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

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel, and the organic compound has a structure represented by a formula (1) or a formula (2): # imgabs0 # imgabs1 #. According to the present invention, by introducing a group which enables the overall conjugacy of the compound to be greater into a boron-nitrogen compound, the material performance is improved; the light-emitting efficiency of the organic light-emitting device is improved; and the service life of the organic light-emitting device is prolonged.

Description

Technical Field

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

[0002] Currently, organic electroluminescent elements such as organic light-emitting diodes (OLEDs) generally have an anode, a cathode, and an organic layer located between the two. The organic substances in the organic layer convert electrical energy into light energy, thereby achieving organic electroluminescence. To improve the luminous efficiency and service life of organic electroluminescent elements, the organic layer is often multi-layered, and the organic substances contained in each layer are different. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. A voltage is applied between the anode and the cathode of the organic electroluminescent element. The anode injects holes into the organic layer, and the cathode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, and when the excitons transition back to the ground state, light is emitted, thereby achieving the luminescence of the organic electroluminescent element. Organic electroluminescent elements have the characteristics of self-luminescence, high brightness, high efficiency, low-voltage driving, wide viewing angle, high contrast, and high response. Therefore, organic electroluminescent devices have broad application prospects.

[0003] To improve the luminous efficiency of organic electroluminescent elements, various luminescent material systems based on fluorescence and phosphorescence have been developed. Among them, organic electroluminescent elements using fluorescent materials have the characteristic of high reliability. However, under electrical excitation, due to the branching ratio of the singlet excited state and the triplet excited state of excitons being 1:3, the internal electroluminescent quantum efficiency will be limited within 25%. And organic electroluminescent elements using phosphorescent materials can almost achieve an internal electroluminescent quantum efficiency of 100%. However, phosphorescent materials usually use metal complexes containing iridium and platinum, with expensive raw materials and complex synthesis. Moreover, phosphorescent organic electroluminescent elements also generate a Roll-off (efficiency roll-off) effect, that is, the luminous efficiency rapidly decreases with the increase of current or brightness, limiting their application at high brightness.

[0004] To overcome the above problems, the prior art usually involves various material combinations based on organic compounds, such as composite excited state materials, thermally activated delayed fluorescence (TADF) materials, etc., and uses reverse internal conversion to achieve high efficiency comparable to that of phosphorescent organic electroluminescent elements. However, the performance of traditional organic compounds with TADF is limited in terms of both efficiency and lifespan, resulting in difficulties in improving the luminous efficiency and service life of organic electroluminescent elements using organic compounds with TADF. Summary of the Invention

[0005] This application provides an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel to improve the luminous efficiency and service life of the organic light-emitting device.

[0006] This application provides an organic compound having a structure represented by Formula (1) or Formula (2):

[0007]

[0008] Wherein,

[0009] Ar1 is selected from the structures represented by any one of Formula (X-1) to Formula (X-3), Formula (B-1) to Formula (B-4);

[0010] Ar2 is selected from hydrogen and the structures represented by any one of Formula (B-1) to Formula (B-4);

[0011] Ar3 is selected from the structures represented by any one of Formula (A-1) to Formula (A-5);

[0012] Ar4 is selected from the structures represented by any one of Formula (A-1) to Formula (A-5), Formula (B-1) to Formula (B-4);

[0013] The structures of Formula (X-1) to Formula (X-3), Formula (B-1) to Formula (B-4), and Formula (A-1) to Formula (A-5) are as follows:

[0014]

[0015] R0, R1, R2, and R5 are each independently selected from -H, -D, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a silyl group having 1 to 20 silicon atoms, 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 alkenyl group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a 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;

[0016] X is selected from O, S, N-CH3, N-Ph, or C(CH3)2;

[0017] n0 is any integer from 0 to 14. When n0 is greater than or equal to 2, two adjacent R0 groups may or may not form a ring with each other;

[0018] n1 is any integer from 0 to 14. When n1 is greater than or equal to 2, two adjacent R1 groups may or may not form a ring with each other;

[0019] n2 is any integer from 0 to 14. When n2 is greater than or equal to 2, two adjacent R2 groups may or may not form a ring with each other;

[0020] n5 is any integer from 0 to 14. When n5 is greater than or equal to 2, two adjacent R5 groups may or may not form a ring with each other.

[0021] In some embodiments, when Ar2 represents hydrogen, Ar1 and Ar4 are each independently selected from the structures represented by any one of formulas (B-1) to (B-4), and Ar1 and Ar4 are the same.

[0022] In some embodiments, the organic compound has a structure represented by any one of formulas (2-1) to (2-52):

[0023]

[0024]

[0025]

[0026]

[0027]

[0028] Among them, R3 and R4 are selected from at least one of -H, -D, linear alkyl groups having 1 to 20 carbon atoms, linear alkoxy groups having 1 to 20 carbon atoms, linear thioalkoxy groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, branched alkoxy groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, branched thioalkoxy groups having 3 to 20 carbon atoms, cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, keto groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, -CN, carbamoyl groups, halocarbonyl 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;

[0029] n3 is selected from any integer from 0 to 5. When n3 is greater than or equal to 2, two adjacent R3 groups may form a ring or not form a ring with each other;

[0030] n4 is selected from any integer from 0 to 5. When n4 is greater than or equal to 2, two adjacent R4 groups may form a ring or not form a ring with each other.

[0031] In some embodiments, R1, R2, R3, R4, and R5 are selected from at least one of -H, -D, linear alkyl groups having 1 to 10 carbon atoms, branched alkyl groups having 3 to 10 carbon atoms, cyclic alkyl groups having 3 to 10 carbon atoms, and triphenylsilyl groups.

[0032] In some embodiments, the organic compound is selected from any one of the following compounds:

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] The present application also provides a mixture, which comprises at least one organic functional material and at least one organic compound as described above, and the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a guest material, a host material, and an organic dye.

[0053] The present application also provides a composition, which comprises at least one organic solvent and at least one organic compound as described above, or the composition comprises at least one of the organic solvents and the mixture as described above.

[0054] The present application also provides an organic light-emitting device, which comprises:

[0055] A first electrode;

[0056] A second electrode, which is disposed opposite to the first electrode; and

[0057] An organic functional layer, located between the first electrode and the second electrode;

[0058] Wherein, the material of the organic functional layer includes at least one of the above-mentioned organic compounds, or the material of the organic functional layer includes the above-mentioned mixture, or the material of the organic functional layer includes the above-mentioned composition.

[0059] In some embodiments, the organic functional layer includes a light-emitting layer, the material of the light-emitting layer includes a host material and a guest material, and the guest material includes at least one of the organic compounds.

[0060] This application also provides a display panel, which includes the above-mentioned organic light-emitting device.

[0061] This application provides an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound provided by this application introduces structures such as benzene, naphthalene, triphenylene, benzopentacyclic ring, benzocarbazole, benzofluorene, naphthofuranobenzene, naphthothiophenobenzene, adamantylfluorene, etc. into the boron nitride compound, making the overall molecular conjugation larger and the molecular stability higher, thereby improving the luminous efficiency and service life of the organic light-emitting device using the organic compound; in addition, due to the enhanced molecular rigidity of the organic compound, molecular aggregation can be inhibited, and the introduced large steric hindrance groups can effectively prevent the close packing between molecules, thereby reducing the concentration sensitivity of the material, making the solubility of the molecule better in processes such as inkjet printing, and facilitating the purification of the organic compound, thereby improving the purity of the organic compound to further extend the luminous efficiency and service life of the organic light-emitting device using the organic compound. Description of the Drawings

[0062] In order to more clearly illustrate the technical solutions in the embodiments of this application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of this application. For those skilled in the art, without creative efforts, other drawings can also be obtained based on these drawings.

[0063] Figure 1 It is the first structural schematic diagram of the organic light-emitting device provided by the embodiment of this application;

[0064] Figure 2 It is the second structural schematic diagram of the organic light-emitting device provided by the embodiment of this application;

[0065] Figure 3 It is the nuclear magnetic resonance hydrogen spectrum diagram of the organic compound M40 provided by the embodiment of this application;

[0066] Figure 4It is the nuclear magnetic resonance hydrogen spectrum of organic compound M43 provided by the embodiments of the present application. Detailed implementation manners

[0067] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation manners described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise stated, the orientation words such as "upper" and "lower" usually refer to the upper and lower in the actual use or working state of the device, specifically the drawing direction in the accompanying drawings. In the present application, "optionally", "optional", "optional" mean that it can be either present or absent, that is, it refers to any one of the two parallel options of "present" or "absent". If "optional" appears multiple times in a technical solution, without special instructions and without contradictions or mutual restrictions, each "optional" is independent of each other. In the present application, for the technical features described in an open-ended manner, it includes a closed technical solution composed of the listed features, as well as an open technical solution of the listed features.

[0068] In the present application, the aromatic group, aromatic, and aromatic ring system have the same meaning and can be interchanged.

[0069] In the present application, the heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and can be interchanged.

[0070] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0071] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs, then R can be independently selected from different groups.

[0072] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, where R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group having 1-20 carbon atoms, heterocyclic group having 3-20 ring atoms, aromatic group having 6-20 ring atoms, heteroaromatic group having 5-20 ring atoms, -NR’R”, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art; it can be understood that R’ and R” in -NR’R” are each independently selected from, but not limited to: H, deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group having 1-10 carbon atoms, heterocyclic group having 3-20 ring atoms, aromatic group having 6-20 ring atoms, heteroaromatic group having 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group having 1-10 carbon atoms, heterocyclic group having 3-10 ring atoms, aromatic group having 6-20 ring atoms, heteroaromatic group having 5-20 ring atoms, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0073] In the present application, "number of ring atoms" means the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below under the condition of no special description. 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.

[0074] In the present application, the "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For a polycyclic ring, at least one is an aromatic ring system. For example, the "substituted or unsubstituted aryl group 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, 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, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetraphenylenyl, fluorenyl, binaphthylenyl, acenaphthylenyl, and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (for example, <10% non-H atoms, such as C, N, or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0075] In the present application, the "heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, the "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include but are not limited to: thienyl, furyl, pyrrolyl, imidazolyl, oxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thiophenopyrrolyl, thiophenothiophenyl, furanopyrrolyl, furanofuryl, thiophenofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, perimidinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl, and their derivatives.

[0076] In the present application, the "alkyl group" can represent a straight-chain, branched-chain, and / or cyclic alkyl group. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. A phrase containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group or C9 alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0077] In this application, the abbreviations of substituents 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.

[0078] In this application, "amino group" refers to a derivative of amine, having a structural feature of the formula -N(X)2, where each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0079] 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, halocarbonyl refers to -C(=O)Z (wherein Z represents a halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0080] In the present application, the term "alkoxy" refers to a group having the structure "-O-alkyl", that is, the alkyl group defined above is connected to other groups via an oxygen atom. For phrases containing this term, suitable examples include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-O-C(CH3)3 or -OtBu).

[0081] In the present application, when the connection site is not specified in a group, it means that any optional connection site in the group can be used as the connection site.

[0082] In the present application, when the fusion site is not specified in a group, it means that any optional fusion site in the group can be used as the fusion site, and preferably two or more sites adjacent to each other in the group are used as the fusion site.

[0083] In the present application, when there are multiple substituents with the same symbol on the same group, each substituent can be the same or different from each other. For example The six Rs on the benzene ring can be the same or different from each other.

[0084] In the present application, a single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any position of the ring. For example R in is connected to any substitutable site of the benzene ring; as Indicates Can be combined with To form a fused ring at any position of the benzene ring in.

[0085] In the present application, cyclic alkyl or cycloalkyl have the same meaning and can be interchanged.

[0086] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0087] In the present application, "two adjacent Rs form a ring with each other" means a ring system formed by connecting two adjacent Rs to each other, and the ring system can be selected from an aliphatic hydrocarbon ring, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

[0088] Preferably, it can form

[0089] In the present application, "*" connected to a single bond represents a connection or fusion site.

[0090] This application provides an organic compound, and the organic compound has a structure shown in Formula (1) or Formula (2):

[0091]

[0092] Wherein,

[0093] Ar1 is selected from the structures represented by any one of Formula (X-1) to Formula (X-3), Formula (B-1) to Formula (B-4);

[0094] Ar2 is selected from hydrogen and the structures represented by any one of Formula (B-1) to Formula (B-4);

[0095] Ar3 is selected from the structures represented by any one of Formula (A-1) to Formula (A-5);

[0096] Ar4 is selected from the structures represented by any one of Formula (A-1) to Formula (A-5), Formula (B-1) to Formula (B-4);

[0097] The structures of Formula (X-1) to Formula (X-3), Formula (B-1) to Formula (B-4), and Formula (A-1) to Formula (A-5) are shown as follows:

[0098]

[0099] Wherein the connection sites of Ar2 and Ar3 are carbon atoms on any one of their benzene rings, and the fusion sites of Ar1 and Ar4 are two adjacent carbon atoms on the same benzene ring;

[0100] R0, R1, R2, and R5 are selected from -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, straight-chain thioalkoxy groups having 1 to 20 carbon atoms, branched-chain alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, branched-chain alkoxy groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, branched-chain thioalkoxy groups having 3 to 20 carbon atoms, cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, silyl groups having 1 to 20 silicon atoms, keto groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, -CN, carbamoyl groups, halocarbonyl 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, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, at least one of which;

[0101] X is selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0102] n0 is selected from any integer from 0 to 14. When n0 is greater than or equal to 2, two adjacent R0s may form a ring or not form a ring with each other;

[0103] n1 is selected from any integer from 0 to 14. When n1 is greater than or equal to 2, two adjacent R1s may form a ring or not form a ring with each other;

[0104] n2 is selected from any integer from 0 to 14. When n2 is greater than or equal to 2, two adjacent R2s may form a ring or not form a ring with each other;

[0105] n5 is selected from any integer from 0 to 14. When n5 is greater than or equal to 2, two adjacent R5s may form a ring or not form a ring with each other.

[0106] In some embodiments, Ar1 is selected from the structures represented by any one of Formula (X-1) to Formula (X-3);

[0107] Ar2 is selected from the structures represented by any one of Formula (B-1) to Formula (B-4);

[0108] Ar3 and Ar4 are selected from the structures represented by any one of Formula (A-1) to Formula (A-5).

[0109] In the present application, introducing the structures of Formula (X-1) to Formula (X-3), Formula (B-1) to Formula (B-4), and Formula (A-1) to Formula (A-5) into the boron nitride compound can narrow the full width at half maximum, enhance the lifetime of the organic light-emitting device, and improve the luminous efficiency of the organic light-emitting device.

[0110] In some embodiments, when Ar2 represents hydrogen, Ar1 and Ar4 are selected from the structures represented by any one of Formula (B-1) to Formula (B-4), and Ar1 and Ar4 are the same. The organic compound with this structure can narrow the full width at half maximum, enhance the lifetime of the organic light-emitting device, and improve the luminous efficiency of the organic light-emitting device.

[0111] In some embodiments, the organic compound has a structure represented by any one of Formula (2-1) to Formula (2-52):

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] Among them, R3 and R4 are selected from at least one of -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a 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;

[0118] n3 is selected from any integer from 0 to 5. When n3 is greater than or equal to 2, two adjacent R3 groups may or may not form a ring with each other;

[0119] n4 is selected from any integer from 0 to 5. When n4 is greater than or equal to 2, two adjacent R4 groups may or may not form a ring with each other.

[0120] In some embodiments, R1, R2, R3, R4, and R5 are selected from at least one of -H, -D, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, and a triphenylsilyl group. By introducing an alkyl group into the organic compound in the present application, it is beneficial to improve the solubility of the organic compound in processes such as inkjet printing, facilitate the purification of the organic compound, thereby improving the purity of the organic compound, and further extending the luminous efficiency and service life of the organic light-emitting device using the organic compound. Introducing a triphenylsilyl group into the organic compound can narrow the full width at half maximum, enhance the lifetime of the organic light-emitting device, and improve the luminous efficiency of the organic light-emitting device.

[0121] Further, R1, R2, R3, R4, and R5 are selected from at least one of -H, -D, a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 5 carbon atoms, and a triphenylsilyl group. R1, R2, R3, R4, and R5 groups with suitable molecular weights can further improve the solubility of the organic compound in processes such as inkjet printing and further extend the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0122] In some embodiments, two adjacent R1 groups form a ring with each other; further, two adjacent R1 groups form a 6-membered aromatic ring or aliphatic ring with each other; still further, two adjacent R1 groups form a wherein, * represents the connection site.

[0123] In some embodiments, two adjacent R2 groups form a ring with each other; further, two adjacent R2 groups form a 6-membered aromatic ring or aliphatic ring with each other; still further, two adjacent R2 groups form a wherein, * represents the connection site.

[0124] In some embodiments, two adjacent R3 groups form a ring with each other; further, two adjacent R3 groups form a 6-membered aromatic ring or aliphatic ring with each other; still further, two adjacent R3 groups form a wherein, * represents the connection site.

[0125] In some embodiments, two adjacent R4 groups form a ring with each other; further, two adjacent R4 groups form a 6-membered aromatic ring or aliphatic ring with each other; still further, two adjacent R4 groups form a wherein, * represents the connection site.

[0126] In some embodiments, two adjacent R5 groups form a ring with each other; further, two adjacent R5 groups form a 6-membered aromatic ring or aliphatic ring with each other; still further, two adjacent R5 groups form a wherein, * represents the connection site.

[0127] In some embodiments, the organic compound is selected from any one of the following compounds:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] The organic compound provided by this application is a boron-containing biphenyl organic compound. By introducing structures such as benzene, naphthalene, triphenylene, benzopentacyclic ring, benzocarbazole, benzofluorene, naphthofurobenzene, naphthothiophenobenzene, adamantylfluorene, etc. at the corresponding positions of Ar1, Ar2, Ar3, and Ar4 in the boron-nitrogen compound, the conjugated system of the entire molecule is expanded, making the organic compound have high stability. Furthermore, it can improve the luminous efficiency and service life of the organic light-emitting device using the organic compound. At the same time, the introduction of the above groups can narrow the full width at half maximum, and can further improve the luminous efficiency and service life of the organic light-emitting device using the organic compound. In addition, due to the enhanced molecular rigidity of the organic compound, molecular aggregation can be inhibited. The introduced large steric hindrance groups can effectively prevent the close packing between molecules, thereby reducing the concentration sensitivity of the material, making the solubility of the molecule better in processes such as inkjet printing, facilitating the purification of the organic compound, thereby improving the purity of the organic compound, and further enhancing the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0148] In some embodiments, when the organic compound is used as an organic functional material in an organic light-emitting device, it can be used as a light-emitting layer material in the light-emitting layer. Further, the organic compound can be used as a blue light-emitting material in a blue organic light-emitting device. Since the organic compound has a large conjugated system, high stability, and good solubility, the organic light-emitting device prepared by using the organic compound has high luminous efficiency and service life.

[0149] The present application also provides a mixture, which includes at least one organic functional material and at least one organic compound as described above. The organic functional material is selected from one or more of a hole injection material (Hole Injection Material, HIM), a hole transport material (Hole Transport Material, HTM), an electron transport material (Electron Transport Material, ETM), an electron injection material (Electron Injection Material, EIM), an electron blocking material (Electron Blocking Material, EBM), a hole blocking material (Hole Blocking Material, HBM), a guest material (Guest Emitter), a host material (Host Emitter), or an organic dye.

[0150] The present application also provides a composition, which can be a solution or a suspension, and the composition can include a dispersoid and a dispersant. Wherein, the dispersoid is one or more of the above-mentioned organic compounds and at least one organic solvent; the dispersant is used to disperse the dispersoid and includes at least one organic solvent, and the organic solvent can evaporate from the solvent system to form a functional material thin film.

[0151] In some embodiments, in the composition, the mass fraction of the organic compound can be 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, further preferably 0.5% to 10%, and most preferably 1% to 5%.

[0152] In some embodiments, when the composition is used in a printing process, the composition can be an ink. The viscosity and surface tension of the ink are important parameters. The surface tension parameter of a suitable ink is 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 from 22 dyne / cm to 35 dyne / cm; more preferably from 25 dyne / cm to 33 dyne / cm, which is beneficial for application in an inkjet printing process. In some embodiments, the viscosity of the ink at the working temperature or 25 °C ranges from 1 cps to 100 cps; preferably from 1 cps to 50 cps; more preferably from 1.5 cps to 20 cps; most preferably from 4.0 cps to 20 cps, which is beneficial for application in an inkjet printing process.

[0153] In some embodiments, the Hansen solubility parameters of the dispersant are in the following ranges: the δd (dispersion force) of the dispersant is in the range of 17.0 - 23.2 MPa 1 / 2 preferably in the range of 18.5 - 21.0 MPa 1 / 2 ; the δp (polar force) is in the range of 0.2 - 12.5 MPa 1 / 2 preferably in the range of 2.0 - 6.0 MPa 1 / 2 ; the δh (hydrogen bond force) is in the range of 0.9 - 14.2 MPa 1 / 2 preferably in the range of 2.0 - 6.0 MPa 1 / 2 range.

[0154] 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; still more preferably greater than or equal to 250 °C; further preferably greater than or equal to 275 °C; most preferably greater than or equal to 300 °C. The boiling point of the dispersant being at least greater than or equal to 150 °C is beneficial for preventing nozzle clogging of the inkjet print head during inkjet printing, and the higher the boiling point, the more beneficial it is for preventing clogging.

[0155] In some embodiments, the dispersant includes at least one organic solvent, and the organic solvent may include at least one first organic solvent, and the first organic solvent may be selected from aromatic or heteroaromatic. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0156] The first organic solvent may be selected from aromatic ketone solvents. Specifically, the first organic solvent may be selected from 1-tetralone, 2-tetralone, 2-(phenyloxiranyl)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.

[0157] The first organic solvent may be selected from aromatic ether solvents. Specifically, the first organic solvent may be selected from 3-phenoxytoluene, butoxybenzene, dimethyl acetal of p-anisaldehyde, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzyl 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.

[0158] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may 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 pentyl 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.

[0159] The first organic solvent may be selected from organic ester solvents. Specifically, the first solvent may be selected from alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0160] The organic solvent may further include a second organic solvent, and the second organic solvent may be selected from one or more of solvents such as 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, etc.

[0161] In addition to the dispersoid and the dispersant, the composition may further include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0162] This application also provides an organic light-emitting device 100. Please refer to the following Figure 1 - Figure 2 The organic light-emitting device 100 includes: a first electrode 101, a second electrode 102, and an organic functional layer 103 located between the first electrode 101 and the second electrode 102; wherein, the material of the organic functional layer 103 includes at least one of the organic compounds described above.

[0163] In some embodiments, one of the first electrode 101 and the second electrode 102 is an anode, and the other is a cathode. For example, the first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0164] In some embodiments, the organic light-emitting device 100 may be, but is not limited to: an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc. Preferably, it is an organic light-emitting diode, an organic light-emitting electrochemical cell, or an organic light-emitting field-effect transistor.

[0165] In some embodiments, the organic light-emitting device 100 may be applied to various electronic devices, such as: a display panel, a lighting device, a light source, etc.

[0166] 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 a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a guest material, a host material, or an organic dye. For a detailed description of the various organic functional materials included in the organic functional layer 103, see WO2010135519A1, US20090134784A1, and WO 2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0167] In some embodiments, the guest material is selected from singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), and TADF materials.

[0168] In some embodiments, when the second compound is selected from one or more of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a host material, and an organic dye, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0169] In some embodiments, when the second compound is a guest material, the mass ratio of the first compound to the second compound is from 99:1 to 70:30, preferably from 99:1 to 90:10.

[0170] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is a multi-layer structure, the organic functional layer 103 at least includes a light-emitting layer 107. Further, the organic functional layer 103 further includes at least one of a hole injection layer 104, a hole transport layer 105, an electron blocking layer 106, an electron injection layer 109, an electron transport layer 108, and a hole blocking layer.

[0171] 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. 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 as described above, and the host material includes a fused aromatic derivative or a heteroaromatic compound.

[0172] In some embodiments, the emission wavelength of the organic light-emitting device 100 is between 300 and 1000 nm; further, the emission wavelength of the organic light-emitting device 100 is between 350 and 900 nm; still further, the emission wavelength of the organic light-emitting device 100 is between 400 and 800 nm; even further, the emission wavelength of the organic light-emitting device 100 is within the wavelength range of blue light.

[0173] 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, pyrimidine derivatives. Preferably, the host material is a blue light host material applied to a blue organic light-emitting device; when the host material is a blue light host material, the host material is preferably an anthracene-based organic compound.

[0174] In some embodiments, the mass ratio of the host material to the guest material is from 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc.; preferably from 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 being from 99:1 to 70:30 is beneficial to suppressing the crystallization of the light-emitting layer 107 and suppressing concentration quenching caused by the high concentration of the guest material, thereby improving the light-emitting efficiency of the organic light-emitting device 100.

[0175] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer 103. For example, 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 absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, the hole transport layer, or the electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which can be easily selected and used by those of ordinary skill in the art. The material of the anode can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be pattern-structured. For example, a patterned ITO conductive substrate is commercially available and can be used to fabricate the organic light-emitting device 100 of the present application.

[0176] In some embodiments, the cathode is an electron-injecting electrode, and the cathode can inject electrons into the organic functional layer. For example, the cathode injects electrons into the electron injection layer, the electron transport layer, or the light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the light-emitting material in the light-emitting layer, or the n-type semiconductor material in the electron injection layer, the electron transport layer, or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as the cathode of an organic electronic device may be used as the cathode material of the device of the present application. The material of the cathode includes, but is not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the cathode can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0177] In some embodiments, the hole injection layer 104 is used to facilitate the injection of holes from the anode into the light-emitting layer 107, and the hole injection layer 104 comprises a hole injection material which is a material capable of receiving 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 (such as the hole transport material of the hole transport layer) of the film layer on the side away from the anode of the hole injection. The hole injection material includes but is not limited to at least one of metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0178] 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 comprises a hole transport material which receives holes transported from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material known in the art to have a high hole mobility, and the hole transport material can include but is not limited to at least one of arylamine-based organic materials, conductive polymers, block copolymers having both a conjugated part and a non-conjugated part, etc.

[0179] In some embodiments, the electron transport layer 108 is used to transport electrons. The electron transport layer 108 comprises 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 known in the art to have a high electron mobility, and the electron transport material can include but is not limited to at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, lithium 8-hydroxyquinolate (LiQ), and a benzimidazole-based compound.

[0180] In some embodiments, the electron injection layer 109 is used for injecting electrons. The electron injection layer 109 includes an electron injection material, which 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, has the ability to prevent 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 lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, oxazole, dioxazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc.

[0181] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and generally can have the same formation 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 dioxazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0182] 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 can be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device 100 can be fabricated; the substrate 110 can be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate 110 can include, but is not limited to, plastics, polymers, metals, semiconductor wafers, or glass, etc. Preferably, the substrate 110 has 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 is not limited to, polyethylene terephthalate (PET material) and polyethylene naphthalate (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.

[0183] In some embodiments, the organic light-emitting device 100 can be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by a printing method (such as inkjet printing).

[0184] 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.

[0185] The exemplary preparation methods of the organic compounds provided in the present application are shown in the following exemplary embodiments 1 to 35.

[0186] Example 1

[0187] The synthetic route of organic compound M1 is as follows:

[0188]

[0189] Synthesis of intermediate 1-3:

[0190] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 1-3 with a molar weight of 8.21 mmol and a yield of 82.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 337.

[0191] Synthesis of intermediate 1-5:

[0192] Compound 1-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 1-5 with a molar weight of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS (ASAP) = 481.

[0193] Synthesis of intermediate 1-6:

[0194] Intermediate 1-5 (10 mmol), Compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated, and the organic phase was subjected to column chromatography to obtain Intermediate 1-6 with a molar amount of 5.48 mmol and a yield of 54.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 1-6: MS(ASAP) = 594.

[0195] Synthesis of Intermediate 1-8:

[0196] Intermediate 1-6 (10 mmol), Compound 1-7 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated, and the organic phase was subjected to column chromatography to obtain Intermediate 1-8 with a molar amount of 6.25 mmol and a yield of 62.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 1-8: MS(ASAP) = 760.

[0197] Synthesis of Intermediate 1-10:

[0198] Intermediate 1-8 (10 mmol) and Intermediate 1-9 (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, and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated, and the organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 1-10 with a molar amount of 7.33 mmol and a yield of 73.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 1-10: MS(ASAP) = 942.

[0199] Synthesis of Organic Compound M1:

[0200] Add 10 mmol of intermediate 1-10 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M1, with a yield of 38.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M1: MS(ASAP) = 916.

[0201] Example 2

[0202] The synthetic route of organic compound M2 is as follows:

[0203]

[0204] Synthesis of intermediate 2-2:

[0205] Dissolve intermediate 1-8 (10 mmol) and intermediate 2-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 7.17 mmol of intermediate 2-2, with a yield of 71.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-2: MS(ASAP) = 942.

[0206] Synthesis of organic compound M2:

[0207] Add 10 mmol of intermediate 2-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, and then cool the reaction solution to 0 °C. Add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M2, with a yield of 45.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M2: MS(ASAP) = 916.

[0208] Example 3

[0209] The synthetic route of organic compound M3 is as follows:

[0210]

[0211] Synthesis of intermediate 3-2:

[0212] Dissolve intermediate 1-8 (10 mmol) and intermediate 3-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, remove most of the solvent by rotary evaporation, and then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 6.78 mmol of intermediate 3-2 with a yield of 67.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-2: MS(ASAP) = 942.

[0213] Synthesis of organic compound M3:

[0214] Add 10 mmol of intermediate 3-2 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M3, with a yield of 41.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M3: MS(ASAP) = 916.

[0215] Example 4

[0216] The synthetic route of organic compound M4 is as follows:

[0217]

[0218] Synthesis of intermediate 4-2:

[0219] Dissolve intermediate 1-8 (10 mmol) and intermediate 4-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavap to remove most of the solvent, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 6.55 mmol of intermediate 4-2, with a yield of 65.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-2: MS(ASAP) = 942.

[0220] Synthesis of organic compound M4:

[0221] Add 10 mmol of intermediate 4-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate to evaporate the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M4, with a yield of 48.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M4: MS(ASAP) = 916.

[0222] Example 5

[0223] The synthetic route of organic compound M5 is as follows:

[0224]

[0225] Synthesis of intermediate 5-2:

[0226] Dissolve intermediate 1-8 (10 mmol) and intermediate 5-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotate to evaporate most of the solvent, then extract and wash and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain 6.05 mmol of intermediate 5-2, with a yield of 60.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-2: MS(ASAP) = 942.

[0227] Synthesis of organic compound M5:

[0228] Add 10 mmol of intermediate 5-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, which is purified by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M5, with a yield of 39.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M5: MS(ASAP) = 916.

[0229] Example 6

[0230] The synthetic route of organic compound M6 is as follows:

[0231]

[0232] Synthesis of intermediate 6-2:

[0233] Dissolve intermediate 1-8 (10 mmol) and intermediate 6-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavapor to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain 7.03 mmol of intermediate 6-2, with a yield of 70.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 6-2: MS(ASAP) = 942.

[0234] Synthesis of organic compound M6:

[0235] Add 10 mmol of intermediate 6-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M6, with a yield of 32.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M6: MS(ASAP)=916.

[0236] Example 7

[0237] The synthetic route of organic compound M7 is as follows:

[0238]

[0239] Synthesis of intermediate 7-2:

[0240] Dissolve intermediate 1-8 (10 mmol) and intermediate 7-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavapor to remove most of the solvent, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 5.93 mmol of intermediate 7-2, with a yield of 59.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-2: MS(ASAP)=942.

[0241] Synthesis of organic compound M7:

[0242] Add 10 mmol of intermediate 7-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M7, with a yield of 47.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M7: MS(ASAP) = 916.

[0243] Example 8

[0244] The synthetic route of organic compound M8 is as follows:

[0245]

[0246] Synthesis of intermediate 8-2:

[0247] Dissolve intermediate 1-8 (10 mmol) and intermediate 8-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), and stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, rotavapor to remove most of the solvent, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 5.81 mmol of intermediate 8-2, with a yield of 58.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-2: MS(ASAP) = 942.

[0248] Synthesis of organic compound M8:

[0249] Add 10 mmol of intermediate 8-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M8, with a yield of 51.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M8: MS(ASAP) = 916.

[0250] Example 9

[0251] The synthetic route of organic compound M9 is as follows:

[0252]

[0253] Synthesis of intermediate 9-2:

[0254] Dissolve intermediate 1-8 (10 mmol) and intermediate 9-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 7.88 mmol of intermediate 9-2, with a yield of 78.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-2: MS(ASAP) = 958.

[0255] Synthesis of organic compound M9:

[0256] Add 10 mmol of intermediate 9-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, which is purified by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M9, with a yield of 63.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M9: MS(ASAP) = 932.

[0257] Example 10

[0258] The synthetic route of organic compound M10 is as follows:

[0259]

[0260] Synthesis of intermediate 10-2:

[0261] Dissolve intermediate 1-8 (10 mmol) and intermediate 10-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavapor to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain 6.78 mmol of intermediate 10-2, with a yield of 67.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-2: MS(ASAP) = 958.

[0262] Synthesis of organic compound M10:

[0263] Add 10 mmol of intermediate 10-2 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C and slowly add a n-hexane solution of t-BuLi (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M10, with a yield of 47.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M10: MS(ASAP)=932.

[0264] Example 11

[0265] The synthetic route of organic compound M11 is as follows:

[0266]

[0267] Synthesis of intermediate 11-2:

[0268] Dissolve intermediate 1-8 (10 mmol) and intermediate 11-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavap to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain 8.11 mmol of intermediate 11-2, with a yield of 81.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-2: MS(ASAP)=958.

[0269] Synthesis of organic compound M11:

[0270] Add 10 mmol of intermediate 11-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) dropwise. Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), and stir at room temperature for 0.5 hour. Then, cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M11, with a yield of 41.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M11: MS(ASAP) = 932.

[0271] Example 12

[0272] The synthetic route of organic compound M12 is as follows:

[0273]

[0274] Synthesis of intermediate 12-2:

[0275] Dissolve intermediate 1-8 (10 mmol) and intermediate 12-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 7.43 mmol of intermediate 12-2, with a yield of 74.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-2: MS(ASAP) = 958.

[0276] Synthesis of organic compound M12:

[0277] Add 10 mmol of intermediate 12-2 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M12, with a yield of 49.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M12: MS(ASAP) = 932.

[0278] Example 13

[0279] The synthetic route of organic compound M13 is as follows:

[0280]

[0281] Synthesis of intermediate 13-2:

[0282] Dissolve intermediate 1-8 (10 mmol) and intermediate 13-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavap to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain 7.64 mmol of intermediate 13-2, with a yield of 76.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-2: MS(ASAP) = 955.

[0283] Synthesis of organic compound M13:

[0284] Add 10 mmol of intermediate 13-2 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M13, with a yield of 52.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M13: MS(ASAP) = 929.

[0285] Example 14

[0286] The synthetic route of organic compound M14 is as follows:

[0287]

[0288] Synthesis of intermediate 14-2:

[0289] Dissolve intermediate 1-8 (10 mmol) and intermediate 14-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain 7.54 mmol of intermediate 14-2, with a yield of 75.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-2: MS(ASAP) = 955.

[0290] Synthesis of organic compound M14:

[0291] Add 10 mmol of intermediate 14-2 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M14, with a yield of 22.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M14: MS(ASAP) = 929.

[0292] Example 15

[0293] The synthetic route of organic compound M15 is as follows:

[0294]

[0295] Synthesis of intermediate 15-2:

[0296] Dissolve intermediate 1-8 (10 mmol) and intermediate 15-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotavap to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain 6.83 mmol of intermediate 15-2, with a yield of 68.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 15-2: MS(ASAP) = 1017.

[0297] Synthesis of organic compound M15:

[0298] Add 10 mmol of intermediate 15-2 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate and evaporate the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M15, with a yield of 31.4%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M15: MS(ASAP)=991.

[0299] Example 16

[0300] The synthetic route of organic compound M16 is as follows:

[0301]

[0302] Synthesis of intermediate 16-2:

[0303] Dissolve intermediate 1-8 (10 mmol) and intermediate 16-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h; after cooling, rotate and evaporate most of the solvent, then extract and wash and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain 7.34 mmol of intermediate 16-2, with a yield of 73.4%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 16-2: MS(ASAP)=1017.

[0304] Synthesis of organic compound M16:

[0305] Add 10 mmol of intermediate 16-2 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous solution of sodium carbonate and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M16, with a yield of 33.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M16: MS(ASAP) = 991.

[0306] Example 17

[0307] The synthetic route of organic compound M17 is as follows:

[0308]

[0309] Synthesis of intermediate 17-2:

[0310] Dissolve intermediate 1-6 (10 mmol), compound 17-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. Column chromatograph the organic phase to obtain intermediate 17-2 with a molar amount of 6.35 mmol and a yield of 63.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 17-2: MS(ASAP) = 704.

[0311] Synthesis of intermediate 17-3:

[0312] Intermediate 17-2 (10 mmol) and intermediate 3-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain 7.83 mmol of intermediate 17-3 with a yield of 78.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 17-3: MS(ASAP) = 886.

[0313] Synthesis of organic compound M17:

[0314] 10 mmol of intermediate 17-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature. An aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate gave the product as a pale yellow solid powder, i.e., organic compound M17, with a yield of 45.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M17: MS(ASAP) = 860.

[0315] Example 18

[0316] The synthetic route of organic compound M18 is as follows:

[0317]

[0318] Synthesis of intermediate 18-1:

[0319] Intermediate 17-2 (10 mmol) and intermediate 4-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain 7.23 mmol of intermediate 18-1, with a yield of 72.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-1: MS(ASAP) = 886.

[0320] Synthesis of organic compound M18:

[0321] 10 mmol of intermediate 18-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M18, with a yield of 40.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M18: MS(ASAP) = 860.

[0322] Example 19

[0323] The synthetic route of organic compound M19 is as follows:

[0324]

[0325] Synthesis of intermediate 19-2:

[0326] Intermediate 17-2 (10 mmol) and Intermediate 19-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain 8.21 mmol of Intermediate 19-2, with a yield of 82.1%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of Intermediate 19-2: MS(ASAP) = 886.

[0327] Synthesis of organic compound M19:

[0328] 10 mmol of Intermediate 19-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M19, with a yield of 44.3%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M19: MS(ASAP) = 860.

[0329] Example 20

[0330] The synthesis route of organic compound M20 is as follows:

[0331]

[0332] Synthesis of Intermediate 20-2:

[0333] Intermediate 17-2 (10 mmol) and intermediate 20-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 20-2 with a molar amount of 8.71 mmol and a yield of 87.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 20-2: MS(ASAP) = 886.

[0334] Synthesis of organic compound M20:

[0335] 10 mmol of intermediate 20-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M20, with a yield of 28.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M20: MS(ASAP) = 860.

[0336] Example 21

[0337] The synthetic route of organic compound M21 is as follows:

[0338]

[0339] Synthesis of intermediate 21-2:

[0340] Compound 21-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 21-2 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 21-2 was: MS (ASAP) = 469.

[0341] Synthesis of intermediate 21-3:

[0342] Compound 21-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 21-3 with a molar weight of 7.56 mmol and a yield of 75.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 21-3 was: MS (ASAP) = 613.

[0343] Synthesis of intermediate 21-4:

[0344] Intermediate 21-3 (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 and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 21-4 with a molar weight of 6.73 mmol and a yield of 67.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 21-4 was: MS (ASAP) = 726.

[0345] Synthesis of intermediate 21-5:

[0346] Intermediate 21-4 (10 mmol), compound 1-7 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography to obtain intermediate 21-5 with a molar amount of 7.35 mmol and a yield of 73.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-8: MS(ASAP) = 892.

[0347] Synthesis of intermediate 21-6:

[0348] Intermediate 21-5 (10 mmol) and intermediate 3-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 21-6 with a molar amount of 5.93 mmol and a yield of 59.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 21-6: MS(ASAP) = 1074.

[0349] Synthesis of organic compound M21:

[0350] 10 mmol of intermediate 21-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M21, with a yield of 44.2%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M21: MS(ASAP) = 1048.

[0351] Example 22

[0352] The synthetic route of organic compound M22 is as follows:

[0353]

[0354] Synthesis of intermediate 22-1:

[0355] Dissolve intermediate 21-5 (10 mmol) and intermediate 5-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain 5.36 mmol of intermediate 22-1, with a yield of 53.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 22-1: MS(ASAP) = 1074.

[0356] Synthesis of organic compound M22:

[0357] Add 10 mmol of intermediate 22-1 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 h, then distill off the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 h, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 h. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotary evaporate to remove the solvent to obtain a crude product, which is purified by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M22, with a yield of 30.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M22: MS(ASAP) = 1048.

[0358] Example 23

[0359] The synthetic route of organic compound M23 is as follows:

[0360]

[0361] Synthesis of intermediate 23-2:

[0362] Intermediate 1-5 (10 mmol), compound 23-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated, and the organic phase was subjected to column chromatography to obtain intermediate 23-2 with a molar amount of 5.39 mmol and a yield of 53.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-2: MS(ASAP) = 628.

[0363] Synthesis of intermediate 23-4:

[0364] Intermediate 23-2 (10 mmol), compound 23-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated, and the organic phase was subjected to column chromatography to obtain intermediate 23-4 with a molar amount of 8.21 mmol and a yield of 82.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-4: MS(ASAP) = 836.

[0365] Synthesis of intermediate 23-5:

[0366] Intermediate 23-4 (10 mmol) and intermediate 3-1 (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. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 23-5 with a molar amount of 7.83 mmol and a yield of 78.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-5: MS(ASAP) = 1018.

[0367] Synthesis of organic compound M23:

[0368] Add 10 mmol of intermediate 23-5 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), stir at room temperature for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate and evaporate the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, namely organic compound M23, with a yield of 37.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M23: MS(ASAP) = 992.

[0369] Example 24

[0370] The synthetic route of organic compound M24 is as follows:

[0371]

[0372] Synthesis of intermediate 24-1:

[0373] Dissolve intermediate 23-3 (10 mmol) and intermediate 7-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotate and evaporate most of the solvent, then extract and wash with water and separate the liquid. Purify the organic phase by column chromatography and recrystallize to obtain 7.54 mmol of intermediate 24-1, with a yield of 75.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-1: MS(ASAP) = 1018.

[0374] Synthesis of organic compound M24:

[0375] Add 10 mmol of intermediate 24-1 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the dropwise addition is completed, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate and evaporate to remove the solvent to obtain a crude product, which is purified by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M24, with a yield of 32.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M24: MS(ASAP)=992.

[0376] Example 25

[0377] The synthetic route of organic compound M25 is as follows:

[0378]

[0379] Synthesis of intermediate 25-1:

[0380] Dissolve intermediate 23-3 (10 mmol) and intermediate 5-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h. After cooling, rotate and evaporate to remove most of the solvent, then extract and wash and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain 7.33 mmol of intermediate 25-1, with a yield of 73.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 25-1: MS(ASAP)=1018.

[0381] Synthesis of organic compound M25:

[0382] Add 10 mmol of intermediate 25-1 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, which is organic compound M25, with a yield of 31.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M25: MS(ASAP) = 992.

[0383] Example 26

[0384] The synthetic route of organic compound M26 is as follows:

[0385]

[0386] Synthesis of intermediate 26-1:

[0387] Dissolve intermediate 23-1 (10 mmol) and compound 5-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, stir at 100 °C for 6 h; after cooling, evaporate the solvent by rotary evaporation, extract and wash and separate the liquid. The organic phase is subjected to column chromatography to obtain intermediate 26-1, with a molar amount of 8.76 mmol and a yield of 87.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 26-1: MS(ASAP) = 810.

[0388] Synthesis of intermediate 26-3:

[0389] Intermediate 26-1 (10 mmol), Intermediate 26-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 26-3 with a molar amount of 7.29 mmol and a yield of 72.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 26-3: MS(ASAP) = 1038.

[0390] Synthesis of organic compound M26:

[0391] 10 mmol of Intermediate 26-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, it was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and reacted for 2 h, and the n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and it was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain the product as a pale yellow solid powder, namely organic compound M26, with a yield of 31.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M26: MS(ASAP) = 1012.

[0392] Example 27

[0393] The synthesis route of organic compound M27 is as follows:

[0394]

[0395] Synthesis of Intermediate 27-2:

[0396] Intermediate 26-1 (10 mmol), Intermediate 27-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 27-2 with a molar amount of 8.13 mmol and a yield of 81.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 27-2: MS(ASAP) = 1038.

[0397] Synthesis of organic compound M27:

[0398] 10 mmol of Intermediate 27-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; the reaction was quenched by adding an aqueous sodium carbonate solution and ethyl acetate; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain the product as a pale yellow solid powder, i.e., organic compound M27, with a yield of 33.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M27: MS(ASAP) = 1012.

[0399] Example 28

[0400] The synthesis route of organic compound M28 is as follows:

[0401]

[0402] Synthesis of Intermediate 28-2:

[0403] Compound 28-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 28-2 with a molar weight of 9.03 mmol and a yield of 90.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 28-2 was: MS (ASAP) = 425.

[0404] Synthesis of intermediate 28-4:

[0405] Intermediate 28-2 (10 mmol), compound 28-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 28-4 with a molar weight of 8.31 mmol and a yield of 83.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 28-4 was: MS (ASAP) = 516.

[0406] Synthesis of intermediate 28-5:

[0407] Intermediate 28-4 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 28-5 with a molar weight of 6.71 mmol and a yield of 67.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 28-5 was: MS (ASAP) = 704.

[0408] Synthesis of intermediate 28-6:

[0409] Intermediate 28-5 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 28-6 with a molar amount of 7.82 mmol and a yield of 78.2%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 28-6: MS(ASAP) = 886.

[0410] Synthesis of organic compound M28:

[0411] 10 mmol of intermediate 28-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M28, with a yield of 32.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M28: MS(ASAP) = 860.

[0412] Example 29

[0413] The synthetic route of organic compound M29 is as follows:

[0414]

[0415] Synthesis of intermediate 29-2:

[0416] Intermediate 28-2 (10 mmol), compound 29-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 29-2 with a molar amount of 8.17 mmol and a yield of 81.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-2: MS(ASAP) = 516.

[0417] Synthesis of intermediate 29-3:

[0418] Intermediate 29-3 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 29-3 with a molar amount of 6.53 mmol and a yield of 65.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-3: MS(ASAP) = 704.

[0419] Synthesis of intermediate 29-5:

[0420] Intermediate 29-3 (10 mmol) and intermediate 29-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate 29-5 with a molar amount of 7.66 mmol and a yield of 76.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 29-5: MS(ASAP) = 886.

[0421] Synthesis of organic compound M29:

[0422] Add 10 mmol of intermediate 29-5 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool the mixture to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) dropwise. Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours. Then, cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M29, with a yield of 38.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M29: MS(ASAP) = 860.

[0423] Example 30

[0424] The synthetic route of organic compound M30 is as follows:

[0425]

[0426] Synthesis of intermediate 30-2:

[0427] Dissolve intermediate 30-1 (10 mmol), compound 28-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, remove the solvent by rotary evaporation, extract and wash with water and separate the layers. Purify the organic phase by column chromatography to obtain intermediate 30-2 with a molar amount of 8.87 mmol and a yield of 88.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-2: MS(ASAP) = 309.

[0428] Synthesis of intermediate 30-3:

[0429] Intermediate 30-2 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water, and separated by liquid separation. The organic phase was subjected to column chromatography to obtain intermediate 30-3 with a molar amount of 7.54 mmol and a yield of 75.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-3: MS(ASAP) = 497.

[0430] Synthesis of intermediate 30-4:

[0431] Intermediate 30-3 (10 mmol), compound 1-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water, and separated by liquid separation. The organic phase was subjected to column chromatography to obtain intermediate 30-4 with a molar amount of 6.22 mmol and a yield of 62.2%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-4: MS(ASAP) = 641.

[0432] Synthesis of intermediate 30-5:

[0433] Intermediate 30-4 (10 mmol), intermediate 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water, and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 30-5 with a molar amount of 7.27 mmol and a yield of 72.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 30-5: MS(ASAP) = 754.

[0434] Synthesis of intermediate 30-7:

[0435] Intermediate 30-5 (10 mmol), Intermediate 30-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated, and the organic phase was purified by column chromatography and recrystallized to obtain Intermediate 30-7 with a molar amount of 7.38 mmol and a yield of 73.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 30-7: MS(ASAP) = 982.

[0436] Synthesis of organic compound M30:

[0437] 10 mmol of Intermediate 30-7 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, it was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and reacted for 2 h, and the n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and it was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; it was recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M30, with a yield of 41.2%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M30: MS(ASAP) = 956.

[0438] Example 31

[0439] The synthetic route of organic compound M31 is as follows:

[0440]

[0441] Synthesis of Intermediate 31-2:

[0442] Intermediate 30-5 (10 mmol), Intermediate 31-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium(II) chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 31-2 with a molar amount of 7.15 mmol and a yield of 71.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 31-2: MS(ASAP) = 982.

[0443] Synthesis of organic compound M31:

[0444] 10 mmol of Intermediate 31-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, it was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol) was added dropwise. The temperature was raised to 60 °C and reacted for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M31, with a yield of 34.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M31: MS(ASAP) = 956.

[0445] Example 32

[0446] The synthetic route of organic compound M32 is as follows:

[0447]

[0448] Synthesis of Intermediate 32-2:

[0449] Intermediate 32-1 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium(II) chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 32-2 with a molar amount of 8.37 mmol and a yield of 83.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-2: MS(ASAP) = 357.

[0450] Synthesis of intermediate 32-3:

[0451] Intermediate 32-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium(II) chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 32-3 with a molar amount of 7.51 mmol and a yield of 75.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-3: MS(ASAP) = 501.

[0452] Synthesis of intermediate 32-4:

[0453] Intermediate 32-3 (10 mmol), compound 23-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted, washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 32-4 with a molar amount of 6.25 mmol and a yield of 62.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-4: MS(ASAP) = 648.

[0454] Synthesis of intermediate 32-5:

[0455] Intermediate 32-4 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 32-5 with a molar amount of 7.11 mmol and a yield of 71.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-5: MS(ASAP) = 830.

[0456] Synthesis of intermediate 32-6:

[0457] Intermediate 32-5 (10 mmol), intermediate 17-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 32-6 with a molar amount of 7.18 mmol and a yield of 71.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-6: MS(ASAP) = 940.

[0458] Synthesis of intermediate 32-8:

[0459] Intermediate 32-7 (10 mmol), intermediate 32-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 32-8 with a molar amount of 5.33 mmol and a yield of 53.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 32-8: MS(ASAP) = 1205.

[0460] Synthesis of organic compound M32:

[0461] Add 10 mmol of intermediate 32-9 and 100 ml of dry tert-butylbenzene to a 250-ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Quench the reaction by adding an aqueous sodium carbonate solution and ethyl acetate. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, which is purified by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M32, with a yield of 47.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M32: MS(ASAP) = 1179.

[0462] Example 33

[0463] The synthetic route of organic compound M33 is as follows:

[0464]

[0465] Synthesis of intermediate 33-2:

[0466] Dissolve intermediate 32-5 (10 mmol), intermediate 33-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. Purify the organic phase by column chromatography and recrystallize to obtain 5.18 mmol of intermediate 33-2 with a yield of 51.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 33-2: MS(ASAP) = 1073.

[0467] Synthesis of organic compound M33:

[0468] Add 10 mmol of intermediate 33-2 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, which is organic compound M33, with a yield of 33.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M33: MS(ASAP)=1047.

[0469] Example 34

[0470] The synthetic route of organic compound M34 is as follows:

[0471]

[0472] Synthesis of intermediate 34-2:

[0473] Dissolve intermediate 32-2 (10 mmol), compound 34-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, and stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, evaporate the solvent by rotary evaporation, extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography to obtain intermediate 34-2 with a molar amount of 8.11 mmol and a yield of 81.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 34-2: MS(ASAP)=579.

[0474] Synthesis of intermediate 34-3:

[0475] Intermediate 34-2 (10 mmol), compound 23-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation, and the organic phase was subjected to column chromatography to obtain intermediate 34-3 with a molar amount of 7.25 mmol and a yield of 72.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 34-3: MS(ASAP) = 682.

[0476] Synthesis of intermediate 34-4:

[0477] Intermediate 34-3 (10 mmol) and compound 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. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation, and the organic phase was subjected to column chromatography to obtain intermediate 34-4 with a molar amount of 6.65 mmol and a yield of 66.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 34-4: MS(ASAP) = 996.

[0478] Synthesis of intermediate 34-6:

[0479] Intermediate 34-4 (10 mmol), intermediate 34-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 34-6 with a molar amount of 7.37 mmol and a yield of 73.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 34-6: MS(ASAP) = 1241.

[0480] Synthesis of organic compound M34:

[0481] Add 10 mmol of intermediate 34-6 and 100 ml of dry tert-butylbenzene into a 250-ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then, remove the n-hexane solvent by distillation under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then, cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavapor to remove the solvent to obtain a crude product, and purify it by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M34, with a yield of 29.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M34: MS(ASAP) = 1215.

[0482] Example 35

[0483] The synthetic route of organic compound M35 is as follows:

[0484]

[0485] Synthesis of intermediate 35-2:

[0486] Dissolve intermediate 1-2 (10 mmol), compound 35-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, remove the solvent by rotary evaporation, extract and wash with water and separate the layers. Perform column chromatography on the organic phase to obtain intermediate 35-2 with a molar amount of 8.71 mmol and a yield of 87.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-2: MS(ASAP) = 298.

[0487] Synthesis of intermediate 35-3:

[0488] Intermediate 35-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium(II) chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated. The organic phase was purified by column chromatography to obtain intermediate 35-3 with a molar amount of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-3: MS(ASAP) = 442.

[0489] Synthesis of intermediate 35-4:

[0490] Intermediate 35-3 (10 mmol), compound 1-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated. The organic phase was purified by column chromatography to obtain intermediate 35-4 with a molar amount of 6.23 mmol and a yield of 62.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-4: MS(ASAP) = 555.

[0491] Synthesis of intermediate 35-5:

[0492] Intermediate 35-4 (10 mmol), intermediate 1-7 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water and separated. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 35-5 with a molar amount of 7.29 mmol and a yield of 72.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-5: MS(ASAP) = 721.

[0493] Synthesis of intermediate 35-6:

[0494] Intermediate 35-5 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 35-6 with a molar amount of 7.29 mmol and a yield of 72.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 35-6: MS(ASAP) = 903.

[0495] Synthesis of organic compound M35:

[0496] 10 mmol of intermediate 35-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M35, with a yield of 36.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M35: MS(ASAP) = 877.

[0497] Example 36

[0498] The synthesis route of organic compound M36 is as follows:

[0499]

[0500] Synthesis of intermediate 36-3:

[0501] Intermediate 36-1 (20 mmol), compound 36-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation, and the organic phase was subjected to column chromatography to obtain intermediate 36-3 with a molar amount of 8.18 mmol and a yield of 81.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 36-3: MS(ASAP) = 304.

[0502] Synthesis of intermediate 36-4:

[0503] Intermediate 36-3 (10 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation, and the organic phase was subjected to column chromatography to obtain intermediate 36-4 with a molar amount of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 36-4: MS(ASAP) = 492.

[0504] Synthesis of intermediate 36-5:

[0505] Intermediate 36-4 (10 mmol), compound 1-7 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation, and the organic phase was subjected to column chromatography to obtain intermediate 36-5 with a molar amount of 6.19 mmol and a yield of 61.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 36-5: MS(ASAP) = 658.

[0506] Synthesis of intermediate 36-6:

[0507] Intermediate 36-5 (10 mmol) and intermediate 8-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain 7.88 mmol of intermediate 36-6, with a yield of 78.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 36-6: MS(ASAP) = 840.

[0508] Synthesis of organic compound M36:

[0509] 10 mmol of intermediate 36-6 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M36, with a yield of 34.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M36: MS(ASAP) = 813.

[0510] Example 37

[0511] The synthetic route of organic compound M37 is as follows:

[0512]

[0513] Synthesis of intermediate 37-2:

[0514] Intermediate 1-8 (10 mmol) and Intermediate 37-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 37-2 with a molar amount of 7.187 mmol and a yield of 78.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 37-2: MS(ASAP) = 1010.

[0515] Synthesis of organic compound M37:

[0516] 10 mmol of Intermediate 37-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature. An aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product. The pure product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M37, with a yield of 51.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M37: MS(ASAP) = 984.

[0517] Example 38

[0518] The synthesis route of organic compound M38 is as follows:

[0519]

[0520] Synthesis of Intermediate 38-2:

[0521] Intermediate 32-1 (10 mmol), compound 38-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium(II) chloride, 0.1 mmol), S-Phos (2-bis(cyclohexyl)phosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography to obtain intermediate 38-2 with a molar amount of 8.43 mmol and a yield of 84.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 38-2: MS(ASAP) = 377.

[0522] Synthesis of intermediate 38-3:

[0523] Intermediate 38-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine)palladium(II) chloride, 0.1 mmol), S-Phos (2-bis(cyclohexyl)phosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography to obtain intermediate 38-3 with a molar amount of 7.69 mmol and a yield of 76.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 38-3: MS(ASAP) = 521.

[0524] Synthesis of intermediate 38-4:

[0525] Intermediate 38-3 (10 mmol), compound 23-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bis(cyclohexyl)phosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography to obtain intermediate 38-4 with a molar amount of 6.57 mmol and a yield of 65.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 38-4: MS(ASAP) = 668.

[0526] Synthesis of intermediate 38-5:

[0527] Intermediate 38-4 (10 mmol) and intermediate 37-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 38-5 with a molar amount of 8.21 mmol and a yield of 82.1%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 38-5: MS(ASAP) = 918.

[0528] Synthesis of intermediate 38-7:

[0529] Intermediate 38-5 (10 mmol), intermediate 38-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 38-7 with a molar amount of 6.42 mmol and a yield of 64.2%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 38-7: MS(ASAP) = 1050.

[0530] Synthesis of organic compound M38:

[0531] 10 mmol of intermediate 38-7 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a product as a pale yellow solid powder, namely organic compound M38, with a yield of 55.3%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M38: MS(ASAP) = 1024.

[0532] Example 39

[0533] The synthetic route of organic compound M39 is as follows:

[0534]

[0535] Synthesis of intermediate 39-2:

[0536] Dissolve intermediate 28-2 (10 mmol), compound 39-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography to obtain intermediate 39-2 with a molar amount of 8.61 mmol and a yield of 86.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 39-2: MS(ASAP) = 516.

[0537] Synthesis of intermediate 39-3:

[0538] Dissolve intermediate 39-2 (10 mmol), compound 38-6 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bis(cyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography to obtain intermediate 39-3 with a molar amount of 6.55 mmol and a yield of 65.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 39-3: MS(ASAP) = 648.

[0539] Synthesis of intermediate 39-4:

[0540] Dissolve intermediate 39-3 (10 mmol) and intermediate 37-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol), stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain intermediate 39-4 with a molar amount of 7.57 mmol and a yield of 75.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 39-4: MS(ASAP) = 898.

[0541] Synthesis of Organic Compound M39:

[0542] Add 10 mmol of intermediate 39-4 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotate and evaporate the solvent to obtain a crude product, which is purified by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M39, with a yield of 38.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M39: MS(ASAP) = 872.

[0543] Example 40

[0544] The synthesis route of organic compound M40 is as follows:

[0545]

[0546] Synthesis of intermediate 40-2:

[0547] Dissolve intermediate 1-1 (10 mmol), compound 40-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotate and evaporate the solvent, extract and wash with water and separate the liquid. Perform column chromatography on the organic phase to obtain intermediate 40-2 with a molar amount of 7.34 mmol and a yield of 73.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 40-2: MS(ASAP) = 462.

[0548] Synthesis of intermediate 40-4:

[0549] Intermediate 40-2 (10 mmol) and intermediate 40-3 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 40-4 with a molar amount of 7.33 mmol and a yield of 73.3%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 40-4: MS(ASAP) = 894. 1 H NMR (400 MHz, CDCl3) δ 8.21 (d, J = 7.7 Hz, 2H), 7.61 (t, J = 8.8 Hz, 4H), 7.55 - 7.32 (m, 8H), 7.23 (dd, J = 15.0, 13.3 Hz, 4H), 6.95 - 6.77 (m, 2H), 6.68 (t, J = 7.7 Hz, 3H), 5.99 (d, J = 7.1 Hz, 3H), 1.56 (s, 18H), 1.22 - 1.09 (m, 9H).

[0550] Synthesis of organic compound M40:

[0551] 10 mmol of intermediate 40-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M40, with a yield of 36.9%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M40: MS(ASAP) = 868. The 1H NMR spectrum of organic compound M40 is shown in Figure 3 。

[0552] Example 41

[0553] The synthetic route of organic compound M41 is as follows:

[0554]

[0555] Synthesis of Intermediate 41-2:

[0556] Dissolve Intermediate 40-2 (10 mmol), Compound 41-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography to obtain Intermediate 41-2 with a molar amount of 7.97 mmol and a yield of 79.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Intermediate 41-2: MS(ASAP) = 926.

[0557] Synthesis of Organic Compound M41:

[0558] Add 10 mmol of Intermediate 41-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 h, then distill off the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 h, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 h. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases, rotary evaporate to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely Organic Compound M41, with a yield of 43.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of Organic Compound M41: MS(ASAP) = 900.

[0559] Example 42

[0560] The synthesis route of Organic Compound M42 is as follows:

[0561]

[0562] Synthesis of Intermediate 42-2:

[0563] Dissolve intermediate 40-2 (10 mmol), compound 42-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and perform column chromatography on the organic phase to obtain intermediate 42-2 with a molar amount of 8.34 mmol and a yield of 83.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 42-2: MS(ASAP) = 920.

[0564] Synthesis of organic compound M42:

[0565] Add 10 mmol of intermediate 42-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol). Raise the temperature to 60 °C and react for 2 h, then distill off the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 h, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 h. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases, rotary evaporate to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M42, with a yield of 37.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M42: MS(ASAP) = 894.

[0566] Example 43

[0567] The synthesis route of organic compound M43 is as follows:

[0568]

[0569] Synthesis of intermediate 43-2:

[0570] Intermediate 40-2 (10 mmol), compound 43-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography to obtain intermediate 43-2 with a molar amount of 8.82 mmol and a yield of 88.2%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 43-2: MS(ASAP) = 1030.

[0571] Synthesis of organic compound M43:

[0572] 10 mmol of intermediate 43-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; the reaction was quenched by adding an aqueous sodium carbonate solution and ethyl acetate; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, i.e., organic compound M43, with a yield of 51.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M43: MS(ASAP) = 1004. The 1H NMR spectrum of organic compound M43 is shown in Figure 4 。 1 H NMR (400 MHz, CDCl3) δ 9.32 (s, 1H), 9.13 (s, 1H), 8.19 (d, J = 7.8 Hz, 1H), 8.14 - 8.06 (m, 3H), 7.92 (d, J = 7.4 Hz, 2H), 7.72 (d, J = 5.4 Hz, 2H), 7.61 - 7.34 (m, 9H), 7.05 (s, 3H), 3.75 (q, J = 6.0 Hz, 2H), 2.84 (dt, J = 30.8, 18.2 Hz, 8H), 2.36 (d, J = 14.9 Hz, 2H), 2.25 - 2.10 (m, 3H), 1.94 - 1.76 (m, 13H), 1.55 (s, 9H), 1.46 (s, 9H), 0.98 (s, 9H).

[0573] Example 44

[0574] The synthetic route of organic compound M44 is as follows:

[0575]

[0576] Synthesis of intermediate 44-2:

[0577] Dissolve intermediate 1-5 (10 mmol), compound 44-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography to obtain intermediate 44-2 with a molar amount of 7.89 mmol and a yield of 78.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 44-2: MS(ASAP) = 572.

[0578] Synthesis of intermediate 44-3:

[0579] Dissolve intermediate 44-2 (10 mmol) and intermediate 37-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain intermediate 44-3 with a molar amount of 7.81 mmol and a yield of 78.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 44-3: MS(ASAP) = 822.

[0580] Synthesis of intermediate 44-5:

[0581] Dissolve intermediate 44-3 (10 mmol), compound 44-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography to obtain intermediate 44-5 with a molar amount of 6.21 mmol and a yield of 62.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 44-5: MS(ASAP) = 954.

[0582] Synthesis of organic compound M44:

[0583] Add 10 mmol of intermediate 44-5 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and dropwise add a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the dropwise addition is completed, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M44, with a yield of 45.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M44: MS(ASAP) = 928.

[0584] Example 45

[0585] The synthesis route of organic compound M45 is as follows:

[0586]

[0587] Synthesis of intermediate 45-2:

[0588] Dissolve intermediate 44-3 (10 mmol), compound 45-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, and stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, evaporate the solvent by rotary evaporation, extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography to obtain intermediate 45-2 with a molar amount of 6.73 mmol and a yield of 67.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 45-2: MS(ASAP) = 1156.

[0589] Synthesis of organic compound M45:

[0590] Add 10 mmol of intermediate 45-2 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask. Under a nitrogen atmosphere, cool to -30 °C and slowly add a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, which is purified by flash silica gel column chromatography to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M45, with a yield of 43.1%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M45: MS(ASAP) = 1130.

[0591] Example 46

[0592] The synthetic route of organic compound M46 is as follows:

[0593]

[0594] Synthesis of intermediate 46-2:

[0595] Dissolve intermediate 44-3 (10 mmol), compound 46-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. Column chromatography of the organic phase gives intermediate 46-2 with a molar amount of 5.53 mmol and a yield of 55.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 46-2: MS(ASAP) = 1156.

[0596] Synthesis of organic compound M46:

[0597] Add 10 mmol of intermediate 46-2 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol). Raise the temperature to 60 °C and react for 2 hours. Then distill off the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hour. Then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the dropwise addition is completed, raise the temperature to room temperature and stir, and then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature. Add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavap to remove the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product. Recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, namely organic compound M46, with a yield of 35.3%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M46: MS(ASAP)=1130.

[0598] Example 47

[0599] The synthetic route of organic compound M47 is as follows:

[0600]

[0601] Synthesis of intermediate 47-2:

[0602] Dissolve intermediate 44-3 (10 mmol), compound 47-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the liquid. Column chromatograph the organic phase to obtain intermediate 47-2 with a molar amount of 5.27 mmol and a yield of 52.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 47-2: MS(ASAP)=942.

[0603] Synthesis of intermediate 47-3:

[0604] Intermediate 47-2 (10 mmol) and intermediate 46-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain 7.36 mmol of intermediate 47-3 with a yield of 73.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 47-3: MS(ASAP) = 1232.

[0605] Synthesis of organic compound M47:

[0606] 10 mmol of intermediate 47-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column chromatography to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M47, with a yield of 40.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M47: MS(ASAP) = 1206.

[0607] Example 48

[0608] The synthesis route of organic compound M48 is as follows:

[0609]

[0610] Synthesis of intermediate 48-1:

[0611] Intermediate 47-2 (10 mmol) and intermediate 45-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain 7.29 mmol of intermediate 48-1, with a yield of 72.9%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 48-1: MS(ASAP) = 1232.

[0612] Synthesis of organic compound M48:

[0613] 10 mmol of intermediate 48-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a n-hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 h. The n-hexane solvent was removed by distillation under reduced pressure; the reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. Then the reaction solution was cooled to 0 °C, 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, and then further raised to 120 °C and stirred for 3 h. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product; recrystallization was carried out with toluene and ethyl acetate to obtain a pale yellow solid powder of the product, that is, organic compound M48, with a yield of 46.8%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M48: MS(ASAP) = 1206.

[0614] Example 49

[0615] The synthesis route of organic compound M49 is as follows:

[0616]

[0617] Synthesis of intermediate 49-1:

[0618] Intermediate 44-1 (10 mmol) and intermediate 37-1 (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, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 49-1 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 49-1 was: MS (ASAP) = 377.

[0619] Synthesis of intermediate 49-2:

[0620] Compound 49-1 (10 mmol), compound 44-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 49-2 with a molar weight of 8.31 mmol and a yield of 83.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 49-2 was: MS (ASAP) = 509.

[0621] Synthesis of intermediate 49-3:

[0622] Compound 49-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 49-3 with a molar weight of 7.88 mmol and a yield of 78.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 49-3 was: MS (ASAP) = 653.

[0623] Synthesis of intermediate 49-5:

[0624] Intermediate 49-3 (10 mmol), compound 49-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenyl)phosphine palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 49-5 with a molar amount of 5.29 mmol and a yield of 52.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 49-5: MS(ASAP) = 754.

[0625] Synthesis of intermediate 49-6:

[0626] Intermediate 49-5 (10 mmol) and intermediate 46-1 (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. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h; after cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate 49-6 with a molar amount of 7.46 mmol and a yield of 74.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 49-6: MS(ASAP) = 1044.

[0627] Synthesis of intermediate 49-7:

[0628] Intermediate 49-6 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid-liquid extraction, and the organic phase was purified by column chromatography to obtain intermediate 49-7 with a molar amount of 6.75 mmol and a yield of 67.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 49-7: MS(ASAP) = 1232.

[0629] Synthesis of organic compound M49:

[0630] Add 10 mmol of intermediate 49-7 and 100 ml of dry tert-butylbenzene into a 250 ml three-necked flask. Under a nitrogen atmosphere, cool it to -30 °C, and slowly add dropwise a n-hexane solution of t-BuLi (tert-butyllithium, 21 mmol). Raise the temperature to 60 °C and react for 2 hours. Evaporate the n-hexane solvent under reduced pressure; cool the reaction solution to -30 °C again, add boron tribromide (21 mmol), raise the temperature to room temperature and stir for 0.5 hours, then cool the reaction solution to 0 °C, add 42 mmol of N,N-diisopropylethylamine. After the addition is complete, raise the temperature to room temperature and stir, then continue to raise the temperature to 120 °C and stir for 3 hours. Cool the reaction solution to room temperature; add an aqueous sodium carbonate solution and ethyl acetate to quench the reaction; extract the aqueous phase with ethyl acetate and combine the organic phases. Rotavaporize the solvent to obtain a crude product, and purify it by flash silica gel column to obtain a pure product; recrystallize with toluene and ethyl acetate to obtain a light yellow solid powder of the product, that is, organic compound M49, with a yield of 32.6%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M49: MS(ASAP) = 1206.

[0631] Example 50

[0632] The synthetic route of organic compound M50 is as follows:

[0633]

[0634] Synthesis of intermediate 50-1:

[0635] Dissolve intermediate 49-6 (10 mmol), compound 32-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, and stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the liquid. Subject the organic phase to column chromatography to obtain intermediate 50-1 with a molar amount of 6.37 mmol and a yield of 63.7%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of intermediate 50-1: MS(ASAP) = 1252.

[0636] Synthesis of organic compound M50:

[0637] In a 250 ml three-necked flask, 10 mmol of intermediate 50-1 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C under a nitrogen 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 M50, with a yield of 32.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M50 is: MS (ASAP) = 1226.

[0638] Embodiment 51

[0639] The synthetic route of organic compound M51 is as follows:

[0640]

[0641] Synthesis of intermediate 51-1:

[0642] Compound 49-1 (10 mmol), compound 46-1 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 51-1 with a molar weight of 8.72 mmol and a yield of 87.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 51-1 was: MS (ASAP) = 711.

[0643] Synthesis of intermediate 51-2:

[0644] Compound 51-1 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 51-2 with a molar weight of 7.32 mmol and a yield of 73.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 51-2 was: MS (ASAP) = 855.

[0645] Synthesis of intermediate 51-3:

[0646] Intermediate 51-2 (10 mmol), compound 28-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 51-3 with a molar weight of 5.89 mmol and a yield of 58.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 51-3 was: MS (ASAP) = 1100.

[0647] Synthesis of organic compound M51:

[0648] 10 mmol of intermediate 51-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C under a nitrogen atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was 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 M51, with a yield of 39.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M51 is: MS (ASAP) = 1074.

[0649] Comparative Example 1

[0650] Compound 1 was used as the comparative example for Examples 1 to 51 above. The structural formula of Compound 1 is as follows:

[0651]

[0652] As shown in Table 1, 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 M51 obtained in Examples 1 to 63 and Comparative Compound 1 in Comparative Example 1 can be obtained. Specifically, using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.), the specific simulation method can be referred to WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / SpinSinglet), and then the energy structure of the organic molecule is calculated by the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / SpinSinglet). The HOMO energy level and LUMO energy level are calculated according to the following calibration formula, and the S1 energy level and T1 energy level are directly used.

[0653] HOMO (eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206

[0654] LUMO (eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385

[0655] Among them, HOMO, LUMO, T1, and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree.

[0656] Table 1: Energy level data of organic compounds M1 to M51 and Comparative Compound 1

[0657]

[0658]

[0659] As can be seen from the results in Table 1, the T1 energy level or S1 energy level of the organic compounds M1 to M51 provided in Examples 1 to 51 of the present application is higher than the T1 energy level and S1 energy level of Comparative Compound 1, indicating that compared with Comparative Compound 1, the blue light emitted by the organic compounds M1 to M51 of the present application is more inclined to dark blue, which is beneficial for a blue organic light-emitting device using the organic compounds M1 to M51 as the guest material in the light-emitting layer to obtain better color coordinates.

[0660] The exemplary manufacturing steps of the organic light-emitting device 100 provided in the present application are as follows:

[0661] Taking Figure 2 the structure of the organic light-emitting device 100 as an example, the organic light-emitting device 100 provided in this embodiment includes a substrate 110, a first electrode (anode) 101, a hole injection layer 104, a hole transport layer 105, a light-emitting layer 107, an electron transport layer 108, and a first electrode (cathode) 102 stacked in sequence, wherein ITO (indium tin oxide) is used as the anode, PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) is used as the material of the hole injection layer 104, PVK (Sigma Aldrich, average Mn 25,000 - 50,000) is used as the material of the hole transport layer 105, BH-1 to BH-3 are used as the host materials in the light-emitting layer 107 of the corresponding organic light-emitting devices respectively, the organic compounds M1 to M51 in Examples 1 to 51 and Comparative Compound 1 in Comparative Example 1 are used as the guest materials in the light-emitting layer of the corresponding organic light-emitting devices respectively, ET and Liq (lithium 8-hydroxyquinoline) are used as the materials of the electron transport layer 108, and Al is used as the cathode. The specific preparation steps are as follows:

[0662] a. Cleaning of the ITO anode: Clean the ITO conductive glass with chloroform, acetone, and / or isopropanol, and then perform ultraviolet ozone treatment;

[0663] b. Formation of the hole injection layer: Spin-coat the hole injection layer material PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) on the ITO anode and treat it on a hot plate at 180°C for 10 minutes, wherein the thickness of the hole injection layer is 40 nm;

[0664] c. Formation of the hole transport layer: Spin-coat a toluene solution of PVK (Sigma Aldrich, Mn25,000 - 50,000) with a concentration of 5 mg / ml on the hole injection layer, and then treat it on a hot plate at 180°C for 60 minutes, wherein the thickness of the hole transport layer is 20 nm;

[0665] d. Forming the light-emitting layer: In a nitrogen glove box, a light-emitting layer material was spin-coated on the hole-transporting layer and then treated on a hot plate at 140 °C for 10 minutes. The host materials in the light-emitting layers of different organic light-emitting devices corresponded to BH-1, BH-2, or BH-3 respectively, and the guest materials in the light-emitting layers of different organic light-emitting devices corresponded to one of organic compounds M1 to organic compound M51. The solvent was methyl benzoate solution. The mass ratio of the host material to the guest material was 95:5. The concentration of the light-emitting layer material was 15 mg / ml, and the finally formed light-emitting layer had a thickness of 40 nm.

[0666] e. Forming the electron-transporting layer: In a vacuum chamber, above the light-emitting layer, ET and Liq were placed in different evaporation units, and co-deposited at a weight ratio of 50:50 in a high-vacuum (1×10-6 mbar) environment to form an electron-transporting layer with a thickness of 20 nm.

[0667] f. Forming the cathode layer: Above the electron-transporting layer, Al was deposited to obtain an Al cathode with a thickness of 100 nm.

[0668] g. Encapsulation: The device was encapsulated with an ultraviolet-curing resin in a nitrogen glove box.

[0669] Organic light-emitting devices 1 to 55 and comparative elements 1 to 3 were obtained through the above steps. Among them, the guest materials used in organic light-emitting devices 1 to 51 were organic compounds M1 to organic compound M51, and the host material was BH-1; the guest materials used in organic light-emitting devices 52 and 54 were organic compound M5, and the host materials were BH-2 and BH-3 respectively; the guest materials used in organic light-emitting devices 53 and 55 were organic compound M20, and the host materials were BH-2 and BH-3 respectively; the guest materials used in comparative elements 1 to 3 were comparative compound 1, and the host materials were BH-1, BH-2, and BH-3 respectively.

[0670] Among them, the chemical structural formulas of BH-1, BH-2, BH-3, ET, and Liq are as follows:

[0671]

[0672] In this embodiment, current-voltage (J-V) characteristic tests were performed on organic light-emitting devices 1 to 55 and comparative elements 1 to 3, and the CIE chromaticity coordinates (x, y), driving voltage at 1 knit brightness (voltage @ 1 knit [V]), and current density of 10 mA / cm of each organic light-emitting device and comparative element were obtained. 2The luminous efficiency (CE@1knits [cd / A]) obtained at that time, and the time (LT90@1knits [h]) it takes for the luminance to decrease from the initial luminance of 1knits to 90% of the initial luminance. The specific results are shown in Table 2.

[0673] Table 2: Performance data of Organic Light-Emitting Devices 1 to 55 and Comparative Elements 1 to 3

[0674]

[0675]

[0676] As can be seen from Table 2, the Organic Light-Emitting Devices 1 to 55 obtained by using Host Materials M1 to M51 in the light-emitting layer in this application have more excellent color coordinates compared to Comparative Elements 1 to 3.

[0677] As can be seen from Table 2, the luminous efficiencies of Organic Light-Emitting Devices 1 to 55 are all in the range of 5.6 cd / A to 6.4 cd / A, indicating that the luminous efficiencies of Organic Light-Emitting Devices 1 to 55 are much higher than those of Comparative Elements 1 to 3.

[0678] As can be seen from Table 2, the times it takes for the luminances of Organic Light-Emitting Devices 1 to 55 to decrease from the initial luminance of 1knits to 90% of the initial luminance are all in the range of 135 h to 177 h. Compared with the results of the times it takes for Comparative Elements 1 to 3 to decrease from the initial luminance of 1knits to 90% of the initial luminance, the improvement range is from 50% to 100%, indicating that the lifetimes of Organic Light-Emitting Devices 1 to 55 are significantly improved.

[0679] Compared with Comparative Example 1, in the Organic Compounds M1 to M51 of the embodiments of this application, the introduction of structures such as biphenyl ring + naphthofuranobenzene and biphenyl ring + adamantylfluorene makes the overall molecular solubility better, which is conducive to the purification of the compound, thereby improving the compound purity, and further improving the efficiency and lifetime of the fabricated organic light-emitting device.

[0680] Among them, the biphenyl ring + naphthofuranobenzene structure refers to the structure in which the biphenyl ring connected to the nitrogen atom in the boron nitride compound is connected to naphthofuranobenzene, such as etc.; the biphenyl ring + adamantylfluorene structure refers to the structure in which the biphenyl ring connected to the nitrogen atom in the boron nitride compound is connected to adamantylfluorene, such as etc.

[0681] In addition, the luminous efficiencies of the organic light-emitting devices 1-7, 44-51 are all in the range of 6.0-6.4 cd / A, and the lifetimes are all about 170 h. This is because compared with the guest materials in other organic light-emitting devices, the overall molecular conjugation of M1-M7, M44-M51 is larger, and the improvement of the lifetime efficiency of the arylamine combination of benzothiophene + biphenyl ring + naphthofuranobenzene (or adamantylfluorene) is significantly higher than that of the combination of benzothiophene + benzene in the comparative example, and the number of solubilizing groups is larger, which improves the solubility of the guest material and further improves the luminous efficiency and lifetime of the organic light-emitting device.

[0682] In the embodiments of the present application, a boron nitride compound is used as the organic compound applied to the organic light-emitting device. By introducing groups that make the overall conjugation of the organic compound larger, such as biphenyl ring, benzocarbazole, benzofluorene, naphthofuranobenzene, naphthothiophenobenzene, adamantylfluorene, etc. at specified positions in the boron nitride compound, the rigidity of the molecule is enhanced, the molecular stability is increased, the solubility of the molecule is improved, the performance of the material is improved, and thus the luminous efficiency of the organic light-emitting device is improved and the service life of the organic light-emitting device is extended.

[0683] The present application also provides a display panel, which includes the organic light-emitting device as described above.

[0684] The display panel further includes an array substrate on one side of the organic light-emitting device, and a packaging layer on the side of the organic light-emitting device away from the array substrate and covering the organic light-emitting device. The display panel further includes a polarizer layer on the side of the packaging layer away from the organic light-emitting device and a cover plate layer on the side of the polarizer layer away from the organic light-emitting device. Among them, the polarizer layer can be replaced by a color film layer, and the color film layer can include a plurality of color resistors and black matrices on both sides of the color resistors.

[0685] The display panel disclosed in the embodiments of the present application, by using an organic light-emitting device containing a boron nitride compound and introducing groups that make the overall conjugation of the compound larger in the boron nitride compound, enhances the conjugation effect of the material applied to the organic light-emitting device, improves the material performance, improves the luminous efficiency of the display panel and extends the service life of the display panel.

[0686] The technical features of the above embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered to be within the scope described in this specification.

[0687] The above-described embodiments merely represent several implementation manners of the present application. The description thereof is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present application, several modifications and improvements can still be made, and these all fall within the protection scope of the present application. Therefore, the protection scope of the patent of the present application shall be subject to the appended claims.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in formula (1) or formula (2): in, Ar1 is selected from the structure represented by any one of formula (X-1) to formula (X-3) and formula (B-1) to formula (B-4); Ar2 is selected from hydrogen, a structure represented by any one of formula (B-1) to formula (B-4); Ar3 is selected from the structure represented by any one of formula (A-1) to formula (A-5); Ar4 is selected from the structure represented by any one of formula (A-1) to formula (A-5) and formula (B-1) to formula (B-4); The structures of formula (X-1) to (X-3), formula (B-1) to (B-4), and formula (A-1) to (A-5) are as follows: R0, R1, R2, and R5 are selected from -H, -D, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a silyl group having 1 to 20 silicon atoms, a ketone group having 1 to 20 carbon atoms at least one of -C, -C, -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; X is selected from O, S, N-CH3, N-Ph or C(CH3)2; n0 is selected from any integer from 0 to 14. When n0 is greater than or equal to 2, two adjacent R0s may or may not form a ring with each other; n1 is selected from any integer from 0 to 14. When n1 is greater than or equal to 2, two adjacent R1s may or may not form a ring with each other; n2 is selected from any integer from 0 to 14. When n2 is greater than or equal to 2, two adjacent R2s may or may not form a ring with each other; n5 is selected from any integer from 0 to 14. When n5 is greater than or equal to 2, two adjacent R5s may or may not form a ring with each other.

2. The organic compound according to claim 1, characterized in that When Ar2 represents hydrogen, Ar1 and Ar4 are selected from the structure represented by any one of formula (B-1) to formula (B-4), and Ar1 and Ar4 are the same.

3. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of formula (2-1) to formula (2-52): wherein R3 and R4 are selected from -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, a 2 to 20 carbon atom group ... at least one of an alkoxycarbonyl group having 5 to 30 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 isocyanate group, an isocyanate group, an isothiocyanate 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 selected from any integer from 0 to 5. When n3 is greater than or equal to 2, two adjacent R3s may or may not form a ring with each other; n4 is selected from any integer from 0 to 5. When n4 is greater than or equal to 2, two adjacent R4s may or may not form a ring with each other.

4. The organic compound according to claim 3, characterized in that R1, R2, R3, R4, and R5 are at least one 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, a cyclic alkyl group having 3 to 10 carbon atoms, and a triphenylsilyl group.

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

6. A mixture, characterized in that The mixture comprises at least one organic functional material and at least one organic compound as described in any one of claims 1 to 5, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, guest materials, host materials and organic dyes.

7. A composition, characterized in that The composition comprises at least one organic solvent and at least one organic compound according to any one of claims 1 to 5, or the composition comprises at least one organic solvent and a mixture according to claim 6.

8. 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 at least one organic compound as described in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture as described in claim 6, or the material of the organic functional layer includes the composition as described in claim 7.

9. The organic light emitting device according to claim 8, characterized in that: The organic functional layer 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 at least one of the organic compounds.

10. A display panel, characterized in that: Comprising the organic light-emitting device as claimed in claim 8 or 9.

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