An organic compound with a boron-containing heterocyclic structure and an organic light-emitting device prepared therefrom

Abstract

The present invention relates to an organic compound containing a boron heterocyclic structure and an organic light-emitting device prepared therefrom, belonging to the field of semiconductor technology. The structure of the compound of the present invention is shown in the general formula (1): The compound of the present invention has a narrow full width at half maximum, a high fluorescence quantum yield, a high glass transition temperature and molecular thermal stability, and has appropriate HOMO and LUMO energy levels. When used as a doping material in the light-emitting layer material of an OLED light-emitting device, the current efficiency and external quantum efficiency of the device are significantly improved, and at the same time, the emission color purity and the device life are also greatly improved.

Description

Technical Field

[0001] The present invention relates to the technical field of semiconductor materials, and particularly to an organic compound as an OLED doping material and an organic light-emitting device prepared therefrom. Background Art

[0002] Limited by early technologies, traditional fluorescent doping materials 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 significant gap compared with the efficiency of phosphorescent devices. Due to the strong spin-orbit coupling of heavy atom centers, phosphorescent materials enhance intersystem crossing and 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%.

[0003] With the advent of the 5G era, higher requirements are put forward for color rendering standards. In addition to high efficiency and stability, luminescent materials also require a narrower full width at half maximum (FWHM) to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum yields and narrow FWHMs through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, with the FWHM of boron-based materials being reduced to less than 30 nm. In the green region, which is more sensitive to the human eye, 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 high-efficiency green fluorescent doping materials with narrow FWHMs to meet higher color rendering standards.

[0004] In addition, the TADF sensitized fluorescence technology (TSF) combines TADF materials with fluorescent doping materials. Using TADF materials as exciton sensitization media, triplet excitons formed by electrical excitation are converted into singlet excitons, and the energy is transferred to the fluorescent doping materials through long-range energy transfer of singlet excitons. Similarly, the internal quantum efficiency of the device can reach 100%. This technology can compensate for the deficiency of 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-containing compounds with resonance structures are more likely to achieve narrow full-width at half-maximum (FWHM) luminescence. When such materials are applied to thermally activated delayed fluorescence (TADF) sensitized fluorescence technology, devices with high efficiency and narrow FWHM emission can be fabricated. 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 is disclosed, which uses an exciplex as the host and a boron-containing material as the dopant; both can achieve efficiency comparable to phosphorescence and relatively narrow FWHM. Therefore, developing TADF sensitized fluorescence technology based on narrow FWHM boron-containing luminescent materials has unique advantages and strong potential for meeting the BT.2020 display standards. SUMMARY OF THE INVENTION

[0006] In view of the above problems existing in the prior art, the present invention provides an organic compound containing a boron heterocyclic structure and its applications. The compound of the present invention has a narrow FWHM, a high fluorescence quantum yield, and strong molecular stability, and can be used as a luminescent layer doping material for organic light-emitting devices, thereby improving the color purity and lifespan of the devices.

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

[0008]

[0009] In the general formula (1), Z1-Z8 represent CH or C(R1), and each occurrence of R1 represents, the same or differently, a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 alkoxy, a substituted or unsubstituted C1-C 10 aryloxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; adjacent R1s can also be connected to form a ring;

[0010] M1 and M2 represent, the same or differently, a substituted or unsubstituted C6-C 30 aryl ring, a substituted or unsubstituted C4-C 30 heteroaryl ring;

[0011] X1 and X2 each independently represent O, S, or N(R2), and each occurrence of R2 represents, the same or differently, a substituted or unsubstituted C1-C10 An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 One of a heteroaryl group, and R2 in X2 can also be connected to adjacent M1 or M2 to form a ring; R2 in X2 can also be connected to R1 connected to Z1 and / or Z2 to form a ring;

[0012] The substituents for the substituting groups are deuterium, halogen, cyano group, C1-C 10 An alkyl group, C3-C 10 A cycloalkyl group, C6-C 30 An aryl group, C2-C 30 One or more of a heteroaryl group.

[0013] In a preferred embodiment, M1 and M2 are represented as a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-heterocarbazolyl group.

[0014] R1 is represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a cyano group, a methoxy group, a substituted or unsubstituted anilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-heterocarbazolyl group.

[0015] R2 is represented by one of a substituted or unsubstituted phenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted benzofuryl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted dibenzofuryl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted carbazolyl, and a substituted or unsubstituted N-heterocarbazolyl.

[0016] The substituents for the substituting groups are each independently selected from: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyano, methoxy, phenyl, pyridyl, triazinyl, biphenyl, naphthyl.

[0017] R1 and X2 may be connected by a single bond.

[0018] Preferably, the structure of the compound is shown as any one of general formulas (1-1) to (1-26):

[0019]

[0020]

[0021]

[0022] X3 is represented by one of O, S, and N-R3; R3 is represented by one of a substituted or unsubstituted C6-C 12 aryl, and a substituted or unsubstituted C4-C 12 heteroaryl;

[0023] Z is represented by C(R4), and R4 is the same or different each time it appears and is represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 alkoxy, a substituted or unsubstituted C1-C 10 aryloxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; adjacent R4s may also be connected to form a ring;

[0024] The substituents for the substitution groups are each independently selected from one or more of: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyano, methoxy, phenyl, pyridyl, triazinyl, biphenyl, naphthyl; the definitions of X1, X2, Z1-Z8 are the same as those defined above.

[0025] Preferably, the structure of the compound is shown as any one of general formulas (2) to (6):

[0026]

[0027] In general formulas (2) to (6), Z1-Z8 are represented as CH or C(R1), and each occurrence of R1 is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C1-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; adjacent R1s can also be connected to form a ring;

[0028] X1, X2, X3 are each independently represented as O, S or N(R2), and each occurrence of R2 is the same or different and represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0029] R a 、R b each occurrence is the same or different and represents a hydrogen atom, a deuterium atom, a halogen, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group;

[0030] m, n are represented as 0, 1, 2, 3, 4;

[0031] The substituents for the substitution groups are deuterium, halogen, cyano, C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group.

[0032] In a preferred embodiment, the structure of the compound is represented by any one of general formulas (7) to (16):

[0033]

[0034] In general formulas (7) to (16), Z1-Z8 represent CH or C(R1), and each occurrence of R1, which may be the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C1-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; adjacent R1 groups may also be joined to form a ring;

[0035] R a and R b , each occurrence of which, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group, or one or more of them; m and n represent 0, 1, 2, 3, or 4;

[0036] The substituents for the substituent groups are deuterium, a halogen, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group, or one or more of them.

[0037] In a preferred embodiment, the R1, R a and R bIt is represented by one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a cyano group, a methoxy group, a substituted or unsubstituted anilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-heterocarbazolyl group;

[0038] Said R2 is represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-heterocarbazolyl group;

[0039] The substituents for the substituting groups are each independently selected from one or more of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a cyano group, a methoxy group, a phenyl group, a pyridyl group, a triazinyl group, a biphenyl group, and a naphthyl group.

[0040] In a preferred embodiment, the specific structural formula of the organic compound is any one of the following structures:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] An organic light-emitting device includes a cathode, an anode, and a functional layer. The functional layer is located between the cathode and the anode, and the functional layer contains the organic compound with the boron-containing heterocyclic structure.

[0053] In a preferred embodiment, the functional layer includes a light-emitting layer, and the doping material of the light-emitting layer is the organic compound with the boron-containing heterocyclic structure.

[0054] More preferably, the light-emitting layer includes 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 organic compound with the boron-containing heterocyclic structure.

[0055] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0056] (1) The compound of the present invention can be used as a doping material for the light-emitting layer material when applied to an OLED device, and can emit fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

[0057] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0058] (3) The spectral FWHM of the compound of the present invention is narrow, which can effectively improve the color gamut of the device and the light-emitting efficiency of the device;

[0059] (4) 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.

[0060] (5) The compound of the present invention can significantly increase the oscillator strength of the excited state and reduce the reorganization energy of the molecule, thereby achieving the effects of reducing the Stokes shift and narrowing the full width at half maximum. Description of the Drawings

[0061] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0062] 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 Embodiments

[0063] The present invention will be specifically described below with reference to the accompanying drawings and embodiments.

[0064] In the present invention, unless otherwise specified, HOMO means the highest occupied molecular orbital, and LUMO means the lowest unoccupied molecular orbital. In addition, in the present invention, the HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the absolute values. Those skilled in the art know that the larger the absolute value of the energy level, the lower the energy of that energy level.

[0065] Any numerical range listed herein is intended to include all sub-ranges having the same numerical precision within the listed range. For example, "1.0 to 10.0" means to include all sub-ranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and including 1.0 and 10.0), that is, all sub-ranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limitation listed herein is intended to include all smaller numerical limitations incorporated herein, and any minimum numerical limitation listed herein is intended to include all larger numerical limitations incorporated herein. Therefore, the applicant reserves the right to modify this specification, including the claims, to clearly describe any sub-range that falls within the range clearly described herein.

[0066] 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.

[0067] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms indicating orientation such as "upper", "lower", "top", and "bottom" only represent the orientation in a specific state, and do not mean that the relevant structure can only exist in the described orientation; on the contrary, if the structure can be transformed in position, for example, inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the 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.

[0068] 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.

[0069] A first electrode is formed on the substrate, and the first electrode and the second electrode can be opposite to 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 usually 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0070] 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.

[0071] In this article, the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0072] 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.

[0073] Examples of the above materials may 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 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 vinylene and its derivatives, polythiophene and its 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.

[0074] Furthermore, according to the requirements of device configuration, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer that constitutes the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this article, for the above-mentioned hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0075] 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.

[0076] In view of the above empirical summaries, for hole-type 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] The light-emitting layer may comprise a host material and a doping material. The host material can be a common green host material in the art, and the doping material is an organic compound with a boron-containing heterocyclic structure represented by the general formula (1) of the present invention.

[0084] 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. The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and 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.

[0085] 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 provided on the light-emitting layer, but not limited thereto.

[0086] 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 lifespan of the device and improving the device's efficiency. The hole blocking layer of the present invention can be disposed above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art with hole blocking effects 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-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 ) and other pyrimidine derivatives, etc. The thickness of the hole blocking layer of the present invention can be 2 - 200 nm, preferably 5 - 150 nm and more preferably 10 - 100 nm, but the thickness is not limited to this range.

[0087] The electron transport layer can be disposed above the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. A material with a high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices 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-(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 can be 10 - 80 nm, preferably 20 - 60 nm and more preferably 25 - 45 nm, but the thickness is not limited to this range.

[0088] The electron injection layer can be disposed on the electron transport layer. The material of the electron injection layer is generally preferably a material having a low work function, such that electrons can be easily injected into the organic functional material layer. As the material of the electron injection layer of the organic electroluminescent device of the present invention, materials known in the prior art for the electron injection layer of 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.

[0089] 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.

[0090] 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.

[0091] 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, and optionally a covering layer on a substrate. 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 of the layers. Those skilled in the art can conventionally select each process condition in the vacuum evaporation method according to actual needs.

[0092] 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;

[0093] Synthesis of Compound 3 in Example 1:

[0094]

[0095] (1) Add raw material A1 (20 mmol), raw material A2 (80 mmol), Pd2(dba)3 (0.5 mmol), S-Phos (1.0 mmol), K2CO3 (200 mmol), and toluene (250 mL) into the flask in sequence. Then replace the gas with nitrogen for protection, stir overnight at 110 °C. After the reaction is completed, cool to room temperature, add ethyl acetate to dilute the reaction solution, quench with water. Extract the aqueous phase with ethyl acetate three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, concentrate the organic phase, and purify by silica gel column chromatography to obtain raw material A3.

[0096] (2) Add raw material A3 (15 mmol), raw material A4 (35 mmol), Pd(AcO)2 (0.5 mmol), DPEPhos (1.0 mmol), AcONa (150 mmol), and toluene (250 mL) into the flask in sequence. Then replace the gas with nitrogen for protection, reflux overnight. After the reaction is completed, cool to room temperature, add ethyl acetate to dilute the reaction solution, quench with water. Extract the aqueous phase with ethyl acetate three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, concentrate the organic phase, and purify by silica gel column chromatography to obtain raw material A5.

[0097] (3) Add raw material A5 (13 mmol), raw material A6 (28 mmol), Pd(PPh3)4 (0.5 mmol), THF (100 mL), and saturated aqueous solution of K2CO3 (150 mmol) into the flask in sequence. Then reflux overnight under nitrogen protection. After the reaction is completed, cool to room temperature, extract with dichloromethane three times, combine the organic phases, add anhydrous sodium sulfate for drying, concentrate the organic phase, and purify by silica gel column chromatography to obtain raw material A7.

[0098] (4) Add raw material A7 (10 mmol) and o-dichlorobenzene (80 mmol) into the three-necked flask. Add BBr3 (12 mmol) under nitrogen protection, then stir overnight at 160 °C. After the reaction is completed, directly evaporate to dryness under reduced pressure. Separate the residue by silica gel column chromatography to obtain Compound 3.

[0099] Example 2 Synthesis of Compound 11:

[0100]

[0101] The preparation of raw material B3, raw material B6, raw material B7, raw material B8, and Compound 11 refers to Example 1.

[0102] Example 3 Synthesis of Compound 13:

[0103]

[0104] The preparation of raw material C2, raw material C5, raw material C6 and compound 13 refers to Reference Example 1.

[0105] Synthesis of Compound 34 in Example 4:

[0106]

[0107] Add raw material D4 (15 mmol), raw material D5 (7 mmol), CuI (2 mmol), tetramethylethylenediamine (1.0 mmol), Cs2CO3 (50 mmol), and DMF into the reaction flask in sequence. Then, under nitrogen protection, stir overnight at 120 °C. After the reaction is completed, cool to room temperature, dilute the reaction solution with ethyl acetate, filter, and wash the filter residue with ethyl acetate; combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, concentrate, and separate the obtained residue by silica gel column chromatography to obtain raw material D6.

[0108] The synthesis of raw material D3, raw material D4 and compound 34 refers to Reference Example 1.

[0109] Synthesis of Compound 43 in Example 5:

[0110]

[0111] Add raw material E2 (10 mmol), raw material E3 (20 mmol), Pd2(dba)3 (0.3 mmol), S-Phos (0.6 mmol), K2CO3 (100 mmol), and toluene (150 mL) into the flask in sequence. Then, replace the nitrogen and protect it, stir overnight at 110 °C. After the reaction is completed, cool to room temperature, add ethyl acetate to dilute the reaction solution, quench with water, extract the aqueous phase with ethyl acetate three times, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, concentrate the organic phase and purify it by silica gel column chromatography to obtain raw material E4.

[0112] The synthesis of raw material E2 and compound 43 refers to Reference Example 1.

[0113] Synthesis of Compound 46 in Example 6:

[0114]

[0115] The synthesis of raw material F2, raw material F3 and compound 46 refers to Reference Example 1.

[0116] Synthesis of Compound 47 in Example 6:

[0117]

[0118] The synthesis of raw material G1, raw material G2 and compound 47 refers to Reference Example 1.

[0119] Synthesis of Compound 54 in Example 7:

[0120]

[0121] For the synthesis method of starting material H1, starting material H2 and Compound 54, refer to Example 1.

[0122] Synthesis of Compound 63 in Example 8:

[0123]

[0124] (1) Charge the reaction flask with starting material E1 (50 mmol), anhydrous dichloromethane (200 mL), di-tert-butyl dicarbonate (55 mmol), and DIPEA (20 mL) at once, stir the reaction overnight at room temperature. After the reaction is completed, directly evaporate to dryness under reduced pressure, add dichloromethane for dilution, wash with saturated sodium bicarbonate solution, and concentrate to obtain the crude product, which is purified by trituration (ethyl acetate / petroleum ether) to obtain starting material I1.

[0125] (2) Charge the single-necked flask with starting material I2 (20 mmol) and dichloromethane (100 mL) in sequence, slowly add trifluoroacetic acid (50 mL), stir overnight at room temperature. After the reaction is completed, evaporate the solvent to dryness under reduced pressure, then add dichloromethane, wash with potassium carbonate solution, dry the organic phase over anhydrous sodium sulfate, and concentrate to obtain the crude product, which is purified by trituration (ethyl acetate / petroleum ether) to obtain starting material I3.

[0126] For the synthesis of starting material I5, refer to Example 4; for the synthesis of starting material I2, starting material I6, starting material I7 and Compound 63, refer to Example 1.

[0127] Synthesis of Compound 72 in Example 9:

[0128]

[0129] For the synthesis of starting material J1 and Compound 72, refer to Example 1.

[0130] Synthesis of Compound 133 in Example 10:

[0131]

[0132] For the synthesis of starting material K4, refer to Example 4; for the synthesis of starting material K3, starting material K5, starting material K6 and Compound 133, refer to Example 1.

[0133] Synthesis of Compound 156 in Example 11:

[0134]

[0135] For the synthesis of starting material L2 and Compound 156, refer to Example 1.

[0136] Synthesis of Compound 170 in Example 12:

[0137]

[0138] For the synthesis of starting material M2 and Compound 170, refer to Example 1.

[0139] Synthesis of Compound 178 in Example 13:

[0140]

[0141] For the synthesis of starting material N2 and Compound 178, refer to Example 1.

[0142] Synthesis of Compound 179 in Example 14:

[0143]

[0144] For the synthesis of starting material O2 and Compound 179, refer to Example 1.

[0145] Synthesis of Compound 212 in Example 15:

[0146]

[0147] (1) Add starting material P6 (8 mmol), CuI (2 mmol), Cs2CO3 (50 mmol), NMP (350 mL) to the reaction flask, and finally add TMEDA (1 mL). Protect with nitrogen, then stir at 120 °C for 2 hours, then raise the temperature to 160 °C and stir overnight. After the reaction is completed, cool to room temperature, filter, wash with saturated brine, extract with ethyl acetate, dry the organic phase over anhydrous sodium sulfate, and concentrate the obtained residue. The residue is separated by silica gel column chromatography to obtain starting material P7.

[0148] For the synthesis of starting material P3, starting material P5, starting material P6 and Compound 212, refer to Example 1.

[0149] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0150] Table 1

[0151]

[0152]

[0153]

[0154] The compounds of the present invention can be used in light-emitting devices and can be used as a doping material for the light-emitting layer. The physicochemical properties of the compounds prepared in the above examples of the present invention were tested, and the test results are shown in Table 2:

[0155] Table 2

[0156]

[0157] Note: The glass transition temperature Tg 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 Td is the temperature at which the weight loss is 1% in a nitrogen atmosphere, and it was measured on a TGA-50H thermogravimetric analyzer from Shimadzu Corporation of 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.

[0158] From the data in the above table, it can be seen that the compounds of the present invention have relatively high glass transition temperature and decomposition temperature. When used as a doping material for the light-emitting layer, it can inhibit the crystallization and phase separation of the material; at the same time, it can also inhibit the decomposition of the material at high brightness and improve the device working life. In addition, the compounds of the present application have relatively shallow 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 main guest energy transfer efficiency, and thus improve the device light-emitting efficiency.

[0159] The compounds of the present invention have relatively high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; at the same time, the spectral FWHM of the material is relatively narrow, which can effectively improve the device color gamut and the device light-emitting efficiency; finally, the evaporation decomposition temperature of the material is relatively high, which can inhibit the evaporation decomposition of the material and effectively improve the device life.

[0160] The application effects of the OLED materials synthesized by the present invention in the device are described in detail below through device examples 1-32 and device comparative examples 1-6. The manufacturing processes of device examples 2-16 and device comparative examples 1-3 of the present invention are exactly the same as those of device example 1. The manufacturing processes of device examples 18-32 and device comparative examples 4-6 of the present invention are exactly the same as those of device example 17 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.

[0161] Device Example 1

[0162] 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 light-emitting device is fabricated. CBP is used as the host material and compound 3 is used as the doping material, and the mass ratio of CBP and compound 3 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 evaporated by vacuum evaporation, 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 evaporated by vacuum evaporation, 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 by 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 by 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.

[0163] Device Example 17

[0164] 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 double host materials, and compound 3 is used as the doping material. The mass ratio of CBP, DMAC-BP, and compound 3 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.

[0165] The molecular structural formulas of the related materials are as follows:

[0166]

[0167]

[0168] After the OLED light-emitting device is completed as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency, emission peak, and device 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, emission peak, and lifetime of the obtained devices are shown in Table 4.

[0169] Table 3

[0170]

[0171]

[0172]

[0173] Table 4

[0174]

[0175] Note: The voltage, current efficiency, and emission peak are measured using an IVL (Current-Voltage-Brightness) test system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C OLED device lifetime tester from System Technology Research Co., Ltd. of Japan; LT95 refers to the time when the device brightness decays to 95%; all data are measured at 10 mA / cm 2 under the test.

[0176] From the device data results in Table 4, it can be seen that compared with Device Comparative Examples 1-3, both the current efficiency and device lifetime of Examples 1-16 of the organic light-emitting device of the present invention have been significantly improved compared to OLED devices of known materials.

[0177] By comparing Examples 17-32 with Comparative Examples 4-6, it can be seen that both the current efficiency and device lifetime of Examples 17-32 of the organic light-emitting device of the present invention have been significantly improved compared to OLED devices of known materials.

[0178] 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 substitutions, 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. An organic compound with a boron-containing heterocyclic structure, characterized in that The structure of the organic compound is shown as any one of general formulas (2) to (6): In General Formulas (2) to (6), Z1-Z8 represent CH or C(R1), and each occurrence of R1, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; X1, X2, and X3 each independently represent O, S, or N(R2), where R2, each occurrence being the same or different, represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; R a and R b each occurrence, independently, is hydrogen, deuterium, halogen, cyano, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 heteroaryl, or combinations thereof; m and n represent 0, 1, 2, 3, or 4; The substituents for the substituting groups are deuterium, halogen, cyano, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 one or more of heteroaryl.

2. The organic compound according to claim 1, characterized in that, The structure of the organic compound is shown as any one of general formulas (7) to (16): In General Formulas (7) to (16), Z1 - Z8 represent CH or C(R1), and each occurrence of R1, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen, a substituted or unsubstituted C1 - C 10 alkyl group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C1 - C 10 alkoxy group, a substituted or unsubstituted C6 - C 30 aryl group, a substituted or unsubstituted C2 - C 30 heteroaryl group; R a and R b each occurrence, independently of one another, is hydrogen, deuterium, halogen, cyano, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 heteroaryl, or a combination thereof; m and n represent 0, 1, 2, 3, or 4; The substituents for the substituting groups are deuterium, halogen, cyano, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 one or more of heteroaryl.

3. The organic compound according to claim 1, wherein R1 represents one of a hydrogen atom, a deuterium atom, a halogen, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-heterocarbazolyl group; The R a , R b is represented by one of a hydrogen atom, a deuterium atom, a halogen, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a cyano group, a phenyl group, a pyridyl group, a triazinyl group, a biphenyl group, a naphthyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a furyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, a carbazolyl group, and an N-heterocarbazolyl group; R2 represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-heterocarbazolyl group; The substituents for the substituent groups are each independently selected from: a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a cyano group, a methoxy group, a phenyl group, a pyridyl group, a triazinyl group, a biphenyl group, and a naphthyl group.

4. An organic compound with a boron-containing heterocyclic structure, characterized in that The specific structural formula of the organic compound is any one of the following structures:

5. An organic light-emitting device, comprising a cathode, an anode, and a functional layer, the functional layer being located between the cathode and the anode, characterized in that, The functional layer contains the organic compound with a boron-containing heterocyclic structure as described in any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5, wherein the functional layer includes a light-emitting layer, characterized in that, The doping material of the light-emitting layer is the organic compound with a boron-containing heterocyclic structure as described in any one of claims 1 to 4.

7. The organic light emitting device according to claim 6, wherein, The light-emitting layer contains 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 organic compound with a boron-containing heterocyclic structure as described in any one of claims 1 to 4.

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