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 (A-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 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] Traditional fluorescent doping materials are limited by early technologies and can only utilize 25% of the singlet excitons formed by electrical excitation for luminescence. The internal quantum efficiency of the device is relatively low (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a large gap compared with the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling of heavy atom centers that enhances intersystem crossing, can effectively utilize both singlet excitons and triplet excitons formed by electrical excitation for luminescence, 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, the luminescent material also requires a narrower full width at half maximum to improve the color purity of the device luminescence. Fluorescent doping materials can achieve high fluorescence quantum and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum 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, the research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape by simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study highly efficient green fluorescent doping materials with a narrow full width at half maximum.

[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, it fully utilizes triplet excitons and transfers the energy to the fluorescent doping material through energy transfer, and 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) luminescence. 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 the lowest singlet and lowest 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 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 indicators. 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 (A-1):

[0008]

[0009] In the general formula (A-1), R 1 -R 19 Each occurrence, 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 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;

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

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

[0012] Ar 1 、Ar 2Each occurrence, the same or different, represents one of a hydrogen atom, 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;

[0013] M 1 、M 2 、M 3 、M 4 、M 5 Each independently represents one of 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 C6-C10 aliphatic ring;

[0014] X represents C or Si;

[0015] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium or tritium, a C6-C30 aryl group, a C6-C30 aryl group substituted with deuterium or tritium, a C2-C30 heteroaryl group, or a C2-C30 heteroaryl group substituted with deuterium or tritium.

[0016] In a preferred embodiment, in the general formula (A-1), any two adjacent ones of R 1 -R 17 can be linked 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.

[0017] In a preferred embodiment, in the general formula (A-1), R 1 -R 19 each occurrence, the same or different, represents:

[0018] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group;

[0019] Each occurrence, the same or different, Ar 1 、Ar 2 represents:

[0020] a methyl group, any one of;

[0021] The said M 1 、M 2 、M 3 is represented as any one of the following ring structures:

[0022]

[0023] The said M 4 、M 5 is represented as the following ring structure:

[0024]

[0025] The said Z is represented as C-R a ;

[0026] R a Each occurrence is independently represented as: a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group;

[0027] X is represented as C, Si.

[0028] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in the general formula (A):

[0029]

[0030] In the general formula (A), R 1 -R 19 Each occurrence, which may be the same or different, is 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 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;

[0031] R 1 -R 14 Any two adjacent ones in them can be connected to form a ring;

[0032] R 18 and R 19 can be connected to form a ring;

[0033] Ar 1 、Ar 2Each occurrence of the same or different ones is 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;

[0034] M 1 represented as a substituted or unsubstituted C 6 ~C 30 aromatic ring or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring;

[0035] X is represented as C, Si;

[0036] The substituent for the substituent group is arbitrarily selected from deuterium, tritium, a halogen atom, a cyano group, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium or tritium, a C6-C30 aryl group, a C6-C30 aryl group substituted with deuterium or tritium, a C5-C30 heteroaryl group, and a C2-C30 heteroaryl group substituted with deuterium or tritium.

[0037] In a preferred embodiment, in the general formula (A), any two adjacent ones in 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.

[0038] In a preferred embodiment, in the general formula (A), R 1 -R 19 each occurrence of the same or different ones is represented as:

[0039] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group;

[0040] Each occurrence of the same or different ones of the Ar 1 and Ar 2 is represented as:

[0041] a methyl group, any one of;

[0042] Each occurrence of the same or different ones of the M 1 is represented as any one of the following ring structures:

[0043]

[0044] The Z is represented as C-R a ;

[0045] R a Each occurrence is independently represented as: a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or any one of phenyl;

[0046] X is represented as C or Si.

[0047] Preferably, the structure of the boron-containing organic compound is shown by any one of general formulas (1-1) to (1-2):

[0048]

[0049] In general formulas (1-1) to (1-2), R 1 -R 21 Each occurrence, the same or different, is 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 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;

[0050] R 1 -R 21 Any two adjacent ones in them can be connected to form a ring;

[0051] Ar 1 、Ar 2 Each occurrence, the same or different, is represented as 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;

[0052] X is represented as C or Si;

[0053] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium or tritium, a C6-C30 aryl group, a C6-C30 aryl group substituted with deuterium or tritium, a C5-C30 heteroaryl group, a C2-C30 heteroaryl group substituted with deuterium or tritium.

[0054] Preferably, in general formulas (1-1) and (1-2), R 1 -R 21Any two adjacent ones among 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.

[0055] In a preferred embodiment, R in the general formula (1-1) and the general formula (1-2) 1 -R 21 Each occurrence, which may be the same or different, represents:

[0056] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group;

[0057] The Ar 1 、Ar 2 Each occurrence, which may be the same or different, represents:

[0058] a methyl group, any one of;

[0059] X represents C or Si.

[0060] In a preferred embodiment, the structure of the boron-containing organic compound is represented by any one of the general formula (1-3) to the general formula (1-4):

[0061]

[0062] In the general formula (1-3) to the general formula (1-4), 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;

[0063] R 1 -R 19 Any two adjacent ones among them can be connected to form a ring;

[0064] Ar 1 、Ar 2Each occurrence of the same or different represents one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C1-C10 alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0065] X represents C, Si;

[0066] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C1-C10 alkyl, deuterium- or tritium-substituted C1-C10 alkyl, C6-C30 aryl, deuterium- or tritium-substituted C6-C30 aryl, C2-C30 heteroaryl, deuterium- or tritium-substituted C2-C30 heteroaryl.

[0067] In a preferred embodiment, in general formula (1-3) and general formula (1-4), R 1 -R 19 Any two adjacent ones of which can be linked 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.

[0068] In a preferred embodiment, R in general formula (1-3) and general formula (1-4) 1 -R 19 Each occurrence of the same or different represents:

[0069] A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, Or a phenyl group;

[0070] Said Ar 1 、Ar 2 Each occurrence of the same or different represents:

[0071] A methyl group, Any one of;

[0072] X represents C, Si.

[0073] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in general formula (2):

[0074]

[0075] In general formula (2), R 2 、R7 , R 10 , R 13 , R 16 , R 18 , Ar 1 , Ar 2 , X has the same definition as that in the general formula (A) above.

[0076] In a preferred embodiment, R 2 , R 7 , R 10 , R 13 , R 16 , R 18 are each independently represented as:

[0077] a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or any one of phenyl groups;

[0078] Each occurrence of said Ar 1 , Ar 2 is the same or different each time and is represented as:

[0079] a methyl group, any one of;

[0080] X is represented as C or Si.

[0081] In a preferred embodiment, the structure of the boron-containing organic compound is shown by any one of general formulas (2-1) to (2-2):

[0082]

[0083] In general formulas (2-1) to (2-2), R 2 , R 7 , R 10 , R 13 , R 18 , Ar 1 , Ar 2 , X has the same definition as that in the general formula (A) above.

[0084] In a preferred embodiment, R 2 , R 7 , R 10 , R 13 , R 18 are each independently represented as:

[0085] A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group;

[0086] Said Ar 1 and Ar 2 Each occurrence, whether the same or different, represents:

[0087] A methyl group, any one of;

[0088] X represents C or Si.

[0089] In a preferred embodiment, the structure of the boron-containing organic compound is represented by the general formula (3-1):

[0090]

[0091] In the general formula (3-1), each occurrence of R, whether 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;

[0092] X represents C or Si;

[0093] The substituents for the substituents are each independently selected from deuterium, tritium, a halogen atom, a cyano group, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium or tritium, a C6-C30 aryl group, a C6-C30 aryl group substituted with deuterium or tritium, a C5-C30 heteroaryl group, or a C2-C30 heteroaryl group substituted with deuterium or tritium.

[0094] In a preferred embodiment, each occurrence of R in the general formula (3-1), whether the same or different, independently represents:

[0095] A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group.

[0096] In a preferred embodiment, said R, R 1 -R 21Independently 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 anthraquinonyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group.

[0097] The said Ar 1 and Ar 2 are independently 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 anthraquinonyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group;

[0098] The said M 1 and M2 , M 3 , M 4 , M 5 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, 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;

[0099] The substituents substituting the above-mentioned substitutable 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, 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, or one or more thereof.

[0100] In a preferred embodiment, the R, R 1 -R 21 are each independently represented by the following structures:

[0101] A hydrogen atom, a cyano group, any one of;

[0102] The Ar 1 , Ar 2 is represented by any one of the following structures:

[0103] any one of;

[0104] The M 1 , M 2 , M 3 is represented by any one of the following ring structures:

[0105]

[0106] The M 4 , M 5 is represented by any one of the following ring structures:

[0107]

[0108] Z is represented as C-R a ;

[0109] R a Each occurrence is independently represented as a 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, 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, phenyl-substituted amino group, tert-butylbenzene-substituted amino group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl, xanthenone group, phenyl-substituted triazine group, phenyl-substituted boranyl group, methoxy group, tert-butoxy group, or one of the following.

[0110] In a preferred embodiment, R and R 1 -R 21 are each independently represented by the following structures:

[0111] a hydrogen atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, trifluoromethyl group, or any one of the following;

[0112] Ar 1 and Ar 2 are represented by the following structures:

[0113] a methyl group, or any one of the following;

[0114] M 1 and M 2 and M 3 are represented by the following ring structures:

[0115]

[0116] The M 4 , M 5 is represented by any one of the following ring structures:

[0117]

[0118] The Z is represented by C-R a ;

[0119] R a 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, or any one of them.

[0120] In a preferred embodiment, the specific structural formula of the boron-containing organic compound is any one of the following structures:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141] Preferred embodiment, the specific structural formula of the boron-containing organic compound is any one of the following structures:

[0142]

[0143]

[0144]

[0145] The present invention provides an organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer comprising a light-emitting layer, the light-emitting layer containing the boron-containing organic compound.

[0146] Preferred embodiment, the organic electroluminescent device sequentially comprises a substrate, an anode, an organic light-emitting functional layer and a cathode, the organic light-emitting functional layer comprising a light-emitting layer, the light-emitting layer containing the boron-containing organic compound.

[0147] Preferred embodiment, the organic electroluminescent device sequentially comprises a substrate, a cathode, an organic light-emitting functional layer and an anode, the organic light-emitting functional layer comprising a light-emitting layer, the light-emitting layer containing the boron-containing organic compound.

[0148] Preferred embodiment, the light-emitting layer comprises a host material and a doping material, the doping material containing the boron-containing organic compound.

[0149] Preferred embodiment, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material being a TADF material, the doping material being the boron-containing organic compound.

[0150] Preferred embodiment, the light-emitting layer comprises a host material, an exciton sensitizing material and a doping material, the exciton sensitizing material being a metal element-containing complex, the doping material being the boron-containing organic compound.

[0151] A material for an organic electroluminescent device, containing the boron-containing organic compound described above in the present invention.

[0152] An application of the boron-containing organic compound, applied to an organic electroluminescent device.

[0153] In a preferred embodiment, the organic light-emitting functional layer includes a light-emitting layer, and the boron-containing organic compound of the present invention is applied to the light-emitting layer.

[0154] A display element includes the organic electroluminescent device of the present invention.

[0155] A lighting device includes the organic electroluminescent device of the present invention.

[0156] An electronic device is equipped with the organic electroluminescent device of the present invention.

[0157] The beneficial technical effects of the present invention are as follows:

[0158] (1) The compound of the present invention is applied to an OLED device and can be used as a doping material for a light-emitting layer material. Under the action of an electric field, it can emit green fluorescence and can be applied to the fields of OLED lighting or OLED display;

[0159] (2) As a doping material, the compound of the present invention can significantly improve the device lifetime. BRIEF DESCRIPTION OF THE DRAWINGS

[0160] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0161] 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;

[0162] Figure 2 It is the spectral diagram of Compound 222;

[0163] Figure 3 It is the NMR spectrum of Compound 222;

[0164] Figure 4 It is the spectral diagram of Compound 186;

[0165] Figure 5 It is the NMR spectrum of Compound 186;

[0166] Figure 6 It is the spectral diagram of Compound 226;

[0167] Figure 7 It is the NMR spectrum of Compound 226;

[0168] Figure 8 It is the NMR spectrum of Compound 273;

[0169] Figure 9 It is the mass spectrum of Compound 273;

[0170] Figure 10 is the NMR spectrum of Compound 116;

[0171] Figure 11 is the NMR spectrum of Compound 190;

[0172] Figure 12 is the NMR spectrum of Compound 275;

[0173] Figure 13 is the NMR spectrum of Compound 331;

[0174] Figure 14 is the NMR spectrum of Compound 367. Detailed implementation manners

[0175] Next, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with 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 in conjunction with the accompanying drawings and specific embodiments, but it is not a limitation of the present invention.

[0176] 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, for example, 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.

[0177] 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 yl, substituted or unsubstituted bi-p-terphenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl, but not limited thereto.

[0178] 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, combinations thereof or fused rings of combinations of the foregoing groups, but not limited thereto.

[0179] 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.

[0180] 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.

[0181] In the present invention, substituted or unsubstituted C 5 -C 30Heteroaryl refers to substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, their combinations or fused rings of the foregoing group combinations, but not limited thereto.

[0182] The C1-C10 alkenyl group described in the present invention is preferably a C2-C8 alkenyl group, more preferably a C2-C5 alkenyl group, and its non-limiting examples may include vinyl, propenyl, isobutenyl, n-pentenyl, isopentenyl, neopenteneyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylethylene, 1,2-diphenylethylene, 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 not limited thereto.

[0183] The C1-C10 alkynyl group described in the present invention is preferably a C2-C8 alkynyl group, more preferably a C2-C5 alkynyl group, and its non-limiting examples may include ethynyl, propynyl, n-butynyl, isobutynyl, n-pentynyl, isopentynyl, neopentynyl, etc., but not limited thereto.

[0184] In the present invention, "can be connected to form a ring" means that two adjacent groups do not form a ring or are connected to form a ring with each other.

[0185] Preferably, it can be connected to form a substituted or unsubstituted aromatic ring of 6 to 30 members, a substituted or unsubstituted heteroaromatic ring of 5 to 30 members, or a substituted or unsubstituted aliphatic ring of 5 to 30 members.

[0186] In the present invention, the substituted or unsubstituted arylamino group described in the present invention means wherein Q 4 、Q 5 represent substituted or unsubstituted aromatic groups, and Q 4 、Q 5 are preferably represented as substituted or unsubstituted C 6 -C 30Aryl or substituted or unsubstituted C 2 -C 30 heteroaryl.

[0187] The halogen atom in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0188] The C 1 -C 10 alkoxy group refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, etc., but is not limited thereto.

[0189] In the present invention, the substituted or unsubstituted C 6 -C 30 aromatic ring refers to a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, but is not limited thereto.

[0190] 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 fluoranthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a combination thereof or a fused ring of the combination of the foregoing groups, but is not limited thereto.

[0191] The present invention provides a boron-containing organic compound and an organic light-emitting 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 light-emitting device, thereby greatly improving the lifespan of the device.

[0192] The organic light-emitting device of the present invention can be a bottom-emitting organic light-emitting device, a top-emitting organic light-emitting device, or a stacked organic light-emitting device, and there is no specific limitation thereto.

[0193] The organic light-emitting 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.

[0194] As the substrate of the organic light-emitting device of the present invention, any substrate commonly used in organic light-emitting 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 smoothnesses, and water resistances. Depending on the properties of the substrate, its usage directions are different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0195] The first electrode is formed on the 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 usually 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0196] The organic functional material layer disposed between the first electrode and the second electrode includes a hole transport region, a light-emitting layer, and an electron transport region in sequence from bottom to top.

[0197] In this article, the hole transport region constituting the organic light-emitting device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0198] 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.

[0199] Examples of the above materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinolone derivatives, styryl anthracene derivatives, styrylamine derivatives and other styrene compounds such as fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinylenes and their derivatives, polythiophenes and their derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other 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)quaterphenyls, 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.

[0200] Furthermore, 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 above-mentioned hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0201] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material, so as to be expected to achieve the occurrence of the 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 the hole injection conduction.

[0202] 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.

[0203] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further comprises a P-type doping material with charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetri(cyanomethanylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0204] 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.

[0205] 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.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] The light-emitting layer may comprise 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 the boron-containing organic compound represented by the general formula (1) of the present invention.

[0210] The light-emitting layer may comprise a single host material or a dual host material;

[0211] The dual host material comprises 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;

[0212] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy difference between the first singlet excited state and the first triplet excited state. Therefore, singlet excitons and triplet excitons generated simultaneously can be utilized in the device, enabling the exciton utilization rate generated electrochemically inside the device to approach 100% as much as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0213] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0214] An exciton sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to fully utilize electrochemically generated excitons, thereby enabling the light-emitting layer to finally generate the emission spectrum of the sensitized material. The exciton sensitizer may undertake functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing organic compound shown in the general formula (1) of the present invention is used in combination with the exciton sensitizing material, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0215] 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.

[0216] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0217] In the present invention, the electron transport region may sequentially include a hole blocking layer, an electron transport layer, and an electron injection layer disposed above the light-emitting layer from bottom to top, but is not limited thereto.

[0218] 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 efficacy of the device. The hole blocking layer of the present invention may be disposed above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art with hole blocking effects can be used, such as 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.

[0219] The electron transport layer can be disposed above the light-emitting layer or, if present, the hole-blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. A material with a high electron mobility is preferably used. As the electron transport layer of the organic electroluminescent device of the present invention, 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, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-bis(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201) and other imidazole derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon 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.

[0220] The electron injection layer can be disposed above the electron transport layer. The electron injection layer material is usually preferably a material with a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials known in the prior art for organic electroluminescent devices 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.

[0221] 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, 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.

[0222] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0223] The method for preparing the organic electroluminescent device of the present invention comprises 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 successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0224] The raw materials involved in the synthesis examples of the present invention can be purchased from the market or prepared by conventional preparation methods in the art;

[0225] Intermediate synthesis:

[0226] Synthesis of intermediate A series:

[0227]

[0228] Synthesis of intermediate A2: Add raw material N1 (2.05 g, 6.31 mmol), raw material M1 (1.54 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, 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.

[0229]

[0230] Synthesis of intermediate A3: Add raw material N1 (2.05 g, 6.31 mmol), raw material M2 (1.54 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, 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 A3.

[0231]

[0232] Synthesis of Intermediate A7: Refer to the synthesis of Intermediate A2, with the difference that raw material M3 is used to replace raw material M1.

[0233] Synthesis of Intermediate R series:

[0234]

[0235] Synthesis of Intermediate R5: Dissolve raw material S1 (0.76 g, 3.6 mmol) and raw material S2 (1.15 g, 4.3 mmol) in THF (80 ml), and sequentially add PdCl 2 (PPh 3 ) 2 (0.11 g, 0.15 mmol), CuI (0.07 g, 0.36 mmol) and triethylamine (40 ml). After displacing nitrogen three times, slowly heat the mixture to 80 °C and maintain for 12 hours. After cooling to room temperature, filter the reaction mixture to remove inorganic salts, and rotary evaporate to remove triethylamine. Pour the product into acidic water, wash the precipitate five times with deionized water, and dry overnight at 80 °C under vacuum. The crude product is subjected to silica gel column chromatography, using petroleum ether as the eluent to obtain the crude product, and then recrystallized to obtain Intermediate R5.

[0236]

[0237] Synthesis of Intermediate S5: Add raw material S3 (10 mmol, 3.39 g) and raw material S4 (10 mmol, 3.16 g) into a three-necked flask, dissolve with a mixed solvent (70 mL of 1,4-dioxane / water (volume ratio: 4:1), 35 mL of ethanol), then add Pd(dppf)Cl 2 (0.10 mmol, 0.07 g), 15 mL of 3 mol / L K 2 CO 3 aqueous solution, and heat under reflux for 4 hours under nitrogen protection. Take a sample for TLC to confirm the completion of the reaction. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, wash with chloroform, and evaporate the obtained filtrate under vacuum. Purify the obtained residue by column chromatography on silica gel, using hexane / toluene as the eluent, to obtain Intermediate S5.

[0238]

[0239] Synthesis of Intermediate R6: The preparation of Intermediate R6 refers to the synthesis of Intermediate R5, with the same reaction conditions and the same reactant equivalents, except that raw materials S1 and S2 of the reactants are replaced with raw material S6 and Intermediate S5, respectively.

[0240] Synthesis of Intermediate G series:

[0241]

[0242] Synthesis of Intermediate G1: Add raw material R1 (4.46 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P1 (5.54 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G1.

[0243]

[0244] Synthesis of Intermediate G2: Add raw material R2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P1 (5.54 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G2.

[0245]

[0246] Synthesis of Intermediate P2-1: Add raw material P2 (8.69 g, 30.80 mmol), copper(I) iodide (0.29 g, 1.54 mmol), diethylenetriamine (0.32 g, 3.08 mmol), sodium iodide (9.02 g, 60.16 mmol) into a two-necked flask, add 300 ml of anhydrous acetonitrile, reflux at heating for 24 h. After cooling, extract with ethyl acetate and wash with saturated brine to remove acetonitrile. Dry the organic phase with anhydrous sodium sulfate, rotary evaporate the solvent, then slurry with methanol, and recrystallize the solid with dichloromethane-methanol to obtain Intermediate P2-1.

[0247] Synthesis of Intermediate G3: Add raw material R2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add Intermediate P2-1 (8.23 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G3.

[0248]

[0249] Synthesis of Intermediate G4: Add raw material R1 (4.46 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P3 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain intermediate G4.

[0250]

[0251] Synthesis of Intermediate G5: Add raw material R2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P3 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain intermediate G5.

[0252]

[0253] Synthesis of Intermediate G6: Add raw material R3 (1.35 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P3 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain intermediate G6.

[0254]

[0255] Synthesis of Intermediate G7: Add raw material R1 (4.46 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P4 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G7.

[0256]

[0257] Synthesis of Intermediate G8: Add raw material R2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P4 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G8.

[0258]

[0259] Synthesis of Intermediate G10: Add raw material R4 (5.16 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P3 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G10.

[0260]

[0261] Synthesis of Intermediate G11: Add raw material R4 (5.16 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P4 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G11.

[0262]

[0263] Synthesis of Intermediate G12: Add intermediate R5 (9.97 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P3 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain intermediate G12.

[0264]

[0265] Synthesis of Intermediate G13: Add intermediate R5 (9.97 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P4 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain intermediate G13.

[0266]

[0267] Synthesis of Intermediate G14: Add intermediate R6 (11.97 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P3 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain intermediate G14.

[0268] Example 1: Synthesis of Compound 5:

[0269]

[0270] 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 intermediate 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.

[0271] 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.

[0272] Synthesis of intermediate D1: Under nitrogen protection, intermediate C1 (1.58 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and intermediate G1 (0.67 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.

[0273] Synthesis of Compound 5: Dissolve intermediate D1 (10.24 g, 12.5 mmol) in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, slowly add 10 mL of a 1.6 M solution of tert-butyllithium in n-pentane. Stir at 60 °C for 2 hours, then add boron tribromide (6.26 g, 25 mmol) at 0 °C. Stir the reaction mixture at room temperature for 1 hour. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0 °C and wait for the reaction mixture to reach room temperature. Stir at 130 °C for 6 hours, then cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 . Separate the mixture and extract with water and dichloromethane. The combined organic layers are condensed in vacuo, purified by column chromatography to obtain Compound 5.

[0274] Synthesis of Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, and their corresponding compounds 17, 41, 154, 182, 183, 186, 188, 204, 222, 268, 280, 327, 331, 343, 367, 321:

[0275] Synthesize the following target compounds by referring to the preparation process of Compound 5 in Example 1; the reaction conditions are the same, and the starting material E1 used is the same. The difference lies in using the intermediates / starting materials A, starting material F, and intermediate G listed in Table 2-1 below;

[0276] Table 2-1

[0277]

[0278]

[0279]

[0280]

[0281] Example 18: Synthesis of Compound 320:

[0282]

[0283] Synthesis of intermediate B2: Add starting material E2 (1.22 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) to a two-necked flask. Under nitrogen protection, add 50 mL of anhydrous DMF and stir at room temperature for 30 min. Under nitrogen protection, add intermediate A6 (1.79 g, 5 mmol) and stir at 140 °C for 12 h. Filter, wash with water, dry, and purify by column chromatography 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 stirred at N 2 Under the condition of 0℃, 10mL of hexane solution of n-butyl lithium (1.6M) was added dropwise; the mixture was stirred at 0℃ for 1 hour, and then 100mL of anhydrous toluene solution of raw material F3 (2.91g, 8.00mmol) was added dropwise; the reaction mixture was stirred at 35℃ 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 anhydrous Na 2 SO 4 After drying, filtration and evaporation, intermediate C2 was obtained by column chromatography.

[0285] Synthesis of intermediate D2: Under nitrogen protection, intermediate C2 (3.50 g, 4.9 mmol) was dissolved in 50 mL of toluene solution, and intermediate G4 (1.60 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 refluxed at 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 320: Intermediate D2 (12.47 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 9 mL of a n-pentane solution of tert-butyl lithium (1.6 M) was slowly added. The mixture was stirred at 60°C for 2 hours. Boron tribromide (6.26 g, 25 mmol) was added at 0°C, and 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 320.

[0287] Example 19: Synthesis of Compound 324:

[0288]

[0289] 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 intermediate A6 (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.

[0290] Synthesis of intermediate C3: N 2 Under atmosphere, 10 mL of n-butyl lithium (1.6 M) in hexane was added dropwise with stirring to 30 mL of anhydrous ether solution of intermediate B2 (4.19 g, 7.2 mmol); the mixture was stirred at 0°C for 1 hour, and then 10 mL of anhydrous toluene solution of raw material F5 (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 C3 was obtained by column chromatography.

[0291] Synthesis of intermediate D3: Under nitrogen protection, intermediate C3 (2.95 g, 4.9 mmol) was dissolved in 50 mL toluene solution, and intermediate G4 (1.60 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 returned 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 D3.

[0292] Synthesis of compound 324: Under nitrogen atmosphere at 0°C, 9 mL of a n-pentane solution of tert-butyllithium (1.6 M) was slowly added to 300 mL of a tert-butylbenzene solution of intermediate D3 (11.07 g, 12.5 mmol). After stirring at 60°C for 2 hours, the n-pentane was removed in vacuo. 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 (DIEA) (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 3Separate the mixture and extract it with water and dichloromethane. The combined organic layer was condensed in vacuo, chromatographed, and Compound 324 was obtained.

[0293] Synthesis of Examples 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and their corresponding compounds 83, 116, 190, 212, 226, 264, 273, 275, 409, 417, 481:

[0294] Refer to the preparation process of Compound 5 in Example 1 to synthesize the following target compounds; the reaction conditions are the same, and the starting material E1 used is the same, except that the intermediates / starting materials A, starting material F, and intermediate G listed in Table 2-2 below are used;

[0295] Table 2-2

[0296]

[0297]

[0298] The structural characterization, mass spectrometry analysis, and test results of the physical and chemical properties of the compounds obtained in each example are as follows:

[0299] The structural formula of Compound 5 (C 59 H 45 BN 2 ) Theoretical values: C, 89.38; H, 5.72; N, 3.53; Test values: C, 89.41; H, 5.64; N, 3.54. LC-MS: Measured value: 793.25 ([M+H] + )), exact mass: 792.37. PLQY is 98%, and FWHM is 25 nm.

[0300] The structural formula of Compound 17 (C 61 H 49 BN 2 ) Theoretical values: C, 89.25; H, 6.02; N, 3.41; Test values: C, 89.23; H, 6.09; N, 3.37. LC-MS: Measured value: 821.42 ([M+H]+), exact mass: 820.40. PLQY is 96%, and FWHM is 27 nm.

[0301] The structural formula of Compound 41 (C 67 H 61 BN 2)Theoretical values: C, 88.92; H, 6.79; N, 3.10; Measured values: C, 88.99; H, 6.86; N, 3.00. LC-MS: Measured value: 905.46 ([M+H]+), Exact mass: 904.49. PLQY is 97%, FWHM is 28 nm.

[0302] Structural formula of Compound 154 (C 77 H 79 BN 2 )Theoretical values: C, 88.65; H, 7.63; N, 2.69; Measured values: C, 88.57; H, 7.58; N, 2.72. LC-MS: Measured value: 1043.86 ([M+H]+), Exact mass: 1042.63. PLQY is 94%, FWHM is 26 nm.

[0303] Structural formula of Compound 182 (C 55 H 31 BN 2 )Theoretical values: C, 90.41; H, 4.28; N, 3.83; Measured values: C, 90.44; H, 4.20; N, 3.92. LC-MS: Measured value: 731.16 ([M+H]+), Exact mass: 730.26. PLQY is 98%, FWHM is 27 nm.

[0304] Structural formula of Compound 183 (C 57 H 35 BN 2 )Theoretical values: C, 90.23; H, 4.65; N, 3.69; Measured values: C, 90.19; H, 4.59; N, 3.74. LC-MS: Measured value: 759.40 ([M+H]+), Exact mass: 758.29. PLQY is 96%, FWHM is 24 nm.

[0305] Structural formula of Compound 186 (C 63 H 47 BN 2 )Theoretical values: C, 89.77; H, 5.62; N, 3.32; Measured values: C, 89.75; H, 5.52; N, 3.33. LC-MS: Measured value: 843.30 ([M+H]+), Exact mass: 842.38. PLQY is 94%, FWHM is 24 nm.

[0306] Figure 4 is the spectrogram of Compound 186, Test conditions (toluene solution, 5×10 -5 M), Test equipment: Horiba Fluorolog-3 scientific research grade fluorescence spectrometer.

[0307] Figure 5 It is the NMR spectrum of compound 186.

[0308] The structural formula of compound 188 (C 65 H 51 BN 2 ): Theoretical values: C, 89.64; H, 5.90; N, 3.22; Measured values: C, 89.61; H, 5.80; N, 3.18. LC-MS: Measured value: 871.29 ([M+H]+), Exact mass: 870.41. PLQY is 97%, FWHM is 26 nm.

[0309] The structural formula of compound 204 (C 65 H 51 BN 2 ): Theoretical values: C, 89.64; H, 5.90; N, 3.22; Measured values: C, 89.60; H, 5.86; N, 3.13. LC-MS: Measured value: 871.62 ([M+H]+), Exact mass: 870.41. PLQY is 93%, FWHM is 25 nm.

[0310] The structural formula of compound 222 (C 71 H 63 BN 2 ): Theoretical values: C, 89.29; H, 6.65; N, 2.93; Measured values: C, 89.38; H, 6.75; N, 2.98. LC-MS: Measured value: 955.30 ([M+H]+), Exact mass: 954.51. PLQY is 97%, FWHM is 26 nm.

[0311] Figure 2 It is the spectrogram of compound 222, test conditions (toluene solution, 5×10 -5 M), test equipment: Horiba Fluorolog-3 scientific research grade fluorescence spectrometer.

[0312] Figure 3 It is the NMR spectrum of compound 222.

[0313] The structural formula of compound 268 (C 71 H 63 BN 2 ): Theoretical values: C, 89.29; H, 6.65; N, 2.93; Measured values: C, 89.30; H, 6.67; N, 2.98. LC-MS: Measured value: 955.77 ([M+H]+), Exact mass: 954.51. PLQY is 98%, FWHM is 27 nm.

[0314] The structural formula of compound 280 (C53 H 43 BN 2 ) Theoretical values: C, 88.57; H, 6.03; N, 3.90; Measured values: C, 88.53; H, 6.11; N, 3.98. LC-MS: Measured value: 719.40 ([M+H]+), Exact mass: 718.35. PLQY is 97%, FWHM is 28 nm.

[0315] Structural formula of compound 320 (C 70 H 63 BN 2 Si) Theoretical values: C, 86.57; H, 6.54; N, 2.88; Measured values: C, 86.48; H, 6.58; N, 2.87. LC-MS: Measured value: 971.48 ([M+H] + ) Exact mass: 970.49. PLQY is 93%, FWHM is 25 nm.

[0316] Structural formula of compound 324 (C 62 H 47 BN 2 Si) Theoretical values: C, 86.70; H, 5.52; N, 3.26; Si, 3.27; Measured values: C, 86.67; H, 5.43; N, 3.30; Si, 3.26. LC-MS: Measured value: 859.54 ([M+H] + ) Exact mass: 858.36. PLQY is 97%, FWHM is 29 nm.

[0317] Structural formula of compound 327 (C 55 H 31 BN 2 ) Theoretical values: C, 90.41; H, 4.28; N, 3.83; Measured values: C, 90.47; H, 4.25; N, 3.86. LC-MS: Measured value: 731.15 ([M+H]+), Exact mass: 730.26. PLQY is 97%, FWHM is 28 nm.

[0318] Structural formula of compound 331 (C 63 H 47 BN 2 ) Theoretical values: C, 89.77; H, 5.62; N, 3.32; Measured values: C, 89.83; H, 5.56; N, 3.37. LC-MS: Measured value: 843.63 ([M+H] + ) Exact mass: 842.38. PLQY is 94%, FWHM is 25 nm.

[0319] Figure 13It is the NMR spectrum of Compound 331.

[0320] The structural formula of Compound 343 (C 65 H 51 BN 2 ): Theoretical values: C, 89.64; H, 5.90; N, 3.22; Measured values: C, 89.60; H, 5.84; N, 3.24. LC-MS: Measured value: 871.38 ([M+H]+), Exact mass: 870.41. PLQY is 97%, FWHM is 25 nm.

[0321] The structural formula of Compound 367 (C 71 H 63 BN 2 ): Theoretical values: C, 89.29; H, 6.65; N, 2.93; Measured values: C, 89.27; H, 6.72; N, 3.01. LC-MS: Measured value: 955.67 ([M+H]+), Exact mass: 954.51. PLQY is 97%, FWHM is 24 nm.

[0322] Figure 14 It is the NMR spectrum of Compound 367.

[0323] The structural formula of Compound 321 (C 79 H 79 BN 2 ): Theoretical values: C, 88.90; H, 7.46; N, 2.62; Measured values: C, 88.88; H, 7.36; N, 2.56. LC-MS: Measured value: 1067.61 ([M+H] + ), Exact mass: 1066.63. PLQY is 96%, FWHM is 28 nm.

[0324] The structural formula of Compound 83 (C 56 H 39 BN 2 ): Theoretical values: C, 89.59; H, 5.24; N, 3.73; Measured values: C, 89.56; H, 5.23; N, 3.74. LC-MS: Measured value: 751.41 ([M+H]+), Exact mass: 750.32.

[0325] The structural formula of Compound 116 (C 71 H 69 BN 2 ): Theoretical values: C, 88.72; H, 7.24; N, 2.91; Measured values: C, 88.71; H, 7.22; N, 2.89. LC-MS: Measured value: 961.72 ([M+H]+), Exact mass: 960.56.

[0326] Figure 10 It is the NMR spectrum of Compound 116.

[0327] The structural formula of Compound 190 (C 65 H 51 BN 2 ) Theoretical values: C, 89.64; H, 5.90; N, 3.22; Measured values: C, 89.60; H, 5.89; N, 3.17. LC-MS: Measured value: 871.28 ([M+H]+), Exact mass: 870.41.

[0328] Figure 11 It is the NMR spectrum of Compound 190.

[0329] The structural formula of Compound 212 (C 58 H 37 BN 2 ) Theoretical values: C, 90.15; H, 4.83; N, 3.63; Measured values: C, 90.21; H, 4.79; N, 3.61. LC-MS: Measured value: 773.33 ([M+H]+), Exact mass: 772.30.

[0330] The structural formula of Compound 226 (C 73 H 67 BN 2 ) Theoretical values: C, 89.18; H, 6.87; N, 2.85; Measured values: C, 89.24; H, 6.86; N, 2.86. LC-MS: Measured value: 983.66 ([M+H]+), Exact mass: 982.54.

[0331] Figure 6 It is the spectrum of Compound 226, test conditions (toluene solution, 5×10 -5 M), Test equipment: Horiba Fluorolog-3 scientific research grade fluorescence spectrometer.

[0332] Figure 7 It is the NMR spectrum of Compound 226.

[0333] The structural formula of Compound 264 (C 60 H 41 BN 2 ) Theoretical values: C, 89.99; H, 5.16; N, 3.50; Measured values: C, 89.96; H, 5.18; N, 3.52. LC-MS: Measured value: 801.20 ([M+H]+), Exact mass: 800.34.

[0334] The structural formula of Compound 273 (C 79 H 75 BN2 ) Theoretical values: C, 89.24; H, 7.11; N, 2.63; Measured values: C, 89.23; H, 7.08; N, 2.73. LC-MS: Measured value: 1063.74 ([M+H]+), Exact mass: 1062.60.

[0335] Figure 8 It is the NMR spectrum of compound 273.

[0336] Figure 9 It is the mass spectrum of compound 273.

[0337] Structural formula of compound 275 (C 79 H 79 BN 2 ) Theoretical values: C, 88.90; H, 7.46; N, 2.62; Measured values: C, 88.86; H, 7.49; N, 2.58. LC-MS: Measured value: 1067.81 ([M+H]+), Exact mass: 1066.63.

[0338] Figure 12 It is the NMR spectrum of compound 275.

[0339] Structural formula of compound 409 (C 60 H 41 BN 2 ) Theoretical values: C, 89.99; H, 5.16; N, 3.50; Measured values: C, 89.98; H, 5.22; N, 3.51. LC-MS: Measured value: 801.43 ([M+H]+), Exact mass: 800.34.

[0340] Structural formula of compound 417 (C 79 H 75 BN 2 ) Theoretical values: C, 89.24; H, 7.11; N, 2.63; Measured values: C, 89.14; H, 7.14; N, 2.64. LC-MS: Measured value: 1063.90 ([M+H]+), Exact mass: 1062.60.

[0341] Structural formula of compound 481 (C 85 H 83 BN 2 ) Theoretical values: C, 89.29; H, 7.32; N, 2.45; Measured values: C, 89.33; H, 7.29; N, 2.38. LC-MS: Measured value: 1143.54 ([M+H]+), Exact mass: 1142.66.

[0342] 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.

[0343] From the above compound data, it can be seen that the compounds of the present invention have 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.

[0344] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-30 and Device Comparative Examples 1-5. The manufacturing processes of the devices in Device Examples 1-30 of the present invention are exactly the same as those in Device Comparative Examples 1-5, 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 Table 3 and Table 4 respectively.

[0345] Device Example 1

[0346] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness: 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), pure water, and dried in sequence, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED device is fabricated. GH-1 and GH-2 are used as the host materials, and Compound 5 is used as the doping material. The mass ratio of GH-1, GH-2, and Compound 5 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 with a film thickness of 5 nm is continuously evaporated by vacuum evaporation. This layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq with a mass ratio of 1:1 and a film thickness of 30 nm are continuously evaporated by vacuum evaporation. 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 by a vacuum evaporation device. 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 and a mass ratio of Mg and Ag of 1:9 is fabricated by a vacuum evaporation device. This layer is used as the cathode layer 10.

[0347] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 31-60 and Device Comparative Examples 6-10. The manufacturing processes of the devices in Device Examples 31-60 of the present invention are exactly the same as those in Device Comparative Examples 6-10, and the same substrate materials and electrode materials are used. 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 Table 3 and Table 4 respectively.

[0348] Device Example 31

[0349] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first doping material, and Compound 5 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and Compound 5 is 66:30:3:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0350] The molecular structural formulas of the related materials are as follows:

[0351]

[0352] The comparative compounds ref-1, ref-2, ref-3, ref-4, and ref-5 are prepared according to the methods described in the prior art.

[0353] After completing the OLED light-emitting device as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency and the lifetime of the device are measured. Device examples and comparative examples prepared by the same method are shown in Table 3; the test results of the current efficiency and lifetime of the obtained devices are shown in Table 4.

[0354] Table 3

[0355]

[0356]

[0357]

[0358] Table 4

[0359]

[0360]

[0361] Note: The current efficiency and emission peak are measured using an IVL (current-voltage-luminance) test system (Suzhou Fosida Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester of System Technology Research Co., Ltd. in Japan; LT95 refers to the time when the device luminance decays to 95%; all data are tested at 10 mA / cm 2 under.

[0362] From the device data results in Table 4, it can be seen that compared with Comparative Examples 1-5 of the device, the device lifetime of the compound of the present invention in the single-doping system device is higher than that of Comparative Examples 1-5; in the single-doping system device, the device efficiency also shows good results; compared with Comparative Examples 6-10 of the device, in the double-doping system device using an exciton sensitizing material as the first doping, both the current efficiency and the device lifetime of the device are greatly improved compared with the OLED device of the known material, and in the double-doping device, the device efficiency is also significantly improved compared with that in the single-doping case.

[0363] 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 in the general formula (A-1): In the general formula (A-1), 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; Ar 1 、Ar 2 Each occurrence, the same or different, is one of a hydrogen atom, 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 2 、M 3 、M 4 、M 5 are each independently represented by an aromatic ring of C 6 ~C 30 which is substituted or unsubstituted, or a 5- to 30-membered heteroaromatic ring which is substituted or unsubstituted; X represents C or Si; The substituent for the substitutable group is arbitrarily selected from any one of deuterium, a halogen atom, a cyano group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a C2-C30 heteroaryl group, and a deuterium-substituted C2-C30 heteroaryl group.

2. The boron-containing organic compound according to claim 1, characterized in that the structure of the boron-containing organic compound is shown in the general formula (A): In general formula (A), R 1 -R 19 each occurrence, independently of the others, is 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; Ar 1 、Ar 2 each occurrence is independently one of the same or different substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heteroaryl; M 1 represents one of a substituted or unsubstituted aryl ring of C 6 to C 30 and a substituted or unsubstituted 5- to 30-membered heteroaryl ring; 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 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, and any one of them.

3. A boron-containing organic compound, characterized in that the structure of the boron-containing organic compound is shown in any one of the general formulas (1-1) to (1-2): In General Formulas (1-1) to (1-2), R 1 -R 21 Each occurrence, which may be the same or different, 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 1 、Ar 2 each occurrence is independently one of the same or different substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, 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, 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.

4. The boron-containing organic compound according to claim 1, characterized in that the structure of the boron-containing organic compound is shown in any one of the general formulas (1-3) to (1-4): In General Formulas (1-3) to (1-4), 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; Ar 1 、Ar 2 each occurrence is independently 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, or a substituted or unsubstituted C2-C30 heteroaryl group, which may be the same or different; 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, and any one of them.

5. The boron-containing organic compound according to claim 2, characterized in that the structure of the boron-containing organic compound is shown in the general formula (2): In general formula (2), R 2 , R 7 , R 10 , R 13 , R 16 , R 18 , Ar 1 , Ar 2 , and X have the same meanings as defined in claim 2.

6. The boron-containing organic compound according to claim 2, characterized in that the structure of the boron-containing organic compound is shown in any one of the general formulas (2-1) to (2-2): In General Formulas (2-1) to (2-2), the meanings of R 2 , R 7 , R 10 , R 13 , R 18 , Ar 1 , Ar 2 and X are the same as those defined in Claim 2.

7. The boron-containing organic compound according to claim 2, characterized in that the structure of the boron-containing organic compound is shown in the general formula (3-1): In the general formula (3-1), each occurrence of R, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-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; 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 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, 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 oxanthrone group, a phenyl-substituted triazinyl group; The Ar 1 , Ar 2 are each independently represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, 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, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl; The M 1 , M 2 , M 3 , M 4 , M 5 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 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; the substituent for the above-mentioned substitutable group is arbitrarily selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

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, 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 1 and Ar 2 each independently represents 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, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl; The M 1 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 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; The substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

10. The boron-containing organic compound according to claim 3, wherein, The R 1 -R 21 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 1 and Ar 2 each independently represents 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, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl; the substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

11. The boron-containing organic compound according to claim 4, wherein, 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 xanthone group, a phenyl-substituted triazine group; The Ar 1 and Ar 2 each independently represents phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, 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, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl; the substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

12. The boron-containing organic compound according to claim 5, wherein, The R 2 , R 7 , R 10 , R 13 , R 16 , R 18 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 group, an oxanthrone group, a phenyl-substituted triazinyl group; Said Ar 1 and Ar 2 each independently represents 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, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl;​ the substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

13. The boron-containing organic compound according to claim 6, wherein, The R 2 , R 7 , R 10 , R 13 , R 18 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 group, an xanthone group, a phenyl-substituted triazine group; The Ar 1 and Ar 2 each independently represents 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, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl; The substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl 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 dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

14. The boron-containing organic compound according to claim 7, wherein, each of the Rs independently represents 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 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 tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl group, an xanthenone group, and a phenyl-substituted triazinyl group; The substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a tert-pentyl group, a butyl 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 dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

15. The boron-containing organic compound according to claim 1, wherein, The said R 1 -R 19 are respectively independently represented as the following structures: A hydrogen atom, a cyano group, any one of; The said Ar 1 , Ar 2 is represented in the following structure: any one of; The said M 1 , M 2 , M 3 is represented as any one of the following ring structures: The said M 4 , M 5 is represented as any one of the following ring structures: wherein Z is represented as C-R a ; R a Each occurrence is independently represented by one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl 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 phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a 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.

16. The boron-containing organic compound according to claim 2, wherein, Said R 1 -R 19 Are each independently represented by the following structures: A hydrogen atom, a cyano group, any one of; The Ar 1 , Ar 2 is represented in the following structure: any one of; The said M 1 is represented as any one of the following ring structures: wherein Z is represented as C-R a ; R a Each occurrence is independently represented by one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl 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 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, and a spirofluorene group.

17. The boron-containing organic compound according to claim 3, wherein, The said R 1 -R 21 are each independently represented by the following structures: Hydrogen atom, cyano group, any one of; The described Ar 1 , Ar 2 is represented in the following structure: Any one of them.

18. The boron-containing organic compound according to claim 4, wherein, The said R 1 -R 19 are each independently represented by the following structures: a hydrogen atom, a cyano group, any one of; The Ar 1 , Ar 2 is represented in the following structure: Any one of them.

19. The boron-containing organic compound according to claim 5, wherein, The said R 2 , R 7 , R 10 , R 13 , R 16 , R 18 are each independently represented as the following structures: A hydrogen atom, a cyano group, any one of; The Ar 1 , Ar 2 is represented in the following structure: Any one of them.

20. The boron-containing organic compound according to claim 6, wherein, The said R 2 , R 7 , R 10 , R 13 , R 18 are each independently represented as the following structures: A hydrogen atom, a cyano group, any one of; The Ar 1 , Ar 2 is represented as the following structure: Any one of them.

21. The boron-containing organic compound according to claim 7, wherein, R is independently represented by the following structures respectively: A hydrogen atom, a cyano group, any one of them.

22. A boron-containing organic compound, characterized in that the structure of the boron-containing organic compound is represented by the general formula (A-1): The said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 Each time the same or different appearance is represented as: A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; The said Ar 1 and Ar 2 Each occurrence, whether the same or different, is represented as: methyl any one of; The said M 1 , M 2 , M 3 is represented as any one of the following ring structures: The said M 4 , M 5 is represented as the following ring structure: wherein Z is represented as C-R a ; R a Each occurrence is independently represented as: a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or any one of phenyl groups; X is represented by C or Si.

23. The boron-containing organic compound according to claim 22, characterized in that the structure of the boron-containing organic compound is represented by the general formula (A): Said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 Each occurrence, whether the same or different, is represented as: A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; The described Ar 1 and Ar 2 Each occurrence, whether the same or different, is represented as: methyl any one of; The said M 1 is represented as any one of the following ring structures: wherein Z is represented as C-R a ; R a Each occurrence is independently represented as: a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; X is represented by C or Si.

24. The boron-containing organic compound according to claim 22, characterized in that the structure of the boron-containing organic compound is represented by any one of the general formulas (1-1) to (1-2): The said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 Each occurrence, whether the same or different, is represented as: A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; The said Ar 1 and Ar 2 Each occurrence, whether the same or different, is represented as: methyl any one of X is represented by C or Si.

25. The boron-containing organic compound according to claim 22, characterized in that the structure of the boron-containing organic compound is represented by any one of the general formulas (1-3) to (1-4): The said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 Each time the same or different appearance is represented as: Any one of a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; The described Ar 1 and Ar 2 Each occurrence, whether the same or different, is represented as: methyl any one of; X is represented by C or Si.

26. The boron-containing organic compound according to claim 22, characterized in that the structure of the boron-containing organic compound is represented by the general formula (2): The said R 2 、R 7 、R 10 、R 13 、R 16 、R 18 Each occurrence, whether the same or different, is represented as: A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; The Ar 1 and Ar 2 Each occurrence, whether the same or different, is represented as: methyl any one of; X is represented by C or Si.

27. The boron-containing organic compound according to claim 22, characterized in that the structure of the boron-containing organic compound is represented by any one of the general formulas (2-1) to (2-2): Said R 2 、R 7 、R 10 、R 13 、R 18 Each occurrence, whether the same or different, is represented as: A hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, or a phenyl group; The said Ar 1 and Ar 2 Each occurrence, whether the same or different, is represented as: methyl any one of; X is represented by C or Si.

28. 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:

29. An organic electroluminescent device, including a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer including a light-emitting layer, characterized in that the light-emitting layer contains the boron-containing organic compound according to any one of claims 1-28.

30. The organic electroluminescent device according to claim 29, characterized in that the light-emitting layer contains a host material and a doping material, and the doping material contains the boron-containing organic compound according to any one of claims 1-28.

31. The organic electroluminescent device according to claim 29, the light-emitting layer contains a first host material, a second host material and a doping material, characterized in that at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-28.

32. The organic electroluminescent device according to claim 29, the light-emitting layer contains 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 the boron-containing organic compound according to any one of claims 1-28.

33. A material for an organic electroluminescent device, characterized in that it contains the boron-containing organic compound according to any one of claims 1-28.

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

35. The application according to claim 34, characterized in that the organic light-emitting functional layer in the organic electroluminescent device includes a light-emitting layer, and the boron-containing organic compound according to any one of claims 1-28 is applied to the light-emitting layer.

36. A display element, characterized in that, it includes the organic electroluminescent device according to any one of claims 29-32.

37. A lighting device, characterized in that, it includes the organic electroluminescent device according to any one of claims 29-32.

38. An electronic device, characterized in that, it is equipped with the organic electroluminescent device according to any one of claims 29-32.

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