A boron-containing organic compound and an organic electroluminescent device prepared therefrom

Abstract

The present invention discloses a boron-containing organic compound and an organic electroluminescent device prepared therefrom, belonging to the field of semiconductor technology. The structure of the organic compound of the present invention is shown in general formula (1), and the compound of the present invention can be used as a green light doping material of the light-emitting layer of the organic electroluminescent device, thereby improving the efficiency and life of the device.

Description

[0001] This invention application is based on the prior application number: 202211306424.1, the application date: October 25, 2022, and the invention name is: A divisional application for a boron-containing organic compound and an organic electroluminescent device prepared therefrom. Technical Field

[0002] The present invention relates to the field of semiconductor technology, and in particular to a boron-containing organic compound as an OLED doping material and an organic electroluminescent device containing the same. Background Art

[0003] Traditional fluorescent doped materials are limited by early technologies and can only use 25% of singlet excitons formed by electrical excitation to emit light. The internal quantum efficiency of the device is low (up to 25%), and the external quantum efficiency is generally less than 5%, which is far behind the efficiency of phosphorescent devices. Since the strong spin-orbit coupling of the heavy atom center enhances intersystem crossing, phosphorescent materials can effectively use singlet and triplet excitons formed by electrical excitation to emit light, making the internal quantum efficiency of the device reach 100%. However, most phosphorescent materials are expensive, have poor material stability, poor color purity, and serious device efficiency roll-off, which limits their application in OLEDs.

[0004] With the advent of the 5G era, higher requirements are placed on color rendering standards. In addition to being efficient and stable, luminescent materials also require a narrower half-width to improve the purity of the device's luminescent color. Fluorescent doped materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doped materials have achieved a phased breakthrough, and the half-width of boron materials can be reduced to below 30nm. In the green light region, which is more sensitive to the human eye, research is mainly focused on phosphorescent doped materials, but their luminescent peak shape is difficult to narrow by simple methods. Therefore, in order to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doped materials with narrow half-width.

[0005] In addition, the sensitization technology combines triplet exciton-sensitizing materials with fluorescent doping materials, uses triplet exciton-sensitizing materials as exciton-sensitizing media, makes full use of triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0006] Boron compounds with a resonant structure are more likely to achieve narrow half-width luminescence. This type of material is used in sensitization technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN 110492006A disclose a luminescent layer combination technology with a TADF material having a difference between the lowest singlet and the lowest triplet energy level of less than or equal to 0.2eV as the main body and a boron-containing material as the doping; CN 110492005 A and CN 110492009A disclose a luminescent layer combination scheme with an exciplex as the main body and a boron-containing material as the doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. The development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators.

[0007] Patent CN114315875 A reports a green light-emitting diboron compound having a narrow luminescence half-width, but the device efficiency and device life need to be further improved. Summary of the invention

[0008] 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 for the light-emitting layer of the organic electroluminescent device, thereby improving the efficiency and life of the device.

[0009] 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):

[0010]

[0011] In the general formula (1), R 1 -R 20 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 3 ~C 10 Heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, amino substituted by C1-C20 alkyl, substituted or unsubstituted C2-C30 heteroaryl containing one or more heteroatoms;

[0012] R 1 -R 20 At least 4 of them are not hydrogen atoms;

[0013] R 1 -R 20Any adjacent groups in can be connected to form a ring;

[0014] The substituents used for substitution are selected from deuterium atoms, halogens, C1-C10 alkyl groups, C 3 ~C 10 Any one of a cycloalkyl group, a deuterium- or fluorine-substituted C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heteroaryl group.

[0015] Preferably, the R 1 -R 20 4 to 6 of them are not hydrogen atoms.

[0016] Preferably, the R 1 -R 20 There are 4 atoms that are not hydrogen atoms.

[0017] Preferably, the R 1 -R 20 Among them, 6 are not hydrogen atoms.

[0018] In a preferred embodiment, the structure of the boron-containing organic compound is shown in general formula (2):

[0019]

[0020] In the general formula (2), R 1 , R 2 , R 3 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 16 , R 19 , R 20 has the same meaning as defined above;

[0021] R 1 , R 2 , R 3 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 16 , R 19 , R 20 At least 4 of them are not hydrogen atoms.

[0022] In a preferred embodiment, the structure of the boron-containing organic compound is shown in general formula (3):

[0023]

[0024] In the general formula (3), R 1 , R 2 , R 3 , R 6 , R 9 , R 11 , R 12 , R 13 , R 16 , R 19 has the same meaning as defined above;

[0025] R 1 , R 2 , R 3 , R 6 , R 9 , R 11 , R 12 , R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms.

[0026] In a preferred embodiment, the structure of the boron-containing organic compound is any one of the general formulas (4-1) to (4-8):

[0027]

[0028] In the general formula (4-1) to the general formula (4-8), R 1 , R 2 , R 3 , R 6 , R 9 , R 11 , R 12 , R 13 , R 16 , R 19 The meaning is the same as defined above; in the general formula (4-1), R 1 , R 6 , R 9 , R 11 , R 16 , R 19 At least 4 of them are not hydrogen atoms;

[0029] In the general formula (4-2), R 2 , R 6 , R 9 , R 12 , R 16 , R 19 At least 4 of them are not hydrogen atoms;

[0030] In the general formula (4-3), R 3 , R 6 , R 9 , R13 , R 16 , R 19 At least 4 of them are not hydrogen atoms;

[0031] In the general formula (4-4), R 2 , R 3 , R 6 , R 9 , R 12 , R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms;

[0032] In the general formula (4-5), R 1 , R 3 , R 6 , R 9 , R 11 , R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms;

[0033] In the general formula (4-6), R 1 , R 2 , R 6 , R 9 , R 11 , R 12 , R 16 , R 19 At least 4 of them are not hydrogen atoms;

[0034] In the general formula (4-7), R 2 , R 6 , R 12 , R 16 Not a hydrogen atom;

[0035] In the general formula (4-8), R 3 , R 6 , R 13 , R 16 Not a hydrogen atom.

[0036] In a preferred embodiment, the structure of the boron-containing organic compound is any one of the general formulas (5-1) to (5-16):

[0037]

[0038]

[0039] In the general formula (5-1) to the general formula (5-2), R 2 , R 3 , R 9 , R 12 , R13 , R 19 are independently represented by a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic amine group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 3 ~C 10 Heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, amino substituted by C1-C20 alkyl, substituted or unsubstituted C2-C30 heteroaryl containing one or more heteroatoms;

[0040] In the general formula (5-3) to the general formula (5-16), R 1 , R 2 , R 3 , R 9 , R 11 , R 12 , R 13 , R 19 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 3 ~C 10 Heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, amino substituted by C1-C20 alkyl, substituted or unsubstituted C4-C30 heteroaryl containing one or more heteroatoms;

[0041] In the general formula (5-3), R 2 , R 3 , R 9 , R 12 , R 13 , R 19 At least 4 of them are not hydrogen atoms;

[0042] In the general formula (5-4), R 1 , R 3 , R 9 , R 11 , R 13 , R 19 At least 4 of them are not hydrogen atoms;

[0043] In the general formula (5-5), the general formula (5-9) and the general formula (5-13), R 2 , R 9 , R 12, R 19 At least 2 of them are not hydrogen atoms;

[0044] In the general formula (5-6), the general formula (5-10), and the general formula (5-14), R 3 , R 9 , R 13 , R 19 At least 2 of them are not hydrogen atoms;

[0045] In the general formula (5-7), the general formula (5-11), and the general formula (5-15), R 2 , R 3 , R 9 , R 12 , R 13 , R 19 At least 2 of them are not hydrogen atoms;

[0046] In the general formula (5-8), the general formula (5-12) and the general formula (5-16), R 1 , R 3 , R 9 , R 11 , R 13 , R 19 At least 2 of them are not hydrogen atoms;

[0047] The substituent used for substitution may be selected from any one of a deuterium atom, a halogen, adamantane, a C1-C10 alkyl group, a deuterium- or fluorine-substituted C1-C10 alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms.

[0048] In a preferred embodiment, R1-R20 are independently represented by a hydrogen atom, a deuterium atom, a fluorine 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 spiro The invention can be selected from the group consisting of fluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy.

[0049] In a preferred embodiment, the R1-R20 are independently represented by any one of the following structures:

[0050] Hydrogen atoms,

[0051] Any one of.

[0052] In a preferred embodiment, the specific structural formula of the organic compound is any one of the following structures:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] An organic electroluminescent device comprises a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0068] In a preferred embodiment, the light-emitting layer comprises a main material and a doping material, and the doping material contains the boron-containing organic compound.

[0069] In a preferred embodiment, the light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing organic compound.

[0070] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material, wherein the exciton-sensitizing material is a complex containing a metal element, and the doping material is the boron-containing organic compound.

[0071] The beneficial technical effects of the present invention are:

[0072] (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;

[0073] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0074] (3) The compound of the present invention is used as a doping material, and a phosphorescent material is introduced as an exciton sensitizer, which can effectively improve the device life;

[0075] (4) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0076] Figure 1This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0077] 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;

[0078] Figure 2 is the NMR spectrum of compound 270;

[0079] Figure 3 is the mass spectrum of compound 270;

[0080] Figure 4 NMR spectrum of compound 271;

[0081] Figure 5 Mass spectrum of compound 271. DETAILED DESCRIPTION

[0082] The technical solutions in the embodiments of the present invention will be described clearly and completely below in conjunction with the drawings in the embodiments of the present invention. In the absence of conflict, the embodiments of the present invention and the features in the embodiments can be combined with each other. The present invention will be further described below in conjunction with the drawings and specific embodiments, but they are not intended to limit the present invention.

[0083] 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.

[0084] In the present invention, substituted or unsubstituted C 6 -C 30 Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted The invention may be a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, or a condensed ring of a combination of the foregoing groups, but is not limited thereto.

[0085] In the present invention, substituted or unsubstituted C 2 -C 30The heteroaryl group refers to a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted The invention also includes substituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or fused rings of combinations of the foregoing groups, but is not limited thereto.

[0086] The C of the present invention 1 -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.

[0087] The halogen atom described in the present invention refers to a chlorine atom, a fluorine atom or a bromine atom, but is not limited thereto.

[0088] The C of the present invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group containing 3 to 10 carbon atoms as ring atoms. 4 -C 9 Cycloalkyl, more preferably C 5 -C 8 Cycloalkyl, particularly preferably C 5 -C 7 Cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, cycloheptyl, and the like, but are not limited thereto.

[0089] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates; flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, its use direction is different. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.

[0090] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr or a metal mixture. The thickness of the first electrode layer depends on the material used, and is typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.

[0091] 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.

[0092] Herein, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0093] As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials used for OLED devices.

[0094] Examples of the above materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quilone derivatives, styryl anthracene derivatives, styrylamine derivatives and the like, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinyl and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and the like, conductive polymer oligomers, aromatic tertiary amine compounds, styrene amination compounds, compounds, triamines, tetraamines, benzidines, propargyl diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamino)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)quaterphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds.

[0095] Furthermore, according to the device matching requirements, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer constituting the organic electroluminescent device can be a single film layer or a superposition structure of multiple hole transport materials. In this article, for the above-mentioned hole carrier conduction film layers with different functions, their film thickness is not particularly limited.

[0096] 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.

[0097] In view of the above empirical summary, for hole-type host materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0098] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer also includes a P-type doping material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited to these.

[0099] 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.

[0100] 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.

[0101] The thickness of the hole transport layer of the present invention may be 5 to 200 nm, preferably 10 to 150 nm, and more preferably 20 to 100 nm, but the thickness is not limited to this range.

[0102] The thickness of the electron blocking layer of the present invention may be 1-20 nm, preferably 5-10 nm, but the thickness is not limited to this range.

[0103] 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.

[0104] 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.

[0105] 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.

[0106] 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 15-30 nm, but the thickness is not limited to this range.

[0107] 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.

[0108] The hole blocking layer is a layer that blocks the holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the efficiency of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, for example, phenanthroline derivatives such as bathocuproin (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis (9H-carbazole) (CAS No.: 1345338-69-3) and other pyrimidine derivatives. The thickness of the hole blocking layer of the present invention may be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0109] 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 material known in the prior art for organic electroluminescent devices can be used, for example, Alq 3 , metal complexes of hydroxyquinoline derivatives represented by BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), imidazole derivatives such as oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. The thickness of the electron transport layer of the present invention can be 10-80nm, preferably 20-60nm and more preferably 25-45nm, but the thickness is not limited to this range.

[0110] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0111] 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, 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, and is typically 10-50 nm, preferably 15-20 nm.

[0112] 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.

[0113] 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.

[0114] 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;

[0115] Intermediate synthesis:

[0116] Synthesis of intermediate A series:

[0117]

[0118] Synthesis of intermediate A1: Under nitrogen protection, 10 mmol of raw material P1, 10 mmol of raw material P2, 10 ml of DMF, 16 mmol of cesium carbonate, 1.25 mmol of o-phenanthroline and 1 mmol of CuI were added to a three-necked flask and refluxed for 30 hours. After the reaction, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate A1.

[0119]

[0120] Synthesis of intermediate A2: In a three-necked flask, add 5 mmol of raw material P3, 5 mmol of raw material P2, 50 mL of toluene, 16 mL of ethanol, 15 mmol of potassium carbonate aqueous solution, 0.2 mmol of Pd(PPh 3 ) 4 , nitrogen protection, reaction at reflux temperature for 8h, cooling to room temperature after reaction, adding water to quench the reaction, extracting three times with ethyl acetate, combining the organic phases, then drying with anhydrous sodium sulfate, filtering and concentrating to obtain a crude product. Intermediate A2 was obtained by recrystallization (ethyl acetate / petroleum ether).

[0121]

[0122] Synthesis of intermediate A3: In a three-necked flask, add 5 mmol of raw material P6, 5 mmol of raw material P2, 50 mL of toluene, 16 mL of ethanol, 15 mmol of potassium carbonate aqueous solution, 0.2 mmol of Pd(PPh 3 ) 4 , nitrogen protection, reaction at reflux temperature for 8h, cooling to room temperature after reaction, quenching the reaction with water, extracting three times with ethyl acetate, combining the organic phases, then drying with anhydrous sodium sulfate, filtering and concentrating to obtain a crude product. Intermediate A3 was obtained by recrystallization (ethyl acetate / petroleum ether).

[0123]

[0124] Synthesis of intermediate A4: Raw material P9 (49 mmol) was dissolved in toluene solution, raw material P8 (50 mmol), tri-tert-butylphosphine (2.5 mmol), sodium tert-butoxide (130 mmol) and palladium acetate (0.8 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105°C for 30 minutes 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. Intermediate A4 was obtained after filtration.

[0125]

[0126] Synthesis of intermediate A5: In a three-necked flask, add 5 mmol of raw material P9, 5 mmol of raw material P2, 50 mL of toluene, 16 mL of ethanol, 15 mmol of potassium carbonate aqueous solution, 0.2 mmol of Pd(PPh 3 ) 4 , nitrogen protection, reaction at reflux temperature for 6h, cooling to room temperature after reaction, adding water to quench the reaction, extracting with ethyl acetate three times, combining the organic phases, then drying with anhydrous sodium sulfate, filtering and concentrating to obtain a crude product. Intermediate A5 was obtained by recrystallization (ethyl acetate / petroleum ether).

[0127] Synthesis of intermediate B series:

[0128]

[0129] Synthesis of intermediate b1: Dissolve the raw material P3 (0.37 mol) in acetonitrile (500 mL), then dissolve NBS (0.39 mol) in acetonitrile (500 mL) and slowly add it. Stir the reaction solution at 0 degrees Celsius for 30 minutes. Concentrate the reaction solution directly. Rinse the residue with petroleum ether and filter and concentrate to obtain intermediate b1 (90%) as a black liquid. LCMS: [M+H] + =214.1

[0130] Synthesis of intermediate b2: Dissolve intermediate b1 (0.25 mol) in NMP (250 mL), then add Cu CN (0.27 mol). Stir the reaction solution at 200 degrees Celsius for 3 hours. Cool to room temperature, dilute the reaction solution with ethyl acetate (3 L), then filter, wash the filtrate with saturated brine, dry over anhydrous sodium sulfate, and concentrate. Intermediate b2 (90%) is obtained as a black liquid. LCMS: [M+H] + =161.1

[0131] Synthesis of intermediate b3: Dissolve intermediate b2 (0.31 mol) in methanol (200 mL) and ethanol (30 mL), then add sodium hydroxide aqueous solution (200 mL, 10 mol / L). Stir the reaction solution at 100 degrees Celsius for 16 hours. Concentrate the reaction solution, adjust the pH value of the residue to 7 with concentrated hydrochloric acid, filter, dissolve the filter cake in ethyl acetate and wash with saturated brine, dry over anhydrous sodium sulfate and concentrate to obtain intermediate b3 (90%) as a black solid. LCMS: [M+H] + =180.1

[0132] Synthesis of intermediate b4: Intermediate b3 (0.28 mol) was dissolved in methanol (300 mL) and DMF (3 mL), and then SOCl was slowly added. 2 (0.33 mol). The reaction solution was stirred at 90 degrees Celsius for 16 hours. The reaction solution was concentrated, and the residue was adjusted to pH 7 with potassium carbonate aqueous solution, dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 30:1) to obtain intermediate b4 (95%) as a black solid. LCMS: [M+H] + =194.1

[0133] Synthesis of intermediate b5: Dissolve intermediate b4 (0.287 mol) and sodium hydride (60% in mineral oil, 0.776 mol) in anhydrous tetrahydrofuran (THF) (1 L), reflux for 5 h under nitrogen protection. After cooling to room temperature, slowly drop a large amount of 1M glacial hydrochloric acid solution into the reaction solution, filter it with suction, and wash it with dichloromethane to obtain intermediate b5 (100%) as a yellow solid. LCMS: [M+H] + =323.2

[0134] Synthesis of intermediate b6: Dissolve intermediate b5 (129 mmol) in chloroform (1000 mL), add phosphorus pentachloride (388 mmol) in an ice-water bath, protect with nitrogen, warm to room temperature, heat under reflux, and react overnight. Cool, filter, spin dry the solvent, and purify by column chromatography (PE:EA=20:1) to obtain intermediate b6 (45%) as a yellow solid. LCMS: [M+H] + =359.1

[0135] Synthesis of intermediate B1: Dissolve intermediate b6 (58.4 mmol) in tetrahydrofuran (THF) (300 mL), add zinc powder (584 mmol), and slowly add trifluoroacetic acid (42 mL) under nitrogen protection in an ice bath. Warm to room temperature and react for 16 hours. Filter, extract with EA, dry and spin dry, wash the crude product with petroleum ether and ethyl acetate to obtain compound intermediate B1 (77%) as a light yellow solid. 1 HNMR (400 MHz, DMSO-d 6 )δ10.82(s,2H),7.53(s,2H),7.36(d,2H),7.05(dd,2H),3.06-2.96(m,2H),1.29(d,12H).

[0136] The following intermediates of series B were synthesized by referring to the preparation process of intermediate B1; the reaction conditions were the same, except that the raw materials P listed in Table 1 below were used;

[0137] Table 1

[0138]

[0139] Example 1: Synthesis of Compound 1:

[0140]

[0141] Synthesis of intermediate c1: Add raw material H1 (50 mmol), raw material G1 (49 mmol), potassium carbonate (50 mmol), and N-methylpyrrolidone into a two-necked flask, stir at 170°C for 12 h under nitrogen protection, cool and extract with ethyl acetate / brine water, dry, and pass through a PE column to obtain intermediate c1 as a colorless oily liquid with a yield of about 60%.

[0142] Synthesis of intermediate c2: Add intermediate B2 (50 mmol) and cesium carbonate (125 mmol) into a two-necked flask, add anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add intermediate c1 (100 mmol) under nitrogen protection, stir at 140°C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a PE:EA=20:1 column to obtain intermediate c2 as a white solid, with a yield of about 45%.

[0143] Synthesis of compound 1: intermediate c2 was added to a two-necked flask, tert-butylbenzene was added under nitrogen protection, the temperature was lowered to -40°C, n-butyllithium (0.25 mol, 2.5 M pentane solution) was added dropwise, the temperature was raised to 70°C and stirred for 2 h, the temperature was lowered to -40°C, boron tribromide (0.125 mol) was added, the temperature was raised to room temperature and stirred for 30 min, the temperature was lowered to 0°C, N,N-diisopropylethylamine (0.2 mol) was added, the temperature was raised to 130°C and stirred for 12 h, the temperature was cooled, extracted, and the solvent was removed, dichloromethane was added to the crude product, heated to reflux for 30 min, and filtered while hot to obtain compound 1 with a yield of about 15%.

[0144] The following target compound was synthesized by referring to the preparation process of compound 1 in Example 1; the reaction conditions were the same, except that the raw material G, raw material H and intermediate B listed in Table 2 below were used;

[0145] Table 2

[0146]

[0147]

[0148]

[0149] The structural characteristics of the compounds obtained in each example are shown in Table 3

[0150] Table 3

[0151]

[0152] The compounds of the present invention are used in light-emitting devices and can be used as doping materials for light-emitting layers. The physical and chemical properties of the compounds prepared in the above embodiments of the present invention were tested, and the test results are shown in Table 4:

[0153] Table 4

[0154] Compound PLQY(%) FWHM(nm) 1 92 27 8 95 24 38 93 27 46 97 26 50 92 25 83 95 28 137 96 29 155 92 28 268 98 27 269 93 27 270 94 28 271 96 26

[0155] Note: PLQY (fluorescence quantum yield) and FWHM (half-maximum width) are measured in thin film state by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0156] It can be seen from the data in Table 4 above that the compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; at the same time, the spectral FWHM of the material is narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device.

[0157] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device examples 1-12 and device comparative examples 1-2. The device manufacturing process of device examples 1-12 of the present invention is exactly the same as that of device comparative examples 1-2, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 5 and Table 6 respectively.

[0158] Device Example 1

[0159] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washing with a cleaning agent (Semiclean M-L20), washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is made, using GH-1 and GH-2 as the main materials, compound 1 as the doping material, the mass ratio of GH-1, GH-2 and compound 1 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.

[0160] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device examples 13-24 and device comparison examples 2-4. The device manufacturing process of device examples 13-24 of the present invention is exactly the same as that of device comparison examples 2-4, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 5 and Table 6 respectively.

[0161] Device Example 11

[0162] 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 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, GD-1 as the first doping material, and compound 1 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 1 is 66:30:3:1, 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.

[0163] The molecular structure formula of the relevant materials is shown below:

[0164]

[0165]

[0166] The comparative compounds ref-1 and ref-2 were prepared by referring to the method described in the prior art CN114315875A, and their structures are characterized as follows:

[0167] Ref-1: Elemental analysis structure (C 46 H 36 B 2 N 2 O 2 ) Theoretical value: C, 82.41; H, 5.41; N, 4.18; Test value: C, 82.21; H, 5.38; N, 4.13. LC-MS: Measured value: 671.42 ([M+H] + ), exact mass: 670.30.

[0168] Ref-2: Elemental analysis structure (C 46H 36 B 2 N 2 O 2 ) Theoretical value: C, 82.41; H, 5.41; N, 4.18; Test value: C, 82.37; H, 5.31; N, 4.12. LC-MS: Measured value: 671.38 ([M+H] + ), exact mass: 670.30.

[0169] After the OLED light emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the voltage, current efficiency and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 5; the test results of the voltage, current efficiency and life of the obtained device are shown in Table 6.

[0170] Table 5

[0171]

[0172]

[0173] Table 6

[0174]

[0175] 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.

[0176] It can be seen from the device data results in Table 6 that, compared with device comparison examples 1-2, the device life of the compounds of the present invention in single-doping system devices is higher than that of comparison examples 1-2; in single-doping system devices, the device efficiency also shows a good effect; compared with device comparison examples 3-4, the compounds of the present invention are in dual-doping system devices using exciton-sensitizing materials as the first doping, and the current efficiency and device life of the device are greatly improved relative to OLED devices of known materials, and in dual-doping devices, the device efficiency is also significantly improved compared to single-doping.

[0177] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that The structure of the boron-containing organic compound is shown in general formula (1): In the general formula (1), R1-R 20 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C3~C 10 Heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl containing one or more heteroatoms; R1-R 20 At least 4 of them are not hydrogen atoms; The substituted or unsubstituted C6-C30 aryl group refers to a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl; The substituted or unsubstituted C2-C30 heteroaryl group refers to a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiophenyl, substituted or unsubstituted 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 phenazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; The substituents used for substitution are selected from deuterium atoms, halogens, C1-C10 alkyl groups, C3-C 10 Any one of a cycloalkyl group, a deuterium- or fluorine-substituted C1-C10 alkyl group, a C6-C30 aryl group, or a C2-C30 heteroaryl group; C1-C 10 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 or 1-butylpentyl; The halogen atom refers to a chlorine atom, a fluorine atom or a bromine atom; The C3-C 10 The cycloalkyl group refers to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl or cycloheptyl.

2. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in general formula (2): In the general formula (2), R1, R2, R3, R6, R9, R 10 , R 11 , R 12 , R 13 , R 16 , R 19 , R 20 has the same meaning as defined in claim 1; R1, R2, R3, R6, R9, R 10 , R 11 , R 12 , R 13 , R 16 , R 19 , R 20 At least 4 of them are not hydrogen atoms.

3. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in general formula (3): In the general formula (3), R1, R2, R3, R6, R9, R 11 , R 12 , R 13 , R 16 , R 19 has the same meaning as defined in claim 1; R1, R2, R3, R6, R9, R 11 , R 12 , R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms.

4. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is any one of the general formulas (4-1) to (4-8): In the general formula (4-1) to the general formula (4-8), R1, R2, R3, R6, R9, R 11 , R 12 , R 13 , R 16 , R 19 has the same meaning as defined in claim 1; In the general formula (4-1), R1, R6, R9, R 11 , R 16 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (4-2), R2, R6, R9, R 12 , R 16 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (4-3), R3, R6, R9, R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (4-4), R2, R3, R6, R9, R 12 , R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (4-5), R1, R3, R6, R9, R 11 , R 13 , R 16 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (4-6), R1, R2, R6, R9, R 11 , R 12 , R 16 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (4-7), R2, R6, R 12 , R 16 Not a hydrogen atom; In the general formula (4-8), R3, R6, R 13 , R 16 Not a hydrogen atom.

5. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is any one of the general formulas (5-1) to (5-16): In the general formula (5-1) to the general formula (5-2), R2, R3, R9, R 12 , R 13 , R 19 are independently represented by a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C3~C 10 Heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, amino substituted by C1-C20 alkyl, substituted or unsubstituted C2-C30 heteroaryl containing one or more heteroatoms; In the general formula (5-3) to the general formula (5-16), R1, R2, R3, R9, R 11 , R 12 , R 13 , R 19 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C3~C 10 Heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, amino substituted by C1-C20 alkyl, substituted or unsubstituted C4-C30 heteroaryl containing one or more heteroatoms; In the general formula (5-3), R2, R3, R9, R 12 , R 13 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (5-4), R1, R3, R9, R 11 , R 13 , R 19 At least 4 of them are not hydrogen atoms; In the general formula (5-5), the general formula (5-9) and the general formula (5-13), R2, R9, R 12 , R 19 At least 2 of them are not hydrogen atoms; In the general formula (5-6), the general formula (5-10), and the general formula (5-14), R3, R9, R 13 , R 19 At least 2 of them are not hydrogen atoms; In the general formula (5-7), the general formula (5-11), and the general formula (5-15), R2, R3, R9, R 12 , R 13 , R 19 At least 2 of them are not hydrogen atoms; In the general formula (5-8), the general formula (5-12), and the general formula (5-16), R1, R3, R9, R 11 , R 13 , R 19 At least 2 of them are not hydrogen atoms; The substituent used for substitution may be selected from any one of a deuterium atom, a halogen, adamantane, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms.

6. The boron-containing organic compound according to claim 1, characterized in that The R1-R 20 and each independently represents a hydrogen atom, a deuterium 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 The invention can be selected from the group consisting of a phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuranyl group, a phenyl-substituted tert-butyl group, a xanthone group, a phenyl-substituted triazine group, a phenyl-substituted boryl group, a methoxy group, and a tert-butoxy group.

7. The boron-containing organic compound according to claim 1, characterized in that The R1-R 20 Each is independently represented as any of the following structures: Hydrogen atoms, Any one of.

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

9. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, characterized in that: The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that: The light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to any one of claims 1 to 8.

11. The organic electroluminescent device according to claim 9, characterized in that: The light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-8.

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

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