-299-1, thus obtaining intermediate sub-299-2 (yield 66%).

[0144] Synthesis of intermediate sub-299-3: The synthesis steps of intermediate sub-299-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-299-2, thus obtaining intermediate sub-299-3 (yield 91%).

[0145] Synthesis of intermediate sub-299-4: The synthesis steps of intermediate sub-299-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-299-3, thus obtaining intermediate sub-299-4 (yield 84%).

[0146] Synthesis of intermediate sub-31-4 (1.10):

[0147] Synthesis of intermediate sub-31-1: The synthesis steps of intermediate sub-31-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-9 and raw material b-1 is replaced with raw material b-2, thus obtaining intermediate sub-31-1 (yield 33%).

[0148] Synthesis of intermediate sub-31-2: The synthesis steps of intermediate sub-31-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-31-1, thus obtaining intermediate sub-31-2 (yield 63%).

[0149] Synthesis of intermediate sub-31-3: The synthesis steps of intermediate sub-31-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-31-2, thus obtaining intermediate sub-31-3 (yield 92%).

[0150] Synthesis of intermediate sub-31-4: The synthesis steps of intermediate sub-31-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-31-3, thus obtaining intermediate sub-31-4 (yield 85%).

[0151] 1.11 Synthesis of intermediate sub-41-4:

[0152] Synthesis of intermediate sub-41-1: The synthesis steps of intermediate sub-41-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-3 and raw material b-1 is replaced with raw material b-8, thus obtaining intermediate sub-41-1 (yield 37%).

[0153] Synthesis of intermediate sub-41-2: The synthesis steps of intermediate sub-41-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-41-1, thus obtaining intermediate sub-41-2 (yield 64%).

[0154] Synthesis of intermediate sub-41-3: The synthesis steps of intermediate sub-41-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-41-2, thus obtaining intermediate sub-41-3 (yield 91%).

[0155] Synthesis of intermediate sub-41-4: The synthesis steps of intermediate sub-41-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-41-3, thus obtaining intermediate sub-41-4 (yield 84%).

[0156] 1.12 Synthesis of intermediate sub-59-4:

[0157] Synthesis of intermediate sub-59-1: The synthesis steps of intermediate sub-59-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-3 and raw material b-1 is replaced with raw material b-9, thus obtaining intermediate sub-59-1 (yield 37%).

[0158] Synthesis of intermediate sub-59-2: The synthesis steps of intermediate sub-59-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-59-1, thus obtaining intermediate sub-59-2 (yield 64%).

[0159] Synthesis of intermediate sub-59-3: The synthesis steps of intermediate sub-59-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-59-2, thus obtaining intermediate sub-59-3 (yield 91%).

[0160] Synthesis of intermediate sub-59-4: The synthesis steps of intermediate sub-59-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-59-3, thus obtaining intermediate sub-59-4 (yield 84%).

[0161] Synthesis of intermediate sub-75-4 (1.13):

[0162] Synthesis of intermediate sub-75-1: The synthesis steps of intermediate sub-75-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-10 and raw material b-1 is replaced with raw material b-2, thus obtaining intermediate sub-75-1 (yield 34%).

[0163] Synthesis of intermediate sub-75-2: The synthesis steps of intermediate sub-75-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-75-1, thus obtaining intermediate sub-75-2 (yield 65%).

[0164] Synthesis of intermediate sub-75-3: The synthesis steps of intermediate sub-75-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-75-2, thus obtaining intermediate sub-75-3 (yield 90%).

[0165] Synthesis of intermediate sub-75-4: The synthesis steps of intermediate sub-75-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-75-3, thus obtaining intermediate sub-75-4 (yield 83%).

[0166] 1.14 Synthesis of intermediate sub-78-4:

[0167] Synthesis of intermediate sub-78-1: The synthesis steps of intermediate sub-78-1 are the same as those of intermediate sub-38-1, except that raw material a-1 is replaced with raw material a-11 and raw material b-1 is replaced with raw material b-7, thus obtaining intermediate sub-78-1 (yield 35%).

[0168] Synthesis of intermediate sub-78-2: The synthesis steps of intermediate sub-78-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-78-1, thus obtaining intermediate sub-78-2 (yield 64%).

[0169] Synthesis of intermediate sub-78-3: The synthesis steps of intermediate sub-78-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-78-2, thus obtaining intermediate sub-78-3 (yield 91%).

[0170] Synthesis of intermediate sub-78-4: The synthesis steps of intermediate sub-78-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-78-3, thus obtaining intermediate sub-78-4 (yield 84%).

[0171] Synthesis of intermediate sub-513-4 (1.15):

[0172] Synthesis of intermediate sub-513-2: The synthesis steps of intermediate sub-513-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-247-1, and raw material c-1 is replaced with raw material c-2, thus obtaining intermediate sub-513-2 (yield 61%).

[0173] Synthesis of intermediate sub-513-3: The synthesis steps of intermediate sub-513-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-513-2, thus obtaining intermediate sub-513-3 (yield 90%).

[0174] Synthesis of intermediate sub-513-4: The synthesis steps of intermediate sub-513-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-513-3, thus obtaining intermediate sub-513-4 (yield 84%).

[0175] Synthesis of intermediate sub-520-4 (1.16):

[0176] Synthesis of intermediate sub-520-2: The synthesis steps of intermediate sub-520-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-96-1, and raw material c-1 is replaced with raw material c-3, thus obtaining intermediate sub-520-2 (yield 63%).

[0177] Synthesis of intermediate sub-520-3: The synthesis steps of intermediate sub-520-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-520-2, thus obtaining intermediate sub-520-3 (yield 90%).

[0178] Synthesis of intermediate sub-520-4: The synthesis steps of intermediate sub-520-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-520-3, thus obtaining intermediate sub-520-4 (yield 82%).

[0179] 1.17 Synthesis of intermediate sub-522-4:

[0180] Synthesis of intermediate sub-522-2: The synthesis steps of intermediate sub-522-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-299-1, and raw material c-1 is replaced with raw material c-4, thus obtaining intermediate sub-522-2 (yield 60%).

[0181] Synthesis of intermediate sub-522-3: The synthesis steps of intermediate sub-522-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-522-2, thus obtaining intermediate sub-522-3 (yield 91%).

[0182] Synthesis of intermediate sub-522-4: The synthesis steps of intermediate sub-522-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-522-3, thus obtaining intermediate sub-522-4 (yield 83%).

[0183] Synthesis of intermediate sub-532-4 (1.18):

[0184] Synthesis of intermediate sub-532-2: The synthesis steps of intermediate sub-532-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-8-1, and raw material c-1 is replaced with raw material c-5, thus obtaining intermediate sub-532-2 (yield 60%).

[0185] Synthesis of intermediate sub-532-3: The synthesis steps of intermediate sub-532-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-532-2, thus obtaining intermediate sub-532-3 (yield 90%).

[0186] Synthesis of intermediate sub-532-4: The synthesis steps of intermediate sub-532-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-532-3, thus obtaining intermediate sub-532-4 (yield 84%).

[0187] Synthesis of intermediate sub-536-4 (1.19):

[0188] Synthesis of intermediate sub-536-2: The synthesis steps of intermediate sub-536-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-271-1, and raw material c-1 is replaced with raw material c-6, thus obtaining intermediate sub-536-2 (yield 62%).

[0189] Synthesis of intermediate sub-536-3: The synthesis steps of intermediate sub-536-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-536-2, thus obtaining intermediate sub-536-3 (yield 91%).

[0190] Synthesis of intermediate sub-536-4: The synthesis steps of intermediate sub-536-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-536-3, thus obtaining intermediate sub-536-4 (yield 83%).

[0191] Synthesis of intermediate sub-552-4 (1.20):

[0192] Synthesis of intermediate sub-552-2: The synthesis steps of intermediate sub-552-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-82-1, and raw material c-1 is replaced with raw material c-7, thus obtaining intermediate sub-552-2 (yield 64%).

[0193] Synthesis of intermediate sub-552-3: The synthesis steps of intermediate sub-552-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-552-2, thus obtaining intermediate sub-552-3 (yield 89%).

[0194] Synthesis of intermediate sub-552-4: The synthesis steps of intermediate sub-552-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-552-3, thus obtaining intermediate sub-552-4 (yield 82%).

[0195] 1.21 Synthesis of intermediate sub-561-4:

[0196] Synthesis of intermediate sub-561-2: The synthesis steps of intermediate sub-561-2 are the same as those of intermediate sub-38-2, except that intermediate sub-38-1 is replaced with intermediate sub-229-1, and raw material c-1 is replaced with raw material c-8, thus obtaining intermediate sub-561-2 (yield 63%).

[0197] Synthesis of intermediate sub-561-3: The synthesis steps of intermediate sub-561-3 are the same as those of intermediate sub-38-3, except that intermediate sub-38-2 is replaced with intermediate sub-561-2, thus obtaining intermediate sub-561-3 (yield 93%).

[0198] Synthesis of intermediate sub-561-4: The synthesis steps of intermediate sub-561-4 are the same as those of intermediate sub-38-4, except that intermediate sub-38-3 is replaced with intermediate sub-561-3, thus obtaining intermediate sub-561-4 (yield 81%).

[0199] 2. Examples of the synthesis of compound Nn:

[0200] 2.1 The synthesis of compound N-8 includes the following steps:

[0201] Synthesis of intermediate sub-8-5: A 500 mL three-necked round-bottom flask was fitted with a stir bar and a reflux duct. Under nitrogen protection, intermediate sub-8-4 (30.4 mmol), starting material d-1 (36.5 mmol), t-BuONa (60.8 mmol), S-Phos (1.2 mmol), Pd2(dba)3 (0.6 mmol), and toluene (100 mL) were added sequentially. The mixture was heated to 110 °C and stirred for 2 h. After the reaction was complete, the heating was turned off, and the mixture was cooled to 80 °C. The reaction was quenched with water, and the mixture was extracted with ethyl acetate and water. The organic phase was concentrated, and 100 mL of n-hexane was added to crystallize the phase. The crystals were dried to obtain intermediate sub-8-5 in 87% yield.

[0202] Synthesis of compound N-8: A 500 mL three-necked round-bottom flask was fitted with a stir bar and a reflux duct. Under nitrogen protection, intermediate sub-8-5 (25.9 mmol), starting material e-1 (25.9 mmol), Pd2(dba)3 (0.5 mmol), Sphos (1.0 mmol), t-BuONa (51.9 mmol), and xylene (100 mL) were added sequentially. The mixture was heated to 120 °C and stirred for 3 h. After the reaction was complete, the heating was turned off, and the mixture was cooled to 80 °C. The reaction was quenched with water, and the mixture was extracted with ethyl acetate and water. The organic phase was concentrated, and 100 mL of ethanol was added to crystallize the mixture. The crystals were dried to obtain compound N-8, yield: 78%.

[0203] Elemental analysis: C 41 H 26 N2O2; Theoretical values: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured values: C, 85.07; H, 4.50; N, 4.88; HRMS(ESI) m / z [M+H]+: Theoretical value: 578.20; Measured value: 579.21.

[0204] 2.2 The synthesis of compound N-12 includes the following steps:

[0205] Synthesis of intermediate sub-12-5: The synthesis steps of intermediate sub-12-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-12-4, thus obtaining sub-12-5 (yield 86%).

[0206] Synthesis of compound N-12: The synthesis steps of compound N-12 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-12-5, thus obtaining compound N-12 (yield 82%).

[0207] Elemental analysis: C41 H 26 Theoretical N2O2 values: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured values: C, 85.07; H, 4.50; N, 4.88; HRMS(ESI) m / z [M+H]+: Theoretical value: 578.20; Measured value: 579.21.

[0208] 2.3 The synthesis of compound N-31 includes the following steps:

[0209] Synthesis of intermediate sub-31-5: The synthesis steps of intermediate sub-31-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with the raw material sub-31-4, thus obtaining sub-31-5 (yield 82%).

[0210] Synthesis of compound N-31: The synthesis steps of compound N-31 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-31-5, and starting material e-1 is replaced with starting material e-8, thus obtaining compound N-31 (yield 82%).

[0211] Elemental analysis: C 41 H 26 Theoretical N2O2 values: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured values: C, 85.08; H, 4.51; N, 4.82; HRMS(ESI) m / z [M+H]+: Theoretical value: 578.67; Measured value: 579.94.

[0212] 2.4 The synthesis of compound N-38 includes the following steps:

[0213] Synthesis of intermediate sub-38-5: The synthesis steps of intermediate sub-38-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-38-4, thus obtaining sub-38-5 (yield 86%).

[0214] Synthesis of compound N-38: The synthesis steps of compound N-38 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-38-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-38 (yield 81%).

[0215] Elemental analysis: C 47 H 30Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.22; H, 4.62; N, 4.28; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.23.

[0216] 2.5 The synthesis of compound N-41 includes the following steps:

[0217] Synthesis of intermediate sub-41-5: The synthesis steps of intermediate sub-41-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-41-4, and raw material d-1 is replaced with raw material d-7, thus obtaining sub-41-5 (yield 83%).

[0218] Synthesis of compound N-41: The synthesis steps of compound N-41 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-41-5, and starting material e-1 is replaced with starting material e-7, thus obtaining compound N-41 (yield 83%).

[0219] Elemental analysis: C 51 H 32 Theoretical N2O2 values: C, 86.91; H, 4.58; N, 3.97; O, 4.54; Measured values: C, 86.93; H, 4.59; N, 3.94; HRMS(ESI) m / z [M+H]+: Theoretical value: 704.83; Measured value: 706.38.

[0220] 2.6 The synthesis of compound N-59 includes the following steps:

[0221] Synthesis of intermediate sub-59-5: The synthesis steps of intermediate sub-59-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with the raw material sub-59-4, thus obtaining sub-59-5 (yield 83%).

[0222] Synthesis of compound N-59: The synthesis steps of compound N-59 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-59-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-59 (yield 81%). Elemental analysis: C 47 H 30Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.21; H, 4.59; N, 4.32; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.77; Measured value: 656.01.

[0223] 2.7 The synthesis of compound N-75 includes the following steps:

[0224] Synthesis of intermediate sub-75-5: The synthesis steps of intermediate sub-75-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with the raw material sub-75-4, thus obtaining sub-75-5 (yield 82%).

[0225] Synthesis of compound N-75: The synthesis steps of compound N-75 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-75-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-75 (yield 80%).

[0226] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.23; H, 4.61; N, 4.30; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.77; Measured value: 655.92.

[0227] 2.8 The synthesis of compound N-78 includes the following steps:

[0228] Synthesis of intermediate sub-78-5: The synthesis steps of intermediate sub-78-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with the raw material sub-78-4, thus obtaining sub-78-5 (yield 83%).

[0229] Synthesis of compound N-78: The synthesis steps of compound N-78 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-78-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-78 (yield 81%).

[0230] Elemental analysis: C 47 H 30Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.23; H, 4.62; N, 4.29; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.77; Measured value: 656.07.

[0231] 2.9 The synthesis of compound N-82 includes the following steps:

[0232] Synthesis of intermediate sub-82-5: The synthesis steps of intermediate sub-82-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-82-4, thus obtaining sub-82-5 (yield 84%).

[0233] Synthesis of compound N-82: The synthesis steps of compound N-82 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-82-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-82 (yield 83%).

[0234] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.22; H, 4.62; N, 4.28; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.22.

[0235] 2.10 The synthesis of compound N-96 includes the following steps:

[0236] Synthesis of intermediate sub-96-5: The synthesis steps of intermediate sub-96-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-96-4, thus obtaining sub-96-5 (yield 84%).

[0237] Synthesis of compound N-96: The synthesis steps of compound N-96 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-96-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-96 (yield 84%).

[0238] Elemental analysis: C 47 H 30Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.20; H, 4.59; N, 4.32; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.21.

[0239] 2.11 The synthesis of compound N-106 includes the following steps:

[0240] Synthesis of compound N-106: The synthesis steps of compound N-106 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-38-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-106 (yield 83%).

[0241] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.20; H, 4.59; N, 4.32; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.21.

[0242] 2.12 The synthesis of compound N-136 includes the following steps:

[0243] Synthesis of intermediate sub-136-5: The synthesis steps of intermediate sub-136-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-136-4, thus obtaining sub-136-5 (yield 82%).

[0244] Synthesis of compound N-136: The synthesis steps of compound N-136 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-136-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-136 (yield 85%).

[0245] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.20; H, 4.59; N, 4.32; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.21.

[0246] 2.13 The synthesis of compound N-154 includes the following steps:

[0247] Synthesis of intermediate sub-154-5: The synthesis steps of intermediate sub-154-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-8-4, and starting material d-1 is replaced with starting material d-2, thus obtaining sub-154-5 (yield 84%).

[0248] Synthesis of compound N-154: The synthesis steps of compound N-154 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-154-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-154 (yield 83%).

[0249] Elemental analysis: C 53 H 34 Theoretical N2O2 values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.07; H, 4.65; N, 3.88; HRMS(ESI) m / z [M+H]+: Theoretical value: 730.26; Measured value: 731.24.

[0250] 2.14 The synthesis of compound N-171 includes the following steps:

[0251] Synthesis of intermediate sub-171-5: The synthesis steps of intermediate sub-171-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-38-4, and starting material d-1 is replaced with starting material d-3, thus obtaining sub-171-5 (yield 84%).

[0252] Synthesis of compound N-171: The synthesis steps of compound N-171 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-171-5, and starting material e-1 is replaced with starting material e-4, thus obtaining compound N-171 (yield 83%).

[0253] Elemental analysis: C 53 H 34 Theoretical N2O2 values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.08; H, 4.67; N, 3.86; HRMS(ESI) m / z [M+H]+: Theoretical value: 730.26; Measured value: 731.24.

[0254] 2.15 The synthesis of compound N-247 includes the following steps:

[0255] Synthesis of intermediate sub-247-5: The synthesis steps of intermediate sub-247-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-247-4, and raw material d-1 is replaced with raw material d-4, thus obtaining sub-247-5 (yield 81%).

[0256] Synthesis of compound N-247: The synthesis steps of compound N-247 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-247-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-247 (yield 86%).

[0257] Elemental analysis: C 53 H 32 Theoretical N2O3 values: C, 85.46; H, 4.33; N, 3.76; O, 6.44; Measured values: C, 85.43; H, 4.31; N, 3.79; HRMS(ESI) m / z [M+H]+: Theoretical value: 744.24; Measured value: 745.23.

[0258] 2.16 The synthesis of compound N-271 includes the following steps:

[0259] Synthesis of intermediate sub-271-5: The synthesis steps of intermediate sub-271-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-271-4, thus obtaining sub-271-5 (yield 83%).

[0260] Synthesis of compound N-271: The synthesis steps of compound N-271 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-271-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-271 (yield 86%).

[0261] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.22; H, 4.62; N, 4.28; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.23.

[0262] 2.17 The synthesis of compound N-287 includes the following steps:

[0263] Synthesis of intermediate sub-287-5: The synthesis steps of intermediate sub-287-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-247-4, and starting material d-1 is replaced with starting material d-5, thus obtaining sub-287-5 (yield 83%).

[0264] Synthesis of compound N-287: The synthesis steps of compound N-287 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-287-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-287 (yield 86%).

[0265] Elemental analysis: C 53 H 34 Theoretical N2O2 values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.07; H, 4.66; N, 3.86; HRMS(ESI) m / z [M+H]+: Theoretical value: 730.26; Measured value: 731.25.

[0266] 2.18 The synthesis of compound N-299 includes the following steps:

[0267] Synthesis of intermediate sub-299-5: The synthesis steps of intermediate sub-299-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-299-4, thus obtaining sub-299-5 (yield 83%).

[0268] Synthesis of compound N-299: The synthesis steps of compound N-299 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-299-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-299 (yield 86%).

[0269] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.22; H, 4.62; N, 4.28; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.23; Measured value: 655.23.

[0270] 2.19 The synthesis of compound N-336 includes the following steps:

[0271] Synthesis of intermediate sub-336-5: The synthesis steps of intermediate sub-336-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-299-4, and starting material d-1 is replaced with starting material d-6, thus obtaining sub-336-5 (yield 84%).

[0272] Synthesis of compound N-336: The synthesis steps of compound N-336 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-336-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-336 (yield 86%).

[0273] Elemental analysis: C 47 H 25 Theoretical values ​​for D5N2O2: C, 85.56; H, 5.35; N, 4.25; O, 4.85; Measured values: C, 85.53; H, 5.33; N, 4.29; HRMS(ESI) m / z[M+H]+: Theoretical value: 659.26; Measured value: 660.24.

[0274] The synthesis of compound N-347, denoted as 2.20, includes the following steps:

[0275] Synthesis of intermediate sub-347-5: The synthesis steps of intermediate sub-347-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material f-1, thus obtaining sub-347-5 (yield 89%).

[0276] Synthesis of compound N-347: The synthesis steps of compound N-347 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-347-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-347 (yield 83%).

[0277] Elemental analysis: C 43 H 28 Theoretical N2O2 values: C, 85.41; H, 4.67; N, 4.63; O, 5.29; Measured values: C, 85.31; H, 4.68; N, 4.62; HRMS(ESI) m / z [M+H]+: Theoretical value: 604.71; Measured value: 605.98.

[0278] 2.21 The synthesis of compound N-353 includes the following steps:

[0279] Synthesis of intermediate sub-353-5: The synthesis steps of intermediate sub-353-5 are the same as those of intermediate sub-8-5, except that the starting material d-1 is replaced with the starting material d-5, thus obtaining sub-353-5 (yield 82%).

[0280] Synthesis of compound N-353: The synthesis steps of compound N-353 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-353-5, and starting material e-1 is replaced with starting material e-5, thus obtaining compound N-353 (yield 83%).

[0281] Elemental analysis: C 53 H 34 Theoretical N2O2 values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.07; H, 4.71; N, 3.84; HRMS(ESI) m / z [M+H]+: Theoretical value: 730.87; Measured value: 731.77.

[0282] 2.22 The synthesis of compound N-358 includes the following steps:

[0283] Synthesis of intermediate sub-358-5: The synthesis steps of intermediate sub-358-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-271-4, and raw material d-1 is replaced with raw material d-7, thus obtaining sub-358-5 (yield 83%).

[0284] Synthesis of compound N-358: The synthesis steps of compound N-358 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-358-5, and starting material e-1 is replaced with starting material e-6, thus obtaining compound N-358 (yield 83%).

[0285] Elemental analysis: C 57 H 36 Theoretical N2O2 values: C, 87.67; H, 4.65; N, 3.59; O, 4.10; Measured values: C, 87.678; H, 4.62; N, 3.61; HRMS(ESI) m / z [M+H]+: Theoretical value: 780.93; Measured value: 782.05.

[0286] 2.23 The synthesis of compound N-382 includes the following steps:

[0287] Synthesis of compound N-382: The synthesis steps of compound N-382 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-154-5, and starting material e-1 is replaced with starting material e-7, thus obtaining compound N-382 (yield 86%).

[0288] Elemental analysis: C 47 H 30 Theoretical N2O2 values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.21; H, 4.65; N, 4.29; HRMS(ESI) m / z [M+H]+: Theoretical value: 654.77; Measured value: 655.90.

[0289] 2.24 The synthesis of compound N-459 includes the following steps:

[0290] Synthesis of intermediate sub-459-5: The synthesis steps of intermediate sub-459-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-271-4, and raw material d-1 is replaced with raw material d-8, thus obtaining sub-459-5 (yield 83%).

[0291] Synthesis of compound N-459: The synthesis steps of compound N-459 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-459-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-459 (yield 82%).

[0292] Elemental analysis: C 55 H 34 Theoretical N2O2 values: C, 87.51; H, 4.54; N, 3.71; O, 4.24; Measured values: C, 87.49; H, 4.56; N, 3.70; HRMS(ESI) m / z [M+H]+: Theoretical value: 754.89; Measured value: 756.21.

[0293] 2.25 The synthesis of compound N-462 includes the following steps:

[0294] Synthesis of intermediate sub-462-5: The synthesis steps of intermediate sub-462-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-136-4, and raw material d-1 is replaced with raw material d-5, thus obtaining sub-462-5 (yield 83%).

[0295] Synthesis of compound N-462: The synthesis steps of compound N-462 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-462-5, and starting material e-1 is replaced with starting material e-9, thus obtaining compound N-462 (yield 82%).

[0296] Elemental analysis: C 57 H 36 Theoretical N2O2 values: C, 87.67; H, 4.65; N, 3.59; O, 4.10; Measured values: C, 87.69; H, 4.67; N, 3.54; HRMS(ESI) m / z [M+H]+: Theoretical value: 780.92; Measured value: 782.12.

[0297] 2.26 The synthesis of compound N-469 includes the following steps:

[0298] Synthesis of intermediate sub-469-5: The synthesis steps of intermediate sub-469-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-247-4, and raw material d-1 is replaced with raw material d-9, thus obtaining sub-469-5 (yield 84%).

[0299] Synthesis of compound N-469: The synthesis steps of compound N-469 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-469-5, and starting material e-1 is replaced with starting material e-10, thus obtaining compound N-469 (yield 81%).

[0300] Elemental analysis: C 59 H 34 Theoretical values ​​of N2O3S: C, 83.27; H, 4.03; N, 3.29; O, 5.64; S, 3.77; Measured values: C, 83.28; H, 4.01; N, 3.30; S, 3.75; HRMS(ESI) m / z [M+H]+: Theoretical value: 850.99; Measured value: 852.24.

[0301] 2.27 The synthesis of compound N-476 includes the following steps:

[0302] Synthesis of intermediate sub-476-5: The synthesis steps of intermediate sub-476-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-38-4, and raw material d-1 is replaced with raw material d-10, thus obtaining sub-476-5 (yield 83%).

[0303] Synthesis of compound N-476: The synthesis steps of compound N-476 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-476-5, and starting material e-1 is replaced with starting material e-11, thus obtaining compound N-476 (yield 81%).

[0304] Elemental analysis: C 57 H 34 Theoretical N2OS2 values: C, 82.78; H, 4.14; N, 3.39; O, 1.93; S, 7.75; Measured values: C, 82.79; H, 4.11; N, 3.41; S, 7.72; HRMS(ESI) m / z[M+H]+: Theoretical value: 827.03; Measured value: 828.41.

[0305] 2.28 The synthesis of compound N-488 includes the following steps:

[0306] Synthesis of intermediate sub-488-5: The synthesis steps of intermediate sub-488-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-247-4, and raw material d-1 is replaced with raw material d-11, thus obtaining sub-488-5 (yield 84%).

[0307] Synthesis of compound N-488: The synthesis steps of compound N-488 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-488-5, and starting material e-1 is replaced with starting material e-12, thus obtaining compound N-488 (yield 81%).

[0308] Elemental analysis: C 53 H 32 Theoretical N2OS values: C, 85.46; H, 4.33; N, 3.76; O, 2.15; S, 4.30; Measured values: C, 85.45; H, 4.34; N, 3.71; S, 4.32; HRMS(ESI) m / z[M+H]+: Theoretical value: 744.91; Measured value: 746.09.

[0309] 2.29 The synthesis of compound N-504 includes the following steps:

[0310] Synthesis of intermediate sub-504-5: The synthesis steps of intermediate sub-504-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material f-2 and raw material d-1 is replaced with raw material d-5, thus obtaining sub-504-5 (yield 88%).

[0311] Synthesis of compound N-504: The synthesis steps of compound N-504 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-504-5, and starting material e-1 is replaced with starting material e-13, thus obtaining compound N-504 (yield 84%).

[0312] Elemental analysis: C 49 H 32 Theoretical N2O2 values: C, 86.45; H, 4.74; N, 4.11; O, 4.70; Measured values: C, 86.43; H, 4.75; N, 4.10; HRMS(ESI) m / z [M+H]+: Theoretical value: 680.81; Measured value: 682.33.

[0313] 2.30 The synthesis of compound N-506 includes the following steps:

[0314] Synthesis of intermediate sub-506-5: The synthesis steps of intermediate sub-506-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material f-3 and raw material d-1 is replaced with raw material d-12, thus obtaining sub-506-5 (yield 88%).

[0315] Synthesis of compound N-506: The synthesis steps of compound N-506 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-506-5, and starting material e-1 is replaced with starting material e-14, thus obtaining compound N-506 (yield 83%).

[0316] Elemental analysis: C 55 H 34 Theoretical N2O3 values: C, 85.69; H, 4.45; N, 3.63; O, 6.23; Measured values: C, 85.71; H, 4.47; N, 3.60; HRMS(ESI) m / z [M+H]+: Theoretical value: 770.89; Measured value: 771.28.

[0317] 2.31 The synthesis of compound N-513 includes the following steps:

[0318] Synthesis of intermediate sub-513-5: The synthesis steps of intermediate sub-513-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-513-4, thus obtaining sub-513-5 (yield 82%).

[0319] Synthesis of compound N-513: The synthesis steps of compound N-513 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-513-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-513 (yield 84%).

[0320] Elemental analysis: C 51 H 32 Theoretical N2O2 values: C, 86.91; H, 4.58; N, 3.97; O, 4.54; Measured values: C, 86.90; H, 4.61; N, 3.96; HRMS(ESI) m / z [M+H]+: Theoretical value: 704.83; Measured value: 705.97.

[0321] 2.32 The synthesis of compound N-520 includes the following steps:

[0322] Synthesis of intermediate sub-520-5: The synthesis steps of intermediate sub-520-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-520-4, and raw material d-1 is replaced with raw material d-5, thus obtaining sub-520-5 (yield 83%).

[0323] Synthesis of compound N-520: The synthesis steps of compound N-520 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-520-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-520 (yield 83%).

[0324] Elemental analysis: C 59 H 38 Theoretical N2O2 values: C, 87.82; H, 4.75; N, 3.47; O, 3.97; Measured values: C, 87.80; H, 4.76; N, 3.46; HRMS(ESI) m / z [M+H]+: Theoretical value: 806.97; Measured value: 808.31.

[0325] 2.33 The synthesis of compound N-522 includes the following steps:

[0326] Synthesis of intermediate sub-522-5: The synthesis steps of intermediate sub-522-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-522-4, and raw material d-1 is replaced with raw material d-7, thus obtaining sub-522-5 (yield 84%).

[0327] Synthesis of compound N-522: The synthesis steps of compound N-522 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-522-5, and starting material e-1 is replaced with starting material e-6, thus obtaining compound N-522 (yield 83%).

[0328] Elemental analysis: C 65 H 40 Theoretical N2O2 values: C, 88.61; H, 4.58; N, 3.18; O, 3.63; Measured values: C, 88.66; H, 4.56; N, 3.17; HRMS(ESI) m / z [M+H]+: Theoretical value: 881.05; Measured value: 882.28.

[0329] 2.34 The synthesis of compound N-532 includes the following steps:

[0330] Synthesis of intermediate sub-532-5: The synthesis steps of intermediate sub-532-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-532-4, and raw material d-1 is replaced with raw material d-4, thus obtaining sub-532-5 (yield 81%).

[0331] Synthesis of compound N-532: The synthesis steps of compound N-532 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-532-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-532 (yield 84%).

[0332] Elemental analysis: C 65 H 40 Theoretical N2O3 values: C, 87.03; H, 4.49; N, 3.12; O, 5.35; Measured values: C, 87.06; H, 4.50; N, 3.13; HRMS(ESI) m / z [M+H]+: Theoretical value: 897.05; Measured value: 898.28.

[0333] 2.35 The synthesis of compound N-536 includes the following steps:

[0334] Synthesis of intermediate sub-536-5: The synthesis steps of intermediate sub-536-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with the raw material sub-536-4, thus obtaining sub-536-5 (yield 84%).

[0335] Synthesis of compound N-536: The synthesis steps of compound N-536 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-536-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-536 (yield 82%).

[0336] Elemental analysis: C 53 H 32 Theoretical N2O3 values: C, 85.46; H, 4.33; N, 3.76; O, 6.44; Measured values: C, 85.47; H, 4.36; N, 3.74; HRMS(ESI) m / z [M+H]+: Theoretical value: 744.85; Measured value: 745.99.

[0337] 2.36 The synthesis of compound N-552 includes the following steps:

[0338] Synthesis of intermediate sub-552-5: The synthesis steps of intermediate sub-552-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-552-4, and raw material d-1 is replaced with raw material d-2, thus obtaining sub-552-5 (yield 83%).

[0339] Synthesis of compound N-552: The synthesis steps of compound N-552 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-552-5, and starting material e-1 is replaced with starting material e-3, thus obtaining compound N-552 (yield 83%).

[0340] Elemental analysis: C 59 H 36 Theoretical values ​​of N2O2S: C, 84.66; H, 4.34; N, 3.35; O, 3.82; S, 3.83; Measured values: C, 84.64; H, 4.36; N, 3.32; S, 3.84; HRMS(ESI) m / z [M+H]+: Theoretical value: 837.01; Measured value: 838.41.

[0341] 2.37 The synthesis of compound N-561 includes the following steps:

[0342] Synthesis of intermediate sub-561-5: The synthesis steps of intermediate sub-561-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-561-4, and raw material d-1 is replaced with raw material d-5, thus obtaining sub-561-5 (yield 81%).

[0343] Synthesis of compound N-561: The synthesis steps of compound N-561 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-561-5, and starting material e-1 is replaced with starting material e-5, thus obtaining compound N-561 (yield 82%).

[0344] Elemental analysis: C 63 H 40 Theoretical N2O2 values: C, 88.29; H, 4.70; N, 3.27; O, 3.73; Measured values: C, 88.31; H, 4.67; N, 3.25; HRMS(ESI) m / z [M+H]+: Theoretical value: 857.03; Measured value: 858.40.

[0345] 2.38 The synthesis of compound N-388 includes the following steps:

[0346] Synthesis of intermediate sub-388-5: The synthesis steps of intermediate sub-388-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-247-4, and raw material d-1 is replaced with raw material d-13, thus obtaining sub-388-5 (yield 80%).

[0347] Synthesis of compound N-388: The synthesis steps of compound N-388 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-388-5, thus obtaining compound N-388 (yield 83%).

[0348] Elemental analysis: C 50 H 34 Theoretical N2O2 values: C, 86.43; H, 4.93; N, 4.03; O, 4.61; Measured values: C, 86.42; H, 4.95; N, 4.01; HRMS(ESI) m / z [M+H]+: Theoretical value: 694.83; Measured value: 696.07.

[0349] The synthesis of compound N-402, 2.39, includes the following steps:

[0350] Synthesis of intermediate sub-402-5: The synthesis steps of intermediate sub-402-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-247-4, and raw material d-1 is replaced with raw material d-14, thus obtaining sub-402-5 (yield 80%).

[0351] Synthesis of compound N-402: The synthesis steps of compound N-402 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-402-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-402 (yield 85%).

[0352] Elemental analysis: C 66 H 40 Theoretical N2O2 values: C, 88.77; H, 4.51; N, 3.14; O, 3.58; Measured values: C, 88.79; H, 4.53; N, 3.11; HRMS(ESI) m / z [M+H]+: Theoretical value: 893.06; Measured value: 894.23.

[0353] 2.40 The synthesis of compound N-570 includes the following steps:

[0354] Synthesis of intermediate sub-570-5: The synthesis steps of intermediate sub-570-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with intermediate sub-299-4, and starting material d-1 is replaced with starting material d-15, thus obtaining sub-570-5 (yield 81%).

[0355] Synthesis of compound N-570: The synthesis steps of compound N-570 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-570-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-570 (yield 84%).

[0356] Elemental analysis: C 59 H 42 Theoretical N2O2 values: C, 87.38; H, 5.22; N, 3.45; O, 3.95; Measured values: C, 87.40; H, 5.25; N, 3.41; HRMS(ESI) m / z [M+H]+: Theoretical value: 811.00; Measured value: 812.31.

[0357] 2.41 The synthesis of compound N-576 includes the following steps:

[0358] Synthesis of intermediate sub-576-5: The synthesis steps of intermediate sub-576-5 are the same as those of intermediate sub-8-5, except that intermediate sub-8-4 is replaced with raw material sub-271-4, and raw material d-1 is replaced with raw material d-16, thus obtaining sub-576-5 (yield 80%).

[0359] Synthesis of compound N-576: The synthesis steps of compound N-576 are the same as those of compound N-8, except that intermediate sub-8-5 is replaced with intermediate sub-576-5, and starting material e-1 is replaced with starting material e-2, thus obtaining compound N-576 (yield 82%).

[0360] Elemental analysis: C 58 H 40 Theoretical N2O2 values: C, 87.41; H, 5.06; N, 3.52; O, 4.01; Measured values: C, 87.43; H, 5.04; N, 3.50; HRMS(ESI) m / z [M+H]+: Theoretical value: 796.97; Measured value: 798.09.

[0361] Device Example

[0362] The device example provides an organic electroluminescent device composed of different organic electroluminescent materials, as shown in Figure 1. It includes an anode 2, a hole injection layer 3, a hole transport layer 4, an emissive layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8, which are sequentially stacked on a substrate 1. The device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / emissive layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0363] The main material structures used in the device embodiments and comparative examples are shown in Table 1 below:

[0364] Table 1

[0365] The specific fabrication process of device embodiment 1 is shown below:

[0366] (1) Substrate cleaning:

[0367] 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%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0368] (2) Evaporation of organic light-emitting functional layer:

[0369] 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 -4 Pa, a mixture of HI-2 and HT-12 is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of HI-2 to HT-12 is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0370] HT-12 was deposited on the hole injection layer as a hole transport layer, with a film thickness of 80 nm.

[0371] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: the light-emitting host material (M-1 and N-8) and the guest material (RD-16) are vacuum deposited by co-evaporation, wherein the mass ratio of M-1:N-8:RD-16 is 47.5:47.5:5, and the total film thickness is 35nm.

[0372] An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: ET-7 and LiQ are vacuum deposited by co-evaporation, wherein the mass ratio of ET-7 and LiQ is 50:50 and the total film thickness is 30nm.

[0373] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0374] Al was deposited on the electron injection layer as a cathode, with a total film thickness of 90 nm.

[0375] The preparation methods of Device Examples 2-41 and Comparative Examples 1-2 are the same as those of Device Example 1, except that the luminescent host material N-8 in the luminescent layer is replaced. The compounds that replace the luminescent host material N-8 in Device Examples 2-41 are, in order: N-12, N-31, N-38, N-41, N-59, N-75, N-78, N-82, N-96, N-106, N-136, N-154, N-171, N-247, N-271, N-287, N... -299, N-336, N-347, N-353, N-358, N-382, N-459, N-462, N-469, N-476, N-488, N-504, N-506, N-513, N-520, N-522, N-532, N-536, N-552, N-561, N-388, N-402, N-570, N-576; In Comparative Examples 1 and 2, the compounds that replaced the luminescent host material N-8 were REF-1 and REF-2 in order.

[0376] The organic electroluminescent devices obtained in Device Examples 1-41 and Device Comparative Examples 1-2 were tested.

[0377] 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;

[0378] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0379] Lifetime test: current density 50mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0380] The device performance test results are shown in Table 2:

[0381] Table 2

[0382] Table 2

[0383] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0384] 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, The organic compound has the structure shown in formula (1): In equation (1), Y1 and Y2 are each independently selected from O or S; Ring A may or may not exist, and if ring A is present, it is selected from the benzene ring; Ar 1 Ar 2 They may be the same or different, and each is independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; L 1 L 2 Whether the same or different, each is independently selected from single-bonded, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; R1 and R2 are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; n1 is selected from any integer from 1 to 9. When n1 equals 1, R1 is a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C3-C60 heteroaryl. When n1 is greater than 1, R1 is the same or different, and at least one of R1 is a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C3-C60 heteroaryl. n2 is selected from any integer between 0 and 3. When n2 is greater than 1, each R2 may be the same or different. The substituents of the substituted C6-C60 arylene, substituted C3-C60 heteroarylene, substituted C6-C60 aryl, and substituted C3-C60 heteroarylene 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 heteroarylene, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the structures of formulas 1-1 to 1-16, wherein Y1, Y2, and Ar 1 Ar 2 L 1 L 2 The definitions of R1, R2, n1, and n2 are the same as in claim 1:

3. The organic compound according to claim 1, characterized in that, When ring A does not exist, Ar 1 Selected from substituted or unsubstituted C6-C24 aryl groups, substituted or unsubstituted C3-C24 heteroaryl groups with O as a heteroatom, and substituted or unsubstituted C3-C24 heteroaryl groups with S as a heteroatom; The substituents of the substituted C6-C24 aryl, the substituted O-as heteroatom C3-C24 heteroaryl, and the substituted S-as heteroatom C3-C24 heteroaryl 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 amino.

4. The organic compound according to claim 1, characterized in that, When ring A does not exist, L 1 For substituted C6-C60 arylene, substituted C3-C60 heteroarylene; The substituted C6-C60 arylene and the substituted C3-C60 heteroarylene 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 amino.

5. The organic compound according to claim 1, characterized in that, Ar 1 Ar 2 They may be the same or different, each independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups; and / or, L 1 L 2 They may be identical or different, each independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; and / or, R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C30 aryl, and substituted C3-C30 heteroarylene 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 heteroarylene, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

6. The organic compound according to claim 1, characterized in that, Ar 1 Ar 2 Whether identical or different, each is independently selected from substituted or unsubstituted A groups, wherein the A group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzospirodifluorenyl, benzofuran Brønsted, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, N-phenylcarbazoyl, benzocarbazoyl, N-phenylbenzocarbazoyl, dibenzocarbazoyl, N-biphenylcarbazoyl, benzooxazolyl, naphthooxazolyl, phenanthreneoxazolyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, N-phenylbenzofuran-carbazoyl; Wherein, the substituents in the substituted A 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 arylamine, and C3-C60 heteroarylamine; and / or, L 1 L 2 Whether the groups are the same or different, each group is independently selected from single-bonded, substituted or unsubstituted B groups, wherein the B groups are selected from: phenylene, naphthylene, phenanthrene, binatrimethylene, dibenzofuranyl, dibenzothiophene, benzonaphthiophene, and benzonaphthiophene. Wherein, the substituents in 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 arylamine, and C3-C60 heteroarylamine; and / or, R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen, cyano, substituted or unsubstituted C groups; wherein the C group is selected from: phenyl, naphthyl, phenanthryl, anthraceneyl, fluoranyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzo[] Spirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, N-phenylcarbazoyl, benzocarbazoyl, N-phenylbenzocarbazoyl, dibenzocarbazoyl, biphenylcarbazoyl, benzooxazolyl, naphthooxazolyl, phenanthreneoxazolyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, N-phenylbenzofuran-carbazoyl; The substituents in the substituted C 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 heteroaryl.

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

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

9. 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 1-7 or an organic electroluminescent material as described in claim 8.

10. The organic electroluminescent device according to claim 9, characterized in that, 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 auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

11. The organic electroluminescent device according to claim 9 or 10, characterized in that, The organic layer includes a light-emitting layer, which comprises an organic compound as described in any one of claims 1-7 or an organic electroluminescent material as described in claim 8.

12. The organic electroluminescent device according to claim 11, characterized in that, 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 1-7 or an organic electroluminescent material as described in any one of claims 8.

13. An electronic device, characterized in that, The electronic device includes an organic electroluminescent device as described in any one of claims 9-12, an organic electroluminescent material as described in claim 8, or an organic compound as described in any one of claims 1-7.

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