A boron-containing organic compound and an organic electroluminescent device prepared therefrom

Abstract

The present invention discloses a boron-containing organic compound and an organic electroluminescent device prepared therefrom, belonging to the technical field of semiconductors. The structure of the organic compound of the present invention is shown in the general formula (B-1). The compound of the present invention is used as a green light doping material for the light-emitting layer of an organic electroluminescent device, which can greatly improve the lifespan of the device.

Description

Technical Field

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

[0002] Limited by early technologies, traditional fluorescent doping materials can only utilize 25% of singlet excitons formed by electrical excitation for luminescence, resulting in a relatively low internal quantum efficiency of the device (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a significant gap compared with the efficiency of phosphorescent devices. Phosphorescent materials can effectively utilize singlet excitons and triplet excitons formed by electrical excitation for luminescence due to the strong spin-orbit coupling of heavy atom centers enhancing intersystem crossing, enabling the internal quantum efficiency of the device to reach 100%. However, most phosphorescent materials are expensive, with poor material stability, poor color purity, and serious efficiency roll-off of the device, which limit their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are put forward for the color rendering standard. In addition to being efficient and stable, luminescent materials also require a narrower full width at half maximum (FWHM) to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum yield and narrow FWHM through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the FWHM of boron-based materials can be reduced to less than 30 nm. In the green light region, to which the human eye is more sensitive, research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape by simple methods. Therefore, it is of great significance to study highly efficient green fluorescent doping materials with narrow FWHM to meet higher color rendering standards.

[0004] In addition, the sensitization technology combines a triplet exciton sensitizing material with a fluorescent doping material. Using the triplet exciton sensitizing material as an exciton sensitization medium, triplet excitons are fully utilized, and the energy is transferred to the fluorescent doping material 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 exert 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.

[0005] Boron compounds with resonance structures are more likely to achieve narrow full-width at half-maximum (FWHM) emission. When such materials are applied in sensitization technologies, devices with high efficiency and narrow FWHM emission can be fabricated. For example, in CN 107507921 A and CN 110492006 A, a luminescent layer combination technology is disclosed, which uses a thermally activated delayed fluorescence (TADF) material with a lowest singlet-triplet energy level difference less than or equal to 0.2 eV as the host and a boron-containing material as the dopant; in CN 110492005 A and CN 110492009 A, a luminescent layer combination scheme is disclosed, which uses an exciplex as the host and a boron-containing material as the dopant; both can achieve efficiency comparable to phosphorescence and a relatively narrow FWHM. Developing sensitization technologies based on narrow FWHM boron-based luminescent materials has unique advantages and strong potential in meeting the BT.2020 display standards. Summary of the Invention

[0006] In view of the above problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a green light doping material for the luminescent layer of an organic electroluminescent device.

[0007] The technical solution of the present invention is as follows: A boron-containing organic compound, the structure of the boron-containing organic compound is shown in the general formula (B-1):

[0008]

[0009] In the general formula (B-1), R 1 -R 19 Each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C1-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0010] R 1 -R 17 Any two adjacent ones in R may be connected to form a ring;

[0011] R 18 and R 19 may be connected to form a ring;

[0012] M 1 、M 3 、M 4 、M 5 、M 6 、M7 Represents a substituted or unsubstituted C 6 ~C 30 Aromatic ring, substituted or unsubstituted 5- to 30-membered heteroaromatic ring or substituted or unsubstituted C 6 ~C 30 Aliphatic ring;

[0013] M 2 Represents a substituted or unsubstituted five-membered ring;

[0014] M 2 And M 3 Are fused-ring connected;

[0015] X represents C, Si;

[0016] The substituents for the substituting groups are each independently selected from deuterium, tritium, halogen atoms, cyano group, C 1 ~C 10 Alkyl, deuterium- or tritium-substituted C 1 ~C 10 Alkyl, C 6 ~C 30 Aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 2 ~C 30 Heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 Any one of heteroaryl.

[0017] In a preferred embodiment, in the general formula (B-1), any two adjacent ones of R 1 -R 17 Can be connected to form a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring or a substituted or unsubstituted C6-C30 aliphatic ring.

[0018] In a preferred embodiment, R in the general formula (B-1) 1 -R 19 Each occurrence, whether the same or different, represents:

[0019] A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, Any one of phenyl;

[0020] The said M 1 、M 4 、M 5 Represents a benzene ring;

[0021] The said M 2 Represents the following ring structure:

[0022]

[0023] any one of;

[0024] The Ar 3 is represented as:

[0025] any one of;

[0026] The Ar 3 means that it can be connected to M 3 to form a five-membered ring through a single bond;

[0027] The M 3 , M 6 , M 7 is represented as a benzene ring;

[0028] X is represented as C, Si.

[0029] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in the general formula (B):

[0030]

[0031] In the general formula (B), R 1 -R 19 each occurrence, the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group;

[0032] R 1 -R 14 any two adjacent ones of which can be connected to form a ring;

[0033] R 18 and R 19 can be connected to form a ring;

[0034] M 1 , M 3 is represented as a substituted or unsubstituted C 6 -C 30 aryl ring, a substituted or unsubstituted 5- to 30-membered heteroaryl ring;

[0035] M 2 is represented as a substituted or unsubstituted five-membered ring;

[0036] M 2 and M 3 are fused-ring connected;

[0037] X is represented as C, Si;

[0038] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium- or tritium-substituted C 1 ~C 10 alkyl, C 6 ~C 30 aryl, deuterium- or tritium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 heteroaryl, and any one of them.

[0039] In a preferred embodiment, in general formula (B), any two adjacent ones of R 1 -R 14 can be connected to form a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, or a substituted or unsubstituted C6-C30 aliphatic ring.

[0040] In a preferred embodiment, R 1 -R 19 each occurrence, whether the same or different, is represented as:

[0041] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group;

[0042] The M 1 is represented as a benzene ring;

[0043] The M 2 is represented as the following ring structure:

[0044]

[0045] any one of them;

[0046] The Ar 3 is represented as:

[0047] any one of them;

[0048] The Ar 3 can be connected to M 3 by a single bond to form a five-membered ring;

[0049] The M 3 is represented as a benzene ring;

[0050] X is represented as C, Si.

[0051] Preferred embodiment, the structure of the boron-containing organic compound is shown by the general formula (B-2):

[0052]

[0053] In the general formula (B-2), R 1 -R 19 Each occurrence, which is the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C1-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0054] R 1 -R 17 Any two adjacent ones in R-R can be connected to form a ring;

[0055] R 18 and R 19 can be connected to form a ring;

[0056] M 1 、M 3 represent a substituted or unsubstituted C 6 ~C 30 aromatic ring, a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, or a substituted or unsubstituted C 6 ~C 30 aliphatic ring;

[0057] X represents C, Si;

[0058] Y represents O, S, N-Ar 3 、C-(RaRb) or Si-(RcRd);

[0059] Ar 3 represents a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C1-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0060] Ra, Rb, Rc, and Rd each independently represent one of a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 aryloxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group;

[0061] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium- or tritium-substituted C 1 -C 10 alkyl group, a C 6 -C 30 aryl group, a deuterium- or tritium-substituted C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, and a deuterium- or tritium-substituted C 2 -C 30 heteroaryl group.

[0062] In a preferred embodiment, in general formula (B-2), any two adjacent ones of R 1 -R 17 can be connected to form a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, or a substituted or unsubstituted C6-C30 aliphatic ring.

[0063] In a preferred embodiment, the Ar 3 and M 3 can be connected to form a ring.

[0064] In a preferred embodiment, Ra and Rb can be connected by a single bond to form a five-membered ring, and Rc and Rd can be connected by a single bond to form a five-membered ring.

[0065] In a preferred embodiment, each occurrence of R 1 -R 19 in general formula (B-2), whether the same or different, represents:

[0066] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group;

[0067] The M 1 represents a benzene ring;

[0068] Y represents O, S, N-Ar 3 、C-(RaRb) or Si-(RcRd);

[0069] The Ar 3 represents:

[0070] any one of;

[0071] The said Ar 3 represents that it can be connected to M 3 to form a five-membered ring through a single bond;

[0072] Ra, Rb, Rc, and Rd each independently represent phenyl, and Ra and Rb can be connected to form a five-membered ring through a single bond, and Rc and Rd can be connected to form a five-membered ring through a single bond;

[0073] The said M 3 represents a benzene ring;

[0074] X represents C or Si.

[0075] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in the general formula (1-1):

[0076]

[0077] In the general formula (1-1), R 1 -R 23 each occurrence, the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0078] R 1 -R 23 any two adjacent ones in it can be connected to form a ring;

[0079] Ar 3 represents a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0080] X represents C or Si;

[0081] The substituents for the substituent groups are each independently selected from deuterium, tritium, halogen atoms, cyano groups, C 1 -C 10 alkyl groups, deuterium- or tritium-substituted C 1 -C 10 alkyl groups, C 6 -C 30An aryl, deuterium or tritium-substituted C 6 ~C 30 An aryl, C 5 ~C 30 A heteroaryl, deuterium or tritium-substituted C 2 ~C 30 Any one of the heteroaryls.

[0082] In a preferred embodiment, in general formula (1-1), any two adjacent R 1 -R 23 s can be connected to form a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring or a substituted or unsubstituted C6-C30 aliphatic ring.

[0083] In a preferred embodiment, each occurrence of R 1 -R 23 in general formula (1-1) is the same or different and represents:

[0084] A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, Any one of a phenyl group;

[0085] Said Ar 3 represents:

[0086] Any one of;

[0087] X represents C, Si.

[0088] In a preferred embodiment, the structure of the boron-containing organic compound is represented by any one of general formula (1-2) to general formula (1-3):

[0089]

[0090] In general formula (1-2) and general formula (1-3), each occurrence of R 1 -R 26 is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C1-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group;

[0091] R 1 -R 26 Any two adjacent ones can be connected to form a ring;

[0092] X is represented as C or Si;

[0093] The said Z is represented as C-R 0 ;

[0094] R 0 Each occurrence is independently represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C1-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0095] The substituents for the substitution groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C 1 -C 10 alkyl group, a deuterium- or tritium-substituted C 1 -C 10 alkyl group, a C 6 -C 30 aryl group, a deuterium- or tritium-substituted C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a deuterium- or tritium-substituted C 2 -C 30 heteroaryl group;

[0096] In a preferred embodiment, in general formula (1-2) and general formula (1-3), R 1 -R 26 Any two adjacent ones of them can be connected to form a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, or a substituted or unsubstituted C6-C30 aliphatic ring.

[0097] In a preferred embodiment, in general formula (1-2) to general formula (1-3), R 1 -R 26 Each occurrence, which may be the same or different, is represented as:

[0098] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group;

[0099] X is represented as C or Si.

[0100] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in general formula (2-1):

[0101]

[0102] In general formula (2-1), R 2 , R 7 , R 9 , R 10 , R 13 , R 16 , R 18 , R 22 , X has the same meaning as defined in the above text;

[0103] Ar 3 represents one of a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group;

[0104] The substituents for the substituent groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C 1 -C 10 alkyl group, a deuterium- or tritium-substituted C 1 -C 10 alkyl group, C 6 -C 30 aryl group, a deuterium- or tritium-substituted C 6 -C 30 aryl group, C 5 -C 30 heteroaryl group, a deuterium- or tritium-substituted C 2 -C 30 heteroaryl group.

[0105] In a preferred embodiment, R 2 , R 7 , R 9 , R 10 , R 13 , R 16 , R 18 , R 22 each occurrence, whether the same or different, represents:

[0106] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group;

[0107] X represents C or Si.

[0108] In a preferred embodiment, the structure of the boron-containing organic compound is represented by any one of general formulas (3-1) to (3-2):

[0109]

[0110] In General Formulas (3-1) to (3-2), each occurrence of R, which may be the same or different, represents one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group;

[0111] X represents C or Si;

[0112] The substituents for the substitution groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium- or tritium-substituted C 1 -C 10 alkyl group, a C 6 -C 30 aryl group, a deuterium- or tritium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, and a deuterium- or tritium-substituted C 2 -C 30 heteroaryl group.

[0113] In a preferred embodiment, each occurrence of R in General Formulas (3-1) to (3-2), which may be the same or different, represents:

[0114] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

[0115] In a preferred embodiment, the R, R 1 -R 26Are independently represented by one of a hydrogen atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted borane group, a methoxy group, a tert-butoxy group;

[0116] Said Ar 3 Is represented by one of a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted borane group, a methoxy group, a tert-butoxy group;

[0117] Said M 1 、M 3 、M4 , M 5 , M 6 , M 7 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, xanthenone group;

[0118] The above-mentioned M 2 is represented by one of furyl, thienyl, pyrrolyl, 1-phenylpyrrolyl;

[0119] The above-mentioned R 0 is represented by one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, adamantyl group, methyl group, deuterated methyl group, tritiated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, tritiated ethyl group, isopropyl group, deuterated isopropyl group, tritiated isopropyl group, tert-butyl group, deuterated tert-butyl group, tritiated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, tritiated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, tritiated phenyl group, biphenyl group, deuterated biphenyl group, tritiated biphenyl group, terphenyl group, deuterated terphenyl group, tritiated terphenyl group, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl group, anthryl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, phenyl-substituted amino group, tert-butylbenzene-substituted amino group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl group, xanthenone group, phenyl-substituted triazine group, phenyl-substituted borane group, methoxy group, tert-butoxy group;

[0120] Ra, Rb, Rc, and Rd are each independently represented by an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthenone group, a phenyl-substituted triazine group, a phenyl-substituted boranyl group, a methoxy group, or a tert-butoxy group;

[0121] The substituents substituting the above-mentioned substituable 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, or an azaphenanthryl group.

[0122] In a preferred embodiment, R and R 1 -R 26 are each independently represented by the following structures:

[0123] a hydrogen atom, a cyano group, any one of;

[0124] Ar 3 is represented by the following structure:

[0125] any one of;

[0126] said M 1 and M 4 and M 5 is represented as any one of the following ring structures:

[0127]

[0128] said M 2 is represented as any one of the following ring structures:

[0129]

[0130] said M 3 and M 6 and M 7 is represented as any one of the following ring structures:

[0131]

[0132] said Z is represented as C-R 0 ;

[0133] R 0 each occurrence is independently represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thiophenyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group.

[0134] Preferred embodiment, R and R 1 -R 26 are each independently represented by the following structures:

[0135] a hydrogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a phenyl group, any one of;

[0136] Ar 3 is represented by the following structure:

[0137] a methyl group, any one of;

[0138] M 1 , M 4 , M 5 is represented by the following ring structure:

[0139]

[0140] M 2 is represented by any one of the following ring structures:

[0141]

[0142] M 3 , M 6 , M 7 is represented by any one of the following ring structures:

[0143]

[0144] Z is represented as C-R 0 ;

[0145] R 0 each occurrence is independently represented by a hydrogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, any one of.

[0146] Preferred embodiment, the specific structural formula of the boron-containing organic compound is any one of the following structures:

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] In a preferred embodiment, the specific structural formula of the boron-containing organic compound is any one of the following structures:

[0164]

[0165]

[0166] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0167] In a preferred embodiment, the organic electroluminescent device sequentially includes a substrate, an anode, an organic light-emitting functional layer, and a cathode. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0168] In a preferred embodiment, the organic electroluminescent device sequentially includes a substrate, a cathode, an organic light-emitting functional layer, and an anode. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0169] In a preferred embodiment, the light-emitting layer includes a host material and a dopant material, and the dopant material contains the boron-containing organic compound.

[0170] In a preferred embodiment, the light-emitting layer comprises a first host material, a second host material, and a dopant material, at least one of the first host material and the second host material being a TADF material, and the dopant material being the boron-containing organic compound described above.

[0171] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, the exciton-sensitizing material being a metal-element-containing complex, and the dopant material being the boron-containing organic compound described above.

[0172] A material for an organic electroluminescent device contains the boron-containing organic compound described above in the present invention.

[0173] An application of the boron-containing organic compound is in an organic electroluminescent device.

[0174] In a preferred embodiment, the organic light-emitting functional layer includes a light-emitting layer, and the application of the boron-containing organic compound in the present invention is to the light-emitting layer.

[0175] A display element includes the organic electroluminescent device described above in the present invention.

[0176] A lighting device includes the organic electroluminescent device described above in the present invention.

[0177] An electronic device is equipped with the organic electroluminescent device described above in the present invention.

[0178] The beneficial technical effects of the present invention are as follows:

[0179] (1) When the compound of the present invention is applied to an OLED device, it can be used as a dopant material for the light-emitting layer material, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

[0180] (2) As a dopant material, the compound of the present invention can significantly improve the device lifetime. Description of the Drawings

[0181] Figure 1 It is a schematic structural diagram of the application of the materials listed in the present invention to an OLED device;

[0182] 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.

[0183] Figure 2 It is the spectral diagram of Compound 139;

[0184] Figure 3 It is the 1H NMR spectrum diagram of Compound 139;

[0185] Figure 4 Spectrum of Compound 171;

[0186] Figure 5 1H NMR spectrum of Compound 171;

[0187] Figure 6 1H NMR spectrum of Compound 353. Detailed implementation mode

[0188] The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. Without conflict, the embodiments and features in the embodiments of the present invention can be combined with each other. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but it is not limited to the present invention.

[0189] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, the orientation words such as "upper", "lower", "top", and "bottom" only represent the orientation in a certain specific state, and do not mean that the relevant structures can only exist in the described orientation; on the contrary, if the structure can be transformed in position, such as being inverted, the orientation of the structure will be changed 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 far from the substrate is the "top" and "upper" sides.

[0190] In the present invention, substituted or unsubstituted C 6 -C 30 aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted group, substituted or unsubstituted bi-p-terphenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl, but not limited thereto.

[0191] In the present invention, substituted or unsubstituted C 2 -C 30Heteroaryl refers to 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.

[0192] The C described in the present invention 1 -C 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to 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.

[0193] The C described in the present invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In this article, C 4 -C 9 cycloalkyl is preferably used, more preferably C 5 -C 8 cycloalkyl, particularly preferably C 5 -C 7 cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, etc., but not limited thereto.

[0194] The C1-C10 alkenyl groups described in the present invention are preferably C2-C8 alkenyl groups, more preferably C2-C5 alkenyl groups, and non-limiting examples thereof may include vinyl, propenyl, isobutenyl, n-pentenyl, isopentenyl, neopentenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, etc., but are not limited thereto.

[0195] The C1-C10 alkynyl groups described in the present invention are preferably C2-C8 alkynyl groups, more preferably C2-C5 alkynyl groups, and non-limiting examples thereof may include ethynyl, propynyl, n-butynyl, isobutynyl, n-pentynyl, isopentynyl, neopentynyl, etc., but are not limited thereto.

[0196] "Can be connected to form a ring" as described in the present invention means that two adjacent groups do not form a ring or are connected to form a ring, preferably can be connected to form a substituted or unsubstituted aromatic ring with 6 to 30 members, a substituted or unsubstituted heteroaromatic ring with 5 to 30 members, or a substituted or unsubstituted aliphatic ring with 5 to 30 members.

[0197] In the present invention, the substituted or unsubstituted arylamino group described in the present invention means where Q 4 and Q 5 represent substituted or unsubstituted aromatic groups, and Q 4 and Q 5 are preferably represented as substituted or unsubstituted C 6 -C 30 aryl or substituted or unsubstituted C 2 -C 30 heteroaryl.

[0198] The halogen atom described in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0199] The C 1 -C 10 alkoxy group refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, etc., but is not limited thereto.

[0200] In the present invention, the substituted or unsubstituted 5- to 30-membered heteroaromatic ring refers to a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a combination thereof or a fused ring of a combination of the foregoing groups, but not limited thereto.

[0201] The present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby greatly improving the lifespan of the device.

[0202] The organic electroluminescent device of the present invention can be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a stacked organic electroluminescent device, and no specific limitation is imposed thereon.

[0203] The organic electroluminescent device of the present invention includes a substrate, a first electrode, an organic light-emitting functional layer, and a second electrode. Among them, the organic light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer. In addition, a CPL layer can be provided on the second electrode.

[0204] 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 plastic substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothness, and water resistances. 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.

[0205] 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 Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a metal mixture. The thickness of the first electrode layer depends on the material used and is generally 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0206] 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.

[0207] In this article, examples of the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0208] 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 OLED devices for use.

[0209] Examples of the above materials can be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styryl anthracene derivatives, styrylamine derivatives, etc., such as styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinylene and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers, etc., conductive polymer oligomers, aromatic tertiary amine compounds, styrylamine compounds, triamines, tetraamines, benzidine compounds, propynediamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamino)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenyl sulfides, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0210] Further, according to the device matching requirements, the hole transport film layer between the electron blocking layer and the hole injection layer that constitutes the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this article, for the hole carrier conduction film layers with various different functions described above, their film thicknesses are not particularly limited.

[0211] The hole injection layer contains a host organic material capable of conducting holes and also contains a P-type doping material with a deep HOMO energy level (and a correspondingly deep LUMO energy level). 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 for conducting 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 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] Therefore, in an embodiment of the present invention, in order to better inject holes, the hole injection layer further contains a charge-conductive P-type doping material 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-trimethylenetri(cyanomethanylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0214] 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.

[0215] 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.

[0216] 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.

[0217] 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.

[0218] 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.

[0219] The light-emitting layer may include a host material and a doping material. The host material may use a common green host material in the art, and the doping material uses a boron-containing organic compound represented by the general formula (1) of the present invention.

[0220] The light-emitting layer may include a single host material or a dual host material;

[0221] 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;

[0222] The TADF material refers to a material with thermally activated delayed fluorescence properties, characterized by having a small energy difference between the first excited singlet state and the first excited triplet state. Therefore, singlet excitons and triplet excitons generated can be utilized simultaneously in the device, making the utilization rate of excitons generated electro-optically in the device as close to 100% as possible. Compared with traditional fluorescent materials, the TADF material has a higher exciton utilization rate.

[0223] The light-emitting layer may include a host material, an exciton sensitizing material and a doping material;

[0224] The exciton sensitizing material refers to a material that can enable the light-emitting material in the light-emitting layer to fully utilize 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 organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0225] 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.

[0226] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and the 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.

[0227] In the present invention, the electron transport region may sequentially include a hole blocking layer, an electron transport layer and an electron injection layer provided above the light-emitting layer from bottom to top, but is not limited thereto.

[0228] 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 extending the lifespan of the device and improving the device's efficiency. The hole blocking layer of the present invention can be disposed above the light-emitting layer. As the hole blocking layer material for the organic electroluminescent device of the present invention, compounds known to have a hole blocking effect in the prior art can be used. For example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum(III) bis(2-methyl-8-quinolinolato)-4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives such as 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole blocking layer of the present invention can be 2 - 200 nm, preferably 5 - 150 nm, but the thickness is not limited to this range.

[0229] 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 easily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. A material with a high electron mobility is preferred. As the electron transport layer for the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used. For example, metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq, and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. 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.

[0230] The electron injection layer can be disposed above the electron transport layer. The material of the electron injection layer is generally preferably a material having a low work function, such that electrons can be easily injected into the organic functional material layer. As the material of the electron injection layer of the organic electroluminescent device of the present invention, the materials known in the prior art for the electron injection layer of the organic electroluminescent device can be used, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. 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.

[0231] The second electrode can be disposed above the electron transport region. The second electrode can be a cathode. The second electrode can be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF 2 , Ba, Ag or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode can 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.

[0232] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure can be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure can 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.

[0233] A method for preparing the organic electroluminescent 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 on a substrate, and optionally a covering layer. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI can be used, but are not limited thereto. In the present invention, it is preferred to use the vacuum evaporation method 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.

[0234] The raw materials involved in the synthesis examples of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0235] Intermediate synthesis:

[0236]

[0237] Synthesis of intermediate A2: Add raw material Y1 (1.61 g, 6.31 mmol), raw material Y2 (13.25 mmol), tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol), tri-tert-butylphosphine (0.12 g, 0.57 mmol), potassium carbonate (0.17 g, 1.23 mmol.), 50 ml of toluene, and 10 ml of water into a two-necked flask, react at 110 °C under nitrogen for 24 h, cool, extract with ethyl acetate, wash with saturated brine, dry, and pass through a column with PE:EA=20:1 to obtain intermediate A2.

[0238]

[0239] Synthesis of intermediate Q3: In a three-necked flask, add raw material S3 (0.36 g, 2 mmol), raw material S4 (0.58 g, 2 mmol), 50 mL toluene, 16 mL ethanol, 8 ml water, potassium carbonate (0.83 g, 6 mmol), Pd(PPh 3 ) 4 (0.12 g, 0.1 mmol), nitrogen protection, reaction at reflux temperature for 8 h, cooling to room temperature after the reaction, quenching the reaction with water, extracting three times with ethyl acetate, combining the organic phases, then drying with anhydrous sodium sulfate, filtering and concentrating to obtain the crude product. The intermediate Q3 was obtained by recrystallization (EA / PE) purification.

[0240]

[0241] Synthesis of intermediate Q4: In a three-necked flask, add raw material S1 (0.36 g, 2 mmol), raw material S2 (0.69 g, 2 mmol), 50 mL toluene, 16 mL ethanol, 8 ml water, potassium carbonate (0.83 g, 6 mmol), Pd(PPh 3 ) 4 (0.12 g, 0.1 mmol) was protected by nitrogen and reacted at reflux temperature for 8 h. After the reaction was completed, the mixture was cooled to room temperature, and water was added to quench the reaction. The mixture was extracted three times with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. The intermediate Q4 was purified by recrystallization (EA / PE).

[0242]

[0243] Synthesis of intermediate K2: Add raw material N1 (2.30 g, 6.31 mmol), raw material M1 (1.48 g, 13.25 mmol), tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol), tri-tert-butylphosphine (0.12 g, 0.57 mmol), potassium carbonate (0.17 g, 1.23 mmol.), 50 ml of toluene, 10 ml of water into a two-necked bottle, react at 110 ° C under nitrogen environment for 24 hours, cool and extract with ethyl acetate, wash with saturated brine, dry, and pass through a column with PE:EA=20:1 to obtain intermediate K2.

[0244]

[0245] Preparation of intermediate K4: Under nitrogen protection, raw material U1 (0.50 g, 2 mmol), raw material V1 (0.58 g, 2.5 mmol), Li 2 CO 3 (0.44 mg, 6 mmol) and PdCl 2 (CH 3 CN) 2 The catalyst (0.03 g, 0.1 mmol) was dissolved in 50 mL of 1,4-dioxane and stirred at 140°C for 18 hours. The suspension was filtered and the solid was washed with 20 mL of tetrahydrofuran and 40 mL of ethyl acetate to obtain intermediate K4.

[0246] Synthesis of intermediate G1

[0247]

[0248] Synthesis of intermediate M2: In a three-necked flask, (5.16 g, 25 mmol) of raw material K1, (7.36 g, 25 mmol) of raw material Q1, (6.01 g, 60 mmol) of calcium carbonate and (0.016 g, 0.25 mmol) of Cu powder catalyst were added in sequence under nitrogen, and 200 mL of anhydrous DMF was added. The obtained suspension was heated to 130°C with silicone oil, stirred for 12 hours, extracted three times with ethyl acetate, the organic phases were combined, and then dried with anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. Intermediate M2 was obtained by purification through recrystallization (ethyl acetate / petroleum ether).

[0249] Synthesis of Intermediate G1: Under a nitrogen atmosphere in a three-necked flask, (9.32 g, 25 mmol) of Intermediate M2, (0.42 g, 1.5 mmol) of tricyclohexylphosphine, (19.55 g, 60 mmol) of cesium carbonate, and (0.059 g, 0.25 mmol) of palladium acetate were successively added. 300 mL of DMA was added, and the resulting suspension was heated to 160 °C with silicone oil and stirred for 9 hours. It was extracted three times with ethyl acetate, the organic phases were combined, then dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the crude product. Intermediate G1 was obtained by purification through recrystallization (ethyl acetate / petroleum ether).

[0250] Synthesis of Intermediate G2: Referring to the synthetic route of Intermediate G1, the reaction conditions are the same, except that Intermediate K2 will be used to replace raw material K1 as shown in Table 2-1:

[0251] Table 2-1

[0252]

[0253] Synthesis of Intermediate G3

[0254]

[0255] Preparation of Intermediate N2: Under nitrogen protection, raw material K3 (0.54 g, 2 mmol), (Boc) 2 O (0.55 g, 2.5 mmol) were dissolved in 50 mL of tetrahydrofuran, DMAP (0.06 g, 0.5 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The suspension was filtered, and the solid was washed with 20 mL of tetrahydrofuran and 40 mL of ethyl acetate to obtain Intermediate N2.

[0256] Preparation of Intermediate M3: Intermediate N2 (1.12 g, 3 mmol) was dissolved in 50 mL of a tetrahydrofuran (THF) solution. Under a nitrogen atmosphere at 0 °C, 3.8 mL of a 1.6 M n-butyllithium solution in hexane was slowly added; after stirring at 0 °C for 2 hours, 10 mL of a tetrahydrofuran solution of raw material F1 (2.29 g, 12.7 mmol) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture, the aqueous layer was separated, and it was 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 quenched slowly with an aqueous NaHCO 3 aqueous solution. Then the aqueous layer was separated and extracted with dichloromethane. It was dried over sodium sulfate, filtered, and evaporated by rotary evaporation, and purified by column chromatography to obtain Intermediate M3.

[0257] Preparation of intermediate G3: In a three-necked flask, under nitrogen protection, intermediate M3 (0.46 g, 1 mmol) was dissolved in 20 mL of dichloromethane, followed by addition of 10 mL of trifluoroacetic acid and stirring at room temperature for 23 hours. The reaction was then quenched with a saturated sodium bicarbonate solution, washed with dichloromethane, separated and collected organic phases, dried over anhydrous sodium sulfate, and concentrated. Purified by a silica gel column (ethyl acetate: petroleum ether = 1:10) to obtain intermediate G3.

[0258] The synthesis of intermediate G4 refers to the synthesis route of intermediate G3, and the reaction conditions are the same, except that intermediate K4 is used to replace raw material K3 as shown in Table 2-2:

[0259] Table 2-2

[0260]

[0261]

[0262] Synthesis of intermediate G5: Dissolve the raw material Q2 (5.33 g, 25 mmol) in 100 mL of toluene solution, add raw material K1 (5.16 g, 25 mmol), tri-tert-butylphosphine (0.3 g, 1.5 mmol), sodium tert-butoxide (6.25 g, 65 mmol) and palladium acetate (0.09 g, 0.4 mmol), and stir vigorously. Reflux the resulting mixture at 105 ° C for 10 hours and then allow it to reach room temperature. Then add ethyl acetate (100 mL). The mixture is washed with deionized water (100 mL) 3 times. After drying over anhydrous magnesium sulfate overnight, ethyl acetate is evaporated under reduced pressure. Pour the remaining mixture into 100 mL of petroleum ether under stirring. After filtration, intermediate G5 is obtained.

[0263] The synthesis of intermediates G6 and G7 refers to the synthesis route of intermediate G5. The reaction conditions are the same, except that the reactants are intermediates Q3 and Q4 instead of raw material Q2, as shown in Table 2-3:

[0264] Table 2-3

[0265]

[0266]

[0267] Synthesis of intermediate G8

[0268]

[0269] Synthesis of intermediate G8: Dissolve the raw material Q5 (7.08 g, 25 mmol) in 100 mL of toluene solution, add raw material K1 (5.16 g, 25 mmol), tri-tert-butylphosphine (0.3 g, 1.5 mmol), sodium tert-butoxide (6.25 g, 65 mmol) and palladium acetate (0.09 g, 0.4 mmol), and stir vigorously. Reflux the resulting mixture at 105 ° C for 10 hours and then allow it to reach room temperature. Then add ethyl acetate (100 mL). The mixture is washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate is evaporated under reduced pressure. Pour the remaining mixture into 100 mL of petroleum ether under stirring. After filtration, intermediate G8 is obtained.

[0270] Example 1: Synthesis of Compound 131:

[0271]

[0272] Synthesis of intermediate B1: Add raw material E1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material A1 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate B1.

[0273] Synthesis of intermediate C1: Intermediate B1 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution, and 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added under nitrogen at 0°C; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material F1 (0.99 g, 5.5 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted three times with ethyl acetate. The combined organic layer was 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 treated with NaHCO 3 The aqueous solution was slowly quenched. The aqueous layer was then separated and extracted with dichloromethane. It was dried over sodium sulfate, filtered, and evaporated by rotary concentrator and passed through a column to obtain intermediate C1.

[0274] Synthesis of intermediate D1: Intermediate C1 (1.58 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and intermediate G5 (0.85 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 10 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate D1.

[0275] Synthesis of compound 131: Intermediate D1 (11.11 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene solution, and 10 mL of tert-butyl lithium (1.6 M) in n-pentane was slowly added under a nitrogen atmosphere at 0°C, and stirred at 60°C for 2 hours. After adding boron tribromide (6.26 g, 25 mmol) at 0°C, the reaction mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in vacuo and passed through a column to give compound 131.

[0276] Synthesis of the corresponding compounds 139, 171, 173, 285, 287, 353, 357, 359, 365 in Examples 2, 3, 4, 5, 6, 7, 8, 9, 10:

[0277] The following target compound was synthesized by referring to the preparation process of compound 131 in Example 1; the reaction conditions were the same, and the raw materials E1 and F1 used were the same, except that the raw materials A and intermediate G listed in Table 2-4 below were used;

[0278] Table 2-4

[0279]

[0280]

[0281] Example 11: Synthesis of Compound 142:

[0282]

[0283] Synthesis of intermediate B2: Add raw material E2 (1.22 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material A2 (1.79 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate B2.

[0284] Synthesis of intermediate C2: Intermediate B2 (4.19 g, 7.2 mmol) was dissolved in 30 mL of anhydrous ether and heated at 0 °C under N 2 Under the atmosphere, 10 mL of a hexane solution of n-butyl lithium (1.6 M) was added dropwise with stirring; the mixture was stirred at 0°C for 1 hour, and then 10 mL of an anhydrous toluene solution of raw material F2 (2.01 g, 8.00 mmol) was added dropwise; the reaction mixture was stirred at 35°C for 2 hours, and then cooled to room temperature; after adding water, the product was extracted with ethyl acetate. The combined organic layer was washed with brine and precipitated with anhydrous Na 2 SO 4 After drying, filtration and evaporation, intermediate C2 was obtained by column chromatography.

[0285] Synthesis of intermediate D2: Intermediate C2 (2.95 g, 4.9 mmol) was dissolved in 50 mL of toluene solution, and intermediate G4 (2.340 g, 5 mmol), tri-tert-butylphosphine (0.051 g, 0.25 mmol), sodium tert-butoxide (1.25 g, 13 mmol) and palladium acetate (0.018 g, 0.08 mmol) were added and stirred vigorously. The resulting mixture was heated to 105 ° C for 9 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate D2.

[0286] Synthesis of compound 142: Intermediate D2 (12.92 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of tert-butyl lithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, the n-pentane was removed in a vacuum. After adding boron tribromide (6.26 g, 25 mmol) at 0°C, the reaction mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 142.

[0287] Example 12: Synthesis of Compound 369:

[0288]

[0289] Synthesis of intermediate B1: Add raw material E1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material A1 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate B1.

[0290] Synthesis of intermediate C3: Intermediate B1 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution, and 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added under nitrogen at 0°C; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material F3 (5.5 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted three times with ethyl acetate. The combined organic layer was 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 treated with NaHCO 3 The aqueous solution was slowly quenched. The aqueous layer was then separated and extracted with dichloromethane. It was dried over sodium sulfate, filtered, and evaporated by rotary concentrator and passed through a column to obtain intermediate C3.

[0291] Synthesis of intermediate D3: Intermediate C3 (1.86 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and intermediate G8 (1.02 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 10 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate D3.

[0292] Synthesis of Compound 369: Intermediate D3 (13.38 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene solution. Under a nitrogen atmosphere at 0 °C, 10 mL of a 1.6 M solution of tert-butyllithium in n-pentane was slowly added, and the mixture was stirred at 60 °C for 2 hours. After adding boron tribromide (6.26 g, 25 mmol) at 0 °C, the reaction mixture was stirred at room temperature for 1 hour. N,N-Diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr 3 . The mixture was separated, and extraction was carried out with water and dichloromethane. The combined organic layers were condensed in vacuo and purified by column chromatography to obtain Compound 369.

[0293] The test results of the structural characterization, mass spectrometry analysis, and physical and chemical properties of the compounds in each example are as follows:

[0294] The structural formula of Compound 131 (C 63 H 52 BN 3 ): Theoretical values: C, 87.79; H, 6.08; N, 4.88; Measured values: C, 87.77; H, 6.07; N, 4.86. LC-MS: Measured value: 862.45 ([M+H] + ), Exact mass: 861.43. PLQY is 98%, and FWHM is 25 nm.

[0295] The structural formula of Compound 139 (C 66 H 47 BN 2 ): Theoretical values: C, 90.19; H, 5.39; N, 3.19; Measured values: C, 90.18; H, 5.38; N, 3.17. LC-MS: Measured value: 879.40 ([M+H] + ), Exact mass: 878.38. PLQY is 91%, and FWHM is 29 nm.

[0296] Figure 2 is the spectrogram of Compound 139. Test conditions (toluene solution, 5×10 -5 M), Test equipment: Horiba Fluorolog-3 scientific-grade fluorescence spectrometer;

[0297] Figure 3 is the 1H NMR spectrum of Compound 139.

[0298] The structural formula of Compound 171 (C 63 H 50 BN 3) Theoretical values: C, 88.00; H, 5.86; N, 4.89; Test values: C, 87.96; H, 5.92; N, 4.85. LC-MS: Measured value: 860.45 ([M+H] + ), Exact mass: 859.41. PLQY is 97%, FWHM is 28 nm.

[0299] Figure 4 Is the spectrogram of Compound 171, test conditions (toluene solution, 5×10 -5 M), Test equipment: Horiba Fluorolog-3 scientific-grade fluorescence spectrometer;

[0300] Figure 5 Is the 1H NMR spectrum of Compound 171.

[0301] The structural formula of Compound 173 (C 71 H 66 BN 3 ) Theoretical values: C, 87.72; H, 6.84; N, 4.32; Test values: C, 87.62; H, 6.85; N, 4.35. LC-MS: Measured value: 972.61 ([M+H] + ), Exact mass: 971.53. PLQY is 94%, FWHM is 26 nm.

[0302] The structural formula of Compound 285 (C 68 H 47 D 4 BN 2 ) Theoretical values: C, 89.65; H, 6.08; N, 3.08; Test values: C, 89.74; H, 6.06; N, 3.12. LC-MS: Measured value: 911.42 ([M+H] + ), Exact mass: 910.44. PLQY is 98%, FWHM is 25 nm.

[0303] The structural formula of Compound 287 (C 60 H 29 D 6 BN 2 ) Theoretical values: C, 89.99; H, 5.16; N, 3.50; Test values: C, 89.94; H, 5.13; N, 3.58. LC-MS: Measured value: 801.35 ([M+H] + ), Exact mass: 800.33. PLQY is 96%, FWHM is 28 nm.

[0304] The structural formula of Compound 353 (C 73 H 64 BN 3) Theoretical values: C, 88.20; H, 6.49; N, 4.23; Test values: C, 88.21; H, 6.47; N, 4.27. LC-MS: Measured value: 994.75 ([M+H] + ) and the exact mass is 993.52. The PLQY is 97% and the FWHM is 29 nm.

[0305] Figure 6 This is the 1H NMR spectrum of compound 353.

[0306] The structural formula of compound 357 (C 75 H 64 D 4 BN 3 ) Theoretical values: C, 87.78; H, 7.07; N, 4.09; Test values: C, 87.80; H, 7.11; N, 4.16. LC-MS: Measured value: 1026.67 ([M+H] + ) and the exact mass is 1025.58. The PLQY is 93% and the FWHM is 25 nm.

[0307] The structural formula of compound 359 (C 67 H 46 D 6 BN 3 ) Theoretical values: C, 87.85; H, 6.38; N, 4.59; Test values: C, 87.81; H, 6.40; N, 4.65. LC-MS: Measured value: 916.42 ([M+H] + ) and the exact mass is 915.46. The PLQY is 97% and the FWHM is 25 nm.

[0308] The structural formula of compound 365 (C 79 H 70 D 4 BN 3 ) Theoretical values: C, 87.83; H, 7.28; N, 3.89; Test values: C, 87.77; H, 7.24; N, 3.93. LC-MS: Measured value: 1080.68 ([M+H] + ) and the exact mass is 1079.62. The PLQY is 93% and the FWHM is 25 nm.

[0309] The structural formula of compound 142 (C 73 H 63 BN 2 Si) Theoretical values: C, 87.05; H, 6.30; N, 2.78; Test values: C, 87.14; H, 6.35; N, 2.81. LC-MS: Measured value: 1007.43 ([M+H] +), Exact mass: 1006.49. PLQY is 97%, FWHM is 25 nm.

[0310] The structural formula of Compound 369 (C 76 H 78 BN 3 ). Theoretical values: C, 87.41; H, 7.53; N, 4.02; Measured values: C, 87.47; H, 7.47; N, 3.96. LC-MS: Measured value: 1044.67 ([M+H] + ), Exact mass: 1043.63. PLQY is 91%, FWHM is 29 nm.

[0311] Note: PLQY (photoluminescence quantum yield) and FWHM (full width at half maximum) were measured by a Horiba Fluorolog-3 series fluorescence spectrometer in the thin film state.

[0312] From the above compound data, it can be seen that the compounds of the present invention have a high fluorescence quantum efficiency as doping materials, and the fluorescence quantum efficiency of the materials is close to 100%; at the same time, the spectral FWHM of the materials is narrow, which can effectively improve the color gamut of the device and the luminous efficiency of the device.

[0313] The application effects of the synthesized OLED 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 the devices in Device Examples 1-12 of the present invention are exactly the same as those in Device Comparative Examples 1-4, 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 light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3 and 4 respectively.

[0314] Device Example 1

[0315] As Figure 1As 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 successively with a cleaning agent (Semiclean M-L20), pure water, and 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 and compound 131 as the doping material, and the mass ratio of GH-1, GH-2, and compound 131 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, and the film thickness is 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.

[0316] The application effects of the OLED materials synthesized by the present invention in the device are described in detail below through Device Examples 13-24 and Device Comparative Examples 5-8. The manufacturing processes of the devices in Device Examples 13-24 of the present invention are exactly the same as those in Device Comparative Examples 5-8, 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 light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3 and 4 respectively.

[0317] Device Example 13

[0318] 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-mentioned 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-mentioned electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first doping material, and compound 131 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 131 is 66:30:3:1, and the film thickness of the light-emitting layer is 30 nm. After the above-mentioned 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-mentioned 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.

[0319] The molecular structural formulas of the related materials are as follows:

[0320]

[0321] The comparative compounds ref-1, ref-2, ref-3, and ref-4 are prepared by referring to the methods described in the prior art.

[0322] After completing the OLED light-emitting device as described above, the anode and the cathode are connected by a well-known driving circuit, and the voltage, current efficiency, and device lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 3; the test results of the voltage, current efficiency, and lifetime of the obtained devices are shown in Table 4.

[0323] Table 3

[0324]

[0325]

[0326] Table 4

[0327]

[0328] Note: The current efficiency and emission peak are measured using an IVL (current-voltage-luminance) test system (Suzhou Fosda Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester from System Technology Research Co., Ltd. in Japan; LT95 refers to the time it takes for the device luminance to decay to 95%; all data are measured at 10 mA / cm 2 under the test.

[0329] From the device data results in Table 4, it can be seen that compared with Device Comparative Examples 1-4, the device lifetime of the compound of the present invention in the single-doping system device is higher than that of Comparative Examples 1-4; in the single-doping system device, the device efficiency also shows good results; compared with Device Comparative Examples 5-8, in the double-doping system device using an exciton sensitizing material as the first doping, both the current efficiency and device lifetime of the device are significantly improved compared to the OLED devices of known materials, and in the double-doping device, the device efficiency is also significantly improved compared to the single-doping case.

[0330] 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 replacements, improvements, etc. made within the spirit and principles of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, the structure of the boron-containing organic compound is shown by the general formula (B-1): In general formula (B-1), R 1 -R 19 Each occurrence, independently of the others, represents one selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; M 1 、M 3 、M 4 、M 5 、M 6 、M 7 is represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted biphenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, and a tert-butyl-substituted dibenzofuranyl group; M 2 represents a substituted or unsubstituted five-membered ring; M 2 and M 3 are connected by annulation; X represents C or Si; The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 2 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, any one of them.

2. The boron-containing organic compound according to claim 1, characterized in that, the structure of the boron-containing organic compound is shown by the general formula (B): In general formula (B), R 1 -R 19 each occurrence is the same or different and represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; M 1 、M 3 is represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted biphenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, and a tert-butyl-substituted dibenzofuranyl group; M 2 represents a substituted or unsubstituted five-membered ring; M 2 and M 3 are connected by a spiro linkage; X represents C or Si; The substituents for the substituent groups are each independently selected from deuterium, a halogen atom, a cyano group, C 1 to C 10 alkyl, deuterium-substituted C 1 to C 10 alkyl, C 6 to C 30 aryl, deuterium-substituted C 6 to C 30 aryl, C 5 to C 30 heteroaryl, deuterium-substituted C 2 to C 30 heteroaryl, any one of them.

3. The boron-containing organic compound according to claim 1, characterized in that, the structure of the boron-containing organic compound is shown by the general formula (B-2): In general formula (B-2), R 1 -R 19 Each occurrence, independently of the others, represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; M 1 、M 3 is represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted biphenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, and a tert-butyl-substituted dibenzofuranyl group; X represents C or Si; Y is represented as O, S, N-Ar 3 or CRaRb; Ar 3 is one of C1-C10 alkyl, C6-C30 aryl, and C2-C30 heteroaryl; Ra and Rb each independently represent one of C1-C10 alkyl, C6-C30 aryl, and C2-C30 heteroaryl; The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 2 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, and any one of them.

4. A boron-containing organic compound, characterized in that, the structure of the boron-containing organic compound is shown by the general formula (1-1): In general formula (1-1), R 1 -R 23 Each occurrence is the same or different and represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; Ar 3 is one of a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; X represents C or Si; The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, a C 1 to C 10 alkyl group, a deuterium-substituted C 1 to C 10 alkyl group, a C 6 to C 30 aryl group, a deuterium-substituted C 6 to C 30 aryl group, a C 5 to C 30 heteroaryl group, a deuterium-substituted C 2 to C 30 heteroaryl group, and any one of them.

5. A boron-containing organic compound, characterized in that, the structure of the boron-containing organic compound is shown by any one of the general formulas (1-2) to (1-3): In General Formulas (1-2) and (1-3), R 1 -R 26 Each occurrence, independently of the others, represents one selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; X represents C or Si; wherein Z is represented by C-R 0 ; R 0 Each occurrence is independently represented by one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, a C 1 to C 10 alkyl group, a deuterium-substituted C 1 to C 10 alkyl group, a C 6 to C 30 aryl group, a deuterium-substituted C 6 to C 30 aryl group, a C 2 to C 30 heteroaryl group, a deuterium-substituted C 2 to C 30 heteroaryl group, and any one of them.

6. The boron-containing organic compound according to claim 4, characterized in that, the structure of the boron-containing organic compound is shown by the general formula (2-1): In general formula (2-1), the meanings of R 2 , R 7 , R 9 , R 10 , R 13 , R 16 , R 18 , R 22 , and X are the same as those defined in claim 4; Ar 3 is one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, and any one of them.

7. A boron-containing organic compound, characterized in that, the structure of the boron-containing organic compound is shown by any one of the general formulas (3-1) to (3-2): In the general formulas (3-1) to (3-2), each occurrence of R is the same or different and represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; X represents C or Si; The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium-substituted C 1 -C 10 alkyl group, a C 6 -C 30 aryl group, a deuterium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a deuterium-substituted C 2 -C 30 heteroaryl group, and any one of them.

8. The boron-containing organic compound according to claim 1, characterized in that, The R 1 -R 19 are each independently represented by a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthenone group, a phenyl-substituted triazinyl group; The M 1 , M 3 , M 4 , M 5 , M 6 , M 7 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, pyridyl, phenyl-substituted pyridyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl; The M 2 is represented as one of furyl, thienyl, pyrrolyl, 1-phenylpyrrolyl.

9. The boron-containing organic compound according to claim 2, characterized in that, The R 1 -R 19 are each independently represented by a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an oxanthrone group, a phenyl-substituted triazinyl group; The M 1 , M 3 is represented as one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, pyridyl, phenyl-substituted pyridyl, benzofuryl, dibenzofuryl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl; The M 2 is represented as one of furyl, thienyl, pyrrolyl, 1-phenylpyrrolyl.

10. The boron-containing organic compound according to claim 3, characterized in that, The R 1 -R 19 are each independently represented by a hydrogen atom, deuterium atom, fluorine atom, cyano group, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl, xanthenone group, phenyl-substituted triazinyl group; The Ar 3 is represented by one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, xanthenone; The said M 1 , M 3 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, pyridyl, phenyl-substituted pyridyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl; Ra and Rb each independently represent one of methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, and xanthenone.

11. The boron-containing organic compound according to claim 4, characterized in that, The R 1 -R 23 are each independently represented by a hydrogen atom, deuterium atom, fluorine atom, cyano group, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl, xanthone group, phenyl-substituted triazinyl group; The Ar 3 is one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl.

12. The boron-containing organic compound according to claim 5, characterized in that, The R 1 -R 26 are each independently represented by a hydrogen atom, deuterium atom, fluorine atom, cyano group, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl, xanthone group, phenyl-substituted triazinyl group; The R 0 represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group.

13. The boron-containing organic compound according to claim 6, characterized in that, The R 2 , R 7 , R 9 , R 10 , R 13 , R 16 , R 18 , R 22 are each independently represented by one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an oxanthrone group, a phenyl-substituted triazinyl group; The Ar 3 is one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazine.

14. The boron-containing organic compound according to claim 7, characterized in that, R is independently represented by a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl group, an xanthenone group, a phenyl-substituted triazine group, or the like.

15. A boron-containing organic compound characterized in that the structure of the boron-containing organic compound is represented by the general formula (B-1): In general formula (B-1), the R 1 -R 19 each independently represents the following structure: Hydrogen atom, cyano group, any one of; said M 1 , M 4 , M 5 is represented as any one of the following ring structures: The said M 2 is represented as any one of the following ring structures: Said M 3 , M 6 , M 7 is represented as any one of the following ring structures: wherein Z is represented as C-R 0 ; R 0 Each occurrence, independently, represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazinyl group; M 2 and M 3 are connected by annulation; X is represented by C or Si.

16. A boron-containing organic compound characterized in that the structure of the boron-containing organic compound is represented by the general formula (B): In general formula (B), the R 1 -R 19 are each independently represented by the following structures: Hydrogen atom, cyano group, any one of; The M 1 is represented as any one of the following ring structures: The said M 2 is represented as any one of the following ring structures: The said M 3 is represented as any one of the following ring structures: wherein Z is represented as C-R 0 ; R 0 Each occurrence is independently represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuranyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, tert-butyl-substituted dibenzofuranyl group, phenyl-substituted tert-butyl, xanthone group, phenyl-substituted triazinyl group; M 2 and M 3 are connected by annulation; X is represented by C or Si.

17. A boron-containing organic compound characterized in that the structure of the boron-containing organic compound is represented by the general formula (B-2): In general formula (B-2), the R 1 -R 19 are each independently represented by the following structures: Hydrogen atom, cyano group, any one of; X is represented by C or Si; Y is represented by O, S or N-Ar 3 ; The Ar 3 is represented in the following structure: any one of; said M 1 is represented as any one of the following ring structures: The M 3 is represented as any one of the following ring structures: wherein Z is represented as C-R 0 ; R 0 Each occurrence is independently represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl, xanthenone group, phenyl-substituted triazinyl group.

18. The boron-containing organic compound according to claim 4 characterized in that The said R 1 -R 23 are each independently represented as the following structures: A hydrogen atom, a cyano group, any one of; The Ar 3 is represented as the following structure: Any one of them.

19. The boron-containing organic compound according to claim 5 characterized in that The said R 1 -R 26 are each independently represented as the following structures: Hydrogen atom, cyano group, any one of; R 0 Each occurrence is independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group.

20. The boron-containing organic compound according to claim 6 characterized in that The said R 2 , R 7 , R 9 , R 10 , R 13 , R 16 , R 18 , R 22 are each independently represented as the following structures: Hydrogen atom, cyano group, any one of; The Ar 3 is represented in the following structure: Any one of them.

21. The boron-containing organic compound according to claim 7 characterized in that The R's are each independently represented by the following structures: a hydrogen atom, a cyano group, Any one of them.

22. A boron-containing organic compound characterized in that the specific structural formula of the boron-containing organic compound is any one of the following structures:

23. An organic electroluminescent device comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer includes a light-emitting layer characterized in that the light-emitting layer contains the boron-containing organic compound according to any one of claims 1-22.

24. The organic electroluminescent device according to claim 23 characterized in that the light-emitting layer contains a host material and a dopant material, and the dopant material contains the boron-containing organic compound according to any one of claims 1-22.

25. The organic electroluminescent device according to claim 23, wherein the light-emitting layer contains a first host material, a second host material, and a dopant material characterized in that at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound according to any one of claims 1-22.

26. The organic electroluminescent device according to claim 23, wherein the light-emitting layer comprises a host material, an exciton sensitizing material, and a doping material, characterized in that, the exciton sensitizing material is a metal element-containing complex, and the doping material is a boron-containing organic compound according to any one of claims 1-22.

27. A material for an organic electroluminescent device, characterized in that, it contains a boron-containing organic compound according to any one of claims 1-22.

28. An application of a boron-containing organic compound according to any one of claims 1-22, characterized in that, it is applied to an organic electroluminescent device.

29. The application according to claim 28, characterized in that, the organic light-emitting functional layer in the organic electroluminescent device comprises a light-emitting layer, and the boron-containing organic compound according to any one of claims 1-22 is applied to the light-emitting layer.

30. A display element, characterized in that, it comprises an organic electroluminescent device according to any one of claims 23-26.

31. A lighting device, characterized in that, it comprises an organic electroluminescent device according to any one of claims 23-26.

32. An electronic device, characterized in that, it is equipped with an organic electroluminescent device according to any one of claims 23-26.

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