Organic compound containing benzofuranopyrimidine and application thereof

Abstract

The invention relates to the technical field of semiconductor material preparation, in particular to an organic compound containing a benzofuro pyrimidine group and application thereof. According to the invention, a novel benzofuranopyrimidine mother nucleus structure is introduced, and a benzofuranopyrimidine mother nucleus group and a polypyridine group are specifically linked through a bridging group and a linking site thereof, so that the compound has good electron mobility and stability; the compound has good electron tolerance and triplet state exciton inhibition capability, and can effectively reduce the driving voltage of the device, improve the efficiency of the device and prolong the service life of the device when being applied to the organic electroluminescent device as an electron transport material.

Description

Technical Field

[0001] This invention relates to the field of semiconductor material preparation technology, and in particular to an organic compound containing a benzofuran-pyrimidine group and its applications. Background Technology

[0002] Organic light-emitting diode (OLED) technology can be used to manufacture novel display products and lighting products, and it holds promise as a replacement for existing liquid crystal displays and fluorescent lighting, with a wide range of applications. OLED devices have a sandwich-like structure, consisting of electrode material layers and organic functional materials sandwiched between different electrode material layers. Various organic functional materials are stacked together according to their intended use to form the OLED light-emitting device. As a current-emitting device, when a voltage is applied to its two electrodes, and an electric field is applied to the positive and negative charges in the organic functional material layers, the positive and negative charges recombine in the light-emitting layer, thus generating OLED electroluminescence.

[0003] OLED optoelectronic functional materials used in OLED devices can be broadly categorized into two types based on their applications: charge injection transport materials and luminescent materials. Further, charge injection transport materials can be classified into electron injection transport materials, electron blocking materials, hole injection transport materials, and hole blocking materials. As charge transport materials, they require excellent carrier mobility and high glass transition temperature. In OLED devices, electrons are injected from the cathode and then transported through the electron transport layer to the host material, where they recombine with holes to generate excitons. Electron transport materials are currently a hot research topic among experts and scholars. By efficiently transporting electrons to the luminescent region, they facilitate electron-hole recombination, thereby improving the material's performance. However, existing electron transport materials still have shortcomings in improving device performance. Even with the combination of multiple materials, display technology still suffers from high driving voltage and short display lifespan, severely hindering the further practical application of this technology. For example, prior art CN113840822A discloses an electron transport material with a triazine and pyridine structure, wherein the pyridine structure is terpyridine, which is directly linked to the triazine via a phenyl group. This linkage results in insufficient steric hindrance between the triazine and pyridine, particularly the inability to effectively separate the electron density between the two groups, leading to insufficient electron mobility and poor electron tolerance of the material. Ultimately, this results in a high device drive voltage and reduced device efficiency and lifetime. CN117384134A discloses an electron transport material with a triazine and pyridine structure, wherein the branched chain is a monopyridine structure, linked by the triazine and monopyridine structures. The molecular structure constructed by the monopyridine and triazine cannot produce effective electron density separation. During electron injection, the electron density on the monopyridine becomes enriched, resulting in insufficient electron tolerance of the material, ultimately leading to reduced device efficiency and lifetime.

[0004] Therefore, the performance of electron transport materials is continuously improved by innovating molecular groups and optimizing molecular linkages. In particular, improving the electron transport capability, electron tolerance, triplet exciton suppression capability, glass transition temperature, and stability of electron transport materials has become the focus and challenge of high-performance electron transport material research. Summary of the Invention

[0005] To address the technical problems existing in the prior art, this invention provides an organic compound containing a benzofuran-pyrimidine group and its applications. By introducing a novel benzofuran-pyrimidine core structure, the benzofuran-pyrimidine core group and the polypyridine group are specifically linked through bridging groups and their binding sites, resulting in a compound with good electron mobility and stability, as well as good electron tolerance and triplet exciton suppression capability. When used as an electron transport material in organic electroluminescent devices, it can effectively reduce the device driving voltage and improve device efficiency and lifetime.

[0006] The technical solution of this invention is as follows: According to one or more embodiments, the present invention provides an organic compound containing a benzofuranopyrimidine group, said organic compound having a structure as shown in formula (1): ; In equation (1), L1 and L2 are represented as single bonds or C6-C36 arylene groups, respectively, either the same or different. Ar and R1 are selected from substituted or unsubstituted C6-C36 aryl groups and substituted or unsubstituted C5-C36 heteroaryl groups, whether they are the same or different. When substituted, the substituted group is independently selected from deuterium or cyano. X1-X2, Y1-Y3, and Y4-Y6 are each selected as nitrogen atoms, and the others are carbon atoms.

[0007] L1 and L2 are represented by single bonds or phenylene bonds, respectively, either identically or differently.

[0008] Preferably, Ar and R1 are selected from any one or more of cyano-substituted or unsubstituted phenyl, biphenyl, naphthyl, and pyridyl groups, whether the same or different.

[0009] Preferably, the organic compound has any one of the structures shown in formulas (I-1) to (I-3): ; The substitution choices for L1, L2, Ar, R1, X1-X2, Y1-Y6 are as defined in equation (I).

[0010] Preferably, in equations (I), (I-1) to (I-3) The structure is selected from the following: .

[0011] According to one or more embodiments, the present invention provides an organic compound selected from any of the following chemical structures:

[0012] According to one or more embodiments, the present invention also provides the use of organic compounds with the structure shown in formula (I) above in the preparation of electronic devices. Further, the electronic device is an organic electroluminescent device.

[0013] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises: Substrate layer; first electrode, the first electrode being on the substrate layer; An organic functional layer is disposed on the first electrode; A second electrode is provided on the organic functional layer. and a light extraction layer above the second electrode; The organic functional layer comprises one or more organic compounds with the structure shown in formula (I) above.

[0014] Furthermore, the organic functional layer includes an electron transport layer, which contains one or more organic compounds with the structure shown in formula (I) above.

[0015] The present invention also provides a composition comprising an organic compound having the structure shown in formula (I) above.

[0016] The present invention also provides a formulation comprising an organic compound with the structure shown in formula (I) above and at least one solvent. The solvent is not particularly limited and may be any solvent well known to those skilled in the art.

[0017] The present invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices described above.

[0018] Compared with the prior art, the technical advantages of this invention are: The compounds of this invention link benzofuranopyrimidine groups and pyridine through specific bridging groups and their binding sites, resulting in compounds with high electron mobility and stability, as well as good electron tolerance and triplet exciton suppression capabilities. They can be used as electron transport materials in organic light-emitting devices (OLEDs) to effectively reduce device driving voltage and improve device efficiency and lifetime. Attached Figure Description

[0019] Figure 1 This is a cross-sectional structural diagram of an application device structure of the compound of the present invention: wherein 100 is a substrate, 200 is a first electrode, 300 is an organic functional layer, 400 is a second electrode, and 500 is a light extraction layer. Figure 2This is a cross-sectional schematic diagram of the organic functional layer 300 in the application device structure; wherein, 310 is the hole injection layer, 320 is the hole transport layer, 330 is the electron blocking layer, 340 is the light-emitting layer, 350 is the hole blocking layer, 360 is the electron transport layer, and 370 is the electron injection layer. Detailed Implementation

[0020] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples.

[0021] In this invention, "aryl" refers to an unsaturated aromatic carbon ring having 6-36 carbon atoms and being a monocyclic (e.g., phenyl) or polycyclic fused (e.g., naphthyl or anthracene) ring, preferably having 6-18 carbon atoms, more preferably 6-12 carbon atoms. Preferred aryl groups include phenyl, biphenyl, naphthyl, phenanthryl, terphenyl, etc. Unless otherwise defined for individual substituents, such aryl groups may optionally be substituted with 1-3 of the following substituents: hydroxyl, acyl, alkyl, alkoxy, alkynyl, aryl, carboxyl, carboxyl ester, cyano, halogen, nitro, heteroaryl, heterocyclic, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, trihalomethyl, and thioalkoxy. However, this is not a limitation.

[0022] The term "heteroaryl" as used in this invention refers to a group consisting of 5-36 carbon atoms in a aryl group, wherein one or more aromatic carbon atoms are replaced by heteroatoms, preferably 5-18 carbon atoms. The heteroatoms include, but are not limited to, oxygen (O), sulfur (S), nitrogen (N), or silicon (Si) atoms. The heteroaryl can be a monocyclic heteroaryl or a fused-ring heteroaryl. Examples include pyridyl, pyrrole, pyridyl, thiophene, furanyl, indolyl, quinolinyl, quinoxalinyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, etc., but are not limited thereto.

[0023] In this specification, unless explicitly stated otherwise, the term "including" any component shall be construed as including other elements, not excluding any other elements. Furthermore, it should be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" or "above" another element, it may be "directly on" the other element, or there may be intermediate elements present. Additionally, "on" or "above" means located above the target portion, and not necessarily above it in the direction of gravity.

[0024] Figure 1 This is a cross-sectional structural diagram of an application device structure of the compound of the present invention: wherein 100 is a substrate, 200 is a first electrode, 300 is an organic functional layer, 400 is a second electrode, and 500 is a light extraction layer. Figure 2 This is a cross-sectional schematic diagram of the organic functional layer 300 in the applied device structure; wherein, 310 is the hole injection layer, 320 is the hole transport layer, 330 is the electron blocking layer, 340 is the light-emitting layer, 350 is the hole blocking layer, 360 is the electron transport layer, and 370 is the electron injection layer. Figure 1 As shown, substrate 100 can be any substrate typically used in organic light-emitting devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties.

[0025] A first electrode 200 is formed on the substrate 100. The first electrode 200 can be either a cathode or an anode. Here, the first electrode 200 can be simply a reflective electrode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), or their alloys, or it can be an electrode composed of a reflective film and a transparent or semi-transparent electrode, for example, a transparent or semi-transparent electrode layer with high work function formed on the reflective film. The transparent or semi-transparent electrode layer can be formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2); it can also be composed of a combination of metal and oxide, such as ITO / Ag / ITO, IGO / Al / IGO, or AZO / Ag / AZO.

[0026] like Figure 2 As shown, the organic functional layer 300 may include a light-emitting layer 340 (EML), and if the first electrode 200 is an anode, a hole transport region may be formed between the EML and the first electrode 200, and an electron transport region may be formed between the EML and the second electrode layer 400; if the first electrode 200 is a cathode, an electron transport region may be formed between the EML and the first electrode 200, and a hole transport region may be formed between the EML and the second electrode layer 400. The hole transport region may include at least one of a hole injection layer 310 (HIL), a hole transport layer 320 (HTL), and an electron blocking layer 330 (EBL). The electron transport region may include at least one of a hole blocking layer 350 (HBL), an electron transport layer 360 (ETL), and an electron injection layer 370 (EIL). Therefore, the organic functional layer 300 includes a light-emitting layer and a combination of at least two of the following layers: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The thickness of the organic functional layer 300 is 50nm-1000nm.

[0027] The hole injection layer 310 (HIL) may contain a hole injection material and a p-type doped material. The hole injection material may be selected from conventional hole injection materials in the prior art, preferably the same organic material as the hole transport layer. P-type doped materials are selected from charge-conducting compounds disclosed in the prior art, and may be selected from, but not limited to, compounds disclosed in the following patent documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2011120709A1, US20100096600A1, CN101728485A and WO2012095143A1.

[0028] The thickness of the hole injection layer of the present invention can be 1-50 nm, preferably 5-30 nm and more preferably 5-20 nm.

[0029] The hole transport layer 320 (HTL) is preferably made of a material with high hole mobility, which enables holes to be transferred from the anode or hole injection layer to the light-emitting layer. Materials such as triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, and carbazole derivatives can be selected. Preferably, the hole transport layer material of the present invention is selected from compounds with hole transport characteristics disclosed in the prior art, and may also be selected from compounds disclosed in the following patent documents, but not limited thereto: JP1996048656, CN1702065A, CN108250083A, CN101535256A, CN101638377A, CN103108859A, CN104114672A, JP2013214094, KR1020140132287, KR1020130088044, US20120112176A1, JP1989142657A, JP2014039015, DE102010045405A1 or CN110467536A.

[0030] The thickness of the hole transport layer of the present invention can be 10-200 nm, preferably 20-170 nm, and more preferably 40-140 nm.

[0031] The electron blocking layer 330 (EBL) requires a triplet energy level higher than that of the host material in the emitting layer, effectively blocking energy loss from the emitting layer material. The electron blocking layer material also possesses high hole mobility, facilitating hole injection and transport. Suitable electron blocking layer materials include triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, and carbazole derivatives. Preferably, the electron blocking layer material of the present invention may be selected from the compounds disclosed in the prior art, but is not limited thereto: CN102046613A, CN103782410A, CN105408448A, KR1020160049955A, CN105712962A, CN103108859A, KR1020130106255, CN107849001A, WO2014079527A1, CN102224150A, CN108369996A, US20170018710A1 or JP2008299983.

[0032] The thickness of the electron blocking layer of the present invention can be 1-100 nm, preferably 5-50 nm, and more preferably 5-30 nm.

[0033] The emissive layer 340 (EML) is located between the electron blocking layer and the hole blocking layer. The material of the emissive layer is one that emits visible light by receiving holes from the hole transport region and electrons from the electron transport region, and then combining the received holes and electrons. To obtain a high-efficiency OLED device, the emissive layer can use the same dopant material or multiple dopant materials. The dopant materials can be simple fluorescent materials, delayed fluorescence (TADF) materials, or phosphorescent materials, or a combination of different fluorescent materials, TADF materials, and phosphorescent materials. The emissive layer 340 can be a single emissive layer material or a composite emissive layer material stacked laterally or vertically. The host material can be classified as a red light host material, a green light host material, a blue light host material, etc., and the dopant materials can be classified as red light dopant materials, green light dopant materials, blue light dopant materials, etc. Taking a blue light-emitting device as an example, this invention uses the following materials as the host and guest materials for the light-emitting layer of the organic electroluminescent device: the host material can be one or a combination of two of anthracene derivatives, quinoxaline derivatives, triazine derivatives, xanthone derivatives, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives, or pyrimidine derivatives. The guest material can be a pyrene derivative, boron derivative, chrysodium derivative, spirofluorene derivative, iridium complex, or platinum complex.

[0034] Preferably, the main material of the light-emitting layer of the present invention may be selected from the following compounds disclosed in the prior art, but is not limited thereto: JP2002243545, CN1871192A, CN101980395A, WO2007110129A1, US20130119354A1, EP3896754A1, US20160359122A1, CN113816996A, US20200111968A1, US20220238817A1, WO2020209292A1, US20190305227A1, WO2016171429A2 or KR1020210051439A.

[0035] Preferably, the doping material for the light-emitting layer of the present invention may be selected from the compounds disclosed in the prior art, but is not limited thereto: JPWO2015102118A1, JP2016009488, CN108017662A, KR1020180151781, KR1020180151781, JP2022164618A, KR1020200009047, US10957869B2, CN10427707 5A, US20160133859A1, CN109721628A, US20020034656, WO2010028151, US20100244004, US20070190359 , US20070103060, CN115148914A, CN107573383A, US20190036045A1, KR1020190055166 or WO2011051404.

[0036] The thickness of the light-emitting layer of the present invention can be 5-70 nm, preferably 10-60 nm, and more preferably 20-50 nm.

[0037] A hole blocking layer 350 (HBL) can be disposed above the light-emitting layer. The triplet energy level of the hole blocking layer material is higher than that of the main material of the light-emitting layer, which can block energy loss from the light-emitting layer material; the hole blocking layer material has high electron mobility, which is beneficial to electron transport and reduces the driving voltage of the device. It can be selected as a triazine derivative, pyridine derivative, pyrimidine derivative, benzimidazole derivative, benzoxazole derivative, or phenanthroline derivative, etc. Preferably, the hole-blocking layer material of the present invention may be selected from the following compounds disclosed in the prior art, but is not limited thereto: JP2015111679, KR1020180043220A, CN107108529A, CN103380508A, CN109564982A, CN106132937A, KR1020140040818, KR1020180065246A, JP2011063584A or KR1020120110303.

[0038] The thickness of the hole blocking layer of the present invention can be 2-100nm, preferably 5-50nm, and more preferably 5-40nm.

[0039] An electron transport layer 360 (ETL) is disposed above the hole blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. The electron transport layer comprises one or more organic compounds of the present invention. Preferably, the electron transport layer consists of the compound of the present invention and other electron transport layer materials. More preferably, the other electron transport layer materials are commonly used electron transport materials in the art. Most preferably, the electron transport layer consists of the compound of the present invention and LiQ, and the ratio of the organic compound of the present invention to the other electron transport layer materials is 1:9-9:1, preferably 2:8-8:2, more preferably 4:6-6:4, and most preferably 5:5.

[0040] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm, and more preferably 20-40 nm.

[0041] An electron injection layer 370 (EIL) is disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal. As the electron injection layer material for the organic electroluminescent device of the present invention, materials disclosed in the prior art for organic electroluminescent devices can be used, but are not limited to: LiF, Cs₂CO₃, CsF, Csq, NaF, MgF₂, CaF₂, Al₂O₃, or Yb.

[0042] 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 1-2 nm.

[0043] The second electrode 400 is disposed above the electron injection layer. In this invention, the second electrode is used as the cathode. The material used to form the cathode can be a material with a low work function, such as a metal, alloy, conductive compound, or a mixture thereof. Non-limiting examples of cathode materials may include lithium (Li), ytterbium (Yb), magnesium (Mg), aluminum (Al), calcium (Ca), as well as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The thickness of the cathode depends on the material used, typically 5-100 nm, preferably 10-50 nm, and more preferably 10-30 nm.

[0044] The light extraction layer 500 can effectively enhance the microcavity resonance effect of the device, reduce the total internal reflection effect, and improve the luminous efficiency of the device. To further improve the light extraction efficiency of organic electroluminescent devices, a light extraction layer can be added above the second electrode (i.e., the cathode). The light extraction layer material can be a triarylamine derivative, a triazine derivative, a benzimidazole derivative, a benzoxazole derivative, a benzothiazole derivative, a dibenzofuran derivative, or a carbazole derivative, etc. Preferably, the light extraction layer material of the present invention may be selected from the compounds disclosed in the prior art, but is not limited thereto: JP1995126615A, WO2011043083A1, CN107275370A, CN103828485A, CN106946859A, KR1020170116927A, JP2017244969, CN110229145A or KR1020170116927A.

[0045] The thickness of the light extraction layer of the present invention can be 10-200nm, preferably 30-120nm, and more preferably 50-90nm.

[0046] Method for fabricating organic electroluminescent devices: The method for fabricating the above-mentioned organic electroluminescent devices according to the present invention includes sequentially laminating a first electrode, a multilayer organic thin film layer, and a second electrode on a substrate. The multilayer organic thin film layer is formed by sequentially laminating a hole transport region, a light-emitting layer, and an electron transport region on the first electrode from bottom to top. The hole transport region is formed by sequentially laminating a hole injection layer, a hole transport layer, and an electron blocking layer on the first electrode from bottom to top. The electron transport region is formed by sequentially laminating a hole blocking layer, an electron transport layer, and an electron injection layer on the light-emitting layer from bottom to top. Optionally, a light extraction layer may also be laminated on the second electrode to improve the light extraction efficiency of the organic electroluminescent device.

[0047] Exemplary embodiments have been disclosed herein. While specific terminology has been used, it is intended and interpreted in a general and descriptive sense only, and not for limiting purposes. In some instances, as will be apparent to those skilled in the art upon the filing of this application, features, characteristics, and / or elements described in connection with particular embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless specifically indicated otherwise. Accordingly, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the invention.

[0048] The following examples are intended to better explain the present invention, but the scope of the invention is not limited thereto.

[0049] Example 1: Preparation of Compound O2

[0050] Preparation of intermediate M-1: In a 250 mL three-necked round-bottom flask, add 0.05 mol of starting material A-1, 0.07 mol of starting material B-1, 0.07 mol of sodium bisulfite, and 150 mL of N,N-dimethylacetamide. Start stirring and then heat to reflux for 20 hours. TLC monitoring showed complete reaction of the starting materials. Stop heating and pour the hot reaction mixture into ice water. After the solid precipitates, filter using a Buchner funnel to obtain the crude product. Recrystallize using a 1:1 mixture of toluene and ethanol. Wash the resulting solid with anhydrous ethanol to obtain intermediate M-1. Elemental analysis: Theoretical values: C, 73.27; H, 3.84; N, 10.68; Measured values: C, 73.31; H, 3.80; N, 10.71. LC-MS: Theoretical value: 262.07; Measured value: 263.24 ([M+H]) + ).

[0051] Preparation of intermediate N-1: In a 250 ml three-necked round-bottom flask, add 0.03 mol of intermediate M-1, 0.045 mol of triethylamine, and 150 ml of dichloromethane. Stir to dissolve, then slowly introduce sulfur dioxide fluoride gas while stirring, and react for 6 hours. TLC monitoring showed that the starting material reacted completely. Subsequently, remove residual sulfur dioxide fluoride gas by purging with argon gas. Transfer the reaction solution to a beaker, add 200 ml of 1 mol / L hydrochloric acid solution, and stir continuously for 30 min. After standing and separation, extract the aqueous phase twice with dichloromethane, combine the organic phases, add anhydrous magnesium sulfate to the organic phase for drying, remove the solvent by rotary evaporation, and perform column chromatography with a dichloromethane:petroleum ether = 1:4 mixture to obtain the fluorosulfonate of intermediate M-1. Next, 0.02 mol of the fluorosulfonate of intermediate M-1, 0.1 mol of lithium bromide, and 0.002 mol of the catalyst chloro(pentamethylcyclopentadiene)(cyclooctadiene)ruthenium(II) (CAS: 92390-26-6) were added sequentially to a dry Schlenk tube (with a screw cap), and the mixture was purged with argon for 10 min. Then, 10 mL of 0.25 mol / L 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone was added, and the mixture was stirred and refluxed under argon for 16 hours. TLC monitoring showed that the reactants had reacted completely, so heating was stopped, the mixture was cooled to room temperature, and then 20 mL of distilled water was added. The mixture was allowed to stand and separated. The aqueous phase was extracted twice with ethyl acetate, and the organic phases were combined. Anhydrous magnesium sulfate was added to the organic phase for drying, and the solvent was removed by rotary evaporation. The mixture was then subjected to column chromatography with a 1:4 mixture of dichloromethane and petroleum ether to obtain intermediate N-1. Elemental analysis: Theoretical values: C, 59.10; H, 2.79; N, 8.62; Measured values: C, 59.13; H, 2.75; N, 8.66. LC-MS: Theoretical value: 323.99; Measured value: 234.86 ([M+H]). + ).

[0052] Preparation of intermediate P-1: In a 250 ml three-necked round-bottom flask, add 0.03 mol of intermediate N-1, 0.033 mol of pinacol diboronate (CAS: 73183-34-3), 0.045 mol of potassium acetate, and 2.0 × 10⁻⁶ mol of sodium hydroxide. -3 mol of Pd(dba)2, 3.0 × 10 -31 mol of PCy3 and 150 ml of dioxane were added, stirred, and purged with nitrogen for 15 minutes. The temperature was raised to 80°C, and the system was kept under nitrogen atmosphere for 14 hours. TLC monitoring showed that intermediate N-1 reacted completely. Heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The solution was filtered, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:5 mixture of dichloromethane and petroleum ether to obtain intermediate P-1. Elemental analysis: Theoretical values: C, 70.99; H, 5.69; N, 7.53; Measured values: C, 70.95; H, 5.72; N, 7.48. LC-MS theoretical value: 372.16; Measured value: 373.10 ([M+H]). + ).

[0053] Preparation of intermediate H-1: In a 250 ml three-necked round-bottom flask, add 0.05 mol of raw material C-1, 0.06 mol of raw material D-1, 0.15 mol of sodium carbonate, and 5 × 10⁻⁶ mol of sodium carbonate. -4 50 ml of Pd(PPh3)4, 50 ml of toluene, 50 ml of ethanol, and 50 ml of distilled water were added. Stirring was started, and nitrogen was purged for 15 minutes. The mixture was then heated to reflux, and the system was kept under nitrogen atmosphere for 13 hours. TLC monitoring showed complete reaction of the starting materials. Heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The mixture was filtered, and 200 ml of dichloromethane was added to the filtrate. The mixture was then transferred to a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted twice with 100 ml of ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Column chromatography was performed using a toluene:petroleum ether mixture of 1:3 to obtain intermediate H-1. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.83; H, 3.04. LC-MS: Theoretical value: 265.95; Measured value: 266.85 ([M+H]). + ).

[0054] Preparation of intermediate G-1: In a 250 ml three-necked round-bottom flask, add 0.05 mol of intermediate H-1, 0.06 mol of intermediate P-1, 0.15 mol of potassium carbonate, and 6 × 10⁻⁶ mol of sodium carbonate. -41 mol of Pd(PPh3)4, 50 ml of distilled water, and 100 ml of tetrahydrofuran were added. Stirring was started, and nitrogen was purged for 15 minutes. The mixture was then heated to reflux, and the system was kept under nitrogen atmosphere for 20 hours. TLC monitoring confirmed complete reaction of the starting materials. Heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The mixture was filtered, and 200 ml of dichloromethane was added to the filtrate. The mixture was then transferred to a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted twice with 100 ml of ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:5 mixture of dichloromethane and petroleum ether to obtain intermediate G-1. Elemental analysis: Theoretical values: C, 77.69; H, 3.96; N, 6.47; Measured values: C, 77.65; H, 3.93; N, 6.50. LC-MS: Theoretical value: 432.10; Measured value: 433.22 ([M+H]) + ).

[0055] Preparation of intermediate L-1: In a 250 ml three-necked round-bottom flask, add 0.05 mol of intermediate E-1, 0.06 mol of pinacol diboronate (CAS: 73183-34-3), 0.075 mol of potassium acetate, and 4.0 × 10⁻⁶ mol of sodium hydroxide solution. -3 mol of Pd(dba)2, 5.0 × 10 -3 1 mol of PCy3 and 150 ml of dioxane were added, stirred, and purged with nitrogen for 15 minutes. The temperature was raised to 80°C, and the system was kept under nitrogen atmosphere for 10 hours. TLC monitoring showed that the reactants had reacted completely, so the heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The solution was filtered, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:4 mixture of dichloromethane and petroleum ether to obtain intermediate L-1. Elemental analysis: Theoretical values: C, 71.57; H, 5.78; N, 12.84; Measured values: C, 71.52; H, 5.80; N, 12.86. LC-MS theoretical value: 436.21; Measured value: 437.08 ([M+H]). + ).

[0056] Preparation of compound 02: In a 250 ml three-necked round-bottom flask, add 0.06 mol of intermediate L-1, 0.05 mol of intermediate G-1, 0.20 mol of potassium carbonate, and 8 × 10⁻⁶ mol of precipitate. -4mol of Pd(PPh3)4, 50 ml of distilled water, and 100 ml of tetrahydrofuran were added. Stirring was started, and nitrogen was purged for 15 minutes. The mixture was then heated to reflux, and the system was kept under nitrogen atmosphere for 21 hours. TLC monitoring confirmed complete reaction of the starting materials. Heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The mixture was filtered, and 200 ml of dichloromethane was added to the filtrate. The mixture was then transferred to a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted twice with 100 ml of dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:5 mixture of dichloromethane and petroleum ether to obtain compound O2. Elemental analysis: Theoretical values: C, 81.57; H, 4.28; N, 11.89; Measured values: C, 81.56; H, 4.25; N, 11.92. LC-MS: Theoretical value: 706.25; Measured value: 707.14 ([M+H]) + ).

[0057] Example 2: Preparation of Compound 18

[0058] Preparation of intermediate L-2: Refer to the preparation of intermediate L-1, except that raw material E-2 is used instead of E-1. Elemental analysis: Theoretical values: C, 71.57; H, 5.78; N, 12.84; Measured values: C, 71.55; H, 5.76; N, 12.90. LC-MS theoretical value: 436.21; Measured value: 437.35 ([M+H]). + Preparation of Compound 18: The preparation method for Compound 02 was the same as that for Compound 02, except that intermediate L-2 replaced intermediate L-1. Elemental Analysis: Theoretical values: C, 81.57; H, 4.28; N, 11.89; Measured values: C, 81.53; H, 4.30; N, 11.90. LC-MS: Theoretical value: 706.25; Measured value: 707.34 ([M+H]). + ).

[0059] Example 3: Preparation of Compound 46

[0060] Preparation of intermediate F-1: In a 250 ml three-necked round-bottom flask, add 0.05 mol of starting material N-1, 0.06 mol of starting material 2-chlorophenylboronic acid, 0.20 mol of sodium carbonate, and 8 × 10⁸ ml of hot water. -41 mol of Pd(PPh3)4, 50 ml of toluene, 50 ml of ethanol, and 50 ml of distilled water were added. Stirring was started, and nitrogen was purged for 15 minutes. The mixture was then heated to reflux, and the system was kept under nitrogen atmosphere for 16 hours. TLC monitoring confirmed complete reaction of the starting materials. Heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The mixture was filtered, and 200 ml of dichloromethane was added to the filtrate. The mixture was then transferred to a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted twice with 100 ml of ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:5 mixture of dichloromethane and petroleum ether to obtain intermediate F-1. Elemental analysis: Theoretical values: C, 74.06; H, 3.67; N, 7.85; Measured values: C, 74.02; H, 3.71; N, 7.83. LC-MS: Theoretical value: 356.07; Measured value: 357.19 ([M+H]) + ).

[0061] Preparation of intermediate K-1: In a 250 ml three-necked round-bottom flask, add 0.04 mol of intermediate F-1, 0.044 mol of pinacol diboronate (CAS: 73183-34-3), 0.05 mol of potassium acetate, and 3.0 × 10⁻⁶ mol of sodium hydroxide solution. -3 mol of Pd(dba)2, 4.0 × 10 - 3 1 mol of PCy3 and 150 ml of dioxane were added, stirred, and purged with nitrogen for 15 minutes. The temperature was raised to 80°C, and the system was kept under nitrogen atmosphere for 18 hours. TLC monitoring showed that the reactants had reacted completely, so the heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The mixture was filtered, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:4 mixture of dichloromethane and petroleum ether to obtain intermediate K-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.62; N, 6.25; Measured values: C, 75.05; H, 5.60; N, 6.23. LC-MS theoretical value: 448.20; Measured value: 449.11 ([M+H]). + ).

[0062] Preparation of intermediate G-2: Refer to the preparation of intermediate G-1, except that raw material P-1 is replaced with raw material K-1. Elemental analysis: Theoretical values: C, 80.23; H, 4.16; N, 5.50; Measured values: C, 80.20; H, 4.20; N, 5.47. LC-MS theoretical value: 508.13; Measured value: 509.07 ([M+H]). +Preparation of intermediate L-3: Refer to the preparation of intermediate L-1, except that raw material E-3 was used instead of E-1. Elemental analysis: Theoretical values: C, 71.57; H, 5.78; N, 12.84; Measured values: C, 71.62; H, 5.80; N, 12.88. LC-MS theoretical value: 436.21; Measured value: 437.40 ([M+H]). + Preparation of Compound 46: The preparation method was the same as that of Compound 02, except that intermediate L-3 replaced intermediate L-1, and intermediate G-2 replaced intermediate G-1. Elemental Analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.82; H, 4.36; N, 10.70. LC-MS: Theoretical value: 782.28; Measured value: 783.19 ([M+H]). + ).

[0063] Example 4: Preparation of Compound 83

[0064] Preparation of intermediate H-2: Refer to the preparation of intermediate H-1, except that starting material C-2 is used instead of starting material C-1. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.80; H, 3.05. LC-MS: Theoretical value: 265.95; Measured value: 266.91 ([M+H]). + ).

[0065] Preparation of intermediate G-3: Similar to the preparation of intermediate G-1, except that raw material H-2 replaces raw material H-1, and raw material K-1 replaces raw material P-1. Elemental analysis: Theoretical values: C, 80.23; H, 4.16; N, 5.50; Measured values: C, 80.26; H, 4.18; N, 5.44. LC-MS theoretical value: 508.13; Measured value: 509.24 ([M+H]). + ).

[0066] Preparation of intermediate I-1: In a 250 ml three-necked round-bottom flask, add 0.05 mol of starting material E-4, 0.06 mol of starting material 2-chlorophenylboronic acid, 0.25 mol of sodium carbonate, and 6 × 10⁻⁶ mol of sodium carbonate. -41 mol of Pd(PPh3)4, 50 ml of toluene, 50 ml of ethanol, and 50 ml of distilled water were added. Stirring was started, and nitrogen was purged for 15 minutes. The mixture was then heated to reflux, and the system was kept under nitrogen atmosphere for 11 hours. TLC monitoring showed complete reaction of the starting materials. Heating was stopped, and the reaction solution was allowed to cool naturally to room temperature. The mixture was filtered, and 200 ml of dichloromethane was added to the filtrate. The mixture was then transferred to a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted twice with 100 ml of ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Column chromatography was performed using a 1:5 mixture of dichloromethane and petroleum ether to obtain intermediate I-1. Elemental analysis: Theoretical values: C, 74.19; H, 4.07; N, 13.31; Measured values: C, 74.21; H, 4.09; N, 13.26. LC-MS: Theoretical value: 420.11; Measured value: 421.18 ([M+H]) + ).

[0067] Preparation of intermediate L-4: Refer to the preparation of intermediate L-1, except that raw material I-1 is used instead of raw material E-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.70; N, 10.93; Measured values: C, 75.05; H, 5.72; N, 10.88. LC-MS theoretical value: 512.24; Measured value: 513.12 ([M+H]). + ).

[0068] Preparation of Compound 83: The preparation method for Compound 02 was the same, except that intermediate L-4 replaced intermediate L-1, and intermediate G-3 replaced intermediate G-1. Elemental Analysis: Theoretical values: C, 83.89; H, 4.46; N, 9.78; Measured values: C, 83.91; H, 4.42; N, 9.81. LC-MS: Theoretical value: 858.31; Measured value: 859.16 ([M+H]). + ).

[0069] Example 5: Preparation of Compound 108

[0070] Preparation of Intermediate I-2: The preparation method for Intermediate I-1 was the same, except that 1-chlorophenylboronic acid was used instead of 2-chlorophenylboronic acid. Elemental analysis: Theoretical values: C, 74.19; H, 4.07; N, 13.31; Measured values: C, 74.23; H, 4.04; N, 13.29. LC-MS: Theoretical value: 420.11; Measured value: 421.27 ([M+H]). +Preparation of intermediate L-5: Refer to the preparation of intermediate L-1, except that raw material I-2 was used instead of raw material E-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.70; N, 10.93; Measured values: C, 74.96; H, 5.68; N, 10.96. LC-MS theoretical value: 512.24; Measured value: 513.33 ([M+H]). + Preparation of compound 108: The preparation method for compound 02 was the same, except that intermediate L-5 replaced intermediate L-1. Elemental analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.80; H, 4.41; N, 10.69. LC-MS: Theoretical value: 782.28; Measured value: 783.36 ([M+H]). + ).

[0071] Example 6: Preparation of Compound 128

[0072] Preparation of intermediate F-2: Similar to the preparation of intermediate F-1, except that 1-chlorophenylboronic acid was used instead of 2-chlorophenylboronic acid. Elemental analysis: Theoretical values: C, 74.06; H, 3.67; N, 7.85; Measured values: C, 74.09; H, 3.70; N, 7.82. LC-MS: Theoretical value: 356.07; Measured value: 357.23 ([M+H]). + Preparation of intermediate K-2: Refer to the preparation of intermediate K-1, except that raw material F-2 is used instead of F-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.62; N, 6.25; Measured values: C, 75.06; H, 5.58; N, 6.21. LC-MS theoretical value: 448.20; Measured value: 449.32 ([M+H]). + Preparation of intermediate H-3: Refer to the preparation of intermediate H-1, except that starting material C-1 is replaced with starting material C-3. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.92; H, 2.97. LC-MS: Theoretical value: 265.95; Measured value: 266.86 ([M+H]). +Preparation of intermediate G-4: Refer to the preparation of intermediate G-1, except that raw material H-3 replaces raw material H-1, and raw material K-2 replaces raw material P-1. Elemental analysis: Theoretical values: C, 80.23; H, 4.16; N, 5.50; Measured values: C, 80.30; H, 4.10; N, 5.55. LC-MS theoretical value: 508.13; Measured value: 509.26 ([M+H]). + Preparation of Compound 128: The preparation method was the same as that of Compound 02, except that intermediate L-2 replaced intermediate L-1, and intermediate G-4 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.78; H, 4.35; N, 10.75. LC-MS: Theoretical value: 782.28; Measured value: 783.20 ([M+H]). + ).

[0073] Example 7: Preparation of Compound 153

[0074] Preparation of intermediate H-4: Refer to the preparation of intermediate H-1, except that starting material C-4 is used instead of C-1. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.82; H, 2.99. LC-MS: Theoretical value: 265.95; Measured value: 266.90 ([M+H]). + Preparation of intermediate G-5: Refer to the preparation of intermediate G-1, except that raw material H-4 is used instead of H-1. Elemental analysis: Theoretical values: C, 77.69; H, 3.96; N, 6.47; Measured values: C, 77.75; H, 3.99; N, 6.45. LC-MS: Theoretical value: 432.10; Measured value: 433.17 ([M+H]). + Preparation of intermediate L-6: Refer to the preparation of intermediate L-1, except that raw material E-5 was used instead of E-1. Elemental analysis: Theoretical values: C, 71.57; H, 5.78; N, 12.84; Measured values: C, 71.60; H, 5.75; N, 12.88. LC-MS theoretical value: 436.21; Measured value: 437.30 ([M+H]). +Preparation of Compound 153: The preparation method was the same as that of Compound 02, except that intermediate L-6 replaced intermediate L-1, and intermediate G-5 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 81.57; H, 4.28; N, 11.89; Measured values: C, 81.52; H, 4.33; N, 11.90. LC-MS: Theoretical value: 706.25; Measured value: 707.36 ([M+H]). + ).

[0075] Example 8: Preparation of compound 204

[0076] Preparation of intermediate I-3: The preparation method for intermediate I-1 was the same, except that raw material E-2 was used instead of raw material E-4. Elemental analysis: Theoretical values: C, 74.19; H, 4.07; N, 13.31; Measured values: C, 74.26; H, 4.09; N, 13.24. LC-MS: Theoretical value: 420.11; Measured value: 421.02 ([M+H]). + Preparation of intermediate L-7: Refer to the preparation of intermediate L-1, except that raw material I-3 was used instead of raw material E-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.70; N, 10.93; Measured values: C, 74.96; H, 5.68; N, 10.96. LC-MS theoretical value: 512.24; Measured value: 513.20 ([M+H]). + Preparation of compound 204: The preparation method was the same as that of compound 02, except that intermediate L-7 replaced intermediate L-1, and intermediate G-5 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.80; H, 4.40; N, 10.70. LC-MS: Theoretical value: 782.28; Measured value: 783.45 ([M+H]). + ).

[0077] Example 9: Preparation of Compound 222

[0078] Preparation of intermediate H-5: Refer to the preparation of intermediate H-1, except that starting material C-5 is used instead of C-1. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.93; H, 3.06. LC-MS: Theoretical value: 265.95; Measured value: 266.89 ([M+H]). +Preparation of intermediate G-6: Refer to the preparation of intermediate G-1, except that raw material H-5 is used instead of H-1. Elemental analysis: Theoretical values: C, 80.23; H, 4.16; N, 5.50; Measured values: C, 80.18; H, 4.14; N, 5.51. LC-MS theoretical value: 508.13; Measured value: 509.19 ([M+H]). + Preparation of Compound 222: The preparation method for Compound 02 was the same, except that intermediate L-5 replaced intermediate L-1, and intermediate G-6 replaced intermediate G-1. Elemental Analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.90; H, 4.42; N, 10.65. LC-MS: Theoretical value: 782.28; Measured value: 783.33 ([M+H]). + ).

[0079] Example 10: Preparation of Compound 246

[0080] Preparation of intermediate H-6: Refer to the preparation of intermediate H-1, except that starting material C-6 is used instead of C-1. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.81; H, 3.05. LC-MS: Theoretical value: 265.95; Measured value: 266.75 ([M+H]). + Preparation of intermediate Q-1: Refer to the preparation of intermediate G-2, except that raw material H-6 replaces raw material H-1, and raw material L-2 replaces the original K-1. Elemental analysis: Theoretical values: C, 77.33; H, 4.26; N, 11.27; Measured values: C, 77.30; H, 4.29; N, 11.25. LC-MS theoretical value: 496.15; Measured value: 497.30 ([M+H]). + Preparation of Compound 246: The preparation method was the same as that of Compound 02, except that intermediate N-1 replaced intermediate L-1, and intermediate K-1 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.78; H, 4.35; N, 10.80. LC-MS: Theoretical value: 782.28; Measured value: 783.41 ([M+H]). + ).

[0081] Example 11: Preparation of Compound 266

[0082] Preparation of intermediate I-4: The preparation method for intermediate I-1 was the same, except that raw material E-3 was used instead of raw material E-4. Elemental analysis: Theoretical values: C, 74.19; H, 4.07; N, 13.31; Measured values: C, 74.14; H, 4.05; N, 13.36. LC-MS: Theoretical value: 420.11; Measured value: 421.33 ([M+H]). + Preparation of intermediate L-8: Refer to the preparation of intermediate L-1, except that raw material I-4 was used instead of raw material E-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.70; N, 10.93; Measured values: C, 75.05; H, 5.68; N, 10.92. LC-MS theoretical value: 512.24; Measured value: 513.41 ([M+H] + Preparation of intermediate H-7: Refer to the preparation of intermediate H-1, except that starting material C-7 is used instead of C-1. Elemental analysis: Theoretical values: C, 53.87; H, 3.01; Measured values: C, 53.83; H, 3.03. LC-MS: Theoretical value: 265.95; Measured value: 266.68 ([M+H]). + Preparation of intermediate Q-2: Refer to the preparation of intermediate N-1, except that raw material H-7 replaces raw material H-6, and raw material L-8 replaces raw material L-2. Elemental analysis: Theoretical values: C, 79.64; H, 4.40; N, 9.78; Measured values: C, 79.60; H, 4.42; N, 9.81. LC-MS theoretical value: 572.18; Measured value: 573.30 ([M+H]). + Preparation of Compound 266: The preparation method was the same as that of Compound 02, except that intermediate P-1 replaced intermediate L-1, and intermediate Q-2 replaced intermediate G-1. Elemental Analysis: Theoretical values: C, 82.84; H, 4.38; N, 10.73; Measured values: C, 82.75; H, 4.44; N, 10.75. LC-MS: Theoretical value: 782.28; Measured value: 783.50 ([M+H]). + ).

[0083] Example 12: Preparation of compound 299

[0084] Following the preparation method of intermediate I-2, intermediate I-5 was prepared by replacing raw material E-1 with raw material E-6. Elemental analysis: Theoretical values: C, 74.19; H, 4.07; N, 13.31; Measured values: C, 74.17; H, 4.10; N, 13.35. LC-MS: Theoretical value: 420.11; Measured value: 421.44 ([M+H]). + Preparation of intermediate L-9: Refer to the preparation of intermediate L-1, except that raw material I-5 was used instead of raw material E-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.70; N, 10.93; Measured values: C, 75.03; H, 5.77; N, 10.90. LC-MS theoretical value: 512.24; Measured value: 513.34 ([M+H]). + Preparation of intermediate G-7: Refer to the preparation of intermediate G-1, except that raw material H-7 replaces raw material H-1, and raw material K-1 replaces raw material P-1. Elemental analysis: Theoretical values: C, 80.23; H, 4.16; N, 5.50; Measured values: C, 80.26; H, 4.13; N, 5.53. LC-MS theoretical value: 508.13; Measured value: 509.29 ([M+H]). + Preparation of Compound 299: The preparation method for Compound 02 was the same, except that intermediate L-9 replaced intermediate L-1, and intermediate G-7 replaced intermediate G-1. Elemental Analysis: Theoretical values: C, 83.89; H, 4.46; N, 9.78; Measured values: C, 83.92; H, 4.43; N, 9.80. LC-MS: Theoretical value: 858.31; Measured value: 859.18 ([M+H]). + ).

[0085] Example 13: Preparation of compound 314

[0086] Preparation of intermediate M-2: Refer to the preparation of intermediate M-1, except that raw material B-2 is used instead of raw material B-1. Elemental analysis: Theoretical values: C, 78.09; H, 4.17; N, 8.28; Measured values: C, 78.10; H, 4.20; N, 8.24. LC-MS: Theoretical value: 338.11; Measured value: 339.20 ([M+H]). +Preparation of intermediate N-2: Refer to the preparation of intermediate N-1, except that starting material M-2 is used instead of starting material M-1. Elemental analysis: Theoretical values: C, 65.85; H, 3.27; N, 6.98; Measured values: C, 65.850; H, 3.30; N, 6.95. LC-MS: Theoretical value: 400.02; Measured value: 401.18 ([M+H]) + Preparation of intermediate P-2: Refer to the preparation of intermediate P-1, except that starting material N-2 is used instead of N-1. Elemental analysis: Theoretical values: C, 75.01; H, 5.62; N, 6.25; Measured values: C, 75.04; H, 5.60; N, 6.27. LC-MS theoretical value: 448.20; Measured value: 449.31 ([M+H]). + Preparation of intermediate H-8: Refer to the preparation of intermediate H-1, except that starting material D-2 is used instead of D-1. Elemental analysis: Theoretical values: C, 53.37; H, 2.41; N, 4.79; Measured values: C, 53.35; H, 2.40; N, 4.77. LC-MS: Theoretical value: 290.95; Measured value: 291.84 ([M+H]). + Preparation of intermediate G-8: Refer to the preparation of intermediate G-1, except that raw material H-8 replaces raw material H-1, and raw material P-2 replaces raw material P-1. Elemental analysis: Theoretical values: C, 78.72; H, 3.78; N, 7.87; Measured values: C, 78.70; H, 3.75; N, 7.89. LC-MS theoretical value: 533.13; Measured value: 534.22 ([M+H]). + ).

[0087] Preparation of compound 314: The preparation method was the same as that of compound 02, except that intermediate L-6 replaced intermediate L-1, and intermediate G-8 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 81.77; H, 4.12; N, 12.14; Measured values: C, 81.75; H, 4.10; N, 12.16. LC-MS: Theoretical value: 807.27; Measured value: 808.30 ([M+H]). + ).

[0088] Example 14: Preparation of compound 332

[0089] Preparation of intermediate M-3: Refer to the preparation of intermediate M-1, except that raw material B-3 is used instead of raw material B-1. Elemental analysis: Theoretical values: C, 76.91; H, 3.87; N, 8.97; Measured values: C, 76.95; H, 3.84; N, 8.95. LC-MS: Theoretical value: 312.09; Measured value: 313.21 ([M+H]) + ).

[0090] Preparation of intermediate N-3: Refer to the preparation of intermediate N-1, except that starting material M-3 is used instead of M-1. Elemental analysis: Theoretical values: C, 64.02; H, 2.96; N, 7.47; Measured values: C, 64.06; H, 2.93; N, 7.45. LC-MS: Theoretical value: 374.01; Measured value: 375.10 ([M+H]). + ).

[0091] Preparation of intermediate P-3: Similar to the preparation of intermediate P-1, except that starting material N-3 was used instead of N-1. Elemental analysis: Theoretical values: C, 73.95; H, 5.49; N, 6.63; Measured values: C, 73.98; H, 5.45; N, 6.60. LC-MS theoretical value: 422.18; Measured value: 423.35 ([M+H]). + ).

[0092] Preparation of intermediate H-9: Refer to the preparation of intermediate H-1, except that raw material D-3 is used instead of raw material D-1. Elemental analysis: Theoretical values: C, 49.20; H, 2.63; N, 5.22; Measured values: C, 49.22; H, 2.66; N, 5.17. LC-MS: Theoretical value: 266.95; Measured value: 267.77 ([M+H]). + ).

[0093] Preparation of intermediate G-9: Similar to the preparation of intermediate G-1, except that raw material H-9 replaces raw material H-1, and raw material P-3 replaces raw material P-1. Elemental analysis: Theoretical values: C, 76.94; H, 3.75; N, 8.68; Measured values: C, 76.90; H, 3.79; N, 8.66. LC-MS theoretical value: 483.11; Measured value: 484.02 ([M+H]). + ).

[0094] Preparation of compound 332: The preparation method was the same as that of compound 02, except that intermediate L-7 replaced intermediate L-1, and intermediate G-9 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 82.09; H, 4.23; N, 11.76; Measured values: C, 82.04; H, 4.26; N, 11.74. LC-MS: Theoretical value: 833.29; Measured value: 834.45 ([M+H]). + ).

[0095] Example 15: Preparation of compound 349

[0096] Preparation of intermediate M-4: Refer to the preparation of intermediate M-1, except that raw material B-4 is used instead of raw material B-1. Elemental analysis: Theoretical values: C, 68.44; H, 3.45; N, 15.96; Measured values: C, 68.41; H, 3.48; N, 15.93. LC-MS: Theoretical value: 263.07; Measured value: 264.28 ([M+H]). + ).

[0097] Preparation of intermediate N-4: Refer to the preparation of intermediate N-1, except that starting material M-4 is used instead of M-1. Elemental analysis: Theoretical values: C, 55.24; H, 2.47; N, 12.88; Measured values: C, 55.20; H, 2.49; N, 12.89. LC-MS: Theoretical value: 324.99; Measured value: 325.87 ([M+H]). + ).

[0098] Preparation of intermediate P-4: Refer to the preparation of intermediate P-1, except that starting material N-4 is used instead of starting material N-1. Elemental analysis: Theoretical values: C, 67.58; H, 5.40; N, 11.26; Measured values: C, 67.55; H, 5.44; N, 11.24. LC-MS theoretical value: 373.16; Measured value: 374.43 ([M+H]). + ).

[0099] Preparation of intermediate G-10: Similar to the preparation of intermediate G-1, except that raw material H-8 replaces raw material H-1, and raw material P-4 replaces raw material P-1. Elemental analysis: Theoretical values: C, 73.28; H, 3.29; N, 12.21; Measured values: C, 73.27; H, 3.26; N, 12.25. LC-MS theoretical value: 458.09; Measured value: 459.26 ([M+H]). + ).

[0100] Preparation of compound 349: The preparation method was the same as that of compound 02, except that intermediate L-7 replaced intermediate L-1, and intermediate G-10 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 80.18; H, 3.99; N, 13.85; Measured values: C, 80.13; H, 3.96; N, 13.89. LC-MS: Theoretical value: 808.27; Measured value: 809.13 ([M+H]). + ).

[0101] Example 16: Preparation of Compound 362

[0102] Preparation of intermediate M-5: Refer to the preparation of intermediate M-1, except that raw material B-5 is used instead of raw material B-1. Elemental analysis: Theoretical values: C, 71.08; H, 3.16; N, 14.63; Measured values: C, 71.11; H, 3.15; N, 14.60. LC-MS: Theoretical value: 287.07; Measured value: 288.15 ([M+H]). + ).

[0103] Preparation of intermediate N-5: Refer to the preparation of intermediate N-1, except that starting material M-5 is used instead of M-1. Elemental analysis: Theoretical values: C, 58.31; H, 2.30; N, 12.00; Measured values: C, 58.32; H, 2.35; N, 11.95. LC-MS: Theoretical value: 348.99; Measured value: 348.92 ([M+H]). + ).

[0104] Preparation of intermediate P-5: Refer to the preparation of intermediate P-1, except that starting material N-5 is used instead of N-1. Elemental analysis: Theoretical values: C, 69.54; H, 5.08; N, 10.58; Measured values: C, 69.50; H, 5.09; N, 10.55. LC-MS theoretical value: 397.16; Measured value: 398.33 ([M+H]). + ).

[0105] Preparation of intermediate H-10: Similar to the preparation of intermediate H-1, except that raw material D-4 replaces raw material D-1, and raw material C-8 replaces raw material C-1. Elemental analysis: Theoretical values: C, 62.91; H, 3.52; Measured values: C, 62.94; H, 3.50. LC-MS: Theoretical value: 341.98; Measured value: 342.82 ([M+H]). + ).

[0106] Preparation of intermediate G-11: Similar to the preparation of intermediate G-1, except that raw material H-10 replaces raw material H-1, and raw material P-5 replaces raw material P-1. Elemental analysis: Theoretical values: C, 78.72; H, 3.78; N, 7.87; Measured values: C, 78.70; H, 3.75; N, 7.89. LC-MS theoretical value: 533.13; Measured value: 534.20 ([M+H]). + ).

[0107] Preparation of compound 362: The preparation method was the same as that of compound 02, except that intermediate L-6 replaced intermediate L-1, and intermediate G-11 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 81.77; H, 4.12; N, 12.14; Measured values: C, 81.75; H, 4.16; N, 12.10. LC-MS: Theoretical value: 807.27; Measured value: 808.29 ([M+H]). + ).

[0108] Example 17: Preparation of Compound 380

[0109] Preparation of intermediate M-6: Refer to the preparation of intermediate M-1, except that raw material B-6 is used instead of raw material B-1. Elemental analysis: Theoretical values: C, 68.44; H, 3.45; N, 15.96; Measured values: C, 68.40; H, 3.44; N, 15.92. LC-MS: Theoretical value: 263.07; Measured value: 264.39 ([M+H]). + ).

[0110] Preparation of intermediate N-6: Refer to the preparation of intermediate N-1, except that starting material M-6 is used instead of M-1. Elemental analysis: Theoretical values: C, 55.24; H, 2.47; N, 12.88; Measured values: C, 55.20; H, 2.49; N, 12.85. LC-MS: Theoretical value: 324.99; Measured value: 325.86 ([M+H]). + ).

[0111] Preparation of intermediate F-3: Refer to the preparation of intermediate F-1, except that raw material N-6 is used instead of the original N-1. Elemental analysis: Theoretical values: C, 70.50; H, 3.38; N, 11.74; Measured values: C, 70.54; H, 3.35; N, 11.72. LC-MS: Theoretical value: 357.07; Measured value: 358.28 ([M+H]). + ).

[0112] Preparation of intermediate K-3: Similar to the preparation of intermediate K-1, except that raw material F-1 was replaced with raw material F-3. Elemental analysis: Theoretical values: C, 72.18; H, 5.38; N, 9.35; Measured values: C, 72.16; H, 5.36; N, 9.33. LC-MS theoretical value: 449.19; Measured value: 450.36 ([M+H]). + ).

[0113] Preparation of intermediate H-11: Similar to the preparation of intermediate H-1, except that raw material D-5 replaces raw material D-1, and raw material C-9 replaces raw material C-1. Elemental analysis: Theoretical values: C, 49.20; H, 2.63; N, 5.22; Measured values: C, 49.24; H, 2.65; N, 5.18. LC-MS: Theoretical value: 266.95; Measured value: 267.98 ([M+H]). + ).

[0114] Preparation of intermediate G-12: Similar to the preparation of intermediate G-1, except that raw material H-11 was used instead of raw material H-1, and raw material K-3 was used instead of raw material P-1. Elemental analysis: Theoretical values: C, 75.22; H, 3.75; N, 10.96; Measured values: C, 75.20; H, 3.73; N, 10.95. LC-MS theoretical value: 510.12; Measured value: 511.15 ([M+H]). + ).

[0115] Preparation of Compound 380: The preparation method was the same as that of Compound 02, except that intermediate L-6 replaced intermediate L-1, and intermediate G-12 replaced intermediate G-1. Elemental Analysis: Theoretical values: C, 79.58; H, 4.11; N, 14.28; Measured values: C, 79.56; H, 4.14; N, 14.25. LC-MS: Theoretical value: 784.27; Measured value: 785.38 ([M+H]). + ).

[0116] Example 18: Preparation of compound 393

[0117] Preparation of intermediate M-7: Refer to the preparation of intermediate M-1, except that raw material B-7 is used instead of raw material B-1. Elemental analysis: Theoretical values: C, 71.08; H, 3.16; N, 14.63; Measured values: C, 71.05; H, 3.13; N, 14.67. LC-MS: Theoretical value: 287.07; Measured value: 288.132 ([M+H]) + Preparation of intermediate N-7: Refer to the preparation of intermediate N-1, except that starting material M-7 is used instead of M-1. Elemental analysis: Theoretical values: C, 58.31; H, 2.30; N, 12.00; Measured values: C, 58.34; H, 2.25; N, 12.04. LC-MS: Theoretical value: 348.99; Measured value: 349.87 ([M+H]). + Preparation of intermediate F-4: Refer to the preparation of intermediate F-1, except that raw material N-7 is used instead of the original N-1. Elemental analysis: Theoretical values: C, 72.35; H, 3.17; N, 11.01; Measured values: C, 72.30; H, 3.19; N, 11.03. LC-MS: Theoretical value: 381.07; Measured value: 382.31 ([M+H]). + Preparation of intermediate K-4: Refer to the preparation of intermediate K-1, except that raw material F-4 is used instead of F-1. Elemental analysis: Theoretical values: C, 73.59; H, 5.11; N, 8.88; Measured values: C, 73.55; H, 5.13; N, 8.90. LC-MS theoretical value: 473.19; Measured value: 474.06 ([M+H]). + ).

[0118] Preparation of intermediate H-12: Refer to the preparation of intermediate H-1, except that starting material D-6 is used instead of D-1. Elemental analysis: Theoretical values: C, 60.51; H, 3.17; Measured values: C, 60.54; H, 3.15. LC-MS: Theoretical value: 315.97; Measured value: 316.90 ([M+H]). + ).

[0119] Preparation of intermediate G-13: Similar to the preparation of intermediate G-1, except that raw material H-12 replaces raw material H-1, and raw material K-4 replaces raw material P-1. Elemental analysis: Theoretical values: C, 80.20; H, 3.80; N, 7.19; Measured values: C, 80.17; H, 3.82; N, 7.22. LC-MS theoretical value: 583.15; Measured value: 584.22 ([M+H]). + Preparation of compound 393: The preparation method was the same as that of compound 02, except that intermediate L-6 replaced intermediate L-1, and intermediate G-13 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 82.60; H, 4.11; N, 11.43; Measured values: C, 82.64; H, 4.08; N, 11.46. LC-MS: Theoretical value: 857.29; Measured value: 858.14 ([M+H]). + ).

[0120] Example 19: Preparation of Compound 414

[0121] Preparation of intermediate H-13: Similar to the preparation of intermediate H-1, except that raw material D-2 replaces raw material D-1, and raw material C-4 replaces raw material C-1. Elemental analysis: Theoretical values: C, 53.37; H, 2.41; N, 4.79; Measured values: C, 53.35; H, 2.44; N, 4.80. LC-MS: Theoretical value: 290.95; Measured value: 291.93 ([M+H]). + ).

[0122] Preparation of intermediate G-14: Similar to the preparation of intermediate G-1, except that raw material H-13 replaces raw material H-1, and raw material P-2 replaces raw material P-1. Elemental analysis: Theoretical values: C, 78.72; H, 3.78; N, 7.87; Measured values: C, 78.76; H, 3.75; N, 7.85. LC-MS theoretical value: 533.13; Measured value: 534.39 ([M+H]). + ).

[0123] Preparation of compound 414: The preparation method was the same as that of compound 02, except that intermediate L-7 replaced intermediate L-1, and intermediate G-14 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 82.88; H, 4.22; N, 11.09; Measured values: C, 82.86; H, 4.20; N, 11.11. LC-MS: Theoretical value: 883.31; Measured value: 884.16 ([M+H]).+ ).

[0124] Example 20: Preparation of Compound 431

[0125] Preparation of intermediate H-14: Similar to the preparation of intermediate H-1, except that raw material D-6 replaces raw material D-1, and raw material C-4 replaces raw material C-1. Elemental analysis: Theoretical values: C, 60.51; H, 3.17; Measured values: C, 60.48; H, 3.19. LC-MS: Theoretical value: 315.97; Measured value: 316.94 ([M+H]). + ).

[0126] Preparation of intermediate G-15: Similar to the preparation of intermediate G-1, except that raw material H-14 replaces raw material H-1, and raw material P-3 replaces raw material P-1. Elemental analysis: Theoretical values: C, 81.12; H, 3.97; N, 5.26; Measured values: C, 81.16; H, 3.95; N, 5.29. LC-MS theoretical value: 532.13; Measured value: 533.17 ([M+H]). + ).

[0127] Preparation of compound 431: The preparation method was the same as that of compound 02, except that intermediate L-6 replaced intermediate L-1, and intermediate G-15 replaced intermediate G-1. Elemental analysis: Theoretical values: C, 83.36; H, 4.25; N, 10.42; Measured values: C, 83.40; H, 4.22; N, 10.40. LC-MS: Theoretical value: 806.28; Measured value: 807.12 ([M+H]). + ).

[0128] Device Examples: The following device examples further illustrate the beneficial technical effects of applying the compounds of the present invention as electron transport layer materials in OLED devices. The materials, equipment, and testing methods used in the examples are either commercially available or synthesized by referring to existing literature.

[0129] The molecular structural formulas of the relevant materials are shown below:

[0130] Device Example: Structure of Device Example 1: Substrate layer 100 / First electrode (anode) layer 200 (Ag (100nm)) / Hole injection layer 310 (HT-1:P-1 = 98:2 mass ratio, thickness 10nm) / Hole transport layer 320 (HT-1, thickness 130nm) / Electron blocking layer 330 (EB-1, thickness 5nm) / Light emitting layer 340 (BH-1:BD-1 = 98:2 mass ratio, thickness 30nm) / Hole blocking layer 350 (HB-1, thickness 5nm) / Electron transport layer 360 (Compound O2:LiQ = 1:1 mass ratio, thickness 30nm) / Electron injection layer 370 (Yb, thickness 1nm) / Second electrode (cathode) layer 400 (Mg:Ag = 1:9 mass ratio, thickness 18nm) / Extraction layer 500 (CP-1, thickness 65nm).

[0131] Fabrication method of device embodiment 1: The transparent substrate layer 100 is transparent glass, and the first electrode (anode) layer 200 is Ag (100nm). The first electrode (anode) layer 200 is washed to remove organic residues from the surface. Then, on the anode layer 200, a hole injection layer 310 with a thickness of 10nm of HT-1 and P-1 is deposited, with a mass ratio of HT-1 to P-1 of 98:2. Next, a hole transport layer 320 with a thickness of 130nm of HT-1 is deposited. Subsequently, an electron blocking layer 330 with a thickness of 5nm of EB-1 is deposited. Next, a light-emitting layer 340 is deposited, which uses BH-1 as the host material and BD-1 as the dopant material, with a doping ratio of 2% by weight, and a film thickness of 30nm. After the light-emitting layer 340, HB-1 is deposited to a thickness of 5nm as a hole blocking layer 350. On top of the hole-blocking layer 350, compound O2 and LiQ of the present invention are deposited by vacuum evaporation at a mass ratio of 1:1. The vacuum-deposited film thickness of this layer is 30 nm, and this layer is the electron transport layer 360. On the electron transport layer 360, a Yb layer with a thickness of 1 nm is formed by vacuum evaporation, and this layer is the electron injection layer 370. On the electron injection layer 370, a Mg:Ag electrode layer with a thickness of 18 nm is formed by vacuum evaporation, with a Mg:Ag mass ratio of 1:9, and this layer is the second electrode (cathode) layer 400. On the cathode layer, a light extraction layer 500 is then deposited by vacuum evaporation, with a CP-1 layer having a thickness of 65 nm as the light extraction layer.

[0132] Device Examples 2-20 and Comparative Examples 1-4 are identical to Device Example 1 in terms of fabrication process and use the same substrate and electrode materials. The only difference is the change in the electron transport layer material. Performance tests were performed on the fabricated device examples and comparative examples. The current of the device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and the current density of the OLED device at different voltages was obtained by dividing the current by the emitting area. The current density and luminance of the OLED device at different voltages were measured using a Konica Minolta CS-2000 spectroradiometer, obtaining the luminance at the same current density (10 mA / cm²). 2 The operating voltage and device efficiency (BI) of the device are considered important parameters for measuring blue light luminescence efficiency. Device lifetime is defined as the device current density at 20 mA / cm². 2 The time required for the brightness to decay to 95% of the initial brightness under the operating current. The device test data are shown in Table 1.

[0133] Table 1. Light emission characteristics data of representative devices

[0134] The comparative compounds ET-1 to ET-4 used in the comparative examples have similar structural formulas to those of the present invention. However, as can be seen from the device test data in Table 1, compared with devices using ET-1 to ET-4 as electron transport layer materials, devices prepared using the representative compounds of the present invention as electron transport layers show significant improvements in driving voltage, device efficiency (BI), and device lifetime. The compounds of the present invention, by introducing a novel benzofuran-pyrimidine group core structure and a polypyridine group branched structure, and by altering the bridging groups and their connection sites between the benzofuran-pyrimidine group and pyridine, exhibit superior electron mobility, electron tolerance, and triplet exciton suppression capability. When used as electron transport materials in organic electroluminescent devices, they effectively reduce device driving voltage and improve device efficiency and lifetime. The compounds of the present invention achieve unexpectedly superior technical effects compared to the comparative compounds.

[0135] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are exhaustively listed. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0136] For those skilled in the art, various modifications and improvements can be made without departing from the concept of the present invention, and these modifications and improvements are all within the scope of protection of the present invention. The scope of protection of the present invention is defined by the appended claims.

Claims

1. An organic compound containing a benzofuranopyrimidine group, characterized in that, The organic compound has a structure as shown in formula (1): ； In equation (1), L1 and L2 are represented as single bonds or C6-C36 arylene groups, respectively, either the same or different. Ar and R1 are selected from substituted or unsubstituted C6-C36 aryl groups and substituted or unsubstituted C5-C36 heteroaryl groups, whether they are the same or different. When substituted, the substituted group is independently selected from deuterium or cyano. X1-X2, Y1-Y3, and Y4-Y6 are each selected as nitrogen atoms, and the others are carbon atoms.

2. The organic compound according to claim 1, characterized in that, L1 and L2 are represented by single bonds or phenylene, respectively, or in the same or different ways; Ar and R1 are selected from any one or more of cyano-substituted or unsubstituted phenyl, biphenyl, naphthyl, and pyridyl groups.

3. The organic compound according to claim 1, characterized in that, The organic compound has any one of the structures shown in formulas (I-1) to (I-3): ； The alternatives to L1, L2, Ar, R1, X1-X2, Y1-Y6 are as defined in claim (I).

4. The organic compound according to claim 1, characterized in that, The formula (I) described The structure is selected from the following: 。 5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any of the following chemical structures:

6. The use of the organic compound according to any one of claims 1-5 in the preparation of organic electroluminescent devices.

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: Substrate layer; A first electrode, which is on the substrate layer; An organic functional layer is disposed on the first electrode; A second electrode is provided on the organic functional layer. And a light extraction layer above the second electrode; the organic functional layer contains an organic compound as described in any one of claims 1-5.

8. An organic electroluminescent device, characterized in that, The organic functional layer includes an electron transport layer, wherein the electron transport layer contains the organic compound according to any one of claims 1-5.

9. A composition, characterized in that, The composition comprises one or more of the organic compounds according to any one of claims 1-5.

10. A display or lighting device, characterized in that, The display or lighting device includes one or more of the organic electroluminescent devices of claim 7.

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