Boron-containing organic compounds, mixtures, compositions and organic electronic devices

Abstract

Disclosed are a boron-containing organic compound, a mixture, a composition, and an organic electronic device. The structure of the boron-containing organic compound is shown in general formula (1). The boron-containing organic compound can be used as a light-emitting material in a functional layer of an electronic device to improve the efficiency and lifetime of the device.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence, and in particular to a boron-containing organic compound, mixture, composition, and organic electronic device. Background Technology

[0002] Organic semiconductor materials offer diverse synthesis options, relatively low manufacturing costs, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) possess advantages such as wide viewing angles, fast response times, low operating voltages, and thin panel thicknesses in optoelectronic devices (e.g., flat panel displays and lighting), thus demonstrating broad development potential.

[0003] To improve the luminous efficiency of organic light-emitting diodes (OLEDs), various luminescent material systems based on fluorescence and phosphorescence have been developed. Among these, OLEDs using fluorescent materials exhibit high reliability, but their internal electroluminescence quantum efficiency under electrical excitation is limited to 25% due to the 1:3 branching ratio of singlet to triplet excited states of the exciton. OLEDs using phosphorescent materials have achieved nearly 100% internal electroluminescence quantum efficiency, but phosphorescent OLEDs face a major challenge: the roll-off effect, where luminous efficiency rapidly decreases with increasing current or brightness, which is particularly detrimental to high-brightness applications.

[0004] To date, conventional phosphorescent materials with practical application value are iridium- and platinum-containing complexes. However, these raw materials are rare and expensive, and the synthesis of these complexes is complex, resulting in high costs. To overcome these problems, Adachi proposed the concept of reverse internal conversion, which allows the use of organic compounds, i.e., without the use of metal complexes, to achieve high efficiency comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as: 1) using composite excited-state materials; 2) using thermally excited delayed fluorescence (TADF) materials.

[0005] However, traditional blue TADF materials still lag behind phosphorescent materials in terms of both efficiency and lifespan. Summary of the Invention

[0006] Based on this, the present invention provides a boron-containing organic compound that can be used as a luminescent material in the functional layer of electronic devices to extend the luminous efficiency and lifespan of the devices.

[0007] The present invention is achieved through the following technical solution.

[0008] A boron-containing organic compound, the structure of which is shown in general formula (1):

[0009]

[0010] in:

[0011] Each time Z appears, it is independently selected from N, P, P=O, As, Te, or Bi;

[0012] Ar 2 Selected from any one of the groups (A-1) to (A-3):

[0013]

[0014] Each time X appears, it is independently selected from CR1 or N;

[0015] Y is independently selected from NR2, CR2R3, SiR2R3, O, S, S(=O)2, S(=O);

[0016] Ar 3 Selected from any one of the groups (B-1) to (B-3):

[0017]

[0018] Each time X1 appears, it is independently selected from CR, CR4, or N;

[0019] Y1 is independently selected from NR5, CR5R6, SiR5R6, O, S, S(=O)2, S(=O);

[0020] At least one X1 in (B-1) is selected from CR;

[0021] In (B-2), at least one X1 is selected from CR, or Y1 is selected from CR5R6 and R5 is -F or -CF3;

[0022] (B-3) At least one X1 is selected from CR, or Y1 is selected from CR5R6 and R5 is -F or -CF3;

[0023] R is either -F or -CF3;

[0024] R1 through R6 are each independently selected from: -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, thioalkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, alkoxy groups having 3 to 20 carbon atoms, thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano groups, and carbamoyl groups. Haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 50 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 50 ring atoms, aryloxy groups having 6 to 50 ring atoms, heteroaryloxy groups having 5 to 50 ring atoms, or combinations of these groups; two adjacent R4 groups may be cyclic or acyclic with each other;

[0025] Ar 1 Ar 4 Ar 5 Ar 6 Each is independently selected from: substituted or unsubstituted aromatic groups having 6 to 60 C atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 cyclic atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 30 cyclic atoms;

[0026] * indicates a fusion site.

[0027] The present invention also provides a mixture comprising the boron-containing organic compound as described above, and at least one organic functional material selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, light emitters, host materials, or organic dyes.

[0028] The present invention also provides a composition comprising a boron-containing organic compound as described above or a mixture thereof, and at least one organic solvent.

[0029] The present invention also provides an organic electronic device comprising, as described above, a boron-containing organic compound, a mixture as described above, or a composition as described above.

[0030] Compared with the prior art, the boron-containing organic compounds of the present invention have the following beneficial effects:

[0031] The boron-containing organic compounds described in this invention, as blue light-emitting materials, possess suitable HOMO and LUMO, and have a large band gap (|HOMO-LUMO|), which facilitates the accumulation of holes and electrons in the light-emitting layer, thereby improving the luminous efficiency of the device. Furthermore, the introduction of F or CF3 into the compounds in this application raises their Td temperature, making them easier to sublimate and thus easier to purify. This also allows for shorter emission wavelengths, resulting in a narrow full width at half maximum (FWHM) emission spectrum with deep blue fluorescence. Attached Figure Description

[0032] Figure 1 This is a schematic diagram of an organic light-emitting device structure provided in an embodiment of the present invention; in the figure, 101 is a substrate, 102 is an anode, 103 is a hole injection layer, 104 is a hole transport layer, 105 is a light-emitting layer, 106 is an electron transport layer, and 107 is a cathode. Detailed Implementation

[0033] To facilitate understanding of the present invention, a more complete description will be given below with reference to relevant embodiments. Preferred embodiments of the invention are shown in the embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a thorough and complete understanding of the disclosure of the present invention.

[0034] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0035] In this invention, the terms "composition" and "printing ink" or "ink" have the same meaning and can be used interchangeably.

[0036] In this invention, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0037] In this invention, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0038] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0039] In this invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R. # Instead, the R# Selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, C 1-30 Alkyl groups, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R"", silyl groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, halocarbamoyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and the above groups may be further substituted with substituents acceptable in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to: H, deuterium, cyano, isocyano, nitro or halogen, C 1-10 Alkyl groups, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, and heteroaromatic groups containing 5-20 ring atoms.

[0040] In this invention, "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 substituted 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" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0041] "Aryl or aromatic group" 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, 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.

[0042] "Heteroaryl or heteroaromatic group" 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, imidazole, triazolyl, imidazole, diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridine, pyridazinyl, pyridinyl, etc. Azinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, pyrazinylpyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzothiopheneyl, benzofuranyl, indolyl, carbazoleyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolol, furanol, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, o-diazonaphthyl, quinoxalinyl, phenanthridine, primidyl, quinazolinyl, quinazolinone, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0043] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl groups. The number of carbon atoms in an alkyl group can be 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, adamantyl, etc.

[0044] "Halogen" or "halogen group" refers to F, Cl, Br or I.

[0045] The term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above that is attached to the parent nucleus via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0046] In this invention, "*" represents a connection site.

[0047] In this invention, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... Six Rs on the benzene ring 1 They can be the same as or different from each other.

[0048] In this invention, the single bond connecting the substituents extends 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; such as express Can be with A fused ring can be formed at any position on the benzene ring.

[0049] The cyclic alkyl or cycloalkyl groups used in accordance with this invention have the same meaning and can be used interchangeably.

[0050] In the embodiments of this invention, the energy level structure of organic materials, specifically the triplet energy levels ET, HOMO, and LUMO, plays a crucial role. These energy levels are described below:

[0051] HOMO and LUMO energy levels can be measured using the photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0052] The triplet energy level ET1 of organic materials can be measured by low-temperature time-resolved emission spectroscopy or obtained by quantum simulation calculations (such as by Time-dependent DFT), such as using commercial software Gaussian 03W (Gaussian Inc.). For specific simulation methods, please refer to WO2011141110 or the following examples.

[0053] It should be noted that the absolute values ​​of HOMO, LUMO, and ET1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as those at the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. In the description of the embodiments of this invention, the values ​​of HOMO, LUMO, and ET1 are based on Time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0054] In this invention, (HOMO-1) is defined as the second highest occupied orbital energy level, (HOMO-2) as the third highest occupied orbital energy level, and so on. (LUMO+1) is defined as the second lowest unoccupied orbital energy level, (LUMO+2) as the third lowest occupied orbital energy level, and so on.

[0055] This invention provides a boron-containing organic compound with the structure shown in general formula (1):

[0056]

[0057] in:

[0058] Each time Z appears, it is independently selected from N, P, P=O, As, Te, or Bi;

[0059] Ar 2 Selected from any one of the groups (A-1) to (A-3):

[0060]

[0061] Each time X appears, it is independently selected from CR1 or N;

[0062] Y is independently selected from NR2, CR2R3, SiR2R3, O, S, S(=O)2, S(=O);

[0063] Ar 3 Selected from any one of the groups (B-1) to (B-3):

[0064]

[0065] Each time X1 appears, it is independently selected from CR, CR4, or N;

[0066] Y1 is independently selected from NR5, CR5R6, SiR5R6, O, S, S(=O)2, S(=O);

[0067] At least one X1 in (B-1) is selected from CR;

[0068] In (B-2), at least one X1 is selected from CR, or Y1 is selected from CR5R6 and R5 is -F or -CF3;

[0069] (B-3) At least one X1 is selected from CR, or Y1 is selected from CR5R6 and R5 is -F or -CF3;

[0070] R is either -F or -CF3;

[0071] R1 through R6 are each independently selected from: -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, thioalkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, alkoxy groups having 3 to 20 carbon atoms, thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano groups, and carbamoyl groups. Haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 50 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 50 ring atoms, aryloxy groups having 6 to 50 ring atoms, heteroaryloxy groups having 5 to 50 ring atoms, or combinations of these groups; two adjacent R4 groups may be cyclic or acyclic with each other;

[0072] Ar 1 Ar 4 Ar 5 Ar 6 Each is independently selected from: substituted or unsubstituted aromatic groups having 6 to 60 C atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 cyclic atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 30 cyclic atoms;

[0073] * indicates a fusion site.

[0074] In a specific example, the structure of the boron-containing organic compound is selected from any of the structures shown in general formulas (2-1) to (2-4):

[0075]

[0076] Wherein: R5 in equation (2-1) is selected from -F or -CF3; R in equations (2-2)-(2-4) is selected from -F or -CF3.

[0077] In one embodiment, X1 in formulas (2-1) to (2-4) is independently selected from CR4 or N each time it appears; preferably, R4 is selected from -H, -D, cyano, nitro, -CF3, -Cl, -Br, -F, -I, straight-chain alkyl having 1 to 10 C atoms, branched or cyclic alkyl having 3 to 10 C atoms, amino, and R ** Substituted or unsubstituted aromatic groups having 6 to 10 carbon atoms, and R ** Substituted or unsubstituted heteroaromatic groups having 5 to 13 ring atoms; wherein: R **It is selected from -D, cyano, nitro, -CF3, -Cl, -Br, -F, -I, straight-chain alkyl with 1 to 10 carbon atoms, or branched or cyclic alkyl with 3 to 10 carbon atoms.

[0078] In a specific example, the structure of the boron-containing organic compound is selected from any of the structures shown in general formulas (3-1) to (3-17):

[0079]

[0080] In a specific example, each occurrence of Z is independently selected from N or P.

[0081] In a specific example, Z is selected from N.

[0082] In one embodiment, X is independently selected from CR1 or N each time it appears; preferably, R1 is selected from -H, -D, cyano, nitro, -CF3, -Cl, -Br, -F, -I, straight-chain alkyl having 1 to 10 carbon atoms, branched or cyclic alkyl having 3 to 10 carbon atoms, amino, and R. ** Substituted or unsubstituted aromatic groups having 6 to 10 carbon atoms, and R ** Substituted or unsubstituted heteroaromatic groups having 5 to 13 ring atoms; wherein: R ** It is selected from -D, cyano, nitro, -CF3, -Cl, -Br, -F, -I, straight-chain alkyl with 1 to 10 carbon atoms, or branched or cyclic alkyl with 3 to 10 carbon atoms.

[0083] In a specific example, Ar 1 Ar 4 Ar 5 Ar 6 Each occurrence is independently selected from any one of the following groups or a combination of the following groups:

[0084]

[0085] in:

[0086] Each time X2 appears, it is independently selected from N or CR7;

[0087] Each occurrence of Y2 is independently selected from CR8R9, SiR8R9, NR8, PR8, C=O, S, or O;

[0088] R7, R8, and R9, each appearing independently, are selected from: -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, thioalkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, alkoxy groups having 3 to 20 carbon atoms, thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, and groups having 7 to 20 carbon atoms. Aryloxycarbonyl, cyano, carbamoyl, halocarbamoyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 50 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 50 ring atoms, aryloxy groups having 6 to 50 ring atoms, heteroaryloxy groups having 5 to 50 ring atoms, or combinations of these groups.

[0089] In one embodiment, the amino group of the present invention is selected from -NR'R"; wherein: R' and R" are selected from substituted or unsubstituted aromatic groups having 6 to 20 C atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms; further, R' and R" are selected from: R * Substituted or unsubstituted aromatic groups having 6 to 10 carbon atoms, or R * Aromatic groups, substituted or unsubstituted, having 6 to 13 carbon atoms; wherein: R * Selected from -D, straight-chain alkyl with 1 to 20 carbon atoms, branched or cyclic alkyl with 3 to 20 carbon atoms, cyano, isocyano, nitro, amino, -CF3, -Cl, -Br, -F, or phenyl, or pyridyl, or pyrimidinyl, or triazine, or biphenyl, or terphenyl, or naphthyl.

[0090] In a specific example, Ar 1 Each occurrence is independently selected from (C-1); further, Ar 1 Each time it appears, it is selected independently. * indicates a connection site; furthermore, Ar 1 Each time it appears, it is selected independently. Furthermore, each occurrence of R7 is independently selected from: -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, cyano, isocyano, nitro, amino, -CF3, -Cl, -Br, -F, and R. * Substituted or unsubstituted aromatic groups having 6 to 10 carbon atoms, or R * Aromatic groups, substituted or unsubstituted, having 6 to 13 carbon atoms; wherein: R * The meaning is the same as described above.

[0091] In a specific example, Ar 6 Each occurrence is independently selected from (C-1); further, Ar 6 Each time it appears, it is selected independently. * indicates a connection site; furthermore, Ar 6 Each time it appears, it is selected independently. Furthermore, each occurrence of R7 is independently selected from: -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, cyano, isocyano, nitro, amino, -CF3, -Cl, -Br, -F, and R. * Substituted or unsubstituted aromatic groups having 6 to 10 carbon atoms, or R * Aromatic groups, substituted or unsubstituted, having 6 to 13 carbon atoms; wherein: R * The meaning is the same as described above.

[0092] In a specific example, the structure of the boron-containing organic compound is selected from any of the structures shown in general formulas (4-1) to (4-17):

[0093]

[0094] In a specific example, each time X appears in general formulas (4-1) to (4-17), it is independently selected from CR1; the meaning of R1 is the same as described above.

[0095] In a specific example, X2 in general formulas (4-1) to (4-17) is selected independently from CR7 each time it appears; the meaning of R7 is the same as described above.

[0096] In a specific example, each occurrence of Y and Y1 is independently selected from: O, S, C(CH3)2, NH, C(F)2, C(H)2, N-CH3, or N-Ph.

[0097] In a specific example, R1, R4, and R7 in general formulas (4-1) to (4-17) are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, cyano, isocyano, nitro, amino, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0098] In a specific example, R1, R4, and R7 in general formulas (4-1) to (4-17) are independently selected from: -H, -D, straight-chain alkyl groups having 1 to 10 carbon atoms, branched or cyclic alkyl groups having 3 to 10 carbon atoms, cyano, isocyano, nitro, amino, -CF3, -Cl, -Br, -F, and R... ** Substituted or unsubstituted aromatic groups having 6 to 10 carbon atoms, or R ** Aromatic groups, substituted or unsubstituted, having 6 to 13 carbon atoms; wherein: R ** The meaning is the same as described above.

[0099] In a specific example, R1, R4, and R7 in general formulas (4-1) to (4-17) are independently selected from: -H, -D, -CH3, -CF3, -F, -t-Am, -t-Bu, -N(Ph)2 substituted with t-Am or t-Bu, aromatic groups having 6 to 10 ring atoms substituted with t-Am, t-Bu, -CH3, -CF3, or -F, and heteroaromatic groups having 6 to 13 ring atoms.

[0100] It should be noted that t-Am represents 2-(2-methyl)butyl; t-Bu represents tert-butyl.

[0101] In a specific example, Ar 4 Ar 5 Each occurrence is independently selected from (C-1), (C-3), or (C-6). In one embodiment, Ar 4 Ar 5 Selected from the same group.

[0102] In one embodiment, the structure of the boron-containing organic compound is selected from any of the structures shown in general formulas (5-1) to (5-19):

[0103]

[0104]

[0105] In a specific example, R1, R4, and R7 are independently selected from -H, -D, -CH3, -CF3, -F, -t-Am, -t-Bu, or the following groups:

[0106]

[0107] Where: # represents the connection site.

[0108] Specifically, the boron-containing organic compounds according to the present invention are selected from, but not limited to, the following structures:

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] The compounds invented can be used as functional materials in electronic devices, especially OLED devices. Organic functional materials can be classified into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), emitters, hosts, and organic dyes.

[0121] In a specific example, the boron-containing organic compound according to the present invention is used in the light-emitting layer, preferably as a guest material in the light-emitting layer.

[0122] In one specific example, a boron-containing organic compound according to the present invention is used as a blue light-emitting material in the light-emitting layer.

[0123] This invention also provides a mixture comprising the aforementioned boron-containing organic compound and at least one organic functional material. The organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, or organic dyes. The luminescent material is selected from singlet luminescent materials (fluorescent materials), triplet luminescent materials (phosphorescent materials), and organic thermally excited delayed fluorescence materials (TADF materials). For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO 2011110277A1, the entire contents of which are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0124] In one specific example, another organic functional material is selected from the host material; further, another organic functional material is selected from the blue light host material.

[0125] The present invention also provides a composition comprising the above-mentioned boron-containing organic compound or mixture thereof, and at least one organic solvent.

[0126] The composition may also be referred to as ink.

[0127] When used in printing processes, ink viscosity and surface tension are important parameters. Appropriate ink surface tension parameters are suitable for specific substrates and printing methods.

[0128] In a preferred example, the ink according to the invention has a surface tension of about 19 dyne / cm to 50 dyne / cm at the operating temperature or at 25°C; more preferably, it is in the range of 22 dyne / cm to 35 dyne / cm; and most preferably, it is in the range of 25 dyne / cm to 33 dyne / cm.

[0129] In another preferred example, the ink according to the invention has a viscosity of about 1 cps to 100 cps at the operating temperature or 25°C; preferably in the range of 1 cps to 50 cps; more preferably in the range of 1.5 cps to 20 cps; and most preferably in the range of 4.0 cps to 20 cps. The composition thus formulated will facilitate inkjet printing.

[0130] Viscosity can be adjusted by various methods, such as by selecting a suitable solvent and adjusting the concentration of the functional material in the ink. The inks according to the present invention, containing the aforementioned organometallic complexes or polymers, allow for convenient adjustment of the printing ink within an appropriate range according to the printing method used. Generally, the composition according to the present invention contains functional materials in a weight ratio ranging from 0.3% to 30 wt%, preferably from 0.5% to 20 wt%, more preferably from 0.5% to 15 wt%, even more preferably from 0.5% to 10 wt%, and most preferably from 1% to 5 wt%.

[0131] In some examples, in the compositions according to the invention, at least one organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate esters or phosphate esters, or mixtures of two or more solvents.

[0132] In a preferred example, in a composition according to the invention, at least one organic solvent is selected from aromatic or heteroaromatic solvents.

[0133] Examples of aromatic or heteroaromatic solvents suitable for this invention include, but are not limited to: 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, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanoate, ethyl 2-furanoate, etc.

[0134] Examples of aromatic ketone-based solvents suitable for the present invention include, but are not limited to: 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.

[0135] Examples of aromatic ether solvents suitable for this invention include, but are not limited to: 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.

[0136] In some preferred embodiments, the composition according to the invention contains at least one solvent 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.

[0137] In other preferred embodiments, the composition according to the invention contains at least one solvent selected from ester-based solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Particularly preferred are octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0138] The solvent may be used alone or as a mixture of two or more organic solvents.

[0139] In a preferred example, another example of an organic solvent includes (but is not limited to): 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, indene, and / or mixtures thereof.

[0140] In a preferred example, solvents particularly suitable for the present invention are those with Hansen solubility parameters within the following ranges:

[0141] δd (dispersion force) is in the range of 17.0–23.2 MPa. 1 / 2 The range, especially in the range of 18.5–21.0 MPa 1 / 2 Scope;

[0142] δp (polar force) is in the range of 0.2–12.5 MPa. 1 / 2 The range, especially in the range of 2.0–6.0 MPa 1 / 2 Scope;

[0143] δh (hydrogen bond strength) ranges from 0.9 to 14.2 MPa. 1 / 2 The range, especially 2.0–6.0 MPa 1 / 2 The range.

[0144] In the compositions according to the present invention, the boiling point parameter of the organic solvent must be considered when selecting it. In the present invention, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead. The organic solvent can evaporate from the solvent system to form a thin film containing the functional material.

[0145] In a preferred embodiment, the composition according to the invention is a solution.

[0146] In a preferred embodiment, the composition according to the invention is a suspension.

[0147] The compositions in the embodiments of the present invention may include 0.01 to 10 wt% of boron-containing compounds or mixtures according to the present invention, preferably 0.1 to 5 wt%, more preferably 0.2 to 5 wt%, and most preferably 0.25 to 3 wt%.

[0148] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, particularly preferably by a preparation method of printing or coating.

[0149] Suitable printing or coating technologies include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing or pad printing, slot-loaded coating, etc. Gravure printing, inkjet printing, and other similar techniques are preferred. The solution or suspension may additionally include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, binders, etc., to adjust viscosity, film-forming properties, and improve adhesion. The printing technology and its related requirements for the solution, such as solvent and concentration, viscosity, etc., are also important considerations.

[0150] This invention also provides the application of the above-mentioned boron-containing organic compounds, mixtures, or compositions in organic electronic devices. These organic electronic devices can be selected from, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, with OLEDs being particularly preferred. In embodiments of this invention, the organic compound is preferably used in the light-emitting layer of an OLED device.

[0151] The present invention also provides an organic electronic device comprising the above-mentioned boron-containing organic compounds, the above-mentioned mixtures, or prepared from the above-mentioned compositions.

[0152] Further, the organic electronic device includes a cathode, an anode, and at least one functional layer, said functional layer comprising a boron-containing organic compound or mixture as described above, or prepared from the above-described composition. The functional layer is selected from hole injection layer (HIL), hole transport layer (HTL), light-emitting layer (EML), electron blocking layer (EBL), electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL); preferably, the functional layer is selected from light-emitting layer.

[0153] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, with organic electroluminescent devices such as OLEDs, OLEECs, and organic light-emitting field-effect transistors being particularly preferred.

[0154] The aforementioned light-emitting device, particularly an OLED, includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0155] The substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface. A substrate without surface defects is particularly desirable. In a preferred example, the substrate is flexible and can be a polymer film or plastic with a glass transition temperature (Tg) of 150°C or higher, preferably 200°C, more preferably 250°C, and most preferably 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0156] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. Holes can be readily injected into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In one example, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be readily selected by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to the invention.

[0157] The cathode may comprise a conductive metal or metal oxide. Electrons can be readily injected into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the luminescent material in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials suitable for use as cathodes in OLEDs can be used as cathode materials for the devices of this invention. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0158] OLEDs may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0159] In a preferred example, in the light-emitting device according to the invention, the light-emitting layer is prepared by means of a composition according to the invention.

[0160] The light-emitting device according to the present invention has an emission wavelength between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0161] The present invention also relates to the application of the organic electronic devices according to the invention in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0162] The present invention also relates to electronic devices comprising organic electronic devices according to the present invention, including but not limited to display devices, lighting devices, light sources, sensors, etc. Specific Implementation

[0164] The boron-containing organic compounds of the present invention will be further described in detail below with reference to specific embodiments. Unless otherwise specified, all raw materials used in the following embodiments are commercially available products.

[0165] Example 1

[0166] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0167]

[0168] Synthesis of intermediates 1-3:

[0169] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 1-3 in a molar amount of 5.68 mmol, yield: 56.8%. MS (ASAP) = 410.2.

[0170] Synthesis of intermediates 1-5:

[0171] Under a nitrogen atmosphere, 1 mmol of intermediate 1-3 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.71 mmol of intermediate 1-5. The reaction yield was 71%, and the MS (ASAP) value was 582.1.

[0172] Synthesis of compound (1):

[0173] In a 250 mL three-necked flask, 10 mmol of intermediate 1-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 52.2%, and MS(ASAP) = 512.3.

[0174] Example 2

[0175] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0176]

[0177] Synthesis of intermediates 2-3:

[0178] Under a nitrogen atmosphere, 10 mmol of intermediate 2-1 and 10 mmol of intermediate 2-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 2-3 in a molar amount of 7.84 mmol, yield: 78.4%. MS (ASAP) = 679.3.

[0179] Synthesis of intermediates 2-5:

[0180] Under a nitrogen atmosphere, 1 mmol of intermediate 2-3 and 1 mmol of intermediate 2-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.57 mmol of intermediate 2-5. The reaction yield was 57%, and the MS (ASAP) value was 905.9.

[0181] Synthesis of compound (2):

[0182] In a 250 mL three-necked flask, 10 mmol of intermediate 2-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 67.4%, and MS(ASAP) = 835.1.

[0183] Example 3

[0184] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0185]

[0186] Synthesis of part 3-2:

[0187] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 3-2 in a molar amount of 6.72 mmol, yield: 67.2%. MS (ASAP) = 342.1.

[0188] Synthesis of intermediate 3-3:

[0189] Under a nitrogen atmosphere, 1 mmol of intermediate 2-2 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.76 mmol of intermediate 3-3. The reaction yield was 76%, and the MS (ASAP) value was 514.3.

[0190] Synthesis of compound (3):

[0191] In a 250 mL three-necked flask, 10 mmol of intermediate 3-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 66.2%, and MS(ASAP) = 444.6.

[0192] Example 4

[0193] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0194]

[0195] Synthesis of intermediates 1-3:

[0196] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 1-3 in a molar amount of 5.68 mmol, yield: 56.8%. MS (ASAP) = 410.2.

[0197] Synthesis of intermediate 4-2:

[0198] Under a nitrogen atmosphere, 1 mmol of intermediate 1-3 and 1 mmol of intermediate 4-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. The molar amount of intermediate 4-2 was 0.73 mmol by recrystallization from ethyl acetate. The reaction yield was 73%, and the MS (ASAP) value was 588.2.

[0199] Synthesis of compound (4):

[0200] In a 250 mL three-necked flask, 10 mmol of intermediate 4-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 59.7%, and MS(ASAP) = 518.4.

[0201] Example 5

[0202] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0203]

[0204] Synthesis of part 3-2:

[0205] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 3-2 in a molar amount of 6.72 mmol, yield: 67.2%. MS (ASAP) = 342.1.

[0206] Synthesis of intermediate 5-1:

[0207] Under a nitrogen atmosphere, 1 mmol of intermediate 3-2 and 1 mmol of intermediate 4-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. The molar amount of intermediate 5-1 was 0.64 mmol by recrystallization from ethyl acetate. The reaction yield was 64%, and the MS (ASAP) value was 520.3.

[0208] Synthesis of compound (5):

[0209] In a 250 mL three-necked flask, 10 mmol of intermediate 5-1 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 51.3%, and MS(ASAP) = 450.6.

[0210] Example 6

[0211] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0212]

[0213] Synthesis of intermediate 6-2:

[0214] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 6-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 6-2 in a molar amount of 7.31 mmol, yield: 73.1%. MS (ASAP) = 410.2.

[0215] Synthesis of intermediate 6-3:

[0216] Under a nitrogen atmosphere, 1 mmol of intermediate 6-2 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.59 mmol of intermediate 6-3. The reaction yield was 59%, and the MS (ASAP) value was 582.1.

[0217] Synthesis of compound (6):

[0218] In a 250 mL three-necked flask, 10 mmol of intermediate 6-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 67.8%, and MS(ASAP) = 512.3.

[0219] Example 7

[0220] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0221]

[0222] Synthesis of intermediate 6-2:

[0223] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 6-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 6-2 in a molar amount of 7.31 mmol, yield: 73.1%. MS (ASAP) = 410.2.

[0224] Synthesis of intermediate 7-1:

[0225] Under a nitrogen atmosphere, 1 mmol of intermediate 6-2 and 1 mmol of intermediate 4-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.51 mmol of intermediate 7-1. The reaction yield was 51%, and the MS (ASAP) value was 588.4.

[0226] Synthesis of compound (7):

[0227] In a 250 mL three-necked flask, 10 mmol of intermediate 7-1 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 73.8%, and MS(ASAP) = 518.6.

[0228] Example 8

[0229] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0230]

[0231] Synthesis of intermediate 8-2:

[0232] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 8-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 8-2 in a molar amount of 6.84 mmol, yield: 68.4%. MS (ASAP) = 342.6.

[0233] Synthesis of intermediate 8-3:

[0234] Under a nitrogen atmosphere, 1 mmol of intermediate 8-2 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.77 mmol of intermediate 8-3. The reaction yield was 77%, and the MS (ASAP) value was 514.6.

[0235] Synthesis of compound (8):

[0236] In a 250 mL three-necked flask, 10 mmol of intermediate 8-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 72.9%, and MS(ASAP) = 444.7.

[0237] Example 9

[0238] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0239]

[0240] Synthesis of intermediate 8-2:

[0241] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 8-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 8-2 in a molar amount of 6.84 mmol, yield: 68.4%. MS (ASAP) = 342.6.

[0242] Synthesis of intermediate 9-1:

[0243] Under a nitrogen atmosphere, 1 mmol of intermediate 8-2 and 1 mmol of intermediate 4-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.65 mmol of intermediate 9-1. The reaction yield was 65%, and the MS (ASAP) value was 520.1.

[0244] Synthesis of compound (9):

[0245] In a 250 mL three-necked flask, 10 mmol of intermediate 9-1 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 78.6%, and MS(ASAP) = 450.3.

[0246] Example 10

[0247] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0248]

[0249] Synthesis of part 3-2:

[0250] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 3-2 in a molar amount of 6.72 mmol, yield: 67.2%. MS (ASAP) = 342.1.

[0251] Synthesis of intermediate 5-1:

[0252] Under a nitrogen atmosphere, 1 mmol of intermediate 3-2 and 1 mmol of intermediate 4-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. The molar amount of intermediate 5-1 was 0.64 mmol by recrystallization from ethyl acetate. The reaction yield was 64%, and the MS (ASAP) value was 520.3.

[0253] Synthesis of compound (10):

[0254] In a 250 mL three-necked flask, 10 mmol of intermediate 5-1 and 100 mL of dry tert-butylbenzene were added. The mixture was cooled to -30 °C under a nitrogen atmosphere, and (61.2 mmol) of n-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 51.3%, and MS(ASAP) = 450.6.

[0255] Example 11

[0256] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0257]

[0258] Synthesis of part 3-2:

[0259] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 3-2 in a molar amount of 6.72 mmol, yield: 67.2%. MS (ASAP) = 342.1.

[0260] Synthesis of intermediate 3-3:

[0261] Under a nitrogen atmosphere, 1 mmol of intermediate 2-2 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.76 mmol of intermediate 3-3. The reaction yield was 76%, and the MS (ASAP) value was 514.3.

[0262] Synthesis of compound (11):

[0263] In a 250 mL three-necked flask, 10 mmol of intermediate 3-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of n-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 66.2%, and MS(ASAP) = 444.6.

[0264] Example 12

[0265] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0266]

[0267] Synthesis of intermediate 12-2:

[0268] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 12-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 12-2 in a molar amount of 5.68 mmol, yield: 75.6%. MS (ASAP) = 394.3.

[0269] Synthesis of intermediate 12-3:

[0270] Under a nitrogen atmosphere, 1 mmol of intermediate 12-2 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.81 mmol of intermediate 12-3. The reaction yield was 81%, and the MS (ASAP) value was 566.1.

[0271] Synthesis of compound (12):

[0272] In a 250 mL three-necked flask, 10 mmol of intermediate 12-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 81.6%, and MS(ASAP) = 496.5.

[0273] Example 13

[0274] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0275]

[0276] Synthesis of intermediate 13-2:

[0277] Under a nitrogen atmosphere, 10 mmol of intermediate 2-1 and 10 mmol of intermediate 13-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 13-2 in a molar amount of 7.77 mmol, yield: 78.4%. MS (ASAP) = 663.1.

[0278] Synthesis of intermediate 13-3:

[0279] Under a nitrogen atmosphere, 1 mmol of intermediate 13-2 and 1 mmol of intermediate 2-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.68 mmol of intermediate 13-3. The reaction yield was 68%, and the MS (ASAP) value was 889.9.

[0280] Synthesis of compound (13):

[0281] In a 250 mL three-necked flask, 10 mmol of intermediate 13-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 55.2%, and MS(ASAP) = 819.3.

[0282] Example 14

[0283] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0284]

[0285] Synthesis of intermediate 14-2:

[0286] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 14-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was extinguished by water extraction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 14-2 in a molar amount of 6.33 mmol, yield: 63.3%. MS (ASAP) = 460.2.

[0287] Synthesis of intermediate 14-4:

[0288] Under a nitrogen atmosphere, 1 mmol of intermediate 14-2 and 1 mmol of intermediate 14-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.54 mmol of intermediate 14-4. The reaction yield was 54%, and the MS (ASAP) value was 682.3.

[0289] Synthesis of compound (14):

[0290] In a 250 mL three-necked flask, 10 mmol of intermediate 14-4 and 100 mL of dry tert-butylbenzene were added. The mixture was cooled to -30 °C under a nitrogen atmosphere, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 65.9%, and MS(ASAP) = 612.4.

[0291] Example 15

[0292] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0293]

[0294] Synthesis of intermediate 15-2:

[0295] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 15-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain 7.06 mmol of intermediate 15-2, yield: 70.6%. MS (ASAP) = 444.2.

[0296] Synthesis of intermediate 15-3:

[0297] Under a nitrogen atmosphere, 1 mmol of intermediate 15-2 and 1 mmol of intermediate 14-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.51 mmol of intermediate 15-3. The reaction yield was 51%, and the MS (ASAP) value was 666.4.

[0298] Synthesis of compound (15):

[0299] In a 250 mL three-necked flask, 10 mmol of intermediate 15-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 75.3%, and MS(ASAP) = 596.4.

[0300] Example 16

[0301] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0302]

[0303] Synthesis of intermediate 16-2:

[0304] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 16-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 16-2 in a molar amount of 8.14 mmol, yield: 81.4%. MS (ASAP) = 392.3.

[0305] Synthesis of intermediate 16-4:

[0306] Under a nitrogen atmosphere, 1 mmol of intermediate 16-2 and 1 mmol of intermediate 14-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.67 mmol of intermediate 16-4. The reaction yield was 67%, and the MS (ASAP) value was 614.2.

[0307] Synthesis of compound (16):

[0308] In a 250 mL three-necked flask, 10 mmol of intermediate 16-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 78.4%, and MS(ASAP) = 544.4.

[0309] Example 17

[0310] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0311]

[0312] Synthesis of intermediate 17-2:

[0313] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 17-1 and 10 mmol of intermediate 16-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain 8.35 mmol of intermediate 17-2, with a yield of 83.5%. MS (ASAP) = 476.2.

[0314] Synthesis of intermediate 17-3:

[0315] Under a nitrogen atmosphere, 1 mmol of intermediate 17-2 and 1 mmol of intermediate 14-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.88 mmol of intermediate 17-3. The reaction yield was 88%, and the MS (ASAP) value was 698.2.

[0316] Synthesis of compound (18):

[0317] In a 250 mL three-necked flask, 10 mmol of intermediate 17-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 60.5%, and MS(ASAP) = 628.4.

[0318] Example 18

[0319] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0320]

[0321] Synthesis of intermediate 18-3:

[0322] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 18-1 and 10 mmol of intermediate 18-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 18-3 in a molar amount of 7.05 mmol, yield: 70.5%. MS (ASAP) = 810.3.

[0323] Synthesis of intermediate 18-4:

[0324] Under a nitrogen atmosphere, 1 mmol of intermediate 18-3 and 1 mmol of intermediate 1-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.54 mmol of intermediate 18-4. The reaction yield was 54%, and the MS (ASAP) value was 982.5.

[0325] Synthesis of compound (18):

[0326] In a 250 mL three-necked flask, 10 mmol of intermediate 18-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 77.3%, and MS(ASAP) = 912.6.

[0327] Example 19

[0328] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0329]

[0330] Synthesis of intermediate 19-3:

[0331] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 19-1 and 10 mmol of intermediate 19-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 19-3 in a molar amount of 7.76 mmol, yield: 77.6%. MS (ASAP) = 826.1.

[0332] Synthesis of intermediate 19-4:

[0333] Under a nitrogen atmosphere, 1 mmol of intermediate 19-3 and 1 mmol of intermediate 14-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.82 mmol of intermediate 19-4. The reaction yield was 82%, and the MS (ASAP) value was 1048.2.

[0334] Synthesis of compound (19):

[0335] In a 250 mL three-necked flask, 10 mmol of intermediate 19-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further raised to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 60.8%, and MS(ASAP) = 978.3.

[0336] Example 20

[0337] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0338]

[0339] Synthesis of intermediate 20-3:

[0340] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 20-1 and 10 mmol of intermediate 20-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 20-3 in a molar amount of 7.32 mmol, yield: 73.2%. MS (ASAP) = 574.2.

[0341] Synthesis of intermediate 20-5:

[0342] Under a nitrogen atmosphere, 1 mmol of intermediate 20-3 and 1 mmol of intermediate 20-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.57 mmol of intermediate 20-5. The reaction yield was 57%, and the MS (ASAP) value was 734.7.

[0343] Synthesis of compound (20):

[0344] In a 250 mL three-necked flask, 10 mmol of intermediate 20-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 54.6%, and MS(ASAP) = 664.5.

[0345] Example 21

[0346] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0347]

[0348] Synthesis of intermediate 21-3:

[0349] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 21-1 and 10 mmol of intermediate 21-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 21-3 in a molar amount of 8.25 mmol, yield: 82.5%. MS (ASAP) = 492.1.

[0350] Synthesis of intermediate 21-5:

[0351] Under a nitrogen atmosphere, 1 mmol of intermediate 21-3 and 1 mmol of intermediate 21-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.55 mmol of intermediate 21-5. The reaction yield was 55%, and the MS (ASAP) value was 702.1.

[0352] Synthesis of compound (21):

[0353] In a 250 mL three-necked flask, 10 mmol of intermediate 21-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further raised to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 64.9%, and MS(ASAP) = 632.4.

[0354] Example 22

[0355] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0356]

[0357] Synthesis of intermediate 22-3:

[0358] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 22-1 and 10 mmol of intermediate 22-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 22-3 in a molar amount of 8.25 mmol, yield: 82.5%. MS (ASAP) = 536.2.

[0359] Synthesis of intermediate 22-5:

[0360] Under a nitrogen atmosphere, 1 mmol of intermediate 22-3 and 1 mmol of intermediate 22-4 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.62 mmol of intermediate 22-5. The reaction yield was 62%, and the MS (ASAP) value was 698.3.

[0361] Synthesis of compound (22):

[0362] In a 250 mL three-necked flask, 10 mmol of intermediate 22-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 57.8%, and MS(ASAP) = 628.4.

[0363] Example 23

[0364] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0365]

[0366] Synthesis of intermediate 23-2:

[0367] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 23-1 and 10 mmol of intermediate 16-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 23-2 in a molar amount of 7.45 mmol, yield: 74.5%. MS (ASAP) = 624.8.

[0368] Synthesis of intermediate 23-4:

[0369] Under a nitrogen atmosphere, 1 mmol of intermediate 23-2 and 1 mmol of intermediate 23-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.59 mmol of intermediate 23-4. The reaction yield was 59%, and the MS (ASAP) value was 852.4.

[0370] Synthesis of compound (23):

[0371] In a 250 mL three-necked flask, 10 mmol of intermediate 23-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 45.8%, and MS(ASAP) = 782.3.

[0372] Example 24

[0373] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0374]

[0375] Synthesis of intermediate 24-1:

[0376] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 20-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 24-1 in a molar amount of 5.56 mmol, yield: 55.6%. MS (ASAP) = 376.2.

[0377] Synthesis of intermediate 24-3:

[0378] Under a nitrogen atmosphere, 1 mmol of intermediate 24-1 and 1 mmol of intermediate 24-2 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.68 mmol of intermediate 24-3. The reaction yield was 68%, and the MS (ASAP) value was 536.4.

[0379] Synthesis of compound (24):

[0380] In a 250 mL three-necked flask, 10 mmol of intermediate 24-3 and 100 mL of dry tert-butylbenzene were added. The mixture was cooled to -30 °C under a nitrogen atmosphere, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 57.2%, and MS(ASAP) = 466.2.

[0381] Example 25

[0382] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0383]

[0384] Synthesis of intermediate 25-2:

[0385] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 25-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 25-2 in a molar amount of 6.66 mmol, yield: 66.6%. MS (ASAP) = 326.2.

[0386] Synthesis of intermediate 25-3:

[0387] Under a nitrogen atmosphere, 1 mmol of intermediate 25-2 and 1 mmol of intermediate 24-2 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.61 mmol of intermediate 25-3. The reaction yield was 61%, and the MS (ASAP) value was 486.4.

[0388] Synthesis of compound (25):

[0389] In a 250 mL three-necked flask, 10 mmol of intermediate 25-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 74.9%, and MS(ASAP) = 416.2.

[0390] Example 26

[0391] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0392]

[0393] Synthesis of intermediate 25-2:

[0394] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 25-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 25-2 in a molar amount of 6.66 mmol, yield: 66.6%. MS (ASAP) = 326.2.

[0395] Synthesis of intermediate 26-2:

[0396] Under a nitrogen atmosphere, 1 mmol of intermediate 25-2 and 1 mmol of intermediate 26-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.78 mmol of intermediate 26-2. The reaction yield was 78%, and the MS (ASAP) value was 534.2.

[0397] Synthesis of compound (26):

[0398] In a 250 mL three-necked flask, 10 mmol of intermediate 26-2 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 80.4%, and MS(ASAP) = 416.2.

[0399] Example 27

[0400] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0401]

[0402] Synthesis of intermediate 27-2:

[0403] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 27-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 27-2 in a molar amount of 8.45 mmol, yield: 84.5%. MS (ASAP) = 326.2.

[0404] Synthesis of intermediate 27-4:

[0405] Under a nitrogen atmosphere, 1 mmol of intermediate 27-2 and 1 mmol of intermediate 27-3 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.74 mmol of intermediate 27-4. The reaction yield was 74%, and the MS (ASAP) value was 489.3.

[0406] Synthesis of compound (27):

[0407] In a 250 mL three-necked flask, 10 mmol of intermediate 27-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 81.6%, and MS(ASAP) = 418.5.

[0408] Example 28

[0409] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0410]

[0411] Synthesis of intermediate 25-2:

[0412] Under a nitrogen atmosphere, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 25-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 80 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 25-2 in a molar amount of 6.66 mmol, yield: 66.6%. MS (ASAP) = 326.2.

[0413] Synthesis of intermediate 28-2:

[0414] Under a nitrogen atmosphere, 1 mmol of intermediate 25-2 and 1 mmol of intermediate 28-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.81 mmol of intermediate 28-2. The reaction yield was 81%, and the MS (ASAP) value was 536.2.

[0415] Synthesis of compound (28):

[0416] In a 250 mL three-necked flask, 10 mmol of intermediate 28-2 and 100 mL of dry tert-butylbenzene were added. The mixture was cooled to -30 °C under a nitrogen atmosphere, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 70.6%, and MS(ASAP) = 418.5.

[0417] Example 29

[0418] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0419]

[0420] Synthesis of intermediate 24-1:

[0421] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 20-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 24-1 in a molar amount of 5.56 mmol, yield: 55.6%. MS (ASAP) = 376.2.

[0422] Synthesis of intermediate 29-1:

[0423] Under a nitrogen atmosphere, 1 mmol of intermediate 24-1 and 1 mmol of intermediate 28-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added sequentially. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.71 mmol of intermediate 29-1. The reaction yield was 71%, and the MS (ASAP) value was 586.3.

[0424] Synthesis of compound (29):

[0425] In a 250 mL three-necked flask, 10 mmol of intermediate 29-1 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 63.5%, and MS(ASAP) = 468.3.

[0426] Example 30

[0427] This embodiment provides a boron-containing organic compound, and the specific synthetic route is as follows:

[0428]

[0429] Synthesis of intermediate 30-2:

[0430] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-1 and 10 mmol of intermediate 30-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 80 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 30-2 in a molar amount of 7.34 mmol, yield: 73.4%. MS (ASAP) = 376.2.

[0431] Synthesis of intermediate 30-3:

[0432] Under a nitrogen atmosphere, 1 mmol of intermediate 30-2 and 1 mmol of intermediate 28-1 were added to a dry three-necked flask, 100 mL of DMSO was added as solvent, and dry K2CO3 was added as base. The reaction was carried out at 120 °C for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and water and dichloromethane were added in sequence. The reaction solution was washed with water several times, and the aqueous phase was extracted with dichloromethane several times. The organic phases were combined, dried with anhydrous Na2CO3, filtered, and the reaction solution was evaporated to dryness to obtain the crude product. Recrystallization from ethyl acetate yielded 0.78 mmol of intermediate 30-3. The reaction yield was 78%, and the MS (ASAP) value was 586.3.

[0433] Synthesis of compound (30):

[0434] In a 250 mL three-necked flask, 10 mmol of intermediate 30-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (30.6 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 °C, and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 10.5 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 21 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by rapid silica gel column chromatography to obtain a pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder. The yield was 76.3%, and MS(ASAP) = 468.3.

[0435] Fabrication and characterization of OLED devices

[0436] The energy levels of organic compound materials can be obtained through quantum computing, such as using TD-DFT (time-dependent density functional theory) via Gaussian09W (Gaussian Inc.). Specific simulation methods can be found in WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule is calculated using TD-DFT (time-dependent density functional theory) to obtain "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). HOMO and LUMO energy levels are calculated according to the following calibration formulas, with S1, T1, and the resonance factor f(S1) used directly.

[0437] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0438] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0439] HOMO, LUMO, T1, and S1 are direct calculation results of Gaussian 09W, in Hartree units, as shown in Table 1.

[0440] Table 1

[0441] Compound 1 -5.31 -2.33 2.51 3.11 Compound 2 -5.21 -2.36 2.58 3.01 Compound 3 -5.27 -2.11 2.62 2.90 Compound 4 -5.25 -2.35 2.60 2.95 Compound 5 -5.21 -2.32 2.55 3.01 Compound 6 -5.36 -2.29 2.59 3.03 Compound 7 -5.13 -2.33 2.62 3.06 Compound 8 -5.29 -2.38 2.58 2.99 Compound 9 -5.19 -2.21 2.63 3.03 Compound 10 -5.32 -2.18 2.65 3.03 Compound 11 -5.18 -2.23 2.60 2.97 Compound 12 -5.21 -2.35 2.58 2.99 Compound 13 -5.25 -2.21 2.56 3.01 Compound 14 -5.41 -2.28 2.62 3.00 Compound 15 -5.31 -2.13 2.55 3.03 Compound 16 -5.32 -2.34 2.59 3.08 Compound 17 -5.34 -2.31 2.63 3.09 Compound 18 -5.29 -2.25 2.64 2.99 Compound 19 -5.26 -2.30 2.61 2.96 Compound 20 -5.26 -2.29 2.56 3.05 Compound 21 -5.25 -2.29 2.56 2.93 Compound 22 -5.16 -2.30 2.66 3.01 Compound 23 -5.28 -2.35 2.57 3.04 Compound 24 -5.16 -2.31 2.69 3.01 Compound 25 -5.30 -2.28 2.68 3.01 Compound 26 -5.19 -2.29 2.65 2.99 Compound 27 -5.23 -2.25 2.60 2.98 Compound 28 -5.23 -2.29 2.59 3.09 Compound 29 -5.38 -2.31 2.60 3.00 Compound 30 -5.31 -2.31 2.59 3.01 BD-Ref1 -5.07 -2.31 2.59 3.01 BD-Ref2 -5.07 -2.24 2.58 3.08 BD-Ref3 -5.03 -2.41 2.66 3.02

[0442] 2. Fabrication and Characterization of OLED Devices

[0443]

[0444] The aforementioned materials BH, ET, Liq, and BD-Ref are all commercially available, or their synthesis methods are existing technologies, as detailed in the references within the existing technologies, and will not be elaborated upon here. BH is used as the host material, ET as the electron transport material, and Liq as the electron injection material.

[0445] The fabrication process of the OLED device using the above-described compound is described in detail below through specific embodiments. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode, and its schematic diagram is shown below. Figure 1 As shown, 101 is the substrate, 102 is the anode, 103 is the hole injection layer (HIL), 104 is the hole transport layer (HTL), 105 is the light-emitting layer, 106 is the electron transport layer (ETL), and 107 is the cathode. The fabrication steps are as follows:

[0446] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrate: Clean with various solvents (such as one or more of chloroform, acetone or isopropanol), and then perform ultraviolet ozone treatment.

[0447] b. HIL (hole injection layer, 40nm): 60nm PEDOT (polyethylene dioxythiophene, Clevios) TM AI4083 was spin-coated as HIL in a cleanroom and then treated on a hot plate at 180°C for 10 minutes.

[0448] c. HTL (hole transport layer, 20nm): 20nm PVK (Sigma Aldrich, average Mn 25,000-50,000) was spin-coated in a nitrogen glove box. The solution used was TFB added to toluene solvent at a concentration of 5mg / ml. Then it was treated on a hot plate at 180°C for 60 minutes.

[0449] d. EML (Organic Light Emitting Layer, 40nm): The EML was formed by spin coating in a nitrogen glove box. The solution used was a methyl benzoate solution with different host and guest components (the weight ratio of host and guest components was 95:5), with a solution concentration of 15mg / ml. It was then treated on a hot plate at 140°C for 10 minutes. The host material was BH, and the guest components were the compounds listed in the embodiments of this patent and the comparative compounds (see Table 2). All other implementation schemes were the same.

[0450] e. Electron transport layer and cathode: The heat-treated substrate is transferred to a vacuum chamber, and then ET and LiQ are placed in different evaporation units under high vacuum (1×10⁻⁶). -6 The light-emitting layer was co-deposited in a 50% by weight ratio in a 100nm mol / L solution to form a 20nm electron transport layer on the light-emitting layer, followed by the deposition of a 100nm thick Al cathode.

[0451] f. Encapsulation: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0452] The current-voltage (JV) characteristics of each OLED device were characterized using characterization equipment, and important parameters such as efficiency, lifetime, and external quantum efficiency were recorded, as shown in Table 2.

[0453] Table 2

[0454]

[0455]

[0456] The current-voltage (JV) characteristics of each OLED device were characterized using characterization equipment, and important parameters such as efficiency, lifetime, and external quantum efficiency were recorded, as shown in Table 1. Testing revealed that the blue light-emitting devices prepared using compounds 1-30 as guest materials in the EML layer exhibited superior color coordinates compared to the control compounds 1-3. Furthermore, the blue light-emitting devices prepared using compounds 1-30 as guest materials in the EML layer all achieved luminous efficiencies in the range of 5.7-6.5 cd / A, demonstrating superior luminous efficiency. The blue light-emitting devices prepared using compounds 1-30 as guest materials in the EML layer also exhibited luminous efficiencies in the range of 5.7-6.5 cd / A and lifetimes in the range of 155-177 h, demonstrating excellent luminous efficiency and lifetime. The fluorine groups or trifluoromethyl groups introduced into the compounds of this invention increase the overall Td temperature of the compounds, making them easier to sublimate, thereby improving the purity of the compounds and enhancing device performance. At the same time, the molecular weight is also significantly increased (compared to BD-Ref1-BD-Ref3). Blue light devices prepared using compounds 1-30 as guest materials in the EML layer have a significantly better lifetime than those prepared using compounds 1-3 (generally 50%-100% higher).

[0457] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0458] The embodiments described above are merely illustrative of several implementations of the present invention, designed to facilitate a detailed understanding of the technical solutions of the present invention, but should not be construed as limiting the scope of protection of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the scope of protection of the present invention. It should be understood that technical solutions obtained by those skilled in the art based on the technical solutions provided by the present invention through logical analysis, reasoning, or limited experimentation are all within the scope of protection of the appended claims. Therefore, the scope of protection of this invention patent should be determined by the content of the appended claims, and the specification and drawings can be used to interpret the content of the claims.

Claims

1. A boron-containing organic compound, characterized in that, The boron-containing organic compound is selected from any one of the following structures: 。 2. A mixture, characterized in that, The mixture comprises the boron-containing organic compound of claim 1, and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, or organic dyes.

3. A composition, characterized in that, The composition comprises the boron-containing organic compound of claim 1 or the mixture of claim 2, and at least one organic solvent.

4. An organic electronic device, characterized in that, The organic electronic device comprises the boron-containing organic compound of claim 1, the mixture of claim 2, or the composition of claim 3.

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