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 (1), # imgabs0. When the compound is used as a doping material in a luminescent layer material of an OLED luminescent device, the compound can be used as a luminescent layer green light doping material of the OLED luminescent device, and green light emission is achieved.

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 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 / s41566-022-01083-y, DOI:10.1038 / s41467-022-32607-3, DOI:10.1002 / anie.202202380, etc., showing the high color purity and efficiency of this type of material, which has become 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, CN 107507921 A 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 0.2 eV as the main body and boron-containing materials as doping; CN 110492005 A and CN 110492009A 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-peak width. Therefore, the development of sensitization technology based on narrow half-peak 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 prepared therefrom. The compound of the present invention can be used as a green light doping material of the light-emitting layer of an organic electroluminescent device by introducing an eight-membered ring characteristic donor structure containing para-aromatic amine on a boron-nitrogen fused ring mother core to achieve green light emission.

[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), Z represents CR;

[0009] R, which is the same or different each time, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane;

[0010] Adjacent R can be connected to form substituted or unsubstituted C6~C 30Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0011] Z1, Z2, and Z3 are represented by C-Ra, C-Rb, and C-Rc, respectively;

[0012] Ra, Rb, and Rc are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane;

[0013] Ra, Rb, and Rc can be linked to each other to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring;

[0014] Q1 represents substituted or unsubstituted 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;

[0015] Q2 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 5-30 membered heteroaryl, borane, substituted or unsubstituted C4-C 30 Alkenyl, substituted or unsubstituted C3-C 30 One of the carbon-nitrogen double bonds;

[0016] M1 and M2 represent substituted or unsubstituted C6~C 30 one of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0017] Q1 and M1, Q1 and the adjacent R can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 Aliphatic ring, substituted or unsubstituted C5~C 30 spiral ring;

[0018] Q2 and M2, Q2 and the adjacent Rc can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 Aliphatic ring, substituted or unsubstituted C5~C 30 spiral ring;

[0019] The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane;

[0020] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0021] Furthermore, the structure of the boron-containing organic compound is as shown in any one of the general formulas (1-1) to (1-3):

[0022]

[0023] In general formula (1-1) to general formula (1-3), Z, Z1, Z2, Z3, M1, M2, and Q1 have the same meanings as defined in general formula (1);

[0024] M3, M4, and M5 represent substituted or unsubstituted C6~C 30 one of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0025] Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane;

[0026] The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane;

[0027] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0028] Furthermore, the structure of the boron-containing organic compound is as shown in any one of the general formulas (2) to (4):

[0029]

[0030] In general formula (2) to general formula (4), Z, Z1, Z2, Z3, M2, Q1, Q2 have the same meanings as defined in general formula (1);

[0031] X is represented by one of O or S;

[0032] Preferably, the general formula (2) is represented by the general formula (2-1):

[0033]

[0034] In the general formula (2-1), Z, Z1, Z2, Z3, M2, and Q1 have the same meanings as those defined in the general formula (1);

[0035] Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane;

[0036] The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane;

[0037] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0038] Furthermore, the structure of the boron-containing organic compound is as shown in any one of the general formulas (5) to (19):

[0039]

[0040]

[0041] In general formulae (5) to (19), Z, Z1, Z2, Z3, Q1, and Q2 have the same meanings as those defined in general formula (1);

[0042] X is represented by one of O or S;

[0043] X2 represents one of O, S, C(Rd)(Re), Si(Rf)(Rg);

[0044] Rd, Re, Rf, and Rg represent substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, borane, substituted or unsubstituted C4-C 30 Alkenyl, substituted or unsubstituted C3-C 30 One of the carbon-nitrogen double bonds;

[0045] Rd and Re, Rf and Rg can be connected to form a ring;

[0046] Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane;

[0047] The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane;

[0048] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0049] Furthermore, the structure of the boron-containing organic compound is as shown in any one of the general formulas (20) to (28):

[0050]

[0051] In general formulae (20) to (28), Z, Z1, and Q1 have the same meanings as defined in general formula (1);

[0052] X and X3 represent one of O and S.

[0053] Furthermore, the structure of the boron-containing organic compound is as shown in any one of the general formulas (29) to (41):

[0054]

[0055]

[0056] In general formulae (29) to (41), Z, Q1, Z1, Z2, and Z3 have the same meanings as defined in general formula (1);

[0057] X is represented by one of O or S;

[0058] Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, 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, borane, substituted or unsubstituted C4-C 30 Alkenyl, substituted or unsubstituted C3-C 30 One of the carbon-nitrogen double bonds;

[0059] The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane;

[0060] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0061] Further, the R, Ra, Rb, and Rc are represented by the following structure:

[0062] Hydrogen atom, deuterium atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, Any of;

[0063] The Rd, Re, R f , R g , Q3, and Q4 are independently expressed as the following structural features:

[0064] Any of;

[0065] The Q1 and Q2 are independently represented by the following structural features:

[0066] Any of;

[0067] The M1, M2, M3, M4, and M5 are independently represented by any of the following ring structures:

[0068]

[0069] The meaning of Z is the same as defined in the general formula (1), and the asterisk indicates a linkable site.

[0070] Further, R, Ra, Rb, and Rc are independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group , 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;

[0071] The Rd, Re, R f , R g Each of the following independently represents adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated 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 The present invention is one of the following: 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, tert-butyl substituted phenyl, xanthone, phenyl substituted triazine, phenyl substituted borane, methoxy, tert-butoxy, diphenylamine;

[0072] The Q3, Q4, M1, M2, M3, M4, and M5 are represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone;

[0073] The Q1 and Q2 are phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, xanthone, One of;

[0074] 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.

[0075] Furthermore, the specific structure of the boron-containing organic compound is any one of the following structures:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] The present invention also discloses 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 of the present invention;

[0092] Preferably, 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;

[0093] 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 described in the present invention.

[0094] Furthermore, 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.

[0095] Compared with the prior art, the beneficial technical effects of the present invention are:

[0096] (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;

[0097] (2) The compounds of the present invention have excellent structural stability, which helps to improve the life of the device;

[0098] (3) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

[0099] (4) The compound of the present invention is used as a doping material to introduce a phosphorescent sensitizer, which can effectively improve the efficiency and life of the device;

[0100] (5) The spectral FWHM of the compounds of the present invention is relatively narrow, which can effectively improve the color gamut of the device; BRIEF DESCRIPTION OF THE DRAWINGS

[0101] 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;

[0102] 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

[0103] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0104] 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.

[0105] In the present invention, the substituted or unsubstituted aromatic amine group described in the present invention refers to Wherein Q5 and Q6 represent substituted or unsubstituted aromatic groups, and Q5 and Q6 preferably represent substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C2-C 30 Heteroaryl.

[0106] 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.

[0107] In the present invention, the substituted or unsubstituted 5-30 membered heteroaryl group or 5-30 membered heteroaryl ring refers to a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted The invention may include substituted benzimidazolyl, 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.

[0108] 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.

[0109] 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.

[0110] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0111] 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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.

[0126] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0127] JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN103108859A.

[0128] 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.

[0129] 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.

[0130] 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:

[0131] CN102046613A, CN105408448A, KR1020160049955A, CN103108859A, KR1020130106255A, EP2922932A1, CN102224150A, US20170018710A1.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] The light-emitting layer may contain a single host material or a dual host material;

[0136] 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;

[0137] 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.

[0138] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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, a compound with a hole blocking effect known in the prior art can be used, such as the following compounds disclosed in the prior art:

[0144] Appl.Phys.Lett.75,4(1999), Appl.Phys.Lett.83,3858(2003), JP2015111679A, KR1020180043220A, CN109564982A, KR1020180065246A.

[0145] 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.

[0146] The electron transport layer may be disposed on the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials for organic electroluminescent devices disclosed in the prior art can be used, for example, the compounds disclosed in the following prior art: CN1784388A, CN1625552A, CN107431141A, CN107431141A, KR1020160149041A, KR1020160149041A, CN103827256A, KR101847347B1, KR1020190050658A, CN102574813A, CN107721979A, KR1020100073954A.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] Synthesis Example

[0155] 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;

[0156]

[0157] Synthesis of intermediate a-1:

[0158] In a three-necked flask, raw material A-1 (0.74 g, 2.5 mmol) was dissolved in 50 mL of toluene solution under nitrogen, and raw material B-1 (0.65 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 22 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate a-1.

[0159] Synthesis of intermediate Q1:

[0160] In a three-necked flask, under nitrogen, (1.2 g, 2.5 mmol) of intermediate a-1, (0.05 g, 0.2 mmol) of tricyclohexylphosphine, (2.0 g, 6 mmol) of cesium carbonate, (0.006 g, 0.025 mmol) of palladium acetate were added in sequence, and 300 mL of DMA was added. The resulting suspension was heated to 160 ° C with silicone oil, stirred for 7 hours, extracted three times with ethyl acetate, and the organic phases were combined, then dried with anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. Intermediate Q1 was obtained by purification through recrystallization (ethyl acetate / petroleum ether).

[0161]

[0162] Synthesis of intermediate a-2:

[0163] In a three-necked flask, raw material A-2 (0.59 g, 2.5 mmol) was dissolved in 50 mL of toluene solution under nitrogen, and raw material B-2 (0.84 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 18 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate a-2.

[0164] Synthesis of intermediate b-2:

[0165] Under nitrogen in a three-necked flask, the intermediate a-2 (1.12 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and raw material A-1 (0.74 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 24 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate b-2.

[0166] Synthesis of intermediate Q2:

[0167] In a three-necked flask, under nitrogen, (1.66 g, 2.5 mmol) of intermediate b-2, (0.05 g, 0.2 mmol) of tricyclohexylphosphine, (2.0 g, 6 mmol) of cesium carbonate, (0.006 g, 0.025 mmol) of palladium acetate were added in sequence, and 300 mL of DMA was added. The resulting suspension was heated to 160 ° C with silicone oil, stirred for 10 hours, extracted three times with ethyl acetate, and the organic phases were combined, then dried with anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. The intermediate Q2 was obtained by purification through recrystallization (ethyl acetate / petroleum ether).

[0168] Synthesis of intermediate Q3:

[0169]

[0170] Under nitrogen protection, raw material C-1 (4.46 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) were added to a two-necked bottle, 100 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 30 min. Raw material A-3 (6.73 g, 25 mmol) was added under nitrogen protection, and the mixture was stirred at 140 ° C for 12 h under nitrogen protection. The mixture was filtered, washed with water, dried, and passed through a column with PE:EA=20:1 to obtain intermediate Q3.

[0171] Synthesis of intermediate Q4:

[0172]

[0173] Under nitrogen protection, raw material C-2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) were added to a two-necked bottle, 100 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 30 min. Raw material A-3 (6.73 g, 25 mmol) was added under nitrogen protection, and the mixture was stirred at 140 ° C for 12 h under nitrogen protection. The mixture was filtered, washed with water, dried, and passed through a column with PE:EA=20:1 to obtain intermediate Q4.

[0174] Synthesis of intermediate Q5:

[0175]

[0176] Under nitrogen protection, raw material C-1 (4.46 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) were added to a two-necked bottle, 100 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 30 min. Raw material A-4 (6.73 g, 25 mmol) was added under nitrogen protection, and the mixture was stirred at 140 ° C for 10 h under nitrogen protection. The mixture was filtered, washed with water, dried, and passed through a column with PE:EA=20:1 to obtain intermediate Q5.

[0177] Synthesis of intermediate Q6:

[0178]

[0179] Under nitrogen protection, raw material C-2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) were added to a two-necked flask, 100 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 30 min. Raw material A-4 (6.73 g, 25 mmol) was added under nitrogen protection, and the mixture was stirred at 140 ° C for 9 h under nitrogen protection. The mixture was filtered, washed with water, dried, and passed through a column with PE:EA=20:1 to obtain intermediate Q6.

[0180] Example 1 Synthesis of Compound 99:

[0181]

[0182] Preparation of intermediate c-1:

[0183] Under nitrogen protection, 4.4 g (10 mmol) of intermediate Q1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 100 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 2.7 g (10 mmol) of raw material A-5 dissolved in 30 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 2 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate c-1.

[0184] Preparation of intermediate d-1:

[0185] Under nitrogen protection, 2.8 g (10 mmol) of raw material B-3, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 6.9 g (10 mmol) of intermediate c-1 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 10 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-1.

[0186] Preparation of compound 99:

[0187] The intermediate d-1 (11.8 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60°C for 0.5 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 2 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 4 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 99. The half-peak width of compound 99 in toluene solution was 23 nm (1×10 -5 M, toluene solution). 1 H NMR (400 MHz, deuterated chloroform) δ8.55 (d, 1H), 8.30 (d, 1H), 7.91–7.82 (m, 5H), 7.80–7.74 (m, 1H), 7.66 (dd, 1H), 7.63–7.51 (m, 4H), 7.47–7.40 (m, 5H), 7.35–7.19 (m, 7H), 7.17–7.12 (m, 2H), 1.45 (s, 9H), 1.42 (s, 9H), 1.38 (s, 9H).

[0188] Example 2 Synthesis of Compound 116:

[0189]

[0190] Preparation of intermediate d-2:

[0191] Under nitrogen protection, 3.6 g (10 mmol) of raw material A-6, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 70 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 6.9 g (10 mmol) of intermediate c-1 dissolved in 30 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 8 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-2.

[0192] Preparation of compound 116:

[0193] The intermediate d-2 (12.8 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of n-butyl lithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 3 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 12 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 116. The half-peak width of compound 116 in toluene solution was 25 nm (1×10 -5 M, toluene solution). 1 H NMR (400 MHz, deuterated chloroform) δ 8.15 (dd, 1H), 7.93–7.85 (m, 5H), 7.82 (dd, 2H), 7.77–7.70 (m, 1H), 7.67–7.58 (m, 4H), 7.54–7.11 (m, 21H), 7.06–6.95 (m, 3H), 1.35 (s, 9H).

[0194] Example 3 Synthesis of Compound 147:

[0195]

[0196] Preparation of intermediate a-2:

[0197] Add raw material A-6 (1.67 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-3 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, and dry through a column to obtain intermediate a-2.

[0198] Preparation of intermediate b-2:

[0199] The intermediate a-2 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen gas at 0°C, 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material D-1 (0.99 g, 5.5 mmol) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate and filtered. After the solvent was removed under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. Then the water layer was separated and extracted with dichloromethane. Drying with sodium sulfate, filtering, and evaporation by rotary concentration, column, to obtain intermediate b-2.

[0200] Preparation of intermediate d-3:

[0201] Under nitrogen in a three-necked flask, the intermediate b-2 (1.6 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and the intermediate Q1 (1.1 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 10 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring and filtered to obtain the intermediate d-3.

[0202] Preparation of compound 147:

[0203] The intermediate d-3 (12.4 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of tert-butyl lithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 2 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 5 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 147. The half-peak width of compound 147 in toluene solution was 22 nm (1×10 -5 M, toluene solution).

[0204] Example 4 Synthesis of Compound 261:

[0205]

[0206] Preparation of intermediate c-2:

[0207] Under nitrogen protection, 4.4 g (10 mmol) of intermediate Q1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 2.5 g (10 mmol) of raw material A-7 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 7 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate c-2.

[0208] Preparation of intermediate d-4:

[0209] Under nitrogen protection, 3.2 g (10 mmol) of intermediate Q3, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 60 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted at room temperature for 0.5 hours, and 6.7 g (10 mmol) of intermediate c-2 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 12 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-4.

[0210] Preparation of compound 261:

[0211] The intermediate d-4 (12.1 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 2 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 8 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 261. The half-peak width of compound 261 in toluene solution was 20 nm (1×10 -5 M, toluene solution).

[0212] Example 5 Synthesis of Compound 284:

[0213]

[0214] Preparation of intermediate d-5:

[0215] Under nitrogen protection, 3.2 g (10 mmol) of intermediate Q5, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted at room temperature for 0.5 hours, and 6.9 g (10 mmol) of intermediate c-1 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 6 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-5.

[0216] Preparation of compound 284:

[0217] The intermediate d-5 (12.3 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 3 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 12 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 284. The half-peak width of compound 284 in toluene solution was 22 nm (1×10 -5M, toluene solution). 1 H NMR (400 MHz, deuterated chloroform) δ 7.96–7.89 (m, 4H), 7.83–7.72 (m, 4H), 7.66–7.54 (m, 4H), 7.50–7.48 (m, 2H), 7.47–7.37 (m, 12H), 7.35–7.23 (m, 7H), 7.16 (m, 4H), 1.4 (s, 9H).

[0218] Example 6 Synthesis of Compound 301:

[0219]

[0220] Preparation of intermediate d-6:

[0221] Under nitrogen protection, 4.3 g (10 mmol) of intermediate Q4, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 6.7 g (10 mmol) of intermediate c-2 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 6 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-6.

[0222] Preparation of compound 301:

[0223] The intermediate d-6 (13.5 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 3 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 8 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 301. The half-peak width of compound 301 in toluene solution was 21 nm (1×10 -5 M, toluene solution).

[0224] Example 7 Synthesis of Compound 304:

[0225]

[0226] Preparation of intermediate d-7:

[0227] Under nitrogen protection, 4.3 g (10 mmol) of intermediate Q6, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted at room temperature for 0.5 hours, and 6.6 g (10 mmol) of intermediate c-2 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 10 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-7.

[0228] Preparation of compound 304:

[0229] The intermediate d-7 (13.5 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of n-butyl lithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 3 hours. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 5 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 304. The half-peak width of compound 304 in toluene solution was 20 nm (1×10 -5 M, toluene solution). 1 H NMR (400 MHz, deuterated chloroform) δ7.92–7.88 (m, 3H), 7.86–7.73 (m, 3H), 7.64–7.59 (m, 4H), 7.58 (d, 1H), 7.55–7.52 (m, 5H), 7.45–7.41 (m, 4H), 7.39–7.26 (m, 6H), 7.23 (m, 4H), 1.45–1.40 (m, 27H), 1.37 (s, 9H).

[0230] Example 8 Synthesis of Compound 365:

[0231]

[0232] Preparation of intermediate c-3:

[0233] Under nitrogen protection, 6.3 g (10 mmol) of intermediate Q2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted at room temperature for 0.5 hours, and 2.5 g (10 mmol) of raw material A-7 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 6 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate c-3.

[0234] Preparation of intermediate d-8:

[0235] Under nitrogen protection, 3.2 g (10 mmol) of intermediate Q3, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted at room temperature for 0.5 hours, and 8.5 g (10 mmol) of intermediate c-3 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 11 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate d-8.

[0236] Preparation of compound 365:

[0237] The intermediate d-8 (14.4 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0°C, 10 mL of a n-pentane solution of tert-butyl lithium (1.6 M) was slowly added. After stirring at 60°C for 2 hours, boron tribromide (6.26 g, 25 mmol) was added at 0°C, and the reaction mixture was stirred at room temperature for 1 hour. N, N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was added at 0°C, and the reaction mixture was allowed to reach room temperature. After stirring at 130°C for 7 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 365. The half-peak width of compound 365 in toluene solution was 21 nm (1×10 -5 M, toluene solution).

[0238] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0239] Table 1

[0240]

[0241] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-8 and device comparative examples 1-2. The device manufacturing process of device embodiments 2-8 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:

[0242] Device Example 1

[0243] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washing with a cleaning agent (Semiclean M-L20), washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 99 as the doping material, GH-1, GH-2 and compound 99 The mass ratio 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.

[0244] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 9-16 and device comparative examples 3-4. The device manufacturing process of device embodiments 10-16 and device comparative examples 3-4 of the present invention is exactly the same as that of device embodiment 9, 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 2-2 and Table 3 respectively:

[0245] Device Example 9

[0246] 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 99 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 99 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 80 nm was produced by a vacuum evaporation device. The mass ratio of Mg to Ag was 1:9. This layer was used as the cathode layer 10 .

[0247] The molecular structure formula of the relevant materials is shown below:

[0248]

[0249]

[0250] 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.

[0251] Table 2-1

[0252]

[0253] Table 2-2

[0254]

[0255] Table 3

[0256]

[0257] 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.

[0258] It can be seen from the device data results in Table 3 that, compared with the comparative compounds ref-1 and ref-2, the luminescence peak of the compound of the present invention is between 510 and 550 nm, and the green luminescence effect can be well achieved; compared with device comparison examples 1-4, the organic light-emitting device of the present invention, whether in a single-doping system or a double-doping system, has a greatly improved current efficiency and lifespan relative to OLED devices of known materials; when using an exciton-sensitizing material as the first doping, the device efficiency is significantly improved compared with a single-doping system.

[0259] 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), Z represents CR; R, which is the same or different each time, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane; Adjacent R can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; Z1, Z2, and Z3 are represented by C-Ra, C-Rb, and C-Rc, respectively; Ra, Rb, and Rc are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane; Ra, Rb, and Rc can be linked to each other to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 aliphatic ring; Q1 represents substituted or unsubstituted 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; Q2 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 5-30 membered heteroaryl, borane, substituted or unsubstituted C4-C 30 Alkenyl, substituted or unsubstituted C3-C 30 One of the carbon-nitrogen double bonds; M1 and M2 represent substituted or unsubstituted C6~C 30 one of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Q1 and M1, Q1 and the adjacent R can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 Aliphatic ring, substituted or unsubstituted C5~C 30 spiral ring; Q2 and M2, Q2 and the adjacent Rc can be connected to form substituted or unsubstituted C6~C 30 Aromatic ring, substituted or unsubstituted 5-30 membered heteroaromatic ring, substituted or unsubstituted C5~C 30 Aliphatic ring, substituted or unsubstituted C5~C 30 spiral ring; The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane; 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 (1-1) to (1-3): In general formula (1-1) to general formula (1-3), Z, Z1, Z2, Z3, M1, M2, and Q1 have the same meanings as defined in general formula (1); M3, M4, and M5 represent substituted or unsubstituted C6~C 30 one of aryl, substituted or unsubstituted 5-30 membered heteroaryl; Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane; The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane; 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 (2) to (4): In general formula (2) to general formula (4), Z, Z1, Z2, Z3, M2, Q1, Q2 have the same meanings as defined in general formula (1); X is represented by one of O or S; Preferably, the general formula (2) is represented by the general formula (2-1): In the general formula (2-1), Z, Z1, Z2, Z3, M2, and Q1 have the same meanings as those defined in the general formula (1); Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane; The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane; 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 (5) to (19): In general formulae (5) to (19), Z, Z1, Z2, Z3, Q1, and Q2 have the same meanings as those defined in general formula (1); X is represented by one of O or S; X2 represents one of O, S, C(Rd)(Re), Si(Rf)(Rg); Rd, Re, Rf, and Rg represent substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, borane, substituted or unsubstituted C4-C 30 Alkenyl, substituted or unsubstituted C3-C 30 One of the carbon-nitrogen double bonds; Rd and Re, Rf and Rg can be connected to form a ring; Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane; The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane; 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 (20) to (28): In general formulae (20) to (28), Z, Z1, and Q1 have the same meanings as defined in general formula (1); X and X3 represent one of O and S.

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 (29) to (41): In general formulae (29) to (41), Z, Q1, Z1, Z2, and Z3 have the same meanings as defined in general formula (1); X is represented by one of O or S; Q3 and Q4 represent hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, 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, borane, substituted or unsubstituted C4-C 30 Alkenyl, substituted or unsubstituted C3-C 30 One of the carbon-nitrogen double bonds; The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C1~C 10 Alkoxy, C1~C 10 Aryloxy, C6~C 30 One or more of aryl, 5-30 membered heteroaryl, arylamine, and borane; 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 The R, Ra, Rb, and Rc are represented by the following structure: Hydrogen atom, deuterium atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, Any of; The Rd, Re, R f , R g , Q3, and Q4 are independently expressed as the following structural features: Any of; The Q1 and Q2 are independently represented by the following structural features: Any of; The M1, M2, M3, M4, and M5 are independently represented by any of the following ring structures: The meaning of Z is the same as defined in the general formula (1), and the asterisk indicates a linkable site.

8. The boron-containing organic compound according to any one of claims 1 to 6, characterized in that R, Ra, Rb, and Rc are independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl substituted phenyl, 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, tert-butyl substituted phenyl, xanthone, phenyl substituted triazine, phenyl substituted boryl, methoxy, tert-butoxy, diphenylamine; The Rd, Re, R f , R g Each of the following independently represents adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated 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 The present invention is one of the following: 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, tert-butyl substituted phenyl, xanthone, phenyl substituted triazine, phenyl substituted borane, methoxy, tert-butoxy, diphenylamine; The Q3, Q4, M1, M2, M3, M4, and M5 are represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone; The Q1 and Q2 are phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, xanthone, One of; 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.

9. 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:

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

11. The organic electroluminescent device according to claim 10, 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 9.

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