Organic compound, mixture, composition, organic light-emitting device and display panel

Abstract

An organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. The organic compound has a structure as shown in general formula (1) or (2). By means of introducing a group that enhances the overall conjugation of a compound into a boron-nitrogen compound, the material performance is improved, the luminous efficiency of the organic light-emitting device is improved, and the service life of the organic light-emitting device is prolonged.

Description

Organic compound, mixture, composition, organic light-emitting device and display panel Technical Field

[0001] The present application relates to the field of display, and in particular to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. Background Art

[0002] Currently, organic electroluminescent devices, such as OLEDs (Organic Light-Emitting Diodes), typically have an anode, a cathode, and an organic layer located between them. The organic materials in the organic layer convert electrical energy into light energy, thereby achieving organic electroluminescence. To improve the luminous efficiency and service life of organic electroluminescent devices, the organic layers are often multi-layered, with different organic materials in each layer. Specifically, the organic layers mainly include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the anode and cathode of the organic electroluminescent device, the anode injects holes into the organic layer, and the cathode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state, thereby achieving the light emission of the organic electroluminescent device. Organic electroluminescent devices have the characteristics of autonomous luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response. Therefore, organic electroluminescent devices have broad application prospects.

[0003] In order to improve the luminous efficiency of organic electroluminescent elements, various luminescent material systems based on fluorescence and phosphorescence have been developed. Among them, organic electroluminescent elements using fluorescent materials have the characteristics of high reliability, but under electrical excitation, due to the branching ratio of the singlet excited state and the triplet excited state of the exciton is 1:3, the internal electroluminescent quantum efficiency will be limited to less than 25%, while organic electroluminescent elements using phosphorescent materials can achieve almost 100% internal electroluminescent quantum efficiency. However, phosphorescent materials usually use metal complexes containing iridium and platinum, the raw materials are expensive and the synthesis is complex, and phosphorescent organic electroluminescent elements will also produce a roll-off effect, that is, the luminous efficiency decreases rapidly with the increase of current or brightness, which limits its application under high brightness.

[0004] To overcome these issues, existing technologies typically employ various material combinations based on organic compounds, such as composite excited-state materials and thermally activated delayed fluorescence (TADF) materials, attempting to utilize reverse internal conversion to achieve high efficiencies comparable to those of phosphorescent organic electroluminescent devices. However, conventional organic compounds with TADF have limited performance improvements in terms of both efficiency and lifespan, making it difficult to improve the luminous efficiency and lifespan of organic electroluminescent devices using organic compounds with TADF.

[0005] Therefore, there is an urgent need for an organic compound for an organic light-emitting device to solve the above technical problems. Technical issues

[0006] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device and a display panel, which can improve the luminous efficiency and life of an organic electroluminescent element. Technical Solutions

[0007] To solve the above problems, the technical solutions provided by this application are as follows:

[0008] The present application provides an organic compound having a structure as shown in general formula (1) or (2):

[0009] wherein Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-2):

[0010] Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5):

[0011] When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formulas (A-2) to (A-5);

[0012] The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position on the same benzene ring;

[0013] Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4):

[0014] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0015] n0, n1, n2, and n5 are each independently selected from a positive integer between 0 and 14;

[0016] Any of R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0017] When n0 is greater than or equal to 2, two adjacent R0s may form a ring with each other or not; when n1 is greater than or equal to 2, two adjacent R1s may form a ring with each other or not; when n2 is greater than or equal to 2, two adjacent R2s may form a ring with each other or not; when n5 is greater than or equal to 2, two adjacent R5s may form a ring with each other or not.

[0018] Preferably, the organic compound has a structure as shown in any one of the general formulas (2-1) to (2-28):

[0019] wherein any one of R3 and R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0020] n3 is greater than or equal to 0 and less than or equal to 5;

[0021] When n3 is greater than or equal to 2, two adjacent R3s may form a ring or not;

[0022] n4 is greater than or equal to 0 and less than or equal to 5;

[0023] When n4 is greater than or equal to 2, two adjacent R4s may form a ring or not.

[0024] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms.

[0025] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 5 carbon atoms.

[0026] Preferably, when Ar2 contains a structure represented by formula (B-2), the structure represented by formula (B-2) is selected from:

[0027] as well as At least one of .

[0028] Preferably, the organic compound is a blue light-emitting material.

[0029] Preferably, the organic compound is selected from the following compounds:

[0030] The present application also provides a mixture comprising an organic compound and at least one organic functional material, wherein the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent material, a host material or an organic dye;

[0031] Wherein, the organic compound has a structure as shown in general formula (1) or (2):

[0032] wherein Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3):

[0033] Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5):

[0034] When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formulas (A-2) to (A-5);

[0035] The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position on the same benzene ring;

[0036] Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4):

[0037] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0038] n0, n1, n2, and n5 are each independently selected from a positive integer between 0 and 14;

[0039] Any of R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0040] When n0 is greater than or equal to 2, two adjacent R0s may form a ring with each other or not; when n1 is greater than or equal to 2, two adjacent R1s may form a ring with each other or not; when n2 is greater than or equal to 2, two adjacent R2s may form a ring with each other or not; when n5 is greater than or equal to 2, two adjacent R5s may form a ring with each other or not.

[0041] The present application also provides a composition comprising an organic compound or mixture, and at least one organic solvent;

[0042] The mixture comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes;

[0043] The organic compound has a structure as shown in general formula (1) or (2):

[0044] wherein Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3):

[0045] Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5):

[0046] When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formulas (A-2) to (A-5);

[0047] The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position on the same benzene ring;

[0048] Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4):

[0049] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0050] n0, n1, n2, and n5 are each independently selected from a positive integer between 0 and 14;

[0051] Any of R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0052] When n0 is greater than or equal to 2, two adjacent R0s may form a ring with each other or not; when n1 is greater than or equal to 2, two adjacent R1s may form a ring with each other or not; when n2 is greater than or equal to 2, two adjacent R2s may form a ring with each other or not; when n5 is greater than or equal to 2, two adjacent R5s may form a ring with each other or not.

[0053] The present application also provides an organic light-emitting device, comprising:

[0054] a first electrode;

[0055] a second electrode, disposed opposite to the first electrode; and

[0056] an organic functional layer, located between the first electrode and the second electrode;

[0057] Wherein, the material of the organic functional layer includes one or more organic compounds, or a mixture, or is prepared from a combination;

[0058] The composition comprises the organic compound or the mixture, and at least one organic solvent;

[0059] The mixture comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes;

[0060] The organic compound has a structure as shown in general formula (1) or (2):

[0061] wherein Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3):

[0062] Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5):

[0063] When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formulas (A-2) to (A-5);

[0064] The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position on the same benzene ring;

[0065] Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4):

[0066] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0067] n0, n1, n2, and n5 are each independently selected from a positive integer between 0 and 14;

[0068] Any of R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0069] When n0 is greater than or equal to 2, two adjacent R0s may form a ring with each other or not; when n1 is greater than or equal to 2, two adjacent R1s may form a ring with each other or not; when n2 is greater than or equal to 2, two adjacent R2s may form a ring with each other or not; when n5 is greater than or equal to 2, two adjacent R5s may form a ring with each other or not.

[0070] Preferably, the organic functional layer at least includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, the guest material is one or more of the organic compounds, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

[0071] Preferably, the host material includes one or more of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0072] Preferably, the mass ratio of the host material to the guest material is 99:1 to 70:30.

[0073] The present application also provides a display panel, including an organic light-emitting device, wherein the organic light-emitting device includes:

[0074] a first electrode;

[0075] a second electrode, disposed opposite to the first electrode; and

[0076] an organic functional layer, located between the first electrode and the second electrode;

[0077] Wherein, the material of the organic functional layer includes one or more organic compounds, or a mixture, or is prepared from a combination;

[0078] The composition comprises the organic compound or the mixture, and at least one organic solvent;

[0079] The mixture comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes;

[0080] The organic compound has a structure as shown in general formula (1) or (2):

[0081] wherein Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3):

[0082] Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5):

[0083] When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formulas (A-2) to (A-5);

[0084] The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position on the same benzene ring;

[0085] Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4):

[0086] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0087] n0, n1, n2, and n5 are each independently selected from a positive integer between 0 and 14;

[0088] Any of R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0089] When n0 is greater than or equal to 2, two adjacent R0s may form a ring with each other or not; when n1 is greater than or equal to 2, two adjacent R1s may form a ring with each other or not; when n2 is greater than or equal to 2, two adjacent R2s may form a ring with each other or not; when n5 is greater than or equal to 2, two adjacent R5s may form a ring with each other or not.

[0090] Preferably, the organic compound has a structure as shown in any one of the general formulas (2-1) to (2-28):

[0091] wherein any one of R3 and R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0092] n3 is greater than or equal to 0 and less than or equal to 5;

[0093] When n3 is greater than or equal to 2, two adjacent R3s may form a ring or not;

[0094] n4 is greater than or equal to 0 and less than or equal to 5;

[0095] When n4 is greater than or equal to 2, two adjacent R4s may form a ring or not.

[0096] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms.

[0097] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 5 carbon atoms.

[0098] Preferably, when Ar2 contains a structure represented by formula (B-2), the structure represented by formula (B-2) is selected from:

[0099] as well as At least one of .

[0100] Preferably, the organic functional layer at least includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, the guest material is one or more of the organic compounds, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

[0101] Preferably, the host material includes one or more of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Beneficial effects

[0102] The present application improves material properties, increases the luminous efficiency of organic light-emitting devices, and prolongs the service life of organic light-emitting devices by introducing groups into boron nitrogen compounds that increase the overall conjugation of the compounds. BRIEF DESCRIPTION OF THE DRAWINGS

[0103] FIG1 is a schematic diagram of a first structure of an organic light-emitting device provided in an embodiment of the present application;

[0104] FIG2 is a schematic diagram of a second structure of an organic light-emitting device provided in an embodiment of the present application;

[0105] FIG3 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M16 provided in an example of the present application;

[0106] FIG4 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M25 provided in an example of the present application;

[0107] FIG5 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M277 provided in an example of the present application;

[0108] FIG6 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M290 provided in an example of the present application. Modes for Carrying Out the Invention

[0109] The present application provides an organic compound, mixture, composition, organic light-emitting device, and display panel. To make the objectives, technical solutions, and effects of the present application more clear and explicit, the present application is further described in detail below with reference to the accompanying drawings and examples. It should be understood that the specific examples described herein are intended only to illustrate the present application and are not intended to limit the present application.

[0110] The present invention provides an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. Each of these is described in detail below. It should be noted that the order in which the following embodiments are described does not limit the preferred order of the embodiments.

[0111] In this application, aromatic group, aromatic series, and aromatic ring system have the same meaning and can be interchanged.

[0112] In the present application, heteroaromatic group, heteroaromatic family and heteroaromatic ring system have the same meaning and can be interchanged.

[0113] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0114] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0115] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, , cyano, isocyano, nitro or halogen, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from but not limited to: a deuterium atom, cyano, isocyano, nitro or halogen, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0116] In this application, the "number of ring atoms" represents the number of atoms among the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0117] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0118] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom on the basis of aryl is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidine 1-Hydroxy-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine,

[0119] In this application, "alkyl" may refer to a straight chain, branched chain and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl at each occurrence. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 1,2-D-HEXYL OCTYL, 2-HYDROX ...

[0120] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0121] As used herein, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amino groups include -NH2, -N(alkyl), -NH(alkyl), -N(cycloalkyl), -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0122] In this application, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, an amino group refers to -NH2, a formyl group refers to -C(=O)H, a haloformyl group refers to -C(=O)Z (wherein Z represents a halogen), a carbamoyl group refers to -C(=O)NH2, an isocyanate group refers to -NCO, and an isothiocyanate group refers to -NCS.

[0123] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", i.e., an alkyl group as defined above connected to another group via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0124] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0125] In the present application, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0126] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the adjacent position in the group are fusion sites.

[0127] In this application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0128] In the present application, the single bond connecting the substituent runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0129] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0130] In the present application, "adjacent groups" refers to two substituents with no substitutable sites between them.

[0131] In the present application, "two adjacent R1 or R3 or R5 form a ring with each other" means a ring system formed by two adjacent 1 or 3 or R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0132] The present invention provides an organic compound having a structure as shown in general formula (1) or (2):

[0133] wherein Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3):

[0134] Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5):

[0135] When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formulas (A-2) to (A-5);

[0136] The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position on the same benzene ring;

[0137] Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4):

[0138] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0139] n0, n1, n2, and n5 are each independently selected from a positive integer between 0 and 14;

[0140] Any of R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0141] When n0 is greater than or equal to 2, two adjacent R0s may form a ring with each other or not; when n1 is greater than or equal to 2, two adjacent R1s may form a ring with each other or not; when n2 is greater than or equal to 2, two adjacent R2s may form a ring with each other or not; when n5 is greater than or equal to 2, two adjacent R5s may form a ring with each other or not.

[0142] Optionally, the organic compound has a structure as shown in any one of the general formulas (2-1) to (2-28):

[0143] wherein any one of R3 and R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0144] n3 is greater than or equal to 0 and less than or equal to 5;

[0145] When n3 is greater than or equal to 2, two adjacent R3s may form a ring or not;

[0146] n4 is greater than or equal to 0 and less than or equal to 5;

[0147] When n4 is greater than or equal to 2, two adjacent R4s may form a ring or not.

[0148] Optionally, any one of R1, R2, R3, R4 or R5 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms.

[0149] Optionally, any one of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched-chain alkyl group having 3 to 5 carbon atoms.

[0150] By introducing an alkyl group into the organic compound, the solubility of the organic compound in processes such as inkjet printing is improved, and the product quality of the organic light-emitting device using the organic compound is improved.

[0151] In some embodiments, two adjacent R1s form a ring with each other; further, two adjacent R1s form a ring with each other to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R1s form a ring with each other to form Wherein, * indicates the attachment site.

[0152] In some embodiments, two adjacent R2s are mutually cyclic; further, two adjacent R2s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R2s are mutually cyclic to form Wherein, * indicates the attachment site.

[0153] In some embodiments, two adjacent R3s are mutually cyclic; further, two adjacent R3s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R3s are mutually cyclic to form Wherein, * indicates the attachment site.

[0154] In some embodiments, two adjacent R4s are mutually cyclic; further, two adjacent R4s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R4s are mutually cyclic to form Wherein, * indicates the attachment site.

[0155] In some embodiments, two adjacent R5s are mutually cyclic; further, two adjacent R5s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R5s are mutually cyclic to form Wherein, * indicates the attachment site.

[0156] In some embodiments, when the structure represented by formula (B-2) exists in Ar2, the structure represented by formula (B-2) is preferably:

[0157] as well as At least one of the above is beneficial to improving the luminous efficiency and service life of an organic light-emitting device using the organic compound.

[0158] In some embodiments, the organic compound is a blue light-emitting material.

[0159] In some embodiments, the organic compound is selected from the following compounds:

[0160] The boron-containing biphenyl organic compound provided in the embodiments of the present application introduces structures such as dibenzofuran, dibenzothiophene, carbazole, benzopentacyclic ring, triphenylene and / or naphthalene into the boron nitrogen compound, thereby making the overall molecular conjugation greater, thereby improving the luminous efficiency and service life of the organic light-emitting device using the organic compound; at the same time, the introduction of structures such as tetralin and / or indane into the boron nitrogen compound makes the molecule more soluble in processes such as inkjet printing, facilitates compound purification, thereby improving the purity of the organic compound, and further extending the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0161] Referring to Figures 1 and 2 , the present application further provides an organic light-emitting device 100, comprising: a first electrode 101 and a second electrode 102; and an organic functional layer 103 positioned between the first electrode 101 and the second electrode 102. The material of the organic functional layer 103 comprises one or more of the organic compounds described above. The first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0162] In some embodiments, the organic light-emitting device 100 can be used for an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emission diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, and an organic light-emitting field-effect transistor.

[0163] In some embodiments, the organic light-emitting device 100 can be applied to various electronic devices, such as display panels, lighting devices, light sources, etc.

[0164] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer comprising a first compound and a second compound, wherein the first compound is selected from one or more of the organic compounds described above, and the second compound is selected from one or more of a hole injection material, a hole transport material, an electron transport material, a hole blocking material, a luminescent guest material, a luminescent host material, and an organic dye. Detailed descriptions of the various organic functional materials included in the organic functional layer 103 are provided in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0165] The luminescent guest material is selected from a singlet light emitter (fluorescent light emitter), a triplet light emitter (phosphorescent light emitter) and a TADF material.

[0166] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0167] When the second compound is a light-emitting guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0168] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multi-layered, the organic functional layer 103 includes at least a light-emitting layer 107. Preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, a light-emitting layer 107, an electron blocking layer 106, an electron injection layer 109, an electron transport layer 108, or a hole blocking layer.

[0169] In some embodiments, the organic light-emitting device 100 can be a blue organic light-emitting device, a green organic light-emitting device, or a red organic light-emitting device, and the light-emitting layer 107 can include a host material and a guest material, the guest material being one or more of the organic compounds described above, and the host material including a fused aromatic derivative or a heteroaromatic compound.

[0170] The light-emitting wavelength of the organic light-emitting device 100 is between 300 and 1000 nm; further, the light-emitting wavelength of the organic light-emitting device 100 is between 350 and 900 nm; further, the light-emitting wavelength of the organic light-emitting device 100 is between 400 and 800 nm; further, the light-emitting wavelength of the organic light-emitting device 100 is within the wavelength range of blue light.

[0171] In some embodiments, the host material includes at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Preferably, the host material is a blue light host material for a blue organic light-emitting device; when the host material is a blue light host material, the host material is preferably an anthracene organic compound.

[0172] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc., and preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which helps to inhibit crystallization of the light-emitting layer 107 and concentration quenching caused by high concentrations of the guest material, thereby improving the luminous efficiency of the organic light-emitting device 100.

[0173] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer 103, such as injecting holes into the hole injection layer, the hole transport layer, or the light-emitting layer. The anode can include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, hole transport layer, or electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which can be easily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, such as patterned ITO conductive substrates that are commercially available and can be used to prepare the organic light-emitting device 100 of the present application.

[0174] In some embodiments, the cathode is an electron-injecting electrode, and the cathode can inject electrons into the organic functional layer, such as injecting electrons into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the luminescent material in the light-emitting layer, or the n-type semiconductor material serving as the electron injection layer, electron transport layer, or hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes for organic electronic devices may be used as cathode materials for the device of the present application, and the cathode materials include but are not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0175] In some embodiments, the hole injection layer 104 is used to promote the injection of holes from the anode into the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material, which is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the functional material of the film layer on the side away from the anode (such as the hole transport material of the hole transport layer). The hole injection material includes but is not limited to at least one of metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0176] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transmitted from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material known in the art having high hole mobility, and the hole transport material may include but is not limited to at least one of an arylamine-based organic material, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, and the like.

[0177] In some embodiments, the electron transport layer 108 is used to transport electrons. The electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material known in the art with high electron mobility, and may include, but is not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0178] In some embodiments, the electron injection layer 109 is used to inject electrons. The electron injection layer 109 includes an electron injection material. The electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material, and has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer, and also has an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0179] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0180] In some embodiments, the organic light-emitting device 100 further includes a substrate 110, on which the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked. The substrate 110 can be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device 100 can be fabricated. The substrate 110 can be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 110 can include, but is not limited to, plastic, polymer, metal, semiconductor wafer, or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode. More preferably, the surface is free of surface defects. Preferably, the material of the substrate 110 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0181] In some embodiments, the organic light-emitting device 100 may be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by printing (eg, inkjet printing).

[0182] In some embodiments, the mixture layer or the light-emitting layer can be formed by a printing or coating process of the composition. Printing or coating processes include inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slot extrusion coating, etc. Preferably, gravure printing, nozzle printing and inkjet printing are used.

[0183] The composition may be a solution or a suspension, and may include a dispersant and a dispersant, wherein the dispersant is one or more of the organic compounds described above and at least one organic solvent, and the dispersant is used to disperse the dispersant.

[0184] In the composition, the mass fraction of the organic compound described above may be 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, further preferably 0.5% to 10%, and most preferably 1% to 5%.

[0185] When the composition is used in a printing process, the composition can be an ink. The viscosity and surface tension of the ink are important parameters. The surface tension parameters of the appropriate ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the ink at operating temperature or at 25°C ranges from 19 dyne / cm to 50 dyne / cm; preferably, from 22 dyne / cm to 35 dyne / cm; and more preferably, from 25 dyne / cm to 33 dyne / cm, which is advantageous for use in an inkjet printing process. In some embodiments, the viscosity of the ink at operating temperature or at 25°C ranges from 1 cps to 100 cps; preferably, from 1 cps to 50 cps; more preferably, from 1.5 cps to 20 cps; and most preferably, from 4.0 cps to 20 cps, which is advantageous for use in an inkjet printing process.

[0186] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The range is preferably 18.5 to 21.0 MPa 1 / 2 range; δp (polar force) is 0.2~12.5MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa 1 / 2 range; δh (hydrogen bond force) is 0.9~14.2MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa 1 / 2 range.

[0187] In some embodiments, the boiling point of the dispersant is greater than or equal to 150°C, preferably greater than or equal to 180°C, more preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, further preferably greater than or equal to 275°C, and most preferably greater than or equal to 300°C. The boiling point of the dispersant is at least greater than or equal to 150°C, which helps prevent nozzle clogging of the inkjet print head during inkjet printing, and a higher boiling point is more effective in preventing clogging.

[0188] The dispersant may include at least one organic solvent, and the organic solvent may be evaporated from the solvent system to form a film containing functional materials. The organic solvent may include at least one first organic solvent, and the first organic solvent may be selected from aromatic or heteroaromatic. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropyl Biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0189] The first organic solvent can be selected from aromatic ketone solvents. Specifically, the first organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0190] The first organic solvent can be selected from aromatic ether solvents. Specifically, the first organic solvent can be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0191] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0192] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0193] The organic solvent may further include a second organic solvent, which may be selected from one or more of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and the like.

[0194] In addition to the dispersoid and the dispersant, the composition may further include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0195] The exemplary preparation methods of the organic compounds provided herein are shown in the following exemplary embodiments 1 to 63.

[0196] Example 1

[0197] The synthetic route of organic compound M1 is as follows:

[0198] Synthesis of intermediate 1-3:

[0199] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 1-3 with a molar weight of 8.21 mmol and a yield of 82.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 337.

[0200] Synthesis of intermediate 1-5:

[0201] Compound 1-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-5 with a molar weight of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS (ASAP) = 481.

[0202] Synthesis of intermediate 1-7:

[0203] Intermediate 1-5 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100° C. for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-7 with a molar weight of 5.45 mmol and a yield of 54.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-7 was: MS (ASAP) = 608.

[0204] Synthesis of intermediate 1-9:

[0205] Intermediate 1-7 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-9 with a molar weight of 6.25 mmol and a yield of 62.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-9 was: MS (ASAP) = 774.

[0206] Synthesis of intermediate 1-11:

[0207] Intermediate 1-9 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 1-11 with a molar weight of 7.81 mmol and a yield of 78.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-11 was: MS (ASAP) = 966.

[0208] Synthesis of organic compound M1:

[0209] A 250 ml three-necked flask was charged with 10 mmol of intermediate 1-11 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M1, with a yield of 38.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M1 was: MS (ASAP) = 940.

[0210] Example 2

[0211] The synthetic route of organic compound M2 is as follows:

[0212] Synthesis of intermediate 2-2:

[0213] Intermediate 1-5 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100° C. for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-2 with a molar weight of 6.47 mmol and a yield of 64.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS (ASAP) = 580.

[0214] Synthesis of intermediate 2-3:

[0215] Intermediate 2-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-3 with a molar weight of 8.36 mmol and a yield of 83.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 2-3 was: MS (ASAP) = 746.

[0216] Synthesis of intermediate 2-4:

[0217] Intermediate 2-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-4 with a molar weight of 7.09 mmol and a yield of 70.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 2-4 was: MS (ASAP) = 938.

[0218] Synthesis of organic compound M2:

[0219] 10 mmol of intermediate 2-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M2, with a yield of 36.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M2 was: MS (ASAP) = 912.

[0220] Example 3

[0221] The synthetic route of organic compound M3 is as follows:

[0222] Synthesis of intermediate 3-2:

[0223] Intermediate 1-5 (10 mmol), compound 3-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100° C. for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 3-2 with a molar weight of 7.83 mmol and a yield of 78.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS (ASAP) = 566.

[0224] Synthesis of intermediate 3-3:

[0225] Intermediate 3-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 3-3 with a molar weight of 8.51 mmol and a yield of 85.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 3-3 was: MS (ASAP) = 732.

[0226] Synthesis of intermediate 3-4:

[0227] Intermediate 3-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-4 with a molar weight of 5.97 mmol and a yield of 59.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 3-4 was: MS (ASAP) = 924.

[0228] Synthesis of organic compound M3:

[0229] 10 mmol of intermediate 2-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M3, with a yield of 40.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M3 was: MS (ASAP) = 898.

[0230] Example 4

[0231] The synthetic route of organic compound M16 is as follows:

[0232] Synthesis of intermediate 16-2:

[0233] Intermediate 16-1 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 16-2 with a molar weight of 9.22 mmol and a yield of 92.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-2 was: MS (ASAP) = 375.

[0234] Synthesis of intermediate 16-4:

[0235] Compound 16-2 (10 mmol), compound 16-3 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 16-4 with a molar weight of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-4 was: MS (ASAP) = 507.

[0236] Synthesis of intermediate 16-5:

[0237] Compound 16-4 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 16-5 with a molar weight of 6.97 mmol and a yield of 69.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-5 was: MS (ASAP) = 651.

[0238] Synthesis of intermediate 16-8:

[0239] Intermediate 16-6 (10 mmol), compound 16-7 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 16-8 with a molar weight of 5.42 mmol and a yield of 54.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-8 was: MS (ASAP) = 281.

[0240] Synthesis of intermediate 16-9:

[0241] Intermediate 16-8 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 16-9 with a molar weight of 5.97 mmol and a yield of 59.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-9 was: MS (ASAP) = 469.

[0242] Synthesis of intermediate 16-10:

[0243] Intermediate 16-9 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120° C. for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 16-10 with a molar weight of 7.27 mmol and a yield of 72.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-10 was: MS (ASAP) = 1084.

[0244] Synthesis of organic compound M16:

[0245] A 250 ml three-necked flask was charged with 10 mmol of intermediate 16-10 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined and the solvent was evaporated to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M16, with a yield of 33.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M16 was: MS (ASAP) = 1058.1H NMR (400MHz, CDCl3) δ8.17(d,J=8.6Hz,6H),8.02(s,6H),7.87(d,J=13.4Hz,6H),7.0 2(t,J=7.6Hz,6H),6.73(d,J=17.7Hz,6H),6.38(t,J=7.5Hz,6H),1.78(s,18H),1.73 (s,9H),1.69(s,9H,1.56(s,9H).

[0246] Example 5

[0247] The synthetic route of organic compound M20 is as follows:

[0248] Synthesis of intermediate 20-2:

[0249] Intermediate 16-6 (10 mmol), compound 20-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 20-2 with a molar weight of 6.94 mmol and a yield of 69.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 20-2 was: MS (ASAP) = 281.

[0250] Synthesis of intermediate 20-3:

[0251] Intermediate 20-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 20-3 with a molar weight of 6.33 mmol and a yield of 63.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 20-3 was: MS (ASAP) = 469.

[0252] Synthesis of intermediate 20-4:

[0253] Intermediate 20-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120° C. for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 20-4 with a molar weight of 5.47 mmol and a yield of 54.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 20-4 was: MS (ASAP) = 1084.

[0254] Synthesis of organic compound M20:

[0255] 10 mmol of intermediate 20-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, and boron tribromide (21 mmol) was added. The reaction solution was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M20, with a yield of 31.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M20 was: MS (ASAP) = 1058.

[0256] Example 6

[0257] The synthetic route of organic compound M24 is as follows:

[0258] Synthesis of intermediate 24-2:

[0259] Intermediate 16-6 (10 mmol), compound 24-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100° C. for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-2 with a molar weight of 7.63 mmol and a yield of 76.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 24-2 was: MS (ASAP) = 281.

[0260] Synthesis of intermediate 24-3:

[0261] Intermediate 24-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 24-3 with a molar weight of 6.55 mmol and a yield of 65.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 24-3 was: MS (ASAP) = 469.

[0262] Synthesis of intermediate 24-4:

[0263] Intermediate 24-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120° C. for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 24-4 with a molar weight of 5.02 mmol and a yield of 50.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 24-4 was: MS (ASAP) = 1084.

[0264] Synthesis of organic compound M24:

[0265] 10 mmol of intermediate 24-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, and boron tribromide (21 mmol) was added. The reaction solution was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M24, with a yield of 36.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M24 was: MS (ASAP) = 1058.

[0266] Example 7

[0267] The synthetic route of organic compound M25 is as follows:

[0268] Synthesis of intermediate 25-1:

[0269] Intermediate 1-5 (10 mmol), compound 24-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 25-1 with a molar weight of 8.47 mmol and a yield of 84.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 25-1 was: MS (ASAP) = 726.

[0270] Synthesis of intermediate 25-2:

[0271] Intermediate 25-1 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 25-2 with a molar weight of 6.48 mmol and a yield of 64.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 25-2 was: MS (ASAP) = 892.

[0272] Synthesis of intermediate 25-3:

[0273] Intermediate 25-2 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 25-3 with a molar weight of 7.75 mmol and a yield of 77.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 25-3 was: MS (ASAP) = 1084.

[0274] Synthesis of organic compound M25:

[0275] 10 mmol of intermediate 25-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M25, with a yield of 42.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M25 was: MS (ASAP) = 1058.1H NMR(400MHz, CDCl3)δ9.02(s,1H),8.57(s,1H),8.51–8.39(m,4H),7.91(s,1H),7.89– 7.68(m,1H),7.62(d,J=8.5Hz,7H),7.52(d,J=9.1Hz,1H),7.49–7.32(m,2H),7.25(d,J =7.9Hz, 8H), 7.26 (d, J = 13.4Hz, 1H), 7.06 (d, J = 15.4Hz, 1H), 6.49 (s, 1H), 6.44 (d, J = 8. 1Hz, 1H), 6.31 (d, J = 14.2Hz, 1H), 1.58 (s, 9H), 1.50 (s, 9H), 1.47 (s, 18H), 1.06 (s, 9H).

[0276] Example 8

[0277] The synthetic route of organic compound M26 is as follows:

[0278] Synthesis of intermediate 26-1:

[0279] Intermediate 1-5 (10 mmol), compound 16-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100° C. for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 26-1 with a molar weight of 8.66 mmol and a yield of 86.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 26-1 was: MS (ASAP) = 726.

[0280] Synthesis of intermediate 26-2:

[0281] Intermediate 26-1 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 26-2 with a molar weight of 6.09 mmol and a yield of 60.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 26-2 was: MS (ASAP) = 892.

[0282] Synthesis of intermediate 26-3:

[0283] Intermediate 26-2 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 26-3 with a molar weight of 7.54 mmol and a yield of 75.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 26-3 was: MS (ASAP) = 1084.

[0284] Synthesis of organic compound M26:

[0285] A 250 ml three-necked flask was charged with 10 mmol of intermediate 26-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M26, with a yield of 39.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M26 was: MS (ASAP) = 1058.

[0286] Example 9

[0287] The synthetic route of organic compound M96 is as follows:

[0288] Synthesis of intermediate 96-3:

[0289] Intermediate 96-1 (20 mmol) and compound 96-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 96-3 with a molar weight of 7.29 mmol and a yield of 72.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 96-3 was: MS (ASAP) = 357.

[0290] Synthesis of intermediate 96-4:

[0291] Intermediate 96-3 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 96-4 with a molar weight of 6.12 mmol and a yield of 61.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 96-4 was: MS (ASAP) = 545.

[0292] Synthesis of intermediate 96-5:

[0293] Intermediate 96-4 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 96-5 with a molar weight of 5.38 mmol and a yield of 53.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 96-5 was: MS (ASAP) = 1160.

[0294] Synthesis of organic compound M96:

[0295] A 250 ml three-necked flask was charged with 10 mmol of intermediate 96-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M96, with a yield of 43.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M96 was: MS (ASAP) = 1134.

[0296] Example 10

[0297] The synthetic route of organic compound M100 is as follows:

[0298] Synthesis of intermediate 100-2:

[0299] Intermediate 96-1 (20 mmol) and compound 100-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 100-2 with a molar weight of 7.67 mmol and a yield of 76.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 100-2 was: MS (ASAP) = 357.

[0300] Synthesis of intermediate 100-3:

[0301] Intermediate 100-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 100-3 with a molar weight of 6.59 mmol and a yield of 65.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 100-3 was: MS (ASAP) = 545.

[0302] Synthesis of intermediate 100-4:

[0303] Intermediate 100-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 100-4 with a molar weight of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 100-4 was: MS (ASAP) = 1160.

[0304] Synthesis of organic compound M100:

[0305] A 250 ml three-necked flask was charged with 10 mmol of intermediate 100-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M100, with a yield of 41.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M100 was: MS (ASAP) = 1134.

[0306] Example 11

[0307] The synthetic route of organic compound M104 is as follows:

[0308] Synthesis of intermediate 104-2:

[0309] Intermediate 96-1 (20 mmol) and compound 104-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 104-2 with a molar weight of 7.11 mmol and a yield of 71.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 104-2 was: MS (ASAP) = 357.

[0310] Synthesis of intermediate 104-3:

[0311] Intermediate 104-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 104-3 with a molar weight of 5.71 mmol and a yield of 57.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 104-3 was: MS (ASAP) = 545.

[0312] Synthesis of intermediate 104-4:

[0313] Intermediate 104-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 104-4 with a molar weight of 6.57 mmol and a yield of 65.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 104-4 was: MS (ASAP) = 1160.

[0314] Synthesis of organic compound M104:

[0315] A 250 ml three-necked flask was charged with 10 mmol of intermediate 104-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed by evaporation under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M104, with a yield of 45.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M104 was: MS (ASAP) = 1134.

[0316] Example 12

[0317] The synthetic route of organic compound M122 is as follows:

[0318] Synthesis of intermediate 122-2:

[0319] Intermediate 1-5 (10 mmol), compound 122-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 122-2 with a molar weight of 8.36 mmol and a yield of 83.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 122-2 was: MS (ASAP) = 690.

[0320] Synthesis of intermediate 122-3:

[0321] Intermediate 122-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 122-3 with a molar weight of 54.9 mmol and a yield of 54.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 122-3 was: MS (ASAP) = 856.

[0322] Synthesis of intermediate 122-4:

[0323] Intermediate 122-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 122-4 with a molar weight of 6.47 mmol and a yield of 64.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 122-4 was: MS (ASAP) = 1048.

[0324] Synthesis of organic compound M122:

[0325] A 250 ml three-necked flask was charged with 10 mmol of intermediate 122-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M124, with a yield of 31.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M124 was: MS (ASAP) = 1022.

[0326] Example 13

[0327] The synthetic route of organic compound M128 is as follows:

[0328] Synthesis of intermediate 128-1:

[0329] Compound 3-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 128-1 with a molar weight of 8.37 mmol and a yield of 83.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 128-1 was: MS (ASAP) = 309.

[0330] Synthesis of intermediate 128-2:

[0331] Compound 128-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 128-2 with a molar weight of 7.05 mmol and a yield of 70.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 128-2 was: MS (ASAP) = 453.

[0332] Synthesis of intermediate 128-3:

[0333] Intermediate 128-2 (10 mmol), compound 122-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 128-3 with a molar weight of 6.83 mmol and a yield of 68.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 128-3 was: MS (ASAP) = 662.

[0334] Synthesis of intermediate 128-4:

[0335] Intermediate 128-3 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 128-4 with a molar weight of 6.68 mmol and a yield of 66.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 128-4 was: MS (ASAP) = 828.

[0336] Synthesis of intermediate 128-5:

[0337] Intermediate 128-4 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 128-5 with a molar weight of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 128-5 was: MS (ASAP) = 1020.

[0338] Synthesis of organic compound M128:

[0339] A 250 ml three-necked flask was charged with 10 mmol of intermediate 128-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M128, with a yield of 40.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M128 was: MS (ASAP) = 994.

[0340] Example 14

[0341] The synthetic route of organic compound M129 is as follows:

[0342] Synthesis of intermediate 129-1:

[0343] Compound 2-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 129-1 with a molar weight of 7.69 mmol and a yield of 76.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 129-1 was: MS (ASAP) = 323.

[0344] Synthesis of intermediate 129-2:

[0345] Compound 129-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 129-2 with a molar weight of 7.59 mmol and a yield of 75.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 129-2 was: MS (ASAP) = 467.

[0346] Synthesis of intermediate 129-3:

[0347] Intermediate 129-2 (10 mmol), compound 104-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 129-3 with a molar weight of 6.12 mmol and a yield of 61.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 129-3 was: MS (ASAP) = 788.

[0348] Synthesis of intermediate 129-4:

[0349] Intermediate 129-3 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 129-4 with a molar weight of 6.51 mmol and a yield of 65.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 129-4 was: MS (ASAP) = 954.

[0350] Synthesis of intermediate 129-5:

[0351] Intermediate 129-4 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 129-5 with a molar weight of 7.34 mmol and a yield of 73.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 129-5 was: MS (ASAP) = 1146.

[0352] Synthesis of organic compound M129:

[0353] A 250 ml three-necked flask was charged with 10 mmol of intermediate 129-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M129, with a yield of 29.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M129 was: MS (ASAP) = 1120.

[0354] Example 15

[0355] The synthetic route of organic compound M132 is as follows:

[0356] Synthesis of intermediate 132-1:

[0357] Compound 2-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 132-1 with a molar weight of 8.41 mmol and a yield of 84.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 132-1 was: MS (ASAP) = 351.

[0358] Synthesis of intermediate 132-2:

[0359] Compound 132-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 132-2 with a molar weight of 6.79 mmol and a yield of 67.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 132-2 was: MS (ASAP) = 495.

[0360] Synthesis of intermediate 132-3:

[0361] Intermediate 132-2 (10 mmol), compound 104-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 132-3 with a molar weight of 7.84 mmol and a yield of 78.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 132-3 was: MS (ASAP) = 816.

[0362] Synthesis of intermediate 132-4:

[0363] Intermediate 132-3 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 132-4 with a molar weight of 5.96 mmol and a yield of 59.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 132-4 was: MS (ASAP) = 982.

[0364] Synthesis of intermediate 132-5:

[0365] Intermediate 132-4 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 132-5 with a molar weight of 6.47 mmol and a yield of 64.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 132-5 was: MS (ASAP) = 1174.

[0366] Synthesis of organic compound M132:

[0367] A 250 ml three-necked flask was charged with 10 mmol of intermediate 132-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M132, with a yield of 33.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M132 was: MS (ASAP) = 1148.

[0368] Example 16

[0369] The synthetic route of organic compound M147 is as follows:

[0370] Synthesis of intermediate 147-2:

[0371] Intermediate 25-2 (10 mmol) and intermediate 147-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 147-2 with a molar weight of 7.36 mmol and a yield of 73.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 147-2 was: MS (ASAP) = 1024.

[0372] Synthesis of organic compound M147:

[0373] A 250 ml three-necked flask was charged with 10 mmol of intermediate 147-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M147, with a yield of 34.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M147 was: MS (ASAP) = 998.

[0374] Example 17

[0375] The synthetic route of organic compound M162 is as follows:

[0376] Synthesis of intermediate 162-1:

[0377] Intermediate 24-3 (10 mmol), intermediate 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 162-1 with a molar weight of 5.35 mmol and a yield of 53.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 162-1 was: MS (ASAP) = 613.

[0378] Synthesis of intermediate 162-2:

[0379] Intermediate 162-1 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 162-2 with a molar weight of 7.34 mmol and a yield of 73.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 162-2 was: MS (ASAP) = 726.

[0380] Synthesis of intermediate 162-3:

[0381] Intermediate 162-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 162-3 with a molar weight of 5.78 mmol and a yield of 57.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 162-3 was: MS (ASAP) = 896.

[0382] Synthesis of intermediate 162-5:

[0383] Intermediate 162-3 (10 mmol) and intermediate 162-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 162-5 with a molar weight of 6.17 mmol and a yield of 61.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 162-5 was: MS (ASAP) = 1040.

[0384] Synthesis of organic compound M162:

[0385] A 250 ml three-necked flask was charged with 10 mmol of intermediate 162-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M162, with a yield of 35.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M162 was: MS (ASAP) = 1014.

[0386] Example 18

[0387] The synthetic route of organic compound M165 is as follows:

[0388] Synthesis of intermediate 165-2:

[0389] Intermediate 1-9 (10 mmol) and intermediate 165-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 165-2 with a molar weight of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 165-2 was: MS (ASAP) = 919.

[0390] Synthesis of organic compound M165:

[0391] A 250 ml three-necked flask was charged with 10 mmol of intermediate 165-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the dropwise addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M165, with a yield of 29.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M165 was: MS (ASAP) = 893.

[0392] Example 19

[0393] The synthetic route of organic compound M193 is as follows:

[0394] Synthesis of intermediate 193-1:

[0395] Intermediate 16-9 (10 mmol), intermediate 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 193-1 with a molar weight of 7.56 mmol and a yield of 75.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 193-1 was: MS (ASAP) = 613.

[0396] Synthesis of intermediate 193-2:

[0397] Intermediate 193-1 (10 mmol), intermediate 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 193-2 with a molar weight of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 193-2 was: MS (ASAP) = 726.

[0398] Synthesis of intermediate 193-3:

[0399] Intermediate 193-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 193-3 with a molar weight of 5.29 mmol and a yield of 52.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 193-3 was: MS (ASAP) = 892.

[0400] Synthesis of intermediate 193-5:

[0401] Intermediate 193-3 (10 mmol) and intermediate 193-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 193-5 with a molar weight of 6.56 mmol and a yield of 65.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 193-5 was: MS (ASAP) = 988.

[0402] Synthesis of organic compound M193:

[0403] A 250 ml three-necked flask was charged with 10 mmol of intermediate 193-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M193, with a yield of 29.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M193 was: MS (ASAP) = 962.

[0404] Example 20

[0405] The synthetic route of organic compound M210 is as follows:

[0406] Synthesis of intermediate 210-2:

[0407] Intermediate 162-3 (10 mmol) and intermediate 210-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 210-2 with a molar weight of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 210-2 was: MS (ASAP) = 974.

[0408] Synthesis of organic compound M210:

[0409] A 250 ml three-necked flask was charged with 10 mmol of intermediate 210-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M210, with a yield of 32.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M210 was: MS (ASAP) = 948.

[0410] Example 21

[0411] The synthetic route of organic compound M234 is as follows:

[0412] Synthesis of intermediate 234-2:

[0413] Intermediate 24-3 (10 mmol), intermediate 234-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 234-2 with a molar weight of 6.58 mmol and a yield of 65.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 234-2 was: MS (ASAP) = 691.

[0414] Synthesis of intermediate 234-3:

[0415] Intermediate 234-2 (10 mmol), compound 16-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 234-3 with a molar weight of 7.07 mmol and a yield of 70.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 234-3 was: MS (ASAP) = 1118.

[0416] Synthesis of intermediate 234-5:

[0417] Intermediate 234-3 (10 mmol), compound 234-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 234-5 with a molar weight of 5.06 mmol and a yield of 50.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 234-5 was: MS (ASAP) = 1251.

[0418] Synthesis of organic compound M234:

[0419] A 250 ml three-necked flask was charged with 10 mmol of intermediate 234-5 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed by evaporation under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M234, with a yield of 22.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M234 was: MS (ASAP) = 1225.

[0420] Example 22

[0421] The synthetic route of organic compound M253 is as follows:

[0422] Synthesis of intermediate 253-2:

[0423] Intermediate 253-1 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 253-2 with a molar weight of 7.69 mmol and a yield of 76.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 253-2 was: MS (ASAP) = 375.

[0424] Synthesis of intermediate 253-3:

[0425] Compound 253-2 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 253-3 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 253-3 was: MS (ASAP) = 563.

[0426] Synthesis of intermediate 253-4:

[0427] Compound 253-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 253-4 with a molar weight of 6.75 mmol and a yield of 67.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 253-4 was: MS (ASAP) = 707.

[0428] Synthesis of intermediate 253-5:

[0429] Intermediate 253-4 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 253-5 with a molar weight of 7.24 mmol and a yield of 72.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 253-5 was: MS (ASAP) = 820.

[0430] Synthesis of intermediate 253-7:

[0431] Intermediate 253-5 (10 mmol), compound 253-6 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 253-7 with a molar weight of 5.38 mmol and a yield of 53.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 253-7 was: MS (ASAP) = 1084.

[0432] Synthesis of organic compound M253:

[0433] A 250 ml three-necked flask was charged with 10 mmol of intermediate 253-7 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M253, with a yield of 38.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M253 was: MS (ASAP) = 1058.

[0434] Example 23

[0435] The synthetic route of organic compound M254 is as follows:

[0436] Synthesis of intermediate 254-2:

[0437] Intermediate 253-5 (10 mmol), compound 254-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 254-2 with a molar weight of 5.19 mmol and a yield of 51.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 254-2 was: MS (ASAP) = 1084.

[0438] Synthesis of organic compound M254:

[0439] A 250 ml three-necked flask was charged with 10 mmol of intermediate 254-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M254, with a yield of 42.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M254 was: MS (ASAP) = 1058.

[0440] Example 24

[0441] The synthetic route of organic compound M255 is as follows:

[0442] Synthesis of intermediate 255-2:

[0443] Intermediate 253-5 (10 mmol), compound 255-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 255-2 with a molar weight of 6.28 mmol and a yield of 62.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 255-2 was: MS (ASAP) = 1084.

[0444] Synthesis of organic compound M255:

[0445] A 250 ml three-necked flask was charged with 10 mmol of intermediate 255-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M255, with a yield of 47.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M255 was: MS (ASAP) = 1058.

[0446] Example 25

[0447] The synthetic route of organic compound M266 is as follows:

[0448] Synthesis of intermediate 266-2:

[0449] Intermediate 253-4 (10 mmol), compound 266-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 266-2 with a molar weight of 6.37 mmol and a yield of 63.7%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 266-2 was: MS (ASAP) = 1216.

[0450] Synthesis of organic compound M266:

[0451] A 250 ml three-necked flask was charged with 10 mmol of intermediate 266-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M266, with a yield of 36.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M266 was: MS (ASAP) = 1190.

[0452] Example 26

[0453] The synthetic route of organic compound M268 is as follows:

[0454] Synthesis of intermediate 268-2:

[0455] Compound 16-2 (10 mmol), compound 268-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 268-2 with a molar weight of 7.32 mmol and a yield of 73.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 268-2 was: MS (ASAP) = 527.

[0456] Synthesis of intermediate 268-3:

[0457] Compound 268-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 268-3 with a molar weight of 6.51 mmol and a yield of 65.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 268-3 was: MS (ASAP) = 671.

[0458] Synthesis of intermediate 268-6:

[0459] Intermediate 268-4 (20 mmol), compound 268-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 268-6 with a molar weight of 5.27 mmol and a yield of 52.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 268-6 was: MS (ASAP) = 357.

[0460] Synthesis of intermediate 268-7:

[0461] Intermediate 268-6 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 268-7 with a molar weight of 5.17 mmol and a yield of 51.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 268-7 was: MS (ASAP) = 545.

[0462] Synthesis of intermediate 268-8:

[0463] Intermediate 268-7 (10 mmol), intermediate 268-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 268-8 with a molar weight of 7.02 mmol and a yield of 70.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 268-8 was: MS (ASAP) = 1180.

[0464] Synthesis of organic compound M268:

[0465] A 250 ml three-necked flask was charged with 10 mmol of intermediate 268-8 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M268, with a yield of 30.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M268 was: MS (ASAP) = 1154.

[0466] Example 27

[0467] The synthetic route of organic compound M269 is as follows:

[0468] Synthesis of intermediate 269-2:

[0469] Compound 16-2 (10 mmol), compound 269-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 269-2 with a molar weight of 6.45 mmol and a yield of 64.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 269-2 was: MS (ASAP) = 583.

[0470] Synthesis of intermediate 269-3:

[0471] Compound 269-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 269-3 with a molar weight of 6.91 mmol and a yield of 69.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 269-3 was: MS (ASAP) = 727.

[0472] Synthesis of intermediate 269-6:

[0473] Intermediate 269-4 (20 mmol), compound 269-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 269-6 with a molar weight of 5.54 mmol and a yield of 55.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 269-6 was: MS (ASAP) = 301.

[0474] Synthesis of intermediate 269-7:

[0475] Intermediate 269-6 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 268-7 with a molar weight of 5.49 mmol and a yield of 54.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 269-7 was: MS (ASAP) = 489.

[0476] Synthesis of intermediate 269-8:

[0477] Intermediate 269-7 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 269-8 with a molar weight of 7.55 mmol and a yield of 75.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 269-8 was: MS (ASAP) = 1180.

[0478] Synthesis of organic compound M269:

[0479] A 250 ml three-necked flask was charged with 10 mmol of intermediate 269-8 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M269, with a yield of 29.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M269 was: MS (ASAP) = 1154.

[0480] Example 28

[0481] The synthetic route of organic compound M270 is as follows:

[0482] Synthesis of intermediate 270-1:

[0483] Intermediate 269-4 (20 mmol), compound 268-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 269-6 with a molar weight of 5.76 mmol and a yield of 57.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 269-6 was: MS (ASAP) = 245.

[0484] Synthesis of intermediate 270-2:

[0485] Intermediate 270-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 270-2 with a molar weight of 4.97 mmol and a yield of 49.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 270-2 was: MS (ASAP) = 433.

[0486] Synthesis of intermediate 270-3:

[0487] Intermediate 269-7 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 270-3 with a molar weight of 8.47 mmol and a yield of 84.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 270-3 was: MS (ASAP) = 1124.

[0488] Synthesis of organic compound M270:

[0489] A 250 ml three-necked flask was charged with 10 mmol of intermediate 270-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M270, with a yield of 35.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M270 was: MS (ASAP) = 1098.

[0490] Example 29

[0491] The synthetic route of organic compound M271 is as follows:

[0492] Synthesis of intermediate 271-2:

[0493] Intermediate 271-1 (20 mmol), compound 269-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 271-2 with a molar weight of 5.87 mmol and a yield of 58.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 271-2 was: MS (ASAP) = 311.

[0494] Synthesis of intermediate 271-3:

[0495] Intermediate 271-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 271-3 with a molar weight of 6.78 mmol and a yield of 67.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 271-3 was: MS (ASAP) = 499.

[0496] Synthesis of intermediate 271-4:

[0497] Intermediate 271-3 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 271-4 with a molar weight of 8.09 mmol and a yield of 80.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 271-4 was: MS (ASAP) = 1190.

[0498] Synthesis of organic compound M271:

[0499] A 250 ml three-necked flask was charged with 10 mmol of intermediate 271-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M271, with a yield of 37.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M271 was: MS (ASAP) = 1164.

[0500] Example 30

[0501] The synthetic route of organic compound M274 is as follows:

[0502] Synthesis of intermediate 274-2:

[0503] Intermediate 268-4 (10 mmol), compound 274-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 274-2 with a molar weight of 6.34 mmol and a yield of 63.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 274-2 was: MS (ASAP) = 225.

[0504] Synthesis of intermediate 274-3:

[0505] Intermediate 274-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 274-3 with a molar weight of 6.18 mmol and a yield of 61.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 274-3 was: MS (ASAP) = 413.

[0506] Synthesis of intermediate 274-4:

[0507] Intermediate 274-3 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 274-4 with a molar weight of 8.39 mmol and a yield of 83.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 274-4 was: MS (ASAP) = 1104.

[0508] Synthesis of organic compound M274:

[0509] A 250 ml three-necked flask was charged with 10 mmol of intermediate 274-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M274, with a yield of 32.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M274 was: MS (ASAP) = 1078.

[0510] Example 31

[0511] The synthetic route of organic compound M277 is as follows:

[0512] Synthesis of intermediate 277-1:

[0513] Intermediate 1-3 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 277-1 with a molar weight of 8.15 mmol and a yield of 81.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 277-1 was: MS (ASAP) = 1028.

[0514] Synthesis of organic compound M277:

[0515] A 250 ml three-necked flask was charged with 10 mmol of intermediate 277-1 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M277, with a yield of 32.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M277 was: MS (ASAP) = 1002.1H NMR (400MHz, CDCl3) δ9.01 (s, 1H), 8.55 (s, 1H), 8.42 (dd, J = 19.1, 9.7Hz, 4H), 7. 91(s,1H),7.78(dt,J=19.1,10.1Hz,7H),7.59(t,J=10.3Hz,3H),7.55–7.33(m, 9H),7.23(t,J=7.4Hz,1H),7.04(d,J=8.8Hz,1H),6.49(s,1H),6.42(d,J=7.9Hz ,1H),6.31(d,J=8.5Hz,1H),1.58(s,9H),1.50(s,9H),1.44(s,9H),1.07(s,9H).

[0516] Example 32

[0517] The synthetic route of organic compound M278 is as follows:

[0518] Synthesis of intermediate 278-1:

[0519] Intermediate 1-1 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 278-1 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 278-1 was: MS (ASAP) = 840.

[0520] Synthesis of intermediate 278-2:

[0521] Intermediate 278-1 (10 mmol) and 50 mL of acetonitrile were added to a three-necked flask. 20 mmol of CuCl and 30 mmol of t-butyl nitrite (t-BuONO) were added at 65°C. Gas evolution was observed. After the addition was complete, gas evolution ceased, and the mixture was cooled to room temperature and stirred for 1 hour. After extraction with dichloromethane and spin drying, the mixture was dissolved in petroleum ether and filtered through silica gel to obtain Intermediate 278-2 with a molar weight of 8.76 mmol and a yield of 87.6%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) of Intermediate 278-2 showed MS (ASAP) = 320.

[0522] Synthesis of intermediate 278-3:

[0523] Intermediate 278-1 (10 mmol), intermediate 278-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 278-3 with a molar weight of 7.54 mmol and a yield of 75.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 278-3 was: MS (ASAP) = 1124.

[0524] Synthesis of organic compound M278:

[0525] A 250 ml three-necked flask was charged with 10 mmol of intermediate 278-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M278, with a yield of 37.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M278 was: MS (ASAP) = 1098.

[0526] Example 33

[0527] The synthetic route of organic compound M279 is as follows:

[0528] Synthesis of intermediate 279-2:

[0529] Intermediate 279-1 (10 mmol), intermediate 268-4 (20 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 279-2 with a molar weight of 8.09 mmol and a yield of 80.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 279-2 was: MS (ASAP) = 432.

[0530] Synthesis of intermediate 279-3:

[0531] Intermediate 279-2 (10 mmol), intermediate 278-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 279-3 with a molar weight of 7.33 mmol and a yield of 73.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 279-3 was: MS (ASAP) = 1236.

[0532] Synthesis of organic compound M279:

[0533] A 250 ml three-necked flask was charged with 10 mmol of intermediate 279-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M279, with a yield of 45.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M279 was: MS (ASAP) = 1210.

[0534] Example 34

[0535] The synthetic route of organic compound M280 is as follows:

[0536] Synthesis of intermediate 280-1:

[0537] Intermediate 274-2 (10 mmol) and 50 mL of acetonitrile were added to a three-necked flask. CuCl (20 mmol) and t-butyl nitrite (t-BuONO) (30 mmol) were added at 65°C. Gas evolution was observed. After the addition was complete, gas evolution ceased, and the mixture was cooled to room temperature and stirred for 1 hour. After extraction with dichloromethane and spin drying, the mixture was dissolved in petroleum ether and filtered through silica gel to obtain Intermediate 280-1 (8.92 mmol, yield: 89.2%). Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) of Intermediate 280-1 yielded: MS (ASAP) = 244.

[0538] Synthesis of intermediate 280-2:

[0539] Intermediate 280-1 (10 mmol), intermediate 278-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 280-2 with a molar weight of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 280-2 was: MS (ASAP) = 1048.

[0540] Synthesis of organic compound M280:

[0541] A 250 ml three-necked flask was charged with 10 mmol of intermediate 280-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M280, with a yield of 34.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M280 was: MS (ASAP) = 1022.

[0542] Example 35

[0543] The synthetic route of organic compound M281 is as follows:

[0544] Synthesis of intermediate 281-2:

[0545] Intermediate 281-1 (10 mmol), intermediate 269-4 (20 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 281-2 with a molar weight of 8.38 mmol and a yield of 83.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 281-2 was: MS (ASAP) = 244.

[0546] Synthesis of intermediate 281-3:

[0547] Intermediate 281-2 (10 mmol), intermediate 278-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 281-3 with a molar weight of 6.79 mmol and a yield of 67.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 281-3 was: MS (ASAP) = 1048.

[0548] Synthesis of organic compound M281:

[0549] A 250 ml three-necked flask was charged with 10 mmol of intermediate 281-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M281, with a yield of 42.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M281 was: MS (ASAP) = 1022.

[0550] Example 36

[0551] The synthetic route of organic compound M282 is as follows:

[0552] Synthesis of intermediate 282-1:

[0553] Intermediate 281-1 (10 mmol), intermediate 268-4 (20 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 282-1 with a molar weight of 7.46 mmol and a yield of 74.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 282-1 was: MS (ASAP) = 300.

[0554] Synthesis of intermediate 282-2:

[0555] Intermediate 281-2 (10 mmol), intermediate 278-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 282-2 with a molar weight of 6.13 mmol and a yield of 61.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 282-2 was: MS (ASAP) = 1104.

[0556] Synthesis of organic compound M282:

[0557] A 250 ml three-necked flask was charged with 10 mmol of intermediate 282-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed by evaporation under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M282, with a yield of 33.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M282 was: MS (ASAP) = 1078.

[0558] Example 37

[0559] The synthetic route of organic compound M283 is as follows:

[0560] Synthesis of intermediate 283-1:

[0561] Intermediate 268-6 (10 mmol) and 50 mL of acetonitrile were added to a three-necked flask. CuCl (20 mmol) and t-butyl nitrite (t-BuONO) (30 mmol) were added at 65°C. Gas evolution was observed. After the addition was complete, gas evolution ceased, and the mixture was cooled to room temperature and stirred for 1 hour. After extraction with dichloromethane and spin drying, the mixture was dissolved in petroleum ether and filtered through silica gel to obtain Intermediate 283-1 (9.02 mmol, 90.2% yield). Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) of Intermediate 283-1 yielded: MS (ASAP) = 376.

[0562] Synthesis of intermediate 283-2:

[0563] Intermediate 283-1 (10 mmol), intermediate 278-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 283-2 with a molar weight of 6.97 mmol and a yield of 69.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 283-2 was: MS (ASAP) = 1180.

[0564] Synthesis of organic compound M283:

[0565] A 250 ml three-necked flask was charged with 10 mmol of intermediate 283-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M283, with a yield of 36.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M283 was: MS (ASAP) = 1154.

[0566] Example 38

[0567] The synthetic route of organic compound M284 is as follows:

[0568] Synthesis of intermediate 284-1:

[0569] Intermediate 1-1 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 284-1 with a molar weight of 8.25 mmol and a yield of 82.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 284-1 was: MS (ASAP) = 764.

[0570] Synthesis of intermediate 284-2:

[0571] Intermediate 284-1 (10 mmol), intermediate 281-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 284-2 with a molar weight of 7.31 mmol and a yield of 73.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 284-2 was: MS (ASAP) = 972.

[0572] Synthesis of organic compound M284:

[0573] A 250 ml three-necked flask was charged with 10 mmol of intermediate 284-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M284, with a yield of 47.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M284 was: MS (ASAP) = 946.

[0574] Example 39

[0575] The synthetic route of organic compound M285 is as follows:

[0576] Synthesis of intermediate 285-1:

[0577] Intermediate 284-1 (10 mmol), intermediate 282-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 285-1 with a molar weight of 8.97 mmol and a yield of 89.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 285-1 was: MS (ASAP) = 1028.

[0578] Synthesis of organic compound M285:

[0579] A 250 ml three-necked flask was charged with 10 mmol of intermediate 285-1 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M285, with a yield of 40.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M285 was: MS (ASAP) = 1002.

[0580] Example 40

[0581] The synthetic route of organic compound M286 is as follows:

[0582] Synthesis of intermediate 286-1:

[0583] Intermediate 284-1 (10 mmol), intermediate 278-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 286-1 with a molar weight of 8.45 mmol and a yield of 84.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 286-1 was: MS (ASAP) = 1048.

[0584] Synthesis of organic compound M286:

[0585] A 250 ml three-necked flask was charged with 10 mmol of intermediate 286-1 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M286, with a yield of 47.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M286 was: MS (ASAP) = 1022.

[0586] Example 41

[0587] The synthetic route of organic compound M287 is as follows:

[0588] Synthesis of intermediate 287-1:

[0589] Intermediate 284-1 (10 mmol), intermediate 280-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 287-1 with a molar weight of 8.22 mmol and a yield of 82.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 287-1 was: MS (ASAP) = 972.

[0590] Synthesis of organic compound M287:

[0591] A 250 ml three-necked flask was charged with 10 mmol of intermediate 287-1 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M287, with a yield of 36.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M287 was: MS (ASAP) = 946.

[0592] Example 42

[0593] The synthetic route of organic compound M288 is as follows:

[0594] Synthesis of intermediate 288-1:

[0595] Intermediate 284-1 (10 mmol), intermediate 283-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 288-1 with a molar weight of 9.12 mmol and a yield of 91.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 288-1 was: MS (ASAP) = 1104.

[0596] Synthesis of organic compound M288:

[0597] A 250 ml three-necked flask was charged with 10 mmol of intermediate 288-1 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M288, with a yield of 35.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M288 was: MS (ASAP) = 1078.

[0598] Example 43

[0599] The synthetic route of organic compound M289 is as follows:

[0600] Synthesis of intermediate 289-1:

[0601] Intermediate 284-1 (10 mmol), intermediate 279-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 289-1 with a molar weight of 8.06 mmol and a yield of 80.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 289-1 was: MS (ASAP) = 1160.

[0602] Synthesis of organic compound M289:

[0603] A 250 ml three-necked flask was charged with 10 mmol of intermediate 288-1 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M289, with a yield of 33.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M289 was: MS (ASAP) = 1134.

[0604] Example 44

[0605] The synthetic route of organic compound M290 is as follows:

[0606] Synthesis of intermediate 290-2:

[0607] Intermediate 290-1 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 290-2 with a molar weight of 8.15 mmol and a yield of 81.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 290-2 was: MS (ASAP) = 840.

[0608] Synthesis of intermediate 290-3:

[0609] Intermediate 290-2 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 290-3 with a molar weight of 7.39 mmol and a yield of 73.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 290-3 was: MS (ASAP) = 1028.

[0610] Synthesis of organic compound M290:

[0611] A 250 ml three-necked flask was charged with 10 mmol of intermediate 290-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M290, with a yield of 33.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M290 was: MS (ASAP) = 1002.1H NMR(400MHz, CDCl3)δ9.02(s,1H),8.57(d,J=18.8Hz,1H),8.48–8.36(m,4H),7.92(s,1H),7.87–7.75(m,5H),7.72(d,J=7.8Hz,6H),7.69–7.6 1(m,4H),7.53–7.32(m,4H),7.20(d,J=16.8Hz,1H),7.09–6.96(m,1H), 6.51–6.26(m,3H),1.58(s,9H),1.44(s,9H),1.39(s,9H),1.06(s,9H).

[0612] Example 45

[0613] The synthetic route of organic compound M291 is as follows:

[0614] Synthesis of intermediate 291-2:

[0615] Intermediate 291-1 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 291-2 with a molar weight of 8.84 mmol and a yield of 88.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 291-2 was: MS (ASAP) = 784.

[0616] Synthesis of intermediate 291-3:

[0617] Intermediate 291-2 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 291-3 with a molar weight of 7.22 mmol and a yield of 72.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 291-3 was: MS (ASAP) = 972.

[0618] Synthesis of organic compound M291:

[0619] A 250 ml three-necked flask was charged with 10 mmol of intermediate 291-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M291, with a yield of 38.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M291 was: MS (ASAP) = 946.

[0620] Example 46

[0621] The synthetic route of organic compound M292 is as follows:

[0622] Synthesis of intermediate 292-1:

[0623] Intermediate 253-4 (10 mmol), compound 290-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 292-1 with a molar weight of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 292-1 was: MS (ASAP) = 820.

[0624] Synthesis of intermediate 292-2:

[0625] Intermediate 292-1 (10 mmol), compound 269-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 292-2 with a molar weight of 6.62 mmol and a yield of 66.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 292-2 was: MS (ASAP) = 1028.

[0626] Synthesis of organic compound M292:

[0627] A 250 ml three-necked flask was charged with 10 mmol of intermediate 292-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed by evaporation under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M292, with a yield of 43.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M292 was: MS (ASAP) = 1002.

[0628] Example 47

[0629] The synthetic route of organic compound M293 is as follows:

[0630] Synthesis of intermediate 293-1:

[0631] Intermediate 253-4 (10 mmol), compound 291-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 293-1 with a molar weight of 7.08 mmol and a yield of 70.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 293-1 was: MS (ASAP) = 764.

[0632] Synthesis of intermediate 293-2:

[0633] Intermediate 293-1 (10 mmol), compound 269-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 293-2 with a molar weight of 6.51 mmol and a yield of 65.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 293-2 was: MS (ASAP) = 972.

[0634] Synthesis of organic compound M293:

[0635] A 250 ml three-necked flask was charged with 10 mmol of intermediate 293-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed by evaporation under reduced pressure. The reaction mixture was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M293, with a yield of 41.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M293 was: MS (ASAP) = 946.

[0636] Example 48

[0637] The synthetic route of organic compound M294 is as follows:

[0638] Synthesis of intermediate 294-1:

[0639] Intermediate 253-4 (10 mmol), compound 268-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 294-1 with a molar weight of 7.37 mmol and a yield of 73.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 294-1 was: MS (ASAP) = 1028.

[0640] Synthesis of intermediate 294-2:

[0641] Intermediate 294-1 (10 mmol), compound 269-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 294-2 with a molar weight of 6.89 mmol and a yield of 68.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 294-2 was: MS (ASAP) = 1236.

[0642] Synthesis of organic compound M294:

[0643] A 250 ml three-necked flask was charged with 10 mmol of intermediate 294-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M294, with a yield of 43.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M294 was: MS (ASAP) = 1210.

[0644] Example 49

[0645] The synthetic route of organic compound M295 is as follows:

[0646] Synthesis of intermediate 295-1:

[0647] Intermediate 253-4 (10 mmol), compound 269-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 295-1 with a molar weight of 8.23 ​​mmol and a yield of 82.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 295-1 was: MS (ASAP) = 972.

[0648] Synthesis of intermediate 295-2:

[0649] Intermediate 295-1 (10 mmol), compound 269-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 295-2 with a molar weight of 7.46 mmol and a yield of 74.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 295-2 was: MS (ASAP) = 1180.

[0650] Synthesis of organic compound M295:

[0651] A 250 ml three-necked flask was charged with 10 mmol of intermediate 295-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M295, with a yield of 36.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M295 was: MS (ASAP) = 1154.

[0652] Example 50

[0653] The synthetic route of organic compound M296 is as follows:

[0654] Synthesis of intermediate 296-2:

[0655] Intermediate 296-1 (10 mmol), intermediate 269-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 296-2 with a molar weight of 8.89 mmol and a yield of 88.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 296-2 was: MS (ASAP) = 840.

[0656] Synthesis of intermediate 296-3:

[0657] Intermediate 296-2 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 296-3 with a molar weight of 7.97 mmol and a yield of 79.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 296-3 was: MS (ASAP) = 1028.

[0658] Synthesis of organic compound M296:

[0659] A 250 ml three-necked flask was charged with 10 mmol of intermediate 296-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M296, with a yield of 39.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M296 was: MS (ASAP) = 1002.

[0660] Example 51

[0661] The synthetic route of organic compound M297 is as follows:

[0662] Synthesis of intermediate 297-1:

[0663] Intermediate 253-4 (10 mmol), compound 296-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 297-1 with a molar weight of 7.81 mmol and a yield of 78.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 297-1 was: MS (ASAP) = 820.

[0664] Synthesis of intermediate 297-2:

[0665] Intermediate 297-1 (10 mmol), compound 269-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 297-2 with a molar weight of 6.81 mmol and a yield of 68.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 297-2 was: MS (ASAP) = 1028.

[0666] Synthesis of organic compound M297:

[0667] A 250 ml three-necked flask was charged with 10 mmol of intermediate 297-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M297, with a yield of 39.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M297 was: MS (ASAP) = 1002.

[0668] Example 52

[0669] The synthetic route of organic compound M298 is as follows:

[0670] Synthesis of intermediate 298-1:

[0671] Compound 290-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 298-1 with a molar weight of 7.33 mmol and a yield of 73.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 298-1 was: MS (ASAP) = 337.

[0672] Synthesis of intermediate 298-2:

[0673] Compound 298-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 298-2 with a molar weight of 8.25 mmol and a yield of 82.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 298-2 was: MS (ASAP) = 481.

[0674] Synthesis of intermediate 298-3:

[0675] Intermediate 2982 (10 mmol), compound 24-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 298-3 with a molar weight of 6.54 mmol and a yield of 65.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 298-3 was: MS (ASAP) = 726.

[0676] Synthesis of intermediate 298-5:

[0677] Intermediate 298-3 (10 mmol), compound 298-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 298-5 with a molar weight of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 298-5 was: MS (ASAP) = 850.

[0678] Synthesis of intermediate 298-6:

[0679] Intermediate 298-5 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 298-6 with a molar weight of 8.76 mmol and a yield of 87.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 298-6 was: MS (ASAP) = 1042.

[0680] Synthesis of organic compound M298:

[0681] A 250 ml three-necked flask was charged with 10 mmol of intermediate 298-6 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M298, with a yield of 33.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M298 was: MS (ASAP) = 1016.

[0682] Example 53

[0683] The synthetic route of organic compound M299 is as follows:

[0684] Synthesis of intermediate 299-2:

[0685] Intermediate 298-3 (10 mmol), compound 299-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 299-2 with a molar weight of 7.10 mmol and a yield of 71.0%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 299-2 was: MS (ASAP) = 836.

[0686] Synthesis of intermediate 299-3:

[0687] Intermediate 299-2 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 299-3 with a molar weight of 8.11 mmol and a yield of 81.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 299-3 was: MS (ASAP) = 1028.

[0688] Synthesis of organic compound M299:

[0689] A 250 ml three-necked flask was charged with 10 mmol of intermediate 299-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M299, with a yield of 39.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M299 was: MS (ASAP) = 1002.

[0690] Example 54

[0691] The synthetic route of organic compound M300 is as follows:

[0692] Synthesis of intermediate 300-2:

[0693] Intermediate 1-5 (10 mmol), compound 300-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 300-2 with a molar weight of 7.26 mmol and a yield of 72.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 300-2 was: MS (ASAP) = 670.

[0694] Synthesis of intermediate 300-3:

[0695] Intermediate 300-2 (10 mmol), compound 298-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 300-3 with a molar weight of 6.85 mmol and a yield of 68.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 300-3 was: MS (ASAP) = 794.

[0696] Synthesis of intermediate 300-4:

[0697] Intermediate 300-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallization to obtain intermediate 300-4 with a molar weight of 7.79 mmol and a yield of 77.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 300-4 was: MS (ASAP) = 986.

[0698] Synthesis of organic compound M300:

[0699] A 250 ml three-necked flask was charged with 10 mmol of intermediate 300-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120° C. with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M300, with a yield of 36.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M300 was: MS (ASAP) = 960.

[0700] Example 55

[0701] The synthetic route of organic compound M301 is as follows:

[0702] Synthesis of intermediate 301-1:

[0703] Intermediate 1-5 (10 mmol), compound 24-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 301-1 with a molar weight of 7.88 mmol and a yield of 78.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 301-1 was: MS (ASAP) = 726.

[0704] Synthesis of intermediate 301-2:

[0705] Intermediate 301-1 (10 mmol), compound 298-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 301-2 with a molar weight of 6.21 mmol and a yield of 62.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 301-2 was: MS (ASAP) = 850.

[0706] Synthesis of intermediate 301-3:

[0707] Intermediate 301-2 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 301-3 with a molar weight of 7.53 mmol and a yield of 75.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 301-3 was: MS (ASAP) = 1042.

[0708] Synthesis of organic compound M301:

[0709] A 250 ml three-necked flask was charged with 10 mmol of intermediate 301-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M301, with a yield of 37.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M301 was: MS (ASAP) = 1016.

[0710] Example 56

[0711] The synthetic route of organic compound M302 is as follows:

[0712] Synthesis of intermediate 302-1:

[0713] Intermediate 253-4 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 302-1 with a molar weight of 8.45 mmol and a yield of 84.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 302-1 was: MS (ASAP) = 820.

[0714] Synthesis of intermediate 302-3:

[0715] Intermediate 302-1 (10 mmol), compound 302-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 302-3 with a molar weight of 7.59 mmol and a yield of 75.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 302-3 was: MS (ASAP) = 1048.

[0716] Synthesis of organic compound M302:

[0717] A 250 ml three-necked flask was charged with 10 mmol of intermediate 302-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was evaporated to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M302, with a yield of 36.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M302 was: MS (ASAP) = 1022.

[0718] Example 57

[0719] The synthetic route of organic compound M303 is as follows:

[0720] Synthesis of intermediate 303-2:

[0721] Intermediate 253-4 (10 mmol), compound 303-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 303-2 with a molar weight of 8.31 mmol and a yield of 83.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 303-2 was: MS (ASAP) = 916.

[0722] Synthesis of intermediate 303-3:

[0723] Intermediate 303-2 (10 mmol), compound 302-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 303-3 with a molar weight of 7.17 mmol and a yield of 71.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 303-3 was: MS (ASAP) = 1144.

[0724] Synthesis of organic compound M303:

[0725] A 250 ml three-necked flask was charged with 10 mmol of intermediate 303-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M303, with a yield of 37.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M303 was: MS (ASAP) = 1118.

[0726] Example 58

[0727] The synthetic route of organic compound M304 is as follows:

[0728] Synthesis of intermediate 304-2:

[0729] Compound 129-1 (10 mmol), compound 304-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 304-2 with a molar weight of 7.03 mmol and a yield of 70.3%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 304-2 was: MS (ASAP) = 481.

[0730] Synthesis of intermediate 304-3:

[0731] Intermediate 304-2 (10 mmol), compound 303-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 304-3 with a molar weight of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 304-3 was: MS (ASAP) = 690.

[0732] Synthesis of intermediate 304-4:

[0733] Intermediate 304-3 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 304-4 with a molar weight of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 304-4 was: MS (ASAP) = 856.

[0734] Synthesis of intermediate 304-6:

[0735] Intermediate 304-4 (10 mmol) and intermediate 304-5 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 304-6 with a molar weight of 7.22 mmol and a yield of 72.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 304-6 was: MS (ASAP) = 1048.

[0736] Synthesis of organic compound M304:

[0737] A 250 ml three-necked flask was charged with 10 mmol of intermediate 304-6 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M304, with a yield of 34.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M304 was: MS (ASAP) = 1022.

[0738] Example 59

[0739] The synthetic route of organic compound M305 is as follows:

[0740] Synthesis of intermediate 305-1:

[0741] Intermediate 20-2 (10 mmol) and compound 16-5 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 305-1 with a molar weight of 8.27 mmol and a yield of 82.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 305-1 was: MS (ASAP) = 896.

[0742] Synthesis of intermediate 305-3:

[0743] Intermediate 305-1 (10 mmol), compound 305-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 305-3 with a molar weight of 7.69 mmol and a yield of 76.9%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 305-3 was: MS (ASAP) = 1104.

[0744] Synthesis of organic compound M305:

[0745] A 250 ml three-necked flask was charged with 10 mmol of intermediate 305-3 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M305, with a yield of 51.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M305 was: MS (ASAP) = 1078.

[0746] Example 60

[0747] The synthetic route of organic compound M306 is as follows:

[0748] Synthesis of intermediate 306-1:

[0749] Intermediate 1-1 (10 mmol) and compound 16-5 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 306-1 with a molar weight of 8.89 mmol and a yield of 88.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 306-1 was: MS (ASAP) = 764

[0750] Synthesis of intermediate 306-2:

[0751] Intermediate 306-1 (10 mmol), compound 305-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 306-2 with a molar weight of 7.33 mmol and a yield of 73.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 306-2 was: MS (ASAP) = 972

[0752] Synthesis of organic compound M306:

[0753] A 250 ml three-necked flask was charged with 10 mmol of intermediate 306-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, organic compound M306, with a yield of 46.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M306 was: MS (ASAP) = 946

[0754] Example 61

[0755] The synthetic route of organic compound M307 is as follows:

[0756] Synthesis of intermediate 307-1:

[0757] Intermediate 16-8 (10 mmol) and compound 16-5 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 307-1 with a molar weight of 8.41 mmol and a yield of 84.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 307-1 was: MS (ASAP) = 896.

[0758] Synthesis of intermediate 307-2:

[0759] Intermediate 307-1 (10 mmol), compound 305-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 307-2 with a molar weight of 7.89 mmol and a yield of 78.9%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 307-2 was: MS (ASAP) = 1104.

[0760] Synthesis of organic compound M307:

[0761] A 250 ml three-necked flask was charged with 10 mmol of intermediate 307-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction mixture was cooled to -30°C again and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M307, with a yield of 44.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M307 was: MS (ASAP) = 1078.

[0762] Example 62

[0763] The synthetic route of organic compound M308 is as follows:

[0764] Synthesis of intermediate 308-1:

[0765] Intermediate 24-2 (10 mmol) and compound 16-5 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 308-1 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 308-1 was: MS (ASAP) = 896.

[0766] Synthesis of intermediate 308-2:

[0767] Intermediate 308-1 (10 mmol), compound 305-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 308-2 with a molar weight of 7.93 mmol and a yield of 79.3%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 308-2 was: MS (ASAP) = 1104.

[0768] Synthesis of organic compound M308:

[0769] A 250 ml three-necked flask was charged with 10 mmol of intermediate 308-2 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction mixture was cooled to -30°C again and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M308, with a yield of 41.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M308 was: MS (ASAP) = 1078.

[0770] Example 63

[0771] The synthetic route of organic compound M309 is as follows:

[0772] Synthesis of intermediate 309-1:

[0773] Intermediate 280-1 (10 mmol), intermediate 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 309-1 with a molar weight of 7.89 mmol and a yield of 78.9%. Atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) of intermediate 309-1 showed an MS (ASAP) value of 357.

[0774] Synthesis of intermediate 309-2:

[0775] Intermediate 309-1 (10 mmol), intermediate 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 309-2 with a molar weight of 7.56 mmol and a yield of 75.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 309-1 was: MS (ASAP) = 501.

[0776] Synthesis of intermediate 309-4:

[0777] Intermediate 309-2 (10 mmol), intermediate 309-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 309-4 with a molar weight of 7.11 mmol and a yield of 71.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 309-4 was: MS (ASAP) = 592.

[0778] Synthesis of intermediate 309-5:

[0779] Intermediate 309-4 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 309-5 with a molar weight of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 309-5 was: MS (ASAP) = 784.

[0780] Synthesis of intermediate 309-6:

[0781] Intermediate 309-5 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120°C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 309-6 with a molar weight of 7.97 mmol and a yield of 79.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 309-6 was: MS (ASAP) = 972.

[0782] Synthesis of organic compound M309:

[0783] A 250 ml three-necked flask was charged with 10 mmol of intermediate 309-6 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a nitrogen atmosphere. A 21 mmol n-hexane solution of t-BuLi (tert-butyl lithium) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M309, with a yield of 42.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M309 was: MS (ASAP) = 946.

[0784] Comparative Example 1

[0785] Comparative Compound 1 was used as a comparative example for Examples 1 to 63. The structural formula of Comparative Compound 1 is:

[0786] As shown in Table 1, the HOMO (Highest Occupied Molecular Orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital) energy level, T1 (first excited triplet state) energy level, and S1 (first excited singlet state) energy level of compounds M1 to M309 obtained in Examples 1 to 63 and the comparative compound 1 in Comparative Example 1 can be obtained by quantum calculation. Specifically, TD-DFT (time-dependent density functional theory) was used with Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110. First, the molecular geometry was optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule was calculated using the TD-DFT (time-dependent density functional theory) method using "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels were calculated using the following calibration formula, and the S1 and T1 energy levels were used directly.

[0787] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0788] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0789] Among them, HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree.

[0790] Table 1: Calculation results of HOMO energy level, LUMO energy level, S1 energy level and T1 energy level of organic compounds M1 to M309 and comparative compound 1

[0791] As can be seen from the results in Table 1, the T1 energy level and S1 energy level of the organic compounds M1 to M309 provided in Examples 1 to 63 of the present application are all higher than the T1 energy level and S1 energy level of the comparative compound 1, indicating that compared with the comparative compound 1, the blue light emitted by the organic compounds M1 to M309 is more inclined to deep blue, which is conducive to obtaining better color coordinates for blue organic light-emitting devices using the organic compounds M1 to M309 as guest materials in the light-emitting layer.

[0792] The exemplary manufacturing steps of the organic light-emitting device 100 provided in this application are shown in the following exemplary embodiment 1.

[0793] Example 1

[0794] In the organic light-emitting device provided in this embodiment, ITO (indium tin oxide) is used as the anode, PEDOT (polyethylenedioxythiophene, Clevios AI4083) is used as the material for the hole injection layer, PVK (Sigma Aldrich, average Mn 25,000-50,000) is used as the material for the hole transport layer, BH-1 to BH-3 are respectively used as the host materials in the light-emitting layers of the corresponding organic light-emitting devices, the organic compounds M1 to M309 in Examples 1 to Example 67 and the comparative compound 1 in Comparative Example 1 are respectively used as the guest materials in the light-emitting layers of the corresponding organic light-emitting devices, ET and Liq (lithium 8-hydroxyquinoline) are used as the materials for the electron transport layer, and Al is used as the cathode. The specific preparation steps are as follows: ...

Claims

1. An organic compound, wherein The organic compound has a structure as shown in general formula (1) or (2): Wherein, Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3): Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5): When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formula (A-2) to formula (A-5); The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring; Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4): X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2; n0, n1, n2, n5 are each independently selected from a positive integer between 0 and 14; Any R0, R1, R2 or R5 is independently selected from: -H, -D, having 1 to 20 carbon atoms a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, -CN, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; When n0 is greater than or equal to 2, two adjacent R0s may or may not form a ring with each other; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a ring with each other; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a ring with each other; when n5 is greater than or equal to 2, two adjacent R5s may or may not form a ring with each other.

2. The organic compound according to claim 1, wherein The organic compound has a structure as shown in any one of the general formulas (2-1) to (2-28): Wherein, any R3, R4 are independently selected from: -H, -D, a straight chain having 1 to 20 carbon atoms a cycloalkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, -CN, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; n3 is greater than or equal to 0 and less than or equal to 5; When n3 is greater than or equal to 2, two adjacent R3s may or may not form a ring with each other; n4 is greater than or equal to 0 and less than or equal to 5; When n4 is greater than or equal to 2, two adjacent R4s may or may not form a ring with each other.

3. The organic compound according to claim 2, wherein Any of R1, R2, R3, R4 or R5 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms.

4. The organic compound according to claim 3, wherein Any of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, a straight chain alkyl group having 1 to 4 carbon atoms, a branched chain alkyl group having 3 to 5 carbon atoms.

5. The organic compound according to claim 1, wherein When Ar2 contains a structure represented by the formula (B-2), the structure represented by the formula (B-2) is selected from: as well as At least one of .

6. The organic compound according to claim 1, wherein The organic compound is a blue light emitting material.

7. The organic compound according to claim 1, wherein The organic compound is selected from the following compounds:

8. A mixture, wherein comprising an organic compound and at least one organic functional material, wherein the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent material, a host material or an organic dye; Wherein, the organic compound has a structure as shown in general formula (1) or (2): Wherein, Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3): Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5): When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formula (A-2) to formula (A-5); The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring; Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4): X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2; n0, n1, n2, n5 are each independently selected from a positive integer between 0 and 14; Any R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic an alkoxy group, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; When n0 is greater than or equal to 2, two adjacent R0s may or may not form a ring with each other; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a ring with each other; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a ring with each other; when n5 is greater than or equal to 2, two adjacent R5s may or may not form a ring with each other.

9. A composition, wherein comprising an organic compound or mixture, and at least one organic solvent; The mixture comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes; The organic compound has a structure as shown in general formula (1) or (2): Wherein, Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3): Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5): When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formula (A-2) to formula (A-5); The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring; Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4): X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2; n0, n1, n2, n5 are each independently selected from a positive integer between 0 and 14; Any R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; When n0 is greater than or equal to 2, two adjacent R0s may or may not form a ring with each other; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a ring with each other; when n2 is greater than or equal to 2, two adjacent When n5 is greater than or equal to 2, two adjacent R5s may or may not form a ring with each other.

10. An organic light emitting device, wherein: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; Wherein, the material of the organic functional layer includes one or more organic compounds, or a mixture, or is prepared from a combination; The composition comprises the organic compound or the mixture, and at least one organic solvent; The mixture comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes; The organic compound has a structure as shown in general formula (1) or (2): Wherein, Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3): Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5): When Ar1 is selected from Formula X-2, Ar4 is independently selected from the structure represented by any one of Formulas (A-2) to (A-5). structure; The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring; Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4): X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2; n0, n1, n2, n5 are each independently selected from a positive integer between 0 and 14; Any R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; When n0 is greater than or equal to 2, two adjacent R0s may or may not form a ring with each other; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a ring with each other; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a ring with each other; when n5 is greater than or equal to 2, two adjacent R5s may or may not form a ring with each other.

11. The organic light emitting device according to claim 10, wherein: The organic functional layer at least includes a light-emitting layer, and the light-emitting layer includes a host material and a guest material. The guest material is one or more of the organic compounds, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

12. The organic light emitting device according to claim 11, wherein: The host material includes one or more of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

13. The organic light emitting device according to claim 11, wherein: The mass ratio of the host material to the guest material is 99:1 to 70:

30.

14. A display panel, wherein: An organic light-emitting device is included, wherein the organic light-emitting device includes: a first electrode; a second electrode, disposed opposite to the first electrode; and an organic functional layer, located between the first electrode and the second electrode; Wherein, the material of the organic functional layer includes one or more organic compounds, or a mixture, or is prepared from a combination; The composition comprises the organic compound or the mixture, and at least one organic solvent; The mixture comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes; The organic compound has a structure as shown in general formula (1) or (2): Wherein, Ar1 is independently selected from the structure represented by any one of formula (X-1) to formula (X-3): Ar3 and A r4 Each independently selected from the structure represented by any one of formula (A-1) to formula (A-5): When Ar1 is selected from formula X-2, Ar4 is independently selected from the structure represented by any one of formula (A-2) to formula (A-5); The attachment site of Ar3 is a carbon atom on any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring; Ar2 is selected from the structure represented by any one of formula (B-1) to formula (B-4): X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2; n0, n1, n2, n5 are each independently selected from a positive integer between 0 and 14; Any R0, R1, R2 or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; When n0 is greater than or equal to 2, two adjacent R0s may or may not form a ring with each other; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a ring with each other; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a ring with each other. When n5 is greater than or equal to 2, two adjacent R5s may form a ring or may not form a ring.

15. The display panel according to claim 14, wherein: The organic compound has a structure as shown in any one of the general formulas (2-1) to (2-28): Wherein, any R3, R4 are independently selected from: -H, -D, a straight chain having 1 to 20 carbon atoms a cycloalkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, -CN, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; n3 is greater than or equal to 0 and less than or equal to 5; When n3 is greater than or equal to 2, two adjacent R3s may or may not form a ring with each other; n4 is greater than or equal to 0 and less than or equal to 5; When n4 is greater than or equal to 2, two adjacent R4s may or may not form a ring with each other.

16. The display panel according to claim 15, wherein: Any of R1, R2, R3, R4 or R5 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms.

17. The display panel according to claim 16, wherein: Any of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, a straight chain alkyl group having 1 to 4 carbon atoms, a branched chain alkyl group having 3 to 5 carbon atoms.

18. The display panel according to claim 14, wherein: When Ar2 contains a structure represented by the formula (B-2), the structure represented by the formula (B-2) is selected from: as well as At least one of .

19. The display panel according to claim 14, wherein: The organic functional layer at least includes a light-emitting layer, and the light-emitting layer includes a host material and a guest material. The guest material is one or more of the organic compounds, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

20. The display panel according to claim 19, wherein: The host material includes one or more of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

Images