Boron-containing organic compound and organic electroluminescent device containing the same

Abstract

The present invention discloses a boron-containing organic compound and an organic electroluminescent device containing the same, belonging to the field of semiconductor technology. 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 half-width and a high fluorescence quantum yield. It can be used as a green light doping material in the light-emitting layer of an organic electroluminescent device, thereby improving the luminescent color purity and lifespan of the device.

Description

Technical Field

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

[0002] Traditional fluorescent doping materials, limited by early technology, can only utilize the 25% of singlet excitons formed by electrical excitation to emit light. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lagging behind the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom center that enhances intersystem crossing, can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light, achieving a device internal quantum efficiency of 100%. However, the high cost of most phosphorescent materials, poor material stability, low color purity, and severe device efficiency roll-off have limited their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are being placed on color rendering standards. In addition to being efficient and stable, luminescent materials also need to have a narrower half-width to improve the color purity of the device's luminescent color. Fluorescent doping materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doping materials have achieved a phased breakthrough, and the half-width of boron-based materials can be reduced to below 30nm. However, research in the green light region, to which the human eye is more sensitive, has mainly focused on phosphorescent doping materials. However, their luminescent peak shape is difficult to narrow through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doping materials with narrow half-width.

[0004] 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 internal quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLED applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width luminescence. Such materials are used in sensitization technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN107507921A and CN110492006A disclose a TADF material with a difference between the lowest singlet state and the lowest triplet state energy level of less than or equal to 0.2eV as the main body, and a boron-containing material as the doping luminescent layer combination technology; CN110492005A and CN110492009A 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. Therefore, the development of sensitization technology based on narrow half-width boron-containing luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the Invention

[0006] In response to the above-mentioned problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device containing the same. The boron-containing organic compound of the present invention can be used as a green light doping material in the light-emitting layer of the organic electroluminescent device, thereby improving the luminous color purity and life of the device.

[0007] 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):

[0008]

[0009] In the general formula (1), Z represents the same or different C-R1;

[0010] X represents -O-, -S-, -N(R2)- or -C(R3)(R4)-;

[0011] R, R1 represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 Heteroaryl, adjacent R1 can be connected to form a ring;

[0012] R2, R3, and R4 represent substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C30 heteroaryl;

[0013] Ar represents a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0014] M1 and M2 rings are substituted or unsubstituted C6-C 30 Aromatic ring, substituted or unsubstituted C4-C 30 heteroaromatic rings;

[0015] The substituents of the substituted group may be selected from deuterium atoms, tritium atoms, halogens, cyano groups, C1-C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Heteroaryl.

[0016] Preferably, the structure of the organic compound is any one of the general formulas (1-1) to (1-2):

[0017]

[0018] In general formula (1-1) to general formula (1-2), the meanings of Z, R, X, R1, R2, R3, R4, Ar, M1, and M2 are the same as defined above.

[0019] Preferably, the structure of the organic compound is any one of the general formulas (1-3) to (1-6):

[0020]

[0021] In general formula (1-3) to general formula (1-6), the meanings of Z, R, X, R1, R2, R3, R4, Ar, M1, and M2 are the same as defined above.

[0022] In a preferred embodiment, the structure of the organic compound is any one of the general formulas (1-7) to (1-10):

[0023]

[0024] In general formulae (1-7) to (1-10), the meanings of Z, R, X, R1, R2, R3, R4, and Ar are the same as those defined above.

[0025] In a preferred embodiment, the structure of the organic compound is any one of the general formulas (1-11) to (1-14):

[0026]

[0027] In general formula (1-11) to general formula (1-14), the meanings of Z, R, X, R1, R2, R3, R4, and Ar are the same as those defined above;

[0028] R a 、R b 、R c 、R d Represented by hydrogen atom, deuterium atom, tritium atom, halogen, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl;

[0029] The substituents of the substituted group may be selected from deuterium atoms, tritium atoms, halogens, cyano groups, C1-C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Heteroaryl.

[0030] Preferably, the structure of the organic compound is any one of the general formulas (2-1) to (2-6):

[0031] In general formulae (2-1) to (2-6), the meanings of M1, Z, R, R1, and Ar are the same as those defined above.

[0032] In a preferred embodiment, the structure of the organic compound is shown in general formula (3-1) to general formula (3-5):

[0033]

[0034] In general formulae (3-1) to (3-5), X, M1, Z, and Ar have the same meanings as defined above.

[0035] Preferably, the structure of the organic compound is any one of the general formulas (4-1) to (4-3):

[0036]

[0037] In general formulae (4-1) to (4-3), X, M, Z, and Ar have the same meanings as defined above.

[0038] Preferably, the structure of the organic compound is shown in the general formula (5-1):

[0039]

[0040] In (5-1), X, Z, R, and Ar have the same meanings as defined above.

[0041] In a preferred embodiment, the structure of the organic compound is shown in general formulas (6-1) to (6-3):

[0042]

[0043]

[0044] In (6-1) to (6-3), X, Z, R, and Ar have the same meanings as defined above.

[0045] Preferably, the R, R1, R a 、R b 、R c 、R d Each occurrence of the same or different radicals represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, or a phenyl group. , deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy;

[0046] Said R2, R3, R4, Ar represent adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, Biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethyl Fluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, tert-butoxy;

[0047] M1 and M2 rings are represented by benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, quinoline ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, N-phenylcarbazole ring, 9,9-dimethylfluorene ring, spirofluorene ring;

[0048] The substituent of the substituted group can be selected from one of a deuterium atom, a tritium atom, a fluorine atom, an adamantyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a quinolyl group, a furyl 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, and a spirofluorenyl group.

[0049] Preferably, Ar and R2 are represented by the following structure:

[0050]

[0051] The R, R1, R a 、R b 、R c 、R d It is represented by the following structure:

[0052]

[0053] Preferably, the specific structural formula of the organic compound is any one of the following structures:

[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 host 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 host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound.

[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 is used as a doping material, and the phosphorescent material is introduced as an exciton sensitizer, which can effectively improve the device life;

[0074] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and enhance the luminous efficiency of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0075] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0076] 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

[0077] The following will be combined with the accompanying drawings in the embodiments of the present invention to clearly and completely describe the technical solutions 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 following will further illustrate the present invention with reference to the accompanying drawings and specific embodiments, but it is not intended to limit the present invention.

[0078] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms such as "upper," "lower," "top," and "bottom" that indicate orientation refer only to a particular state and do not imply that the structure can exist only in the described orientation. Conversely, if the structure can be repositioned, such as inverted, the orientation of the structure will change accordingly. Specifically, in the present invention, the "bottom" or "lower" side of an electrode refers to the side of the electrode closest to the substrate during fabrication, while the opposite side, farther from the substrate, is the "top" or "upper" side.

[0079] In the present invention, substituted or unsubstituted C6-C 30 Aryl and / or substituted or unsubstituted C2-C 30 Heteroaryl 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 substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted indenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted 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 phenanthrazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or fused rings of combinations thereof, but are not limited thereto.

[0080] The C1-C of the present invention 10 Alkyl (including straight-chain alkyl and branched-chain 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 is not limited thereto.

[0081] The halogen mentioned in the present invention refers to a chlorine atom, a fluorine atom or a bromine atom, but is not limited thereto.

[0082] The C3-C 10 A cycloalkyl group refers to a monovalent monocyclic saturated hydrocarbon group containing 3 to 10 carbon atoms as ring atoms. In this article, a C4-C9 cycloalkyl group is preferably used, a C5-C8 cycloalkyl group is more preferably used, and a C5-C7 cycloalkyl group is particularly preferably used. Non-limiting examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0083] As the substrate for the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples include transparent substrates such as glass or transparent plastic substrates, and opaque substrates such as silicon substrates. Different substrates have varying mechanical strength, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use varies. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0084] 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 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0085] 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.

[0086] 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.

[0087] As materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.

[0088] Examples of the above materials include 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 quilone derivatives, styrylanthracene derivatives, styrylamine derivatives and other styrene compounds, 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 other 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.

[0089] Furthermore, depending on the device configuration, the hole transport layer between the electron blocking and hole injection layers of the organic electroluminescent device can be a single layer or a stacked structure of multiple hole transport materials. In this document, the thickness of the various hole carrier conducting layers with different functions described above is not particularly limited.

[0090] The hole injection layer contains a host 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 hole injection from the anode to the organic film layer, the HOMO energy level of the host organic material used in the anode interface buffer layer must have certain characteristics with the P-doped material. Only then can the charge transfer state between the host material and the dopant material be achieved, and ohmic contact between the buffer layer and the anode can be achieved, achieving efficient injection and conduction of holes from the electrode.

[0091] 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.

[0092] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further includes a P-type dopant material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0093] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0094] 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.

[0095] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0096] The thickness of the electron blocking layer of the present invention may be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0097] 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.

[0098] 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 resonance-type organic compound represented by the general formula (1) of the present invention.

[0099] The light-emitting layer may contain a single host material or a dual host material;

[0100] The dual host material comprises a first host material and a second host material, wherein at least one of the first host material and the second host material is preferably a TADF material;

[0101] TADF materials exhibit thermally activated delayed fluorescence (TADF), characterized by a small energy difference between the first excited singlet and triplet states. This allows for simultaneous utilization of both singlet and triplet excitons within the device, resulting in a near 100% utilization rate of electrically generated excitons within the device. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0102] The light-emitting layer may comprise a host material, an exciton-sensitizing material, and a dopant material;

[0103] Exciton-sensitizing materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electrically induced excitons, thereby ultimately producing an emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing organic compound represented by general formula (1) of the present invention, when used in combination with an exciton-sensitizing material, significantly improves device efficiency, prevents exciton annihilation in the device, and reduces efficiency.

[0104] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0105] The thickness of the light-emitting layer can be adjusted to optimize the luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-40 nm, but the thickness is not limited to this range.

[0106] 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.

[0107] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be arranged above 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 bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis(2-methyl-8-quinolinol)-4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives such as 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0108] The electron transport layer can be disposed on the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that readily accepts 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, electron transport layer materials for organic electroluminescent devices known in the prior art can be used, for example, metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-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.

[0109] The electron injection layer may be provided 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 materials 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 such as 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.

[0110] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include, but is not limited to, 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. The thickness of the cathode depends on the material used.

[0111] 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 or metal can, or a thin film covering the entire surface of the organic layer.

[0112] The method for preparing an organic electroluminescent device of the present invention comprises sequentially 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, and optionally a cover layer, on a substrate. 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, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0113] 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;

[0114] Synthesis of raw material A2:

[0115]

[0116] Add raw material M1 (5.0 mmol) to a bottle, followed by raw material N1 (5.0 mmol), saturated aqueous K2CO3 solution (25.0 mmol), THF (80 mL), and Pd(PPh3)4 (0.2 mmol). Reflux under nitrogen for 24 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane (150 mL x 3). Dry with anhydrous sodium sulfate, filter, and concentrate the organic phase. The resulting residue is purified by silica gel column chromatography to obtain raw material A2.

[0117] Synthesis of raw material D4:

[0118]

[0119] Raw material M2 (5.0 mmol) was added to a bottle, followed by raw material N2 (5.0 mmol), saturated aqueous K2CO3 (25.0 mmol), THF (80 mL), and Pd(PPh3)4 (0.2 mmol). The mixture was refluxed under nitrogen for 36 hours. After the reaction, the mixture was cooled to room temperature and extracted with dichloromethane (150 mL x 3). The mixture was then dried over anhydrous sodium sulfate, filtered, and the organic phase was concentrated. The resulting residue was purified by silica gel column chromatography to obtain raw material D4.

[0120] Synthesis of intermediate E1:

[0121]

[0122] Under nitrogen, 0.90 mmol of starting material A1, 1.35 mmol of starting material B1, 5.20 mmol of K2CO3, and 20 mL of DMF were added to a three-necked flask and then heated to 110°C. After stirring for 2 hours, the reaction mixture was cooled to room temperature and poured into a large amount of MeOH to produce a precipitate. After filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate C1;

[0123] Under nitrogen, 1.0 mmol of intermediate C1, 1.0 mmol of starting material D1, 5.0 mmol of KCO, and 20 mL of DMF were added to a three-necked flask and heated to 110°C. After stirring for 3 hours, the reaction mixture was cooled to room temperature and poured into a large amount of MeOH to produce a precipitate. After filtration, the resulting solid was washed with MeOH, and the filtrate was evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to provide intermediate E1.

[0124] Referring to the preparation process of intermediate E1, the following E series intermediates were synthesized; the reaction conditions were the same, except that the raw materials A, B and C listed in Table 1 below were used:

[0125] Table 1: Synthesis of Intermediate E Series

[0126]

[0127]

[0128] Example 1: Synthesis of Compound 9:

[0129]

[0130] Under nitrogen, 1.0 mmol of intermediate E1, 1.0 mmol of starting material F1, 5.0 mmol of KCO, and 20 mL of DMF were added to a three-necked flask and heated to 120°C. After stirring for 5 hours, the reaction mixture was cooled to room temperature and poured into a large amount of MeOH to produce a precipitate. After filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE:DCM = 5:1) to obtain intermediate G1.

[0131] In a three-necked flask, under nitrogen, 2.0 mmol of boron tribromide and 1.0 mmol of intermediate G1 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 pH 6 sodium phosphate buffer 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 / CH2Cl2 = 5 / 1) to obtain the target compound 9.

[0132] The following target compound was synthesized by referring to the preparation process of target compound 1 in Example 1; the reaction conditions were the same, except that the intermediate E and raw material F listed in Table 2-1 below were used;

[0133] Table 2-1

[0134]

[0135]

[0136] Table 2-2

[0137]

[0138] The compounds of the present invention can be used in light-emitting devices as dopants for the light-emitting layer. The compounds prepared in the above examples of the present invention were tested for their full width at half maximum (FWHM). The full width at half maximum (FWHM) of compounds 9, 35, 46, 48, 63, 123, 239, 248, 300, and 301 were 25 nm, 26 nm, 25 nm, 25 nm, 26 nm, 29 nm, 24 nm, 24 nm, 27 nm, and 26 nm, respectively.

[0139] The FWHM (full width at half maximum) is measured by Horiba's Fluorolog-3 series fluorescence spectrometer in a thin film state. The spectral FWHM of the compound of the present invention is narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device.

[0140] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 1-10 and Comparative Examples 1-4. The device fabrication processes for Device Examples 2-10 and Comparative Examples 1-4 are identical to those of Device Example 1, utilizing the same substrate and electrode materials, with the same electrode thickness. The only difference is the material used in the light-emitting layer. The layer structures and test results for each device example are shown in Tables 3 and 4, respectively.

[0141] Device Example 1

[0142] 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, washed with a detergent (SemicleanM-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 9 as the doping material, the mass ratio of GH-1, GH-2 and compound 9 is 69:30:1, and the light-emitting layer thickness is 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick film. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0143] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 11-20 and Comparative Example 5. The device fabrication processes for Device Examples 12-20 and Comparative Example 5 are identical to those for Device Example 11, utilizing the same substrate and electrode materials, with the same electrode thickness. The only difference is the material used in the light-emitting layer. The layer structures and test results for each device example are shown in Tables 3 and 4, respectively.

[0144] Device Example 11

[0145] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed, that is, washed with a detergent (SemicleanM-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 are evaporated with a thickness of 10nm as the hole injection layer 3 using a vacuum evaporation device. The mass ratio of HT-1 to HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. EB-1 with a thickness of 30nm is then evaporated as the electron blocking layer 5. After the above electron blocking material evaporation is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared. GH-1 and GH-2 are used as the main materials, GD-1 is used as the first dopant material, and compound 9 is used as the second dopant material. The mass ratio of GH-1, GH-2, GD-1 and compound 9 is 66:30:3:1, and the light-emitting layer thickness is 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick film. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0146] The molecular structure formula of the relevant materials is shown below:

[0147]

[0148] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known drive circuit, and the device voltage, current efficiency, and device lifespan were measured. Examples and comparative examples of devices prepared using the same method are shown in Table 3; the test results for the voltage, current efficiency, and lifespan of the resulting devices are shown in Table 4.

[0149] Table 3

[0150]

[0151]

[0152] Table 4

[0153]

[0154] Note: Voltage, current efficiency, and luminescence peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the lifespan test system was an EAS-62C OLED device lifespan tester from Japan System Giken Co., Ltd.; LT95 refers to the time it takes for the device's luminance to decay to 95%; all data are measured at 10 mA / cm 2 Next test.

[0155] It can be seen from the device data results in Table 4 that, compared with device comparison examples 1-4, the device life of the compounds of the present invention in single-doping system devices is longer than that of the comparative examples; in single-doping system devices, the device efficiency also shows a good effect, which is because such boron-nitrogen fused ring mother core can enhance the resonance intensity and improve the device efficiency without changing the light color; compared with device comparison example 5, the compound of the present invention uses an exciton-sensitized material as the first doping in a dual-doping system device. The current efficiency and device life of the device are greatly improved compared to OLED devices with known materials, and in the dual-doping device, the device efficiency is also significantly improved compared to the single-doping case.

[0156] In summary, the above are only 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 should be included in the scope of protection of the present invention.

Claims

1. A boron-containing organic compound, characterized in that The structure of the organic compound is any one of the general formulas (1-7) to (1-10): In general formula (1-7) to general formula (1-10), Z represents the same or different C-R1; X represents -O-, -S- or -N(R2)-; R, R1 represents a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl; R2 represents a substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl; Ar represents a substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents of the substituted group may be selected from deuterium atoms, halogens, cyano groups, C1-C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Heteroaryl.

2. The boron-containing organic compound according to claim 1, characterized in that The structure of the organic compound is any one of the general formulas (1-11) to (1-14): In general formula (1-11) to general formula (1-14), the Z represents the same or different C-R1; R1 represents a hydrogen atom or a deuterium atom; X represents -O-, -S- or -N(R2)-; R represents a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl; R2 represents a substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl; Ar represents a substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R a 、R b 、R c 、R d Represented by hydrogen atom, deuterium atom, halogen, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl; The substituents of the substituted group may be selected from deuterium atoms, halogens, cyano groups, C1-C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Heteroaryl.

3. The boron-containing organic compound according to claim 1, characterized in that The structure of the organic compound is any one of the general formulas (2-1) to (2-6): In general formula (2-1) to general formula (2-6), Z represents the same or different C-R1; R1 represents a hydrogen atom, a deuterium atom, a halogen, a cyano group, a C1-C 10 Alkyl, C6~C 30 Aryl, C2~C 30 heteroaryl; R represents a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl; Ar represents a substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The M1 ring represents a substituted or unsubstituted benzene ring; The substituents of the substituted group may be selected from deuterium atoms, halogens, cyano groups, C1-C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Heteroaryl.

4. The boron-containing organic compound according to claim 1, characterized in that The R and R1 appearing each time are the same or different and represent a hydrogen atom, a deuterium atom, a halogen atom, 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 naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted one of deuterated phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert-butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated ethyl substituted biphenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted biphenyl, phenyl substituted amino, tert-butylbenzene substituted amino, tert-butyl substituted dibenzofuranyl, phenyl substituted tert-butyl, xanthone, phenyl substituted triazinyl, methoxy, and tert-butoxy; Said R2 and Ar represent adamantyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, One of 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, xanthone group, and phenyl-substituted triazinyl.

5. The boron-containing organic compound according to claim 2, characterized in that The R, R a 、R b 、R c 、R d Each occurrence of the same or different radicals represents a hydrogen atom, a deuterium atom, a halogen atom, 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 naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group 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-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, and tert-butoxy; Said R2 and Ar represent adamantyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, One of 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, xanthone group, and phenyl-substituted triazinyl.

6. The boron-containing organic compound according to claim 3, characterized in that Each occurrence of R, which is the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, 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 naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted One of 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-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, and tert-butoxy; The R1 each time appears the same or different represents one of a hydrogen atom, a deuterium atom, a halogen atom, an adamantyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a quinolyl group, a furyl 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, and a xanthone group; The Ar is represented by adamantyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl benzophenone, benzothiophene ... One of 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, xanthone group, and phenyl-substituted triazinyl group.

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

8. 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 7.

9. The organic electroluminescent device according to claim 8, 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 7.

10. The organic electroluminescent device according to claim 8, wherein the light-emitting layer comprises a first host material, a second host material and a doping material, wherein: At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1 to 7.

11. The organic light-emitting device according to claim 8, 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 the boron-containing organic compound according to any one of claims 1 to 7.

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