Boron-containing organic compound and organic electroluminescent device containing 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 (1), # imgabs0. When the compound is used as a doping material in a light-emitting layer material of an OLED light-emitting device, the compound can be used as a light-emitting layer green light doping material of the organic light-emitting device, so that the light-emitting efficiency of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and in particular to a boron-containing organic compound and an organic electroluminescent device containing the same. 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 DCIP3) can no longer meet the high-quality technical development needs of display products. In order to achieve the performance requirements of ultra-high definition and higher picture quality 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 commercialized OLED red, green and blue color rendering technologies, blue light uses traditional fluorescent triplet-triplet conversion (TTF) technology, which has low efficiency but high color purity and basically meets the BT.2020 display indicators; green and red light use phosphorescence technology, which has high efficiency. Red light is close to the BT.2020 display indicators, while green light is limited by the wider emission spectrum of phosphorescence, which is quite different from the requirements of high-definition display indicators. Therefore, it is very critical to develop high-color-purity green light OLED materials.

[0003] Since 2020, green light materials with narrow half-width (half-width <30nm) based on boron-nitrogen resonance structures have been reported one after another: DOI:10.1002 / adom.201902142, DOI:10.1002 / anie.202008264, DOI:10.1021 / jacs.0c10081, DOI:10.1038 / s41467-022-32607-3, DOI:10.1002 / anie.202202380, etc., showing the extremely high color purity and efficiency of this type of material, becoming the development trend of high color purity green light OLEDs. However, there are still many technical difficulties in the development of green light ultra-high color purity materials containing boron and nitrogen structures. The existing materials also have the defects that their efficiency and lifespan cannot meet the needs of mass production. The development of narrow half-width green light materials based on boron and nitrogen resonance structures that can meet practical applications is a key technical point for the next generation of high color purity, high color gamut coverage, high efficiency and high immersion display devices.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials, utilizes triplet exciton-sensitizing materials as exciton-sensitizing media, fully utilizes triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device internal quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications. For example, CN107507921A and CN110492006A disclose a luminescent layer combination technology with TADF materials with a difference of the lowest singlet and triplet energy levels of less than or equal to 0.2eV as the main body and boron-containing materials as doping; CN110492005A and CN110492009A disclose a luminescent layer combination scheme with an exciplex as the main body and boron-containing materials as doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the invention

[0005] 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 containing the same. The compound of the present invention is used as a doping material for the light-emitting layer of the organic electroluminescent device to emit green light.

[0006] The technical solution of the present invention is as follows: a boron-containing organic compound, the structure of which is shown in general formula (1):

[0007]

[0008] In the general formula (1), R1 and R2, which are the same or different each time, represent 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0009] R1 and R2 can be connected to form substituted or unsubstituted C6~C30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0010] Each occurrence of M1, M2, M3, M4, M5, and M6, which is the same or different, indicates that C6 to C6 is substituted or unsubstituted by one or more R. 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings;

[0011] R, which is the same or different each time it appears, represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0012] The substitution mode of R is a single bond or a ring connection;

[0013] Each occurrence of X, whether the same or different, represents a carbon atom or a silicon atom;

[0014] Each occurrence of Y, whether the same or different, is represented by one of C(Ra)(Rb), Si(Rc)(Rd), N-Re, O, and S;

[0015] Each occurrence of Ra, Rb, Rc, Rd, and Re that is the same or different indicates substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0016] Ra and Rb can be connected to form a ring;

[0017] Rc and Rd can be connected to form a ring;

[0018] The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups;

[0019] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0020] In a preferred embodiment, the structure of the boron-containing organic compound is shown in general formula (2):

[0021]

[0022] In the general formula (2), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0023] R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0024] M1 and M6 represent C6-C substituted or unsubstituted by one or more R 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings;

[0025] R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0026] The substitution mode of R is a single bond or a ring connection;

[0027] Each occurrence of X independently represents a carbon atom or a silicon atom;

[0028] Each occurrence of Y is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S;

[0029] R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0030] Ra and Rb can be connected to form a ring;

[0031] Rc and Rd can be connected to form a ring;

[0032] The substituents for substituting the above substitutable groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups;

[0033] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0034] In a preferred embodiment, the structure of the boron-containing organic compound is shown in general formula (3):

[0035]

[0036] In the general formula (3), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0037] R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0038] M6 represents a C6-C6-substituted or unsubstituted C6-C6-substituted 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings;

[0039] R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0040] The substitution mode of R is a single bond or a ring connection;

[0041] Each occurrence of X independently represents a carbon atom or a silicon atom;

[0042] Each occurrence of Y is represented independently as C(R a)(R b )、Si(R c )(R d )、N(R e ), O or S;

[0043] R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0044] Ra and Rb can be connected to form a ring;

[0045] Rc and Rd can be connected to form a ring;

[0046] The substituents for substituting the above substitutable groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups;

[0047] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0048] Preferably, the structure of the boron-containing organic compound is as shown in general formula (4-1) or general formula (4-2):

[0049]

[0050] In the general formula (4-1) and the general formula (4-2), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0051] R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0052] M1 represents a C6-C 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings;

[0053] R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0054] The substitution mode of R is a single bond or a ring connection;

[0055] Each occurrence of X independently represents a carbon atom or a silicon atom;

[0056] Each occurrence of Y and Y1 is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S;

[0057] R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0058] Ra and Rb can be connected to form a ring;

[0059] Rc and Rd can be connected to form a ring;

[0060] The substituents for substituting the above substitutable groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups;

[0061] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0062] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (5-1) to (5-4):

[0063]

[0064] In the general formula (5-1) to the general formula (5-4), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0065] R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0066] Z is represented by CH or CR;

[0067] R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0068] Each occurrence of X independently represents a carbon atom or a silicon atom;

[0069] Each occurrence of Y and Y1 is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S;

[0070] R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0071] The substituents for substituting the above substitutable groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups;

[0072] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0073] In a preferred embodiment, M1, M2, M3, M4, M5, and M6 are represented by R substituted or unsubstituted groups: any one of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indole [3,2,1-jk] carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl;

[0074] The R represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, linoyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0075] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23Each of the above is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0076] Said Ra, Rb, Rc, Rd, and Re are independently represented by substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0077] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

[0078] In a preferred embodiment, M1, M2, and M3 are represented by any one of the following ring structures:

[0079]

[0080] The M4, M5, and M6 are represented by any of the following ring structures:

[0081]

[0082] Each occurrence of Z is independently represented as CH or CR;

[0083] The R is represented by the following structure:

[0084] Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl,

[0085] Any of;

[0086] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 They are independently represented as follows:

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

[0088] Any of;

[0089] The Ra, Rb, Rc, Rd and Re are represented by the following structure:

[0090] Methyl, isopropyl, tert-butyl, Any one of.

[0091] In a preferred embodiment, the specific structure of the boron-containing organic compound is any one of the following structures:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] The present invention also provides 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 comprises a light-emitting layer, wherein the light-emitting layer contains the boron-containing organic compound of the present invention;

[0104] In a preferred embodiment, the light-emitting layer comprises a main material and a doping material, and the doping material comprises the boron-containing organic compound described in the present invention;

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

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

[0107] Compared with the prior art, the beneficial technical effects of the present invention are:

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

[0109] (2) The compound of the present invention is used as a doping material and introduced into a phosphorescent sensitizer, which can effectively improve the efficiency and life of the device;

[0110] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and enhance the luminous efficiency of the device;

[0111] (4) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

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

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

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

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

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

[0117] In the present invention, the term “can be connected to form a ring” means that the two groups may be unconnected or mutually connected to form a ring, preferably connected to form a five-membered ring or a six-membered ring through a C-C 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 C2-C 30 Heteroaryl.

[0118] In the present invention, the substituted or unsubstituted aromatic amine group described in the present invention refers to Wherein Q4 and Q5 represent substituted or unsubstituted aromatic groups, and Q4 and Q5 preferably represent substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C2-C 30 Heteroaryl.

[0119] 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.

[0120] In the present invention, substituted or unsubstituted C2-C 30 Heteroaryl (C2 means that the number of carbon atoms contained is 2) refers to substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, The invention also includes but is not limited to oxazolyl, 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 fused rings of combinations of the foregoing groups, but are not limited thereto.

[0121] 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.

[0122] The C3-C 10Cycloalkyl 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.

[0123] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0124] 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.

[0125] The C2-C 10 Alkenyl 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.

[0126] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

[0127] 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 PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] Preferably, the main organic material of the hole injection layer of the present invention can be selected from the compounds disclosed in the following prior arts: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] 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.

[0139] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0140]

[0141] 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.

[0142] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0143] 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:

[0144]

[0145]

[0146] 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.

[0147] 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.

[0148] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of the present invention.

[0149] The light-emitting layer may contain a single host material or a dual host material;

[0150] The dual-host material comprises a first host material and a second host material, and preferably at least one of the first host material and the second host material is a TADF material;

[0151] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy level difference between the first excited singlet state and the first excited triplet state, so that the singlet excitons and triplet excitons generated can be used simultaneously in the device, making the utilization rate of the excitons generated by the device as close to 100% as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0152] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0153] Exciton sensitizing materials refer to materials that can make the luminescent material in the luminescent layer fully utilize the electroexcitons, so that the luminescent layer finally produces the emission spectrum of the sensitized material. Exciton sensitizers may undertake functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has a significant improvement effect on the problems of device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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:

[0158]

[0159]

[0160] 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.

[0161] 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:

[0162]

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] Synthesis Example

[0171] 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;

[0172] Example 1 Synthesis of Compound 7:

[0173]

[0174] Preparation of raw material 1b:

[0175] Add raw material 1a (31.0 g, 110.0 mmol) to acetonitrile (600 mL), add hydrochloric acid (6N, 400 mL) under ice bath, add sodium nitrite aqueous solution (9.1 g, 132.0 mmol) (50 mL) dropwise, stir under ice bath for 1 hour, then add potassium iodide aqueous solution (182.6 g, 1.1 mol) (500 mL), continue stirring under ice bath for 1 hour. After the reaction is completed, filter, wash the residue with methanol / petroleum ether, and dry under reduced pressure to obtain raw material 1b (40.0 g) as a white solid.

[0176] Preparation of intermediate 1d:

[0177] Add raw material 1b (19.62 g, 50.0 mmol), raw material 1c (10.31 g, 50.0 mmol), DMF (500 mL), copper powder (9.53 g, 150.0 mmol), calcium carbonate (15.0 g, 150 mmol) into the bottle, and stir the reaction solution at 80 degrees Celsius for 48 hours under nitrogen protection. After the reaction, cool to room temperature. Then pour into water, extract with ethyl acetate, combine the organic phases and wash with saturated brine, dry over anhydrous Na2SO4, concentrate under reduced pressure, and purify by column chromatography (petroleum ether / ethyl acetate = 20 / 1) to obtain intermediate 1d (21.9 g, 46.5 mmol) as a white solid.

[0178]

[0179] Preparation of 1g of raw material:

[0180] To the reaction flask, raw material 1e (33.5 g, 100.0 mmol), raw material 1f (28.0 g, 100.0 mmol), Pd2(dba)3 (2.0 g, 2.2 mmol), S-phos (1.8 g, 4.4 mmol), potassium carbonate (41.5 g, 300 mmol), and toluene (800 mL) were added in sequence; then, the mixture was protected with nitrogen and refluxed overnight. After the reaction was completed, the mixture was cooled to room temperature, ethyl acetate was added to dilute the reaction solution, and the solution was washed with saturated brine, concentrated, and separated by silica gel column chromatography to obtain raw material 1g.

[0181] Preparation of intermediate 1q:

[0182] To the reaction flask, 1 g (9.74 g, 20 mmol) of raw material and anhydrous THF (150 mL) were added in sequence, and the mixture was protected by nitrogen. The temperature was lowered to -78 °C, and n-butyl lithium (9 mL, 22.5 mmol, 2.5 M) was added. The temperature was then raised to -10 °C and the reaction was allowed to react for two hours. The raw material 1h (3.92 g, 20 mmol) was added, and the stirring was continued at room temperature overnight. The mixture was quenched by adding aqueous ammonium chloride solution, extracted with ethyl acetate, and the organic phases were combined and concentrated to dryness to obtain a solid. Dichloromethane (300 mL) was then added to dissolve the solid, and hydrochloric acid (50 mL) was added at 0 °C. The mixture was protected by nitrogen and stirred at room temperature for 2 h. The reaction was directly spin-dried and separated by silica gel column chromatography to obtain intermediate 1q.

[0183] Preparation of intermediate 1k:

[0184] Add intermediate 1q (9.67 g, 16.5 mmol), intermediate 1d (7.77 g, 16.5 mmol), Cs2CO3 (16.1 g, 49.5 mmol), DMF (200 mL) to the reaction flask in sequence, protect with nitrogen, stir at 140 degrees Celsius for 8 hours, and cool down after the reaction is completed. Add ethyl acetate to dilute the reaction solution, add saturated brine to wash away DMF, extract the aqueous phase with ethyl acetate, combine and concentrate the organic phases, and separate the intermediate 1K through silica gel column chromatography. LC-MS: theoretical value: 1035.49; measured value: 1036.55 ([M+H] + ).

[0185] Preparation of compound 7:

[0186] The intermediate 1k (11.72 g, 11.3 mmol) and anhydrous o-dichlorobenzene (140 mL) were added to the reaction flask in sequence, the temperature was lowered to -78 ° C under nitrogen protection, t-BuLi (20 mL, 2.6 mmol, 1.3 M) was added, and then the temperature was raised to room temperature and stirred for one hour, BBr3 (8.5 g, 34.0 mmol) was added at -40 ° C, DIPEA (10.0 ml, 60.0 mmol) was added, and then stirred at 150 ° C overnight. After the reaction was completed, it was quenched with a saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phase was concentrated and chromatographed on a silica gel column to obtain compound 7.

[0187] 1 H NMR(400MHz,Chloroform-d)δ8.75(s,1H),8.25(d,H),7.95-7.91(m,2H),7. 62-7.41(m,10H),7.35-7.20(m,8H),7.08-6.98(m,6H),1.36-1.31(m,36H).

[0188] Example 2 Synthesis of Compound 78:

[0189]

[0190] Preparation of raw material 2b:

[0191] The synthesis of starting material 2b refers to the synthesis of intermediate 1d, except that starting material 2a is used instead of starting material 1b.

[0192] Preparation of raw material 2c:

[0193] The raw material 2b (3.73 g, 10.0 mmol) was dissolved in N, N-dimethylacetamide (50 mL), and tricyclohexylphosphine (0.84 g, 3.0 mmol), palladium acetate (0.33 g, 1.5 mmol), and cesium carbonate (6.53 g, 20.0 mmol) were added in sequence. Under nitrogen protection, the mixture was stirred at 160 degrees for 9 h, and the reaction was cooled to room temperature after completion. The mixture was then poured into water and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, concentrated under reduced pressure, and separated by column chromatography to obtain the raw material 2c.

[0194]

[0195] Preparation of intermediate 2k:

[0196] The preparation of intermediate 2k refers to the preparation of intermediate 1k, except that raw material 2c is used instead of intermediate 1d. LC-MS: theoretical value: 901.38; measured value: 902.33 ([M+H] + ).

[0197] Preparation of compound 78:

[0198] The preparation of compound 78 was carried out by referring to the preparation of compound 7, except that intermediate 2k was used instead of intermediate 1k.

[0199] 1 H NMR(400MHz,Chloroform-d)δ8.92(s,1H),8.43-8.14(m,4H),7.90-7.88(m,2H),7.60 -7.48(m,5H),7.33-7.22(m,5H),7.16-6.98(m,6H),1.46(s,9H),1.29-1.28(m,18H).

[0200] Example 3 Synthesis of Compound 80:

[0201]

[0202] Preparation of raw material 3b:

[0203] To the reaction flask, add raw material 3a (20.73 g, 100 mmol), NaH (6.0 g, 150 mmol, 60%) and THF (150 mL) in sequence under nitrogen protection and stir at reflux temperature for 3 days. After the reaction, pour the reaction solution into saturated brine, extract with ethyl acetate, and separate through silica gel column to obtain raw material 3b.

[0204] Preparation of raw material 3d:

[0205] Add raw material 3b (21.0 g, 60 mmol), chloroform (200 mL), PCl5 (25.0 g, 120 mmol) to the bottle, reflux for 4 h under nitrogen protection; after the reaction, evaporate to dryness under reduced pressure to obtain raw material 3c (crude product), then directly add THF (150 mL), trifluoroacetic acid (100 mL), ice bath, slowly add Zn powder (9.8 g, 150 mmol) under nitrogen flow, stir overnight at reflux temperature. After the reaction, cool to room temperature, pour the reaction solution into saturated brine, extract with ethyl acetate, combine the organic phases, concentrate and separate by silica gel column chromatography to obtain raw material 3d (white powder).

[0206] Preparation of raw material 3e:

[0207] The synthesis of raw material 3e refers to the synthesis of intermediate 1d, except that raw material 3d is used instead of raw material 1c, and raw material 2a is used instead of raw material 1b.

[0208] Preparation of raw material 3f:

[0209] The synthesis of raw material 3f refers to the synthesis of raw material 2c, except that raw material 3e is used instead of raw material 2b.

[0210]

[0211] Preparation of raw material 3k:

[0212] The synthesis of raw material 3k refers to the synthesis of intermediate 1k, except that raw material 3f is used instead of intermediate 1d. LC-MS: theoretical value: 1013.51; measured value: 1014.63 ([M+H] + ).

[0213] Preparation of compound 80:

[0214] The preparation of compound 80 was carried out by referring to the preparation of compound 7, except that intermediate 3k was used instead of intermediate 1k.

[0215] 1 H NMR(400MHz,Chloroform-d)δ8.73(s,1H),8.31-7.92(m,5H),7.54-7.48(m, 4H),7.33-7.20(m,4H),7.09-6.99(m,7H),1.42(s,9H),1.33-1.31(m,36H).

[0216] Example 4 Synthesis of Compound 86:

[0217]

[0218] Preparation of intermediate 4b:

[0219] The synthesis of intermediate 4b refers to the synthesis of intermediate 1q, except that starting material 4a is used instead of starting material 1h.

[0220] Preparation of intermediate 4k:

[0221] The synthesis of intermediate 4k refers to the synthesis of intermediate 1k, except that intermediate 4b is used instead of intermediate 1q, and raw material 2c is used instead of intermediate 1d. LC-MS: theoretical value: 917.36; measured value: 918.51 ([M+H] + ).

[0222] Preparation of compound 86:

[0223] The synthesis of compound 86 was based on the synthesis of compound 7, except that intermediate 4k was used instead of intermediate 1k.

[0224] 1H NMR(400MHz,Chloroform-d)δ8.79(s,1H),8.41-8.25(m,3H),8.11-8.09(d,1H),7.90-7.88(s,1H),7.59 -7.52(m,3H),7.48-7.46(m,2H),7.38-7.20(m,10H),7.08-7.06(m,2H),1.38(s,9H),1.28-1.26(m,18H).

[0225] Example 5 Synthesis of Compound 123:

[0226]

[0227] Preparation of intermediate 5k:

[0228] The synthesis of intermediate 5k refers to the synthesis of intermediate 1k, except that raw material 5a is used instead of intermediate 1d. LC-MS: theoretical value: 920.35; measured value: 921.38 ([M+H] + ).

[0229] Preparation of compound 123:

[0230] The synthesis of compound 123 was based on the synthesis of compound 7, except that intermediate 5k was used instead of intermediate 1k.

[0231] 1 H NMR(400MHz,Chloroform-d)δ8.52(s,1H),8.25-8.10(m,3H),7.52-7.36(m,6H) ),7.32-7.19(m,9H),7.11-7.05(m,4H),7.0-6.93(m,6H),1.26-1.24(m,18H).

[0232] Example 6 Synthesis of Compound 128:

[0233]

[0234] Synthesis of intermediate 6k:

[0235] The synthesis of intermediate 6k was based on the synthesis of intermediate 1k, except that raw material 1f was used instead of intermediate 1d. LC-MS: theoretical value: 844.42; measured value: 845.45 ([M+H] + ).

[0236] Synthesis of compound 128:

[0237] The synthesis of compound 128 was based on the synthesis of compound 7, except that intermediate 6k was used instead of intermediate 1k.

[0238] 1 H NMR(400MHz,Chloroform-d)δ8.63(s,1H),8.32-8.25(m,2H),7.91(s,1H),7.75-7 .73(d,2H),7.50-7.22(m,8H),7.12-7.00(m,5H),1.38(s,9H),1.30-1.29(m,27H).

[0239] Example 7 Synthesis of Compound 132:

[0240]

[0241] Synthesis of intermediate 7k:

[0242] The synthesis of intermediate 7k refers to the synthesis of intermediate 1k, except that intermediate 4b is used instead of intermediate 1q; raw material 1f is used instead of intermediate 1d. LC-MS: theoretical value: 860.39; measured value: 861.37 ([M+H] + ).

[0243] Synthesis of compound 132:

[0244] The synthesis of compound 132 was based on the synthesis of compound 7, except that intermediate 7k was used instead of intermediate 1k.

[0245] 1 H NMR(400MHz,Chloroform-d)δ8.75-8.67(m,2H),8.32-8.25(m,2H),7.69-7.67(d,2H),7 .48-7.31(m,7H),7.24-7.20(m,4H),7.08-7.06(m,2H),1.43(s,9H),1.28-1.14(m,27H).

[0246] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0247] Table 1

[0248]

[0249] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-7 and device comparative examples 1-2. The device manufacturing process of device embodiments 2-7 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 2-1 and Table 3 respectively:

[0250] Device Example 1

[0251] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washing with a cleaning agent (Semiclean M-L20), washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is made, using GH-1 and GH-2 as the main materials, compound 7 as the doping material, the mass ratio of GH-1, GH-2 and compound 7 is 69:30:1, and the film thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0252] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 8-14 and device comparative examples 3-4. The device manufacturing process of device embodiments 9-14 and device comparative examples 3-4 of the present invention is exactly the same as that of device embodiment 8, and the same substrate material and electrode material are used. The film thickness of the electrode material is also consistent. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-2 and Table 3 respectively:

[0253] Device Example 8

[0254] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 to HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Then, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, GD-1 as the first doping material, and compound 7 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 7 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 is vacuum-deposited with a film thickness of 5nm. This layer is the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq are vacuum-deposited. The mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1nm is prepared by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80nm is prepared by a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0255] The molecular structure formula of the relevant materials is shown below:

[0256]

[0257]

[0258] 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 value and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2-1 and Table 2-2; the test results of the current efficiency, luminous peak value and life of the obtained device are shown in Table 3.

[0259] Table 2-1

[0260]

[0261] Table 2-2

[0262]

[0263] Table 3

[0264]

[0265] 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.

[0266] It can be seen from the device data results in Table 3 that the luminescence peak of the compound of the present invention is between 510 and 540 nm, which can well achieve the effect of green luminescence;

[0267] Compared with device comparative example 1-2, device example 1-7 has a significantly improved overall lifespan, and device example 1-7 shows higher efficiency than comparative example 1-2. Compared with device comparative examples 3-4, device examples 8-14 show that when GD-1 is introduced, the lifespan stability of the compound of synthetic example 1-7 is much higher than that of comparative example compounds ref-1 and ref-2.

[0268] The organic light-emitting device of the present invention has a greatly improved current efficiency and lifespan compared to OLED devices of known materials, whether in a single-doping system or a double-doping system; when an exciton-sensitizing material is used as the first doping, the device efficiency is significantly improved compared to a single-doping system.

[0269] 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 (1): In the general formula (1), R1 and R2, which are the same or different each time, represent 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; R1 and R2 can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; Each occurrence of M1, M2, M3, M4, M5, and M6, which is the same or different, indicates that C6 to C6 is substituted or unsubstituted by one or more R. 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings; R, which is the same or different each time it appears, represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The substitution mode of R is a single bond or a ring connection; Each occurrence of X, whether the same or different, represents a carbon atom or a silicon atom; Each occurrence of Y, whether the same or different, is represented by one of C(Ra)(Rb), Si(Rc)(Rd), N-Re, O, and S; Each occurrence of Ra, Rb, Rc, Rd, and Re that is the same or different indicates substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ra and Rb can be connected to form a ring; Rc and Rd can be connected to form a ring; 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, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more 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 general formula (2): In the general formula (2), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; M1 and M6 represent C6-C substituted or unsubstituted by one or more R 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings; R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The substitution mode of R is a single bond or a ring connection; Each occurrence of X independently represents a carbon atom or a silicon atom; Each occurrence of Y is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S; R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ra and Rb can be connected to form a ring; Rc and Rd can be connected to form a ring; The substituents for substituting the above substitutable groups may be selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more 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 general formula (3): In the general formula (3), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; M6 represents a C6-C6-substituted or unsubstituted C6-C6-substituted 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings; R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The substitution mode of R is a single bond or a ring connection; Each occurrence of X independently represents a carbon atom or a silicon atom; Each occurrence of Y is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S; R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ra and Rb can be connected to form a ring; Rc and Rd can be connected to form a ring; The substituents for substituting the above substitutable groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more 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 general formula (4-1) or general formula (4-2): In the general formula (4-1) and the general formula (4-2), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; M1 represents a C6-C 30 aromatic ring, substituted or unsubstituted C2-C 30 One of the heteroaromatic rings; R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The substitution mode of R is a single bond or a ring connection; Each occurrence of X independently represents a carbon atom or a silicon atom; Each occurrence of Y and Y1 is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S; R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ra and Rb can be connected to form a ring; Rc and Rd can be connected to form a ring; The substituents for substituting the above substitutable groups may be selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more 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 (5-1) to (5-4): In the general formula (5-1) to the general formula (5-4), R1 to R 23 Each occurrence independently represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; R1~R 23 Any two adjacent groups can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted C2~C 30 Heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; Z is represented by CH or CR; R represents 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~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; Each occurrence of X independently represents a carbon atom or a silicon atom; Each occurrence of Y and Y1 is represented independently as C(R a )(R b )、Si(R c )(R d )、N(R e ), O or S; R a , R b , R c , R d , R e Each occurrence independently represents substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents for substituting the above substitutable groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium-substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

6. The boron-containing organic compound according to any one of claims 1 to 5, characterized in that The M1, M2, M3, M4, M5, and M6 represent any of the following groups substituted or unsubstituted by R: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl; The R represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, linoyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 Each of the above is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; Said Ra, Rb, Rc, Rd, and Re are independently represented by substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

7. The boron-containing organic compound according to any one of claims 1 to 5, characterized in that The M1, M2, and M3 are represented by any of the following ring structures: The M4, M5, and M6 are represented by any of the following ring structures: Each occurrence of Z is independently represented as CH or CR; The R is represented by the following structure: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 They are independently represented as follows: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of; The Ra, Rb, Rc, Rd and Re are represented by the following structure: Methyl, isopropyl, tert-butyl, 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; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to any one of claims 1 to 8; Preferably, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-8.

10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material, an exciton sensitizing material and a doping material, wherein: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing organic compound according to any one of claims 1 to 8.

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