Organic compounds, mixtures, compositions, organic light-emitting devices, and display panels

Abstract

Embodiments of the present application disclose an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel having a structure represented by General Formula (1) or General Formula (2). The present application improves material properties, improves the luminous efficiency of the organic light-emitting device, and extends the service life of the organic light-emitting device by introducing a group that increases the conjugation of the entire compound into the boron-nitrogen compound. JPEG2025523278000181.jpg33170

Description

Technical Field

[0001] This application relates to the field of displays, and in particular, to organic compounds, mixtures, compositions, organic light-emitting devices, and display panels.

Background Art

[0002] Currently, organic electroluminescence devices such as OLEDs (Organic Light-Emitting Diodes) usually have an anode, a cathode, and an organic layer located therebetween, and realize organic electroluminescence by converting electrical energy into light energy using the organic substances in the organic layer. In order to improve the luminous efficiency and service life of the organic electroluminescence device, there are many multiple layers in the organic layer, and the organic substances are different for each layer. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied between the anode and the cathode of the organic electroluminescence device, the anode injects holes into the organic layer, the cathode injects electrons into the organic layer, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state, thereby realizing the light emission of the organic electroluminescence device. The organic electroluminescence device has characteristics such as self-luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response. Therefore, the organic electroluminescence device has broad application prospects.

[0003] In order to improve the luminous efficiency of organic electroluminescent devices, various luminescent material systems based on fluorescence and phosphorescence have been developed. Among them, organic electroluminescent devices using fluorescent materials have the characteristic of high reliability. However, under electrical excitation, since the branching ratio of the singlet excited state and the triplet excited state of excitons is 1:3, the internal electroluminescence quantum efficiency is limited within 25%. On the other hand, organic electroluminescent devices using phosphorescent materials can obtain an internal electroluminescence quantum efficiency of almost 100%. However, phosphorescent materials usually use metal complexes containing iridium or platinum, the raw materials are expensive and the synthesis is complex. Phosphorescent organic electroluminescent devices also exhibit a roll-off effect in which the luminous efficiency rapidly decreases with an increase in current or luminance, and their application at high luminance is limited.

[0004] In order to overcome such problems, in the prior art, attempts have generally been made to utilize reverse internal conversion to achieve high efficiency comparable to that of phosphorescent organic electroluminescent devices based on various combinations of organic compounds such as composite excited state materials and thermally activated delayed fluorescence (TADF) materials. However, conventional organic compounds having TADF have limitations in improving their performance in terms of efficiency and service life, and it has been difficult to improve the luminous efficiency and service life of organic electroluminescent devices using organic compounds having TADF.

[0005] Therefore, in order to solve the above technical problems, there is an urgent need for organic compounds for organic light-emitting devices.

Summary of the Invention

Problems to be Solved by the Invention

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

Means for Solving the Problems

[0007] To solve the above problems, the technical solution provided by the present application is as follows.

[0008] The present application provides an organic compound having a structure represented by general formula (1) or (2).

[0009]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0010] Any one of R0, R1, R2, or R5 is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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 2 or more, two adjacent R0s may form a ring with each other or may not form a ring. When n1 is 2 or more, two adjacent R1s may form a ring with each other or may not form a ring. When n2 is 2 or more, two adjacent R2s may form a ring with each other or may not form a ring. When n5 is 2 or more, two adjacent R5s may form a ring with each other or may not form a ring.

[0011] The organic compound preferably has a structure represented by any one of general formulas (2-1) to (2-28).

Chemical formula

Chemical formula

Chemical formula

[0012] When n3 is 2 or more, two adjacent R3s may or may not form a ring with each other. n4 is 0 or more and 5 or less.

[0013] When n4 is 2 or more, two adjacent R4s may or may not form a ring with each other.

[0014] 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, and a cyclic alkyl group having 3 to 10 carbon atoms.

[0015] 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, and a branched alkyl group having 3 to 5 carbon atoms.

[0016] Preferably, when the structure represented by the formula (B-2) is present in Ar2, the structure represented by the formula (B-2) is

Chemical formula

[0017] Preferably, the organic compound is a blue light-emitting material.

[0018] Preferably, the organic compound is

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0019] Furthermore, the present application provides a mixture comprising an organic compound and at least one organic functional material 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 light emitting material, a host material or an organic dye.

[0020] Here, the organic compound has a structure represented by the general formula (1) or (2),

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0021] Any one of R0, R1, R2 or R5 is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, When n0 is 2 or more, two adjacent R0s may or may not form a ring with each other; when n1 is 2 or more, two adjacent R1s may or may not form a ring with each other; when n2 is 2 or more, two adjacent R2s may or may not form a ring with each other; when n5 is 2 or more, two adjacent R5s may or may not form a ring with each other.

[0022] The present application also provides a composition comprising an organic compound or mixture and at least one organic solvent.

[0023] The mixture provides a mixture comprising the organic compound and at least one organic functional material 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 light emitting material, a host material or an organic dye.

[0024] The organic compound has a structure represented by general formula (1) or (2).

[0025]

Chemical formula

Chemical formula

[0026] Ar3 and Ar4 are each independently selected from structures represented by any of formulae (A-1) to (A-5).

Chemical formula

[0027] When Ar1 is selected from formula X-2, Ar4 is independently selected from structures represented by any of formulae (A-2) to (A-5). The linking site of Ar3 is a carbon atom on any benzene ring, and the condensation site of Ar4 is at two ortho-position carbon atoms in the same benzene ring. Ar2 is selected from structures represented by any of formulae (B-1) to (B-4).

Chemical formula

[0028] Any one of R0, R1, R2 or R5 is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, When n0 is 2 or more, two adjacent R0s may or may not form a ring with each other. When n1 is 2 or more, two adjacent R1s may or may not form a ring with each other. When n2 is 2 or more, two adjacent R2s may or may not form a ring with each other. When n5 is 2 or more, two adjacent R5s may or may not form a ring with each other.

[0029] In addition, this application relates to a first electrode, a second electrode provided opposite to the first electrode, and an organic functional layer positioned between the first electrode and the second electrode, and provides an organic light-emitting device including the same. Here, the material of the organic functional layer includes one or more kinds of organic compounds, or a mixture, or is manufactured from a composition. The composition contains the organic compound or the mixture, and at least one organic solvent, The mixture contains the organic compound and at least one organic functional material 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 light-emitting material, a host material, or an organic dye.

[0030] The organic compound has a structure represented by general formula (1) or (2).

[0031]

Chemical formula

Chemical formula

[0032] Ar3 and Ar4 are each independently selected from structures represented by any of formulas (A-1) to (A-5),

Chemical formula

[0033] When Ar1 is selected from formula X-2, Ar4 is independently selected from structures represented by any of formulas (A-2) to (A-5), The linking site of Ar3 is a carbon atom on any benzene ring, and the condensation site of Ar4 is at two ortho-carbon atoms on the same benzene ring, Ar2 is selected from structures represented by any of formulas (B-1) to (B-4),

Chemical formula

[0034] Any one of R0, R1, R2 or R5 is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, When n0 is 2 or more, two adjacent R0s may or may not form a ring with each other; when n1 is 2 or more, two adjacent R1s may or may not form a ring with each other; when n2 is 2 or more, two adjacent R2s may or may not form a ring with each other; when n5 is 2 or more, two adjacent R5s may or may not form a ring with each other.

[0035] Preferably, the organic functional layer includes at least a light-emitting layer, the light-emitting layer includes a host material and a guest material which is one or more of the organic compounds, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

[0036] 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.

[0037] Preferably, the mass ratio of the host material to the guest material is 99:1 to 70:30.

[0038] In addition, the present application provides a display panel including an organic light-emitting device, and the organic light-emitting device includes a first electrode, a second electrode provided 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 manufactured from a composition, the composition includes the organic compound or the mixture, and at least one organic solvent, the mixture includes the organic compound and at least one organic functional material 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 light-emitting material, a host material, or an organic dye.

[0039] The organic compound has a structure represented by general formula (1) or (2).

[0040]

Chemical formula

Chemical formula

Chemical formula

Chemical Formula

[0041] Any one of R0, R1, R2, or R5 is independently -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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. When n0 is 2 or more, two adjacent R0s may form a ring with each other or may not form a ring. When n1 is 2 or more, two adjacent R1s may form a ring with each other or may not form a ring. When n2 is 2 or more, two adjacent R2s may form a ring with each other or may not form a ring. When n5 is 2 or more, two adjacent R5s may form a ring with each other or may not form a ring.

[0042] The organic compound preferably has a structure represented by any one of general formulas (2-1) to (2-28).

Chemical formula

Chemical formula

Chemical formula

[0043] When n3 is 2 or more, two adjacent R3s either form a ring with each other or do not form a ring. n4 is 0 or more and 5 or less.

[0044] When n4 is 2 or more, two adjacent R4s either form a ring with each other or do not form a ring.

[0045] 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, and a cyclic alkyl group having 3 to 10 carbon atoms.

[0046] 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, and a branched alkyl group having 3 to 5 carbon atoms.

[0047] Preferably, when the structure represented by the formula (B-2) is present in Ar2, the structure represented by the formula (B-2) is

Chemical formula

[0048] Preferably, the organic functional layer includes at least a light-emitting layer, the light-emitting layer includes a host material and a guest material which is one or more of the organic compounds, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

[0049] Preferably, the host material includes one or more of an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, and a pyrimidine derivative.

Advantages of the Invention

[0050] The present invention improves material properties, improves the luminous efficiency of an organic light-emitting device, and extends the service life of the organic light-emitting device by introducing a group that increases the conjugation of the entire compound into a boron-nitrogen compound.

Brief Description of the Drawings

[0051]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Modes for Carrying Out the Invention

[0052] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. In order to make the objectives, technical solutions, and effects of the present application clearer and more definite, the present application will be described in more detail below with reference to the drawings and by way of examples. It should be understood that the specific examples described in this specification are merely for the purpose of explaining the present application and are not intended to limit the present application.

[0053] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. Each will be described in detail below. It should be noted that the order of description of the following examples does not limit the preferred order of the examples.

[0054] In the present application, the aromatic group, the aromatic, and the aromatic ring system have the same meaning and are interchangeable.

[0055] In the present application, the heteroaromatic group, the heteroaromatic, and the heteroaromatic ring system have the same meaning and are interchangeable.

[0056] In the present application, "substituted" means that a hydrogen atom in the substituent is substituted with a substituent.

[0057] In the present application, when the same substituent is present multiple times, it can be independently selected from different groups. When the general formula contains a plurality of Rs, R can be independently selected from different groups.

[0058] In the present application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it can be understood that the defined group may be substituted with one or more substituents R, and the R is a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group having 1 to 20 carbon atoms, a heterocyclyl group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, -NR’R’’, a silyl 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 hydroxy group, a trifluoromethyl group, but is not limited thereto, and these groups may be further substituted with substituents acceptable in the art. In -NR’R’’, R’ and R’’ are each independently selected from H, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group having 1 to 10 carbon atoms, a heterocyclyl group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, but is not limited thereto. Preferably, R is selected from a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclyl group having 3 to 10 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, a silyl 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 hydroxy group, a trifluoromethyl group, but is not limited thereto, and these groups may be further substituted with substituents acceptable in the art.

[0059] In the present application, the "number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound in which atomic bonds are synthesized in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, 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.

[0060] In the present application, the "aryl or aromatic group" means an aromatic hydrocarbon group obtained by removing one hydrogen atom from an aromatic ring compound, and may be a monocyclic aryl group, a condensed ring aryl group, or a polycyclic aryl group, and at least one of the polycyclic rings is an aromatic ring system. For example, the "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means 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, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and is optionally further substituted in the aryl group. Preferred examples include, but are not limited to, phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, tetraphenyl, fluorenyl, perylene, acenaphthylenyl and their derivatives. The plurality of aryl groups may be interrupted by short non-aromatic units (for example, <10% of non-H atoms such as C, N, or O atoms), and in particular, it is understood that acenaphthylene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems must also be included in the definition of the aryl group.

[0061] In the present application, the "heteroaryl or heteroaromatic group" means that under the aryl group, at least one carbon atom is substituted by a non-carbon atom which 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 heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include thienyl, furanyl, pyrrolyl, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofurazinyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furopyrrolyl, furofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-diazonaphthalene, phenanthridinyl, pyrimidine, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl group and its derivatives, but not limited thereto.

[0062] In the present application, "alkyl" can represent a linear, branched and / or cyclic alkyl group. The number of carbon atoms of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Terms including this term are, for example, "C" 1-9"Alkyl" means an alkyl group containing 1 to 9 carbon atoms, and in each occurrence, independently of one another, can be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. 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, sec-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexy eicosyl, 2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexy eicosyl, 2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexy eicosyl,2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyldecosyl, 2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexadecyl, n-heptacosyl, n-octacosyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyldecosyl, 2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyldecosyl, 2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-octacosyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyldecosyl, 2-octyleicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-octacosyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyln-triacontyl group, etc. are included.

[0063] In the present application, the abbreviations of substituents are as follows. n - normal, sec - secondary, i - isomeric, t - tertiary, o - ortho, m - meta, p - para, Me - methyl, Et - ethyl, Pr - propyl, Bu - butyl, Am - n - pentyl, Hx - hexyl, Cy - cyclohexyl.

[0064] As used herein, "amine" means an amine derivative having a structural feature 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 amine groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl)2, -NH(heterocyclyl), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0065] In the present application, unless otherwise defined, a hydroxy group is -OH, a carboxy group is -COOH, a carbonyl group is -C(=O)-, an amino is -NH2, a formyl is -C(=O)H, a haloformyl is -C(=O)Z (wherein Z represents a halogen), a carbamoyl is -C(=O)NH2, an isocyanate group is -NCO, and an isothiocyanate group is -NCS.

[0066] In the present application, the term "alkoxy" refers to a group having the structure "-O-alkyl", i.e., a group in which the alkyl group defined above is bonded to another group through an oxygen atom. Preferred 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 (-O-C(CH3)3 or -OtBu).

[0067] In the present application, "*" bonded to a single bond indicates a bonding or condensation site.

[0068] In the present application, when the linking site in a group is not clearly specified, any linkable site is indicated as the linking site in the group.

[0069] In the present application, when the condensation site is not clearly specified, it means that any condensable site in the group is regarded as the condensation site, and preferably, two or more sites ortho to each other in the group are the condensation sites.

[0070] In the present application, when a group has a plurality of substituents with the same symbol on the same group, each substituent may be the same as or different from each other. For example,

Chemical formula

[0071] In the present application, the single bond to which the substituent is attached means that it penetrates the corresponding ring and the substituent can be attached to any position of the ring. For example,

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0072] The cyclic alkyl or cycloalkyl according to the present application has the same meaning and is interchangeable.

[0073] In this specification, "adjacent groups" means that there is no substitutable site between two substituents.

[0074] In the present application, "two adjacent R1 or R3 or R5 form a ring with each other" means a ring system formed by the connection of two adjacent 1 or 3 or R5 with each other, and the ring system can be selected from an aliphatic hydrocarbon ring, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Preferably,

Chemical formula

[0075] The present application provides an organic compound having a structure represented by general formula (1) or general formula (2).

[0076]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0077] Any one of R0, R1, R2 or R5 is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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 2 or more, two adjacent R0s may form a ring with each other or may not form a ring. When n1 is 2 or more, two adjacent R1s may form a ring with each other or may not form a ring. When n2 is 2 or more, two adjacent R2s may form a ring with each other or may not form a ring. When n5 is 2 or more, two adjacent R5s may form a ring with each other or may not form a ring.

[0078] Alternatively, the organic compound has a structure represented by any one of general formulas (2-1) to (2-28).

Chemical formula

Chemical formula

Chemical formula

[0079] Here, either R3 or R4 is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy 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, n3 is 0 or more and 5 or less.

[0080] When n3 is 2 or more, two adjacent R3s may form a ring with each other or may not form a ring. n4 is 0 or more and 5 or less.

[0081] When n4 is 2 or more, two adjacent R4s may form a ring with each other or may not form a ring.

[0082] Alternatively, 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, and a cyclic alkyl group having 3 to 10 carbon atoms.

[0083] Alternatively, 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, and a branched alkyl group having 3 to 5 carbon atoms.

[0084] By introducing an alkyl group into the organic compound, the solubility of the organic compound used in processes such as inkjet printing is improved, and the product quality of the organic light-emitting device to which the organic compound is applied is improved.

[0085] 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 an aliphatic ring. Further, two adjacent R1s form a ring with each other to

Chemical formula

[0086] In some embodiments, two adjacent R2s form a ring with each other. Further, two adjacent R2s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring. Further, two adjacent R2s form a ring with each other to

Chemical formula

[0087] In some embodiments, two adjacent R3s form a ring with each other. Further, two adjacent R3s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring. Further, two adjacent R3s form a ring with each other to

Chemical formula

[0088] In some embodiments, two adjacent R4s form a ring with each other. Further, two adjacent R4s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring. Further, two adjacent R4s form a ring with each other

Chemical formula

[0089] In some embodiments, two adjacent R5s form a ring with each other. Further, two adjacent R5s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring. Further, two adjacent R5s form a ring with each other

Chemical formula

[0090] In some embodiments, when the structure represented by the formula (B-2) is present in Ar2, the structure represented by the formula (B-2) is

Chemical formula

[0091] In some embodiments, the organic compound is a blue light-emitting material.

[0092] In some embodiments, the organic compound is

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0093] The boron-containing biphenyl organic compound provided by the examples of the present application introduces structures such as dibenzofuran, dibenzothiophene, carbazole, benzofive-membered ring, triphenylene and / or naphthalene into the boron-nitrogen compound, increases the overall molecular conjugation, and improves the luminous efficiency and service life of the organic light-emitting device applying the organic compound. At the same time, when structures such as tetrahydronaphthalene and / or indane are introduced into the boron-nitrogen compound, the solubility of the molecule in processes such as inkjet printing becomes better, the purification of the compound is easy, the purity of the organic compound is improved, and further the luminous efficiency and service life of the organic light-emitting device applying the organic compound are extended.

[0094] Referring to FIGS. 1 and 2, the present application further provides an organic light-emitting device 100, which includes a first electrode 101 and a second electrode 102, and an organic functional layer 103 located between the first electrode 101 and the second electrode 102. Here, the material of the organic functional layer 103 includes one or more of the organic compounds as described above. The first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0095] In some embodiments, the organic light emitting device 100 can be used in an organic light emitting diode, an organic photovoltaic cell, an organic light emitting battery, an organic field effect tube, an organic light emitting field effect tube, an organic laser, an organic spin electronics, an organic sensor, an organic plasmonic light emitting diode, or the like, preferably an organic light emitting diode, an organic light emitting battery, or an organic light emitting field effect tube.

[0096] In some embodiments, the organic light emitting device 100 may be applied to various electronic devices, such as, for example, a display panel, a lighting device, a light source, and the like.

[0097] In some embodiments, the organic functional layer 103 may be a single layer, in which case the organic functional layer 103 is a mixture layer, comprising a first compound selected from one or more of the organic compounds described above, and a second compound selected from one or more of a hole injection material, a hole transport material, an electron transport material, a hole blocking material, an emissive guest material, an emissive host material, and an organic dye. A detailed description of the various organic functional materials contained in the organic functional layer 103 is described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, all of which are incorporated herein by reference in their entirety.

[0098] The emissive guest material is selected from singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters) and TADF materials.

[0099] When 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 light emitting host material, and an organic dye, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0100] 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, and preferably 99:1 to 90:10.

[0101] In some embodiments, the organic functional layer 103 can include a plurality of layers. When the organic functional layer 103 is a plurality of layers, 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.

[0102]

[0102] In some embodiments, the organic light-emitting device 100 may 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 that is one or more of the organic compounds as described above, and a host material that includes a condensed aromatic derivative or a heteroaromatic compound.

[0103] The emission wavelength of the organic light-emitting device 100 is 300 to 1000 nm; further, the emission wavelength of the organic light-emitting device 100 is 350 to 900 nm. Further, the emission wavelength of the organic light-emitting device 100 is 400 to 800 nm. Further, the emission wavelength of the organic light-emitting device 100 is within the wavelength range of blue light.

[0104]

[0104] In some embodiments, the host material includes at least one of an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, a carbazole derivative, a dibenzofuran derivative, a ladder-type fluorene compound, and a pyrimidine derivative. Preferably, the host material is a blue light host material applied to a blue organic light-emitting device. When the host material is a blue host material, the host material is preferably an anthracene-based organic compound.

[0105] In some embodiments, the mass ratio of the host material to the guest material is from 99:1 to 70:30, for example, 90:10, 85:15, 80:20, 75:25, etc. Preferably, it is from 99:1 to 90:10, for example, 97:3, 96:4, 95:5, 93:7, 92:8, etc. When the guest material is dispersed in the host material and the mass ratio of the host material to the guest material is from 99:1 to 70:30, it is advantageous for suppressing the crystallization of the light-emitting layer 107 and suppressing concentration quenching due to the high concentration of the guest material, and can improve the light-emitting efficiency of the organic light-emitting device 100.

[0106] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer 103. The anode injects 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) level or valence band 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, more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be easily selected and used by those skilled in the art. The material of the anode can be deposited using any suitable technique such as a suitable physical vapor deposition method including high-frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be pattern-structured. For example, a patterned ITO conductive substrate is commercially available and can be used in the manufacture of the organic light-emitting device 100 of the present application.

[0107] In some embodiments, the cathode is an electron injection electrode, and the cathode can inject electrons into the organic functional layer. For example, the cathode injects electrons into the electron injection layer, the electron transport layer, or the light-emitting layer. The cathode can 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 the conduction band level of the light-emitting material of the light-emitting layer, or the n-type semiconductor material as the electron injection layer, the electron transport layer, or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV. All materials useful as the cathode of the organic electronic device are possible as the cathode material of the device filed in this application. The cathode material includes, but is 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 material of the cathode can be deposited using any suitable technique such as a suitable physical vapor deposition method including high-frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0108] In some embodiments, the hole injection layer 104 functions to promote the injection of holes from the anode into the light-emitting layer 107. The hole injection layer 104 includes a hole injection material that can receive holes injected from the anode at a low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the functional material (e.g., the hole transport material of the hole transport layer) into which the holes are injected from the anode to the film layer on the far side. Examples of the hole injection material include, but are not limited to, at least one of metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based, and polythiophene-based conductive polymers.

[0109] 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 contains a hole transport material that receives holes transported from the anode or the hole injection layer and moves the holes to the light emitting layer. The hole transport material is a material known in the art having a high hole mobility and can include at least one of, but is not limited to, arylamine-based organic materials, conductive polymers, and blocking copolymers having both a conjugated portion and a non-conjugated portion.

[0110] In some embodiments, the electron transport layer 108 functions to transport electrons. The electron transport layer 108 contains 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 having a high electron mobility and can include, but is not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, lithium 8-hydroxyquinolate (LiQ), and a benzimidazole-based compound.

[0111] In some embodiments, the electron injection layer 109 is for injecting electrons. The electron injection layer 109 contains an electron injection material. The electron injection material 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 luminescent substance, prevents excitons generated by the light emitting layer 107 from moving to the hole injection layer, and is preferably a material having an excellent ability to form a film. Examples of the electron injection material include, but are not limited to, at least one of lithium 8-hydroxyquinolate (LiQ), fluorenone, anthraquinone dimethane, biphenyl quinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoromethylenemethane, anthrone, and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc.

[0112] In some embodiments, the hole blocking layer functions to block holes from reaching the negative electrode and generally can be formed under the same conditions as the hole injection layer 104. The hole blocking layer contains a hole blocking material, and the hole blocking material includes, but is not limited to, at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, etc.

[0113] In some embodiments, the organic light-emitting device 100 further includes a substrate 110, and 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 on the substrate 110. The substrate 110 may 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 may be a rigid substrate or a flexible substrate having elasticity. The material of the substrate 110 can include, but is not limited to, plastic, polymer, metal, semiconductor wafer, or glass, etc. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on its surface. More preferably, the surface has no 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 150 °C or higher, preferably 200 °C or higher, more preferably 250 °C or higher, and most preferably 300 °C or higher.

[0114] 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 fabricated by printing (for example, inkjet printing).

[0115] In some embodiments, the mixture layer or the light-emitting layer can be formed by a printing or coating process of a composition. The printing or coating process includes inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, cylinder printing, twist roll printing, lithography, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slot extrusion coating, etc. Gravure printing, nozzle printing, and inkjet printing are preferred.

[0116] The composition may be a solution or a suspension, and the composition may contain a dispersoid and a dispersant. Here, the dispersoid is one or more of the organic compounds described above and at least one organic solvent, and the dispersant is for dispersing the dispersoid.

[0117] In the composition, the mass fraction of the organic compound described above may be 0.3 to 30% by mass, preferably 0.5 to 20% by mass, more preferably 0.5 to 15% by mass, still more preferably 0.5 to 10% by mass, and most preferably 1 to 5% by mass.

[0118] When the composition is used in a printing process, the composition is an ink, and the viscosity and surface tension of the ink are important parameters. Appropriate surface tension parameters of the ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the ink at the operating temperature or 25 °C ranges from 19 dyne / cm to 50 dyne / cm. Preferably, it is from 22 dyne / cm to 35 dyne / cm. More preferably, it is from 25 dyne / cm to 33 dyne / cm, which is advantageous for application to an inkjet printing process. In some embodiments, the viscosity of the ink at the operating temperature or 25 °C ranges from 1 cps to 100 cps. Preferably, it is from 1 cps to 50 cps, more preferably from 1.5 cps to 20 cps. Most preferably, it is from 4.0 cps to 20 cps, which is advantageous for application to an inkjet printing process.

[0119] In some embodiments, the Hansen solubility parameters of the dispersant are within the following ranges. The δd (dispersion force) of the dispersant is in the range of 17.0 to 23.2 MPa 1 / 2 Preferably in the range of 18.5 to 21.0 MPa 1 / 2 The δp (polar force) is in the range of 0.2 to 12.5 MPa 1 / 2 Preferably in the range of 2.0 to 6.0 MPa 1 / 2 The δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa 1 / 2 Preferably in the range of 2.0 to 6.0 MPa 1 / 2 And is in the range of.

[0120] In some embodiments, the boiling point of the dispersant is 150 °C or higher, preferably 180 °C or higher, more preferably 200 °C or higher, more preferably 250 °C or lower, still more preferably 275 °C or higher, and most preferably 300 °C or higher. When the boiling point of the dispersant is at least 150 °C or higher, it is advantageous for preventing clogging of the nozzles of the inkjet print head during inkjet printing, and the higher the boiling point, the more advantageous it is for preventing clogging.

[0121] The dispersant can include at least one organic solvent that can be evaporated from a solvent system to form a film containing a functional material. The organic solvent can include at least one first organic solvent selected from aromatic or heteroaromatic. Specifically, the first organic solvent can be selected from p-diisopropylbenzene, amylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumylbenzene, dipentylbenzene, tripentylbenzene, amyltoluene, 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-isopropylbiphenyl, p-methylcumene, 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-furancarboxylate, ethyl 2-furancarboxylate, and the like.

[0122] 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-(methyloxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like.

[0123] 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-ethylbenzene ether, 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, and the like.

[0124] The first organic solvent can be selected from aliphatic ketones. Specifically, the first organic solvent can be an aliphatic ketone such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, pulegone, menthone, isophorone, di-n-amyl ketone, etc., or an aliphatic ether such as 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, and the like.

[0125] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0126] The organic solvent can include one or more second organic solvents selected from solvents such as methanol, ethanol, 2-methoxyethanol, methylene dichloride, trichloromethane, 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, tetrahydronaphthalene, decalin, indene, etc.

[0127] In addition to the dispersoid and the dispersant, the composition can include one or more components such as a surfactant compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, a binder, etc. for adjusting viscosity, film-forming performance, improving adhesion, etc.

Examples

[0128] Exemplary production methods of the organic compounds provided by this application are shown in the following exemplary Examples 1 to 63.

[0129] Example 1 The synthetic route of organic compound M1 is as follows.

Chemical formula

[0130] Synthesis of Intermediate 1-3 Compound 1-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 1-3 with a molar amount of 8.21 mmol and a yield of 82.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 1-3 was MS(ASAP) = 337.

[0131] Synthesis of Intermediate 1-5 Compound 1-3 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 1-5 with a molar amount of 7.28 mmol and a yield of 72.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 1-5 was MS(ASAP) = 481.

[0132] Synthesis of Intermediate 1-7 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 1-7, with a molar amount of 5.45 mmol and a yield of 54.5%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 1-7 was MS(ASAP) = 608.

[0133] Synthesis of Intermediate 1-9 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 1-9, with a molar amount of 6.25 mmol and a yield of 62.5%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 1-9 was MS(ASAP) = 774.

[0134] Synthesis of Intermediate 1-11 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and the organic phase was subjected to column chromatography and recrystallization. The molar amount of Intermediate 1-11 was 7.81 mmol, the yield was 78.1%, and the result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 1-11 was MS(ASAP)=966.

[0135] Synthesis of Organic Compound M1 10 mmol of Intermediate 1-11 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour, then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and the crude product was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M1, with a yield of 38.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M1 was MS(ASAP)=940.

[0136] Example 2 The synthesis route of organic compound M2 is as follows.

Chemical formula

[0137] Synthesis of Intermediate 2-2 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-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 2-2. The molar amount was 6.47 mmol and the yield was 64.7%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 2-2 was MS(ASAP) = 580.

[0138] Synthesis of Intermediate 2-3 Intermediate 2-2 (10 mmol), Compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 2-3. The molar amount was 8.36 mmol and the yield was 83.6%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 2-3 was MS(ASAP) = 746.

[0139] Synthesis of Intermediate 2-4 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and purification by column chromatography and recrystallization of the organic phase. The molar amount of Intermediate 2-4 was 7.09 mmol, the yield was 70.9%, and the result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 2-4 was MS(ASAP)=938.

[0140] Synthesis of Organic Compound M2 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 an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, Organic Compound M2, with a yield of 36.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M2 was MS(ASAP)=912.

[0141] Example 3 The synthesis route of Organic Compound M3 is as follows.

Chemical formula

[0142] Synthesis of Intermediate 3-2 Intermediate 1-5 (10 mmol), Compound 3-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 3-2. The molar amount was 7.83 mmol and the yield was 78.3%. The result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 3-2 was MS(ASAP) = 566.

[0143] Synthesis of Intermediate 3-3 Intermediate 3-2 (10 mmol), Compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 3-3. The molar amount was 8.51 mmol and the yield was 85.1%. The result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 3-3 was MS(ASAP) = 732.

[0144] Synthesis of Intermediate 3-4 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and purification by organic phase column chromatography and recrystallization. The molar amount of Intermediate 3-4 was 5.97 mmol, the yield was 59.7%, and the result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 3-4 was MS(ASAP)=924.

[0145] Synthesis of Organic Compound M3 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 an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M3, with a yield of 40.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M3 was MS(ASAP)=898.

[0146] Example 4 The synthesis route of organic compound M16 is as follows.

[0147]

Chemical formula

[0148] Synthesis of Intermediate 16-4 Compound 16-2 (10 mmol), Compound 16-3 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. Column chromatography of the organic phase was performed to obtain Intermediate 16-4, with a molar amount of 7.68 mmol and a yield of 76.8%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 16-4 being MS(ASAP) = 507.

[0149] Synthesis of Intermediate 16-5 Compound 16-4 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 16-5. The molar amount was 6.97 mmol and the yield was 69.7%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 16-5 was MS(ASAP) = 651.

[0150] Synthesis of Intermediate 16-8 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 16-8. The molar amount was 5.42 mmol and the yield was 54.2%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 16-8 was MS(ASAP) = 281.

[0151] Synthesis of Intermediate 16-9 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 16-9 with a molar amount of 5.97 mmol and a yield of 59.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 16-9 was MS(ASAP) = 469.

[0152] Synthesis of Intermediate 16-10 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and column chromatography and recrystallization of the organic phase were performed to obtain Intermediate 16-10 with a molar amount of 7.27 mmol, a yield of 72.7%, and the result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 16-10 was MS(ASAP) = 1084.

[0153] Synthesis of Organic Compound M16 Add 10 mmol of Intermediate 16-10 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C under a N2 atmosphere, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate distill the solvent in it to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M16, with a yield of 33.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M16 is MS(ASAP)=1058. 1H NMR(400MHz,CDCl3)δ 8.17(d,J=8.6Hz,6H),8.02(s,6H),7.87(d,J=13.4Hz,6H),7.02(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).

[0154] Example 5 The synthetic route of organic compound M20 is as follows.

Chemical Structure

[0155] Synthesis of Intermediate 20-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 20-2 with a molar amount of 6.94 mmol and a yield of 69.4%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 20-2 was MS(ASAP) = 281.

[0156] Synthesis of Intermediate 20-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 20-3 with a molar amount of 6.33 mmol and a yield of 63.3%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 20-3 was MS(ASAP) = 469.

[0157] Synthesis of Intermediate 20-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography and recrystallization. The molar amount of Intermediate 20-4 was 5.47 mmol, the yield was 54.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 20-4 was MS(ASAP) = 1084.

[0158] Synthesis of Organic Compound M20 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 an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one drop at a time. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a pure product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M20, with a yield of 31.9%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M20 was MS(ASAP) = 1058.

[0159] Example 6 The synthetic route of organic compound M24 is as follows. [Chemistry]

[0160] Synthesis of Intermediate 24-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 24-2. The molar amount was 7.63 mmol and the yield was 76.3%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 24-2 was MS(ASAP) = 281.

[0161] Synthesis of Intermediate 24-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 24-3. The molar amount was 6.55 mmol and the yield was 65.5%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 24-3 was MS(ASAP) = 469.

[0162] Synthesis of Intermediate 24-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization. The molar amount of Intermediate 24-4 was 5.02 mmol, the yield was 50.2%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 24-4 was MS(ASAP) = 1084.

[0163] Synthesis of Organic Compound M24 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 an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M24, with a yield of 36.5%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M24 was MS(ASAP) = 1058.

[0164] Example 7 The synthetic route of organic compound M25 is as follows. [Chem.]

[0165] Synthesis of Intermediate 25-1 Intermediate 1-5 (10 mmol), Compound 24-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 25-1. The molar amount was 8.47 mmol and the yield was 84.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 25-1 was MS(ASAP) = 726.

[0166] Synthesis of Intermediate 25-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 25-2. The molar amount was 6.48 mmol and the yield was 64.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 25-2 was MS(ASAP) = 892.

[0167] Synthesis of Intermediate 25-3 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 25-3 with a molar amount of 7.75 mmol, a yield of 77.5%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 25-3 was MS(ASAP)=1084.

[0168] Synthesis of Organic Compound M25 Add 10 mmol of Intermediate 25-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C under an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely Organic Compound M25, with a yield of 42.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M25 is MS(ASAP)=1058. 1H NMR(400MHz,CDCl3)δ 9.02(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).

[0169] Example 8 The synthetic route of Organic Compound M26 is as follows.

Chemical Structure

[0170] Synthesis of Intermediate 26-1 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 26-1. The molar amount was 8.66 mmol and the yield was 86.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 26-1 was MS(ASAP) = 726.

[0171] Synthesis of Intermediate 26-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 26-2. The molar amount was 6.09 mmol and the yield was 60.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 26-2 was MS(ASAP) = 892.

[0172] Synthesis of Intermediate 26-3 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization to obtain Intermediate 26-3. The molar amount was 7.54 mmol, the yield was 75.4%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 26-3 was MS(ASAP) = 1084.

[0173] Synthesis of Organic Compound M26 10 mmol of Intermediate 26-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and the reaction was carried out for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M26. The yield was 39.6%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M26 was MS(ASAP) = 1058.

[0174] Example 9 The synthesis route of organic compound M96 is as follows.

Chemical formula

[0175] Synthesis of Intermediate 96-3 Intermediate 96-1 (20 mmol) and Compound 96-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2:1 / 2 ml). Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 96-3. The molar amount was 7.29 mmol and the yield was 72.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 96-3 was MS(ASAP) = 357.

[0176] Synthesis of Intermediate 96-4 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 96-4. The molar amount was 6.12 mmol and the yield was 61.2%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 96-4 was MS(ASAP) = 545.

[0177] Synthesis of Intermediate 96-5 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization to obtain Intermediate 96-5 with a molar amount of 5.38 mmol, a yield of 53.8%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of MS(ASAP) = 1160 for Intermediate 96-5.

[0178] Synthesis of Organic Compound M96 10 mmol of Intermediate 96-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M96, with a yield of 43.6%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of MS(ASAP) = 1134 for organic compound M96.

[0179] Example 10 The synthesis route of organic compound M100 is as follows. [Chemistry]

[0180] Synthesis of Intermediate 100-2 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). Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography to obtain Intermediate 100-2. The molar amount was 7.67 mmol and the yield was 76.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 100-2 was MS(ASAP) = 357.

[0181] Synthesis of Intermediate 100-3 Intermediate 100-2 (10 mmol), Compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-biscyclohexylphosphine-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography to obtain Intermediate 100-3. The molar amount was 6.59 mmol and the yield was 65.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 100-3 was MS(ASAP) = 545.

[0182] Synthesis of Intermediate 100-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 100-4. The molar amount was 6.87 mmol, the yield was 68.7%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 100-4 was MS(ASAP)=1160.

[0183] Synthesis of Organic Compound M100 10 mmol of Intermediate 100-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M100. The yield was 41.4%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M100 was MS(ASAP)=1134.

[0184] Example 11 The synthetic route of organic compound M104 is as follows. [Chemical formula]

[0185] Synthesis of Intermediate 104-2 Intermediate 96-1 (20 mmol) and Intermediate 104-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 104-2. The molar amount was 7.11 mmol and the yield was 71.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 104-2 was MS(ASAP) = 357.

[0186] Synthesis of Intermediate 104-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 104-3. The molar amount was 5.71 mmol and the yield was 57.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 104-3 was MS(ASAP) = 545.

[0187] Synthesis of Intermediate 104-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 104-4 with a molar amount of 6.57 mmol, a yield of 65.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 104-4 was MS(ASAP)=1160.

[0188] Synthesis of Organic Compound M104 10 mmol of Intermediate 104-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and the crude product was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M104, with a yield of 45.4%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M104 was MS(ASAP)=1134.

[0189] Example 12 The synthetic route of organic compound M122 is as follows.

Chemical formula

[0190] Synthesis of Intermediate 122-2 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 122-2. The molar amount was 8.36 mmol and the yield was 83.6%. The result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 122-2 was MS(ASAP) = 690.

[0191] Synthesis of Intermediate 122-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 122-3. The molar amount was 54.9 mmol and the yield was 54.9%. The result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 122-3 was MS(ASAP) = 856.

[0192] Synthesis of Intermediate 122-4 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and the organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 122-4 with a molar amount of 6.47 mmol, a yield of 64.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 122-4 was MS(ASAP)=1048.

[0193] Synthesis of Organic Compound M122 10 mmol of Intermediate 122-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour, then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, Organic Compound M124, with a yield of 31.8%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M124 was MS(ASAP)=1022.

[0194] Example 13 The synthetic route of Organic Compound M128 is as follows.

Chemical formula

[0195] Synthesis of Intermediate 128-1 Compound 3-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 128-1. The molar amount was 8.37 mmol and the yield was 83.7%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 128-1 was MS(ASAP) = 309.

[0196] Synthesis of Intermediate 128-2 Compound 128-1 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 128-2. The molar amount was 7.05 mmol and the yield was 70.5%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 128-2 was MS(ASAP) = 453.

[0197] Synthesis of Intermediate 128-3 Intermediate 128-2 (10 mmol), Compound 122-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 128-3 with a molar amount of 6.83 mmol and a yield of 68.3%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 128-3 was MS(ASAP) = 662.

[0198] Synthesis of Intermediate 128-4 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 128-4 with a molar amount of 6.68 mmol and a yield of 66.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 128-4 was MS(ASAP) = 828.

[0199] Synthesis of Intermediate 128-5 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and then organic phase column chromatography and recrystallization to obtain Intermediate 128-5. The molar amount was 7.68 mmol, the yield was 76.8%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 128-5 was MS(ASAP) = 1020.

[0200] Synthesis of Organic Compound M128 10 mmol of Intermediate 128-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C under an N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M128. The yield was 40.7%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M128 was MS(ASAP) = 994.

[0201] Example 14 The synthetic route of organic compound M129 is as follows.

Chemical formula

[0202] Synthesis of Intermediate 129-1 Compound 2-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 129-1. The molar amount was 7.69 mmol, the yield was 76.9%, and the result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 129-1 was MS(ASAP) = 323.

[0203] Synthesis of Intermediate 129-2 Compound 129-1 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 129-2. The molar amount was 7.59 mmol, the yield was 75.9%, and the result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 129-2 was MS(ASAP) = 467.

[0204] Synthesis of Intermediate 129-3 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-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 129-3. The molar amount was 6.12 mmol and the yield was 61.2%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 129-3 was MS(ASAP) = 788.

[0205] Synthesis of Intermediate 129-4 Intermediate 129-3 (10 mmol), Compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 129-4. The molar amount was 6.51 mmol and the yield was 65.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 129-4 was MS(ASAP) = 954.

[0206] Synthesis of Intermediate 129-5 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization to obtain Intermediate 129-5. The molar amount was 7.34 mmol, the yield was 73.4%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 129-5 was MS(ASAP)=1146.

[0207] Synthesis of Organic Compound M129 10 mmol of Intermediate 129-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour, then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M129. The yield was 29.7%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M129 was MS(ASAP)=1120.

[0208] Example 15 The synthetic route of organic compound M132 is as follows.

Chemical formula

[0209] Synthesis of Intermediate 132-1 Compound 2-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 132-1. The molar amount was 8.41 mmol and the yield was 84.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 132-1 was MS(ASAP) = 351.

[0210] Synthesis of Intermediate 132-2 Compound 132-1 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 132-2. The molar amount was 6.79 mmol and the yield was 67.9%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 132-2 was MS(ASAP) = 495.

[0211] Synthesis of Intermediate 132-3 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-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 132-3 with a molar amount of 7.84 mmol and a yield of 78.4%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 132-3 was MS(ASAP) = 816.

[0212] Synthesis of Intermediate 132-4 Intermediate 132-3 (10 mmol), Compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 132-4 with a molar amount of 5.96 mmol and a yield of 59.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 132-4 was MS(ASAP) = 982.

[0213] Synthesis of Intermediate 132-5 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase, and recrystallization to obtain Intermediate 132-5. The molar amount was 6.47 mmol, the yield was 64.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 132-5 was MS(ASAP)=1174.

[0214] Synthesis of Organic Compound M132 10 mmol of Intermediate 132-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M132. The yield was 33.7%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M132 was MS(ASAP)=1148.

[0215] Example 16 The synthesis route of organic compound M147 is as follows.

Chemical formula

[0216] Synthesis of Intermediate 147-2 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization. The molar amount of Intermediate 147-2 was 7.36 mmol, the yield was 73.6%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 147-2 was MS(ASAP) = 1024.

[0217] Synthesis of Organic Compound M147 10 mmol of Intermediate 147-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M147, with a yield of 34.7%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M147 was MS(ASAP) = 998.

[0218] Example 17 The synthesis route of organic compound M162 is as follows.

Chemical formula

[0219] Synthesis of Intermediate 162-1 Intermediate 24-3 (10 mmol), Intermediate 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization to obtain Intermediate 162-1 with a molar amount of 5.35 mmol, a yield of 53.5%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of MS(ASAP) = 613 for Intermediate 162-1.

[0220] Synthesis of Intermediate 162-2 Intermediate 162-1 (10 mmol), Compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, liquid separated by washing with water, and organic phase column chromatography was performed to obtain Intermediate 162-2 with a molar amount of 7.34 mmol and a yield of 73.4%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of MS(ASAP) = 726 for Intermediate 162-2.

[0221] Synthesis of Intermediate 162-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 162-3. The molar amount was 5.78 mmol and the yield was 57.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 162-3 was MS(ASAP) = 896.

[0222] Synthesis of Intermediate 162-5 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and column chromatography and recrystallization of the organic phase were performed to obtain Intermediate 162-5. The molar amount was 6.17 mmol, the yield was 61.7%, and the result of the atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 162-5 was MS(ASAP) = 1040.

[0223] Synthesis of Organic Compound M162 Add 10 mmol of intermediate 162-5 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool to -30 °C under a N2 atmosphere, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M162, with a yield of 35.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M162 is MS(ASAP)=1014.

[0224] Example 18 The synthetic route of organic compound M165 is as follows.

[0225] [Chemical formula] Synthesis of intermediate 165-2 Dissolve 10 mmol of intermediate 1-9 and 10 mmol of intermediate 165-1 in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), and stir at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, remove most of the solvent with a rotary evaporator, then extract, separate the liquid by washing with water, and perform organic phase column chromatography and recrystallization. The molar amount of intermediate 165-2 is 7.38 mmol, the yield is 73.8%, and the result of the atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of intermediate 165-2 is MS(ASAP)=919.

[0226] Synthesis of Organic Compound M165 Add 10 mmol of Intermediate 165-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C in an N₂ atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent in it to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M165, with a yield of 29.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M165 is MS(ASAP)=893.

[0227] Example 19 The synthesis route of organic compound M193 is as follows.

Chemical formula

[0228] Synthesis of Intermediate 193-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by washing with water, and the organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 193-1 with a molar amount of 7.56 mmol, a yield of 75.6%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 193-1 was MS(ASAP)=613.

[0229] Synthesis of Intermediate 193-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by washing with water, and the organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 193-2 with a molar amount of 7.13 mmol, a yield of 71.3%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 193-2 was MS(ASAP)=726.

[0230] Synthesis of Intermediate 193-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 193-3 in a molar amount of 5.29 mmol and a yield of 52.9%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 193-3 was MS(ASAP) = 892.

[0231] Synthesis of Intermediate 193-5 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 193-5 in a molar amount of 6.56 mmol, a yield of 65.6%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 193-5 was MS(ASAP) = 988.

[0232] Synthesis of Organic Compound M193 Add 10 mmol of intermediate 193-5 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C in an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane one drop at a time. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M193, with a yield of 29.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M193 is MS(ASAP)=962.

[0233] Example 20 The synthetic route of organic compound M210 is as follows.

Chemical formula

[0234] Synthesis of intermediate 210-2 Dissolve 10 mmol of intermediate 162-3 and 10 mmol of intermediate 210-1 in a mixed solvent of 1,4-dioxane and water (21 / 2 ml). Add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), and stir at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, remove most of the solvent with a rotary evaporator, then extract, separate by washing with water, and perform organic phase column chromatography and recrystallization. The molar amount of intermediate 210-2 is 7.38 mmol, the yield is 73.8%, and the result of the atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of intermediate 210-2 is MS(ASAP)=974.

[0235] Synthesis of Organic Compound M210 Add 10 mmol of Intermediate 210-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C under a N2 atmosphere, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent in it to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M210, with a yield of 32.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M210 is MS(ASAP)=948.

[0236] Example 21 The synthesis route of organic compound M234 is as follows.

Chemical formula

[0237] Synthesis of Intermediate 234-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. Column chromatography and recrystallization of the organic phase were performed. The molar amount of Intermediate 234-2 was 6.58 mmol, the yield was 65.8%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 234-2 was MS(ASAP) = 691.

[0238] Synthesis of Intermediate 234-3 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. Column chromatography of the organic phase was performed to obtain Intermediate 234-3. The molar amount was 7.07 mmol and the yield was 70.7%. The result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 234-3 was MS(ASAP) = 1118.

[0239] Synthesis of Intermediate 234-5 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and the organic phase was subjected to column chromatography to obtain Intermediate 234-5 with a molar amount of 5.06 mmol and a yield of 50.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 234-5 was MS(ASAP) = 1251.

[0240] Synthesis of Organic Compound M234 10 mmol of Intermediate 234-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the dropping was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, Organic Compound M234, with a yield of 22.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M234 was MS(ASAP) = 1225.

[0241] Example 22 The synthetic route of Organic Compound M253 is as follows.

Chemical formula

[0242] Synthesis of Intermediate 253-2 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization. The molar amount of Intermediate 253-2 was 7.69 mmol, the yield was 76.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 253-2 was MS(ASAP) = 375.

[0243] Synthesis of Intermediate 253-3 Compound 253-2 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography to obtain Intermediate 253-3. The molar amount was 8.33 mmol, the yield was 83.3%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 253-3 was MS(ASAP) = 563.

[0244] Synthesis of Intermediate 253-4 Compound 253-3 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 253-4. The molar amount was 6.75 mmol and the yield was 67.5%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 253-4 was MS(ASAP) = 707.

[0245] Synthesis of Intermediate 253-5 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 253-5. The molar amount was 7.24 mmol and the yield was 72.4%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 253-5 was MS(ASAP) = 820.

[0246] Synthesis of Intermediate 253-7 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 253-7. The molar amount was 5.38 mmol and the yield was 53.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 253-7 was MS(ASAP) = 1084.

[0247] Synthesis of Organic Compound M253 10 mmol of Intermediate 253-7 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the dropping was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, Organic Compound M253. The yield was 38.6%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Organic Compound M253 was MS(ASAP) = 1058.

[0248] Example 23 The synthetic route of Organic Compound M254 is as follows.

Chemical formula

[0249] Synthesis of Intermediate 254-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 254-2 with a molar amount of 5.19 mmol and a yield of 51.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 254-2 was MS(ASAP) = 1084.

[0250] Synthesis of Organic Compound M254 10 mmol of Intermediate 254-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and purified by high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, Organic Compound M254, with a yield of 42.5%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M254 was MS(ASAP) = 1058.

[0251] Example 24 The synthetic route of organic compound M255 is as follows. [Chemical formula]

[0252] Synthesis of Intermediate 255-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography to obtain Intermediate 255-2. The molar amount was 6.28 mmol and the yield was 62.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 255-2 was MS(ASAP)=1084.

[0253] Synthesis of Organic Compound M255 Add 10 mmol of intermediate 255-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C in an N₂ atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M255, with a yield of 47.3%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M255 is MS(ASAP)=1058.

[0254] Example 25 The synthetic route of organic compound M266 is as follows.

Chemical formula

[0255] Synthesis of intermediate 266-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 266-2. The molar amount was 6.37 mmol and the yield was 63.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 266-2 was MS(ASAP) = 1216.

[0256] Synthesis of Organic Compound M266 10 mmol of Intermediate 266-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, Organic Compound M266. The yield was 36.4%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M266 was MS(ASAP) = 1190.

[0257] Example 26 The synthesis route of Organic Compound M268 is as follows.

Chemical formula

[0258] Synthesis of Intermediate 268-2 Compound 16-2 (10 mmol), Compound 268-1 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 268-2. The molar amount was 7.32 mmol and the yield was 73.2%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 268-2 was MS(ASAP) = 527.

[0259] Synthesis of Intermediate 268-3 Compound 268-2 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 268-3. The molar amount was 6.51 mmol and the yield was 65.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 268-3 was MS(ASAP) = 671.

[0260] Synthesis of Intermediate 268-6 Intermediate 268-4 (20 mmol), Compound 268-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 268-6. The molar amount was 5.27 mmol and the yield was 52.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 268-6 was MS(ASAP) = 357.

[0261] Synthesis of Intermediate 268-7 Intermediate 268-6 (10 mmol), Compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 268-7. The molar amount was 5.17 mmol and the yield was 51.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 268-7 was MS(ASAP) = 545.

[0262] Synthesis of Intermediate 268-8 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 268-8 with a molar amount of 7.02 mmol, a yield of 70.2%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 268-8 was MS(ASAP)=1180.

[0263] Synthesis of Organic Compound M268 10 mmol of Intermediate 268-8 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M268, with a yield of 30.1%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M268 was MS(ASAP)=1154.

[0264] Example 27 The synthetic route of organic compound M269 is as follows.

Chemical formula

[0265] Synthesis of Intermediate 269-2 Compound 16-2 (10 mmol), Compound 269-1 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 269-2. The molar amount was 6.45 mmol and the yield was 64.5%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 269-2 was MS(ASAP) = 583.

[0266] Synthesis of Intermediate 269-3 Compound 269-2 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 269-3. The molar amount was 6.91 mmol and the yield was 69.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 269-3 was MS(ASAP) = 727.

[0267] Synthesis of Intermediate 269-6 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 269-6 with a molar amount of 5.54 mmol and a yield of 55.4%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 269-6 was MS(ASAP) = 301.

[0268] Synthesis of Intermediate 269-7 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 268-7 with a molar amount of 5.49 mmol and a yield of 54.9%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 269-7 was MS(ASAP) = 489.

[0269] Synthesis of Intermediate 269-8 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 269-8 with a molar amount of 7.55 mmol, a yield of 75.5%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 269-8 was MS(ASAP)=1180.

[0270] Synthesis of Organic Compound M269 10 mmol of Intermediate 269-8 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M269, with a yield of 29.6%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M269 was MS(ASAP)=1154.

[0271] Example 28 The synthetic route of organic compound M270 is as follows. [Chemical formula]

[0272] Synthesis of Intermediate 270-1 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 269-6 with a molar amount of 5.76 mmol and a yield of 57.6%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 269-6 was MS(ASAP) = 245.

[0273] Synthesis of Intermediate 270-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 270-2 with a molar amount of 4.97 mmol and a yield of 49.7%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 270-2 was MS(ASAP) = 433.

[0274] Synthesis of Intermediate 270-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 270-3. The molar amount was 8.47 mmol, the yield was 84.7%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 270-3 was MS(ASAP)=1124.

[0275] Synthesis of Organic Compound M270 10 mmol of Intermediate 270-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one drop at a time. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and the crude product was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M270. The yield was 35.7%, and the result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of organic compound M270 was MS(ASAP)=1098.

[0276] Example 29 The synthetic route of organic compound M271 is as follows. [Chemical formula]

[0277] Synthesis of Intermediate 271-2 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 271-2. The molar amount was 5.87 mmol and the yield was 58.7%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 271-2 was MS(ASAP) = 311.

[0278] Synthesis of Intermediate 271-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 271-3. The molar amount was 6.78 mmol and the yield was 67.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 271-3 was MS(ASAP) = 499.

[0279] Synthesis of Intermediate 271-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization to obtain Intermediate 271-4 with a molar amount of 8.09 mmol, a yield of 80.9%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of MS(ASAP) = 1190 for Intermediate 271-4.

[0280] Synthesis of Organic Compound M271 10 mmol of Intermediate 271-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one drop at a time. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and the crude product was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M271, with a yield of 37.1%, and the result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of MS(ASAP) = 1164 for organic compound M271.

[0281] Example 30 The synthetic route of organic compound M274 is as follows.

Chemical formula

[0282] Synthesis of Intermediate 274-2 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 274-2. The molar amount was 6.34 mmol and the yield was 63.4%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 274-2 was MS(ASAP)=225.

[0283] Synthesis of Intermediate 274-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 274-3. The molar amount was 6.18 mmol and the yield was 61.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 274-3 was MS(ASAP)=413.

[0284] Synthesis of Intermediate 274-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 274-4. The molar amount was 8.39 mmol, the yield was 83.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 274-4 was MS(ASAP)=1104.

[0285] Synthesis of Organic Compound M274 10 mmol of Intermediate 274-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M274. The yield was 32.1%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M274 was MS(ASAP)=1078.

[0286] Example 31 The synthetic route of organic compound M277 is as follows. [Chemical formula]

[0287] Synthesis of Intermediate 277-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and the organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 277-1 with a molar amount of 8.15 mmol, a yield of 81.5%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of MS(ASAP) = 1028 for Intermediate 277-1.

[0288] Synthesis of Organic Compound M277 Add 10 mmol of intermediate 277-1 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C under an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M277, with a yield of 32.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M277 is MS(ASAP)=1002. 1H NMR (400 MHz, CDCl3) δ 9.01 (s, 1H), 8.55 (s, 1H), 8.42 (dd, J = 19.1, 9.7 Hz, 4H), 7.91 (s, 1H), 7.78 (dt, J = 19.1, 10.1 Hz, 7H), 7.59 (t, J = 10.3 Hz, 3H), 7.55 - 7.33 (m, 9H), 7.23 (t, J = 7.4 Hz, 1H), 7.04 (d, J = 8.8 Hz, 1H), 6.49 (s, 1H), 6.42 (d, J = 7.9 Hz, 1H), 6.31 (d, J = 8.5 Hz, 1H), 1.58 (s, 9H), 1.50 (s, 9H), 1.44 (s, 9H), 1.07 (s, 9H).

[0289] Example 32 The synthetic route of organic compound M278 is as follows.

[0290] [Chemical formula]

[0291] Synthesis of intermediate 278-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 278-1, with a molar amount of 8.33 mmol, a yield of 83.3%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 278-1 being MS(ASAP) = 840.

[0292] Synthesis of Intermediate 278-2 Intermediate 278-1 (10 mmol) and 50 mL of acetonitrile were placed in a three-necked flask. 20 mmol of CuCl and 30 mmol of tert-butyl nitrite (t-BuONO) were added at 65 °C. Gas leakage was observed. After the addition was complete, the gas evolution was stopped, the mixture was cooled to room temperature, and stirred for 1 hour. After extraction with dichloromethane and rotary drying, it was dissolved in petroleum ether and then passed through silica gel to obtain Intermediate 278-2, with a molar amount of 8.76 mmol, a yield of 87.6%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 278-2 being MS(ASAP) = 320.

[0293] Synthesis of Intermediate 278-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 278-3. The molar amount was 7.54 mmol, the yield was 75.4%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 278-3 was MS(ASAP)=1124.

[0294] Synthesis of Organic Compound M278 10 mmol of Intermediate 278-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M278. The yield was 37.6%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M278 was MS(ASAP)=1098.

[0295] Example 33 The synthetic route of organic compound M279 is as follows. [Chemical formula]

[0296] Synthesis of Intermediate 279-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 279-2 with a molar amount of 8.09 mmol, a yield of 80.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 279-2 was MS(ASAP) = 432.

[0297] Synthesis of Intermediate 279-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 279-3 with a molar amount of 7.33 mmol, a yield of 73.3%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 279-3 was MS(ASAP) = 1236.

[0298] Synthesis of Organic Compound M279 Add 10 mmol of intermediate 279-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C in an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate distill the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M279, with a yield of 45.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M279 is MS(ASAP)=1210.

[0299] Example 34 The synthetic route of organic compound M280 is as follows.

Chemical formula

[0300] Synthesis of intermediate 280-1 Put 10 mmol of intermediate 274-2 and 50 mL of acetonitrile into a three-necked flask. Add 20 mmol of CuCl and 30 mmol of tert-butyl nitrite (t-BuONO) at 65 °C. Gas leakage was observed. After the addition was complete, stop the gas evolution, cool the mixture to room temperature, and stir for 1 hour. After extraction with dichloromethane and rotary drying, dissolve it in petroleum ether and pass through silica gel to obtain intermediate 280-1 with a molar amount of 8.92 mmol, a yield of 89.2%. The result of the atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of intermediate 280-1 is MS(ASAP)=244.

[0301] Synthesis of Intermediate 280-2 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-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 280-2 in a molar amount of 7.13 mmol, a yield of 71.3%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 280-2 was MS(ASAP) = 1048.

[0302] Synthesis of Organic Compound M280 10 mmol of Intermediate 280-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour, then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and the crude product was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., Organic Compound M280, with a yield of 34.8%, and the result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Organic Compound M280 was MS(ASAP) = 1022.

[0303] Example 35 The synthetic route of organic compound M281 is as follows.

Chemical formula

[0304] Synthesis of Intermediate 281-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 281-2 with a molar amount of 8.38 mmol, a yield of 83.8%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 281-2 was MS(ASAP) = 244.

[0305] Synthesis of Intermediate 281-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 281-3 with a molar amount of 6.79 mmol, a yield of 67.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 281-3 was MS(ASAP) = 1048.

[0306] Synthesis of Organic Compound M281 Add 10 mmol of intermediate 281-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool to -30 °C under a N2 atmosphere, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M281, with a yield of 42.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M281 is MS(ASAP)=1022.

[0307] Example 36 The synthetic route of organic compound M282 is as follows.

Chemical formula

[0308] Synthesis of intermediate 282-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization to obtain Intermediate 282-1. The molar amount was 7.46 mmol, the yield was 74.6%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 282-1 was MS(ASAP)=300.

[0309] Synthesis of Intermediate 282-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization to obtain Intermediate 282-2. The molar amount was 6.13 mmol, the yield was 61.3%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 282-2 was MS(ASAP)=1104.

[0310] Synthesis of Organic Compound M282 Add 10 mmol of intermediate 282-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30°C in an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60°C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0°C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120°C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent in it to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M282, with a yield of 33.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M282 is MS(ASAP)=1078.

[0311] Example 37 The synthetic route of organic compound M283 is as follows.

Chemical formula

[0312] Synthesis of intermediate 283-1 Put 10 mmol of intermediate 268-6 and 50 mL of acetonitrile into a three-necked flask. Add 20 mmol of CuCl and 30 mmol of tert-butyl nitrite (t-BuONO) at 65°C. Gas leakage was observed. After the addition was complete, stop the gas evolution, cool the mixture to room temperature and stir for 1 hour. After extraction with dichloromethane and rotary drying, dissolve it in petroleum ether and then pass through silica gel to obtain intermediate 283-1, with a molar amount of 9.02 mmol, a yield of 90.2%. The result of the atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of intermediate 283-1 is MS(ASAP)=376.

[0313] Synthesis of Intermediate 283-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography and recrystallization. The molar amount of Intermediate 283-2 was 6.97 mmol, the yield was 69.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 283-2 was MS(ASAP) = 1180.

[0314] Synthesis of Organic Compound M283 10 mmol of Intermediate 283-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M283. The yield was 36.8%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M283 was MS(ASAP) = 1154.

[0315] Example 38 The synthetic route of organic compound M284 is as follows.

Chemical formula

[0316] Synthesis of Intermediate 284-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization to obtain Intermediate 284-1. The molar amount was 8.25 mmol, the yield was 82.5%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 284-1 was MS(ASAP) = 764.

[0317] Synthesis of Intermediate 284-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization to obtain Intermediate 284-2. The molar amount was 7.31 mmol, the yield was 73.1%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 284-2 was MS(ASAP) = 972.

[0318] Synthesis of Organic Compound M284 Add 10 mmol of intermediate 284-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C under a N2 atmosphere, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent therein under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the dropping is completed, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent therein by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M284, with a yield of 47.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M284 is MS(ASAP)=946.

[0319] Example 39 The synthetic route of organic compound M285 is as follows.

Chemical formula

[0320] Synthesis of intermediate 285-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, organic phase column chromatography, and recrystallization to obtain Intermediate 285-1. The molar amount was 8.97 mmol, the yield was 89.7%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 285-1 was MS(ASAP) = 1028.

[0321] Synthesis of Organic Compound M285 10 mmol of Intermediate 285-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M285. The yield was 40.8%, and the result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of organic compound M285 was MS(ASAP) = 1002.

[0322] Example 40 The synthetic route of organic compound M286 is as follows.

Chemical formula

[0323] Synthesis of Intermediate 286-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and purified by organic phase column chromatography and recrystallization to obtain Intermediate 286-1 with a molar amount of 8.45 mmol, a yield of 84.5%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of MS(ASAP) = 1048 for Intermediate 286-1.

[0324] Synthesis of Organic Compound M286 Add 10 mmol of Intermediate 286-1 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30°C under an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60°C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0°C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, further raise the temperature to 120°C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution to quench with ethyl acetate, extract the aqueous phase with ethyl acetate, combine the organic phases, distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M286, with a yield of 47.3%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M286 is MS(ASAP)=1022.

[0325] Example 41 The synthetic route of organic compound M287 is as follows.

Chemical formula

[0326] Synthesis of Intermediate 287-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to column chromatography and recrystallization of the organic phase. The molar amount of Intermediate 287-1 was 8.22 mmol, the yield was 82.2%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 287-1 was MS(ASAP) = 972.

[0327] Synthesis of Organic Compound M287 10 mmol of Intermediate 287-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M287, with a yield of 36.7%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M287 was MS(ASAP) = 946.

[0328] Example 42 The synthesis route of organic compound M288 is as follows. [Chem.]

[0329] Synthesis of Intermediate 288-1 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-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and organic phase column chromatography and recrystallization. The molar amount of Intermediate 288-1 was 9.12 mmol, the yield was 91.2%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 288-1 was MS(ASAP) = 1104.

[0330] Synthesis of Organic Compound M288 Add 10 mmol of intermediate 288-1 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C in an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M288, with a yield of 35.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M288 is MS(ASAP)=1078.

[0331] Example 43 The synthetic route of organic compound M289 is as follows.

Chemical Structure

[0332] Synthesis of intermediate 289-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and then organic phase column chromatography and recrystallization to obtain Intermediate 289-1 with a molar amount of 8.06 mmol, a yield of 80.6%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 289-1 was MS(ASAP) = 1160.

[0333] Synthesis of Organic Compound M289 10 mmol of Intermediate 288-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M289, with a yield of 33.6%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M289 was MS(ASAP) = 1134.

[0334] Example 44 The synthetic route of organic compound M290 is as follows. [Chemical formula]

[0335] Synthesis of Intermediate 290-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. Column chromatography and recrystallization of the organic phase were performed. The molar amount of Intermediate 290-2 was 8.15 mmol, the yield was 81.5%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 290-2 was MS(ASAP) = 840.

[0336] Synthesis of Intermediate 290-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. Column chromatography and recrystallization of the organic phase were performed. The molar amount of Intermediate 290-3 was 7.39 mmol, the yield was 73.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 290-3 was MS(ASAP) = 1028.

[0337] Synthesis of Organic Compound M290 Add 10 mmol of intermediate 290-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30°C under a N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60°C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0°C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120°C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M290, with a yield of 33.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M290 is MS(ASAP)=1002. 1H NMR(400MHz,CDCl3)δ 9.02(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),7.69-7.61(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).

[0338] Example 45 The synthetic route of organic compound M291 is as follows.

Chemical Structure

[0339] Synthesis of intermediate 291-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by washing with water, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 291-2 with a molar amount of 8.84 mmol, a yield of 88.4%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 291-2 was MS(ASAP)=784.

[0340] Synthesis of Intermediate 291-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by washing with water, and subjected to organic phase column chromatography and recrystallization to obtain Intermediate 291-3 with a molar amount of 7.22 mmol, a yield of 72.2%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 291-3 was MS(ASAP)=972.

[0341] Synthesis of Organic Compound M291 Add 10 mmol of Intermediate 291-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool it to -30 °C under a N2 atmosphere, dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop, raise the temperature to 60 °C and react for 2 hours, and distill off the n-hexane solvent therein under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine, after the dropping is completed, raise the temperature to room temperature and stir, further raise the temperature to 120 °C and stir for 3 hours, cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate, extract the aqueous phase with ethyl acetate and combine the organic phases, distill off the solvent therein by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M291, with a yield of 38.9%, and the result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M291 is MS(ASAP)=946.

[0342] Example 46 The synthetic route of organic compound M292 is as follows.

Chemical formula

[0343] Synthesis of Intermediate 292-1 Intermediate 253-4 (10 mmol), Compound 290-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 292-1. The molar amount was 7.38 mmol and the yield was 73.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 292-1 was MS(ASAP)=820.

[0344] Synthesis of Intermediate 292-2 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 292-2. The molar amount was 6.62 mmol and the yield was 66.2%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 292-2 was MS(ASAP)=1028.

[0345] Synthesis of Organic Compound M292 Add 10 mmol of Intermediate 292-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30°C in an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60°C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0°C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120°C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M292, with a yield of 43.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M292 is MS(ASAP)=1002.

[0346] Example 47 The synthesis route of organic compound M293 is as follows. [Chemical formula]

[0347] Synthesis of Intermediate 293-1 Intermediate 253-4 (10 mmol), Compound 291-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography to obtain Intermediate 293-1. The molar amount was 7.08 mmol and the yield was 70.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 293-1 was MS(ASAP) = 764.

[0348] Synthesis of Intermediate 293-2 Intermediate 293-1 (10 mmol), Compound 269-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography to obtain Intermediate 293-2. The molar amount was 6.51 mmol and the yield was 65.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 293-2 was MS(ASAP) = 972.

[0349] Synthesis of Organic Compound M293 Add 10 mmol of intermediate 293-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C under a N2 atmosphere, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent therein under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent therein by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M293, with a yield of 41.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M293 is MS(ASAP)=946.

[0350] Example 48 The synthetic route of organic compound M294 is as follows.

Chemical formula

[0351] Synthesis of intermediate 294-1 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 294-1 with a molar amount of 7.37 mmol and a yield of 73.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 294-1 was MS(ASAP)=1028.

[0352] Synthesis of Intermediate 294-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 294-2 with a molar amount of 6.89 mmol and a yield of 68.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 294-2 was MS(ASAP)=1236.

[0353] Synthesis of Organic Compound M294 Add 10 mmol of Intermediate 294-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C under a N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M294, with a yield of 43.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M294 is MS(ASAP)=1210.

[0354] Example 49 The synthetic route of organic compound M295 is as follows.

Chemical formula

[0355] Synthesis of Intermediate 295-1 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 295-1, with a molar amount of 8.23 mmol and a yield of 82.3%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 295-1 was MS(ASAP) = 972.

[0356] Synthesis of Intermediate 295-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 295-2, with a molar amount of 7.46 mmol and a yield of 74.6%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 295-2 was MS(ASAP) = 1180.

[0357] Synthesis of Organic Compound M295 Add 10 mmol of intermediate 295-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C in an N₂ atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M295, with a yield of 36.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M295 is MS(ASAP)=1154.

[0358] Example 50 The synthetic route of organic compound M296 is as follows.

Chemical formula

[0359] Synthesis of intermediate 296-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 296-2, with a molar amount of 8.89 mmol, a yield of 88.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 296-2 being MS(ASAP) = 840.

[0360] Synthesis of Intermediate 296-3 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction and liquid separation by washing with water. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 296-3, with a molar amount of 7.97 mmol, a yield of 79.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 296-3 being MS(ASAP) = 1028.

[0361] Synthesis of Organic Compound M296 Add 10 mmol of intermediate 296-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C in an N₂ atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M296, with a yield of 39.2%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M296 is MS(ASAP)=1002.

[0362] Example 51 The synthesis route of organic compound M297 is as follows.

Chemical formula

[0363] Synthesis of intermediate 297-1 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 297-1 with a molar amount of 7.81 mmol and a yield of 78.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 297-1 was MS(ASAP) = 820.

[0364] Synthesis of Intermediate 297-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 297-2 with a molar amount of 6.81 mmol and a yield of 68.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 297-2 was MS(ASAP) = 1028.

[0365] Synthesis of Organic Compound M297 Add 10 mmol of Intermediate 297-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C in an N₂ atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate distill the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M297, with a yield of 39.5%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M297 is MS(ASAP)=1002.

[0366] Example 52 The synthetic route of organic compound M298 is as follows.

Chemical formula

[0367] Synthesis of Intermediate 298-1 Compound 290-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 298-1. The molar amount was 7.33 mmol and the yield was 73.3%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 298-1 was MS(ASAP) = 337.

[0368] Synthesis of Intermediate 298-2 Compound 298-1 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and column chromatography of the organic phase was performed to obtain Intermediate 298-2. The molar amount was 8.25 mmol and the yield was 82.5%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 298-2 was MS(ASAP) = 481.

[0369] Synthesis of Intermediate 298-3 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 298-3. The molar amount was 6.54 mmol and the yield was 65.4%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 298-3 was MS(ASAP) = 726.

[0370] Synthesis of Intermediate 298-5 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 298-5. The molar amount was 7.38 mmol and the yield was 73.8%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 298-5 was MS(ASAP) = 850.

[0371] Synthesis of Intermediate 298-6 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization to obtain Intermediate 298-6 with a molar amount of 8.76 mmol, a yield of 87.6%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 298-6 was MS(ASAP)=1042.

[0372] Synthesis of Organic Compound M298 10 mmol of Intermediate 298-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the solvent therein was rotary distilled to obtain a crude product, and the crude product was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M298, with a yield of 33.7%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M298 was MS(ASAP)=1016.

[0373] Example 53 The synthetic route of organic compound M299 is as follows.

Chemical formula

[0374] Synthesis of Intermediate 299-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 299-2. The molar amount was 7.10 mmol and the yield was 71.0%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 299-2 was MS(ASAP) = 836.

[0375] Synthesis of Intermediate 299-3 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid separation with water washing, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 299-3. The molar amount was 8.11 mmol, the yield was 81.1%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 299-3 was MS(ASAP) = 1028.

[0376] Synthesis of Organic Compound M299 Add 10 mmol of Intermediate 299-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool it to -30 °C in an N2 atmosphere, dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop, raise the temperature to 60 °C and react for 2 hours, and distill off the n-hexane solvent therein under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine, after the addition is complete, raise the temperature to room temperature and stir, further raise the temperature to 120 °C and stir for 3 hours, cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate, extract the aqueous phase with ethyl acetate and combine the organic phases, rotary evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely Organic Compound M299, with a yield of 39.6%, and the result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M299 is MS(ASAP)=1002.

[0377] Example 54 The synthetic route of Organic Compound M300 is as follows.

Chemical formula

[0378] Synthesis of Intermediate 300-2 Intermediate 1-5 (10 mmol), Compound 300-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 300-2 with a molar amount of 7.26 mmol and a yield of 72.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 300-2 was MS(ASAP) = 670.

[0379] Synthesis of Intermediate 300-3 Intermediate 300-2 (10 mmol), Compound 298-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 300-3 with a molar amount of 6.85 mmol and a yield of 68.5%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 300-3 was MS(ASAP) = 794.

[0380] Synthesis of Intermediate 300-4 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, and then organic phase column chromatography and recrystallization to obtain Intermediate 300-4. The molar amount was 7.79 mmol, the yield was 77.9%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 300-4 was MS(ASAP)=986.

[0381] Synthesis of Organic Compound M300 10 mmol of Intermediate 300-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M300. The yield was 36.7%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M300 was MS(ASAP)=960.

[0382] Example 55 The synthesis route of organic compound M301 is as follows.

Chemical formula

[0383] Synthesis of Intermediate 301-1 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 301-1. The molar amount was 7.88 mmol and the yield was 78.8%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 301-1 was MS(ASAP) = 726.

[0384] Synthesis of Intermediate 301-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 301-2. The molar amount was 6.21 mmol and the yield was 62.1%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 301-2 was MS(ASAP) = 850.

[0385] Synthesis of Intermediate 301-3 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). Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase, and recrystallization to obtain Intermediate 301-3 with a molar amount of 7.53 mmol, a yield of 75.3%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 301-3 was MS(ASAP) = 1042.

[0386] Synthesis of Organic Compound M301 10 mmol of Intermediate 301-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30 °C under an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M301, with a yield of 37.9%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M301 was MS(ASAP) = 1016.

[0387] Example 56 The synthetic route of organic compound M302 is as follows.

Chemical formula

[0388] Synthesis of Intermediate 302-1 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 302-1. The molar amount was 8.45 mmol and the yield was 84.5%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 302-1 was MS(ASAP) = 820.

[0389] Synthesis of Intermediate 302-3 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and subjected to column chromatography of the organic phase to obtain Intermediate 302-3. The molar amount was 7.59 mmol and the yield was 75.9%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 302-3 was MS(ASAP) = 1048.

[0390] Synthesis of Organic Compound M302 Add 10 mmol of intermediate 302-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C under a N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M302, with a yield of 36.3%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M302 is MS(ASAP)=1022.

[0391] Example 57 The synthetic route of organic compound M303 is as follows.

Chemical formula

[0392] Synthesis of intermediate 303-2 Intermediate 253-4 (10 mmol), Compound 303-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 303-2, with a molar amount of 8.31 mmol and a yield of 83.1%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 303-2 was MS(ASAP) = 916.

[0393] Synthesis of Intermediate 303-3 Intermediate 303-2 (10 mmol), Compound 302-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and column chromatography of the organic phase was performed to obtain Intermediate 303-3, with a molar amount of 7.17 mmol and a yield of 71.7%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 303-3 was MS(ASAP) = 1144.

[0394] Synthesis of Organic Compound M303 Add 10 mmol of intermediate 303-3 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30°C under a nitrogen atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60°C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0°C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then further raise the temperature to 120°C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M303, with a yield of 37.4%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M303 is MS(ASAP)=1118.

[0395] Example 58 The synthetic route of organic compound M304 is as follows.

Chemical formula

[0396] Synthesis of intermediate 304-2 Compound 129-1 (10 mmol), Compound 304-1 (10 mmol), Pd(dba)2 (palladium dibenzylideneacetone, 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 304-2 with a molar amount of 7.03 mmol and a yield of 70.3%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 304-2 was MS(ASAP) = 481.

[0397] Synthesis of Intermediate 304-3 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 for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 304-3 with a molar amount of 6.87 mmol and a yield of 68.7%. The result of the atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 304-3 was MS(ASAP) = 690.

[0398] Synthesis of Intermediate 304-4 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and purified by column chromatography of the organic phase to obtain Intermediate 304-4 with a molar amount of 6.87 mmol and a yield of 68.7%. The result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 304-4 was MS(ASAP) = 856.

[0399] Synthesis of Intermediate 304-6 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by liquid-liquid extraction with water washing, and purified by column chromatography and recrystallization of the organic phase. The molar amount of Intermediate 304-6 was 7.22 mmol, the yield was 72.2%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 304-6 was MS(ASAP) = 1048.

[0400] Synthesis of Organic Compound M304 Add 10 mmol of intermediate 304-6 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool to -30 °C under an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M304, with a yield of 34.8%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M304 is MS(ASAP)=1022.

[0401] Example 59 The synthetic route of organic compound M305 is as follows.

Chemical formula

[0402] Synthesis of intermediate 305-1 Dissolve 10 mmol of intermediate 20-2 and 10 mmol of intermediate 16-5 in a mixed solvent of 1,4-dioxane and water (21 / 2 ml). Add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), and stir at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, remove the solvent with a rotary evaporator, extract, separate the liquid by washing with water, and perform organic phase column chromatography to obtain intermediate 305-1, with a molar amount of 8.27 mmol and a yield of 82.7%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of intermediate 305-1 is MS(ASAP)=896.

[0403] Synthesis of Intermediate 305-3 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and the organic phase was subjected to column chromatography to obtain Intermediate 305-3 in a molar amount of 7.69 mmol and a yield of 76.9%. The result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Intermediate 305-3 was MS(ASAP) = 1104.

[0404] Synthesis of Organic Compound M305 10 mmol of Intermediate 305-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by high-speed silica gel column to obtain a purified product. Recrystallization was performed with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., Organic Compound M305, with a yield of 51.2%. The result of atmospheric pressure solids analysis probe mass spectrum (ASAP-MS) of Organic Compound M305 was MS(ASAP) = 1078.

[0405] Example 60 The synthetic route of Organic Compound M306 is as follows.

Chem.

[0406] Synthesis of Intermediate 306-1 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 306-1. The molar amount was 8.89 mmol and the yield was 88.9%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 306-1 was MS(ASAP) = 764.

[0407] Synthesis of Intermediate 306-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by washing with water, and subjected to organic phase column chromatography to obtain Intermediate 306-2. The molar amount was 7.33 mmol and the yield was 73.3%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 306-2 was MS(ASAP) = 972.

[0408] Synthesis of Organic Compound M306 Add 10 mmol of intermediate 306-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool to -30 °C under a N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours, then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine, after the addition is complete, raise the temperature to room temperature and stir, further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate, extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate evaporate the solvent therein to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M306, with a yield of 46.4%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M306 is MS(ASAP)=946.

[0409] Example 61 The synthesis route of organic compound M307 is as follows.

Chemical formula

[0410] Synthesis of intermediate 307-1 Dissolve intermediate 16-8 (10 mmol) and compound 16-5 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), and stir at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, remove the solvent with a rotary evaporator, extract, separate the liquid by washing with water, and perform organic phase column chromatography to obtain intermediate 307-1. The molar amount is 8.41 mmol and the yield is 84.1%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of intermediate 307-1 is MS(ASAP)=896.

[0411] Synthesis of Intermediate 307-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid separation with water washing, and subjected to organic phase column chromatography to obtain Intermediate 307-2. The molar amount was 7.89 mmol and the yield was 78.9%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 307-2 was MS(ASAP) = 1104.

[0412] Synthesis of Organic Compound M307 10 mmol of Intermediate 307-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the dropping was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, Organic Compound M307, and the yield was 44.1%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Organic Compound M307 was MS(ASAP) = 1078.

[0413] Example 62 The synthetic route of Organic Compound M308 is as follows. [Chemistry]

[0414] Synthesis of Intermediate 308-1 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and subjected to organic phase column chromatography to obtain Intermediate 308-1. The molar amount was 8.33 mmol and the yield was 83.3%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 308-1 was MS(ASAP) = 896.

[0415] Synthesis of Intermediate 308-2 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 hours under a nitrogen atmosphere. After cooling, the solvent was removed by a rotary evaporator, extracted, separated by liquid-liquid extraction with water washing, and subjected to organic phase column chromatography to obtain Intermediate 308-2. The molar amount was 7.93 mmol and the yield was 79.3%. The result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of Intermediate 308-2 was MS(ASAP) = 1104.

[0416] Synthesis of Organic Compound M308 Add 10 mmol of intermediate 308-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Cool it to -30 °C under an N2 atmosphere, and dropwise add a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane drop by drop. Raise the temperature to 60 °C and react for 2 hours. Distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and further raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature, add an aqueous sodium carbonate solution and quench with ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Distill off the solvent by rotary evaporation to obtain a crude product, and purify it by high-speed silica gel column to obtain a purified product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M308, with a yield of 41.6%. The result of the atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of organic compound M308 is MS(ASAP)=1078.

[0417] Example 63 The synthetic route of organic compound M309 is as follows.

Chemical formula

[0418] Synthesis of intermediate 309-1 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization to obtain Intermediate 309-1, the molar amount of which was 7.89 mmol, the yield was 78.9%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 309-1 was MS(ASAP)=357.

[0419] Synthesis of Intermediate 309-2 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase and recrystallization to obtain Intermediate 309-2, the molar amount of which was 7.56 mmol, the yield was 75.6%, and the result of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of Intermediate 309-1 was MS(ASAP)=501.

[0420] Synthesis of Intermediate 309-4 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by washing with water, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 309-4 with a molar amount of 7.11 mmol, a yield of 71.1%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 309-4 was MS(ASAP) = 592.

[0421] Synthesis of Intermediate 309-5 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), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the mixture was stirred at 100 °C for 6 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, then extracted, separated by washing with water, and subjected to column chromatography and recrystallization of the organic phase to obtain Intermediate 309-5 with a molar amount of 6.87 mmol, a yield of 68.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of Intermediate 309-5 was MS(ASAP) = 784.

[0422] Synthesis of Intermediate 309-6 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 hours under a nitrogen atmosphere. After cooling, most of the solvent was removed by a rotary evaporator, followed by extraction, liquid separation by washing with water, column chromatography of the organic phase, and recrystallization to obtain Intermediate 309-6 with a molar amount of 7.97 mmol, a yield of 79.7%, and the result of atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) of MS(ASAP) = 972 for Intermediate 309-6.

[0423] Synthesis of Organic Compound M309 10 mmol of Intermediate 309-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 °C in an N2 atmosphere, and a solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise one by one. The temperature was raised to 60 °C and reacted for 2 hours, and the n-hexane solvent therein was distilled off under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was completed, the temperature was raised to room temperature and stirred, and further raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, an aqueous sodium carbonate solution was added to quench with ethyl acetate, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent therein was rotary distilled to obtain a crude product, which was purified by a high-speed silica gel column to obtain a purified product. Recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M309, with a yield of 42.5%, and the result of atmospheric pressure solid analysis probe mass spectrum (ASAP-MS) of MS(ASAP) = 946 for organic compound M309.

[0424] Comparative Example 1 Comparative Compound 1 was used as the comparative example in Examples 1 to 63 above. The structural formula of Comparative Compound 1 is as follows. [Chemical Formula]

[0425] As shown in Table 1, the HOMO (Highest Occupied Molecular Orbital) energy levels, LUMO (Lowest Unoccupied Molecular Orbital) energy levels, T1 (first excited triplet state) energy levels, and S1 (first excited singlet state) energy levels of Compounds M1 to M309 obtained in Examples 1 to 63 and Comparative Compound 1 of Comparative Example 1 were determined by quantum calculation. Specifically, using TD-DFT (time-dependent density functional theory) with Gaussian09W (Gaussian Inc.) (for the specific simulation method, see WO 2011141110), 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 from the TD-DFT (time-dependent density functional theory) method as "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO energy level and LUMO energy level were calculated according to the following formula, and the S1 level and T1 level were directly used.

[0426] HOMO (eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206 LUMO (eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385 Here, HOMO, LUMO, T1, and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree.

[0427] [Table 1A]

Table 1B

[0428] From the results in Table 1, the T1 level and S1 level of the organic compounds M1 to M309 provided by Examples 1 to 63 of the present application are both higher than the T1 level and S1 level of Comparative Compound 1, and the blue light emitted by the organic compounds M1 to M309 is biased towards a darker blue than Comparative Compound 1, indicating that it is advantageous for obtaining good color coordinates of the blue organic light-emitting device by applying the organic compounds M1 to M309 as the guest material in the light-emitting layer.

[0429] Exemplary manufacturing steps of the organic light-emitting device 100 provided in the present application are shown in Exemplary Example 1 below.

[0430] Example 1 In the organic light-emitting device provided in this example, ITO (indium tin oxide) is used as the anode, PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) is used as the material of the hole injection layer, PVK (Sigma Aldrich, average Mn 25,000 - 50,000) is used as the material of the hole transport layer, BH-1 to BH-3 are used as the host materials of the light-emitting layer of the organic light-emitting device respectively, the organic compounds M1 to M309 of Examples 1 to 67 and Comparative Compound 1 of Comparative Example 1 are used as the guest materials of the light-emitting layer of the organic light-emitting device respectively, ET and Liq (lithium 8-hydroxyquinoline) are used as the materials of the electron transport layer, and Al is used as the cathode. The specific manufacturing steps are as follows. a. Cleaning of the ITO anode Clean the ITO conductive glass with chloroform, acetone and / or isopropanol, and then perform ultraviolet ozone treatment.

[0431] b. Formation of the hole injection layer The hole injection layer material PEDOT (polyethylenedioxythiophene, Clevios) was spin-coated on the ITO anode and treated on a hot plate at 180 °C for 10 minutes. The thickness of the hole injection layer is 40 nm. TM AI4083)

[0432] c. Formation of the hole transport layer A toluene solution of PVK (Sigma Aldrich, Mn 25,000 - 50,000) with a concentration of 5 mg / ml was spin-coated on the hole injection layer and then treated on a hot plate at 180 °C for 60 minutes to make the thickness of the hole transport layer 20 nm.

[0433] d. Formation of the light-emitting layer In a nitrogen glove box, the light-emitting layer material was spin-coated on the hole transport layer and then treated on a hot plate at 140 °C for 10 minutes. The host materials in the light-emitting layers of different organic light-emitting devices correspond to BH-1, BH-2, or BH-3 respectively, and the guest materials in the light-emitting layers of different organic light-emitting devices corres...

Claims

1. An organic compound having a structure represented by general formula (1) or (2), 【Chemical 1】 In the formula, Ar １ is independently selected from structures represented by any of formulas (X-1) to (X-3), 【Chemical Formula 2】 Ar ３ and Ar ４ are each independently selected from structures represented by any of formulas (A-1) to (A-5), [Chemical 3] Ar １ When Ar is selected from Formula X-2, ４ Ar is independently selected from structures represented by any of Formula (A-2) to Formula (A-5), Ar ３ The linking site of Ar is a carbon atom on any benzene ring, and Ar ４ 's condensation sites are at two ortho-position carbon atoms in the same benzene ring, Ar ２ is selected from the structures represented by any of formula (B-1) to formula (B-4), 【Chemical Formula 4】 X is independently O, S, N-CH ３ , N-Ph or C(CH ３ ) ２ selected from, n ０ 、n １ 、n ２ 、n ５ are each independently selected from positive integers of 0 to 14, R ０ 、 R １ 、 R ２ or R ５ is each independently selected from -H, -D, 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 ketone 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 alkylene 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 hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms n ０ When n is 2 or more, two adjacent Rs ０ either form a ring with each other or do not form a ring. When n １ is 2 or more, two adjacent Rs １ either form a ring with each other or do not form a ring. When n ２ is 2 or more, two adjacent Rs ２ either form a ring with each other or do not form a ring. When n ５ is 2 or more, two adjacent Rs ５ either form a ring with each other or do not form a ring, an organic compound.

2. wherein the organic compound has a structure represented by any one of general formulas (2-1) to (2-28), 【Chemical Formula 5】 [Chemical Formula 6] 【Chemical Formula 7】 In the formula, R ３ , R ４ Each of them is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, and is selected from n ３ is 0 or more and 5 or less, n ３ When n is 2 or more, two adjacent Rs ３ either form a ring with each other or do not form a ring, n ４ is 0 or more and 5 or less, n ４ When n is 2 or more, two adjacent Rs ４ either form a ring with each other or do not form a ring, the organic compound according to claim 1.

3. R １ 、 R ２ 、 R ３ 、 R ４ or R ５ Any one of which 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, and a cyclic alkyl group having 3 to 10 carbon atoms, The organic compound according to claim 2.

4. R １ 、R ２ 、R ３ 、R ４ or R ５ Any one of which is independently selected from -H, -D, a linear alkyl group having 1 to 4 carbon atoms, and a branched alkyl group having 3 to 5 carbon atoms, the organic compound according to claim 3.

5. Ar ２ When the structure represented by the formula (B-2) exists in , the structure represented by the formula (B-2) is 【Chemical 8】 The organic compound according to claim 1, selected from at least one of them.

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, which is selected from the compounds of 【Chemical Formula 9】 【Chemical 10】 【Chemical 11】 【Chemical 12】 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical 18】 【Chemical 19】 The organic compound according to claim 1.

8. A mixture comprising an organic compound and at least one organic functional material 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 light-emitting material, a host material or an organic dye, wherein the organic compound has a structure represented by general formula (1) or (2), 【Chemical 20】 In the formula, Ar １ is independently selected from the structures represented by any of formulas (X-1) to (X-3), 【Chemical 21】 Ar ３ and Ar ４ are each independently selected from structures represented by any of formulas (A-1) to (A-5), 【Chemical 22】 Ar １ When Ar is selected from Formula X-2, ４ Ar is independently selected from the structures represented by any of Formula (A-2) to Formula (A-5), Ar ３ The linking site of Ar is a carbon atom on any benzene ring, and Ar ４ The condensation site is at two ortho-position carbon atoms in the same benzene ring, Ar ２ is selected from the structures represented by any one of formulas (B-1) to (B-4), 【Chemical 23】 X is independently O, S, N-CH ３ , N-Ph or C(CH ３ ), ２ selected from, n ０ 、 n １ 、 n ２ 、 n ５ are each independently selected from positive integers between 0 and 14, R ０、 R １ , R ２ or R ５ Any of them is independently selected from -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, and is selected from n ０ When n is 2 or more, two adjacent Rs ０ either form a ring with each other or do not form a ring, and when n １ is 2 or more, two adjacent Rs １ either form a ring with each other or do not form a ring, and when n ２ is 2 or more, two adjacent Rs ２ either form a ring with each other or do not form a ring, and when n ５ is 2 or more, two adjacent Rs ５ either form a ring with each other or do not form a ring, a mixture.

9. A composition comprising an organic compound or a mixture and at least one organic solvent, wherein the mixture comprises the organic compound and at least one organic functional material 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 light-emitting material, a host material or an organic dye, wherein the organic compound has a structure represented by general formula (1) or (2), 【Chemical Formula 24】 In the formula, Ar １ is independently selected from the structures represented by any of formulas (X-1) to (X-3), 【Chemical 25】 Ar ３ and Ar ４ are each independently selected from the structures represented by any of formulas (A-1) to (A-5), 【Chemical 26】 Ar １ When Ar is selected from Formula X-2, ４ Ar is independently selected from the structures represented by any of Formula (A-2) to Formula (A-5), Ar ３ The linking site of Ar is a carbon atom on any benzene ring, and Ar ４ The condensation sites are at two ortho-position carbon atoms in the same benzene ring, Ar ２ is selected from the structures represented by any of Formula (B-1) to Formula (B-4), 【Chemical 27】 X is independently O, S, N-CH ３ , N-Ph or C(CH ３ ) ２ selected from, n ０ 、n １ 、n ２ 、n ５ are each independently selected from positive integers of 0 to 14, R ０ , R １ , R ２ or R ５ is, independently of one another, -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, and is selected from n ０ When n is 2 or more, two adjacent Rs ０ either form a ring with each other or do not form a ring, and when n １ is 2 or more, two adjacent Rs １ either form a ring with each other or do not form a ring, and when n ２ is 2 or more, two adjacent Rs ２ either form a ring with each other or do not form a ring, and when n ５ is 2 or more, two adjacent Rs ５ either form a ring with each other or do not form a ring, a composition.

10. An organic light-emitting device, a first electrode, a second electrode provided 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 comprises one or more kinds of organic compounds or a mixture, or is manufactured from a composition, wherein the composition comprises the organic compound or the mixture and at least one organic solvent, wherein the mixture comprises the organic compound and at least one organic functional material 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 light-emitting material, a host material or an organic dye, wherein the organic compound has a structure represented by general formula (1) or (2), ​ In the formula, Ar １ is independently selected from the structures represented by any one of formulas (X-1) to (X-3), 【Chemical 29】 Ar ３ and Ar ４ are each independently selected from the structures represented by any of formulas (A-1) to (A-5), 【Chemical 30】 Ar １ When Ar is selected from Formula X-2, ４ Ar is independently selected from the structures represented by any of Formula (A-2) to Formula (A-5), Ar ３ The linking site of Ar is a carbon atom on any benzene ring, and Ar ４ 's condensation sites are at two ortho-position carbon atoms in the same benzene ring, Ar ２ is selected from the structures represented by any one of Formula (B-1) to Formula (B-4), 【Chemical 31】 X is O, S, N-CH ３ , N-Ph or C(CH ３ ) ２ and each is independently selected from n ０ 、n １ 、n ２ 、n ５ are each independently selected from positive integers of 0 to 14, R ０ 、 R １ 、 R ２ or R ５ Each of which is independently -H, -D, 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 ketone 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 alkylene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, and is selected from n ０ When n is 2 or more, two adjacent Rs ０ either form a ring with each other or do not form a ring, and when n １ is 2 or more, two adjacent Rs １ either form a ring with each other or do not form a ring, and when n ２ is 2 or more, two adjacent Rs ２ either form a ring with each other or do not form a ring, and when n ５ is 2 or more, two adjacent Rs ５ either form a ring with each other or do not form a ring, an organic light-emitting device.

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

12. The organic light-emitting device according to claim 11, wherein the host material contains one or more of an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, and a pyrimidine derivative.

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 including an organic light-emitting device, wherein the organic light-emitting device a first electrode, a second electrode provided 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 contains one or more organic compounds or a mixture, or is manufactured from a composition, the composition contains the organic compound or the mixture, and at least one organic solvent, the mixture contains the organic compound and at least one organic functional material 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 light-emitting material, a host material, or an organic dye, the organic compound has a structure represented by general formula (1) or (2), 【Chemical 32】 wherein Ar １ is independently selected from the structures represented by any of Formula (X-1) to Formula (X-3), 【Chemical 33】 Ar ３ and Ar ４ are each independently selected from the structures represented by any one of Formula (A-1) to Formula (A-5), 【Chemical 34】 Ar １ When Ar is selected from Formula X-2, ４ Ar is independently selected from the structures represented by any of Formula (A-2) to Formula (A-5), Ar ３ The linking site of Ar is a carbon atom on any benzene ring, and Ar ４ The condensation sites are at two ortho-position carbon atoms in the same benzene ring, Ar ２ is selected from the structures represented by any one of formulae (B-1) to (B-4), 【Chemical 35】 、 X is independently O, S, N-CH ３ , N-Ph or C(CH ３ ) ２ selected from, n ０ 、n １ 、n ２ 、n ５ are each independently selected from positive integers between 0 and 14, R ０ 、R １ 、R ２ or R ５ Each of which is independently -H, -D, 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 ketone 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 alkylene 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 hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, and is selected from n ０ When n is 2 or more, two adjacent Rs ０ either form a ring with each other or do not form a ring, and when n １ is 2 or more, two adjacent Rs １ either form a ring with each other or do not form a ring, and when n ２ is 2 or more, two adjacent Rs ２ either form a ring with each other or do not form a ring, and when n ５ is 2 or more, two adjacent Rs ５ either form a ring with each other or do not form a ring, display panel.

15. The organic compound has a structure represented by any one of general formulas (2-1) to (2-28). 【Chemical Formula 36】 【Chemical 37】 【Chemical Formula 38】 wherein R ３ , R ４ is each independently selected from -H, -D, 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 ketone 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 alkylene 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 hydroxy group, a nitro group, -CF ３ , -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, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, n ３ is 0 or more and 5 or less, n ３ When n is 2 or more, two adjacent Rs ３ either form a ring with each other or do not form a ring, n ４ is 0 or more and 5 or less, n ４ When n is 2 or more, two adjacent Rs ４ either form a ring with each other or do not form a ring, the display panel according to claim 14.

16. R １ 、 R ２ 、 R ３ 、 R ４ or R ５ Any one of which 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, and a cyclic alkyl group having 3 to 10 carbon atoms, the display panel according to claim 15.

17. R １ 、R ２ 、R ３ 、R ４ or R ５ Any one of which is independently selected from -H, -D, a linear alkyl group having 1 to 4 carbon atoms, and a branched alkyl group having 3 to 5 carbon atoms, the display panel according to claim 16.

18. Ar ２ When the structure represented by the formula (B-2) exists in [it], the structure represented by the formula (B-2) is 【Chemical 39】 The display panel according to claim 14, which is selected from at least one of the above.

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

20. The display panel according to claim 19, wherein the host material contains one or more of an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, and a pyrimidine derivative.

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