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

Abstract

The invention discloses an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound has a structure as shown in a general formula (1) or a general formula (2): # imgabs0 # imgabs1 #. The organic compound has better overall molecular solubility and is easy to purify, so that the purity of the organic compound is improved, and the efficiency and the service life of an organic light-emitting device prepared from the organic compound are further improved.

Description

Technical Field

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

[0002] At present, organic electroluminescent devices usually have an anode, a cathode and an organic layer located between the two, and use the organic material of the organic layer to convert electrical energy into light energy, thereby realizing organic electroluminescence. In order to improve the luminous efficiency and service life of organic electroluminescent devices, the organic layer is often multi-layered, and the organic material of each layer is 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. 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 meet with the electrons to form excitons, and the excitons emit light when they transition back to the ground state, thereby realizing the luminescence of the organic electroluminescent device. Organic electroluminescent devices have the characteristics of autonomous luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast and high response. Therefore, organic electroluminescent devices have broad application prospects.

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

[0004] In order to overcome the above problems, the current luminescent materials are usually various material combinations based on organic compounds, such as composite excited state materials, thermally activated delayed fluorescence (TADF) materials, etc., trying to use reverse internal conversion to achieve high efficiency comparable to phosphorescent organic electroluminescent devices. However, the performance improvement of traditional organic compounds with TADF is limited in terms of efficiency and life, resulting in difficulty in improving the luminous efficiency and service life of organic electroluminescent devices using organic compounds with TADF.

[0005] Therefore, an organic compound for an organic light-emitting device is needed to solve the above technical problems. Summary of the invention

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

[0007] An embodiment of the present application provides an organic compound having a structure as shown in general formula (1) or general formula (2):

[0008]

[0009] Wherein, 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;

[0010] Ar3 and Ar4 are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms;

[0011] R1 and R2 are selected from 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 carbon atom is a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0012] At least one of Ar1, Ar2, Ar3, Ar4, R1 and R2 has a silicon group or a deuterated phenyl group;

[0013] n1 is selected from 0, 1, 2 or 3;

[0014] n2 is selected from 0, 1, 2, 3 or 4.

[0015] In one embodiment of the present application, Ar1 is selected from a group represented by any one of formula (X-1) to formula (X-4):

[0016]

[0017] Ar2 is selected from the group represented by any one of formula (A-1) to formula (A-4):

[0018]

[0019] Ar3 and Ar4 are selected from the group represented by any one of formula (B-1) to formula (B-5):

[0020]

[0021] The attachment site of Ar2 is on a carbon atom of any benzene ring, the attachment site of Ar3 is on a carbon atom of any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring;

[0022] X is selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0023] R0 and L are selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain or branched silicon group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched 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 a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0024] n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0025] a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0026] In one embodiment of the present application, when Ar1 is selected from the group represented by formula (X-2), Ar4 is selected from the group represented by any one of formulas (B-2) to (B-5).

[0027] In one embodiment of the present application, when n0 is greater than or equal to 2, two adjacent R0s and the atoms to which they are connected together form a ring or do not form a ring;

[0028] When n1 is greater than or equal to 2, two adjacent R1s and the ring atoms to which they are connected together form a ring or do not form a ring;

[0029] When n2 is greater than or equal to 2, two adjacent R2s and the ring atoms to which they are connected together form a ring or do not form a ring;

[0030] When a is greater than or equal to 2, two adjacent L's together with the atoms to which they are connected may or may not form a ring.

[0031] In one embodiment of the present application, the organic compound has a structure as shown in any one of the general formulas (2-1) to (2-31):

[0032]

[0033]

[0034] wherein R3 and R4 are selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain or branched silicon group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched 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 carbon atom a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0035] n3 is greater than or equal to 0 and less than or equal to 5. When n3 is greater than or equal to 2, two adjacent R3s and the atoms to which they are connected together may or may not form a ring;

[0036] n4 is greater than or equal to 0 and less than or equal to 5. When n4 is greater than or equal to 2, two adjacent R4s and the atoms to which they are connected may or may not form a ring.

[0037] In one embodiment of the present application, R1, R2, R3, R4 and L are selected from H, D, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, and a cyclic alkyl group having 3 to 10 carbon atoms.

[0038] In one embodiment of the present application, R1, R2, R3, R4 and L are selected from H, D, a straight-chain alkyl group having 1 to 4 carbon atoms, and a branched-chain alkyl group having 3 to 5 carbon atoms.

[0039] In one embodiment of the present application, the organic compound is a blue light-emitting material.

[0040] In one embodiment of the present application, the organic compound is selected from the following compounds 1 to 168:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047] According to the above-mentioned purpose of the present application, an embodiment of the present application also provides a mixture, which includes the organic compound and at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

[0048] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition, which includes the organic compound and at least one organic solvent, or the composition includes the mixture and at least one organic solvent.

[0049] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides an organic light-emitting device, which includes:

[0050] a first electrode;

[0051] a second electrode, disposed opposite to the first electrode; and

[0052] an organic functional layer, located between the first electrode and the second electrode;

[0053] The material of the organic functional layer includes one or more of the organic compounds, or the material of the organic functional layer includes the mixture, or the material of the organic functional layer includes the combination.

[0054] In one embodiment of the present application, the organic functional layer at least includes a light-emitting layer, and 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.

[0055] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a display panel, which includes the organic light-emitting device.

[0056] The embodiments of the present application can effectively increase the molecular weight of the organic compound by adding aromatic rings, silicon groups and / or deuterated phenyl groups to the organic compound, and make the molecular configuration of the organic compound larger, and the molecular gap also larger, thereby making the overall molecular solubility of the organic compound better and facilitating the purification of the organic compound, thereby improving the purity of the organic compound and further improving the efficiency and life of the organic light-emitting device made of the organic compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0057] Figure 1 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M165 provided in the examples of the present application;

[0058] Figure 2 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M166 provided in the examples of the present application;

[0059] Figure 3 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M167 provided in the examples of the present application;

[0060] Figure 4 is a schematic diagram of a structure of an organic light-emitting device provided in an embodiment of the present application;

[0061] Figure 5 It is a schematic diagram of another structure of an organic light-emitting device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0062] The present application will be further described in detail below in conjunction with the accompanying drawings provided by the embodiments of the present application. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application. The description order of the following embodiments is not used as a limitation on the preferred order of the embodiments.

[0063] Unless otherwise defined, all terms (including technical and scientific terms) used in this document have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0064] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0065] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0066] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0067] In the present application, when the same substituent appears multiple times, it can be independently selected from the same or different groups. If the general formula contains multiple R, then R can be independently selected from different or the same groups.

[0068] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen (e.g., F, Cl, Br or I), alkyl group containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, cyano group, isocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group. Preferably, R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen (such as F, Cl, Br or I), alkyl group containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0069] In the present application, "ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0070] In the present application, "aryl" or "aromatic group" refers to an aromatic hydrocarbon group whose ring atoms derived from an aromatic ring compound by removing a hydrogen atom are all carbon atoms. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthyl, fluorenyl, acenaphthene and derivatives thereof. It is understood that multiple aromatic groups may also 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 <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0071] In the present application, "heteroaryl" or "heteroaromatic group" means that at least one carbon atom on the ring skeleton is replaced by a non-carbon atom on the basis of the aryl, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. That is, the ring atoms of the heteroaryl include one or more non-carbon atoms selected from N atoms, O atoms, and S atoms. For example, "substituted or unsubstituted heteroaryl with 5 to 40 ring atoms" refers to a heteroaryl with 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl with 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl with 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl with 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, furidinyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0072] In this application, "alkyl" may refer to a fully saturated straight chain, branched chain and / or cyclic aliphatic hydrocarbon group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0073] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0074] In the present application, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0075] Herein, the term "cycloalkyl" or "cyclic alkyl" refers to a monovalent group having one or more saturated rings in which all ring members are carbon, wherein the term "alkyl" has the same meaning as described above.

[0076] In the present application, the term "heterocyclyl", "heterocyclic" or "heterocycle" refers to a fully saturated or partially unsaturated, but non-aromatic cyclic group having one or more oxygen, sulfur, silicon or nitrogen heteroatoms in the ring, the nitrogen and sulfur heteroatoms may be optionally oxidized and the nitrogen heteroatom may be optionally quaternized. The heterocyclic group may be attached at any atom or carbon atom of the ring or ring system and may be unsubstituted or substituted with one or more moieties as described above for the aryl group.

[0077] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents a halogen (e.g., F, Cl, Br or I)), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0078] In the present application, the term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0079] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0080] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site.

[0081] In the present application, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0082] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0083] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0084] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0085] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0086] In the present application, "two adjacent R1 or two adjacent R3 or two adjacent R5 form a ring with each other" means a ring system formed by two adjacent R1 or two adjacent R3 or two adjacent R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0087] An embodiment of the present application provides an organic compound having a structure as shown in general formula (1) or general formula (2):

[0088]

[0089] Wherein, 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;

[0090] Ar3 and Ar4 are selected from substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms;

[0091] R1 and R2 are selected from 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 carbon atom is a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0092] At least one of Ar1, Ar2, Ar3, Ar4, R1 and R2 has a silicon group or a deuterated phenyl group;

[0093] n1 is selected from 0, 1, 2 or 3;

[0094] n2 is selected from 0, 1, 2, 3 or 4.

[0095] In the implementation process, the embodiments of the present application can effectively increase the molecular weight of the organic compound by adding aromatic rings, silicon groups and / or deuterated phenyl groups to the organic compound, and make the molecular configuration larger and the molecular gap larger, thereby making the overall molecular solubility of the organic compound better and facilitating the purification of the organic compound, thereby improving the purity of the organic compound and further improving the efficiency and life of the organic light-emitting device made of the organic compound.

[0096] Specifically, in some embodiments, Ar1 is selected from a group represented by any one of formula (X-1) to formula (X-4):

[0097]

[0098] Ar2 is selected from the group represented by any one of formula (A-1) to formula (A-4):

[0099]

[0100] Ar3 and Ar4 are selected from the group represented by any one of formula (B-1) to formula (B-5):

[0101]

[0102] The attachment site of Ar2 is on a carbon atom of any benzene ring, the attachment site of Ar3 is on a carbon atom of any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring.

[0103] X is selected from O, S, N-CH3, N-Ph or C(CH3)2.

[0104] R0 and L are selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain or branched silicon group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched 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 a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms.

[0105] n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0106] a is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0107] It should be noted that, each time R0 appears in the above general formula (1) or general formula (2), it can be selected as the same group or different groups, and the group selections between them do not affect each other; similarly, each time R1 appears, it can be selected as the same group or different groups, and the group selections between them do not affect each other; each time R2 appears, it can be selected as the same group or different groups, and the group selections between them do not affect each other; each time L appears, it can be selected as the same group or different groups, and the group selections between them do not affect each other.

[0108] In some embodiments, at least one of Ar1, Ar2, Ar3, Ar4, R0, R1, R2 and L has a silicon group or a deuterated phenyl group; wherein, Ar2 includes L, and when L is selected as D or a deuterated phenyl group, then Ar2 may include a deuterated phenyl group, and similarly, Ar3 and Ar4 include R0, and when R0 is selected as D or a deuterated phenyl group, then Ar3 and Ar4 may include a deuterated phenyl group.

[0109] In some embodiments, at least one of Ar1, Ar2, Ar3, Ar4, R0, R1, R2 and L has a triphenylsilyl group, which can effectively increase the molecular configuration of the organic compound, make the molecular gap larger, make the organic compound have better solubility, facilitate the compound purification, further improve the purity of the organic compound, and thus improve the efficiency and life of the organic light-emitting device made of the organic compound.

[0110] In some embodiments, when Ar1 is selected from the group represented by formula (X-2), Ar4 is selected from the group represented by any one of formula (B-2) to formula (B-5).

[0111] In some embodiments, when n0 is greater than or equal to 2, two adjacent R0s and the atoms to which they are connected form a ring or not; when n1 is greater than or equal to 2, two adjacent R1s and the ring atoms to which they are connected form a ring or not; when n2 is greater than or equal to 2, two adjacent R2s and the ring atoms to which they are connected form a ring or not; when a is greater than or equal to 2, two adjacent Ls and the atoms to which they are connected form a ring or not.

[0112] In some embodiments, two adjacent R0s are mutually cyclic; further, two adjacent R0s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R0s are mutually cyclic to form Wherein, * indicates the connection site.

[0113] In some embodiments, two adjacent R1s are mutually cyclic; further, two adjacent R1s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R1s are mutually cyclic to form Wherein, * indicates the connection site.

[0114] In some embodiments, two adjacent R2s are mutually cyclic; further, two adjacent R2s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R2s are mutually cyclic to form Wherein, * indicates the connection site.

[0115] In some embodiments, two adjacent Ls are mutually cyclic; further, two adjacent Ls are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent Ls are mutually cyclic to form Wherein, * indicates the connection site.

[0116] In some embodiments, the organic compound has a structure as shown in any one of Formula (2-1) to Formula (2-31):

[0117]

[0118]

[0119] wherein R3 and R4 are selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain or branched silicon group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched 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 carbon atom The present invention also includes but is not limited to ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, olefin groups having 1 to 20 carbon atoms, CN, 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 having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms.

[0120] n3 is greater than or equal to 0 and less than or equal to 5. When n3 is greater than or equal to 2, two adjacent R3s and the atoms to which they are connected may or may not form a ring.

[0121] n4 is greater than or equal to 0 and less than or equal to 5. When n4 is greater than or equal to 2, two adjacent R4s and the atoms to which they are connected may or may not form a ring.

[0122] It should be noted that, each time R3 in the above general formula (1) or general formula (2) appears, it can be selected as the same group or different groups, and the group selections do not affect each other; similarly, each time R4 appears, it can be selected as the same group or different groups, and the group selections do not affect each other.

[0123] In some embodiments, two adjacent R3s are mutually cyclic; further, two adjacent R3s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R3s are mutually cyclic to form Wherein, * indicates the connection site.

[0124] In some embodiments, two adjacent R4s are mutually cyclic; further, two adjacent R4s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R4s are mutually cyclic to form Wherein, * indicates the connection site.

[0125] In some embodiments, R1, R2, R3, R4 and L are 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.

[0126] In some embodiments, R1, R2, R3, R4 and L are 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.

[0127] As mentioned above, the embodiments of the present application introduce an alkyl group into the organic compound, which is beneficial to improving the solubility of the organic compound in processes such as inkjet printing, and improving the product quality of the organic light-emitting device using the organic compound.

[0128] In some embodiments, at least one of Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4 and L has a silicon group or a deuterated phenyl group; wherein, Ar2 includes L, and when L is selected as D or a deuterated phenyl group, Ar2 may include a deuterated phenyl group, and similarly, Ar3 and Ar4 include R3 and R4 respectively, and when R3 and R4 are selected as D or a deuterated phenyl group, Ar3 and Ar4 may include a deuterated phenyl group.

[0129] In some embodiments, when Ar2 is selected from a group represented by formula (A-2), the formula (A-2) is selected from at least one of the following groups: Among them, organic compounds containing oxygen, sulfur and nitrogen have better hole transport properties, which is beneficial to improving the luminous efficiency and service life of organic light-emitting devices using the organic compounds.

[0130] In some embodiments, the organic compound is a blue light emitting material.

[0131] In some embodiments, the organic compound is selected from at least one of the following compounds 1 to 168:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] The embodiments of the present application improve the overall molecular solubility of the organic compound and facilitate compound purification by adding biphenyl rings, aromatic rings, silicon groups and / or deuterated phenyl groups to the organic compound, thereby improving the purity of the compound and further improving the efficiency and life of the manufactured organic light-emitting device.

[0140] Furthermore, the embodiments of the present application also provide the preparation process of the organic compounds described in the above embodiments, and provide Examples 1 to 35 to describe in detail the preparation process of the organic compounds provided in the embodiments of the present application.

[0141] Example 1

[0142] The synthetic route of organic compound M1 is as follows:

[0143]

[0144] Synthesis of intermediate 1-3:

[0145] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-3 with a molar weight of 8.21 mmol and a yield of 82.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 337.

[0146] Synthesis of intermediate 1-5:

[0147] Compound 1-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-5 with a molar weight of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS (ASAP) = 481.

[0148] Synthesis of intermediate 1-7:

[0149] Intermediate 1-5 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100° C. under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-7 with a molar weight of 6.51 mmol and a yield of 65.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-7 was: MS (ASAP) = 582.

[0150] Synthesis of intermediate 1-9:

[0151] Intermediate 1-7 (10 mmol) and compound 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-9 with a molar weight of 6.33 mmol and a yield of 63.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-9 was: MS (ASAP) = 796.

[0152] Synthesis of intermediate 1-11:

[0153] Intermediate 1-9 (10 mmol), intermediate 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100° C. and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-11 with a molar weight of 7.76 mmol and a yield of 77.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-11 was: MS (ASAP) = 962.

[0154] Synthesis of intermediate 1-13:

[0155] Intermediate 1-11 (10 mmol) and intermediate 1-12 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-13 with a molar weight of 5.68 mmol and a yield of 56.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-13 was: MS (ASAP) = 1154.

[0156] Synthesis of organic compound M1:

[0157] 10 mmol of intermediate 1-13 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M1, with a yield of 33.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M1 is: MS (ASAP) = 1128.

[0158] Example 2

[0159] The synthetic route of organic compound M12 is as follows:

[0160]

[0161] Synthesis of intermediate 2-1:

[0162] Compound 1-6 (10 mmol) and compound 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-1 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-1 was: MS (ASAP) = 351.

[0163] Synthesis of intermediate 2-2:

[0164] Compound 2-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-2 with a molar weight of 7.39 mmol and a yield of 73.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS (ASAP) = 539.

[0165] Synthesis of intermediate 2-3:

[0166] Intermediate 2-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100° C. under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-3 with a molar weight of 6.72 mmol and a yield of 67.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-3 was: MS (ASAP) = 683.

[0167] Synthesis of intermediate 2-4:

[0168] Intermediate 2-3 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-4 with a molar weight of 6.71 mmol and a yield of 67.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-4 was: MS (ASAP) = 796.

[0169] Synthesis of intermediate 2-5:

[0170] Intermediate 2-4 (10 mmol), intermediate 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-5 with a molar weight of 7.35 mmol and a yield of 73.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-5 was: MS (ASAP) = 962.

[0171] Synthesis of intermediate 2-6:

[0172] Intermediate 2-5 (10 mmol) and intermediate 1-12 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-6 with a molar weight of 5.12 mmol and a yield of 51.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-6 was: MS (ASAP) = 1154.

[0173] Synthesis of organic compound M12:

[0174] In a 250 ml three-necked flask, 10 mmol of intermediate 2-6 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M12, with a yield of 43.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M12 is: MS (ASAP) = 1128.

[0175] Example 3

[0176] The synthetic route of organic compound M15 is as follows:

[0177]

[0178] Synthesis of intermediate 3-2:

[0179] The intermediate 2-3 (10 mmol), compound 3-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 3-2 with a molar weight of 7.89 mmol and a yield of 78.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 3-2 was: MS (ASAP) = 928.

[0180] Synthesis of intermediate 3-3:

[0181] Intermediate 3-2 (10 mmol), intermediate 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-3 with a molar weight of 7.71 mmol and a yield of 77.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-3 was: MS (ASAP) = 1094.

[0182] Synthesis of intermediate 3-4:

[0183] Intermediate 3-3 (10 mmol) and intermediate 1-12 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-4 with a molar weight of 5.41 mmol and a yield of 54.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-4 was: MS (ASAP) = 1154.

[0184] Synthesis of organic compound M15:

[0185] 10 mmol of intermediate 3-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M15, with a yield of 41.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M15 is: MS (ASAP) = 1260.

[0186] Example 4

[0187] The synthetic route of organic compound M16 is as follows:

[0188]

[0189] Synthesis of intermediate 4-1:

[0190] Compound 3-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 4-1 with a molar weight of 8.73 mmol and a yield of 87.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-1 was: MS (ASAP) = 469.

[0191] Synthesis of intermediate 4-2:

[0192] Compound 4-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 4-2 with a molar weight of 7.86 mmol and a yield of 78.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-2 was: MS (ASAP) = 613.

[0193] Synthesis of intermediate 4-3:

[0194] Intermediate 4-2 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100° C. under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 4-3 with a molar weight of 6.82 mmol and a yield of 68.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-3 was: MS (ASAP) = 714.

[0195] Synthesis of intermediate 4-4:

[0196] The intermediate 4-3 (10 mmol) and compound 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and the temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction liquid was cooled, the solvent was removed by rotary evaporation, the reaction liquid was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 4-4 with a molar weight of 5.63 mmol and a yield of 56.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 4-4 was: MS (ASAP) = 928.

[0197] Synthesis of intermediate 4-5:

[0198] Intermediate 4-4 (10 mmol), intermediate 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 4-5 with a molar weight of 7.76 mmol and a yield of 77.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-5 was: MS (ASAP) = 1094.

[0199] Synthesis of intermediate 4-6:

[0200] Intermediate 4-5 (10 mmol) and intermediate 1-12 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 4-6 with a molar weight of 5.11 mmol and a yield of 51.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-6 was: MS (ASAP) = 1286.

[0201] Synthesis of organic compound M16:

[0202] In a 250 ml three-necked flask, 10 mmol of intermediate 4-6 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was removed by evaporation under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M16, with a yield of 37.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M16 is: MS (ASAP) = 1260.

[0203] Example 5

[0204] The synthetic route of organic compound M60 is as follows:

[0205]

[0206] Synthesis of intermediate 5-2:

[0207] Intermediate 3-3 (10 mmol) and intermediate 5-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-2 with a molar weight of 5.28 mmol and a yield of 52.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-4 was: MS (ASAP) = 1190.

[0208] Synthesis of organic compound M60:

[0209] 10 mmol of intermediate 5-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M60, with a yield of 32.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M60 is: MS (ASAP) = 1164.

[0210] Example 6

[0211] The synthetic route of organic compound M64 is as follows:

[0212]

[0213] Synthesis of intermediate 6-2:

[0214] Intermediate 4-5 (10 mmol) and intermediate 6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-2 with a molar weight of 5.93 mmol and a yield of 59.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 6-2 was: MS (ASAP) = 1190.

[0215] Synthesis of organic compound M64:

[0216] 10 mmol of intermediate 6-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M64, with a yield of 32.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M64 is: MS (ASAP) = 1164.

[0217] Example 7

[0218] The synthetic route of organic compound M68 is as follows:

[0219]

[0220] Synthesis of intermediate 7-2:

[0221] Compound 7-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 7-2 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-2 was: MS (ASAP) = 469.

[0222] Synthesis of intermediate 7-3:

[0223] Compound 7-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 7-3 with a molar weight of 7.21 mmol and a yield of 72.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-3 was: MS (ASAP) = 613.

[0224] Synthesis of intermediate 7-4:

[0225] The intermediate 7-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 7-4 with a molar weight of 6.52 mmol and a yield of 65.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 7-4 was: MS (ASAP) = 714.

[0226] Synthesis of intermediate 7-5:

[0227] The intermediate 7-4 (10 mmol) and compound 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 7-5 with a molar weight of 5.13 mmol and a yield of 51.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 7-5 was: MS (ASAP) = 928.

[0228] Synthesis of intermediate 7-6:

[0229] Intermediate 7-5 (10 mmol), intermediate 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-6 with a molar weight of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-6 was: MS (ASAP) = 1094.

[0230] Synthesis of intermediate 7-8:

[0231] Intermediate 7-6 (10 mmol) and intermediate 7-7 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-8 with a molar weight of 5.56 mmol and a yield of 55.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-8 was: MS (ASAP) = 1176.

[0232] Synthesis of organic compound M68:

[0233] 10 mmol of intermediate 7-8 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M68, with a yield of 32.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M68 is: MS (ASAP) = 1150.

[0234] Example 8

[0235] The synthetic route of organic compound M72 is as follows:

[0236]

[0237] Synthesis of intermediate 8-1:

[0238] Intermediate 2-3 (10 mmol), compound 7-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 8-1 with a molar weight of 7.21 mmol and a yield of 72.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-1 was: MS (ASAP) = 928.

[0239] Synthesis of intermediate 8-2:

[0240] Intermediate 8-1 (10 mmol), intermediate 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-2 with a molar weight of 7.21 mmol and a yield of 72.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-2 was: MS (ASAP) = 1094.

[0241] Synthesis of intermediate 8-4:

[0242] Intermediate 8-2 (10 mmol) and intermediate 8-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-4 with a molar weight of 5.22 mmol and a yield of 52.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-4 was: MS (ASAP) = 1176.

[0243] Synthesis of organic compound M72:

[0244] In a 250 ml three-necked flask, 10 mmol of intermediate 8-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a N2 atmosphere. A solution of t-BuLi (tert-butyl lithium) (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M72, with a yield of 25.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M72 is: MS (ASAP) = 1150.

[0245] Example 9

[0246] The synthetic route of organic compound M89 is as follows:

[0247]

[0248] Synthesis of intermediate 9-1:

[0249] Intermediate 1-6 (10 mmol) and compound 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-1 with a molar weight of 8.93 mmol and a yield of 89.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-1 was: MS (ASAP) = 351.

[0250] Synthesis of intermediate 9-3:

[0251] Compound 9-1 (10 mmol), compound 9-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-3 with a molar weight of 8.53 mmol and a yield of 85.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-3 was: MS (ASAP) = 573.

[0252] Synthesis of intermediate 9-4:

[0253] Compound 9-3 (10 mmol), compound 3-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-4 with a molar weight of 6.27 mmol and a yield of 62.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-4 was: MS (ASAP) = 774.

[0254] Synthesis of intermediate 9-5:

[0255] Intermediate 9-4 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-5 with a molar weight of 6.71 mmol and a yield of 67.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-5 was: MS (ASAP) = 962.

[0256] Synthesis of intermediate 9-6:

[0257] Intermediate 9-5 (10 mmol), compound 1-10 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-6 with a molar weight of 5.96 mmol and a yield of 59.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-6 was: MS (ASAP) = 1128.

[0258] Synthesis of intermediate 9-8:

[0259] Intermediate 9-6 (10 mmol) and intermediate 9-7 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-8 with a molar weight of 7.93 mmol and a yield of 79.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-8 was: MS (ASAP) = 1276.

[0260] Synthesis of intermediate 9-10:

[0261] Intermediate 9-8 (10 mmol), intermediate 9-9 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-10 with a molar weight of 5.03 mmol and a yield of 50.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-10 was: MS (ASAP) = 1409.

[0262] Synthesis of organic compound M89:

[0263] In a 250 ml three-necked flask, 10 mmol of intermediate 9-10 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M89, with a yield of 29.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M89 is: MS (ASAP) = 1383.

[0264] Example 10

[0265] The synthetic route of organic compound M90 is as follows:

[0266]

[0267] Synthesis of intermediate 10-1:

[0268] Compound 9-3 (10 mmol), compound 1-3 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 10-1 with a molar weight of 7.89 mmol and a yield of 78.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-1 was: MS (ASAP) = 830.

[0269] Synthesis of intermediate 10-2:

[0270] Intermediate 10-1 (10 mmol), compound 1-10 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 10-2 with a molar weight of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-2 was: MS (ASAP) = 996.

[0271] Synthesis of intermediate 10-4:

[0272] Intermediate 10-2 (10 mmol) and compound 10-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 10-4 with a molar weight of 5.71 mmol and a yield of 57.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-4 was: MS (ASAP) = 1141.

[0273] Synthesis of intermediate 10-5:

[0274] Intermediate 10-4 (10 mmol), intermediate 9-9 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 10-5 with a molar weight of 5.63 mmol and a yield of 56.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-5 was: MS (ASAP) = 1274.

[0275] Synthesis of organic compound M90:

[0276] 10 mmol of intermediate 10-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M90, with a yield of 36.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M90 is: MS (ASAP) = 1248.

[0277] Embodiment 11

[0278] The synthetic route of organic compound M99 is as follows:

[0279]

[0280] Synthesis of intermediate 11-1:

[0281] Compound 9-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 11-1 with a molar weight of 8.43 mmol and a yield of 84.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-1 was: MS (ASAP) = 539.

[0282] Synthesis of intermediate 11-3:

[0283] Compound 11-1 (10 mmol), compound 11-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 11-3 with a molar weight of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-3 was: MS (ASAP) = 759.

[0284] Synthesis of intermediate 11-5:

[0285] Intermediate 11-3 (10 mmol), compound 11-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 11-5 with a molar weight of 7.89 mmol and a yield of 78.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-5 was: MS (ASAP) = 906.

[0286] Synthesis of intermediate 11-6:

[0287] The intermediate 11-5 (10 mmol), compound 1-2 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 11-6 with a molar weight of 7.91 mmol and a yield of 79.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 11-6 was: MS (ASAP) = 1094.

[0288] Synthesis of intermediate 11-8:

[0289] Intermediate 11-6 (10 mmol) and intermediate 11-7 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 11-8 with a molar weight of 7.93 mmol and a yield of 79.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-8 was: MS (ASAP) = 1226.

[0290] Synthesis of organic compound M99:

[0291] 10 mmol of intermediate 11-8 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M99, with a yield of 43.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M99 is: MS (ASAP) = 1200.

[0292] Example 12

[0293] The synthetic route of organic compound M116 is as follows:

[0294]

[0295] Synthesis of intermediate 12-2:

[0296] Intermediate 1-6 (10 mmol) and compound 12-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 12-2 with a molar weight of 8.73 mmol and a yield of 87.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-2 was: MS (ASAP) = 427.

[0297] Synthesis of intermediate 12-3:

[0298] Compound 12-2 (10 mmol), compound 1-10 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 12-3 with a molar weight of 8.84 mmol and a yield of 88.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-3 was: MS (ASAP) = 593.

[0299] Synthesis of intermediate 12-4:

[0300] Compound 12-3 (10 mmol), compound 1-12 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 12-4 with a molar weight of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-4 was: MS (ASAP) = 785.

[0301] Synthesis of intermediate 12-5:

[0302] Intermediate 12-4 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 12-5 with a molar weight of 7.31 mmol and a yield of 73.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-5 was: MS (ASAP) = 929.

[0303] Synthesis of intermediate 12-7:

[0304] Intermediate 12-5 (10 mmol), compound 12-6 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 12-7 with a molar weight of 6.16 mmol and a yield of 61.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-7 was: MS (ASAP) = 1110.

[0305] Synthesis of intermediate 12-8:

[0306] Intermediate 12-7 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 12-8 with a molar weight of 7.33 mmol and a yield of 73.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-8 was: MS (ASAP) = 1298.

[0307] Synthesis of intermediate 12-10:

[0308] Intermediate 12-8 (10 mmol) and intermediate 12-9 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 12-10 with a molar weight of 5.73 mmol and a yield of 57.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-10 was: MS (ASAP) = 1392.

[0309] Synthesis of organic compound M116:

[0310] In a 250 ml three-necked flask, 10 mmol of intermediate 12-10 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a N2 atmosphere. A n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M116, with a yield of 38.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M116 is: MS (ASAP) = 1366.

[0311] Example 13

[0312] The synthetic route of organic compound M120 is as follows:

[0313]

[0314] Synthesis of intermediate 13-1:

[0315] Intermediate 12-4 (10 mmol), compound 9-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 13-1 with a molar weight of 7.88 mmol and a yield of 78.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-1 was: MS (ASAP) = 963.

[0316] Synthesis of intermediate 13-3:

[0317] The intermediate 13-1 (10 mmol), compound 13-2 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 13-3 with a molar weight of 6.96 mmol and a yield of 69.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 13-3 was: MS (ASAP) = 1096.

[0318] Synthesis of intermediate 13-4:

[0319] Intermediate 13-3 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 13-4 with a molar weight of 7.71 mmol and a yield of 77.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-4 was: MS (ASAP) = 1284.

[0320] Synthesis of intermediate 13-5:

[0321] Intermediate 13-4 (10 mmol) and intermediate 12-9 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 13-5 with a molar weight of 5.81 mmol and a yield of 58.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-5 was: MS (ASAP) = 1331.

[0322] Synthesis of organic compound M120:

[0323] 10 mmol of intermediate 13-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M120, with a yield of 33.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M120 is: MS (ASAP) = 1305.

[0324] Embodiment 14

[0325] The synthetic route of organic compound M145 is as follows:

[0326]

[0327] Synthesis of intermediate 14-2:

[0328] Intermediate 14-1 (10 mmol) and compound 12-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 14-2 with a molar weight of 8.12 mmol and a yield of 81.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-2 was: MS (ASAP) = 375.

[0329] Synthesis of intermediate 14-3:

[0330] Compound 14-2 (10 mmol), compound 12-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 14-3 with a molar weight of 8.54 mmol and a yield of 85.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-3 was: MS (ASAP) = 709.

[0331] Synthesis of intermediate 14-4:

[0332] Compound 14-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 14-4 with a molar weight of 6.57 mmol and a yield of 65.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-4 was: MS (ASAP) = 853.

[0333] Synthesis of intermediate 14-5:

[0334] Intermediate 14-4 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 14-5 with a molar weight of 7.81 mmol and a yield of 78.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-5 was: MS (ASAP) = 966.

[0335] Synthesis of intermediate 14-7:

[0336] Intermediate 14-5 (10 mmol), compound 14-6 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 14-7 with a molar weight of 5.86 mmol and a yield of 58.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-7 was: MS (ASAP) = 1174.

[0337] Synthesis of organic compound M145:

[0338] 10 mmol of intermediate 14-7 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M145, with a yield of 36.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M145 is: MS (ASAP) = 1148.

[0339] Embodiment 15

[0340] The synthetic route of organic compound M148 is as follows:

[0341]

[0342] Synthesis of intermediate 15-2:

[0343] Intermediate 15-1 (10 mmol) and compound 12-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 15-2 with a molar weight of 8.42 mmol and a yield of 84.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 15-2 was: MS (ASAP) = 559.

[0344] Synthesis of intermediate 15-3:

[0345] Compound 15-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 15-3 with a molar weight of 8.94 mmol and a yield of 89.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 15-3 was: MS (ASAP) = 703.

[0346] Synthesis of intermediate 15-5:

[0347] Compound 15-3 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 15-5 with a molar weight of 6.77 mmol and a yield of 67.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 15-5 was: MS (ASAP) = 794.

[0348] Synthesis of intermediate 15-6:

[0349] Intermediate 15-5 (10 mmol), compound 1-12 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 15-6 with a molar weight of 7.53 mmol and a yield of 75.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 15-6 was: MS (ASAP) = 986.

[0350] Synthesis of intermediate 15-7:

[0351] Intermediate 15-6 (10 mmol), compound 1-2 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 15-7 with a molar weight of 5.49 mmol and a yield of 54.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 15-7 was: MS (ASAP) = 1174.

[0352] Synthesis of organic compound M148:

[0353] 10 mmol of intermediate 15-7 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M148, with a yield of 39.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M148 is: MS (ASAP) = 1148.

[0354] Example 16

[0355] The synthetic route of organic compound M149 is as follows:

[0356]

[0357] Synthesis of intermediate 16-2:

[0358] Intermediate 14-5 (10 mmol), compound 16-1 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 16-2 with a molar weight of 7.59 mmol and a yield of 75.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 16-2 was: MS (ASAP) = 1110.

[0359] Synthesis of intermediate 16-4:

[0360] Intermediate 16-2 (10 mmol) and compound 16-3 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 16-4 with a molar weight of 8.83 mmol and a yield of 88.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 16-4 was: MS (ASAP) = 1306.

[0361] Synthesis of organic compound M149:

[0362] 10 mmol of intermediate 16-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M149, with a yield of 43.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M149 is: MS (ASAP) = 1280.

[0363] Embodiment 17

[0364] The synthetic route of organic compound M150 is as follows:

[0365]

[0366] Synthesis of intermediate 17-2:

[0367] Intermediate 14-5 (10 mmol), compound 17-1 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 17-2 with a molar weight of 7.93 mmol and a yield of 79.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 17-2 was: MS (ASAP) = 1174.

[0368] Synthesis of organic compound M150:

[0369] 10 mmol of intermediate 17-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M150, with a yield of 36.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M150 is: MS (ASAP) = 1148.

[0370] Embodiment 18

[0371] The synthetic route of organic compound M151 is as follows:

[0372]

[0373] Synthesis of intermediate 18-2:

[0374] Compound 14-2 (10 mmol), compound 18-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 18-2 with a molar weight of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-2 was: MS (ASAP) = 507.

[0375] Synthesis of intermediate 18-3:

[0376] Compound 18-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 18-3 with a molar weight of 6.97 mmol and a yield of 69.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-3 was: MS (ASAP) = 651.

[0377] Synthesis of intermediate 18-4:

[0378] Intermediate 18-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 18-4 with a molar weight of 7.42 mmol and a yield of 74.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-4 was: MS (ASAP) = 752.

[0379] Synthesis of intermediate 18-6:

[0380] Intermediate 18-4 (10 mmol), compound 18-5 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 18-6 with a molar weight of 5.97 mmol and a yield of 59.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-6 was: MS (ASAP) = 1042.

[0381] Synthesis of intermediate 18-7:

[0382] Intermediate 18-6 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 18-7 with a molar weight of 7.27 mmol and a yield of 72.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-7 was: MS (ASAP) = 1230.

[0383] Synthesis of organic compound M151:

[0384] 10 mmol of intermediate 18-7 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M151, with a yield of 33.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M151 is: MS (ASAP) = 1204.

[0385] Embodiment 19

[0386] The synthetic route of organic compound M152 is as follows:

[0387]

[0388] Synthesis of intermediate 19-2:

[0389] Compound 14-2 (10 mmol), compound 19-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 19-2 with a molar weight of 6.45 mmol and a yield of 64.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 19-2 was: MS (ASAP) = 583.

[0390] Synthesis of intermediate 19-3:

[0391] Compound 19-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 19-3 with a molar weight of 6.91 mmol and a yield of 69.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 19-3 was: MS (ASAP) = 727.

[0392] Synthesis of intermediate 19-4:

[0393] Intermediate 19-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 19-4 with a molar weight of 5.54 mmol and a yield of 55.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 19-4 was: MS (ASAP) = 828.

[0394] Synthesis of intermediate 19-5:

[0395] Intermediate 19-4 (10 mmol), compound 18-5 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 19-5 with a molar weight of 5.49 mmol and a yield of 54.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 19-5 was: MS (ASAP) = 1118.

[0396] Synthesis of intermediate 19-6:

[0397] Intermediate 19-5 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 19-6 with a molar weight of 7.55 mmol and a yield of 75.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 19-6 was: MS (ASAP) = 1306.

[0398] Synthesis of organic compound M152:

[0399] 10 mmol of intermediate 19-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M152, with a yield of 29.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M152 is: MS (ASAP) = 1280.

[0400] Embodiment 20

[0401] The synthetic route of organic compound M153 is as follows:

[0402]

[0403] Synthesis of intermediate 20-1:

[0404] Intermediate 18-6 (10 mmol), intermediate 14-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 20-1 with a molar weight of 7.76 mmol and a yield of 77.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 20-1 was: MS (ASAP) = 1250.

[0405] Synthesis of organic compound M153:

[0406] 10 mmol of intermediate 20-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M153, with a yield of 36.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M153 is: MS (ASAP) = 1224.

[0407] Embodiment 21

[0408] The synthetic route of organic compound M154 is as follows:

[0409]

[0410] Synthesis of intermediate 21-1:

[0411] Intermediate 19-5 (10 mmol), intermediate 14-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 21-1 with a molar weight of 6.53 mmol and a yield of 65.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 21-1 was: MS (ASAP) = 1326.

[0412] Synthesis of organic compound M154:

[0413] 10 mmol of intermediate 21-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M154, with a yield of 31.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M154 is: MS (ASAP) = 1300.

[0414] Embodiment 22

[0415] The synthetic route of organic compound M155 is as follows:

[0416]

[0417] Synthesis of intermediate 22-1:

[0418] Compound 14-2 (10 mmol), compound 18-5 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 22-1 with a molar weight of 5.67 mmol and a yield of 56.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 22-1 was: MS (ASAP) = 709.

[0419] Synthesis of intermediate 22-3:

[0420] Compound 22-1 (10 mmol), compound 22-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 22-3 with a molar weight of 6.18 mmol and a yield of 61.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 22-3 was: MS (ASAP) = 978.

[0421] Synthesis of intermediate 22-4:

[0422] Intermediate 22-3 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 22-4 with a molar weight of 7.27 mmol and a yield of 72.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 22-4 was: MS (ASAP) = 1235.

[0423] Synthesis of organic compound M155:

[0424] 10 mmol of intermediate 22-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M155, with a yield of 28.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M155 is: MS (ASAP) = 1209.

[0425] Embodiment 23

[0426] The synthetic route of organic compound M156 is as follows:

[0427]

[0428] Synthesis of intermediate 23-2:

[0429] Intermediate 14-4 (10 mmol), intermediate 23-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 23-2 with a molar weight of 7.86 mmol and a yield of 78.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-2 was: MS (ASAP) = 967.

[0430] Synthesis of intermediate 23-3:

[0431] Compound 23-2 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 23-3 with a molar weight of 5.23 mmol and a yield of 52.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-3 was: MS (ASAP) = 1155.

[0432] Synthesis of organic compound M156:

[0433] 10 mmol of intermediate 23-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M156, with a yield of 43.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M156 is: MS (ASAP) = 1129.

[0434] Embodiment 24

[0435] The synthetic route of organic compound M157 is as follows:

[0436]

[0437] Synthesis of intermediate 24-2:

[0438] Intermediate 14-4 (10 mmol), intermediate 24-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 24-2 with a molar weight of 7.37 mmol and a yield of 73.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-2 was: MS (ASAP) = 989.

[0439] Synthesis of intermediate 24-4:

[0440] Intermediate 24-2 (10 mmol) and compound 24-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-4 with a molar weight of 8.61 mmol and a yield of 86.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-4 was: MS (ASAP) = 991.

[0441] Synthesis of intermediate 24-5:

[0442] Compound 24-4 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-5 with a molar weight of 5.63 mmol and a yield of 56.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-5 was: MS (ASAP) = 1179.

[0443] Synthesis of organic compound M157:

[0444] 10 mmol of intermediate 24-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M157, with a yield of 41.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M157 is: MS (ASAP) = 1153.

[0445] Embodiment 25

[0446] The synthetic route of organic compound M158 is as follows:

[0447]

[0448] Synthesis of intermediate 25-1:

[0449] Compound 18-2 (10 mmol), compound 22-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 25-1 with a molar weight of 6.33 mmol and a yield of 63.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 25-1 was: MS (ASAP) = 776.

[0450] Synthesis of intermediate 25-2:

[0451] Intermediate 25-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 25-2 with a molar weight of 8.36 mmol and a yield of 83.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 25-2 was: MS (ASAP) = 1033.

[0452] Synthesis of organic compound M158:

[0453] 10 mmol of intermediate 25-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M158, with a yield of 36.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M158 is: MS (ASAP) = 1007.

[0454] Embodiment 26

[0455] The synthetic route of organic compound M159 is as follows:

[0456]

[0457] Synthesis of intermediate 26-1:

[0458] Compound 25-1 (10 mmol), compound 23-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 26-1 with a molar weight of 6.89 mmol and a yield of 68.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 26-1 was: MS (ASAP) = 846.

[0459] Synthesis of intermediate 26-2:

[0460] Intermediate 26-1 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 26-2 with a molar weight of 8.11 mmol and a yield of 81.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 26-2 was: MS (ASAP) = 1034.

[0461] Synthesis of organic compound M159:

[0462] 10 mmol of intermediate 26-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise, the temperature was raised to 60 ° C for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M159, with a yield of 37.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M159 is: MS (ASAP) = 1008.

[0463] Embodiment 27

[0464] The synthetic route of organic compound M160 is as follows:

[0465]

[0466] Synthesis of intermediate 27-2:

[0467] Compound 14-2 (10 mmol), compound 27-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 27-2 with a molar weight of 5.80 mmol and a yield of 58.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 27-2 was: MS (ASAP) = 709.

[0468] Synthesis of intermediate 27-3:

[0469] Compound 27-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 27-3 with a molar weight of 8.63 mmol and a yield of 86.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 27-3 was: MS (ASAP) = 853.

[0470] Synthesis of intermediate 27-4:

[0471] Compound 27-3 (10 mmol), compound 23-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 27-4 with a molar weight of 6.84 mmol and a yield of 68.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 27-4 was: MS (ASAP) = 967.

[0472] Synthesis of intermediate 27-5:

[0473] Intermediate 27-4 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 27-5 with a molar weight of 7.69 mmol and a yield of 76.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 27-5 was: MS (ASAP) = 1155.

[0474] Synthesis of organic compound M160:

[0475] 10 mmol of intermediate 27-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M160, with a yield of 37.0%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M160 is: MS (ASAP) = 1129.

[0476] Embodiment 28

[0477] The synthetic route of organic compound M161 is as follows:

[0478]

[0479] Synthesis of intermediate 28-2:

[0480] Compound 14-2 (10 mmol), compound 28-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 28-2 with a molar weight of 6.90 mmol and a yield of 69.0%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 28-2 was: MS (ASAP) = 730.

[0481] Synthesis of intermediate 28-3:

[0482] Compound 28-2 (10 mmol), compound 22-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 28-3 with a molar weight of 8.12 mmol and a yield of 81.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 28-3 was: MS (ASAP) = 999.

[0483] Synthesis of intermediate 28-4:

[0484] Compound 28-3 (10 mmol), compound 23-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 28-4 with a molar weight of 7.53 mmol and a yield of 75.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 28-4 was: MS (ASAP) = 1069.

[0485] Synthesis of intermediate 28-5:

[0486] Intermediate 28-4 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 28-5 with a molar weight of 7.20 mmol and a yield of 72.0%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 28-5 was: MS (ASAP) = 1257.

[0487] Synthesis of organic compound M161:

[0488] 10 mmol of intermediate 28-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M161, with a yield of 32.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M161 is: MS (ASAP) = 1231.

[0489] Embodiment 29

[0490] The synthetic route of organic compound M162 is as follows:

[0491]

[0492] Synthesis of intermediate 29-2:

[0493] Compound 14-2 (10 mmol), compound 29-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 29-2 with a molar weight of 7.92 mmol and a yield of 79.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-2 was: MS (ASAP) = 532.

[0494] Synthesis of intermediate 29-3:

[0495] Compound 29-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 29-3 with a molar weight of 8.56 mmol and a yield of 85.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-3 was: MS (ASAP) = 676.

[0496] Synthesis of intermediate 29-5:

[0497] Compound 29-3 (10 mmol), compound 29-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 29-5 with a molar weight of 7.21 mmol and a yield of 72.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-5 was: MS (ASAP) = 921.

[0498] Synthesis of intermediate 29-6:

[0499] Intermediate 29-5 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 29-6 with a molar weight of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-6 was: MS (ASAP) = 1109.

[0500] Synthesis of organic compound M162:

[0501] 10 mmol of intermediate 29-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M162, with a yield of 36.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M162 is: MS (ASAP) = 1083.

[0502] Embodiment 30

[0503] The synthetic route of organic compound M163 is as follows:

[0504]

[0505] Synthesis of intermediate 30-2:

[0506] Compound 14-2 (10 mmol), compound 30-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 30-2 with a molar weight of 7.35 mmol and a yield of 73.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-2 was: MS (ASAP) = 639.

[0507] Synthesis of intermediate 30-3:

[0508] Compound 30-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 30-3 with a molar weight of 8.22 mmol and a yield of 82.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-3 was: MS (ASAP) = 783.

[0509] Synthesis of intermediate 30-4:

[0510] Compound 30-3 (10 mmol), compound 24-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 30-4 with a molar weight of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-4 was: MS (ASAP) = 919.

[0511] Synthesis of intermediate 30-5:

[0512] The intermediate 30-4 (10 mmol) and compound 24-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 30-5 with a molar weight of 8.09 mmol and a yield of 80.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 30-5 was: MS (ASAP) = 922.

[0513] Synthesis of intermediate 30-6:

[0514] Intermediate 30-5 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 30-6 with a molar weight of 7.85 mmol and a yield of 78.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-6 was: MS (ASAP) = 1110.

[0515] Synthesis of organic compound M163:

[0516] In a 250 ml three-necked flask, 10 mmol of intermediate 30-6 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a N2 atmosphere. A solution of t-BuLi (tert-butyl lithium) (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M163, with a yield of 36.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M163 is: MS (ASAP) = 1084.

[0517] Embodiment 31

[0518] The synthetic route of organic compound M164 is as follows:

[0519]

[0520] Synthesis of intermediate 31-2:

[0521] Compound 30-3 (10 mmol), compound 31-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 31-2 with a molar weight of 7.96 mmol and a yield of 79.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 31-2 was: MS (ASAP) = 996.

[0522] Synthesis of intermediate 31-3:

[0523] The intermediate 31-3 (10 mmol) and compound 24-3 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C under a nitrogen atmosphere and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 31-3 with a molar weight of 8.57 mmol and a yield of 85.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 31-3 was: MS (ASAP) = 1002.

[0524] Synthesis of intermediate 31-4:

[0525] Intermediate 31-3 (10 mmol), intermediate 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 31-4 with a molar weight of 7.25 mmol and a yield of 72.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 31-4 was: MS (ASAP) = 1190.

[0526] Synthesis of organic compound M164:

[0527] 10 mmol of intermediate 31-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M164, with a yield of 44.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M164 is: MS (ASAP) = 1164.

[0528] Embodiment 32

[0529] The synthetic route of organic compound M165 is as follows:

[0530]

[0531] Synthesis of intermediate 32-2:

[0532] Compound 22-1 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 32-2 with a molar weight of 6.59 mmol and a yield of 65.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-2 was: MS (ASAP) = 1111.

[0533] Synthesis of intermediate 32-3:

[0534] Intermediate 32-2 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 32-3 with a molar weight of 7.93 mmol and a yield of 79.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-3 was: MS (ASAP) = 1412.

[0535] Synthesis of organic compound M165:

[0536] 10 mmol of intermediate 32-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120°C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, namely organic compound M165, with a yield of 37.7%. The hydrogen nuclear magnetic resonance spectrum of organic compound M165 is shown as follows: Figure 1 As shown, the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M165 is: MS (ASAP) = 1386.

[0537] Embodiment 33

[0538] The synthetic route of organic compound M166 is as follows:

[0539]

[0540] Synthesis of intermediate 33-1:

[0541] Compound 18-2 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 33-1 with a molar weight of 6.59 mmol and a yield of 65.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 33-1 was: MS (ASAP) = 909.

[0542] Synthesis of intermediate 33-2:

[0543] Intermediate 33-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 33-2 with a molar weight of 7.54 mmol and a yield of 75.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 33-2 was: MS (ASAP) = 1210.

[0544] Synthesis of organic compound M166:

[0545] 10 mmol of intermediate 33-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120°C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; the product was recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, namely organic compound M166, with a yield of 32.8%. The hydrogen nuclear magnetic resonance spectrum of organic compound M166 is shown as follows: Figure 2As shown, the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M166 is: MS (ASAP) = 1184.

[0546] Embodiment 34

[0547] The synthetic route of organic compound M167 is as follows:

[0548]

[0549] Synthesis of intermediate 34-1:

[0550] Compound 19-2 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 34-1 with a molar weight of 8.41 mmol and a yield of 84.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 34-1 was: MS (ASAP) = 985.

[0551] Synthesis of intermediate 34-2:

[0552] Intermediate 34-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 34-2 with a molar weight of 8.03 mmol and a yield of 80.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 34-2 was: MS (ASAP) = 1286.

[0553] Synthesis of organic compound M167:

[0554] 10 mmol of intermediate 34-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120°C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; the product was recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, namely organic compound M167, with a yield of 38.3%. The hydrogen nuclear magnetic resonance spectrum of organic compound M167 is shown as follows: Figure 3 As shown, the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M167 is: MS (ASAP) = 1260.

[0555] Embodiment 35

[0556] The synthetic route of organic compound M168 is as follows:

[0557]

[0558] Synthesis of intermediate 35-1:

[0559] Compound 30-2 (10 mmol), compound 32-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 35-1 with a molar weight of 8.17 mmol and a yield of 81.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-1 was: MS (ASAP) = 1041.

[0560] Synthesis of intermediate 35-2:

[0561] Intermediate 35-1 (10 mmol), intermediate 1-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 120°C and stirred for 3 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 35-2 with a molar weight of 7.29 mmol and a yield of 72.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-2 was: MS (ASAP) = 1342.

[0562] Synthesis of organic compound M168:

[0563] 10 mmol of intermediate 35-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then the reaction solution was cooled to 0 ° C, and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M168, with a yield of 39.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M168 is: MS (ASAP) = 1316.

[0564] As mentioned above, the boron-containing biphenyl organic compound provided in the embodiments of the present application introduces structures such as dibenzofuran, dibenzothiophene, carbazole, benzopentacyclic ring, triphenylene and / or naphthalene into the boron nitrogen compound, so that the overall molecular conjugation is greater, thereby improving the luminous efficiency and service life of the organic light-emitting device using the organic compound; at the same time, the introduction of structures such as tetralin and / or indane into the boron nitrogen compound makes the molecule more soluble in processes such as inkjet printing, facilitates compound purification, thereby improving the purity of the organic compound, and further improving the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0565] An embodiment of the present application also provides a mixture, which includes the organic compound described in the above embodiment and at least one organic functional material; in some embodiments, when the mixture provided by the embodiment of the present application is 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, luminescent materials, host materials or organic dyes.

[0566] In addition, embodiments of the present application further provide a composition, which includes the organic compound described in the above embodiments and at least one organic solvent, or the composition includes the mixture described in the above embodiments and at least one organic solvent.

[0567] In some embodiments, the composition may be a solution or a suspension, and the composition may include a dispersant and a dispersant, wherein the dispersant is one or more of the organic compounds described above and at least one organic solvent, or the dispersant is a mixture described above, and the dispersant is used to disperse the dispersant.

[0568] In the composition, the mass fraction of the organic compound as described above may be 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, further preferably 0.5% to 10%, most preferably 1% to 5%.

[0569] When the composition is used in a printing process, the composition can be an ink, and the viscosity and surface tension of the ink are important parameters. The surface tension parameters of the appropriate ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the ink at the working temperature or at 25°C ranges from 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 use in an inkjet printing process. In some embodiments, the viscosity of the ink at the working temperature or at 25°C ranges from 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 use in an inkjet printing process.

[0570] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is within the range of 17.0 to 23.2 MPa1 / 2, preferably within the range of 18.5 to 21.0 MPa1 / 2; the δp (polar force) is within the range of 0.2 to 12.5 MPa1 / 2, preferably within the range of 2.0 to 6.0 MPa1 / 2; the δh (hydrogen bonding force) is within the range of 0.9 to 14.2 MPa1 / 2, preferably within the range of 2.0 to 6.0 MPa1 / 2.

[0571] In some embodiments, the boiling point of the dispersant is greater than or equal to 150° C., preferably greater than or equal to 180° C., more preferably greater than or equal to 200° C., more preferably greater than or equal to 250° C., further preferably greater than or equal to 275° C., and most preferably greater than or equal to 300° C. The boiling point of the dispersant is at least greater than or equal to 150° C., which is beneficial to preventing the nozzle of the inkjet print head from being blocked during inkjet printing, and the higher the boiling point, the more beneficial it is to preventing blockage.

[0572] The dispersant may include at least one organic solvent, which may be evaporated from the solvent system to form a film containing the functional material. The organic solvent may be selected from aromatic or heteroaromatic. Specifically, the organic solvent may be selected from p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, Benzene, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0573] The organic solvent can also be selected from aromatic ketone solvents. Specifically, the organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0574] The organic solvent can also be selected from aromatic ether solvents. Specifically, the organic solvent can be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0575] The organic solvent can 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, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; 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, tetraethylene glycol dimethyl ether, etc.

[0576] The organic solvent can also be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0577] The organic solvent can also be selected from one or more of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and the like.

[0578] In addition to the dispersoid and the dispersant, the composition may also include one or more components such as surfactant compounds, lubricants, wetting agents, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0579] In addition, please refer to Figure 4, an embodiment of the present application further provides an organic light-emitting device 100, the organic light-emitting device 100 comprising: a first electrode 101 and a second electrode 102; 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 embodiments, or the material of the organic functional layer 103 comprises the mixture described in the above embodiments, or the material of the organic functional layer 103 comprises the combination described in the above embodiments.

[0580] In some embodiments, the first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0581] In some embodiments, the organic light-emitting device 100 can be used for an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emission diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, and an organic light-emitting field effect transistor.

[0582] In some embodiments, the organic light-emitting device 100 can be applied to a variety of electronic devices, such as display panels, lighting devices, light sources, etc.

[0583] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer, and the mixture layer includes a first compound and a second compound. The first compound is selected from one or more of the organic compounds described above, and the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes. Detailed descriptions of various organic functional materials included in the organic functional layer 103 are detailed in WO2010135519A1, US20090134784A1, and WO 2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0584] The luminescent guest material is selected from a singlet luminescent body (fluorescent luminescent body), a triplet luminescent body (phosphorescent luminescent body) and a TADF material.

[0585] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0586] When the second compound is a light-emitting guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0587] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multiple layers, the organic functional layer 103 at least includes a light-emitting layer 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, an electron blocking layer 106, a light-emitting 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 include a hole blocking layer disposed between the light-emitting layer 107 and the electron transport layer 108.

[0588] 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 is one or more of the organic compounds described above, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

[0589] The light emitting wavelength of the organic light emitting device 100 is between 300nm and 1000nm; further, the light emitting wavelength of the organic light emitting device 100 is between 350nm and 900nm; further, the light emitting wavelength of the organic light emitting device 100 is between 400nm and 800nm; further, the light emitting wavelength of the organic light emitting device 100 is within the wavelength range of blue light.

[0590] In some embodiments, the host material includes at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Preferably, the host material is a blue light host material used in a blue organic light-emitting device; when the host material is a blue light host material, the host material is preferably an anthracene organic compound.

[0591] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc.; preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which is conducive to inhibiting the crystallization of the light-emitting layer 107 and inhibiting the concentration quenching of the guest material due to high concentration, thereby improving the luminous efficiency of the organic light-emitting device 100.

[0592] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer 103, such as: the anode injects holes into the hole injection layer, the hole transport layer or the light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, 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 as the hole injection layer, or 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 the electron blocking layer are less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes but is not limited to at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, indium tin oxide (ITO), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which can be easily selected and used by ordinary technicians in this field. The material of the anode can be deposited using any suitable technology, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, such as: patterned ITO conductive substrates are available on the market and can be used to prepare the organic light-emitting device 100 of the present application.

[0593] In some embodiments, the cathode is an electrode for injecting electrons, and the cathode can inject electrons into the organic functional layer, such as: the cathode injects electrons into the electron injection layer, the electron transport layer, or the light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of an n-type semiconductor material as an electron injection layer, or the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of an n-type semiconductor material of an electron injection layer and an electron transport layer or a hole blocking layer are 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 of organic electronic devices may be used as cathode materials of the device of the present application, and the cathode materials include but are not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0594] In some embodiments, the hole injection layer 104 is used to promote 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 that can receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the functional material of the film layer (such as the hole transport material of the hole transport layer) into which the holes are injected away from the anode. The hole injection material includes but is not limited to at least one of metal porphyrin, oligothiophene, organic material based on arylamine, organic material based on hexanitrile hexaazatriphenylene, organic material based on quinacridone, organic material based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0595] 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, which receives holes transmitted from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and the hole transport material may include but is not limited to at least one of an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, and the like.

[0596] In some embodiments, the electron transport layer 108 is used to transport electrons, and the electron transport layer 108 includes an electron transport material, which receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material with high electron mobility known in the art, and the electron transport material may include but is not limited to: at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0597] In some embodiments, the electron injection layer 109 is used to inject electrons, and the electron injection layer 109 includes an electron injection material, and the electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material, and has the ability to prevent the excitons generated by the light-emitting layer 107 from moving to the hole injection layer, and also has an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, pyrazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc.

[0598] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like.

[0599] In some embodiments, the organic light-emitting device 100 further includes a substrate 110, and the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked on the substrate 110. The substrate 110 may be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device 100 may be manufactured; the substrate 110 may be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate 110 may include but is not limited to plastic, polymer, metal, semiconductor wafer or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface has no surface defects. Preferably, the material of the substrate 110 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0600] In some embodiments, the organic light-emitting device 100 may be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by printing (eg, inkjet printing).

[0601] In some embodiments, the mixture layer or the luminescent layer can be formed by a printing or coating process of the composition. The printing or coating process includes inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slit extrusion coating, etc. Preferably, it is gravure printing, nozzle printing and inkjet printing.

[0602] As mentioned above, the boron-containing biphenyl organic compound provided in the embodiments of the present application introduces structures such as dibenzofuran, dibenzothiophene, carbazole, benzopentacyclic ring, triphenylene and / or naphthalene into the boron nitrogen compound, so that the overall molecular conjugation is greater, thereby improving the luminous efficiency and service life of the organic light-emitting device using the organic compound; at the same time, the introduction of structures such as tetralin and / or indane into the boron nitrogen compound makes the molecule more soluble in processes such as inkjet printing, facilitates compound purification, thereby improving the purity of the organic compound, and further improving the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0603] Furthermore, the examples of the present application calculate the HOMO energy level, LUMO energy level, S1 energy level and T1 energy level of the organic compounds shown in the above-mentioned Examples 1 to 39 and the comparative compound 1 in Comparative Example 1 to verify the performance of the organic compounds provided by the examples of the present application.

[0604] The structural formula of the comparative compound 1 in Comparative Example 1 is:

[0605]

[0606] Through quantum calculation, the HOMO (Highest Occupied Molecular Orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital) energy level, T1 (first excited triplet state) energy level, and S1 (first excited singlet state) energy level of compounds M1 to M168 obtained in Examples 1 to 35 and the comparative compound 1 in Comparative Example 1 can be obtained. Specifically, TD-DFT (time-dependent density functional theory) is used through Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110. First, the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet) is used to optimize the molecular geometry. Then the energy structure of the organic molecule is calculated by TD-DFT (time-dependent density functional theory) and "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO energy level and the LUMO energy level are calculated according to the following calibration formula, and the S1 energy level and the T1 energy level are used directly.

[0607] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0608] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0609] Among them, HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree.

[0610] Based on the above, the calculation results shown in Table 1 are obtained.

[0611] Table 1 Energy level data table

[0612]

[0613]

[0614] As can be seen from Table 1, the T1 energy levels and S1 energy levels of the organic compounds M1 to M168 provided in Examples 1 to 35 provided in the present application are all higher than the T1 energy level and S1 energy level of the comparative compound 1, indicating that, compared with the comparative compound 1, the blue light emitted by the organic compounds M1 to M168 is more inclined to dark blue, which is beneficial for the blue organic light-emitting device using the organic compounds M1 to M168 as the guest material in the light-emitting layer to obtain better color coordinates.

[0615] For further information, please refer to Figure 5 , the embodiments of the present application provide Figure 5 The exemplary manufacturing steps of the organic light-emitting device 200 are shown in the following exemplary embodiment 1.

[0616] Example 1

[0617] In the organic light-emitting device provided in this embodiment, ITO (indium tin oxide) is used as the anode, PEDOT (polyethylene dioxythiophene, Clevios TM AI4083) is used as a material for the hole injection layer, PVK (poly (9-vinyl carbazole, Sigma Aldrich, average Mn 25,000-50,000) is used as a material for the hole transport layer, BH-1 to BH-3 (whose structural formulas are shown below) are respectively used as host materials in the light-emitting layers of the corresponding organic light-emitting devices, the organic compounds M1 to M168 in Examples 1 to 31 and the comparative compound 1 in Comparative Example 1 are respectively used as guest materials in the light-emitting layers of the corresponding organic light-emitting devices, ET and Liq (8-hydroxyquinoline lithium) are used as materials for the electron transport layer, and Al is used as a cathode. The specific preparation steps are as follows:

[0618] a. Cleaning of the ITO anode 202: using chloroform, acetone and / or isopropyl alcohol to clean the ITO conductive glass, and then performing ultraviolet ozone treatment, wherein the conductive glass includes a substrate 201 and an anode 202 formed on the substrate 201;

[0619] b. Forming the hole injection layer 203: Spin-coating the hole injection layer material PEDOT (polyethylene dioxythiophene, Clevios TM AI4083), and treated on a hot plate at 180°C for 10 minutes, the thickness of the hole injection layer 203 is 40 nm;

[0620] c. Forming the hole transport layer 204: Spin-coating a toluene solution of PVK (Sigma Aldrich, Mn 25,000-50,000) with a concentration of 5 mg / ml on the hole injection layer 203, and then treating on a hot plate at 180° C. for 60 minutes. The thickness of the hole transport layer 204 is 20 nm.

[0621] d. Forming the light-emitting layer 205: In a nitrogen glove box, spin-coating the light-emitting layer material on the hole transport layer 204, and then treating it on a hot plate at 140° C. for 10 minutes, the main material in the light-emitting layer 205 of different organic light-emitting devices 200 corresponds to BH-1, BH-2 or BH-3, respectively, and the guest material in the light-emitting layer 205 of different organic light-emitting devices 200 corresponds to one of organic compounds M1 to organic compounds M168, respectively, the solvent is methyl benzoate solution, the mass ratio of the main material to the guest material is 95:5, the concentration of the material of the light-emitting layer 205 is 15 mg / ml, and the thickness of the light-emitting layer 205 finally formed is 40 nm.

[0622] e. Forming an electron transport layer 206: In a vacuum chamber, on the light-emitting layer 205, ET and Liq are placed in different evaporation units, and ET and Liq are co-deposited at a weight ratio of 50:50 under a high vacuum (1×10-6 mbar) environment to form an electron transport layer 206 with a thickness of 20 nm;

[0623] f. Forming a cathode layer 207: depositing Al on the electron transport layer 206 to obtain an Al cathode 207 with a thickness of 100 nm;

[0624] g. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0625] Specifically, in this embodiment, the above steps are used to obtain organic light-emitting devices 1 to 39, and comparative elements 1 to 3. Among them, the guest materials used in the 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 in the organic light-emitting devices 36 and 38 are organic compounds M16, respectively, and the host materials used in the organic light-emitting devices 36 and 38 are BH-2 and BH-3, respectively; the guest materials used in the organic light-emitting devices 37 and 39 are organic compounds M64, and the host materials used in the organic light-emitting devices 37 and 39 are BH-2 and BH-3, respectively; the guest materials used in the comparative elements 1 to 3 are comparative compound 1, and the host materials are BH-1, BH-2 and BH-3, respectively.

[0626] Specifically, the chemical structures of BH-1, BH-2, BH-3, ET and Liq are as follows:

[0627]

[0628] In this embodiment, the current-voltage (JV) characteristic test was performed on the organic light-emitting devices 1 to 39 and the comparative elements 1 to 3, and the CIE color coordinates (x, y), the driving voltage at 1 knits brightness (voltage@1 knits[V]), the luminous efficiency obtained when the current density was 10 mA / cm2 (CE@1 knits[cd / A]), and the time taken for the brightness to drop from the initial brightness of 1 knits to 90% of the initial brightness (LT90@1 knits[h]) of each organic light-emitting device and the comparative element were obtained. The specific results are shown in Table 2.

[0629] Table 2 Performance data of organic light-emitting devices

[0630]

[0631]

[0632] It can be seen from Table 2 that, compared with comparative elements 1 to comparative elements 3, the organic light-emitting devices 1 to 39 obtained by applying guest materials M1 to guest materials M168 to the light-emitting layer in the embodiments of the present application have better color coordinates; further, the luminous efficiency of organic light-emitting devices 1 to 39 is in the range of 5.7 to 6.6 cd / A, indicating that the luminous efficiency thereof is much higher than that of comparative elements 1 to 3; further, compared with the time taken for the brightness of comparative elements 1 to 3 to decrease from the initial brightness of 1 knits to 90% of the initial brightness, the time taken for the brightness of organic light-emitting devices 1 to 39 to decrease from the initial brightness of 1 knits to 90% of the initial brightness is in the range of 133 to 176 h, which is 50% to 100% higher than the time taken for the brightness of comparative elements 1 to 3 to decrease from the initial brightness of 1 knits to 90% of the initial brightness, indicating that the organic light-emitting devices 1 to 39 have significantly improved lifespan.

[0633] At the same time, compared with comparative example 1, the organic compounds M1 to M168 have better overall molecular solubility and are easy to purify the organic compounds by introducing biphenyl rings, aromatic rings, and silicon groups (deuterated phenyl groups), thereby improving the purity of the organic compounds and further improving the efficiency and life of the manufactured organic light-emitting devices.

[0634] In addition, the luminous efficiency of the organic light-emitting devices 1-4 and 151-168 are all in the range of 6.1 to 6.5 cd / A, and the lifespan is about 170 h. This is because compared with the guest materials in other organic light-emitting devices, the guest material provided in the embodiment of the present application contains a triphenylene group, which makes the overall molecular conjugation greater, and the aromatic amine life efficiency of the combination of benzothiophene and triphenylene groups is significantly better than that of the combination of benzothiophene and dibenzothiophene (furan). In addition, the number of solubilizing groups in the guest material provided in the embodiment of the present application is greater, which improves the solubility of the guest material and further improves the luminous efficiency and lifespan of the organic light-emitting device.

[0635] The organic light-emitting device disclosed in the embodiments of the present application improves material properties, increases the luminous efficiency of the organic light-emitting device and prolongs the service life of the organic light-emitting device by using boron nitrogen compounds and introducing aromatic amines of biphenyl and benzothiophene and silicon-containing groups into the boron nitrogen compounds to make the overall conjugation of the compound greater.

[0636] An embodiment of the present application further discloses a display panel, which includes the organic light-emitting device described in the above embodiment.

[0637] The display panel further includes an array substrate located on one side of the organic light-emitting device, and an encapsulation layer located on a 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 polarizer layer located on a side of the encapsulation layer away from the organic light-emitting device, and a cover layer located on a side of the polarizer layer away from the organic light-emitting device. The polarizer layer may be replaced by a color filter layer, and the color filter layer may include a plurality of color resists and a black matrix located on both sides of the color resists.

[0638] The display panel disclosed in the embodiment of the present application uses an organic light-emitting device containing a boron nitrogen compound, and introduces a silicon-containing group into the boron nitrogen compound to make the overall conjugation of the compound greater, thereby enhancing the conjugation effect of the material used in the organic light-emitting device, improving the material properties, improving the luminous efficiency of the display panel and extending the service life of the display panel.

[0639] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0640] The above is a detailed introduction to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the technical solution and its core idea of ​​the present application. Ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein; and these modifications or replacements do not make the essence of the corresponding technical solution deviate from the scope of the technical solution of the embodiments of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in general formula (1) or general formula (2): Wherein, 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 selected from 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 carbon atom is a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; At least one of Ar1, Ar2, Ar3, Ar4, R1 and R2 has a silicon group 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. The organic compound according to claim 1, characterized in that Ar1 is selected from the group represented by any one of formula (X-1) to formula (X-4): Ar2 is selected from the group represented by any one of formula (A-1) to formula (A-4): Ar3 and Ar4 are selected from the group represented by any one of formula (B-1) to formula (B-5): The attachment site of Ar2 is on a carbon atom of any benzene ring, the attachment site of Ar3 is on a carbon atom of any benzene ring, and the fusion site of Ar4 is on two carbon atoms in the ortho position in the same benzene ring; X is selected from O, S, N-CH3, N-Ph or C(CH3)2; R0 and L are selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain or branched silicon group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched 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 a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; 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.

3. The organic compound according to claim 2, characterized in that When Ar1 is selected from the group represented by formula (X-2), Ar4 is selected from the group represented by any one of formula (B-2) to formula (B-5).

4. The organic compound according to claim 2, characterized in that When n0 is greater than or equal to 2, two adjacent R0s and the atoms to which they are connected may or may not form a ring with each other; When n1 is greater than or equal to 2, two adjacent R1s and the ring atoms to which they are connected together form a ring or do not form a ring; When n2 is greater than or equal to 2, two adjacent R2s and the ring atoms to which they are connected together form a ring or do not form a ring; When a is greater than or equal to 2, two adjacent L's together with the atoms to which they are connected may or may not form a ring.

5. The organic compound according to claim 2, characterized in that The organic compound has a structure as shown in any one of the general formulas (2-1) to (2-31): wherein R3 and R4 are selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain or branched silicon group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched 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 carbon atom a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; n3 is greater than or equal to 0 and less than or equal to 5. When n3 is greater than or equal to 2, two adjacent R3s and the atoms to which they are connected together may or may not form a ring; n4 is greater than or equal to 0 and less than or equal to 5. When n4 is greater than or equal to 2, two adjacent R4s and the atoms to which they are connected may or may not form a ring.

6. The organic compound according to claim 5, characterized in that R1, R2, R3, R4 and L are 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.

7. The organic compound according to claim 5, characterized in that R1, R2, R3, R4 and L are 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.

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

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

10. A mixture, characterized in that The mixture comprises the organic compound according to any one of claims 1 to 9 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

11. A composition, characterized in that The composition comprises the organic compound according to any one of claims 1 to 9 and at least one organic solvent, or the composition comprises the mixture according to claim 10 and at least one organic solvent.

12. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; The material of the organic functional layer includes one or more of the organic compounds described in any one of claims 1 to 9, or the material of the organic functional layer includes the mixture described in claim 10, or the material of the organic functional layer includes the composition described in claim 11.

13. The organic light emitting device according to claim 12, characterized in that: The organic functional layer at least includes a light-emitting layer, and 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.

14. A display panel, characterized in that: The display panel comprises the organic light emitting device according to claim 12 or 13.

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