Deuterated boron-containing organic compound and organic electroluminescent device prepared from deuterated boron-containing organic compound

Abstract

The invention discloses a deuterated boron-containing organic compound and an organic electroluminescent device prepared from the deuterated boron-containing organic compound, and belongs to the technical field of semiconductors. The structure of the organic compound is shown as a general formula (1), # imgabs0. The compound is used as a luminescent layer green light doping material of an organic electroluminescent device, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The invention relates to the field of semiconductor technology, and in particular to a deuterated boron-containing organic compound 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. This type of material is 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 110492006A 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; CN 110492005 A and CN 110492009A 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. 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 deuterated boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a green light doping material for the light-emitting layer of the organic electroluminescent device.

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

[0008]

[0009] In the general formula (1), each occurrence of R1-R2 is the same or different and represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0010] Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0011] M1, M2, M3, M4, and M5 are each independently R-substituted or unsubstituted C6-C 30 One of an aromatic ring of R, a 5- to 30-membered heteroaromatic ring substituted or unsubstituted by R, and a C6-C10 aliphatic ring substituted or unsubstituted by R;

[0012] R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0013] X represents C, Si;

[0014] a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 10;

[0015] a, b, c, d, e, f, g, h, k are not all 0 at the same time;

[0016] The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

[0017] Preferably, a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 7;

[0018] Preferably, a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 5;

[0019] Preferably, a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 3;

[0020] Preferably, a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 2;

[0021] Preferably, a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 1;

[0022] In a preferred embodiment, the structure of the deuterated boron-containing organic compound is shown in the general formula (1-1):

[0023]

[0024] In the general formula (1-1), R1-R2, which are the same or different each time, represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0025] Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0026] M1 represents R substituted or unsubstituted C6~C 30 One of an aromatic ring of R, a 5- to 30-membered heteroaromatic ring substituted or unsubstituted by R, and a C6-C10 aliphatic ring substituted or unsubstituted by R;

[0027] R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0028] X represents C, Si;

[0029] e, f, g, h, and k are each independently an integer from 0 to 10;

[0030] a1, b1, a2, b2 are each independently an integer from 0 to 3;

[0031] c1, d1, c2, d2 are each independently an integer from 0 to 4;

[0032] a1, b1, c1, d1, e, f, g, h, k are not all 0 at the same time;

[0033] The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

[0034] In a preferred embodiment, the structure of the deuterated boron-containing organic compound is represented by any one of the general formulas (2-1) to (2-3):

[0035]

[0036] In the general formula (2-1) to the general formula (2-3), R1-R2 are the same or different each time and represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0037] Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0038] R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0039] X represents C, Si;

[0040] f, g, h, and k are each independently an integer from 0 to 10;

[0041] a1, b1, a2, b2, e1 are each independently an integer from 0 to 3;

[0042] c1, d1, c2, d2 are each independently an integer of 0-4; e2 is an integer of 0-5;

[0043] a1, b1, c1, d1, e1, f, g, h, k are not all 0 at the same time;

[0044] a1, b1, c1, d1, e2, f, g, h, k are not all 0 at the same time;

[0045] The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

[0046] In a preferred embodiment, the structure of the deuterated boron-containing organic compound is shown in any one of the general formulas (3-1) to (3-3):

[0047]

[0048] In the general formula (3-1) to the general formula (3-3), R1-R2 are the same or different each time and represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0049] Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0050] R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0051] X represents C, Si;

[0052] f, g, h, and k are each independently an integer from 0 to 10;

[0053] a1, b1, a2, b2, e1 are each independently an integer from 0 to 3;

[0054] c1, d1, c2, d2 are each independently an integer of 0-4; e2 is an integer of 0-5;

[0055] a1, b1, c1, d1, e1, f, g, h, k are not all 0 at the same time;

[0056] a1, b1, c1, d1, e2, f, g, h, k are not all 0 at the same time;

[0057] The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

[0058] In a preferred embodiment, the structure of the deuterated boron-containing organic compound is shown in any one of the general formulas (4-1) to (4-3):

[0059]

[0060] In the general formula (4-1) to the general formula (4-3), R1-R2 are the same or different each time and represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0061] Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0062] R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0063] X represents C, Si;

[0064] f, g, h, and k are each independently an integer from 0 to 10;

[0065] e1 is each independently an integer from 0 to 3;

[0066] c1, d1, c2, d2 are each independently an integer from 0 to 4;

[0067] e2 is an integer from 0 to 5;

[0068] The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

[0069] In a preferred embodiment, the structure of the deuterated boron-containing organic compound is represented by any one of the general formulas (5-1) to (5-9):

[0070]

[0071]

[0072] In general formula (5-1) to general formula (5-6), R is the same or different each time and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group;

[0073] R3, which is the same or different each time, represents one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C10 alkyl group;

[0074] X represents C, Si;

[0075] f and g are each independently an integer from 0 to 5;

[0076] a1, b1, a2, b2, e1 are each independently an integer from 0 to 3;

[0077] c1, d1, c2, d2 are each independently an integer from 0 to 4;

[0078] e2 is an integer from 0 to 5;

[0079] The substituent for the substituent group may be selected from any one of a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

[0080] In a preferred embodiment, R is a deuterium atom, a tritium atom, a fluorine atom, a cyano group, 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 benzene group, 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 biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, tert-butoxy;

[0081] R1 and R2 are independently hydrogen, deuterium, tritium, fluorine, cyano, adamantyl, methyl, deuterated methyl, tritated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritated ethyl, isopropyl, deuterated isopropyl, tritated isopropyl, tert-butyl, deuterated tert-butyl, tritated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritated 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, carbamide Azolyl, 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 tert-butyl, xanthone, phenyl-substituted triazine, phenyl-substituted boryl, methoxy, tert-butoxy;

[0082] Ar1 and Ar2 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 biphenyl, tertiary butyl substituted ... Phenyl, 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;

[0083] The M1, M2, M3, M4, and M5 are 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 replacing the above-mentioned substitutable group may be 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 carbazoline group, and an azaphenanthryl group.

[0085] Preferably, the R is represented by the structure shown below:

[0086] Deuterium atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, cyclopentyl group,

[0087] Any of;

[0088] The R1 and R2 are independently represented by the following structures:

[0089] Hydrogen atom, deuterium atom, cyano group,

[0090]

[0091] Any of;

[0092] The Ar1 and Ar2 are represented by the following structures:

[0093] Methyl, isopropyl, tert-butyl,

[0094] Any of;

[0095] The M1, M2, and M3 are represented by any of the following ring structures:

[0096]

[0097] The M4 and M5 are represented by any of the following ring structures:

[0098]

[0099] The Z is represented by CR a ;

[0100] R a Each occurrence independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a benzene group, a 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 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.

[0101] In a preferred embodiment, the specific structural formula of the deuterated boron-containing organic compound is any one of the following structures:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] The above compounds (1) to (184), with compound (1) For example, D represents deuterium atom, D1-D29 represents 1 to 29 hydrogen atoms are replaced by deuterium atoms.

[0123]

[0124]

[0125]

[0126] The present invention also provides 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, and the light-emitting layer contains the deuterated boron-containing organic compound.

[0127] In a preferred embodiment, the light-emitting layer comprises a main material and a doping material, and the doping material contains the deuterated boron-containing organic compound.

[0128] 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 deuterated boron-containing organic compound.

[0129] 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 is the deuterated boron-containing organic compound.

[0130] The beneficial technical effects of the present invention are:

[0131] (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;

[0132] (2) The compound of the present invention can be used as a doping material to significantly improve the life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0133] 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;

[0134] 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

[0135] The technical solutions in the embodiments of the present invention will be described clearly and completely below in conjunction with the drawings in the embodiments of the present invention. In the absence of conflict, the embodiments of the present invention and the features in the embodiments can be combined with each other. The present invention will be further described below in conjunction with the drawings and specific embodiments, but they are not intended to limit the present invention.

[0136] 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.

[0137] In the present invention, the substituted or unsubstituted aromatic amine group described in the present invention refers to Wherein Q4 and Q5 represent substituted or unsubstituted aromatic groups, and Q4 and Q5 preferably represent substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C2-C 30 Heteroaryl.

[0138] 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.

[0139] In the present invention, the substituted or unsubstituted 5-30 membered heteroaryl group refers to a substituted or unsubstituted furyl, 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 benzo imidazolyl, substituted or unsubstituted 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 fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or condensed rings of combinations of the foregoing groups, but are not limited thereto.

[0140] The C1-C 10Alkyl (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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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 deuterated boron-containing organic compound represented by the general formula (1) of the present invention.

[0158] The light-emitting layer may contain a single host material or a dual host material;

[0159] 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;

[0160] 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.

[0161] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0162] Exciton sensitizing materials refer to materials that can make the luminescent material in the luminescent layer fully utilize the electroinduced excitons, 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 deuterated 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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, a light-emitting layer, a hole blocking 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.

[0172] 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;

[0173] Intermediate synthesis:

[0174] Synthesis of intermediate G series:

[0175]

[0176] Synthesis of intermediate G1: Dissolve the raw material A1 (0.98 g, 5 mmol) in 100 mL of 99.9% heavy water solution, add PtO2 (0.045 g, 0.2 mmol) and stir. The resulting mixture is placed in a polytetrafluoroethylene reactor at 250 ° C for 8 hours and then allowed to reach room temperature. Then add ethyl acetate (100 mL). The mixture is washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate is evaporated under reduced pressure. Pour the remaining mixture into 100 mL of petroleum ether with stirring. Intermediate G1 is obtained after filtration.

[0177] The following target intermediate B series compounds (B1, B2 and B3) were synthesized by referring to the preparation process of intermediate G1; the reaction conditions were the same, except that the raw materials A listed in Table 1 below were used:

[0178] Table 1

[0179]

[0180] Synthesis of intermediate D1: Pd(PPh3)4 (0.29 g, 0.25 mmol), 1,4-bis(diphenylphosphino)butane (0.21 g, 0.5 mmol), raw material C1 (2.17 g, 10 mmol) and raw material R1 (0.57 g, 5 mmol) were mixed with DBU (1.52 g, 10 mmol) in a round-bottom flask; DMSO (30 mL) was added and stirred at 110°C for 3 hours; the mixture was cooled to room temperature, poured into a saturated ammonia hydrochloric acid solution (50 mL), and extracted with ethyl acetate (300 mL). The organic phase was washed with brine (3×100 mL), dried over Na2SO4 and filtered. The solvent was removed to obtain a crude product, which was purified by silica gel column chromatography and eluted with n-hexane to obtain intermediate D1.

[0181]

[0182] Synthesis of intermediate G2: Add intermediate B1 (1.13 g, 5 mmol), potassium carbonate (2.76 g, 20 mmol), tricyclohexylphosphine (0.28 g, 1 mmol), palladium acetate (0.045 g, 0.2 mmol) into a two-necked flask, add 100 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add intermediate D1 (1.49 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection; cool the mixture to room temperature and extract with ethyl acetate (300 mL); wash the organic phase with brine (3×100 mL), dry over Na2SO4 and filter. Remove the solvent to obtain a crude product, purify by silica gel column chromatography, and elute with n-hexane to obtain intermediate G2.

[0183] The following target intermediate G series compounds were synthesized by referring to the preparation process of intermediate G2; the reaction conditions were the same, except that intermediate B, raw material A and intermediate or raw material D listed in Table 2 below were used:

[0184] Table 2

[0185]

[0186]

[0187]

[0188] Example 1: Synthesis of Compound 185:

[0189]

[0190] Synthesis of intermediate K1: Add raw material N1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material E1 (1.43 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate K1.

[0191] Synthesis of intermediate L1: Intermediate K1 (3.05 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution, and 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added under nitrogen at 0°C; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material F1 (2.39 g, 12.7 mmol) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. Then the water layer was separated and extracted with dichloromethane. Drying with sodium sulfate, filtering, and evaporation by rotary concentration and column column gave intermediate L1.

[0192] Synthesis of intermediate M1: Intermediate L1 (1.61 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and intermediate G2 (0.98 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 10 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate M1.

[0193] Synthesis of compound 185: Under nitrogen atmosphere at 0°C, 16 mL of a n-pentane solution of tert-butyl lithium (1.6 M) was slowly added to 30 mL of a tert-butylbenzene solution of intermediate M1 (11.95 g, 12.5 mmol). After stirring at 60°C for 2 hours, n-pentane was removed in vacuo. After adding boron tribromide (6.26 g, 25 mmol) at 0°C, the reaction mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIEA) (3.25 g, 25.2 mmol) was added at 0°C and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in vacuo and passed through a column to obtain compound 185.

[0194] The target compounds of the following examples (2-17) were synthesized by referring to the preparation process of compound 185 in Example 1; the reaction conditions were the same, the raw material N1 used was the same, and the difference was that the raw material E, raw material F and intermediate G listed in Table 3 below were used;

[0195] Table 3

[0196]

[0197]

[0198]

[0199]

[0200] The structural characterization, mass spectrometry analysis and physicochemical property test results of the compounds obtained in each example are as follows:

[0201] The structural formula of compound 185 (C 67 H 38 D 23 BN2) theoretical value: C, 86.70; H, 9.12; N, 3.02; test value: C, 86.72; H, 9.10; N, 2.95. LC-MS: Found: 928.62 ([M+H] + ), exact mass: 927.64.

[0202] The structural formula of compound 186 (C 67 H 57 D4BN2) theoretical value: C, 88.52; H, 7.21; N, 3.08; test value: C, 88.50; H, 7.19; N, 3.06. LC-MS: Found: 909.73 ([M+H] + ), exact mass: 908.52.

[0203] The structural formula of compound 187 (C 63 H 20 D 27 BN2) theoretical value: C, 86.97; H, 8.57; N, 3.22; test value: C, 86.93; H, 8.60; N, 3.30. LC-MS: Measured value: 870.65 ([M+H] + ), exact mass: 869.55.

[0204] The structural formula of compound 188 (C 63 H 43 D4BN2) theoretical value: C, 89.35; H, 6.07; N, 3.31; test value: C, 89.32; H, 6.13; N, 3.40. LC-MS: Found: 847.35 ([M+H] + ), exact mass: 846.41.

[0205] The structural formula of compound 189 (C 63 H 38 D9BN2) theoretical value: C, 88.82; H, 6.62; N, 3.29; test value: C, 88.87; H, 6.56; N, 3.19. LC-MS: Measured value: 852.43 ([M+H] + ), exact mass: 851.44.

[0206] The structural formula of compound 190 (C 63 H 28 D 19 BN2) theoretical value: C, 87.78; H, 7.71; N, 3.25; test value: C, 87.84; H, 7.77; N, 3.16. LC-MS: Measured value: 862.55 ([M+H] + ), exact mass: 861.50.

[0207] The structural formula of compound 191 (C 71 H 38 D 25 BN2) theoretical value: C, 87.00; H, 9.04; N, 2.86; test value: C, 87.01; H, 9.14; N, 2.95. LC-MS: Found: 980.89 ([M+H] + ), exact mass: 979.67.

[0208] The structural formula of compound 192 (C 71 H 54D9BN2) theoretical value: C, 88.45; H, 7.53; N, 2.91; test value: C, 88.53; H, 7.47; N, 2.96. LC-MS: Found: 964.54 ([M+H] + ), exact mass: 963.56.

[0209] The structural formula of compound 193 (C 63 H2D 45 BN2) theoretical value: C, 85.20; H, 10.43; N, 3.15; test value: C, 85.23; H, 10.51; N, 3.14. LC-MS: Found: 888.62 ([M+H] + ), exact mass: 887.67.

[0210] The structural formula of compound 194 (C 53 H 20 D 23 BN2) theoretical value: C, 85.81; H, 8.96; N, 3.78; test value: C, 85.72; H, 8.88; N, 3.75. LC-MS: Measured value: 742.77 ([M+H] + ), exact mass: 741.50.

[0211] The structural formula of compound 195 (C 63 H 20 D 27 BN2) theoretical value: C, 86.97; H, 8.57; N, 3.22; test value: C, 86.94; H, 8.53; N, 3.13. LC-MS: Found: 870.64 ([M+H] + ), exact mass: 869.55.

[0212] The structural formula of compound 196 (C 63 H 43 D4BN2) theoretical value: C, 89.35; H, 6.07; N, 3.31; test value: C, 89.28; H, 6.17; N, 3.35. LC-MS: Found: 847.43 ([M+H] + ), exact mass: 846.41.

[0213] The structural formula of compound 197 (C 63 H 38 D9BN2) theoretical value: C, 88.82; H, 6.62; N, 3.29; test value: C, 88.80; H, 6.63; N, 3.22. LC-MS: Measured value: 852.49 ([M+H] + ), exact mass: 851.44.

[0214] The structural formula of compound 198 (C 63 H 28 D 19 BN2) theoretical value: C, 87.78; H, 7.71; N, 3.25; test value: C, 87.82; H, 7.80; N, 3.28. LC-MS: Measured value: 862.67 ([M+H] + ), exact mass: 861.50.

[0215] The structural formula of compound 199 (C 63 H2D 45 BN2) theoretical value: C, 85.20; H, 10.43; N, 3.15; test value: C, 85.11; H, 10.35; N, 3.23. LC-MS: Measured value: 888.85 ([M+H] + ), exact mass: 887.67.

[0216] The structural formula of compound 200 (C 71 H 38 D 25 BN2) theoretical value: C, 87.00; H, 9.04; N, 2.86; test value: C, 86.95; H, 9.01; N, 2.94. LC-MS: Found: 980.56 ([M+H] + ), exact mass: 979.67.

[0217] The structural formula of compound 201 (C 71 H 54 D9BN2) theoretical value: C, 88.45; H, 7.53; N, 2.91; test value: C, 88.47; H, 7.54; N, 2.95. LC-MS: Found: 964.66 ([M+H] + ), exact mass: 963.56.

[0218] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device examples 1-17 and device comparative examples 1-2. The device manufacturing process of device examples 1-17 of the present invention is exactly the same as that of device comparative examples 1-2, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. 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 4 and Table 5 respectively.

[0219] Device Example 1

[0220] like Figure 1As 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 185 as the doping material, the mass ratio of GH-1, GH-2 and compound 185 is 69:30:1, and the film thickness of the light-emitting layer is 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.

[0221] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device examples 18-34 and device comparison examples 2-4. The device manufacturing process of device examples 18-34 of the present invention is exactly the same as that of device comparison examples 2-4, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. 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 4 and Table 5 respectively.

[0222] Device Example 18

[0223] 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 185 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 185 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.

[0224] The molecular structure formula of the relevant materials is shown below:

[0225]

[0226] Comparative compounds ref-1 and ref-2 were prepared by referring to the methods described in the prior art.

[0227] After the OLED light emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the voltage, current efficiency and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 4; the test results of the voltage, current efficiency and life of the obtained device are shown in Table 5.

[0228] Table 4

[0229]

[0230]

[0231] Table 5

[0232]

[0233]

[0234] 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.

[0235] It can be seen from the device data results in Table 5 that, compared with device comparison examples 1-2, the device life of the compounds of the present invention in single-doping system devices is higher than that of comparison examples 1-2; in single-doping system devices, the device efficiency also shows a good effect; compared with device comparison examples 3-4, the compounds of the present invention are in dual-doping system devices using exciton-sensitizing materials as the first doping, and the current efficiency and device life of the device are greatly improved relative to OLED devices of known materials, and in dual-doping devices, the device efficiency is also significantly improved compared to single doping.

[0236] 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 deuterated boron-containing organic compound, characterized in that: The structure of the deuterated boron-containing organic compound is shown in general formula (1): In the general formula (1), each occurrence of R1-R2 is the same or different and represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; M1, M2, M3, M4, and M5 are each independently R-substituted or unsubstituted C6-C 30 One of an aromatic ring of R, a 5- to 30-membered heteroaromatic ring substituted or unsubstituted by R, and a C6-C10 aliphatic ring substituted or unsubstituted by R; R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; X represents C, Si; a, b, c, d, e, f, g, h, and k are each independently an integer from 0 to 10; a, b, c, d, e, f, g, h, k are not all 0 at the same time; The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

2. The deuterated boron-containing organic compound according to claim 1, characterized in that: The structure of the deuterated boron-containing organic compound is shown in the general formula (1-1): In the general formula (1-1), each occurrence of R1-R2 is the same or different and represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; M1 represents R substituted or unsubstituted C6~C 30 One of an aromatic ring of R, a 5- to 30-membered heteroaromatic ring substituted or unsubstituted by R, and a C6-C10 aliphatic ring substituted or unsubstituted by R; R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; X represents C, Si; e, f, g, h, and k are each independently an integer from 0 to 10; a1, b1, a2, b2 are each independently an integer from 0 to 3; c1, d1, c2, d2 are each independently an integer from 0 to 4; a1, b1, c1, d1, e, f, g, h, k are not all 0 at the same time; The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

3. The deuterated boron-containing organic compound according to claim 1, characterized in that: The structure of the deuterated boron-containing organic compound is shown in any one of the general formulas (2-1) to (2-3): In the general formula (2-1) to the general formula (2-3), R1-R2 are the same or different each time and represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; X represents C, Si; f, g, h, and k are each independently an integer from 0 to 10; a1, b1, a2, b2, e1 are each independently an integer from 0 to 3; c1, d1, c2, d2 are each independently an integer from 0 to 4; e2 is an integer from 0 to 5; a1, b1, c1, d1, e1, f, g, h, k are not all 0 at the same time; a1, b1, c1, d1, e2, f, g, h, k are not all 0 at the same time; The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

4. The deuterated boron-containing organic compound according to claim 1, characterized in that: The structure of the deuterated boron-containing organic compound is shown in any one of the general formulas (3-1) to (3-3): In the general formula (3-1) to the general formula (3-3), R1-R2 are the same or different each time and represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; X represents C, Si; f, g, h, and k are each independently an integer from 0 to 10; a1, b1, a2, b2, e1 are each independently an integer from 0 to 3; c1, d1, c2, d2 are each independently an integer from 0 to 4; e2 is an integer from 0 to 5; a1, b1, c1, d1, e1, f, g, h, k are not all 0 at the same time; a1, b1, c1, d1, e2, f, g, h, k are not all 0 at the same time; The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

5. The deuterated boron-containing organic compound according to claim 1, characterized in that: The structure of the deuterated boron-containing organic compound is shown in any one of the general formulas (4-1) to (4-3): In the general formula (4-1) to the general formula (4-3), R1-R2 are the same or different each time and represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; Ar1 and Ar2, which are the same or different each time, represent one of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; R is the same or different each time it appears and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; X represents C, Si; f, g, h, and k are each independently an integer from 0 to 10; e1 is each independently an integer from 0 to 3; c1, d1, c2, d2 are each independently an integer from 0 to 4; e2 is an integer from 0 to 5; The substituent for the substituent group may be selected from any one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

6. The deuterated boron-containing organic compound according to claim 1, characterized in that: The structure of the deuterated boron-containing organic compound is shown in any one of the general formulas (5-1) to (5-9): In general formula (5-1) to general formula (5-6), R is the same or different each time and represents one of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted 5-30 membered heteroaryl group; R3, which is the same or different each time, represents one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C10 alkyl group; X represents C, Si; f and g are each independently an integer from 0 to 5; a1, b1, a2, b2, e1 are each independently an integer from 0 to 3; c1, d1, c2, d2 are each independently an integer from 0 to 4; e2 is an integer from 0 to 5; The substituent for the substituent group may be selected from any one of a halogen atom, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a 5-30 membered heteroaryl group.

7. The deuterated boron-containing organic compound according to any one of claims 1 to 6, characterized in that: R represents a deuterium atom, a tritium atom, a fluorine atom, a cyano group, 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 substituted 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-phenyl one of carbazolyl, 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 tert-butyl, xanthone, phenyl-substituted triazine, phenyl-substituted boryl, methoxy, and tert-butoxy; R1 and R2 are independently hydrogen, deuterium, tritium, fluorine, cyano, adamantyl, methyl, deuterated methyl, tritated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritated ethyl, isopropyl, deuterated isopropyl, tritated isopropyl, tert-butyl, deuterated tert-butyl, tritated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritated 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, carbamide Azolyl, 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 tert-butyl, xanthone, phenyl-substituted triazine, phenyl-substituted boryl, methoxy, tert-butoxy; Ar1 and Ar2 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 biphenyl, tertiary butyl substituted ... Phenyl, 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; The M1, M2, M3, M4, and M5 are 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; The substituent replacing the above-mentioned substitutable group may be 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 carbazoline group, and an azaphenanthryl group.

8. The deuterated boron-containing organic compound according to any one of claims 1 to 6, characterized in that: The R is represented by the following structure: Deuterium atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, cyclopentyl group, Any of; The R1 and R2 are independently represented by the following structures: Hydrogen atom, deuterium atom, cyano group, Any of; The Ar1 and Ar2 are represented by the following structures: Methyl, isopropyl, tert-butyl, Any one of; said M1, M2, M3 are represented by any one of the following ring structures: The M4 and M5 are represented by any of the following ring structures: The Z is represented by CR a ; R a Each occurrence independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a benzene group, a 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 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.

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

10. 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 deuterated boron-containing organic compound according to any one of claims 1 to 9; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the deuterated boron-containing organic compound according to any one of claims 1 to 9; Preferably, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is a deuterated boron-containing organic compound according to any one of claims 1 to 9; Preferably, 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 is the deuterated boron-containing organic compound according to any one of claims 1 to 9.

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