Boron-containing resonance type organic compound and organic electroluminescent device containing same

Abstract

The invention relates to a boron-containing resonance type organic compound and an organic light-emitting device containing the same, and belongs to the technical field of semiconductors, and the structure of the compound provided by the invention is as shown in a general formula (1): # imgabs0. The compound provided by the invention is used as a doping material in a light-emitting layer material of an OLED (Organic Light-Emitting Diode) light-emitting device; the material can be used as a luminescent layer green light doping material of an organic electroluminescent device, so that the service life of the device is prolonged.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing resonant organic compound and an organic electroluminescent device comprising the same. Background Art

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has technical advantages such as lighter and thinner, high color contrast, low power consumption, fast response, high clarity, and flexibility, and is considered to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. The early lower color gamut standards (BT.709 and DCIP3) can no longer meet the high-quality technical development requirements of display products. To achieve the performance requirements of ultra-high definition and higher picture quality of display products, the new generation of display standard (BT.2020) drives OLED luminescent materials to develop towards high color purity, which requires the core luminescent materials to have a narrower emission spectrum. Among the current commercial OLED red, green, and blue color display technologies, the blue light uses the triplet-triplet conversion (TTF) technology of traditional fluorescence. Although this technology has low efficiency, it has high color purity and basically meets the BT.2020 display index; the green and red lights use phosphorescent emission technology. This technology has high efficiency, and the red light is close to the BT.2020 display index. However, the green light is limited by the relatively wide emission spectrum of phosphorescence, which is quite different from the requirements of the high-definition display index. Therefore, it is very crucial to develop high-color-purity green OLED materials.

[0003] Since 2020, green light materials with a narrow full width at half maximum (FWHM < 30 nm) based on the boron-nitrogen resonance structure have been successively reported: DOI: 10.1002 / adom.201902142, DOI: 10.1002 / anie.202008264, DOI: 10.1021 / jacs.0c10081, DOI: 10.1038 / s41467-022-32607-3, DOI: 10.1002 / anie.202202380, etc., showing extremely high color purity and efficiency of this type of material, and becoming the development trend of high-color-purity green OLEDs. However, there are still many technical difficulties in the development of green ultra-high-color-purity materials containing boron-nitrogen structures, and the existing materials also have the defect that their efficiency and lifespan cannot meet the requirements of mass production. Developing narrow-FWHM green light materials based on the boron-nitrogen resonance structure that can meet practical applications is the key technical point for the next generation of display devices with high color purity, high color gamut coverage, high efficiency, and high immersion.

[0004] In addition, the sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. Using the triplet exciton sensitizing materials as the exciton sensitization medium, the triplet excitons are fully utilized, and the energy is transferred to the fluorescent doping materials through energy transfer, which can also achieve a 100% internal quantum efficiency of the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively utilize the characteristics of high fluorescence quantum yield, high device stability, high color purity and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs. For example, in CN107507921A and CN110492006A, a light-emitting layer combination technology is disclosed with a TADF material having a minimum singlet and minimum triplet energy level difference less than or equal to 0.2 eV as the main body and a boron-containing material as the dopant; in CN110492005A and CN110492009A, a light-emitting layer combination scheme with an exciplex as the main body and a boron-containing material as the dopant is disclosed; both can achieve efficiency comparable to that of phosphorescence and a relatively narrow full width at half maximum. Therefore, developing a sensitization technology based on narrow full width at half maximum boron-based luminescent materials has unique advantages and strong potential for meeting the BT.2020 display standards. SUMMARY OF THE INVENTION

[0005] In view of the above problems existing in the prior art, the present invention provides a boron-containing resonance organic compound and an organic electroluminescent device comprising the same. The compound of the present invention can emit green light when used as a light-emitting layer doping material for an organic electroluminescent device.

[0006] The technical solution of the present invention is as follows: A boron-containing resonance organic compound, the structure of the boron-containing resonance organic compound is shown in the general formula (1):

[0007]

[0008] In the general formula (1), Z each occurrence is the same or different and represents C-(H) or C-(R0); R0 each occurrence is independently represented as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group;

[0009] Any adjacent R0s can be connected to form a ring;

[0010] Each occurrence of R1 and R2 independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group;

[0011] R1 and R2 can be connected to form a ring;

[0012] Each occurrence of Ar1, Ar2, Ar3, and Ar4 independently represents a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0013] Ar1 and Ar2 can be connected to form a ring; Ar2 and Ar4 can be connected to form a ring;

[0014] M1, M2, and M3 each independently represent a C6-C 30 aryl ring substituted or unsubstituted by one or more Rs, a 5-30 membered heteroaryl ring substituted or unsubstituted by one or more Rs, a C6-C 10 aliphatic ring;

[0015] Each occurrence of R independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C10 An alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group;

[0016] Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom;

[0017] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group; any one or more of them;

[0018] The heteroatoms in the heteroaryl group are each independently selected from one or more of O, S, N, Si, and B.

[0019] Furthermore, the boron-containing resonance organic compound has a structure shown by general formula (1-1) or general formula (1-2):

[0020]

[0021] In general formula (1-1) and general formula (1-2), each occurrence of Z is the same or different and represents C-(H) or C-(R0); each occurrence of R0 is independently a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group;

[0022] Any adjacent R0s can be connected to form a ring;

[0023] R1 and R2 each independently represent, each time they appear, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group;

[0024] R1 and R2 may be linked to form a ring;

[0025] Ar1, Ar2, Ar3, and Ar4 each independently represent, each time they appear, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0026] Ar1 and Ar2 may be linked to form a ring; Ar2 and Ar4 may be linked to form a ring;

[0027] M1 and M3 each independently represent a substituted or unsubstituted C6-C 30 aryl ring substituted with one or more Rs, a 5-30 membered heteroaryl ring substituted with one or more Rs, a C6-C 10 aliphatic ring substituted with one or more Rs;

[0028] R each independently represents, each time it appears, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10An aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, or a substituted or unsubstituted silyl group;

[0029] Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom;

[0030] Each occurrence of X1 is the same or different and represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e );

[0031] R a , R b , R c , R d , R e Each occurrence is the same or different and represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0032] R a and M3 can be connected to form a ring; R b and R c , R d and R e can be connected to form a ring;

[0033] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group;

[0034] The heteroatoms in the heteroaryl group are each independently selected from one or more of O, S, N, Si, and B.

[0035] Furthermore, the boron-containing resonance-type organic compound has a structure as shown in any one of General Formulas (A-1) to (A-6):

[0036]

[0037] In General Formulas (A-1) to (A-6), Z each occurrence is the same or different and represents C-(H) or C-(R0); R0 each occurrence is independently represented as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group;

[0038] Any adjacent R0s can be connected to form a ring;

[0039] R1 and R2 each occurrence is the same or different and represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group;

[0040] R1 and R2 can be connected to form a ring;

[0041] Ar5 and Ar6 each occurrence is the same or different and represents a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 One of aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0042] M1 and M3 each independently represent a substituted or unsubstituted C6-C aryl ring, a 5-30 membered heteroaryl ring substituted or unsubstituted with one or more Rs, or a substituted or unsubstituted C6-C 30 alicyclic ring; 10 One of aryl, substituted or unsubstituted C2-C

[0043] Each occurrence of R, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, or a substituted or unsubstituted silyl group;

[0044] Each occurrence of X, which may be the same or different, represents one of a carbon atom or a silicon atom;

[0045] Each occurrence of X1, which may be the same or different, represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e );

[0046] R a 、R b 、R c 、R d 、R e Each occurrence of R, which may be the same or different, represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, or a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30One of heteroaryls;

[0047] R a Can be linked with M3 to form a ring; R b With R c 、R d With R e Can be linked to form a ring;

[0048] The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, C1-C 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 Aryl, deuterium-substituted C6-C 30 Aryl, C5-C 30 Heteroaryl, deuterium-substituted C2-C 30 One or more of heteroaryls;

[0049] The heteroatoms in the heteroaryl are each independently selected from one or more of O, S, N, Si, B.

[0050] Furthermore, the boron-containing resonance organic compound has a structure shown in any one of general formula (B-1) to general formula (B-3):

[0051]

[0052] In general formula (B-1) to general formula (B-3), Z represents C-(H) or C-(R0) each time it appears, the same or different; R0 represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, a substituted or unsubstituted C3-C 10 Cycloalkyl, a substituted or unsubstituted C2-C 10 Alkenyl, a substituted or unsubstituted C2-C 10 Alkynyl, a substituted or unsubstituted C1-C 10 Alkoxy, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 Aryl, a substituted or unsubstituted C2-C 30 Heteroaryl, a substituted or unsubstituted boranyl;

[0053] Any adjacent R0s can be linked to form a ring;

[0054] R1 and R2 each represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, a substituted or unsubstituted C3-C 10 Cycloalkyl, a substituted or unsubstituted C2-C 10An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group, or a substituted or unsubstituted boranyl group;

[0055] R1 and R2 may be linked to form a ring;

[0056] Each occurrence of Ar1, Ar2, Ar3, and Ar4, which may be the same or different, represents a hydrogen atom, a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C2-C 10 An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group;

[0057] Each occurrence of X, which may be the same or different, represents either a carbon atom or a silicon atom;

[0058] Each occurrence of X1, which may be the same or different, represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e );

[0059] R a 、R b 、R c 、R d 、R e Each occurrence of which, which may be the same or different, represents a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C2-C 10 An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group;

[0060] R aIt can be connected to an adjacent Z to form a ring; R b With R c 、R d With R e Can be connected to form a ring;

[0061] The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more of them;

[0062] The heteroatoms in the heteroaryl group are each independently selected from one or more of O, S, N, Si, B;

[0063] Preferably, the boron-containing resonance organic compound has a structure represented by any one of General Formulas (B-4) to (B-12):

[0064]

[0065]

[0066] In General Formulas (B-4) to (B-12), Z is the same or different each time and represents C-(H) or C-(R0); R0 is the same or different each time and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group;

[0067] Any adjacent R0s can be connected to form a ring;

[0068] R1 and R2 are the same or different each time and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group, or a substituted or unsubstituted boranyl group;

[0069] R1 and R2 may be connected to form a ring;

[0070] Each occurrence of Ar1, Ar2, Ar3, and Ar4 is the same or different and represents a hydrogen atom, a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C2-C 10 An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group;

[0071] Ar1 and Ar2 may be connected to form a ring; Ar2 and Ar4 may be connected to form a ring;

[0072] Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom;

[0073] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 An alkyl group, a deuterium-substituted C1-C 10 An alkyl group, a C3-C 10 Of cycloalkyl group, C6-C 30 An aryl group, a deuterium-substituted C6-C 30 An aryl group, a C5-C 30 A heteroaryl group, a deuterium-substituted C2-C 30 Any one or more of heteroaryl groups;

[0074] The heteroatoms in the heteroaryl groups are each independently selected from one or more of O, S, N, Si, and B.

[0075] Furthermore, the boron-containing resonance-type organic compound has a structure as shown in any one of general formulas (B-13) to (B-18):

[0076]

[0077] In General Formulas (B-13) to (B-18), each occurrence of R1 and R2, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group;

[0078] R1 and R2 may be linked to form a ring;

[0079] Each occurrence of Ar1, Ar2, Ar3, and Ar4, which may be the same or different, represents a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0080] Each occurrence of X represents one of a carbon atom or a silicon atom;

[0081] Each occurrence of R3, R4, R5, R6, R7, and R8, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group;

[0082] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10An alkyl group, a deuterium-substituted C1-C 10 An alkyl group, a C3-C 10 Cycloalkyl group of, a C6-C 30 An aryl group, a deuterium-substituted C6-C 30 An aryl group, a C5-C 30 A heteroaryl group, a deuterium-substituted C2-C 30 Any one or more of a heteroaryl group;

[0083] The heteroatoms in the heteroaryl group are each independently selected from one or more of O, S, N, Si, and B.

[0084] Furthermore, the boron-containing resonance-type organic compound has a structure represented by any one of general formulas (C-1) to (C-2):

[0085]

[0086] In general formulas (C-1) and (C-2), Z is the same or different each time and represents C-(H) or C-(R0); R0 is each independently a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 Cycloalkyl group of, a substituted or unsubstituted C2-C 10 An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group, a substituted or unsubstituted boranyl group;

[0087] Any adjacent R0s can be connected to form a ring;

[0088] R1 and R2 are the same or different each time and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 Cycloalkyl group of, a substituted or unsubstituted C2-C 10 An alkenyl group, a substituted or unsubstituted C2-C 10 An alkynyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group, a substituted or unsubstituted boranyl group;

[0089] R1 and R2 can be connected to form a ring;

[0090] X represents, each occurrence being the same or different, one of a carbon atom or a silicon atom;

[0091] X1 represents, each occurrence being the same or different, O, S, N(R a ), C(R b )(R c ), Si(R d )(R e );

[0092] R a , R b , R c , R d , R e represents, each occurrence being the same or different, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0093] R a may be linked to the adjacent Z to form a ring; R b and R c , R d and R e may be linked to form a ring;

[0094] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group;

[0095] The heteroatoms in the heteroaryl group are each independently selected from one or more of O, S, N, Si, B;

[0096] Preferably, the boron-containing resonance organic compound has a structure represented by any one of Formulas (C-3) to (C-10):

[0097]

[0098] In general formulas (C-3) to (C-10), Z is the same or different each time it appears and represents C-(H) or C-(R0); R0 is each independently a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of substituted or unsubstituted boranyl groups;

[0099] Any adjacent R0s can be joined to form a ring;

[0100] R1 and R2 are the same or different each time they appear and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of substituted or unsubstituted boranyl groups;

[0101] R1 and R2 can be joined to form a ring;

[0102] X is the same or different each time it appears and represents one of a carbon atom or a silicon atom;

[0103] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more of them;

[0104] The heteroatoms in the heteroaryl groups are each independently selected from one or more of O, S, N, Si, and B.

[0105] Further, the structure of the boron-containing resonance organic compound is as shown in General Formulas (D-1) to (D-8):

[0106]

[0107]

[0108] In General Formulas (D-1) to (D-8), Z is the same or different each time and is represented as C-(H) or C-(R0); R0 is independently represented as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of substituted or unsubstituted boranyl groups; any adjacent R0s can be connected to form a ring;

[0109] R3, R4, R5, R6, R7, and R8 are the same or different each time and are represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of substituted or unsubstituted boranyl groups;

[0110] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more of them;

[0111] The heteroatom in the heteroaryl is optionally selected from one or more of O, S, N, Si, and B.

[0112] Furthermore, the boron-containing resonance organic compound has a structure represented by any one of general formulas (E-1) to (E-6):

[0113]

[0114]

[0115] In general formulas (E-1) to (E-6), Z is the same or different each time and represents C-(H) or C-(R0); R0 is independently represented as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group;

[0116] Any adjacent R0s can be connected to form a ring;

[0117] R1, R2, R3, R4, R5, R6, and R7 are the same or different each time and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group;

[0118] R1 and R2 can be connected to form a ring;

[0119] Ar1, Ar2, Ar3, and Ar4 are the same or different each time and represent a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl;

[0120] Ar1 and Ar2 can be connected to form a ring; Ar2 and Ar4 can be connected to form a ring;

[0121] M1 and M3 each independently represent a substituted or unsubstituted C6-C aromatic ring substituted by one or more Rs, a 5-30 membered heteroaromatic ring substituted by one or more Rs, or a C6-C aliphatic ring substituted by one or more Rs; 30 One of an aromatic ring, a 5-30 membered heteroaromatic ring substituted by one or more Rs, or a C6-C aliphatic ring substituted by one or more Rs; 10 One of an aromatic ring, a 5-30 membered heteroaromatic ring substituted by one or more Rs, or a C6-C aliphatic ring substituted by one or more Rs;

[0122] Each occurrence of R is the same or different and represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C alkyl, a substituted or unsubstituted C3-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C2-C 10 alkenyl, a substituted or unsubstituted C2-C 10 alkynyl, a substituted or unsubstituted C1-C 10 alkoxy, a substituted or unsubstituted C6-C 10 aryloxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl, a substituted or unsubstituted boranyl, or a substituted or unsubstituted silyl;

[0123] Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom;

[0124] Each occurrence of X1 is the same or different and represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e );

[0125] R a 、R b 、R c 、R d 、R e Each occurrence of R is the same or different and represents a substituted or unsubstituted C1-C alkyl, a substituted or unsubstituted C3-C 10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2 - C 10 alkenyl, substituted or unsubstituted C2 - C 10 alkynyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1 - C 10 alkoxy, substituted or unsubstituted C6 - C 30 aryl, substituted or unsubstituted C2 - C 30 heteroaryl;

[0126] R a can be connected to M3 to form a ring; R b with R c , R d with R e can be connected to form a ring;

[0127] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, C1 - C 10 alkyl, deuterium-substituted C1 - C 10 alkyl, C3 - C 10 cycloalkyl, C6 - C 30 aryl, deuterium-substituted C6 - C 30 aryl, C5 - C 30 heteroaryl, deuterium-substituted C2 - C 30 heteroaryl, or any one or more of them;

[0128] The heteroatoms in the heteroaryl are each independently selected from one or more of O, S, N, Si, B.

[0129] Preferably, any adjacent R0s are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R i )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )-;

[0130] R1 and R2 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R i )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )-;

[0131] Ar1 and Ar2 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(Ri )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )- connected;

[0132] There is no connection between Ar2 and Ar4 or they are connected by a single bond, a double bond, -O-, -S-, -N(R i )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )- connected;

[0133] R a There is no connection between R and M3 or they are connected by a single bond, a double bond, -O-, -S-, -N(R i )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )- connected;

[0134] R a There is no connection between R and the adjacent Z or they are connected by a single bond, a double bond, -O-, -S-, -N(R i )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )- connected;

[0135] R b and R c There is no connection between them or they are connected by a single bond, a double bond, -O-, -S-, -N(R i )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )- connected;

[0136] R d and R e There is no connection between them or they are connected by a single bond, a double bond, -O-, -S-, -N(Ri )-, -C(R m R n )-, -Si(R p R q )- or -C(R j )=C(R k )-linked;

[0137] Said R i , R m , R n , R p , R q , R j , R k are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0138] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group;

[0139] The heteroatoms in the said heteroaryl group are each independently selected from one or more of O, S, N, Si, B.

[0140] Furthermore, said M1, M2, M3 are represented as the following groups substituted or unsubstituted by R: phenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, pyrrolyl, furyl, thienyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indolo[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, spirofluorene;

[0141] Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is the same as or different from one another and represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted triazinyl group;

[0142] Each occurrence of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is the same as or different from one another and represents a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted triazinyl group;

[0143] Each occurrence of R and R0, which may be the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, or a substituted or unsubstituted triazinyl group;

[0144] Said R a , R b , R c , R d , R e , R i , R m , R n , R p , R q , R k Each occurrence, which may be the same or different, represents a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, or a substituted or unsubstituted triazinyl group;

[0145] The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group;

[0146] Preferably, R, R0, R1, R2, R3, R4, R5, R6, R7, R8 are represented by the following structures:

[0147] a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyano group, a trifluoromethyl group, any one of;

[0148] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are represented by the following structures:

[0149] a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, any one of;

[0150] The R a , R b , R c , R d , R e are represented by the following structures:

[0151]

[0152] any one of.

[0153] Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] The present invention also provides an organic light-emitting device, which sequentially includes a substrate, a first electrode, a second electrode, and a functional layer. The functional layer is located between the first electrode and the second electrode, and the functional layer contains the boron-containing resonance-type organic compound of the present invention;

[0183] Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a doping material, and the doping material is the boron-containing resonance organic compound of the present invention;

[0184] Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing resonance organic compound of the present invention.

[0185] Furthermore, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material, an exciton sensitizing material and a doping material, the exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing resonance organic compound of the present invention.

[0186] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0187] (1) The compound of the present invention is applied to an OLED device and can be used as a doping material for the light-emitting layer material. Under the action of an electric field, it can emit green fluorescence and can be applied to the fields of OLED lighting or OLED display;

[0188] (2) As a doping material, the compound of the present invention introduces a phosphorus photosensitizer, which can effectively improve the device efficiency and lifespan;

[0189] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the device color gamut and enhance the device light-emitting efficiency;

[0190] (4) As a doping material, the compound of the present invention introduces a TADF sensitizer as the second host, which can effectively improve the device efficiency;

[0191] The compound of the present invention has the characteristic of a narrow full width at half maximum and can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the device efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0192] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0193] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer; DETAILED DESCRIPTION OF THE EMBODIMENTS

[0194] The present invention will be specifically described below with reference to the drawings and embodiments.

[0195] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms indicating orientation such as "upper", "lower", "top", and "bottom" only represent the orientation in a specific state, and do not mean that the related structures can only exist in the stated orientation; on the contrary, if the structure can change its position, for example, be inverted, the orientation of the structure changes accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" sides.

[0196] In the present invention, the substituted or unsubstituted arylamino group as described in the present invention means wherein Q1 and Q2 represent substituted or unsubstituted aromatic groups, and Q1 and Q2 preferably represent substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 heteroaryl.

[0197] In the present invention, the substituted or unsubstituted C6-C 30 aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 10 carbon atoms, preferably an aryl group having 8 to 10 carbon atoms, preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted bi-p-terphenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a combination thereof or a condensed ring of the foregoing group combinations, but not limited thereto.

[0198] In the present invention, the substituted or unsubstituted C2-C 30Heteroaryl refers to heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 4 to 20 carbon atoms, preferably heteroaryl having 5 to 20 carbon atoms, preferably heteroaryl having 4 to 10 carbon atoms, preferably heteroaryl having 5 to 10 carbon atoms, preferably substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, their combinations or fused rings of the foregoing group combinations, but not limited thereto.

[0199] In the present invention, the substituted or unsubstituted C2-C 30 The number of heteroatoms in the heteroaryl is 1-5, preferably 1-4. Preferably 1-3, preferably 1-2.

[0200] The C1-C described in the present invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to alkyl having 1 to 10 carbon atoms, preferably alkyl having 1 to 5 carbon atoms, preferably alkyl having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but not limited thereto.

[0201] The C3-C described in the present invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In the present text, C4-C9 cycloalkyl is preferably used, more preferably C5-C8 cycloalkyl, and particularly preferably C5-C7 cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, etc., but not limited thereto.

[0202] The halogen atom in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0203] The C1-C 10 alkoxy group refers to a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an isopropoxy group, etc., but is not limited thereto.

[0204] The C2-C 10 alkenyl group refers to a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylethenyl group, a styryl group, a 2,2-diphenylethenyl group, a 1,2-diphenylethenyl group, a 1,1-dimethylallyl group, a 1-methylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 2-phenylallyl group, a 3,3-diphenylallyl group, a 1,2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group, etc., but is not limited thereto.

[0205] The substituent is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuryl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group.

[0206] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent PI film substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothness, water repellencies. Depending on the nature of the substrate, its usage direction is different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0207] A first electrode is formed on a substrate, and the first electrode and the second electrode can face each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it can be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, and can also be an alloy of several metals, or a combination of a metal, a metal oxide, and a metal alloy. The thickness of the first electrode layer depends on the materials used and is generally 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0208] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0209] In the present invention, examples of the hole transport region constituting the organic electroluminescent device include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0210] As the materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials for organic electroluminescent devices for use.

[0211] The hole injection layer contains a host organic material that can conduct holes and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material in order to expect the occurrence of a charge transfer state between the host material and the doping material, achieve ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection conduction.

[0212] In view of the above empirical summaries, for hole-type host organic materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0213] Preferably, as the host organic material of the hole injection layer of the present invention, any compound disclosed in the following prior arts can be optionally selected: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0214] Preferably, the p-type doping material is a compound having charge conductivity selected from those disclosed in the prior art, and the p-type dopant can be selected from the compounds disclosed in any one of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE102007031220A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited thereto.

[0215] In one embodiment of the present invention, the hole injection layer comprises a p-type doping material having charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanomethylene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0216] In the hole injection layer of the present invention, the ratio of the hole transport material to the p-type doping material used is 99:1 - 95:5, preferably 99:1 - 97:3, based on mass.

[0217] The thickness of the hole injection layer of the present invention can be 5 - 100 nm, preferably 5 - 50 nm, and more preferably 5 - 20 nm, but the thickness is not limited to this range.

[0218] Preferably, as the hole transport layer material of the present invention, any compound disclosed in the following prior arts can be optionally selected:

[0219] JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN103108859A.

[0220] Preferably, the hole transport layer material and the host organic material in the hole injection layer of the present invention are selected from the same compound.

[0221] The thickness of the hole transport layer of the present invention can be 5 - 200 nm, preferably 10 - 150 nm, and more preferably 20 - 100 nm, but the thickness is not limited to this range.

[0222] In one embodiment of the present invention, as the electron blocking layer material of the present invention, any compound disclosed in the following prior arts can be optionally selected:

[0223] CN102046613A, CN105408448A, KR1020160049955A, CN103108859A, KR1020130106255A, EP2922932A1, CN102224150A, US20170018710A1.

[0224] The thickness of the electron blocking layer of the present invention can be 1 - 50 nm, preferably 5 - 40 nm, but the thickness is not limited to this range.

[0225] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light emitting layer is formed on the electron blocking layer.

[0226] The light emitting layer may include a host material and a doping material. The host material can use common green light host materials in the art, and the doping material uses a boron-containing resonance organic compound represented by the general formula (1) of the present invention.

[0227] The light emitting layer may include a single host material or a dual host material;

[0228] The dual host material includes a first host material and a second host material. At least one of the first host material and the second host material is preferably a TADF material;

[0229] The TADF material refers to a material with thermally activated delayed fluorescence properties, characterized by having a small energy level difference between the first excited singlet state and the first excited triplet state. Therefore, singlet excitons and triplet excitons generated can be simultaneously utilized in the device, enabling the utilization rate of excitons generated electro-optically inside the device to approach 100% as much as possible. Compared with traditional fluorescent materials, the TADF material has a higher exciton utilization rate.

[0230] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0231] The exciton-sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to make full use of electro-generated excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may perform functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing resonance-type organic compound shown in the general formula (1) of the present invention is used in combination with the exciton-sensitizing material, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0232] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1 - 70:30, preferably 99:1 - 85:15, and more preferably 97:3 - 87:13, based on mass.

[0233] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0234] In the present invention, the electron transport region may sequentially include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer provided above the light-emitting layer, but is not limited thereto.

[0235] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby prolonging the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be provided above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art having a hole blocking effect can be used, such as the compounds disclosed in the following prior art: Appl.Phys.Lett.75,4(1999), Appl.Phys.Lett.83,3858(2003), JP2015111679A, KR1020180043220A, CN109564982A, KR1020180065246A.

[0236] The thickness of the hole blocking layer of the present invention can be 2 - 200 nm, preferably 5 - 150 nm, and more preferably 5 - 50 nm, but the thickness is not limited to this range.

[0237] The electron transport layer can be disposed above the light-emitting layer or, if present, the hole blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. A material with a high electron mobility is preferably used. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as the compounds disclosed in the following prior art: CN1784388A, CN1625552A, CN107431141A, CN107431141A, KR1020160149041A, KR1020160149041A, CN103827256A, KR101847347B1, KR1020190050658A, CN102574813A, CN107721979A, KR1020100073954A.

[0238] In a preferred embodiment of the present invention, the electron transport layer further includes other compounds conventionally used in the electron transport layer, such as, for example, Alq3, LiQ, preferably LiQ.

[0239] The thickness of the electron transport layer of the present invention can be 10 - 80 nm, preferably 20 - 60 nm, and more preferably 25 - 45 nm, but the thickness is not limited to this range.

[0240] The electron injection layer can be disposed above the electron transport layer. The electron injection layer material is generally a material preferably having a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as: LiF, Cs2CO3, CsF, Csq, NaF, MgF2, CaF2, Al2O3, Yb, etc.

[0241] The thickness of the electron injection layer of the present invention can be 0.1 - 5 nm, preferably 0.5 - 3 nm, and more preferably 0.8 - 1.5 nm, but the thickness is not limited to this range.

[0242] The second electrode may be disposed over the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0243] The organic light-emitting device of the present invention may further include a packaging structure. The packaging structure may be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layers of the organic light-emitting device. The packaging structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0244] A method for preparing the organic light-emitting device of the present invention includes successively laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a covering layer on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, the LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, the vacuum evaporation method is preferably used to form each of the layers. Those skilled in the art can conventionally select each process condition in the vacuum evaporation method according to actual needs.

[0245] Preparation of Compounds

[0246] 1. Synthesis of Intermediate P

[0247] Synthesis of Intermediate P1:

[0248]

[0249] To a two-necked flask, add raw material T1 (18.4 mmol, 4.25 g), cesium carbonate (55.2 mmol, 18.0 g), add 120 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 minutes, add raw material R1 (20.2 mmol, 4.17 g) under nitrogen protection, reflux the solution under magnetic stirring for 24 hours, cool, filter, wash with water, dry, and purify by column chromatography to obtain intermediate X1.

[0250] Add intermediate X1 (10.0 mmol, 4.17 g), tetrabutylammonium bromide (nBu4NBr) (1.0 mmol, 0.32 g), triphenylphosphine (0.5 mmol, 0.13 g), palladium acetate catalyst (0.2 mmol, 0.05 g), potassium carbonate (20.0 mmol, 2.76 g), and DMAc (50 mL) into a sealed pressure-resistant tube in sequence. Subsequently, under nitrogen protection, heat under reflux and stir for 48 hours. After cooling, separate the liquid by liquid separation and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase. Separate the compound by silica gel column to obtain intermediate P1.

[0251] Synthesis of intermediate P2:

[0252]

[0253] Under nitrogen protection, dissolve raw material R2 (2.0 mmol, 0.54 g) and di-tert-butyl dicarbonate (2.5 mmol, 0.55 g) in 50 mL of tetrahydrofuran, add DMAP (0.5 mmol, 0.06 g) and stir at room temperature for 2 hours. Filter the suspension, wash the solid with 20 mL of tetrahydrofuran and 40 mL of ethyl acetate to obtain intermediate X2.

[0254] Dissolve intermediate X2 (5.1 mmol, 1.9 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of passing nitrogen at -78 °C, slowly add 4.7 mL of a 2.5 M n-butyllithium hexane solution; after stirring at -78 °C for 3 hours, slowly add 15 mL of a tetrahydrofuran solution of raw material T2 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1.0 M) solution, distilled water, and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried with sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight, and then slowly quench it with an aqueous sodium bicarbonate (NaHCO3) solution. Then separate the aqueous layer, extract it with dichloromethane, dry it with sodium sulfate, filter, and distill under reduced pressure. Purify by column chromatography to obtain intermediate X3.

[0255] In a three-necked flask, under nitrogen protection, dissolve intermediate X3 (5.0 mmol, 2.28 g) in 40 mL of dichloromethane, then add 15 mL of trifluoroacetic acid and stir at room temperature for 23 hours. Then quench the reaction with a saturated sodium bicarbonate solution, wash and separate with dichloromethane to collect the organic phase, dry it with anhydrous sodium sulfate, and concentrate. Purify by silica gel column to obtain intermediate P2.

[0256] Synthesis of Intermediate P3:

[0257]

[0258] Add raw material R3 (239 mmol, 40.0 g) and anhydrous zinc chloride (837 mmol, 114.1 g) into a 1 L three-necked flask, and then add 400 mL of nitromethane. After purging with nitrogen, dropwise add raw material T3 (837 mmol, 103 mL), and react at room temperature for 48 hours. After the reaction is completed, quench with 1 M HCl, extract, wash the organic phase with an aqueous sodium bicarbonate solution, dry, concentrate, and purify by column chromatography to obtain intermediate X4.

[0259] Under nitrogen protection and at 0 °C, add anhydrous aluminum chloride solid (65.58 mmol, 8.74 g) in portions to a 1 L three-necked flask containing 100 mL of anhydrous THF, and then add LiAlD4 (131.17 mmol, 5.51 g) solid in portions and stir for 10 minutes. Then dropwise add a THF (50 mL) solution of intermediate X4 (32.79 mmol, 11.0 g). Subsequently, heat the reaction to 50 °C and react for 3 hours. After the reaction is complete, cool to room temperature. Slowly pour the reaction solution into ice cubes to quench, add ethyl acetate for extraction, dry the combined organic phase over anhydrous sodium sulfate, concentrate, and purify by column chromatography to obtain intermediate P3.

[0260] Synthesis of Intermediate P4:

[0261]

[0262] Dissolve raw material R4 (287 mmol, 59.5 g) and 60% sodium hydride dissolved in mineral oil (776 mmol, 31.0 g) in 1 L of anhydrous tetrahydrofuran, and reflux for 5 hours under nitrogen protection. After cooling to room temperature, slowly drop a large amount of 1 M ice hydrochloric acid solution into the reaction solution, filter by suction, and wash to obtain intermediate X5.

[0263] Dissolve intermediate X5 (129 mmol, 45.2 g) in 1 L of chloroform, add phosphorus pentachloride (388 mmol, 80.8 g) in an ice-water bath, raise the temperature to room temperature under nitrogen protection, and then heat to reflux and react overnight. Cool, filter, rotary evaporate the solvent, and purify by column chromatography to obtain intermediate X6.

[0264] Dissolve intermediate X6 (58.4 mmol, 22.6 g) in 300 mL of tetrahydrofuran, add zinc powder (584 mmol, 38.2 g), slowly add 42 mL of trifluoroacetic acid in an ice bath under nitrogen protection, and then raise the temperature to room temperature and react for 16 hours. Filter, extract, rotary evaporate, and wash to obtain intermediate X7.

[0265] Add raw material T1 (18.4 mmol, 4.25 g), cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Under nitrogen protection, add 120 mL of anhydrous DMF, stir at room temperature for 30 minutes. Under nitrogen protection, add intermediate X7 (20.2 mmol, 6.43 g). The solution is refluxed with magnetic stirring for 26 hours, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate X8.

[0266] Add intermediate X8 (10.0 mmol, 5.3 g), tetrabutylammonium bromide (nBu4NBr) (1.0 mmol, 0.32 g), triphenylphosphine (0.5 mmol, 0.13 g), palladium acetate catalyst (0.2 mmol, 0.04 g), potassium carbonate (20.0 mmol, 2.76 g), DMAc (60 mL) to a sealed pressure-resistant tube in sequence. Subsequently, under nitrogen protection, heat and reflux with stirring for 50 hours. After cooling, separate the liquid by liquid separation and collect the organic phase. Dry it with anhydrous sodium sulfate, then filter and concentrate it. Separate the compound by silica gel column to obtain intermediate P1.

[0267] Synthesis of intermediate P5:

[0268]

[0269] Add raw material T4 (18.4 mmol, 3.22 g), cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Under nitrogen protection, add 120 mL of anhydrous DMF, stir at room temperature for 30 minutes. Under nitrogen protection, add raw material R1 (20.2 mmol, 4.17 g). The solution is refluxed with magnetic stirring for 24 hours, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate X9.

[0270] Add intermediate X9 (10.0 mmol, 3.61 g), tetrabutylammonium bromide (nBu4NBr) (1.0 mmol, 0.32 g), triphenylphosphine (0.5 mmol, 0.13 g), palladium acetate catalyst (0.2 mmol, 0.04 g), potassium carbonate (20.0 mmol, 2.76 g), DMAc (50 mL) to a sealed pressure-resistant tube in sequence. Subsequently, under nitrogen protection, heat and reflux with stirring for 42 hours. After cooling, separate the liquid by liquid separation and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase. Separate the compound by silica gel column to obtain intermediate P5.

[0271] 2. Synthesis of intermediate Q

[0272] Synthesis of intermediate Q1:

[0273]

[0274] Into a two-necked flask, add raw material M1 (18.4 mmol, 6.2 g), cesium carbonate (55.2 mmol, 18.0 g). Under nitrogen protection, add 120 mL of anhydrous DMF, stir at room temperature for 30 minutes. Under nitrogen protection, add raw material M2 (20.2 mmol, 5.6 g). The solution is refluxed for 24 hours under magnetic stirring, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate Y1.

[0275]

[0276] Dissolve intermediate Y1 (5.1 mmol, 3.0 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen bubbling at -78 °C, slowly add 4.7 mL of a 2.5 M n-butyllithium solution in hexane (11.7 mmol). After stirring at -78 °C for 4 hours, slowly add 15 mL of a THF solution of raw material M3 (5.5 mmol, 2.1 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1.0 M) solution, distilled water, and ethyl acetate to the reaction mixture. Separate the aqueous layer and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight, and then slowly quench it with an aqueous sodium bicarbonate (NaHCO3) solution. Then separate the aqueous layer, extract it with dichloromethane, dry it over sodium sulfate, filter, and distill under reduced pressure. Purify by column chromatography to obtain intermediate Q1.

[0277] Synthesis of intermediate Q2:

[0278]

[0279] Dissolve intermediate Y1 (5.1 mmol, 3.0 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen bubbling at -78 °C, slowly add 4.7 mL of a 2.5 M n-butyllithium solution in hexane (11.7 mmol). After stirring at -78 °C for 2 hours, slowly add 20 mL of a THF solution of raw material M4 (5.5 mmol, 1.55 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1.0 M) solution, distilled water, and ethyl acetate to the reaction mixture. Separate the aqueous layer and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight, and then slowly quench it with an aqueous sodium bicarbonate (NaHCO3) solution. Then separate the aqueous layer, extract it with dichloromethane, dry it over sodium sulfate, filter, and distill under reduced pressure. Purify by column chromatography to obtain intermediate Q2.

[0280] Synthesis of Intermediate Q3:

[0281]

[0282] Into a two-necked flask, add raw material M1 (18.4 mmol, 6.2 g), cesium carbonate (55.2 mmol, 18.0 g). Under nitrogen protection, add 120 mL of anhydrous DMF, stir at room temperature for 30 minutes. Under nitrogen protection, add intermediate P3 (20.2 mmol, 6.3 g). The solution is refluxed with magnetic stirring for 28 hours, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate Y2.

[0283]

[0284] Dissolve intermediate Y2 (5.1 mmol, 3.2 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 4.7 mL of a 2.5 M n-butyllithium hexane solution; after stirring at -78 °C for 2 hours, slowly add 20 mL of a tetrahydrofuran solution of raw material M4 (5.5 mmol, 1.55 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1.0 M) solution, distilled water, and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. The reaction mixture is stirred overnight, and then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Then separate the aqueous layer, extract it with dichloromethane, dry it over sodium sulfate, filter, and distill under reduced pressure, and purify by column chromatography to obtain intermediate Q3.

[0285] Synthesis of Intermediate Q4:

[0286]

[0287] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) hexane solution was slowly added. After stirring at -78 °C for 3 hours, 25 mL of the THF solution of raw material M5 (5.5 mmol, 2.17 g) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M) solution, distilled water and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Then the aqueous layer was separated, extracted with dichloromethane, dried over sodium sulfate, filtered, distilled under reduced pressure, and purified by column chromatography to obtain intermediate Q4.

[0288] Synthesis of intermediate Q5:

[0289]

[0290] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) hexane solution was slowly added. After stirring at -78 °C for 3 hours, 20 mL of the THF solution of raw material M6 (5.5 mmol, 1.83 g) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M) solution, distilled water and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Then the aqueous layer was separated, extracted with dichloromethane, dried over sodium sulfate, filtered, distilled under reduced pressure, and purified by column chromatography to obtain intermediate Q5.

[0291] 3. Synthesis of Examples

[0292] Synthesis of compound 60 in Example 1:

[0293]

[0294] To a three-necked flask, add intermediate Q1 (5.5mmol, 4.59g), raw material A1 (5mmol, 1.04g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 24 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and vacuum dried to obtain intermediate J1.

[0295]

[0296] In a three-necked flask, under nitrogen protection, intermediate J1 (2mmol, 1.92g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 6 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly warmed to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 12 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 60. In toluene solution (1×10 -5 The half-peak width is 22 nm. 1 H NMR (400MHz, Chloroform-d) δ8.95(d,1H),8.44–8.29(m,1H),8.12–7.97(m,1H),7.77–7.52(m,8H),7.50–7.03(m,22H),2.30(d,18H).

[0297] Example 2 Synthesis of Compound 96:

[0298]

[0299] To a three-necked flask, add intermediate Q1 (5.5mmol, 4.59g), raw material A2 (5mmol, 1.12g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 15 hours. When the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J2.

[0300]

[0301] In a three-necked flask, under nitrogen protection, intermediate J2 (2mmol, 1.96g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 8 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.8mL) was added to the system at 0°C, heated to 120°C and continued to react for 12 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 96. In toluene solution (1×10 -5 The half-peak width is 23 nm. 1 H NMR(400MHz,Chloroform-d)δ8.97(d,1H),8.42–8.26(m,1H),8.04(m,1H),7.95–7. 84(m,1H),7.79–7.64(m,2H),7.61–7.53(m,5H),7.51–7.05(m,22H),2.33(d,18H).

[0302] Example 3 Synthesis of Compound 159:

[0303]

[0304] To a three-necked flask, add intermediate Q1 (5.5mmol, 4.59g), intermediate P1 (5mmol, 1.68g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 16 hours. When the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J3.

[0305]

[0306] In a three-necked flask, under nitrogen protection, intermediate J3 (2mmol, 2.18g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 6 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 9 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 12 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 159. In toluene solution (1×10 -5 The half-peak width is 24 nm.

[0307] Example 4 Synthesis of Compound 177:

[0308]

[0309] To a three-necked flask, add intermediate Q1 (5.5mmol, 4.59g), intermediate P2 (5mmol, 1.78g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 18 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J4.

[0310]

[0311] In a three-necked flask, under nitrogen protection, intermediate J4 (2mmol, 2.22g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 6 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 16 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 177. In toluene solution (1×10 -5 The half-peak width is 24 nm.

[0312] Example 5 Synthesis of Compound 206:

[0313]

[0314] To a three-necked flask, add intermediate Q2 (5.5mmol, 4.03g), raw material A3 (5mmol, 1.69g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 22 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J5.

[0315]

[0316] In a three-necked flask, under nitrogen protection, intermediate J5 (2mmol, 1.98g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 6 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 8 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 10 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 206. In toluene solution (1×10 -5 The half-peak width is 23 nm. 1H NMR (400MHz, Chloroform-d) δ9.02(d,1H),8.82–8.68(m,2H),8.48–8.30(m,1H),7.73–7.50(m,3H),7.49–7.00(m,24H),2.72–1.91(m,27H).

[0317] Example 6 Synthesis of Compound 218:

[0318]

[0319] To a three-necked flask, add intermediate Q2 (5.5mmol, 4.03g), raw material A1 (5mmol, 1.04g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 17 hours. When the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J6.

[0320]

[0321] In a three-necked flask, under nitrogen protection, intermediate J6 (2mmol, 1.72g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 6 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly warmed to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 15 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 218. In toluene solution (1×10 -5 The half-peak width is 23 nm.

[0322] Example 7 Synthesis of Compound 237:

[0323]

[0324] To a three-necked flask, add intermediate Q3 (5.5mmol, 4.21g), raw material A1 (5mmol, 1.04g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 30 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J7.

[0325]

[0326] In a three-necked flask, under nitrogen protection, intermediate J7 (2mmol, 1.78g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 8 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 8 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 20 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 237. In toluene solution (1×10 -5 The half-peak width is 22 nm.

[0327] Example 8 Synthesis of Compound 295:

[0328]

[0329] To a three-necked flask, add intermediate Q2 (5.5mmol, 4.03g), intermediate P1 (5mmol, 1.68g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 24 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J8.

[0330]

[0331] In a three-necked flask, under nitrogen protection, intermediate J8 (2mmol, 1.98g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 7 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 7 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 12 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 295. In toluene solution (1×10 -5 The half-peak width is 24 nm.

[0332] Example 9 Synthesis of Compound 298:

[0333]

[0334] To a three-necked flask, add intermediate Q2 (5.5mmol, 4.03g), intermediate P4 (5mmol, 2.24g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 20 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J9.

[0335]

[0336] In a three-necked flask, under nitrogen protection, intermediate J9 (2mmol, 2.2g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 9 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 10 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 12 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 298. In toluene solution (1×10 -5 The half-peak width is 23 nm.

[0337] Example 10 Synthesis of Compound 313:

[0338]

[0339] To a three-necked flask, add intermediate Q4 (5.5mmol, 4.65g), intermediate P1 (5mmol, 1.68g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 24 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J10.

[0340]

[0341] In a three-necked flask, under nitrogen protection, intermediate J10 (2mmol, 2.2g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 8 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 14 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 313. In toluene solution (1×10 -5 The half-peak width is 23 nm. 1 H NMR(400MHz,Chloroform-d)δ8.90(d,1H),8.74(m,1H),8.36(m,2H),8.10(m,1H),7.92–7 .80(m,4H),7.74–7.53(m,3H),7.50–7.35(m,5H),7.31–7.06(m,10H),2.70–2.01(m,45H).

[0342] Example 11 Synthesis of Compound 384:

[0343]

[0344] To a three-necked flask, add intermediate Q5 (5.5mmol, 4.31g), intermediate P5 (5mmol, 1.4g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 20 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J11.

[0345]

[0346] In a three-necked flask, under nitrogen protection, intermediate J11 (2mmol, 1.97g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 6 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 10 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 384. In toluene solution (1×10 -5 The half-peak width is 24 nm. 1 H NMR(400MHz,Chloroform-d)δ8.93(d,1H),8.71(m,1H),8.43–8.32(m,1H),8.22(m,1H),8.15–8.07 (m,2H),8.03–7.92(m,1H),7.77–7.58(m,6H),7.49–7.21(m,13H),7.18–7.05(m,6H),2.28(d,18H).

[0347] Example 12 Synthesis of Compound 471:

[0348]

[0349] To a three-necked flask, add intermediate Q2 (5.5mmol, 4.03g), raw material A4 (5mmol, 1.04g), Pd2(dba)3 (0.5mmol, 0.46g), tri-tert-butylphosphine tetrafluoroborate (1mmol, 0.29g), sodium tert-butoxide (15mmol, 1.44g), and toluene (80mL) in sequence. The mixture was degassed by a "vacuum-nitrogen" cycle, and then heated to reflux for 21 hours. After the reaction system was cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated in vacuo. The crude product was further purified by a chromatographic column and dried in vacuo to obtain intermediate J12.

[0350]

[0351] In a three-necked flask, under nitrogen protection, intermediate J12 (2mmol, 1.72g) and 60mL of tert-butylbenzene were added. 1.6M tert-butyl lithium pentane solution (5mmol, 3.1mL) was slowly added at -40°C, the system was heated to 60°C and reacted for 5 hours, then boron tribromide (5mmol, 0.5mL) was added at -40°C, and the mixture was slowly heated to room temperature and continued to react for 6 hours, then N,N-diisopropylethylamine (5mmol, 0.9mL) was added to the system at 0°C, heated to 120°C and continued to react for 10 hours. After the reaction, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography and vacuum dried to obtain compound 471. In toluene solution (1×10 -5 The half-peak width is 28 nm. 1 H NMR(400MHz,Chloroform-d)δ8.98(d,1H),8.49–8.31(m,1H),8.09–7.98(m,1H),7.90( m,1H),7.67(d,1H),7.56(d,1H),7.50–7.33(m,6H),7.30–7.02(m,15H),2.36(d,18H).

[0352] Note: The half-peak width (FWHM) is obtained by testing the Fluorolog-3 series fluorescence spectrometer of Horiba.

[0353] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0354] Table 1

[0355]

[0356]

[0357] The application effects of the synthesized organic electroluminescent materials of the present invention in devices are described in detail below through Device Examples 1-12 and Device Comparative Examples 1-4. The manufacturing processes of Device Examples 2-12 and Device Comparative Examples 1-4 of the present invention are exactly the same as those of Device Example 1, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the doping materials in the light-emitting layer of the device are replaced. The layer structures and test results of each device example are shown in Table 2-1 and Table 3 respectively.

[0358] Device Example 1

[0359] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED device is fabricated. GH-1 and GH-2 are used as the host materials, and Compound 60 is used as the doping material. The mass ratio of GH-1, GH-2, and Compound 60 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0360] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 13-24 and Device Comparative Examples 5-8. The manufacturing processes of Device Examples 14-24 and Device Comparative Examples 5-8 of the present invention are exactly the same as those of Device Example 13, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the doping materials in the light-emitting layer of the device are replaced. The layer structures and test results of each device example are shown in Table 2-2 and Table 3 respectively.

[0361] Device Embodiment 13

[0362] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials, GD-1 as the first doping material, and compound 60 as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 60 is 66.5:30:3:0.5, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0363] The molecular structural formulas of the related materials are as follows:

[0364]

[0365] After the OLED light-emitting device is completed as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency and the lifetime of the device are measured. The device embodiments and comparative examples prepared by the same method are shown in Tables 2-1 and 2-2; the test results of the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0366] Table 2-1

[0367]

[0368]

[0369] Table 2-2

[0370]

[0371]

[0372] Table 3

[0373]

[0374]

[0375] Note: The current efficiency and emission peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fosida Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester of System Technology Research Co., Ltd. in Japan; LT95 refers to the time taken for the device luminance to decay to 95%; all data were measured at 10 mA / cm 2 as follows.

[0376] From the device data results in Table 3, it can be seen that the emission peak of the compound of the present invention is between 510 and 550 nm, and the green emission effect can be well achieved; compared with device comparative examples 1-8, the organic light-emitting device of the present invention has a relatively large improvement in lifetime in both the single-doping system and the double-doping system compared to OLED devices of known materials; when using an exciton sensitizing material as the first dopant, the device efficiency and lifetime are significantly improved compared to the single-doping case.

[0377] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing resonance-type organic compound, characterized in that: The structure of the boron-containing resonance organic compound is as shown in the general formula (1): In general formula (1), Z is the same or different each time and represents C-(H) or C-(R0); each occurrence of R0 independently represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; Any adjacent R0s can be connected to form a ring; Each occurrence of R1 and R2, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; R1 and R2 can be connected to form a ring; Ar1, Ar2, Ar3, and Ar4 each independently represent, the same or different each time they appear, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Ar1 and Ar2 can be connected to form a ring; Ar2 and Ar4 can be connected to form a ring; M1, M2, and M3 each independently represent one of a C6-C 30 aryl ring which may or may not be substituted by one or more Rs, a 5-30 membered heteroaryl ring which may or may not be substituted by one or more Rs, a C6-C 10 alicyclic ring which may or may not be substituted by one or more Rs; R is the same or different each time and represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; The substituents of the above-mentioned substitutable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B.

2. The boron-containing resonance-type organic compound according to claim 1, characterized in that, The structure of the boron-containing resonance organic compound is as shown in the general formula (1-1) or the general formula (1-2): In General Formula (1-1) and General Formula (1-2), Z is the same or different each time it appears and represents C-(H) or C-(R0); R0 is independently represented each time it appears as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; Any adjacent R0s can be connected to form a ring; R1 and R2 each independently represent, the same or different in each occurrence, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; Ar1, Ar2, Ar3, and Ar4 each independently represent, each time they appear, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Ar1 and Ar2 can be connected to form a ring; Ar2 and Ar4 can be connected to form a ring; M1 and M3 each independently represent a substituted or unsubstituted C6-C 30 aryl ring substituted or unsubstituted by one or more Rs, a 5-30 membered heteroaryl ring substituted or unsubstituted by one or more Rs, a C6-C 10 alicyclic ring, one of them; R is the same as or different from each other each time it appears and represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; X1 is each time the same or different and represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e ); R a 、R b 、R c 、R d 、R e Each occurrence, the same or different, represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; R a can be connected with M3 to form a loop; R b with R c 、R d with R e can be connected to form a loop; The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B.

3. The boron-containing resonance-type organic compound according to claim 2, wherein The structure of the boron-containing resonance organic compound is as shown in any one of the general formulas (A-1) to (A-6): In General Formulas (A-1) to (A-6), Z represents C-(H) or C-(R0) each time it appears, either the same or different; each occurrence of R0 independently represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; Any adjacent R0s can be connected to form a ring; Each occurrence of R1 and R2, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; Ar5 and Ar6 each independently represent, the same or different in each occurrence, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; M1 and M3 each independently represent a substituted or unsubstituted C6-C 30 aryl ring substituted or unsubstituted with one or more Rs, a 5-30 membered heteroaryl ring substituted or unsubstituted with one or more Rs, a C6-C 10 aliphatic ring; R is each time the same or different and represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; X1 is each time the same or different and represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e ); R a 、R b 、R c 、R d 、R e Each time it appears, it is the same or different and represents a substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C2-C 10 alkenyl group, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted boranyl group, substituted or unsubstituted C1-C 10 alkoxy group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl group; R a can be connected with M3 to form a ring; R b with R c 、R d with R e can be connected to form a ring; The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B.

4. The boron-containing resonance-type organic compound according to claim 2, characterized in that, The structure of the boron-containing resonance organic compound is as shown in any one of the general formulas (B-1) to (B-3): In General Formulas (B-1) to (B-3), Z is the same or different each time it appears and represents C-(H) or C-(R0); R0 is independently represented each time it appears as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; Any adjacent R0s can be connected to form a ring; Each occurrence of R1 and R2, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; Ar1, Ar2, Ar3, and Ar4 each independently represent, each time they appear, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; X1 is each time the same or different and represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e ); R a 、R b 、R c 、R d 、R e Each occurrence, the same or different, represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; R a can be connected to the adjacent Z to form a ring; R b With R c , R d With R e can be connected to form a ring; The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B; Preferably, the structure of the boron-containing resonance organic compound is as shown in any one of the general formulas (B-4) to (B-12): In General Formulas (B-4) to (B-12), Z is the same or different each time it appears and represents C-(H) or C-(R0); R0 is independently represented each time it appears as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of substituted or unsubstituted boranyl groups; Any adjacent R0s can be connected to form a ring; Each occurrence of R1 and R2, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; Ar1, Ar2, Ar3, and Ar4 each independently represent, each time they appear, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Ar1 and Ar2 can be connected to form a ring; Ar2 and Ar4 can be connected to form a ring; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B.

5. The boron-containing resonance-type organic compound according to claim 1, wherein The structure of the boron-containing resonance organic compound is as shown in any one of the general formulas (B-13) to (B-18): In General Formulas (B-13) to (B-18), each occurrence of R1 and R2 independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; Ar1, Ar2, Ar3, and Ar4 each independently represent, each time they appear, a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; R3, R4, R5, R6, R7, and R8 each independently represent, each time they appear, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; The substituents of the above-mentioned substitutable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B.

6. The boron-containing resonance-type organic compound according to claim 1, wherein The structure of the boron-containing resonance organic compound is as shown in any one of the general formulas (C-1) to (C-2): In general formula (C-1) and general formula (C-2), Z is the same or different each time it appears and represents C-(H) or C-(R0); each occurrence of R0 independently represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; Any adjacent R0s can be connected to form a ring; Each occurrence of R1 and R2, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; Each occurrence of X is the same or different and represents one of a carbon atom or a silicon atom; X1, each occurrence being the same or different, represents O, S, N(R a ), C(R b )(R c ), Si(R d )(R e ); R a and R b and R c and R d and R e Each occurrence is the same or different and represents a substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C2-C 10 alkynyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl; R a can be connected to the adjacent Z to form a ring; R b With R c 、R d With R e can be connected to form a ring; The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl group is arbitrarily selected from one or more of O, S, N, Si, and B; Preferably, the structure of the boron-containing resonance organic compound is as shown in any one of the general formulas (C-3) to (C-10): In General Formulas (C-3) to (C-10), Z is the same or different each time it appears and represents C-(H) or C-(R0); R0 is independently represented each time it appears as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; Any adjacent R0s can be connected to form a ring; R1 and R2 each independently represent, the same or different each time they appear, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or a substituted or unsubstituted boranyl group; R1 and R2 can be connected to form a ring; X is each time the same or different and represents one of a carbon atom or a silicon atom; The substituents of the above-mentioned substitutable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl is optionally selected from one or more of O, S, N, Si, and B.

7. The boron-containing resonance-type organic compound according to claim 1, wherein The boron-containing resonance organic compound has a structure as shown in any one of General Formulas (D-1) to (D-8): In general formulas (D-1) to (D-8), Z is the same or different each time it appears and represents C-(H) or C-(R0); R0 is independently represented as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; any adjacent R0s may be connected to form a ring; R3, R4, R5, R6, R7, R8 each independently represents, the same or different each time it appears, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, or one of a substituted or unsubstituted boranyl group; The substituents of the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof; The heteroatom in the heteroaryl is optionally selected from one or more of O, S, N, Si, and B.

8. The boron-containing resonance-type organic compound according to any one of claims 1-7, characterized in that, M1, M2, and M3 are represented as the following groups which are substituted or unsubstituted: phenyl, naphthyl, anthryl, phenanthryl, pyridyl, quinolinyl, pyrrolyl, furyl, thienyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indolo[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, spirofluorene, any one of them; R1, R2, R3, R4, R5, R6, R7, and R8 are each time the same or different and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazine group; Each occurrence of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6, which may be the same or different, represents a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group; Each occurrence of R and R0, which may be the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group; The R a , R b , R c , R d , R e Each occurrence, independently of the others, represents a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorene, substituted or unsubstituted amino, substituted or unsubstituted triazinyl; The substituents for the substituted groups are each independently selected from a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuryl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, or a combination of one or more thereof; Preferably, R, R0, R1, R2, R3, R4, R5, R6, R7, and R8 are represented by the following structures: A hydrogen atom, a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyano group, a trifluoromethyl group, any one of; Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are represented by the following structures: A hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, any one of; The said R a , R b , R c , R d , R e are represented in the following structure: Any one of them.

9. The boron-containing resonance organic compound according to claim 1, wherein: The specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

10. An organic light-emitting device sequentially includes a substrate, a first electrode, a second electrode, and a functional layer, the functional layer being located between the first electrode and the second electrode, and characterized in that: The functional layer contains the boron-containing resonance organic compound according to any one of claims 1-9; Preferably, the functional layer includes a light-emitting layer, the light-emitting layer contains a host material and a doping material, and the doping material is the boron-containing resonance organic compound according to any one of claims 1-9; Preferably, the functional layer includes a light-emitting layer, the light-emitting layer contains a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing resonance organic compound according to any one of claims 1-9.

11. The organic light-emitting device according to claim 10, wherein the functional layer includes a light-emitting layer, the light-emitting layer contains a host material, an exciton sensitizing material and a doping material, the exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing resonance organic compound according to any one of claims 1-9.

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