Double-boron fused ring compound and organic electroluminescent device containing same

Abstract

The invention discloses a double-boron fused ring compound and an organic electroluminescent device containing the same, and belongs to the technical field of semiconductors. The structure of the diboron fused ring compound takes an aromatic ring or a heteroaromatic ring with a specific carbon atom number as a core and is fused with two boron-containing groups with the same skeleton, so that the diboron fused ring compound has narrow half-peak width, high fluorescence quantum yield, high glass-transition temperature and molecular thermal stability, and proper HOMO and LUMO energy levels, and can be used for preparing a fluorescent material. The material can be used as a luminescent layer doping material of an organic electroluminescent device, thereby improving luminescent color purity and service life of the device.

Description

[0001] This invention application is based on the prior application number: 2021110986820, the application date: September 18, 2021, and the invention name is: A divisional application for a diboron fused ring compound and an organic electroluminescent device containing the same. Technical Field

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

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

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

[0005] In addition, TADF sensitized fluorescence technology (TSF) combines TADF materials with fluorescent doping materials, and uses TADF materials as exciton sensitization media to convert triplet excitons formed by electrical excitation into singlet excitons, and transfers energy to fluorescent doping materials through long-range energy transfer of singlet excitons. It can also achieve 100% device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0006] Boron compounds with a resonant structure are more likely to achieve narrow half-width luminescence. This type of material is used in TADF-sensitized fluorescence technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN110492006 A disclose a luminescent layer combination technology with a TADF material having a difference in energy levels between the lowest singlet state and the lowest triplet state of less than or equal to 0.2eV as the main body and a boron-containing material as the doping; CN 110492005 A and CN 110492009 A 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 TADF-sensitized fluorescence technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the invention

[0007] In view of the above problems existing in the prior art, the applicant of the present invention provides a diboron fused ring compound. The diboron fused ring compound of the present invention has an aromatic ring or heteroaromatic ring with a specific number of carbon atoms as the core and is fused with two boron-containing groups with the same skeleton, so that it has a narrow half-peak width, a high fluorescence quantum yield, a high glass transition temperature and molecular thermal stability, and suitable HOMO and LUMO energy levels, and can be used as a doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the luminescent color purity and life of the device.

[0008] The technical solution of the present invention is as follows: a diboron fused ring compound, the structure of the diboron fused ring compound is shown in the general formula (1):

[0009]

[0010] In the general formula (1), X 1 , X 2 Each independently represents an O atom, a S atom or a N(R 1 );

[0011] A represents substituted or unsubstituted C 10 -C 30 Aromatic ring, substituted or unsubstituted C 12 -C 30 Heteroaromatic rings;

[0012] Each occurrence of Z is independently represented by a N atom or C(R), each occurrence of R is the same or different, and two adjacent Rs may be bonded to each other to form a ring;

[0013] R 1 The adjacent R can also be connected by a single bond;

[0014] R 1 Indicated as substituted or unsubstituted C1 ~C 10 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted C 2 ~C 30 Any of the heteroaryl groups;

[0015] R represents hydrogen, deuterium, tritium, cyano, halogen, adamantane, substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 30 Aryloxy, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted C 2 ~C 30 Any of a heteroaryl group and an arylamine group;

[0016] The substituents of the substituent group are selected from deuterium, tritium, cyano, halogen, adamantane, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, deuterium, tritium or fluorine substituted C 1 ~C 10 Alkyl, C 6 ~C 30 Aryl, C 2 ~C 30 Any of the heteroaryl groups;

[0017] The heteroatom in the heteroaryl group is selected from one or more of oxygen, sulfur, boron or nitrogen atoms.

[0018] Further, the A is represented by substituted or unsubstituted C 14 -C 30 Aromatic ring, substituted or unsubstituted C 12 -C 30 Heteroaromatic ring.

[0019] Furthermore, the X 1 , X 2 are represented by the same group.

[0020] Furthermore, A represents a substituted or unsubstituted C 14 Aromatic ring, substituted or unsubstituted C 16Aromatic ring, substituted or unsubstituted C 18 Aromatic ring, substituted or unsubstituted C 20 Aromatic ring, substituted or unsubstituted C 10 Heteroaromatic ring, substituted or unsubstituted C 14 Heteroaromatic ring, substituted or unsubstituted C 16 Heteroaromatic ring, substituted or unsubstituted C 18 Heteroaromatic ring, substituted or unsubstituted C 22 Heteroaromatic ring.

[0021] Furthermore, the A represents an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a fluoranthene ring, a tetracene ring, or an indolocarbazole ring.

[0022] Further, the A is represented by the following ring structure:

[0023]

[0024] The asterisks in the above loop structures indicate ligation sites.

[0025] Furthermore, the structure of the diboron fused ring compound is shown in any one of the general formulas (I-1) to (I-15):

[0026]

[0027]

[0028] Among them, Z, X 1 , X 2 The definition of is the same as that in the above general formula (1).

[0029] Furthermore, the structure of the diboron fused ring compound is shown in any one of the general formulas (II-1) to (II-9):

[0030]

[0031] The definition of Z is the same as that in the above general formula (1), and the dotted line indicates connection or non-connection.

[0032] Further, R represents hydrogen, deuterium, tritium, fluorine atom, cyano group, methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl Phenyl, deuterated biphenyl, deuterated terphenyl, deuterated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 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, tritiated methyl-substituted phenyl, tritiated ethyl-substituted phenyl, tritiated isopropyl-substituted phenyl, tritiated tert-butyl-substituted phenyl, tritiated methyl-substituted biphenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl, tritiated tert-butyl-substituted biphenyl, diphenylamino, dibiphenylamino, and triphenylamino;

[0033] The R 1Methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated tert-butyl Phenyl, tritiated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl One of 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, tritiated methyl substituted phenyl, tritiated ethyl substituted phenyl, tritiated isopropyl substituted phenyl, tritiated tert-butyl substituted phenyl, tritiated methyl substituted biphenyl, tritiated ethyl substituted biphenyl, tritiated isopropyl substituted biphenyl, tritiated tert-butyl substituted biphenyl;

[0034] The substituent of the substituent group may be selected from any one of deuterium, tritium, cyano, fluorine, adamantane, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, carbazolyl, and dibenzofuranyl.

[0035] Furthermore, the specific structural formula of the diboron fused ring compound is any one of the following structures:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047] An organic light-emitting device comprises a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, and the functional layer of the organic light-emitting device comprises the diboron condensed ring compound.

[0048] In a preferred embodiment, the functional layer of the organic light-emitting device comprises a light-emitting layer, and the doping material of the light-emitting layer is the diboron fused-ring compound.

[0049] Further preferably, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the diboron fused ring compound.

[0050] The beneficial technical effects of the present invention are:

[0051] (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 fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields. The compounds of the present invention have a high fluorescence quantum efficiency as doping materials, and the fluorescence quantum efficiency of the material is close to 100%;

[0052] (2) The compound of the present invention is used as a doping material and a TADF sensitizer is introduced as a second main body, which can effectively improve the efficiency of the device; the spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device; the evaporation decomposition temperature of the compound of the present invention is relatively high, which can inhibit the evaporation decomposition of the material and effectively improve the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0053] 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;

[0054] 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

[0055] The principles and features of the present invention are described below in conjunction with the accompanying drawings. The examples given are only used to explain the present invention and are not used to limit the scope of the present invention.

[0056] In the present invention, unless otherwise specified, HOMO means the highest occupied molecular orbital of a molecule, and LUMO means the lowest unoccupied molecular orbital of a molecule.

[0057] In this specification, substituted or unsubstituted C 6 -C 30 Aryl and / or substituted or unsubstituted C 2 -C 30 The heteroaryl group 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 para-terphenyl, substituted or unsubstituted meta-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 benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or condensed rings of combinations of the foregoing groups, but are not limited thereto.

[0058] The C of the present invention 1 -C 10 Alkyl (including straight-chain alkyl and branched alkyl) refers to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl and the like, but is not limited thereto.

[0059] The halogen atom described in the present invention refers to a chlorine atom, a fluorine atom or a bromine atom, but is not limited thereto.

[0060] The C of the present invention 1 -C 10 The alkoxy group refers to a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an isopropoxy group or the like, but is not limited thereto.

[0061] The C of the present invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group containing 3 to 10 carbon atoms as ring atoms. 4 -C 9 Cycloalkyl, more preferably C 5 -C 8 Cycloalkyl, particularly preferably C 5 -C 7 Cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl. As used herein, C 3 -C 10 Cycloalkylene refers to C 3 -C 10 The cycloalkyl group has a divalent group of the same structure.

[0062] The present invention provides an organic electroluminescent device, which comprises, from bottom to top, a substrate, an anode, an organic functional material layer and a cathode, wherein the organic functional material layer comprises:

[0063] a hole transport region, which is located above the anode;

[0064] A light-emitting layer, which is located above the hole transport region, and includes a main material and a doping material;

[0065] an electron transport region, which is located above the light-emitting layer;

[0066] The cathode is located above the electron transport region.

[0067] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates; flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, its use direction is different. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.

[0068] An anode is formed on a substrate. The anode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the anode 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 anode 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 anode layer depends on the material used, typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.

[0069] The organic functional material layer disposed between the anode and the cathode includes, from bottom to top, a hole transport region, a light emitting layer and an electron transport region.

[0070] 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.

[0071] As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials used for OLED devices.

[0072] Examples of the above materials may include monoaromatic amines, bistriarylamines, triamines, tetraamines, benzidines, and the like.

[0073] Furthermore, according to the device matching requirements, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer constituting the organic electroluminescent device can be a single film layer or a superposition structure of multiple hole transport materials. In this article, for the above-mentioned hole carrier conduction film layers with different functions, their film thickness is not particularly limited.

[0074] The hole injection layer includes a main organic material that can conduct holes, and may also include a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep), such as quinone derivatives, tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl), but not limited to these.

[0075] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0076] 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.

[0077] The thickness of the hole transport layer of the present invention may be 5 to 200 nm, preferably 10 to 150 nm, and more preferably 20 to 100 nm, but the thickness is not limited to this range.

[0078] The thickness of the electron blocking layer of the present invention may be 1-20 nm, preferably 5-10 nm, but the thickness is not limited to this range.

[0079] 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.

[0080] 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.

[0081] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the efficiency of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, for example, oxazole derivatives, triazole derivatives, triazine derivatives, etc. The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm and more preferably 10-100nm, but the thickness is not limited to this range.

[0082] The electron transport layer may be disposed on the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer material known in the prior art for organic electroluminescent devices can be used, for example, Alq 3, metal complexes of hydroxyquinoline derivatives represented by BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), imidazole derivatives such as oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. The thickness of the electron transport layer of the present invention can be 10-80nm, preferably 20-60nm and more preferably 25-45nm, but the thickness is not limited to this range.

[0083] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0084] The cathode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the cathode is a transmissive electrode, the cathode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag or a compound or mixture thereof; when the cathode is a semi-transmissive electrode or a reflective electrode, the cathode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used, and is typically 10-50 nm, preferably 15-20 nm.

[0085] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0086] The method for preparing an organic electroluminescent device of the present invention may use vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods, but is not limited thereto. In the present invention, preferably vacuum evaporation is used to form the various layers. Those skilled in the art may conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0087] In addition, it should be noted that the materials used to form each layer described in the present invention can be formed into a film alone and used as a single layer, or can be mixed with other materials to form a film and used as a single layer. It can also be a stacked structure between layers formed into films alone, a stacked structure between layers formed into films after mixing, or a stacked structure of layers formed into films alone and layers formed into films after mixing.

[0088] The light-emitting layer may contain a host material and a guest material.

[0089] In one embodiment of the present invention, the light-emitting film layer comprises one or two host material compounds.

[0090] In the light-emitting layer of the present invention, the ratio of the host material to the guest material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0091] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and the driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-30 nm, but the thickness is not limited to this range.

[0092] The raw materials involved in the synthesis examples of the present invention were purchased from China Energy Conservation Wanrun Co., Ltd.

[0093] Example 1 Synthesis of Compound 6:

[0094]

[0095] (1) In a three-necked flask, under nitrogen protection, add 0.01 mol of A-1, 0.025 mol of B-1, and 150 ml of toluene, stir and mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03 mol sodium tert-butoxide, heated to 105°C, refluxed for 16 hours, the sampling point plate showed no brominated product remaining, and the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated until there was no fraction, and passed through a neutral silica gel column (developing solvent: toluene and heptane) to obtain C-1 (MS: 660.29).

[0096] (2) Under nitrogen atmosphere, add 0.01 mol of C-1 to a three-necked flask, then add 150 ml of tert-butylbenzene to dissolve it, cool to 0°C and maintain, slowly add 20 ml of pentane solution of 0.03 mol of tert-butyl lithium, and then heat to 80°C, 100°C, and 120°C in turn for 1 hour each. After the reaction is completed, cool to -30°C, slowly add 0.03 mol of boron tribromide, and continue stirring at room temperature for 0.5 hour. Add 0.04 mol of N, N-diisopropylethylamine at room temperature, and continue to react at 125°C for 5 hours before stopping. Vacuum dry the solvent, pass through a silica gel column (developing solvent: methanol and acetonitrile) to obtain compound 6.

[0097] Example 2 Synthesis of Compound 1:

[0098]

[0099] Under nitrogen atmosphere, 0.01 mol C-2 was added to a three-necked flask, and then 150 ml of tert-butylbenzene was added to dissolve it, the temperature was lowered to 0 ° C and maintained, 20 ml of pentane solution of 0.03 mol tert-butyl lithium was slowly added, and then the temperature was raised to 80 ° C, 100 ° C, and 120 ° C in turn for 1 hour each. After the reaction was completed, the temperature was lowered to -30 ° C, 0.03 mol of boron tribromide was slowly added, and stirring was continued at room temperature for 0.5 hours. 0.04 mol N, N-diisopropylethylamine was added at room temperature, and the reaction was continued at 125 ° C for 5 hours before stopping. The solvent was dried under vacuum and passed through a silica gel column (developing solvent: methanol and acetonitrile) to obtain compound 1.

[0100] Example 3 Synthesis of Compound 41:

[0101]

[0102] (1) Add 0.01 mol of A-3, 0.024 mol of B-3, and 0.015 mol of NaH to a three-necked flask, then add 90 ml of dimethyl sulfoxide to dissolve it, heat to 140°C, stir and reflux for 5 hours, and observe the reaction by TLC until the reaction is complete and the solution is separated. Cool naturally to room temperature, separate the liquids, filter and dry to obtain C-3 (MS: 518.32).

[0103] (2) Under nitrogen atmosphere, 0.01 mol C-3 was added to a three-necked flask, and then 150 ml of tert-butylbenzene was added to dissolve it. The temperature was lowered to 0°C and maintained, and 20 ml of pentane solution of 0.03 mol tert-butyl lithium was slowly added, and then the temperature was raised to 80°C, 100°C, and 120°C in turn for 1 hour each. After the reaction was completed, the temperature was lowered to -30°C, and 0.03 mol of boron tribromide was slowly added, and stirring was continued at room temperature for 0.5 hour. 0.04 mol N, N-diisopropylethylamine was added at room temperature, and the reaction was continued at 125°C for 5 hours before stopping. The solvent was dried under vacuum, and passed through a silica gel column (developing solvent: methanol and acetonitrile) to obtain compound 41.

[0104] Example 4 Synthesis of Compound 26:

[0105]

[0106] The preparation method of compound 26 is the same as that of Example 3, except that A-4 is used to replace A-3. A-4 and B-3 are used as reaction raw materials to prepare intermediate C-4 (MS: 518.32).

[0107] Example 5 Synthesis of Compound 29:

[0108]

[0109] The preparation method of compound 29 is the same as that of Example 1, except that A-4 is used to replace A-1, B-5 ​​is used to replace B-1, and A-4 and B-5 are used as reaction raw materials to prepare intermediate C-5 (MS: 668.24).

[0110] Example 6 Synthesis of Compound 56:

[0111]

[0112] The preparation method of compound 56 is the same as that of Example 2, except that C-2 is replaced by C-6.

[0113] Example 7 Synthesis of Compound 60:

[0114]

[0115] The preparation method of compound 60 is the same as that of Example 7, except that A-7 is used to replace A-1, B-5 ​​is used to replace B-1, and A-7 and B-5 are used as reaction raw materials to prepare intermediate C-7 (MS: 742.27).

[0116] Example 8 Synthesis of Compound 81:

[0117]

[0118] The preparation method of compound 81 is the same as that of Example 3, except that A-8 is used to replace A-3. A-8 and B-3 are used as reaction raw materials to prepare intermediate C-8 (MS: 538.24).

[0119] Example 9 Synthesis of Compound 86:

[0120]

[0121] The preparation method of compound 86 is the same as that of Example 3, except that A-9 is used to replace A-3. A-9 and B-3 are used as reaction raw materials to prepare intermediate C-9 (MS: 538.24).

[0122] Example 10 Synthesis of Compound 170:

[0123]

[0124] The preparation method of compound 170 is the same as that of Example 2, except that C-2 is replaced by C-10.

[0125] Example 11 Synthesis of Compound 141:

[0126]

[0127] The preparation method of compound 141 is the same as that of Example 1, except that A-1 is replaced by A-11, B-1 is replaced by B-5, and A-11 and B-5 are used as reaction raw materials to prepare intermediate C-11 (MS: 664.33).

[0128] Example 12 Synthesis of Compound 232:

[0129]

[0130] The preparation method of compound 232 is the same as that of Example 2, except that C-2 is replaced by C-12.

[0131] Example 13 Synthesis of Compound 234:

[0132]

[0133] The preparation method of compound 234 is the same as that of Example 1, except that A-1 is replaced by A-13, B-1 is replaced by B-5, and A-13 and B-5 are used as reaction raw materials to prepare intermediate C-13 (MS: 744.39).

[0134] Example 14 Synthesis of Compound 238:

[0135]

[0136] The preparation method of compound 238 is the same as that of Example 1, except that A-1 is replaced by A-14, B-1 is replaced by B-5, and A-14 and B-5 are used as reaction raw materials to prepare intermediate C-14 (MS: 688.34).

[0137] Example 15 Synthesis of Compound 254:

[0138]

[0139] The preparation method of compound 254 is the same as that of Example 1, except that B-1 is replaced by B-15. A-1 and B-15 are used as reaction raw materials to obtain intermediate C-16 (MS: 974.31).

[0140] Example 16 Synthesis of Compound 258:

[0141]

[0142] The preparation method of compound 258 is the same as that of Example 1, except that B-1 is replaced by B-16. A-1 and B-16 are used as reaction raw materials to prepare intermediate C-19 (MS: 764.24).

[0143] Example 17 Synthesis of Compound 276:

[0144]

[0145] The preparation method of compound 276 is the same as that of Example 1, except that A-1 is replaced by A-17, B-1 is replaced by B-17, and A-17 and B-17 are used as reaction raw materials to prepare intermediate C-17 (MS: 742.31).

[0146] Example 18 Synthesis of Compound 287:

[0147]

[0148] The preparation method of compound 287 is the same as that of Example 1, except that A-1 is replaced by A-18, B-1 is replaced by B-18, and A-18 and B-18 are used as reaction raw materials to prepare intermediate C-18 (MS: 694.33).

[0149] Example 19 Synthesis of Compound 265:

[0150]

[0151] (1) Add 0.01 mol of A-19, 0.024 mol of B-3, and 0.015 mol of NaH to a three-necked flask, then add 90 ml of dimethyl sulfoxide to dissolve it, heat to 140°C, stir and reflux for 5 hours, and observe the reaction by TLC until the reaction is complete and the solution is separated. Cool naturally to room temperature, separate the liquids, filter and dry to obtain M-19 (MS: 366.23).

[0152] (2) In a three-necked flask, under nitrogen protection, add 0.01 mol of M-19, 0.025 mol of N-19, and 150 ml of toluene, stir and mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03 mol sodium tert-butoxide, heated to 110°C, refluxed for 18 hours, sampling point plate, showing no brominated product remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was evaporated until there was no fraction, passed through a neutral silica gel column (developing solvent: toluene and heptane), to obtain C-19 (MS: 980.33).

[0153] (3) Under nitrogen atmosphere, 0.01 mol C-19 was added to a three-necked flask, and then 150 ml of tert-butylbenzene was added to dissolve it. The temperature was lowered to 0°C and maintained, and 20 ml of pentane solution of 0.03 mol tert-butyl lithium was slowly added, and then the temperature was raised to 80°C, 100°C, and 120°C in turn for 1 hour each. After the reaction was completed, the temperature was lowered to -30°C, and 0.03 mol of boron tribromide was slowly added, and stirring was continued at room temperature for 0.5 hour. 0.04 mol N, N-diisopropylethylamine was added at room temperature, and the reaction was continued at 125°C for 5 hours before stopping. The solvent was dried under vacuum, and the mixture was passed through a silica gel column (developing solvent: methanol and acetonitrile) to obtain compound 265.

[0154] Example 20 Synthesis of Compound 30:

[0155]

[0156] The preparation method of compound 30 is the same as that of Example 19, except that B-20 is used to replace B-3, N-20 is used to replace N-19, A-19 and B-20 are used as reaction raw materials to prepare intermediate M-20 (MS: 398.06), and N-20 and M-20 are used as reaction raw materials to prepare intermediate C-20 (MS: 880.34).

[0157] Example 21 Synthesis of Compound 7:

[0158]

[0159] (1) In a three-necked flask, nitrogen was introduced, 0.02 mol of A-21, 150 ml of DMF, 0.043 mol of B-21, and 0.0002 mol of palladium acetate were added, stirred, and then 3 mL of 0.01 mol / mL K 3 PO 4 Aqueous solution, heated under reflux at 150°C for 20 hours, sampled, the reaction was complete, cooled naturally, 120 mL of water was added, the mixture was filtered and the filter cake was dried in a vacuum oven, the residue was purified by silica gel column to obtain C-21 (MS: 998.38);

[0160] (2) Under nitrogen atmosphere, 0.01 mol C-21 was added to a three-necked flask, and then 150 ml of tert-butylbenzene was added to dissolve it. The temperature was lowered to 0°C and maintained, and 20 ml of pentane solution of 0.03 mol tert-butyl lithium was slowly added, and then the temperature was raised to 80°C, 100°C, and 120°C in turn for 1 hour each. After the reaction was completed, the temperature was lowered to -30°C, and 0.03 mol of boron tribromide was slowly added, and stirring was continued at room temperature for 0.5 hour. 0.04 mol N, N-diisopropylethylamine was added at room temperature, and the reaction was continued at 125°C for 5 hours before stopping. The solvent was dried under vacuum, and passed through a silica gel column (developing solvent: methanol and acetonitrile) to obtain compound 7.

[0161] For structural analysis of the compounds prepared in Examples 1 to 21, LC-MS was used for structural confirmation.

[0162] Table 1

[0163]

[0164]

[0165] The compounds of the present invention are used in light-emitting devices and can be used as doping materials for light-emitting layers. The physical and chemical properties of the compounds prepared in the above embodiments of the present invention were tested, and the test results are shown in Table 2:

[0166] Table 2

[0167]

[0168]

[0169] 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 is measured on a TGA-50H thermogravimetric analyzer from Shimadzu, 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) in a nitrogen environment; Eg was tested by a double-beam UV-visible spectrophotometer (model: TU-1901), LUMO=HOMO+Eg; PLQY and FWHM were tested by Horiba's Fluorolog-3 series fluorescence spectrometer in a single-component film state, and the film thickness was 80 nm.

[0170] It can be seen from the data in the above table that compared with the existing material ref-1, the compound of the present invention has a higher glass transition temperature and decomposition temperature. When used as a doping material for the light-emitting layer, it can inhibit the crystallization and film phase separation of the material; at the same time, it can also inhibit the decomposition of the material at high brightness and improve the working life of the device. In addition, the compound of the present application has a shallow HOMO energy level. When doped into the main material as a doping material, it is beneficial to inhibit the generation of carrier traps, improve the host-guest energy transfer efficiency, and thus improve the luminous efficiency of the device.

[0171] The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; at the same time, the spectral FWHM of the material is narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device; finally, the evaporation decomposition temperature of the material is high, which can inhibit the evaporation decomposition of the material and effectively improve the life of the device.

[0172] The application effects of the OLED materials synthesized in the present invention in devices are described in detail below through device examples 1-42 and device comparison examples 1-6.

[0173] Device Example 1

[0174] 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 cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as the hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as the electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is made, using CBP as the main material and compound 6 as the doping material. The mass ratio of CBP and compound 6 is 97:3, and the film thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0175] The device embodiments 2-21 of the present invention and the device comparative examples 1 and 3-6 are made in the same manufacturing process as the device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 3-1 and Table 4 respectively.

[0176] Device Example 22

[0177] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, and its structure includes CBP and DMAC-BP used in the OLED light-emitting layer 6 as dual main materials, compound 6 as a doping material, CBP, DMAC-BP and compound 6 The mass ratio is 67:30:3, and the film thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0178] The device embodiments 23-42 of the present invention and the device comparative example 2 are completely identical in manufacturing process to the device embodiment 22, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also the same, except that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 3-2 and Table 4, respectively.

[0179] The molecular structure formula of the relevant materials is shown below:

[0180]

[0181] After the OLED light-emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency, external quantum efficiency and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 3-1 and Table 3-2; the test results of the current efficiency, external quantum efficiency and life of the obtained device are shown in Table 4.

[0182] Table 3-1

[0183]

[0184]

[0185] Table 3-2

[0186]

[0187]

[0188]

[0189] Table 4

[0190]

[0191]

[0192] Note: Voltage, current efficiency, and luminous peak are measured using IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the life test system is EAS-62C OLED device life tester from Japan System Technology Co., Ltd.; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are at 10mA / cm 2 Next test.

[0193] It can be seen from the device data results in Table 4 that, compared with device comparison examples 1-6, the current efficiency, external quantum efficiency and device life of the organic light-emitting device of the present invention are greatly improved compared with OLED devices of known materials.

[0194] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A diboron fused ring compound, characterized in that: The structure of the diboron fused ring compound is shown in any one of the general formula (I-1), general formula (I-3), general formula (I-5) or general formula (I-7): X1 and X2 are independently represented by an O atom, a S atom or N(R1); Each occurrence of Z is independently represented by a N atom or C(R), and each occurrence of R is the same or different; R1 and the adjacent R can also be connected by a single bond; R1 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 Any of the heteroaryl groups; R represents hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 Any of a heteroaryl group and an arylamine group; The substituent of the substituent group is selected from deuterium, cyano, halogen, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, deuterium or fluorine substituted C1~C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Any of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of oxygen, sulfur, boron or nitrogen atoms.

2. A diboron fused ring compound, characterized in that: The structure of the biboron fused ring compound is shown in any one of the general formulas (II-1), (II-3), (II-5), (II-7) or (II-9): The dotted line indicates connection or non-connection; Each occurrence of Z is independently represented by a N atom or C(R), and each occurrence of R is the same or different; R represents hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 Any of heteroaryl and arylamine; The substituent of the substituent group is selected from deuterium, cyano, halogen, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, deuterium or fluorine substituted C1~C 10 Alkyl, C6~C 30 Aryl, C2~C 30 Any of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of oxygen, sulfur, boron or nitrogen atoms.

3. The diboron fused ring compound according to claim 1 or 2, characterized in that: The R represents hydrogen, deuterium, a fluorine atom, a cyano group, a methyl group, a deuterated methyl 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 deuterated cyclopentyl group, a cyclohexyl group, a cyclopentyl group, an adamantyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a methyl-substituted benzene group The present invention is one of the following: 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, diphenylamino, dibiphenylamino, and triphenylamino; The R1 is methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, deuterated cyclopentyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, deuterated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 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; The substituent of the substituent group may be selected from any one of deuterium, cyano, fluorine, adamantane, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, carbazolyl, and dibenzofuranyl.

4. The diboron fused ring compound according to claim 1 or 2, characterized in that: The specific structural formula of the diboron fused ring compound is any one of the following structures:

5. An organic light-emitting device comprising a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, characterized in that: The functional layer of the organic light-emitting device comprises the diboron fused ring compound according to any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5, wherein the functional layer comprises a light-emitting layer, characterized in that: The doping material of the light-emitting layer is the diboron fused ring compound according to any one of claims 1 to 4.

7. The organic light-emitting device according to claim 6, 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 main material and the second main material is a TADF material, and the doping material is the diboron fused ring compound according to any one of claims 1-4.

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