An organic compound and use thereof

Abstract

The present application relates to the technical field of display, in particular to an organic compound and application thereof. The present application provides an organic compound, which has the following structure: the organic electroluminescent device containing the organic compound has lower driving voltage, higher luminous efficiency and longer service life.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of display, in particular to an organic compound and application thereof. BACKGROUND

[0002] An organic electroluminescence device (OLED) is a device that changes electric energy into light by applying electricity to an organic electroluminescence material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (which comprises a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified as hole injection materials, hole transport materials, electron blocking materials, light emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. by their functions. In the organic EL device, due to the applied voltage, holes are injected from the anode into the light emitting layer, and electrons are injected from the cathode into the light emitting layer, and high-energy excitons are formed by the recombination of holes and electrons. By this energy, the organic light emitting compound reaches the excited state, and light is emitted by the energy generated by the excited state of the organic light emitting compound returning to the ground state to produce luminescence.

[0003] The most important factor determining the light emitting efficiency in the organic EL device is the light emitting material. The light emitting material must have high quantum efficiency, as well as high electron and hole mobility, and the formed light emitting material layer must be uniform and stable. The light emitting material is divided into blue light emitting material, green light emitting material, and red light emitting material according to the color of light emission, and in addition, yellow light emitting material or orange light emitting material. In addition, the light emitting material can also be divided into host material and dopant material according to its function.

[0004] However, the existing organic electroluminescence material has poor hole transport ability, which further causes the problems of high driving voltage, low light emitting efficiency, and short service life of the organic electroluminescence device containing the organic electroluminescence material, which seriously limits the application of the organic electroluminescence device. SUMMARY

[0005] The present application aims to overcome the problem of poor hole transport ability of the existing organic electroluminescence material, which causes the problems of high driving voltage, low light emitting efficiency, and short service life of the organic electroluminescence device containing the organic electroluminescence material, and further provides an organic compound and application thereof.

[0006] In the definition of the substituent terms of the present application:

[0007] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can comprise at least one compound. If desired, the organic electroluminescent material can be comprised in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary 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.

[0008] The term "a plurality of organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which can be comprised in any layer constituting the organic electroluminescent device. It can mean both materials before being comprised in the organic electroluminescent device (e.g., before vapor deposition) and materials after being comprised in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of organic electroluminescent materials can be a combination of at least two compounds, which can be comprised in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting 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 can be comprised in the same layer or different layers, and can be mixed-vaporized or co-vaporized, or can be vaporized individually.

[0009] In the present application, the description "each... is independently selected from" and "each... is independently" and "each... is independently" can be interchangeable, and should be interpreted broadly, which can mean that the specific options expressed between the same symbols in different groups do not affect each other, or can mean that the specific options expressed between the same symbols in the same group do not affect each other.

[0010] In the present application, the term "substituent" has the usual meaning known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to the parent core group.

[0011] In the present application, the term "substituted or unsubstituted" means that the functional group recited after the term can or can not have a substituent (hereinafter, the substituents will be collectively referred to as Rcfor convenience of description). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc, or aryl which is not substituted. The substituents Rcmentioned above, for example, can be deuterium, a halogen, a cyano group, a C1-C60 alkyl group, a C3-C60 cycloalkyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, and the like, and optionally, for example, deuterium, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a trialkylsilyl group, a deuterated alkyl group, an aryl group, a heteroaryl group, and the like. Of course, the number of substituents Rcmay be one or more. When two substituents Rcare attached to the same atom, the two substituents Rcmay be present independently or connected to each other to form a ring with the atom; when two substituents Rcexist adjacent to each other on a functional group, the two adjacent substituents Rcmay be present independently or fused with the functional group to which they are attached to form a ring.

[0012] In the present application, the term "alkyl" whether used alone or as part of another term, refers to a saturated hydrocarbon group, which can be straight or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight or branched saturated hydrocarbon having from 1 to 60 carbon atoms, preferably from 1 to 40 carbon atoms, and more preferably from 1 to 20 carbon atoms, and examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, and hexyl.

[0013] In the present application, the term "aryl" and "arylene" includes monocyclic, polycyclic, or fused ring aryl groups, which can be interrupted by short non-aromatic units between the rings, and can contain a spiro structure, and aryl includes, but is not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, and the like, and arylene includes, but is not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene, and the like.

[0014] In the present application, the term "heteroaryl" includes monocyclic, polycyclic or fused ring heteroaryl, the rings of which can be interrupted by short non-aromatic units, the heteroatoms of which include nitrogen, oxygen, sulfur, the heteroaryl in the present application includes but is not limited to furanyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoaxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof and the like; heteroarylene includes but is not limited to furanylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylylene, pyrazinylyene, pyrimidinylene, pyridazinylyene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, dibenzothiophenylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoaxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylyene, dihydroacridinylene, derivatives thereof and the like. As used in the present application, the term "substituted" means that a hydrogen atom in the compound is substituted with another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be substituted with the substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0015] In the present application, the term "halogen" means an atom selected from fluorine, chlorine, bromine, iodine.

[0016] In the present application, unless otherwise specified, a hydrogen atom includes protium, deuterium and tritium.

[0017] In the present application, the range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms thereof is any integer within the defined range, for example, C6-C60 aryl, the number of carbon atoms of the 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, and the like.

[0018] In the present application, unless otherwise specified, the substituents do not form a ring with the group to which they are attached.

[0019] In the present application, unless otherwise specified, the groups are unsubstituted.

[0020] The scheme adopted by the present application is as follows:

[0021] In a first aspect, the present application provides an organic compound having a structure shown in formula (1):

[0022]

[0023] Formula (1)

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

[0025] Ring A is present or absent, and when present, is selected from a benzene ring;

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

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

[0028] R1, 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 is equal to 1, R1 is substituted or unsubstituted C6-C60 aryl, 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 substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0030] n2 is selected from any integer from 0 to 3, when n2 is greater than 1, R2 is the same or different;

[0031] wherein the substituents of the substituted C6-C60 arylene, substituted C3-C60 heteroarylene, substituted C6-C60 aryl, and substituted C3-C60 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine.

[0032] It is understood that when ring A is present, ring A is fused to the benzene ring to which it is attached; .

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

[0034] wherein the substituents in the substituted phenyl are selected from one or a combination of two or more of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine.

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

[0036]

[0037]

[0038]

[0039] .

[0040] Preferably, the organic compound of formula (1) is selected from any one of the structures of formula A-1 to formula A-84, wherein Y1, Y2, Ar 1 , Ar 2 , L 1 , L 2 , R1, R2, n1, n2 are defined as the same as the above definitions:

[0041] A-1A-2A-3A-4

[0042] A-5A-6A-7A-8

[0043] A-9A-10A-11A-12

[0044] A-13A-14A-15A-16

[0045] A-17 A-18 A-19 A-20

[0046] A-21 A-22 A-23 A-24

[0047] A-25 A-26 A-27 A-28

[0048] A-29 A-30 A-31 A-32

[0049] A-33 A-34 A-35 A-36

[0050] A-37 A-38 A-39 A-40

[0051] A-41 A-42 A-43 A-44

[0052] A-45 A-46 A-47 A-48

[0053] A-49 A-50 A-51 A-52

[0054] A-53 A-54 A-55 A-56

[0055] A-57 A-58 A-59 A-60

[0056] A-61 A-62 A-63 A-64

[0057] A-65 A-66 A-67 A-68

[0058] A-69 A-70 A-71 A-72

[0059] A-73 A-74 A-75 A-76

[0060] A-77 A-78 A-79 A-80

[0061] A-81 A-82 A-83 A-84.

[0062] Preferably, when ring A is absent, Ar1is selected from substituted or unsubstituted C6-C24aryl, substituted or unsubstituted O-heteroatom C3-C24heteroaryl, substituted or unsubstituted S-heteroatom C3-C24heteroaryl;

[0063] Preferably, the substituents of the substituted C6-C30arylene, substituted C3-C30heteroarylene, substituted C6-C30aryl, and substituted C3-C30heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60alkyl, C3-C60cycloalkyl, C6-C60aryl, C3-C60heteroaryl, C6-C60arylamino, and C3-C60heteroarylamino.

[0064] Preferably, when ring A is absent, L1is not a single bond.

[0065] Preferably, in formula (1) or formula 1-1 to formula 1-16, Ar 1 , Ar 2 are the same or different, each independently selected from substituted or unsubstituted C6-C30aryl and substituted or unsubstituted C3-C30heteroaryl.

[0066] Preferably, L 1 , L 2 are the same or different, each independently selected from a single bond, substituted or unsubstituted C6-C30arylene, and substituted or unsubstituted C3-C30heteroarylene.

[0067] Preferably, R1and R2are the same or different, each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C6-C30aryl, and substituted or unsubstituted C3-C30heteroaryl.

[0068] Preferably, the substituents of the substituted C6-C30arylene, substituted C3-C30heteroarylene, substituted C6-C30aryl, and substituted C3-C30heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60alkyl, C3-C60cycloalkyl, C6-C60aryl, C3-C60heteroaryl, C6-C60arylamino, and C3-C60heteroarylamino.

[0069] Preferably, in formula (1) or formula 1-1 to formula 1-16, Ar 1 , Ar 2the same or different, each independently selected from a substituted or unsubstituted A group, wherein the A group is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, pyrenyl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzospirofluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, diphenylcarbazolyl, biphenylylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, N-phenylbenzofurocarbazolyl;

[0070] wherein the substituents in the substituted A group are selected from the group consisting of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine, one or a combination of at least two thereof;

[0071] More preferably, the substituents in the substituted A group are selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthryl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, benzocarbazolyl, one or a combination of at least two thereof;

[0072] Preferably, L 1 , L 2 the same or different, each independently selected from a single bond, a substituted or unsubstituted B group, wherein the B group is selected from the group consisting of phenylene, naphthylene, phenanthrylene, binaphthylene, dibenzofuranylene, dibenzothiophenylene, benzonaphthofuranylene, benzonaphthothiophenylene;

[0073] wherein the substituents in the substituted B group are selected from the group consisting of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine, one or a combination of at least two thereof;

[0074] More preferably, the substituents of the substituted B group are selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthryl, fluorenyl, pyrenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzonaphthofuranyl, benzonaphthothienyl, carbazolyl, benzocarbazolyl, in combination of one or at least two.

[0075] Preferably, R1, R2 are the same or different, each independently selected from the group consisting of deuterium, halogen, cyano, a substituted or unsubstituted C group; wherein the C group is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, pyrenyl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzospirofluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, dibenzocarbazolyl, biphenylylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, N-phenylbenzofurocarbazolyl;

[0076] wherein the substituents of the substituted C group are selected from the group consisting of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine, in combination of one or at least two.

[0077] More preferably, the substituents of the substituted C group are selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthryl, fluorenyl, pyrenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzonaphthofuranyl, benzonaphthothienyl, carbazolyl, benzocarbazolyl, in combination of one or at least two.

[0078] Preferably, the organic compound of formula (1) or formula 1-1 to formula 1-16 is selected from any one of the following structures:

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] .

[0116] In a second aspect, the present application provides a method for preparing the above-mentioned organic compound, which comprises the following steps:

[0117] The compound N-n can be obtained by the following synthetic route:

[0118] Synthetic route 1:

[0119]

[0120] Synthetic route 2:

[0121]

[0122] Synthetic route 3:

[0123] Synthesis Route 4:

[0124]

[0125] Synthesis Route 5:

[0126]

[0127] Synthesis Route 6:

[0128]

[0129] Synthesis Route 7:

[0130]

[0131] Synthesis Route 8:

[0132]

[0133] Synthesis Route 9:

[0134]

[0135] Synthesis Route 10:

[0136]

[0137] Synthesis Route 11:

[0138]

[0139] Synthesis Route 12:

[0140]

[0141] Synthesis Route 13:

[0142]

[0143] wherein one of X1, X2 is boronic acid group and the other is iodine group.

[0144] The starting materials a-x, b-x, c-x, d-x, e-x, f-x can be purchased directly or synthesized by conventional reaction routes and conditions according to the reported methods in the prior art.

[0145] In a third aspect, the present application also provides an organic electroluminescent material comprising the organic compound as described above.

[0146] In a fourth aspect, the present application provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises the organic compound or the organic electroluminescent material as described above.

[0147] Preferably, the organic layer between the cathode and the anode comprises any one or a combination of at least two of 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.

[0148] Optionally, the organic layer comprises a hole injection layer to enhance the ability of injecting holes into the hole transport layer. The hole injection layer can be selected from diphenylamine derivatives, arylamine compounds, phthalocyanine derivatives, or other materials, which are not particularly limited in the present application. The material of the hole injection layer comprises, but is not limited to, the following compounds:

[0149] .

[0150] Optionally, the organic layer comprises a hole transport layer, which can comprise one or more hole transport materials selected from carbazole polymers, carbazole-attached triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. The material of the hole injection layer comprises, but is not limited to, the following compounds:

[0151]

[0152]

[0153]

[0154]

[0155] .

[0156] Optionally, the organic layer comprises a light-emitting auxiliary layer, which can be a single layer or a multi-layer structure.

[0157] Preferably, the organic layer comprises a light-emitting layer, which comprises the organic compound as shown in formula (1).

[0158] Preferably, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a guest material, the host material comprises a multi-host material or a single-host material, the multi-host material or the single-host material comprises, but is not limited to, an aromatic amine compound and its derivative, a triazine compound and its derivative, a carbazole compound and its derivative, an organic compound as shown in formula (1), and the like, and the present application does not make special limitations on this; the host material is also referred to as a matrix material.

[0159] The guest material can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials, and the present application does not make special limitations on this; the guest material is also referred to as a dopant material or a dopant. The guest material comprises, but is not limited to, the following structures:

[0160]

[0161]

[0162] .

[0163] Optionally, the organic layer comprises a hole-blocking layer, and the hole-blocking layer can be a single layer or a multi-layer structure.

[0164] Optionally, the organic layer comprises an electron-transporting layer, and the electron-transporting layer can be a single layer structure or a multi-layer structure, and it can comprise one or more electron-transporting materials, which can be selected from, but not limited to, LiQ, a benzimidazole derivative, an oxadiazole derivative, a quinoxaline derivative, or other electron-transporting materials, and the present application does not make special limitations on this. The material of the electron-transporting layer comprises, but is not limited to, the following structures:

[0165]

[0166]

[0167]

[0168]

[0169] .

[0170] Optionally, an electron-injection layer is further provided between the cathode and the electron-transporting layer to enhance the ability of injecting electrons into the electron-transporting layer. The electron-injection layer can comprise inorganic materials such as alkali metal sulfides and alkali metal halides, or can comprise a complex of alkali metal and organic matter.

[0171] In a fifth aspect, the present application also provides an electronic device comprising the organic electroluminescent device as described above or the organic electroluminescent material as described above or the organic compound as shown in formula (1).

[0172] The electronic device includes, but is not limited to, a mobile phone, a wearable watch, a fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light emitting field effect transistor, an image sensor, or a dye laser, etc.

[0173] Advantages of the present application:

[0174] The organic compound provided by the present application, based on the structure of formula (1), introduces specific substituents on the dibenzofuran, dibenzothiophene, benzonaphthofuran, and benzonaphthothiophene structural fragments, which can make the overall configuration of the molecule more three-dimensional, thereby effectively increasing the dipole moment of the molecule, and further enhancing the overall hole transport ability of the molecular structure, and further making the organic electroluminescent device containing the organic compound have lower driving voltage, higher luminous efficiency, and longer service life. BRIEF DESCRIPTION OF DRAWINGS

[0175] In order to more clearly illustrate the specific embodiments of the present application or the technical solutions in the prior art, the drawings needed in the specific embodiments or prior art description will be briefly introduced below. Obviously, the drawings in the following description are some embodiments of the present application, and those skilled in the art can also obtain other drawings according to these drawings without creative labor.

[0176] Figure 1 Structure diagram of the organic electroluminescent device in the device embodiment of the present application;

[0177] 1-Substrate; 2-Anode; 3-Hole injection layer; 4-Hole transport layer; 5-Emission layer; 6-Electron transport layer; 7-Electron injection layer; 8-Cathode. DETAILED DESCRIPTION

[0178] If the specific experimental steps or conditions are not specified in the embodiments, the operations or conditions can be performed according to the conventional experimental steps described in the literature in the art. If the reagents or instruments are not specified by the manufacturer, they are conventional reagent products that can be obtained by purchase.

[0179] Those skilled in the art will appreciate that the chemical reactions described in the application can be performed on a wide variety of synthetic precursors and intermediates to prepare many of the compounds of the application, and that the application is intended to embrace such alternatives unless otherwise specifically conveyed in the description. For example, where appropriate, the synthetic precursors and intermediates can be further modified into other synthetic precursors and intermediates using procedures and reactions described herein or known in the art. Unless otherwise described, the compounds of the application described in the application are prepared using commercially available starting materials or precursors.

[0180] Unless otherwise indicated, conventional methods of chemistry and biochemistry were used in the practice of the application. Unless otherwise indicated, the practice of the application employs reagents, materials and techniques of biochemistry, molecular biology, microbiology, cell biology, and immunology, which are specifically prescribed in the literature and which are generally available to those skilled in the art. Unless otherwise indicated, the practice of the application employs reagents, materials and techniques of synthetic organic chemistry, which are specifically prescribed in the literature and which are generally available to those skilled in the art.

[0181] Those skilled in the art will appreciate that the chemical reactions described in the application can be performed on a wide variety of synthetic precursors and intermediates to prepare many of the compounds of the application, and that the application is intended to embrace such alternatives unless otherwise specifically conveyed in the description. For example, where appropriate, the synthetic precursors and intermediates can be further modified into other synthetic precursors and intermediates using procedures and reactions described herein or known in the art. Unless otherwise described, the compounds of the application described in the application are prepared using commercially available starting materials or precursors.

[0182] The starting materials a-x of the embodiments of the application comprise the following structures:

[0183]

[0184]

[0185]

[0186] The starting materials b-x of the embodiments of the application comprise the following structures:

[0187]

[0188]

[0189] The starting materials c-x of the embodiments of the application comprise the following structures:

[0190]

[0191] The starting materials d-x of the embodiments of the application comprise the following structures:

[0192]

[0193]

[0194] The raw material e-x in the embodiment of the present application comprises the following structure:

[0195]

[0196]

[0197] The raw material f-x in the embodiment of the present application comprises the following structure:

[0198]

[0199] The synthesis of the raw material e-10 can refer to the following method:

[0200]

[0201] Preparation of the intermediate sub-e-10-3: take a 100-milliliter three-necked round-bottom flask and put a stirring rod and an upper reflux tube into it, and then sequentially add the raw material sub-e-10-1 (1.0 mmol), the raw material sub-e-10-2 (1.1 mmol), Pd (dppf) Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL), and then heat to 90°C for 5 hours, after the reaction is completed, reduce to room temperature, quench with a saturated aqueous ammonium chloride solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent by using a rotary evaporator, separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50), and obtain the intermediate sub-e-10-3 (yield 82 %).

[0202] Preparation of the compound e-10: take a 100-milliliter three-necked round-bottom flask and put a stirring rod and an upper reflux tube into it, and then sequentially add the intermediate sub-e-10-3 (1.0 mmol), the raw material sub-e-10-4 (1.1 mmol), Pd (dppf) Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL), and then heat to 90°C for 5 hours, after the reaction is completed, reduce to room temperature, quench with a saturated aqueous ammonium chloride solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent by using a rotary evaporator, separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50), and obtain the intermediate e-10 (yield 78 %).

[0203] 1. Synthesis of the intermediate sub-n-4:

[0204] 1.1 Synthesis of the intermediate sub-38-4:

[0205]

[0206] Synthesis of intermediate sub-38-1 : Take a 500 mL three-necked round-bottom flask and put a stir bar and an adapter for refluxing. Add raw material a-1 (275.5 mmol), raw 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) successively under nitrogen protection. Heat to 90 ± 2°C under nitrogen protection. React for 24 h. After the reaction, extract with ethyl acetate and water. Dry the organic layer over MgSO4and concentrate. Then, purify the resulting compound by silica gel column chromatography and recrystallization to obtain intermediate sub-38-1 in a yield of 34%.

[0207] Synthesis of intermediate sub-38-2: Take a 500 mL three-necked round-bottom flask and put a stir bar and an adapter for refluxing. Add 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) successively under nitrogen protection. Heat to 90 ± 2°C under nitrogen protection. React for 24 h. After the reaction, extract with ethyl acetate and water. Dry the organic layer over MgSO4and concentrate. Then, purify the resulting compound by silica gel column chromatography and recrystallization to obtain intermediate sub-38-2 in a yield of 68%.

[0208] Synthesis of intermediate sub-38-3: Take a 500 mL three-necked round-bottom flask and put a stir bar and an adapter for refluxing. Add intermediate sub-38-2 (46.9 mmol), dichloromethane (100 mL), and stir at a low temperature (-10°C) for 20 min. Slowly add 71.2 mmol of BBr3, and control the internal temperature at -10-0°C. After the addition, continue to stir for 30 min. After the reaction, pour the reaction solution into ice water, extract with dichloromethane and water, dry the organic layer over MgSO4, and concentrate. Then, recrystallize the resulting compound with n-hexane to obtain intermediate sub-38-3 in a yield of 92%.

[0209] Synthesis of intermediate sub-38-4: Take 500 mL three-necked round-bottom flask and put it into a stirring sub with an upper reflux tube, under nitrogen protection, add intermediate sub-38-3 (33.0 mmol), K2CO3 (65.9 mmol), NMP (100 mL) successively, heat to 140 °C, react for 6 h. After the reaction is completed, quench with water, add sodium chloride, extract with ethyl acetate and water, dry the formed organic layer with magnesium sulfate (MgSO4) and concentrate to obtain intermediate sub-38-4, yield: 87%.

[0210] 1.2 Synthesis of intermediate sub-8-4:

[0211]

[0212] 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 the raw material a-1 is replaced by the raw material a-2, to obtain intermediate sub-8-1 (yield 33%).

[0213] 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 by intermediate sub-8-1, to obtain intermediate sub-8-2 (yield 65%).

[0214] 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 by intermediate sub-8-2, to obtain intermediate sub-8-3 (yield 91%).

[0215] 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 by intermediate sub-8-3, to obtain intermediate sub-8-4 (yield 83%).

[0216] 1.3 Synthesis of intermediate sub-12-4:

[0217]

[0218] 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 the raw material a-1 is replaced by the raw material a-3, and the raw material b-1 is replaced by the raw material b-3, to obtain intermediate sub-12-1 (yield 34%).

[0219] Synthesis of intermediate sub-12-2: The synthesis of intermediate sub-12-2 followed the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-12-1, to give intermediate sub-12-2 (yield 67%).

[0220] Synthesis of intermediate sub-12-3: The synthesis of intermediate sub-12-3 followed the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-12-2, to give intermediate sub-12-3 (yield 92%).

[0221] Synthesis of intermediate sub-12-4: The synthesis of intermediate sub-12-4 followed the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-12-3, to give intermediate sub-12-4 (yield 86%).

[0222] 1.4 Synthesis of intermediate sub-82-4:

[0223]

[0224] Synthesis of intermediate sub-82-1: The synthesis of intermediate sub-82-1 followed the same procedure as for intermediate sub-38-1, except raw material a-1 was replaced by raw material a-4, and raw material b-1 was replaced by raw material b-7, to give intermediate sub-82-1 (yield 36%).

[0225] Synthesis of intermediate sub-82-2: The synthesis of intermediate sub-82-2 followed the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-82-1, to give intermediate sub-82-2 (yield 64%).

[0226] Synthesis of intermediate sub-82-3: The synthesis of intermediate sub-82-3 followed the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-82-2, to give intermediate sub-82-3 (yield 90%).

[0227] Synthesis of intermediate sub-82-4: The synthesis of intermediate sub-82-4 followed the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-82-3, to give intermediate sub-82-4 (yield 85%).

[0228] 1.5 Synthesis of intermediate sub-96-4:

[0229]

[0230] Synthesis of intermediate sub-96-1 : The synthesis of intermediate sub-96-1 was carried out following the same procedure as for intermediate sub-38-1, except intermediate a-1 was replaced by intermediate a-8 and intermediate b-1 was replaced by intermediate b-7, to afford intermediate sub-96-1 (yield 37%).

[0231] Synthesis of intermediate sub-96-2: The synthesis of intermediate sub-96-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-96-1, to afford intermediate sub-96-2 (yield 63%).

[0232] Synthesis of intermediate sub-96-3: The synthesis of intermediate sub-96-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-96-2, to afford intermediate sub-96-3 (yield 91 %).

[0233] Synthesis of intermediate sub-96-4: The synthesis of intermediate sub-96-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-96-3, to afford intermediate sub-96-4 (yield 85%).

[0234] 1.6 Synthesis of intermediate sub-136-4:

[0235]

[0236] Synthesis of intermediate sub-136-1 : The synthesis of intermediate sub-136-1 was carried out following the same procedure as for intermediate sub-38-1, except intermediate a-1 was replaced by intermediate a-4 and intermediate b-1 was replaced by intermediate b-4, to afford intermediate sub-136-1 (yield 36%).

[0237] Synthesis of intermediate sub-136-2: The synthesis of intermediate sub-136-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-136-1, to afford intermediate sub-136-2 (yield 67%).

[0238] Synthesis of intermediate sub-136-3: The synthesis of intermediate sub-136-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-136-2, to give intermediate sub-136-3 in 90% yield.

[0239] Synthesis of intermediate sub-136-4: The synthesis of intermediate sub-136-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-136-3, to give intermediate sub-136-4 in 83% yield.

[0240] 1.7 Synthesis of intermediate sub-247-4:

[0241]

[0242] Synthesis of intermediate sub-247-1 : The synthesis of intermediate sub-247-1 was carried out following the same procedure as for intermediate sub-38-1, except raw material a-1 was replaced by raw material a-5 and raw material b-1 was replaced by raw material b-5, to give intermediate sub-247-1 in 34% yield.

[0243] Synthesis of intermediate sub-247-2: The synthesis of intermediate sub-247-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-247-1, to give intermediate sub-247-2 in 65% yield.

[0244] Synthesis of intermediate sub-247-3: The synthesis of intermediate sub-247-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-247-2, to give intermediate sub-247-3 in 91% yield.

[0245] Synthesis of intermediate sub-247-4: The synthesis of intermediate sub-247-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-247-3, to give intermediate sub-247-4 in 81% yield.

[0246] 1.8 Synthesis of intermediate sub-271-4:

[0247]

[0248] Synthesis of intermediate sub-271-1 : The synthesis of intermediate sub-271-1 was performed following the same synthetic procedure as for intermediate sub-38-1, except intermediate a-1 was replaced by intermediate a-6 and intermediate b-1 was replaced by intermediate b-6, to afford intermediate sub-271-1 in 31% yield.

[0249] Synthesis of intermediate sub-271-2: The synthesis of intermediate sub-271-2 was performed following the same synthetic procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-271-1, to afford intermediate sub-271-2 in 66% yield.

[0250] Synthesis of intermediate sub-271-3: The synthesis of intermediate sub-271-3 was performed following the same synthetic procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-271-2, to afford intermediate sub-271-3 in 90% yield.

[0251] Synthesis of intermediate sub-271-4: The synthesis of intermediate sub-271-4 was performed following the same synthetic procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-271-3, to afford intermediate sub-271-4 in 82% yield.

[0252] 1.9 Synthesis of intermediate sub-299-4:

[0253]

[0254] Synthesis of intermediate sub-299-1 : The synthesis of intermediate sub-299-1 was performed following the same synthetic procedure as for intermediate sub-38-1, except intermediate a-1 was replaced by intermediate a-7 and intermediate b-1 was replaced by intermediate b-6, to afford intermediate sub-299-1 in 33% yield.

[0255] Synthesis of intermediate sub-299-2: The synthesis of intermediate sub-299-2 was performed following the same synthetic procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-299-1, to afford intermediate sub-299-2 in 66% yield.

[0256] Synthesis of intermediate sub-299-3: The synthesis of intermediate sub-299-3 was performed following the same synthetic procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-299-2, to afford intermediate sub-299-3 in 91% yield.

[0257] Synthesis of intermediate sub-299-4: The synthesis of intermediate sub-299-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-299-3, affording intermediate sub-299-4 in 84% yield.

[0258] 1.10 Synthesis of intermediate sub-31-4:

[0259]

[0260] Synthesis of intermediate sub-31-1 : The synthesis of intermediate sub-31-1 was carried out following the same procedure as for intermediate sub-38-1, except raw material a-1 was replaced by raw material a-9, and raw material b-1 was replaced by raw material b-2, affording intermediate sub-31-1 in 33% yield.

[0261] Synthesis of intermediate sub-31-2: The synthesis of intermediate sub-31-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-31-1, affording intermediate sub-31-2 in 63% yield.

[0262] Synthesis of intermediate sub-31-3: The synthesis of intermediate sub-31-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-31-2, affording intermediate sub-31-3 in 92% yield.

[0263] Synthesis of intermediate sub-31-4: The synthesis of intermediate sub-31-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-31-3, affording intermediate sub-31-4 in 85% yield.

[0264] 1.11 Synthesis of intermediate sub-41-4:

[0265]

[0266] Synthesis of intermediate sub-41-1 : The synthesis of intermediate sub-41-1 was carried out following the same procedure as for intermediate sub-38-1, except raw material a-1 was replaced by raw material a-3, and raw material b-1 was replaced by raw material b-8, affording intermediate sub-41-1 in 37% yield.

[0267] Synthesis of intermediate sub-41-2: The synthesis of intermediate sub-41-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-41-1 to afford intermediate sub-41-2 in 64% yield.

[0268] Synthesis of intermediate sub-41-3: The synthesis of intermediate sub-41-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-41-2 to afford intermediate sub-41-3 in 91% yield.

[0269] Synthesis of intermediate sub-41-4: The synthesis of intermediate sub-41-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-41-3 to afford intermediate sub-41-4 in 84% yield.

[0270] 1.12 Synthesis of intermediate sub-59-4:

[0271]

[0272] Synthesis of intermediate sub-59-1: The synthesis of intermediate sub-59-1 was carried out following the same procedure as for intermediate sub-38-1, except raw material a-1 was replaced by raw material a-3, and raw material b-1 was replaced by raw material b-9 to afford intermediate sub-59-1 in 37% yield.

[0273] Synthesis of intermediate sub-59-2: The synthesis of intermediate sub-59-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-59-1 to afford intermediate sub-59-2 in 64% yield.

[0274] Synthesis of intermediate sub-59-3: The synthesis of intermediate sub-59-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-59-2 to afford intermediate sub-59-3 in 91% yield.

[0275] Synthesis of intermediate sub-59-4: The synthesis of intermediate sub-59-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-59-3 to afford intermediate sub-59-4 in 84% yield.

[0276] 1.13 Synthesis of intermediate sub-75-4:

[0277]

[0278] Synthesis of intermediate sub-75-1 : The synthesis of intermediate sub-75-1 was carried out following the same procedure as for intermediate sub-38-1, except intermediate a-1 was replaced by intermediate a-10 and intermediate b-1 was replaced by intermediate b-2, to afford intermediate sub-75-1 (yield 34%).

[0279] Synthesis of intermediate sub-75-2: The synthesis of intermediate sub-75-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-75-1, to afford intermediate sub-75-2 (yield 65%).

[0280] Synthesis of intermediate sub-75-3: The synthesis of intermediate sub-75-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-75-2, to afford intermediate sub-75-3 (yield 90%).

[0281] Synthesis of intermediate sub-75-4: The synthesis of intermediate sub-75-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-75-3, to afford intermediate sub-75-4 (yield 83%).

[0282] 1.14 Synthesis of intermediate sub-78-4:

[0283]

[0284] Synthesis of intermediate sub-78-1 : The synthesis of intermediate sub-78-1 was carried out following the same procedure as for intermediate sub-38-1, except intermediate a-1 was replaced by intermediate a-11 and intermediate b-1 was replaced by intermediate b-7, to afford intermediate sub-78-1 (yield 35%).

[0285] Synthesis of intermediate sub-78-2: The synthesis of intermediate sub-78-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-78-1, to afford intermediate sub-78-2 (yield 64%).

[0286] Synthesis of intermediate sub-78-3: The synthesis of intermediate sub-78-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-78-2, affording intermediate sub-78-3 in 91% yield.

[0287] Synthesis of intermediate sub-78-4: The synthesis of intermediate sub-78-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-78-3, affording intermediate sub-78-4 in 84% yield.

[0288] 1.15 Synthesis of intermediate sub-513-4:

[0289]

[0290] Synthesis of intermediate sub-513-2: The synthesis of intermediate sub-513-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-247-1, and starting material c-1 was replaced by starting material c-2, affording intermediate sub-513-2 in 61% yield.

[0291] Synthesis of intermediate sub-513-3: The synthesis of intermediate sub-513-3 was carried out following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-513-2, affording intermediate sub-513-3 in 90% yield.

[0292] Synthesis of intermediate sub-513-4: The synthesis of intermediate sub-513-4 was carried out following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-513-3, affording intermediate sub-513-4 in 84% yield.

[0293] 1.16 Synthesis of intermediate sub-520-4:

[0294]

[0295] Synthesis of intermediate sub-520-2: The synthesis of intermediate sub-520-2 was carried out following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-96-1, and starting material c-1 was replaced by starting material c-3, affording intermediate sub-520-2 in 63% yield.

[0296] Synthesis of intermediate sub-520-3: The synthesis of intermediate sub-520-3 was performed following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-520-2 to afford intermediate sub-520-3 in 90% yield.

[0297] Synthesis of intermediate sub-520-4: The synthesis of intermediate sub-520-4 was performed following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-520-3 to afford intermediate sub-520-4 in 82% yield.

[0298] 1.17 Synthesis of intermediate sub-522-4:

[0299]

[0300] Synthesis of intermediate sub-522-2: The synthesis of intermediate sub-522-2 was performed following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-299-1 and starting material c-1 was replaced by starting material c-4 to afford intermediate sub-522-2 in 60% yield.

[0301] Synthesis of intermediate sub-522-3: The synthesis of intermediate sub-522-3 was performed following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-522-2 to afford intermediate sub-522-3 in 91% yield.

[0302] Synthesis of intermediate sub-522-4: The synthesis of intermediate sub-522-4 was performed following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-522-3 to afford intermediate sub-522-4 in 83% yield.

[0303] 1.18 Synthesis of intermediate sub-532-4:

[0304]

[0305] Synthesis of intermediate sub-532-2: The synthesis of intermediate sub-532-2 was performed following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-8-1 and starting material c-1 was replaced by starting material c-5 to afford intermediate sub-532-2 in 60% yield.

[0306] Synthesis of intermediate sub-532-3: The synthesis of intermediate sub-532-3 was performed following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-532-2 to afford intermediate sub-532-3 in 90% yield.

[0307] Synthesis of intermediate sub-532-4: The synthesis of intermediate sub-532-4 was performed following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-532-3 to afford intermediate sub-532-4 in 84% yield.

[0308] 1.19 Synthesis of intermediate sub-536-4:

[0309]

[0310] Synthesis of intermediate sub-536-2: The synthesis of intermediate sub-536-2 was performed following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-271-1 and starting material c-1 was replaced by starting material c-6 to afford intermediate sub-536-2 in 62% yield.

[0311] Synthesis of intermediate sub-536-3: The synthesis of intermediate sub-536-3 was performed following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-536-2 to afford intermediate sub-536-3 in 91% yield.

[0312] Synthesis of intermediate sub-536-4: The synthesis of intermediate sub-536-4 was performed following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-536-3 to afford intermediate sub-536-4 in 83% yield.

[0313] 1.20 Synthesis of intermediate sub-552-4:

[0314]

[0315] Synthesis of intermediate sub-552-2: The synthesis of intermediate sub-552-2 was performed following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-82-1 and starting material c-1 was replaced by starting material c-7 to afford intermediate sub-552-2 in 64% yield.

[0316] Synthesis of intermediate sub-552-3: The synthesis of intermediate sub-552-3 was performed following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-552-2 to afford intermediate sub-552-3 in 89% yield.

[0317] Synthesis of intermediate sub-552-4: The synthesis of intermediate sub-552-4 was performed following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-552-3 to afford intermediate sub-552-4 in 82% yield.

[0318] 1.21 Synthesis of intermediate sub-561-4:

[0319]

[0320] Synthesis of intermediate sub-561-2: The synthesis of intermediate sub-561-2 was performed following the same procedure as for intermediate sub-38-2, except intermediate sub-38-1 was replaced by intermediate sub-229-1 and starting material c-1 was replaced by starting material c-8 to afford intermediate sub-561-2 in 63% yield.

[0321] Synthesis of intermediate sub-561-3: The synthesis of intermediate sub-561-3 was performed following the same procedure as for intermediate sub-38-3, except intermediate sub-38-2 was replaced by intermediate sub-561-2 to afford intermediate sub-561-3 in 93% yield.

[0322] Synthesis of intermediate sub-561-4: The synthesis of intermediate sub-561-4 was performed following the same procedure as for intermediate sub-38-4, except intermediate sub-38-3 was replaced by intermediate sub-561-3 to afford intermediate sub-561-4 in 81% yield.

[0323] 2. Synthesis of compound N-n:

[0324] 2.1 Synthesis of compound N-8, comprising the following steps:

[0325]

[0326] Synthesis of intermediate sub-8-5: Take a 500 mL three-necked round-bottom flask and put a stirring bar and an upper reflux tube. Add intermediate sub-8-4 (30.4 mmol), raw material d-1 (36.5 mmol), t-BuONa (60.8 mmol), S-Phos (1.2 mmol), Pd2(dba)3(0.6 mmol), toluene (100 mL) in sequence under nitrogen protection. Heat to 110°C and stir for 2 h. After the reaction is completed, turn off the heat and cool to 80°C. Quench the reaction with water and extract with ethyl acetate and water. Concentrate the organic phase, add 100 mL of n-hexane to crystallize, and dry to obtain intermediate sub-8-5 in a yield of 87%.

[0327] Synthesis of compound N-8: Take a 500 mL three-necked round-bottom flask and put a stirring bar and an upper reflux tube. Add intermediate sub-8-5 (25.9 mmol), raw material e-1 (25.9 mmol), Pd2(dba)3(0.5 mmol), Sphos (1.0 mmol), t-BuONa (51.9 mmol), xylene (100 mL) in sequence under nitrogen protection. Heat to 120°C and stir for 3 h. After the reaction is completed, turn off the heat and cool to 80°C. Quench the reaction with water and extract with ethyl acetate and water. Concentrate the organic phase, add 100 mL of ethanol to crystallize, and dry to obtain compound N-8 in a yield of 78%.

[0328] Elemental analysis: C 41 H 26 N2O2; Theoretical value: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured value: C, 85.07; H, 4.50; N, 4.88; HRMS (ESI) m / z [M+H]+: Theoretical value: 578.20; Measured value: 579.21.

[0329] 2.2 Synthesis of compound N-12, including the following steps:

[0330]

[0331] 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 by intermediate sub-12-4, i.e., sub-12-5 (yield 86%) is obtained.

[0332] 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%).

[0333] Elemental analysis: C 41 H 26 Theoretical N2O2 values: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured values: C, 85.07; H, 4.50; N, 4.88; HRMS(ESI) m / z [M+H]+: Theoretical value: 578.20; Measured value: 579.21.

[0334] 2.3 The synthesis of compound N-31 includes the following steps:

[0335]

[0336] 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%).

[0337] 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%).

[0338] 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.

[0339] 2.4 The synthesis of compound N-38 includes the following steps:

[0340]

[0341] 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%).

[0342] Synthesis of compound N-38: The synthesis of compound N-38 followed the same procedure as that of compound N-8, except that intermediate sub-8-5 was replaced by intermediate sub-38-5, while raw material e-1 was replaced by raw material e-2, to give compound N-38 (yield 81%).

[0343] Elemental analysis: C 47 H 30 N2O2 Theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.22; H, 4.62; N, 4.28; HRMS (ESI) m / z [M+H]+: Theoretical value: 654.23; Found: 655.23.

[0344] 2.5 Synthesis of compound N-41, comprising the following steps:

[0345]

[0346] Synthesis of intermediate sub-41-5: The synthesis of intermediate sub-41-5 followed the same procedure as that of intermediate sub-8-5, except that intermediate sub-8-4 was replaced by raw material sub-41-4, while raw material d-1 was replaced by raw material d-7, to give sub-41-5 (yield 83%).

[0347] Synthesis of compound N-41: The synthesis of compound N-41 followed the same procedure as that of compound N-8, except that intermediate sub-8-5 was replaced by intermediate sub-41-5, while raw material e-1 was replaced by raw material e-7, to give compound N-41 (yield 83%).

[0348] Elemental analysis: C 51 H 32 N2O2 Theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; Found: C, 86.93; H, 4.59; N, 3.94; HRMS (ESI) m / z [M+H]+: Theoretical value: 704.83; Found: 706.38.

[0349] 2.6 Synthesis of compound N-59, comprising the following steps:

[0350]

[0351] Synthesis of intermediate sub-59-5: The synthesis of intermediate sub-59-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced by starting material sub-59-4, to give sub-59-5 (yield 83%).

[0352] Synthesis of compound N-59: The synthesis of compound N-59 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-59-5, and starting material e-1 was replaced by starting material e-2, to give compound N-59 (yield 81%).

[0353] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.21; H, 4.59; N, 4.32; HRMS (ESI) m / z [M+H]+: Theoretical: 654.77; Found: 656.01.

[0354] 2.7 Synthesis of compound N-75, comprising the following steps:

[0355]

[0356] Synthesis of intermediate sub-75-5: The synthesis of intermediate sub-75-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced by starting material sub-75-4, to give sub-75-5 (yield 82%).

[0357] Synthesis of compound N-75: The synthesis of compound N-75 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-75-5, and starting material e-1 was replaced by starting material e-2, to give compound N-75 (yield 80%).

[0358] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.23; H, 4.61; N, 4.30; HRMS (ESI) m / z [M+H]+: Theoretical: 654.77; Found: 655.92.

[0359] 2.8 Synthesis of compound N-78, comprising the following steps:

[0360]

[0361] Synthesis of intermediate sub-78-5: The synthesis of intermediate sub-78-5 followed the same procedure as the synthesis of intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-78-4, affording sub-78-5 (yield 83%).

[0362] Synthesis of compound N-78: The synthesis of compound N-78 followed the same procedure as the synthesis of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-78-5, and starting material e-1 was replaced with starting material e-2, affording compound N-78 (yield 81%).

[0363] Elemental Analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.23; H, 4.62; N, 4.29; HRMS (ESI) m / z [M+H]+: Theoretical: 654.77; Found: 656.07.

[0364] 2.9 Synthesis of compound N-82, comprising the following steps:

[0365]

[0366] Synthesis of intermediate sub-82-5: The synthesis of intermediate sub-82-5 followed the same procedure as the synthesis of intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-82-4, affording sub-82-5 (yield 84%).

[0367] Synthesis of compound N-82: The synthesis of compound N-82 followed the same procedure as the synthesis of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-82-5, and starting material e-1 was replaced with starting material e-2, affording compound N-82 (yield 83%).

[0368] Elemental Analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.22; H, 4.62; N, 4.28; HRMS (ESI) m / z [M+H]+: Theoretical: 654.23; Found: 655.22.

[0369] 2.10 Synthesis of compound N-96, comprising the following steps:

[0370]

[0371] Synthesis of intermediate sub-96-5: The synthesis of intermediate sub-96-5 followed the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced by intermediate sub-96-4, to give sub-96-5 (84% yield).

[0372] Synthesis of compound N-96: The synthesis of compound N-96 followed the same procedure as for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-96-5, and starting material e-1 was replaced by starting material e-2, to give compound N-96 (84% yield).

[0373] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.20; H, 4.59; N, 4.32; HRMS (ESI) m / z [M+H]+: Theoretical: 654.23; Found: 655.21.

[0374] 2.11 Synthesis of compound N-106, comprising the following steps:

[0375]

[0376] Synthesis of compound N-106: The synthesis of compound N-106 followed the same procedure as for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-38-5, and starting material e-1 was replaced by starting material e-3, to give compound N-106 (83% yield).

[0377] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.20; H, 4.59; N, 4.32; HRMS (ESI) m / z [M+H]+: Theoretical: 654.23; Found: 655.21.

[0378] 2.12 Synthesis of compound N-136, comprising the following steps:

[0379]

[0380] Synthesis of intermediate sub-136-5: The synthesis of intermediate sub-136-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-136-4, to give sub-136-5 (yield 82%).

[0381] Synthesis of compound N-136: The synthesis of compound N-136 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-136-5, and starting material e-1 was replaced with starting material e-3, to give compound N-136 (yield 85%).

[0382] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.20; H, 4.59; N, 4.32; HRMS (ESI) m / z [M+H]+: Theoretical: 654.23; Found: 655.21.

[0383] 2.13 Synthesis of compound N-154, comprising the following steps:

[0384]

[0385] Synthesis of intermediate sub-154-5: The synthesis of intermediate sub-154-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-8-4, and starting material d-1 was replaced with starting material d-2, to give sub-154-5 (yield 84%).

[0386] Synthesis of compound N-154: The synthesis of compound N-154 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-154-5, and starting material e-1 was replaced with starting material e-3, to give compound N-154 (yield 83%).

[0387] Elemental analysis: C 53 H 34 N2O2 Theoretical: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Found: C, 87.07; H, 4.65; N, 3.88; HRMS (ESI) m / z [M+H]+: Theoretical: 730.26; Found: 731.24.

[0388] 2.14 Synthesis of compound N-171, comprising the following steps:

[0389]

[0390] Synthesis of intermediate sub-171-5: The synthesis of intermediate sub-171-5 followed the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-38-4, and starting material d-1 was replaced with starting material d-3, to give sub-171-5 (84% yield).

[0391] Synthesis of compound N-171: The synthesis of compound N-171 followed the same procedure as for compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-171-5, and starting material e-1 was replaced with starting material e-4, to give compound N-171 (83% yield).

[0392] Elemental analysis: C 53 H 34 N2O2 Calc: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Found: C, 87.08; H, 4.67; N, 3.86; HRMS (ESI) m / z [M+H]+: Calc: 730.26; Found: 731.24.

[0393] 2.15 Synthesis of compound N-247, comprising the following steps:

[0394]

[0395] Synthesis of intermediate sub-247-5: The synthesis of intermediate sub-247-5 followed the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-247-4, and starting material d-1 was replaced with starting material d-4, to give sub-247-5 (81% yield).

[0396] Synthesis of compound N-247: The synthesis of compound N-247 followed the same procedure as for compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-247-5, and starting material e-1 was replaced with starting material e-2, to give compound N-247 (86% yield).

[0397] Elemental analysis: C 53 H 32 N2O3 Calc: C, 85.46; H, 4.33; N, 3.76; O, 6.44; Found: C, 85.43; H, 4.31; N, 3.79; HRMS (ESI) m / z [M+H]+: Calc: 744.24; Found: 745.23.

[0398] 2.16 Synthesis of compound N-271 comprising the following steps:

[0399]

[0400] Synthesis of intermediate sub-271-5: The synthesis of intermediate sub-271-5 was carried out according to the same procedure as described for intermediate sub-8-5 except intermediate sub-8-4 was replaced by intermediate sub-271-4 to give sub-271-5 (yield 83%).

[0401] Synthesis of compound N-271: The synthesis of compound N-271 was carried out according to the same procedure as described for compound N-8 except intermediate sub-8-5 was replaced by intermediate sub-271-5 and starting material e-1 was replaced by starting material e-2 to give compound N-271 (yield 86%).

[0402] Elemental analysis: C 47 H 30 N2O2 Calc: C, 86.22; H, 4.62; N, 4.28; O, 4.89. Found: C, 86.22; H, 4.62; N, 4.28. HRMS (ESI) m / z [M+H]+: Calcd: 654.23; Found: 655.23.

[0403] 2.17 Synthesis of compound N-287 comprising the following steps:

[0404]

[0405] Synthesis of intermediate sub-287-5: The synthesis of intermediate sub-287-5 was carried out according to the same procedure as described for intermediate sub-8-5 except intermediate sub-8-4 was replaced by intermediate sub-247-4 and starting material d-1 was replaced by starting material d-5 to give sub-287-5 (yield 83%).

[0406] Synthesis of compound N-287: The synthesis of compound N-287 was carried out according to the same procedure as described for compound N-8 except intermediate sub-8-5 was replaced by intermediate sub-287-5 and starting material e-1 was replaced by starting material e-3 to give compound N-287 (yield 86%).

[0407] Elemental analysis: C 53 H 34N2O2 Theoretical: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Found: C, 87.07; H, 4.66; N, 3.86; HRMS (ESI) m / z [M+H]+: Calcd for C36H34N4O2, 730.26; Found, 731.25.

[0408] 2.18 Synthesis of compound N-299, comprising the following steps:

[0409]

[0410] Synthesis of intermediate sub-336-5: The synthesis of intermediate sub-336-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced by intermediate sub-299-4 and raw material d-1 was replaced by raw material d-6, to afford sub-336-5 in 84% yield.

[0411] Synthesis of compound N-336: The synthesis of compound N-336 was performed following the same procedure as for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-336-5 and raw material e-1 was replaced by raw material e-2, to afford compound N-336 in 86% yield.

[0412] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Found: C, 87.07; H, 4.66; N, 3.86; HRMS (ESI) m / z [M+H]+: Calcd for C36H34N4O2, 730.26; Found, 731.25.

[0413] 2.19 Synthesis of compound N-336, comprising the following steps:

[0414]

[0415] Synthesis of intermediate sub-336-5: The synthesis of intermediate sub-336-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced by intermediate sub-299-4 and raw material d-1 was replaced by raw material d-6, to afford sub-336-5 in 84% yield.

[0416] Synthesis of compound N-336: The synthesis of compound N-336 was performed following the same procedure as for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-336-5 and raw material e-1 was replaced by raw material e-2, to afford compound N-336 in 86% yield.

[0417] 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.

[0418] The synthesis of compound N-347, denoted as 2.20, includes the following steps:

[0419]

[0420] 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%).

[0421] 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%).

[0422] 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.

[0423] 2.21 The synthesis of compound N-353 includes the following steps:

[0424]

[0425] 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%).

[0426] 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%).

[0427] 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.

[0428] 2.22 The synthesis of compound N-358 includes the following steps:

[0429]

[0430] 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%).

[0431] 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%).

[0432] 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.

[0433] 2.23 The synthesis of compound N-382 includes the following steps:

[0434]

[0435] Synthesis of compound N-382: The synthesis of compound N-382 followed the same procedure as for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-154-5, while raw material e-1 was replaced by raw material e-7, to give compound N-382 (yield 86%).

[0436] Elemental analysis: C 47 H 30 N2O2 Theoretical: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.21; H, 4.65; N, 4.29; HRMS (ESI) m / z [M+H]+: Theoretical: 654.77; Found: 655.90.

[0437] 2.24 Synthesis of compound N-459, comprising the following steps:

[0438]

[0439] Synthesis of intermediate sub-459-5: The synthesis of intermediate sub-459-5 followed the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced by raw material sub-271-4, while raw material d-1 was replaced by raw material d-8, to give sub-459-5 (yield 83%).

[0440] Synthesis of compound N-459: The synthesis of compound N-459 followed the same procedure as for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-459-5, while raw material e-1 was replaced by raw material e-2, to give compound N-459 (yield 82%).

[0441] Elemental analysis: C 55 H 34 N2O2 Theoretical: C, 87.51; H, 4.54; N, 3.71; O, 4.24; Found: C, 87.49; H, 4.56; N, 3.70; HRMS (ESI) m / z [M+H]+: Theoretical: 754.89; Found: 756.21.

[0442] 2.25 Synthesis of compound N-462, comprising the following steps:

[0443]

[0444] Synthesis of intermediate sub-462-5: The synthesis of intermediate sub-462-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-136-4, and starting material d-1 was replaced with starting material d-5, to give sub-462-5 (83% yield).

[0445] Synthesis of compound N-462: The synthesis of compound N-462 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-462-5, and starting material e-1 was replaced with starting material e-9, to give compound N-462 (82% yield).

[0446] Elemental analysis: C 57 H 36 N2O2 Calc: C, 87.67; H, 4.65; N, 3.59; O, 4.10; Found: C, 87.69; H, 4.67; N, 3.54; HRMS (ESI) m / z [M+H]+: Calcd: 780.92; Found: 782.12.

[0447] 2.26 Synthesis of compound N-469, comprising the following steps:

[0448] 1

[0449] Synthesis of intermediate sub-469-5: The synthesis of intermediate sub-469-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-247-4, and starting material d-1 was replaced with starting material d-9, to give sub-469-5 (84% yield).

[0450] Synthesis of compound N-469: The synthesis of compound N-469 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-469-5, and starting material e-1 was replaced with starting material e-10, to give compound N-469 (81% yield).

[0451] Elemental analysis: C 59 H 34 N2O3S Calc: C, 83.27; H, 4.03; N, 3.29; O, 5.64; S, 3.77; Found: C, 83.28; H, 4.01; N, 3.30; S, 3.75; HRMS (ESI) m / z [M+H]+: Calcd: 850.99; Found: 852.24.

[0452] 2.27 Synthesis of compound N-476 comprising the following steps:

[0453]

[0454] Synthesis of intermediate sub-488-5: The synthesis of intermediate sub-488-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-247-4, and starting material d-1 was replaced with starting material d-11 to afford sub-488-5 in 84% yield.

[0455] Synthesis of compound N-488: The synthesis of compound N-488 was performed following the same procedure as for compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-488-5, and starting material e-1 was replaced with starting material e-12 to afford compound N-488 in 81% yield.

[0456] Elemental analysis: C 57 H 34 N2OS2 Calc: C, 82.78; H, 4.14; N, 3.39; O, 1.93; S, 7.75; Found: C, 82.79; H, 4.11; N, 3.41; S, 7.72; HRMS (ESI) m / z [M+H]+: Calcd: 827.03; Found: 828.41.

[0457] 2.28 Synthesis of compound N-488 comprising the following steps:

[0458]

[0459] Synthesis of intermediate sub-488-5: The synthesis of intermediate sub-488-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-247-4, and starting material d-1 was replaced with starting material d-11 to afford sub-488-5 in 84% yield.

[0460] Synthesis of compound N-488: The synthesis of compound N-488 was performed following the same procedure as for compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-488-5, and starting material e-1 was replaced with starting material e-12 to afford compound N-488 in 81% yield.

[0461] Elemental analysis: C 53 H 32N2O2theoretical: C, 86.45; H, 4.74; N, 4.11; O, 4.70; found: C, 86.43; H, 4.75; N, 4.10; HRMS (ESI) m / z [M+H]+: Calcd for C32H32N4O2: 680.81; Found: 682.33.

[0462] 2.29 Synthesis of compound N-504, comprising the following steps:

[0463]

[0464] Synthesis of intermediate sub-506-5: The synthesis of intermediate sub-506-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material f-3 and starting material d-1 was replaced with starting material d-12 to afford sub-506-5 in 88% yield.

[0465] Synthesis of compound N-506: The synthesis of compound N-506 was performed following the same procedure as for compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-506-5 and starting material e-1 was replaced with starting material e-13 to afford compound N-506 in 84% yield.

[0466] Elemental Analysis: C 49 H 32 N2O2theoretical: C, 86.45; H, 4.74; N, 4.11; O, 4.70; found: C, 86.43; H, 4.75; N, 4.10; HRMS (ESI) m / z [M+H]+: Calcd for C32H32N4O2: 680.81; Found: 682.33.

[0467] 2.30 Synthesis of compound N-506, comprising the following steps:

[0468]

[0469] Synthesis of intermediate sub-506-5: The synthesis of intermediate sub-506-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material f-3 and starting material d-1 was replaced with starting material d-12 to afford sub-506-5 in 88% yield.

[0470] Synthesis of compound N-506: The synthesis of compound N-506 followed the same procedure as for compound N-8, except that intermediate sub-8-5 was replaced by intermediate sub-506-5, while raw material e-1 was replaced by raw material e,14, to give compound N-506 (yield 83%).

[0471] Elemental analysis: C 55 H 34 N2O3 Calc: C, 85.69; H, 4.45; N, 3.63; O, 6.23. Found: C, 85.71; H, 4.47; N, 3.60. HRMS (ESI) m / z [M+H]+: Calcd: 770.89; Found: 771.28.

[0472] 2.31 Synthesis of compound N-513, comprising the following steps:

[0473]

[0474] Synthesis of intermediate sub-513-5: The synthesis of intermediate sub-513-5 followed the same procedure as for intermediate sub-8-5, except that intermediate sub-8-4 was replaced by intermediate sub-513-4, to give sub-513-5 (yield 82%).

[0475] Synthesis of compound N-513: The synthesis of compound N-513 followed the same procedure as for compound N-8, except that intermediate sub-8-5 was replaced by intermediate sub-513-5, while raw material e-1 was replaced by raw material e-3, to give compound N-513 (yield 84%).

[0476] Elemental analysis: C 51 H 32 N2O2 Calc: C, 86.91; H, 4.58; N, 3.97; O, 4.54. Found: C, 86.90; H, 4.61; N, 3.96. HRMS (ESI) m / z [M+H]+: Calcd: 704.83; Found: 705.97.

[0477] 2.32 Synthesis of compound N-520, comprising the following steps:

[0478]

[0479] Synthesis of intermediate sub-520-5: The synthesis of intermediate sub-520-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-520-4, and starting material d-1 was replaced with starting material d-5, to give sub-520-5 (83% yield).

[0480] Synthesis of compound N-520: The synthesis of compound N-520 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-520-5, and starting material e-1 was replaced with starting material e-3, to give compound N-520 (83% yield).

[0481] Elemental analysis: C 59 H 38 N2O2 Theory: C, 87.82; H, 4.75; N, 3.47; O, 3.97; Found: C, 87.80; H, 4.76; N, 3.46; HRMS (ESI) m / z [M+H]+: Calcd for C52H46N2O2, 806.97; Found, 808.31.

[0482] 2.33 Synthesis of compound N-522, comprising the following steps:

[0483]

[0484] Synthesis of intermediate sub-522-5: The synthesis of intermediate sub-522-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-522-4, and starting material d-1 was replaced with starting material d-7, to give sub-522-5 (84% yield).

[0485] Synthesis of compound N-522: The synthesis of compound N-522 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-522-5, and starting material e-1 was replaced with starting material e-6, to give compound N-522 (83% yield).

[0486] Elemental analysis: C 65 H 40 N2O2 Theory: C, 88.61; H, 4.58; N, 3.18; O, 3.63; Found: C, 88.66; H, 4.56; N, 3.17; HRMS (ESI) m / z [M+H]+: Calcd for C53H48N2O2, 881.05; Found, 882.28.

[0487] 2.34 Synthesis of compound N-532, comprising the following steps:

[0488]

[0489] Synthesis of intermediate sub-532-5: The synthesis of intermediate sub-532-5 was performed according to the same procedure as described for intermediate sub-8-5, except intermediate sub-8-4 was replaced by starting material sub-532-4, and starting material d-1 was replaced by starting material d-4, to afford sub-532-5 (81% yield).

[0490] Synthesis of compound N-532: The synthesis of compound N-532 was performed according to the same procedure as described for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-532-5, and starting material e-1 was replaced by starting material e-2, to afford compound N-532 (84% yield).

[0491] Elemental analysis: C 65 H 40 N2O3 Calc: C, 87.03; H, 4.49; N, 3.12; O, 5.35. Found: C, 87.06; H, 4.50; N, 3.13. HRMS (ESI) m / z [M+H]+: Calcd: 897.05; Found: 898.28.

[0492] 2.35 Synthesis of compound N-536, comprising the following steps:

[0493]

[0494] Synthesis of intermediate sub-536-5: The synthesis of intermediate sub-536-5 was performed according to the same procedure as described for intermediate sub-8-5, except intermediate sub-8-4 was replaced by starting material sub-536-4, to afford sub-536-5 (84% yield).

[0495] Synthesis of compound N-536: The synthesis of compound N-536 was performed according to the same procedure as described for compound N-8, except intermediate sub-8-5 was replaced by intermediate sub-536-5, and starting material e-1 was replaced by starting material e-2, to afford compound N-536 (82% yield).

[0496] Elemental analysis: C 53 H 32N2O3 Theoretical: C, 85.46; H, 4.33; N, 3.76; O, 6.44; Found: C, 85.47; H, 4.36; N, 3.74; HRMS (ESI) m / z [M+H]+: Theoretical: 744.85; Found: 745.99.

[0497] 2.36 Synthesis of compound N-552, comprising the following steps:

[0498]

[0499] Synthesis of intermediate sub-552-5: The synthesis of intermediate sub-552-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-552-4, and starting material d-1 was replaced with starting material d-2, to afford sub-552-5 (83% yield).

[0500] Synthesis of compound N-552: The synthesis of compound N-552 was performed following the same procedure as for compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-552-5, and starting material e-1 was replaced with starting material e-3, to afford compound N-552 (83% yield).

[0501] Elemental Analysis: C 59 H 36 N2O2S Theoretical: C, 84.66; H, 4.34; N, 3.35; O, 3.82; S, 3.83; Found: C, 84.64; H, 4.36; N, 3.32; S, 3.84; HRMS (ESI) m / z [M+H]+: Theoretical: 837.01; Found: 838.41.

[0502] 2.37 Synthesis of compound N-561, comprising the following steps:

[0503]

[0504] Synthesis of intermediate sub-561-5: The synthesis of intermediate sub-561-5 was performed following the same procedure as for intermediate sub-8-5, except intermediate sub-8-4 was replaced with starting material sub-561-4, and starting material d-1 was replaced with starting material d-5, to afford sub-561-5 (81% yield).

[0505] Synthesis of compound N-561 : The synthesis of compound N-561 followed the same procedure as for compound N-8, except that intermediate sub-8-5 was replaced by intermediate sub-561-5, while raw material e-1 was replaced by raw material e-5, to give compound N-561 (yield 82%).

[0506] Elemental analysis: C 63 H 40 N2O2 Theoretical: C, 88.29; H, 4.70; N, 3.27; O, 3.73; Found: C, 88.31; H, 4.67; N, 3.25; HRMS (ESI) m / z [M+H]+: Theoretical: 857.03; Found: 858.40.

[0507] 2.38 Synthesis of compound N-388, comprising the following steps:

[0508]

[0509] Synthesis of intermediate sub-388-5: The synthesis of intermediate sub-388-5 followed the same procedure as for intermediate sub-8-5, except that intermediate sub-8-4 was replaced by raw material sub-247-4, while raw material d-1 was replaced by raw material d-13, to give sub-388-5 (yield 80%).

[0510] Synthesis of compound N-388: The synthesis of compound N-388 followed the same procedure as for compound N-8, except that intermediate sub-8-5 was replaced by intermediate sub-388-5, to give compound N-388 (yield 83%).

[0511] Elemental analysis: C 50 H 34 N2O2 Theoretical: C, 86.43; H, 4.93; N, 4.03; O, 4.61; Found: C, 86.42; H, 4.95; N, 4.01; HRMS (ESI) m / z [M+H]+: Theoretical: 694.83; Found: 696.07.

[0512] 2.39 Synthesis of compound N-402, comprising the following steps:

[0513]

[0514] Synthesis of intermediate sub-402-5: The synthesis of intermediate sub-402-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-247-4, and raw material d-1 was replaced with raw material d-14, to give sub-402-5 (yield 80%).

[0515] Synthesis of compound N-402: The synthesis of compound N-402 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-402-5, and raw material e-1 was replaced with raw material e-2, to give compound N-402 (yield 85%).

[0516] Elemental analysis: C 66 H 40 N2O2 Theoretical: C, 88.77; H, 4.51; N, 3.14; O, 3.58; Found: C, 88.79; H, 4.53; N, 3.11; HRMS (ESI) m / z [M+H]+: Theoretical: 893.06; Found: 894.23.

[0517] 2.40 Synthesis of compound N-570, comprising the following steps:

[0518]

[0519] Synthesis of intermediate sub-570-5: The synthesis of intermediate sub-570-5 followed the same procedure as that of intermediate sub-8-5, except intermediate sub-8-4 was replaced with intermediate sub-299-4, and raw material d-1 was replaced with raw material d-15, to give sub-570-5 (yield 81%).

[0520] Synthesis of compound N-570: The synthesis of compound N-570 followed the same procedure as that of compound N-8, except intermediate sub-8-5 was replaced with intermediate sub-570-5, and raw material e-1 was replaced with raw material e-2, to give compound N-570 (yield 84%).

[0521] Elemental analysis: C 59 H 42 N2O2 Theoretical: C, 87.38; H, 5.22; N, 3.45; O, 3.95; Found: C, 87.40; H, 5.25; N, 3.41; HRMS (ESI) m / z [M+H]+: Theoretical: 811.00; Found: 812.31.

[0522] 2.41 Synthesis of compound N-576, comprising the following steps:

[0523]

[0524] 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 by starting material sub-271-4, and starting material d-1 is replaced by starting material d-16, to give sub-576-5 (yield 80%).

[0525] 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 by intermediate sub-576-5, and starting material e-1 is replaced by starting material e-2, to give compound N-576 (yield 82%).

[0526] Elemental analysis: C 58 H 40 N2O2 Theoretical value: C, 87.41; H, 5.06; N, 3.52; O, 4.01; Found: C, 87.43; H, 5.04; N, 3.50; HRMS (ESI) m / z [M+H]+: Theoretical value: 796.97; Found: 798.09.

[0527] Device Example

[0528] The device example provides an organic electroluminescent device composed of different organic electroluminescent materials, such as Figure 1 As shown in the device structure: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0529] The main materials used in the device examples and comparative examples are shown in Table 1 below:

[0530]

[0531] The specific preparation process of device example 1 is shown as follows:

[0532] (1) Substrate cleaning:

[0533] 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.

[0534] (2) Evaporation of organic light-emitting functional layer:

[0535] 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.

[0536] HT-12 was deposited on the hole injection layer as a hole transport layer, with a film thickness of 80 nm.

[0537] A 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.

[0538] 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.

[0539] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0540] Al was deposited on the electron injection layer as a cathode, with a total film thickness of 90 nm.

[0541] 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.

[0542] The organic electroluminescent devices obtained in Device Examples 1-41 and Device Comparative Examples 1-2 were tested.

[0543] 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;

[0544] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0545] 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.

[0546] The device performance test results are shown in Table 2:

[0547] Table 2

[0548]

[0549] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0550] Obviously, the above embodiments are merely example for clearly illustrating but not limitation to the embodiments. Based on the above description, other different forms of changes or variations can be made by those skilled in the art. Here, all the embodiments need not and can not be enumerated. The obvious changes or variations derived from the above description are still within the protection scope of the present application.

Claims

1. An organic compound, characterized by, The organic compound has a structure shown in formula (1): Formula (1) In formula (1), Y1, Y2 are each independently selected from O or S; Ring A is present and is selected from a benzene ring; Ar 1 , Ar 2 are identical or different, each independently selected from the group consisting of substituted or unsubstituted C6-C30aryl, unsubstituted C3-C30heteroaryl; L 1 , L 2 are identical or different, each independently selected from the group consisting of a single bond, phenylene; R1 is selected from substituted or unsubstituted C6-C20 aryl, dibenzofuranyl, dibenzothiophenyl; R2 is selected from deuterium; n1 is 1; n2 is any integer from 0 to 3; wherein the substituents of the substituted C6-C20 aryl, the substituted C6-C30 aryl are selected from one or a combination of at least two of deuterium, methyl, cyclohexane, cyclopentane, C6-C30 aryl.

2. The organic compound according to claim 1, characterized by The organic compound is selected from any one of the structures of Formula 1-5 to Formula 1-16, wherein Y1, Y2, Ar 1 , Ar 2 , L 1 , L 2 , R1, R2, n1, n2 are defined the same as in claim 1: 。 3. The organic compound according to claim 1 or 2, characterized by Ar 1 , Ar 2 are the same or different, each independently selected from a substituted or unsubstituted A group, wherein the A group is selected from the group consisting of phenyl, naphthyl, phenanthryl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, benzospibfluorenyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, N-phenylcarbazolyl, N-biphenylcarbazolyl; wherein the substituents of the substituted A group are selected from one or a combination of at least two of deuterium, methyl, cyclohexane, cyclopentane, C6-C30 aryl.

4. The organic compound according to claim 1 or 2, characterized by R1 is selected from naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, substituted or unsubstituted phenyl; The substituents of the substituted phenyl are selected from one or a combination of at least two of phenyl, biphenyl, naphthyl.

5. The organic compound according to claim 1 or 2, characterized by The organic compound is selected from any one of the following structures: 。 6. An organic electroluminescent material, characterized by The organic electroluminescent material comprises the organic compound according to any one of claims 1-5.

7. An organic electroluminescent device, characterized by The organic electroluminescent device comprises an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising the organic compound according to any one of claims 1-5 or the organic electroluminescent material according to claim 6.

8. The organic electroluminescent device according to claim 7, characterized in that The organic layer comprises any one or a combination of at least two of 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.

9. The organic electroluminescent device according to claim 7 or 8, characterized in that, The organic layer comprises a light-emitting layer, the light-emitting layer comprising the organic compound according to any one of claims 1-5 or the organic electroluminescent material according to claim 6.

10. The organic electroluminescent device according to claim 9, characterized in that The light-emitting layer comprises a host material and a guest material, the host material comprising the organic compound according to any one of claims 1-5 or the organic electroluminescent material according to any one of claim 6.

11. An electronic device, comprising: The electronic device comprises the organic electroluminescent device according to any one of claims 7-10 or the organic electroluminescent material according to claim 6 or the organic compound according to any one of claims 1-5.

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