Boron-containing organic compound and organic electroluminescent device prepared from same

Abstract

The invention discloses a boron-containing organic compound and an organic electroluminescent device prepared from the same, and belongs to the technical field of semiconductors. The structure of the organic compound is shown as a general formula (A), # imgabs0. When the compound is used as a doping material in a luminescent layer material of an organic electroluminescent device, the compound can be used as a blue light doping material of the luminescent layer of the organic electroluminescent device to emit blue light.

Description

Technical Field

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

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has technical advantages such as lighter and thinner, high color contrast, low power consumption, fast response, high clarity, and flexibility, and is believed to dominate future display terminal products. With the advent of the 5G era, the new information display industry is in urgent need of iterative development. The early lower color gamut standards (BT.709 and DCI P3) can no longer meet the high-quality technical development needs of display products. In order to achieve ultra-high definition and higher picture quality performance requirements of display products, the new generation of display standards (BT.2020) drives OLED luminescent materials to develop towards high color purity, which requires the core luminescent materials to have a narrower emission spectrum. Among the three commercial OLED red, green and blue color rendering technologies, blue light uses the traditional fluorescent triplet-triplet conversion (TTF) technology, which has low efficiency and has high technical requirements for blue light luminescent materials. In order to meet the demand for blue light display, especially for the BT.2020 display indicators, very high requirements are placed on the color purity and life of the blue light emitting material itself.

[0003] Since 2006, blue light materials with narrow half-width (half-width <20nm) based on boron nitride resonance structures have been reported one after another: DOI:10.1002 / adma.201505491, DOI:10.1038 / s41566-019-0476-5, DOI:10.1002 / anie.202108283, DOI:10.1002 / adma.202107951, DOI:10.1021 / jacs.1c11659, DOI:10.1002 / anie.202201588, etc., showing the high color purity and efficiency of this type of material, which has become the development trend of high color purity blue light OLEDs. However, there are still many technical difficulties in the development of blue light ultra-high color purity materials containing boron nitrogen structure, especially in suppressing the relative intensity of shoulder peak and reducing the degree of spectral tailing, which are key technical points for the next generation of high-efficiency display devices. Summary of the invention

[0004] In view of the above problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can achieve blue light emission.

[0005] The technical solution of the present invention is as follows: a boron-containing organic compound, the structure of the boron-containing organic compound is shown in general formula (A):

[0006]

[0007] In the general formula (A), each occurrence of M1, M2, and M3 that is the same or different represents R-substituted or unsubstituted C6-C 30 One of aryl, R substituted or unsubstituted 5-30 membered heteroaryl;

[0008] X1 represents C-Ar2 or N;

[0009] Ar0 appears the same or different each time to represent substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0010] Ar1 and Ar2, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0011] Ar1 and Ar2 can also bond to form an R-substituted or unsubstituted five-membered ring;

[0012] Z represents N, CH or CR;

[0013] The R may be the same or different each time and may represent a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0014] The substitution mode of R is a single bond or a ring connection;

[0015] The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine;

[0016] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0017] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (A-1) to (A-3):

[0018]

[0019] In the general formula (A-1) to the general formula (A-3), R6-R 20 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0020] R6-R 20 Any two adjacent ones can be connected to form a ring;

[0021] X1 represents C-Ar2 or N;

[0022] Ar0 appears the same or different each time to represent substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0023] Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0024] X2 is represented by C(R a )(R b)、Si(R c )(R d ), NR e , O, S;

[0025] R a -R d Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of an aryl group, a substituted or unsubstituted arylamine group, and a substituted or unsubstituted 5-30-membered heteroaryl group;

[0026] R a With R b , R c With R d Can be connected into a ring;

[0027] R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0028] R e , Ar4 can also be connected to form a ring;

[0029] The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine;

[0030] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0031] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (A-4) to (A-7):

[0032]

[0033] In the general formula (A-4), Z represents CH or CR;

[0034] The R may be the same or different each time and may represent a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 Alkyl, substituted or unsubstituted C3~C 10 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-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0035] In the general formula (A-4) to the general formula (A-7), R6-R 20 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0036] R6-R 20 Any two adjacent ones can be connected to form a ring;

[0037] Ar0 appears the same or different each time to represent substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0038] Ar1 and Ar2 appear the same or different each time, indicating substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0039] X2 is represented by C(R a )(R b )、Si(R c )(Rd ), NR e , O, S;

[0040] R a -R d Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of an aryl group, a substituted or unsubstituted arylamine group, and a substituted or unsubstituted 5-30-membered heteroaryl group;

[0041] R a With R b , R c With R d Can be connected into a ring;

[0042] R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0043] The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine;

[0044] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0045] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (1) to (3):

[0046]

[0047] In the general formula (1) to the general formula (3), R1-R 20 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0048] R1-R 20 Any two adjacent ones can be connected to form a ring;

[0049] X1 represents C-Ar2 or N;

[0050] Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0051] Ar3 and Ar4 can be connected to form a ring;

[0052] X2 is represented by C(R a )(R b )、Si(R c )(R d ), NR e , O, S;

[0053] R a -R d Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of an aryl group, a substituted or unsubstituted arylamine group, and a substituted or unsubstituted 5-30-membered heteroaryl group;

[0054] R a With R b , R c With R d Can be connected into a ring;

[0055] R e Each occurrence of the same or different C1~C 10Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0056] R e , Ar4 can also be connected to form a ring;

[0057] The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine;

[0058] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0059] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (4) to (10):

[0060]

[0061] In the general formula (4) to the general formula (10), R1-R 16 , R 22 -R 29 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0062] R1-R 16 , R 22 -R 29 Any two adjacent ones can be connected to form a ring;

[0063] R e Each occurrence of the same or different C1~C10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0064] Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0065] The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine;

[0066] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0067] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (11) to (32):

[0068]

[0069]

[0070] In the general formula (11) to the general formula (32), R1-R5, R7-R 10 , R 13 -R 16 , R 23 , R 24 , R 27 , R 28 , R 30 -R 54 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl;

[0071] R1-R5, R7-R 10 , R 13 -R 16 , R 23 , R 24 , R 27 , R 28 , R 30 -R 54 Any two adjacent ones can be connected to form a ring;

[0072] R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0073] The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 One or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl, and arylamine;

[0074] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0075] Preferably, the R, R1-R 54The same or different occurrences of each of the above radicals are represented by 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, 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-phenylcarbazolyl , 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, diphenylamine;

[0076] The R a -R eEach occurrence of the same or different radicals is represented by adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl , deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spiro Fluorenyl, 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, diphenylamine;

[0077] Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl , deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9, 9-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, diphenylamine;

[0078] The Ar0 is phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, 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 one of a deuterated bisphenyl group, a deuterated bisphenyl group, an ethyl substituted bisphenyl group, an isopropyl substituted bisphenyl group, a tert-butyl substituted bisphenyl group, a deuterated methyl substituted phenyl group, a deuterated ethyl substituted phenyl group, a deuterated isopropyl substituted phenyl group, a deuterated tert-butyl substituted phenyl group, a deuterated methyl substituted bisphenyl group, a deuterated ethyl substituted bisphenyl group, a deuterated isopropyl substituted bisphenyl group, a deuterated tert-butyl substituted bisphenyl group, a tert-butyl substituted dibenzofuranyl group, a phenyl substituted tert-butyl group, a xanthone group, and a phenyl substituted triazine group;

[0079] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, and a diphenylamine group;

[0080] Preferably, the R, R1-R 54 They are independently represented as follows:

[0081] Hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group,

[0082]

[0083] Any of;

[0084] The R e Each occurrence of the same or different is represented by:

[0085] Any of;

[0086] The same or different occurrences of Ar1, Ar2, Ar3, and Ar4 are represented as follows:

[0087] Hydrogen atom, methyl, ethyl, isopropyl, tert-butyl,

[0088] Any of;

[0089] The same or different Ar0 is represented by:

[0090]

[0091] Any one of.

[0092] In a preferred embodiment, the specific structure of the boron-containing organic compound is any one of the following structures:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] The present invention also provides an organic electroluminescent device, which comprises a substrate, a first electrode, an organic light-emitting functional layer and a second electrode in sequence, wherein the organic light-emitting functional layer is located between the first electrode and the second electrode, and the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound;

[0105] Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material contains the boron-containing organic compound.

[0106] Compared with the prior art, the beneficial technical effects of the present invention are:

[0107] (1) The compound of the present invention is applied to OLED devices and can be used as a doping material for a light-emitting layer material. It can emit blue fluorescence under the action of an electric field and can be applied to the field of OLED lighting or OLED display. BRIEF DESCRIPTION OF THE DRAWINGS

[0108] 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;

[0109] 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, 10 is a cathode layer, and 11 is a CPL layer. DETAILED DESCRIPTION

[0110] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0111] 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.

[0112] In the present invention, the term "can be connected to form a ring" means that the two groups may be unconnected or connected to each other to form a ring, preferably connected to form a ring through a CC single bond, a C=C double bond, an O atom, an S atom, CQ1Q2, or NQ3, wherein Q1, Q2, or Q3 represents a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl.

[0113] 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 5-30 membered heteroaryl.

[0114] 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 also includes, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a combination thereof, or a condensed ring of a combination of the foregoing groups.

[0115] 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.

[0116] The C1-C 10 Alkyl (including straight-chain alkyl and branched alkyl) refers to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl and the like, but is not limited thereto.

[0117] 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.

[0118] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0119] The C1-C 10 The alkoxy group refers to a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an isopropoxy group or the like, but is not limited thereto.

[0120] The C2-C 10Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl and 3-phenyl-1-butenyl, etc., but is not limited thereto.

[0121] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent PI film 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 glass substrate is preferably used. The thickness of the substrate is not particularly limited.

[0122] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir or Cr, or an alloy of several metals, or a combination of metals, metal oxides and metal alloys. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm and more preferably 100-200 nm.

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

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

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

[0126] 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.

[0127] In view of the above empirical summary, for hole-type host organic 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.

[0128] Preferably, the main organic material of the hole injection layer of the present invention can be selected from the following compounds disclosed in the prior art: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A.

[0129] Preferably, the P-type doping material is selected from the compounds with charge conductivity disclosed in the prior art, and the P-type dopant can be selected from the compounds disclosed in any one of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but are not limited thereto.

[0130] In one embodiment of the present invention, the hole injection layer comprises a P-type dopant material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited to these.

[0131] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1-95:5, preferably 99:1-97:3, based on mass.

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

[0133] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0134]

[0135] Preferably, the hole transport layer material and the host organic material in the hole injection layer of the present invention are selected from the same compound.

[0136] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, but the thickness is not limited to this range.

[0137] In one embodiment of the present invention, the electron blocking layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0138]

[0139] 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.

[0140] 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.

[0141] The light-emitting layer may include a host material and a dopant material. The host material may be a common blue light host material in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of the present invention.

[0142] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

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

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

[0145] The hole blocking layer is a layer that blocks 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 performance 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 function known in the prior art can be used, for example:

[0146]

[0147] The thickness of the hole blocking layer of the present invention may be 2-200 nm, preferably 5-150 nm, more preferably 5-50 nm, but the thickness is not limited to this range.

[0148] 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. A material having a high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials for organic electroluminescent devices disclosed in the prior art can be used, for example:

[0149]

[0150] In a preferred embodiment of the present invention, the electron transport layer further comprises other compounds conventionally used in electron transport layers, for example, Alq3, LiQ, preferably LiQ.

[0151] 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.

[0152] The electron injection layer may be disposed on 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 disclosed in the prior art can be used, for example: LiF, Cs2CO3, CsF, Csq, NaF, MgF2, CaF2, Al2O3, Yb, etc.

[0153] 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.

[0154] 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.

[0155] Optionally, in order to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (ie, CPL layer) may be added on the second electrode (ie, cathode) of the device. The compounds disclosed in the prior art CN103828485A and CN110229145A may be used as CPL layer materials.

[0156] The thickness of the CPL layer is generally 5-300 nm, preferably 20-100 nm and more preferably 40-80 nm.

[0157] 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.

[0158] The method for preparing the organic electroluminescent device of the present invention comprises laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0159] Synthesis Example

[0160] 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;

[0161] Example 1 Synthesis of Compound 21:

[0162]

[0163] Preparation of intermediate a-1:

[0164] Add raw material A-1 (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 B-1 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a PE:EA column to obtain intermediate a-1.

[0165] Preparation of intermediate b-1:

[0166] Dissolve the intermediate a-1 (3.03 g, 5.1 mmol) in 50 mL of tetrahydrofuran (THF) solution, slowly add 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution at -78 ° C under nitrogen gas; after stirring at -78 ° C for 2 hours, slowly add 0.48 mL of BBr3 (5 mol), react at -78 ° C for 2 hours, continue to add 1.04 mL of N, N-diisopropylethylamine (DIPEA) (6 mmol), heat the system to 150 ° C and react for 5 hours, and continue to add 10 mL of tetrahydrofuran solution dissolved in raw material C-1 (1.22 g, 5.5 mmol). Then slowly heat the reaction mixture to room temperature and stir overnight. Add dilute hydrochloric acid solution, distilled water and ethyl acetate to the reaction mixture, separate the water layer, and extract it three times with ethyl acetate. The combined organic layer is 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 an aqueous solution of NaHCO3. The aqueous layer was then separated and extracted with dichloromethane. Drying with sodium sulfate, filtering, and evaporation by rotary concentration and column to obtain intermediate b-1.

[0167] Preparation of intermediate c-1:

[0168] Under nitrogen protection, 6.0 g (10 mmol) of intermediate b-1, 4.3 g (12 mmol) of raw material B-2, 2.1 g (15 mmol) of potassium carbonate, 0.1 g (0.5 mmol) of palladium acetate, 0.4 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate and 100 mL of DMAC were added to a three-necked flask and refluxed for 12 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-1.

[0169] Preparation of compound 21:

[0170] In a sealed pressure tube, under nitrogen protection, 8.7g (10mmol) of intermediate c-1 and 75mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 3 hours, the reaction was cooled to -42°C, 1.4mL (15mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 4 hours. After cooling to 0°C, 3.5mL (20mmol) of ultra-dry N,N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180°C for reaction for 10 hours. Cool to room temperature, remove low-boiling solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate, separate and purify with column chromatography to obtain compound 21. Compound 21 was dissolved in toluene solution (1×10 -5M) The half-peak width is 16 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0171] Example 2 Synthesis of Compound 27:

[0172]

[0173] Preparation of intermediate d-1:

[0174] Under nitrogen protection, 2.1 g (10 mmol) of raw material B-3, 3.2 g (12 mmol) of raw material E-1, 2.1 g (15 mmol) of potassium carbonate, 0.1 g (0.5 mmol) of palladium acetate, 0.4 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate and 100 mL of DMAC were added to a three-necked flask and refluxed for 10 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate d-1.

[0175] Preparation of intermediate c-2:

[0176] Under nitrogen protection, 6.0 g (10 mmol) of intermediate b-1, 4.7 g (12 mmol) of intermediate d-1, 2.1 g (15 mmol) of potassium carbonate, 0.1 g (0.5 mmol) of palladium acetate, 0.4 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate and 100 mL of DMAC were added to a three-necked flask and refluxed for 17 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-2.

[0177] Preparation of compound 27:

[0178] In a sealed pressure tube, under nitrogen protection, 9.1g (10mmol) of intermediate c-2 and 75mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 2 hours, the reaction was cooled to -42°C, 1.4mL (15mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 2 hours. After cooling to 0°C, 3.5mL (20mmol) of ultra-dry N,N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180°C for reaction for 11 hours. Cool to room temperature, remove low-boiling solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate, separate and purify with column chromatography to obtain compound 27. Compound 27 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 17 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1H NMR (400 MHz, deuterated chloroform): δ8.47 (d, 1H), 8.31 (d, 1H), 7.90 (m, 2H), 7.65–7.57 (m, 2H), 7.45 (d, 1H), 7.33–7.17 (m, 7H), 7.04 (d, 2H), 6.99 (s, 2H), 2.37 (s, 3H), 2.35 (s, 6H), 1.88–1.71 (m, 4H), 1.32–1.28 (m, 30H).

[0179] Example 3 Synthesis of Compound 149:

[0180]

[0181] Preparation of intermediate c-3:

[0182] Under nitrogen protection, 6.0g (10mmol) of intermediate b-1, 3.8g (12mmol) of raw material B-4, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 15 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-3.

[0183] Preparation of compound 149:

[0184] In a sealed pressure tube, under nitrogen protection, 8.3g (10mmol) of intermediate c-3 and 75mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 2 hours, the reaction was cooled to -42°C, 1.4mL (15mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 2.5 hours. After cooling to 0°C, 3.5mL (20mmol) of ultra-dry N,N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180°C for 11 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate, separate and purify with column chromatography to obtain compound 149. Compound 149 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 15 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0185] Example 4 Synthesis of Compound 156:

[0186]

[0187] Preparation of intermediate c-4:

[0188] Under nitrogen protection, 6.0 g (10 mmol) of intermediate b-1, 3.4 g (12 mmol) of raw material B-5, 2.1 g (15 mmol) of potassium carbonate, 0.1 g (0.5 mmol) of palladium acetate, 0.4 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate and 100 mL of DMAC were added to a three-necked flask and refluxed for 10 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-4.

[0189] Preparation of compound 156:

[0190] In a sealed pressure tube, under nitrogen protection, 8.0 g (10 mmol) of intermediate c-4 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 ° C, 4.8 mL of 2.5 M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60 ° C for reaction for 2 hours, the reaction was cooled to -42 ° C, 1.4 mL (15 mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 3 hours. After cooling to 0 ° C, 3.5 mL (20 mmol) of ultra-dry N, N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180 ° C for 13 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate and separate and purify with column chromatography to obtain compound 156. Compound 156 in toluene solution (1×10 -5 M) The half-peak width is 14 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0191] Example 5 Synthesis of Compound 165:

[0192]

[0193] Preparation of intermediate b-2:

[0194] Dissolve the intermediate a-1 (3.0 g, 5.1 mmol) in 50 mL of tetrahydrofuran (THF) solution, slowly add 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution at -78 ° C under nitrogen gas; after stirring at -78 ° C for 3 hours, slowly add 0.48 mL of BBr3 (5 mol), react at -78 ° C for 2 hours, continue to add 1.04 mL of N, N-diisopropylethylamine (DIPEA) (6 mmol), heat the system to 150 ° C and react for 4.5 hours, and continue to add 10 mL of tetrahydrofuran solution in which the raw material C-2 (1.7 g, 5.5 mmol) is dissolved. Then slowly heat the reaction mixture to room temperature and stir overnight. Add dilute hydrochloric acid solution, distilled water and ethyl acetate to the reaction mixture, separate the water layer, and extract it three times with ethyl acetate. The combined organic layer is 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 an aqueous solution of NaHCO3. The aqueous layer was then separated and extracted with dichloromethane. Drying with sodium sulfate, filtering, and evaporation by rotary concentration and column to obtain intermediate b-2.

[0195] Preparation of intermediate c-5:

[0196] Under nitrogen protection, 6.8g (10mmol) of intermediate b-2, 3.8g (12mmol) of raw material B-4, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 10 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-5.

[0197] Preparation of compound 165:

[0198] In a sealed pressure tube, under nitrogen protection, 9.2g (10mmol) of intermediate c-5 and 75mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 2.5 hours, the reaction was cooled to -42°C, 1.4mL (15mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 4 hours. After cooling to 0°C, 3.5mL (20mmol) of ultra-dry N,N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180°C for reaction for 15 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate, separate and purify with column chromatography to obtain compound 165. Compound 165 was dissolved in toluene solution (1×10 -5M) The half-peak width is 15 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0199] Example 6 Synthesis of Compound 172:

[0200]

[0201] Preparation of intermediate c-6:

[0202] Under nitrogen protection, 6.8g (10mmol) of intermediate b-2, 3.4g (12mmol) of raw material B-5, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 13 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-6.

[0203] Preparation of compound 172:

[0204] In a sealed pressure tube, under nitrogen protection, 8.8 g (10 mmol) of intermediate c-6 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 ° C, 4.8 mL of 2.5 M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60 ° C for 2 hours, the reaction was cooled to -42 ° C, 1.4 mL (15 mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 4 hours. After cooling to 0 ° C, 3.5 mL (20 mmol) of ultra-dry N, N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180 ° C for 16 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate and separate and purify with column chromatography to obtain compound 172. Compound 172 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 22nm, which is measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform) δ 8.76 (d, 1H), 8.31 (d, 1H), 8.07 (m, 2H), 7.82 (m, 2H), 7.63 (dd, 1H), 7.59–7.36 (m, 7H), 7.23 (dd, 2H), 7.11 (d, 2H), 3.12–2.98 (m, 3H), 1.39–1.33 (m, 30H), 1.29 (d, 6H).

[0205] Example 7 Synthesis of Compound 188:

[0206]

[0207] Preparation of intermediate b-3:

[0208] Dissolve the intermediate a-1 (3.0 g, 5.1 mmol) in 50 mL of tetrahydrofuran (THF) solution, slowly add 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution at -78 ° C under nitrogen gas; after stirring at -78 ° C for 3 hours, slowly add 0.48 mL of BBr3 (5 mol), react at -78 ° C for 2 hours, continue to add 1.04 mL of N, N-diisopropylethylamine (DIPEA) (6 mmol), heat the system to 150 ° C and react for 4.5 hours, and continue to add 15 mL of tetrahydrofuran solution in which the raw material C-3 (1.9 g, 5.5 mmol) is dissolved. Then slowly heat the reaction mixture to room temperature and stir overnight. Add dilute hydrochloric acid solution, distilled water and ethyl acetate to the reaction mixture, separate the water layer, and extract it three times with ethyl acetate. The combined organic layer is 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 an aqueous solution of NaHCO3. The aqueous layer was then separated and extracted with dichloromethane. Drying with sodium sulfate, filtering, and evaporation by rotary concentration and column to obtain intermediate b-3.

[0209] Preparation of intermediate c-7:

[0210] Under nitrogen protection, 7.1g (10mmol) of intermediate b-3, 3.4g (12mmol) of raw material B-5, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 17 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-7.

[0211] Preparation of compound 188:

[0212] In a sealed pressure tube, under nitrogen protection, 9.2g (10mmol) of intermediate c-7 and 75mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 2 hours, the reaction was cooled to -42°C, 1.4mL (15mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 3 hours. After cooling to 0°C, 3.5mL (20mmol) of ultra-dry N,N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180°C for reaction for 8 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate, separate and purify with column chromatography to obtain compound 188. Compound 188 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 23 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0213] Example 8 Synthesis of Compound 195:

[0214]

[0215] Preparation of intermediate d-1:

[0216] Under nitrogen protection, 4.4 g (10 mmol) of raw material D-1, 2.4 g (12 mmol) of raw material E-2, 2.1 g (15 mmol) of potassium carbonate, 0.6 g (0.5 mmol) of tetrakis (triphenylphosphine) palladium, 100 mL of tetrahydrofuran, and 10 mL of water were added to a three-necked flask and refluxed for 12 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate d-1.

[0217] Preparation of intermediate c-8:

[0218] Under nitrogen protection, 6.0 g (10 mmol) of intermediate b-1, 5.2 g (12 mmol) of intermediate d-1, 2.1 g (15 mmol) of potassium carbonate, 0.1 g (0.5 mmol) of palladium acetate, 0.4 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate and 100 mL of DMAC were added to a three-necked flask and refluxed for 15 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-8.

[0219] Preparation of compound 195:

[0220] In a sealed pressure tube, under nitrogen protection, 9.5 g (10 mmol) of intermediate c-8 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 ° C, 4.8 mL of 2.5 M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60 ° C for 2 hours, the reaction was cooled to -42 ° C, 1.4 mL (15 mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 2 hours. After cooling to 0 ° C, 3.5 mL (20 mmol) of ultra-dry N, N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180 ° C for 8 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate and separate and purify with column chromatography to obtain compound 195. Compound 195 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 14 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ8.72 (d, 1H), 8.30 (d, 1H), 7.82 (m, 3H), 7.74 (dd, 1H), 7.60 (m, 3H), 7.53 (d, 1H), 7.48–7.45 (m, 2H), 7.41–7.35 (m, 2H), 7.34 (m, 2H), 7.22 (m, 3H), 7.14 (dd, 2H), 7.02 (d, 3H), 6.98 (dd, 2H), 2.37 (s, 3H), 2.21 (s, 6H), 1.35 (d, 18H).

[0221] Example 9 Synthesis of Compound 250:

[0222]

[0223] Preparation of intermediate c-9:

[0224] Under nitrogen protection, 7.1g (10mmol) of intermediate b-3, 3.6g (12mmol) of raw material B-6, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 12 hours. After the reaction, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-9.

[0225] Preparation of compound 250:

[0226] In a sealed pressure tube, under nitrogen protection, 9.3g (10mmol) of intermediate c-9 and 75mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 4.8mL of 2.5M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 3 hours, the reaction was cooled to -42°C, 1.4mL (15mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 4 hours. After cooling to 0°C, 3.5mL (20mmol) of ultra-dry N,N-dimethyldiisopropylamine was added dropwise, and the reaction solution was heated to 180°C for reaction for 18 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate and separate and purify with column chromatography to obtain compound 250. Compound 250 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 16 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ8.53 (d, 1H), 8.44 (d, 1H), 8.35 (dd, 1H), 7.84 (dd, 1H), 7.81–7.70 (m, 2H), 7.68 (dd, 1H), 7.66–7.59 (m, 2H), 7.55–7.33 (m, 10H), 7.25 (s, 2H), 7.12 (dd, 2H), 3.17–3.05 (m, 2H), 1.39–1.31 (m, 30H).

[0227] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0228] Table 1

[0229]

[0230]

[0231] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-9 and device comparative examples 1-2. The device manufacturing process of device embodiments 2-9 and device comparative examples 1-2 of the present invention is exactly the same as that of device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also 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 2 and Table 3 respectively:

[0232] Device Example 1

[0233] like Figure 1As shown, the glass substrate layer 1 is an anode layer 2 (Ag (100nm)) formed by vacuum evaporation. On the anode layer 2, HT-1 and HI-1 with a thickness of 10nm are evaporated by a vacuum evaporation device as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then HT-1 with a thickness of 120nm is evaporated as a hole transport layer 4. Then EB-1 with a thickness of 10nm is evaporated as an electron blocking layer 5. After the evaporation of the above-mentioned electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared, using BH-1 as the main material, compound 21 as the doping material, the doping ratio of the doping material is 3% by weight, and the thickness of the light-emitting layer is 20nm. After the above-mentioned light-emitting layer 6, HB-1 is vacuum evaporated continuously, and the film thickness is 5nm. This layer is the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq are vacuum evaporated continuously, and 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 thickness of 1 nm was formed by a vacuum evaporation device, and this layer was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 16 nm was formed by a vacuum evaporation device, and the mass ratio of Mg to Ag was 1:9, and this layer was used as the cathode layer 10. On the cathode layer 10, 65 nm of CPL-1 was vacuum evaporated as the CPL layer 11.

[0234] The molecular structure formula of the relevant materials is shown below:

[0235]

[0236]

[0237] After the OLED light emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency, luminous peak and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2; the test results of the Index value (cd / A / CIEy), CIEy and life of the obtained device are shown in Table 3.

[0238] Table 2

[0239]

[0240] Table 3

[0241] Device Embodiment Blue Index(cd / A / CIEy) CIE <![CDATA[LT95 Lifetime (Hrs) @ 30 mA / cm 2 > Example 1 206.79 0.0480 197.2 Example 2 212.66 0.0483 221.4 Example 3 211.2 0.0453 209.7 Example 4 202.63 0.0461 199.7 Example 5 204.84 0.0449 224.9 Example 6 200.77 0.0458 196.2 Example 7 203.39 0.0432 209.7 Example 8 205.19 0.0472 221.3 Example 9 205.87 0.0443 219.6 Comparative Example 1 182.76 0.0544 133.2 Comparative Example 2 181.39 0.0573 110.0

[0242] 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.

[0243] It can be seen from the device data results in Table 3 that, compared with the comparative compounds ref-1 and ref-2, the boron-containing organic compound of the present invention can well achieve the effect of blue light emission and has a higher Blue Index efficiency; compared with the device comparison examples 1-2, the organic light-emitting device of the present invention has a greatly improved current efficiency and lifespan relative to the OLED device of the known materials, especially a very significant improvement in lifespan.

[0244] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that The structure of the boron-containing organic compound is shown in general formula (A): In the general formula (A), each occurrence of M1, M2, and M3 that is the same or different represents R-substituted or unsubstituted C6-C 30 One of aryl, R substituted or unsubstituted 5-30 membered heteroaryl; X1 represents C-Ar2 or N; Ar0 appears the same or different each time to represent substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Ar1 and Ar2, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Ar1 and Ar2 can also bond to form an R-substituted or unsubstituted five-membered ring; Z represents N, CH or CR; The R may be the same or different each time and may represent a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; The substitution mode of R is a single bond or a ring connection; The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

2. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (A-1) to (A-3): In the general formula (A-1) to the general formula (A-3), R6-R 20 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; R6-R 20 Any two adjacent ones can be connected to form a ring; X1 represents C-Ar2 or N; Ar0 appears the same or different each time to represent substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; X2 is represented by C(R a )(R b )、Si(R c )(R d ), NR e , O, S; R a -R d Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of an aryl group, a substituted or unsubstituted arylamine group, and a substituted or unsubstituted 5-30-membered heteroaryl group; R a With R b , R c With R d Can be connected into a ring; R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; R e , Ar4 can also be connected to form a ring; The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

3. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (A-4) to (A-7): In the general formula (A-4), Z represents CH or CR; The R may be the same or different each time and may represent a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; In the general formula (A-4) to the general formula (A-7), R6-R 20 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; R6-R 20 Any two adjacent ones can be connected to form a ring; Ar0 appears the same or different each time to represent substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Ar1 and Ar2 appear the same or different each time, indicating substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; X2 is represented by C(R a )(R b )、Si(R c )(R d ), NR e , O, S; R a -R d Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of an aryl group, a substituted or unsubstituted arylamine group, and a substituted or unsubstituted 5-30-membered heteroaryl group; R a With R b , R c With R d Can be connected into a ring; R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

4. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1) to (3): In the general formula (1) to the general formula (3), R1-R 20 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; R1-R 20 Any two adjacent ones can be connected to form a ring; X1 represents C-Ar2 or N; Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Ar3 and Ar4 can be connected to form a ring; X2 is represented by C(R a )(R b )、Si(R c )(R d ), NR e , O, S; R a -R d Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of an aryl group, a substituted or unsubstituted arylamine group, and a substituted or unsubstituted 5-30-membered heteroaryl group; R a With R b , R c With R d Can be connected into a ring; R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; R e , Ar4 can also be connected to form a ring; The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

5. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (4) to (10): In the general formula (4) to the general formula (10), R1-R 16 , R 22 -R 29 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; R1-R 16 , R 22 -R 29 Any two adjacent ones can be connected to form a ring; R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen atoms, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one of aryl, 5-30 membered heteroaryl, 5-30 membered heteroaryl substituted by deuterium or tritium, and arylamine; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

6. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (11) to (32): In the general formula (11) to the general formula (32), R1-R5, R7-R 10 , R 13 -R 16 , R 23 , R 24 , R 27 , R 28 , R 30 -R 54 Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted borane, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, B(R0)2, R0 represents a substituted or unsubstituted C6-C 30 Aryl; R1-R5, R7-R 10 , R 13 -R 16 , R 23 , R 24 , R 27 , R 28 , R 30 -R 54 Any two adjacent ones can be connected to form a ring; R e Each occurrence of the same or different C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; The substituents for the substituent groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 One or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl, and arylamine; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

7. The boron-containing organic compound according to any one of claims 1 to 6, characterized in that R, R1-R 54 The same or different occurrences of each of the above radicals are represented by 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, 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-phenylcarbazolyl , 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, diphenylamine; The R a -R e Each occurrence of the same or different radicals is represented by adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl , deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spiro Fluorenyl, 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, diphenylamine; Ar1, Ar2, Ar3, Ar4, which are the same or different each time, represent hydrogen, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl , deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9, 9-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, diphenylamine; The Ar0 is phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, 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 one of a deuterated bisphenyl group, a deuterated bisphenyl group, an ethyl substituted bisphenyl group, an isopropyl substituted bisphenyl group, a tert-butyl substituted bisphenyl group, a deuterated methyl substituted phenyl group, a deuterated ethyl substituted phenyl group, a deuterated isopropyl substituted phenyl group, a deuterated tert-butyl substituted phenyl group, a deuterated methyl substituted bisphenyl group, a deuterated ethyl substituted bisphenyl group, a deuterated isopropyl substituted bisphenyl group, a deuterated tert-butyl substituted bisphenyl group, a tert-butyl substituted dibenzofuranyl group, a phenyl substituted tert-butyl group, a xanthone group, and a phenyl substituted triazine group; The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, and a diphenylamine group; Preferably, the R, R1-R 54 They are independently represented as follows: Hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group, Any of; The R e Each occurrence of the same or different is represented by: Any of; The same or different occurrences of Ar1, Ar2, Ar3, and Ar4 are represented as follows: Hydrogen atom, methyl, ethyl, isopropyl, tert-butyl, Any of; The same or different Ar0 is represented by: Any one of.

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

9. An organic electroluminescent device, comprising a substrate, a first electrode, an organic light-emitting functional layer and a second electrode in sequence, wherein the organic light-emitting functional layer is located between the first electrode and the second electrode, and the organic light-emitting functional layer includes a light-emitting layer, characterized in that: The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 8. 10 . The organic electroluminescent device according to claim 9 , wherein the light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to claim 1 .

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