Light emitting element and display panel

Abstract

The application discloses a light-emitting element and a display panel. The light-emitting element comprises a first electrode, a second electrode and a light-emitting layer between the first electrode and the second electrode. The material of the light-emitting layer comprises a guest material and a host material. The guest material comprises at least one compound represented by a general formula (1) and at least one compound represented by a general formula (2-1). The host material comprises at least two compounds represented by a general formula (3-1). The application forms the guest material of at least two boron atom fused ring compounds and the host material of at least two anthracene derivatives in the light-emitting layer, so that the carrier balance in the light-emitting layer is higher, the light-emitting efficiency of the light-emitting element is improved, and the light-emitting life of the light-emitting element is prolonged.

Description

Technical Field

[0001] This application relates to the field of display technology, specifically to a light-emitting element and a display panel. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs) typically consist of a positive electrode, a negative electrode, and an organic layer between them. The organic material in the organic layer converts electrical energy into light energy, thus achieving organic electroluminescence. To improve the luminous efficiency and lifespan of OLEDs, the organic layer is often multi-layered, with each layer containing different organic materials. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the positive and negative electrodes of the OLED, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. The injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state, thus realizing the light emission of the OLED. Organic light-emitting devices possess characteristics such as self-illumination, high brightness, high efficiency, low voltage driving, wide viewing angle, high contrast, and high response, therefore, they have broad application prospects.

[0003] Correspondingly, the development of materials for Organic Light Emitting Diodes (OLEDs) has attracted widespread attention due to their advantages such as diverse synthesis methods and simple composition and processing. Meanwhile, to improve the luminous efficiency of organic electroluminescent devices, various material systems with different energy transfer and conversion mechanisms have been explored. However, the luminous efficiency, stability, and lifetime of luminescent materials used in OLED devices (especially those for blue-emitting OLEDs) remain relatively low, limiting the improvement of OLED device performance. Summary of the Invention

[0004] This application provides a light-emitting element and a display panel, which can improve the luminous efficiency of the light-emitting element and extend its luminous life.

[0005] This application provides a light-emitting element, which includes a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode. The material of the light-emitting layer includes a guest material and a host material. The guest material includes at least one compound represented by general formula (1) and at least one compound represented by general formula (2-1). The host material includes at least two compounds represented by general formula (3-1).

[0006] ;

[0007] In the general formula (1):

[0008] Ring A 101 Ring A 102 And Ring A 103 Each is independently selected from at least one of substituted or unsubstituted aromatic groups having 6-60 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 2-60 carbon atoms;

[0009] Z is selected from CR 102 R 103 NR 104 , O or S;

[0010] X1 and Y1 are independently selected from O, S, Se, and NR, respectively. 105 or CR 106 R 107 ;

[0011] R 102 To R 107 Each is independently selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0012] R 102 R 103 They are either independent of each other or connected in a ring;

[0013] R 105 With ring A 101 Ring A 102 And Ring A 103 One of them may be connected to form a first ring structure or not form a ring, wherein the first ring structure is selected from aliphatic or aromatic monocyclic or polycyclic rings;

[0014] R 101 It is selected from at least one of H, D, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 2-30 carbon atoms, substituted or unsubstituted amino groups containing two aryl groups having 6-30 carbon atoms, substituted or unsubstituted amino groups containing aryl groups having 6-30 carbon atoms and heteroaromatic groups having 2-30 carbon atoms, and substituted or unsubstituted amino groups containing two heteroaromatic groups having 2-30 carbon atoms;

[0015] n101 represents any integer from 0 to 2. When n equals 2, R 101 They are either independent of each other or connected in a ring;

[0016] In the general formula (2-1):

[0017] Ring A202 And Ring A 203 Each is independently selected from at least one of substituted or unsubstituted aromatic groups having 6-60 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 2-60 carbon atoms;

[0018] X2 and Y2 are independently selected from O, S, Se, and NR, respectively. 201 or CR 202 R 203 ;

[0019] R 201 To R 203 It is selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0020] R 201 With ring A 202 And Ring A 203 One of them may be connected to form a second ring structure or not form a ring, wherein the second ring structure is selected from aliphatic or aromatic monocyclic or polycyclic rings;

[0021] In the general formula (3-1):

[0022] Ar 301 Selected from deuterated aromatic groups having 6 to 15 carbon atoms;

[0023] L 303 Selected from substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms;

[0024] L 304 Selected from single bonds, substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms;

[0025] L 303 and L 304 It does not contain deuterium;

[0026] A 303 Selected from any of the following groups:

[0027] ;

[0028] V is selected from O or S;

[0029] R 309 At least one selected from H, alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted phenyl groups, and substituted or unsubstituted biphenyl groups;

[0030] n301 is selected from any integer from 0 to 7;

[0031] n302 is any integer from 0 to 9.

[0032] In accordance with the above-mentioned objectives of this application, embodiments of this application also provide a display panel, the display panel including the light-emitting element as described above.

[0033] This application provides a light-emitting element and a display panel. By forming at least two guest materials of boron atom fused ring compounds and at least two host materials of anthracene derivatives in the light-emitting layer, the carrier balance in the light-emitting layer is improved, thereby increasing the luminous efficiency of the light-emitting element and extending its luminous lifetime. Attached Figure Description

[0034] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0035] Figure 1 This is a schematic diagram of a light-emitting element provided in an embodiment of this application. Detailed Implementation

[0036] The technical solutions in the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only a part of the embodiments of this application, and not all of the embodiments. Based on the embodiments in this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. In addition, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application. In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in actual use or operation, specifically the drawing direction in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In this application, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without" parallel solutions. If multiple "optional" options appear in a technical solution, unless otherwise specified and there is no contradiction or mutual constraint relationship, each "optional" option is independent. In this application, the technical features described in an open-ended manner include both closed technical solutions consisting of the listed features and open technical solutions that include the listed features.

[0037] In this application, aromatic group, aromatic group, and aromatic ring system have the same meaning and are interchangeable. "Aryl or aromatic group or aromatic ring system" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" means an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. Understandably, multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0038] In this application, the terms "heteroaryl group," "heteroaryl group," and "heteroaryl ring system" have the same meaning and are interchangeable. "Heteroaryl or heteroaryl group or heteroaryl ring system" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazole, pyridinyl, bipyridinyl, pyrimidinyl, etc. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidineyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolololyl, furanolofuranyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0039] In this application, "substitution" means that one or more hydrogen atoms in the substituent are replaced by the substituent. When the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R, then R can be independently selected from different groups. In the embodiments of this application, "substituted or unsubstituted" means that the defined group can be substituted or not substituted; when the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R. The substituent R is selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R'', silyl, carbonyl, alkoxy The groups include alkyl carbonyl, aryloxy carbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, and trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art; wherein, R' and R'' in -NR'R'' are independently selected from, but not limited to: H, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 C atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted with substituents acceptable in the art.

[0040] In this application, "amine group" refers to a derivative of amine with the structural feature of formula -NR'R'', where R' and R'' have the same meaning as described above.

[0041] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is replaced by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" mentioned below unless otherwise specified. For example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thiophene group is 5.

[0042] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be from 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0043] In this application, an asterisk (*) connected to a single bond indicates a linking or fusion site; when no linking site is specified in the group, any linking site in the group is selected as the linking site; when the same group contains multiple substituents with the same symbol, the substituents can be the same or different from each other, for example... The six R's on the benzene ring can be the same or different from each other; the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0044] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be connected to any position on the ring, for example... R is attached to any substituted site on the benzene ring. For example... express Can be with The benzene ring is fused at any position to form a fused ring, preferably with adjacent C atoms on the benzene ring.

[0045] Currently, due to the low luminous efficiency, stability, and lifespan of the luminescent materials used in OLED devices, there is a problem that makes it difficult to improve the performance of OLED devices.

[0046] Please refer to Figure 1 This application provides a light-emitting element, which includes a first electrode 101, a second electrode 102, and a light-emitting layer 107 located between the first electrode 101 and the second electrode 102. The material of the light-emitting layer 107 includes a guest material and a host material. The guest material includes at least one compound represented by general formula (1) and at least one compound represented by general formula (2-1). The host material includes at least two compounds represented by general formula (3-1).

[0047] ;

[0048] In the general formula (1):

[0049] Ring A 101 Ring A 102 And Ring A 103 Each is independently selected from at least one of substituted or unsubstituted aromatic groups having 6-60 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 2-60 carbon atoms;

[0050] Z is selected from CR 102 R 103 NR 104 , O or S;

[0051] X1 and Y1 are independently selected from O, S, Se, and NR, respectively. 105 or CR 106 R 107 ;

[0052] R 102 To R 107 Each is independently selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0053] R 102 R 103 They are either independent of each other or connected in a ring;

[0054] R 105 With ring A 101 Ring A 102 And Ring A 103One of them may be connected to form a first ring structure or not form a ring, wherein the first ring structure is selected from aliphatic or aromatic monocyclic or polycyclic rings;

[0055] R 101 It is selected from at least one of H, D, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 2-30 carbon atoms, substituted or unsubstituted amino groups containing two aryl groups having 6-30 carbon atoms, substituted or unsubstituted amino groups containing aryl groups having 6-30 carbon atoms and heteroaromatic groups having 2-30 carbon atoms, and substituted or unsubstituted amino groups containing two heteroaromatic groups having 2-30 carbon atoms;

[0056] n101 represents any integer from 0 to 2. When n equals 2, R 101 They are either independent of each other or connected in a ring;

[0057] In the general formula (2-1):

[0058] Ring A 202 And Ring A 203 Each is independently selected from at least one of substituted or unsubstituted aromatic groups having 6-60 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 2-60 carbon atoms;

[0059] X2 and Y2 are independently selected from O, S, Se, and NR, respectively. 201 or CR 202 R 203 ;

[0060] R 201 To R 203 It is selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0061] R 201 With ring A 202 And Ring A 203 One of them may be connected to form a second ring structure or not form a ring, wherein the second ring structure is selected from aliphatic or aromatic monocyclic or polycyclic rings;

[0062] In the general formula (3-1):

[0063] Ar 301 Selected from deuterated aromatic groups having 6 to 15 carbon atoms;

[0064] L 303 Selected from substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms;

[0065] L 304 Selected from single bonds, substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms;

[0066] L 303 and L 304 It does not contain deuterium;

[0067] A 303 Selected from any of the following groups:

[0068] ;

[0069] V is selected from O or S;

[0070] R 309 At least one selected from H, alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted phenyl groups, and substituted or unsubstituted biphenyl groups;

[0071] n301 is selected from any integer from 0 to 7;

[0072] n302 is any integer from 0 to 9.

[0073] In the implementation and application process, the embodiments of this application form at least two guest materials of boron atom fused ring compounds and at least two host materials of anthracene derivatives in the light-emitting layer, thereby improving the carrier balance in the light-emitting layer, thus improving the luminous efficiency of the light-emitting element and extending the luminous lifetime of the light-emitting element.

[0074] Specifically, the structures of the above general formulas (1), (2-1), and (3-1) are narrowed down below with reference to specific embodiments.

[0075] In some embodiments, the compound represented by general formula (1) is selected from the structure represented by general formula (1-1):

[0076] ;

[0077] In general formula (1-1):

[0078] Ring A 101 And Ring A 102 Each is independently selected from at least one of substituted or unsubstituted aromatic groups having 6-60 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 2-60 carbon atoms;

[0079] Z is selected from CR 102 R 103 NR 104 , O or S;

[0080] X1 and Y1 are independently selected from O or NR respectively.105 ;

[0081] R 102 -R 105 Each is independently selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0082] R 102 R 103 They are either independent of each other or connected in a ring;

[0083] R 105 With ring A 101 Or ring A 102 They can be connected to form the first ring structure or not form a ring;

[0084] R 108 It is selected from at least one of H, D, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms.

[0085] Ar 101 To Ar 103 It is selected from at least one of H, D, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms.

[0086] n102, n103, and n104 represent any integer from 0 to 5;

[0087] Ar 104 and Ar 105 Each is independently selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0088] Ar 104 Ar 105 They are either independent of each other or connected in a ring.

[0089] In some embodiments, the compound represented by general formula (1-1) is selected from the structures represented by any of general formulas (1-2) to (1-7):

[0090] .

[0091] Furthermore, in some embodiments, the fusion sites and linkage sites in the above structural formulas are selected, and the compound represented by general formula (1-1) is selected from structures represented by any one of general formulas (1-8) to (1-13):

[0092] .

[0093] In some embodiments, Z is selected from CR 102 R 103 NR 104 , O or S;

[0094] X1 and Y1 are independently selected from O or NR respectively. 105 ;

[0095] R 102 To R 105 Each group is independently selected from substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-20 carbon atoms.

[0096] Ar 101 To Ar 103 Selected from H, D, methyl, isopropyl, tert-butyl, tert-amyl, substituted or unsubstituted phenyl, naphthyl, dibenzofuran, dibenzothiophene, fluorenyl, carbazole, or amino groups;

[0097] A 101 A 102 Each is independently selected from at least one of substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, carbazoyl, substituted or unsubstituted amino, substituted or unsubstituted benzothiophene;

[0098] Ar 104 and Ar 105 Each is independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, biphenyl, carbazolyl, or methyl.

[0099] In some embodiments, R 105 It is selected from methyl, tert-butyl, substituted or unsubstituted phenyl, naphthyl, dibenzofuran, dibenzothiophene, fluorenyl or carbazolyl.

[0100] Continuing from the above, in some embodiments, Ar 101 To Ar 103 Selected from H, D, and methyl.

[0101] In some embodiments, A 101It is selected from any one of a phenyl group substituted with at least one alkyl group having 1 to 5 carbon atoms, a triphenylamino group substituted with at least one alkyl group having 1 to 5 carbon atoms, a benzothiophene group substituted with at least one alkyl group having 1 to 5 carbon atoms, and a triphenylamino group substituted with a phenyl group and at least one alkyl group having 1 to 5 carbon atoms.

[0102] In some embodiments, A 102 Selected from phenyl or D-substituted phenyl.

[0103] In some embodiments, Ar 104 and Ar 105 Each is independently selected from phenyl groups substituted with at least one alkyl group having 1 to 5 carbon atoms; and Ar 104 and Ar 105 They can form five-membered heterocycles or be independent of each other.

[0104] In some embodiments, R 102 and R 103 Each is independently selected from methyl; R 104 Selected from methyl; R 105 Selected from methyl or tert-butyl; R 108 Selected from H or D.

[0105] In some embodiments, the compound represented by general formula (1-1) is selected from structures represented by general formula (1-14):

[0106] ;

[0107] Among them, Ar 106 It is selected from at least one of substituted or unsubstituted aromatic groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 2 to 60 carbon atoms;

[0108] Ar 107 and Ar 108 Each is independently selected from at least one of the following: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms;

[0109] Ar 107 and Ar 108 They are either independent of each other or connected in a ring.

[0110] In some embodiments, Ar 106 To Ar 108 Each is independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, biphenyl, carbazolyl, or methyl.

[0111] Furthermore, in some embodiments, Ar 106 Selected from phenyl; Ar 107 and Ar 108 Each is independently selected from biphenyl or phenyl substituted with at least one alkyl group having 1 to 5 carbon atoms.

[0112] In some embodiments, the compound represented by general formula (1) is selected from at least one of the following compounds:

[0113]

[0114]

[0115]

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[0260]

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[0266]

[0267] .

[0268] Furthermore, the compound represented by general formula (2-1) is selected from the structures represented by general formula (2-2) or general formula (2-3):

[0269] ;

[0270] Among them, Ar 201 Selected from tert-butyl or structures represented by any of formulas (B201) to (B208):

[0271] ;

[0272] Ar 202 The structure is selected from any one of equations (C201) to (C209):

[0273] ;

[0274] When Ar 202 When selecting the structure represented by formula (C209), Ar 201 The structure is selected from any one of the formulas (B201) to (B207);

[0275] Ar 203 The structure is selected from any one of the formulas (B201) to (B207);

[0276] W is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0277] n201 is independently selected from any integer from 0 to 10;

[0278] Any R 204Each is independently selected from: -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain or branched silyl 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 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, trimethylsilyl groups, triphenylsilyl groups, and others. Ketones with 1 to 20 carbon atoms, alkoxycarbonyls with 2 to 20 carbon atoms, aryloxycarbonyls with 7 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms, -CN, carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms.

[0279] It should be noted that in the embodiments of this application, the dashed lines connecting the groups represent connection sites. For example, the dashed lines in the above formulas (B201) to (B208) and formulas (C201) to (C209) represent connection sites.

[0280] In some embodiments, R 204 Selected from H, methyl, or phenyl.

[0281] In some embodiments, the compound represented by general formula (2-1) is selected from at least one of the following compounds:

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321] .

[0322] Furthermore, in some embodiments, in the general formula (3-1):

[0323] Ar 301 Selected from at least one of the following groups:

[0324] ;

[0325] L 303 Selected from at least one of the following groups:

[0326] ;

[0327] L 304 Selected from single bonds or at least one of the following groups:

[0328] .

[0329] In the general formula (3-1), the substituents on the substituted or unsubstituted phenyl group include alkyl groups having 1 to 6 carbon atoms.

[0330] In the substituted or unsubstituted biphenyl, the substituents on the biphenyl include alkyl groups having 1 to 6 carbon atoms.

[0331] In some embodiments, R 309 Each time it appears, it is independently selected from H, D, cyclohexyl, phenyl, or tert-butyl.

[0332] In some embodiments, L 304 Selected from single keys.

[0333] In some embodiments, the compound represented by general formula (3-1) is selected from at least one of the following compounds:

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412] .

[0413] As described above, the embodiments of this application can select guest materials and host materials from the above-mentioned compounds. By forming at least two boron atom fused ring compound guest materials and at least two anthracene derivative host materials in the light-emitting layer, the carrier balance in the light-emitting layer is improved, thereby increasing the luminous efficiency of the light-emitting element and extending the luminous lifetime of the light-emitting element.

[0414] In some embodiments, the light-emitting element provided in this application includes a first electrode 101 and a second electrode 102, and an organic functional layer 103 located between the first electrode 101 and the second electrode 102. The organic functional layer 103 includes a light-emitting layer 107, which is a mixture layer containing a guest material and a host material. The guest material includes at least one compound represented by general formula (1) and at least one compound represented by general formula (2-1), and the host material includes at least two compounds represented by general formula (3-1). That is, the material of the organic functional layer 103 includes multiple organic compounds as described above. The first electrode 101 can be one of an anode and a cathode, and the second electrode 102 can be the other of an anode and a cathode. In this application embodiment, the first electrode 101 is used as the anode and the second electrode 102 as the cathode for illustration.

[0415] In the light-emitting layer 107, the mass ratio of the host material to the guest material in the mixture of the light-emitting layer 107 ranges from 99:1 to 70:30, preferably from 99:1 to 80:20, and more preferably from 99:1 to 90:10. Preferably, the host material in the mixture of the light-emitting layer 107 consists of two types, with a mass ratio of 99:1 to 1:99. Similarly, the guest material in the mixture of the light-emitting layer 107 consists of two types, with a mass ratio of 99:1 to 1:99. This helps to suppress crystallization of the light-emitting layer 107 and suppress concentration quenching caused by high concentration of the guest material, thereby improving the luminous efficiency of the light-emitting element.

[0416] In some embodiments, the light-emitting element can be an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spin light-emitting element, an organic sensor, and an organic plasmon emitting diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, or an organic light-emitting field-effect transistor.

[0417] In some embodiments, the light-emitting element can be applied to various electronic devices, such as display panels, lighting devices, and light sources.

[0418] In some embodiments, the organic functional layer 103 may be a mixture layer, which includes a first compound and a second compound. The first compound is selected from a variety of organic compounds as described above, and the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting guest materials, light-emitting host materials, and organic dyes.

[0419] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multilayered, the organic functional layer 103 includes at least a light-emitting layer 107; preferably, the organic functional layer 103 may also include a hole injection layer 104, a hole transport layer 105, a light-emitting layer 107, an electron blocking layer 106, an electron injection layer 109, an electron transport layer 108, or a hole blocking layer.

[0420] The hole injection layer 104 is disposed between the first electrode 101 and the second electrode 102, the hole transport layer 105 is disposed between the hole injection layer 104 and the second electrode 102, the electron blocking layer 106 is disposed between the hole transport layer 105 and the second electrode 102, the light-emitting layer 107 is disposed between the electron blocking layer 106 and the second electrode 102, the electron transport layer 108 is disposed between the light-emitting layer 107 and the second electrode 102, and the electron injection layer 109 is disposed between the electron transport layer 108 and the second electrode 102.

[0421] In some embodiments, the first electrode 101 is an anode, and the anode is an electrode for injecting holes. The anode can inject holes into the organic functional layer 103, such as by injecting holes into the hole injection layer 104, the hole transport layer 105, or the light-emitting layer 107. 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) level or valence band level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer 104, hole transport layer 105, or electron blocking layer 106, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The anode material includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (indium tin oxide), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be readily selected by those skilled in the art. The anode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, for example, patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to this application.

[0422] In some embodiments, the second electrode 102 is a cathode, and the cathode is an electrode for injecting electrons. The cathode can inject electrons into the organic functional layer 103, such as by injecting electrons into the electron injection layer 109, the electron transport layer 108, or the light-emitting layer 107. 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) level or conduction band level of the light-emitting material in the light-emitting layer, or the n-type semiconductor material serving as the electron injection layer 109, the electron transport layer 108, 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 suitable for use as cathodes in organic light-emitting elements may be used as cathode materials for the devices described in this application. These cathode materials include, but are not limited to, at least one of the following: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0423] In some embodiments, the hole injection layer 104 facilitates hole injection from the anode to the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material that can receive holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material lies between the work function of the anode material and the HOMO of the functional material of the film layer on the side away from the anode (e.g., the hole transport material of the hole transport layer). The hole injection material includes, but is not limited to, at least one of metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based conductive polymers, and polythiophene-based conductive polymers.

[0424] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transported from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and may include, but is not limited to, at least one of arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0425] In some embodiments, the electron transport layer 108 is used to transport electrons. The electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material with high electron mobility known in the art, and may include, but is not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.

[0426] 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, the effect of injecting electrons from the negative electrode, and the excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material. It also has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer and has excellent thin film formation capabilities. The electron injection material includes, but is not limited to, at least one of lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0427] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can typically be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes, but is not limited to, at least one of diazole or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0428] Preferably, the light-emitting layer 107 includes a host material and a guest material, and the host material and the guest material can be selected according to the general structure described in the above embodiments.

[0429] The light-emitting element has an emission wavelength between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm. The light emitted by the light-emitting element can be red, green, or blue, preferably blue.

[0430] In some embodiments, the light-emitting element further includes a substrate, wherein 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, and the first electrode 101 may be located between the substrate and the second electrode 102. The substrate may be a transparent substrate or an opaque substrate. When the substrate is transparent, a transparent light-emitting element can be fabricated. The substrate may be a rigid substrate or a flexible substrate with elasticity. The material of the substrate may include, but is not limited to, plastics, polymers, metals, semiconductor wafers, or glass. Preferably, the substrate includes at least one smooth surface for forming the anode on the surface. More preferably, the surface is free of surface defects. Preferably, the substrate is made of polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate 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.

[0431] In some embodiments, the mixture layer or the light-emitting layer can be formed by a printing or coating process of the composition. Printing or coating processes include inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Preferably, gravure printing, inkjet printing, and other similar processes are used.

[0432] The composition may be a solution or a suspension, and may include a dispersed phase and a dispersant. The dispersed phase is one or more of the organic compounds of general formulas (1), (2-1), and (3-1) as described in the above embodiments, and the dispersant is used to disperse the dispersed phase.

[0433] In the composition, the mass fraction of the organic compound as described above can be from 0.01% to 10%, preferably from 0.1% to 15%, more preferably from 0.2% to 5%, and most preferably from 0.25% to 3%.

[0434] Preferably, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is 17.0~23.2 MPa. 1 / 2 The preferred range is 18.5~21.0 MPa. 1 / 2 The range; δp (polar force) is 0.2~12.5 MPa. 1 / 2The preferred range is 2.0 to 6.0 MPa. 1 / 2 The range; δh (hydrogen bond force) is in the range of 0.9~14.2 MPa. 1 / 2 The preferred range is 2.0 to 6.0 MPa. 1 / 2 The range.

[0435] Preferably, the dispersant has a boiling point greater than or equal to 150°C; more preferably greater than or equal to 180°C; even more preferably greater than or equal to 200°C; more preferably greater than or equal to 250°C; further preferably greater than or equal to 275°C; and most preferably greater than or equal to 300°C. A boiling point of at least 150°C is beneficial in preventing nozzle clogging of the inkjet printhead during inkjet printing, and a higher boiling point is more conducive to preventing clogging.

[0436] The dispersant may include at least one organic solvent, which can evaporate from the solvent system to form a thin film containing the functional material. The organic solvent may include at least one first organic solvent, which may be selected from aromatic or heteroaromatic compounds. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentamene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentene, tripentene, pentamethylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butyric acid, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbenzene... Biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanate, ethyl 2-furanate, etc.

[0437] The first organic solvent may be selected from aromatic ketone solvents. Specifically, the first organic solvent may be selected from 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0438] The first organic solvent may be selected from aromatic ether solvents. Specifically, the first organic solvent may be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0439] 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, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentanyl ether, hexane 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.

[0440] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0441] The organic solvent may further include a second organic solvent, which may be selected from one or more solvents such as methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthane, and indene.

[0442] In addition to the dispersed phase and the dispersant, the composition may also include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0443] Furthermore, the preparation process of the organic compounds represented by general formulas (1), (2-1), and (3-1) provided in the embodiments of this application will be described below with reference to specific embodiments.

[0444] The exemplary preparation methods of the organic compounds provided in this application are shown in the following exemplary embodiments M1 to M17, N1 to N32 and P1 to P22, wherein, embodiments M1 to M17 are organic compounds corresponding to general formula (1), embodiments N1 to N32 are organic compounds corresponding to general formula (2-1) and embodiments P1 to P22 are organic compounds corresponding to general formula (3-1).

[0445] Example M1

[0446] Organic compound M1 ( Synthesis of )

[0447] The synthetic route for organic compound M1 is as follows:

[0448]

[0449] The specific synthetic steps of organic compound M1 are as follows:

[0450] Synthesis of intermediate M1-3: Under nitrogen atmosphere, (28.2 g, 100 mmol) of compound M1-1, (28.1 g, 100 mmol) of compound M1-2, (2.76 g, 3 mmol) of compound Pd2(dba)3, (1.2 g, 6 mmol) of compound tri-tert-butylphosphine, (18.2 g, 200 mmol) of compound sodium tert-butoxide, and 250 mL of anhydrous toluene solvent were mixed and heated to 60 °C, stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent. The solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel, yielding 75%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M1-3: mass-to-charge ratio 482 [M + ].

[0451] Synthesis of intermediate M1-6: Under nitrogen atmosphere, (19.7 g, 100 mmol) of compound M1-4, (48.4 g, 100 mmol) of compound M1-5, (2.76 g, 3 mmol) of compound Pd2(dba)3, (1.2 g, 6 mmol) of compound tri-tert-butylphosphine, (18.2 g, 200 mmol) of compound sodium tert-butoxide, and 250 mL of anhydrous toluene solvent were mixed and heated to 110 °C. The mixture was stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent. The solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 68%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M1-6: mass-to-charge ratio 601 [M + ].

[0452] Synthesis of intermediate M1-8: Under nitrogen atmosphere, (30.0 g, 50 mmol) of compound M1-6, (7.5 g, 50 mmol) of compound M1-7, (1.38 g, 1.5 mmol) of compound Pd2(dba)3, (1.4 g, 3 mmol) of compound X-Phos, (9.6 g, 100 mmol) of sodium tert-butoxide, and 250 mL of anhydrous toluene solvent were mixed and heated to 60 °C, stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent. The solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel, yielding 88%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M1-8: mass-to-charge ratio 714 [M + ].

[0453] Synthesis of intermediate M1-9: Under nitrogen atmosphere, (28.5 g, 40 mmol) of compound M1-8, (19.3 g, 40 mmol) of compound M1-3, (1.10 g, 1.2 mmol) of compound Pd2(dba)3, (1.1 g, 2.4 mmol) of compound X-Phos, (7.7 g, 80 mmol) of compound sodium tert-butoxide, and 250 mL of anhydrous toluene solvent were mixed and heated to 110 °C. The mixture was stirred for 6 hours, cooled to room temperature, quenched with water, and most of the solvent was removed by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 78%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M1-9: mass-to-charge ratio was 1159 [M + ].

[0454] Synthesis of organic compound M1: Under nitrogen atmosphere, (34.8 g, 30 mmol) of compound M1-9 was mixed with 300 mL of toluene. 120 mmol of tert-butyllithium solution was slowly added dropwise at room temperature. After the addition was complete, the reaction was heated to 60 °C and stirred for 2 hours. The reaction was then cooled to -30 °C, and 180 mmol of boron tribromide was added in one step. The reaction was allowed to naturally return to room temperature for 1 hour. Then, 240 mmol of N,N-diisopropylethylamine was added, and the reaction was slowly heated to room temperature for 1 hour. The reaction was then stopped, cooled to room temperature, and the reaction was quenched with sodium acetate aqueous solution. Most of the solvent was removed by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The collected organic liquid was purified by column chromatography after rotary evaporation, yielding 17%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) results of organic compound M1: mass-to-charge ratio 1132 [M + ].

[0455] Example M2

[0456] Organic compound M2 ( Synthesis of )

[0457] The synthetic route for organic compound M2 is as follows:

[0458]

[0459] The specific synthetic steps of organic compound M2 are as follows:

[0460] Synthesis of intermediate M2-1: Under nitrogen atmosphere, (28.2 g, 100 mmol) of compound M1-1, (19.7 g, 100 mmol) of compound palladium acetate, (0.45 g, 2 mmol) of compound S-Phos, (60 mL, 120 mmol) of compound LDA (2.0 M in THF), and 200 mL of anhydrous toluene solvent were mixed and heated to 110 °C, stirred for 12 h, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent. The solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 48%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M2-1: mass-to-charge ratio was 398 [M + ].

[0461] Synthesis of intermediate M2-3: Following the synthetic method of compound M2-1, compound M2-2 was substituted for compound M1-1, with a yield of 49%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M2-3: mass-to-charge ratio 308 [M + ].

[0462] Synthesis of intermediate M2-4: Following the synthetic method for compound M1-8, compound M2-3 was substituted for compound M1-6, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M2-4: mass-to-charge ratio 421 [M + ].

[0463] Synthesis of intermediate M2-5: Following the synthetic method for compound M1-6, compound M2-4 was substituted for compound M1-4, with a yield of 69%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M2-5: mass-to-charge ratio 824 [M + ].

[0464] Synthesis of intermediate M2-6: Following the synthetic method for compound M1-8, compound M2-5 was substituted for compound M1-6, with a yield of 78%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M2-6: mass-to-charge ratio 937 [M + ].

[0465] Synthesis of intermediate M2-7: Following the synthetic method for compound M1-9, compounds M2-6 and M2-1 were used to replace compounds M1-8 and M1-3, respectively, with a yield of 74%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M2-7: mass-to-charge ratio 1298 [M + ].

[0466] Synthesis of organic compound M2: Following the synthetic method of organic compound M1, compound M2-7 was used to replace compound M1-9, with a yield of 15%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M1: mass-to-charge ratio of 1272 [M]. + ].

[0467] Example M3

[0468] Organic compound M3 ( Synthesis of )

[0469] The synthetic route for organic compound M3 is as follows:

[0470]

[0471] The specific synthetic steps of organic compound M3 are as follows:

[0472] Synthesis of intermediate M3-2: Following the synthetic method of compound M2-1, compound M3-1 and the substituted compound M1-1 were synthesized in 45% yield. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-2: mass-to-charge ratio 398 [M + ].

[0473] Synthesis of intermediate M3-4: Following the synthetic method of compound M2-4, compound M3-3 was used to replace compound M1-7, with a yield of 78%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-4: mass-to-charge ratio 393 [M + ].

[0474] Synthesis of intermediate M3-7: Under nitrogen atmosphere, (54.1 g, 200 mmol) of compound M3-5 was mixed with 200 mL of anhydrous tetrahydrofuran solvent, cooled to -78 °C, and 220 mmol of n-butyllithium solution was slowly added dropwise while maintaining the temperature and stirring for 1 h. Then, (54.9 g, 200 mmol) of compound M3-6 was added in one go, and the mixture was allowed to return to room temperature naturally for 1 h. The reaction was quenched with water, and most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel, yielding 51%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-7: mass-to-charge ratio 464 [M + ].

[0475] Synthesis of intermediate M3-8: Under nitrogen atmosphere, 46.4 g (100 mmol) of compound M3-7 was mixed with 200 mL of anhydrous tetrahydrofuran solvent, cooled to -78 °C, and 120 mmol of LDA solution was slowly added dropwise while maintaining the temperature and stirring for 1 h. Then, 120 mmol of hexachloroethane was added in a single batch, and the mixture was allowed to return to room temperature naturally for 1 h. The reaction was quenched with water, and most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel, yielding 65%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-8: mass-to-charge ratio 498 [M + ].

[0476] Synthesis of intermediate M3-9: Following the synthetic method for compound M2-5, compounds M3-8 and M3-4 were used to replace compounds M1-5 and M2-4, respectively, with a yield of 74%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-9: mass-to-charge ratio 810 [M + ].

[0477] Synthesis of intermediate M3-10: Following the synthetic method for compound M2-6, compound M2-5 was replaced by compound M3-9, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-10: mass-to-charge ratio 923 [M + ].

[0478] Synthesis of intermediate M3-11: Following the synthetic method for compound M2-7, compounds M3-9 and M3-2 were used to replace compounds M2-6 and M2-1, respectively, with a yield of 75%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M3-11: mass-to-charge ratio of 1284 [M + ].

[0479] Synthesis of organic compound M3: Following the synthetic method of compound M1, compound M1-9 was replaced by compound M3-11, with a yield of 18%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M3: mass-to-charge ratio: 1258 [M + ].

[0480] Example M4

[0481] Organic compound M4 ( Synthesis of )

[0482] The synthetic route for organic compound M4 is as follows:

[0483]

[0484] The specific synthetic steps of organic compound M4 are as follows:

[0485] Synthesis of intermediate M4-2: Following the synthetic method of compound M2-1, compound M4-1 was substituted for compound M1-1, with a yield of 47%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M4-2: mass-to-charge ratio 424 [M + ].

[0486] Synthesis of intermediate M4-3: Following the synthetic method for compound M1-6, compounds M3-8 and M2-4 were used to replace compounds M1-5 and 1-4, respectively, with a yield of 73%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M4-3: mass-to-charge ratio 838 [M + ].

[0487] Synthesis of intermediate M4-4: Following the synthetic method of compound M1-8, compound M4-3 was substituted for compound M1-6, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M4-4: mass-to-charge ratio 951 [M + ].

[0488] Synthesis of intermediate M4-5: Following the synthetic method for compound M1-9, compounds M4-4 and M4-2 were used to replace compounds M1-8 and 1-3, respectively, with a yield of 71%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M4-5: mass-to-charge ratio of 1338 [M + ].

[0489] Synthesis of organic compound M4: Following the synthetic method of compound M1, compound M4-5 was substituted for compound M1-9, with a yield of 17%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M4: mass-to-charge ratio: 1312 [M + ].

[0490] Example M5

[0491] Organic compound M5 ( Synthesis of )

[0492] The synthetic route for organic compound M5 is as follows:

[0493]

[0494] The specific synthetic steps of organic compound M5 are as follows:

[0495] Synthesis of intermediate M5-3: Under nitrogen atmosphere, (28 g, 100 mmol) of compound M5-1, (6 g, 150 mmol) of NaOH, and 100 mL of dimethylformamide were added to a 250 mL two-necked flask and stirred for 1 hour. Then, (14.2 g, 100 mmol) of compound M5-2 was added all at once, and the mixture was stirred for 4 hours. After the reaction was complete, the reaction solution was poured into 400 mL of purified water, stirred, and filtered to obtain a solid. The solid was purified by recrystallization with a mixture of ethanol and dichloromethane, with a yield of 84%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) results of intermediate M5-3: mass-to-charge ratio of 295 [M + ].

[0496] Synthesis of intermediate M5-4: Following the synthetic method of compound M2-1, compound M5-3 was substituted for compound M1-1, with a yield of 50%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M5-4: mass-to-charge ratio 411 [M+ ].

[0497] Synthesis of intermediate M5-6: Following the synthetic method for compound M3-7, compound M5-5 was substituted for compound M3-6, with a yield of 56%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M5-6: mass-to-charge ratio 465 [M + ].

[0498] Synthesis of intermediate M5-7: Following the synthetic method for compound M3-8, compound M5-6 was used to replace compound M3-7, with a yield of 64%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M5-7: mass-to-charge ratio 499 [M + ].

[0499] Synthesis of intermediate M5-8: Following the synthetic method for compound M3-9, compounds M5-7 and M2-4 were substituted for compounds M3-8 and M3-4, respectively, with a yield of 83%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M5-8: mass-to-charge ratio 839 [M + ].

[0500] Synthesis of intermediate M5-9: Following the synthetic method for compound M3-10, compound M5-8 was substituted for compound M3-9, with a yield of 80%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M5-9: mass-to-charge ratio 952 [M + ].

[0501] Synthesis of intermediate M5-10: Following the synthetic method for compound M3-11, compounds M5-9 and M5-4 were used to replace compounds M3-10 and M3-2, respectively, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M5-10: mass-to-charge ratio 1326 [M + ].

[0502] Synthesis of organic compound M5: Following the synthetic method of compound M1, compound M5-10 was used to replace compound M1-9, with a yield of 16%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M4: Mass-to-charge ratio: 1300 [M + ].

[0503] Example M6

[0504] Organic compound M6 ( Synthesis of )

[0505] The synthetic route for organic compound M6 is as follows:

[0506]

[0507] The specific synthetic steps of organic compound M6 are as follows:

[0508] Synthesis of intermediate M6-2: Following the synthetic method of compound M2-1, compound M6-1 was substituted for compound M1-1, with a yield of 46%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M6-2: mass-to-charge ratio 414 [M + ].

[0509] Synthesis of intermediate M6-3: Following the synthetic method for compound M5-10, compound M6-2 was substituted for compound M5-4, with a yield of 72%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M6-3: mass-to-charge ratio 1329 [M]. + ].

[0510] Synthesis of organic compound M6: Following the synthetic method of compound M1, compound M6-3 was substituted for compound M1-9, with a yield of 18%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M6: mass-to-charge ratio: 1303 [M + ].

[0511] Example M7

[0512] Organic compound M7 ( Synthesis of )

[0513] The synthetic route for organic compound M7 is as follows:

[0514]

[0515] The specific synthetic steps of organic compound M7 are as follows:

[0516] Synthesis of intermediate M7-2: Following the synthetic method of compound M2-1, compound M7-1 was substituted for compound M1-1, with a yield of 46%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M7-2: mass-to-charge ratio 398 [M]. + ].

[0517] Synthesis of intermediate M7-3: Following the synthetic method for compound M5-10, compound M7-2 was substituted for compound M5-4, with a yield of 72%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M7-3: mass-to-charge ratio 1313 [M + ].

[0518] Synthesis of organic compound M7: Following the synthetic method of compound M1, compound M7-3 was used to replace compound M1-9, with a yield of 19%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M6: Mass-to-charge ratio: 1287 [M] + ].

[0519] Example M8

[0520] Organic compound M8 ( Synthesis of )

[0521] The synthetic route for organic compound M8 is as follows:

[0522]

[0523] The specific synthetic steps of organic compound M8 are as follows:

[0524] Synthesis of intermediate M8-2: Under nitrogen atmosphere, (48.4 g, 100 mmol) of compound M1-5, (15 g, 100 mmol) of compound M8-1, (0.57 g, 3 mmol) of CuI, (13.8 g, 100 mmol) of potassium carbonate, and 150 mL of dimethylformamide were mixed, heated to 110 °C, and stirred for 12 hours. After cooling to room temperature, most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 61%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M8-2: mass-to-charge ratio was 554 [M + ].

[0525] Synthesis of intermediate M8-3: Following the synthetic method of compound M1-8, compound M8-2 was substituted for compound M1-6, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M8-3: mass-to-charge ratio 666 [M + ].

[0526] Synthesis of intermediate M8-4: Following the synthetic method of compound M1-9, compound M8-3 was substituted for compound M1-8, with a yield of 75%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M8-4: mass-to-charge ratio 1112 [M + ].

[0527] Synthesis of organic compound M8: Following the synthetic method of compound M1, compound M8-4 was substituted for compound M1-9, with a yield of 23%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M8: mass-to-charge ratio: 1085 [M + ].

[0528] Example M9

[0529] Organic compound M9 ( Synthesis of )

[0530] The synthetic route for organic compound M9 is as follows:

[0531]

[0532] The specific synthetic steps of organic compound M9 are as follows:

[0533] Synthesis of intermediate M9-3: Under nitrogen atmosphere, (42.3 g, 100 mmol) of compound M9-1, (17.3 g, 100 mmol) of compound M9-2, (65.2 g, 200 mmol) of cesium carbonate, and 200 mL of dimethylformamide were mixed and heated under reflux for 12 hours. After the reaction was completed, the reaction solution was allowed to cool to room temperature, most of the solvent was evaporated by rotary evaporation, and the mixture was extracted with dichloromethane, washed three times with water, and the organic liquid was collected and purified by column chromatography with silica gel. The yield was 62%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M9-3: mass-to-charge ratio was 576 [M + ].

[0534] Synthesis of intermediate M9-4: Following the synthetic method of compound M2-1, compound M9-3 was substituted for compound M1-1, with a yield of 45%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M9-4: mass-to-charge ratio 693 [M + ].

[0535] Synthesis of intermediate M9-5: Following the synthetic method for compound M2-6, compound M9-4 was substituted for compound M2-5, with a yield of 75%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M9-5: mass-to-charge ratio 806 [M + ].

[0536] Synthesis of intermediate M9-6: Following the synthetic method for compound M2-7, compound M9-5 was substituted for compound M2-6, with a yield of 66%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M9-6: mass-to-charge ratio 1167 [M + ].

[0537] Synthesis of compound M9: Following the synthetic method of compound M1, compound M9-6 was used to replace compound M1-9, with a yield of 24%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M9: mass-to-charge ratio: 1140 [M +].

[0538] Example M10

[0539] Organic compound M10 ( Synthesis of )

[0540] The synthetic route for organic compound M10 is as follows:

[0541]

[0542] The specific synthetic steps of organic compound M10 are as follows:

[0543] Synthesis of intermediate M10-3: Following the synthetic method for compound M3-7, compounds M10-1 and M10-2 were used to replace compounds M3-5 and M3-6, respectively, with a yield of 54%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M10-3: mass-to-charge ratio 407 [M + ].

[0544] Synthesis of intermediate M10-4: Following the synthetic method for compound M9-3, compound M10-3 was used to replace compound M9-1, with a yield of 62%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M10-4: mass-to-charge ratio 560 [M + ].

[0545] Synthesis of intermediate M10-6: Following the synthetic method for compound M9-3, compounds M10-4 and M10-5 were used to replace compounds M9-1 and M9-2, respectively, with a yield of 55%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M10-6: mass-to-charge ratio 803 [M + ].

[0546] Synthesis of intermediate M10-7: Following the synthetic method of compound M2-1, compound M10-6 was used to replace compound M1-1 and 2 molar equivalents of compound M1-4, with a yield of 55%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M10-7: mass-to-charge ratio 1036 [M + ].

[0547] Synthesis of organic compound M10: Following the synthetic method of compound M1, compound M10-7 was substituted for compound M1-9, with a yield of 26%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M10: mass-to-charge ratio: 1009 [M + ].

[0548] Example M11

[0549] Organic compound M11 ( Synthesis of )

[0550] The synthetic route for organic compound M11 is as follows:

[0551]

[0552] The specific synthetic steps of organic compound M11 are as follows:

[0553] Synthesis of intermediate M11-1: Following the synthetic method for compound M3-7, compounds M10-1 and M5-5 were used to replace compounds M3-5 and M3-6, respectively, with a yield of 54%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M11-1: mass-to-charge ratio of 422 [M + ].

[0554] Synthesis of intermediate M11-2: Following the synthetic method of compound M9-3, compound M11-1 was substituted for compound M9-1, with a yield of 62%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M11-2: mass-to-charge ratio 575 [M + ].

[0555] Synthesis of intermediate M11-4: Following the synthetic method for compound M9-3, compounds M11-2 and M11-3 were used to replace compounds M9-1 and M9-2, respectively, with a yield of 55%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M11-4: mass-to-charge ratio of 844 [M + ].

[0556] Synthesis of intermediate M11-5: Following the synthetic method for compound M10-7, compound M11-4 was substituted for compound M10-6, yielding 45%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M11-5: mass-to-charge ratio 1077 [M + ].

[0557] Synthesis of organic compound M11: Following the synthetic method for compound M1, compound M11-5 was substituted for compound M1-9, yielding 25%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M11: mass-to-charge ratio: 1050 [M + ].

[0558] Example M12

[0559] Organic compound M12 ( Synthesis of )

[0560] The synthetic route for organic compound M12 is as follows:

[0561]

[0562] The specific synthesis steps of organic compound M12 are as follows:

[0563] Synthesis of intermediate M12-2: Following the synthetic method of compound M1-3, compound M12-1 was substituted for compound M1-1, with a yield of 78%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M12-2: mass-to-charge ratio of 498 [M]. + ].

[0564] Synthesis of intermediate M12-3: Following the synthetic method of compound M2-5, compounds M1-7 and M1-5 were substituted for compounds M2-4 and M1-5, respectively. The reaction temperature was adjusted to 80℃, and the yield was 76%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of organic compound M12-3: mass-to-charge ratio was 553 [M + ].

[0565] Synthesis of intermediate M12-5: Following the synthetic method for compound M2-5, compounds M12-3 and M12-4 were used to replace compounds M2-4 and M1-5, respectively, with a yield of 78%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M12-5: mass-to-charge ratio 741 [M + ].

[0566] Synthesis of intermediate M12-6: Following the synthetic method for compound M1-8, compound M12-5 was substituted for compound M1-6, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M12-6: mass-to-charge ratio 854 [M + ].

[0567] Synthesis of intermediate M12-7: Following the synthetic method for compound M1-9, compounds M12-6 and M12-2 were used to replace compounds M1-8 and M1-3, respectively, with a yield of 83%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M12-7: mass-to-charge ratio 1315 [M + ].

[0568] Synthesis of organic compound M12: Following the synthetic method of compound M1, compound M12-7 was substituted for compound M1-9, with a yield of 14%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M12: mass-to-charge ratio: 1289 [M] + ].

[0569] Example M13

[0570] Organic compound M13 ( Synthesis of )

[0571] The synthetic route for organic compound M13 is as follows:

[0572]

[0573] The specific synthetic steps of organic compound M13 are as follows:

[0574] Synthesis of intermediate M13-1: Following the synthetic method for compound M8-2, compounds M5-7 and M10-5 were used to replace compounds M1-5 and M8-1, respectively, with a yield of 55%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M13-1: mass-to-charge ratio 682 [M + ].

[0575] Synthesis of intermediate M13-2: Following the synthetic method of compound M2-1, compound M1-1 was substituted for compound M1-1, with a yield of 49%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M13-2: mass-to-charge ratio 798 [M + ].

[0576] Synthesis of intermediate M13-3: Following the synthetic method of compound M1-9, compounds M13-2 and M2-4 were used to replace compounds M1-3 and M1-8, respectively, with a yield of 82%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M13-3: mass-to-charge ratio of 1182 [M + ].

[0577] Synthesis of organic compound M13: Following the synthetic method of compound M1, compound M13-3 was used to replace compound M1-9, with a yield of 23%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M13: mass-to-charge ratio: 1155 [M + ].

[0578] Example M14

[0579] Organic compound M14 ( Synthesis of )

[0580] The synthetic route for organic compound M14 is as follows:

[0581]

[0582] The specific synthetic steps of organic compound M14 are as follows:

[0583] Synthesis of intermediate M14-3: Under nitrogen atmosphere, (46.6 g, 200 mmol) of compound M14-1, (29.8 g, 200 mmol) of compound M14-2, (1.83 g, 2 mmol) of Pd2(dba)3, (8.1 mL, 4 mmol) of TTBP (10% inTOL), (38.4 g, 400 mmol) of sodium tert-butoxide, and 400 mL of toluene were mixed and reacted at 70 °C for 4 hours. After the reaction, the reaction solution was allowed to cool to room temperature, most of the solvent was evaporated by rotary evaporation, and the mixture was extracted with dichloromethane, washed three times with water, and the organic liquid was collected and purified by column chromatography with silica gel. The yield was 82%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results of intermediate M14-3: mass-to-charge ratio was 301 [M + ].

[0584] Synthesis of intermediate M14-4: Following the synthetic method of compound M2-3, compound M14-3 was used to replace compound M1-4, with a yield of 52%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M14-4: mass-to-charge ratio 412 [M + ].

[0585] Synthesis of intermediate M14-5: Following the synthetic method for compound M2-4, compound M14-4 was used to replace compound M2-3, with a yield of 85%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M14-5: mass-to-charge ratio 525 [M + ].

[0586] Synthesis of intermediate M14-6: Following the synthetic method for compound M2-5, compound M14-5 was used to replace compound M2-4, with a yield of 80%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M14-6: mass-to-charge ratio 928 [M + ].

[0587] Synthesis of intermediate M14-7: Following the synthetic method for compound M2-6, compound M14-6 was used to replace compound M2-5, with a yield of 75%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M14-7: mass-to-charge ratio 1041 [M + ].

[0588] Synthesis of intermediate M14-8: Following the synthetic method for compound M2-7, compound M14-7 was used to replace compound M2-6, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M14-8: mass-to-charge ratio 1487 [M + ].

[0589] Synthesis of organic compound M14: Following the synthetic method of compound M1, compound M14-8 was used to replace compound M1-9, with a yield of 20%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M14: mass-to-charge ratio: 1460 [M + ].

[0590] Example M15

[0591] Organic compound M15 ( Synthesis of )

[0592] The synthetic route for organic compound M15 is as follows:

[0593]

[0594] The specific synthetic steps of organic compound M15 are as follows:

[0595] Synthesis of intermediate M15-2: Following the synthetic method of compound M2-1, compound M15-1 was used to replace compound M1-4, with a yield of 47%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M15-2: mass-to-charge ratio of 424 [M + ].

[0596] Synthesis of intermediate M15-3: Following the synthetic method for compound M2-7, compounds M15-2 and M14-7 were used to replace compounds M2-1 and M2-6, respectively, with a yield of 79%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M15-3: mass-to-charge ratio of 1428 [M + ].

[0597] Synthesis of organic compound M15: Following the synthetic method of compound M1, compound M15-3 was used to replace compound M1-9, with a yield of 19%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M15: mass-to-charge ratio: 1402 [M + ].

[0598] Example M16

[0599] Organic compound M16 ( Synthesis of )

[0600] The synthetic route for organic compound M16 is as follows:

[0601]

[0602] The specific synthetic steps of organic compound M16 are as follows:

[0603] Synthesis of intermediate M16-2: Following the synthetic method of compound M2-1, compound M1-1 was substituted for compound M1-1, with a yield of 52%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M16-2: mass-to-charge ratio 404 [M + ].

[0604] Synthesis of intermediate M16-3: Following the synthetic method for compound M1-9, compounds M16-2 and M2-6 were used to replace compounds M1-3 and M1-6, respectively, with a yield of 74%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M16-3: mass-to-charge ratio 1303 [M + ].

[0605] Synthesis of organic compound M16: Following the synthetic method of organic compound M1, compound M16-3 was used to replace compound M1-9, with a yield of 17%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M1: mass-to-charge ratio of 1277 [M]. + ].

[0606] Example M17

[0607] Organic compound M17 ( Synthesis of )

[0608] The synthetic route for organic compound M17 is as follows:

[0609]

[0610] The specific synthetic steps of organic compound M17 are as follows:

[0611] Synthesis of intermediate M17-1: Following the synthetic method for compound M2-1, compounds M15-1 and M16-1 were substituted for compounds M1-4 and M1-1, respectively, with a yield of 45%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-1: mass-to-charge ratio of 430 [M + ].

[0612] Synthesis of intermediate M17-2: Following the synthetic method for compound M14-3, compound M14-2 was replaced with compound M1-7, yielding 89%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-2: mass-to-charge ratio 301 [M + ].

[0613] Synthesis of intermediate M17-3: Following the synthetic method of compound M2-3, compound M17-2 was substituted for compound M1-4, with a yield of 55%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-3: mass-to-charge ratio 412 [M + ].

[0614] Synthesis of intermediate M17-4: Following the synthetic method for compound M2-4, compound M17-3 was substituted for compound M2-3, with a yield of 86%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-4: mass-to-charge ratio 525 [M + ].

[0615] Synthesis of intermediate M17-5: Following the synthetic method for compound M2-5, compound M17-4 was substituted for compound M2-4, with a yield of 80%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-5: mass-to-charge ratio 928 [M + ].

[0616] Synthesis of intermediate M17-6: Following the synthetic method for compound M2-6, compound M17-5 was substituted for compound M2-5, with a yield of 77%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-6: mass-to-charge ratio 1041 [M + ].

[0617] Synthesis of intermediate M17-7: Following the synthetic method for compound M2-7, compound M17-6 was substituted for compound M2-6, with a yield of 81%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate M17-7: mass-to-charge ratio 1433 [M + ].

[0618] Synthesis of organic compound M17: Following the synthetic method of compound M1, compound M17-7 was used to replace compound M1-9, with a yield of 15%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for organic compound M14: Mass-to-charge ratio: 1407 [M + ].

[0619] Example N1

[0620] The synthetic route for organic compound N1 is as follows:

[0621]

[0622] Synthesis of intermediate N1-3:

[0623] Compound N1-1 (10 mmol), compound N1-2 (20 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 1-3 with a molar amount of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N1-3 was: MS(ASAP) = 372.

[0624] Synthesis of intermediate N1-5:

[0625] Compound N1-3 (10 mmol), compound N1-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to give intermediate N1-5 with a molar amount of 7.57 mmol and a yield of 75.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N1-5 was: MS(ASAP) = 524.

[0626] Synthesis of intermediate N1-7:

[0627] Intermediate N1-5 (10 mmol), compound N1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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. Organic phase column chromatography was performed to obtain intermediate N1-7 with a molar amount of 6.32 mmol and a yield of 63.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N1-7 was: MS(ASAP) = 926.

[0628] Synthesis of intermediate N1-9:

[0629] Intermediate N1-7 (10 mmol), compound N1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate 1-9 with a molar amount of 6.37 mmol and a yield of 63.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N1-9 was: MS(ASAP) = 1027.

[0630] Synthesis of intermediate N1-11:

[0631] Intermediates N1-9 (10 mmol) and N1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate N1-11 with a molar amount of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N1-11 was MS(ASAP)=1131.

[0632] Synthesis of intermediate N1-13:

[0633] Intermediate N1-11 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N1-13 with a molar amount of 5.39 mmol and a yield of 53.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N1-13 was MS(ASAP) = 1319.

[0634] Synthesis of organic compound N1:

[0635] In a 250 mL three-necked flask, 10 mmol of intermediate N1-13 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N1, with a yield of 47.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N1 was: MS(ASAP)=1293.

[0636] Example N2

[0637] The synthetic route for the organic compound N2 is as follows:

[0638]

[0639] Synthesis of intermediate N2-2:

[0640] Compounds N1-9 (10 mmol) and N2-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N2-2 with a molar amount of 8.38 mmol and a yield of 83.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N2-2 was: MS(ASAP) = 1317.

[0641] Synthesis of intermediate N2-3:

[0642] Intermediate N2-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N2-3 with a molar amount of 5.81 mmol and a yield of 58.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N2-3 was MS(ASAP) = 1505.

[0643] Synthesis of organic compound N2:

[0644] In a 250 mL three-necked flask, 10 mmol of intermediate N2-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N2, with a yield of 39.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N2 was: MS(ASAP)=1479.

[0645] Example N3

[0646] The synthetic route for organic compound N3 is as follows:

[0647]

[0648] Synthesis of intermediate N3-2:

[0649] Compounds N1-9 (10 mmol) and N3-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N3-2 with a molar amount of 8.64 mmol and a yield of 86.4%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N3-2 was: MS(ASAP) = 1149.

[0650] Synthesis of intermediate N3-3:

[0651] Intermediate N3-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N3-3 with a molar amount of 6.43 mmol and a yield of 64.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N3-3 was MS(ASAP) = 1337.

[0652] Synthesis of organic compound N3:

[0653] In a 250 mL three-necked flask, 10 mmol of intermediate N3-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N3, with a yield of 34.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N3 was: MS(ASAP)=1311.

[0654] Example N4

[0655] The synthetic route for organic compound N4 is as follows:

[0656]

[0657] Synthesis of intermediate N4-2:

[0658] Compounds N1-9 (10 mmol) and N4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N4-2 with a molar amount of 8.31 mmol and a yield of 83.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N4-2 was: MS(ASAP) = 1165.

[0659] Synthesis of intermediate N4-3:

[0660] Intermediate N4-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N4-3 with a molar amount of 6.15 mmol and a yield of 61.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N4-3 was MS(ASAP) = 1353.

[0661] Synthesis of organic compound N4:

[0662] In a 250 mL three-necked flask, 10 mmol of intermediate N4-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N4, with a yield of 42.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N4 was: MS(ASAP)=1327.

[0663] Example N5

[0664] The synthetic route for organic compound N5 is as follows:

[0665]

[0666] Synthesis of intermediate N5-2:

[0667] Compounds N1-9 (10 mmol) and N5-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N5-2 with a molar amount of 8.24 mmol and a yield of 82.4%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N5-2 was: MS(ASAP) = 1162.

[0668] Synthesis of intermediate N5-3:

[0669] Intermediate N5-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N5-3 with a molar amount of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N5-3 was: MS(ASAP) = 1350.

[0670] Synthesis of organic compound N5:

[0671] In a 250 mL three-necked flask, 10 mmol of intermediate N5-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N5, with a yield of 38.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N5 was: MS(ASAP)=1324.

[0672] Example N6

[0673] The synthetic route for organic compound N6 is as follows:

[0674]

[0675] Synthesis of intermediate 6-2:

[0676] Compounds N1-9 (10 mmol) and N6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N6-2 with a molar amount of 6.52 mmol and a yield of 65.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N6-2 was: MS(ASAP) = 1224.

[0677] Synthesis of intermediate N6-3:

[0678] Intermediate N6-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N6-3 with a molar amount of 8.34 mmol and a yield of 83.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N6-3 was MS(ASAP) = 1412.

[0679] Synthesis of organic compound N6:

[0680] In a 250 mL three-necked flask, 10 mmol of intermediate N6-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N6, with a yield of 45.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N6 was: MS(ASAP)=1386.

[0681] Example N7

[0682] The synthetic route for organic compound N7 is as follows:

[0683]

[0684] Synthesis of intermediate 7-2:

[0685] Compounds N1-9 (10 mmol) and N7-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N7-2 with a molar amount of 7.46 mmol and a yield of 74.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N7-2 was: MS(ASAP) = 1149.

[0686] Synthesis of intermediate N7-3:

[0687] Intermediate N7-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N7-3 with a molar amount of 8.59 mmol and a yield of 85.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N7-3 was MS(ASAP) = 1337.

[0688] Synthesis of organic compound N7:

[0689] In a 250 mL three-necked flask, 10 mmol of intermediate N7-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N7, with a yield of 41.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N7 was: MS(ASAP)=1311.

[0690] Example N8

[0691] The synthetic route for organic compound N8 is as follows:

[0692]

[0693] Synthesis of intermediate N8-2:

[0694] Compounds N1-9 (10 mmol) and N8-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N8-2 with a molar amount of 7.58 mmol and a yield of 75.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N8-2 was: MS(ASAP) = 1149.

[0695] Synthesis of intermediate N8-3:

[0696] Intermediate N8-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N8-3 with a molar amount of 8.13 mmol and a yield of 81.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N8-3 was MS(ASAP) = 1337.

[0697] Synthesis of organic compound N8:

[0698] In a 250 mL three-necked flask, 10 mmol of intermediate N8-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N8, with a yield of 49.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N8 was: MS(ASAP)=1311.

[0699] Example N9

[0700] The synthetic route for organic compound N9 is as follows:

[0701]

[0702] Synthesis of intermediate N9-2:

[0703] Compounds N1-9 (10 mmol) and N9-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N9-2 with a molar amount of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N9-2 was: MS(ASAP) = 1149.

[0704] Synthesis of intermediate N9-3:

[0705] Intermediate N9-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N9-3 with a molar amount of 7.59 mmol and a yield of 75.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N9-3 was MS(ASAP) = 1337.

[0706] Synthesis of organic compound N9:

[0707] In a 250 mL three-necked flask, 10 mmol of intermediate N9-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N9, with a yield of 44.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N9 was: MS(ASAP)=1311.

[0708] Example N10

[0709] The synthetic route for organic compound N10 is as follows:

[0710]

[0711] Synthesis of intermediate N10-2:

[0712] Intermediate N1-7 (10 mmol), compound N10-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N10-2 with a molar amount of 8.18 mmol and a yield of 81.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N10-2 was: MS(ASAP) = 1027.

[0713] Synthesis of intermediate N10-3:

[0714] Intermediates N10-2 (10 mmol) and N4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N10-3 with a molar amount of 6.57 mmol and a yield of 65.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N10-3 was MS(ASAP) = 1165.

[0715] Synthesis of intermediate N10-4:

[0716] Intermediate N10-3 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N10-4 with a molar amount of 7.43 mmol and a yield of 74.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N10-4 was MS(ASAP) = 1353.

[0717] Synthesis of organic compound N10:

[0718] In a 250 mL three-necked flask, 10 mmol of intermediate N10-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N10, with a yield of 32.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N10 was: MS(ASAP)=1327.

[0719] Example N11

[0720] The synthetic route for organic compound N11 is as follows:

[0721]

[0722] Synthesis of intermediate N11-2:

[0723] Intermediate N10-2 (10 mmol) and intermediate N11-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction and washing with water. The mixture was then subjected to organic phase column chromatography and recrystallization to obtain intermediate N11-2 with a molar amount of 6.36 mmol and a yield of 63.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N11-2 was MS(ASAP) = 1165.

[0724] Synthesis of intermediate N11-3:

[0725] Intermediate N11-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N11-3 with a molar amount of 7.22 mmol and a yield of 72.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N11-3 was MS(ASAP) = 1353.

[0726] Synthesis of organic compound N11:

[0727] In a 250 mL three-necked flask, 10 mmol of intermediate N11-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N11, with a yield of 35.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N11 was: MS(ASAP)=1327.

[0728] Example N12

[0729] The synthetic route for the organic compound N12 is as follows:

[0730]

[0731] Synthesis of intermediate N12-2:

[0732] Intermediate N10-2 (10 mmol) and intermediate N12-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N12-2 with a molar amount of 8.59 mmol and a yield of 85.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N12-2 was MS(ASAP) = 1165.

[0733] Synthesis of intermediate N12-3:

[0734] Intermediate N12-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N12-3 with a molar amount of 6.89 mmol and a yield of 68.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N12-3 was: MS(ASAP) = 1353.

[0735] Synthesis of organic compound N12:

[0736] In a 250 mL three-necked flask, 10 mmol of intermediate N12-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N12, with a yield of 37.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N12 was: MS(ASAP)=1327.

[0737] Example N13

[0738] The synthetic route for organic compound N13 is as follows:

[0739]

[0740] Synthesis of intermediate N13-2:

[0741] Intermediate N10-2 (10 mmol) and intermediate N13-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N13-2 with a molar amount of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N13-2 was MS(ASAP)=1165.

[0742] Synthesis of intermediate N13-3:

[0743] Intermediate N13-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N13-3 with a molar amount of 6.16 mmol and a yield of 61.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N13-3 was MS(ASAP) = 1353.

[0744] Synthesis of organic compound N13:

[0745] In a 250 mL three-necked flask, 10 mmol of intermediate N13-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N13, with a yield of 32.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N13 was: MS(ASAP)=1327.

[0746] Example N14

[0747] The synthetic route for organic compound N14 is as follows:

[0748]

[0749] Synthesis of intermediate N14-2:

[0750] Intermediate N1-7 (10 mmol), compound N14-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N14-2 with a molar amount of 8.36 mmol and a yield of 83.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N14-2 was: MS(ASAP) = 1027.

[0751] Synthesis of intermediate N14-3:

[0752] Intermediates N14-2 (10 mmol) and N5-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N14-3 with a molar amount of 6.09 mmol and a yield of 60.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N14-3 was MS(ASAP) = 1162.

[0753] Synthesis of intermediate N14-4:

[0754] Intermediate N14-3 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N14-4 with a molar amount of 8.93 mmol and a yield of 89.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N14-4 was MS(ASAP) = 1350.

[0755] Synthesis of organic compound N14:

[0756] In a 250 mL three-necked flask, 10 mmol of intermediate N14-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N14, with a yield of 44.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N14 was: MS(ASAP)=1324.

[0757] Example N15

[0758] The synthetic route for organic compound N15 is as follows:

[0759]

[0760] Synthesis of intermediate N15-2:

[0761] Intermediate N14-2 (10 mmol) and intermediate N15-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N15-2 with a molar amount of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N15-2 was MS(ASAP) = 1162.

[0762] Synthesis of intermediate N15-3:

[0763] Intermediate N15-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N15-3 with a molar amount of 8.37 mmol and a yield of 83.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N15-3 was: MS(ASAP) = 1350.

[0764] Synthesis of organic compound N15:

[0765] In a 250 mL three-necked flask, 10 mmol of intermediate N15-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N15, with a yield of 50.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N15 was: MS(ASAP)=1324.

[0766] Example N16

[0767] The synthetic route for organic compound N16 is as follows:

[0768]

[0769] Synthesis of intermediate N16-2:

[0770] Intermediate N14-2 (10 mmol) and intermediate N16-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction and washing with water. The mixture was then subjected to organic phase column chromatography and recrystallization to obtain intermediate N16-2 with a molar amount of 7.21 mmol and a yield of 72.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N16-2 was MS(ASAP) = 1162.

[0771] Synthesis of intermediate N16-3:

[0772] Intermediate N16-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N16-3 with a molar amount of 8.15 mmol and a yield of 81.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N16-3 was MS(ASAP) = 1350.

[0773] Synthesis of organic compound N16:

[0774] In a 250 mL three-necked flask, 10 mmol of intermediate N16-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N16, with a yield of 34.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N16 was: MS(ASAP)=1324.

[0775] Example N17

[0776] The synthetic route for organic compound N17 is as follows:

[0777]

[0778] Synthesis of intermediate N17-2:

[0779] Intermediate N14-2 (10 mmol) and intermediate N17-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N17-2 with a molar amount of 6.87 mmol and a yield of 68.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N17-2 was MS(ASAP) = 1162.

[0780] Synthesis of intermediate N17-3:

[0781] Intermediate N17-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N17-3 with a molar amount of 8.49 mmol and a yield of 84.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N17-3 was MS(ASAP) = 1350.

[0782] Synthesis of organic compound N17:

[0783] In a 250 mL three-necked flask, 10 mmol of intermediate N17-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N17, with a yield of 32.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N17 was: MS(ASAP)=1324.

[0784] Example N18

[0785] The synthetic route for organic compound N18 is as follows:

[0786]

[0787] Synthesis of intermediate N18-2:

[0788] Intermediate N1-7 (10 mmol), compound N18-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N18-2 with a molar amount of 7.52 mmol and a yield of 75.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N18-2 was: MS(ASAP) = 1150.

[0789] Synthesis of intermediate N18-3:

[0790] Intermediate N18-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N18-3 with a molar amount of 8.18 mmol and a yield of 81.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N18-3 was MS(ASAP) = 1338.

[0791] Synthesis of organic compound N18:

[0792] In a 250 mL three-necked flask, 10 mmol of intermediate N18-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N18, with a yield of 42.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N18 was: MS(ASAP)=1312.

[0793] Example N19

[0794] The synthetic route for organic compound N19 is as follows:

[0795]

[0796] Synthesis of intermediate N19-2:

[0797] Intermediate N1-7 (10 mmol), compound N19-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N19-2 with a molar amount of 7.86 mmol and a yield of 78.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N19-2 was: MS(ASAP) = 1150.

[0798] Synthesis of intermediate N19-3:

[0799] Intermediate N19-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N19-3 with a molar amount of 8.67 mmol and a yield of 86.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N19-3 was MS(ASAP) = 1338.

[0800] Synthesis of organic compound N19:

[0801] In a 250 mL three-necked flask, 10 mmol of intermediate 19-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N19, with a yield of 45.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N19 was: MS(ASAP)=1312.

[0802] Example N20

[0803] The synthetic route for the organic compound N20 is as follows:

[0804]

[0805] Synthesis of intermediate N20-2:

[0806] Intermediate N1-7 (10 mmol), compound N20-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N20-2 with a molar amount of 7.20 mmol and a yield of 72.0%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N20-2 was: MS(ASAP) = 1037.

[0807] Synthesis of intermediate N20-3:

[0808] Intermediate N20-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N20-3 with a molar amount of 8.18 mmol and a yield of 81.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N20-3 was MS(ASAP) = 1225.

[0809] Synthesis of organic compound N20:

[0810] In a 250 mL three-necked flask, 10 mmol of intermediate N2O-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N20, with a yield of 48.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N20 was: MS(ASAP)=1199.

[0811] Example N21

[0812] The synthetic route for organic compound N21 is as follows:

[0813]

[0814] Synthesis of intermediate N21-2:

[0815] Intermediate N1-7 (10 mmol), compound N21-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N21-2 with a molar amount of 7.48 mmol and a yield of 74.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N21-2 was: MS(ASAP) = 1023.

[0816] Synthesis of intermediate N21-3:

[0817] Intermediate N21-2 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N21-3 with a molar amount of 8.55 mmol and a yield of 85.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N21-3 was: MS(ASAP) = 1211.

[0818] Synthesis of organic compound N21:

[0819] In a 250 mL three-necked flask, 10 mmol of intermediate N21-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N21, with a yield of 40.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N21 was: MS(ASAP)=1185.

[0820] Example N22

[0821] The synthetic route for the organic compound N22 is as follows:

[0822]

[0823] Synthesis of intermediate N22-2:

[0824] Intermediate N1-5 (10 mmol), compound N22-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N22-2 with a molar amount of 6.29 mmol and a yield of 62.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N22-2 was: MS(ASAP) = 746.

[0825] Synthesis of intermediate N22-4:

[0826] Intermediate N22-2 (10 mmol), compound N22-3 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N22-4 with a molar amount of 7.59 mmol and a yield of 75.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N22-4 was: MS(ASAP) = 1003.

[0827] Synthesis of intermediate N22-5:

[0828] Intermediate N22-4 (10 mmol), pinacol diborate (20 mmol), palladium acetate (0.1 mmol), and potassium acetate (30 mmol) were dissolved in 1,4-dioxane and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N22-5 with a molar amount of 7.34 mmol and a yield of 73.4%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N22-5 was: MS(ASAP) = 1095.

[0829] Synthesis of intermediate N22-7:

[0830] Intermediates N22-5 (10 mmol) and N22-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N22-7 with a molar amount of 7.36 mmol and a yield of 73.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N22-7 was MS(ASAP) = 1208.

[0831] Synthesis of organic compound N22:

[0832] In a 250 mL three-necked flask, 10 mmol of intermediate N22-7 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N22, with a yield of 43.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N22 was: MS(ASAP)=1182.

[0833] Example N23

[0834] The synthetic route for organic compound N23 is as follows:

[0835]

[0836] Synthesis of intermediate N23-1:

[0837] Compounds N1-9 (10 mmol) and N22-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N23-1 with a molar amount of 7.87 mmol and a yield of 78.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N23-1 was: MS(ASAP)=1222.

[0838] Synthesis of intermediate N23-2:

[0839] Intermediate N23-1 (10 mmol), intermediate N1-12 (10 mmol), Pd(dba)2 (bis(dibenzylacetone palladium, 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, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N23-2 with a molar amount of 8.29 mmol and a yield of 82.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N23-2 was MS(ASAP) = 1410.

[0840] Synthesis of organic compound N23:

[0841] In a 250 mL three-necked flask, 10 mmol of intermediate N23-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N23, with a yield of 35.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N23 was: MS(ASAP)=1384.

[0842] Example N24

[0843] The synthetic route for the organic compound N24 is as follows:

[0844]

[0845] Synthesis of intermediate N24-2:

[0846] Intermediates N22-5 (10 mmol) and N24-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N24-2 with a molar amount of 8.24 mmol and a yield of 82.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N24-2 was MS(ASAP)=1221.

[0847] Synthesis of organic compound N24:

[0848] In a 250 mL three-necked flask, 10 mmol of intermediate N24-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N24, with a yield of 41.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N24 was: MS(ASAP)=1195.

[0849] Example N25

[0850] The synthetic route for organic compound N25 is as follows:

[0851]

[0852] Synthesis of intermediate N25-2:

[0853] Intermediate N22-5 (10 mmol) and intermediate N25-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N25-2 with a molar amount of 8.86 mmol and a yield of 88.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N25-2 was MS(ASAP) = 1375.

[0854] Synthesis of organic compound N25:

[0855] In a 250 mL three-necked flask, 10 mmol of intermediate N25-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N25, with a yield of 44.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N25 was: MS(ASAP)=1349.

[0856] Example N26

[0857] The synthetic route for the organic compound N26 is as follows:

[0858]

[0859] Synthesis of intermediate N26-2:

[0860] Intermediate N22-4 (10 mmol) and intermediate N26-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N26-2 with a molar amount of 8.17 mmol and a yield of 81.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N26-2 was MS(ASAP) = 1299.

[0861] Synthesis of organic compound N26:

[0862] In a 250 mL three-necked flask, 10 mmol of intermediate N26-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N26, with a yield of 34.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N26 was: MS(ASAP)=1273.

[0863] Example N27

[0864] The synthetic route for organic compound N27 is as follows:

[0865]

[0866] Synthesis of intermediate N27-2:

[0867] Intermediate N22-4 (10 mmol) and intermediate N27-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction and washing with water. The mixture was then subjected to organic phase column chromatography and recrystallization to obtain intermediate N27-2 with a molar amount of 8.35 mmol and a yield of 83.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate N27-2 was MS(ASAP) = 1299.

[0868] Synthesis of organic compound N27:

[0869] In a 250 mL three-necked flask, 10 mmol of intermediate N27-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N27, with a yield of 39.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N27 was: MS(ASAP)=1273.

[0870] Example N28

[0871] The synthetic route for organic compound N28 is as follows:

[0872]

[0873] Synthesis of intermediate N28-2:

[0874] Intermediate N22-4 (10 mmol) and intermediate N28-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N28-2 with a molar amount of 8.54 mmol and a yield of 85.4%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N28-2 was MS(ASAP)=1299.

[0875] Synthesis of organic compound N28:

[0876] In a 250 mL three-necked flask, 10 mmol of intermediate N28-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N28, with a yield of 38.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N28 was: MS(ASAP)=1273.

[0877] Example N29

[0878] The synthetic route for organic compound N29 is as follows:

[0879]

[0880] Synthesis of intermediate N29-2:

[0881] Intermediate N22-4 (10 mmol) and intermediate N29-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate N29-2 with a molar amount of 7.45 mmol and a yield of 74.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N29-2 was MS(ASAP) = 1250.

[0882] Synthesis of organic compound N29:

[0883] In a 250 mL three-necked flask, 10 mmol of intermediate N29-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N29, with a yield of 31.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N29 was: MS(ASAP)=1224.

[0884] Example N30

[0885] The synthetic route for organic compound N30 is as follows:

[0886]

[0887] Synthesis of intermediate N30-2:

[0888] Intermediate N22-5 (10 mmol) and intermediate N30-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 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, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate N30-2 with a molar amount of 8.14 mmol and a yield of 81.4%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N30-2 was MS(ASAP) = 1197.

[0889] Synthesis of organic compound N30:

[0890] In a 250 mL three-necked flask, 10 mmol of intermediate N30-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N30, with a yield of 42.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N30 was: MS(ASAP)=1171.

[0891] Example N31

[0892] The synthetic route for organic compound N31 is as follows:

[0893]

[0894] Synthesis of intermediate N31-2:

[0895] Intermediate N1-5 (10 mmol), compound N31-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate N31-2 with a molar amount of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N31-2 was: MS(ASAP) = 788.

[0896] Synthesis of intermediate N31-3:

[0897] Intermediate N31-2 (10 mmol), compound N18-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N31-3 with a molar amount of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N31-3 was: MS(ASAP) = 966.

[0898] Synthesis of intermediate N31-4:

[0899] Intermediate N31-3 (10 mmol), compound N1-12 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N31-4 with a molar amount of 7.86 mmol and a yield of 78.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N31-4 was: MS(ASAP) = 1154.

[0900] Synthesis of organic compound N31:

[0901] In a 250 mL three-necked flask, 10 mmol of intermediate N31-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N31, with a yield of 42.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N31 was: MS(ASAP)=1128.

[0902] Example N32

[0903] The synthetic route for the organic compound N32 is as follows:

[0904]

[0905] Synthesis of intermediate N32-1:

[0906] Intermediate N31-2 (10 mmol), compound N19-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N32-1 with a molar amount of 7.55 mmol and a yield of 75.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N32-1 was: MS(ASAP) = 968.

[0907] Synthesis of intermediate N32-2:

[0908] Intermediate N32-1 (10 mmol), compound N1-12 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 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, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate N32-2 with a molar amount of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate N32-2 was: MS(ASAP) = 1156.

[0909] Synthesis of organic compound N32:

[0910] In a 250 mL three-necked flask, 10 mmol of intermediate N32-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a 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 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was 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 the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound N32, with a yield of 45.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound N32 was: MS(ASAP)=1130.

[0911] Example P1

[0912] Compound P1 ( Synthesis of )

[0913] Synthesis route:

[0914]

[0915] Synthesis of compound P1: Under nitrogen atmosphere, 30 mL of aqueous solution of (5.97 g, 30 mmol) compound P1-1, (12.9 g, 30 mmol) compound P1-2, (1.65 g, 1.5 mmol) tetrakis(triphenylphosphine)palladium, and (8.4 g, 60 mmol) potassium carbonate, along with 150 mL of toluene, were added to a 500 mL three-necked flask. The mixture was heated and stirred at 110 °C for 12 hours. After the reaction was stopped, the mixture was cooled to room temperature, and the filtrate was filtered. Most of the solvent was removed by rotary evaporation. The filtrate was dissolved in dichloromethane, washed three times with water, and the organic liquid was collected and purified by column chromatography on silica gel. The yield was 84%. MS (ASAP): 506.

[0916] Example P2

[0917] Compound P2 ( Synthesis of )

[0918] Synthesis route:

[0919]

[0920] Synthesis of compound P2: Following the synthetic method of compound P1, compound P2-1 was substituted for compound P1-1, yield 82%. MS (ASAP): 560.

[0921] Example P3

[0922] Compound P3 ( Synthesis of )

[0923] Synthesis route:

[0924]

[0925] Synthesis of compound P3: Following the synthetic method of compound P1, compound P3-1 was substituted for compound P1-1, yield 85%. MS (ASAP): 562.

[0926] Example P4

[0927] Compound P4 ( Synthesis of )

[0928] Synthesis route:

[0929]

[0930] Synthesis of compound P4: Following the synthetic method of compound P1, compound P4-1 was substituted for compound P1-1, yield 83%. MS (ASAP): 562.

[0931] Example P5

[0932] Compound P5 ( Synthesis of )

[0933] Synthesis route:

[0934]

[0935] Synthesis of compound P5-3: Following the synthetic method of compound P1, compounds P5-1 and P5-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 76%. MS (ASAP): 192.

[0936] Synthesis of intermediate P5-4: Under nitrogen atmosphere, (9.6 g, 50 mmol) of compound P5-3, (12.7 g, 50 mmol) pinacol diborate, (9.8 g, 100 mmol) potassium acetate, (2.2 g, 3 mmol) Pd(ppf)Cl2, and 150 mL of 1,4-dioxane as solvent were added to a 250 mL three-necked flask. The mixture was heated to 110 °C and reacted for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the filtrate was filtered. Most of the solvent was removed by rotary evaporation, and the filtrate was dissolved in dichloromethane, washed three times with water, and the organic liquid was collected and purified by column chromatography with silica gel. The yield was 75%. MS (ASAP): 283.

[0937] Synthesis of compound P5: Following the synthetic method of compound P1, compounds P5-4 and P5-5 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 524.

[0938] Example P6

[0939] Compound P6 ( Synthesis of )

[0940] Synthesis route:

[0941]

[0942] Synthesis of compound P6-3: Following the synthetic method of compound P1, compounds P6-1 and P6-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 73%. MS (ASAP): 290.

[0943] Synthesis of intermediate P6-4: Following the synthetic method of compound P5-4, compound P6-3 was substituted for compound P5-3, yield 72%. MS (ASAP): 381.

[0944] Synthesis of compound P6: Following the synthetic method of compound P1, compounds P1-1 and P1-2 were replaced by compounds P6-4 and P5-5, respectively, with a yield of 70%. MS (ASAP): 622.

[0945] Example P7

[0946] Compound P7 ( Synthesis of )

[0947] Synthesis route:

[0948]

[0949] Synthesis of intermediate P7-3: Following the synthetic method of compound P1, compounds P7-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 77%. MS (ASAP): 482.

[0950] Synthesis of compound P7: Following the synthetic method of compound P1, compounds P7-4 and P7-3 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 82%. MS (ASAP): 560.

[0951] Example P8

[0952] Compound P8 ( Synthesis of )

[0953] Synthesis route:

[0954]

[0955] Synthesis of intermediate P8-2: Following the synthetic method of compound P1, compounds P8-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 72%. MS (ASAP): 482.

[0956] Synthesis of compound P8: Following the synthetic method of compound P1, compounds P8-3 and P8-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 560.

[0957] Example P9

[0958] Compound P9 ( Synthesis of )

[0959] Synthesis route:

[0960]

[0961] Synthesis of compound P9: Following the synthetic method of compound P1, compounds P2-1 and P7-3 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 610.

[0962] Example P10

[0963] Compound P10 ( Synthesis of )

[0964] Synthesis route:

[0965]

[0966] Synthesis of intermediate P10-2: Following the synthetic method of compound P1, compounds P10-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 70%. MS (ASAP): 498.

[0967] Synthesis of intermediate P10-4: Under nitrogen atmosphere, (27 g, 100 mmol) of compound P10-3 and 100 mL of anhydrous tetrahydrofuran solvent were added to a 300 mL three-necked flask, stirred to dissolve, cooled to -78 °C, and 210 mmol of n-butyllithium was slowly added dropwise. The reaction was allowed to proceed for 2 hours, and then 250 mmol of deuterated water was added at once. The reaction solution was allowed to slowly rise to room temperature, and the reaction was continued with stirring for 4 hours. After the reaction was completed, most of the solvent was evaporated by rotary evaporation, the solution was washed three times with water dissolved in dichloromethane, and the organic liquid was collected and purified by column chromatography on silica gel. The yield was 75%. MS (ASAP): 115.

[0968] Synthesis of intermediate P10-5: Following the synthetic method of compound P5-4, compound P10-4 was used to replace compound P5-3, with a yield of 79%. MS (ASAP): 206.

[0969] Synthesis of intermediate P10-7: Following the synthetic method of compound P1, compounds P10-5 and P10-6 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 191.

[0970] Synthesis of intermediate P10-8: Following the synthetic method of compound P5-4, compound P10-7 was substituted for compound P5-3, yield 82%. MS (ASAP): 282.

[0971] Synthesis of compound P10: Following the synthetic method of compound P1, compounds P10-8 and P10-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 81%. MS (ASAP): 573.

[0972] Example P11

[0973] Compound P11 ( Synthesis of )

[0974] Synthesis route:

[0975]

[0976] Synthesis of compound P11-2: Under nitrogen atmosphere, 24.2 g (100 mmol) of compound P11-1 and 100 mL of anhydrous tetrahydrofuran solvent were added to a 300 mL three-necked flask, stirred to dissolve, cooled to -78 °C, and 110 mmol of n-butyllithium was slowly added dropwise. The reaction was allowed to proceed for 2 hours, and then 120 mmol of deuterated water was added at once. The reaction solution was allowed to slowly rise to room temperature, and the reaction was continued with stirring for 4 hours. After the reaction was complete, most of the solvent was evaporated by rotary evaporation, the solution was washed three times with water dissolved in dichloromethane, and the organic liquid was collected and purified by column chromatography on silica gel. The yield was 82%. MS (ASAP): 164.

[0977] Synthesis of compound P11-3: Following the synthesis method of compound P5-4, compound P11-2 was substituted for compound P5-3, yield 78%. MS (ASAP): 255.

[0978] Synthesis of compound P11-4: Following the synthetic method of compound P1, compounds P11-3 and P10-6 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 76%. MS (ASAP): 240.

[0979] Synthesis of compound P11-5: Following the synthetic method of compound P5-4, compound P11-4 was used to replace compound P5-3, with a yield of 81%. MS (ASAP): 331.

[0980] Synthesis of compound P11: Following the synthetic method of compound P1, compounds P11-5 and P11-6 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 82%. MS (ASAP): 556.

[0981] Example P12

[0982] Compound P12 ( Synthesis of )

[0983] Synthesis route:

[0984]

[0985] Synthesis of compound P12-2: Following the synthesis method of compound P5-4, compound P12-1 was substituted for compound P5-3, yield 76%. MS (ASAP): 255.

[0986] Synthesis of compound P12-4: Following the synthetic method of compound P1, compounds P12-2 and P12-3 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 240.

[0987] Synthesis of compound P12-5: Following the synthetic method of compound P5-4, compound P12-4 was used to replace compound P5-3, with a yield of 83%. MS (ASAP): 331.

[0988] Synthesis of compound P12: Following the synthetic method of compound P1, compounds P12-5 and P12-6 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 82%. MS (ASAP): 572.

[0989] Example P13

[0990] Compound P13 ( Synthesis of )

[0991] Synthesis route:

[0992]

[0993] Synthesis of intermediate P13-2: Following the synthetic method of compound P1, compounds P13-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 72%. MS (ASAP): 482.

[0994] Synthesis of intermediate P13-4: Following the synthetic method of compound P1, compounds P13-3 and P10-6 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 81%. MS (ASAP): 191.

[0995] Synthesis of intermediate P13-5: Following the synthetic method of compound P5-4, compound P13-4 was used to replace compound P5-3, with a yield of 80%. MS (ASAP): 282.

[0996] Synthesis of compound P13: Following the synthetic method of compound P1, compounds P13-5 and P13-2 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 79%. MS (ASAP): 557.

[0997] Example P14

[0998] Compound P14 ( Synthesis of )

[0999] Synthesis route:

[1000]

[1001] Synthesis of intermediate P14-2: Following the synthetic method of compound M1, compounds P14-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 75%. MS (ASAP): 498.

[1002] Synthesis of compound P14: Following the synthetic method of compound P1, compounds P14-3 and P14-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 73%. MS (ASAP): 628.

[1003] Example P15

[1004] Compound P15 ( Synthesis of )

[1005] Synthesis route:

[1006]

[1007] Synthesis of intermediate P15-3: Following the synthetic method of compound P1, compounds P15-1 and P1-2 were substituted with compounds P15-1 and P1-2 respectively, with a yield of 76%. MS (ASAP): 242.

[1008] Synthesis of intermediate P15-4: Following the synthetic method of compound P5-4, compound P15-3 was substituted for compound P5-3, yield 73%. MS (ASAP): 333.

[1009] Synthesis of compound P15: Following the synthetic method of compound P1, compounds P15-4 and P15-5 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 74%. MS (ASAP): 558.

[1010] Example P16

[1011] Compound P16 ( Synthesis of )

[1012] Synthesis route:

[1013]

[1014] Synthesis of intermediate P16-3: Following the synthetic method of compound P1, compounds P16-1 and P1-2 were substituted with compounds P16-1 and P1-2 respectively, with a yield of 82%. MS (ASAP): 377.

[1015] Synthesis of intermediate P6-4: Following the synthetic method of compound P5-4, compound P16-3 was substituted for compound P5-3, yield 78%. MS (ASAP): 467.

[1016] Synthesis of intermediate P6-5: Following the synthetic method of compound P1, compounds P16-4 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 75%. MS (ASAP): 606.

[1017] Synthesis of compound P16: Following the synthetic method of compound P1, compounds P7-4 and P16-5 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 79%. MS (ASAP): 684.

[1018] Example P17

[1019] Compound P17 ( Synthesis of )

[1020] Synthesis route:

[1021]

[1022] Synthesis of intermediate P17-2: Following the synthetic method of compound P1, compounds P17-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 80%. MS (ASAP): 558.

[1023] Synthesis of compound P17: Following the synthetic method of compound P1, compound P2-1 was substituted for compound P17-2, yield 82%. MS (ASAP): 686.

[1024] Example P18

[1025] Compound P18 ( Synthesis of )

[1026] Synthesis route:

[1027]

[1028] Synthesis of intermediate P18-2: Following the synthetic method of compound P1, compounds P18-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 498.

[1029] Synthesis of compound P18: Following the synthetic method of compound P1, compounds P18-2 and P7-4 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 83%. MS (ASAP): 576.

[1030] Example P19

[1031] Compound P19 ( Synthesis of )

[1032] Synthesis route:

[1033]

[1034] Synthesis of intermediate P19-1: Following the synthetic method of compound P1, compounds P10-5 and P11-1 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 81%. MS (ASAP): 241.

[1035] Synthesis of intermediate P19-1: Following the synthetic method of compound P5-4, compound P19-1 was used to replace compound P5-3, with a yield of 83%. MS (ASAP): 332.

[1036] Synthesis of compound P19: Following the synthetic method of compound P1, compounds P19-2 and P19-3 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 557.

[1037] Example P20

[1038] Compound P20 ( Synthesis of )

[1039] Synthesis route:

[1040]

[1041] Synthesis of intermediate P20-1: Following the synthetic method of compound P1, compounds P20-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 77%. MS (ASAP): 560.

[1042] Synthesis of compound P20: Following the synthetic method of compound P1, compounds P20-3 and P20-2 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 81%. MS (ASAP): 684.

[1043] Example P21

[1044] Compound P21 ( Synthesis of )

[1045] Synthesis route:

[1046]

[1047] Synthesis of intermediate P21-2: Following the synthetic method of compound P1, compounds P21-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 75%. MS (ASAP): 482.

[1048] Synthesis of intermediate P21-3: Following the synthetic method of compound P5-4, compound P21-3 was substituted for compound P5-3, with a yield of 80%. MS (ASAP): 387.

[1049] Synthesis of compound P21: Following the synthetic method of compound P1, compounds P21-4 and P21-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 73%. MS (ASAP): 662.

[1050] Example P22

[1051] Compound P22 ( Synthesis of )

[1052] Synthesis route:

[1053]

[1054] Synthesis of intermediate P22-1: Following the synthetic method of compound P1, compounds P22-1 and P7-2 were substituted for compounds P1-1 and P1-2, respectively, with a yield of 73%. MS (ASAP): 574.

[1055] Synthesis of compound P22: Following the synthetic method of compound P1, compounds P7-4 and P22-2 were used to replace compounds P1-1 and P1-2, respectively, with a yield of 78%. MS (ASAP): 652.

[1056] The exemplary manufacturing steps of the light-emitting element provided in this application are shown in the following exemplary embodiment.

[1057] In this embodiment, the fabrication steps of the light-emitting element having an anode (ITO) / hole injection layer (40nm) / hole transport layer (100nm) / light-emitting layer (50nm) (main material: 3% (mass ratio) guest material) / electron transport layer (25nm) / cathode (LiQ (1nm) / Al (150nm)) are as follows:

[1058] a. Cleaning of conductive glass substrate: When using it for the first time, it can be cleaned with various solvents, such as chloroform, ketone, and isopropanol, and then treated with ultraviolet ozone plasma.

[1059] b. Following the order of hole injection layer (40nm), hole transport layer (100nm), light-emitting layer (50nm), and electron transport layer (25nm), sequentially apply the layers in a high vacuum (1×10⁻⁶ nm). -6 Film deposition by thermal evaporation at mbar;

[1060] c. Cathode: LiQ (1nm) / Al (150nm) in high vacuum (1×10⁻⁶) -6It is formed by thermal evaporation in mbar;

[1061] d. Encapsulation: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[1062] In this embodiment, the object material is BD-ref and the host material is BH-ref to form the contrast element 1. The exemplary embodiments M1 to M17, embodiments N1 to N32 and embodiments P1 to P22 are combined as shown in Table 1 to form the light-emitting elements 1-40.

[1063] Of the light-emitting elements 1-40, and the comparison element 1:

[1064] The structure of BD-ref is: .

[1065] The structural formula for BH-ref is: .

[1066] The structural formula of the material of the hole injection layer is: .

[1067] The structural formula of the material of the hole transport layer is: .

[1068] The structural formula of the material of the electron transport layer is: .

[1069] The structural formula of LiQ is: .

[1070] In this embodiment, external quantum efficiency (EQE) and luminous lifetime (T90@1000 nits, which refers to the time it takes for the device under test to decay from 1000 nits to 900 nits) were tested on light-emitting elements 1-32 and comparison element 1. The results are shown in Table 1 and Table 2.

[1071] Table 1

[1072]

[1073] Table 2

[1074]

[1075] As shown in Tables 1 and 2, when the external quantum efficiency and luminescence lifetime of comparison element 1 are taken as a baseline value 1, the external quantum efficiency of light-emitting elements 1 to 40 are significantly improved, and the luminescence lifetime is also effectively extended. The external quantum efficiency and luminescence lifetime of light-emitting elements 33 to 38 are smaller than those of light-emitting elements 1 to 32 because they only have one type of guest material, resulting in insufficient conversion of excitons from the host material to the guest material. Compared to light-emitting elements 1 to 32 with dual host materials, light-emitting elements 39 to 40 have smaller increases in external quantum efficiency and luminescence lifetime because they have two host materials with similar structures and high energy level overlap, resulting in more excitons converted to the guest material. This indicates that including a compound combination of at least two boron atom fused ring compound guest materials and two or more anthracene derivative host materials in the light-emitting layer results in a higher carrier balance in the light-emitting layer, thereby effectively improving the luminescence efficiency and luminescence lifetime of the light-emitting elements.

[1076] The light-emitting element disclosed in this application improves the luminous efficiency and extends the luminous lifetime of the light-emitting element by including a compound combination of at least two boron atom fused ring compound guest materials and two or more anthracene derivative host materials in the light-emitting layer, thereby achieving a higher carrier balance in the light-emitting layer.

[1077] In addition, embodiments of this application also disclose a display panel, which includes any of the light-emitting elements described above.

[1078] In some embodiments, the display panel further includes an array substrate located on one side of the light-emitting element and an encapsulation layer located on the side of the light-emitting element away from the array substrate and covering the light-emitting element.

[1079] In some embodiments, the display panel further includes a polarizer layer located on the side of the encapsulation layer away from the light-emitting element and a cover plate layer located on the side of the polarizer layer away from the light-emitting element. The polarizer layer may be replaced by a color filter layer, which may include a plurality of color resists and black matrices located on both sides of the color resists.

[1080] In summary, the light-emitting element and display panel provided in this application improve the luminous efficiency and extend the luminous lifetime of the light-emitting element by forming at least two boron atom fused ring compound guest materials and at least two anthracene derivative host materials in the light-emitting layer.

[1081] The above provides a detailed description of a light-emitting element and a display panel provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. A light emitting element characterized by comprising: The light emitting element includes a first electrode, a second electrode, and a light emitting layer between the first electrode and the second electrode, a material of the light emitting layer includes a guest material and a host material, the guest material includes at least one compound represented by general formula (1-1) or general formula (1-14) and at least one compound represented by general formula (2-2) or general formula (2-3), and the host material includes at least two compounds represented by general formula (3-1). ； In the general formula (1-1): Ar 101 to Ar 103 selected from H, D, methyl; Ar 104 and Ar 105 is selected from phenyl substituted by at least one alkyl group having 1 to 5 carbon atoms, and Ar 104 and Ar 105 form a five-membered heterocyclic ring or are independent of each other; Ar 106 selected from phenyl; Ar 107 and Ar 108 is selected from a biphenyl group or a phenyl group substituted by at least one alkyl group having 1 to 5 carbon atoms; A 101 any one selected from the group consisting of phenyl substituted by at least one alkyl group having 1 to 5 carbon atoms, benzothiophenyl substituted by at least one alkyl group having 1 to 5 carbon atoms; A 102 selected from phenyl or phenyl substituted with D; Z is selected from CR 102 R 103 , NR 104 , O or S; X1, Y1are each independently selected from O or NR 105 ; R 102 and R 103 is selected from methyl; R 104 selected from methyl; R 105 selected from phenyl substituted by methyl or tert-butyl; R 108 selected from H or D; n102, n103, n104 each independently represent any one integer from 0 to 5; In the general formula (2-2) and general formula (2-3): Ar 201 is selected from tert-butyl or a structure represented by any one of Formula (B205) and Formula (B206): ； Ar 202 is selected from any one of the structures represented by formula (C201) to formula (C209): ； Ar 203 is selected from any one of the structures represented by formula (B201) to formula (B207); ； W is each independently selected from O, S, N-CH3, or N-Ph; n201 is each independently selected from any one integer from 0 to 10; R 204 selected from H, methyl or phenyl; In the general formula (3-1): Ar 301 at least one selected from the group consisting of ； L 303 at least one selected from the group consisting of ； L 304 at least one selected from a single bond or the following groups: ； L 303 and L 304 not containing deuterium; A 303 any one selected from the group consisting of ； V is selected from O or S; R 309 is selected from H, methyl, phenyl or tert-butyl; n301 is selected from any one integer from 0 to 7; n302 is selected from any one integer from 0 to 9.

2. The light-emitting element according to claim 1, wherein The compound represented by the general formula (1-1) is selected from any one of structures represented by general formula (1-2) to general formula (1-7): 。 3. The light-emitting element according to claim 1, wherein The compound represented by the general formula (1-1) is selected from any one of structures represented by general formula (1-8) to general formula (1-13): 。 4. The light-emitting element according to claim 1, wherein The compound represented by the general formula (1-1) and general formula (1-14) is selected from at least one of the following compounds: 。 5. The light-emitting element according to claim 1, wherein The compound represented by the general formula (2-2) and general formula (2-3) is selected from at least one of the following compounds: 。 6. The light-emitting element according to claim 1, wherein The compound represented by the general formula (3-1) is selected from at least one of the following compounds: 。 7. The light-emitting element according to claim 1, wherein In the light emitting layer, a mass ratio of the host material to the guest material ranges from 99:1 to 70:

30.

8. The light-emitting element according to claim 1, wherein In the light emitting layer, the host material is two kinds, and a mass ratio of the two kinds of host material ranges from 99:1 to 1:

99.

9. The light-emitting element according to claim 1, wherein In the light emitting layer, the guest material is two kinds, and a mass ratio of the two kinds of guest material ranges from 99:1 to 1:

99.

10. A display panel, characterized by, The light emitting element includes a first electrode, a second electrode, and a light emitting layer between the first electrode and the second electrode, a material of the light emitting layer includes a guest material and a host material, the guest material includes at least one compound represented by general formula (1-1) or general formula (1-14) and at least one compound represented by general formula (2-2) or general formula (2-3), and the host material includes at least two compounds represented by general formula (3-1).

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