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 technical field of semiconductors. The structure of the organic compound of the present invention is shown in general formula (1). The compound of the present invention has a narrow full width at half maximum, a high fluorescence quantum yield, and appropriate HOMO and LUMO energy levels, and can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the color purity and efficiency of the device.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing organic compound as an OLED doping material and an organic electroluminescent device comprising the same. Background Art

[0002] Traditional fluorescent doping materials are limited by early technologies and can only utilize 25% of the singlet excitons formed by electrical excitation for luminescence. The internal quantum efficiency of the device is relatively low (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a large gap compared with the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling of heavy atom centers that enhances intersystem crossing, can effectively utilize both singlet excitons and triplet excitons formed by electrical excitation for luminescence, enabling the internal quantum efficiency of the device to reach 100%. However, most phosphorescent materials are expensive, have poor material stability, poor color purity, and serious device efficiency roll-off, which limit their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are put forward for the color rendering standard. In addition to being efficient and stable, luminescent materials also require a narrower full width at half maximum to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum yield and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum of boron-based materials can be reduced to less than 30 nm. In the green light region, to which the human eye is more sensitive, research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape through simple methods. Therefore, it is of great significance to study efficient green fluorescent doping materials with narrow full width at half maximum to meet higher color rendering standards.

[0004] In addition, the TADF sensitized fluorescence technology (TSF) combines a TADF material with a fluorescent doping material. Using the TADF material as an exciton sensitization medium, the triplet excitons formed by electrical excitation are converted into singlet excitons, and the energy is transferred to the fluorescent doping material through long-range energy transfer of singlet excitons, which can also achieve an internal quantum efficiency of 100% for the device. This technology can make up for the deficiency of low exciton utilization rate of fluorescent doping materials and effectively utilize the characteristics of high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs.

[0005] Boron compounds with resonance structures are more likely to achieve narrow full-width at half-maximum (FWHM) emission. When such materials are applied to thermally activated delayed fluorescence (TADF) sensitized fluorescence technology, high-efficiency and narrow-FWHM emission device fabrication can be realized. For example, in CN 107507921 A and CN110492006 A, a luminescent layer combination technology is disclosed, which uses a TADF material with a singlet-triplet energy gap less than or equal to 0.2 eV as the host and a boron-containing material as the dopant; in CN 110492005 A and CN 110492009 A, a luminescent layer combination scheme using exciplex as the host and a boron-containing material as the dopant is disclosed; both can achieve efficiency comparable to phosphorescence and relatively narrow FWHM. Therefore, developing TADF sensitized fluorescence technology based on narrow-FWHM boron-based luminescent materials has unique advantages and strong potential in meeting the BT.2020 display specifications. Summary of the Invention

[0006] 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 has a narrow FWHM and a high fluorescence quantum yield, and can be used as a green dopant material for the luminescent layer of an organic electroluminescent device, thereby improving the color purity and lifespan of the device.

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

[0008]

[0009] In the general formula (1), the M1 and M2 rings independently represent a substituted or unsubstituted C 6 -C 30 aromatic ring, a substituted or unsubstituted C 2 -C 30 heteroaromatic ring;

[0010] X 1 、X 2 independently represent O, S, N(R 1 ) or C(R 2 )(R 3 );

[0011] X 3 、X 4 independently represent O, S, N(R 1 );

[0012] R 1 、R 2 、R 3 each occurrence, whether the same or different, represents a substituted or unsubstituted C 1 ~C 10Alkyl, substituted or unsubstituted C 1 ~C 10 Alkenyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 1 ~C 10 Aryloxy, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted C 2 ~C 30 Heteroaryl,

[0013] and R 1 、R 2 、R 3 can be respectively connected to M1 or M2 to form a ring;

[0014] The substituents of the above-mentioned "substituted or unsubstituted" groups are each independently selected from one or more of a deuterium atom, an alkyl group of C 1 -C 10 , a cycloalkyl group of C 3 -C 10 , an aryl group of C 6 -C 30 , a heteroaryl group of C 2 -C 30 , and an amino group;

[0015] The heteroatoms in the heteroaryl group are each independently selected from one or more of an oxygen atom, a sulfur atom, and a nitrogen atom.

[0016] Preferably, the structure of the organic compound is represented by any one of General Formulas (2) to (13):

[0017]

[0018] In General Formulas (2) to (13), the meanings of the M1 ring, the M2 ring, R 1 , R 2 , and R 3 are the same as those defined in General Formula (1).

[0019] Preferably, the structure of the organic compound is represented by General Formula (II):

[0020]

[0021] In General Formula (II), X 1 , X 2 are each independently represented by O, S, N(R 1 ) or C(R 2 )(R 3 );

[0022] X 3 、X 4 are each independently represented as O, S, N(R 1 ));

[0023] Z1 - Z8 are each independently represented as a nitrogen atom, C - H or C - R;

[0024] R 1 、R 2 、R 3 each occurrence, whether the same or different, is represented as a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group;

[0025] Each occurrence of R is independently represented as a deuterium atom, a halogen atom, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, or one or more of them;

[0026] And R 1 、R 2 、R 3 can be respectively connected to R to form a ring;

[0027] The substituents of the "substituted or unsubstituted" above - mentioned groups are each independently selected from a deuterium atom, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, an amino group, or one or more of them;

[0028] The heteroatoms in the said heteroaryl group are each independently selected from one or more of oxygen, sulfur, and nitrogen atoms.

[0029] In a preferred embodiment, the structure of the said organic compound is represented by General Formula (II - 1) to General Formula (II - 7) as follows:

[0030]

[0031]

[0032] In general formulas (II-1) to (II-7),

[0033] Z1-Z8 each independently represent a nitrogen atom, C-H or C-R;

[0034] R 1 each occurrence, independently of one another, represents a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group;

[0035] Each occurrence of R independently represents a deuterium atom, a halogen atom, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, an amino group, or one or more of these;

[0036] R a and R b each independently represent a hydrogen atom, a deuterium atom, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, an amino group, or one or more of these;

[0037] m and n each independently represent 0, 1, 2, or 3;

[0038] The substituents of the "substituted or unsubstituted" above-mentioned groups are each independently selected from a deuterium atom, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, an amino group, or one or more of these;

[0039] The heteroatoms in the heteroaryl group are each independently selected from one or more of oxygen, sulfur, and nitrogen atoms.

[0040] In a preferred embodiment, the R1 , R 2 , R 3 , R a , R b are represented as adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene group, 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 dibenzofuryl, phenyl-substituted tert-butyl, xanthone group, phenyl-substituted triazine group, phenyl-substituted borane group, methoxy, tert-butoxy;

[0041] R is represented as adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone group, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, tert-butoxy.

[0042] Preferably, X 1 and X 2 are the same, and X 3 and X 4 are the same.

[0043] Preferably, the specific structural formula of the organic compound is any one of the following structures:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] The present invention provides an organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0057] In a preferred embodiment, the light-emitting layer comprises a host material and a dopant material, and is characterized in that the dopant material contains the boron-containing organic compound.

[0058] In a preferred embodiment, the light-emitting layer comprises a first host material, a second host material and a dopant material, at least one of the first host material and the second host material being a TADF material, and the dopant material being the boron-containing organic compound.

[0059] The beneficial technical effects of the present invention are as follows:

[0060] (1) The compound of the present invention can be used as a dopant material for the light-emitting layer material in an OLED device, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

[0061] (2) The compound of the present invention has a high fluorescence quantum efficiency as a dopant material, and the fluorescence quantum efficiency of the material is close to 100%;

[0062] (3) As a dopant material, the compound of the present invention introduces a TADF sensitizer as the second host, which can effectively improve the device efficiency;

[0063] (4) The spectral FWHM of the compound of the present invention is narrow, which can effectively improve the device color gamut and the light-emitting efficiency of the device;

[0064] (5) The evaporation decomposition temperature of the compound of the present invention is high, which can inhibit the evaporation decomposition of the material and effectively improve the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] Figure 1 is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0066] 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 OF THE INVENTION

[0067] The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. Without conflict, the embodiments in the present invention and the features in the embodiments may be combined with each other. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but it is not limited to the present invention.

[0068] In the present invention, unless otherwise specified, HOMO means the highest occupied molecular orbital of a molecule, and LUMO means the lowest unoccupied molecular orbital of a molecule. In addition, in the present invention, the HOMO and LUMO energy levels are represented by absolute values, and the comparison between energy levels is also a comparison of the magnitudes of their absolute values. Those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of that energy level.

[0069] In the drawings, for clarity, the dimensions of layers and regions may be exaggerated. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, the layer or element may be directly on the other layer or substrate, or an intermediate layer may also be present. In addition, it will also be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intermediate layers may also be present. The same reference numerals throughout the text denote the same elements.

[0070] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms indicating directions such as "upper", "lower", "top", and "bottom" only represent the directions in a certain specific state, and do not mean that the relevant structures can only exist in the stated directions; on the contrary, if the structure can be transformed in position, such as being inverted, the directions of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of an electrode refer 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" and "upper" sides.

[0071] In the present invention, substituted or unsubstituted C 6 -C 30 aryl and / or substituted or unsubstituted C 2 -C 30 heteroaryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted A base, a substituted or unsubstituted terphenyl, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, 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 benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a fused ring of a combination of the foregoing groups, but not limited thereto.

[0072] The C described in the present invention 1 -C 10 The alkyl group (including linear 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, etc., but not limited thereto.

[0073] The halogen atom described in the present invention refers to a chlorine atom, a fluorine atom, a bromine atom, etc., but not limited thereto.

[0074] The C described in the present invention 3 -C 10 The cycloalkyl group refers to a monovalent monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms as ring-forming atoms. In the present text, C 4 -C 9 cycloalkyl is preferably used, and more preferably C 5 -C 8 cycloalkyl, and particularly preferably C 5 -C 7 cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, etc., but not limited thereto.

[0075] 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 stabilities, transparencies, surface smoothness, and water resistances. Depending on the nature of the substrate, its usage directions are different. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.

[0076] A first electrode is formed on the substrate, and the first electrode and the second electrode can face each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it can 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), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can 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 generally 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0077] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0078] In this article, the hole transport regions constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0079] As the materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials for OLED devices for use.

[0080] Examples of the above materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinolone derivatives, styryl anthracene derivatives, styrylamine derivatives and other styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinylenes and their derivatives, polythiophenes and their derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymer oligomers, aromatic tertiary amine compounds, styrylamine compounds, triamines, tetraamines, benzidine compounds, propynediamine 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)diphenyl sulfides, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes or 2,2-diphenylethylene compounds, etc.

[0081] 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 stacked structure of a plurality of different hole transport materials. In this article, for the above various hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0082] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material, so as to expect the occurrence of a charge transfer state between the host material and the doping material, achieve ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection conduction.

[0083] In view of the above empirical summaries, for hole host materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0084] Thus, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further comprises 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(cyanomethanylylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0085] 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, by mass.

[0086] The thickness of the hole injection layer of the present invention can be 5 - 100 nm, preferably 5 - 50 nm, and more preferably 5 - 20 nm, but the thickness is not limited to this range.

[0087] The thickness of the hole transport layer of the present invention can be 5 - 200 nm, preferably 10 - 150 nm, and more preferably 20 - 100 nm, but the thickness is not limited to this range.

[0088] The thickness of the electron blocking layer of the present invention can be 1 - 20 nm, preferably 5 - 10 nm, but the thickness is not limited to this range.

[0089] 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.

[0090] The light-emitting layer can comprise a host material and a doping material. The host material can use a common green host material in the art, and the doping material uses the boron-containing organic compound represented by the general formula (1) of the present invention.

[0091] 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, by mass.

[0092] 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, further preferably 10 - 50 nm, and more preferably 15 - 30 nm, but the thickness is not limited to this range.

[0093] In the present invention, the electron transport region may sequentially include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed above the light emitting layer, but is not limited thereto.

[0094] 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 efficiency of the device. The hole blocking layer of the present invention may be disposed above the light emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds having a hole blocking effect known in the prior art may be used. For example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum(III) bis(2-methyl-8-quinolinolato)-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) etc. pyrimidine derivatives, etc. The thickness of the hole blocking layer of the present invention may be 2 - 200 nm, preferably 5 - 150 nm, and more preferably 10 - 100 nm, but the thickness is not limited to this range.

[0095] The electron transport layer may be disposed above the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light emitting layer. A material with a high electron mobility is preferred. As the electron transport layer material of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices may be used. For example, metal complexes of hydroxyquinoline derivatives represented by Alq 3 、BAlq and Liq, various rare earth metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201) and other imidazole derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. The thickness of the electron transport layer of the present invention may be 10 - 80 nm, preferably 20 - 60 nm, and more preferably 25 - 45 nm, but the thickness is not limited to this range.

[0096] The electron injection layer can be disposed on the electron transport layer. The material of the electron injection layer is generally preferably a material with a low work function, so that electrons can be 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 materials known in the prior art for organic electroluminescent devices can be used, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, 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 can 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.

[0097] The second electrode can be disposed on the electron transport region. The second electrode can be a cathode. The second electrode can be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode can 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 can 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 generally 10 - 50 nm, preferably 15 - 20 nm.

[0098] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure can be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure can 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.

[0099] A method for preparing the organic electroluminescent device of the present invention includes successively 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 on a substrate, and optionally a covering layer. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI can be used, but are not limited thereto. In the present invention, it is preferred to use the vacuum evaporation method to form each layer. Those skilled in the art can conventionally select each process condition in the vacuum evaporation method according to actual needs.

[0100] The raw materials involved in the synthesis examples of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0101] Synthesis of Compound 1 in Example 1:

[0102]

[0103] Under nitrogen protection, 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-1, and 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 3 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated under vacuum. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-1. LC-MS: Measured value: 531.13 ([M+H] + ), theoretical value: 530.05.

[0104] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-1 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-1. LC-MS: Measured value: 539.01 ([M+H] + ), theoretical value: 538.03.

[0105] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-1, 2.88 mmol of raw material C-1, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added, and stirred at 90 °C for 12 hours. The reaction mixture was cooled to room temperature, the mixture was extracted with Et 2 O and washed with water, then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-1. LC-MS: Measured value: 707.48 ([M+H] + ), theoretical value: 706.42.

[0106] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-1 were dissolved in 10 mL of o-dichlorobenzene. Stir at 150 °C for 12 hours. After cooling to room temperature, quench with methanol and concentrate under reduced pressure. Then purify by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 1.

[0107] Synthesis of Compound 17 in Example 2:

[0108]

[0109] Under nitrogen protection, 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-2, 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 4 hours, cool the reaction mixture to room temperature. Pour the reaction mixture into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-2. LC-MS: Measured value: 789.35 ([M+H] + ), theoretical value: 788.23.

[0110] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-2 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 23 hours, dilute the reaction mixture with dichloromethane (50 mL), and add 100 mL of sodium phosphate buffer solution with pH = 6 at 0 °C. Separate the aqueous layer and extract with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-2. LC-MS: Measured value: 797.26 ([M+H] + ), theoretical value: 796.22.

[0111] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-2, 2.88 mmol of raw material C-2, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added, and stirred at 90 °C for 14 hours. Cool the reaction mixture to room temperature, and use Et 2Extract the mixture with O and wash with water. Then dry the organic phase with anhydrous magnesium sulfate, remove the solvent under reduced pressure, and purify by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-2. LC-MS: measured value: 853.56 ([M+H] + )), theoretical value: 852.48.

[0112] In a three-necked flask, under nitrogen protection, dissolve 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-2 in 10 mL of o-dichlorobenzene. Stir at 150 °C for 11 hours, cool to room temperature, quench with methanol and concentrate under reduced pressure, then purify by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 17.

[0113] Example 3 Synthesis of Compound 67:

[0114]

[0115] Under nitrogen protection, add 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-3, 5.20 mmol of K 2 CO 3 and 20 mL of DMF to a three-necked flask, and then heat to 110 °C. After stirring for 4 hours, cool the reaction mixture to room temperature, pour the reaction mixture into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid is washed with MeOH, and the obtained filtrate is evaporated in vacuo. The obtained residue is purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-3. LC-MS: measured value: 733.25 ([M+H] + )), theoretical value: 732.17.

[0116] In a three-necked flask, under nitrogen protection, dissolve 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-3 in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 22 hours, dilute the reaction mixture with dichloromethane (50 mL), and add 100 mL of sodium phosphate buffer solution with pH = 6 at 0 °C. Separate the aqueous layer and extract with dichloromethane (100 mL, three times). The crude product is purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-3. LC-MS: measured value: 741.28 ([M+H] + )), theoretical value: 740.16.

[0117] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-3, 2.88 mmol of raw material C-2, and 5.77 mmol of K were added respectively. 2 CO 3 、0.072 mmol of Pd(PPh 3 ) 4 、25 ml of toluene and aqueous solution (7 mL:7 mL, degassed), and stirred at 90 °C for 13 hours. The reaction mixture was cooled to room temperature, and the mixture was extracted with Et 2 O and rinsed with water, then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 =2:1) to obtain intermediate c-3. LC-MS: measured value: 797.46 ([M+H] + ), theoretical value: 796.42.

[0118] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-3 were dissolved in 10 mL of o-dichlorobenzene. Stirred at 150 °C for 13 hours, after cooling to room temperature, quenched with methanol and concentrated under reduced pressure, then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 67.

[0119] Example 4 Synthesis of Compound 83:

[0120] (1) Synthesis of raw material C-4:

[0121]

[0122] Under nitrogen protection, in a three-necked flask, 10 mmol of raw material F-4 was dissolved in 40 mL of anhydrous tetrahydrofuran, the temperature of the reactant was lowered to -78 °C, 4 mL of 2.5 M n-butyllithium was slowly added dropwise, the reactant was stirred at 0 °C for 1 hour, then the temperature of the reactant was lowered to -78 °C again, 12 mmol of trimethyl borate was added dropwise, and stirred at room temperature for 12 hours. After the reaction was completed, 2 mol / L HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. Then the water in the organic layer was removed with anhydrous magnesium sulfate, after suction filtration, the compound obtained by concentrating the organic solution was purified by silica gel column chromatography (eluent: Hex∶EA = 5∶1) to obtain raw material C-4. LC-MS: measured value: 225.18 ([M+H] + ), theoretical value: 224.10.

[0123] (2) Synthesis of Compound 83:

[0124]

[0125] Under nitrogen protection, 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-4, 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 3.5 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-4. LC-MS: Measured value: 563.13 ([M+H] + ), theoretical value: 562.00.

[0126] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-4 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 21 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-4. LC-MS: Measured value: 570.91 ([M+H] + ), theoretical value: 569.99.

[0127] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-4, 2.88 mmol of raw material C-4, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added, and stirred at 90 °C for 14 hours. The reaction mixture was cooled to room temperature, the mixture was extracted with Et 2 O and washed with water, then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-4. LC-MS: Measured value: 771.37 ([M+H] + ), theoretical value: 770.33.

[0128] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-4 were dissolved in 10 mL of o-dichlorobenzene. Stir at 150 °C for 15 hours, cool to room temperature, quench with methanol and concentrate under reduced pressure, and then purify by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 83.

[0129] Synthesis of Compound 95 in Example 5:

[0130] (1) Synthesis of Raw Material B-5:

[0131]

[0132] Under nitrogen protection, in a three-necked flask, 6.4 mmol of raw material E-5, 6.4 mmol of raw material F-5, 100 mL of toluene, 0.16 mmol of Pd(dba) 3 , 0.32 mmol of Xphos and 24.01 mmol of sodium tert-butoxide were added, heated to 108 °C, stirred for 3 h, then cooled to room temperature. The reaction solution was washed with water and then with anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. Then the crude product was recrystallized and purified using a toluene system to obtain raw material B-5. LC-MS: Measured value: 284.15 ([M+H] + ), theoretical value: 283.23.

[0133] (2) Synthesis of Compound 95:

[0134]

[0135] Under nitrogen protection, 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-5, 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 5 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into a large amount of MeOH to form a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated under vacuum. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-5. LC-MS: Measured value: 797.35 ([M+H] + ), theoretical value: 796.30.

[0136] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-5 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 23 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and the organic layer was extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-5. LC-MS: Measured value: 805.36 ([M+H] + ), Theoretical value: 804.28.

[0137] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-5, 2.88 mmol of raw material C-5, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added, and the mixture was stirred at 90 °C for 14 h. The reaction mixture was cooled to room temperature, the mixture was extracted with Et 2 O and washed with water, then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-5. LC-MS: Measured value: 893.62 ([M+H] + ), Theoretical value: 892.50.

[0138] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-5 were dissolved in 10 mL of o-dichlorobenzene. After stirring at 150 °C for 13 hours, the reaction mixture was cooled to room temperature, quenched with methanol and concentrated under reduced pressure, and then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 95.

[0139] Synthesis of Compound 134 in Example 6:

[0140] (1) Synthesis of Raw Material C-6:

[0141]

[0142] Under nitrogen protection, in a three-necked flask, 10 mmol of raw material F-6 was dissolved in 40 mL of anhydrous tetrahydrofuran. The temperature of the reactants was lowered to -78 °C, and 4 mL of 2.5 M n-butyllithium was slowly added dropwise. The reactants were stirred at 0 °C for 1 hour, then the temperature of the reactants was lowered to -78 °C, and 12 mmol of trimethyl borate was added dropwise. The mixture was stirred at room temperature for 14 hours. After the reaction was completed, 2 mol / L HCl aqueous solution was added, and the mixture was stirred for 30 minutes and extracted with ether. Then anhydrous magnesium sulfate was used to remove the moisture in the organic layer. After suction filtration, the concentrated organic solution was purified by silica gel column chromatography (eluent: Hex∶EA = 5∶1) to obtain raw material C-6. LC-MS: measured value: 324.19 ([M+H] + ), theoretical value: 323.21.

[0143] (2) Synthesis of compound 134:

[0144]

[0145] Under nitrogen protection, 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-1, 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 3 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-1. LC-MS: measured value: 531.13 ([M+H] + ), theoretical value: 530.05.

[0146] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-1 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-1. LC-MS: measured value: 539.01 ([M+H] + ), theoretical value: 538.03.

[0147] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-1, 2.88 mmol of raw material C-6, 5.77 mmol of K2 CO 3 , 0.072 mmol Pd(PPh 3 ) 4 , 25 ml of toluene and aqueous solution (7 mL:7 mL, degassed), stirred at 90 °C for 13 h. The reaction mixture was cooled to room temperature, and the mixture was extracted with Et 2 O and washed with water, then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by silica gel column chromatography (eluent: hexane: CH 2 Cl 2 = 2:1) to obtain intermediate c-6. LC-MS: found: 937.62 ([M+H] + ), theoretical: 936.58.

[0148] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-6 were dissolved in 10 mL of o-dichlorobenzene. Stirred at 150 °C for 14 h, cooled to room temperature, quenched with methanol and concentrated under reduced pressure, then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 134.

[0149] Example 7 Synthesis of Compound 136:

[0150] (1) Synthesis of starting material C-7:

[0151]

[0152] Under nitrogen protection, in a three-necked flask, 10 mmol of starting material F-7 was dissolved in 40 mL of anhydrous tetrahydrofuran, the temperature of the reactant was lowered to -78 °C, 4 mL of 2.5 M n-butyllithium was slowly added dropwise, the reactant was stirred at 0 °C for 1 h, then the temperature of the reactant was lowered to -78 °C, 12 mmol of trimethyl borate was added dropwise, and stirred at room temperature for 15 h. After the reaction was completed, 2 mol / L HCl aqueous solution was added, stirred for 30 min, and extracted with diethyl ether. Then, the water in the organic layer was removed with anhydrous magnesium sulfate, filtered by suction, and the concentrated organic solution was purified by silica gel column chromatography (eluent: Hex∶EA = 5∶1) to obtain starting material C-7. LC-MS: found: 326.36 ([M+H] + ), theoretical: 325.22.

[0153] (2) Synthesis of compound 136:

[0154]

[0155] Under nitrogen protection, 0.90 mmol of starting material A-1, 2.70 mmol of starting material B-1, 5.20 mmol of K 2 CO3 20 mL of DMF was added to a three-necked flask, and then the mixture was heated to 110 °C. After stirring for 3 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into a large amount of MeOH to form a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated under vacuum. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-1. LC-MS: measured value: 531.13 ([M+H] + ), theoretical value: 530.05.

[0156] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-1 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-1. LC-MS: measured value: 539.01 ([M+H] + ), theoretical value: 538.03.

[0157] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-1, 2.88 mmol of raw material C-7, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ), 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added respectively, and the mixture was stirred at 90 °C for 14 hours. The reaction mixture was cooled to room temperature, the mixture was extracted with Et 4 O and washed with water, then the organic phase was dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-7. LC-MS: measured value: 941.55 ([M+H] 2 ), theoretical value: 940.61. + )

[0158] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-7 were dissolved in 10 mL of o-dichlorobenzene. After stirring at 150 °C for 13 hours, after cooling to room temperature, the reaction was quenched with methanol and concentrated under reduced pressure, and then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 136.

[0159] Synthesis of Compound 205 in Example 8:

[0160] (1) Synthesis of Starting Material C-6:

[0161]

[0162] Under nitrogen protection, in a three-necked flask, dissolve 10 mmol of starting material F-6 in 40 mL of anhydrous tetrahydrofuran. Cool the reaction mixture to -78 °C, slowly add dropwise 4 mL of 2.5 M n-butyllithium, stir the reaction mixture at 0 °C for 1 hour, then cool the reaction mixture to -78 °C again, and add dropwise 12 mmol of trimethyl borate. Stir at room temperature for 14 hours. After the reaction is completed, add 2 mol / L HCl aqueous solution, stir for 30 minutes, and extract with diethyl ether. Then remove the moisture in the organic layer with anhydrous magnesium sulfate, filter by suction, and concentrate the organic solution. The obtained compound is purified by silica gel column chromatography (eluent: Hex∶EA = 5∶1) to obtain starting material C-6. LC-MS: Measured value: 324.19 ([M+H] + ), Theoretical value: 323.21.

[0163] (2) Synthesis of Compound 205:

[0164]

[0165] Under nitrogen protection, add 0.90 mmol of starting material A-1, 2.70 mmol of starting material B-2, 5.20 mmol of K 2 CO 3 and 20 mL of DMF into a three-necked flask, and then heat to 110 °C. After stirring for 4 hours, cool the reaction mixture to room temperature, pour the reaction mixture into a large amount of MeOH to form a precipitate. After filtration, the obtained solid is washed with MeOH, and the obtained filtrate is evaporated under vacuum. The obtained residue is purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-2. LC-MS: Measured value: 789.35 ([M+H] + ), Theoretical value: 788.23.

[0166] In a three-necked flask, under nitrogen protection, dissolve 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-2 in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 23 hours, dilute the reaction mixture with dichloromethane (50 mL), and add 100 mL of sodium phosphate buffer solution with pH = 6 at 0 °C. Separate the aqueous layer and extract with dichloromethane (100 mL, three times). The crude product is purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2= 5 / 1) Purification to obtain intermediate b-2. LC-MS: Measured value: 797.26 ([M+H] + ) with a theoretical value of 796.22.

[0167] Under nitrogen protection, in a three-necked flask, add 0.721 mmol of intermediate b-2, 2.88 mmol of raw material C-6, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed), and stir at 90 °C for 11 h. Cool the reaction mixture to room temperature, extract the mixture with Et 2 O and wash with water, then dry the organic phase with anhydrous magnesium sulfate, remove the solvent under reduced pressure, and purify by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-8. LC-MS: Measured value: 1195.70 ([M+H] + ) with a theoretical value of 1194.76.

[0168] In a three-necked flask, under nitrogen protection, dissolve 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-8 in 10 mL of o-dichlorobenzene. Stir at 150 °C for 11 hours, cool to room temperature, quench with methanol and concentrate under reduced pressure, then purify by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 205.

[0169] Example 9 Synthesis of Compound 247:

[0170] (1) Synthesis of raw material C-6:

[0171]

[0172] Under nitrogen protection, in a three-necked flask, dissolve 10 mmol of raw material F-6 in 40 mL of anhydrous tetrahydrofuran, lower the temperature of the reactant to -78 °C, slowly add 4 mL of 2.5 M n-butyllithium dropwise, stir the reactant at 0 °C for 1 hour, then lower the temperature of the reactant to -78 °C again, and add 12 mmol of trimethyl borate dropwise, and stir at room temperature for 14 hours. After the reaction is completed, add 2 mol / L aqueous HCl solution, stir for 30 minutes, and extract with ether. Then remove the moisture in the organic layer with anhydrous magnesium sulfate, filter by suction, and the compound obtained by concentrating the organic solution is purified by silica gel column chromatography (eluent: Hex∶EA = 5∶1) to obtain raw material C-6. LC-MS: Measured value: 324.19 ([M+H] + ) with a theoretical value of 323.21.

[0173] (2) Synthesis of Compound 247:

[0174]

[0175] Under nitrogen protection, 0.90 mmol of starting material A-1, 2.70 mmol of starting material B-9, 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 4 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-9. LC-MS: Measured value: 793.15 ([M+H] + ), theoretical value: 792.27.

[0176] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-9 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-9. LC-MS: Measured value: 801.33 ([M+H] + ), theoretical value: 800.25.

[0177] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-9, 2.88 mmol of starting material C-6, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added, and stirred at 90 °C for 14 hours. The reaction mixture was cooled to room temperature, and the mixture was extracted with Et 2 O and washed with water, then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-9. LC-MS: Measured value: 1199.88 ([M+H] + ), theoretical value: 1198.80.

[0178] In a three-necked flask, under nitrogen protection, 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-9 were dissolved in 10 mL of o-dichlorobenzene. Stir at 150 °C for 12 hours, cool to room temperature, quench with methanol and concentrate under reduced pressure, and then purify by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 247.

[0179] Synthesis of Compound 29 in Example 10:

[0180]

[0181] Under nitrogen protection, 0.90 mmol of raw material A-1, 2.70 mmol of raw material B-10, 5.20 mmol of K 2 CO 3 and 20 mL of DMF were added to a three-necked flask, and then heated to 110 °C. After stirring for 4 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to produce a precipitate. After filtration, the obtained solid was washed with MeOH, and the obtained filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate a-10. LC-MS: Measured value: 633.26 ([M+H] + ), theoretical value: 632.14.

[0182] In a three-necked flask, under nitrogen protection, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-10 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 22 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography (eluent: hexane / CH 2 Cl 2 = 5 / 1) to obtain intermediate b-10. LC-MS: Measured value: 641.02 ([M+H] + ), theoretical value: 640.13.

[0183] Under nitrogen protection, in a three-necked flask, 0.721 mmol of intermediate b-10, 2.88 mmol of raw material C-2, 5.77 mmol of K 2 CO 3 , 0.072 mmol of Pd(PPh 3 ) 4 , 25 ml of toluene and an aqueous solution (7 mL:7 mL, degassed) were added, and stirred at 90 °C for 14 hours. The reaction mixture was cooled to room temperature, and Et 2Extract the mixture and wash with water. Then dry the organic phase with anhydrous magnesium sulfate. Remove the solvent under reduced pressure. Purify by silica gel column chromatography (eluent: hexane:CH 2 Cl 2 = 2:1) to obtain intermediate c-10. LC-MS: Measured value: 697.30 ([M+H] + ), theoretical value: 696.39.

[0184] In a three-necked flask, under nitrogen protection, dissolve 0.32 mmol of boron tribromide and 0.212 mmol of intermediate c-10 in 10 mL of o-dichlorobenzene. Stir at 150 °C for 13 hours. After cooling to room temperature, quench with methanol and concentrate under reduced pressure. Then purify by silica gel column chromatography using dichloromethane as the eluent to obtain the target compound 29.

[0185] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0186] Table 1

[0187]

[0188] The compounds of the present invention can be used in light-emitting devices and can be used as doping materials for the light-emitting layer. The physical and chemical properties of the compounds prepared in the above examples of the present invention were tested, and the test results are shown in Table 2:

[0189] Table 2

[0190]

[0191]

[0192] Note: The glass transition temperature T g was measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter from Netzsch, Germany), with a heating rate of 10 °C / min; the thermal weight loss temperature T d is the temperature at which 1% weight loss occurs in a nitrogen atmosphere and was measured on a TGA-50H thermogravimetric analyzer from Shimadzu Corporation, Japan, with a nitrogen flow rate of 20 mL / min; the highest occupied molecular orbital HOMO energy level was tested by an ionization energy test system (IPS-3), and the test was carried out in a nitrogen environment; Eg was tested by a double-beam ultraviolet-visible spectrophotometer (model: TU-1901), and LUMO = HOMO + Eg; PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were obtained by testing with a Fluorolog-3 series fluorescence spectrometer from Horiba in the thin film state. τ (transient) was obtained by testing with a Fluorolog-3 series fluorescence spectrometer from Horiba in the thin film state, and k r (radiative transition rate) = 1 / τ.

[0193] As can be seen from the data in Table 2 above, the compounds of the present invention have relatively high glass transition temperatures and decomposition temperatures. When used as a doping material for the light-emitting layer, they can inhibit the crystallization and phase separation of the material; at the same time, they can also inhibit the decomposition of the material at high brightness, thereby extending the device lifetime. In addition, the compounds of the present application have appropriate HOMO energy levels. When doped into the host material as a doping material, it is beneficial to inhibit the generation of carrier traps, improve the host-guest energy transfer efficiency, and thus enhance the device luminescence efficiency.

[0194] The compounds of the present invention have relatively high fluorescence quantum efficiencies as doping materials, and the fluorescence quantum efficiency of the material is close to 100%; at the same time, the spectral FWHM of the material is relatively narrow, which can effectively improve the device color gamut and the device luminescence efficiency; finally, the evaporation decomposition temperature of the material is relatively high, which can inhibit the evaporation decomposition of the material, and the radiative transition rate of the material is relatively high, which can effectively extend the device lifetime.

[0195] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-10 and Device Comparative Examples 1-3. The manufacturing processes of Device Examples 2-10 and Device Comparative Examples 1-3 of the present invention are exactly the same as those of Device Example 1, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Table 3 and Table 4 respectively.

[0196] Device Example 1

[0197] As Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then 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, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED device is fabricated. CBP is used as the host material and compound 1 is used as the doping material, and the mass ratio of CBP and compound 1 is 97:3, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and 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 is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0198] The application effects of the synthesized OLED materials of the present invention in the devices are described in detail below through device examples 11-20 and device comparative examples 4-6. The manufacturing processes of the devices in device examples 12-20 and device comparative examples 4-6 of the present invention are exactly the same as those in device example 11, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3 and 4 respectively.

[0199] Device Example 11

[0200] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then 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, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. CBP and DMAC-BP are used as the dual host materials, and compound 1 is used as the doping material. The mass ratio of CBP, DMAC-BP, and compound 1 is 67:30:3, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and 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 is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0201] The molecular structural formulas of the related materials are as follows:

[0202]

[0203] After completing the OLED light-emitting device as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency, external quantum efficiency, and lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 3; the test results of the current efficiency, external quantum efficiency, and lifetime of the obtained devices are shown in Table 4.

[0204] Table 3

[0205]

[0206]

[0207]

[0208] Table 4

[0209]

[0210] Note: The voltage, current efficiency, and emission peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime test system was the EAS-62C OLED device lifetime tester from System Technology Research Co., Ltd. of Japan; LT95 refers to the time it takes for the device luminance to decay to 95%; all data were measured at 10 mA / cm 2 under the test.

[0211] From the device data results in Table 4, it can be seen that compared with Device Comparative Examples 1-3, the compounds of the present invention have higher current efficiency and device lifetime in the single-host system devices compared with the comparative examples; in the double-host system devices, the device efficiency also shows good results. This is because such a boron-nitrogen fused-ring mother nucleus can enhance the resonance intensity and improve the device efficiency without changing the light color; compared with Device Comparative Examples 4-6, the compounds of the present invention have significantly improved current efficiency and device lifetime in the double-host system devices compared with the OLED devices of known materials.

[0212] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included within 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 the general formula (1): In general formula (1), rings M1 and M2 each independently represent a substituted or unsubstituted aromatic ring of C 6 ; X 1 and X 2 are each independently represented as O, S, N(R 1 ); X 3 、X 4 are each independently represented as O, S, N(R 1 ); R 1 represents substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 heteroaryl; The substituents of the "substituted or unsubstituted" above-mentioned groups are each independently selected from one or more of a deuterium atom, an alkyl group of C 1 -C 10 an alkyl group of C 3 -C 10 a cycloalkyl group of C 6 -C 30 an aryl group of C 2 -C 30 a heteroaryl group; the heteroatom in the heteroaryl is optionally selected from one or more of oxygen, sulfur, and nitrogen atoms.

2. The boron-containing organic compound according to claim 1, characterized in that, the structure of the boron-containing organic compound is represented by any one of general formulas (2) to (4), general formulas (6) to (8), and general formulas (10) to (12): In General Formulas (2) to (13), the meanings of Ring M1, Ring M2, and R 1 are the same as those defined in Claim 1.

3. A boron-containing organic compound, characterized in that, the structure of the boron-containing organic compound is represented by the general formula (II): In general formula (II), X 1 , X 2 each independently represents O, S, N(R 1 ); X 3 、X 4 are each independently represented as O, S, N(R 1 ); Z 1 -Z 8 are independently represented as a nitrogen atom, C-H or C-R, respectively; R 1 represents substituted or unsubstituted C 6 -C 30 -aryl, substituted or unsubstituted C 2 -C 30 -heteroaryl; Each occurrence of R independently represents a deuterium atom, a halogen atom, an alkyl group of C 1 -C 10 , a cycloalkyl group of C 3 -C 10 , an aryl group of C 6 -C 30 , or a heteroaryl group of C 2 -C 30 , or one or more of them; The substituents of the "substituted or unsubstituted" above-mentioned groups are each independently selected from one or more of a deuterium atom, C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 6 -C 30 aryl, C 2 -C 30 heteroaryl; the heteroatom in the heteroaryl is optionally selected from one or more of oxygen, sulfur, and nitrogen atoms.

4. A boron-containing organic compound, characterized in that, the structure of the boron-containing organic compound is represented by general formulas (II-1) to (II-7): In general formulas (II-1) to (II-7), Z 1 -Z 8 Are separately and independently represented as a nitrogen atom, C-H or C-R; R 1 Each occurrence of the same or different, represented as substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 heteroaryl; Each occurrence of R independently represents a deuterium atom, a halogen atom, an alkyl group of C 1 -C 10 , an alkyl group of C 3 -C 10 , a cycloalkyl group of C 6 -C 30 , an aryl group, a C 2 -C 30 heteroaryl group, or one or more of the foregoing; R a and R b each independently represents one or more of a hydrogen atom, a deuterium atom, an alkyl group of C 1 -C 10 , a cycloalkyl group of C 3 -C 10 , an aryl group of C 6 -C 30 , or a heteroaryl group of C 2 -C 30 ; m and n independently represent 0, 1, 2, or 3; The substituents of the "substituted or unsubstituted" above-mentioned groups are each independently selected from one or more of a deuterium atom, C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 6 -C 30 aryl, C 2 -C 30 heteroaryl; the heteroatom in the heteroaryl is optionally selected from one or more of oxygen, sulfur, and nitrogen atoms.

5. The boron-containing organic compound according to claim 1 or 2, characterized in that, The R 1 is represented as phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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 dibenzofuryl, xanthenone, phenyl-substituted triazinyl.

6. The boron-containing organic compound according to claim 3, characterized in that, The R 1 is represented as phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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 dibenzofuryl, xanthenone, phenyl-substituted triazinyl; R is represented by adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene.

7. The boron-containing organic compound according to claim 4, characterized in that, The R 1 is represented as phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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, xanthenone, phenyl-substituted triazinyl; Said R a , R b is represented as adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene; R is represented by adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene.

8. The boron-containing organic compound according to claim 1, characterized in that, The said X 1 and X 2 are the same, X 3 and X 4 are the same.

9. A boron-containing organic compound, characterized in that, the specific structural formula of the boron-containing organic compound is any one of the following structures:

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

11. The organic electroluminescent device according to claim 10, characterized in that, the light-emitting layer contains a host material and a dopant material, and is characterized in that the dopant material contains the boron-containing organic compound according to any one of claims 1-9.

12. The organic electroluminescent device according to claim 10, the light-emitting layer contains a first host material, a second host material, and a dopant material, characterized in that, At least one of the first host material and the second host material is a TADF material, and the doping material is a boron-containing organic compound according to any one of claims 1-9.

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