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

Abstract

The present invention provides organic compounds, mixtures, compositions, organic light-emitting devices, and display panels that can improve the luminous efficiency and lifespan of organic light-emitting devices. [Solution] The organic compound has a structure represented by general formula (1) or general formula (2). TIFF2026082747000095.tif38162 This invention improves the overall solubility of organic compounds, facilitates the purification of organic compounds, thereby increasing their purity, and further improves the efficiency of organic light-emitting devices made from such organic compounds, thereby extending their lifespan.

Description

Technical Field

[0001] This application claims priority based on a Chinese patent application filed with the China National Intellectual Property Administration on November 06, 2024, with an application number of 202411574952.4, the content of which is incorporated herein by reference.

[0002] This application relates to the display field, and in particular, to organic compounds, mixtures, compositions, organic light-emitting devices, and display panels.

Background Art

[0003] Currently, an organic electroluminescent device usually includes an anode, a cathode, and an organic layer located between both of them. By using the organic substances in the organic layer to convert electrical energy into light energy, organic electroluminescence is realized. In order to improve the luminous efficiency of the organic electroluminescent device and extend its lifespan, the organic layer is often multilayered, and the organic substances in each layer are different. 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 electroluminescent device, the anode injects holes into the organic layer, and the cathode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, and when the excitons transition to the ground state, light is emitted, thereby realizing the light emission of the organic electroluminescent device. Since the organic electroluminescent device has characteristics such as self-emission, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and fast response, its future application potential is highly anticipated.

[0004] To improve the luminescence efficiency of organic electroluminescent devices, various systems of luminescent materials based on fluorescence and phosphorescence have been developed. Among these, organic electroluminescent devices using fluorescent materials are characterized by high reliability, but under electrical excitation, the branching ratio between the singlet and triplet excited states of excitons is 1:3, so the internal electroluminescence quantum efficiency is limited to within 25%. On the other hand, organic electroluminescent devices using phosphorescent materials can achieve an internal electroluminescence quantum efficiency of almost 100%. However, phosphorescent materials usually use metal complexes containing iridium or platinum, and these raw materials are expensive and their synthesis is complex. Furthermore, phosphorescent organic electroluminescent devices exhibit a roll-off effect, meaning that the luminescence efficiency decreases sharply with increasing current and brightness, thus limiting their application at high brightness levels. [Overview of the project] [Problems that the invention aims to solve]

[0005] Current light-emitting materials typically consist of various combinations of organic compounds, such as composite excited-state materials and thermally activated delayed fluorescence (TADF) materials, and attempts have been made to achieve high efficiencies comparable to phosphorescent organic electroluminescent devices by utilizing inverse internal conversion. However, there have been limitations in both efficiency and lifetime of improving the performance of conventional TADF-containing organic compounds, making it difficult to improve the luminescence efficiency and lifetime of organic electroluminescent devices using TADF-containing organic compounds.

[0006] Therefore, organic compounds for organic light-emitting devices are needed to solve the above technical challenges.

[0007] This application provides organic compounds, mixtures, compositions, organic light-emitting devices, and display panels that can improve the luminescence efficiency and lifespan of organic light-emitting devices. [Means for solving the problem]

[0008] The embodiments of the present application provide an organic compound having a structure represented by general formula (1) or general formula (2). TIFF2026082747000002.tif38162 (where Ar1 and Ar2 are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 60 carbon atoms, Ar3 and Ar4 are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms. R1 and R2 are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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 ketone group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, and a carbon number Selected from aryloxycarbonyl groups with 7-20 carbon atoms, alkenyl groups with 2-20 carbon atoms, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, CF3, Cl, Br, F, substituted or unsubstituted aromatic groups with 6-30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5-30 ring atoms, substituted or unsubstituted aryloxy groups with 6-30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5-30 ring atoms. At least one of Ar1, Ar2, Ar3, Ar4, R1, and R2 has a linear or branched silicon group or a deuterated phenyl group having 1 to 20 carbon atoms. n1 is selected from 0, 1, 2, or 3. n2 is selected from 0, 1, 2, 3, or 4.

[0009] In one embodiment of the present application, R1 and R2 are selected from silyl groups, and at least one of Ar1, Ar2, Ar3, Ar4, R1, and R2 has a silyl group or a deuterated phenyl group.

[0010] In one embodiment of the present application, R1 and R2 are selected from a trimethylsilyl group and a triphenylsilyl group, and at least one of Ar1, Ar2, Ar3, Ar4, R1, and R2 has a trimethylsilyl group, a triphenylsilyl group, or a deuterated phenyl group.

[0011] In one embodiment of the present invention, Ar1 is a group represented by any one selected from formulas (X-1) to (X-4), Ar2 is a group represented by any one selected from formulas (A-1) to (A-4), Ar3 and Ar4 are groups represented by any one of the formulas (B-1) to (B-5) selected from each of these formulas. TIFF2026082747000003.tif23170 TIFF2026082747000004.tif25162 TIFF2026082747000005.tif35166(where --- in equations (X-1) to (X-4) represents a link that connects to general equation (1) or general equation (2), The linking site of Ar2 is located on a carbon atom in any of the rings, the linking site of Ar3 is located on a carbon atom in any of the rings, and the condensation site of Ar4 is located on two carbon atoms in the ottl position within the same ring. X is selected from O, S, N-CH3, N-Ph, or C(CH3)2. R0 and L are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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 trimethylsilyl group, a triphenylsilyl group, a ketone group having 1 to 20 carbon atoms, or an alkoxy group having 2 to 20 carbon atoms. Selected from xycarbonyl groups, aryloxycarbonyl groups with 7 to 20 carbon atoms, alkenyl groups with 2 to 20 carbon atoms, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, CF3, Cl, Br, F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5 to 30 ring atoms. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. (a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.)

[0012] In one embodiment of the present invention, if Ar1 is selected from the group represented by formula (X-2), then Ar4 is a group represented by any one of the groups selected from formulas (B-2) to (B-5). In one embodiment of the present application, Ar2 is It is at least one selected from TIFF2026082747000006.tif1477. (Here, L and a in these bases have the same definitions as L and a in equations (A-1) to (A-4).)

[0013] In one embodiment of this application, If n1 is 2 or greater, two adjacent R1 atoms may or may not form a ring with the ring atoms connected to them. If n2 is 2 or greater, two adjacent R2 atoms may or may not form a ring with the ring atoms connected to them. If a is 2 or greater, two adjacent L atoms may or may not form a ring with the atoms connected to them.

[0014] In one embodiment of the present invention, the organic compound has a structure represented by any one of general formulas (2-1) to (2-31). TIFF2026082747000007.tif246160TIFF2026082747000008.tif81159 (Here, L, R3, and R4 in general formulas (2-1) to (2-31) are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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 trimethylsilyl group, a triphenylsilyl group, or a 1 to 20 carbon atom Selected from ton group, alkoxycarbonyl group having 2-20 carbon atoms, aryloxycarbonyl group having 7-20 carbon atoms, alkenyl group having 2-20 carbon atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF3, Cl, Br, F, substituted or unsubstituted aromatic group having 6-30 ring atoms, substituted or unsubstituted heteroaromatic group having 5-30 ring atoms, substituted or unsubstituted aryloxy group having 6-30 ring atoms, and substituted or unsubstituted heteroaryloxy group having 5-30 ring atoms. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. n3 is 0 or more and 5 or less, and when n3 is 2 or more, two adjacent R3s, together with the atoms connected thereto, form a ring with each other or do not form a ring. n4 is 0 or more and 5 or less, and when n4 is 2 or more, two adjacent R4s, together with the atoms connected thereto, form a ring with each other or do not form a ring.

[0015] In one embodiment of the present application, R1, R2, R3, R4, and L are selected from H, D, linear alkyl groups having 1 to 10 carbon atoms, branched alkyl groups having 3 to 10 carbon atoms, and cyclic alkyl groups having 3 to 10 carbon atoms.

[0016] In one embodiment of the present application, R1, R2, R3, R4, and L are selected from H, D, linear alkyl groups having 1 to 4 carbon atoms, and branched alkyl groups having 3 to 5 carbon atoms.

[0017] In one embodiment of the present application, the organic compound is a blue light-emitting material.

[0018] In one embodiment of the present application, the organic compound is selected from the following Compound 1 to Compound 168. TIFF202\ 608\ 2747\ 000009.tif227\ 161 TIFF202\ 608\ 2747\ 000010.tif243\ 160TIFF202\ 608\ 2747\ 000011.tif245\ 159TIFF202\ 608\ 2747\ 000012.tif227\ 158TIFF202\ 608\ 2747\ 000013.tif231\ 159TIFF202\ 608\ 2747\ 000014.tif196\ 152

[0019] According to the above object of the present application, an embodiment of the present application also provides a mixture, the mixture including the organic compound and at least one organic functional material, and the organic functional material being 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] To the purposes of the present application, the embodiments of the present application also provide compositions comprising the organic compound and at least one organic solvent, or compositions comprising the mixture and at least one organic solvent.

[0021] According to the above-mentioned objectives of this application, the embodiments of this application also include, First electrode and, A second electrode positioned opposite the aforementioned first electrode, The invention includes an organic functional layer located between the first electrode and the second electrode, The present invention provides an organic light-emitting device in which the material of the organic functional layer comprises one or more of the organic compounds, or the material of the organic functional layer comprises the mixture, or the material of the organic functional layer comprises the composition.

[0022] In one embodiment of the present application, the organic functional layer includes at least a light-emitting layer, the material of the light-emitting layer includes a host material and a guest material, the guest material includes one or more of the organic compounds.

[0023] In accordance with the above-mentioned objectives of the present application, embodiments of the present application also provide a display panel, the display panel including the organic light-emitting device. [Effects of the Invention]

[0024] In the embodiments of this invention, by adding an aromatic ring, a silicon group, and / or a deuterated phenyl group to an organic compound, the relative molecular mass of the organic compound can be effectively increased, the molecular structure of the organic compound can be enlarged, and the intermolecular gaps can be enlarged, thereby improving the overall solubility of the organic compound, facilitating the purification of the organic compound, improving the purity of the organic compound, and further improving the efficiency and extending the lifespan of organic light-emitting devices made from the organic compound. [Brief explanation of the drawing]

[0025] [Figure 1]This is the hydrogen nuclear magnetic resonance spectrum of the organic compound M165 provided in the embodiments of the present application. [Figure 2] This is the hydrogen nuclear magnetic resonance spectrum of the organic compound M166 provided in the embodiments of the present application. [Figure 3] This is the hydrogen nuclear magnetic resonance spectrum of the organic compound M167 provided in the embodiments of the present application. [Figure 4] This is a schematic diagram of the structure of an example of an organic light-emitting device provided in the embodiments of the present application. [Figure 5] This is a schematic diagram of the structure of another example of an organic light-emitting device provided in the embodiments of the present application. [Modes for carrying out the invention]

[0026] The present application will be described in further detail below with reference to the drawings provided in the embodiments thereof. It should be understood that the specific embodiments described herein are for interpretive purposes only and are not intended to limit the present application, and the order in which the embodiments are described below is not intended to limit the preferred order of the embodiments.

[0027] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as those generally understood by those skilled in the art in the field to which this general inventive concept belongs. Furthermore, terms as defined in commonly used dictionaries should be interpreted in a sense consistent with their meaning in the context of the relevant art and the content of this disclosure, and should not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0028] In this application, aromatic group, aromatic, and aromatic ring system have the same meaning and are interchangeable.

[0029] In this application, heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and are interchangeable.

[0030] In this application, "substitution" means that a hydrogen atom of the group to be substituted is replaced by a substituent.

[0031] In this application, if the same substituent appears multiple times, they may be independently selected from the same or different groups. If the general formula contains multiple R groups, R may be independently selected from the same or different groups.

[0032] In this application, “substituted or unsubstituted” means that the defined group may be substituted or unsubstituted. If the defined group is substituted, it should be understood that the defined group may be substituted with one or more substituents R. The R is selected from, but is not limited to, a deuterium atom, a cyano group, an isocyanone group, a nitro group, or a halogen (e.g., F, Cl, Br, or I), an alkyl group containing 1 to 20 carbon atoms, a heterocyclyl group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, -NR'R'', a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, or a trifluoromethyl group, and the above groups may be further substituted with substituents permitted in the art. In -NR'R'', R' and R'' are independently selected from, but are not limited to, H, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen (e.g., F, Cl, Br, or I), an alkyl group containing 1 to 10 carbon atoms, a heterocyclyl group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, and a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from, but is not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen (e.g., F, Cl, Br, or I), an alkyl group containing 1 to 10 carbon atoms, a heterocyclyl group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, or a trifluoromethyl group, and the above groups may be further substituted with substituents permitted in the art.

[0033] In this application, "ring atom number" refers to the number of atoms that constitute the ring itself in a compound with a structure in which atoms are bonded to form a ring (e.g., monocyclic compounds, fused cyclic compounds, bridged compounds, carbocyclic compounds, heterocyclic compounds). If the ring is substituted with substituents, the atoms included in the substituents are not included in the ring-forming atoms. Unless otherwise specified, the same applies to the "ring atom number" described below. For example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thienyl group is 5.

[0034] In this application, "aryl group" or "aromatic group" refers to an aromatic hydrocarbon group in which all ring atoms are carbon atoms, derived by removing one hydrogen atom from an aromatic ring compound, and can be a monocyclic aryl group, a fused aryl group, or a polycyclic aryl group. In the case of a polycyclic ring, at least one is an aromatic ring system. For example, “substituted or unsubstituted aryl groups having 6 to 40 ring atoms” refers to aryl groups containing 6 to 40 ring atoms, preferably substituted or unsubstituted aryl groups having 6 to 30 ring atoms, more preferably substituted or unsubstituted aryl groups having 6 to 18 ring atoms, and particularly preferably substituted or unsubstituted aryl groups having 6 to 14 ring atoms. The aryl groups may be further optionally substituted, and suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenantrenyl, fluoranthenyl, triphenylene, pyrenyl, perilenyl, tetracenyl, fluorenyl, acenaphthenyl, and their derivatives. It is understood that multiple aryl groups may be interrupted by short non-aromatic units (for example, based on the total number of atoms in the system, the non-aromatic units preferably contain less than 10% non-H atoms such as C, N, or O atoms). Specifically, 9,9-diarylfluorene, triarylamines, and diaryl ethers should also be included in the definition of an aryl group.

[0035] In this application, "heteroaryl group" or "heteroaromatic group" refers to an aryl group in which at least one carbon atom on the ring skeleton is substituted with a non-carbon atom, which may be an N atom, an O atom, an S atom, etc. That is, the ring atoms of the heteroaryl group include one or more non-carbon atoms selected from N atoms, O atoms, and S atoms. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. Furthermore, the heteroaryl group may be further optionally substituted, suitable examples of which include a thienyl group, a furanyl group, Pyrrolyl group, imidazolyl group, diazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidinyl group, triazinyl group, acridinyl group, pyridadinyl group, pyrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyradinyl group, benzothiophenyl group, benzofuranyl group, indolyl group, pyrroloimidazolyl group, pyrrolopyrrolyl group, thienopyrrolyl group, thienothiphenyl group, furanopyrrolyl group This includes, but is not limited to, the following groups: furanofuranyl group, thienofuranyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzimidazolyl group, synnolinyl group, phenantridinyl group, perimidinyl group, quinazolinyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, and their derivatives.

[0036] In this application, “alkyl group” may mean a fully saturated linear, branched, and / or cyclic aliphatic hydrocarbon group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. This term is not used in phrases such as “C 1~9An alkyl group refers to an alkyl group containing 1 to 9 carbon atoms, which may independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group, or C9 alkyl group each time it appears. Non-limiting examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, isobutyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group, n-hexyl group, 1-methylpentyl group Xyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2- This includes octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, 2-ethyleicosyl group, 2-butyleicosyl group, 2-hexyleicosyl group, 2-octyleicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, n-triacontyl group, and others.

[0037] In this application, the abbreviations for substituents correspond to n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meth, p-para, Me-methyl group, Et-ethyl group, Pr-propyl group, Bu-butyl group, Amn-pentyl group, Hx-hexyl group, Cy-cyclohexyl group, and Ph-phenyl group.

[0038] In this application, "amine group" refers to an amine derivative having the structural characteristics of formula -N(X)2, where each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclyl group, 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.

[0039] In this application, the terms "cycloalkyl group" or "cyclic alkyl group" refer to a monovalent group having one or more saturated rings in which all ring members are carbon, and the term "alkyl group" has the same meaning as above.

[0040] In this application, the terms “heterocyclyl group,” “heterocyclic,” or “heterocyclic” refer to a fully saturated or partially unsaturated but non-aromatic cyclic group having one or more heteroatoms of oxygen, sulfur, silicon, or nitrogen within the ring, wherein the nitrogen and sulfur heteroatoms may be optionally oxidized, and the nitrogen heteroatom may be optionally quaternized. The heterocyclyl group may be linked to any atom or carbon atom of the ring or cyclic system, and may be unsubstituted or substituted with one or more parts of the aryl group as described above.

[0041] In this application, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, and an amino group refers to -NH2. finger The formyl group refers to -C(=O)H, the haloformyl group refers to -C(=O)Z (where Z represents a halogen (e.g., F, Cl, Br, or I)), the carbamoyl group refers to -C(=O)NH2, the isocyanate group refers to -NCO, and the isothiocyanate group refers to -NCS.

[0042] In this application, the term "alkoxy group" refers to a group whose structure is "-O-alkyl," that is, a group in which the alkyl group defined above is linked to another group via an oxygen atom. Examples of appropriate phrases containing this term include, but are not limited to, the methoxy group (-O-CH3 or -OMe), the ethoxy group (-O-CH2CH3 or -OEt), and the tert-butoxy group (-OC(CH3)3 or -OtBu).

[0043] In this application, the asterisk (*) connected to a single bond indicates a linkage site or a condensation site.

[0044] In this application, if no connecting portion is specified in the base, it means that any connectable portion of the base can be used as a connecting portion.

[0045] In this application, if no condensation sites are specified in the base, it means that any condensation site in the base can be used as a condensation site, preferably two or more sites in the ortho position of the base are the condensation sites.

[0046] In this application, when a group contains multiple substituents with the same sign, each substituent may be the same as or different from one another, for example. In TIFF2026082747000015.tif4239, the six Rs in the benzene ring may be the same or different from one another.

[0047] In this application, the single bond connected to the substituent penetrates the corresponding ring, meaning that the substituent may be connected at any position on the ring, for example, In TIFF2026082747000016.tif3139, R is connected to any of the substituted sites of the benzene ring, for example, TIFF2026082747000017.tif3770 is, TIFF2026082747000018.tif4258 It may form a fused ring with any position on the benzene ring of TIFF2026082747000019.tif4039.

[0048] The cyclic alkyl groups or cycloalkyl groups described in this application have the same meaning and are interchangeable.

[0049] In this application, "adjacent groups" means that there are no substitutable sites between the two substituents.

[0050] In this application, "two adjacent R1s, two adjacent R3s, or two adjacent R5s form a ring with each other" means that two adjacent R1s, two adjacent R3s, or two adjacent R5s are linked to each other to form a ring system, and the ring system may be selected from an aliphatic hydrocarbon ring, an aliphatic heterocycle, an aromatic hydrocarbon ring, or an aromatic heterocycle. Preferably, TIFF2026082747000020.tif3481 or TIFF2026082747000021.tif3839 may be formed.

[0051] The embodiments of the present application provide an organic compound having a structure represented by general formula (1) or general formula (2). TIFF2026082747000022.tif38162 (where Ar1 and Ar2 are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 60 carbon atoms, Ar3 and Ar4 are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms. R1 and R2 are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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 ketone group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, and a C7 group. Selected from ~20 aryloxycarbonyl groups, C2-C20 alkenyl groups, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, CF3, Cl, Br, F, substituted or unsubstituted aromatic groups with 6-30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5-30 ring atoms, substituted or unsubstituted aryloxy groups with 6-30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5-30 ring atoms. At least one of Ar1, Ar2, Ar3, Ar4, R1, and R2 has a linear or branched silicon group or a deuterated phenyl group having 1 to 20 carbon atoms. n1 is selected from 0, 1, 2, or 3. n2 is selected from 0, 1, 2, 3, or 4.

[0052] The embodiments of this application, in the process of implementation and application, effectively increase the relative molecular mass of an organic compound by adding an aromatic ring, a silicon group, and / or a deuterated phenyl group to the organic compound, thereby enlarging the molecular structure and increasing the intermolecular gaps. This improves the overall solubility of the organic compound, facilitates the purification of the organic compound, thereby improving the purity of the organic compound, and further improves the efficiency and lifespan of organic light-emitting devices made from the organic compound. In some embodiments, R1 and R2 are selected from silyl groups, and at least one of Ar1, Ar2, Ar3, Ar4, R1, and R2 has a silyl group or a deuterated phenyl group. In some embodiments, R1 and R2 are selected from a trimethylsilyl group and a triphenylsilyl group, and at least one of Ar1, Ar2, Ar3, Ar4, R1, and R2 has a trimethylsilyl group, a triphenylsilyl group, or a deuterated phenyl group.

[0053] In some embodiments, Ar1 is a group represented by any one selected from formulas (X-1) to (X-4), Ar2 is a group represented by any one selected from formulas (A-1) to (A-4), Ar3 and Ar4 are groups represented by any one of the formulas (B-1) to (B-5) selected from each of these formulas. TIFF2026082747000023.tif23170TIFF2026082747000024.tif25162TIFF2026082747000025.tif35166 (In equations (X-1) to (X-4), --- represents a link that connects to general equation (1) or general equation (2), The linking sites for Ar2 are located on carbon atoms in any of the rings, the linking sites for Ar3 are located on carbon atoms in any of the rings, and the condensation sites for Ar4 are located on two carbon atoms in the ottl position within the same ring. X is selected from O, S, N-CH3, N-Ph, or C(CH3)2. R0 and L are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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 trimethylsilyl group, a triphenylsilyl group, a ketone group having 1 to 20 carbon atoms, or an alkoxy group having 2 to 20 carbon atoms. Selected from xycarbonyl groups, aryloxycarbonyl groups with 7 to 20 carbon atoms, alkenyl groups with 2 to 20 carbon atoms, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, CF3, Cl, Br, F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5 to 30 ring atoms. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. (a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.)

[0054] In equations (B-1) to (B-5) above, each time R0 appears, the same or a different group may be selected, and the selection of these groups does not affect each other. In equations (A-1) to (A-4), each time L appears, the same or a different group may be selected, and the selection of these groups does not affect each other. Similarly, each time R1 appears, the same or a different group may be selected, and the selection of these groups does not affect each other. Each time R2 appears, the same or a different group may be selected, and the selection of these groups does not affect each other.

[0055] In some embodiments, at least one of Ar1, Ar2, Ar3, Ar4, R0, R1, R2, and L has a silicon group such as a trimethylsilyl group or a deuterated phenyl group, where Ar2 includes L, and if L is selected as D or a deuterated phenyl group, Ar2 may also include a deuterated phenyl group; similarly, Ar3 and Ar4 include R0, and if R0 is selected as D or a deuterated phenyl group, Ar3 and Ar4 may also include deuterated phenyl groups.

[0056] In some embodiments, at least one of Ar1, Ar2, Ar3, Ar4, R0, R1, R2, and L has a triphenylsilyl group, which effectively enlarges the molecular structure of the organic compound and increases the intermolecular gaps, thereby improving the solubility of the organic compound, facilitating the purification of the compound, improving the purity of the organic compound, and further improving the efficiency and lifespan of organic light-emitting devices made from the organic compound.

[0057] In some embodiments, when Ar1 is selected from the group represented by formula (X-2), Ar4 is a group represented by any one of the groups selected from formulas (B-2) to (B-5).

[0058] In some embodiments, when n1 is 2 or more, two adjacent R1 atoms may or may not form a ring with the ring atoms connected to them; when n2 is 2 or more, two adjacent R2 atoms may or may not form a ring with the ring atoms connected to them; and when a is 2 or more, two adjacent L atoms may or may not form a ring with the atoms connected to them.

[0059] In some embodiments, two adjacent R1 atoms form a ring with each other, and further, two adjacent R1 atoms form a ring with each other to form a six-membered aromatic ring or an aliphatic ring, and even further, two adjacent R1 atoms form a ring with each other. The file TIFF2026082747000026.tif3839 is formed, where * indicates a connection point.

[0060] In some embodiments, two adjacent R2s form a ring with each other, and further, two adjacent R2s form a ring with each other to form a six-membered aromatic ring or an aliphatic ring, and even further, two adjacent R2s form a ring with each other. The file TIFF2026082747000027.tif3839 is formed, where * indicates a connection point.

[0061] In some embodiments, two adjacent Ls form a ring with each other, and further, two adjacent Ls form a ring with each other to form a six-membered aromatic ring or an aliphatic ring, and even further, two adjacent Ls form a ring with each other. The file TIFF2026082747000028.tif3839 is formed, where * indicates a connection point.

[0062] In some embodiments, the organic compound has a structure represented by any one of the general formulas (2-1) to (2-31). TIFF2026082747000029.tif165161TIFF2026082747000030.tif162162 (where L, R3, and R4 are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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 branched alkoxy group having 3 to 20 carbon atoms, a cyclic 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 trimethylsilyl group, Selected from: riphenylsilyl group, ketone group having 1 to 20 carbon atoms, alkoxycarbonyl group having 2 to 20 carbon atoms, aryloxycarbonyl group having 7 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF3, Cl, Br, F, substituted or unsubstituted aromatic group having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. n3 is between 0 and 5, and if n3 is 2 or greater, two adjacent R3 atoms may or may not form a ring with the atoms connected to them. n4 is between 0 and 5, and if n4 is 2 or greater, two adjacent R4 atoms may or may not form a ring with the atoms connected to them.

[0063] Note that each time R3 appears in the general formulas (2-1) to (2-31) above, the same or a different group may be selected, and these selections do not affect each other. Similarly, each time R4 appears, the same or a different group may be selected, and these selections do not affect each other.

[0064] In some embodiments, two adjacent R3s form a ring with each other, and further, two adjacent R3s form a ring with each other to form a six-membered aromatic ring or an aliphatic ring, and even further, two adjacent R3s form a ring with each other. The file TIFF2026082747000031.tif3839 is formed, where * indicates a connection point.

[0065] In some embodiments, two adjacent R4s form a ring with each other, and further, two adjacent R4s form a ring with each other to form a six-membered aromatic ring or an aliphatic ring, and even further, two adjacent R4s form a ring with each other. The file TIFF2026082747000032.tif3839 is formed, where * indicates a connection point.

[0066] In some embodiments, R1, R2, R3, R4, and L are selected from H, D, linear alkyl groups having 1 to 10 carbon atoms, branched alkyl groups having 3 to 10 carbon atoms, and cyclic alkyl groups having 3 to 10 carbon atoms.

[0067] In some embodiments, R1, R2, R3, R4, and L are selected from H, D, linear alkyl groups having 1 to 4 carbon atoms, and branched alkyl groups having 3 to 5 carbon atoms.

[0068] As described above, the embodiments of the present application are advantageous in improving the solubility of the organic compound in processes such as inkjet printing by introducing an alkyl group into the organic compound, thereby improving the quality of organic light-emitting devices using the organic compound.

[0069] In some embodiments, at least one of Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, and L has a silicon group such as a trimethylsilyl group or a triphenylsilyl group, where Ar2 includes L, and if L is selected as D or a deuterated phenyl group, Ar2 may also include a deuterated phenyl group. Similarly, Ar3 and Ar4 include R3 and R4, respectively, and if R3 and R4 are selected as D or a deuterated phenyl group, Ar3 and Ar4 may also include deuterated phenyl groups.

[0070] In some embodiments, when Ar2 is selected from the group represented by formula (A-2), then formula (A-2) is: At least one selected from TIFF2026082747000033.tif30166, where L and a in these groups have the same definitions as L and a in formulas (A-1) to (A-4). Here, organic compounds having oxygen, sulfur, and nitrogen are advantageous in improving the luminescence efficiency and extending the lifespan of organic light-emitting devices using such organic compounds because they have superior hole transport properties.

[0071] In some embodiments, the organic compound is a blue light-emitting material.

[0072] In some embodiments, the organic compound is at least one selected from the following compounds 1 to 168. TIFF2026082747000034.tif227161 TIFF2026082747000035.tif243160TIFF2026082747000036.tif245159TIFF20260827470 00037.tif227158TIFF2026082747000038.tif231159TIFF2026082747000039.tif196152

[0073] In the embodiments of this application, by adding a biphenyl ring, an aromatic ring, a silicon group, and / or a deuterated phenyl group to an organic compound, the overall solubility of the organic compound molecule is improved, the purification of the compound is facilitated, the purity of the compound is increased, and furthermore, the efficiency of the fabricated organic light-emitting device is improved, extending its lifespan.

[0074] Furthermore, the embodiments of this application also provide a process for producing the organic compounds described in the embodiments described above, and further, Examples 1 to 35 are provided to illustrate in detail the process for producing the organic compounds provided in the embodiments of this application. Example 1

[0075] The synthesis route for organic compound M1 is as follows: TIFF2026082747000040.tif67167 Synthesis of Intermediates 1-3: Compound 1-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After the reaction was complete, the reaction mixture was cooled, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The resulting organic phase was subjected to column chromatography to obtain intermediate 1-3 in molar amount 8.21 mmol, with a yield of 82.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 1-3 solid sample at atmospheric pressure: MS(ASAP) = 337. Synthesis of intermediates 1-5: Intermediate 1-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 1-5 in molar amount 7.28 mmol, with a yield of 72.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 1-5 solid samples at atmospheric pressure: MS(ASAP) = 481. Synthesis of intermediates 1-7: Intermediate 1-5 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 1-7 in molar amount 6.51 mmol, with a yield of 65.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 1-7 solid sample at atmospheric pressure: MS(ASAP) = 582. Synthesis of intermediates 1-9: Intermediate 1-7 (10 mmol) and compound 1-8 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 1-9 in molar volume of 6.33 mmol and yield of 63.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 1-9 solid sample at atmospheric pressure: MS(ASAP) = 796. Synthesis of intermediates 1-11: Intermediate 1-9 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was recrystallized by column chromatography to obtain intermediate 1-11 in molar volume of 7.76 mmol and yield of 77.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 1-11 solid sample at atmospheric pressure: MS(ASAP) = 962. Synthesis of intermediates 1-13: Intermediate 1-11 (10 mmol) and compound 1-12 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 1-13 in molar volume of 5.68 mmol with a yield of 56.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 1-13 solid sample at atmospheric pressure: MS(ASAP) = 1154. Synthesis of organic compound M1: 10 mmol of intermediate 1-13 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was then removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (BBr3, 21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine (EtN(i-Pr)2) was added, and the mixture was heated to room temperature and stirred. The temperature was further raised to 120°C and stirred for 3 hours, and the reaction mixture was cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was added. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified using a high-speed silica gel column to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M1, in 33.1% yield. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M1 at atmospheric pressure: MS(ASAP) = 1128. Example 2

[0076] The synthesis route for organic compound M12 is as follows: JPEG2026082747000041.jpg60169 Synthesis of Intermediate 2-1: Compounds 1-6 (10 mmol) and 1-8 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 2-1 in molar volume of 8.33 mmol and yield of 83.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 2-1 solid sample at atmospheric pressure: MS(ASAP) = 351. Synthesis of intermediate 2-2: Intermediate 2-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 2-2 in molar amount 7.39 mmol and yield 73.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 2-2 solid sample at atmospheric pressure: MS(ASAP) = 539. Synthesis of intermediates 2-3: Intermediate 2-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 2-3 in molar amount 6.72 mmol, with a yield of 67.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 2-3 solid sample at atmospheric pressure: MS(ASAP) = 683. Synthesis of intermediates 2-4: Intermediate 2-3 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 2-4 in molar amount 6.71 mmol, with a yield of 67.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 2-4 solid sample at atmospheric pressure: MS(ASAP) = 796. Synthesis of intermediates 2-5: Intermediate 2-4 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 2-5 in molar volume of 7.35 mmol and yield of 73.5%. Probe-mass spectrometry (ASAP-MS) results for intermediate 2-5 solid sample at atmospheric pressure: MS(ASAP) = 962. Synthesis of intermediates 2-6: Intermediate 2-5 (10 mmol) and compound 1-12 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 2-6 in molar volume of 5.12 mmol and yield of 51.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 2-6 solid sample at atmospheric pressure: MS(ASAP) = 1154. Synthesis of organic compound M12: 10 mmol of intermediate 2-6 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M12, in a yield of 43.7%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M12: MS(ASAP) = 1128. Example 3

[0077] The synthesis route for organic compound M15 is as follows: JPEG2026082747000042.jpg31169 Synthesis of Intermediate 3-2: Intermediate 2-3 (10 mmol), compound 3-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 3-2 in molar amount 7.89 mmol and yield 78.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 3-2 solid sample at atmospheric pressure: MS(ASAP) = 928. Synthesis of intermediate 3-3: Intermediate 3-2 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 3-3 in molar volume 7.71 mmol and yield 77.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 3-3 solid sample at atmospheric pressure: MS(ASAP) = 10⁹⁴. Synthesis of intermediates 3-4: Intermediate 3-3 (10 mmol) and compound 1-12 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 3-4 in molar volume of 5.41 mmol and yield of 54.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 3-4 solid sample at atmospheric pressure: MS(ASAP) = 1154. Synthesis of organic compound M15: 10 mmol of intermediate 3-4 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M15, in a yield of 41.3%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M15: MS(ASAP) = 1260. Example 4

[0078] The synthesis route for organic compound M16 is as follows: JPEG2026082747000043.jpg71169 Synthesis of Intermediate 4-1: Compound 3-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 4-1 in molar amount 8.73 mmol and yield 87.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 4-1 solid sample at atmospheric pressure: MS(ASAP) = 469. Synthesis of intermediate 4-2: Intermediate 4-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 4-2 in molar amount 7.86 mmol and yield 78.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 4-2 at atmospheric pressure solid sample: MS(ASAP) = 613. Synthesis of intermediate 4-3: Intermediate 4-2 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 4-3 in molar amount 6.82 mmol, with a yield of 68.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 4-3 solid sample at atmospheric pressure: MS(ASAP) = 714. Synthesis of intermediate 4-4: Intermediate 4-3 (10 mmol) and compound 1-8 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 4-4 in molar volume of 5.63 mmol and yield of 56.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 4-4 solid sample at atmospheric pressure: MS(ASAP) = 928. Synthesis of intermediates 4-5: Intermediate 4-4 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 4-5 in molar volume 7.76 mmol and yield 77.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 4-5 solid sample at atmospheric pressure: MS(ASAP) = 10⁹⁴. Synthesis of intermediates 4-6: Intermediate 4-5 (10 mmol) and compound 1-12 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 4-6 in molar volume of 5.11 mmol and yield of 51.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 4-6 solid sample at atmospheric pressure: MS(ASAP) = 1286. Synthesis of organic compound M16: 10 mmol of intermediate 4-6 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M16, in a yield of 37.6%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M16: MS(ASAP) = 1260. Example 5

[0079] The synthesis route for organic compound M60 is as follows: JPEG2026082747000044.jpg42168 Synthesis of Intermediate 5-2: Intermediate 3-3 (10 mmol) and intermediate 5-1 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 5-2 in molar volume of 5.28 mmol and yield of 52.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 5-2 solid sample at atmospheric pressure: MS(ASAP) = 1190. Synthesis of organic compound M60: 10 mmol of intermediate 5-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M60, in a yield of 32.7%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M60 at atmospheric pressure: MS(ASAP) = 1164. Example 6

[0080] The synthesis route for organic compound M64 is as follows: JPEG2026082747000045.jpg39167 Synthesis of Intermediate 6-2: Intermediate 4-5 (10 mmol) and intermediate 6-1 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 6-2 in molar volume of 5.93 mmol and yield of 59.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 6-2 as a solid sample at atmospheric pressure: MS(ASAP) = 1190. Synthesis of organic compound M64: 10 mmol of intermediate 6-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M64, in a yield of 32.9%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M64: MS(ASAP) = 1164. Example 7

[0081] The synthesis route for organic compound M68 is as follows: JPEG2026082747000046.jpg64169 Synthesis of intermediate 7-2: Compound 7-1 (10 mmol), Compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 7-2 in molar amount 8.33 mmol and yield 83.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 7-2 at atmospheric pressure solid sample: MS(ASAP) = 469. Synthesis of intermediate 7-3: Intermediate 7-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 7-3 in molar amount 7.21 mmol and yield 72.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 7-3 solid sample at atmospheric pressure: MS(ASAP) = 613. Synthesis of intermediate 7-4: Intermediate 7-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 7-4 in molar amount 6.52 mmol, with a yield of 65.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 7-4 solid sample at atmospheric pressure: MS(ASAP) = 714. Synthesis of intermediates 7-5: Intermediate 7-4 (10 mmol) and compound 1-8 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 7-5 in molar volume of 5.13 mmol and yield of 51.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 7-5 solid sample at atmospheric pressure: MS(ASAP) = 928. Synthesis of intermediates 7-6: Intermediate 7-5 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 7-6 in molar volume of 7.13 mmol and yield of 71.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 7-6 solid sample at atmospheric pressure: MS(ASAP) = 10⁹⁴. Synthesis of intermediates 7-8: Intermediate 7-6 (10 mmol) and compound 7-7 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 7-8 in molar volume of 5.56 mmol and yield of 55.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 7-8 solid sample at atmospheric pressure: MS(ASAP) = 1176. Synthesis of organic compound M68: 10 mmol of intermediate 7-8 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M68, in a yield of 32.3%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M68: MS(ASAP) = 1150. Example 8

[0082] The synthesis route for organic compound M72 is as follows: Synthesis of intermediate 8-1 in JPEG2026082747000047.jpg30169: Intermediate 2-3 (10 mmol), compound 7-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 8-1 in molar amount 7.21 mmol, with a yield of 72.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 8-1 solid sample at atmospheric pressure: MS(ASAP) = 928. Synthesis of intermediate 8-2: Intermediate 8-1 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 8-2 in molar amount 7.21 mmol, with a yield of 72.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 8-2 solid sample at atmospheric pressure: MS(ASAP) = 10⁹⁴. Synthesis of intermediate 8-4: Intermediate 8-2 (10 mmol) and compound 8-3 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 8-4 in molar volume of 5.22 mmol and yield of 52.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 8-4 solid sample at atmospheric pressure: MS(ASAP) = 1176. Synthesis of organic compound M72: 10 mmol of intermediate 8-4 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M72, in a yield of 25.3%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M72 at atmospheric pressure: MS(ASAP) = 1150. Example 9

[0083] The synthesis route for organic compound M89 is as follows: JPEG2026082747000048.jpg63168 Synthesis of Intermediate 9-1: Compounds 1-6 (10 mmol) and 1-8 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 9-1 in molar amount 8.93 mmol and yield 89.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-1 solid sample at atmospheric pressure: MS(ASAP) = 351. Synthesis of intermediate 9-3: Intermediate 9-1 (10 mmol), compound 9-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 9-3 in molar amount 8.53 mmol and yield 85.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-3 solid sample at atmospheric pressure: MS(ASAP) = 573. Synthesis of intermediate 9-4: Intermediate 9-3 (10 mmol), compound 3-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 9-4 in molar amount 6.27 mmol and yield 62.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-4 solid sample at atmospheric pressure: MS(ASAP) = 774. Synthesis of intermediate 9-5: Intermediate 9-4 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 9-5 in molar amount 6.71 mmol, with a yield of 67.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-5 solid sample at atmospheric pressure: MS(ASAP) = 962. Synthesis of intermediates 9-6: Intermediate 9-5 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 9-6 in molar amount 5.96 mmol, with a yield of 59.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-6 solid sample at atmospheric pressure: MS(ASAP) = 1128. Synthesis of intermediates 9-8: Intermediate 9-6 (10 mmol) and compound 9-7 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 9-8 in molar volume of 7.93 mmol and yield of 79.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-8 solid sample at atmospheric pressure: MS(ASAP) = 1276. Synthesis of intermediates 9-10: Intermediate 9-8 (10 mmol), compound 9-9 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 9-10 in molar volume of 5.03 mmol and yield of 50.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 9-10 solid sample at atmospheric pressure: MS(ASAP) = 1409. Synthesis of organic compound M89: 10 mmol of intermediate 9-10 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M89, in a yield of 29.1%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M89 at atmospheric pressure: MS(ASAP) = 1383. Example 10

[0084] The synthesis route for organic compound M90 is as follows: JPEG2026082747000049.jpg74170 Synthesis of intermediate 10-1: Intermediate 9-3 (10 mmol), intermediate 1-3 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 10-1 in molar amount 7.89 mmol, with a yield of 78.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 10-1 solid sample at atmospheric pressure: MS(ASAP) = 830. Synthesis of intermediate 10-2: Intermediate 10-1 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 10-2 in molar amount 7.13 mmol, with a yield of 71.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 10-2 solid sample at atmospheric pressure: MS(ASAP) = 996. Synthesis of intermediate 10-4: Intermediate 10-2 (10 mmol) and compound 10-3 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 10-4 in molar volume of 5.71 mmol and yield of 57.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 10-4 solid sample at atmospheric pressure: MS(ASAP) = 1141. Synthesis of intermediate 10-5: Intermediate 10-4 (10 mmol), intermediate 9-9 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 10-5 in molar volume of 5.63 mmol and yield of 56.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 10-5 solid sample at atmospheric pressure: MS(ASAP) = 1274. Synthesis of organic compound M90: 10 mmol of intermediate 10-5 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask and cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction mixture was cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the temperature was raised to room temperature and stirred, then further raised to 120°C and stirred for 3 hours, and the reaction mixture was cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined. The solvent was removed by rotary evaporation to obtain the crude product, which was purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M90, in a yield of 36.1%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M90 at atmospheric pressure: MS(ASAP) = 1248. Example 11

[0085] The synthesis route for organic compound M99 is as follows: JPEG2026082747000050.jpg64169 Synthesis of Intermediate 11-1: Intermediate 9-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-sodium butoxide (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 11-1 in molar amount 8.43 mmol and yield 84.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 11-1 solid sample at atmospheric pressure: MS(ASAP) = 539. Synthesis of intermediate 11-3: Intermediate 11-1 (10 mmol), compound 11-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-sodium butoxide (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 11-3 in molar amount 6.87 mmol and yield 68.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 11-3 solid sample at atmospheric pressure: MS(ASAP) = 759. Synthesis of intermediates 11-5: Intermediate 11-3 (10 mmol), compound 11-4 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 11-5 in molar amount 7.89 mmol and yield 78.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 11-5 solid sample at atmospheric pressure: MS(ASAP) = 906. Synthesis of intermediates 11-6: Intermediate 11-5 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 11-6 in molar amount 7.91 mmol, with a yield of 79.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 11-6 solid sample at atmospheric pressure: MS(ASAP) = 10⁹⁴. Synthesis of intermediates 11-8: Intermediate 11-6 (10 mmol) and compound 11-7 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 11-8 in molar volume of 7.93 mmol and yield of 79.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 11-8 solid sample at atmospheric pressure: MS(ASAP) = 1226. Synthesis of organic compound M99: 10 mmol of intermediate 11-8 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M99, in a yield of 43.2%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M99 at atmospheric pressure: MS(ASAP) = 1200. Example 12

[0086] The synthesis route for organic compound M116 is as follows: JPEG2026082747000051.jpg76168 Synthesis of Intermediate 12-2: Compounds 1-6 (10 mmol) and 12-1 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 12-2 in molar volume of 8.73 mmol and yield of 87.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-2 as a solid sample at atmospheric pressure: MS(ASAP) = 427. Synthesis of intermediate 12-3: Compound 12-2 (10 mmol), Compound 1-10 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 12-3 in molar volume 8.84 mmol and yield 88.4%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-3 solid sample at atmospheric pressure: MS(ASAP) = 593. Synthesis of intermediate 12-4: Intermediate 12-3 (10 mmol), compound 1-12 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 12-4 in molar amount 6.87 mmol and yield 68.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-4 solid sample at atmospheric pressure: MS(ASAP) = 785. Synthesis of intermediates 12-5: Intermediate 12-4 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 12-5 in molar amount 7.31 mmol, with a yield of 73.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-5 solid sample at atmospheric pressure: MS(ASAP) = 929. Synthesis of intermediates 12-7: Intermediate 12-5 (10 mmol), compound 12-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 12-7 in molar amount 6.16 mmol, with a yield of 61.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-7 (at atmospheric pressure solid sample): MS(ASAP) = 1110. Synthesis of intermediates 12-8: Intermediate 12-7 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 12-8 in molar volume 7.33 mmol and yield 73.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-8 solid sample at atmospheric pressure: MS(ASAP) = 1298. Synthesis of intermediates 12-10: Intermediate 12-8 (10 mmol) and compound 12-9 (20 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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid. The organic phase was recrystallized by column chromatography to obtain intermediate 12-10 in molar volume of 5.73 mmol and yield of 57.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 12-10 solid sample at atmospheric pressure: MS(ASAP) = 1392. Synthesis of organic compound M116: 10 mmol of intermediate 12-10 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M116, in a yield of 38.3%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M116 at atmospheric pressure: MS(ASAP) = 1366. Example 13

[0087] The synthesis route for organic compound M120 is as follows: JPEG2026082747000052.jpg34164 Synthesis of Intermediate 13-1: Intermediate 12-4 (10 mmol), compound 9-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 13-1 in molar amount 7.88 mmol, with a yield of 78.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 13-1 solid sample at atmospheric pressure: MS(ASAP) = 963. Synthesis of intermediate 13-3: Intermediate 13-1 (10 mmol), compound 13-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 13-3 in molar amount 6.96 mmol and yield 69.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 13-3 solid sample at atmospheric pressure: MS(ASAP) = 10⁹⁶. Synthesis of intermediate 13-4: Intermediate 13-3 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 13-4 in molar volume 7.71 mmol and yield 77.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 13-4 solid sample at atmospheric pressure: MS(ASAP) = 1284. Synthesis of intermediate 13-5: Intermediate 13-4 (10 mmol) and compound 12-9 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was then extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 13-5 in molar volume of 5.81 mmol and yield of 58.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 13-5 solid sample at atmospheric pressure: MS(ASAP) = 1331. Synthesis of organic compound M120: 10 mmol of intermediate 13-5 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M120, in a yield of 33.4%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M120: MS(ASAP) = 1305. Example 14

[0088] The synthesis route for organic compound M145 is as follows: JPEG2026082747000053.jpg30169 Synthesis of Intermediate 14-2: Compound 14-1 (10 mmol) and Compound 12-1 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 14-2 in molar volume of 8.12 mmol and yield of 81.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 14-2 as a solid sample at atmospheric pressure: MS(ASAP) = 375. Synthesis of intermediate 14-3: Intermediate 14-2 (10 mmol), compound 12-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 14-3 in molar amount 8.54 mmol and yield 85.4%. Probe-mass spectrometry (ASAP-MS) results for intermediate 14-3 solid sample at atmospheric pressure: MS(ASAP) = 709. Synthesis of intermediate 14-4: Intermediate 14-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 14-4 in molar amount 6.57 mmol and yield 65.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 14-4 solid sample at atmospheric pressure: MS(ASAP) = 853. Synthesis of intermediates 14-5: Intermediate 14-4 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 14-5 in molar amount 7.81 mmol, with a yield of 78.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 14-5 solid sample at atmospheric pressure: MS(ASAP) = 966. Synthesis of intermediates 14-7: Intermediate 14-5 (10 mmol), compound 14-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 14-7 in molar amount 5.86 mmol, with a yield of 58.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 14-7 (at atmospheric pressure solid sample): MS(ASAP) = 1174. Synthesis of organic compound M145: 10 mmol of intermediate 14-7 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M145, in a yield of 36.1%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M145 at atmospheric pressure: MS(ASAP) = 1148. Example 15

[0089] The synthesis route for organic compound M148 is as follows: JPEG2026082747000054.jpg36169 Synthesis of Intermediate 15-2: Compound 15-1 (10 mmol) and Compound 12-1 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 15-2 in molar volume of 8.42 mmol and yield of 84.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 15-2 as a solid sample at atmospheric pressure: MS(ASAP) = 559. Synthesis of intermediate 15-3: Intermediate 15-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 15-3 in molar amount 8.94 mmol and yield 89.4%. Probe-mass spectrometry (ASAP-MS) results for intermediate 15-3 solid sample at atmospheric pressure: MS(ASAP) = 703. Synthesis of intermediate 15-5: Intermediate 15-3 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 15-5 in molar amount 6.77 mmol and yield 67.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 15-5 solid sample at atmospheric pressure: MS(ASAP) = 794. Synthesis of intermediates 15-6: Intermediate 15-5 (10 mmol), compound 1-12 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 15-6 in molar amount 7.53 mmol and yield 75.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 15-6 solid sample at atmospheric pressure: MS(ASAP) = 986. Synthesis of intermediates 15-7: Intermediate 15-6 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 15-7 in molar amount 5.49 mmol, with a yield of 54.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 15-7 solid sample at atmospheric pressure: MS(ASAP) = 1174. Synthesis of organic compound M148: 10 mmol of intermediate 15-7 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M148, in a yield of 39.3%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M148: MS(ASAP) = 1148. Example 16

[0090] The synthesis route for organic compound M149 is as follows: JPEG2026082747000055.jpg36169 Synthesis of Intermediate 16-2: Intermediate 14-5 (10 mmol), compound 16-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 16-2 in molar amount 7.59 mmol and yield 75.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 16-2 solid sample at atmospheric pressure: MS(ASAP) = 1110. Synthesis of intermediate 16-4: Intermediate 16-2 (10 mmol) and compound 16-3 (20 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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 16-4 in molar volume of 8.83 mmol and yield of 88.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 16-4 solid sample at atmospheric pressure: MS(ASAP) = 1306. Synthesis of organic compound M149: 10 mmol of intermediate 16-4 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M149, in a yield of 43.2%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M149: MS(ASAP) = 1280. Example 17

[0091] The synthesis route for organic compound M150 is as follows: JPEG2026082747000056.jpg49169 Synthesis of Intermediate 17-2: Intermediate 14-5 (10 mmol), compound 17-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 17-2 in molar amount 7.93 mmol and yield 79.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 17-2 solid sample at atmospheric pressure: MS(ASAP) = 1174. Synthesis of organic compound M150: 10 mmol of intermediate 17-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M150, in a yield of 36.3%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M150: MS(ASAP) = 1148. Example 18

[0092] The synthesis route for organic compound M151 is as follows: JPEG2026082747000057.jpg32169 Synthesis of Intermediate 18-2: Intermediate 14-2 (10 mmol), compound 18-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 18-2 in molar amount 7.68 mmol and yield 76.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 18-2 solid sample at atmospheric pressure: MS(ASAP) = 507. Synthesis of intermediate 18-3: Intermediate 18-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 18-3 in molar amount 6.97 mmol and yield 69.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 18-3 solid sample at atmospheric pressure: MS(ASAP) = 651. Synthesis of intermediate 18-4: Intermediate 18-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 18-4 in molar amount 7.42 mmol, with a yield of 74.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 18-4 solid sample at atmospheric pressure: MS(ASAP) = 752. Synthesis of intermediate 18-6: Intermediate 18-4 (10 mmol), compound 18-5 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 18-6 in molar amount 5.97 mmol and yield 59.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 18-6 solid sample at atmospheric pressure: MS(ASAP) = 10⁴². Synthesis of intermediate 18-7: Intermediate 18-6 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 18-7 in molar volume of 7.27 mmol and yield of 72.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 18-7 solid sample at atmospheric pressure: MS(ASAP) = 1230. Synthesis of organic compound M151: 10 mmol of intermediate 18-7 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M151, in a yield of 33.8%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M151: MS(ASAP) = 1204. Example 19

[0093] The synthesis route for organic compound M152 is as follows: JPEG2026082747000058.jpg33169 Synthesis of Intermediate 19-2: Intermediate 14-2 (10 mmol), compound 19-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 19-2 in molar amount 6.45 mmol and yield 64.5%. Probe-mass spectrometry (ASAP-MS) results for intermediate 19-2 solid sample at atmospheric pressure: MS(ASAP) = 583. Synthesis of intermediate 19-3: Intermediate 19-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 19-3 in molar amount 6.91 mmol and yield 69.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 19-3 solid sample at atmospheric pressure: MS(ASAP) = 727. Synthesis of intermediate 19-4: Intermediate 19-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 19-4 in molar amount 5.54 mmol, with a yield of 55.4%. Probe-mass spectrometry (ASAP-MS) results for intermediate 19-4 solid sample at atmospheric pressure: MS(ASAP) = 828. Synthesis of intermediate 19-5: Intermediate 19-4 (10 mmol), compound 18-5 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 19-5 in molar amount 5.49 mmol, with a yield of 54.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 19-5 solid sample at atmospheric pressure: MS(ASAP) = 1118. Synthesis of intermediate 19-6: Intermediate 19-5 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 19-6 in molar volume of 7.55 mmol and yield of 75.5%. Probe-mass spectrometry (ASAP-MS) results for intermediate 19-6 solid sample at atmospheric pressure: MS(ASAP) = 1306. Synthesis of organic compound M152: 10 mmol of intermediate 19-6 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M152, in a yield of 29.6%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M152 at atmospheric pressure: MS(ASAP) = 1280. Example 20

[0094] The synthesis route for organic compound M153 is as follows: JPEG2026082747000059.jpg62169 Synthesis of Intermediate 20-1: Intermediate 18-6 (10 mmol), intermediate 14-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 20-1 in molar volume of 7.76 mmol and yield of 77.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 20-1 solid sample at atmospheric pressure: MS(ASAP) = 1250. Synthesis of organic compound M153: 10 mmol of intermediate 20-1 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere, and a solution of t-BuLi(tert-butyllithium) (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M153, in a yield of 36.3%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M153: MS(ASAP) = 1224. Example 21

[0095] The synthesis route for organic compound M154 is as follows: JPEG2026082747000060.jpg62168 Synthesis of Intermediate 21-1: Intermediate 19-5 (10 mmol), intermediate 14-6 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 21-1 in molar volume of 6.53 mmol and yield of 65.3%. Atmospheric pressure solid sample probe-mass spectrometry (ASAP-MS) result for intermediate 21-1: MS(ASAP) = 1326. Synthesis of organic compound M154: 10 mmol of intermediate 21-1 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi(tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M154, in a yield of 31.2%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M154: MS(ASAP) = 1300. Example 22

[0096] The synthesis route for organic compound M155 is as follows: JPEG2026082747000061.jpg36169 Synthesis of Intermediate 22-1: Intermediate 14-2 (10 mmol), compound 18-5 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 22-1 in molar amount 5.67 mmol, with a yield of 56.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 22-1 solid sample at atmospheric pressure: MS(ASAP) = 709. Synthesis of intermediate 22-3: Intermediate 22-1 (10 mmol), compound 22-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 22-3 in molar amount 6.18 mmol, with a yield of 61.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 22-3 solid sample at atmospheric pressure: MS(ASAP) = 978. Synthesis of intermediate 22-4: Intermediate 22-3 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 22-4 in molar volume of 7.27 mmol and yield of 72.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 22-4 solid sample at atmospheric pressure: MS(ASAP) = 1235. Synthesis of organic compound M155: 10 mmol of intermediate 22-4 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M155, in a yield of 28.9%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M155 at atmospheric pressure: MS(ASAP) = 1209. Example 23

[0097] The synthesis route for organic compound M156 is as follows: JPEG2026082747000062.jpg42169 Synthesis of intermediate 23-2: Intermediate 14-4 (10 mmol), compound 23-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 23-2 in molar volume 7.86 mmol and yield 78.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 23-2 solid sample at atmospheric pressure: MS(ASAP) = 967. Synthesis of intermediate 23-3: Intermediate 23-2 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 23-3 in molar volume 5.23 mmol and yield 52.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 23-3 solid sample at atmospheric pressure: MS(ASAP) = 1155. Synthesis of organic compound M156: 10 mmol of intermediate 23-3 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M156, in a yield of 43.6%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M156 at atmospheric pressure: MS(ASAP) = 1129. Example 24

[0098] The synthesis route for organic compound M157 is as follows: JPEG2026082747000063.jpg33169 Synthesis of intermediate 24-2: Intermediate 14-4 (10 mmol), compound 24-1 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 24-2 in molar volume of 7.37 mmol and yield of 73.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 24-2 solid sample at atmospheric pressure: MS(ASAP) = 989. Synthesis of intermediate 24-4: Intermediate 24-2 (10 mmol) and compound 24-3 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 24-4 in molar volume of 8.61 mmol and yield of 86.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 24-4 solid sample at atmospheric pressure: MS(ASAP) = 991. Synthesis of intermediates 24-5: Intermediate 24-4 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 24-5 in molar amount 5.63 mmol and yield 56.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 24-5 solid sample at atmospheric pressure: MS(ASAP) = 1179. Synthesis of organic compound M157: 10 mmol of intermediate 24-5 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M157, in a yield of 41.1%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M157 at atmospheric pressure: MS(ASAP) = 1153. Example 25

[0099] The synthesis route for organic compound M158 is as follows: JPEG2026082747000064.jpg39169 Synthesis of Intermediate 25-1: Intermediate 18-2 (10 mmol), compound 22-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 25-1 in molar amount 6.33 mmol, with a yield of 63.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 25-1 solid sample at atmospheric pressure: MS(ASAP) = 776. Synthesis of intermediate 25-2: Intermediate 25-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 25-2 in molar volume of 8.36 mmol and yield of 83.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 25-2 solid sample at atmospheric pressure: MS(ASAP) = 10³³. Synthesis of organic compound M158: 10 mmol of intermediate 25-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M158, in a yield of 36.9%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M158 at atmospheric pressure: MS(ASAP) = 1007. Example 26

[0100] The synthesis route for organic compound M159 is as follows: JPEG2026082747000065.jpg35168 Synthesis of Intermediate 26-1: Intermediate 25-1 (10 mmol), compound 23-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 26-1 in molar amount 6.89 mmol and yield 68.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 26-1 solid sample at atmospheric pressure: MS(ASAP) = 846. Synthesis of intermediate 26-2: Intermediate 26-1 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 26-2 in molar volume of 8.11 mmol and yield of 81.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 26-2 solid sample at atmospheric pressure: MS(ASAP) = 10³⁴. Synthesis of organic compound M159: 10 mmol of intermediate 26-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M159, in a yield of 37.3%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M159: MS(ASAP) = 1008. Example 27

[0101] The synthesis route for organic compound M160 is as follows: JPEG2026082747000066.jpg31170 Synthesis of intermediate 27-2: Intermediate 14-2 (10 mmol), compound 27-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 27-2 in molar amount 5.80 mmol and yield 58.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 27-2 solid sample at atmospheric pressure: MS(ASAP) = 709. Synthesis of intermediate 27-3: Intermediate 27-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 27-3 in molar amount 8.63 mmol and yield 86.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 27-3 solid sample at atmospheric pressure: MS(ASAP) = 853. Synthesis of intermediate 27-4: Intermediate 27-3 (10 mmol), compound 23-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 27-4 in molar amount 6.84 mmol and yield 68.4%. Probe-mass spectrometry (ASAP-MS) results for intermediate 27-4 solid sample at atmospheric pressure: MS(ASAP) = 967. Synthesis of intermediate 27-5: Intermediate 27-4 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 27-5 in molar volume 7.69 mmol and yield 76.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 27-5 solid sample at atmospheric pressure: MS(ASAP) = 1155. Synthesis of organic compound M160: 10 mmol of intermediate 27-5 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M160, in a yield of 37.0%. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M160: MS(ASAP) = 1129. Example 28

[0102] The synthesis route for organic compound M161 is as follows: JPEG2026082747000067.jpg31169 Synthesis of Intermediate 28-2: Intermediate 14-2 (10 mmol), compound 28-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 28-2 in molar amount 6.90 mmol and yield 69.0%. Probe-mass spectrometry (ASAP-MS) results for intermediate 28-2 solid sample at atmospheric pressure: MS(ASAP) = 730. Synthesis of intermediate 28-3: Intermediate 28-2 (10 mmol), compound 22-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 28-3 in molar amount 8.12 mmol, with a yield of 81.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 28-3 solid sample at atmospheric pressure: MS(ASAP) = 999. Synthesis of intermediate 28-4: Intermediate 28-3 (10 mmol), compound 23-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 28-4 in molar amount 7.53 mmol and yield 75.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 28-4 solid sample at atmospheric pressure: MS(ASAP) = 10⁶⁹. Synthesis of intermediate 28-5: Intermediate 28-4 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 28-5 in molar volume 7.20 mmol and yield 72.0%. Probe-mass spectrometry (ASAP-MS) results for intermediate 28-5 solid sample at atmospheric pressure: MS(ASAP) = 1257. Synthesis of organic compound M161: 10 mmol of intermediate 28-5 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M161, in a yield of 32.8%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M161: MS(ASAP) = 1231. Example 29

[0103] The synthesis route for organic compound M162 is as follows: JPEG2026082747000068.jpg30169 Synthesis of Intermediate 29-2: Intermediate 14-2 (10 mmol), compound 29-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 29-2 in molar amount 7.92 mmol and yield 79.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 29-2 solid sample at atmospheric pressure: MS(ASAP) = 532. Synthesis of intermediate 29-3: Intermediate 29-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 29-3 in molar amount 8.56 mmol and yield 85.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 29-3 solid sample at atmospheric pressure: MS(ASAP) = 676. Synthesis of intermediate 29-5: Intermediate 29-3 (10 mmol), compound 29-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 29-5 in molar amount 7.21 mmol and yield 72.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 29-5 solid sample at atmospheric pressure: MS(ASAP) = 921. Synthesis of intermediate 29-6: Intermediate 29-5 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 29-6 in molar volume of 7.38 mmol and yield of 73.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 29-6 solid sample at atmospheric pressure: MS(ASAP) = 1109. Synthesis of organic compound M162: 10 mmol of intermediate 29-6 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, i.e., organic compound M162, in a yield of 36.4%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M162: MS(ASAP) = 10⁸³. Example 30

[0104] The synthesis route for organic compound M163 is as follows: JPEG2026082747000069.jpg26169 Synthesis of Intermediate 30-2: Intermediate 14-2 (10 mmol), compound 30-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-sodium butoxide (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 30-2 in molar amount 7.35 mmol and yield 73.5%. Probe-mass spectrometry (ASAP-MS) results for intermediate 30-2 solid sample at atmospheric pressure: MS(ASAP) = 639. Synthesis of intermediate 30-3: Compound 30-2 (10 mmol), Compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 30-3 in molar amount 8.22 mmol and yield 82.2%. Probe-mass spectrometry (ASAP-MS) results for intermediate 30-3 solid sample at atmospheric pressure: MS(ASAP) = 783. Synthesis of intermediate 30-4: Intermediate 30-3 (10 mmol), compound 24-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 30-4 in molar amount 7.38 mmol and yield 73.8%. Probe-mass spectrometry (ASAP-MS) results for intermediate 30-4 solid sample at atmospheric pressure: MS(ASAP) = 919. Synthesis of intermediate 30-5: Intermediate 30-4 (10 mmol) and compound 24-3 (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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 30-5 in molar volume of 8.09 mmol and yield of 80.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 30-5 solid sample at atmospheric pressure: MS(ASAP) = 922. Synthesis of intermediate 30-6: Intermediate 30-5 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphin-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 30-6 in molar volume of 7.85 mmol and yield of 78.5%. Probe-mass spectrometry (ASAP-MS) results for intermediate 30-6 solid sample at atmospheric pressure: MS(ASAP) = 1110. Synthesis of organic compound M163: 10 mmol of intermediate 30-6 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M163, in a yield of 36.9%. Probe-mass spectrometry (ASAP-MS) results for the solid sample of organic compound M163 at atmospheric pressure: MS(ASAP) = 10⁸⁴. Example 31

[0105] The synthesis route for organic compound M164 is as follows: JPEG2026082747000070.jpg29169 Synthesis of intermediate 31-2: Intermediate 30-3 (10 mmol), compound 31-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 31-2 in molar amount 7.96 mmol and yield 79.6%. Probe-mass spectrometry (ASAP-MS) results for intermediate 31-2 solid sample at atmospheric pressure: MS(ASAP) = 996. Synthesis of intermediate 31-3: Intermediate 31-3 (10 mmol) and compound 24-3 (20 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 heated to 100°C under a nitrogen atmosphere and stirred for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 31-3 in molar volume of 8.57 mmol and yield of 85.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 31-3 solid sample at atmospheric pressure: MS(ASAP) = 1002. Synthesis of intermediates 31-4: Intermediate 31-3 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated. The organic phase was recrystallized by column chromatography to obtain intermediate 31-4 in molar volume 7.25 mmol and yield 72.5%. Probe-mass spectrometry (ASAP-MS) results for intermediate 31-4 solid sample at atmospheric pressure: MS(ASAP) = 1190. Synthesis of organic compound M164: 10 mmol of intermediate 31-4 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M164, in a yield of 44.6%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M164: MS(ASAP) = 1164. Example 32

[0106] The synthesis route for organic compound M165 is as follows: JPEG2026082747000071.jpg32169 Synthesis of intermediate 32-2: Intermediate 22-1 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 32-2 in molar amount 6.59 mmol and yield 65.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 32-2 solid sample at atmospheric pressure: MS(ASAP) = 1111. Synthesis of intermediate 32-3: Intermediate 32-2 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 32-3 in molar volume of 7.93 mmol and yield of 79.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 32-3 solid sample at atmospheric pressure: MS(ASAP) = 1412. Synthesis of organic compound M165: 10 mmol of intermediate 32-3 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, 42 mmol of N,N-diisopropylethylamine was added, and after the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M165, in a yield of 37.7%. The hydrogen nuclear magnetic resonance spectrum of organic compound M165 is shown in Figure 1. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M165: MS(ASAP) = 1386. Example 33

[0107] The synthesis route for organic compound M166 is as follows: Synthesis of intermediate 33-1 in JPEG2026082747000072.jpg32169: Intermediate 18-2 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 33-1 in molar amount 6.59 mmol, with a yield of 65.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 33-1 solid sample at atmospheric pressure: MS(ASAP) = 909. Synthesis of intermediate 33-2: Intermediate 33-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 33-2 in molar volume of 7.54 mmol and yield of 75.4%. Atmospheric pressure solid sample probe-mass spectrometry (ASAP-MS) result for intermediate 33-2: MS(ASAP) = 1210. Synthesis of organic compound M166: 10 mmol of intermediate 33-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M166, in a yield of 32.8%. The hydrogen nuclear magnetic resonance spectrum of organic compound M166 is shown in Figure 2. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M166: MS(ASAP) = 1184. Example 34

[0108] The synthesis route for organic compound M167 is as follows: Synthesis of intermediate 34-1 in JPEG2026082747000073.jpg32169: Intermediate 19-2 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-sodium butoxide (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 34-1 in molar amount 8.41 mmol and yield 84.1%. Probe-mass spectrometry (ASAP-MS) results for intermediate 34-1 solid sample at atmospheric pressure: MS(ASAP) = 985. Synthesis of intermediate 34-2: Intermediate 34-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 34-2 in molar volume of 8.03 mmol and yield of 80.3%. Probe-mass spectrometry (ASAP-MS) results for intermediate 34-2 solid sample at atmospheric pressure: MS(ASAP) = 1286. Synthesis of organic compound M167: 10 mmol of intermediate 34-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M167, in a yield of 38.3%. The hydrogen nuclear magnetic resonance spectrum of organic compound M167 is shown in Figure 3. Probe-mass spectrometry (ASAP-MS) results for the atmospheric pressure solid sample of organic compound M167: MS(ASAP)=1260. Example 35

[0109] The synthesis route for organic compound M168 is as follows: Synthesis of intermediate 35-1 in JPEG2026082747000074.jpg30169: Intermediate 30-2 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0), 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 100°C for 6 hours. After cooling the reaction mixture, the solvent was removed by rotary evaporation, the reaction mixture was extracted, washed with water, and liquid-liquid separated. The organic phase was subjected to column chromatography to obtain intermediate 35-1 in molar amount 8.17 mmol, with a yield of 81.7%. Probe-mass spectrometry (ASAP-MS) results for intermediate 35-1 solid sample at atmospheric pressure: MS(ASAP) = 10⁴¹. Synthesis of intermediate 35-2: Intermediate 35-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and tert-butoxide sodium (30 mmol) were dissolved in toluene and stirred under a nitrogen atmosphere at 120°C for 3 hours. After cooling the reaction mixture, most of the solvent was removed by rotary evaporation. The reaction mixture was extracted, washed with water, and separated into liquid and liquid phases. The organic phase was recrystallized by column chromatography to obtain intermediate 35-2 in molar volume of 7.29 mmol and yield of 72.9%. Probe-mass spectrometry (ASAP-MS) results for intermediate 35-2 solid sample at atmospheric pressure: MS(ASAP) = 1342. Synthesis of organic compound M168: 10 mmol of intermediate 35-2 and 100 ml of dried tert-butylbenzene were added to a 250 ml three-necked flask. The mixture was cooled to -30°C in an N2 atmosphere. A solution of t-BuLi (tert-butyllithium) (21 mmol) in n-hexane was added dropwise, and the temperature was raised to 60°C for 2 hours. The n-hexane solvent was removed by reduced-pressure evaporation. The reaction mixture was further cooled to -30°C, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the dropwise addition was complete, the mixture was heated to room temperature and stirred, then further heated to 120°C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched by adding aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phase was combined with the aqueous phase. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by high-speed silica gel column chromatography to obtain the refined product. Recrystallization using toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M168, in a yield of 39.2%. Atmospheric pressure probe-mass spectrometry (ASAP-MS) results for organic compound M168: MS(ASAP) = 1316.

[0110] As described above, the organic compounds relating to Examples 1 to 35 of this application contain boron and biphenyl. By introducing structures such as dibenzofuran, dibenzothiophene, carbazole, benzo five-membered ring, triphenylene, and / or naphthalene into the boron nitrogen compound, the overall conjugation of the molecule is increased, thereby improving the luminescence efficiency of organic light-emitting devices using the organic compound and extending their lifespan. Furthermore, by introducing structures such as tetralin and / or indan into the boron nitrogen compound, the solubility of the molecule in processes such as inkjet printing is improved, facilitating the purification of the compound, thereby improving the purity of the organic compound, and further improving the luminescence efficiency of organic light-emitting devices using the organic compound and extending their lifespan.

[0111] The embodiments of the present application also provide mixtures comprising the organic compounds described in the embodiments above and at least one organic functional material. In some embodiments, when the mixtures provided in the embodiments of the present application are used in an organic light-emitting device, the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, light-emitting materials, or organic dyes.

[0112] The embodiments of the present application also provide compositions comprising the organic compounds described in the above embodiments and at least one organic solvent, or compositions comprising the mixture described in the above embodiments and at least one organic solvent.

[0113] In some embodiments, the composition may be a solution or a suspension, and the composition may include a dispersant and a dispersant. Here, the dispersant is one or more organic compounds as described above and at least one organic solvent, or the dispersant is a mixture as described above, and the dispersant is used to disperse the dispersant.

[0114] In some embodiments, the mass fraction of the above-mentioned organic compounds in the composition is 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, even more preferably 0.5% to 10%, and most preferably 1% to 5%.

[0115] When the composition is used in a printing process, the composition may be an ink, and the viscosity and surface tension of the ink are important parameters, with appropriate ink surface tension parameters suitable for a particular substrate and a particular printing method. In some embodiments, the surface tension range of the ink at operating temperature or 25°C is 19 dyne / cm to 50 dyne / cm, preferably 22 dyne / cm to 35 dyne / cm, more preferably 25 dyne / cm to 33 dyne / cm, which is advantageous for application to an inkjet printing process. In some embodiments, the viscosity range of the ink at operating temperature or 25°C is 1 cps to 100 cps, preferably 1 cps to 50 cps, more preferably 1.5 cps to 20 cps, most preferably 4.0 cps to 20 cps, which is advantageous for application to an inkjet printing process.

[0116] 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 18.5 to 21.0 MPa 1 / 2. The δp (polarity force) is in the range of 0.2 to 12.5 MPa 1 / 2, preferably 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 2.0 to 6.0 MPa 1 / 2.

[0117] 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, even more preferably 250°C or higher, even more preferably 275°C or higher, and most preferably 300°C or higher. The boiling point of the dispersant is at least 150°C, which is advantageous in preventing clogging of the inkjet print head nozzles during inkjet printing, and a higher boiling point is advantageous in preventing clogging.

[0118] In some embodiments, the dispersant may include at least one organic solvent that can evaporate from the solvent system to form a thin film containing the functional material. In some embodiments, the organic solvent may be selected from aromatic or heteroaromatic solvents. Specifically, the organic solvent may be p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene You may choose from benzoate, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoseate, ethyl 2-furoseate, etc.

[0119] In some embodiments, the organic solvent may be selected from aromatic ketone solvents. Specifically, the organic solvent may be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like.

[0120] In some embodiments, the organic solvent may also be selected from aromatic ether solvents. Specifically, the organic solvent may 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-ethylphenethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl 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.

[0121] In some embodiments, the organic solvent may also be selected from aliphatic ketones such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fencone, holone, isophorone, di-n-amyl ketone, or aliphatic ethers 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, and tetraethylene glycol dimethyl ether.

[0122] In some embodiments, the organic solvent may also be selected from organic ester solvents. Specifically, the organic solvent may be selected from alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkylphenyl acetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Particularly preferred are octyl octanoates, diethyl sebacates, diallyl phthalates, and isononyl caprylates.

[0123] In some embodiments, the organic solvent may be one or more solvents selected from methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxanehexane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and the like.

[0124] In some embodiments, the composition may further include, in addition to the dispersed phase and the dispersant, one or more components such as surfactants, lubricants, wetting agents, hydrophobic agents, and adhesives for purposes such as adjusting viscosity, film-forming properties, and improving adhesion.

[0125] Referring further to Figure 4, the embodiment of the present application provides an organic light-emitting device 100 comprising 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, wherein the material of the organic functional layer 103 comprises one or more of the organic compounds described in the above embodiment, or the material of the organic functional layer 103 comprises the mixture described in the above embodiment, or the material of the organic functional layer 103 comprises the composition described in the above embodiment.

[0126] In some embodiments, the first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0127] In some embodiments, the organic light-emitting device 100 can be used as an organic light-emitting diode, organic solar cell, organic light-emitting cell, organic field-effect transistor, organic laser, organic spintronic device, organic sensor, and organic plasmon light-emitting diode, preferably an organic light-emitting diode, organic light-emitting cell, or organic light-emitting field-effect transistor.

[0128] In some embodiments, the organic light-emitting device 100 can be applied to various electronic devices such as display panels, lighting equipment, and light sources.

[0129] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixed layer comprising a first compound and a second compound, wherein the first compound is one or more selected from the organic compounds described above, and the second compound is one or more selected from hole injection materials, hole transport materials, electron transport materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes. A detailed description of the various organic functional materials included in the organic functional layer 103 is provided in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of these three patent documents are incorporated herein by reference.

[0130] The luminescent guest material is selected from singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), and TADF materials.

[0131] If the second compound is one or more selected from hole injection materials, hole transport materials, electron transport materials, hole blocking materials, luminescent host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0132] When the second compound is a luminescent guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0133] In some embodiments, the organic functional layer 103 may comprise multiple layers. When the organic functional layer 103 comprises multiple layers, it includes at least an emissive layer. Preferably, as shown in Figure 4, the organic functional layer 103 comprises a hole injection layer 104, a hole transport layer 105, an electron blocking layer 106, an emissive layer 107, an electron transport layer 108, and an electron injection layer 109. In other embodiments of the present application, the organic functional layer 103 may further comprise a hole blocking layer disposed between the emissive layer 107 and the electron transport layer 108.

[0134] 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 may include a host material and a guest material, the guest material being one or more of the above-mentioned organic compounds, and the host material including a condensed aromatic derivative or a heteroaromatic compound.

[0135] In some embodiments, the emission wavelength of the organic light-emitting device 100 is between 300 nm and 1000 nm. Furthermore, the emission wavelength of the organic light-emitting device 100 is between 350 nm and 900 nm. Moreover, the emission wavelength of the organic light-emitting device 100 is between 400 nm and 800 nm. Furthermore, the emission wavelength of the organic light-emitting device 100 is within the wavelength range of blue light.

[0136] In some embodiments, the host material comprises at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluorantene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Preferably, the host material is a blue light host material applied to a blue organic light-emitting device, and if the host material is a blue light host material, the host material is preferably an anthracene-based organic compound.

[0137] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, and preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which is advantageous in suppressing crystallization of the light-emitting layer 107 and suppressing concentration quenching due to excessively high concentrations of the guest material, thereby improving the luminescence efficiency of the organic light-emitting device 100.

[0138] In some embodiments, the anode is a hole injection electrode that can inject holes into the organic functional layer 103, such as by injecting holes into the hole injection layer, the hole transport layer, or the light-emitting layer. The anode may contain at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the p-type semiconductor material functioning as the hole injection layer, or the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the p-type semiconductor material in the hole injection layer and the hole transport layer or electron blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The anode material includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, indium tin oxide (ITO), aluminum-doped zinc oxide (AZO), or other suitable known anode materials. These can be easily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as suitable physical deposition methods including radio frequency magnetron sputtering, vacuum thermal deposition, or electron beam (e-beam). In some embodiments, the anode can be patterned. For example, patterned ITO conductive substrates are commercially available and can be used in the manufacture of the organic light-emitting device 100 of this application.

[0139] In some embodiments, the cathode is an electron injection electrode that can inject electrons into the organic functional layer 103, such as by injecting electrons into the electron injection layer, the electron transport layer, or the light-emitting layer. The cathode may contain at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the n-type semiconductor material functioning as the electron injection layer, or the absolute difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the n-type semiconductor material of the electron injection layer and electron transport layer or hole blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes in organic electronic devices can be used as cathode materials for the devices of this application, and such cathode materials include, but are not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique such as radio frequency magnetron sputtering, vacuum thermal deposition, electron beam (e-beam) or other suitable physical deposition methods.

[0140] In some embodiments, the hole injection layer 104 is used to facilitate the injection of holes from the anode to the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material which is a material capable of receiving 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 of the film layer on the side farther from the anode to which the holes are injected (e.g., the hole transport material of the hole transport layer). The hole injection material includes, but is not limited to, at least one of metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyanilines, and polythiophenes-based conductive polymers.

[0141] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transported from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material known in the art having high hole mobility and may include, but is not limited to, at least one of an arylamine-based organic material, a conductive polymer, or a block copolymer having both conjugated and unconjugated moieties.

[0142] In some embodiments, the electron transport layer 108 is used to transport electrons and includes an electron transport material that receives electrons injected from the cathode and transports those electrons to the light-emitting layer 107. The electron transport material is a material known in the art having high electron mobility and includes, but is not limited to, at least one of Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, lithium 8-hydroxyquinolinate (LiQ), and compounds based on benzimidazole.

[0143] In some embodiments, the electron injection layer 109 is used to inject electrons, and the electron injection layer 109 comprises an electron injection material, which preferably has electron transport ability, has the effect of injecting electrons from the cathode, has an excellent effect of injecting electrons into the light-emitting layer 107 or light-emitting material, has the effect of preventing excitons generated in the light-emitting layer 107 from moving to the hole injection layer, and is also a material with excellent thin-film formation ability. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinolinate lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiapyran dioxide, pyrazole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc., and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, etc.

[0144] In some embodiments, the hole-blocking layer is used to prevent holes from reaching the cathode and can typically be formed under the same conditions as the hole-injection layer 104. The hole-blocking layer comprises a hole-blocking material, which includes, but is not limited to, at least one of diazole or triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0145] In some embodiments, the organic light-emitting device 100 further includes a base 110 on which the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially laminated. The base 110 may be a transparent base or an opaque base. If the base 110 is a transparent base, a transparent organic light-emitting device can be manufactured. The base 110 may be a rigid base or an elastic flexible base. The material of the base 110 may include, but is not limited to, plastics, polymers, metals, semiconductor wafers, glass, etc. Preferably, the base 110 includes at least one smooth surface for forming the anode. More preferably, the surface is free of surface defects. Preferably, the material of the base 110 is a polymer film or plastic such as polyethylene terephthalate (PET material) or polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the base 110 is 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher.

[0146] 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 manufactured by printing (e.g., inkjet printing).

[0147] In some embodiments, the mixture layer or the light-emitting layer may 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, doctor blade coating, roller printing, twist roller printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slit extrusion coating, etc. Gravure printing, nozzle printing and inkjet printing are preferred.

[0148] As described above, the boron-containing biphenyl organic compounds provided in Examples 1 to 35 of the present application introduce structures such as dibenzofuran, dibenzothiophene, carbazole, benzo five-membered ring, triphenylene, and / or naphthalene into the boron-nitrogen compound, thereby making the conjugation of the whole molecule higher, and thereby improving the luminous efficiency of the organic light-emitting device using the organic compound and extending its lifespan. In addition, by introducing structures such as tetralin and / or indane into the boron-nitrogen compound, the solubility of the molecule in processes such as inkjet printing is made better, the purification of the compound is facilitated, thereby improving the purity of the organic compound, and further improving the luminous efficiency of the organic light-emitting device using the organic compound and extending its lifespan.

[0149] Furthermore, the embodiments of the present application calculated the HOMO energy level, LUMO energy level, S1 energy level and T1 energy level of the organic compounds shown in Examples 1 to 35 and Comparative Compound 1 of Comparative Example 1, and verified the performance of the organic compounds provided in the embodiments of the present application.

[0150] The structural formula of Comparative Compound 1 of Comparative Example 1 is as follows. TIFF2026082747000075.tif69102 Comparative Compound 1

[0151] Quantum computation can be used to obtain the HOMO (Highest Occupied Molecular Orbital) energy levels, LUMO (Lowest Unoccupied Molecular Orbital) energy levels, T1 (First Excited Triplet State) energy level, and S1 (First Excited Singlet State) energy level of compounds M1 to M168 obtained in Examples 1 to 35, and comparative compound 1 from Comparative Example 1. Specifically, TD-DFT (Time-Dependent Density Functional Theory) was used with Gaussian09W (Gaussian Inc.). For details on the simulation method, please refer to WO2011141110. First, the molecular geometry was optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule was calculated using TD-DFT (Time-Dependent Density Functional Theory), "TD-SCF / DFT / Default Spin / B3PW91", and the basis set "6-31G(d)(Charge 0 / Spin Singlet)". The HOMO and LUMO energy levels were calculated according to the following calibration formulas, while the S1 and T1 energy levels were used directly.

[0152] 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 direct calculation results from Gaussian 09W, and the unit is Hartree.

[0153] As described above, the calculation results shown in Table 1 below were obtained.

[0154] [Table 1] TIFF2026082747000077.tif26169

[0155] Table 1 shows that the T1 and S1 energy levels of the organic compounds provided in Examples 1 to 35 of this application are all higher than those of comparative compound 1. This indicates that the blue light emitted by organic compounds M1 to M168 is a deeper blue compared to comparative compound 1. This suggests that a better color coordinate can be obtained in a blue organic light-emitting device using organic compounds M1 to M168 as guest materials for the light-emitting layer.

[0156] Furthermore, referring to Figure 5, the embodiments of the present application provide exemplary manufacturing steps for the organic light-emitting device 200 shown in Figure 5, as shown in the following exemplary embodiment A. Example A

[0157] In the organic light-emitting device 200 provided in this embodiment, ITO (indium tin oxide) is used as the anode 202, and PEDOT (polyethylene dioxythiophene, Clevios) is used as the material for the hole injection layer 203. TM AI4083) was used, PVK (poly(9-vinylcarbazole, Sigma Aldrich, average Mn 25,000~50,000)) was used as the material for the hole transport layer 204, BH-1 to BH-3 (structural formulas shown below) were used as the host material for the light-emitting layer of the corresponding organic light-emitting device, the organic compounds of Examples 1 to 35 and comparative compound 1 of Comparative Example 1 were used as the guest material for the light-emitting layer of the corresponding organic light-emitting device, ET and Liq (8-hydroxyquinolinate lithium) were used as the material for the electron transport layer 206, and Al was used as the cathode 207. The specific manufacturing steps are as follows.

[0158] a. Cleaning of ITO conductive glass: The ITO conductive glass was cleaned using chloroform, acetone, and / or isopropyl alcohol, and then subjected to ultraviolet ozone treatment. The conductive glass comprises a base 201 and an anode 202 formed on the base 201.

[0159] b. Formation of hole injection layer 203: The material of the hole injection layer is PEDOT (polyethylenedioxythiophene, Clevios TM AI4083 was spin-coated onto anode 202 and heated on a hot plate at 180°C for 10 minutes. The thickness of the hole injection layer 203 was 40 nm.

[0160] c. Formation of hole transport layer 204: A toluene solution of PVK (Sigma Aldrich, Mn 25,000-50,000) at a concentration of 5 mg / ml was spin-coated onto the hole injection layer 203 and heated on a hot plate at 180°C for 60 minutes. The thickness of the hole transport layer 204 was 20 nm.

[0161] d. Formation of the luminescent layer 205: The luminescent layer material was spin-coated onto the hole transport layer 204 in a nitrogen glove box and treated on a hot plate at 140°C for 10 minutes. The host material in the luminescent layer 205 of the different organic light-emitting devices 200 corresponds to BH-1, BH-2, or BH-3, respectively. The guest material in the luminescent layer 205 of the different organic light-emitting devices 200 corresponds to one of the organic compounds from Examples 1 to 35, respectively. The solvent was a methyl benzoate solution. The mass ratio of the host material to the guest material was 95:5. The material concentration of the luminescent layer 205 was 15 mg / ml. The final thickness of the formed luminescent layer 205 was 40 nm.

[0162] e. Formation of electron transport layer 206: In a vacuum chamber, ET and Liq are placed on top of the light-emitting layer 205 in different evaporation units, and a high vacuum (1 × 10⁻¹⁶) is created. -6 Under mbar conditions, ET and Liq were co-deposited in a weight ratio of 50:50 to form an electron transport layer 206 with a thickness of 20 nm.

[0163] f. Formation of cathode 207: Al was deposited on the electron transport layer 206 to obtain an Al cathode 207 with a thickness of 100 nm.

[0164] g. Packaging: The device was packaged in a nitrogen glove box using UV-curing resin. Specifically, in this embodiment, by the above steps, organic light-emitting devices 1 to 39 and comparative elements 1 to 3 as shown in Examples 36 to 74 and Comparative Examples 2 to 4 were obtained. Here, the guest materials used for organic light-emitting devices 1 to 35 are organic compounds M1 to M168, respectively, and the host material is BH-1. The guest materials used for organic light-emitting devices 36 and 38 are organic compound M16, respectively, and the host materials used for organic light-emitting devices 36 and 38 are BH-2 and BH-3, respectively. The guest materials used for organic light-emitting devices 37 and 39 are organic compound M64, and the host materials used for organic light-emitting devices 37 and 39 are BH-2 and BH-3, respectively. The guest material used for comparative elements 1 to 3 is comparative compound 1, and the host materials are BH-1, BH-2, and BH-3, respectively. Specifically, the chemical structural formulas of BH-1, BH-2, BH-3, ET, and Liq are as follows. TIFF2026082747000078.tif32160

[0165] In this embodiment, for organic light-emitting devices 1 to 39 and comparative elements 1 to 3, the current-voltage (J-V) characteristics were measured, and for each organic light-emitting device and comparative element, the CIE color coordinates (x, y), the driving voltage at a luminance of 1 knits (voltage @ 1 knits [V]), the luminous efficiency (CE @ 1 knits [cd / A]) obtained at a current density of 10 mA / cm 2 and the time (LT90 @ 1 knits [h]) from an initial luminance of 1 knits to a decrease to 90% of the initial luminance were obtained. The specific results are shown in Table 2.

[0166] Table 2 is data showing the performance of the organic light-emitting devices.

Table 2

[0167] As can be seen from Table 2, compared to comparative elements 1 to 3, the organic light-emitting devices 1 to 39 obtained by applying the organic compounds according to Examples 36 to 74 of this application as guest materials to the light-emitting layer have superior color coordinates. Furthermore, the luminous efficiency of organic light-emitting devices 1 to 39 is all in the range of 5.7 to 6.6 cd / A, which is far higher than that of comparative elements 1 to 3. Moreover, compared to the time it takes for the brightness of comparative elements 1 to 3 to decrease from an initial brightness of 1 knit to 90% of the initial brightness, the time it takes for the brightness of organic light-emitting devices 1 to 39 to decrease from an initial brightness of 1 knit to 90% of the initial brightness is all in the range of 133 to 176 hours, which is a 50% to 100% improvement compared to the time it takes for the brightness of comparative elements 1 to 3 to decrease from an initial brightness of 1 knit to 90% of the initial brightness, clearly demonstrating a significant extension of the lifespan of organic light-emitting devices 1 to 39.

[0168] Furthermore, compared to Comparative Example 1, organic compounds M1 to M168, by introducing biphenyl rings, aromatic rings, and silicon groups (deuterated phenyl groups), exhibit better overall molecular solubility, facilitate the purification of the organic compounds, thereby improving their purity, and further enhancing the efficiency and extending the lifespan of the manufactured organic light-emitting devices.

[0169] Furthermore, the luminous efficiencies of organic light-emitting devices 1-4 and 151-168 are all in the range of 6.1-6.5 cd / A, and their lifetime is approximately 170 hours. This is because, compared to guest materials for other organic light-emitting devices, the guest materials provided in the examples of this application contain a triphenylene group, which increases the overall conjugation of the molecule, and the aromatic amine combining benzothiophene and a triphenylene group exhibits significantly better lifetime and efficiency than the combination of benzothiophene and dibenzothiophene (furan). In addition, the guest materials provided in the examples of this application have a greater number of solubilizing groups, which improves the solubility of the guest materials, further improving the luminous efficiency of the organic light-emitting devices and extending their lifetime.

[0170] The organic light-emitting devices disclosed in the embodiments of this application use a boronitrogen compound and improve the material properties, enhance the luminescence efficiency of the organic light-emitting device, and extend the service life of the organic light-emitting device by introducing the aromatic amines biphenyl and benzothiophene, and silicon-containing groups that further enhance the overall conjugation of the compound, into the boronitrogen compound.

[0171] The embodiments of the present application also disclose a display panel including the organic light-emitting device described in the embodiments above.

[0172] The display panel further includes an array substrate disposed on one side of the organic light-emitting device, and a package layer disposed on the side of the organic light-emitting device away from the array substrate and covering the organic light-emitting device. The display panel further includes a polarizing layer located on the side of the package layer away from the organic light-emitting device, and a cover layer located on the side of the polarizing layer away from the organic light-emitting device. Here, the polarizing layer can be replaced with a color film layer which may include a plurality of color resists and a black matrix located on both sides of the color resists.

[0173] The display panel disclosed in the embodiments of this application uses an organic light-emitting device containing a boronitrogen compound, and by introducing a silicon-containing group into the boronitrogen compound, the overall conjugation of the compound is increased, thereby improving the conjugation effect of the material used in the organic light-emitting device, improving the material properties, increasing the luminous efficiency of the display panel, and extending the service life of the display panel.

[0174] In the above embodiments, each embodiment is described with particular emphasis, and for parts not explained in detail in one embodiment, you can refer to the relevant descriptions in other embodiments.

[0175] The organic compounds, mixtures, compositions, organic light-emitting devices, and display panels provided in the embodiments of this application have been described in detail above. While the principles and embodiments of this application have been described using specific examples, the above description of embodiments is merely intended to aid in understanding the technical solutions and core ideas of this application. Those skilled in the art should understand that they may modify the technical solutions described in the above embodiments or replace some of the technical features therein with equivalent ones. However, these modifications or substitutions will not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of this application.

Claims

1. It is an organic compound, The organic compound is characterized by having a structure represented by general formula (1) or general formula (2). (Here, Ar １ , and Ar ２ These are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 60 carbon atoms. Ar ３ , and Ar ４ These are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms. R １ , and R ２ H, D, linear alkyl groups having 1 to 20 carbon atoms, linear or branched silicon groups having 1 to 20 carbon atoms, linear alkoxy groups having 1 to 20 carbon atoms, linear thioalkoxy groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, branched alkoxy groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, branched thioalkoxy groups having 3 to 20 carbon atoms, cyclic thioalkoxy groups having 3 to 20 carbon atoms, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, CF ３ Selected from Cl, Br, F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5 to 30 ring atoms. Ar １ 、Ar ２ 、Ar ３ 、Ar ４ 、R １ 、and R ２ at least one of which has a linear or branched silicon group having 1 to 20 carbon atoms or a deuterated phenyl group, n1 is selected from 0, 1, 2, or 3. n2 is selected from 0, 1, 2, 3, or 4.

2. R １ , and R ２ It is selected from silyl groups, Ar １ Ar ２ Ar ３ Ar ４ , R １ , and R ２ At least one of them has a silyl group or a deuterated phenyl group. The organic compound according to claim 1.

3. R １ , and R ２ The trimethylsilyl group and the triphenylsilyl group are selected from, Ar １ Ar ２ Ar ３ Ar ４ , R １ , and R ２ At least one of them has a trimethylsilyl group, a triphenylsilyl group, or a deuterated phenyl group. The organic compound according to claim 2.

4. Ar １ is a base represented by any one selected from equations (X-1) to (X-4), Ar ２ It is selected from the base represented by any one of formulas (A-1) to (A-4), Ar ３ , and Ar ４ The organic compound according to claim 1, characterized in that the group is selected from any one of the groups represented by formulas (B-1) to (B-5). (Here, --- in equations (X-1) to (X-4) represents a link that connects to general equation (1) or general equation (2), Ar ２ The linking site is located on a carbon atom of either ring, Ar ３ The linking site is located on a carbon atom of either ring, Ar ４ The condensation site is located at the two carbon atoms in the otol position within the same ring. X is O, S, N-CH ３ , N-Ph, or C(CH ３ ) ２ Selected from, R ０ , and L are H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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, and a ring having 3 to 20 carbon atoms. Thioalkoxy group, silyl group, trimethylsilyl group, triphenylsilyl group, ketone group with 1 to 20 carbon atoms, alkoxycarbonyl group with 2 to 20 carbon atoms, aryloxycarbonyl group with 7 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF ３ Selected from Cl, Br, F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5 to 30 ring atoms. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. (a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.)

5. Ar １ If is selected from the group represented by formula (X-2), Ar ４ The organic compound according to claim 4, characterized in that is a group represented by any one selected from formulas (B-2) to (B-5).

6. Ar ２ teeth, The organic compound according to claim 4, which is at least one selected from the following. (Here, L and a in these bases have the same definitions as L and a in formulas (A-1) to (A-4).)

7. If n1 is 2 or greater, then two adjacent R １ These, together with the ring atoms linked to them, either form a ring with each other or do not form a ring. If n2 is 2 or greater, then two adjacent R ２ These, together with the ring atoms linked to them, either form a ring with each other or do not form a ring. The organic compound according to claim 4, characterized in that when a is 2 or more, two adjacent L atoms may or may not form a ring with the atoms linked to them.

8. The organic compound according to claim 1, characterized in that the organic compound has a structure represented by any one of general formulas (2-1) to (2-31). ； (Here, L and R in general formulas (2-1) to (2-31) ３ , and R ４ This includes H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear or branched silicon 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, and a cyclic thioalkoxy group having 3 to 20 carbon atoms. Oalkoxy group, silyl group, trimethylsilyl group, triphenylsilyl group, ketone group with 1 to 20 carbon atoms, alkoxycarbonyl group with 2 to 20 carbon atoms, aryloxycarbonyl group with 7 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF ３ Selected from Cl, Br, F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy groups with 5 to 30 ring atoms. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. n3 is between 0 and 5, and if n3 is 2 or greater, then two adjacent R ３ These, together with the atoms linked to them, may or may not form rings with each other. n4 is between 0 and 5, and if n4 is 2 or greater, then two adjacent R ４ These atoms, together with the atoms linked to them, may or may not form rings with each other.

9. R １ , R ２ , R ３ , R ４ The organic compound according to claim 8, characterized in that L is 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.

10. R １ , R ２ , R ３ , R ４ The organic compound according to claim 8, characterized in that L is 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.

11. The organic compound according to claim 1, characterized in that the organic compound is a blue light-emitting material.

12. The organic compound according to claim 1, characterized in that the organic compound is one selected from the following compounds 1 to 168.

13. The present invention comprises an organic compound according to any one of claims 1 to 12 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, light-emitting materials, host materials, or organic dyes. mixture.

14. A composition comprising an organic compound according to any one of claims 1 to 12 and at least one organic solvent, or a mixture according to claim 13 and at least one of the organic solvents.

15. Organic light-emitting device, First electrode and, A second electrode positioned opposite the first electrode, The invention includes an organic functional layer located between the first electrode and the second electrode, An organic light-emitting device characterized in that the material of the organic functional layer comprises one or more organic compounds described in any one of claims 1 to 12, or the material of the organic functional layer comprises the mixture described in claim 12, or the material of the organic functional layer comprises the composition described in claim 14.

16. The organic light-emitting device according to claim 15, wherein the organic functional layer includes at least a light-emitting layer, the material of the light-emitting layer includes a host material and a guest material, and the guest material includes one or more of the organic compounds.

17. It is a display panel, The display panel is characterized by including the organic light-emitting device described in claim 15.

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