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 field of semiconductor technology. The structure of the organic compound of the present invention is shown in general formula (1). When the compound of the present invention is used as a doping material in the light-emitting layer material of an OLED light-emitting device, it can be used as a green light doping material of the light-emitting layer of the organic electroluminescent device, thereby improving the light-emitting color purity and efficiency of the device.

Description

Technical Field

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

[0002] Traditional fluorescent doped materials are limited by early technologies and can only use 25% of singlet excitons formed by electrical excitation to emit light. The internal quantum efficiency of the device is low (up to 25%), and the external quantum efficiency is generally less than 5%, which is far behind the efficiency of phosphorescent devices. Since the strong spin-orbit coupling of the heavy atom center enhances intersystem crossing, phosphorescent materials can effectively use singlet and triplet excitons formed by electrical excitation to emit light, making the internal quantum efficiency of the device reach 100%. However, most phosphorescent materials are expensive, have poor material stability, poor color purity, and serious device efficiency roll-off, which limits their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are placed on color rendering standards. In addition to being efficient and stable, luminescent materials also require a narrower half-width to improve the purity of the device's luminescent color. Fluorescent doped materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doped materials have achieved a phased breakthrough, and the half-width of boron materials can be reduced to below 30nm. In the green light region, which is more sensitive to the human eye, research is mainly focused on phosphorescent doped materials, but their luminescent peak shape is difficult to narrow by simple methods. Therefore, in order to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doped materials with narrow half-width.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials with fluorescent doping materials, uses triplet exciton-sensitizing materials as exciton-sensitizing media, makes full use of triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0005] Boron compounds with a resonant structure are more likely to achieve narrow half-width luminescence. Such materials are used in sensitization technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN 110492006 A disclose a luminescent layer combination technology with a TADF material having a difference between the lowest singlet and the lowest triplet energy level of less than or equal to 0.2eV as the main body and a boron-containing material as the doping; CN110492005A and CN 110492009 A disclose a luminescent layer combination scheme with an exciplex as the main body and a boron-containing material as the doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of 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 of the light-emitting layer of the organic electroluminescent device, thereby improving the luminescent color purity and life of the device.

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

[0008]

[0009] In the general formula (1), Z a , Z b , Z c Each occurrence of the same or different is represented by CH or CR b ;

[0010] R b Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0011] M2 is represented by the general formula (1-1);

[0012] In the general formula (1-1), the asterisk indicates the site where the ring can be connected;

[0013] Dashed lines indicate no connection or connection via a single bond, Z d -Z d , Z e -Z e , Z f -Z f Two of the groups are directly connected via CC keys, and the remaining group is not connected;

[0014] Z, Z d , Z e , Z f Each occurrence of the same or different is represented by C, CH or CR a ;

[0015] R a Each occurrence of the same or different atoms may be a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0016] M1 represents a substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0017] Ar1 and Ar2 represent substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0018] X represents one of O, S, N(R1), C(R2)(R3), Si(R4)(R5);

[0019] R1 represents a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0020] R1 can also form a ring with the M1 ring bond;

[0021] R2, R3, R4, and R5 are independently substituted or unsubstituted C1-C 10Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0022] R2 and R3 can also bond to each other to form a ring;

[0023] R4 and R5 can also bond to each other to form a ring;

[0024] The substituent of the above-mentioned substitutable group can be selected from deuterium atom, tritium atom, halogen atom, cyano group, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0025] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0026] In a preferred embodiment, the structure of the boron-containing organic compound is shown in general formula (2):

[0027]

[0028] In the general formula (2), the dashed line indicates no connection or connection through a single bond, Z d -Z d , Z e -Z e , Z f -Z f Two of the groups are directly connected via CC keys, and the remaining group is not connected;

[0029] Z, Z d , Z e , Z f Each occurrence of the same or different is represented by C, CH or CR a ;

[0030] R a Each occurrence of the same or different atoms may be a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0031] Z a , Z b , Z c Each occurrence of the same or different is represented by CH or CR b ;

[0032] R b Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0033] M1 represents a substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0034] Ar1 and Ar2 represent substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0035] X represents one of O, S, N(R1), C(R2)(R3), Si(R4)(R5);

[0036] R1 represents a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0037] R1 can also form a ring with the M1 ring bond;

[0038] R2, R3, R4, and R5 are independently substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0039] R2 and R3 can also bond to each other to form a ring;

[0040] R4 and R5 can also bond to each other to form a ring;

[0041] The substituents for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0042] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0043] In a preferred embodiment, the structure of the organic compound is as shown in general formula (3) to general formula (6):

[0044]

[0045] In the general formula (3) to the general formula (6), Z, M1, X, Ar1, Ar2, Z a , Z b , Z c has the same meaning as defined above.

[0046] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (7) to (16):

[0047]

[0048]

[0049] In the general formulae (7) to (16), Z, X, Ar1, Ar2, Z a , Z b , Z c has the same meaning as defined above;

[0050] Y is represented by one of O and S;

[0051] Each occurrence of Z1, Z2, Z3, Z4, Z5, Z6 is represented by C, CH or CR c ;

[0052] R c Each occurrence of the same or different deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0053] The substituents for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0054] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0055] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of the general formulas (17) to (54):

[0056]

[0057]

[0058]

[0059] In the general formulae (17) to (54), Z, Ar1, Ar2, Z b is as defined above;

[0060] Ar3 and Ar4 represent substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0061] Each occurrence of Z1, Z2, Z3, Z4, Z5, Z6, Z7 is represented by C, CH or CR c ;

[0062] R c Each occurrence of the same or different deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0063] The substituents for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0064] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0065] In a preferred embodiment, the structure of the organic compound is as shown in any one of general formulas (55) to (69):

[0066]

[0067]

[0068] In the general formulas (55) to (69), R b independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0069] Ra1-Ra 111 are independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0070] The substituents for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0071] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0072] Preferably, R1, R a , R b , R c 、Ra1-Ra 111 It is represented by the following structure:

[0073]

[0074]

[0075] In a preferred embodiment, Ar1, Ar2, Ar3, and Ar4 are represented by the following structure:

[0076]

[0077] Preferably, the M1 is represented by any one of the following ring structures:

[0078]

[0079] The definition of Z is the same as above.

[0080] Preferably, the R a , R b , R c 、Ra1-Ra 111Each of the following is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated benzene group phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9, 9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, tert-butoxy;

[0081] R1, R2, R3, R4, and R5 are independently represented by adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl , tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9 - one of dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy;

[0082] The Ar1, Ar2, Ar3, and Ar4 are independently phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted phenyl, tert-butyl ... substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert-butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated ethyl substituted biphenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted biphenyl, phenyl substituted amino, tert-butylbenzene substituted amino, tert-butyl substituted dibenzofuranyl, phenyl substituted tert-butyl, xanthone, phenyl substituted triazine, phenyl substituted boryl, methoxy, tert-butoxy;

[0083] The M1 is represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone;

[0084] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl 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 pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

[0085] In a preferred embodiment, the specific structure of the boron-containing organic compound is any one of the following structures:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] An organic electroluminescent device comprises a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0104] In a preferred embodiment, the light-emitting layer comprises a main material and a doping material, and the doping material contains the boron-containing organic compound.

[0105] In a preferred embodiment, the light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing organic compound.

[0106] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material, wherein the exciton-sensitizing material is a complex containing a metal element, and the doping material contains the boron-containing organic compound.

[0107] The beneficial technical effects of the present invention are:

[0108] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit green fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields;

[0109] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0110] (3) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

[0111] (4) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and the luminous efficiency of the device;

[0112] The compound of the invention has a narrow half-peak width and a high fluorescence quantum yield, and can be used as a green light doping material of a light-emitting layer of an organic electroluminescent device, thereby improving the light-emitting color purity and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0113] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0114] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. DETAILED DESCRIPTION

[0115] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0116] In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, the words "upper", "lower", "top" and "bottom" used to indicate orientation only indicate the orientation in a certain state, and do not mean that the related structure can only exist in the orientation described; on the contrary, if the structure can change its position, such as inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" or "upper" side.

[0117] In the present invention, the substituted or unsubstituted C6-C 30 Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted The invention may include, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, and a substituted or unsubstituted indenyl group.

[0118] In the present invention, substituted or unsubstituted C2-C 30The heteroaryl group refers to a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted The invention also includes substituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, 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 phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or fused rings of combinations of the foregoing groups, but is not limited thereto.

[0119] The C1-C 10 Alkyl (including straight-chain alkyl and branched 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 and the like, but is not limited thereto.

[0120] The C3-C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring atoms. In this article, C4-C9 cycloalkyl is preferably used, C5-C8 cycloalkyl is more preferably used, and C5-C7 cycloalkyl is particularly preferably used. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl and cycloheptyl, but are not limited thereto.

[0121] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use direction is different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0122] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the first electrode is a transmissive electrode, it may 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). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may 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 typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.

[0123] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light emitting layer and an electron transport region.

[0124] Herein, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0125] As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials used for OLED devices.

[0126] Examples of the above materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quilone derivatives, styryl anthracene derivatives, styrylamine derivatives and the like, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinyl and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and the like, conductive polymer oligomers, aromatic tertiary amine compounds, styrene amination compounds, compounds, triamines, tetraamines, benzidines, propargyl diamine 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)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds.

[0127] Furthermore, according to the device matching requirements, the hole transport film layer between the electron blocking layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a superposition structure of multiple hole transport materials. In this article, for the above-mentioned hole carrier conduction film layers with different functions, their film thickness is not particularly limited.

[0128] The hole injection layer contains a main organic material that can conduct holes, and also contains a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the main organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doped material, so that the charge transfer state between the main material and the dopant material can be realized, the ohmic contact between the buffer layer and the anode can be achieved, and the efficient injection from the electrode to the hole injection conduction can be achieved.

[0129] In view of the above empirical summary, for hole-type host materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0130] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer also includes 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-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited to these.

[0131] 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.

[0132] The thickness of the hole injection layer of the present invention may be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0133] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0134] The thickness of the electron blocking layer of the present invention may be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0135] 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.

[0136] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of the present invention.

[0137] The light-emitting layer may contain a single host material or a dual host material;

[0138] The dual-host material comprises a first host material and a second host material, and preferably at least one of the first host material and the second host material is a TADF material;

[0139] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy level difference between the first excited singlet state and the first excited triplet state, so that the singlet excitons and triplet excitons generated can be used simultaneously in the device, making the utilization rate of the excitons generated by the device as close to 100% as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0140] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0141] Exciton sensitizing materials refer to materials that can make the luminescent material in the luminescent layer fully utilize the electroexcitons, so that the luminescent layer finally produces the emission spectrum of the sensitized material. Exciton sensitizers may undertake functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has a significant improvement effect on the problems of device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0142] 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.

[0143] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and the driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-40 nm, but the thickness is not limited to this range.

[0144] In the present invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light emitting layer, but is not limited thereto.

[0145] The hole blocking layer is a layer that blocks the holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the efficiency of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, for example, phenanthroline derivatives such as bathocuproin (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene) bis (9H-carbazole) and the like pyrimidine derivatives. The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, but the thickness is not limited to this range.

[0146] The electron transport layer may be disposed on the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials for organic electroluminescent devices known in the prior art 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-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-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-based compound derivatives, etc. The thickness of the electron transport layer of the present invention may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0147] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, 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 may 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.

[0148] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0149] 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.

[0150] 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.

[0151] Synthesis Example

[0152] 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;

[0153] Synthesis of raw material D-1:

[0154]

[0155]

[0156] Preparation of intermediate a-1:

[0157] Under nitrogen protection, 3.47g of raw material A-1, 0.88g of NaOH and 20mL of methanol were added to a three-necked flask, and 10mL of methanol solution containing 2.18g of raw material B-1 was added dropwise under ice-water bath conditions, and stirred at room temperature for 2 hours. After the reaction, the organic phase was washed with water and collected, concentrated, and then purified by silica gel column chromatography to obtain intermediate a-1. LC-MS: Measured value: 508.15 ([M+H] + ), theoretical value: 507.12.

[0158] Preparation of intermediate b-1:

[0159] Under nitrogen protection, 5.07 g of intermediate a-1, 2.45 g of raw material C-1, 1.68 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 30 mL of anhydrous toluene were added to a three-necked flask and refluxed for 17 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 673.23 ([M+H] + ), theoretical value: 672.18.

[0160] Preparation of intermediate c-1:

[0161] 3.36 g of intermediate b-1, 40 mL of N,N-dimethylformamide (DMAc), 0.11 g of palladium acetate, 3.45 g of potassium carbonate, 0.81 g of tetra-n-butylammonium bromide and 1.97 g of triphenylphosphine were added to a two-necked bottle in sequence, and the mixture was heated under reflux and stirred for 12 hours. The reaction solution was filtered and concentrated, and the compound was separated by passing through a silica gel column with petroleum ether as a developing solvent to obtain intermediate c-1. LC-MS: Measured value: 593.21 ([M+H] + ), theoretical value: 592.25.

[0162] Preparation of intermediate c-2:

[0163] Intermediate c-2 and intermediate c-1 are products of the same reaction. LC-MS: Measured value: 593.29 ([M+H] + ), theoretical value: 592.25.

[0164] Preparation of raw material D-1:

[0165] Under nitrogen protection, 5.92 g of intermediate c-1 and 30 mL of methanol were added to a three-necked flask, and 5 mL of 3M hydrochloric acid solution was slowly added dropwise under ice-water bath conditions. After the reaction was completed, the liquids were separated and extracted with 3×20 mL of dichloromethane. The organic phase was collected, concentrated, and purified by silica gel column chromatography to obtain the raw material D-1. LC-MS: Measured value: 433.25 ([M+H] + ), theoretical value: 432.16.

[0166] Synthesis of raw material D-2:

[0167]

[0168] Preparation of raw material D-2:

[0169] The preparation of raw material D-2 is similar to that of raw material D-1, except that intermediate c-1 is replaced by intermediate c-2. LC-MS: Measured value: 433.11 ([M+H] + ), theoretical value: 432.16.

[0170] Synthesis of raw material D-3:

[0171]

[0172]

[0173] Preparation of intermediate d-1:

[0174] Under nitrogen protection, 5.07 g of intermediate a-1, 1.27 g of raw material E-1, 1.68 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 30 mL of anhydrous toluene were added to a three-necked flask and refluxed for 16 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate d-1. LC-MS: Measured value: 555.47 ([M+H] + ), theoretical value: 554.21.

[0175] Preparation of intermediate e-1:

[0176] 2.77 g of intermediate d-1, 30 mL of N,N-dimethylformamide (DMAc), 0.11 g of palladium acetate, 3.45 g of potassium carbonate, 0.81 g of tetra-n-butylammonium bromide and 1.97 g of triphenylphosphine were added to a two-necked bottle in sequence, and the mixture was heated under reflux and stirred for 10 hours. The reaction solution was filtered and concentrated, and the compound was separated by passing through a silica gel column with petroleum ether as a developing solvent to obtain intermediate e-1. LC-MS: Measured value: 519.30 ([M+H] + ), theoretical value: 518.24.

[0177] Preparation of intermediate f-1:

[0178] Under nitrogen protection, 5.18 g of intermediate e-1, 2.81 g of raw material F-1, 1.68 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 30 mL of anhydrous toluene were added to a three-necked flask and refluxed for 20 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate f-1. LC-MS: Measured value: 673.20 ([M+H] + ), theoretical value: 672.18.

[0179] Preparation of intermediate c-3:

[0180] 3.36 g of intermediate f-1, 30 mL of N,N-dimethylformamide (DMAc), 0.11 g of palladium acetate, 3.45 g of potassium carbonate, 0.81 g of tetra-n-butylammonium bromide and 1.97 g of triphenylphosphine were added to a two-necked bottle in sequence, and the mixture was heated under reflux and stirred for 13 hours. The reaction solution was filtered and concentrated, and the compound was separated by a silica gel column using petroleum ether as a developing solvent to obtain intermediate c-3. LC-MS: Measured value: 593.33 ([M+H] + ), theoretical value: 592.25.

[0181] Preparation of raw material D-3:

[0182] The preparation of raw material D-3 is similar to that of raw material D-1, except that intermediate c-1 is replaced by intermediate c-3. LC-MS: Measured value: 433.19 ([M+H] + ), theoretical value: 432.16.

[0183] Synthesis of raw material D-4:

[0184]

[0185] Preparation of intermediate a-2:

[0186] Under nitrogen protection, 3.03g of raw material A-2, 0.88g of NaOH and 25mL of methanol were added to a three-necked flask, and 10mL of methanol solution in which 2.18g of raw material B-1 was dissolved was added dropwise under ice-water bath conditions, and the mixture was stirred at room temperature for 2.5 hours. After the reaction, the organic phase was washed with water and collected, concentrated, and then purified by silica gel column chromatography to obtain intermediate a-2. LC-MS: Measured value: 464.27 ([M+H] + ), theoretical value: 463.17.

[0187] Preparation of intermediate b-2:

[0188] Under nitrogen protection, 4.63 g of intermediate a-2, 3.57 g of raw material C-2, 1.68 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 30 mL of anhydrous toluene were added to a three-necked flask and refluxed for 16 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-2. LC-MS: Measured value: 785.28 ([M+H] + ), theoretical value: 784.30.

[0189] Preparation of intermediate c-4:

[0190] 3.92 g of intermediate b-2, 30 mL of N,N-dimethylformamide (DMAc), 0.11 g of palladium acetate, 3.45 g of potassium carbonate, 0.81 g of tetra-n-butylammonium bromide and 1.97 g of triphenylphosphine were added to a two-necked bottle in sequence, and the mixture was heated under reflux and stirred for 19 hours. The reaction solution was filtered and concentrated, and the compound was separated by a silica gel column using petroleum ether as a developing solvent to obtain intermediate c-4. LC-MS: Measured value: 705.44 ([M+H] + ), theoretical value: 704.38.

[0191] Preparation of raw material D-4:

[0192] The preparation of raw material D-4 is similar to that of raw material D-1, except that intermediate c-1 is replaced by intermediate c-4. LC-MS: Measured value: 545.27 ([M+H] + ), theoretical value: 544.29.

[0193] Synthesis of raw material D-5:

[0194]

[0195] Preparation of intermediate b-3:

[0196] Under nitrogen protection, 5.07 g of intermediate a-1, 3.57 g of raw material C-2, 1.68 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 30 mL of anhydrous toluene were added to a three-necked flask and refluxed for 28 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate b-3. LC-MS: Measured value: 785.36 ([M+H] + ), theoretical value: 784.30.

[0197] Preparation of intermediate c-5:

[0198] 3.92 g of intermediate b-3, 30 mL of N,N-dimethylformamide (DMAc), 0.11 g of palladium acetate, 3.45 g of potassium carbonate, 0.36 mL of tetra-n-butylammonium bromide and 1.97 g of triphenylphosphine were added to a two-necked bottle in sequence, and the mixture was heated under reflux and stirred for 15 hours. The reaction solution was filtered and concentrated, and the compound was separated by passing through a silica gel column with petroleum ether as a developing solvent to obtain intermediate c-5. LC-MS: Measured value: 705.41 ([M+H] + ), theoretical value: 704.38.

[0199] Preparation of raw material D-5:

[0200] The preparation of raw material D-5 is similar to that of raw material D-1, except that intermediate c-1 is replaced by intermediate c-5. LC-MS: Measured value: 545.34 ([M+H] + ), theoretical value: 544.29.

[0201] Example 1 Synthesis of Compound 114:

[0202]

[0203] Preparation of intermediate g-1:

[0204] Under nitrogen protection, 3.34 g of raw material E-1, 1.22 g of raw material F-1, 2.07 g of potassium carbonate, 0.56 g of Pd(PPh3)4 and 30 mL of anhydrous toluene were added to a three-necked flask and refluxed for 6 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate g-1. LC-MS: Measured value: 284.91 ([M+H] + ), theoretical value: 283.94.

[0205] Preparation of intermediate h-1:

[0206] Under nitrogen protection, 4.32g of raw material D-1, 0.49g of NaH dissolved in mineral oil and 30mL of anhydrous DMF were added to a three-necked flask. After reacting for 2 hours at room temperature, 2.84g of intermediate g-1 solution dissolved in 15mL DMF was slowly added dropwise and the reaction was continued with stirring for 10 hours. After the reaction was completed, 100mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate h-1. LC-MS: Measured value: 697.15 ([M+H] + ), theoretical value: 696.10.

[0207] Preparation of intermediate i-1:

[0208] Under nitrogen protection, 6.96 g of intermediate h-1, 1.49 g of raw material G-1, 2.07 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 12 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate i-1. LC-MS: Measured value: 766.33 ([M+H] + ), theoretical value: 765.29.

[0209] Preparation of intermediate k-1:

[0210] Under nitrogen protection, 7.65 g of intermediate i-1, 2.68 g of raw material H-1, 1.68 g of potassium tert-butoxide, 0.45 g of Pd2(dba)3, 0.36 mL of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 12 hours in the dark. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate k-1. LC-MS: Measured value: 954.41 ([M+H] + ), theoretical value: 953.36.

[0211] Preparation of compound 114:

[0212] In a sealed pressure tube, under nitrogen protection, 9.53g of intermediate k-1 and 35mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M tert-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reverse reaction for 2 hours, the reaction was cooled to -42°C, 1.5mL of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 12 hours. After cooling to 0°C, 3.48mL of ultra-dry N,N-diisopropylethylamine was added dropwise, and the reaction solution was heated to 180°C for 12 hours. Cool to room temperature, remove low-boiling solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate, separate and purify with column chromatography to obtain compound 114. Compound 114 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 26 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ 1.26-1.40 (18H, m), 6.82 (2H, m), 7.10 (2H, m), 7.41-7.73 (11H, m), 7.78-8.20 (9H, m), 8.29-8.42 (2H, m), 8.50 (1H, d), 8.72-8.91 (2H, m), 8.93-9.02 (3H, m).

[0213] Example 2 Synthesis of Compound 116:

[0214]

[0215] Preparation of intermediate h-2:

[0216] Under nitrogen protection, 2.79 g of raw material C-3, 0.48 g of NaH dissolved in mineral oil and 20 mL of anhydrous DMF were added to a three-necked flask. After reacting for 2 hours at room temperature, 2.67 g of raw material E-2 solution dissolved in 15 mL of DMF was slowly added dropwise and the reaction was continued with stirring for 10 hours. After the reaction was completed, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane. After drying and filtering with anhydrous sodium sulfate, the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate h-2. LC-MS: Measured value: 528.20 ([M+H] + ), theoretical value: 527.16.

[0217] Preparation of intermediate k-2:

[0218] Under nitrogen protection, 4.32g of raw material D-3, 0.48g of NaH dissolved in mineral oil and 20mL of anhydrous DMF were added to a three-necked flask. After reacting for 1 hour at room temperature, 5.27g of intermediate h-2 solution dissolved in 15mL DMF was slowly added dropwise and the reaction was continued with stirring for 8 hours. After the reaction was completed, 100mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate k-2. LC-MS: Measured value: 940.41 ([M+H] + ), theoretical value: 939.32.

[0219] Preparation of compound 116:

[0220] In a sealed pressure-resistant tube, under nitrogen protection, 9.40 g of intermediate k-2 and 35 mL of o-dichlorobenzene were added. 4.8 mL of 2.5 M n-butyl lithium in n-hexane solution was added at 0 ° C, heated to 60 ° C and reacted for 2 hours, then 1.5 mL of boron tribromide was added at 0 ° C, transferred to room temperature and continued to react for 4 hours, then 3.48 mL of N, N-diisopropylethylamine was added to the system at 0 ° C, heated to 200 ° C and reacted for 12 hours. After the reaction was completed, the organic layer was reduced pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 116. Compound 116 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 20 nm, which is measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0221] Example 3 Synthesis of Compound 117:

[0222]

[0223] Preparation of intermediate k-3:

[0224] Under nitrogen protection, 4.32g of raw material D-2, 0.49g of NaH dissolved in mineral oil and 30mL of anhydrous DMF were added to a three-necked flask. After reacting at room temperature for 0.5 hours, 5.27g of intermediate h-2 solution dissolved in 15mL of DMF was slowly added dropwise and the reaction was continued with stirring for 12 hours. After the reaction was completed, 100mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate k-3. LC-MS: Measured value: 940.49 ([M+H] + ), theoretical value: 939.32.

[0225] Preparation of compound 117:

[0226] In a sealed pressure-resistant tube, under nitrogen protection, 9.40 g of intermediate k-3 and 35 mL of o-dichlorobenzene were added. 4.8 mL of 2.5 M n-butyl lithium in n-hexane solution was added at 0 ° C, the system was heated to 60 ° C and reacted for 2 hours, then 1.5 mL of boron tribromide was added at 0 ° C, the system was transferred to room temperature and continued to react for 5 hours, then 3.48 mL of N, N-diisopropylethylamine was added to the system at 0 ° C, heated to 200 ° C and reacted for 12 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 117. Compound 117 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 22 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ 2.05-2.15 (18H, d), 7.23-7.45 (11H, m), 7.67-8.09 (11H, m), 8.16-8.25 (2H, m), 8.43-8.59 (5H, m), 9.02 (1H, d).

[0227] Example 4 Synthesis of Compound 120:

[0228]

[0229] Preparation of intermediate h-3:

[0230] Under nitrogen protection, 1.44 g of raw material I-1, 2.68 g of raw material E-2, 4.23 g of cesium carbonate and 20 mL of anhydrous DMF were added to a three-necked flask and heated to reflux for 2 hours. After the reaction, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved with dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate h-3. LC-MS: Measured value: 393.11 ([M+H] + ), theoretical value: 392.02.

[0231] Preparation of intermediate k-4:

[0232] Under nitrogen protection, 4.32 g of raw material D-3, 0.49 g of NaH dissolved in mineral oil and 20 mL of anhydrous DMF were added to a three-necked flask. After reacting for 2 hours at room temperature, a solution of 3.92 g of intermediate h-3 dissolved in 15 mL of DMF was slowly added dropwise and the reaction was continued with stirring for 11 hours. After the reaction was completed, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate k-4. LC-MS: Measured value: 805.26 ([M+H] + ), theoretical value: 804.18.

[0233] Preparation of compound 120:

[0234] In a sealed pressure-resistant tube, under nitrogen protection, 8.04 g of intermediate k-4 and 35 mL of o-dichlorobenzene were added. 4.8 mL of 2.5 M n-butyl lithium in n-hexane solution was added at 0 ° C, the system was heated to 60 ° C and reacted for 2 hours, then 1.5 mL of boron tribromide was added at 0 ° C, the system was transferred to room temperature and continued to react for 2 hours, then 3.48 mL of N, N-diisopropylethylamine was added to the system at 0 ° C, heated to 200 ° C and reacted for 10 hours. After the reaction was completed, the organic layer was reduced pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 120. Compound 120 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 19 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0235] Example 5 Synthesis of Compound 418:

[0236]

[0237] Preparation of intermediate h-4:

[0238] Under nitrogen protection, 1.44 g of raw material I-1, 2.48 g of raw material E-3, 4.23 g of cesium carbonate and 40 mL of anhydrous DMF were added to a three-necked flask and heated to reflux for 4 hours. After the reaction, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved with dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate h-4. LC-MS: Measured value: 373.14 ([M+H] + ), theoretical value: 372.05.

[0239] Preparation of intermediate k-5:

[0240] Under nitrogen protection, 5.44 g of raw material D-4, 0.49 g of NaH dissolved in mineral oil and 20 mL of anhydrous DMF were added to a three-necked flask. After reacting for 2 hours at room temperature, 3.72 g of intermediate h-4 solution dissolved in 15 mL of DMF was slowly added dropwise and the reaction was continued with stirring for 8 hours. After the reaction was completed, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered over anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate k-5. LC-MS: Measured value: 897.50 ([M+H] + ), theoretical value: 896.33.

[0241] Preparation of compound 418:

[0242] In a sealed pressure-resistant tube, under nitrogen protection, 8.97 g of intermediate k-5 and 35 mL of o-dichlorobenzene were added. 4.8 mL of 2.5 M tert-butyl lithium in n-hexane solution was added at 0 ° C, the system was heated to 60 ° C and reacted for 3 hours, then 1.5 mL of boron tribromide was added at 0 ° C, the system was transferred to room temperature and continued to react for 2 hours, then 3.48 mL of N, N-diisopropylethylamine was added to the system at 0 ° C, heated to 200 ° C and reacted for 10 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 418. Compound 418 was dissolved in a toluene solution (1×10 -5 M) The half-peak width is 20 nm, which is measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ 1.82 (9H, s), 1.89-2.10 (18H, d), 7.13 (1H, d), 7.37-7.79 (10H, m), 7.82-8.14 (7H, m), 8.22-8.45 (2H, m), 8.67-8.90 (2H, m), 8.93-9.05 (2H, m).

[0243] Example 6 Synthesis of Compound 423:

[0244]

[0245] Preparation of intermediate h-5:

[0246] Under nitrogen protection, 3.19 g of raw material C-4, 0.49 g of NaH dissolved in mineral oil and 20 mL of anhydrous DMF were added to a three-necked flask. After reacting for 1 hour at room temperature, 2.48 g of raw material E-3 solution dissolved in 15 mL of DMF was slowly added dropwise and the reaction was continued with stirring for 5 hours. After the reaction was completed, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate h-5. LC-MS: Measured value: 548.20 ([M+H] + ), theoretical value: 547.13.

[0247] Preparation of intermediate k-6:

[0248] Under nitrogen protection, 5.44 g of raw material D-5, 0.49 g of NaH dissolved in mineral oil and 30 mL of anhydrous DMF were added to a three-necked flask. After reacting for 1 hour at room temperature, 5.47 g of intermediate h-5 solution dissolved in 15 mL of DMF was slowly added dropwise and the reaction was continued with stirring for 12 hours. After the reaction was completed, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate k-6. LC-MS: Measured value: 1072.55 ([M+H] + ), theoretical value: 1071.41.

[0249] Preparation of compound 423:

[0250] In a sealed pressure tube, under nitrogen protection, 10.72 g of intermediate k-6 and 45 mL of o-dichlorobenzene were added, and 4.8 mL of 2.5 M n-butyl lithium in n-hexane solution was added at 0°C. The system was heated to 60°C and reacted for 3 hours. Then, 1.5 mL of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 3 hours. Then, 3.48 mL of N,N-diisopropylethylamine was added to the system at 0°C, and the reaction was heated to 200°C and reacted for 8 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 423. Compound 423 was dissolved in a toluene solution (1×10 -5 M) The half-peak width is 18 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0251] Example 7 Synthesis of Compound 429:

[0252]

[0253] Preparation of intermediate h-6:

[0254] Under nitrogen protection, 3.19 g of raw material C-4, 2.68 g of raw material E-2, 4.23 g of cesium carbonate and 30 mL of anhydrous DMF were added to a three-necked flask and heated to reflux for 6 hours. After the reaction, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved with dichloromethane, dried and filtered with anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate h-6. LC-MS: Measured value: 568.22 ([M+H] + ), theoretical value: 567.10.

[0255] Preparation of intermediate k-7:

[0256] Under nitrogen protection, 5.44 g of raw material D-5, 0.49 g of NaH dissolved in mineral oil and 30 mL of anhydrous DMF were added to a three-necked flask. After reacting for 2 hours at room temperature, 5.68 g of intermediate h-6 solution dissolved in 15 mL of DMF was slowly added dropwise and the reaction was continued with stirring for 10 hours. After the reaction was completed, 100 mL of water was added, the precipitate was filtered, and the precipitate was dissolved in dichloromethane, dried and filtered over anhydrous sodium sulfate, and the organic phase was concentrated and then purified by silica gel column chromatography to obtain intermediate k-7. LC-MS: Measured value: 1092.41 ([M+H] + ), theoretical value: 1091.38.

[0257] Preparation of compound 429:

[0258] In a sealed pressure-resistant tube, under nitrogen protection, 10.9 g of intermediate k-7 and 45 mL of o-dichlorobenzene were added. 4.8 mL of 2.5 M tert-butyl lithium in n-hexane was added at 0 ° C, the system was heated to 60 ° C and reacted for 2 hours, then 1.5 mL of boron tribromide was added at 0 ° C, the system was transferred to room temperature and continued to react for 4 hours, then 3.48 mL of N, N-diisopropylethylamine was added to the system at 0 ° C, heated to 200 ° C and reacted for 10 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 429. Compound 429 was dissolved in a toluene solution (1×10 -5 M) The half-peak width is 21 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0259] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0260] Table 1

[0261]

[0262]

[0263] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-7 and device comparison examples 1-3. The device manufacturing process of device embodiments 2-7 and device comparison examples 1-3 of the present invention is exactly the same as that of device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also consistent. The difference is that the doping material of the light-emitting layer in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-1 and Table 3 respectively:

[0264] Device Example 1

[0265] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washing with a cleaning agent (Semiclean M-L20), washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 114 as the doping material, the mass ratio of GH-1, GH-2 and compound 114 is 69:30:1, and the light-emitting layer has a film thickness of 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0266] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 8-14 and device comparative examples 4-6. The device manufacturing process of device embodiments 9-14 and device comparative examples 4-6 of the present invention is exactly the same as that of device embodiment 8, and the same substrate material and electrode material are used. The film thickness of the electrode material is also consistent. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-2 and Table 3 respectively:

[0267] Device Example 8

[0268] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 to HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Then, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, GD-1 as the first doping material, and compound 114 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 114 is 66:30:3:1, and the thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 is vacuum-deposited with a film thickness of 5nm. This layer is the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq are vacuum-deposited. The mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1nm is prepared 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 80nm is prepared by a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0269] The molecular structure formula of the relevant materials is shown below:

[0270]

[0271] After the OLED light-emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2-1 and Table 2-2; the test results of the current efficiency and life of the obtained device are shown in Table 3.

[0272] Table 2-1

[0273]

[0274]

[0275] Table 2-2

[0276]

[0277] Table 3

[0278]

[0279] Note: Current efficiency and luminescence peak are tested using IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); life test system is EAS-62C OLED device life tester from Japan System Technology Co., Ltd.; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are at 10mA / cm 2 Next test.

[0280] It can be seen from the device data results in Table 3 that, compared with the comparative compounds ref-1, ref-2, and ref-3, the luminescence peak of the compound of the present invention is between 510 and 550 nm, and the green luminescence effect can be well achieved; compared with device comparison examples 1-6, the organic light-emitting device of the present invention, whether in a single-doping system or a double-doping system, has a greatly improved current efficiency and lifespan relative to OLED devices of known materials; when an exciton-sensitizing material is used as the first doping, the device efficiency is significantly improved compared with a single doping.

[0281] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that The structures of the organic compounds are shown in general formula (3) to general formula (6): In general formula (3) to general formula (6), each occurrence of Z is the same or different and is represented by CH or CR a ; R a Each occurrence of the same or different radicals may be represented by hydrogen atoms, deuterium atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 One of the cycloalkyl groups; Z a , Z b , Z c Each occurrence of the same or different is represented by CH or CR b ; R b Each occurrence of the same or different radicals may be represented by hydrogen atoms, deuterium atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, 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 triazinyl, One of; M1 is represented by any of the following ring structures: Ar1 and Ar2 represent phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, 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, One of; X represents one of O and N(R1); R1 represents phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, 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, One of; The substituent for the substituent group is selected from one or more of a deuterium atom, a cyano group, an adamantyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a phenyl group, a biphenyl group, and a naphthyl 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 any one of general formulas (7) to (16): In the general formulae (7) to (16), Z, X, Ar1, Ar2, Z a , Z b , Z c has the same meaning as defined in claim 1; Y is represented by one of O and S; Each occurrence of Z1, Z2, Z3, Z4, Z5, Z6 is represented by C, CH or CR c ; R c Each occurrence of the same or different deuterium atom, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 One of the cycloalkyl groups; The substituent for the substituent group is selected from one or more of a deuterium atom, adamantyl, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, biphenyl, and naphthyl.

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 (17) to (24) and (33) to (54): In the general formulae (17) to (24) and (33) to (54), each occurrence of Z, which is the same or different, is represented by CH or CR. a ; R a Each occurrence of the same or different radicals may be represented by hydrogen atoms, deuterium atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 One of the cycloalkyl groups; Z b Each occurrence of the same or different is represented by CH or CR b ; R b Each occurrence of the same or different radicals may be represented by hydrogen atoms, deuterium atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, 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 triazinyl, One of; Ar1, Ar2, Ar3, and Ar4 represent phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, and 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, One of; Each occurrence of Z1, Z2, Z3, Z4, Z5, Z6, Z7 is represented by C, CH or CR c ; R c Each occurrence of the same or different deuterium atom, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 One of the cycloalkyl groups; The substituent for the substituent group is selected from one or more of a deuterium atom, a cyano group, an adamantyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a phenyl group, a biphenyl group, and a naphthyl group.

4. The boron-containing organic compound according to claim 3, characterized in that The structure of the organic compound is shown in any one of the general formulas (55) to (69): In the general formulas (55) to (69), R b independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, 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 triazinyl, One of; Ra1-Ra 111 are independently represented by one of a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; The substituent for the substituent group is selected from one or more of a deuterium atom, a cyano group, an adamantyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a phenyl group, a biphenyl group, and a naphthyl group.

5. The boron-containing organic compound according to claim 1, characterized in that The R1 is represented by the following structure: The R b It is represented by the following structure: Hydrogen atoms, The R a It is represented by the following structure: Hydrogen atoms, The Ar1 and Ar2 are represented by the following structures: The M1 is represented by any of the following ring structures: The definition of Z is the same as that in claim 1.

6. The boron-containing organic compound according to claim 2, characterized in that The R1 is represented by the following structure: The R b It is represented by the following structure: Hydrogen atoms, The R a , R c It is represented by the following structure: Hydrogen atoms, The Ar1 and Ar2 are represented by the following structures:

7. The boron-containing organic compound according to claim 3, characterized in that The R b It is represented by the following structure: Hydrogen atoms, The R a , R c It is represented by the following structure: Hydrogen atoms, The Ar1, Ar2, Ar3, and Ar4 are represented by the following structures:

8. The boron-containing organic compound according to claim 1, characterized in that The R b A hydrogen atom, a deuterium atom, 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 dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted benzene group The present invention is one of the following: phenyl substituted with a tert-butyl group, 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, tert-butyl substituted phenyl, and phenyl substituted triazinyl; The R a It is represented by one of a hydrogen atom, a deuterium atom, 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, and a cyclohexyl group; The R1 is phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted bi ... One of propyl-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, tert-butyl-substituted phenyl; The Ar1 and Ar2 are independently phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted diphenyl, tert-butyl ... One of biphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, and tert-butyl substituted phenyl; The M1 represents one of phenyl, deuterated phenyl, naphthyl, benzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, and tert-butyl-substituted phenyl; The substituent for the substituent group is selected from one or more of a deuterium atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, biphenyl, and naphthyl.

9. The boron-containing organic compound according to claim 2, characterized in that The R b The hydrogen atom, deuterium atom, adamantyl group, methyl group, deuterated methyl 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, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted benzene group The present invention is one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 101, 114, 125, 134, 146, 159, 115, 126, 135, 147, 159, 15 The R a , R c are independently represented by one of a hydrogen atom, a deuterium atom, 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, and a cyclohexyl group; The R1 is phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted bi ... One of propyl-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, tert-butyl-substituted phenyl; The Ar1 and Ar2 are independently phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted diphenyl, tert-butyl ... One of biphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, and tert-butyl substituted phenyl; The substituent for the substituent group is selected from one or more of a deuterium atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, biphenyl, and naphthyl.

10. The boron-containing organic compound according to claim 3, characterized in that: The R b The hydrogen atom, deuterium atom, adamantyl group, methyl group, deuterated methyl 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, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted benzene group The present invention is one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 101, 114, 125, 134, 146, 159, 115, 126, 135, 147, 159, 15 The R a , R c are independently represented by one of a hydrogen atom, a deuterium atom, 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, and a cyclohexyl group; The Ar1, Ar2, Ar3, and Ar4 are independently phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl One of 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, tert-butyl substituted phenyl; The substituent for the substituent group is selected from one or more of a deuterium atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, biphenyl, and naphthyl.

11. The boron-containing organic compound according to claim 4, characterized in that The R b The hydrogen atom, deuterium atom, adamantyl group, methyl group, deuterated methyl 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, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted benzene group The present invention is one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 101, 114, 125, 134, 146, 159, 115, 126, 135, 147, 159, 15 Ra1-Ra 111 are independently represented by one of a hydrogen atom, a deuterium atom, an adamantyl group, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; The substituent for the substituent group is selected from one or more of a deuterium atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, biphenyl, and naphthyl.

12. A boron-containing organic compound, characterized in that: The specific structure of the boron-containing organic compound is any one of the following structures:

13. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, characterized in that: The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 12.

14. The organic electroluminescent device according to claim 13, characterized in that: The light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to any one of claims 1 to 12.

15. The organic electroluminescent device according to claim 13, characterized in that: The light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-12.

16. The organic electroluminescent device according to claim 13, characterized in that: The light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material. The exciton-sensitizing material is a complex containing a metal element, and the doping material contains the boron-containing organic compound according to any one of claims 1 to 12.

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